NP-MRD: Showing NP-Card for (+)-Calicoferol I (NP0083025)

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Record Information

Version

2.0

Created at

2022-04-29 04:04:49 UTC

Updated at

2022-04-29 04:04:50 UTC

NP-MRD ID

NP0083025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Calicoferol I

Description

Calicoferol b belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, calicoferol b is considered to be a secosteroid. (+)-Calicoferol I is found in Muricella sp. (+)-Calicoferol I was first documented in 2002 (PMID: 12098293). Based on a literature review very few articles have been published on Calicoferol b.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206042D          

 30 32  0  0  1  0            999 V2000
   -0.9766    5.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    6.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    5.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    4.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667    3.8905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2737    4.0621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5287    4.8467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3356    5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5906    5.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3975    5.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9496    5.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7565    5.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0115    6.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4594    6.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6525    6.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    7.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086    4.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    3.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    2.7345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3805    3.0701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3340    2.6576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0484    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    1.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 21 28  1  1  0  0  0
 19 29  1  1  0  0  0
  5 30  1  1  0  0  0
M  END

     RDKit          3D

 72 74  0  0  0  0  0  0  0  0999 V2000
    5.3386    1.8089    2.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149    1.3911    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3947    1.3198    1.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0520    0.9336   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2848    0.6024   -1.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8730    0.1999   -2.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9084    0.6633   -1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2647    1.0573    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7624    1.0902    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068   -0.1195    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8379   -0.3134    0.8993 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7540   -1.6518    1.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2176   -1.7134    2.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1530   -2.8425    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0056   -2.5736    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3288   -1.0928    0.0098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9339   -0.6843    1.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095   -0.4117   -0.2995 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5371    0.8374   -0.9612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145    0.1743   -2.0751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0160    1.0652   -2.8119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1130   -0.7797   -1.2219 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5417   -0.4834   -1.1221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1833   -0.7539   -2.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0018    0.8133   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4999    0.9076   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0253   -0.1059    0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5240    0.0089    0.7432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2907   -0.1876   -0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9038    1.2664    1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3503    2.2125    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3600    1.0229    3.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9715    2.6482    2.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9647    1.5848    1.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1306    0.8802   -0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0349   -0.7941   -2.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3440    0.3892   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3848    2.0384    0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774    0.9434   -1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086   -1.0217    0.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7244   -0.0668    1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    0.4233    1.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718   -3.4922    1.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9330   -3.4685    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198   -3.1194    0.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2759   -2.9026   -0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5476   -1.3533    2.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.9702    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    0.3258    1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -1.0341   -1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009    1.4607   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    1.4419   -1.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -0.3393   -2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436    0.9105   -3.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0662   -1.7554   -1.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9950   -1.2986   -0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -1.5926   -2.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103    0.1015   -3.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2172   -1.1345   -2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7533    1.6827   -1.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    1.0956    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658    1.9120    0.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    0.8582   -1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5720    0.0636    1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8524   -1.1571    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8091   -0.8466    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0837    0.5941   -1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1006   -1.2103   -0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3679   -0.1317   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0085    1.3064    1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5312    2.1833    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5525    1.1837    2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  1  0
 28 27  1  0
 27 26  1  0
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 20 19  1  0
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  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 22  1  0
 16 18  1  0
  2  8  1  0
 29 67  1  0
 29 68  1  0
 29 69  1  0
 28 66  1  1
 30 70  1  0
 30 71  1  0
 30 72  1  0
 27 64  1  0
 27 65  1  0
 26 62  1  0
 26 63  1  0
 25 60  1  0
 25 61  1  0
 23 56  1  1
 24 57  1  0
 24 58  1  0
 24 59  1  0
 22 55  1  6
 20 53  1  6
 21 54  1  0
 19 51  1  0
 19 52  1  0
 18 50  1  6
 11 42  1  1
 10 40  1  0
 10 41  1  0
  9 38  1  0
  9 39  1  0
  7 37  1  0
  6 36  1  0
  4 35  1  0
  3 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
M  END


