ID: ALA501154

Max Phase: Preclinical

Molecular Formula: C41H32O27

Molecular Weight: 956.68

Molecule Type: Small molecule

Representations

Synonyms (1): Chebulinic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(O)C[C@H]1C(=O)O[C@H]2[C@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@@H](OC(=O)c3cc(O)c(O)c4c3[C@H]1[C@H](O)C(=O)O4)[C@H](OC(=O)c1cc(O)c(O)c(O)c1)O[C@@H]2COC(=O)c1cc(O)c(O)c(O)c1

Standard InChI:  InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22-,24+,30+,31-,33+,34-,41+/m1/s1

Standard InChI Key:  YGVHOSGNOYKRIH-JHSYUSIXSA-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: 956.68

Molecular Weight (Monoisotopic): 956.1131

AlogP: 0.02

#Rotatable Bonds: 9

Polar Surface Area: 447.09

Molecular Species: ACID

HBA: 26

HBD: 13

#RO5 Violations: 3

HBA (Lipinski): 27

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.16

CX Basic pKa:

CX LogP: 3.02

CX LogD: -0.70

Aromatic Rings: 4

Heavy Atoms: 68

QED Weighted: 0.05

Np Likeness Score: 1.30

References

1. Nonaka G, Nishioka I, Nishizawa M, Yamagishi T, Kashiwada Y, Dutschman GE, Bodner AJ, Kilkuskie RE, Cheng YC, Lee KH..  (1990)  Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells.,  53  (3): [PMID:1698933] [10.1021/np50069a008]

2. Li XC, Joshi AS, ElSohly HN, Khan SI, Jacob MR, Zhang Z, Khan IA, Ferreira D, Walker LA, Broedel SE, Raulli RE, Cihlar RL..  (2002)  Fatty acid synthase inhibitors from plants: isolation, structure elucidation, and SAR studies.,  65  (12): [PMID:12502337] [10.1021/np020289t]

3. Abe I, Kashiwagi Y, Noguchi H, Tanaka T, Ikeshiro Y, Kashiwada Y..  (2001)  Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.,  64  (8): [PMID:11520216] [10.1021/np010100y]

4. Kakiuchi N, Hattori M, Namba T, Nishizawa M, Yamagishi T, Okuda T..  (1985)  Inhibitory effect of tannins on reverse transcriptase from RNA tumor virus.,  48  (4): [PMID:2413172] [10.1021/np50040a016]

5. Kashiwada Y, Nonaka G, Nishioka I, Chang JJ, Lee KH..  (1992)  Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.,  55  (8): [PMID:1431932] [10.1021/np50086a002]

6. Lin T, Hsu F, Cheng J.  (1993)  Antihypertensive Activity of Corilagin and Chebulinic Acid, Tannins from Lumnitzera, racemosa,  56  (4): [10.1021/np50094a030]

Source

Source(1):

• Scientific Literature