ID: ALA388529

Max Phase: Preclinical

Molecular Formula: C38H50O6

Molecular Weight: 602.81

Molecule Type: Small molecule

Representations

Synonyms (1): Guttiferone K
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@]2(CC=C(C)C)C(=O)[C@@]1(CC=C(C)C)C(=O)C(C(=O)c1ccc(O)c(O)c1)=C2O

Standard InChI:  InChI=1S/C38H50O6/c1-23(2)11-10-18-36(9)28(14-12-24(3)4)22-37(19-16-25(5)6)33(42)31(32(41)27-13-15-29(39)30(40)21-27)34(43)38(36,35(37)44)20-17-26(7)8/h11-13,15-17,21,28,39-40,42H,10,14,18-20,22H2,1-9H3/t28-,36+,37+,38-/m1/s1

Standard InChI Key:  QKKRBNPMUBNTPA-ZZEFGTIFSA-N

Molecule Features

Natural Product: Yes

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

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: 2.28

References

1. Cao S, Brodie PJ, Miller JS, Ratovoson F, Birkinshaw C, Randrianasolo S, Rakotobe E, Rasamison VE, Kingston DG..  (2007)  Guttiferones K and L, antiproliferative compounds of Rheedia calcicola from the Madagascar rain forest.,  70  (4): [PMID:17348706] [10.1021/np070004i]

2. Xu G, Kan WL, Zhou Y, Song JZ, Han QB, Qiao CF, Cho CH, Rudd JA, Lin G, Xu HX..  (2010)  Cytotoxic acylphloroglucinol derivatives from the twigs of Garcinia cowa.,  73  (2): [PMID:20058933] [10.1021/np9004147]

3. 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]

4. Le DH, Nishimura K, Takenaka Y, Mizushina Y, Tanahashi T..  (2016)  Polyprenylated Benzoylphloroglucinols with DNA Polymerase Inhibitory Activity from the Fruits of Garcinia schomburgkiana.,  79  (7): [PMID:27409517] [10.1021/acs.jnatprod.6b00255]

5. 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