Houttuynoid A

ID: ALA4168424

Chembl Id: CHEMBL4168424

PubChem CID: 57412149

Max Phase: Preclinical

Molecular Formula: C33H38O13

Molecular Weight: 642.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCc1oc2c(O)ccc(-c3oc4cc(O)cc(O)c4c(=O)c3O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)c2c1C=O

Standard InChI:  InChI=1S/C33H38O13/c1-2-3-4-5-6-7-8-9-21-18(14-34)24-17(10-11-19(37)31(24)43-21)30-32(27(40)25-20(38)12-16(36)13-22(25)44-30)46-33-29(42)28(41)26(39)23(15-35)45-33/h10-14,23,26,28-29,33,35-39,41-42H,2-9,15H2,1H3/t23-,26+,28+,29-,33+/m1/s1

Standard InChI Key:  FHNVKCJCSKWUFS-YLUJEXTNSA-N

Alternative Forms

1. Parent:

   

   ALA4168424

   4-[5,7-dihydroxy-4-oxo-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-yl]-7-hydroxy-2-nonyl-1-benzofuran-3-carbaldehyde

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: 642.65

Molecular Weight (Monoisotopic): 642.2312

AlogP: 3.61

#Rotatable Bonds: 13

Polar Surface Area: 220.49

Molecular Species: ACID

HBA: 13

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 5.85

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 1.33

Aromatic Rings: 4

Heavy Atoms: 46

QED Weighted: 0.08

Np Likeness Score: 1.81

References

1. Li JJ, Chen GD, Fan HX, Hu D, Zhou ZQ, Lan KH, Zhang HP, Maeda H, Yao XS, Gao H..  (2017)  Houttuynoid M, an Anti-HSV Active Houttuynoid from Houttuynia cordata Featuring a Bis-houttuynin Chain Tethered to a Flavonoid Core.,  80  (11): [PMID:29099182] [10.1021/acs.jnatprod.7b00620]

2. Jian J, Fan J, Yang H, Lan P, Li M, Liu P, Gao H, Sun P..  (2018)  Total Synthesis of the Flavonoid Natural Product Houttuynoid A.,  81  (2): [PMID:29394065] [10.1021/acs.jnatprod.7b00791]

Source

Source(1):

• Scientific Literature