Guttiferone M

ID: ALA3120621

Chembl Id: CHEMBL3120621

Max Phase: Preclinical

Molecular Formula: C38H50O6

Molecular Weight: 602.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/C[C@@]12C[C@H](CC=C(C)C)C(C)(C)[C@@](CC=C(C)C)(C(=O)C(C(=O)c3ccc(O)c(O)c3)=C1O)C2=O

Standard InChI:  InChI=1S/C38H50O6/c1-23(2)11-10-12-26(7)18-19-37-22-28(15-13-24(3)4)36(8,9)38(35(37)44,20-17-25(5)6)34(43)31(33(37)42)32(41)27-14-16-29(39)30(40)21-27/h11,13-14,16-18,21,28,39-40,42H,10,12,15,19-20,22H2,1-9H3/b26-18+/t28-,37+,38-/m0/s1

Standard InChI Key:  WBBLTYZSPRMLOP-QHHXVQFASA-N

Alternative Forms

1. Parent:

   

   ALA3120621

   ---

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: 602.81

Molecular Weight (Monoisotopic): 602.3607

AlogP: 9.06

#Rotatable Bonds: 11

Polar Surface Area: 111.90

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: ┄

CX LogP: 9.24

CX LogD: 5.73

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.08

Np Likeness Score: 2.43

References

1. Masullo M, Menegazzi M, Di Micco S, Beffy P, Bifulco G, Dal Bosco M, Novelli M, Pizza C, Masiello P, Piacente S..  (2014)  Direct interaction of garcinol and related polyisoprenylated benzophenones of Garcinia cambogia fruits with the transcription factor STAT-1 as a likely mechanism of their inhibitory effect on cytokine signaling pathways.,  77  (3): [PMID:24417609] [10.1021/np400804y]

2. Di Micco S, Masullo M, Bandak AF, Berger JM, Riccio R, Piacente S, Bifulco G..  (2019)  Garcinol and Related Polyisoprenylated Benzophenones as Topoisomerase II Inhibitors: Biochemical and Molecular Modeling Studies.,  82  (10): [PMID:31618025] [10.1021/acs.jnatprod.9b00382]

Source

Source(1):

• Scientific Literature