Isobavachromene

Details

• Internal ID: 5fd0f890-b462-4436-8704-5de0e223972b
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
• IUPAC Name: (E)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=CC(=C2O)C(=O)C=CC3=CC=C(C=C3)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=CC(=C2O)C(=O)/C=C/C3=CC=C(C=C3)O)C
• InChI: InChI=1S/C20H18O4/c1-20(2)12-11-16-18(24-20)10-8-15(19(16)23)17(22)9-5-13-3-6-14(21)7-4-13/h3-12,21,23H,1-2H3/b9-5+
• InChI Key: IQHPDUUSMBMDGN-WEVVVXLNSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₄
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 4-Hydroxylonchocarpin
• 56083-03-5
• 52801-22-6
• CHEMBL362378
• D6S8A779IY
• (E)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 2-Propen-1-one,1-(5-hydroxy-2,2-dimethyl- 2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)-
• 2-Propen-1-one, 1-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-3-(4-hydroxyphenyl)-, (2E)-
• 4-Hydroxylonchocharpin
• D0F3QP
• UNII-D6S8A779IY
• SCHEMBL19960679
• HY-N2208A
• BDBM50240945
• LMPK12120077
• AKOS037515129
• AKOS040760469
• AC-35075
• MS-24777
• CS-0090490
• (2E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• (E)-1-(5-hydroxy-2,2-dimethyl-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 1-(5-Hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxy-phenyl)-propenone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.6920	69.20%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8029	80.29%
OATP2B1 inhibitior	+	0.5624	56.24%
OATP1B1 inhibitior	+	0.8649	86.49%
OATP1B3 inhibitior	+	0.9886	98.86%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8441	84.41%
P-glycoprotein inhibitior	-	0.4779	47.79%
P-glycoprotein substrate	-	0.7602	76.02%
CYP3A4 substrate	+	0.5383	53.83%
CYP2C9 substrate	-	0.7983	79.83%
CYP2D6 substrate	-	0.8506	85.06%
CYP3A4 inhibition	-	0.5074	50.74%
CYP2C9 inhibition	+	0.8131	81.31%
CYP2C19 inhibition	+	0.7176	71.76%
CYP2D6 inhibition	-	0.7913	79.13%
CYP1A2 inhibition	+	0.8427	84.27%
CYP2C8 inhibition	+	0.6783	67.83%
CYP inhibitory promiscuity	+	0.6857	68.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9813	98.13%
Carcinogenicity (trinary)	Non-required	0.5918	59.18%
Eye corrosion	-	0.9886	98.86%
Eye irritation	+	0.7558	75.58%
Skin irritation	-	0.6544	65.44%
Skin corrosion	-	0.9341	93.41%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5394	53.94%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.6884	68.84%
skin sensitisation	-	0.7281	72.81%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5299	52.99%
Acute Oral Toxicity (c)	III	0.6865	68.65%
Estrogen receptor binding	+	0.9592	95.92%
Androgen receptor binding	+	0.8408	84.08%
Thyroid receptor binding	+	0.7820	78.20%
Glucocorticoid receptor binding	+	0.9118	91.18%
Aromatase binding	+	0.8421	84.21%
PPAR gamma	+	0.8828	88.28%
Honey bee toxicity	-	0.8898	88.98%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9827	98.27%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1869	P11926	Ornithine decarboxylase	4700 nM	IC50	PMID: 10075742

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.83%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.50%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	90.63%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.51%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.11%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.80%	96.09%
CHEMBL4208	P20618	Proteasome component C5	87.20%	90.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.48%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	84.27%	94.73%
CHEMBL3194	P02766	Transthyretin	83.88%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.78%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.69%	95.50%

Plants that contains it

• Achillea cretica
• Ageratina riparia
• Brosimum acutifolium
• Cordia americana
• Cullen corylifolium
• Dorstenia barteri
• Dorstenia dinklagei
• Dorstenia mannii
• Dorstenia prorepens
• Glycosmis lanceolata
• Glycyrrhiza
• Glycyrrhiza glabra
• Lactuca floridana
• Lonchocarpus sericeus
• Millettia dura
• Millettia ferruginea
• Mundulea sericea
• Pedicularis semitorta
• Scopolia japonica
• Scorzoneroides autumnalis
• Sophora prostrata
• Ulex minor
• Ventilago leiocarpa

Cross-Links

• PubChem: 5889042
• NPASS: NPC156590
• ChEMBL: CHEMBL362378
• LOTUS: LTS0223233
• wikiData: Q76312324