Ambrosic acid

Details

• Internal ID: d571aeed-9fbf-4a21-bb41-e8230d30daa0
• Taxonomy: Organoheterocyclic compounds > Oxanes
• IUPAC Name: 2-[(1R,5S,7R,8S,10S)-5,10-dimethyl-4-oxo-11-oxatricyclo[6.2.1.01,5]undecan-7-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CC2C(CC3(C1(O2)CCC3=O)C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@H]1C[C@H]2[C@H](C[C@]3([C@@]1(O2)CCC3=O)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H20O4/c1-8-6-11-10(9(2)13(17)18)7-14(3)12(16)4-5-15(8,14)19-11/h8,10-11H,2,4-7H2,1,3H3,(H,17,18)/t8-,10+,11-,14+,15+/m0/s1
• InChI Key: ZONXEWIGPLHXNT-ULEBWITMSA-N
• Popularity: 4 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): 63.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 2.18
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• CHEMBL4473325
• CHEBI:182484
• AKOS040734564
• NCGC00385910-01
• 2-[(1R,5S,7R,8S,10S)-5,10-dimethyl-4-oxo-11-oxatricyclo[6.2.1.01,5]undecan-7-yl]prop-2-enoic acid
• NCGC00385910-01_C15H20O4_1H-3a,6-Epoxyazulene-7-acetic acid, octahydro-4,8a-dimethyl-alpha-methylene-1-oxo-, (3aR,4S,6S,7R,8aS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9621	96.21%
Caco-2	+	0.6402	64.02%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7056	70.56%
OATP2B1 inhibitior	-	0.8524	85.24%
OATP1B1 inhibitior	+	0.9079	90.79%
OATP1B3 inhibitior	+	0.9213	92.13%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	-	0.9309	93.09%
P-glycoprotein inhibitior	-	0.9089	90.89%
P-glycoprotein substrate	-	0.8843	88.43%
CYP3A4 substrate	+	0.5744	57.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8787	87.87%
CYP3A4 inhibition	-	0.7737	77.37%
CYP2C9 inhibition	-	0.9143	91.43%
CYP2C19 inhibition	-	0.9049	90.49%
CYP2D6 inhibition	-	0.9505	95.05%
CYP1A2 inhibition	+	0.6045	60.45%
CYP2C8 inhibition	-	0.8042	80.42%
CYP inhibitory promiscuity	-	0.9677	96.77%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6325	63.25%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.8565	85.65%
Skin irritation	+	0.5728	57.28%
Skin corrosion	-	0.8266	82.66%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7430	74.30%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5835	58.35%
skin sensitisation	-	0.7748	77.48%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5601	56.01%
Acute Oral Toxicity (c)	II	0.5089	50.89%
Estrogen receptor binding	+	0.8031	80.31%
Androgen receptor binding	+	0.5718	57.18%
Thyroid receptor binding	-	0.5624	56.24%
Glucocorticoid receptor binding	+	0.5529	55.29%
Aromatase binding	-	0.5506	55.06%
PPAR gamma	+	0.5783	57.83%
Honey bee toxicity	-	0.8769	87.69%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9913	99.13%

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	96.10%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.80%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.68%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	87.30%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.93%	99.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.80%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	84.37%	91.19%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.12%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.09%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.69%	97.25%

Plants that contains it

• Ambrosia artemisiifolia
• Ambrosia tenuifolia

Cross-Links

• PubChem: 75368818
• LOTUS: LTS0135617
• wikiData: Q105380605