NP-MRD: Showing NP-Card for (2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid (NP0286520)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 15:07:50 UTC

Updated at

2022-09-09 15:07:50 UTC

NP-MRD ID

NP0286520

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid

Description

(2S,3R,4S,4aR,6aS,8aS,9R,12aR,13S,14aS,14bS)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid belongs to the class of organic compounds known as 12-alpha-hydroxysteroids. These are hydroxysteroids carrying a alpha-hydroxyl group at the 12-position. (2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid is found in Atroxima afzeliana. Based on a literature review very few articles have been published on (2S,3R,4S,4aR,6aS,8aS,9R,12aR,13S,14aS,14bS)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092217072D          

 38 42  0  0  1  0            999 V2000
   -3.8416   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7601   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -3.9764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    0.0809    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2026   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0276   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8189   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2182   -2.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -4.0387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 37 14  1  6  0  0  0
  7 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END

     RDKit          3D

 83 87  0  0  0  0  0  0  0  0999 V2000
   -5.3282    2.1375    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086    0.6183   -0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3991    0.2357   -1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5639   -0.1007    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3686   -0.1098    2.0566 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6611   -0.8883    3.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208   -0.5794    1.3459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1945   -1.9927    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135   -2.8088    1.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1530   -2.5622    0.1500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700   -0.3550    2.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1533    0.8934    1.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192    0.7118    0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5067    0.2326   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -0.3501   -1.6099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7360    0.1746   -2.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    1.9083   -3.1254 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3995   -0.3627   -1.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2379   -0.2011   -0.6052 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7955    1.0063    0.1752 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8127    2.3006   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550    1.0271    1.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0504    1.3161    1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6061    0.5502   -0.1354 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6849   -0.3334   -0.8739 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8995   -0.1618   -2.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0456   -1.8248   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4591   -2.0930   -1.1296 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7501   -3.4056   -0.6899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -1.1327   -0.5812 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4142   -1.8502    0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8912   -0.1157    0.3605 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7265   -0.6963    1.7387 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9290    0.9513    0.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4627    1.2616    1.5632 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107    1.6271   -0.6548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8994    0.3590    0.1631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9854    0.2341   -0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618    2.6133   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2463    2.3767    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2735    2.5629   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0080    0.0913   -2.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2304    0.9405   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8439   -0.7609   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9555   -1.1231    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3702    0.4414    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1939    0.9497    2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6647   -1.8334    2.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5007   -3.5013    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2784   -1.2076    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3069   -0.2580    3.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186    1.8270    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3490    0.9121    2.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4404   -1.4336   -1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277   -0.2077   -3.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066   -0.3007   -3.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    0.4003   -2.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6578   -1.3370   -2.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9178   -1.0621    0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    2.3485   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2199    2.7500   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680    3.0424    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976    0.0555    1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164    1.8829    2.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6665    1.1751    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    2.4376    0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9948    1.3297   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0262   -0.1877   -2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -1.0230   -2.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152    0.8188   -2.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858   -2.1984    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3817   -2.3557   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483   -2.1356   -2.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620   -3.4723    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0738   -0.6057   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2236   -1.2901    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2176   -0.0794    2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076   -0.8620    2.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -1.6707    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0290    2.5819   -0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0361    1.3926    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8847    1.0874   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1645   -0.7327   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  6
 32 34  1  1
 34 36  1  0
 34 35  2  0
 14 37  1  0
 37 38  1  0
  7  8  1  6
  8 10  1  0
  8  9  2  0
 38  2  1  0
 37  7  1  0
 20 13  1  0
 20 19  1  0
 24 25  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  1
  6 48  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
 15 54  1  1
 16 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  1
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  6
 29 74  1  0
 30 75  1  6
 31 76  1  0
 33 77  1  0
 33 78  1  0
 33 79  1  0
 24 67  1  6
 23 65  1  0
 23 66  1  0
 22 63  1  0
 22 64  1  0
 21 60  1  0
 21 61  1  0
 21 62  1  0
 36 80  1  0
 37 81  1  1
 38 82  1  0
 38 83  1  0
 10 49  1  0
M  END


