2-[(1R,3S)-9,10a-dihydroxy-4a-(hydroxymethyl)-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid

Details

• Internal ID: 099a131b-50dd-4607-9104-20a815bbf3ca
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
• IUPAC Name: 2-[(1R,3S)-9,10a-dihydroxy-4a-(hydroxymethyl)-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
• InChI: InChI=1S/C19H22O8/c1-2-4-13-19(26)17(25)15-11(5-3-6-12(15)21)16(24)18(19,9-20)8-10(27-13)7-14(22)23/h3,5-6,10,13,20-21,26H,2,4,7-9H2,1H3,(H,22,23)/t10-,13-,18?,19?/m1/s1
• InChI Key: GOXSXIAIEMOZQK-ZDHMDEHUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₈
• Molecular Weight: 378.40 g/mol
• Exact Mass: 378.13146766 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8384	83.84%
Caco-2	-	0.6995	69.95%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7013	70.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8849	88.49%
OATP1B3 inhibitior	+	0.9113	91.13%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.7373	73.73%
P-glycoprotein inhibitior	-	0.8464	84.64%
P-glycoprotein substrate	+	0.5556	55.56%
CYP3A4 substrate	+	0.5936	59.36%
CYP2C9 substrate	-	0.7985	79.85%
CYP2D6 substrate	-	0.8831	88.31%
CYP3A4 inhibition	-	0.6704	67.04%
CYP2C9 inhibition	-	0.8538	85.38%
CYP2C19 inhibition	-	0.8554	85.54%
CYP2D6 inhibition	-	0.9364	93.64%
CYP1A2 inhibition	-	0.7384	73.84%
CYP2C8 inhibition	-	0.5846	58.46%
CYP inhibitory promiscuity	-	0.9317	93.17%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6755	67.55%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8644	86.44%
Skin irritation	-	0.7384	73.84%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6614	66.14%
Micronuclear	-	0.7926	79.26%
Hepatotoxicity	+	0.5399	53.99%
skin sensitisation	-	0.8911	89.11%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6324	63.24%
Acute Oral Toxicity (c)	III	0.5946	59.46%
Estrogen receptor binding	+	0.7617	76.17%
Androgen receptor binding	+	0.6036	60.36%
Thyroid receptor binding	+	0.5181	51.81%
Glucocorticoid receptor binding	+	0.7266	72.66%
Aromatase binding	+	0.5375	53.75%
PPAR gamma	+	0.6255	62.55%
Honey bee toxicity	-	0.9522	95.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8524	85.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.61%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.89%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.95%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.99%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.81%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.31%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.96%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.31%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	84.53%	91.49%
CHEMBL4208	P20618	Proteasome component C5	83.06%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	81.95%	94.73%
CHEMBL1907	P15144	Aminopeptidase N	81.09%	93.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.82%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162820945
• LOTUS: LTS0252291
• wikiData: Q105014693