  Mrv1652304292206042D          

 30 32  0  0  1  0            999 V2000
   -0.9766    5.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    6.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    5.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    4.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667    3.8905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2737    4.0621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5287    4.8467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3356    5.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5906    5.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3975    5.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9496    5.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7565    5.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0115    6.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4594    6.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6525    6.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    7.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086    4.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6862    3.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    2.7345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3805    3.0701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3340    2.6576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0484    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    1.9275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179    3.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 21 28  1  1  0  0  0
 19 29  1  1  0  0  0
  5 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0083025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1[C@@H](O)C[C@H]2[C@H](CCC3=CC(O)=CC=C3C)C(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O3/c1-17(2)7-6-8-19(4)26-25(30)16-23-22(24(29)13-14-27(23,26)5)12-10-20-15-21(28)11-9-18(20)3/h9,11,15,17,19,22-23,25-26,28,30H,6-8,10,12-14,16H2,1-5H3/t19-,22+,23+,25+,26+,27+/m1/s1

> <INCHI_KEY>
USFQLAVWHQCNDG-AYEIPMSGSA-N

> <FORMULA>
C27H42O3

> <MOLECULAR_WEIGHT>
414.63

> <EXACT_MASS>
414.313395212

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.194348477712516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3aS,4S,7aS)-2-hydroxy-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-5-one

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
6.894041805333332

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.935492196205384

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.818564888875343

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6400156408507188

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
123.7554

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.68e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calicoferol B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.823  10.192   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.299  11.656   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.317   9.871   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.159   8.407   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.871   7.262   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.378   7.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.853   9.047   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.360   9.367   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.836  10.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.342  11.152   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.373  10.008   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.879  10.328   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.355  11.793   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.324  12.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.818  12.617   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.787  13.761   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.909   9.183   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.148   6.249   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.117   5.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.710   5.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.623   4.961   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.957   5.731   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.291   4.961   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.624   5.731   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.958   4.961   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.292   5.731   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.958   3.421   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.623   3.421   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.437   3.598   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.593   6.786   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20   30                                             
CONECT    6    5    7   18                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18    6   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19    5   21                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21                                                            
CONECT   29   19                                                            
CONECT   30    5                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₃

Average Mass

414.6300 Da

Monoisotopic Mass

414.31340 Da

IUPAC Name

(1R,2S,3aS,4S,7aS)-2-hydroxy-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-5-one

Traditional Name

calicoferol B

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1[C@@H](O)C[C@H]2[C@H](CCC3=CC(O)=CC=C3C)C(=O)CC[C@]12C

InChI Identifier

InChI=1S/C27H42O3/c1-17(2)7-6-8-19(4)26-25(30)16-23-22(24(29)13-14-27(23,26)5)12-10-20-15-21(28)11-9-18(20)3/h9,11,15,17,19,22-23,25-26,28,30H,6-8,10,12-14,16H2,1-5H3/t19-,22+,23+,25+,26+,27+/m1/s1

InChI Key

USFQLAVWHQCNDG-AYEIPMSGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Muricella sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
P-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Vitamin D3 and derivatives (LMST03020180 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.06	ALOGPS
logP	6.89	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	123.76 m³·mol⁻¹	ChemAxon
Polarizability	51.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7826338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Taber DF, Jiang Q, Chen B, Zhang W, Campbell CL: Synthesis of (-)-calicoferol B. J Org Chem. 2002 Jul 12;67(14):4821-7. doi: 10.1021/jo020103v. [PubMed:12098293 ]

Showing NP-Card for (+)-Calicoferol I (NP0083025)

MOL for NP0083025 ((+)-Calicoferol I)

3D MOL for NP0083025 ((+)-Calicoferol I)

3D SDF for NP0083025 ((+)-Calicoferol I)

3D-SDF for NP0083025 ((+)-Calicoferol I)

PDB for NP0083025 ((+)-Calicoferol I)

3D PDB for NP0083025 ((+)-Calicoferol I)

SMILES for NP0083025 ((+)-Calicoferol I)

INCHI for NP0083025 ((+)-Calicoferol I)

Structure for NP0083025 ((+)-Calicoferol I)

3D Structure for NP0083025 ((+)-Calicoferol I)