MiMeDB: Showing metabocard for 2-Hydroxydeoxyadenosine 5'-triphosphate (MMDBc0030119)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:54:40 UTC

Update Date

2022-08-31 17:39:51 UTC

Metabolite ID

MMDBc0030119

Metabolite Identification

Common Name

2-Hydroxydeoxyadenosine 5'-triphosphate

Description

2-hydroxydeoxyadenosine 5'-triphosphate is a member of the chemical class known as Purine 2'-deoxyribonucleoside Triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking an hydroxyl group at position 2.

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241207062D          

 31 33  0  0  0  0            999 V2000
    1.3687   -2.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.4991   -4.6479    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.3165   -3.4955    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.3467   -4.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -3.1968    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.5045   -4.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -3.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -4.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -3.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -4.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -4.1630    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -3.8642    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -4.0136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  2  5  1  0  0  0  0
  2 25  1  0  0  0  0
  3 12  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  5 26  1  0  0  0  0
  6 15  1  0  0  0  0
  6 26  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 10 17  1  0  0  0  0
 18 29  1  0  0  0  0
 19 29  1  0  0  0  0
 20 29  2  0  0  0  0
 21 30  1  0  0  0  0
 22 30  2  0  0  0  0
 23 31  1  0  0  0  0
 24 31  2  0  0  0  0
 25 30  1  0  0  0  0
 27 29  1  0  0  0  0
 27 31  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  CHG  4  17  -1  18  -1  19  -1  21  -1
M  END

Structure #1
  Mrv0541 02241207062D          

 31 33  0  0  0  0            999 V2000
    1.3687   -2.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.4991   -4.6479    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.3165   -3.4955    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -4.3467   -4.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -3.1968    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.5045   -4.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -3.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -4.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -3.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6568   -4.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8316   -4.1630    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -3.8642    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -4.0136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  2  5  1  0  0  0  0
  2 25  1  0  0  0  0
  3 12  2  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  5 26  1  0  0  0  0
  6 15  1  0  0  0  0
  6 26  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 10 17  1  0  0  0  0
 18 29  1  0  0  0  0
 19 29  1  0  0  0  0
 20 29  2  0  0  0  0
 21 30  1  0  0  0  0
 22 30  2  0  0  0  0
 23 31  1  0  0  0  0
 24 31  2  0  0  0  0
 25 30  1  0  0  0  0
 27 29  1  0  0  0  0
 27 31  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  CHG  4  17  -1  18  -1  19  -1  21  -1
M  END
> <DATABASE_ID>
MMDBc0030119

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=C2N=CN(C3CC(O)C(COP([O-])(=O)OP(O)(=O)OP([O-])([O-])=O)O3)C2=NC([O-])=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N5O13P3/c11-8-7-9(14-10(17)13-8)15(3-12-7)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/p-4

> <INCHI_KEY>
UOACBPRDWRDEHJ-UHFFFAOYSA-J

> <FORMULA>
C10H12N5O13P3

> <MOLECULAR_WEIGHT>
503.1493

> <EXACT_MASS>
502.964445031

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
37.90328442153255

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-9-[4-hydroxy-5-({[hydroxy(phosphonatooxy)phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-9H-purin-2-olate

