2-[(1aR,2'S,2aS,6aS,7S,7aR)-7a-(hydroxymethyl)-2',3,3,6a-tetramethylspiro[1a,2,2a,4,5,6-hexahydronaphtho[2,3-b]oxirene-7,5'-oxolane]-2'-yl]acetic acid

Details

• Internal ID: 81674d61-029b-49ef-947d-939dfa1c47a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-[(1aR,2'S,2aS,6aS,7S,7aR)-7a-(hydroxymethyl)-2',3,3,6a-tetramethylspiro[1a,2,2a,4,5,6-hexahydronaphtho[2,3-b]oxirene-7,5'-oxolane]-2'-yl]acetic acid
• SMILES (Canonical): CC1(CCCC2(C1CC3C(C24CCC(O4)(C)CC(=O)O)(O3)CO)C)C
• SMILES (Isomeric): C[C@]1(CC[C@]2(O1)[C@]3(CCCC([C@@H]3C[C@@H]4[C@]2(O4)CO)(C)C)C)CC(=O)O
• InChI: InChI=1S/C20H32O5/c1-16(2)6-5-7-18(4)13(16)10-14-19(12-21,24-14)20(18)9-8-17(3,25-20)11-15(22)23/h13-14,21H,5-12H2,1-4H3,(H,22,23)/t13-,14+,17-,18-,19+,20-/m0/s1
• InChI Key: YOGHSAKMXHLZPP-FFUZVNMOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.22497412 g/mol
• Topological Polar Surface Area (TPSA): 79.30 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9503	95.03%
Caco-2	+	0.6558	65.58%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6400	64.00%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.8363	83.63%
OATP1B3 inhibitior	+	0.9318	93.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7091	70.91%
P-glycoprotein inhibitior	-	0.7785	77.85%
P-glycoprotein substrate	-	0.8628	86.28%
CYP3A4 substrate	+	0.6218	62.18%
CYP2C9 substrate	-	0.6063	60.63%
CYP2D6 substrate	-	0.8506	85.06%
CYP3A4 inhibition	-	0.8050	80.50%
CYP2C9 inhibition	-	0.7115	71.15%
CYP2C19 inhibition	-	0.8022	80.22%
CYP2D6 inhibition	-	0.9255	92.55%
CYP1A2 inhibition	-	0.8279	82.79%
CYP2C8 inhibition	+	0.4472	44.72%
CYP inhibitory promiscuity	-	0.9004	90.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5776	57.76%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.8343	83.43%
Skin irritation	-	0.7036	70.36%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5398	53.98%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8291	82.91%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5933	59.33%
Acute Oral Toxicity (c)	III	0.5524	55.24%
Estrogen receptor binding	+	0.8948	89.48%
Androgen receptor binding	+	0.6596	65.96%
Thyroid receptor binding	+	0.7030	70.30%
Glucocorticoid receptor binding	+	0.6065	60.65%
Aromatase binding	+	0.8200	82.00%
PPAR gamma	+	0.6770	67.70%
Honey bee toxicity	-	0.9105	91.05%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8932	89.32%

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	96.40%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.73%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.63%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.84%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	88.85%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.44%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.93%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	83.80%	90.17%

Plants that contains it

• Chrysoma pauciflosculosa

Cross-Links

• PubChem: 162916298
• LOTUS: LTS0020290
• wikiData: Q105351298