NP-MRD: Showing NP-Card for (1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one (NP0303753)

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Record Information

Version

2.0

Created at

2022-09-10 18:22:30 UTC

Updated at

2022-09-10 18:22:30 UTC

NP-MRD ID

NP0303753

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one

Description

2Alpha,3beta,4beta,18-Tetrahydroxypregna-5-ene-16-one belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. (1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one is found in Melia azedarach. Based on a literature review very few articles have been published on 2alpha,3beta,4beta,18-Tetrahydroxypregna-5-ene-16-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220222D          

 26 29  0  0  1  0            999 V2000
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959   -3.9415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  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  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    4.3689   -3.0637   -2.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3585   -2.9903   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3918   -1.9284   -1.3771 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6518   -2.1878   -2.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596   -2.8821   -3.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3473   -1.4536   -2.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010   -0.7994   -1.2944 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8614   -0.4953   -0.5661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8924    0.1965   -1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213    1.6603   -1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8585    2.1103    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9986    3.5473    0.4518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3807    3.8123    0.6016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2656    4.0591    1.6273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1378    4.8147    2.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5501    3.0155    2.4516 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7659    2.8326    2.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2956    1.7226    2.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5407    1.0682    1.2132 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7924    0.2112    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911    0.3153    0.6444 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3600   -0.5657    1.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6138   -1.0556    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2247   -1.7429   -0.4455 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6148   -3.0655   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -3.7630   -1.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3584   -3.3383   -1.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3761   -2.1209   -2.7615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613   -3.8704   -2.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8795   -2.8031   -0.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210   -4.0064   -0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -0.9277   -1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5131   -2.1222   -2.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318   -0.6992   -3.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9929    0.1551   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851   -1.4490   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725   -0.3044   -1.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5160    0.1850   -2.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556    2.3733   -1.8322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    4.1769   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5222    4.7897    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4722    4.7950    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    5.6271    1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853    3.4259    3.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0301    3.6759    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8292    1.0739    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    1.9752    2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6093   -0.8517    1.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6131    0.5447    0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2389    0.3059    2.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270    1.0814    0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353   -0.1105    2.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528   -1.4549    1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0567   -1.8329    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798   -0.2040    0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248   -3.0425    0.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3991   -3.6922    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2075   -4.7270   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 25 26  1  0
 24  3  1  0
 24  7  1  0
 21  8  1  0
 19 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  6 33  1  0
  6 34  1  0
  7 35  1  6
  8 36  1  1
  9 37  1  0
  9 38  1  0
 10 39  1  0
 12 40  1  6
 13 41  1  0
 14 42  1  6
 15 43  1  0
 16 44  1  1
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  6
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
M  END


  Mrv1652309102220222D          

 26 29  0  0  1  0            999 V2000
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959   -3.9415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  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  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C(=O)C[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-3-12-16(23)8-15-11-4-5-14-18(25)19(26)17(24)9-20(14,2)13(11)6-7-21(12,15)10-22/h5,11-13,15,17-19,22,24-26H,3-4,6-10H2,1-2H3/t11-,12+,13+,15+,17-,18-,19+,20-,21+/m1/s1

> <INCHI_KEY>
FDYFHSWLEFIUMG-APKYNJKKSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.00351657540327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5S,6R,10R,11S,14R,15R)-14-ethyl-4,5,6-trihydroxy-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

> <JCHEM_LOGP>
0.562654724

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.206121117838052

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.97159822819117

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7655251450227762

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
98.12629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5S,6R,10R,11S,14R,15R)-14-ethyl-4,5,6-trihydroxy-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.459  -7.358   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   11   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    8   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7    3   25                                             
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
2a,3b,4b,18-Tetrahydroxypregna-5-ene-16-one	Generator
2Α,3β,4β,18-tetrahydroxypregna-5-ene-16-one	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

(1S,2R,4R,5S,6R,10R,11S,14R,15R)-14-ethyl-4,5,6-trihydroxy-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

Traditional Name

(1S,2R,4R,5S,6R,10R,11S,14R,15R)-14-ethyl-4,5,6-trihydroxy-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

CAS Registry Number

Not Available

SMILES

CC[C@H]1C(=O)C[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@]12CO

InChI Identifier

InChI=1S/C21H32O5/c1-3-12-16(23)8-15-11-4-5-14-18(25)19(26)17(24)9-20(14,2)13(11)6-7-21(12,15)10-22/h5,11-13,15,17-19,22,24-26H,3-4,6-10H2,1-2H3/t11-,12+,13+,15+,17-,18-,19+,20-,21+/m1/s1

InChI Key

FDYFHSWLEFIUMG-APKYNJKKSA-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
Melia azedarach	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
18-hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
4-hydroxysteroid
2-hydroxysteroid
Oxosteroid
16-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclitol or derivatives
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Ketone
Polyol
Organooxygen compound
Primary alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
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	0.56	ChemAxon
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.13 m³·mol⁻¹	ChemAxon
Polarizability	41 Å³	ChemAxon
Number of Rings	4	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

46211478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one (NP0303753)

MOL for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

3D MOL for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

3D SDF for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

3D-SDF for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

PDB for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

3D PDB for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

SMILES for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

INCHI for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

Structure for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)

3D Structure for NP0303753 ((1r,3as,3br,6r,7s,8r,9ar,9bs,11ar)-1-ethyl-6,7,8-trihydroxy-11a-(hydroxymethyl)-9a-methyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one)