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

ID: ALA499655

Chembl Id: CHEMBL499655

PubChem CID: 44561411

Max Phase: Preclinical

Molecular Formula: C33H48O12

Molecular Weight: 636.74

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

Standard InChI:  InChI=1S/C33H48O12/c1-5-6-16-32(45-31(41)14-12-28(36)37)18-19-33(44-26(32)10-8-22(2)20-29(38)39)17-15-24(4)25(43-33)9-7-23(3)21-42-30(40)13-11-27(34)35/h7-8,10,20,24-26H,5-6,9,11-19,21H2,1-4H3,(H,34,35)(H,36,37)(H,38,39)/b10-8+,22-20+,23-7+/t24-,25+,26-,32+,33-/m0/s1

Standard InChI Key:  YNLYBWKKCRIWOI-AKXZREBKSA-N

Alternative Forms

1. Parent:

   

   ALA499655

   (2E,4E)-5-[(2S,3R,6S,8R,9S)-3-butyl-3-(3-carboxypropanoyloxy)-8-[(E)-4-(3-carboxypropanoyloxy)-3-methylbut-2-enyl]-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: 636.74

Molecular Weight (Monoisotopic): 636.3146

AlogP: 5.35

#Rotatable Bonds: 17

Polar Surface Area: 182.96

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.60

CX Basic pKa: ┄

CX LogP: 4.81

CX LogD: -4.47

Aromatic Rings: ┄

Heavy Atoms: 45

QED Weighted: 0.08

Np Likeness Score: 1.48

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