Warangalone

Details

• Internal ID: 6fed709a-f1f8-4021-b502-16b2405fdeda
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC=C(C=C4)O)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C3=C1OC=C(C3=O)C4=CC=C(C=C4)O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C25H24O5/c1-14(2)5-10-18-23-17(11-12-25(3,4)30-23)21(27)20-22(28)19(13-29-24(18)20)15-6-8-16(26)9-7-15/h5-9,11-13,26-27H,10H2,1-4H3
• InChI Key: HGHOPAZIUPORIN-UHFFFAOYSA-N
• Popularity: 17 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₅
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.16237386 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.56
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 4449-55-2
• Scandenolone
• Scandenone
• 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)pyrano[3,2-g]chromen-6-one
• 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
• 2H,6H-Benzo[1,2-b:5,4-b']dipyran-6-one, 5-hydroxy-7-(p-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
• 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-2H,6H-pyrano[3,2-g]chromen-6-one
• Warangalon
• 2H,6H-Benzo(1,2-b:5,4-b')dipyran-6-one, 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-
• SCHEMBL571534
• CHEMBL458134
• DTXSID40196193
• HGHOPAZIUPORIN-UHFFFAOYSA-N
• HY-N1074
• LMPK12050205
• AKOS015896248
• CS-8196
• MS-26917
• XW161525
• FT-0655477
• A826605
• B0005-418142
• 5-Hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-2H,6H-pyrano[3,2-g]chromen-6-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9940	99.40%
Caco-2	-	0.5160	51.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8357	83.57%
OATP2B1 inhibitior	-	0.5738	57.38%
OATP1B1 inhibitior	+	0.8864	88.64%
OATP1B3 inhibitior	+	0.9222	92.22%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8952	89.52%
P-glycoprotein inhibitior	+	0.7585	75.85%
P-glycoprotein substrate	-	0.6250	62.50%
CYP3A4 substrate	+	0.6333	63.33%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.8059	80.59%
CYP2C9 inhibition	+	0.9229	92.29%
CYP2C19 inhibition	+	0.9178	91.78%
CYP2D6 inhibition	-	0.8898	88.98%
CYP1A2 inhibition	-	0.6166	61.66%
CYP2C8 inhibition	+	0.6844	68.44%
CYP inhibitory promiscuity	+	0.8853	88.53%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6082	60.82%
Eye corrosion	-	0.9922	99.22%
Eye irritation	+	0.6381	63.81%
Skin irritation	-	0.7200	72.00%
Skin corrosion	-	0.9454	94.54%
Ames mutagenesis	-	0.5537	55.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7346	73.46%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5081	50.81%
skin sensitisation	-	0.7295	72.95%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5062	50.62%
Acute Oral Toxicity (c)	III	0.7360	73.60%
Estrogen receptor binding	+	0.9301	93.01%
Androgen receptor binding	+	0.8476	84.76%
Thyroid receptor binding	+	0.7281	72.81%
Glucocorticoid receptor binding	+	0.8539	85.39%
Aromatase binding	+	0.7429	74.29%
PPAR gamma	+	0.8909	89.09%
Honey bee toxicity	-	0.7934	79.34%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9939	99.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.19%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.30%	98.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	93.34%	93.10%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.96%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.49%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	92.35%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	88.94%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.89%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.81%	91.71%
CHEMBL3038469	P24941	CDK2/Cyclin A	86.99%	91.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.51%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.32%	97.28%
CHEMBL242	Q92731	Estrogen receptor beta	82.73%	98.35%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.46%	95.89%

Plants that contains it

• Anthotroche myoporoides
• Astragalus flexus
• Brachypterum scandens
• Deguelia scandens
• Erythrina addisoniae
• Erythrina fusca
• Erythrina senegalensis
• Erythrina sigmoidea
• Erythrina variegata
• Erythrina vogelii
• Euchresta horsfieldii
• Euchresta japonica
• Helenium virginicum
• Heliotropium digynum
• Hypericum caprifoliatum
• Maclura pomifera
• Millettia extensa
• Millettia pachycarpa
• Nannoglottis ravida
• Ormosia monosperma
• Tephrosia elata

Cross-Links

• PubChem: 5379679
• NPASS: NPC237635
• ChEMBL: CHEMBL458134
• LOTUS: LTS0132135
• wikiData: Q72516518