7,7,8,12,13,22-hexahydroxy-21-hydroxymethyl-3,6,16-trioxo-19-(3,4,5-trihydroxyphenylcarbonyloxy)-2,17,20,23-tetraoxapentacyclo[16.3.1.18,11.04,9.010,15]tricosa-4,10,12,14-tetraene

ID: ALA1159461

PubChem CID: 46905119

Max Phase: Preclinical

Molecular Formula: C27H22O19

Molecular Weight: 650.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O[C@H]2[C@H](O)[C@@H](OC(=O)c3cc(O)c(O)c4c3C3C1=CC(=O)C(O)(O)C3(O)O4)[C@@H](OC(=O)c1cc(O)c(O)c(O)c1)O[C@@H]2CO

Standard InChI:  InChI=1S/C27H22O19/c28-5-12-19-18(35)21(25(42-12)45-22(36)6-1-9(29)16(33)10(30)2-6)44-23(37)7-3-11(31)17(34)20-14(7)15-8(24(38)43-19)4-13(32)26(39,40)27(15,41)46-20/h1-4,12,15,18-19,21,25,28-31,33-35,39-41H,5H2/t12-,15?,18+,19-,21-,25-,27?/m1/s1

Standard InChI Key:  CXTMLIMZRPKULL-YHZURHLKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1159461

   [(1S,18R,19R,21R,22S)-7,7,8,12,13,22-hexahydroxy-21-(hydroxymethyl)-3,6,16-trioxo-2,17,20,23-tetraoxapentacyclo[16.3.1.18,11.04,9.010,15]tricosa-4,10,12,14-tetraen-19-yl] 3,4,5-trihydroxybenzoate

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

Calculated Properties

Molecular Weight: 650.45

Molecular Weight (Monoisotopic): 650.0755

AlogP: -3.04

#Rotatable Bonds: 3

Polar Surface Area: 316.73

Molecular Species: NEUTRAL

HBA: 19

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.80

CX Basic pKa: ┄

CX LogP: -0.24

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.07

Np Likeness Score: 2.22

References

1. Kashiwada Y, Nonaka G, Nishioka I, Ballas LM, Jiang JB, Janzen WP, Lee K.  (1992)  Tannins as selective inhibitors of protein kinase C,  2  (3): [10.1016/S0960-894X(01)81072-6]

Source

Source(1):

• Scientific Literature