Pepstatin

Details

• Internal ID: 5b6eca4e-06a1-426c-b40e-0e06862e6fbe
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (3S,4S)-3-hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid
• InChI: InChI=1S/C34H63N5O9/c1-17(2)12-23(37-33(47)31(21(9)10)39-34(48)30(20(7)8)38-27(42)14-19(5)6)25(40)15-28(43)35-22(11)32(46)36-24(13-18(3)4)26(41)16-29(44)45/h17-26,30-31,40-41H,12-16H2,1-11H3,(H,35,43)(H,36,46)(H,37,47)(H,38,42)(H,39,48)(H,44,45)/t22-,23-,24-,25-,26-,30-,31-/m0/s1
• InChI Key: FAXGPCHRFPCXOO-LXTPJMTPSA-N
• Popularity: 12,392 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₆₃N₅O₉
• Molecular Weight: 685.90 g/mol
• Exact Mass: 685.46257860 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 8
• H-Bond Donor: 8
• Rotatable Bonds: 22

Synonyms

• pepstatin
• 26305-03-3
• Pepstatine
• Pepstatina
• Ahpatinin C
• Pepstatinum
• Procidin S 735A
• Pepsin inhibitor S 735A
• DTXSID7046095
• V6Y2T27Q1U
• NSC-272671
• CHEBI:7989
• (3S,4S)-3-hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid
• DTXCID5026095
• N-Isovaleryl-L-valyl-L-valyl-3-hydroxy-6-methyl-gamma-aminoheptanoyl-L-alanyl-3-hydroxy-6-methyl-gamma-aminoheptanoic acid
• NSC272671
• (3S,4S)-3-hydroxy-4-(((2S)-2-(((3S,4S)-3-hydroxy-6-methyl-4-(((2S)-3-methyl-2-(((2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl)amino)butanoyl)amino)heptanoyl)amino)propanoyl)amino)-6-methylheptanoic acid
• RefChem:860129
• 247-600-0
• Pepstatin (nonspecific)
• MFCD00060740
• Pepstatin (VAN)
• CCRIS 3603
• 39324-30-6
• Iva-Val-Val-Sta-Ala-Sta-OH
• MLS002222329
• CHEMBL296588
• (3S,4S)-3-hydroxy-4-[(2S)-2-[(3S,4S)-3-hydroxy-6-methyl-4-[(2S)-3-methyl-2-[(2S)-3-methyl-2-(3-methylbutanamido)butanamido]butanamido]heptanamido]propanamido]-6-methylheptanoic acid
• (6S,9S,12S,13S,17S,20S,21S)-13,21-dihydroxy-12,20-diisobutyl-6,9-diisopropyl-2,17-dimethyl-4,7,10,15,18-pentaoxo-5,8,11,16,19-pentaazatricosan-23-oic acid
• L-Alaninamide,N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-
• NCGC00161670-06
• C34H63N5O9
• 3-hydroxy-4-[2-[[3-hydroxy-6-methyl-4-[[3-methyl-2-[[3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoylamino]-6-methylheptanoic acid
• N-(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-L-alaninamide
• N-(3-methylbutanoyl)-L-valyl-N-[(3S,4S)-1-{[(2S)-1-{[(2S,3S)-1-carboxy-2-hydroxy-5-methylhexan-3-yl]amino}-1-oxopropan-2-yl]amino}-3-hydroxy-6-methyl-1-oxoheptan-4-yl]-L-valinamide
• N-[(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl]-4-amino-3-hydroxy-6-methylheptanoic acid
• SMR000059191
• Pepstatin [USAN:INN]
• Pepstatine [INN-French]
• Pepstatinum [INN-Latin]
• Pepstatina [INN-Spanish]
• UNII-V6Y2T27Q1U
• 1lyb
• 1sme
• 6apr
• N-(3-Methyl-1-oxobutyl)-L-valyl-L-valyl-4-amino-3-hydroxy-6-methylheptanoyl-L-alanyl-4-amino-3-hydroxy-6-methylheptanoic acid
• EINECS 247-600-0
• CAS-26305-03-3
• NSC 272671
• BRN 2201362
• 4er2
• PEPSTATIN [INN]
• PEPSTATIN [MI]
• Pepstatin (USAN/INN)
• PEPSTATIN [USAN]
• Pepstatin A (Synthetic)
• Prestwick3_000405
• Iva-Val-Val-Sta-Ala-Sta
• UPCMLD-DP141
• PEPSTATIN [WHO-DD]
• SCHEMBL50324
• BDBM912
• BSPBio_000330
• BSPBio_001000
• KBioGR_000340
• KBioSS_000340
• MLS000069747
• MLS002207302
• MLS006010748
• BPBio1_000364
• orb1303884
• UPCMLD-DP141:001
• UPCMLD-DP141:002
• IPA-3998-PI
• KBio2_000340
• KBio2_002908
• KBio2_005476
• KBio3_000679
• KBio3_000680
• Bio1_000404
• Bio1_000893
• Bio1_001382
• Bio2_000340
• Bio2_000820
• GLXC-23556
• HMS1362B21
• HMS1792B21
• HMS1990B21
• HMS2096A12
• HMS2233I07
• HMS3403B21
• HMS3713A12
• EX-A4027
• HY-P0018
• IPA-4397
• Pepstatin, from Streptomyces species
• Tox21_111747
• HB3359
• s7381
• Pepstatin A, >=100,000 U/mg
• AKOS024456453
• Tox21_111747_1
• AC-8820
• CCG-207852
• CS-4202
• EBC-616912
• FP29630
• IDI1_002095
• NCGC00160128-02
• NCGC00161670-01
• NCGC00161670-02
• NCGC00161670-03
• NCGC00161670-04
• BS-16753
• DA-76723
• Heptanoic acid, N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-3-hydroxy-6-methyl-4-aminoheptanoyl-L-alanyl-(3S,4S)-3-hydroxy-6-methyl-4-amino-
• L-Alaninamide, N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-[(1S)-1-[(1S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-
• SMR001307268
• SY067712
• Pepstatin A, microbial, >=75% (HPLC)
• Pepstatin A, microbial, >=90% (HPLC)
