13-Episclareol

Details

• Internal ID: 29c06a61-dd4f-4e3c-ae24-4660fb6056db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,2R,4aS,8aS)-1-(3-hydroxy-3-methylpent-4-enyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• SMILES (Canonical): CC1(CCCC2(C1CCC(C2CCC(C)(C=C)O)(C)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CC[C@@]([C@@H]2CCC(C)(C=C)O)(C)O)(C)C
• InChI: InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18?,19-,20+/m0/s1
• InChI Key: XVULBTBTFGYVRC-SVPXJYONSA-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: 4.90
• Atomic LogP (AlogP): 4.70
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• A1A2FI1KEJ
• 4630-08-4
• (1R,2R,4aS,8aS)-1-(3-hydroxy-3-methylpent-4-enyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
• (1R,2R,4AS,8AS)-1-[(3R)-3-HYDROXY-3-METHYL-4-PENTEN-1-YL]-2,5,5,8A-TETRAMETHYLDECAHYDRO-2-NAPHTHALENOL
• EPISCLAREOL
• ISOSCLAREOL
• UNII-A1A2FI1KEJ
• SCHEMBL15503382
• (13S)-Labd-14-ene-8,13-diol
• AKOS040790448
• Labd-14-ene-8,13-diol, (13S)-
• PD132214
• (.ALPHA.S,1R,2R,4AS,8AS)-.ALPHA.-ETHENYLDECAHYDRO-2-HYDROXY-.ALPHA.,2,5,5,8A-PENTAMETHYL-1-NAPHTHALENEPROPANOL
• 1-NAPHTHALENEPROPANOL, .ALPHA.-ETHENYLDECAHYDRO-2-HYDROXY-.ALPHA.,2,5,5,8A-PENTAMETHYL-, (.ALPHA.S,1R,2R,4AS,8AS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.7019	70.19%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.5506	55.06%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8078	80.78%
OATP1B3 inhibitior	+	0.9513	95.13%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6512	65.12%
P-glycoprotein inhibitior	-	0.8449	84.49%
P-glycoprotein substrate	-	0.8777	87.77%
CYP3A4 substrate	+	0.6062	60.62%
CYP2C9 substrate	+	0.5024	50.24%
CYP2D6 substrate	-	0.7533	75.33%
CYP3A4 inhibition	-	0.7771	77.71%
CYP2C9 inhibition	-	0.9100	91.00%
CYP2C19 inhibition	-	0.5331	53.31%
CYP2D6 inhibition	-	0.9555	95.55%
CYP1A2 inhibition	-	0.7300	73.00%
CYP2C8 inhibition	+	0.4715	47.15%
CYP inhibitory promiscuity	-	0.7710	77.10%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.7195	71.95%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.8516	85.16%
Skin irritation	-	0.5516	55.16%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3941	39.41%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.6345	63.45%
skin sensitisation	+	0.6306	63.06%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7669	76.69%
Acute Oral Toxicity (c)	III	0.8254	82.54%
Estrogen receptor binding	+	0.6524	65.24%
Androgen receptor binding	-	0.5752	57.52%
Thyroid receptor binding	-	0.5255	52.55%
Glucocorticoid receptor binding	+	0.6552	65.52%
Aromatase binding	-	0.5851	58.51%
PPAR gamma	+	0.5435	54.35%
Honey bee toxicity	-	0.8856	88.56%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9896	98.96%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	158.5 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.46%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.85%	91.11%
CHEMBL325	Q13547	Histone deacetylase 1	93.19%	95.92%
CHEMBL1937	Q92769	Histone deacetylase 2	91.04%	94.75%
CHEMBL206	P03372	Estrogen receptor alpha	91.00%	97.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.77%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.20%	96.09%
CHEMBL233	P35372	Mu opioid receptor	87.74%	97.93%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	87.27%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.24%	100.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.04%	90.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.72%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.68%	95.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.61%	92.94%
CHEMBL4302	P08183	P-glycoprotein 1	85.45%	92.98%
CHEMBL1902	P62942	FK506-binding protein 1A	84.93%	97.05%
CHEMBL3524	P56524	Histone deacetylase 4	84.17%	92.97%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.97%	99.18%
CHEMBL2581	P07339	Cathepsin D	83.26%	98.95%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	83.18%	94.01%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.05%	95.50%
CHEMBL1871	P10275	Androgen Receptor	83.03%	96.43%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.17%	91.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.84%	91.07%
CHEMBL1977	P11473	Vitamin D receptor	81.51%	99.43%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.52%	100.00%

Plants that contains it

• Astragalus brachystachys
• Cistus × incanus
• Cistus creticus
• Jungermannia hattoriana
• Jungermannia infusca
• Jungermannia truncata
• Nicotiana glutinosa
• Polemonium viscosum
• Pseudognaphalium cheiranthifolium
• Pseudognaphalium schraderi
• Pseudognaphalium viscosum
• Ptychanthus striatus
• Sagittaria trifolia
• Salvia atropatana
• Salvia palaestina
• Salvia sahendica
• Salvia sclarea
• Stachys rosea
• Vitex agnus-castus

Cross-Links

• PubChem: 56842011
• LOTUS: LTS0173518
• wikiData: Q104251412