NP-MRD: Showing NP-Card for 3-Formyl-1-butyl pyrophosphate (NP0001813)

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Record Information

Version

2.0

Created at

2020-10-21 16:38:47 UTC

Updated at

2021-07-15 16:45:20 UTC

NP-MRD ID

NP0001813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Formyl-1-butyl pyrophosphate

Provided By

NPAtlas

Description

3-Formylbutyl diphosphate is also known as tubagl. 3-Formyl-1-butyl pyrophosphate is found in Mycobacterium. 3-Formyl-1-butyl pyrophosphate was first documented in 1999 (PMID: 10542241). Based on a literature review very few articles have been published on 3-formylbutyl diphosphate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

 27 26  0  0  0  0            999 V2000
   -4.2214    0.6599   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811   -0.0557   -0.5088 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7968   -1.2577    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0335   -1.1646    1.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    0.8503   -0.4890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7888    0.2799    0.5004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    1.0816    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030    0.1676    0.1012 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.4858   -1.3057    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    0.3383   -1.5569 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716    0.7474    0.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3649   -0.2286    0.4091 P   0  0  2  0  0  5  0  0  0  0  0  0
    4.2582   -1.5580    1.1062 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.5170    0.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -0.5092   -1.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233   -0.0160    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.9549   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601    1.6001    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -0.3997   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -2.2027   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0521    1.8856   -0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921    0.8724   -1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859    0.3317    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694   -0.7615    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7130   -0.4219   -2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    0.5618    1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.9672   -1.5684 H   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
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  6  0  0  0
  3 20  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  6 23  1  0  0  0  0
  6 24  1  0  0  0  0
 10 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  0  0  0  0
M  END


  Mrv1652306242117443D          

 27 26  0  0  0  0            999 V2000
   -4.2214    0.6599   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811   -0.0557   -0.5088 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7968   -1.2577    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0335   -1.1646    1.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822    0.8503   -0.4890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7888    0.2799    0.5004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    1.0816    0.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7030    0.1676    0.1012 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.4858   -1.3057    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334    0.3383   -1.5569 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716    0.7474    0.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3649   -0.2286    0.4091 P   0  0  2  0  0  5  0  0  0  0  0  0
    4.2582   -1.5580    1.1062 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501    0.5170    0.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -0.5092   -1.2467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8233   -0.0160    0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.9549   -0.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601    1.6001    0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1548   -0.3997   -1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -2.2027   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0521    1.8856   -0.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2921    0.8724   -1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1859    0.3317    1.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694   -0.7615    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7130   -0.4219   -2.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    0.5618    1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.9672   -1.5684 H   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
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  6  0  0  0
  3 20  1  0  0  0  0
  5 21  1  0  0  0  0
  5 22  1  0  0  0  0
  6 23  1  0  0  0  0
  6 24  1  0  0  0  0
 10 25  1  0  0  0  0
 14 26  1  0  0  0  0
 15 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[P](=O)(O[H])O[P@](=O)(O[H])OC([H])([H])C([H])([H])[C@@]([H])(C([H])=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h4-5H,2-3H2,1H3,(H,10,11)(H2,7,8,9)/t5-/m0/s1

> <INCHI_KEY>
KIJIIIDYDGXWFJ-UHFFFAOYSA-N

> <FORMULA>
C5H12O8P2

> <MOLECULAR_WEIGHT>
262.091

> <EXACT_MASS>
262.000741342

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.828019409024556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
({hydroxy[(3S)-3-methyl-4-oxobutoxy]phosphoryl}oxy)phosphonic acid

