4,4'-Linked Secalonic Acid A; Dimethyl (5S,5'S,6R,6'R,10aS,10a'S)-1,1',5,5',8,8'-hexahydroxy-6,6'-dimethyl-9,9'-dioxo-5,5',6,6',7,7',9,9'-octahydro-10aH,10a'H-[4,4'-bixanthene]-10a,10a'-dicarboxylate

ID: ALA5078761

Chembl Id: CHEMBL5078761

PubChem CID: 12309482

Max Phase: Preclinical

Molecular Formula: C32H30O14

Molecular Weight: 638.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12Oc3c(-c4ccc(O)c5c4O[C@@]4(C(=O)OC)C(=C(O)C[C@@H](C)[C@@H]4O)C5=O)ccc(O)c3C(=O)C1=C(O)C[C@@H](C)[C@@H]2O

Standard InChI:  InChI=1S/C32H30O14/c1-11-9-17(35)21-23(37)19-15(33)7-5-13(25(19)45-31(21,27(11)39)29(41)43-3)14-6-8-16(34)20-24(38)22-18(36)10-12(2)28(40)32(22,30(42)44-4)46-26(14)20/h5-8,11-12,27-28,33-36,39-40H,9-10H2,1-4H3/t11-,12-,27+,28+,31+,32+/m1/s1

Standard InChI Key:  ISZKIEBUBOALCU-ZKHWAINJSA-N

Alternative Forms

1. Parent:

   

   ALA5078761

   methyl (3R,4S,4aS)-5-[(5S,6R,10aS)-1,5,9-trihydroxy-10a-methoxycarbonyl-6-methyl-8-oxo-6,7-dihydro-5H-xanthen-4-yl]-4,8,9-trihydroxy-3-methyl-1-oxo-3,4-dihydro-2H-xanthene-4a-carboxylate

Molecule Features

Natural Product: Yes

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: 638.58

Molecular Weight (Monoisotopic): 638.1636

AlogP: 2.16

#Rotatable Bonds: 3

Polar Surface Area: 226.58

Molecular Species: NEUTRAL

HBA: 14

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.62

CX Basic pKa:

CX LogP: 2.25

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.27

Np Likeness Score: 1.25

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