Phosphoramidon

HCID 445114

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Basic information

CAS: 36357-77-4
Standard SMILES: CC(C)C[C@H](NP(=O)(O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O
InChIKey: ZPHBZEQOLSRPAK-XLCYBJAPSA-N
Molecular formula: C23H34N3O10P
Average molar mass: 543.5 g/mol
Monoisotopic mass: 543.19818129

Overview

Phosphoramidon is a dipeptide isolated from the cultures of Streptomyces tanashiensis. It has a role as a bacterial metabolite, an EC 3.4.24.11 (neprilysin) inhibitor and an EC 3.4.24.71 (endothelin-converting enzyme 1) inhibitor. It is a deoxyaldohexose phosphate and a dipeptide.

Names & identifiers

Preferred name: Phosphoramidon
IUPAC: (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
English name: PHOSPHORAMIDON
Molecular formula: C23H34N3O10P
Molecular weight: 543.51

Names & synonyms

phosphoramidon36357-77-4T3G94E2LB1DTXSID601317292CHEBI:45353N-(alpha-l-rhamnopyranosyloxyhydroxyphosphinyl)-l-leucyl-l-tryptophanL-Tryptophan, N-(N-(((6-deoxy-alpha-L-mannopyranosyl)oxy)hydroxyphosphinyl)-L-leucyl)-(2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid(2S)-2-(((2S)-2-((hydroxy-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-phosphoryl)amino)-4-methyl-pentanoyl)amino)-3-(1H-indol-3-yl)propanoic acid(2S)-2-(((2S)-2-((hydroxy-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl)amino)-4-methylpentanoyl)amino)-3-(1H-indol-3-yl)propanoic acid(2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phosphoryl]amino]-4-methyl-pentanoyl]amino]-3-(1H-indol-3-yl)propanoic acidRefChem:862372

Show more names

eucyl)-yptophanPHOSPHORAMIDON SODIUM SALTPhosphoramidon (0.5 mg vial)PHOSPHORAMIDON DISODIUM SALT DIHYDRATEZ-Val-Ala-Asp(OMe)-CH2Fv [Z-VAD-FMK] (1mg vial)N-(A-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRPN-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP-OHN-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP 2NA

DTXCID001747112252-996-3PhosphramidonPhosporamidonN-ALPHA-L-RHAMNOPYRANOSYLOXY(HYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHANCHEMBL479579N-(N-(((6-Deoxy-alpha-L-mannopyranosyl)oxy)hydroxyphosphinyl)-L-leucyl)-L-tryptophan(2S)-2-((2S)-2-((Hydroxy(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)amino)-4-methylpentanamido)-3-(1H-indol-3-yl)propanoic acid

Database identifiers

CAS: 36357-77-4
PubChem CID: 445114
DTXSID: DTXSID601317292
ChEMBL: CHEMBL479579
ChEBI: CHEBI:45353
UNII: T3G94E2LB1
EC Number: 252-996-3
Nikkaji: J18.388A

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 211 Å²
Hydrogen bond donors: 8
Hydrogen bond acceptors: 11
Rotatable bonds: 11
Heavy atoms: 37
Formal charge: 0
Complexity: 848

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Density: 1.48 · 1.48±0.1 g/cm3(Predicted)
storage temp.: 20 °C · −20°C
solubility: 2 O: · H2O: 1 mM Stock solution stable for 1 month at –20° C.
pka: -0.66 · -0.66±0.50(Predicted)
FDA UNII: 3 G94E2LB1 · T3G94E2LB1
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
F: 10 · 10-21

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F: 10-21
wgk: 3
safety_code: 22-24/25

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).

Substances that inhibit the growth or reproduction of BACTERIA.

Applications · 1 item

UsesPhosphoramidon, a microbial metabolite, is a specific metalloprotease thermolysin inhibitor with an IC50 of 0.4 μg/mL. Phosphoramidon also inhibits endothelin-converting enzyme (ECE), neutral endopeptidase (NEP), and angiotensin-converting enzyme (ACE) with IC50 values of 3.5, 0.034, and 78 μM, respectively[1][2][3].

Suppliers13 total

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

武汉易泰科技有限公司上海分公司18930552037 · [email protected]

张家港阿拉宁生化技术有限公司512-58900862 400-0707518 · [email protected]

四川库利南科技有限公司400-1166-196 18981987031 · [email protected]

上海谱科生物技术有限公司021-64705760 18027310741 · [email protected]

Additional notes

DefinitionChEBI: A dipeptide isolated from the cultures of Streptomyces tanashiensis.

Related reactions

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Compound notes

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