Levomenol

Details

• Internal ID: 600a5932-f3c3-45f4-9cf6-97484dea0332
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
• SMILES (Canonical): CC1=CCC(CC1)C(C)(CCC=C(C)C)O
• SMILES (Isomeric): CC1=CC[C@H](CC1)[C@](C)(CCC=C(C)C)O
• InChI: InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1
• InChI Key: RGZSQWQPBWRIAQ-CABCVRRESA-N
• Popularity: 305 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: 3.80
• Atomic LogP (AlogP): 4.23
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 23089-26-1
• (-)-alpha-Bisabolol
• alpha-(-)-Bisabolol
• Levomenolum
• Kamilosan
• 1-alpha-Bisabolol
• alpha-Bisabolol, L-
• alpha-Bisabolol (-)-form
• UNII-24WE03BX2T
• 24WE03BX2T
• CCRIS 9081
• (-)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol
• DTXSID4042094
• EINECS 245-423-3
• Levomenolum [INN-Latin]
• DTXCID2022094
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (alphaS,1S)-
• Levomenolum (INN-Latin)
• LEVOMENOL (MART.)
• LEVOMENOL [MART.]
• LEVOMENOL (USP-RS)
• LEVOMENOL [USP-RS]
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (S-(theta,theta))-
• PurpleU BAOBAB FACE
• RefChem:40862
• BISABOLOL, (-)-alpha
• alpha-BISABOLOL, (-)-
• (alphaS,1S)-alpha-BISABOLOL
• (-)-alpha-BISABOLOL (CONSTITUENT OF CHAMOMILE)
• 5-HEPTEN-2-OL, 6-METHYL-2-(4-METHYL-3-CYCLOHEXEN-1-YL), (-)-
• 245-423-3
• 3-CYCLOHEXENE-1-METHANOL, alpha,4-DIMETHYL-alpha-(4-METHYL-3-PENTEN-1-YL)-, (alphaS,1S)-
• Kamillosan
• alpha-Bisabolol
• .alpha.-Bisabolol
• Levomenol [INN]
• (2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
• 3-Cyclohexene-1-methanol, a,4-dimethyl-a-(4-methyl-3-pentenyl)-,(aS,1S)-
• (-)-.alpha.-Bisabolol
• MFCD03412455
• Bisabolol, (-)-.alpha.
• .alpha.-bisabolol, (-)-
• CHEBI:125
• .alpha.-Bisabolol (-)-form
• FEMA NO. 4666
• (S)-6-Methyl-2-((S)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
• (.alpha.s,1s)-.alpha.-bisabolol
• Dragosantol (>80%)
• Dragosantol
• Camilol
• Levomenol; (-)-a-Bisabolol
• Hydagen B
• (-)-|A-Bisabolol
• ((-))-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol
• BISABOLOL, ALPHA
• BISABOLOL, .ALPHA.
• RACEMIC ALFA-BISABOLOL
• Bisbalol
• BISABOLA-1,12-DIEN-8-OL
• L-alpha-Bisabolol
• Levomenol, INN
• 3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, [S-(R*,R*)]-
• (-)-a-Bisabolol
• l-.alpha.-Bisabolol
• Levomenol (Standard)
• (-)-?-Bisabolol
• (?)-|A-Bisabolol
• .alpha.-Bisabolol, L-
• (-)- alpha -Bisabolol
• .alpha.-(-)-Bisabolol
• BISABOLOL [VANDF]
• (-)--BISABOLOL
• ALPHA-(-)BISABOLOL
• LEVOMENOL [WHO-DD]
• SCHEMBL24989
• orb1685377
• CHEMBL1096927
• HY-N6967R
• (-)-(4S,8S)-alpha-Bisabolol
• (-)-alpha-Bisabolol (Levomenol)
• GLXC-20390
• HY-N6967
• [S-(R*,R*)]-.alpha.-Bisabolol
• Tox21_301375
• 5-Hepten-2-ol, 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-, (-)-
• BDBM50382730
• NSC782530
• Levomenol 100 microg/mL in Methanol
• DB13153
• FB75117
• LMPR0103060001
• NSC-782530
• (-)-alpha-Bisabolol, >=93% (GC)
• (-)-Alpha-bisabolol(-)-alpha-bisabolol
• NCGC00255987-01
• (-)-alpha-Bisabolol, analytical standard
• DA-74979
• TS-09816
• .ALPHA.-BISABOLOL (-)-FORM [MI]
• CAS-23089-26-1
• CS-0028206
• NS00068750
• C09621
• G13201
• EN300-19632355
• Q179896
• BRD-K62751771-001-01-3
• (-)-alpha-Bisabolol, primary pharmaceutical reference standard
• Levomenol, United States Pharmacopeia (USP) Reference Standard
• (-)-.ALPHA.-BISABOLOL (CONSTITUENT OF CHAMOMILE) [DSC]
• 6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol, (-)-
• 5-HEPTEN-2-OL, 6-METHYL-2-(4- METHYL-3-CYCLOHEXEN-1-YL), (-)-
• [S-(R*,R*)]-.alpha.,4-Dimethyl-.alpha.-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol
• 3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, (-)-
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (.alpha.S,1S)-
• alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-(alphaS,1S)-3-Cyclohexene-1-methanol
• 3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL-3-PENTEN-1-YL)-, (.ALPHA.S,1S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.8567	85.67%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4275	42.75%
OATP2B1 inhibitior	-	0.8487	84.87%
OATP1B1 inhibitior	+	0.9368	93.68%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.7619	76.19%
P-glycoprotein inhibitior	-	0.9714	97.14%
P-glycoprotein substrate	-	0.8727	87.27%
CYP3A4 substrate	-	0.5206	52.06%
CYP2C9 substrate	-	0.5790	57.90%
CYP2D6 substrate	-	0.7630	76.30%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.7372	73.72%
CYP2C19 inhibition	-	0.7863	78.63%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	-	0.7807	78.07%
CYP2C8 inhibition	-	0.7676	76.76%
CYP inhibitory promiscuity	-	0.7213	72.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7928	79.28%
Carcinogenicity (trinary)	Non-required	0.6310	63.10%
Eye corrosion	-	0.9199	91.99%
Eye irritation	+	0.7597	75.97%
Skin irritation	+	0.6357	63.57%
Skin corrosion	-	0.9768	97.68%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5390	53.90%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	+	0.9229	92.29%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	-	0.7556	75.56%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.5866	58.66%
Acute Oral Toxicity (c)	III	0.8480	84.80%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.8402	84.02%
Thyroid receptor binding	-	0.6613	66.13%
Glucocorticoid receptor binding	-	0.6694	66.94%
Aromatase binding	-	0.7937	79.37%
PPAR gamma	-	0.6124	61.24%
Honey bee toxicity	-	0.9151	91.51%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9536	95.36%

