Citreohybriddione B

ID: ALA5219093

Chembl Id: CHEMBL5219093

PubChem CID: 21674268

Max Phase: Preclinical

Molecular Formula: C28H34O9

Molecular Weight: 514.57

Names and Identifiers

Canonical SMILES:  C=C1C=C2[C@]34CC[C@H](OC(C)=O)C(C)(C)[C@H]3[C@H](C[C@]2(C)[C@]2(C(=O)OC)C(=O)[C@](C)(O)C(=O)[C@]12C)OC4=O

Standard InChI:  InChI=1S/C28H34O9/c1-13-11-16-24(5,28(22(33)35-8)20(31)26(7,34)19(30)25(13,28)6)12-15-18-23(3,4)17(36-14(2)29)9-10-27(16,18)21(32)37-15/h11,15,17-18,34H,1,9-10,12H2,2-8H3/t15-,17-,18+,24-,25-,26+,27+,28+/m0/s1

Standard InChI Key:  PJBZWVDHHJBMHH-IMCZMANMSA-N

Alternative Forms

1. Parent:

   

   ALA5219093

   methyl (1S,5R,7R,9R,10S,12S,13R,15S)-15-acetyloxy-7-hydroxy-5,7,10,14,14-pentamethyl-4-methylidene-6,8,18-trioxo-19-oxapentacyclo[10.5.2.01,13.02,10.05,9]nonadec-2-ene-9-carboxylate

Molecule Features

Natural Product: Yes

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: 514.57

Molecular Weight (Monoisotopic): 514.2203

AlogP: 2.24

#Rotatable Bonds: 2

Polar Surface Area: 133.27

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.49

CX Basic pKa:

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 0

Heavy Atoms: 37

QED Weighted: 0.33

Np Likeness Score: 2.44

References

1. Leshchenko EV, Antonov AS, Dyshlovoy SA, Berdyshev DV, Hauschild J, Zhuravleva OI, Borkunov GV, Menshov AS, Kirichuk NN, Popov RS, Gerasimenko AV, Udovenko AA, Graefen M, Bokemeyer C, von Amsberg G, Yurchenko AN..  (2022)  Meroantarctines A-C, Meroterpenoids with Rearranged Skeletons from the Alga-Derived Fungus Penicillium antarcticum KMM 4685 with Potent p-Glycoprotein Inhibitory Activity.,  85  (12.0): [PMID:36413729] [10.1021/acs.jnatprod.2c00677]

Source

Source(1):

• Scientific Literature