[(2S,3aS,3bS,5R,6aR,7S,7aR)-2,3a,7-trihydroxy-4,4,6a-trimethyl-3-methylidene-2,3b,5,6,7,7a-hexahydro-1H-cyclopenta[a]pentalen-5-yl] acetate

Details

• Internal ID: 654a366b-72c4-4c47-be1b-a124b11bcfec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Triquinane sesquiterpenoids > Linear triquinanes > Capnellane and isocapnellane sesquiterpenoids
• IUPAC Name: [(2S,3aS,3bS,5R,6aR,7S,7aR)-2,3a,7-trihydroxy-4,4,6a-trimethyl-3-methylidene-2,3b,5,6,7,7a-hexahydro-1H-cyclopenta[a]pentalen-5-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2(C(C3CC(C(=C)C3(C2C1(C)C)O)O)O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@]2([C@H]([C@H]3C[C@@H](C(=C)[C@@]3([C@H]2C1(C)C)O)O)O)C
• InChI: InChI=1S/C17H26O5/c1-8-11(19)6-10-13(20)16(5)7-12(22-9(2)18)15(3,4)14(16)17(8,10)21/h10-14,19-21H,1,6-7H2,2-5H3/t10-,11+,12-,13+,14+,16+,17-/m1/s1
• InChI Key: MMUAIEFHRONVGA-HMSCMIGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.17802393 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9834	98.34%
Caco-2	-	0.6854	68.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5713	57.13%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	+	0.9151	91.51%
OATP1B3 inhibitior	-	0.2799	27.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9351	93.51%
P-glycoprotein inhibitior	-	0.9056	90.56%
P-glycoprotein substrate	-	0.8259	82.59%
CYP3A4 substrate	+	0.6385	63.85%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8629	86.29%
CYP3A4 inhibition	-	0.7992	79.92%
CYP2C9 inhibition	-	0.7644	76.44%
CYP2C19 inhibition	-	0.7874	78.74%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.7433	74.33%
CYP2C8 inhibition	-	0.8384	83.84%
CYP inhibitory promiscuity	-	0.9037	90.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9118	91.18%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	-	0.5570	55.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6604	66.04%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5782	57.82%
skin sensitisation	-	0.6240	62.40%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7167	71.67%
Acute Oral Toxicity (c)	I	0.3670	36.70%
Estrogen receptor binding	+	0.6896	68.96%
Androgen receptor binding	+	0.5935	59.35%
Thyroid receptor binding	+	0.5233	52.33%
Glucocorticoid receptor binding	+	0.5451	54.51%
Aromatase binding	+	0.5280	52.80%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.6840	68.40%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	+	0.9889	98.89%

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	97.21%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.59%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.04%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.92%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.37%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	85.70%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.61%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.16%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.28%	91.07%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163101086
• LOTUS: LTS0108833
• wikiData: Q105168076