Pedunculagin

ID: ALA506204

Chembl Id: CHEMBL506204

Cas Number: 7045-42-3

PubChem CID: 442688

Max Phase: Preclinical

Molecular Formula: C34H24O22

Molecular Weight: 784.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pedunculagin | Pedunculagin|CHEBI:7948|CHEMBL506204|7045-42-3|C10236|DTXSID20990656|BDBM50242262|Q7160092|(1R,2S,19R,22R)-7,8,9,12,13,14,20,28,29,30,33,34,35-tridecahydroxy-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.02,19.05,10.011,16.026,31.032,37]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaene-4,17,25,38-tetrone

Canonical SMILES:  O=C1OC[C@H]2OC(O)[C@@H]3OC(=O)c4cc(O)c(O)c(O)c4-c4c(cc(O)c(O)c4O)C(=O)O[C@H]3[C@@H]2OC(=O)c2cc(O)c(O)c(O)c2-c2c1cc(O)c(O)c2O

Standard InChI:  InChI=1S/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34?/m1/s1

Standard InChI Key:  IYMHVUYNBVWXKH-ZITZVVOASA-N

Alternative Forms

1. Parent:

   

   ALA506204

   PEDUNCULAGIN

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: 784.54

Molecular Weight (Monoisotopic): 784.0759

AlogP: 0.67

#Rotatable Bonds: ┄

Polar Surface Area: 377.42

Molecular Species: NEUTRAL

HBA: 22

HBD: 13

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 6.86

CX Basic pKa: ┄

CX LogP: 1.95

CX LogD: 0.98

Aromatic Rings: 4

Heavy Atoms: 56

QED Weighted: 0.07

Np Likeness Score: 0.96

References

1. König M, Scholz E, Hartmann R, Lehmann W, Rimpler H..  (1994)  Ellagitannins and complex tannins from Quercus petraea bark.,  57  (10): [PMID:7807126] [10.1021/np50112a010]

2. 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]

3. 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]

4. 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]

5. Dong H, Chen SX, Kini RM, Xu HX..  (1998)  Effects of tannins from Geum japonicum on the catalytic activity of thrombin and factor Xa of blood coagulation cascade.,  61  (11): [PMID:9834152] [10.1021/np9801458]

6. Huang SS, Yeh SF, Hong CY..  (1995)  Effect of anthraquinone derivatives on lipid peroxidation in rat heart mitochondria: structure-activity relationship.,  58  (9): [PMID:7494143] [10.1021/np50123a005]

7. Tamura S, Yang GM, Yasueda N, Matsuura Y, Komoda Y, Murakami N..  (2010)  Tellimagrandin I, HCV invasion inhibitor from Rosae Rugosae Flos.,  20  (5): [PMID:20144544] [10.1016/j.bmcl.2010.01.084]

Source

Source(1):

• Scientific Literature