(3R,4S,4aR)-7-(2-(3-carboxy-1-hydroxy-2-methylpropyl)-5-hydroxy-2-(methoxycarbonyl)-4-oxochroman-6-yl)-4,8,9a-trihydroxy-3-methyl-1,9-dioxo-1,2,3,4,9,9a-hexahydro-4aH-xanthene-4a-carboxylic acid

ID: ALA5082626

Chembl Id: CHEMBL5082626

PubChem CID: 166629125

Max Phase: Preclinical

Molecular Formula: C31H32O16

Molecular Weight: 660.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]1(C(O)C(C)CC(=O)O)CC(=O)c2c(ccc(-c3ccc4c(c3O)C(=O)C3(O)C(O)C[C@@H](C)[C@H](O)[C@@]3(C(=O)O)O4)c2O)O1

Standard InChI:  InChI=1S/C31H32O16/c1-11-8-18(33)30(44)26(40)21-17(47-31(30,25(11)39)27(41)42)7-5-14(23(21)37)13-4-6-16-20(22(13)36)15(32)10-29(46-16,28(43)45-3)24(38)12(2)9-19(34)35/h4-7,11-12,18,24-25,33,36-39,44H,8-10H2,1-3H3,(H,34,35)(H,41,42)/t11-,12?,18?,24?,25+,29+,30?,31+/m1/s1

Standard InChI Key:  YZKVDIADVLETMZ-YDNPYTSASA-N

Alternative Forms

1. Parent:

   

   ALA5082626

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 660.58

Molecular Weight (Monoisotopic): 660.1690

AlogP: 0.00

#Rotatable Bonds: 7

Polar Surface Area: 274.88

Molecular Species: ACID

HBA: 14

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.81

CX Basic pKa:

CX LogP: 1.28

CX LogD: -5.65

Aromatic Rings: 2

Heavy Atoms: 47

QED Weighted: 0.18

Np Likeness Score: 1.54

References

1. Lünne F, Köhler J, Stroh C, Müller L, Daniliuc CG, Mück-Lichtenfeld C, Würthwein EU, Esselen M, Humpf HU, Kalinina SA..  (2021)  Insights into Ergochromes of the Plant Pathogen Claviceps purpurea.,  84  (10.0): [PMID:34553942] [10.1021/acs.jnatprod.1c00264]

Source

Source(1):

• Scientific Literature