Valhidepsin A

ID: ALA5286325

Chembl Id: CHEMBL5286325

Max Phase: Preclinical

Molecular Formula: C40H66N8O8

Molecular Weight: 787.02

Names and Identifiers

Canonical SMILES:  CCCCCC/C=C\CC(=O)N[C@H]1COC(=O)[C@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2c[nH]cn2)NC(=O)[C@@H](C(C)C)NC1=O

Standard InChI:  InChI=1S/C40H66N8O8/c1-10-11-12-13-14-15-16-17-31(49)43-30-21-56-40(55)34(26(8)9)48-35(50)28(18-23(2)3)44-38(53)32(24(4)5)46-36(51)29(19-27-20-41-22-42-27)45-39(54)33(25(6)7)47-37(30)52/h15-16,20,22-26,28-30,32-34H,10-14,17-19,21H2,1-9H3,(H,41,42)(H,43,49)(H,44,53)(H,45,54)(H,46,51)(H,47,52)(H,48,50)/b16-15-/t28-,29+,30+,32+,33-,34+/m1/s1

Standard InChI Key:  YXYRBEYIYZAXSD-YGERNHPLSA-N

Alternative Forms

1. Parent:

   

   ALA5286325

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 787.02

Molecular Weight (Monoisotopic): 786.5004

AlogP: 2.35

#Rotatable Bonds: 15

Polar Surface Area: 229.58

Molecular Species: NEUTRAL

HBA: 9

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.40

CX Basic pKa: 6.53

CX LogP: 3.11

CX LogD: 3.06

Aromatic Rings: 1

Heavy Atoms: 56

QED Weighted: 0.08

Np Likeness Score: 1.02

References

1. Pistorius D, Buntin K, Richard E, Rust M, Bouquet C, Wollbrett S, Weber E, Dietschin D, Bruccoleri R, Oakeley E, Petersen F..  (2023)  Valhidepsin Lipopeptides from Chromobacterium vaccinii: Structures, Biosynthesis, and Coregulation with FR900359 Production.,  86  (2.0): [PMID:36745695] [10.1021/acs.jnatprod.2c00825]

Source

Source(1):

• Scientific Literature