Perillaldehyde, (-)-

Details

• Internal ID: ee76d218-89ab-4f91-bf43-950f0b7484eb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde
• SMILES (Canonical): CC(=C)C1CCC(=CC1)C=O
• SMILES (Isomeric): CC(=C)[C@H]1CCC(=CC1)C=O
• InChI: InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,7,10H,1,4-6H2,2H3/t10-/m1/s1
• InChI Key: RUMOYJJNUMEFDD-SNVBAGLBSA-N
• Popularity: 37 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22 g/mol
• Exact Mass: 150.104465066 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.49
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• (-)-Perillaldehyde
• l-Perillaldehyde
• (S)-(-)-Perillaldehyde
• (S)-4-(prop-1-en-2-yl)cyclohex-1-enecarbaldehyde
• (s)-perillaldehyde
• 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethenyl)-, (4S)-
• (-)-Perillaaldehyde
• 1-Perillaldehyde
• Perillaldehyde, (-)-
• (S)-p-Mentha-1,8-dien-7-al
• (-)-Perilla aldehyde
• UNII-5EL0Y7P6LP
• 5EL0Y7P6LP
• (S)-(-)-Perillic aldehyde
• (S)-4-Isopropenyl-cyclohexene-1-carboxaldehyde
• CCRIS 7325
• (4S)-4-prop-1-en-2-ylcyclohexene-1-carbaldehyde
• DTXSID5041190
• (4S)-p-Mentha-1,8-dien-7-al
• (S)-4-Isopropenyl-1-cyclohexene-1-carboxaldehyde
• DTXCID3021190
• 1-CYCLOHEXENE-1-CARBOXALDEHYDE, 4-ISOPROPENYL-, (S)-(-)-
• 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethenyl)-, (S)-(-)-
• (S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
• (4S)-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
• 1-Cyclohexene-1-carboxaldehyde, 4-(1-methylethenyl)-, (S)-
• MFCD00001543
• (?)-Perillaaldehyde
• S(-)-Perillaldehyde
• (-)-perillyl aldehyde
• (4S)-perillyl aldehyde
• bmse000638
• PERILLALDEHYDE L-FORM
• (-)-Perillaldehyde - 95%
• CHEMBL442913
• SCHEMBL1302138
• RUMOYJJNUMEFDD-SNVBAGLBSA-N
• PERILLALDEHYDE L-FORM [MI]
• HY-N2085
• Tox21_300969
• BBL033978
• s3205
• STK801847
• (S)-(-)-Perillaldehyde, >=92%
• AKOS005622599
• DS-4065
• NCGC00248235-01
• NCGC00254872-01
• AC-35084
• XP164875
• CAS-18031-40-8
• (S)-(-)-Perillaldehyde, analytical standard
• CS-0018589
• (4S)-4-isopropenylcyclohexene-1-carbaldehyde
• (4S)-4-Isopropenyl-1-cyclohexen-1-carbaldehyde
• (S)-(-)-Perillaldehyde, technical grade, 92%
• EN300-6764746
• 4-Isopropenyl-1-cyclohexene-1-carbaldehyde, (S)-
• A881122
• Q23766753
• Z1255402618
• (4S)-4-(1-Methylethenyl)-1-cyclohexene-1-carboxaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	+	0.5877	58.77%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.4187	41.87%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.9338	93.38%
OATP1B3 inhibitior	+	0.9190	91.90%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8931	89.31%
P-glycoprotein inhibitior	-	0.9854	98.54%
P-glycoprotein substrate	-	0.9455	94.55%
CYP3A4 substrate	-	0.6014	60.14%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	-	0.8385	83.85%
CYP3A4 inhibition	-	0.9565	95.65%
CYP2C9 inhibition	-	0.9449	94.49%
CYP2C19 inhibition	-	0.8958	89.58%
CYP2D6 inhibition	-	0.9602	96.02%
CYP1A2 inhibition	-	0.7564	75.64%
CYP2C8 inhibition	-	0.9495	94.95%
CYP inhibitory promiscuity	-	0.7745	77.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6800	68.00%
Carcinogenicity (trinary)	Non-required	0.6173	61.73%
Eye corrosion	+	0.9360	93.60%
Eye irritation	+	0.9629	96.29%
Skin irritation	+	0.7918	79.18%
Skin corrosion	-	0.9499	94.99%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5986	59.86%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	+	0.9333	93.33%
Respiratory toxicity	-	0.9111	91.11%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.9750	97.50%
Nephrotoxicity	+	0.6660	66.60%
Acute Oral Toxicity (c)	III	0.7154	71.54%
Estrogen receptor binding	-	0.9400	94.00%
Androgen receptor binding	-	0.8318	83.18%
Thyroid receptor binding	-	0.8778	87.78%
Glucocorticoid receptor binding	-	0.7896	78.96%
Aromatase binding	-	0.7898	78.98%
PPAR gamma	-	0.7782	77.82%
Honey bee toxicity	-	0.9262	92.62%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9900	99.00%

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	92.81%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.45%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.17%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.81%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.41%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.74%	100.00%

Plants that contains it

• Aconitum leucostomum
• Aiouea montana
• Aquilegia ecalcarata
• Artemisia szowitziana
• Blumea axillaris
• Ceanothus velutinus
• Chlorophytum borivilianum
• Citrus × aurantium
• Citrus deliciosa
• Citrus maxima
• Citrus medica
• Dipterocarpus dyeri
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lasianthus fordii
• Ledebouria socialis
• Ligusticum striatum
• Lycopus europaeus
• Perilla frutescens
• Persea barbujana
• Rhodiola rosea
• Zingiber officinale

Cross-Links

• PubChem: 2724159
• NPASS: NPC209431
• LOTUS: LTS0025470
• wikiData: Q23766753