NP-MRD: Showing NP-Card for Vitamin D3 (NP0001049)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-04-19 10:07:12 UTC

NP-MRD ID

NP0001049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vitamin D3

Description

Vitamin D3, also called cholecalciferol, is one of the forms of vitamin D. Vitamin D3 is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of Vitamin A. It is structurally similar to steroids such as testosterone, cholesterol, and cortisol (although vitamin D3, itself, is a secosteroid). Vitamin D3 is a derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. Vitamin D3 can also come from dietary sources, such as beef liver, cheese, egg yolks, and fatty fish (PubChem). The first step involved in the activation of vitamin D3 is a 25-hydroxylation catalyzed by 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyzes the first reaction in the oxidation of the side chain of sterol intermediates. The active form of vitamin D3 (calcitriol) binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by (1) increasing GI absorption of phosphorus and calcium, (2) increasing osteoclastic resorption, and (3) increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through the formation of a calcium-binding protein.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Vitamin D3.mol
  Mrv1652305271900322D          

 30 32  0  0  0  0            999 V2000
   -2.7522   -3.8021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4666   -4.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -3.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7522   -2.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -2.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -1.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -1.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -0.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -0.0896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1759   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608    0.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    0.9903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4308    1.7749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2456    1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    2.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518    3.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666    3.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326    4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088    0.7354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5225    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    1.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -0.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -2.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -2.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    1.1618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -0.9146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  6  0  0  0
 13 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
  4 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 29  1  6  0  0  0
 10 30  1  6  0  0  0
M  END

HMDB0000876
     RDKit          3D
Vitamin D3
 72 74  0  0  0  0  0  0  0  0999 V2000
   -4.4964    2.0982   -0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4231    1.3547   -0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5035    1.9245    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4871    0.7830    0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8240    0.0340   -0.3344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8903   -0.7958   -0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6556   -0.8241   -0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -0.0993   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408   -0.7003   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -0.0416    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738   -0.7261    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9359   -2.1551   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -2.8096   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119   -2.0788    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481   -0.6802    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3291   -0.5400   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -0.0380    0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5227    1.3777    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862    1.5928    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    0.1967    0.5419 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8666    0.2948   -0.3005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5322   -0.9896   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    1.3008    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963    1.7324   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2170    0.9890   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399    0.2995    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165   -0.7886    1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1844   -0.3745    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103    3.1628   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550    1.7141   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0424    2.7447    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0861    2.1765    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4548    1.1687    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1117    0.0493    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0655    0.7661   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6354   -1.5800    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6669   -1.8334   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6921   -0.9346   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2259   -1.7929   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.9811    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073   -2.3100   -1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -2.7671    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.9298   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -3.8420    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331   -2.0785    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -2.6505    0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6119    0.5061   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673   -0.5964   -1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.2835   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -0.1716    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    2.0711    1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    1.7098   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585    2.2041    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736    2.1152   -0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8772   -0.0377    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    0.7234   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -1.5311    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -1.7302   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -0.9444   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    1.0873    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    2.2966    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    2.3484   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280    2.6398    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818    0.3342   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804    1.8275   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3606    1.0263    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8507   -1.2522    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651   -0.4599    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -1.6660    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6890   -1.0234    0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285    0.4240   -0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7622   -0.9983   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
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 21 56  1  6
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
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 25 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

Vitamin D3.mol
  Mrv1652305271900322D          

 30 32  0  0  0  0            999 V2000
   -2.7522   -3.8021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4666   -4.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -3.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7522   -2.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -2.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -1.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -1.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -0.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -0.0896    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1759   -0.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608    0.3229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1759    0.9903    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4308    1.7749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2456    1.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411    2.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561    2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6518    3.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666    3.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326    4.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088    0.7354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5225    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    1.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -0.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -2.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -2.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828    1.1618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -0.9146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  6  0  0  0
 13 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  9 26  1  0  0  0  0
  4 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
 13 29  1  6  0  0  0
 10 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0001049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

> <INCHI_KEY>
QYSXJUFSXHHAJI-YRZJJWOYSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
49.63029019999946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

> <ALOGPS_LOGP>
7.98

> <JCHEM_LOGP>
7.125460754666667

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.384341369959035

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3184890847799178

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
123.22449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.80e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin D3

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000876
     RDKit          3D
Vitamin D3
 72 74  0  0  0  0  0  0  0  0999 V2000
   -4.4964    2.0982   -0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4231    1.3547   -0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5035    1.9245    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4871    0.7830    0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8240    0.0340   -0.3344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8903   -0.7958   -0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6556   -0.8241   -0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -0.0993   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408   -0.7003   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -0.0416    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738   -0.7261    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9359   -2.1551   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -2.8096   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119   -2.0788    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481   -0.6802    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3291   -0.5400   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -0.0380    0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5227    1.3777    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862    1.5928    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    0.1967    0.5419 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8666    0.2948   -0.3005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5322   -0.9896   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    1.3008    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963    1.7324   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2170    0.9890   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399    0.2995    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165   -0.7886    1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1844   -0.3745    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103    3.1628   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550    1.7141   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0424    2.7447    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0861    2.1765    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4548    1.1687    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1117    0.0493    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0655    0.7661   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6354   -1.5800    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6669   -1.8334   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6921   -0.9346   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2259   -1.7929   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.9811    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073   -2.3100   -1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -2.7671    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.9298   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -3.8420    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331   -2.0785    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -2.6505    0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6119    0.5061   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673   -0.5964   -1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.2835   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -0.1716    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    2.0711    1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    1.7098   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585    2.2041    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736    2.1152   -0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8772   -0.0377    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    0.7234   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -1.5311    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -1.7302   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -0.9444   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    1.0873    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    2.2966    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    2.3484   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280    2.6398    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818    0.3342   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804    1.8275   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3606    1.0263    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8507   -1.2522    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651   -0.4599    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -1.6660    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6890   -1.0234    0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285    0.4240   -0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7622   -0.9983   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  6
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Vitamin D3.mol                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -5.137  -7.097   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.471  -7.867   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.804  -7.867   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.470  -7.097   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.137  -5.557   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.804  -4.787   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.804  -3.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.470  -2.477   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.470  -0.937   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.136  -0.167   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.328  -0.643   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.233   0.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.328   1.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.804   3.313   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.325   3.554   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.877   4.992   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.398   5.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.950   6.671   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.471   6.911   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.981   7.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.165   4.510   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.136   1.373   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.975   2.904   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.470   2.143   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.804   1.373   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.804  -0.167   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.470  -5.557   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.136  -4.787   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.835   2.169   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.136  -1.707   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3   27                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   22   30                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22   29                                             
