NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid (NP0285830)

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Record Information

Version

2.0

Created at

2022-09-09 14:10:05 UTC

Updated at

2022-09-09 14:10:05 UTC

NP-MRD ID

NP0285830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid

Description

Phebestin belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. (2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid was first documented in 2003 (PMID: 12751795). Based on a literature review very few articles have been published on Phebestin (PMID: 17786278).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092216102D          

 32 33  0  0  1  0            999 V2000
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    9.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
   -1.0243   -2.9084   -0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -2.0611   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744   -2.1734    1.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1202   -0.6656   -0.5171 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7617    0.2564    0.1397 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    0.9466   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8992    0.8488   -1.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930    1.8523    0.4462 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0232    1.8254    1.7853 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    1.3978    0.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6050    2.3606    1.4064 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214    1.2779   -0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    0.8278   -0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0234    1.7584   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3027    1.3068   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5949   -0.0446    0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5626   -0.9251   -0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2685   -0.5264   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058   -0.1634   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8847    1.1136   -0.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817   -0.9366    0.1655 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7390   -0.4412    0.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4589   -0.3900   -0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8209    0.1135   -0.7865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8624   -0.7463   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1626   -0.3081   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3789    1.0520   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3461    1.9533   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0616    1.4644   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4008   -1.2822    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488   -1.0548    1.7792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.4067    1.8694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -3.7704   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204   -2.3174   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8272   -3.3045   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -2.5336   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5377   -2.4250    2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -1.2357    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0912   -3.0044    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1810   -0.6871   -1.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713    0.0034   -2.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4131    2.9161    0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8044    0.8535    1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213    0.4383    1.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    3.2692    0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9788    2.4530    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1451    0.4708   -1.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944    2.2065   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7579    2.8021   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0690    2.0694    0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6124   -0.3474    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7603   -1.9954   -0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4615   -1.2445   -0.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6623    1.9517   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7246    0.6278    0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8732    0.2592   -1.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -1.4090   -1.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6940   -1.8233   -0.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0033   -0.9615   -0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3984    1.4159   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5706    3.0108   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2771    2.2051   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2842   -3.2153    2.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
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 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22 30  1  0
 30 32  1  0
 30 31  2  0
 18 13  1  0
 29 24  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  6
  7 41  1  0
  8 42  1  6
  9 43  1  0
 10 44  1  1
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 17 52  1  0
 18 53  1  0
 20 54  1  0
 22 55  1  1
 23 56  1  0
 23 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 29 62  1  0
 32 63  1  0
M  END


  Mrv1652309092216102D          

 32 33  0  0  1  0            999 V2000
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    9.4875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H](N=C(O)[C@@H](O)[C@H](N)CC1=CC=CC=C1)C(O)=N[C@@H](CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H31N3O5/c1-15(2)20(22(29)26-19(24(31)32)14-17-11-7-4-8-12-17)27-23(30)21(28)18(25)13-16-9-5-3-6-10-16/h3-12,15,18-21,28H,13-14,25H2,1-2H3,(H,26,29)(H,27,30)(H,31,32)/t18-,19+,20+,21+/m1/s1

> <INCHI_KEY>
GGMURINELPSPEF-ANULTFPQSA-N

> <FORMULA>
C24H31N3O5

> <MOLECULAR_WEIGHT>
441.528

> <EXACT_MASS>
441.22637111

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.006247597344306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid

> <JCHEM_LOGP>
0.9282977208360219

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.773174087138217

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1613084512779324

> <JCHEM_PKA_STRONGEST_BASIC>
9.537477452295894

> <JCHEM_POLAR_SURFACE_AREA>
148.73

> <JCHEM_REFRACTIVITY>
120.33160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       9.336  13.090   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003  11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.336   8.470   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  16.170   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       9.336  16.170   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       9.336  17.710   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  18.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003  17.710   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337  18.480   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670  17.710   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.670  16.170   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337  15.400   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  18.480   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  20.020   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668  17.710   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    4   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   22   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl-valyl-phenylalanine	MeSH

Chemical Formula

C₂₄H₃₁N₃O₅

Average Mass

441.5280 Da

Monoisotopic Mass

441.22637 Da

IUPAC Name

(2S)-2-{[(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](N=C(O)[C@@H](O)[C@H](N)CC1=CC=CC=C1)C(O)=N[C@@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C24H31N3O5/c1-15(2)20(22(29)26-19(24(31)32)14-17-11-7-4-8-12-17)27-23(30)21(28)18(25)13-16-9-5-3-6-10-16/h3-12,15,18-21,28H,13-14,25H2,1-2H3,(H,26,29)(H,27,30)(H,31,32)/t18-,19+,20+,21+/m1/s1

InChI Key

GGMURINELPSPEF-ANULTFPQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Alpha-dipeptide
Phenylalanine or derivatives
Valine or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Beta amino acid or derivatives
3-phenylpropanoic-acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Monosaccharide
N-acyl-amine
Fatty acyl
Benzenoid
Secondary alcohol
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Primary aliphatic amine
Alcohol
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.93	ChemAxon
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	148.73 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.33 m³·mol⁻¹	ChemAxon
Polarizability	47.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016297

Chemspider ID

2334271

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3075601

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bank U, Tadje J, Tager M, Wolke C, Bukowska A, Ittenson A, Reinhold D, Helmuth M, Ansorge S, Shakespeare A, Vieth M, Malfertheiner P, Naumann M, Lendeckel U: Inhibition of alanyl-aminopeptidase on CD4+CD25+ regulatory T-cells enhances expression of FoxP3 and TGF-beta1 and ameliorates acute colitis in mice. Int J Mol Med. 2007 Oct;20(4):483-92. [PubMed:17786278 ]
Bukowska A, Tadje J, Arndt M, Wolke C, Kahne T, Bartsch J, Faust J, Neubert K, Hashimoto Y, Lendeckel U: Transcriptional regulation of cytosol and membrane alanyl-aminopeptidase in human T cell subsets. Biol Chem. 2003 Apr;384(4):657-65. doi: 10.1515/BC.2003.073. [PubMed:12751795 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid (NP0285830)

MOL for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

3D MOL for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

3D SDF for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

3D-SDF for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

PDB for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

3D PDB for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

SMILES for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

INCHI for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

Structure for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)

3D Structure for NP0285830 ((2s)-2-{[(2s)-2-{[(2s,3r)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-phenylpropanoic acid)