(1R,2R,4As,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol

Details

• Internal ID: 76c9f0d5-eba9-4fbb-b038-83a8d0fde84b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,2R,4aS,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• SMILES (Canonical): CC(CCC1C2(CCCC(C2CCC1(C)O)(C)C)C)CCO
• SMILES (Isomeric): C[C@@H](CC[C@@H]1[C@]2(CCCC([C@@H]2CC[C@@]1(C)O)(C)C)C)CCO
• InChI: InChI=1S/C20H38O2/c1-15(10-14-21)7-8-17-19(4)12-6-11-18(2,3)16(19)9-13-20(17,5)22/h15-17,21-22H,6-14H2,1-5H3/t15-,16-,17+,19-,20+/m0/s1
• InChI Key: MCHQEVJMCLOQAZ-VBYALHQYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₈O₂
• Molecular Weight: 310.50 g/mol
• Exact Mass: 310.287180451 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.78
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• (1R,2R,4As,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• (13S)-Labdane-8,15-diol
• CHEMBL1172098
• SCHEMBL20658669
• MCHQEVJMCLOQAZ-VBYALHQYSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.6304	63.04%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6091	60.91%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8777	87.77%
OATP1B3 inhibitior	+	0.9131	91.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6792	67.92%
BSEP inhibitior	-	0.7171	71.71%
P-glycoprotein inhibitior	-	0.8313	83.13%
P-glycoprotein substrate	-	0.7961	79.61%
CYP3A4 substrate	+	0.5690	56.90%
CYP2C9 substrate	-	0.5733	57.33%
CYP2D6 substrate	-	0.7555	75.55%
CYP3A4 inhibition	-	0.8212	82.12%
CYP2C9 inhibition	-	0.8148	81.48%
CYP2C19 inhibition	-	0.8605	86.05%
CYP2D6 inhibition	-	0.9572	95.72%
CYP1A2 inhibition	-	0.5542	55.42%
CYP2C8 inhibition	-	0.8462	84.62%
CYP inhibitory promiscuity	-	0.8626	86.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7333	73.33%
Eye corrosion	-	0.9773	97.73%
Eye irritation	-	0.7589	75.89%
Skin irritation	-	0.7322	73.22%
Skin corrosion	-	0.9729	97.29%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6460	64.60%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	-	0.6443	64.43%
skin sensitisation	-	0.5774	57.74%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6858	68.58%
Acute Oral Toxicity (c)	III	0.8495	84.95%
Estrogen receptor binding	+	0.8195	81.95%
Androgen receptor binding	-	0.6622	66.22%
Thyroid receptor binding	+	0.7011	70.11%
Glucocorticoid receptor binding	+	0.7285	72.85%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5830	58.30%
Honey bee toxicity	-	0.9150	91.50%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8913	89.13%

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	99.39%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.97%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.87%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.76%	82.69%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.67%	89.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.80%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.59%	97.09%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	86.23%	95.36%
CHEMBL1937	Q92769	Histone deacetylase 2	85.94%	94.75%
CHEMBL237	P41145	Kappa opioid receptor	85.85%	98.10%
CHEMBL2581	P07339	Cathepsin D	85.80%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.53%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.47%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.67%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.96%	96.61%
CHEMBL4302	P08183	P-glycoprotein 1	82.56%	92.98%
CHEMBL325	Q13547	Histone deacetylase 1	81.82%	95.92%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.79%	98.33%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	81.56%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.15%	96.38%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.02%	98.05%
CHEMBL4073	P09237	Matrix metalloproteinase 7	80.59%	97.56%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	80.57%	98.46%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.55%	96.47%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.43%	100.00%

Plants that contains it

• Amaranthus hypochondriacus
• Berberis repens
• Cistus ladanifer
• Croton laccifer
• Euphorbia myrsinites
• Haplopappus glutinosus
• Helicteres angustifolia
• Hippeastrum papilio
• Limnocharis flava
• Lycopodium thyoides
• Millettia ferruginea
• Sedum litoreum
• Senecio viscosus
• Senegalia pennata
• Teucrium asiaticum
• Thermopsis dolichocarpa
• Vicia amurensis
• Wyethia mollis
• Zanthoxylum americanum

Cross-Links

• PubChem: 11130717
• NPASS: NPC135438
• ChEMBL: CHEMBL1172098
• LOTUS: LTS0069901
• wikiData: Q105161217