3-Hydroxybakuchiol

Details

• Internal ID: 420c0cd2-f6a9-43dc-abc3-820b7b751218
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Aromatic monoterpenoids
• IUPAC Name: 4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]benzene-1,2-diol
• SMILES (Canonical): CC(=CCCC(C)(C=C)C=CC1=CC(=C(C=C1)O)O)C
• SMILES (Isomeric): CC(=CCC[C@@](C)(C=C)/C=C/C1=CC(=C(C=C1)O)O)C
• InChI: InChI=1S/C18H24O2/c1-5-18(4,11-6-7-14(2)3)12-10-15-8-9-16(19)17(20)13-15/h5,7-10,12-13,19-20H,1,6,11H2,2-4H3/b12-10+/t18-/m1/s1
• InChI Key: ZHKCOGVKHHAUBK-NCUBBLFSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₂
• Molecular Weight: 272.40 g/mol
• Exact Mass: 272.177630004 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 5.05
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 178765-54-3
• 4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]benzene-1,2-diol
• 1,2-Benzenediol, 4-[(1E,3S)-3-ethenyl-3,7-dimethyl-1,6-octadien-1-yl]-
• orb1683598
• SCHEMBL31249561
• HY-N1839
• MFCD28100308
• AKOS040761097
• FS-7918
• DA-60265
• CS-0017693
• 4-[(1E,3S)-3,7-dimethyl-3-vinyl-octa-1,6-dienyl]benzene-1,2-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.7756	77.56%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6375	63.75%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.9291	92.91%
OATP1B3 inhibitior	+	0.9167	91.67%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.5917	59.17%
P-glycoprotein inhibitior	-	0.9269	92.69%
P-glycoprotein substrate	-	0.9131	91.31%
CYP3A4 substrate	-	0.5673	56.73%
CYP2C9 substrate	+	0.5918	59.18%
CYP2D6 substrate	-	0.7317	73.17%
CYP3A4 inhibition	-	0.6511	65.11%
CYP2C9 inhibition	-	0.5731	57.31%
CYP2C19 inhibition	+	0.5266	52.66%
CYP2D6 inhibition	-	0.7516	75.16%
CYP1A2 inhibition	+	0.5802	58.02%
CYP2C8 inhibition	-	0.6807	68.07%
CYP inhibitory promiscuity	+	0.5324	53.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6800	68.00%
Carcinogenicity (trinary)	Non-required	0.6513	65.13%
Eye corrosion	-	0.9391	93.91%
Eye irritation	-	0.6456	64.56%
Skin irritation	-	0.5361	53.61%
Skin corrosion	-	0.7178	71.78%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7830	78.30%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	+	0.8016	80.16%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.8565	85.65%
Estrogen receptor binding	+	0.9123	91.23%
Androgen receptor binding	+	0.7393	73.93%
Thyroid receptor binding	+	0.7578	75.78%
Glucocorticoid receptor binding	+	0.5667	56.67%
Aromatase binding	+	0.8161	81.61%
PPAR gamma	+	0.7836	78.36%
Honey bee toxicity	-	0.8249	82.49%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.36%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.01%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.86%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.13%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.52%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	90.11%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.57%	94.45%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.92%	96.12%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.43%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.75%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.32%	95.56%

Plants that contains it

• Cullen corylifolium

Cross-Links

• PubChem: 56833075
• NPASS: NPC70431