NP-MRD: Showing NP-Card for (2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid (NP0193735)

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Record Information

Version

2.0

Created at

2022-09-04 11:16:21 UTC

Updated at

2022-09-04 11:16:21 UTC

NP-MRD ID

NP0193735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid

Description

Nocardicin D belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. (2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid is found in Apis cerana and Nocardia uniformis. Based on a literature review very few articles have been published on Nocardicin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213162D          

 35 37  0  0  1  0            999 V2000
    9.5841    0.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5841   -0.5834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8696   -0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1551   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4407   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117   -0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    0.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    1.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    1.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    1.8916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    2.7166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2849    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    3.8834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    4.7084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1538    5.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538    5.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394    4.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    5.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    6.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262    6.3584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    5.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    4.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2985   -0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0130   -0.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2985   -1.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  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
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 17 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
  9 31  1  0  0  0  0
 31 32  2  0  0  0  0
  6 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -9.1924   -1.4948   -0.5367 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8874   -0.8263   -0.4165 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7673   -0.2153    0.9567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4351    0.4644    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4212   -0.5220    0.8745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0911   -0.1222    0.9543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    1.1788    1.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196    1.5620    1.3134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    0.6704    1.1119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155    1.1382    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    2.3863    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2099    0.3715    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4482    1.0300    1.1685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235   -0.8702    0.7594 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -1.5828    0.5961 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3964   -1.0574   -0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4379   -1.2355    0.5484 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774   -1.3443    0.4288 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2422   -2.4891   -0.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4569   -2.7869   -0.5537 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3095   -3.2840   -1.0560 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3348   -0.0580   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8495    1.1135    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2085    2.3486   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0545    2.4929   -1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983    3.7587   -1.5976 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5226    1.3290   -1.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1726    0.0663   -1.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774   -1.2506    1.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776   -1.0538    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.6260    0.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0636   -1.0141    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7399    0.2124   -1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6629    0.8074   -1.6360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8258    0.5736   -2.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9160   -0.7566   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3332   -2.0872    0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1293   -1.6262   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8311   -1.0100    1.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5879    0.5154    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3091    1.3710    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3775    0.7706    2.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5568    1.8849    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1541    2.5803    1.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    1.8844    0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3232   -2.6864    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5938   -1.7460   -1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476   -0.0109   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045   -1.4636    1.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6482   -3.8419   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1816    1.0371    1.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194    3.2520    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2350    4.1672   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1870    1.4257   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5588   -0.8148   -1.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -1.3696    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3291   -2.0452    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6840    0.8994   -1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 31  1  0
 31 32  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 18 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  2  0
  2 33  1  0
 33 35  1  0
 33 34  2  0
 32  6  1  0
 29 15  1  0
 28 22  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  6
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
 31 56  1  0
 32 57  1  0
 13 45  1  0
 15 46  1  6
 16 47  1  0
 16 48  1  0
 18 49  1  1
 21 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 27 54  1  0
 28 55  1  0
 35 58  1  0
M  END


  Mrv1652309042213162D          

 35 37  0  0  1  0            999 V2000
    9.5841    0.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5841   -0.5834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8696   -0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1551   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4407   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117   -0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    0.2416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    1.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    1.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    1.8916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    2.7166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2849    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    3.8834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    4.7084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1538    5.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538    5.9459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394    4.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    5.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    6.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262    6.3584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    5.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    4.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2767    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117    0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262    0.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2985   -0.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0130   -0.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2985   -1.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  2  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
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 17 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
  9 31  1  0  0  0  0
 31 32  2  0  0  0  0
  6 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193735

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](CCOC1=CC=C(C=C1)C(=O)C(O)=N[C@H]1CN([C@@H](C(O)=O)C2=CC=C(O)C=C2)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H23N3O9/c24-16(22(31)32)9-10-35-15-7-3-13(4-8-15)19(28)20(29)25-17-11-26(21(17)30)18(23(33)34)12-1-5-14(27)6-2-12/h1-8,16-18,27H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/t16-,17+,18-/m1/s1

> <INCHI_KEY>
QJZHIGKJGFPGRN-FGTMMUONSA-N

> <FORMULA>
C23H23N3O9

> <MOLECULAR_WEIGHT>
485.449

> <EXACT_MASS>
485.143429333

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.93503447538767

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-4-[4-({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid

> <JCHEM_LOGP>
-1.6289181805737243

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.0606076128143673

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.669317204237915

> <JCHEM_PKA_STRONGEST_BASIC>
8.921520871685331

> <JCHEM_POLAR_SURFACE_AREA>
200.04999999999998

> <JCHEM_REFRACTIVITY>
118.5045

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-4-[4-({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  N   UNK     0      17.890   0.451   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      17.890  -1.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.557  -1.859   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.223  -1.089   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.889  -1.859   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.556  -1.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.222  -1.859   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.888  -1.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.888   0.451   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.555   1.221   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.221   0.451   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.555   2.761   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.888   3.531   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       7.221   3.531   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       7.221   5.071   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.132   6.160   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.221   7.249   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.221   8.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.887   9.559   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.887  11.099   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.553   8.789   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.555   9.559   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.555  11.099   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.888  11.869   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.222  11.099   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.556  11.869   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.222   9.559   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.888   8.789   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.310   6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.850   6.160   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.222   1.221   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.556   0.451   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.224  -1.859   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.558  -1.089   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      19.224  -3.399   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   17   15   30                                                  
CONECT   30   29                                                            
CONECT   31    9   32                                                       
CONECT   32   31    6                                                       
CONECT   33    2   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₃N₃O₉

Average Mass

485.4490 Da

Monoisotopic Mass

485.14343 Da

IUPAC Name

(2R)-2-amino-4-[4-({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid

Traditional Name

(2R)-2-amino-4-[4-({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-C-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@H](CCOC1=CC=C(C=C1)C(=O)C(O)=N[C@H]1CN([C@@H](C(O)=O)C2=CC=C(O)C=C2)C1=O)C(O)=O

InChI Identifier

InChI=1S/C23H23N3O9/c24-16(22(31)32)9-10-35-15-7-3-13(4-8-15)19(28)20(29)25-17-11-26(21(17)30)18(23(33)34)12-1-5-14(27)6-2-12/h1-8,16-18,27H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/t16-,17+,18-/m1/s1

InChI Key

QJZHIGKJGFPGRN-FGTMMUONSA-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

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Nocardia uniformis subsp. tsuyamanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Monobactam
N-acyl-alpha amino acid or derivatives
Phenylacetamide
D-alpha-amino acid
Alpha-amino acid or derivatives
Alpha-amino acid
Phenoxy compound
Benzoyl
Phenol ether
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Beta-lactam
Tertiary carboxylic acid amide
Ketone
Amino acid
Azetidine
Carboxamide group
Lactam
Amino acid or derivatives
Secondary carboxylic acid amide
Ether
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monobactam (CHEBI:81023 )

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	-1.6	ChemAxon
pKa (Strongest Acidic)	1.67	ChemAxon
pKa (Strongest Basic)	8.92	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	200.05 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	118.5 m³·mol⁻¹	ChemAxon
Polarizability	47.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2308648

KEGG Compound ID

C17353

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3045997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid (NP0193735)

MOL for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

3D MOL for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

3D SDF for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

3D-SDF for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

PDB for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

3D PDB for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

SMILES for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

INCHI for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

Structure for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)

3D Structure for NP0193735 ((2r)-2-amino-4-[4-({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl}carbonyl)phenoxy]butanoic acid)