ID: ALA436474

Max Phase: Preclinical

Molecular Formula: C20H12O6

Molecular Weight: 348.31

Molecule Type: Small molecule

Representations

Synonyms (1): Helioxanthin
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C1OCc2c1cc1ccc3c(c1c2-c1ccc2c(c1)OCO2)OCO3

Standard InChI:  InChI=1S/C20H12O6/c21-20-12-5-10-2-4-15-19(26-9-24-15)18(10)17(13(12)7-22-20)11-1-3-14-16(6-11)25-8-23-14/h1-6H,7-9H2

Standard InChI Key:  JUBRYHUFFFYTGR-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: 348.31

Molecular Weight (Monoisotopic): 348.0634

AlogP: 3.63

#Rotatable Bonds: 1

Polar Surface Area: 63.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.32

CX Basic pKa:

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: 1.00

References

1. Yeo H, Li Y, Fu L, Zhu JL, Gullen EA, Dutschman GE, Lee Y, Chung R, Huang ES, Austin DJ, Cheng YC..  (2005)  Synthesis and antiviral activity of helioxanthin analogues.,  48  (2): [PMID:15658867] [10.1021/jm034265a]

2. He K, Zeng L, Shi G, Zhao GX, Kozlowski JF, McLaughlin JL..  (1997)  Bioactive compounds from Taiwania cryptomerioides.,  60  (1): [PMID:9014350] [10.1021/np960513c]

3. Olaniyi AA, Powell JW.  (1980)  Lignans From Justicia flava,  43  (4): [10.1021/np50010a008]

4. Janmanchi D, Tseng YP, Wang KC, Huang RL, Lin CH, Yeh SF..  (2010)  Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents.,  18  (3): [PMID:20061158] [10.1016/j.bmc.2009.12.038]

5. Janmanchi D, Lin CH, Hsieh JY, Tseng YP, Chen TA, Jhuang HJ, Yeh SF..  (2013)  Synthesis and biological evaluation of helioxanthin analogues.,  21  (7): [PMID:23465436] [10.1016/j.bmc.2012.11.037]

6. Zhang F, Wang G..  (2014)  A review of non-nucleoside anti-hepatitis B virus agents.,  75  [PMID:24549242] [10.1016/j.ejmech.2014.01.046]

7. Hajdu Z, Haskó J, Krizbai IA, Wilhelm I, Jedlinszki N, Fazakas C, Molnár J, Forgo P, Hohmann J, Csupor D..  (2014)  Evaluation of lignans from Heliopsis helianthoides var. scabra for their potential antimetastatic effects in the brain.,  77  (12): [PMID:25479041] [10.1021/np500508y]

8. Pei Y, Wang C, Yan SF, Liu G..  (2017)  Past, Current, and Future Developments of Therapeutic Agents for Treatment of Chronic Hepatitis B Virus Infection.,  60  (15): [PMID:28383274] [10.1021/acs.jmedchem.6b01442]

Source

Source(1):

• Scientific Literature