(8S,9S,10R,13S,14S,16R,17R)-16-hydroxy-17-((2S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA1173057

PubChem CID: 21673933

Max Phase: Preclinical

Molecular Formula: C27H42O4

Molecular Weight: 430.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CO)CCC(=O)[C@@H](C)[C@H]1[C@H](O)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C27H42O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h13,16-17,20-22,24-25,28,31H,5-12,14-15H2,1-4H3/t16?,17-,20-,21+,22+,24-,25+,26+,27+/m1/s1

Standard InChI Key:  HOQRRDCNLLTOEP-FHUFBSQRSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
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    8.9148  -18.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6285  -19.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6285  -17.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3469  -17.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3434  -18.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0553  -19.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7755  -18.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0624  -17.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7764  -17.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7900  -16.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0660  -16.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5040  -16.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4942  -17.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2758  -17.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.6950  -15.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5192  -15.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2752  -14.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9390  -16.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9235  -14.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7630  -16.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1828  -17.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0070  -17.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7785  -17.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4267  -17.7191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5928  -17.0174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7673  -16.9871    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0577  -18.2142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4862  -18.2280    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117  -16.3324    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
  7  8  1  0
  2 18  2  0
  8 10  1  0
  5 19  1  1
  9 10  1  0
 13 20  1  1
  3  6  2  0
 17 21  1  0
  5  4  1  0
 21 22  1  0
  5  6  1  0
 21 23  1  6
 22 24  1  0
  9 12  1  0
 22 25  2  0
 10 14  1  0
 24 26  1  0
 13 11  1  0
 26 27  1  0
 11 12  1  0
 27 28  1  0
 13 14  1  0
 27 29  1  0
  1  2  1  0
 28 30  1  0
  1  4  1  0
 16 31  1  6
  2  3  1  0
 10 32  1  1
  5  9  1  0
  9 33  1  6
  6  7  1  0
 14 34  1  6
 14 15  1  0
 17 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1173057

   (8S,9S,10R,13S,14S,16R,17R)-16-hydroxy-17-[(2S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 430.63

Molecular Weight (Monoisotopic): 430.3083

AlogP: 4.72

#Rotatable Bonds: 6

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: 2.51

References

1. Kaur K, Jain M, Kaur T, Jain R..  (2009)  Antimalarials from nature.,  17  (9): [PMID:19299148] [10.1016/j.bmc.2009.02.050]

Source

Source(1):

• Scientific Literature