  Mrv1652309092217072D          

 38 42  0  0  1  0            999 V2000
   -3.8416   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7601   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398   -3.9764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    0.0809    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2026   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0276   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8189   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2182   -2.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610   -4.0387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 37 14  1  6  0  0  0
  7 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@@H](O)[C@@]2(CCC3=C([C@@H](CCl)C[C@H]4[C@]5(C)C[C@H](O)[C@H](O)[C@](C)([C@@H]5CC[C@]34C)C(O)=O)[C@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H45ClO7/c1-26(2)11-17-22-15(14-31)10-20-27(3,16(22)6-9-30(17,25(37)38)21(33)13-26)8-7-19-28(20,4)12-18(32)23(34)29(19,5)24(35)36/h15,17-21,23,32-34H,6-14H2,1-5H3,(H,35,36)(H,37,38)/t15-,17-,18+,19-,20-,21-,23+,27-,28-,29+,30+/m1/s1

> <INCHI_KEY>
UPNBJODIQCXYCD-LOTYVWODSA-N

> <FORMULA>
C30H45ClO7

> <MOLECULAR_WEIGHT>
553.13

> <EXACT_MASS>
552.2853815

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
59.482493769376994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,4aR,6aS,8aS,9R,12aR,13S,14aS,14bS)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid

> <JCHEM_LOGP>
3.4199924793333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.949625811178059

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.33482677713124

> <JCHEM_PKA_STRONGEST_BASIC>
-3.05274395203363

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
142.9283

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,4aR,6aS,8aS,9R,12aR,13S,14aS,14bS)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1H-picene-4,8a-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.171  -1.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.438  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.886  -1.990   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.208  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -8.208  -6.517   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.898  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -6.517   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.914  -7.423   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -5.898  -7.851   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.128  -6.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.588  -6.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.818  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.588  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.818  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.588  -1.183   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -2.818   0.151   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -1.278  -2.516   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.508  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.278  -5.184   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.048  -6.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.508  -6.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.032  -6.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.802  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.032  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.262  -2.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.802  -2.516   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.342  -2.516   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.112  -1.183   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.112  -3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.652  -3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.342  -5.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.395  -6.723   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.648  -6.000   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.007  -5.277   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.594  -7.539   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.898  -2.516   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   38                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11   37                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   37                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   14    7   38                                                  
CONECT   38   37    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,4AR,6as,8as,9R,12ar,13S,14as,14BS)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-4,8a-dicarboxylate	Generator

Chemical Formula

C₃₀H₄₅ClO₇

Average Mass

553.1300 Da

Monoisotopic Mass

552.28538 Da

IUPAC Name

Traditional Name

(2S,3R,4S,4aR,6aS,8aS,9R,12aR,13S,14aS,14bS)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1H-picene-4,8a-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)C[C@@H](O)[C@@]2(CCC3=C([C@@H](CCl)C[C@H]4[C@]5(C)C[C@H](O)[C@H](O)[C@](C)([C@@H]5CC[C@]34C)C(O)=O)[C@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C30H45ClO7/c1-26(2)11-17-22-15(14-31)10-20-27(3,16(22)6-9-30(17,25(37)38)21(33)13-26)8-7-19-28(20,4)12-18(32)23(34)29(19,5)24(35)36/h15,17-21,23,32-34H,6-14H2,1-5H3,(H,35,36)(H,37,38)/t15-,17-,18+,19-,20-,21-,23+,27-,28-,29+,30+/m1/s1

InChI Key

UPNBJODIQCXYCD-LOTYVWODSA-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
Atroxima afzeliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 12-alpha-hydroxysteroids. These are hydroxysteroids carrying a alpha-hydroxyl group at the 12-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

12-alpha-hydroxysteroids

Alternative Parents

Substituents

12-alpha-hydroxysteroid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Organochloride
Organohalogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alkyl halide
Alkyl chloride
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	3.42	ChemAxon
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.93 m³·mol⁻¹	ChemAxon
Polarizability	59.48 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162872809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid (NP0286520)

MOL for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

3D MOL for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

3D SDF for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

3D-SDF for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

PDB for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

3D PDB for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

SMILES for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

INCHI for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

Structure for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)

3D Structure for NP0286520 ((2s,3r,4s,4ar,6as,8as,9r,12ar,13s,14as,14bs)-13-(chloromethyl)-2,3,9-trihydroxy-4,6a,11,11,14b-pentamethyl-2,3,4a,5,6,7,8,9,10,12,12a,13,14,14a-tetradecahydro-1h-picene-4,8a-dicarboxylic acid)