((4-(4-Amidinophenoxy)butanoyl)aspartyl)valine

Details

• Internal ID: f00b0af2-e2f2-4d77-bdd9-c0562c21d033
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2S)-2-[[(2S)-2-[4-(4-carbamimidoylphenoxy)butanoylamino]-3-carboxypropanoyl]amino]-3-methylbutanoic acid
• SMILES (Canonical): CC(C)C(C(=O)O)NC(=O)C(CC(=O)O)NC(=O)CCCOC1=CC=C(C=C1)C(=N)N
• SMILES (Isomeric): CC(C)[C@@H](C(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)CCCOC1=CC=C(C=C1)C(=N)N
• InChI: InChI=1S/C20H28N4O7/c1-11(2)17(20(29)30)24-19(28)14(10-16(26)27)23-15(25)4-3-9-31-13-7-5-12(6-8-13)18(21)22/h5-8,11,14,17H,3-4,9-10H2,1-2H3,(H3,21,22)(H,23,25)(H,24,28)(H,26,27)(H,29,30)/t14-,17-/m0/s1
• InChI Key: JFCXCBBSUORTNS-YOEHRIQHSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈N₄O₇
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.19579924 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.31
• H-Bond Acceptor: 6
• H-Bond Donor: 6
• Rotatable Bonds: 13

Synonyms

• Dryofragin
• ((4-(4-Amidinophenoxy)butanoyl)aspartyl)valine
• 147865-49-4
• CHEMBL34901
• 9SP2H336UF
• FK633
• FR-144633
• (2S)-2-[[(2S)-2-[4-(4-carbamimidoylphenoxy)butanoylamino]-3-carboxypropanoyl]amino]-3-methylbutanoic acid
• FK 633
• UNII-9SP2H336UF
• SCHEMBL1710973
• DTXSID00163821
• fr144633
• BDBM50092111
• 4-(4-amidinophenoxy)butanoyl-aspartyl-valine
• L-VALINE, N-(N-(4-(4-(AMINOIMINOMETHYL)PHENOXY)-1-OXOBUTYL)-L-.ALPHA.-ASPARTYL)-
• N-(4-(4-(AMINOIMINOMETHYL)PHENOXY)-1-OXOBUTYL)-L-.ALPHA.-ASPARTYL-L-VALINE
• (2S)-2-((2S)-2-(4-(4-CARBAMIMIDOYLPHENOXY)BUTANAMIDO)-3-CARBOXYPROPANAMIDO)-3-METHYLBUTANOIC ACID
• (S)-2-{(S)-2-[4-(4-Carbamimidoyl-phenoxy)-butyrylamino]-3-carboxy-propionylamino}-3-methyl-butyric acid
• 2-{2-[4-(4-Carbamimidoyl-phenoxy)-butyrylamino]-3-carboxy-propionylamino}-3-methyl-butyric acid (FK633)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8790	87.90%
Caco-2	-	0.8977	89.77%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7938	79.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9210	92.10%
OATP1B3 inhibitior	+	0.9407	94.07%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6255	62.55%
P-glycoprotein inhibitior	-	0.4379	43.79%
P-glycoprotein substrate	+	0.6114	61.14%
CYP3A4 substrate	+	0.5578	55.78%
CYP2C9 substrate	+	0.6048	60.48%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.9477	94.77%
CYP2C9 inhibition	-	0.8688	86.88%
CYP2C19 inhibition	-	0.8223	82.23%
CYP2D6 inhibition	-	0.9252	92.52%
CYP1A2 inhibition	-	0.8546	85.46%
CYP2C8 inhibition	+	0.5692	56.92%
CYP inhibitory promiscuity	-	0.9523	95.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.7091	70.91%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9744	97.44%
Skin irritation	-	0.8098	80.98%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6160	61.60%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6197	61.97%
skin sensitisation	-	0.8650	86.50%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6622	66.22%
Acute Oral Toxicity (c)	III	0.6841	68.41%
Estrogen receptor binding	+	0.5551	55.51%
Androgen receptor binding	+	0.6581	65.81%
Thyroid receptor binding	+	0.5147	51.47%
Glucocorticoid receptor binding	+	0.6183	61.83%
Aromatase binding	+	0.5389	53.89%
PPAR gamma	+	0.6391	63.91%
Honey bee toxicity	-	0.9446	94.46%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	-	0.4947	49.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2093869	P05106	Integrin alpha-IIb/beta-3	88 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3060	Q9Y345	Glycine transporter 2	99.21%	99.17%
CHEMBL2581	P07339	Cathepsin D	97.40%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.21%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	95.03%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.93%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.07%	96.00%
CHEMBL4208	P20618	Proteasome component C5	93.78%	90.00%
CHEMBL3776	Q14790	Caspase-8	92.67%	97.06%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	92.12%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	91.80%	90.20%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.42%	90.71%
CHEMBL209	P07477	Trypsin I	90.08%	90.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	89.17%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.92%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.24%	93.56%
CHEMBL4330	Q9NS75	Cysteinyl leukotriene receptor 2	86.96%	98.00%
CHEMBL4444	P04070	Vitamin K-dependent protein C	85.14%	93.89%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	85.03%	89.33%
CHEMBL2535	P11166	Glucose transporter	84.62%	98.75%
CHEMBL3891	P07384	Calpain 1	84.44%	93.04%
CHEMBL1781	P11387	DNA topoisomerase I	82.90%	97.00%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	81.89%	95.48%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.86%	97.86%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.67%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.46%	90.24%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.37%	97.21%
CHEMBL3401	O75469	Pregnane X receptor	80.52%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.49%	99.15%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	80.47%	98.24%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.17%	93.00%

Plants that contains it

• Dryopteris fragrans

Cross-Links

• PubChem: 132814
• LOTUS: LTS0071598
• wikiData: Q83032806