ID: ALA443681

Max Phase: Preclinical

Molecular Formula: C43H58O6

Molecular Weight: 670.93

Molecule Type: Small molecule

Representations

Synonyms (1): Oblongifolin C
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)=CCC/C(C)=C/C[C@@H]1C[C@]2(CC=C(C)C)C(=O)[C@@](CC=C(C)C)(C(=O)C(C(=O)c3ccc(O)c(O)c3)=C2O)[C@@]1(C)CCC=C(C)C

Standard InChI:  InChI=1S/C43H58O6/c1-27(2)13-11-15-31(9)16-18-33-26-42(23-20-29(5)6)38(47)36(37(46)32-17-19-34(44)35(45)25-32)39(48)43(40(42)49,24-21-30(7)8)41(33,10)22-12-14-28(3)4/h13-14,16-17,19-21,25,33,44-45,47H,11-12,15,18,22-24,26H2,1-10H3/b31-16+/t33-,41+,42+,43-/m1/s1

Standard InChI Key:  XIKKSUTXFFVDEF-SSVAQFLFSA-N

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

Properties

Molecular Weight: 670.93

Molecular Weight (Monoisotopic): 670.4233

AlogP: 10.79

#Rotatable Bonds: 14

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: 3.33

CX Basic pKa:

CX LogP: 10.90

CX LogD: 7.39

Aromatic Rings: 1

Heavy Atoms: 49

QED Weighted: 0.06

Np Likeness Score: 2.26

References

1. 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]

2. Huang SX, Feng C, Zhou Y, Xu G, Han QB, Qiao CF, Chang DC, Luo KQ, Xu HX..  (2009)  Bioassay-guided isolation of xanthones and polycyclic prenylated acylphloroglucinols from Garcinia oblongifolia.,  72  (1): [PMID:19113969] [10.1021/np800496c]

3. 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]

4. Zhang H, Tao L, Fu WW, Liang S, Yang YF, Yuan QH, Yang DJ, Lu AP, Xu HX..  (2014)  Prenylated benzoylphloroglucinols and xanthones from the leaves of Garcinia oblongifolia with antienteroviral activity.,  77  (4): [PMID:24679044] [10.1021/np500124e]

5. Wang L, Wu R, Fu W, Lao Y, Zheng C, Tan H, Xu H..  (2016)  Synthesis and biological evaluation of Oblongifolin C derivatives as c-Met inhibitors.,  24  (18): [PMID:27396929] [10.1016/j.bmc.2016.06.054]

6. Cottet K, Xu B, Coric P, Bouaziz S, Michel S, Vidal M, Lallemand MC, Broussy S..  (2016)  Guttiferone A Aggregates Modulate Silent Information Regulator 1 (SIRT1) Activity.,  59  (20): [PMID:27669815] [10.1021/acs.jmedchem.6b01182]

7. 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]

Source

Source(1):

• Scientific Literature