• AB00513830
• NS00051237
• C74361
• D03818
• Pepstatin A (Purity Higher than 90% by HPLC)
• SR-01000721876
• Q7166509
• SR-01000721876-3
• BRD-K13571841-001-03-7
• BRD-K13571841-001-14-4
• (3S,4S)-3-hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methyl-heptanoic acid
• Isovaleryl-Val-Val-4-amino-3-hydroxy-6-methylheptanoyl-Ala-4-amino-3-hydroxy-6-methylheptanoic Acid
• L-Alaninamide, N-(3-methyl-1-oxobutyl)-L-valyl-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-N-((1S)-1-((1S)-2-carboxy-1-hydroxyethyl)-3-methylbutyl)-
• L-Valinamide, N-(3-methyl-1-oxobutyl)-L-valyl-N-(4-((2-((1-(2-carboxy-1-hydroxyethyl)-3-methylbutyl)amino)-1-methyl-2-oxoethyl)amino)-2-hydroxy-1-(2-methylpropyl)-4-oxobutyl)-, (1S-(1R*,2R*,4(R*(R*(R*)))))-
• N-(3-Methylbutanoyl)-L-valyl-N-[(3S,4S)-1-{[(2S)-1-{[(2S,3S)-1-carboxy-2-hydroxy-5-methyl-3-hexanyl]amino}-1-oxo-2-propanyl]amino}-3-hydroxy-6-methyl-1-oxo-4-heptanyl]-L-valinamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5818	58.18%
Caco-2	-	0.8540	85.40%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7457	74.57%
OATP2B1 inhibitior	-	0.7137	71.37%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5401	54.01%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.5629	56.29%
CYP3A4 substrate	+	0.5119	51.19%
CYP2C9 substrate	+	0.6267	62.67%
CYP2D6 substrate	-	0.8556	85.56%
CYP3A4 inhibition	-	0.8602	86.02%
CYP2C9 inhibition	-	0.9073	90.73%
CYP2C19 inhibition	-	0.9121	91.21%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.9229	92.29%
CYP2C8 inhibition	-	0.9492	94.92%
CYP inhibitory promiscuity	-	0.9751	97.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6592	65.92%
Eye corrosion	-	0.9782	97.82%
Eye irritation	-	0.9096	90.96%
Skin irritation	-	0.8478	84.78%
Skin corrosion	-	0.9780	97.80%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5654	56.54%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.9330	93.30%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	-	0.6531	65.31%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	+	0.5061	50.61%
Acute Oral Toxicity (c)	III	0.6414	64.14%
Estrogen receptor binding	+	0.7317	73.17%
Androgen receptor binding	+	0.5738	57.38%
Thyroid receptor binding	+	0.5410	54.10%
Glucocorticoid receptor binding	+	0.6638	66.38%
Aromatase binding	+	0.6686	66.86%
PPAR gamma	-	0.8545	85.45%
Honey bee toxicity	-	0.9397	93.97%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	-	0.5472	54.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3092	P14091	Cathepsin E	0.08 nM	IC50	via Super-PRED
CHEMBL3837	P07711	Cathepsin L	800 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	89.1 nM	Potency	via Super-PRED
CHEMBL286	P00797	Renin	100 nM	Ki	via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	70.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.55%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	98.67%	83.82%
CHEMBL3776	Q14790	Caspase-8	97.20%	97.06%
CHEMBL221	P23219	Cyclooxygenase-1	97.03%	90.17%
CHEMBL3308	P55212	Caspase-6	95.40%	97.56%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	94.28%	100.00%
CHEMBL3468	P55210	Caspase-7	92.80%	95.68%
CHEMBL4801	P29466	Caspase-1	91.54%	96.85%
CHEMBL230	P35354	Cyclooxygenase-2	90.22%	89.63%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.03%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.54%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.37%	96.47%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.72%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.58%	85.14%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.34%	98.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.58%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.58%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	84.60%	90.20%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.35%	89.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.09%	90.93%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	81.92%	97.23%
CHEMBL332	P03956	Matrix metalloproteinase-1	81.76%	94.50%
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	81.16%	98.33%
CHEMBL2514	O95665	Neurotensin receptor 2	80.28%	100.00%

Plants that contains it

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Cross-Links

• PubChem: 5478883
• LOTUS: LTS0169498
• wikiData: Q7166509