(20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid

ID: ALA477754

PubChem CID: 44575598

Max Phase: Preclinical

Molecular Formula: C30H50O4

Molecular Weight: 474.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@@H]([C@@](C)(O)C/C=C/C(C)(C)O)CC[C@]32C)[C@@]1(C)CCC(=O)O

Standard InChI:  InChI=1S/C30H50O4/c1-20(2)21-12-19-29(7)24(27(21,5)17-14-25(31)32)11-10-22-23(13-18-28(22,29)6)30(8,34)16-9-15-26(3,4)33/h9,15,21-24,33-34H,1,10-14,16-19H2,2-8H3,(H,31,32)/b15-9+/t21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

Standard InChI Key:  IEKMEVXMHYPYPV-DJEZTIHDSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.5510   -3.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -2.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193   -4.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -4.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -3.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -2.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0242   -2.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0242   -3.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8046   -3.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -2.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -1.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8156   -0.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318   -0.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    0.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    1.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2702    1.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0242   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -2.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193   -3.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1193   -2.4177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4076   -3.6552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000   -1.5333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250   -4.8917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651   -2.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9799   -3.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -2.0046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5493   -4.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8358   -5.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0093   -0.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6406   -0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333   -2.4167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8579    2.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 19  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  7 22  1  0
 22 23  1  0
  2 23  1  0
  4 23  1  0
 23 24  1  1
 22 25  1  6
 13 26  1  6
  1  2  1  0
  4 27  1  6
  3  4  1  0
  1 28  1  0
  4  5  1  0
 28 29  1  0
  5  6  1  0
 28 30  2  0
  6  7  1  0
  3 31  2  0
  7  8  1  1
  3 32  1  0
  7  9  1  0
 14 33  1  0
  9 10  1  6
 14 34  1  6
  9 11  1  0
 19 35  1  1
 11 12  1  0
 18 36  1  0
 13 12  1  0
 18 37  1  0
 13 14  1  0
 18 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA477754

   3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(E,2S)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

Molecule Features

Natural Product: No

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: 474.73

Molecular Weight (Monoisotopic): 474.3709

AlogP: 6.76

#Rotatable Bonds: 8

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.97

CX Basic pKa: ┄

CX LogP: 5.74

CX LogD: 3.34

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.34

Np Likeness Score: 2.86

References

1. Rivero-Cruz JF, Chai HB, Kardono LB, Setyowati FM, Afriatini JJ, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD..  (2004)  Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa.,  67  (3): [PMID:15043407] [10.1021/np0304417]

Source

Source(1):

• Scientific Literature