Barbacenic acid

Details

• Internal ID: b8b1c501-14cb-474f-9984-2a282acf94f1
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: 2-[(3aS,5aS,6R,9aR,9bS)-3a-hydroxy-6,9a,9b-trimethyl-3,7-dioxo-2,4,5,5a,8,9-hexahydro-1H-cyclopenta[a]naphthalen-6-yl]acetic acid
• InChI: InChI=1S/C18H26O5/c1-15(10-14(21)22)11-4-9-18(23)13(20)6-8-17(18,3)16(11,2)7-5-12(15)19/h11,23H,4-10H2,1-3H3,(H,21,22)/t11-,15-,16-,17+,18-/m1/s1
• InChI Key: PUZKHWFCLGKPQB-VGLCKJCNSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.40 g/mol
• Exact Mass: 322.17802393 g/mol
• Topological Polar Surface Area (TPSA): 91.70 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 2-[(3aS,5aS,6R,9aR,9bS)-3a-hydroxy-6,9a,9b-trimethyl-3,7-dioxo-2,4,5,5a,8,9-hexahydro-1H-cyclopenta[a]naphthalen-6-yl]acetic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9734	97.34%
Caco-2	+	0.7768	77.68%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8324	83.24%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.9175	91.75%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7997	79.97%
P-glycoprotein inhibitior	-	0.8887	88.87%
P-glycoprotein substrate	-	0.8978	89.78%
CYP3A4 substrate	+	0.5556	55.56%
CYP2C9 substrate	-	0.8300	83.00%
CYP2D6 substrate	-	0.8722	87.22%
CYP3A4 inhibition	-	0.8114	81.14%
CYP2C9 inhibition	-	0.9584	95.84%
CYP2C19 inhibition	-	0.9398	93.98%
CYP2D6 inhibition	-	0.9759	97.59%
CYP1A2 inhibition	-	0.8971	89.71%
CYP2C8 inhibition	-	0.8333	83.33%
CYP inhibitory promiscuity	-	0.9753	97.53%
UGT catelyzed	-	0.5638	56.38%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7463	74.63%
Eye corrosion	-	0.9952	99.52%
Eye irritation	-	0.9210	92.10%
Skin irritation	+	0.7461	74.61%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	-	0.8254	82.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6028	60.28%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5026	50.26%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7459	74.59%
Acute Oral Toxicity (c)	III	0.6236	62.36%
Estrogen receptor binding	+	0.8384	83.84%
Androgen receptor binding	+	0.6878	68.78%
Thyroid receptor binding	+	0.5350	53.50%
Glucocorticoid receptor binding	+	0.7115	71.15%
Aromatase binding	+	0.5963	59.63%
PPAR gamma	+	0.5230	52.30%
Honey bee toxicity	-	0.9452	94.52%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9857	98.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	93.55%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.76%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.47%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.27%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.11%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.10%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.55%	82.69%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.08%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.57%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.34%	91.19%

Plants that contains it

• Barbacenia flava

Cross-Links

• PubChem: 11151421
• LOTUS: LTS0050819
• wikiData: Q105215355