13-Epitorulosol

Details

• Internal ID: 38415861-b75b-490a-a336-da068afc1679
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3S)-5-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-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)CO
• SMILES (Isomeric): C[C@@]1(CCC[C@]2([C@H]1CCC(=C)[C@@H]2CC[C@@](C)(C=C)O)C)CO
• InChI: InChI=1S/C20H34O2/c1-6-19(4,22)13-10-16-15(2)8-9-17-18(3,14-21)11-7-12-20(16,17)5/h6,16-17,21-22H,1-2,7-14H2,3-5H3/t16-,17-,18+,19+,20+/m0/s1
• InChI Key: IERFAZQCIAZODG-CENDIDJXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.50 g/mol
• Exact Mass: 306.255880323 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.47
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Epitorulosol
• DTXSID101110479
• Labda-8(20),14-diene-13,19-diol, (13S)-
• (alphaS,1S,4aR,5S,8aR)-alpha-Ethenyldecahydro-5-(hydroxymethyl)-alpha,5,8a-trimethyl-2-methylene-1-naphthalenepropanol
• 1-Naphthalenepropanol, .alpha.-ethenyldecahydro-5-(hydroxymethyl)-.alpha.,5,8a-trimethyl-2-methylene-, [1S-[1.alpha.(R*),4a.beta.,5.alpha.,8a.alpha.]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9935	99.35%
Caco-2	+	0.7380	73.80%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Lysosomes	0.5726	57.26%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5843	58.43%
BSEP inhibitior	-	0.5882	58.82%
P-glycoprotein inhibitior	-	0.8850	88.50%
P-glycoprotein substrate	-	0.7943	79.43%
CYP3A4 substrate	+	0.6136	61.36%
CYP2C9 substrate	-	0.5471	54.71%
CYP2D6 substrate	-	0.7775	77.75%
CYP3A4 inhibition	+	0.5682	56.82%
CYP2C9 inhibition	-	0.8032	80.32%
CYP2C19 inhibition	-	0.7772	77.72%
CYP2D6 inhibition	-	0.9072	90.72%
CYP1A2 inhibition	-	0.8052	80.52%
CYP2C8 inhibition	+	0.5543	55.43%
CYP inhibitory promiscuity	-	0.6187	61.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6746	67.46%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9223	92.23%
Skin irritation	-	0.7284	72.84%
Skin corrosion	-	0.9724	97.24%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4361	43.61%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.7197	71.97%
skin sensitisation	-	0.5599	55.99%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8151	81.51%
Acute Oral Toxicity (c)	III	0.8266	82.66%
Estrogen receptor binding	+	0.6275	62.75%
Androgen receptor binding	+	0.6333	63.33%
Thyroid receptor binding	+	0.5365	53.65%
Glucocorticoid receptor binding	+	0.7435	74.35%
Aromatase binding	-	0.5364	53.64%
PPAR gamma	-	0.5595	55.95%
Honey bee toxicity	-	0.8711	87.11%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9794	97.94%

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	98.12%	97.25%
CHEMBL1977	P11473	Vitamin D receptor	97.55%	99.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.57%	91.11%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	91.41%	90.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.01%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	87.66%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.29%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.42%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.86%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.17%	95.50%
CHEMBL259	P32245	Melanocortin receptor 4	85.15%	95.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.17%	100.00%
CHEMBL233	P35372	Mu opioid receptor	83.34%	97.93%
CHEMBL1902	P62942	FK506-binding protein 1A	81.29%	97.05%
CHEMBL237	P41145	Kappa opioid receptor	80.92%	98.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.14%	86.33%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.13%	97.50%

Plants that contains it

• Breonia chinensis
• Campylotropis hirtella
• Ceropegia dichotoma
• Crinum moorei
• Crotalaria candicans
• Cryptomeria japonica
• Cupressus torulosa
• Dendrobium loddigesii
• Distephanus angulifolius
• Eucalyptus apodophylla
• Glycosmis macrophylla
• Gypsophila perfoliata
• Halocarpus bidwillii
• Hypericum polyanthemum
• Juniperus drupacea
• Larix decidua
• Larix gmelinii var. gmelinii
• Larix sibirica
• Lophostemon confertus
• Mentha × gentilis
• Ononis spinosa
• Orbivestus karaguensis
• Pentaclethra macrophylla
• Periploca sepium
• Pinalia japonica
• Plectranthus hereroensis
• Pterocaulon virgatum
• Rhodiola semenovii
• Salvia sessei
• Sonneratia caseolaris
• Stephania zippeliana
• Veronica polita

Cross-Links

• PubChem: 12444402
• NPASS: NPC72300
• LOTUS: LTS0139128
• wikiData: Q105111935