(1R,4abeta)-Decahydro-1beta-[(E)-5-hydroxy-3-methyl-3-pentenyl]-2,5,5,8abeta-tetramethylnaphthalen-2alpha-ol

Details

• Internal ID: a1060062-2211-49ab-a5a8-291679b4358d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,2R,4aR,8aS)-1-[(E)-5-hydroxy-3-methylpent-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• SMILES (Canonical): CC(=CCO)CCC1C2(CCCC(C2CCC1(C)O)(C)C)C
• SMILES (Isomeric): C/C(=C\CO)/CC[C@@H]1[C@]2(CCCC([C@H]2CC[C@@]1(C)O)(C)C)C
• InChI: InChI=1S/C20H36O2/c1-15(10-14-21)7-8-17-19(4)12-6-11-18(2,3)16(19)9-13-20(17,5)22/h10,16-17,21-22H,6-9,11-14H2,1-5H3/b15-10+/t16-,17-,19+,20-/m1/s1
• InChI Key: LEOHDQKUMQKLMP-HHQLMWAKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₆O₂
• Molecular Weight: 308.50 g/mol
• Exact Mass: 308.271530387 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.70
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (1R,2R,4aR,8aS)-1-[(E)-5-hydroxy-3-methylpent-3-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• (1R,4abeta)-Decahydro-1beta-[(E)-5-hydroxy-3-methyl-3-pentenyl]-2,5,5,8abeta-tetramethylnaphthalen-2alpha-ol
• LEOHDQKUMQKLMP-HHQLMWAKSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.7579	75.79%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5844	58.44%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.8464	84.64%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6135	61.35%
BSEP inhibitior	+	0.5721	57.21%
P-glycoprotein inhibitior	-	0.7677	76.77%
P-glycoprotein substrate	-	0.8906	89.06%
CYP3A4 substrate	+	0.5829	58.29%
CYP2C9 substrate	-	0.5471	54.71%
CYP2D6 substrate	-	0.7775	77.75%
CYP3A4 inhibition	-	0.7176	71.76%
CYP2C9 inhibition	-	0.8824	88.24%
CYP2C19 inhibition	-	0.8504	85.04%
CYP2D6 inhibition	-	0.9226	92.26%
CYP1A2 inhibition	-	0.8451	84.51%
CYP2C8 inhibition	-	0.6856	68.56%
CYP inhibitory promiscuity	-	0.6747	67.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6668	66.68%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8162	81.62%
Skin irritation	-	0.6712	67.12%
Skin corrosion	-	0.9730	97.30%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3667	36.67%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.7452	74.52%
skin sensitisation	-	0.5535	55.35%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6326	63.26%
Acute Oral Toxicity (c)	III	0.8242	82.42%
Estrogen receptor binding	+	0.7400	74.00%
Androgen receptor binding	-	0.5748	57.48%
Thyroid receptor binding	+	0.6199	61.99%
Glucocorticoid receptor binding	+	0.7390	73.90%
Aromatase binding	+	0.5454	54.54%
PPAR gamma	+	0.7134	71.34%
Honey bee toxicity	-	0.9197	91.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9638	96.38%

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	97.61%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.18%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	90.87%	94.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.21%	95.50%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	89.68%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.50%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	88.41%	95.92%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.61%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.48%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.95%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.42%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.90%	92.94%
CHEMBL233	P35372	Mu opioid receptor	81.88%	97.93%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.83%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.58%	91.24%
CHEMBL4040	P28482	MAP kinase ERK2	80.51%	83.82%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Marrubium anisodon
• Nassauvia cumingii
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Otostegia fruticosa
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 12306731
• NPASS: NPC197011
• LOTUS: LTS0147900
• wikiData: Q105150683