(2R,4aS,6aS,12bS,14aS,14bS)-10,11-dihydroxy-8-(5-methoxy-1H-indol-3-yl)-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

ID: ALA4287461

Chembl Id: CHEMBL4287461

PubChem CID: 145992922

Max Phase: Preclinical

Molecular Formula: C38H47NO5

Molecular Weight: 597.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2[nH]cc(C3C=C4[C@@](C)(CC[C@@]5(C)[C@H]6C[C@](C)(C(=O)O)CC[C@]6(C)CC[C@]45C)c4cc(O)c(O)c(C)c43)c2c1

Standard InChI:  InChI=1S/C38H47NO5/c1-21-31-24(25-20-39-27-9-8-22(44-7)16-23(25)27)17-29-36(4,26(31)18-28(40)32(21)41)13-15-38(6)30-19-35(3,33(42)43)11-10-34(30,2)12-14-37(29,38)5/h8-9,16-18,20,24,30,39-41H,10-15,19H2,1-7H3,(H,42,43)/t24?,30-,34+,35+,36-,37+,38-/m0/s1

Standard InChI Key:  FHKRZRSMJUIFOF-SXRSHKIJSA-N

Alternative Forms

1. Parent:

   

   ALA4287461

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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: 597.80

Molecular Weight (Monoisotopic): 597.3454

AlogP: 8.72

#Rotatable Bonds: 3

Polar Surface Area: 102.78

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.64

CX Basic pKa:

CX LogP: 8.27

CX LogD: 5.57

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.18

Np Likeness Score: 1.96

References

1. Salvador JAR, Leal AS, Valdeira AS, Gonçalves BMF, Alho DPS, Figueiredo SAC, Silvestre SM, Mendes VIS..  (2017)  Oleanane-, ursane-, and quinone methide friedelane-type triterpenoid derivatives: Recent advances in cancer treatment.,  142  [PMID:28754470] [10.1016/j.ejmech.2017.07.013]

Source

Source(1):

• Scientific Literature