ID: ALA502489

Max Phase: Preclinical

Molecular Formula: C38H50O6

Molecular Weight: 602.81

Molecule Type: Small molecule

Representations

Synonyms (2): Camboginol | Garcinol
Synonyms from Alternative Forms(2):

Canonical SMILES:  C=C(C)[C@@H](CC=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/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h11-12,14,16-17,19,27-28,39-40,42H,7,13,15,18,20-21H2,1-6,8-10H3/t27-,28+,37+,38-/m0/s1

Standard InChI Key:  QDKLRKZQSOQWJQ-SMDXAGPFSA-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: 8.91

#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: 3.51

CX Basic pKa:

CX LogP: 9.14

CX LogD: 5.68

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.08

Np Likeness Score: 2.52

References

1. Ito C, Itoigawa M, Miyamoto Y, Onoda S, Rao KS, Mukainaka T, Tokuda H, Nishino H, Furukawa H..  (2003)  Polyprenylated benzophenones from Garcinia assigu and their potential cancer chemopreventive activities.,  66  (2): [PMID:12608850] [10.1021/np020372g]

2. Gorsuch S, Bavetsias V, Rowlands MG, Aherne GW, Workman P, Jarman M, McDonald E..  (2009)  Synthesis of isothiazol-3-one derivatives as inhibitors of histone acetyltransferases (HATs).,  17  (2): [PMID:19101154] [10.1016/j.bmc.2008.11.079]

3. Arif M, Pradhan SK, Thanuja GR, Vedamurthy BM, Agrawal S, Dasgupta D, Kundu TK..  (2009)  Mechanism of p300 specific histone acetyltransferase inhibition by small molecules.,  52  (2): [PMID:19086895] [10.1021/jm800657z]

4. Hamed W, Brajeul S, Mahuteau-Betzer F, Thoison O, Mons S, Delpech B, Nguyen VH, Sévenet T, Marazano C..  (2006)  Oblongifolins A-D, polyprenylated benzoylphloroglucinol derivatives from Garcinia oblongifolia.,  69  (5): [PMID:16724839] [10.1021/np050543s]

5. 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]

6. Jones P.  (2012)  Development of second generation epigenetic agents,  3  (2): [10.1039/C1MD00199J]

7. Bharate SS, Vishwakarma RA..  (2015)  Thermodynamic equilibrium solubility measurements in simulated fluids by 96-well plate method in early drug discovery.,  25  (7): [PMID:25740159] [10.1016/j.bmcl.2015.02.013]

8. Dahlin JL, Nissink JW, Strasser JM, Francis S, Higgins L, Zhou H, Zhang Z, Walters MA..  (2015)  PAINS in the assay: chemical mechanisms of assay interference and promiscuous enzymatic inhibition observed during a sulfhydryl-scavenging HTS.,  58  (5): [PMID:25634295] [10.1021/jm5019093]

9. Stark TD, Salger M, Frank O, Balemba OB, Wakamatsu J, Hofmann T..  (2015)  Antioxidative compounds from Garcinia buchananii stem bark.,  78  (2): [PMID:25625705] [10.1021/np5007873]

Source

Source(1):

• Scientific Literature