Urushiol III

Details

• Internal ID: 87553c46-8292-4c4e-a36f-9900fd5a8d22
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 3-[(8E,11E)-pentadeca-8,11-dienyl]benzene-1,2-diol
• SMILES (Canonical): CCCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)O
• SMILES (Isomeric): CCC/C=C/C/C=C/CCCCCCCC1=C(C(=CC=C1)O)O
• InChI: InChI=1S/C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(22)21(19)23/h4-5,7-8,15,17-18,22-23H,2-3,6,9-14,16H2,1H3/b5-4+,8-7+
• InChI Key: RMTXUPIIESNLPW-AOSYACOCSA-N
• Popularity: 431 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.50 g/mol
• Exact Mass: 316.240230259 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 7.40
• Atomic LogP (AlogP): 6.28
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 12

Synonyms

• 3-(8,11-Pentadecadienyl)-1,2-benzenediol
• 492-91-1
• 3-[(8E,11E)-pentadeca-8,11-dienyl]benzene-1,2-diol
• 1,2-Benzenediol, 3-(8,11-pentadecadienyl)-
• C10839
• 1,2-Benzenediol, 3-(8Z,11Z)-8,11-pentadecadienyl-
• AC1NQZ73
• monomeric urushiol
• SureCN4743862
• Urushiol III (C15:2)
• CHEBI:9909
• SCHEMBL4743862
• Q27108511

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.5400	54.00%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8116	81.16%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.8100	81.00%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5794	57.94%
P-glycoprotein inhibitior	-	0.5190	51.90%
P-glycoprotein substrate	-	0.7088	70.88%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7939	79.39%
CYP2D6 substrate	-	0.6799	67.99%
CYP3A4 inhibition	-	0.6780	67.80%
CYP2C9 inhibition	-	0.5596	55.96%
CYP2C19 inhibition	-	0.5263	52.63%
CYP2D6 inhibition	-	0.8178	81.78%
CYP1A2 inhibition	+	0.6633	66.33%
CYP2C8 inhibition	+	0.5477	54.77%
CYP inhibitory promiscuity	+	0.5429	54.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7000	70.00%
Carcinogenicity (trinary)	Non-required	0.5531	55.31%
Eye corrosion	+	0.4563	45.63%
Eye irritation	-	0.5490	54.90%
Skin irritation	+	0.5280	52.80%
Skin corrosion	+	0.5268	52.68%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8994	89.94%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5717	57.17%
skin sensitisation	+	0.8786	87.86%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5175	51.75%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.8568	85.68%
Acute Oral Toxicity (c)	III	0.7933	79.33%
Estrogen receptor binding	+	0.8442	84.42%
Androgen receptor binding	-	0.5234	52.34%
Thyroid receptor binding	+	0.6833	68.33%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5605	56.05%
PPAR gamma	+	0.8443	84.43%
Honey bee toxicity	-	0.9839	98.39%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6562	65.62%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.51%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.38%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.33%	86.33%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.83%	92.08%
CHEMBL3401	O75469	Pregnane X receptor	90.17%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.73%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.16%	96.09%
CHEMBL230	P35354	Cyclooxygenase-2	88.93%	89.63%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.71%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.58%	95.56%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.55%	96.25%
CHEMBL1951	P21397	Monoamine oxidase A	85.43%	91.49%
CHEMBL1781	P11387	DNA topoisomerase I	81.99%	97.00%

Plants that contains it

• Cornus officinalis
• Eucommia ulmoides
• Forsythia suspensa
• Gardenia jasminoides
• Isodon rubescens
• Ligustrum lucidum
• Paulownia tomentosa
• Plantago asiatica
• Pyrola japonica
• Salvia miltiorrhiza
• Toxicodendron radicans

Cross-Links

• PubChem: 5281862
• NPASS: NPC37859
• LOTUS: LTS0145404
• wikiData: Q27108511