ID: ALA59220

Max Phase: Preclinical

Molecular Formula: C20H20O9

Molecular Weight: 404.37

Molecule Type: Small molecule

Representations

Synonyms (1): 5,4'Dihydroxy-3,6,7,8,3'-Pentamethoxyflavone
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1cc(-c2oc3c(OC)c(OC)c(OC)c(O)c3c(=O)c2OC)ccc1O

Standard InChI:  InChI=1S/C20H20O9/c1-24-11-8-9(6-7-10(11)21)15-17(25-2)13(22)12-14(23)18(26-3)20(28-5)19(27-4)16(12)29-15/h6-8,21,23H,1-5H3

Standard InChI Key:  HCAGTMLWEWVIJA-UHFFFAOYSA-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: 404.37

Molecular Weight (Monoisotopic): 404.1107

AlogP: 2.91

#Rotatable Bonds: 6

Polar Surface Area: 116.82

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.19

CX Basic pKa:

CX LogP: 2.25

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: 1.39

References

1. Wang HK, Bastow KF, Cosentino LM, Lee KH..  (1996)  Antitumor agents. 166. Synthesis and biological evaluation of 5,6,7,8-substituted-2-phenylthiochromen-4-ones.,  39  (10): [PMID:8642556] [10.1021/jm960008c]

2. Beutler JA, Hamel E, Vlietinck AJ, Haemers A, Rajan P, Roitman JN, Cardellina JH, Boyd MR..  (1998)  Structure-activity requirements for flavone cytotoxicity and binding to tubulin.,  41  (13): [PMID:9632366] [10.1021/jm970842h]

3. Lichius JJ, Thoison O, Montagnac A, Païs M, Guéritte-Voegelein F, Sévenet T, Cosson JP, Hadi AH..  (1994)  Antimitotic and cytotoxic flavonols from Zieridium pseudobtusifolium and Acronychia porteri.,  57  (7): [PMID:7964782] [10.1021/np50109a024]

4. Zapata-Torres G, Opazo F, Salgado C, Muñoz JP, Krautwurst H, Mascayano C, Sepúlveda-Boza S, Maccioni RB, Cassels BK..  (2004)  Effects of natural flavones and flavonols on the kinase activity of Cdk5.,  67  (3): [PMID:15043421] [10.1021/np034011s]

5. Shi Q, Chen K, Li L, Chang JJ, Autry C, Kozuka M, Konoshima T, Estes JR, Lin CM, Hamel E..  (1995)  Antitumor agents, 154. Cytotoxic and antimitotic flavonols from Polanisia dodecandra.,  58  (4): [PMID:7623025] [10.1021/np50118a001]

Source

Source(1):

• Scientific Literature