3-Hydroxycitronellic acid

Details

• Internal ID: 552d715b-457b-418e-a7c4-e624b93661ff
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Acyclic monoterpenoids
• IUPAC Name: (3R)-3-hydroxy-3,7-dimethyloct-6-enoic acid
• SMILES (Canonical): CC(=CCCC(C)(CC(=O)O)O)C
• SMILES (Isomeric): CC(=CCC[C@](C)(CC(=O)O)O)C
• InChI: InChI=1S/C10H18O3/c1-8(2)5-4-6-10(3,13)7-9(11)12/h5,13H,4,6-7H2,1-3H3,(H,11,12)/t10-/m1/s1
• InChI Key: BGEHAKLYDDCRJH-SNVBAGLBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₈O₃
• Molecular Weight: 186.25 g/mol
• Exact Mass: 186.125594432 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.96
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• RefChem:94285
• CHEBI:204812
• (3R)-3-hydroxy-3,7-dimethyloct-6-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9597	95.97%
Caco-2	+	0.9202	92.02%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6121	61.21%
OATP2B1 inhibitior	-	0.8471	84.71%
OATP1B1 inhibitior	+	0.9101	91.01%
OATP1B3 inhibitior	+	0.9255	92.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8253	82.53%
P-glycoprotein inhibitior	-	0.9802	98.02%
P-glycoprotein substrate	-	0.9730	97.30%
CYP3A4 substrate	-	0.6295	62.95%
CYP2C9 substrate	-	0.5639	56.39%
CYP2D6 substrate	-	0.8869	88.69%
CYP3A4 inhibition	-	0.8844	88.44%
CYP2C9 inhibition	-	0.6693	66.93%
CYP2C19 inhibition	-	0.7674	76.74%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	-	0.6802	68.02%
CYP2C8 inhibition	-	0.9738	97.38%
CYP inhibitory promiscuity	-	0.7886	78.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.6069	60.69%
Eye corrosion	-	0.9073	90.73%
Eye irritation	+	0.9823	98.23%
Skin irritation	+	0.6515	65.15%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6982	69.82%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.5392	53.92%
skin sensitisation	+	0.5100	51.00%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	-	0.6356	63.56%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	+	0.5121	51.21%
Acute Oral Toxicity (c)	III	0.5824	58.24%
Estrogen receptor binding	-	0.9386	93.86%
Androgen receptor binding	-	0.9083	90.83%
Thyroid receptor binding	-	0.7617	76.17%
Glucocorticoid receptor binding	-	0.8695	86.95%
Aromatase binding	-	0.8980	89.80%
PPAR gamma	-	0.7631	76.31%
Honey bee toxicity	-	0.9190	91.90%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9028	90.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.57%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.67%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.98%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	84.73%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.82%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.12%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.66%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.30%	96.95%

Plants that contains it

• Artemisia gilvescens
• Datura stramonium
• Oenanthe fistulosa

Cross-Links

• PubChem: 92466151
• NPASS: NPC220509
• LOTUS: LTS0027037
• wikiData: Q104935469