(2S,3R,4S,6S)-2-(4-acetoxy-6-(3-acetoxy-2,6,8,10,12-pentamethyloctadeca-4,6,9-trien-2-yl)-2-oxo-2H-pyran-3-yl)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4-diyl diacetate

ID: ALA2269335

PubChem CID: 76323205

Max Phase: Preclinical

Molecular Formula: C44H64O13

Molecular Weight: 800.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCC(C)C/C(C)=C\C(C)/C=C(C)/C=C/C(OC(C)=O)C(C)(C)c1cc(OC(C)=O)c([C@@H]2O[C@H](COC(C)=O)C[C@H](OC(C)=O)[C@H]2OC(C)=O)c(=O)o1

Standard InChI:  InChI=1S/C44H64O13/c1-13-14-15-16-17-26(2)20-28(4)22-29(5)21-27(3)18-19-38(54-33(9)48)44(11,12)39-24-36(52-31(7)46)40(43(50)57-39)42-41(55-34(10)49)37(53-32(8)47)23-35(56-42)25-51-30(6)45/h18-19,21-22,24,26,29,35,37-38,41-42H,13-17,20,23,25H2,1-12H3/b19-18+,27-21+,28-22-/t26?,29?,35-,37-,38?,41+,42-/m0/s1

Standard InChI Key:  ONJLSOFMIOWJIQ-QEFHLRQESA-N

Molfile:  

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Alternative Forms

1. Parent:

   

   ALA2269335

   [(2S,4S,5R,6S)-4,5-diacetyloxy-6-[4-acetyloxy-6-[(4E,6E,9Z)-3-acetyloxy-2,6,8,10,12-pentamethyloctadeca-4,6,9-trien-2-yl]-2-oxopyran-3-yl]oxan-2-yl]methyl acetate

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: 800.98

Molecular Weight (Monoisotopic): 800.4347

AlogP: 8.11

#Rotatable Bonds: 20

Polar Surface Area: 170.94

Molecular Species: NEUTRAL

HBA: 13

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.87

CX LogD: 6.87

Aromatic Rings: 1

Heavy Atoms: 57

QED Weighted: 0.04

Np Likeness Score: 1.76

References

1. Altomare C, Pengue R, Favilla M, Evidente A, Visconti A..  (2004)  Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum.,  52  (10): [PMID:15137845] [10.1021/jf035233z]

Source

Source(1):

• Scientific Literature