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14                                                            
CONECT   22   13   10   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9                                                       
CONECT   27    4    6   28                                                  
CONECT   28   27                                                            
CONECT   29   13                                                            
CONECT   30   10                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0000876
HETATM    1  C1  UNL     1      -4.496   2.098  -0.740  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.423   1.355  -0.178  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.503   1.924   0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.487   0.783   0.929  1.00  0.00           C  
HETATM    5  C5  UNL     1      -7.824   0.034  -0.334  1.00  0.00           C  
HETATM    6  O1  UNL     1      -8.890  -0.796  -0.069  1.00  0.00           O  
HETATM    7  C6  UNL     1      -6.656  -0.824  -0.814  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.394  -0.099  -0.425  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.241  -0.700  -0.249  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.016  -0.042   0.180  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.874  -0.726   0.278  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.936  -2.155  -0.071  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.591  -2.810  -0.174  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.512  -2.079   0.535  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.548  -0.680   0.026  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.329  -0.540  -1.444  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.677  -0.038   0.711  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.523   1.378   0.384  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.986   1.593   0.505  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.600   0.197   0.542  1.00  0.00           C  
HETATM   21  C20 UNL     1       2.867   0.295  -0.300  1.00  0.00           C  
HETATM   22  C21 UNL     1       3.532  -0.990  -0.487  1.00  0.00           C  
HETATM   23  C22 UNL     1       3.711   1.301   0.405  1.00  0.00           C  
HETATM   24  C23 UNL     1       4.996   1.732  -0.081  1.00  0.00           C  
HETATM   25  C24 UNL     1       6.217   0.989  -0.298  1.00  0.00           C  
HETATM   26  C25 UNL     1       6.940   0.300   0.789  1.00  0.00           C  
HETATM   27  C26 UNL     1       6.217  -0.789   1.503  1.00  0.00           C  
HETATM   28  C27 UNL     1       8.184  -0.374   0.153  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.510   3.163  -0.558  1.00  0.00           H  
HETATM   30  H2  UNL     1      -3.755   1.714  -1.395  1.00  0.00           H  
HETATM   31  H3  UNL     1      -7.042   2.745   0.222  1.00  0.00           H  
HETATM   32  H4  UNL     1      -6.086   2.177   1.701  1.00  0.00           H  
HETATM   33  H5  UNL     1      -8.455   1.169   1.335  1.00  0.00           H  
HETATM   34  H6  UNL     1      -7.112   0.049   1.664  1.00  0.00           H  
HETATM   35  H7  UNL     1      -8.065   0.766  -1.118  1.00  0.00           H  
HETATM   36  H8  UNL     1      -8.635  -1.580   0.455  1.00  0.00           H  
HETATM   37  H9  UNL     1      -6.667  -1.833  -0.366  1.00  0.00           H  
HETATM   38  H10 UNL     1      -6.692  -0.935  -1.916  1.00  0.00           H  
HETATM   39  H11 UNL     1      -4.226  -1.793  -0.448  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.020   0.981   0.486  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.407  -2.310  -1.091  1.00  0.00           H  
HETATM   42  H14 UNL     1      -2.558  -2.767   0.613  1.00  0.00           H  
HETATM   43  H15 UNL     1      -0.252  -2.930  -1.239  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.616  -3.842   0.234  1.00  0.00           H  
HETATM   45  H17 UNL     1       0.233  -2.078   1.631  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.428  -2.650   0.459  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.612   0.506  -1.734  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.767  -0.596  -1.717  1.00  0.00           H  
HETATM   49  H21 UNL     1       0.825  -1.284  -2.068  1.00  0.00           H  
HETATM   50  H22 UNL     1      -0.458  -0.172   1.812  1.00  0.00           H  
HETATM   51  H23 UNL     1      -0.979   2.071   1.151  1.00  0.00           H  
HETATM   52  H24 UNL     1      -0.931   1.710  -0.579  1.00  0.00           H  
HETATM   53  H25 UNL     1       1.259   2.204   1.370  1.00  0.00           H  
HETATM   54  H26 UNL     1       1.274   2.115  -0.454  1.00  0.00           H  
HETATM   55  H27 UNL     1       1.877  -0.038   1.569  1.00  0.00           H  
HETATM   56  H28 UNL     1       2.590   0.723  -1.291  1.00  0.00           H  
HETATM   57  H29 UNL     1       3.636  -1.531   0.504  1.00  0.00           H  
HETATM   58  H30 UNL     1       2.979  -1.730  -1.115  1.00  0.00           H  
HETATM   59  H31 UNL     1       4.525  -0.944  -0.925  1.00  0.00           H  
HETATM   60  H32 UNL     1       3.685   1.087   1.534  1.00  0.00           H  
HETATM   61  H33 UNL     1       3.068   2.297   0.441  1.00  0.00           H  
HETATM   62  H34 UNL     1       4.787   2.348  -1.047  1.00  0.00           H  
HETATM   63  H35 UNL     1       5.328   2.640   0.600  1.00  0.00           H  
HETATM   64  H36 UNL     1       6.282   0.334  -1.210  1.00  0.00           H  
HETATM   65  H37 UNL     1       6.980   1.827  -0.673  1.00  0.00           H  
HETATM   66  H38 UNL     1       7.361   1.026   1.549  1.00  0.00           H  
HETATM   67  H39 UNL     1       6.851  -1.252   2.310  1.00  0.00           H  
HETATM   68  H40 UNL     1       5.265  -0.460   1.901  1.00  0.00           H  
HETATM   69  H41 UNL     1       6.002  -1.666   0.816  1.00  0.00           H  
HETATM   70  H42 UNL     1       8.689  -1.023   0.868  1.00  0.00           H  
HETATM   71  H43 UNL     1       8.829   0.424  -0.268  1.00  0.00           H  
HETATM   72  H44 UNL     1       7.762  -0.998  -0.672  1.00  0.00           H  
CONECT    1    2    2   29   30
CONECT    2    3    8
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6    7   35
CONECT    6   36
CONECT    7    8   37   38
CONECT    8    9    9
CONECT    9   10   39
CONECT   10   11   11   40
CONECT   11   12   17
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   17   20
CONECT   16   47   48   49
CONECT   17   18   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   55
CONECT   21   22   23   56
CONECT   22   57   58   59
CONECT   23   24   60   61
CONECT   24   25   62   63
CONECT   25   26   64   65
CONECT   26   27   28   66
CONECT   27   67   68   69
CONECT   28   70   71   72
END

