2-(6,8-Dihydroxy-1-oxo-2,3-dihydrocyclopenta[b]chromen-3a-yl)acetic acid

Details

• Internal ID: 533af32f-74a7-4afd-a593-bd375c2f2a60
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans
• IUPAC Name: 2-(6,8-dihydroxy-1-oxo-2,3-dihydrocyclopenta[b]chromen-3a-yl)acetic acid
• SMILES (Canonical): C1CC2(C(=CC3=C(C=C(C=C3O2)O)O)C1=O)CC(=O)O
• SMILES (Isomeric): C1CC2(C(=CC3=C(C=C(C=C3O2)O)O)C1=O)CC(=O)O
• InChI: InChI=1S/C14H12O6/c15-7-3-11(17)8-5-9-10(16)1-2-14(9,6-13(18)19)20-12(8)4-7/h3-5,15,17H,1-2,6H2,(H,18,19)
• InChI Key: HSDRVWVQKLFYDT-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₆
• Molecular Weight: 276.24 g/mol
• Exact Mass: 276.06338810 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9436	94.36%
Caco-2	-	0.5856	58.56%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8187	81.87%
OATP2B1 inhibitior	-	0.7210	72.10%
OATP1B1 inhibitior	+	0.8978	89.78%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8069	80.69%
BSEP inhibitior	-	0.8116	81.16%
P-glycoprotein inhibitior	-	0.9660	96.60%
P-glycoprotein substrate	-	0.8532	85.32%
CYP3A4 substrate	-	0.5156	51.56%
CYP2C9 substrate	-	0.6054	60.54%
CYP2D6 substrate	-	0.8101	81.01%
CYP3A4 inhibition	-	0.5994	59.94%
CYP2C9 inhibition	-	0.7208	72.08%
CYP2C19 inhibition	-	0.6781	67.81%
CYP2D6 inhibition	-	0.8180	81.80%
CYP1A2 inhibition	-	0.6596	65.96%
CYP2C8 inhibition	+	0.4863	48.63%
CYP inhibitory promiscuity	-	0.7018	70.18%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5587	55.87%
Eye corrosion	-	0.9836	98.36%
Eye irritation	+	0.9644	96.44%
Skin irritation	-	0.6721	67.21%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8304	83.04%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5482	54.82%
skin sensitisation	-	0.7563	75.63%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7143	71.43%
Acute Oral Toxicity (c)	III	0.3450	34.50%
Estrogen receptor binding	+	0.6006	60.06%
Androgen receptor binding	-	0.4877	48.77%
Thyroid receptor binding	-	0.6360	63.60%
Glucocorticoid receptor binding	+	0.5763	57.63%
Aromatase binding	-	0.5423	54.23%
PPAR gamma	+	0.7534	75.34%
Honey bee toxicity	-	0.9284	92.84%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9609	96.09%

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	99.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.92%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.07%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.20%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.72%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.17%	86.33%
CHEMBL4208	P20618	Proteasome component C5	89.12%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.99%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.15%	99.15%
CHEMBL236	P41143	Delta opioid receptor	85.87%	99.35%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.52%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.13%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.50%	90.71%

Plants that contains it

• Tapeinidium pinnatum

Cross-Links

• PubChem: 71439803
• LOTUS: LTS0106760
• wikiData: Q105032990