MiMeDB: Showing metabocard for Nicrophorusamide A (MMDBc0022468)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 12:35:13 UTC

Update Date

2025-10-07 16:07:11 UTC

Metabolite ID

MMDBc0022468

Metabolite Identification

Common Name

Nicrophorusamide A

Description

Nicrophorusamide A is a member of the class of natural products known as amides. Its chemical structure features a unique arrangement of functional groups that contribute to its bioactivity, specifically its antibacterial properties against several Gram-positive bacteria (PMID:29112406 ). The compound has been synthesized through various methods, including the asymmetric synthesis of Fmoc-threo-HOAsn, which plays a crucial role in its total synthesis (PMID:40126535 ). Additionally, the application of the Passerini reaction product Fmoc-protected HOAsn has facilitated the development of Fmoc-solid phase peptide synthesis (Fmoc-SPPS) towards nicrophorusamide A and its analogues, enabling systematic structure-activity relationship (SAR) studies (PMID:40126535 ). The total synthesis of nicrophorusamide A has also led to a structural disproof of the proposed Noursamycin A, highlighting the importance of accurate structural elucidation in the field of natural product chemistry (PMID:37959861 ). Overall, nicrophorusamide A exemplifies the intricate interplay between synthetic chemistry and biological activity, paving the way for further exploration of its potential applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152114352D          

 63 65  0  0  1  0            999 V2000
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M  END


  Mrv1652305152114352D          

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M  END
> <DATABASE_ID>
MMDBc0022468

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](C)(CC)[C@]1([H])N=C(O)[C@@]([H])(CC(C)C)N=C(O)[C@]([H])(N=C(O)[C@]([H])(CC2=CNC3=C2C=C(Cl)C=C3)N=C(O)[C@]([H])(N=C(O)[C@]([H])(CCCN)N=C1O)[C@@]([H])(O)C(O)=N)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C37H56ClN9O8/c1-7-19(6)28-36(54)42-24(9-8-12-39)32(50)47-29(30(48)31(40)49)37(55)44-26(14-20-16-41-23-11-10-21(38)15-22(20)23)34(52)45-27(18(4)5)35(53)43-25(13-17(2)3)33(51)46-28/h10-11,15-19,24-30,41,48H,7-9,12-14,39H2,1-6H3,(H2,40,49)(H,42,54)(H,43,53)(H,44,55)(H,45,52)(H,46,51)(H,47,50)/t19-,24+,25-,26+,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
CUXAULQHGRSWLF-BSCGVUNJSA-N

> <FORMULA>
C37H56ClN9O8

> <MOLECULAR_WEIGHT>
790.36

> <EXACT_MASS>
789.3940375

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
82.39130558004243

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2R,5S,8R,11R,14S,17S)-17-(3-aminopropyl)-14-[(2R)-butan-2-yl]-5-[(5-chloro-1H-indol-3-yl)methyl]-3,6,9,12,15,18-hexahydroxy-11-(2-methylpropyl)-8-(propan-2-yl)-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl]-2-hydroxyethanimidic acid

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.9895674143133553

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.126051497267584

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.614594104519093

> <JCHEM_PKA_STRONGEST_BASIC>
10.205223511081876

> <JCHEM_POLAR_SURFACE_AREA>
301.65999999999997

> <JCHEM_REFRACTIVITY>
216.5343000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2R,5S,8R,11R,14S,17S)-17-(3-aminopropyl)-14-[(2R)-butan-2-yl]-5-[(5-chloro-1H-indol-3-yl)methyl]-3,6,9,12,15,18-hexahydroxy-8-isopropyl-11-(2-methylpropyl)-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl]-2-hydroxyethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -12.522  -5.067   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.125 -10.606   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.571  -7.997   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.087 -12.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.624 -13.351   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.461  -2.778   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.016  -5.387   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.357   0.015   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.388  -1.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.612 -12.574   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.278 -13.344   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.833   1.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.588  -9.781   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.004  -9.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.278 -10.264   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.425 -11.804   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -11.095  -9.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.593 -12.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.986  -4.243   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.480 -10.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.612 -11.034   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.945 -11.034   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.945 -12.574   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.912  -2.595   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.558  -8.637   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.502  -8.773   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.069 -10.742   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.479  -4.563   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.423  -4.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.393  -3.555   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.113  -3.875   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.406  -2.915   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.034  -7.172   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.533  -9.918   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.576 -10.422   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.449  -3.419   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.947  -6.164   0.000  0.00  0.00           C+0
HETATM   38 Cl   UNK     0       5.946 -10.264   0.000  0.00  0.00          Cl+0
HETATM   39  N   UNK     0      -3.803   2.624   0.000  0.00  0.00           N+0
HETATM   40  N   UNK     0       2.144  -2.731   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0       0.480 -13.050   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      -5.942  -3.739   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      -7.052  -8.957   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      -1.978  -7.309   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0      -4.039  -9.597   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      -8.003  -6.028   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      -2.930  -4.379   0.000  0.00  0.00           N+0
HETATM   48  O   UNK     0      -0.869  -2.090   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       1.589  -5.340   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -2.375  -1.770   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -10.540  -6.852   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -2.057 -11.382   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -7.606 -11.566   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -7.925  -1.954   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.559  -6.484   0.000  0.00  0.00           O+0
HETATM   56  H   UNK     0     -11.492  -3.923   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.881  -1.450   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0      -8.082 -10.102   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.472  -7.629   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.563 -11.062   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      -9.510  -5.708   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.899  -3.235   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.083  -5.020   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   19                                                            
CONECT    7    1   19                                                       
CONECT    8    9   12                                                       
CONECT    9    8   24                                                       
CONECT   10   11   21                                                       
CONECT   11   10   23                                                       
CONECT   12    8   39                                                       
CONECT   13   17   25                                                       
CONECT   14   20   26                                                       
CONECT   15   21   22                                                       
CONECT   16   20   41                                                       
CONECT   17    2    3   13                                                  
CONECT   18    4    5   27                                                  
CONECT   19    6    7   28   56                                             
CONECT   20   14   16   22                                                  
CONECT   21   10   15   38                                                  
CONECT   22   15   20   23                                                  
CONECT   23   11   22   41                                                  
CONECT   24    9   32   42   57                                             
CONECT   25   13   33   43   58                                             
CONECT   26   14   34   44   59                                             
CONECT   27   18   35   45   60                                             
CONECT   28   19   36   46   61                                             
CONECT   29   30   37   47   62                                             
CONECT   30   29   31   48   63                                             
CONECT   31   30   40   49                                                  
CONECT   32   24   47   50                                                  
CONECT   33   25   46   51                                                  
CONECT   34   26   45   52                                                  
CONECT   35   27   43   53                                                  
CONECT   36   28   42   54                                                  
CONECT   37   29   44   55                                                  
CONECT   38   21                                                            
CONECT   39   12                                                            
CONECT   40   31                                                            
CONECT   41   16   23                                                       
CONECT   42   24   36                                                       
CONECT   43   25   35                                                       
CONECT   44   26   37                                                       
CONECT   45   27   34                                                       
CONECT   46   28   33                                                       
CONECT   47   29   32                                                       
CONECT   48   30                                                            
CONECT   49   31                                                            
CONECT   50   32                                                            
CONECT   51   33                                                            
CONECT   52   34                                                            
CONECT   53   35                                                            
CONECT   54   36                                                            
CONECT   55   37                                                            
CONECT   56   19                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

Synonyms

Not Available

Molecular Formula

C₃₇H₅₆ClN₉O₈

Average Mass

790.36

Monoisotopic Mass

789.3940375

IUPAC Name

(2R)-2-[(2R,5S,8R,11R,14S,17S)-17-(3-aminopropyl)-14-[(2R)-butan-2-yl]-5-[(5-chloro-1H-indol-3-yl)methyl]-3,6,9,12,15,18-hexahydroxy-11-(2-methylpropyl)-8-(propan-2-yl)-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl]-2-hydroxyethanimidic acid

Traditional Name

(2R)-2-[(2R,5S,8R,11R,14S,17S)-17-(3-aminopropyl)-14-[(2R)-butan-2-yl]-5-[(5-chloro-1H-indol-3-yl)methyl]-3,6,9,12,15,18-hexahydroxy-8-isopropyl-11-(2-methylpropyl)-1,4,7,10,13,16-hexaazacyclooctadeca-1(18),3,6,9,12,15-hexaen-2-yl]-2-hydroxyethanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CC)[C@]1([H])N=C(O)[C@@]([H])(CC(C)C)N=C(O)[C@]([H])(N=C(O)[C@]([H])(CC2=CNC3=C2C=C(Cl)C=C3)N=C(O)[C@]([H])(N=C(O)[C@]([H])(CCCN)N=C1O)[C@@]([H])(O)C(O)=N)C(C)C

InChI Identifier

InChI=1S/C37H56ClN9O8/c1-7-19(6)28-36(54)42-24(9-8-12-39)32(50)47-29(30(48)31(40)49)37(55)44-26(14-20-16-41-23-11-10-21(38)15-22(20)23)34(52)45-27(18(4)5)35(53)43-25(13-17(2)3)33(51)46-28/h10-11,15-19,24-30,41,48H,7-9,12-14,39H2,1-6H3,(H2,40,49)(H,42,54)(H,43,53)(H,44,55)(H,45,52)(H,46,51)(H,47,50)/t19-,24+,25-,26+,27-,28+,29-,30-/m1/s1

