ID: ALA452483

Max Phase: Preclinical

Molecular Formula: C38H50O6

Molecular Weight: 602.81

Molecule Type: Small molecule

Representations

Synonyms (2): Guttiferone A | Guttiferone-A
Synonyms from Alternative Forms(2):

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+/m0/s1

Standard InChI Key:  QKKRBNPMUBNTPA-GHCWVHGPSA-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. Martins FT, Assis DM, Dos Santos MH, Camps I, Veloso MP, Juliano MA, Alves LC, Doriguetto AC..  (2009)  Natural polyprenylated benzophenones inhibiting cysteine and serine proteases.,  44  (3): [PMID:18995931] [10.1016/j.ejmech.2008.09.018]

2. Yang SS, Cragg GM, Newman DJ, Bader JP..  (2001)  Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.,  64  (2): [PMID:11430019] [10.1021/np0003995]

3. Acuña UM, Figueroa M, Kavalier A, Jancovski N, Basile MJ, Kennelly EJ..  (2010)  Benzophenones and biflavonoids from Rheedia edulis.,  73  (11): [PMID:21028890] [10.1021/np100322d]

4. Dias KS, Januário JP, D' Dego JL, Dias AL, dos Santos MH, Camps I, Coelho LF, Viegas C..  (2012)  Semisynthesis and antimicrobial activity of novel guttiferone-A derivatives.,  20  (8): [PMID:22401914] [10.1016/j.bmc.2012.02.023]

5. Fromentin Y, Gaboriaud-Kolar N, Lenta BN, Wansi JD, Buisson D, Mouray E, Grellier P, Loiseau PM, Lallemand MC, Michel S..  (2013)  Synthesis of novel guttiferone A derivatives: in-vitro evaluation toward Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani.,  65  [PMID:23727538] [10.1016/j.ejmech.2013.04.066]

6. Cottet K, Neudörffer A, Kritsanida M, Michel S, Lallemand MC, Largeron M..  (2015)  Polycyclic Polyprenylated Xanthones from Symphonia globulifera: Isolation and Biomimetic Electrosynthesis.,  78  (8): [PMID:26221771] [10.1021/acs.jnatprod.5b00239]

7. 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]

Source

Source(1):

• Scientific Literature