2-[(5,6-Dihydroxy-2-methyl-4,8,9-trioxobenzo[g]chromen-7-yl)methyl-methylamino]acetic acid

Details

• Internal ID: ff47682f-9785-42d8-8606-90b51715805c
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 2-[(5,6-dihydroxy-2-methyl-4,8,9-trioxobenzo[g]chromen-7-yl)methyl-methylamino]acetic acid
• SMILES (Canonical): CC1=CC(=O)C2=C(O1)C=C3C(=C2O)C(=C(C(=O)C3=O)CN(C)CC(=O)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(O1)C=C3C(=C2O)C(=C(C(=O)C3=O)CN(C)CC(=O)O)O
• InChI: InChI=1S/C18H15NO8/c1-7-3-10(20)14-11(27-7)4-8-13(18(14)26)15(23)9(17(25)16(8)24)5-19(2)6-12(21)22/h3-4,23,26H,5-6H2,1-2H3,(H,21,22)
• InChI Key: UXQPXYXSABKRLE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₅NO₈
• Molecular Weight: 373.30 g/mol
• Exact Mass: 373.07976644 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5378	53.78%
Caco-2	-	0.5177	51.77%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4297	42.97%
OATP2B1 inhibitior	-	0.5656	56.56%
OATP1B1 inhibitior	+	0.8450	84.50%
OATP1B3 inhibitior	+	0.9461	94.61%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7799	77.99%
P-glycoprotein inhibitior	-	0.8261	82.61%
P-glycoprotein substrate	-	0.7871	78.71%
CYP3A4 substrate	+	0.5877	58.77%
CYP2C9 substrate	+	0.6090	60.90%
CYP2D6 substrate	-	0.8498	84.98%
CYP3A4 inhibition	-	0.9582	95.82%
CYP2C9 inhibition	-	0.8122	81.22%
CYP2C19 inhibition	-	0.8234	82.34%
CYP2D6 inhibition	-	0.8928	89.28%
CYP1A2 inhibition	+	0.6547	65.47%
CYP2C8 inhibition	-	0.6499	64.99%
CYP inhibitory promiscuity	-	0.8971	89.71%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5109	51.09%
Eye corrosion	-	0.9857	98.57%
Eye irritation	-	0.8805	88.05%
Skin irritation	-	0.7756	77.56%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.5160	51.60%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8421	84.21%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7366	73.66%
Acute Oral Toxicity (c)	III	0.5450	54.50%
Estrogen receptor binding	+	0.5280	52.80%
Androgen receptor binding	+	0.6961	69.61%
Thyroid receptor binding	-	0.6905	69.05%
Glucocorticoid receptor binding	+	0.6546	65.46%
Aromatase binding	-	0.5421	54.21%
PPAR gamma	+	0.5856	58.56%
Honey bee toxicity	-	0.9160	91.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.8537	85.37%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.95%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.97%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.93%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	93.37%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.03%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.37%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.26%	95.64%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.18%	95.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.78%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.70%	90.71%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.44%	89.34%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	85.18%	94.42%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.75%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.76%	99.23%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.45%	96.21%

Plants that contains it

• Digitalis chalcantha
• Forsythia suspensa
• Incarvillea delavayi
• Millingtonia hortensis
• Sesamum alatum

Cross-Links

• PubChem: 53483341
• LOTUS: LTS0053836
• wikiData: Q27155115