Succinic acid mono-[(2S,3R,6S,8R,9S)-3-butyl-2-(4-carboxy-3-methyl-buta-1,3-dienyl)-8-((2E,4E)-6-hydroxy-3-methyl-hexa-2,4-dienyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl] ester

ID: ALA498825

Chembl Id: CHEMBL498825

PubChem CID: 44561410

Max Phase: Preclinical

Molecular Formula: C31H46O9

Molecular Weight: 562.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@@]1(OC(=O)CCC(=O)O)CC[C@]2(CC[C@H](C)[C@@H](C/C=C(C)/C=C/CO)O2)O[C@H]1/C=C/C(C)=C/C(=O)O

Standard InChI:  InChI=1S/C31H46O9/c1-5-6-16-30(40-29(37)14-13-27(33)34)18-19-31(39-26(30)12-10-23(3)21-28(35)36)17-15-24(4)25(38-31)11-9-22(2)8-7-20-32/h7-10,12,21,24-26,32H,5-6,11,13-20H2,1-4H3,(H,33,34)(H,35,36)/b8-7+,12-10+,22-9+,23-21+/t24-,25+,26-,30+,31-/m0/s1

Standard InChI Key:  RHSVBGOFUGMJGR-ALXKAXIDSA-N

Alternative Forms

1. Parent:

   

   ALA498825

   (2E,4E)-5-[(2S,3R,6S,8R,9S)-3-butyl-3-(3-carboxypropanoyloxy)-8-[(2E,4E)-6-hydroxy-3-methylhexa-2,4-dienyl]-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-3-methylpenta-2,4-dienoic 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: 562.70

Molecular Weight (Monoisotopic): 562.3142

AlogP: 5.49

#Rotatable Bonds: 14

Polar Surface Area: 139.59

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.69

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: -1.24

Aromatic Rings: ┄

Heavy Atoms: 40

QED Weighted: 0.14

Np Likeness Score: 1.86

References

1. Shimizu T, Usui T, Fujikura M, Kawatani M, Satoh T, Machida K, Kanoh N, Woo JT, Osada H, Sodeoka M..  (2008)  Synthesis and biological activities of reveromycin A and spirofungin A derivatives.,  18  (13): [PMID:18519164] [10.1016/j.bmcl.2008.05.054]

Source

Source(1):

• Scientific Literature