InChI Key

CUXAULQHGRSWLF-BSCGVUNJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
3-alkylindole
Indole or derivatives
Indole
Benzenoid
Substituted pyrrole
Aryl halide
Aryl chloride
Heteroaromatic compound
Cyclic carboximidic acid
Pyrrole
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.033 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.99	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.61	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	301.66 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	216.53 m³·mol⁻¹	ChemAxon
Polarizability	82.39 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

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	385.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	204.1
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	654.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	432.6
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	496.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	139.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1982.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	123.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	245.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	191.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	106.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	155.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	175.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	137.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	166.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	380.4
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1268.5
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	939.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Nicrophorusamide A_TMS_1	CC[C@@H](C)[C@@H]1N=C(O[Si](C)(C)C)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	234.874
Gas Chromatography	Nicrophorusamide A_TMS_2	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O[Si](C)(C)C)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	2773.76
Gas Chromatography	Nicrophorusamide A_TMS_3	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O[Si](C)(C)C)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	1704.72
Gas Chromatography	Nicrophorusamide A_TMS_4	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O[Si](C)(C)C)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	1957.23
Gas Chromatography	Nicrophorusamide A_TMS_5	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O[Si](C)(C)C)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	3640.39
Gas Chromatography	Nicrophorusamide A_TMS_6	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O[Si](C)(C)C	standard non polar	2025-10-23	996.444
Gas Chromatography	Nicrophorusamide A_TMS_7	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O[Si](C)(C)C)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	1240.0
Gas Chromatography	Nicrophorusamide A_TMS_8	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O[Si](C)(C)C)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	1978.75
Gas Chromatography	Nicrophorusamide A_TMS_9	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN[Si](C)(C)C)N=C1O	standard non polar	2025-10-23	2864.82
Gas Chromatography	Nicrophorusamide A_TMS_10	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=CN([Si](C)(C)C)C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	2809.62
Gas Chromatography	Nicrophorusamide A_TMS_11	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(O)=N[Si](C)(C)C)N=C(O)[C@H](CCCN)N=C1O	standard non polar	2025-10-23	1901.62
Gas Chromatography	Nicrophorusamide A_TMS_1	CC[C@@H](C)[C@@H]1N=C(O[Si](C)(C)C)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	2937.02
Gas Chromatography	Nicrophorusamide A_TMS_2	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O[Si](C)(C)C)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	2915.63
Gas Chromatography	Nicrophorusamide A_TMS_3	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O[Si](C)(C)C)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	2533.34
Gas Chromatography	Nicrophorusamide A_TMS_4	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O[Si](C)(C)C)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	3020.96
Gas Chromatography	Nicrophorusamide A_TMS_5	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O[Si](C)(C)C)[C@H](CCCN)N=C1O	standard polar	2025-10-23	3028.26
Gas Chromatography	Nicrophorusamide A_TMS_6	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O[Si](C)(C)C	standard polar	2025-10-23	2777.45
Gas Chromatography	Nicrophorusamide A_TMS_7	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O[Si](C)(C)C)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	2085.05
Gas Chromatography	Nicrophorusamide A_TMS_8	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O[Si](C)(C)C)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	1606.7
Gas Chromatography	Nicrophorusamide A_TMS_9	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN[Si](C)(C)C)N=C1O	standard polar	2025-10-23	-92.5244
Gas Chromatography	Nicrophorusamide A_TMS_10	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=CN([Si](C)(C)C)C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(=N)O)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	3534.31
Gas Chromatography	Nicrophorusamide A_TMS_11	CC[C@@H](C)[C@@H]1N=C(O)[C@@H](CC(C)C)N=C(O)[C@@H](C(C)C)N=C(O)[C@H](CC2=C[NH]C3=CC=C(Cl)C=C23)N=C(O)[C@@H]([C@@H](O)C(O)=N[Si](C)(C)C)N=C(O)[C@H](CCCN)N=C1O	standard polar	2025-10-23	2569.0

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139589852

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Nicrophorusamide A (MMDBc0022468)

MOL for #<Metabolite:0x00007f2e2c76c4b8>

3D MOL for #<Metabolite:0x00007f2e2c76c4b8>

3D SDF for #<Metabolite:0x00007f2e2c76c4b8>

3D-SDF for #<Metabolite:0x00007f2e2c76c4b8>

PDB for #<Metabolite:0x00007f2e2c76c4b8>

3D PDB for #<Metabolite:0x00007f2e2c76c4b8>

SMILES for #<Metabolite:0x00007f2e2c76c4b8>

INCHI for #<Metabolite:0x00007f2e2c76c4b8>

Structure for #<Metabolite:0x00007f2e2c76c4b8>

3D Structure for #<Metabolite:0x00007f2e2c76c4b8>