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

Details

• Internal ID: 0d958d03-e16a-4f0d-b311-df9f8724fa62
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones > Naphthopyranone glycosides
• IUPAC Name: 2-[(1R,3S,4aS,10aS)-9,10a-dihydroxy-5,10-dioxo-1-propyl-1,3,4,4a-tetrahydrobenzo[g]isochromen-3-yl]acetic acid
• InChI: InChI=1S/C18H20O7/c1-2-4-13-18(24)11(7-9(25-13)8-14(20)21)16(22)10-5-3-6-12(19)15(10)17(18)23/h3,5-6,9,11,13,19,24H,2,4,7-8H2,1H3,(H,20,21)/t9-,11+,13+,18-/m0/s1
• InChI Key: LYPPSIGDDZKHMA-ZLXWJRTRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₇
• Molecular Weight: 348.30 g/mol
• Exact Mass: 348.12090297 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 6
• 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	+	0.9268	92.68%
Caco-2	-	0.5715	57.15%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7944	79.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8865	88.65%
OATP1B3 inhibitior	+	0.9056	90.56%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8350	83.50%
P-glycoprotein inhibitior	-	0.8317	83.17%
P-glycoprotein substrate	-	0.5123	51.23%
CYP3A4 substrate	+	0.5748	57.48%
CYP2C9 substrate	+	0.6258	62.58%
CYP2D6 substrate	-	0.8762	87.62%
CYP3A4 inhibition	-	0.7881	78.81%
CYP2C9 inhibition	-	0.8831	88.31%
CYP2C19 inhibition	-	0.8652	86.52%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.7095	70.95%
CYP2C8 inhibition	-	0.6110	61.10%
CYP inhibitory promiscuity	-	0.9634	96.34%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6053	60.53%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8658	86.58%
Skin irritation	-	0.6488	64.88%
Skin corrosion	-	0.8827	88.27%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6778	67.78%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5858	58.58%
skin sensitisation	-	0.8577	85.77%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.5532	55.32%
Acute Oral Toxicity (c)	III	0.4768	47.68%
Estrogen receptor binding	+	0.6972	69.72%
Androgen receptor binding	+	0.5854	58.54%
Thyroid receptor binding	-	0.5522	55.22%
Glucocorticoid receptor binding	+	0.7825	78.25%
Aromatase binding	-	0.5806	58.06%
PPAR gamma	+	0.6162	61.62%
Honey bee toxicity	-	0.9473	94.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9384	93.84%

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	97.09%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.30%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.19%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.95%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.93%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.54%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.33%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.22%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.00%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.65%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 73355114
• LOTUS: LTS0255636
• wikiData: Q105159472