HMDB0000876
     RDKit          3D
Vitamin D3
 72 74  0  0  0  0  0  0  0  0999 V2000
   -4.4964    2.0982   -0.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4231    1.3547   -0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5035    1.9245    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4871    0.7830    0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8240    0.0340   -0.3344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8903   -0.7958   -0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6556   -0.8241   -0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3935   -0.0993   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408   -0.7003   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -0.0416    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8738   -0.7261    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9359   -2.1551   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5905   -2.8096   -0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119   -2.0788    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5481   -0.6802    0.0258 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3291   -0.5400   -1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -0.0380    0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5227    1.3777    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9862    1.5928    0.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    0.1967    0.5419 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8666    0.2948   -0.3005 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5322   -0.9896   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109    1.3008    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963    1.7324   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2170    0.9890   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399    0.2995    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165   -0.7886    1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1844   -0.3745    0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5103    3.1628   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550    1.7141   -1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0424    2.7447    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0861    2.1765    1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4548    1.1687    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1117    0.0493    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0655    0.7661   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6354   -1.5800    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6669   -1.8334   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6921   -0.9346   -1.9164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2259   -1.7929   -0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199    0.9811    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4073   -2.3100   -1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -2.7671    0.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2521   -2.9298   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6156   -3.8420    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2331   -2.0785    1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4276   -2.6505    0.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6119    0.5061   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7673   -0.5964   -1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.2835   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -0.1716    1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9785    2.0711    1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313    1.7098   -0.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585    2.2041    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736    2.1152   -0.4538 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8772   -0.0377    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    0.7234   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6361   -1.5311    0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -1.7302   -1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5247   -0.9444   -0.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    1.0873    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680    2.2966    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    2.3484   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3280    2.6398    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2818    0.3342   -1.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804    1.8275   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3606    1.0263    1.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8507   -1.2522    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651   -0.4599    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015   -1.6660    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6890   -1.0234    0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285    0.4240   -0.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7622   -0.9983   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
  8  2  1  0
 17 11  1  0
 20 15  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  7 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  1
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  1
 21 56  1  6
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
M  END

