NP-MRD: Showing NP-Card for 3-Deoxy-D-arabino-heptulosonate 7-phosphate (NP0054989)

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Record Information

Version

2.0

Created at

2022-04-28 01:10:22 UTC

Updated at

2022-04-28 01:10:22 UTC

NP-MRD ID

NP0054989

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Deoxy-D-arabino-heptulosonate 7-phosphate

Description

2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate, also known as 2-dahp or 3-deoxy-arabino-heptulonic acid 7-phosphoric acid, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate exists in both E. 3-Deoxy-D-arabino-heptulosonate 7-phosphate is found in Arabidopsis thaliana. Coli (prokaryote) and yeast (eukaryote).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
    4.1492   -1.3348    1.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9143   -0.1398    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7926    0.4226    2.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095    0.6247    0.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6147    1.7943    1.1555 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115   -0.0267   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261    0.8748   -0.6484 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3015    2.0369   -1.2403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    0.1491   -1.6509 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1058    0.9624   -2.0311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4913   -1.1924   -1.1528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2266   -1.8347   -2.1838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938   -1.1204    0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5198   -0.3888   -0.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6234   -0.2212    0.9275 P   0  0  1  0  0  5  0  0  0  0  0  0
   -4.4317   -1.4450    1.1921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745    0.2458    2.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6626    1.0755    0.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7830    0.3706    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413   -0.4000   -0.9973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4783   -0.9124    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411    1.1882    0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174    1.8926   -2.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5744   -0.0276   -2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    1.6781   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663   -1.8628   -0.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070   -1.3989   -3.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455   -0.5404    0.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004   -2.1203    0.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766    0.0483    3.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2961    1.6025   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 13 14  1  0
 15 14  1  6
 15 17  1  0
 15 18  1  0
 15 16  2  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 12 27  1  0
 11 26  1  1
 13 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
  9 24  1  6
 10 25  1  0
  7 22  1  1
  8 23  1  0
  6 20  1  0
  6 21  1  0
  3 19  1  0
M  END


  Mrv0541 02241222022D          

 18 17  0  0  1  0            999 V2000
    6.3519   -8.8641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0646   -9.2762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6350   -9.2762    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3519   -8.0392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7849   -8.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0646  -10.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9188   -8.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350  -10.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4976   -9.2762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3266   -9.2728    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.1549   -9.2728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3266   -8.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3266  -10.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036   -9.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4933   -8.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788   -9.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1994  -10.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891   -8.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  6  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
  7 14  1  0  0  0  0
  1  2  1  0  0  0  0
 14 15  1  0  0  0  0
  1  3  1  0  0  0  0
 15 16  1  0  0  0  0
  1  4  1  6  0  0  0
 14 17  2  0  0  0  0
  2  5  1  0  0  0  0
 15 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0054989

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)CC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/t3-,5-,6+/m1/s1

> <INCHI_KEY>
PJWIPEXIFFQAQZ-PUFIMZNGSA-N

> <FORMULA>
C7H13O10P

> <MOLECULAR_WEIGHT>
288.1459

> <EXACT_MASS>
288.024633148

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
22.367783841238907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid

> <ALOGPS_LOGP>
-2.47

> <JCHEM_LOGP>
-2.5289322136666668

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.9174480444633493

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4688872906407804

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271766798649698

> <JCHEM_POLAR_SURFACE_AREA>
181.82

> <JCHEM_REFRACTIVITY>
53.151700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DAHP

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      11.857 -16.546   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.187 -17.316   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.519 -17.316   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.857 -15.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.532 -16.546   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.187 -18.855   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.182 -16.546   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.519 -18.855   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      15.862 -17.316   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0      17.410 -17.309   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0      18.956 -17.309   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      17.410 -15.763   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      17.410 -18.849   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.847 -17.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.521 -16.546   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.187 -17.314   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.839 -18.849   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.513 -15.003   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    6    1    5                                                  
CONECT    3    7    8    1                                                  
CONECT    4    1                                                            
CONECT    5    9    2                                                       
CONECT    6    2                                                            
CONECT    7    3   14                                                       
CONECT    8    3                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    7   15   17                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
2-Dahp	ChEBI
3-Deoxy-arabino-heptulonate 7-phosphate	ChEBI
3-Deoxy-D-arabino-2-heptulosonic acid 7-(dihydrogen phosphate)	ChEBI
3-Deoxy-D-arabino-hept-2-ulosonate 7-phosphate	ChEBI
3-Deoxy-D-arabino-heptulosonate-7-phosphate	ChEBI
3-Deoxy-D-arabino-heptulosonic acid 7-phosphate	ChEBI
DAHP	ChEBI
3-Deoxy-arabino-heptulonic acid 7-phosphoric acid	Generator
3-Deoxy-D-arabino-2-heptulosonate 7-(dihydrogen phosphate)	Generator
3-Deoxy-D-arabino-2-heptulosonic acid 7-(dihydrogen phosphoric acid)	Generator
3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphoric acid	Generator
3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid	Generator
3-Deoxy-D-arabino-heptulosonate 7-phosphate	Generator
3-Deoxy-D-arabino-heptulosonic acid 7-phosphoric acid	Generator
2-Dehydro-3-deoxy-D-arabino-heptonic acid 7-phosphoric acid	Generator
3-Deoxyarabinoheptulosonate-7-phosphate	MeSH
7-Phospho-2-keto-3-deoxy-D-arabinoheptonate	MeSH
3-Deoxy-D-arabino-2-heptulosonic acid	MeSH
2-Dehydro-3-deoxy-D-arabino-heptulosonic acid-7-phosphate	MeSH
2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate	ChEBI
7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonate	Generator

Chemical Formula

C₇H₁₃O₁₀P

Average Mass

288.1459 Da

Monoisotopic Mass

288.02463 Da

IUPAC Name

(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid

Traditional Name

DAHP

CAS Registry Number

Not Available

SMILES

O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)CC(=O)C(O)=O

InChI Identifier

InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/t3-,5-,6+/m1/s1

InChI Key

PJWIPEXIFFQAQZ-PUFIMZNGSA-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
Arabidopsis thaliana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Heptose monosaccharide
Monosaccharide phosphate
Medium-chain keto acid
Monoalkyl phosphate
Sugar acid
Alpha-keto acid
Alkyl phosphate
Beta-hydroxy ketone
Phosphoric acid ester
Organic phosphoric acid derivative
Keto acid
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Polyol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

ketoaldonic acid phosphate (CHEBI:18150 )

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	-2.5	ALOGPS
logP	-2.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	53.15 m³·mol⁻¹	ChemAxon
Polarizability	22.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	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

FDB030419

KNApSAcK ID

C00007497

Chemspider ID

Not Available

KEGG Compound ID

C04691

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160647

PDB ID

Not Available

ChEBI ID

18150

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Deoxy-D-arabino-heptulosonate 7-phosphate (NP0054989)

MOL for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

3D MOL for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

3D SDF for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

3D-SDF for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

PDB for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

3D PDB for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

SMILES for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

INCHI for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

Structure for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)

3D Structure for NP0054989 (3-Deoxy-D-arabino-heptulosonate 7-phosphate)