NP-MRD: Showing NP-Card for (2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid (NP0314291)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 12:18:53 UTC

Updated at

2022-09-11 12:18:53 UTC

NP-MRD ID

NP0314291

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid

Description

Rhizocticin D, also known as leu-arg-appa, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Based on a literature review very few articles have been published on Rhizocticin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214182D          

 31 30  0  0  1  0            999 V2000
   -0.3829    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -0.1914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3829   -0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -3.9039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3316   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -2.6664    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.9039    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  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  4  0  0  0
 18 20  2  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 64 63  0  0  0  0  0  0  0  0999 V2000
   -1.5170    4.3324   -1.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8586    5.0769   -1.1221 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    5.2464    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2100    6.2559    0.6216 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3488    4.4633    1.1345 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    3.7953    2.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2508    2.6981    1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201    1.7338    0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    0.5913    0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8939   -0.3338   -0.4753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8322   -0.9864    0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1354   -0.8905    1.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121   -1.9400   -0.6683 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5376   -3.2296   -0.0483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1109   -1.4104   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1563   -2.2926   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9557   -2.5011   -2.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3439   -3.5961   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9435   -0.0590    1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -0.7721    2.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252   -0.0315    0.9801 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    0.6154   -0.0355 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3739    0.9157    0.3333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -0.0720    0.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760   -1.4574    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8390   -2.3101   -0.6421 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.6979   -1.6602   -1.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778   -2.1504   -0.2025 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4319   -3.9277   -0.7898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    0.0084   -1.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4970    0.4816   -2.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181   -1.0666   -1.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1144    6.3979    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946    6.8114    1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    4.4046    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205    3.2901    2.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194    4.5029    2.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8166    3.1746    0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783    2.2177    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    1.2875    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476    2.3100    0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010    1.0591   -0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1585   -1.6937    2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3820   -1.9854   -1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9439   -3.1869    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5121   -3.3929    0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410   -0.4394   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3511   -1.2421    0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1297   -1.7278   -1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5013   -3.4529   -2.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4704   -1.7077   -3.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9110   -2.6438   -2.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6667   -4.4026   -0.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3848   -3.9625   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3276   -3.4779    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956   -0.3377    3.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    1.6271   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7314    1.9711    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2321    0.1414    0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7612   -1.6903    0.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9765   -1.9356    1.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7273   -1.1959   -0.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2617   -4.4425   -0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077   -1.8047   -2.2580 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  9 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 28  1  0
 26 29  1  0
 26 27  2  0
 22 30  1  0
 30 32  1  0
 30 31  2  0
 17 50  1  0
 17 51  1  0
 17 52  1  0
 16 49  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 15 47  1  0
 15 48  1  0
 13 44  1  6
 14 45  1  0
 14 46  1  0
 12 43  1  0
  9 42  1  6
  8 40  1  0
  8 41  1  0
  7 38  1  0
  7 39  1  0
  6 36  1  0
  6 37  1  0
  5 35  1  0
  4 33  1  0
  4 34  1  0
  2  1  1  0
 20 56  1  0
 22 57  1  6
 23 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 28 62  1  0
 29 63  1  0
 32 64  1  0
M  END


  Mrv1652309112214182D          

 31 30  0  0  1  0            999 V2000
   -0.3829    1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -0.1914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3829   -0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -0.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -3.9039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3316   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -2.6664    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -5.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -3.9039    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  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  4  0  0  0
 18 20  2  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314291

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H](N)C(O)=N[C@@H](CCCNC(N)=N)C(O)=N[C@@H](\C=C/CP(O)(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H33N6O7P/c1-10(2)9-11(18)14(24)22-12(5-3-7-21-17(19)20)15(25)23-13(16(26)27)6-4-8-31(28,29)30/h4,6,10-13H,3,5,7-9,18H2,1-2H3,(H,22,24)(H,23,25)(H,26,27)(H4,19,20,21)(H2,28,29,30)/b6-4-/t11-,12-,13-/m0/s1

> <INCHI_KEY>
CJJARRUKCLRYDP-DCRFLDTMSA-N

> <FORMULA>
C17H33N6O7P

> <MOLECULAR_WEIGHT>
464.46

> <EXACT_MASS>
464.214834425

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.037618229789004

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3Z)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid

> <JCHEM_LOGP>
-4.112123666876582

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.2114737059587877

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7303846506541056

> <JCHEM_PKA_STRONGEST_BASIC>
11.942355492072853

> <JCHEM_POLAR_SURFACE_AREA>
247.92999999999995

> <JCHEM_REFRACTIVITY>
124.1377

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3Z)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.715   3.493   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.715   1.953   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.048   1.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.619   1.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.619  -0.357   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.715  -1.127   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.953  -1.127   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.286  -0.357   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       1.953  -2.667   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       8.621  -3.437   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.955  -1.127   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      11.288  -3.437   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.286  -4.977   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.620  -5.747   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       1.953  -5.747   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       1.953  -7.287   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.619  -8.057   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.715  -7.287   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.715  -5.747   0.000  0.00  0.00           C+0
HETATM   25  P   UNK     0      -2.048  -4.977   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      -3.382  -4.207   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.278  -3.644   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.818  -6.311   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.286  -8.057   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.286  -9.597   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.620  -7.287   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   21   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

View in JSmol

Synonyms

Value	Source
Leu-arg-appa	MeSH
Leucyl-arginyl-2-amino-5-phosphono-3-pentenoic acid	MeSH

Chemical Formula

C₁₇H₃₃N₆O₇P

Average Mass

464.4600 Da

Monoisotopic Mass

464.21483 Da

IUPAC Name

(2S,3Z)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid

Traditional Name

(2S,3Z)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H](N)C(O)=N[C@@H](CCCNC(N)=N)C(O)=N[C@@H](\C=C/CP(O)(O)=O)C(O)=O

InChI Identifier

InChI=1S/C17H33N6O7P/c1-10(2)9-11(18)14(24)22-12(5-3-7-21-17(19)20)15(25)23-13(16(26)27)6-4-8-31(28,29)30/h4,6,10-13H,3,5,7-9,18H2,1-2H3,(H,22,24)(H,23,25)(H,26,27)(H4,19,20,21)(H2,28,29,30)/b6-4-/t11-,12-,13-/m0/s1

InChI Key

CJJARRUKCLRYDP-DCRFLDTMSA-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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Unsaturated fatty acid
Fatty acid
Fatty acyl
Organophosphonic acid derivative
Organophosphonic acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Primary aliphatic amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Organophosphorus compound
Primary amine
Organic oxygen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-4.1	ChemAxon
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	11.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	247.93 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	124.14 m³·mol⁻¹	ChemAxon
Polarizability	46.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

58837866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14061807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid (NP0314291)

MOL for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

3D MOL for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

3D SDF for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

3D-SDF for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

PDB for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

3D PDB for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

SMILES for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

INCHI for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

Structure for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)

3D Structure for NP0314291 ((2s,3z)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-5-phosphonopent-3-enoic acid)