Succinic acid mono-[(2S,3R,6S,8R,9S)-3-butyl-2-(4-carboxy-3-methyl-buta-1,3-dienyl)-8-((2E,4E)-5-carboxy-3-methyl-penta-2,4-dienyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl] ester

ID: ALA471857

Chembl Id: CHEMBL471857

PubChem CID: 44561412

Max Phase: Preclinical

Molecular Formula: C31H44O10

Molecular Weight: 576.68

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/C(=O)O)O2)O[C@H]1/C=C/C(C)=C/C(=O)O

Standard InChI:  InChI=1S/C31H44O10/c1-5-6-16-30(41-29(38)14-13-27(34)35)18-19-31(40-25(30)11-8-22(3)20-28(36)37)17-15-23(4)24(39-31)10-7-21(2)9-12-26(32)33/h7-9,11-12,20,23-25H,5-6,10,13-19H2,1-4H3,(H,32,33)(H,34,35)(H,36,37)/b11-8+,12-9+,21-7+,22-20+/t23-,24+,25-,30+,31-/m0/s1

Standard InChI Key:  YVQOLECKWISWQG-PQKSZLIQSA-N

Alternative Forms

1. Parent:

   

   ALA471857

   (2E,4E)-6-[(2S,3R,6S,8R,9S)-3-butyl-2-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dienyl]-3-(3-carboxypropanoyloxy)-9-methyl-1,7-dioxaspiro[5.5]undecan-8-yl]-4-methylhexa-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: 576.68

Molecular Weight (Monoisotopic): 576.2934

AlogP: 5.58

#Rotatable Bonds: 14

Polar Surface Area: 156.66

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.58

CX Basic pKa: ┄

CX LogP: 5.39

CX LogD: -3.94

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.14

Np Likeness Score: 1.62

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