NP-MRD: Showing NP-Card for N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate (NP0339998)

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Record Information

Version

2.0

Created at

2024-09-12 00:47:42 UTC

Updated at

2024-09-12 00:47:43 UTC

NP-MRD ID

NP0339998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate

Description

N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Based on a literature review very few articles have been published on N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272303192D          

 28 30  0  0  0  0            999 V2000
 9987.5047 9984.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2953 9984.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.8027 9986.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5185 9985.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2323 9986.2738    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8217 9986.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9480 9985.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6468 9986.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.4166 9986.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.7500 9985.8705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9988.0046 9985.0869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9988.8285 9985.0869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.0831 9985.8705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.0333 9986.2754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0333 9987.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6062 9986.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6062 9987.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3197 9987.5112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8901 9985.8630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1767 9986.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1767 9987.0990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8901 9987.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7450 9989.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0301 9988.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7450 9988.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4600 9988.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1752 9988.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8901 9988.3389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 11  1  1  1  0  0  0
 12  2  1  1  0  0  0
 13  3  1  6  0  0  0
 10 14  1  6  0  0  0
 14 15  1  0  0  0  0
 17 22  1  0  0  0  0
 19 16  1  0  0  0  0
 16 14  1  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 22 28  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 21  2  0  0  0  0
 25 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
M  END


  Mrv2104 05272303192D          

 28 30  0  0  0  0            999 V2000
 9987.5047 9984.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.2953 9984.4116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9989.8027 9986.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.5185 9985.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.2323 9986.2738    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8217 9986.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9480 9985.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.6468 9986.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9988.4166 9986.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9987.7500 9985.8705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9988.0046 9985.0869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9988.8285 9985.0869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9989.0831 9985.8705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.0333 9986.2754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0333 9987.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6062 9986.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6062 9987.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3197 9987.5112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8901 9985.8630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1767 9986.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1767 9987.0990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8901 9987.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7450 9989.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0301 9988.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7450 9988.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4600 9988.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1752 9988.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8901 9988.3389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 11  1  1  1  0  0  0
 12  2  1  1  0  0  0
 13  3  1  6  0  0  0
 10 14  1  6  0  0  0
 14 15  1  0  0  0  0
 17 22  1  0  0  0  0
 19 16  1  0  0  0  0
 16 14  1  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 17 16  2  0  0  0  0
 22 28  1  0  0  0  0
 20 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 21  2  0  0  0  0
 25 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1/C15H22N5O7P/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(22)11(21)9(27-15)5-26-28(23,24)25/h3,6-7,9,11-12,15,21-22H,4-5H2,1-2H3,(H,16,17,18)(H2,23,24,25)/t9-,11-,12-,15-/s2

> <INCHI_KEY>
DUISZFLWBAPRBR-MXPBUBMTNA-N

> <FORMULA>
C15H22N5O7P

> <MOLECULAR_WEIGHT>
415.343

> <EXACT_MASS>
415.125685066

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.73754594865307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid

> <JCHEM_LOGP>
-2.8557442937339026

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.262615716657036

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2253373392051221

> <JCHEM_PKA_STRONGEST_BASIC>
3.7112116678926594

> <JCHEM_POLAR_SURFACE_AREA>
172.07999999999996

> <JCHEM_REFRACTIVITY>
98.6801

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
Isopentenyl-AMP

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  O   UNK     0    8643.3428637.587   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8646.6858637.568   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8647.6328641.045   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8648.9688640.276   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8650.3008641.045   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8649.5348642.379   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8651.6368640.276   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8651.0748642.379   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8645.0448641.196   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8643.8008640.292   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8644.2758638.829   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8645.8138638.829   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8646.2888640.292   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    8642.4628641.047   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    8642.4628642.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8639.7988641.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8639.7988642.585   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8641.1308643.354   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0    8638.4628640.278   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8637.1308641.047   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0    8637.1308642.585   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0    8638.4628643.354   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8634.4578647.210   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8633.1238644.899   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8634.4578645.669   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8635.7928644.899   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8637.1278645.669   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0    8638.4628644.899   0.000  0.00  0.00           N+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    4   13                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   10   13                                                       
CONECT   10   11    9   14                                                  
CONECT   11   10   12    1                                                  
CONECT   12   11   13    2                                                  
CONECT   13   12    9    3                                                  
CONECT   14   10   15   16                                                  
CONECT   15   14   18                                                       
CONECT   16   19   14   17                                                  
CONECT   17   22   18   16                                                  
CONECT   18   15   17                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   17   28   21                                                  
CONECT   23   25                                                            
CONECT   24   25                                                            
CONECT   25   23   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   22   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
N6-(Δ2-isopentenyl)-adenosine 5'-monophosphoric acid	Generator

Chemical Formula

C₁₅H₂₂N₅O₇P

Average Mass

415.3430 Da

Monoisotopic Mass

415.12569 Da

IUPAC Name

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

Isopentenyl-AMP

CAS Registry Number

Not Available

SMILES

CC(C)=CCNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1/C15H22N5O7P/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(22)11(21)9(27-15)5-26-28(23,24)25/h3,6-7,9,11-12,15,21-22H,4-5H2,1-2H3,(H,16,17,18)(H2,23,24,25)/t9-,11-,12-,15-/s2

InChI Key

DUISZFLWBAPRBR-MXPBUBMTNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-alkylaminopurine
6-aminopurine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Secondary aliphatic/aromatic amine
Monoalkyl phosphate
Alkyl phosphate
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Organic phosphoric acid derivative
Phosphoric acid ester
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Secondary amine
Oxacycle
Azacycle
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N(6)-dimethylallyladenosine 5'-monophosphate (CHEBI:15819 )

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	-2.9	ChemAxon
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	3.71	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	98.68 m³·mol⁻¹	ChemAxon
Polarizability	39.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007239

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate (NP0339998)

MOL for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

3D MOL for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

3D SDF for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

3D-SDF for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

PDB for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

3D PDB for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

SMILES for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

INCHI for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

Structure for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)

3D Structure for NP0339998 (N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate)