Coumestrol

Details

• Internal ID: 09d56ad3-c44c-403f-ba3e-fd8434ab3465
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Coumestans
• IUPAC Name: 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
• SMILES (Canonical): C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
• SMILES (Isomeric): C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
• InChI: InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
• InChI Key: ZZIALNLLNHEQPJ-UHFFFAOYSA-N
• Popularity: 1,200 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₈O₅
• Molecular Weight: 268.22 g/mol
• Exact Mass: 268.03717335 g/mol
• Topological Polar Surface Area (TPSA): 79.90 Ų
• XlogP: 2.80

Synonyms

• 479-13-0
• Cumoestrol
• Cumoesterol
• Cumostrol
• 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one
• 3,9-Dihydroxycoumestan
• NSC 22842
• CCRIS 7311
• Cumestrol
• EINECS 207-525-6
• UNII-V7NW98OB34
• BRN 0266702
• CHEBI:3908
• V7NW98OB34
• DTXSID6022399
• C15H8O5
• NSC22842
• 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 3,9-dihydroxy-
• NSC-22842
• 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
• 3,9-dihydroxy-6H-benzofuro[3,2-c]chromen-6-one
• CHEMBL30707
• 3,9-Dihydroxy-6H-benzofuro(3,2-c)(1)benzopyran-6-one
• MLS000738006
• DTXCID102399
• 3,9-dihydroxybenzofuro[3,2-c]chromen-6-one
• 5-19-06-00405 (Beilstein Handbook Reference)
• 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihydroxy-
• 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone
• 7,12-Dihydroxycoumestan
• SMR000059001
• 3,9-dihydroxy-6H-(1)benzofuro(3,2-c)chromen-6-one
• 3,9-dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one
• Coumestrol (COU)
• MFCD00016885
• COUMESTROL [MI]
• D02DML
• NCIMech_000078
• Oprea1_222511
• SCHEMBL22012
• MLS000069446
• BIDD:ER0114
• BDBM23451
• GTPL12437
• HMS2235B05
• HMS3374A07
• 6H-Benzofuro[3, 3,9-dihydroxy-
• Coumestrol, >=95.0% (HPLC)
• HY-N2335
• Tox21_200032
• C15-H8-O5
• CCG-35536
• CCG-36200
• LMPK12090018
• AKOS028111776
• CS-6343
• SMP2_000163
• NCGC00018124-01
• NCGC00018124-02
• NCGC00018124-03
• NCGC00018124-04
• NCGC00018124-05
• NCGC00018124-06
• NCGC00023462-03
• NCGC00023462-04
• NCGC00257586-01
• AS-81377
• CAS-479-13-0
• LS-35394
• NCI60_001863
• FT-0603177
• D85092
• S00280
• US8552057, 3
• 3,9-dihydroxy-[1]benzoxolo[3,2-c]chromen-6-one
• A827386
• Q908865
• A1-00298
• BRD-K97509413-001-01-8
• 3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one #
• 3,9-Dihydroxy-6H-benzo-furo[3,2-c][1]benzopyran-6-one
• 6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 3,9-dihdyroxy-
• Coumestrol, BioReagent, suitable for fluorescence, >=97.5% (HPLC)
• 2-(2,4-dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic acid delta-lactone
• 3-Benzofurancarboxylic acid,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone
• 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, .delta.-lactone
• 3-Benzofurancarboxylic acid, 2-(2,4-dihydroxyphenyl)-6-hydroxy-, delta-lactone (6CI)
• 5,14-dihydroxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	25118.9 nM	Potency	via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	31622.8 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	31622.8 nM; 22387.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	28183.8 nM	Potency	via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	35481.3 nM	Potency	via CMAUP
CHEMBL206	P03372	Estrogen receptor alpha	75.7 nM; 75.7 nM; 75.7 nM; 75.7 nM	IC50; IC50; IC50; IC50	PMID: 15887952; PMID: 15887952; via CMAUP; via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	18.6 nM; 18.6 nM; 18.6 nM; 18.6 nM	IC50; IC50; IC50; IC50	via CMAUP; PMID: 15887952; PMID: 15887952; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	10000 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	10000 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	25118.9 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3401	O75469	Pregnane X receptor	12000 nM	IC50	PMID: 24828006
CHEMBL1293235	P02545	Prelamin-A/C	14125.4 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.13%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.08%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.53%	95.56%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.09%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	87.52%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.29%	86.33%
CHEMBL3194	P02766	Transthyretin	86.96%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	86.44%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.14%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.84%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.46%	94.00%

Plants that contains it

• Atalantia buxifolia
• Bituminaria morisiana
• Campylotropis hirtella
• Cullen corylifolium
• Ducrosia ismaelis
• Elettaria cardamomum
• Glycine canescens
• Glycine max
• Hedysarum polybotrys
• Medicago sativa
• Phaseolus coccineus
• Phaseolus lunatus
• Phaseolus vulgaris
• Pueraria montana var. lobata
• Punica granatum
• Secale cereale
• Spatholobus harmandii
• Spinacia oleracea
• Taraxacum officinale
• Tephrosia purpurea
• Trifolium pratense
• Trifolium repens
• Ziziphus jujuba

Cross-Links

• PubChem: 5281707
• NPASS: NPC41326
• ChEMBL: CHEMBL30707
• LOTUS: LTS0206171
• wikiData: Q105112376