Urospermal

Details

• Internal ID: 94040219-a58c-427b-b291-79812b68d9b3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aR,4S,6E,10Z,11aR)-4-hydroxy-10-(hydroxymethyl)-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-6-carbaldehyde
• SMILES (Canonical): C=C1C2C(CC(=CCCC(=CC2OC1=O)CO)C=O)O
• SMILES (Isomeric): C=C1[C@@H]2[C@H](C/C(=C\CC/C(=C/[C@H]2OC1=O)/CO)/C=O)O
• InChI: InChI=1S/C15H18O5/c1-9-14-12(18)5-10(7-16)3-2-4-11(8-17)6-13(14)20-15(9)19/h3,6-7,12-14,17-18H,1-2,4-5,8H2/b10-3+,11-6-/t12-,13+,14+/m0/s1
• InChI Key: CVISOHZWXIVDFN-SLQKEEQISA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.67
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 28400-14-8
• MEGxp0_001678
• AKOS040735143
• NCGC00385803-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9567	95.67%
Caco-2	-	0.5416	54.16%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7582	75.82%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8811	88.11%
OATP1B3 inhibitior	+	0.9641	96.41%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7363	73.63%
BSEP inhibitior	-	0.9427	94.27%
P-glycoprotein inhibitior	-	0.8831	88.31%
P-glycoprotein substrate	-	0.8172	81.72%
CYP3A4 substrate	+	0.5189	51.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8491	84.91%
CYP3A4 inhibition	-	0.8607	86.07%
CYP2C9 inhibition	-	0.9185	91.85%
CYP2C19 inhibition	-	0.8853	88.53%
CYP2D6 inhibition	-	0.9107	91.07%
CYP1A2 inhibition	-	0.8074	80.74%
CYP2C8 inhibition	-	0.8082	80.82%
CYP inhibitory promiscuity	-	0.9603	96.03%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6892	68.92%
Eye corrosion	-	0.9558	95.58%
Eye irritation	-	0.6312	63.12%
Skin irritation	-	0.7211	72.11%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7233	72.33%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5551	55.51%
skin sensitisation	-	0.8834	88.34%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5875	58.75%
Acute Oral Toxicity (c)	III	0.5114	51.14%
Estrogen receptor binding	+	0.5563	55.63%
Androgen receptor binding	-	0.6081	60.81%
Thyroid receptor binding	-	0.6648	66.48%
Glucocorticoid receptor binding	+	0.7382	73.82%
Aromatase binding	-	0.6642	66.42%
PPAR gamma	-	0.5141	51.41%
Honey bee toxicity	-	0.8295	82.95%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8837	88.37%

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	95.85%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.64%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.61%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.50%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.41%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.32%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.61%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.96%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.81%	96.09%

Plants that contains it

• Anisopappus pinnatifida
• Dicoma tomentosa
• Urospermum picroides

Cross-Links

• PubChem: 14287067
• LOTUS: LTS0089181
• wikiData: Q104402905