Manool

Details

• Internal ID: dcd904cd-feb2-4532-935e-d844c0493b72
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3R)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2CCC(C)(C=C)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CCC(=C)[C@@H]2CC[C@](C)(C=C)O)(C)C
• InChI: InChI=1S/C20H34O/c1-7-19(5,21)14-11-16-15(2)9-10-17-18(3,4)12-8-13-20(16,17)6/h7,16-17,21H,1-2,8-14H2,3-6H3/t16-,17-,19-,20+/m0/s1
• InChI Key: CECREIRZLPLYDM-QGZVKYPTSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O
• Molecular Weight: 290.50 g/mol
• Exact Mass: 290.260965704 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.50
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 596-85-0
• 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-.alpha.,5,5,8a-tetramethyl-2-methylene-, (.alpha.R,1S,4aS,8aS)-
• (+)-manool
• Labda-8(20),14-dien-13-ol, (13R)-
• AT5PJ0PV00
• NSC165961
• NSC-165961
• (13R)-manool
• CHEMBL4162501
• SCHEMBL12658773
• CHEBI:76945
• HY-N1039A
• CCG-208417
• labda-8(17),14-dien-13(R)-ol
• (3R)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-1-en-3-ol
• MS-24149
• (13R)-labda-8(27),14-dien-13-ol
• (13R)-Labda-8(20),14-dien-13-ol
• CS-0132370
• Labda-8 (20),14-dien-13-ol, (13R)-
• SR-05000002258
• SR-05000002258-2
• Q15726184
• (5S,9S,10S,13R)-labda-8(17),14-dien-13-ol
• (.ALPHA.R,1S,4AS,8AS)-.ALPHA.-ETHENYLDECAHYDRO-.ALPHA.,5,5,8A-TETRAMETHYL-2-METHYLENE-1-NAPHTHALENEPROPANOL
• (3R)-3-methyl-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]pent-1-en-3-ol
• (3R)-3-methyl-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl]pent-1-en-3-ol
• (3R)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decalin-1-yl]-3-methyl-pent-1-en-3-ol
• (3R)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-decahydronaphthalen-1-yl]-3-methylpent-1-en-3-ol
• (R)-3-methyl-5-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)pent-1-en-3-ol
• 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-.alpha.,5,5,8a-tetramethyl-2-methylene-, (4aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.7466	74.66%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.5009	50.09%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.8199	81.99%
OATP1B3 inhibitior	+	0.8455	84.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7136	71.36%
P-glycoprotein inhibitior	-	0.8269	82.69%
P-glycoprotein substrate	-	0.8626	86.26%
CYP3A4 substrate	+	0.5987	59.87%
CYP2C9 substrate	+	0.5024	50.24%
CYP2D6 substrate	-	0.7533	75.33%
CYP3A4 inhibition	-	0.6880	68.80%
CYP2C9 inhibition	-	0.8114	81.14%
CYP2C19 inhibition	-	0.7857	78.57%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.8527	85.27%
CYP2C8 inhibition	+	0.5450	54.50%
CYP inhibitory promiscuity	-	0.6787	67.87%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7900	79.00%
Carcinogenicity (trinary)	Non-required	0.6701	67.01%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.8642	86.42%
Skin irritation	-	0.5768	57.68%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6786	67.86%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.6923	69.23%
skin sensitisation	+	0.7983	79.83%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.7434	74.34%
Acute Oral Toxicity (c)	III	0.4642	46.42%
Estrogen receptor binding	+	0.5541	55.41%
Androgen receptor binding	+	0.5685	56.85%
Thyroid receptor binding	-	0.4924	49.24%
Glucocorticoid receptor binding	+	0.6659	66.59%
Aromatase binding	-	0.6103	61.03%
PPAR gamma	-	0.4852	48.52%
Honey bee toxicity	-	0.8959	89.59%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9937	99.37%

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	98.77%	97.25%
CHEMBL1977	P11473	Vitamin D receptor	96.94%	99.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.26%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.63%	97.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	89.12%	90.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.71%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.67%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.01%	95.89%
CHEMBL1871	P10275	Androgen Receptor	83.01%	96.43%
CHEMBL233	P35372	Mu opioid receptor	82.31%	97.93%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.31%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.14%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	81.07%	97.05%
CHEMBL5028	O14672	ADAM10	80.56%	97.50%

Plants that contains it

• Abies chensiensis
• Abies firma
• Abies sachalinensis
• Abies spectabilis
• Cedrus atlantica
• Cedrus libani
• Chamaecyparis pisifera
• Conocephalum conicum
• Cupressus sempervirens
• Halocarpus biformis
• Hamamelis virginiana
• Juniperus communis
• Juniperus monticola
• Larix gmelinii var. olgensis
• Larix laricina
• Leiocarpa leptolepis
• Loropetalum chinense
• Murraya exotica
• Murraya paniculata
• Pinus contorta
• Renealmia alpinia
• Rhizophora mangle
• Salvia candidissima
• Salvia multicaulis
• Salvia officinalis
• Salvia sclarea
• Senecio erubescens
• Senecio variabilis
• Solidago rugosa
• Viguiera dentata
• Vitex agnus-castus

Cross-Links

• PubChem: 3034394
• NPASS: NPC67840
• LOTUS: LTS0075915
• wikiData: Q105225216