Tapinarof

Details

• Internal ID: bbf88826-0c78-4f74-9514-21d4e0bd8b56
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
• InChI: InChI=1S/C17H18O2/c1-12(2)17-15(18)10-14(11-16(17)19)9-8-13-6-4-3-5-7-13/h3-12,18-19H,1-2H3/b9-8+
• InChI Key: ZISJNXNHJRQYJO-CMDGGOBGSA-N
• Popularity: 423 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₂
• Molecular Weight: 254.32 g/mol
• Exact Mass: 254.130679813 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• Tapinarof
• 79338-84-4
• 3,5-Dihydroxy-4-isopropylstilbene
• Vtama
• WBI-1001
• GSK2894512
• GSK-2894512
• 3,5-dihydroxy-4-isopropyl-trans-stilbene
• 5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
• 3,5-DH4IS
• WBI 1001
• (E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol
• 84HW7D0V04
• DTXSID301045262
• 1,3-Benzenediol, 2-(1-methylethyl)-5-(2-phenylethenyl)-, (E)-
• tapinarofum
• 5-((E)-2-phenylethenyl)-2-propan-2-ylbenzene-1,3-diol
• 2-(1-Methylethyl)-5-[(1E)-2-phenylethenyl]-1,3-benzenediol
• 2-(1-METHYLETHYL)-5-((1E)-2-PHENYLETHENYL)-1,3-BENZENEDIOL
• RefChem:57353
• DTXCID101527189
• 5-(2-phenylethenyl)-2-isopropyl-1,3-benzenediol
• (E)-2-isopropyl-5-styrylbenzene-1,3-diol
• 2-Isopropyl-5-styrylbenzene-1,3-diol
• MFCD13193203
• Tapinarof [USAN]
• 115781-08-3
• 1,3-Benzenediol, 2-(1-methylethyl)-5-[(1E)-2-phenylethenyl]-
• (E)-3,5-Dihydroxy-4-isopropylstilbene
• 1,3-Benzenediol, 2-(1-methylethyl)-5-(2-phenylethenyl)-
• 5-[(1E)-2-phenylethenyl]-2-(propan-2-yl)benzene-1,3-diol
• UNII-84HW7D0V04
• (E)-Benvitimod
• Tapinarof (Standard)
• Vtama (TN)
• Benvitimod (Tapinarof)
• TAPINAROF [INN]
• Tapinarof (JAN/USAN)
• TAPINAROF [WHO-DD]
• SCHEMBL918343
• CHEMBL259571
• GTPL9686
• orb1302687
• orb3025055
• CHEBI:215747
• GLXC-20861
• EX-A4877
• BDBM50603566
• MSK163810
• s9700
• AKOS025296109
• DB06083
• HY-109044R
• TN10179
• WB-1001
• AC-36567
• AS-44364
• FD167852
• SY243403
• Tapinarof (Benvitimod; GSK2894512)?
• HY-109044
• CS-0031487
• NS00069997
• 2-isopropyl-5-[(E)-styryl]benzene-1,3-diol
• A11410
• D11365
• F542358
• Q4634086
• 2-ISOPROPYL-5-[(E)-2-PHENYLETHENYL]BENZENE-1,3-DIOL
• 5-[(1E)-2-Phenylethen-1-yl]-2-(propan-2-yl)benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.8732	87.32%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8006	80.06%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9035	90.35%
OATP1B3 inhibitior	+	0.9701	97.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	+	0.6708	67.08%
P-glycoprotein inhibitior	-	0.8329	83.29%
P-glycoprotein substrate	-	0.9728	97.28%
CYP3A4 substrate	-	0.7245	72.45%
CYP2C9 substrate	-	0.5681	56.81%
CYP2D6 substrate	-	0.7360	73.60%
CYP3A4 inhibition	+	0.5395	53.95%
CYP2C9 inhibition	+	0.9250	92.50%
CYP2C19 inhibition	+	0.8900	89.00%
CYP2D6 inhibition	-	0.8521	85.21%
CYP1A2 inhibition	+	0.9679	96.79%
CYP2C8 inhibition	-	0.8734	87.34%
CYP inhibitory promiscuity	+	0.9209	92.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7350	73.50%
Carcinogenicity (trinary)	Non-required	0.7053	70.53%
Eye corrosion	-	0.8697	86.97%
Eye irritation	+	0.8638	86.38%
Skin irritation	-	0.7107	71.07%
Skin corrosion	+	0.8520	85.20%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6751	67.51%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6440	64.40%
skin sensitisation	+	0.9326	93.26%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.5857	58.57%
Acute Oral Toxicity (c)	III	0.6936	69.36%
Estrogen receptor binding	+	0.9247	92.47%
Androgen receptor binding	+	0.8213	82.13%
Thyroid receptor binding	+	0.7898	78.98%
Glucocorticoid receptor binding	-	0.4655	46.55%
Aromatase binding	+	0.8374	83.74%
PPAR gamma	+	0.7472	74.72%
Honey bee toxicity	-	0.9483	94.83%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9869	98.69%

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	97.14%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.56%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.84%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.43%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.28%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.25%	94.73%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.98%	94.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.79%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	85.13%	91.49%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.09%	93.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.18%	94.08%
CHEMBL221	P23219	Cyclooxygenase-1	82.71%	90.17%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6439522
• LOTUS: LTS0196443
• wikiData: Q76386711