Eupatoriochromene

Details

• Internal ID: d3338cc4-1962-46dd-b006-82628e49de51
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > 2,2-dimethyl-1-benzopyrans
• IUPAC Name: 1-(7-hydroxy-2,2-dimethylchromen-6-yl)ethanone
• SMILES (Canonical): CC(=O)C1=C(C=C2C(=C1)C=CC(O2)(C)C)O
• SMILES (Isomeric): CC(=O)C1=C(C=C2C(=C1)C=CC(O2)(C)C)O
• InChI: InChI=1S/C13H14O3/c1-8(14)10-6-9-4-5-13(2,3)16-12(9)7-11(10)15/h4-7,15H,1-3H3
• InChI Key: SVUVYHFYZBCYRF-UHFFFAOYSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.25 g/mol
• Exact Mass: 218.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 19013-03-7
• DEMETHYLENCECALIN
• Desmethylencecalin
• 7-demethylencecalin
• 1-(7-hydroxy-2,2-dimethylchromen-6-yl)ethanone
• Ethanone, 1-(7-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-
• 1-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)ethanone
• O9Y1UY34HC
• CHEBI:4936
• NSC 363789
• NSC-363789
• Spectrum_000670
• SpecPlus_000198
• Spectrum2_000671
• Spectrum3_001246
• Spectrum4_001452
• Spectrum5_000063
• DE(METHYL)ENCECALIN
• UNII-O9Y1UY34HC
• C09006
• BSPBio_002752
• KBioGR_001963
• KBioSS_001150
• SPECTRUM300061
• CHROMENE DERIV (HERZ)
• DivK1c_006294
• SPBio_000761
• CHEMBL443462
• MEGxp0_001834
• KBio1_001238
• KBio2_001150
• KBio2_003718
• KBio2_006286
• KBio3_002252
• DTXSID70172485
• SVUVYHFYZBCYRF-UHFFFAOYSA-N
• HMS1923G11
• CCG-38569
• NSC363789
• AKOS022652862
• CS-W000239
• SDCCGMLS-0066474.P001
• NCGC00095249-01
• NCGC00095249-02
• NCGC00095249-03
• NCGC00095249-04
• 6-acetyl-7-hydroxy-2,2-dimethylchromene
• HY-119596
• CS-0070032
• 1-(7-hydroxy-2,2-dimethyl-chromen-6-yl)ethanone
• BRD-K55704455-001-02-2
• Q27106568
• 1-(7-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-ethanone
• 1-(7-Hydroxy-2,2-dimethyl-2H-chromen-6-yl)ethan-1-one
• 1-(7-Hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-ethanone
• 1-(7-HYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-YL)ETHANONE
• KETONE, 7-HYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-YL METHYL
• InChI=1/C13H14O3/c1-8(14)10-6-9-4-5-13(2,3)16-12(9)7-11(10)15/h4-7,15H,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.8027	80.27%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7772	77.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9913	99.13%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7843	78.43%
P-glycoprotein inhibitior	-	0.9438	94.38%
P-glycoprotein substrate	-	0.8503	85.03%
CYP3A4 substrate	-	0.5456	54.56%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8303	83.03%
CYP3A4 inhibition	-	0.7652	76.52%
CYP2C9 inhibition	-	0.5865	58.65%
CYP2C19 inhibition	+	0.6696	66.96%
CYP2D6 inhibition	-	0.8768	87.68%
CYP1A2 inhibition	+	0.9099	90.99%
CYP2C8 inhibition	-	0.7229	72.29%
CYP inhibitory promiscuity	+	0.5443	54.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.5520	55.20%
Eye corrosion	-	0.9636	96.36%
Eye irritation	+	0.9590	95.90%
Skin irritation	-	0.5193	51.93%
Skin corrosion	-	0.9275	92.75%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6837	68.37%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	-	0.5436	54.36%
skin sensitisation	-	0.6124	61.24%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6367	63.67%
Acute Oral Toxicity (c)	III	0.6060	60.60%
Estrogen receptor binding	+	0.7365	73.65%
Androgen receptor binding	-	0.8490	84.90%
Thyroid receptor binding	+	0.5135	51.35%
Glucocorticoid receptor binding	+	0.5692	56.92%
Aromatase binding	+	0.5489	54.89%
PPAR gamma	+	0.7412	74.12%
Honey bee toxicity	-	0.9513	95.13%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	0.9536	95.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	25118.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	22387.2 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	97.02%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.68%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.07%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.59%	89.00%
CHEMBL2581	P07339	Cathepsin D	87.22%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.30%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	84.82%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.81%	93.65%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.66%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.01%	86.33%

Plants that contains it

• Ageratina adenophora
• Ageratina altissima
• Ageratina glechonophylla
• Ageratina prunellifolia
• Ageratina riparia
• Arnica lanceolata subsp. prima
• Arnica sachalinensis
• Calea jamaicensis
• Calea oxylepis
• Calea rotundifolia
• Calea serrata
• Calea sickii
• Centromadia fitchii
• Encelia californica
• Encelia farinosa
• Eupatorium semiserratum
• Flourensia thurifera
• Helianthella quinquenervis
• Helianthella uniflora
• Helianthus annuus
• Helianthus hirsutus
• Hemizonia congesta
• Madia sativa
• Myroxylon balsamum
• Ophryosporus floribundus
• Ophryosporus heptanthus
• Orthosiphon aristatus var. aristatus
• Piper aduncum
• Pyrrosia davidii
• Sorghum bicolor
• Tithonia diversifolia

Cross-Links

• PubChem: 100768
• NPASS: NPC151113
• ChEMBL: CHEMBL443462
• LOTUS: LTS0077277
• wikiData: Q27106568