View in JSmol

Synonyms

Value	Source
(+)-Vitamin D3	ChEBI
(1S,3Z)-3-[(2E)-2-[(1R,3AR,7as)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol	ChEBI
(3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol	ChEBI
(5Z,7E)-(3S)-9,10-Secocholesta-5,7,10(19)-trien-3-ol	ChEBI
Activated 7-dehydrocholesterol	ChEBI
CC	ChEBI
Cholecalciferol	ChEBI
Colecalciferol	ChEBI
Delta-D	ChEBI
Oleovitamin D3	ChEBI
Calciol	Kegg
(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol	Generator
(3Β,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol	Generator
δ-D	Generator
7-DEHYDROCHOLESTEROL	HMDB
ACTIVATED	HMDB
VITAMIN D	HMDB
Dihydrocholesterol	HMDB
Vitamin D 3	HMDB
(3 beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol	HMDB
Cholecalciferols	HMDB
Vitamin D3	ChEBI

Chemical Formula

C₂₇H₄₄O

Average Mass

384.6377 Da

Monoisotopic Mass

384.33922 Da

IUPAC Name

(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

Traditional Name

vitamin D3

CAS Registry Number

67-97-0

SMILES

[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

InChI Key

QYSXJUFSXHHAJI-YRZJJWOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201.216488466 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	DTU Food
Abramis brama	FooDB	DTU Food
Acipenser	FooDB	USDA
Acipenseridae	FooDB	DTU Food
Actinidia chinensis	FooDB	DTU Food
Agaricus bisporus	FooDB	DTU Food
Allium cepa L.	FooDB	DTU Food
Allium sativum	FooDB	DTU Food
Allium schoenoprasum	FooDB	DTU Food
Alosa sapidissima	FooDB	USDA
Anacardium occidentale	FooDB	DTU Food
Ananas comosus	FooDB	DTU Food
Anarhichas lupus	FooDB	DTU Food
Anatidae	FooDB	DTU Food
Anethum graveolens	FooDB	DTU Food
Anguilla	FooDB	USDA
Anguilliformes	FooDB	DTU Food
Annona cherimola	FooDB	DTU Food
Anthriscus cerefolium	FooDB	DTU Food
Apium graveolens	FooDB	DTU Food
Apium graveolens var. rapaceum	FooDB	DTU Food
Apium graveolens var. secalinum	FooDB	DTU Food
Arachis hypogaea	FooDB	DTU Food
Armoracia rusticana	FooDB	DTU Food
Asparagus officinalis	FooDB	DTU Food
Astacidea	FooDB	DTU Food
Avena sativa L.	FooDB	DTU Food
Averrhoa carambola	FooDB	DTU Food
Belone belone	FooDB	DTU Food
Bertholletia excelsa	FooDB	DTU Food
Beta vulgaris ssp. cicla	FooDB	DTU Food
Bos taurus	FooDB	DTU Food
Brachyura	FooDB	DTU Food
Brassica napus	FooDB	DTU Food
Brassica napus var. napus	FooDB	DTU Food
Brassica oleracea	FooDB	DTU Food
Brassica oleracea var. botrytis	FooDB	DTU Food
Brassica oleracea var. gemmifera	FooDB	DTU Food
Brassica oleracea var. gongylodes	FooDB	DTU Food
Brassica oleracea var. italica	FooDB	DTU Food
Brassica oleracea var. sabauda	FooDB	DTU Food
Brassica rapa	FooDB	DTU Food
Brassica rapa ssp. chinensis	FooDB	DTU Food
Brassica rapa var. rapa	FooDB	DTU Food
Buccinidae	FooDB	USDA
Cantharellus cibarius	FooDB	DTU Food
Capra aegagrus hircus	FooDB	USDA
Capsicum annuum	FooDB	DTU Food
Carica papaya L.	FooDB	DTU Food
Caridea	FooDB	DTU Food
Carthamus tinctorius	FooDB	DTU Food
Carya illinoinensis	FooDB	DTU Food
Castanea	FooDB	DTU Food
Cervidae	FooDB	USDA
Cestrum diurnum	LOTUS Database	35616633
Cicer arietinum	FooDB	DTU Food
Cichlidae	FooDB	USDA
Cichorium endivia	FooDB	DTU Food
Cichorium intybus	FooDB	DTU Food
Cinnamomum	FooDB	DTU Food
Cirsium	FooDB	DTU Food
Citrullus lanatus	FooDB	DTU Food
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	DTU Food
Citrus aurantiifolia	FooDB	DTU Food
Citrus limon	FooDB	DTU Food
Citrus paradisi	FooDB	DTU Food
Citrus reticulata	FooDB	DTU Food
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	DTU Food
Clupea harengus harengus	FooDB	USDA
Clupeinae	FooDB	DTU Food
Cocos nucifera	FooDB	DTU Food
Coffea arabica L.	FooDB	DTU Food
Coffea canephora	FooDB	DTU Food
Columbidae	FooDB	DTU Food
Coregonus	FooDB	DTU Food
Coriandrum sativum L.	FooDB	DTU Food
Corylus	FooDB	DTU Food
Crassostrea virginica	FooDB	USDA
Cucumis melo	FooDB	DTU Food
Cucumis sativus L.	FooDB	DTU Food
Cucurbita	FooDB	DTU Food
Cucurbita maxima	FooDB	DTU Food
Cucurbita pepo	KNApSAcK Database	22123792
Cyclopteridae	FooDB	DTU Food
Cydonia oblonga	FooDB	DTU Food
Cynara scolymus	FooDB	DTU Food
Cyprinus carpio	FooDB	USDA
Daucus carota ssp. sativus	FooDB	DTU Food
Dioscorea	FooDB	DTU Food
Diospyros	FooDB	DTU Food
Elaeis	FooDB	DTU Food
Engraulidae	FooDB	DTU Food
Eriobotrya japonica	FooDB	DTU Food
Esox lucius	FooDB	DTU Food
Eucheuma	FooDB	DTU Food
Fagopyrum esculentum	FooDB	DTU Food
Ficus carica	FooDB	DTU Food
Foeniculum vulgare	FooDB	DTU Food
Fragaria x ananassa	FooDB	DTU Food
Gadiformes	FooDB	DTU Food
Gadus	FooDB	DTU Food
Gadus macrocephalus	FooDB	USDA
Gadus morhua	FooDB	USDA
Gallus gallus	FooDB	DTU Food
Gastropoda	FooDB	DTU Food
Glycine max	FooDB	DTU Food
Gossypium	FooDB	DTU Food
Grifola frondosa	FooDB	USDA
Helianthus annuus L.	FooDB	DTU Food
Helianthus tuberosus	FooDB	DTU Food
Hippoglossus	FooDB	USDA
Hippoglossus hippoglossus	FooDB	DTU Food
Hippoglossus stenolepis	FooDB	USDA
Homarus americanus	FooDB	USDA
Homo sapiens	LOTUS Database	35616633
Hordeum vulgare	FooDB	DTU Food
Ictalurus punctatus	FooDB	USDA
Ipomoea batatas	FooDB	DTU Food
Juglans	FooDB	DTU Food
Juglans nigra L.	FooDB	DTU Food
Lactuca sativa	FooDB	DTU Food
Lagopus muta	FooDB	DTU Food
Lens culinaris	FooDB	DTU Food
Lentinus edodes	FooDB	USDA
Lepidium sativum	FooDB	DTU Food
Leporidae	FooDB	DTU Food
Lepus timidus	FooDB	DTU Food
Limanda limanda	FooDB	DTU Food
Linum usitatissimum	FooDB	DTU Food
Litchi chinensis	FooDB	DTU Food
Lota lota	FooDB	DTU Food
Lutjanidae	FooDB	USDA
Malus	FooDB	DTU Food
Malus pumila	FooDB	DTU Food
Mangifera indica	FooDB	DTU Food
Manihot esculenta	FooDB	DTU Food
Medicago sativa	FooDB	DTU Food
Melanogrammus aeglefinus	FooDB	DTU Food
Meleagris gallopavo	FooDB	DTU Food
Merlangius merlangus	FooDB	DTU Food
Micromesistius poutassou	FooDB	DTU Food
Micropogonias undulatus	FooDB	USDA
Microstomus kitt	FooDB	DTU Food
Molva molva	FooDB	DTU Food
Morchellaceae	FooDB	USDA
Mugil cephalus	FooDB	USDA
Musa x paradisiaca	FooDB	DTU Food
Myristica fragrans	FooDB	DTU Food
Mytilidae	FooDB	DTU Food
Mytilus edulis	FooDB	USDA
Nephropidae	FooDB	DTU Food
Nephrops norvegicus	FooDB	DTU Food
Octopus vulgaris	FooDB	DTU Food
Olea europaea	FooDB	DTU Food
Oncorhynchus gorbuscha	FooDB	USDA
Oncorhynchus kisutch	FooDB	USDA
Oncorhynchus mykiss	FooDB	DTU Food
Oncorhynchus nerka	FooDB	USDA
Opuntia	FooDB	DTU Food
Oryza sativa	FooDB	DTU Food
Osmerus mordax	FooDB	USDA
Ovis aries	FooDB	DTU Food
Panicum miliaceum	FooDB	DTU Food
Papaver	FooDB	DTU Food
Passiflora edulis	FooDB	DTU Food
Pastinaca sativa	FooDB	DTU Food
Pectinidae	FooDB	USDA
Perciformes	FooDB	DTU Food
Persea americana	FooDB	DTU Food
Petroselinum crispum	FooDB	DTU Food
Phaseolus vulgaris	FooDB	DTU Food
Phasianidae	FooDB	USDA
Phoenix dactylifera	FooDB	DTU Food
Phyllostachys edulis	FooDB	DTU Food
Physalis	FooDB	DTU Food
Pinus	FooDB	DTU Food
Piper nigrum L.	FooDB	DTU Food
Pistacia vera	FooDB	DTU Food
Pisum sativum	FooDB	DTU Food
Pleuronectidae	FooDB	DTU Food
Pleuronectiformes	FooDB	DTU Food
Pleurotus ostreatus	FooDB	DTU Food
Pollachius	FooDB	DTU Food
Pollachius pollachius	FooDB	USDA
Prunus armeniaca	FooDB	DTU Food
Prunus avium L.	FooDB	DTU Food
Prunus domestica	FooDB	DTU Food
Prunus dulcis	FooDB	DTU Food
Prunus persica	FooDB	DTU Food
Prunus persica var. nucipersica	FooDB	DTU Food
Psidium guajava	FooDB	DTU Food
Punica granatum	FooDB	DTU Food
Pyrus communis	FooDB	DTU Food
Ranidae	FooDB	DTU Food
Raphanus sativus var. longipinnatus	FooDB	DTU Food
Reinhardtius hippoglossoides	FooDB	DTU Food
Rheum rhabarbarum	FooDB	DTU Food
Ribes nigrum	FooDB	DTU Food
Ribes rubrum	FooDB	DTU Food
Ribes uva-crispa	FooDB	DTU Food
Rosa	FooDB	DTU Food
Rumex acetosa	FooDB	DTU Food
Saccharina japonica	FooDB	DTU Food
Salmonidae	FooDB	DTU Food
Salvelinus	FooDB	DTU Food
Salvelinus namaycush	FooDB	DTU Food
Sambucus nigra L.	FooDB	DTU Food
Sander lucioperca	FooDB	DTU Food
Scomberomorus maculatus	FooDB	USDA
Scombridae	FooDB	DTU Food
Scophthalmus maximus	FooDB	DTU Food
Scorzonera hispanica	FooDB	DTU Food
Sebastes	FooDB	USDA
Sebastes alutus	FooDB	DTU Food
Sebastes viviparus	FooDB	DTU Food
Secale cereale	FooDB	DTU Food
Sechium edule	FooDB	DTU Food
Sesamum indicum	FooDB	DTU Food
Siluriformes	FooDB	DTU Food
Solanum glaucophyllum	LOTUS Database	35616633
Solanum lycopersicum	KNApSAcK Database	22123792
Solanum melongena	KNApSAcK Database	22123792
Solanum tuberosum	KNApSAcK Database	22123792
Soleidae	FooDB	USDA
Spinacia oleracea	FooDB	DTU Food
Squaliformes	FooDB	USDA
Squalus acanthias	FooDB	DTU Food
Stenotomus chrysops	FooDB	USDA
Strombidae	FooDB	USDA
Sus scrofa domestica	FooDB	DTU Food
Tamarindus indica	FooDB	DTU Food
Taraxacum officinale	FooDB	DTU Food
Teuthida	FooDB	USDA
Theobroma cacao	LOTUS Database	35616633
Thunnus	FooDB	DTU Food
Thunnus albacares	FooDB	USDA
Thunnus thynnus	FooDB	USDA
Trachinotus carolinus	FooDB	USDA
Trachurus symmetricus	FooDB	USDA
Trisopterus esmarkii	FooDB	DTU Food
Triticum	FooDB	DTU Food
Triticum durum	FooDB	DTU Food
Vaccinium	FooDB	DTU Food
Vaccinium myrtillus	FooDB	DTU Food
Vaccinium vitis-idaea	FooDB	DTU Food
Vigna angularis	FooDB	DTU Food
Vigna radiata	FooDB	DTU Food
Vitis	FooDB	DTU Food
Xiphias gladius	FooDB	USDA
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	DTU Food

