Bisabolol

Details

• Internal ID: f2cfd893-c7f9-45a6-9f2b-fb03d7e3ff1e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R)-6-methyl-2-[(1R)-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+/m0/s1
• InChI Key: RGZSQWQPBWRIAQ-LSDHHAIUSA-N
• Popularity: 694 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

• Bisabolol
• (+)-alpha-Bisabolol
• 515-69-5
• 23178-88-3
• D-alpha-Bisabolol
• (2R)-6-methyl-2-[(1R)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol
• (+)-(1'R,2R)-alpha-Bisabolol
• alpha-Bisabolol, (+)-
• UNII-36HQN158VC
• Dragosantol
• Camilol
• a-Bisabolol
• 36HQN158VC
• CHEMBL1171719
• DTXSID5045964
• Hydagen B
• UNII-105S6I733Z
• alpha-Bisabolol (+)-form [MI]
• MFCD03846910
• 105S6I733Z
• (2R)-6-Methyl-2-(4-methyl-3-cyclohexenyl)-5-heptene-2-ol
• (R)-6-Methyl-2-((R)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
• 5-HEPTEN-2-OL, 6-METHYL-2-(4-METHYL-3-CYCLOHEXEN-1-YL)-
• alpha,4-Dimethyl-alpha-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol
• 3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, (R*,R*)-
• DTXCID3025964
• EINECS 208-205-9
• EINECS 246-973-7
• rel-(R)-6-Methyl-2-((R)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol
• dl-.alpha.-Bisabolol
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-, (alphaR,1R)-
• 25428-43-7
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-, (alphaR,1R)-rel-
• BISABOLOL, ALPHA
• CAS-515-69-5
• BISABOLOL, .ALPHA.
• RACEMIC ALFA-BISABOLOL
• BISABOLA-1,12-DIEN-8-OL
• (R*,R*)-alpha,4-Dimethyl-alpha-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol
• NCGC00095252-01
• (+)-a-Bisabolol
• (+)-.alpha.-Bisabolol
• BISABOLOL [WHO-DD]
• D-.ALPHA.-BISABOLOL
• SCHEMBL24988
• (AlphaR,1R)-Alpha-Bisabolol
• (+)-6R,7R-alpha-Bisabolol
• .alpha.,4-Dimethyl-.alpha.-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol
• .ALPHA.-BISABOLOL [MI]
• 3-Cyclohexene-1-methanol, ?,4-dimethyl-?-(4-methyl-3-pentenyl)-, (R,R)-
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-
• BISABOLOL, (+/-)-
• (alpha R,1R)-rel-alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol
• (R*, R*)- a, 4- dimethyl- a- (4- methyl- 3- pentenyl)cyclohex- 3- ene- 1- methanol
• (R*,R*)-(1)-alpha,4-Dimethyl-alpha-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol
• (R*,R*)-.alpha.,4-Dimethyl-.alpha.-(4-methyl-3-pentenyl)-3-cyclohexene-1-methanol
• (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)-, (alphaR,1R)-rel-
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (R*,R*)-
• CHEBI:192031
• RGZSQWQPBWRIAQ-LSDHHAIUSA-N
• ALPHA-BISABOLOL, (+-)-
• (R*,R*) - a,4 - dimethyl - a - (4 - methyl - 3 - pentenyl)cyclohex - 3 - ene - 1 - methanol
• 3-ciclohexeno-1-metanol, Alfa,4-Dimetil-Alfa-(4-metil-3-penten-1-il)-, (Alfa R, 1R)-rel-
• 3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-penten-1-yl)-, (.alpha.R,1R)-rel-
• 3-Cyclohexene-1-methanol, alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (theta,theta)-(+/-)-
• (+/-)-.ALPHA.-BISABOLOL
• .ALPHA.-BISABOLOL, (+)-
• Tox21_111490
• BDBM50284328
• s6136
• AKOS015969722
• Tox21_111490_1
• .ALPHA.-BISABOLOL, (+/-)-
• NCGC00095252-05
• ( inverted exclamation markA)-|A-Bisabolol
• .ALPHA.-BISABOLOL (+)-FORM [MI]
• HY-121222
• (+)-(1'R,2R)-.ALPHA.-BISABOLOL
• CS-0081254
• W-105877
• (2R)-6-Methyl-2-[(1R)-4-methyl-3-cyclohexen-1-yl]-5-hepten-2-ol
• (R*,R*)-(+-)-alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol
• alpha,4-Dimethyl-alpha-(4-methyl-3-penten-1-yl)-(alphaR,1R)-3-Cyclohexene-1-methanol
• 3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL- 3-PENTEN-1-YL)-, (.ALPHA.R,1R)-REL-
• 3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL- 3-PENTENYL)-, (.THETA.,.THETA.)-(+/-)-
• 3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL- 3-PENTENYL)-, (R*,R*)-
• 3-CYCLOHEXENE-1-METHANOL, .ALPHA.,4-DIMETHYL-.ALPHA.-(4-METHYL-3-PENTEN-1-YL)-, (.ALPHA.R,1R)-
• 3-Cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, [R-(R*,R*)]-

