d-Piperitone

Details

• Internal ID: d2760d59-914c-4933-bdda-d036772ca6fa
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Menthane monoterpenoids
• IUPAC Name: (6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)C(CC1)C(C)C
• SMILES (Isomeric): CC1=CC(=O)[C@@H](CC1)C(C)C
• InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1
• InChI Key: YSTPAHQEHQSRJD-VIFPVBQESA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23 g/mol
• Exact Mass: 152.120115130 g/mol
• Topological Polar Surface Area (TPSA): 17.10 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.57
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 6091-50-5
• (+)-Piperitone
• PIPERITONE, D-
• Piperitone, alpha-
• d-Piperitone (natural)
• FEMA No. 2910
• (-)-piperitone
• UNII-8ZZ2GU5WBU
• 8ZZ2GU5WBU
• (6S)-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
• 4-Isopropyl-1-methyl-1-cyclohexen-3-one
• 3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one, (S)-
• 2-Cyclohexen-1-one, 3-methyl-6-(1-methyethyl)-, (S)-
• 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-
• (6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
• (R)-Piperitone
• p-Menth-1-en-3-one, ()-
• alpha-Piperitone
• dextro-piperitone
• (S)-piperitone
• (6R)-6-isopropyl-3-methylcyclohex-2-en-1-one
• (S)-(+)-Piperitone
• (6R)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one
• CHEBI:41
• D-PIPERITONE [FHFI]
• 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (6S)-
• SCHEMBL1248697
• DTXSID401317272
• FEMA NO. 2910, D-
• AKOS006271898
• LMPR0102090024
• LS-3054
• (S)-6-isopropyl-3-methylcyclohex-2-enone
• 2-AMINO-4,4,4-TRIFLUOROBUTYRICACID
• C09885
• (S)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one
• Q27105210

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.8838	88.38%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Mitochondria	0.4203	42.03%
OATP2B1 inhibitior	-	0.8500	85.00%
OATP1B1 inhibitior	+	0.9645	96.45%
OATP1B3 inhibitior	+	0.9100	91.00%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.9223	92.23%
P-glycoprotein inhibitior	-	0.9880	98.80%
P-glycoprotein substrate	-	0.9108	91.08%
CYP3A4 substrate	-	0.6213	62.13%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8631	86.31%
CYP3A4 inhibition	-	0.9664	96.64%
CYP2C9 inhibition	-	0.8833	88.33%
CYP2C19 inhibition	-	0.8188	81.88%
CYP2D6 inhibition	-	0.9119	91.19%
CYP1A2 inhibition	-	0.5562	55.62%
CYP2C8 inhibition	-	0.9936	99.36%
CYP inhibitory promiscuity	-	0.7458	74.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7710	77.10%
Carcinogenicity (trinary)	Non-required	0.5395	53.95%
Eye corrosion	-	0.7899	78.99%
Eye irritation	+	0.9144	91.44%
Skin irritation	+	0.8604	86.04%
Skin corrosion	-	0.9014	90.14%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6375	63.75%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	+	0.9395	93.95%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5667	56.67%
Mitochondrial toxicity	-	0.9250	92.50%
Nephrotoxicity	-	0.7201	72.01%
Acute Oral Toxicity (c)	III	0.8168	81.68%
Estrogen receptor binding	-	0.9761	97.61%
Androgen receptor binding	-	0.5274	52.74%
Thyroid receptor binding	-	0.8793	87.93%
Glucocorticoid receptor binding	-	0.7992	79.92%
Aromatase binding	-	0.9349	93.49%
PPAR gamma	-	0.8956	89.56%
Honey bee toxicity	-	0.9237	92.37%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9528	95.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.91%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.13%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.04%	90.71%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.90%	97.25%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.77%	96.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.49%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.75%	93.40%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.63%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.55%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.96%	96.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.08%	90.24%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.46%	86.00%

Plants that contains it

• Artemisia capillaris
• Artemisia gmelinii
• Artemisia judaica
• Artemisia koidzumii
• Chrysactinia mexicana
• Daucus carota
• Eucalyptus dives
• Eucalyptus mitchelliana
• Foeniculum vulgare
• Illicium difengpi
• Litsea cubeba
• Mentha × piperita
• Mentha arvensis
• Mentha canadensis
• Piper aduncum
• Piper cubeba
• Senna alexandrina
• Seriphidium deserti
• Seriphidium herba-alba
• Sideritis lasiantha
• Thymus quinquecostatus
• Thymus vulgaris
• Zanthoxylum bungeanum
• Zanthoxylum schinifolium
• Zanthoxylum spinosum

Cross-Links

• PubChem: 61362
• NPASS: NPC43822
• LOTUS: LTS0086920
• wikiData: Q27105210