(1R,2S,11S)-12,12-dimethyl-6-propan-2-yltricyclo[9.4.0.03,8]pentadeca-3,5,7-triene-1,2,5-triol

Details

• Internal ID: 20104679-dfb0-4bfd-bb30-e1e27e726dc9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (1R,2S,11S)-12,12-dimethyl-6-propan-2-yltricyclo[9.4.0.03,8]pentadeca-3,5,7-triene-1,2,5-triol
• SMILES (Canonical): CC(C)C1=C(C=C2C(C3(CCCC(C3CCC2=C1)(C)C)O)O)O
• SMILES (Isomeric): CC(C)C1=C(C=C2[C@@H]([C@]3(CCCC([C@@H]3CCC2=C1)(C)C)O)O)O
• InChI: InChI=1S/C20H30O3/c1-12(2)14-10-13-6-7-17-19(3,4)8-5-9-20(17,23)18(22)15(13)11-16(14)21/h10-12,17-18,21-23H,5-9H2,1-4H3/t17-,18-,20+/m0/s1
• InChI Key: PNHKTXLBKGDTNY-CMKODMSKSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.05
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• From the seeds of Chamaecyparis pisifera 4aH-Dibenzo[a,d]cycloheptene-4a,5,7-triol, 1,2,3,4,5,10,11,11a-octahydro-1,1-dimethyl- 8-(1-methylethyl)-, [4aR-(4a.alpha.,5.alpha.,11a.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.7244	72.44%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8045	80.45%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.9206	92.06%
OATP1B3 inhibitior	+	0.9524	95.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6462	64.62%
P-glycoprotein inhibitior	-	0.8729	87.29%
P-glycoprotein substrate	-	0.7175	71.75%
CYP3A4 substrate	+	0.6358	63.58%
CYP2C9 substrate	+	0.6370	63.70%
CYP2D6 substrate	+	0.3479	34.79%
CYP3A4 inhibition	-	0.8291	82.91%
CYP2C9 inhibition	-	0.8756	87.56%
CYP2C19 inhibition	-	0.7368	73.68%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	+	0.5059	50.59%
CYP2C8 inhibition	-	0.5871	58.71%
CYP inhibitory promiscuity	-	0.9359	93.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.6900	69.00%
Carcinogenicity (trinary)	Non-required	0.6204	62.04%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9495	94.95%
Skin irritation	-	0.5769	57.69%
Skin corrosion	-	0.9081	90.81%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5591	55.91%
Micronuclear	-	0.9500	95.00%
Hepatotoxicity	-	0.6084	60.84%
skin sensitisation	-	0.7407	74.07%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8959	89.59%
Acute Oral Toxicity (c)	III	0.6744	67.44%
Estrogen receptor binding	+	0.7141	71.41%
Androgen receptor binding	-	0.5629	56.29%
Thyroid receptor binding	+	0.7726	77.26%
Glucocorticoid receptor binding	+	0.7392	73.92%
Aromatase binding	+	0.7241	72.41%
PPAR gamma	+	0.6599	65.99%
Honey bee toxicity	-	0.8473	84.73%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9930	99.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.16%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.69%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.39%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.26%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.67%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.60%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.47%	93.99%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.08%	99.15%
CHEMBL5203	P33316	dUTP pyrophosphatase	88.37%	99.18%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.89%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.72%	93.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.51%	93.40%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.78%	91.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.64%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.24%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.09%	97.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.67%	90.24%
CHEMBL1937	Q92769	Histone deacetylase 2	82.49%	94.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.01%	91.03%
CHEMBL3038469	P24941	CDK2/Cyclin A	81.77%	91.38%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.30%	96.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.94%	82.69%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.39%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.36%	91.07%

Plants that contains it

• Chamaecyparis pisifera

Cross-Links

• PubChem: 101317815
• NPASS: NPC301981
• LOTUS: LTS0125686
• wikiData: Q105211935