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 nephrolepis
• Abies sachalinensis var. mayriana
• Abies sibirica subsp. semenovii
• Acorus calamus
• Adina trichotoma
• Afraegle paniculata
• Agrimonia pilosa
• Angelica pubescens
• Aralia continentalis
• Artemisia annua
• Artemisia argyi
• Artemisia carvifolia
• Artemisia montana
• Artemisia princeps
• Artemisia xanthochroa
• Asarum sieboldii
• Astragalus glycyphyllos
• Athrixia elata
• Atractylodes lancea
• Bupleurum chinense
• Bupleurum falcatum
• Bupleurum scorzonerifolium
• Cassinia subtropica
• Centaurea cheiranthifolia
• Chrysanthemum indicum
• Cinnamomum aromaticum
• Citrus medica
• Cladanthus arabicus
• Colchicum arenarium
• Cratoxylum formosum subsp. pruniflorum
• Curcuma kwangsiensis
• Curcuma longa
• Curcuma phaeocaulis
• Curcuma wenyujin
• Daphnandra johnsonii
• Daucus carota
• Dianella revoluta
• Eleutherococcus senticosus
• Elsholtzia ciliata
• Endopappus macrocarpus subsp. macrocarpus
• Eremanthus incanus
• Erythrina burttii
• Ferula hermonis
• Fokienia hodginsii
• Gyrothyra underwoodiana
• Helichrysum mimetes
• Hippeastrum aulicum
• Hypericum perforatum
• Jacobaea erucifolia subsp. argunensis
• Juniperus virginiana var. silicicola
• Kokoona ochracea
• Lamprolobium fruticosum
• Lasiolaena morii
• Litchi chinensis
• Lonicera japonica
• Lychnophora ericoides
• Machilus obovatifolia
• Magnolia liliiflora
• Mentha pulegium
• Microbiota decussata
• Mikania grazielae
• Mosla chinensis
• Murraya exotica
• Murraya paniculata
• Panax ginseng
• Pellia epiphylla
• Pinus pumila
• Piper callosum
• Piper fimbriulatum
• Piper nigrum
• Pittocaulon bombycophole
• Polyachyrus sphaerocephalus
• Prioria pinnata
• Pseudoconyza viscosa
• Rhododendron dauricum
• Rubus pungens
• Salvia barrelieri
• Sanguisorba minor
• Schisandra chinensis
• Seseli buchtormense
• Seseli transcaucasicum
• Sideritis lanata
• Spatholobus suberectus
• Syzygium cumini
• Tamarix gallica
• Thymus camphoratus
• Valeriana officinalis
• Viola hondoensis
• Wurfbainia neoaurantiaca
• Zingiber officinale

Cross-Links

• PubChem: 1549992
• NPASS: NPC35519
• LOTUS: LTS0087338
• wikiData: Q72443959