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-3.7246645514094996

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.511103225946711

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8199187053754846

> <JCHEM_PKA_STRONGEST_BASIC>
1.5923853040958154

> <JCHEM_POLAR_SURFACE_AREA>
290.45000000000005

> <JCHEM_REFRACTIVITY>
103.41569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-9-[4-hydroxy-5-({[hydroxy(phosphonatooxy)phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]purin-2-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.924   1.777   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       2.126  -7.970   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0     -10.265  -8.676   0.000  0.00  0.00           O-1
HETATM   19  O   UNK     0      -9.924  -6.525   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0      -8.114  -9.017   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.619  -5.967   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0      -2.808  -8.459   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.740  -6.085   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.993  -8.899   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.468  -6.308   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.185  -4.489   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.773  -6.866   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.959  -8.119   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      -9.019  -7.771   0.000  0.00  0.00           P+0
HETATM   30  P   UNK     0      -3.714  -7.213   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      -6.366  -7.492   0.000  0.00  0.00           P+0
CONECT    1    4    6                                                       
CONECT    2    5   25                                                       
CONECT    3   12   15                                                       
CONECT    4    1    5   16                                                  
CONECT    5    2    4   26                                                  
CONECT    6    1   15   26                                                  
CONECT    7    8    9   12                                                  
CONECT    8    7   11   13                                                  
CONECT    9    7   14   15                                                  
CONECT   10   13   14   17                                                  
CONECT   11    8                                                            
CONECT   12    3    7                                                       
CONECT   13    8   10                                                       
CONECT   14    9   10                                                       
CONECT   15    3    6    9                                                  
CONECT   16    4                                                            
CONECT   17   10                                                            
CONECT   18   29                                                            
CONECT   19   29                                                            
CONECT   20   29                                                            
CONECT   21   30                                                            
CONECT   22   30                                                            
CONECT   23   31                                                            
CONECT   24   31                                                            
CONECT   25    2   30                                                       
CONECT   26    5    6                                                       
CONECT   27   29   31                                                       
CONECT   28   30   31                                                       
CONECT   29   18   19   20   27                                             
CONECT   30   21   22   25   28                                             
CONECT   31   23   24   27   28                                             
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

Synonyms

Value	Source
2-Hydroxydeoxyadenosine 5'-triphosphoric acid	Generator

Molecular Formula

C₁₀H₁₂N₅O₁₃P₃

Average Mass

503.1493

Monoisotopic Mass

502.964445031

IUPAC Name

6-amino-9-[4-hydroxy-5-({[hydroxy(phosphonatooxy)phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-9H-purin-2-olate

Traditional Name

6-amino-9-[4-hydroxy-5-({[hydroxy(phosphonatooxy)phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]purin-2-olate

CAS Registry Number

Not Available

SMILES

NC1=C2N=CN(C3CC(O)C(COP([O-])(=O)OP(O)(=O)OP([O-])([O-])=O)O3)C2=NC([O-])=N1

InChI Identifier

InChI=1S/C10H16N5O13P3/c11-8-7-9(14-10(17)13-8)15(3-12-7)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/p-4

InChI Key

UOACBPRDWRDEHJ-UHFFFAOYSA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine deoxyribonucleotides

Direct Parent

Purine 2'-deoxyribonucleoside triphosphates

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside triphosphate
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Imidolactam
Alkyl phosphate
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a purine-related compound (CPD-13851 )
a deoxyribonucleoside triphosphate (CPD-13851 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.84 g/L	ALOGPS
logP	-0.75	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	290.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103.42 m³·mol⁻¹	ChemAxon
Polarizability	37.9 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

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019160	2-Hydroxydeoxyadenosine 5'-triphosphate	2-hydroxy-dAMP	CTP pyrophosphohydrolase	Hydrolysis of bond	PathBank	31602464

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/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25202902

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 2-Hydroxydeoxyadenosine 5'-triphosphate (MMDBc0030119)

MOL for #<Metabolite:0x00007f921193f7d8>

3D MOL for #<Metabolite:0x00007f921193f7d8>

3D SDF for #<Metabolite:0x00007f921193f7d8>

3D-SDF for #<Metabolite:0x00007f921193f7d8>

PDB for #<Metabolite:0x00007f921193f7d8>

3D PDB for #<Metabolite:0x00007f921193f7d8>

SMILES for #<Metabolite:0x00007f921193f7d8>

INCHI for #<Metabolite:0x00007f921193f7d8>

Structure for #<Metabolite:0x00007f921193f7d8>

3D Structure for #<Metabolite:0x00007f921193f7d8>