MiMeDB: Showing metabocard for FAICAR (MMDBc0032111)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:02:52 UTC

Update Date

2022-08-31 18:30:38 UTC

MiMeDB ID

MMDBc0032111

Metabolite Identification

Common Name

FAICAR

Description

Phosphoribosyl formamidocarboxamide (FAICAR) is an intermediate in purine metabolism, where it is the byproduct of phosphoribosylaminoimidazolecarboxamide formyltransferase (EC 2.1.2.3) and IMP cyclohydrolase (EC 3.5.4.10). It is also a byproduct of Ligases (EC 6.3.4.-).

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1533005191515432D          

 25 26  0  0  0  0            999 V2000
   -0.9695   -0.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6369   -0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3820   -1.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5570   -1.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824   -0.2579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499   -0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8173   -0.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5624    0.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374    0.5266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473    1.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    1.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678    1.1079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6019   -0.5128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735   -1.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -1.8718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5581   -1.5748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4216   -0.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -1.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -1.9648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0346   -0.8100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8193   -0.5550    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4323   -1.1071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    0.2518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6477   -1.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
  2 18  1  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  0  0  0  0
 15 17  2  0  0  0  0
 11 12  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 22 23  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 13  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032111

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(=O)NC1=CN(N=C1C(N)=O)C1OC(COP(O)(O)=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N4O9P/c11-9(18)6-4(12-3-15)1-14(13-6)10-8(17)7(16)5(23-10)2-22-24(19,20)21/h1,3,5,7-8,10,16-17H,2H2,(H2,11,18)(H,12,15)(H2,19,20,21)

> <INCHI_KEY>
XUHZFJMJICUKLB-UHFFFAOYSA-N

> <FORMULA>
C10H15N4O9P

> <MOLECULAR_WEIGHT>
366.223

> <EXACT_MASS>
366.057665077

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.22712130429722

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(3-carbamoyl-4-formamido-1H-pyrazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.67

> <JCHEM_LOGP>
-2.5874732041582003

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.250348361425692

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.233630518839643

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4591145145092651

> <JCHEM_POLAR_SURFACE_AREA>
206.45999999999998

> <JCHEM_REFRACTIVITY>
86.61279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(3-carbamoyl-4-formamidopyrazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAY-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAY-15         0                                  
HETATM    1  O   UNK     0      -1.810  -0.052   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.056  -0.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.580  -2.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.040  -2.422   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.564  -0.957   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.900  -0.481   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.146  -1.387   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.392  -0.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.916   0.983   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.376   0.983   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.822   2.229   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.195   3.636   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       5.353   2.068   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       4.857  -0.957   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.177  -2.464   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       4.033  -3.494   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0       6.642  -2.940   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.520  -0.481   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.485  -3.668   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.135  -3.668   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.665  -1.512   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      -7.129  -1.036   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      -8.274  -2.067   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -7.449   0.470   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.809  -2.542   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    3   18    1                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7   10                                                  
CONECT    7    8    6                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   11   10                                                  
CONECT   10    9    6                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   17   14   16                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2   21                                                       
CONECT   19    3                                                            
CONECT   20    4                                                            
CONECT   21   18   22                                                       
CONECT   22   21   24   25   23                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

Synonyms

Not Available

Chemical Formula

C₁₀H₁₅N₄O₉P

Average Molecular Weight

366.223

Monoisotopic Molecular Weight

366.057665077

IUPAC Name

{[5-(3-carbamoyl-4-formamido-1H-pyrazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

[5-(3-carbamoyl-4-formamidopyrazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H]C(=O)NC1=CN(N=C1C(N)=O)C1OC(COP(O)(O)=O)C(O)C1O

InChI Identifier

InChI=1S/C10H15N4O9P/c11-9(18)6-4(12-3-15)1-14(13-6)10-8(17)7(16)5(23-10)2-22-24(19,20)21/h1,3,5,7-8,10,16-17H,2H2,(H2,11,18)(H,12,15)(H2,19,20,21)

InChI Key

XUHZFJMJICUKLB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose-5-phosphate
Pentose phosphate
1-ribofuranosylpyrazole
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
2-heteroaryl carboxamide
Pyrazole-5-carboxamide
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Heteroaromatic compound
Tetrahydrofuran
Pyrazole
Azole
Secondary alcohol
Primary carboxylic acid amide
Carboxamide group
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.14 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-2.6	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	-0.46	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	206.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	86.61 m³·mol⁻¹	ChemAxon
Polarizability	31.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_18) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-1927000000-87bc2d469039bc9f05a4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0c2j-2922000000-0299f534a9f714f2d251	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08mi-4910000000-cb9a0ee853ef5018c8e6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1901000000-b2be67be129148f4164b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-c7fa5890f5465e7f58f8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-0d5c63d4bfe219c98c0d	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5-Formamidoimidazole-4-carboxamide ribotide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for FAICAR (MMDBc0032111)

MOL for #<Metabolite:0x000055b76df73788>

3D MOL for #<Metabolite:0x000055b76df73788>

3D SDF for #<Metabolite:0x000055b76df73788>

3D-SDF for #<Metabolite:0x000055b76df73788>

PDB for #<Metabolite:0x000055b76df73788>

3D PDB for #<Metabolite:0x000055b76df73788>

SMILES for #<Metabolite:0x000055b76df73788>

INCHI for #<Metabolite:0x000055b76df73788>

Structure for #<Metabolite:0x000055b76df73788>

3D Structure for #<Metabolite:0x000055b76df73788>