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
-0.675914303333333

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2211480640820707

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7792791679737103

> <JCHEM_PKA_STRONGEST_BASIC>
-7.01616363324802

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
49.1952

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[hydroxy((3S)-3-methyl-4-oxobutoxy)phosphoryl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.221   0.660  -0.016  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.981  -0.056  -0.509  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.797  -1.258   0.364  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.034  -1.165   1.547  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.782   0.850  -0.489  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.789   0.280   0.500  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.339   1.082   0.471  0.00  0.00           O+0
HETATM    8  P   UNK     0       1.703   0.168   0.101  0.00  0.00           P+0
HETATM    9  O   UNK     0       1.486  -1.306   0.416  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.033   0.338  -1.557  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.072   0.747   0.925  0.00  0.00           O+0
HETATM   12  P   UNK     0       4.365  -0.229   0.409  0.00  0.00           P+0
HETATM   13  O   UNK     0       4.258  -1.558   1.106  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.850   0.517   0.624  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.118  -0.509  -1.247  0.00  0.00           O+0
HETATM   16  H   UNK     0      -4.823  -0.016   0.630  0.00  0.00           H+0
HETATM   17  H   UNK     0      -4.865   0.955  -0.882  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.960   1.600   0.498  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.155  -0.400  -1.552  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.498  -2.203  -0.052  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.052   1.886  -0.239  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.292   0.872  -1.478  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.186   0.332   1.544  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.569  -0.762   0.183  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.713  -0.422  -2.089  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.132   0.562   1.562  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.936  -0.967  -1.568  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    1    3    5   19                                             
CONECT    3    2    4   20                                                  
CONECT    4    3                                                            
CONECT    5    2    6   21   22                                             
CONECT    6    5    7   23   24                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8   25                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12   26                                                       
CONECT   15   12   27                                                       
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    5                                                            
CONECT   22    5                                                            
CONECT   23    6                                                            
CONECT   24    6                                                            
CONECT   25   10                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
TUBAgl	ChEBI
3-Formylbutyl diphosphoric acid	Generator
3-Formyl-1-butyl diphosphate	MeSH
3-Formyl-1-butyl pyrophosphate	MeSH

Chemical Formula

C₅H₁₂O₈P₂

Average Mass

262.0910 Da

Monoisotopic Mass

262.00074 Da

IUPAC Name

({hydroxy[(3S)-3-methyl-4-oxobutoxy]phosphoryl}oxy)phosphonic acid

Traditional Name

[hydroxy((3S)-3-methyl-4-oxobutoxy)phosphoryl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(CCOP(O)(=O)OP(O)(O)=O)C=O

InChI Identifier

InChI=1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h4-5H,2-3H2,1H3,(H,10,11)(H2,7,8,9)

InChI Key

KIJIIIDYDGXWFJ-UHFFFAOYSA-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
Mycobacterium	NPAtlas	10542241

Chemical Taxonomy

Classification

Not classified

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	-0.3	ALOGPS
logP	-0.68	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.2 m³·mol⁻¹	ChemAxon
Polarizability	20.83 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011638

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8097066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9921431

PDB ID

Not Available

ChEBI ID

59398

Good Scents ID

Not Available

References

General References

Belmant C, Espinosa E, Poupot R, Peyrat MA, Guiraud M, Poquet Y, Bonneville M, Fournie JJ: 3-Formyl-1-butyl pyrophosphate A novel mycobacterial metabolite-activating human gammadelta T cells. J Biol Chem. 1999 Nov 5;274(45):32079-84. doi: 10.1074/jbc.274.45.32079. [PubMed:10542241 ]

Showing NP-Card for 3-Formyl-1-butyl pyrophosphate (NP0001813)

MOL for NP0001813 (3-Formyl-1-butyl pyrophosphate)

3D MOL for NP0001813 (3-Formyl-1-butyl pyrophosphate)

3D SDF for NP0001813 (3-Formyl-1-butyl pyrophosphate)

3D-SDF for NP0001813 (3-Formyl-1-butyl pyrophosphate)

PDB for NP0001813 (3-Formyl-1-butyl pyrophosphate)

3D PDB for NP0001813 (3-Formyl-1-butyl pyrophosphate)

SMILES for NP0001813 (3-Formyl-1-butyl pyrophosphate)

INCHI for NP0001813 (3-Formyl-1-butyl pyrophosphate)

Structure for NP0001813 (3-Formyl-1-butyl pyrophosphate)

3D Structure for NP0001813 (3-Formyl-1-butyl pyrophosphate)