(1S,3R,5R,7S,10S,13R)-1,10,13-trihydroxy-3,6,6,10,14-pentamethyltricyclo[10.3.0.05,7]pentadeca-11,14-dien-2-one

Details

• Internal ID: 23198c9e-54bd-42ed-90e8-48c6cda1107d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1S,3R,5R,7S,10S,13R)-1,10,13-trihydroxy-3,6,6,10,14-pentamethyltricyclo[10.3.0.05,7]pentadeca-11,14-dien-2-one
• SMILES (Canonical): CC1CC2C(C2(C)C)CCC(C=C3C(C(=CC3(C1=O)O)C)O)(C)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]2[C@@H](C2(C)C)CC[C@](C=C3[C@@H](C(=C[C@]3(C1=O)O)C)O)(C)O
• InChI: InChI=1S/C20H30O4/c1-11-8-14-13(18(14,3)4)6-7-19(5,23)10-15-16(21)12(2)9-20(15,24)17(11)22/h9-11,13-14,16,21,23-24H,6-8H2,1-5H3/t11-,13+,14-,16-,19+,20+/m1/s1
• InChI Key: SMGFYRJTHUJGEK-KRJCAEJZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	+	0.6423	64.23%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6717	67.17%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8971	89.71%
OATP1B3 inhibitior	+	0.9109	91.09%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5385	53.85%
BSEP inhibitior	-	0.8499	84.99%
P-glycoprotein inhibitior	-	0.8816	88.16%
P-glycoprotein substrate	-	0.7419	74.19%
CYP3A4 substrate	+	0.6683	66.83%
CYP2C9 substrate	-	0.8426	84.26%
CYP2D6 substrate	-	0.8094	80.94%
CYP3A4 inhibition	-	0.8400	84.00%
CYP2C9 inhibition	-	0.6694	66.94%
CYP2C19 inhibition	-	0.7448	74.48%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	-	0.6625	66.25%
CYP2C8 inhibition	-	0.7657	76.57%
CYP inhibitory promiscuity	-	0.9028	90.28%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6045	60.45%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9503	95.03%
Skin irritation	+	0.5978	59.78%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.7770	77.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4738	47.38%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6981	69.81%
skin sensitisation	-	0.7234	72.34%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7535	75.35%
Acute Oral Toxicity (c)	I	0.4069	40.69%
Estrogen receptor binding	+	0.7343	73.43%
Androgen receptor binding	+	0.6460	64.60%
Thyroid receptor binding	+	0.8094	80.94%
Glucocorticoid receptor binding	+	0.8626	86.26%
Aromatase binding	+	0.6181	61.81%
PPAR gamma	-	0.5346	53.46%
Honey bee toxicity	-	0.8775	87.75%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9646	96.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.66%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.54%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.67%	100.00%
CHEMBL1871	P10275	Androgen Receptor	86.40%	96.43%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.90%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.29%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.04%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.98%	82.69%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	83.55%	86.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.58%	95.89%

Plants that contains it

• Jatropha multifida

Cross-Links

• PubChem: 162870391
• LOTUS: LTS0273424
• wikiData: Q105255907