Damcinic acid

Details

• Internal ID: db3e24cc-2c84-4530-9190-5c7c118120f9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Pseudoguaianes
• IUPAC Name: 2-[(3aS,5R,8S,8aS)-3a,8-dimethyl-3-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CCC(CC2(C1CCC2=O)C)C(=C)C(=O)O
• SMILES (Isomeric): C[C@H]1CC[C@H](C[C@]2([C@H]1CCC2=O)C)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O3/c1-9-4-5-11(10(2)14(17)18)8-15(3)12(9)6-7-13(15)16/h9,11-12H,2,4-8H2,1,3H3,(H,17,18)/t9-,11+,12-,15-/m0/s1
• InChI Key: CRXWIWHBLVNJSP-LIBKGXAOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.05
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 2-((3aS,5R,8S,8aS)-3a,8-dimethyl-3-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)prop-2-enoic acid
• 2-[(3aS,5R,8S,8aS)-3a,8-dimethyl-3-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoic acid
• RefChem:130841
• CHEMBL2286470
• SCHEMBL19973122

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	+	0.8669	86.69%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7362	73.62%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9363	93.63%
OATP1B3 inhibitior	+	0.9049	90.49%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	-	0.7955	79.55%
P-glycoprotein inhibitior	-	0.8865	88.65%
P-glycoprotein substrate	-	0.8814	88.14%
CYP3A4 substrate	+	0.5459	54.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8928	89.28%
CYP3A4 inhibition	-	0.8863	88.63%
CYP2C9 inhibition	-	0.9023	90.23%
CYP2C19 inhibition	-	0.9076	90.76%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.5477	54.77%
CYP2C8 inhibition	-	0.6551	65.51%
CYP inhibitory promiscuity	-	0.9717	97.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5769	57.69%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.6398	63.98%
Skin irritation	+	0.6274	62.74%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6427	64.27%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	-	0.5574	55.74%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6302	63.02%
Acute Oral Toxicity (c)	III	0.5447	54.47%
Estrogen receptor binding	+	0.7209	72.09%
Androgen receptor binding	-	0.5626	56.26%
Thyroid receptor binding	-	0.6241	62.41%
Glucocorticoid receptor binding	-	0.5209	52.09%
Aromatase binding	+	0.5795	57.95%
PPAR gamma	-	0.5059	50.59%
Honey bee toxicity	-	0.9403	94.03%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	93.11%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.59%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.50%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.56%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.05%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.85%	85.14%
CHEMBL340	P08684	Cytochrome P450 3A4	83.37%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.17%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.03%	92.94%

Plants that contains it

• Ambrosia ambrosioides
• Ambrosia arborescens
• Ambrosia artemisiifolia
• Ambrosia hispida

Cross-Links

• PubChem: 11747064
• LOTUS: LTS0169007
• wikiData: Q104969003