2-Methyl-butyric acid (1R,3S,5S,6aR,7S,8S,10R)-1,3-diacetoxy-10-hydroxy-7,8-dimethyl-7-((E)-3-methyl-penta-2,4-dienyl)-3,5,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalen-5-yl ester

ID: ALA456075

Chembl Id: CHEMBL456075

PubChem CID: 44584135

Max Phase: Preclinical

Molecular Formula: C29H42O8

Molecular Weight: 518.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/C[C@]1(C)[C@H]2C[C@H](OC(=O)C(C)CC)C=C3[C@H](OC(C)=O)O[C@H](OC(C)=O)[C@@]32[C@H](O)C[C@@H]1C

Standard InChI:  InChI=1S/C29H42O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9,11,14,17-18,21,23-24,26-27,32H,1,10,12-13,15H2,2-8H3/b16-11+/t17?,18-,21+,23+,24+,26+,27-,28-,29-/m0/s1

Standard InChI Key:  FGGPIWICAGRSLN-UQSIVEBGSA-N

Alternative Forms

1. Parent:

   

   ALA456075

   CASEARLUCIN A

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: 518.65

Molecular Weight (Monoisotopic): 518.2880

AlogP: 4.62

#Rotatable Bonds: 8

Polar Surface Area: 108.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.50

CX LogD: 4.50

Aromatic Rings: ┄

Heavy Atoms: 37

QED Weighted: 0.21

Np Likeness Score: 3.48

References

1. Hayashi K, Nakanishi Y, Bastow KF, Cragg G, Nozaki H, Lee KH..  (2002)  Antitumor agents. Part 212. Bucidarasins A-C, three new cytotoxic clerodane diterpenes from Bucida buceras.,  12  (3): [PMID:11814793] [10.1016/s0960-894x(01)00742-9]

2. Sai Prakash CV, Hoch JM, Kingston DG..  (2002)  Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest.,  65  (2): [PMID:11858738] [10.1021/np010405c]

Source

Source(1):

• Scientific Literature