3-((2S,3R,4S,6S)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-6-(3-hydroxy-8-(hydroxymethyl)-2,6,10,12-tetramethyloctadeca-4,6,9-trien-2-yl)-4-methoxy-2H-pyran-2-one

ID: ALA2269332

PubChem CID: 76308672

Max Phase: Preclinical

Molecular Formula: C35H56O9

Molecular Weight: 620.82

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C35H56O9/c1-8-9-10-11-12-22(2)15-24(4)17-25(20-36)16-23(3)13-14-29(39)35(5,6)30-19-28(42-7)31(34(41)44-30)33-32(40)27(38)18-26(21-37)43-33/h13-14,16-17,19,22,25-27,29,32-33,36-40H,8-12,15,18,20-21H2,1-7H3/b14-13+,23-16+,24-17-/t22?,25?,26-,27-,29?,32+,33-/m0/s1

Standard InChI Key:  YZTWXHSWFLKSLQ-MPFYGWOGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2269332

   3-[(2S,3R,4S,6S)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(4E,6E,9Z)-3-hydroxy-8-(hydroxymethyl)-2,6,10,12-tetramethyloctadeca-4,6,9-trien-2-yl]-4-methoxypyran-2-one

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: 620.82

Molecular Weight (Monoisotopic): 620.3924

AlogP: 4.88

#Rotatable Bonds: 17

Polar Surface Area: 149.82

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.03

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.09

Np Likeness Score: 2.12

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