uvaretin

ID: ALA523296

Chembl Id: CHEMBL523296

Cas Number: 58449-06-2

PubChem CID: 73447

Max Phase: Preclinical

Molecular Formula: C23H22O5

Molecular Weight: 378.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Uvaretin | Uvaretin|58449-06-2|1-[2,4-dihydroxy-3-[(2-hydroxyphenyl)methyl]-6-methoxyphenyl]-3-phenylpropan-1-one|VZ5C9UL7V1|CHEBI:9915|NSC241906|NSC-241906|1-(2,4-Dihydroxy-3-((2-hydroxyphenyl)methyl)-6-methoxyphenyl)-3-phenyl-1-propanone|1-[2,4-Dihydroxy-3-[(2-hydroxyphenyl)methyl]-6-methoxyphenyl]-3-phenyl-1-propanone|1-(2,4-Dihydroxy-3-(2-hydroxybenzyl)-6-methoxyphenyl)-3-phenyl-1-propanone|NSC 241906|UNII-VZ5C9UL7V1|NCIMech_000569|CHEMBL523296|MEGxp0_001394|SCHEMBL4743874|ACon1_001408|DTXSIShow More⌵

Canonical SMILES:  COc1cc(O)c(Cc2ccccc2O)c(O)c1C(=O)CCc1ccccc1

Standard InChI:  InChI=1S/C23H22O5/c1-28-21-14-20(26)17(13-16-9-5-6-10-18(16)24)23(27)22(21)19(25)12-11-15-7-3-2-4-8-15/h2-10,14,24,26-27H,11-13H2,1H3

Standard InChI Key:  LQHGGFQNRNEFIG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA523296

   UVARETIN

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: 378.42

Molecular Weight (Monoisotopic): 378.1467

AlogP: 4.22

#Rotatable Bonds: 7

Polar Surface Area: 86.99

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.21

CX Basic pKa:

CX LogP: 5.48

CX LogD: 4.24

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: 0.90

References

1. Mancini SD, Edwards JM..  (1979)  Cytotoxic principles from the sap of Kalmia latifolia.,  42  (5): [PMID:521818] [10.1021/np50005a008]

2. Chanphen R, Thebtaranonth Y, Wanauppathamkul S, Yuthavong Y..  (1998)  Antimalarial principles from Artemisia indica.,  61  (9): [PMID:9748386] [10.1021/np980041x]

3. PubChem BioAssay data set, 

4. Dallman J, Lansakara A, Nguyen T, Weeramange C, Hulangamuwa W, Rafferty RJ..  (2019)  The winding road of the uvaretin class of natural products: from total synthesis to bioactive agent discovery.,  10  (8): [PMID:31673309] [10.1039/C9MD00052F]

5. Maeda G, van der Wal J, Gupta AK, Munissi JJE, Orthaber A, Sunnerhagen P, Nyandoro SS, Erdélyi M..  (2020)  Oxygenated Cyclohexene Derivatives and Other Constituents from the Roots of Monanthotaxis trichocarpa.,  83  (2): [PMID:31986029] [10.1021/acs.jnatprod.9b00363]

6. Jiwacharoenchai N, Saruengkhanphasit R, Niwetmarin W, Seetaha S, Choowongkomon K, Ruchirawat S, Eurtivong C..  (2022)  Discovery of potent antiproliferative agents from selected oxygen heterocycles as EGFR tyrosine kinase inhibitors from the U.S. National Cancer Institute database by in silico screening and bioactivity evaluation.,  58  [PMID:34995690] [10.1016/j.bmcl.2021.128524]

7. Maeda G, Gilissen PJ, Rudenko A, van der Wal J, Bourgard C, Gupta AK, Sunnerhagen P, Munissi JJE, Nyandoro SS, Erdélyi M..  (2021)  Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis.,  84  (12.0): [PMID:34802242] [10.1021/acs.jnatprod.1c00811]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays