NP-MRD: Showing NP-Card for ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid (NP0066125)

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Record Information

Version

2.0

Created at

2022-04-28 10:17:19 UTC

Updated at

2022-04-28 10:17:19 UTC

NP-MRD ID

NP0066125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid

Description

(1S,5S,6R,8aS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid is found in Halimium viscosum. Based on a literature review very few articles have been published on (1S,5S,6R,8aS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212172D          

 31 32  0  0  1  0            999 V2000
   -2.6305    2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    2.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921    2.7519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2795    2.0235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8423    1.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    1.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2296    0.5954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0541    0.5667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4913    1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1040    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4414   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    0.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3717   -0.2296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6572    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -0.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862   -0.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -1.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -1.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -2.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987   -0.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1720   -0.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    3.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6912    3.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2657    4.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6066    3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  6  0  0  0
  7 12  1  1  0  0  0
 12 13  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  2  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  6  0  0  0
 14 26  1  6  0  0  0
  7 27  1  6  0  0  0
  3 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  3 31  1  6  0  0  0
M  END

     RDKit          3D

 69 70  0  0  0  0  0  0  0  0999 V2000
    6.1777    3.1960    1.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893    1.8670    1.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1610    0.8314    1.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    1.7905    1.6035 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3694    0.6534    1.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2115   -0.1684    0.5661 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3715   -0.6672   -0.0398 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -0.3773   -1.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0174   -0.9455   -1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0302    0.3928   -1.9763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3060   -1.3756    0.7760 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2320   -2.1178   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -2.2340    1.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -1.1343    1.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -0.3922    1.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -0.6818    0.0590 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3678   -0.4489   -1.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131    0.3520    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7611    1.5633   -0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6702    2.7401   -0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154    2.4597    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4131    1.0319   -0.2079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2807    0.9179   -1.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8280    0.8672    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2795    0.0976    1.0006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7411    1.6419   -0.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4692    0.1100    0.5525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9200   -1.3028    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -2.1563    1.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6568   -2.0065    0.0607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2387   -2.2389   -1.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2447    3.0574    1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7277    3.9200    1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215    3.5624    0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7748    0.1207    2.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3733    1.0261    2.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7254    0.4603   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7658   -1.3875   -2.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3168   -1.7973   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8477   -0.2167   -1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2997   -2.7618   -0.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -1.5337   -1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0840   -2.8359   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.8648    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8128   -2.1934    1.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4911   -0.7206    2.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -0.3150    2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2276    0.7221    1.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4041   -1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    0.2199   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5681    0.1251   -1.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7378    1.7677   -0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1892    3.5691    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7964    3.0499   -1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7661    3.1705   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9869    2.4166    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716    0.9213   -2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038   -0.0297   -1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9183    1.7326   -2.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0275    2.5427   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269    0.5010    1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4397   -1.6732   -0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6648   -1.4014    1.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0810   -3.2146    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.8180    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9669   -2.8631    0.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1376   -2.9122   -1.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4601   -1.3159   -1.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5167   -2.8920   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
 24 26  1  0
 24 25  2  0
 18 16  1  0
 16 17  1  6
 16 15  1  0
 15 14  1  0
 14 11  1  0
 11 12  1  0
 11 13  1  1
 11  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 16 30  1  0
 22 27  1  0
 31 67  1  0
 31 68  1  0
 31 69  1  0
 30 66  1  1
 29 64  1  0
 29 65  1  0
 28 62  1  0
 28 63  1  0
 27 61  1  1
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 23 57  1  0
 23 58  1  0
 23 59  1  0
 26 60  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 15 47  1  0
 15 48  1  0
 14 45  1  0
 14 46  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
  6 37  1  6
  5 35  1  0
  5 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
M  END


  Mrv1652304282212172D          

 31 32  0  0  1  0            999 V2000
   -2.6305    2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0676    2.7807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921    2.7519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2795    2.0235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8423    1.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    1.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2296    0.5954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0541    0.5667    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4913    1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1040    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4414   -0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5151    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0862    0.1829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3717   -0.2296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6572    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -0.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717    0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4862   -0.2296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -1.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -1.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -2.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0572   -1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6737    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987   -0.5315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1720   -0.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    3.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6912    3.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2657    4.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6066    3.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  6  0  0  0
  7 12  1  1  0  0  0
 12 13  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  2  0  0  0  0
 18 20  1  0  0  0  0
 15 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  6  0  0  0
 14 26  1  6  0  0  0
  7 27  1  6  0  0  0
  3 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  3 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066125

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H]2C(=CCC[C@]2(C)C(O)=O)[C@@]1(C)CC[C@](C)(O)[C@@H](COC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O7/c1-15-9-10-19-18(8-7-11-23(19,5)21(27)28)22(15,4)12-13-24(6,29)20(31-17(3)26)14-30-16(2)25/h8,15,19-20,29H,7,9-14H2,1-6H3,(H,27,28)/t15-,19+,20-,22+,23+,24+/m1/s1

> <INCHI_KEY>
CSEDYVUWKINDQS-OLBDQMJSSA-N

> <FORMULA>
C24H38O7

> <MOLECULAR_WEIGHT>
438.561

> <EXACT_MASS>
438.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
47.456488775631485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5S,6R,8aS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
3.2687425749999997

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.956574085384354

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.578331117530496

> <JCHEM_PKA_STRONGEST_BASIC>
-3.25519449702995

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
115.26309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,6R,8aS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.910   3.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.726   5.191   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.265   5.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.988   3.777   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.172   2.471   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.633   2.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.895   1.111   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.434   1.058   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.250   2.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.527   3.723   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.157  -0.302   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.562   0.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.228   1.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.894   0.341   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.561  -0.429   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.227   0.341   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.107  -0.429   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.441   0.341   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.774  -0.429   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.441   1.881   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.561  -1.969   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.227  -2.739   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.227  -4.279   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.107  -1.969   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.124   1.675   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.664  -0.992   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -7.788  -0.425   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.373   6.673   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.757   7.348   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -6.096   7.534   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -8.599   5.907   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   28   31                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   27                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25   26                                             
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14                                                            
CONECT   26   14                                                            
CONECT   27    7                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    3                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1S,5S,6R,8AS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₂₄H₃₈O₇

Average Mass

438.5610 Da

Monoisotopic Mass

438.26175 Da

IUPAC Name

(1S,5S,6R,8aS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

(1S,5S,6R,8aS)-5-[(3S,4R)-4,5-bis(acetyloxy)-3-hydroxy-3-methylpentyl]-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H]2C(=CCC[C@]2(C)C(O)=O)[C@@]1(C)CC[C@](C)(O)[C@@H](COC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C24H38O7/c1-15-9-10-19-18(8-7-11-23(19,5)21(27)28)22(15,4)12-13-24(6,29)20(31-17(3)26)14-30-16(2)25/h8,15,19-20,29H,7,9-14H2,1-6H3,(H,27,28)/t15-,19+,20-,22+,23+,24+/m1/s1

InChI Key

CSEDYVUWKINDQS-OLBDQMJSSA-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
Halimium viscosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	4.08	ALOGPS
logP	3.27	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	115.26 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162953786

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid (NP0066125)

MOL for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

3D MOL for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

3D SDF for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

3D-SDF for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

PDB for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

3D PDB for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

SMILES for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

INCHI for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

Structure for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)

3D Structure for NP0066125 (ent-13R-Hydroxy-14S,15-diacetoxy-1(10)-halimen-18-oic acid)