NP-MRD: Showing NP-Card for 9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid (NP0328082)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 11:13:47 UTC

Updated at

2022-09-12 11:13:47 UTC

NP-MRD ID

NP0328082

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid

Description

12,17-Dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosane-5,18-dicarboxylic acid belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. 9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid is found in Eleutherococcus trifoliatus. 12,17-Dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosane-5,18-dicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506222D          

 35 39  0  0  0  0            999 V2000
    0.5233   -2.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -2.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163   -2.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -4.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592   -4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -5.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -5.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133   -5.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149   -5.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117   -4.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -3.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -2.9566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615   -4.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -4.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097   -3.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0346   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2611   -4.4355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0129   -5.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -5.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -5.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9912   -6.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2394   -5.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -4.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8925   -6.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -5.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 32  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 79 83  0  0  0  0  0  0  0  0999 V2000
    2.9792    2.0185    2.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299    1.4594    1.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671    2.3157    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7925    0.0365    1.5579 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2105   -0.2096    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0785   -0.3485   -0.4005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.0724   -0.6189 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1599   -2.5199   -0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6904   -3.3258    0.0776 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0156   -2.9093   -1.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921   -0.6851   -1.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6677   -0.3002   -1.8730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -0.8360   -0.7059 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7435   -2.3130   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789   -0.4434    0.5270 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8089   -1.0117    1.6900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6364   -0.6962    1.7307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1455   -1.6470    2.6586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -0.8141    0.3886 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7636   -0.2821    0.4618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2455   -0.4844    1.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -1.2909   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9294   -0.7320   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8471    0.5776   -1.4339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1846    1.0059   -1.6544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2467    1.5702   -0.4854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2279    2.1909    0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2096    3.4630    0.5360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1983    1.5593    1.1547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9674    1.1245    0.1262 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8534    1.7994   -0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733    1.2783   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5149   -0.1928   -0.6831 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0024   -0.2899   -2.0730 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.8492    0.6262 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7256    3.0598    2.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8660    1.4377    3.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6343    2.6498    0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111    3.2902    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1531    1.8871   -0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7597   -0.3600    2.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5414   -1.1762    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9196    0.5597    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258    0.6059   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9461   -0.9370   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954   -3.5602   -2.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    0.1959   -2.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983   -1.4547   -2.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5780    0.8005   -1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018   -0.7364   -2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -2.6651   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4405   -2.6964   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746   -2.9245   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5318    0.6566    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2803   -0.5490    2.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0137   -2.1082    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591    0.2850    2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8190   -2.5467    2.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3877   -1.9246    0.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3686   -1.5727    2.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033    0.0900    2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2892   -0.1086    1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1075   -1.8079   -1.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9327   -2.1595    0.3840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3692   -1.4695   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6666   -0.6497    0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016    0.5951   -2.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2523    1.3493   -2.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747    2.4445   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0611    1.5360    2.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    1.7099    1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    1.8593   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8158    2.8989   -0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2961    1.5167    0.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    1.8678   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4206    0.4823   -2.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7559   -1.2443   -2.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340   -0.0769   -2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9864   -1.8522    1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  6
 26 27  1  0
 27 29  1  0
 27 28  2  0
 15 35  1  0
  7  8  1  6
  8 10  1  0
  8  9  2  0
 35  4  1  0
 35  7  1  0
 33 13  1  0
 33 19  1  0
 30 20  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  1 36  1  0
  1 37  1  0
  4 41  1  1
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 12 50  1  0
 14 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  1
 16 55  1  0
 16 56  1  0
 17 57  1  1
 18 58  1  0
 19 59  1  6
 21 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 26 69  1  6
 30 71  1  1
 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 34 76  1  0
 34 77  1  0
 34 78  1  0
 29 70  1  0
 35 79  1  1
 10 46  1  0
M  END


  Mrv1533004251506222D          

 35 39  0  0  0  0            999 V2000
    0.5233   -2.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -2.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163   -2.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -3.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1855   -4.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592   -4.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -5.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651   -5.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2900   -5.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7133   -5.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1149   -5.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3117   -4.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350   -3.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -2.9566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9615   -4.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7864   -4.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -3.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2097   -3.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0346   -3.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4362   -4.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2611   -4.4355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0129   -5.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1880   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -5.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9398   -5.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5382   -5.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6119   -5.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4145   -5.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9912   -6.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2394   -5.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868   -4.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8925   -6.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506   -5.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
 16 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 32  1  0  0  0  0
  7 32  1  0  0  0  0
  7 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328082

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC2(CCC3(C)C(CC(O)C4C5(C)CCC(O)C(C5CCC34C)C(O)=O)C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O6/c1-15(2)16-6-11-29(25(34)35)13-12-27(4)18(22(16)29)14-20(31)23-26(3)9-8-19(30)21(24(32)33)17(26)7-10-28(23,27)5/h16-23,30-31H,1,6-14H2,2-5H3,(H,32,33)(H,34,35)

> <INCHI_KEY>
XHXRCXXGUWSIQZ-UHFFFAOYSA-N

> <FORMULA>
C29H44O6

> <MOLECULAR_WEIGHT>
488.665

> <EXACT_MASS>
488.313789137

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.502135683706186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,17-dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5,18-dicarboxylic acid

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
3.96665258

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.884033283681808

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.270147591777683

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2845776650414248

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
131.43419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,17-dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5,18-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       0.977  -4.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.105  -5.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.577  -5.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.762  -6.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.346  -7.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.484  -9.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.985  -9.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.735 -10.783   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.275 -10.806   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.065  -9.484   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.814 -10.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.315  -8.139   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.105  -6.817   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.645  -6.841   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.435  -5.519   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.395  -8.186   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.935  -8.209   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.725  -6.888   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.265  -6.911   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.014  -8.256   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.554  -8.280   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.224  -9.578   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.684  -9.555   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.894 -10.876   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.354 -10.853   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.605  -9.508   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.742 -11.042   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.974 -10.923   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.184 -12.245   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.514 -10.947   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.775  -8.116   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.061 -10.670   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.666 -12.086   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.468 -10.485   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   32   33                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   27                                             
CONECT   11   10                                                            
CONECT   12   10   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   27                                                  
CONECT   17   16   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   17   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10   16   28                                             
CONECT   28   27                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   12    4    7                                                  
CONECT   33    7   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
12,17-Dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0,.0,.0,]henicosane-5,18-dicarboxylate	Generator
12,17-Dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5,18-dicarboxylate	Generator

Chemical Formula

C₂₉H₄₄O₆

Average Mass

488.6650 Da

Monoisotopic Mass

488.31379 Da

IUPAC Name

12,17-dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5,18-dicarboxylic acid

Traditional Name

12,17-dihydroxy-1,2,14-trimethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5,18-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC2(CCC3(C)C(CC(O)C4C5(C)CCC(O)C(C5CCC34C)C(O)=O)C12)C(O)=O

InChI Identifier

InChI=1S/C29H44O6/c1-15(2)16-6-11-29(25(34)35)13-12-27(4)18(22(16)29)14-20(31)23-26(3)9-8-19(30)21(24(32)33)17(26)7-10-28(23,27)5/h16-23,30-31H,1,6-14H2,2-5H3,(H,32,33)(H,34,35)

InChI Key

XHXRCXXGUWSIQZ-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Eleutherococcus trifoliatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

18-hydroxysteroid
18-oxosteroid
1-hydroxysteroid
Oxosteroid
6-hydroxysteroid
Hydroxysteroid
15-hydroxysteroid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	2.7	ALOGPS
logP	3.97	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.43 m³·mol⁻¹	ChemAxon
Polarizability	54.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid (NP0328082)

MOL for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

3D MOL for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

3D SDF for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

3D-SDF for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

PDB for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

3D PDB for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

SMILES for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

INCHI for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

Structure for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)

3D Structure for NP0328082 (9,12-dihydroxy-5a,5b,11a-trimethyl-1-(prop-1-en-2-yl)-hexadecahydro-1h-cyclopenta[a]chrysene-3a,8-dicarboxylic acid)