(4R)-4-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-alpha-L-arabino-hexopyranosyl]oxy}valeric acid

Details

• Internal ID: c4602493-7342-4158-b404-e196d21ea107
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indolecarboxylic acids and derivatives
• IUPAC Name: (4R)-4-[(2R,3R,5R,6S)-3-hydroxy-5-(1H-indole-3-carbonyloxy)-6-methyloxan-2-yl]oxypentanoic acid
• SMILES (Canonical): CC1C(CC(C(O1)OC(C)CCC(=O)O)O)OC(=O)C2=CNC3=CC=CC=C32
• SMILES (Isomeric): C[C@H]1[C@@H](C[C@H]([C@@H](O1)O[C@H](C)CCC(=O)O)O)OC(=O)C2=CNC3=CC=CC=C32
• InChI: InChI=1S/C20H25NO7/c1-11(7-8-18(23)24)26-20-16(22)9-17(12(2)27-20)28-19(25)14-10-21-15-6-4-3-5-13(14)15/h3-6,10-12,16-17,20-22H,7-9H2,1-2H3,(H,23,24)/t11-,12+,16-,17-,20-/m1/s1
• InChI Key: GIZBXORWWXIWKX-VEZRURDRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅NO₇
• Molecular Weight: 391.40 g/mol
• Exact Mass: 391.16310214 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 1173933-40-8
• (4R)-4-[[3,6-Dideoxy-4-O-(1H-indol-3-ylcarbonyl)-alpha-L-arabino-hexopyranosyl]oxy]pentanoic acid
• (4R)-4-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-alpha-L-arabino-hexopyranosyl]oxy}pentanoic acid
• CHEBI:79028
• DTXSID401119218
• Q27148102
• (R)-4-[4-O-(1H-Indole-3-ylcarbonyl)-3,6-dideoxy-alpha-L-altropyranosyloxy]pentanoic acid
• (4R)-4-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-alpha-L-arabino-hexopyranosyl]oxy}valeric acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9503	95.03%
Caco-2	-	0.6897	68.97%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6097	60.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8856	88.56%
OATP1B3 inhibitior	+	0.8874	88.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7904	79.04%
P-glycoprotein inhibitior	-	0.5442	54.42%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6949	69.49%
CYP2C9 substrate	+	0.6052	60.52%
CYP2D6 substrate	-	0.8821	88.21%
CYP3A4 inhibition	-	0.7863	78.63%
CYP2C9 inhibition	-	0.9305	93.05%
CYP2C19 inhibition	-	0.8654	86.54%
CYP2D6 inhibition	-	0.9076	90.76%
CYP1A2 inhibition	-	0.6325	63.25%
CYP2C8 inhibition	-	0.6169	61.69%
CYP inhibitory promiscuity	-	0.8548	85.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5254	52.54%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9248	92.48%
Skin irritation	-	0.8047	80.47%
Skin corrosion	-	0.9345	93.45%
Ames mutagenesis	-	0.7078	70.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4594	45.94%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.5306	53.06%
skin sensitisation	-	0.8959	89.59%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.9172	91.72%
Acute Oral Toxicity (c)	III	0.6359	63.59%
Estrogen receptor binding	+	0.6967	69.67%
Androgen receptor binding	-	0.5511	55.11%
Thyroid receptor binding	+	0.6857	68.57%
Glucocorticoid receptor binding	+	0.5718	57.18%
Aromatase binding	-	0.6100	61.00%
PPAR gamma	+	0.6352	63.52%
Honey bee toxicity	-	0.8540	85.40%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.8055	80.55%
Fish aquatic toxicity	+	0.7522	75.22%

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	99.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.71%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.57%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	94.82%	97.79%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.86%	94.62%
CHEMBL221	P23219	Cyclooxygenase-1	92.67%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.63%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.76%	94.08%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	89.47%	94.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.12%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.62%	85.14%
CHEMBL3310	Q96DB2	Histone deacetylase 11	87.78%	88.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.97%	97.36%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.83%	92.67%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	85.30%	83.00%
CHEMBL3401	O75469	Pregnane X receptor	84.93%	94.73%
CHEMBL213	P08588	Beta-1 adrenergic receptor	84.54%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.65%	89.00%
CHEMBL5028	O14672	ADAM10	83.57%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.35%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.19%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.99%	96.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.73%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.89%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.60%	97.25%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.15%	95.50%

Plants that contains it

• Trigonostemon howii

Cross-Links

• PubChem: 44205804
• NPASS: NPC259233
• LOTUS: LTS0008568
• wikiData: Q27148102