(12R,15S,16S)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.02,7.012,16]hexadeca-1(10),2(7),4,8-tetraen-6-one

Details

• Internal ID: e39ba0bf-9dd5-4fff-904f-a2c2b73a4ef7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: (12R,15S,16S)-15-hydroxy-14,14-dimethyl-4-phenyl-3,11,13-trioxatetracyclo[8.6.0.02,7.012,16]hexadeca-1(10),2(7),4,8-tetraen-6-one
• SMILES (Canonical): CC1(C(C2C(O1)OC3=C2C4=C(C=C3)C(=O)C=C(O4)C5=CC=CC=C5)O)C
• SMILES (Isomeric): CC1([C@H]([C@H]2[C@@H](O1)OC3=C2C4=C(C=C3)C(=O)C=C(O4)C5=CC=CC=C5)O)C
• InChI: InChI=1S/C21H18O5/c1-21(2)19(23)17-16-14(25-20(17)26-21)9-8-12-13(22)10-15(24-18(12)16)11-6-4-3-5-7-11/h3-10,17,19-20,23H,1-2H3/t17-,19-,20+/m0/s1
• InChI Key: XBKLVCYSINXGAW-YSIASYRMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₅
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.11542367 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	-	0.5175	51.75%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8216	82.16%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9088	90.88%
OATP1B3 inhibitior	+	0.8873	88.73%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8962	89.62%
P-glycoprotein inhibitior	+	0.7867	78.67%
P-glycoprotein substrate	-	0.6885	68.85%
CYP3A4 substrate	+	0.5982	59.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8269	82.69%
CYP3A4 inhibition	+	0.6560	65.60%
CYP2C9 inhibition	+	0.7672	76.72%
CYP2C19 inhibition	-	0.5234	52.34%
CYP2D6 inhibition	-	0.8410	84.10%
CYP1A2 inhibition	-	0.7530	75.30%
CYP2C8 inhibition	+	0.5670	56.70%
CYP inhibitory promiscuity	-	0.6289	62.89%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4022	40.22%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.7219	72.19%
Skin irritation	-	0.6765	67.65%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5960	59.60%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	-	0.6833	68.33%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6475	64.75%
Acute Oral Toxicity (c)	III	0.5344	53.44%
Estrogen receptor binding	+	0.9268	92.68%
Androgen receptor binding	+	0.8443	84.43%
Thyroid receptor binding	+	0.7255	72.55%
Glucocorticoid receptor binding	+	0.8234	82.34%
Aromatase binding	+	0.7603	76.03%
PPAR gamma	+	0.7675	76.75%
Honey bee toxicity	-	0.8191	81.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9752	97.52%

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	98.91%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.97%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.81%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.17%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.89%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.80%	94.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.42%	95.50%

Plants that contains it

• Tephrosia purpurea
• Tephrosia semiglabra

Cross-Links

• PubChem: 21721920
• LOTUS: LTS0244325
• wikiData: Q105324547