NP-MRD: Showing NP-Card for Nigerloxin (NP0004437)

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Record Information

Version

2.0

Created at

2020-12-09 01:53:59 UTC

Updated at

2021-07-15 16:49:11 UTC

NP-MRD ID

NP0004437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nigerloxin

Provided By

NPAtlas

Description

Nigerloxin belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group. Nigerloxin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Nigerloxin is found in Aspergillus. Nigerloxin was first documented in 2002 (PMID: 12458767). Based on a literature review a small amount of articles have been published on nigerloxin (PMID: 15134145) (PMID: 19504138) (PMID: 22423974) (PMID: 23458199).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118063D          

 34 34  0  0  0  0            999 V2000
    4.5193    0.4757   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.6309   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -0.0930   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.0792   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    0.8843    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.1846    0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.7397    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    1.7209    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    2.7877    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.3856    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -0.5757    1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.1687    0.7865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0118   -1.1854    2.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -1.4169   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771   -2.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -3.6803   -1.0870 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.6336    0.3340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.2455   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -2.2086   -1.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558   -0.1943   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    1.4359   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.0970   -2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3136   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -0.7970   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736    2.9665    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    2.6205   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    2.1379    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    3.7451    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    2.8527    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    2.6366    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713   -0.6764    3.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -4.5021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084   -3.7472   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -3.0550   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18  4  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 13 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 19 34  1  0  0  0  0
M  END

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5193    0.4757   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.6309   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -0.0930   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.0792   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    0.8843    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.1846    0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.7397    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    1.7209    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    2.7877    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.3856    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -0.5757    1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.1687    0.7865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0118   -1.1854    2.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -1.4169   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771   -2.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -3.6803   -1.0870 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.6336    0.3340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.2455   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -2.2086   -1.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558   -0.1943   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    1.4359   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.0970   -2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3136   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -0.7970   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736    2.9665    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    2.6205   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    2.1379    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    3.7451    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    2.8527    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    2.6366    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713   -0.6764    3.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -4.5021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084   -3.7472   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -3.0550   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  2  0
 18 19  1  0
 18  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END


  Mrv1652306242118063D          

 34 34  0  0  0  0            999 V2000
    4.5193    0.4757   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.6309   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -0.0930   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.0792   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    0.8843    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.1846    0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.7397    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    1.7209    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    2.7877    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.3856    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -0.5757    1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.1687    0.7865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0118   -1.1854    2.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -1.4169   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771   -2.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -3.6803   -1.0870 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.6336    0.3340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.2455   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -2.2086   -1.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558   -0.1943   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    1.4359   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.0970   -2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3136   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -0.7970   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736    2.9665    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    2.6205   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    2.1379    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    3.7451    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    2.8527    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    2.6366    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713   -0.6764    3.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -4.5021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084   -3.7472   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -3.0550   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18  4  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  6 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
 13 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 19 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(OC([H])([H])[H])C(=C(\C([H])=C(/[H])C([H])([H])[H])C(O[H])=C1C(=O)N([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO5/c1-4-5-7-6(2)11(19-3)9(13(17)18)8(10(7)15)12(14)16/h4-5,15H,1-3H3,(H2,14,16)(H,17,18)/b5-4+

> <INCHI_KEY>
UOIRNFVLBXIGKH-SNAWJCMRSA-N

> <FORMULA>
C13H15NO5

> <MOLECULAR_WEIGHT>
265.265

> <EXACT_MASS>
265.095022587

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.97363615166209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-carbamoyl-3-hydroxy-6-methoxy-5-methyl-4-[(1E)-prop-1-en-1-yl]benzoic acid

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.3069908829999997

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.710217089794376

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2248794876285745

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6075127976361623

> <JCHEM_POLAR_SURFACE_AREA>
109.85000000000001

> <JCHEM_REFRACTIVITY>
71.2377

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-carbamoyl-3-hydroxy-6-methoxy-5-methyl-4-[(1E)-prop-1-en-1-yl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5193    0.4757   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.6309   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -0.0930   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.0792   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    0.8843    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.1846    0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.7397    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    1.7209    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    2.7877    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.3856    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -0.5757    1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.1687    0.7865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0118   -1.1854    2.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -1.4169   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771   -2.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -3.6803   -1.0870 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.6336    0.3340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.2455   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -2.2086   -1.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558   -0.1943   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    1.4359   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.0970   -2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3136   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -0.7970   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736    2.9665    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    2.6205   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    2.1379    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    3.7451    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    2.8527    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    2.6366    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713   -0.6764    3.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -4.5021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084   -3.7472   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -3.0550   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  2  0
 18 19  1  0
 18  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.519   0.476  -1.633  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.232   0.631  -0.849  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.182  -0.093  -1.135  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.894  -0.079  -0.513  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.417   0.884   0.303  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.081   2.185   0.550  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.835   0.740   0.943  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.336   1.721   1.787  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.141   2.788   1.359  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.583  -0.386   0.738  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.884  -0.576   1.381  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.906  -0.169   0.787  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.012  -1.185   2.614  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.127  -1.417  -0.108  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.977  -2.585  -0.277  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.642  -3.680  -1.087  0.00  0.00           N+0
HETATM   17  O   UNK     0      -3.088  -2.634   0.334  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.093  -1.246  -0.713  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.596  -2.209  -1.548  0.00  0.00           O+0
HETATM   20  H   UNK     0       5.156  -0.194  -1.017  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.048   1.436  -1.722  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.322   0.097  -2.639  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.223   1.314  -0.037  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.356  -0.797  -2.003  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.274   2.966   0.812  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.503   2.620  -0.374  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.744   2.138   1.413  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.787   3.745   1.813  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.219   2.853   0.256  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.172   2.637   1.775  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.271  -0.676   3.463  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.099  -4.502  -0.686  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.908  -3.747  -2.105  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.349  -3.055  -1.885  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3   23                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   25   26   27                                             
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   28   29   30                                             
CONECT   10    7   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   31                                                       
CONECT   14   10   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   32   33                                                  
CONECT   17   15                                                            
CONECT   18   14   19    4                                                  
CONECT   19   18   34                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    6                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    9                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   13                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

RDKit          3D

34 34  0  0  0  0  0  0  0  0999 V2000
    4.5193    0.4757   -1.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320    0.6309   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -0.0930   -1.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8935   -0.0792   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165    0.8843    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0805    2.1846    0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8347    0.7397    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    1.7209    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411    2.7877    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -0.3856    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838   -0.5757    1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.1687    0.7865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0118   -1.1854    2.6135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1273   -1.4169   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771   -2.5849   -0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6423   -3.6803   -1.0870 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0881   -2.6336    0.3340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926   -1.2455   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5959   -2.2086   -1.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1558   -0.1943   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480    1.4359   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220    0.0970   -2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230    1.3136   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3558   -0.7970   -2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2736    2.9665    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5027    2.6205   -0.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    2.1379    1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7869    3.7451    1.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2189    2.8527    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    2.6366    1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2713   -0.6764    3.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0989   -4.5021   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9084   -3.7472   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -3.0550   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  2  0
 18 19  1  0
 18  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 19 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amido-3-hydroxy-6-methoxy-5-methyl-4-(prop-1'-enyl) benzoic acid	MeSH

Chemical Formula

C₁₃H₁₅NO₅

Average Mass

265.2650 Da

Monoisotopic Mass

265.09502 Da

IUPAC Name

2-carbamoyl-3-hydroxy-6-methoxy-5-methyl-4-[(1E)-prop-1-en-1-yl]benzoic acid

Traditional Name

2-carbamoyl-3-hydroxy-6-methoxy-5-methyl-4-[(1E)-prop-1-en-1-yl]benzoic acid

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(\C=C\C)=C(O)C(C(N)=O)=C1C(O)=O

InChI Identifier

InChI=1S/C13H15NO5/c1-4-5-7-6(2)11(19-3)9(13(17)18)8(10(7)15)12(14)16/h4-5,15H,1-3H3,(H2,14,16)(H,17,18)/b5-4+

InChI Key

UOIRNFVLBXIGKH-SNAWJCMRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus	NPAtlas	12458767

Species Where Detected

Species Name	Source	Reference
Aspergillus niger CFR-W-105	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

O-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

O-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Salicylamide
Salicylic acid or derivatives
Benzamide
Benzoic acid
4-alkoxyphenol
P-toluamide
Toluamide
Anisole
Phenoxy compound
Benzoyl
M-cresol
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
Phenol
Toluene
Vinylogous acid
Primary carboxylic acid amide
Carboxamide group
Ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
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	1.97	ALOGPS
logP	2.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.22	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.85 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.24 m³·mol⁻¹	ChemAxon
Polarizability	26.97 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA015913

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015084

Chemspider ID

8553615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

133971

Good Scents ID

Not Available

References

General References

Rao KC, Divakar S, Babu KN, Rao AG, Karanth NG, Sattur AP: Nigerloxin, a novel inhibitor of aldose reductase and lipoxygenase with Free radical scavenging activity from Aspergillus niger CFR-W-105. J Antibiot (Tokyo). 2002 Sep;55(9):789-93. doi: 10.7164/antibiotics.55.789. [PubMed:12458767 ]
Sekhar Rao KC, Appu Rao AG, Sattur AP: A spectroscopic study of the interaction of nigerloxin, a fungal metabolite, with serum albumin. Lipids. 2004 Feb;39(2):173-7. doi: 10.1007/s11745-004-1216-4. [PubMed:15134145 ]
Chakradhar D, Javeed S, Sattur AP: Studies on the production of nigerloxin using agro-industrial residues by solid-state fermentation. J Ind Microbiol Biotechnol. 2009 Sep;36(9):1179-87. doi: 10.1007/s10295-009-0599-7. Epub 2009 Jun 6. [PubMed:19504138 ]
Suresha BS, Sattur AP, Srinivasan K: Beneficial influence of fungal metabolite nigerloxin on eye lens abnormalities in experimental diabetes. Can J Physiol Pharmacol. 2012 Apr;90(4):387-94. doi: 10.1139/y11-135. Epub 2012 Mar 16. [PubMed:22423974 ]
Suresha BS, Vasantha KY, Sattur AP, Srinivasan K: Beneficial influence of fungal metabolite nigerloxin on diabetes-induced oxidative stress in experimental rats. Can J Physiol Pharmacol. 2013 Feb;91(2):149-56. doi: 10.1139/cjpp-2012-0241. Epub 2013 Feb 19. [PubMed:23458199 ]

Showing NP-Card for Nigerloxin (NP0004437)

MOL for NP0004437 (Nigerloxin)

3D MOL for NP0004437 (Nigerloxin)

3D SDF for NP0004437 (Nigerloxin)

3D-SDF for NP0004437 (Nigerloxin)

PDB for NP0004437 (Nigerloxin)

3D PDB for NP0004437 (Nigerloxin)

SMILES for NP0004437 (Nigerloxin)

INCHI for NP0004437 (Nigerloxin)

Structure for NP0004437 (Nigerloxin)

3D Structure for NP0004437 (Nigerloxin)