phosphoramidon

AlkaPlorer ID: AK021154

Synonym: '', 'Talopeptin', '(2S)-2-{(2S)-2-{(S)-hydroxy{(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy}phosphorylamino}-4-methylpentanoylamino}-3-(1H-indol-3-yl)propanoic acid (non-preferred name)', 'N-ALPHA-L-RHAMNOPYRANOSYLOXY(HYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN', 'Phosphoramidon', 'N-(N-(((6-deoxy-alpha-L-mannopyranosyl)oxy)hydroxyphosphinyl)-L-leucyl)-L-tryptophan', 'phosphoramidon'

IUPAC Name: (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

Structure

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](CC1=CNC2=CC=CC=C12)C(=O)O

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InChI: InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18-,19+,20+,23-/m0/s1

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InChIKey: ZPHBZEQOLSRPAK-XLCYBJAPSA-N

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Properties Information

Molecule Weight: 543.5100000000002

TPSA: 214.16

MolLogP: 1.0689000000000004

Number of H-Donors: 8

Number of H-Acceptors: 8

RingCount: 3

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus thermoproteolyticus Thermolysin IC50 33.0 nM 10.1021/jm00012a011
Bacillus thermoproteolyticus Thermolysin Ki 28.0 nM 10.1021/jm00088a002
Bacillus thermoproteolyticus Thermolysin Log Kd -7.56 None 10.1021/jm0105833
Bos taurus Endothelin-converting enzyme 1 IC50 3100.0 nM 10.1016/S0960-894X(01)80341-3
Homo sapiens Endothelin-converting enzyme 1 IC50 0.8 nM 10.1021/jm00012a011
Homo sapiens Endothelin-converting enzyme 1 IC50 17.0 nM 10.1016/j.bmcl.2009.06.064
Homo sapiens Endothelin-converting enzyme 1 IC50 100.0 nM 10.1016/0960-894X(96)00211-9
Homo sapiens Endothelin-converting enzyme 1 IC50 500.0 nM 10.1016/0960-894X(96)00297-1
Homo sapiens Endothelin-converting enzyme 1 IC50 800.0 nM 10.1016/0960-894X(96)00227-2
Homo sapiens Endothelin-converting enzyme 1 IC50 800.0 nM 10.1021/jm040857x
Homo sapiens Endothelin-converting enzyme 1 IC50 1200.0 nM 10.1016/S0960-894X(97)00159-5
Homo sapiens Endothelin-converting enzyme 1 IC50 1200.0 nM 10.1021/jm9010803
Homo sapiens Endothelin-converting enzyme 1 IC50 1200.0 nM 10.1021/jm970787c
Homo sapiens Endothelin-converting enzyme 1 IC50 1200.0 nM 10.1021/jm990507o
Homo sapiens Endothelin-converting enzyme 1 IC50 2000.0 nM 10.1021/jm00053a023
Homo sapiens Endothelin-converting enzyme 1 IC50 4000.0 nM 10.1016/S0960-894X(01)80994-X
Homo sapiens Endothelin-converting enzyme 1 Inhibition 47.0 % 10.1016/S0960-894X(97)00159-5
Homo sapiens Endothelin-converting enzyme 1 Inhibition 47.0 % 10.1021/jm990507o
Homo sapiens Neprilysin IC50 2.0 nM 10.1016/j.bmc.2011.08.064
Homo sapiens Neprilysin IC50 30.0 nM 10.1016/S0960-894X(97)00159-5
Homo sapiens Neprilysin IC50 30.0 nM 10.1021/jm9010803
Homo sapiens Neprilysin IC50 30.0 nM 10.1021/jm970787c
Homo sapiens Neprilysin IC50 100.0 nM 10.1021/jm021089h
Oryctolagus cuniculus Neprilysin IC50 0.4 nM 10.1021/jm00132a005
Oryctolagus cuniculus Neprilysin IC50 2.0 nM 10.1021/jm00012a011
Oryctolagus cuniculus Neprilysin IC50 6.0 nM 10.1021/jm00012a011
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Pseudolysin Ki 57.0 nM 10.1021/acs.jmedchem.5b01698
Rattus norvegicus Neprilysin IC50 0.6 nM 10.1021/jm00132a005
Rattus norvegicus Neprilysin IC50 4.2 nM 10.1016/0960-894X(96)00211-9
Rattus norvegicus Neprilysin IC50 4.2 nM 10.1016/S0960-894X(01)80341-3
Rattus norvegicus Neprilysin IC50 26.0 nM 10.1021/jm00026a009
Rattus norvegicus Neprilysin IC50 27.0 nM 10.1021/jm00030a009
Rattus norvegicus Neprilysin IC50 30.0 nM 10.1021/jm990507o
Rattus norvegicus Neprilysin IC50 34.0 nM 10.1021/acs.jmedchem.0c00441
Rattus norvegicus Neprilysin IC50 200.0 nM 10.1021/jm021089h
Rattus norvegicus Neprilysin Ki 4.0 nM 10.1021/jm00147a015
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 2.55 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.11 % 10.6019/CHEMBL4495565
None Unchecked IC50 600.0 nM 10.1021/np0500631
None Unchecked IC50 2100.0 nM 10.1021/jm701575k
None Unchecked IC50 7630.0 nM 10.1016/j.bmcl.2009.12.059
None Unchecked IC50 13800.0 nM 10.1016/j.bmcl.2007.09.084
None Unchecked IC50 20000.0 nM 10.1016/j.ejmech.2019.111812
None Unchecked IC50 78000.0 nM 10.1021/acs.jmedchem.0c00441
None Unchecked Inhibition 78.0 % 10.1016/j.ejmech.2019.111812
None Unchecked Ki 6980.0 nM 10.1016/j.bmcl.2007.09.084
None Unchecked Ratio 1.4 None 10.1016/S0960-894X(01)80341-3
None Unchecked Selectivity 0.025 None 10.1021/jm970787c
None Unchecked Selectivity 0.025 None 10.1021/jm990507o

Metabolism Information