Perillic acid

Details

• Internal ID: ef5753db-37da-4414-9c31-ebd2f330f68b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: 4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
• SMILES (Canonical): CC(=C)C1CCC(=CC1)C(=O)O
• SMILES (Isomeric): CC(=C)C1CCC(=CC1)C(=O)O
• InChI: InChI=1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)
• InChI Key: CDSMSBUVCWHORP-UHFFFAOYSA-N
• Popularity: 233 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22 g/mol
• Exact Mass: 166.099379685 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 7694-45-3
• (-)-perillic acid
• Perillicacid
• 4-Isopropenylcyclohex-1-enecarboxylic acid
• 4-prop-1-en-2-ylcyclohexene-1-carboxylic acid
• PKS69DU4ZQ
• 4-(1-methylethenyl)-1-cyclohexene-1-carboxylic acid
• CHEBI:36999
• 4-Isopropenyl-1-cyclohexene-1-carboxylic acid
• 1-Cyclohexene-1-carboxylicacid, 4-(1-methylethenyl)-
• 4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid
• 1-Cyclohexene-1-carboxylic acid, 4-(1-methylethenyl)-
• SR-01000076076
• EINECS 231-709-5
• 4-isopropenylcyclohex-1-ene carboxylic acid
• MFCD00062539
• 4-(2-propenyl)-1-cyclohexane-1-carboxylic acid
• UNII-PKS69DU4ZQ
• Lopac0_001001
• PERILLIC ACID [INCI]
• SCHEMBL465998
• CHEMBL1373981
• DTXSID60864105
• CDSMSBUVCWHORP-UHFFFAOYSA-N
• HMS3263I03
• Tox21_501001
• NSC641067
• AKOS006230667
• CCG-205081
• LMPR0102090041
• LP01001
• NSC-641067
• SDCCGSBI-0050974.P002
• NCGC00015832-02
• NCGC00015832-03
• NCGC00015832-04
• NCGC00015832-05
• NCGC00015832-06
• NCGC00015832-07
• NCGC00094295-01
• NCGC00094295-02
• NCGC00094295-03
• NCGC00094295-04
• NCGC00261686-01
• NCI60_013759
• SY316382
• HY-113471
• CS-0062325
• EU-0101001
• FT-0693829
• FT-0771613
• P 7083
• SR-01000076076-1
• SR-01000076076-5
• SR-01000076076-6
• (S)-4-(1-Propen-2-yl)cyclohex-1-enecarboxylic Acid
• Q27104388
• 1A4758DA-6365-4FD5-BAEA-16032D3488FF
• 5-AMINO-1H-PYRAZOLE-1,3-DICARBOXYLICACIDETHYLMETHYLESTER

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	-	0.5938	59.38%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5857	58.57%
OATP2B1 inhibitior	-	0.8450	84.50%
OATP1B1 inhibitior	+	0.9631	96.31%
OATP1B3 inhibitior	+	0.8505	85.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9179	91.79%
P-glycoprotein inhibitior	-	0.9887	98.87%
P-glycoprotein substrate	-	0.9566	95.66%
CYP3A4 substrate	-	0.6610	66.10%
CYP2C9 substrate	+	0.8284	82.84%
CYP2D6 substrate	-	0.9201	92.01%
CYP3A4 inhibition	-	0.9075	90.75%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9435	94.35%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9515	95.15%
CYP inhibitory promiscuity	-	0.9414	94.14%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8163	81.63%
Carcinogenicity (trinary)	Non-required	0.6737	67.37%
Eye corrosion	+	0.7370	73.70%
Eye irritation	+	0.9511	95.11%
Skin irritation	+	0.6148	61.48%
Skin corrosion	-	0.9686	96.86%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7327	73.27%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.6338	63.38%
skin sensitisation	+	0.8348	83.48%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.6598	65.98%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.7901	79.01%
Estrogen receptor binding	-	0.9706	97.06%
Androgen receptor binding	-	0.7620	76.20%
Thyroid receptor binding	-	0.9031	90.31%
Glucocorticoid receptor binding	-	0.8131	81.31%
Aromatase binding	-	0.8680	86.80%
PPAR gamma	-	0.7705	77.05%
Honey bee toxicity	-	0.9457	94.57%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9940	99.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	4.5 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.93%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.98%	91.11%
CHEMBL2581	P07339	Cathepsin D	85.56%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.94%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.41%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.66%	93.00%

Plants that contains it

• Perilla frutescens

Cross-Links

• PubChem: 1256
• LOTUS: LTS0043386
• wikiData: Q27104388