Patchouli alcohol

Details

• Internal ID: a08aefc0-8888-4a3d-93c8-690da9f04968
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Tertiary alcohols
• IUPAC Name: (1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
• SMILES (Canonical): CC1CCC2(C(C3CCC2(C1C3)C)(C)C)O
• SMILES (Isomeric): C[C@H]1CC[C@@]2([C@@]3([C@H]1C[C@H](C2(C)C)CC3)C)O
• InChI: InChI=1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m0/s1
• InChI Key: GGHMUJBZYLPWFD-CUZKYEQNSA-N
• Popularity: 117 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.37 g/mol
• Exact Mass: 222.198365449 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.61
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 5986-55-0
• Patchoulol
• patchouli camphor
• Patchoulic alcohol
• patchoulanol
• (-)-patchouli alcohol
• (-)-patchoulol
• UNII-HHH8CPR1M2
• HHH8CPR1M2
• solid
• EINECS 227-807-2
• 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1R,4S,4aS,6R,8aS)-
• (1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.03,8]undecan-3-ol
• (1R,4S,4aS,6R,8aS)-4,8a,9,9-tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol
• (1r,4s,4as,6r,8as)-octahydro-4,8a,9,9-tetramethyl-1,6-methanonaphthalen-1(2h)-ol
• [1R-(1alpha,4beta,4aalpha,6beta,8aalpha)]-octahydro-4,8a,9,9-tetramethyl-1,6-methano-1(2H)-naphthol
• Patchoulialkohol
• (-)-(1R,3R,6S,7S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.0(3,8)]undecan-3-ol
• 1,6-Methanonaphthalen-1.beta.(2H)-ol, 3,4,4a.beta.,5,6.beta.,7,8,8a-octahydro-4.alpha.,8a.beta.,9,9-tetramethyl-
• crystallization
• pacholol
• patcholol
• patschuli
• white
• Healingwood
• healing wood
• Patchoulol Crist
• Patchouli alkohol
• Patchouli-alcohol
• (1R-(1alpha,4beta,4aalpha,6beta,8aalpha))-Octahydro-4,8a,9,9-tetramethyl-1,6-methano-1(2H)-naphthol
• Patchouli Oil Terpeneless
• SCHEMBL108115
• PATCHOULI ALCOHOL [MI]
• CHEBI:7940
• CHEMBL4588682
• DTXSID9052266
• GGHMUJBZYLPWFD-CUZKYEQNSA-N
• octahydro-4,8a,9,9-tetramethyl-
• (1R - (1a,4b,4aa,6b,8aa)) - octahydro - 4,8a,9,9 - tetramethyl - 1,6 - methano - 1(2H) - naphthol
• [1R-(1alpha,4beta,4aalpha,6beta,8aalpha)]-Octahydro-4,8a,9,9-tetramethyl-1,6-methanonaphthalen-1(2H)-ol
• 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1.alpha.,4.beta.,4a.alpha.,6.beta.,8a.alpha.)-
• 1,6-METHANONAPHTHALEN-1(2H)-OL, OCTAHYDRO-4,8A,9,9-TETRAMETHYL-, (1R-(1.ALPHA.,4.BETA.,4A.ALPHA.,6.BETA.,8A.ALPHA.))-
• 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-, (1R-(1alpha,4beta,4aalpha,6beta,8aalpha))-
• 1,6-Methanonaphthalen-1(2H)-ol, octahydro-4,8a,9,9-tetramethyl-,[1R-(1.alpha.,4.beta.,4a.alpha.,6.beta.,8a.alpha.)]-
• HY-N0207
• s3778
• AKOS015840173
• AKOS016011426
• CCG-266740
• NCGC00482601-01
• Octahydro-Tetramethyl-Methano-1-Naphthol
• AC-34015
• CS-0008254
• FT-0686673
• Q7144372
• (1R-(1a,4b,4aa,6b,8aa))-Octahydro-4,8a,9,9-tetramethyl-1,6-methano-1(2H)-naphthol 1,6-Methanonaphthalene-1(2H)-ol
• [1R-1alpha,4beta,4a-alpha,6beta* 4,8a,9,9-Tetramethyloctahydro-1,6-methanonaphthalen-1(2H)-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9967	99.67%
Caco-2	+	0.7633	76.33%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5059	50.59%
OATP2B1 inhibitior	-	0.8465	84.65%
OATP1B1 inhibitior	+	0.9507	95.07%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8663	86.63%
P-glycoprotein inhibitior	-	0.9441	94.41%
P-glycoprotein substrate	-	0.8632	86.32%
CYP3A4 substrate	+	0.6189	61.89%
CYP2C9 substrate	+	0.6198	61.98%
CYP2D6 substrate	-	0.7531	75.31%
CYP3A4 inhibition	-	0.9032	90.32%
CYP2C9 inhibition	-	0.7446	74.46%
CYP2C19 inhibition	-	0.8232	82.32%
CYP2D6 inhibition	-	0.9685	96.85%
CYP1A2 inhibition	-	0.6354	63.54%
CYP2C8 inhibition	-	0.8306	83.06%
CYP inhibitory promiscuity	-	0.9411	94.11%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6690	66.90%
Eye corrosion	-	0.9532	95.32%
Eye irritation	+	0.6553	65.53%
Skin irritation	+	0.7065	70.65%
Skin corrosion	-	0.8687	86.87%
Ames mutagenesis	-	0.8928	89.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.6274	62.74%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	+	0.5757	57.57%
skin sensitisation	+	0.6536	65.36%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7740	77.40%
Acute Oral Toxicity (c)	III	0.8644	86.44%
Estrogen receptor binding	-	0.4897	48.97%
Androgen receptor binding	+	0.5628	56.28%
Thyroid receptor binding	-	0.6088	60.88%
Glucocorticoid receptor binding	-	0.7244	72.44%
Aromatase binding	-	0.6275	62.75%
PPAR gamma	-	0.7451	74.51%
Honey bee toxicity	-	0.8712	87.12%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9541	95.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.38%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.82%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.81%	82.69%
CHEMBL206	P03372	Estrogen receptor alpha	88.07%	97.64%
CHEMBL233	P35372	Mu opioid receptor	87.57%	97.93%
CHEMBL238	Q01959	Dopamine transporter	87.04%	95.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.38%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.34%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	82.23%	95.38%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	80.64%	95.27%

Plants that contains it

• Agrimonia eupatoria
• Agrimonia pilosa
• Asarum sieboldii
• Astragalus mongholicus
• Homalomena occulta
• Leonurus japonicus
• Panax ginseng
• Pogostemon cablin
• Teucrium leucocladum
• Valeriana jatamansi
• Valeriana officinalis

Cross-Links

• PubChem: 10955174
• NPASS: NPC20306
• LOTUS: LTS0003907
• wikiData: Q7144372