methyl (3S)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoate

Details

• Internal ID: d1888ccc-325d-4c0b-b4f3-5b983c340589
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: methyl (3S)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoate
• SMILES (Canonical): CC(CCC1C2(CCCC(C2CCC1(C)O)(C)C)C)CC(=O)OC
• SMILES (Isomeric): C[C@@H](CC[C@@H]1[C@]2(CCCC([C@@H]2CC[C@@]1(C)O)(C)C)C)CC(=O)OC
• InChI: InChI=1S/C21H38O3/c1-15(14-18(22)24-6)8-9-17-20(4)12-7-11-19(2,3)16(20)10-13-21(17,5)23/h15-17,23H,7-14H2,1-6H3/t15-,16-,17+,20-,21+/m0/s1
• InChI Key: GOECIRGMYVJNBS-CFPPRVJZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₈O₃
• Molecular Weight: 338.50 g/mol
• Exact Mass: 338.28209507 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 4.96
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• methyl (3S)-5-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoate
• (1R,4aalpha,betaS)-Decahydro-2alpha-hydroxy-beta,2,5,5,8abeta-pentamethyl-1-naphthalenepentanoic acid methyl ester
• Labdanic Acid Methyl Ester
• CHEMBL1171377
• GOECIRGMYVJNBS-CFPPRVJZSA-N
• (8R,13S)-8-Hydroxylabdan-15-oic acid methyl ester
• Labdan-15-oic acid, 8-hydroxy-, methyl ester, (8R,13S)-
• 1-Naphthalenepentanoic acid, decahydro-2-hydroxy-.beta.,2,5,5,8a-pentamethyl-, methyl ester, [1R-[1.alpha.(S*),2.beta.,4a.beta.,8a.alpha.]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	+	0.6426	64.26%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8692	86.92%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8753	87.53%
OATP1B3 inhibitior	+	0.9117	91.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.5573	55.73%
P-glycoprotein inhibitior	-	0.7843	78.43%
P-glycoprotein substrate	-	0.7435	74.35%
CYP3A4 substrate	+	0.6465	64.65%
CYP2C9 substrate	-	0.6408	64.08%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	-	0.8186	81.86%
CYP2C9 inhibition	-	0.5142	51.42%
CYP2C19 inhibition	-	0.8948	89.48%
CYP2D6 inhibition	-	0.9717	97.17%
CYP1A2 inhibition	-	0.9140	91.40%
CYP2C8 inhibition	-	0.7833	78.33%
CYP inhibitory promiscuity	-	0.9547	95.47%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7065	70.65%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.6175	61.75%
Skin irritation	-	0.5141	51.41%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5544	55.44%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6206	62.06%
skin sensitisation	-	0.6691	66.91%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5965	59.65%
Acute Oral Toxicity (c)	III	0.7356	73.56%
Estrogen receptor binding	+	0.6628	66.28%
Androgen receptor binding	-	0.5701	57.01%
Thyroid receptor binding	+	0.6264	62.64%
Glucocorticoid receptor binding	+	0.6375	63.75%
Aromatase binding	+	0.5474	54.74%
PPAR gamma	-	0.5883	58.83%
Honey bee toxicity	-	0.8656	86.56%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9725	97.25%

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	97.77%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.19%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	94.36%	96.38%
CHEMBL4040	P28482	MAP kinase ERK2	93.63%	83.82%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.43%	82.69%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.56%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.39%	94.33%
CHEMBL332	P03956	Matrix metalloproteinase-1	87.22%	94.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.95%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.14%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.53%	91.19%
CHEMBL2581	P07339	Cathepsin D	84.63%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.43%	95.50%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.32%	89.05%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.31%	95.71%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.08%	96.47%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.94%	94.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.65%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.46%	91.07%
CHEMBL5255	O00206	Toll-like receptor 4	83.31%	92.50%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	82.69%	95.36%
CHEMBL4073	P09237	Matrix metalloproteinase 7	81.94%	97.56%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.75%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.68%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.73%	91.24%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.45%	93.03%
CHEMBL5028	O14672	ADAM10	80.41%	97.50%

Plants that contains it

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

Cross-Links

• PubChem: 7057547
• NPASS: NPC41542
• ChEMBL: CHEMBL1171377