(3aR,5Z,9Z,13E,15aS)-6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3a,4,7,8,11,12,15,15a-octahydrocyclotetradeca[b]furan-2-one

Details

• Internal ID: f2f206ab-70cf-4a5f-947a-f8ff993d83d4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones > Cembranolides
• IUPAC Name: (3aR,5Z,9Z,13E,15aS)-6-(hydroxymethyl)-10,14-dimethyl-3-methylidene-3a,4,7,8,11,12,15,15a-octahydrocyclotetradeca[b]furan-2-one
• SMILES (Canonical): CC1=CCCC(=CCC2C(CC(=CCC1)C)OC(=O)C2=C)CO
• SMILES (Isomeric): C/C/1=C/CC/C(=C/C[C@H]2[C@H](C/C(=C/CC1)/C)OC(=O)C2=C)/CO
• InChI: InChI=1S/C20H28O3/c1-14-6-4-8-15(2)12-19-18(16(3)20(22)23-19)11-10-17(13-21)9-5-7-14/h7-8,10,18-19,21H,3-6,9,11-13H2,1-2H3/b14-7-,15-8+,17-10-/t18-,19+/m1/s1
• InChI Key: KXVIJXIRUBWYDB-URBVYLMCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.40 g/mol
• Exact Mass: 316.20384475 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 4.25
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9917	99.17%
Caco-2	+	0.6896	68.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6892	68.92%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9150	91.50%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	+	0.5077	50.77%
BSEP inhibitior	-	0.6782	67.82%
P-glycoprotein inhibitior	-	0.7443	74.43%
P-glycoprotein substrate	-	0.8886	88.86%
CYP3A4 substrate	+	0.5352	53.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	-	0.5786	57.86%
CYP2C9 inhibition	-	0.8703	87.03%
CYP2C19 inhibition	-	0.8103	81.03%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.5082	50.82%
CYP2C8 inhibition	-	0.6598	65.98%
CYP inhibitory promiscuity	-	0.8704	87.04%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6710	67.10%
Eye corrosion	-	0.9718	97.18%
Eye irritation	-	0.7804	78.04%
Skin irritation	-	0.6464	64.64%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	-	0.5991	59.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.6749	67.49%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6050	60.50%
skin sensitisation	-	0.7521	75.21%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7336	73.36%
Acute Oral Toxicity (c)	III	0.5405	54.05%
Estrogen receptor binding	-	0.6552	65.52%
Androgen receptor binding	-	0.4933	49.33%
Thyroid receptor binding	-	0.6276	62.76%
Glucocorticoid receptor binding	-	0.4632	46.32%
Aromatase binding	-	0.6380	63.80%
PPAR gamma	-	0.5215	52.15%
Honey bee toxicity	-	0.8825	88.25%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9789	97.89%

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	97.32%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.37%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.08%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.65%	97.09%
CHEMBL4208	P20618	Proteasome component C5	83.20%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.78%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.12%	96.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162910969
• LOTUS: LTS0244468
• wikiData: Q105147548