(1S,2R,4R,7E)-12-(hydroxymethyl)-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradeca-7,11-dien-13-one

Details

• Internal ID: fd6e5c5b-79d1-4113-99be-21ba4d504b89
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (1S,2R,4R,7E)-12-(hydroxymethyl)-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradeca-7,11-dien-13-one
• SMILES (Canonical): CC1=CCCC2(C(O2)C3C(=C(C(=O)O3)CO)CC1)C
• SMILES (Isomeric): C/C/1=C\CC[C@@]2([C@H](O2)[C@@H]3C(=C(C(=O)O3)CO)CC1)C
• InChI: InChI=1S/C15H20O4/c1-9-4-3-7-15(2)13(19-15)12-10(6-5-9)11(8-16)14(17)18-12/h4,12-13,16H,3,5-8H2,1-2H3/b9-4+/t12-,13+,15+/m0/s1
• InChI Key: VKVLIZXYYIZTGG-KURIVACZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 59.10 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 4
• 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	+	0.9712	97.12%
Caco-2	+	0.8211	82.11%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7586	75.86%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9430	94.30%
OATP1B3 inhibitior	+	0.9591	95.91%
MATE1 inhibitior	-	0.8012	80.12%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.7790	77.90%
P-glycoprotein inhibitior	-	0.8343	83.43%
P-glycoprotein substrate	-	0.8805	88.05%
CYP3A4 substrate	+	0.5521	55.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8703	87.03%
CYP3A4 inhibition	-	0.8326	83.26%
CYP2C9 inhibition	-	0.8640	86.40%
CYP2C19 inhibition	-	0.9148	91.48%
CYP2D6 inhibition	-	0.9293	92.93%
CYP1A2 inhibition	-	0.6171	61.71%
CYP2C8 inhibition	-	0.8021	80.21%
CYP inhibitory promiscuity	-	0.9352	93.52%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4884	48.84%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.8148	81.48%
Skin irritation	+	0.5128	51.28%
Skin corrosion	-	0.9225	92.25%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4839	48.39%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5696	56.96%
skin sensitisation	-	0.8570	85.70%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.4588	45.88%
Acute Oral Toxicity (c)	III	0.5723	57.23%
Estrogen receptor binding	-	0.6959	69.59%
Androgen receptor binding	+	0.5432	54.32%
Thyroid receptor binding	+	0.5165	51.65%
Glucocorticoid receptor binding	+	0.5928	59.28%
Aromatase binding	-	0.8127	81.27%
PPAR gamma	+	0.5445	54.45%
Honey bee toxicity	-	0.9039	90.39%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9320	93.20%

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	94.99%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.38%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.70%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL230	P35354	Cyclooxygenase-2	86.81%	89.63%
CHEMBL2581	P07339	Cathepsin D	86.48%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.80%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.58%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.51%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.31%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	80.11%	94.73%

Plants that contains it

• Pentzia pinnatisecta

Cross-Links

• PubChem: 14466147
• LOTUS: LTS0124119
• wikiData: Q105288116