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	96.01%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.59%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.29%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.81%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.35%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.85%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.39%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.83%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.50%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.34%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.30%	95.89%

Plants that contains it

• Abies sibirica subsp. semenovii
• Achillea nobilis
• Acorus calamus
• Agrimonia eupatoria
• Agrimonia pilosa
• Angelica pubescens
• Aralia continentalis
• Artemisia annua
• Artemisia argyi
• Artemisia carvifolia
• Artemisia montana
• Artemisia princeps
• Atractylodes lancea
• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum scorzonerifolium
• Chrysanthemum indicum
• Cinnamomum aromaticum
• Citrus medica
• Curcuma kwangsiensis
• Curcuma longa
• Curcuma phaeocaulis
• Curcuma wenyujin
• Daucus carota
• Eleutherococcus senticosus
• Elsholtzia ciliata
• Eremanthus arboreus
• Eremanthus erythropappus
• Ferula hermonis
• Hypericum perforatum
• Lonicera japonica
• Mosla chinensis
• Murraya paniculata
• Murraya paniculata
• Panax ginseng
• Pinus sibirica
• Piper nigrum
• Pojarkovia pojarkovae
• Rhododendron dauricum
• Santolina canescens
• Schisandra chinensis
• Zingiber officinale

Cross-Links

• PubChem: 442343
• NPASS: NPC157781
• ChEMBL: CHEMBL1096927
• LOTUS: LTS0074733
• wikiData: Q179896