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:28940 )
steroid hormone (CHEBI:28940 )
seco-cholestane (CHEBI:28940 )
hydroxy seco-steroid (CHEBI:28940 )
D3 vitamins (CHEBI:28940 )
Vitamin D3 and derivatives (C05443 )
Fat-soluble vitamins (C05443 )
Vitamin D3 and derivatives (LMST03020000 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	84.5 °C	Not Available
Boiling Point	496.44 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.2e-05 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.085 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	0.00038 g/L	ALOGPS
logP	7.98	ALOGPS
logP	7.13	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.38	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.22 m³·mol⁻¹	ChemAxon
Polarizability	49.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000876

DrugBank ID

DB00169

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

2288999

Wikipedia Link

Cholecalciferol

METLIN ID

Not Available

PubChem Compound

5280795

PDB ID

Not Available

ChEBI ID

28940

Good Scents ID

rw1133511

References

General References

Flanagan JN, Young MV, Persons KS, Wang L, Mathieu JS, Whitlatch LW, Holick MF, Chen TC: Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D. Anticancer Res. 2006 Jul-Aug;26(4A):2567-72. [PubMed:16886665 ]
Rautureau M, Rambaud JC: Aqueous solubilisation of vitamin D3 in normal man. Gut. 1981 May;22(5):393-7. [PubMed:6265326 ]
Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69. [PubMed:227368 ]
Osborne JE, Hutchinson PE: Vitamin D and systemic cancer: is this relevant to malignant melanoma? Br J Dermatol. 2002 Aug;147(2):197-213. [PubMed:12174089 ]
Haddad JG, Jennings AS, Aw TC: Vitamin D uptake and metabolism by perfused rat liver: influences of carrier proteins. Endocrinology. 1988 Jul;123(1):498-504. [PubMed:2838261 ]
Kida K, Goodman DS: Studies on the transport of vitamin D and of 25-hydroxyvitamin D in human plasma. J Lipid Res. 1976 Sep;17(5):485-90. [PubMed:184223 ]
Lips P: Vitamin D deficiency and secondary hyperparathyroidism in the elderly: consequences for bone loss and fractures and therapeutic implications. Endocr Rev. 2001 Aug;22(4):477-501. [PubMed:11493580 ]
Svendsen ML, Daneels G, Geysen J, Binderup L, Kragballe K: Proliferation and differentiation of cultured human keratinocytes is modulated by 1,25(OH)2D3 and synthetic vitamin D3 analogues in a cell density-, calcium- and serum-dependent manner. Pharmacol Toxicol. 1997 Jan;80(1):49-56. [PubMed:9148283 ]
Yetgin S, Yalcin SS: The effect of vitamin D3 on CD34 progenitor cells in vitamin D deficiency rickets. Turk J Pediatr. 2004 Apr-Jun;46(2):164-6. [PubMed:15214747 ]
Astecker N, Reddy GS, Herzig G, Vorisek G, Schuster I: 1alpha,25-Dihydroxy-3-epi-vitamin D3 a physiological metabolite of 1alpha,25-dihydroxyvitamin D3: its production and metabolism in primary human keratinocytes. Mol Cell Endocrinol. 2000 Dec 22;170(1-2):91-101. [PubMed:11162893 ]
Murao N, Ohishi N, Nabuchi Y, Ishigai M, Kawanishi T, Aso Y: The determination of 2beta-(3-hydroxypropoxy)-1alpha,25-dihydroxy vitamin D3 (ED-71) in human serum by high-performance liquid chromatography-electrospray tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 5;823(2):61-8. Epub 2004 Nov 19. [PubMed:16102526 ]
Lippens S, Kockx M, Denecker G, Knaapen M, Verheyen A, Christiaen R, Tschachler E, Vandenabeele P, Declercq W: Vitamin D3 induces caspase-14 expression in psoriatic lesions and enhances caspase-14 processing in organotypic skin cultures. Am J Pathol. 2004 Sep;165(3):833-41. [PubMed:15331408 ]
Bjorkhem I, Holmberg I, Kristiansen T, Pedersen JI: Assay of 1,25-dihydroxy vitamin D3 by isotope dilution--mass fragmentography. Clin Chem. 1979 Apr;25(4):584-8. [PubMed:466767 ]
Matsuoka LY, McConnachie P, Wortsman J, Holick MF: Immunological responses to ultraviolet light B radiation in Black individuals. Life Sci. 1999;64(17):1563-9. [PubMed:10353621 ]
Zimber A, Chedeville A, Abita JP, Barbu V, Gespach C: Functional interactions between bile acids, all-trans retinoic acid, and 1,25-dihydroxy-vitamin D3 on monocytic differentiation and myeloblastin gene down-regulation in HL60 and THP-1 human leukemia cells. Cancer Res. 2000 Feb 1;60(3):672-8. [PubMed:10676652 ]
Baggio B, Budakovic A, Nassuato MA, Vezzoli G, Manzato E, Luisetto G, Zaninotto M: Plasma phospholipid arachidonic acid content and calcium metabolism in idiopathic calcium nephrolithiasis. Kidney Int. 2000 Sep;58(3):1278-84. [PubMed:10972691 ]
MacLaughlin J, Holick MF: Aging decreases the capacity of human skin to produce vitamin D3. J Clin Invest. 1985 Oct;76(4):1536-8. [PubMed:2997282 ]
Lee YF, Young WJ, Lin WJ, Shyr CR, Chang C: Differential regulation of direct repeat 3 vitamin D3 and direct repeat 4 thyroid hormone signaling pathways by the human TR4 orphan receptor. J Biol Chem. 1999 Jun 4;274(23):16198-205. [PubMed:10347174 ]
Okano T, Kuroda E, Nakao H, Kodama S, Matsuo T, Nakamichi Y, Nakajima K, Hirao N, Kobayashi T: Lack of evidence for existence of vitamin D and 25-hydroxyvitamin D sulfates in human breast and cow's milk. J Nutr Sci Vitaminol (Tokyo). 1986 Oct;32(5):449-62. [PubMed:3494111 ]
Mata-Granados JM, Caballo-Lopez A, Luque de Castro MD, Quesada JM: Automated method for the determination of vitamin D3 hydroxymetabolites in serum. Anal Bioanal Chem. 2003 Sep;377(2):287-92. Epub 2003 Jul 9. [PubMed:12955389 ]
Armas LA, Hollis BW, Heaney RP: Vitamin D2 is much less effective than vitamin D3 in humans. J Clin Endocrinol Metab. 2004 Nov;89(11):5387-91. [PubMed:15531486 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for Vitamin D3 (NP0001049)

MOL for NP0001049 (Vitamin D3)

3D MOL for NP0001049 (Vitamin D3)

3D SDF for NP0001049 (Vitamin D3)

3D-SDF for NP0001049 (Vitamin D3)

PDB for NP0001049 (Vitamin D3)

3D PDB for NP0001049 (Vitamin D3)

SMILES for NP0001049 (Vitamin D3)

INCHI for NP0001049 (Vitamin D3)

Structure for NP0001049 (Vitamin D3)

3D Structure for NP0001049 (Vitamin D3)