xanthoangelol B

ID: ALA494082

Chembl Id: CHEMBL494082

Cas Number: 132998-81-3

PubChem CID: 10409180

Max Phase: Preclinical

Molecular Formula: C25H28O5

Molecular Weight: 408.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C(O)CC/C(C)=C/Cc1c(O)ccc(C(=O)/C=C/c2ccc(O)cc2)c1O

Standard InChI:  InChI=1S/C25H28O5/c1-16(2)22(27)13-5-17(3)4-11-20-24(29)15-12-21(25(20)30)23(28)14-8-18-6-9-19(26)10-7-18/h4,6-10,12,14-15,22,26-27,29-30H,1,5,11,13H2,2-3H3/b14-8+,17-4+

Standard InChI Key:  NCHZAFAGBAEJJJ-BAYITLGHSA-N

Alternative Forms

1. Parent:

   

   ALA494082

   XANTHOANGELOL B

Molecule Features

Natural Product: No

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: 408.49

Molecular Weight (Monoisotopic): 408.1937

AlogP: 4.91

#Rotatable Bonds: 9

Polar Surface Area: 97.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.93

CX Basic pKa: ┄

CX LogP: 5.85

CX LogD: 5.23

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.27

Np Likeness Score: 1.93

References

1. Aoki N, Muko M, Ohta E, Ohta S..  (2008)  C-geranylated chalcones from the stems of Angelica keiskei with superoxide-scavenging activity.,  71  (7): [PMID:18558745] [10.1021/np800187f]

2. PubChem BioAssay data set, 

3. Park JY, Jeong HJ, Kim YM, Park SJ, Rho MC, Park KH, Ryu YB, Lee WS..  (2011)  Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition.,  21  (18): [PMID:21824777] [10.1016/j.bmcl.2011.06.130]

4. Mizar P, Arya R, Kim T, Cha S, Ryu KS, Yeo WS, Bae T, Kim DW, Park KH, Kim KK, Lee SS..  (2018)  Total Synthesis of Xanthoangelol B and Its Various Fragments: Toward Inhibition of Virulence Factor Production of Staphylococcus aureus.,  61  (23): [PMID:30388007] [10.1021/acs.jmedchem.8b01012]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays