NP-MRD: Showing NP-Card for 2-Phenylaminoadenosine (NP0000737)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:42:51 UTC

NP-MRD ID

NP0000737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Phenylaminoadenosine

Description

Selective A2 adenosine receptor agonist; potent coronary vasodilator; weak inhibitor of adenosine uptake by rat cerebral cortical synaptosomes; used as a vasodilator agent; is a potent anti-inflammatory agent, acting at its four G protein coupled receptors. Topical treatment of adenosine to foot wounds in diabetes mellitus has been shown in lab animals to drastically increase tissue repair and reconstruction. Topical administration of adenosine for use in wound healing deficiencies and diabetes mellitus in humans is currently under clinical investigation. Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a beta-N9-glycosidic bond.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305261923552D          

 26 29  0  0  0  0            999 V2000
    2.9407   -4.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0802   -3.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7477   -4.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339   -3.7761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -5.1486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745   -5.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0282   -6.3047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802   -5.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1677   -4.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4053   -5.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -4.9771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4053   -4.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802   -4.2626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -3.5482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6427   -3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0552   -2.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802   -2.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2927   -3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802   -4.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0552   -4.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -6.4060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6052   -5.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -3.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -2.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 15 11  2  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 22 17  2  0  0  0  0
 23 12  1  0  0  0  0
 24  1  1  0  0  0  0
 25  2  1  0  0  0  0
 26  6  1  0  0  0  0
M  END

HMDB0001069
     RDKit          3D
2-Phenylaminoadenosine
 44 47  0  0  0  0  0  0  0  0999 V2000
    1.7346    3.8800   -1.4241 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2648    2.5914   -1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    1.6259   -0.6026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.3849   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.6154    0.2524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565   -0.5912    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.4998    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0088    0.5194    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -0.5953    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8610   -1.7327    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117   -1.7223    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    0.1404   -0.4390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    1.0586   -0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    2.3142   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1063    3.0293   -1.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099    2.2273   -1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296    1.0341   -1.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -0.0744   -0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026    0.3115   -0.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.8302    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8810   -0.6529    1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    0.3794    1.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3811   -1.9347    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.5398    1.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1159   -1.1882   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768   -2.0102   -0.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    4.0552   -2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522    4.6331   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9981   -1.5457    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182    1.4020   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5669    1.4233    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6860   -0.5657    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3819   -2.5811    1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -2.6220    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    2.5716   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1274   -0.4649   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927   -1.0531   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741   -0.4319    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4124   -1.5543    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1230    0.6015    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6140   -2.6713   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -3.1283    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -0.7850    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -2.7924   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14  2  1  0
 25 18  1  0
 11  6  1  0
 17 13  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
M  END


  Mrv1652305261923552D          

 26 29  0  0  0  0            999 V2000
    2.9407   -4.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282   -4.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0802   -3.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7477   -4.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339   -3.7761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608   -5.1486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745   -5.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0282   -6.3047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802   -5.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1677   -4.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4053   -5.6916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -4.9771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4053   -4.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802   -4.2626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -3.5482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6427   -3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0552   -2.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802   -2.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2927   -3.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8802   -4.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0552   -4.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8177   -6.4060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6052   -5.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7078   -3.9674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1241   -2.3787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 15 11  2  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  2  0  0  0  0
 22 21  1  0  0  0  0
 22 17  2  0  0  0  0
 23 12  1  0  0  0  0
 24  1  1  0  0  0  0
 25  2  1  0  0  0  0
 26  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2N=CN(C3OC(CO)C(O)C3O)C2=NC(NC2=CC=CC=C2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)

> <INCHI_KEY>
SCNILGOVBBRMBK-UHFFFAOYSA-N

> <FORMULA>
C16H18N6O4

> <MOLECULAR_WEIGHT>
358.3519

> <EXACT_MASS>
358.138953094

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.3382576996023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

> <ALOGPS_LOGP>
0.22

> <JCHEM_LOGP>
0.027747925666666524

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.425237286800439

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.420937979980263

> <JCHEM_PKA_STRONGEST_BASIC>
3.8626235523468253

> <JCHEM_POLAR_SURFACE_AREA>
151.57

> <JCHEM_REFRACTIVITY>
91.62780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[6-amino-2-(phenylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001069
     RDKit          3D
2-Phenylaminoadenosine
 44 47  0  0  0  0  0  0  0  0999 V2000
    1.7346    3.8800   -1.4241 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2648    2.5914   -1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    1.6259   -0.6026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.3849   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.6154    0.2524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565   -0.5912    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.4998    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0088    0.5194    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -0.5953    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8610   -1.7327    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117   -1.7223    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    0.1404   -0.4390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    1.0586   -0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    2.3142   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1063    3.0293   -1.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099    2.2273   -1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296    1.0341   -1.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -0.0744   -0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026    0.3115   -0.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.8302    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8810   -0.6529    1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    0.3794    1.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3811   -1.9347    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.5398    1.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1159   -1.1882   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768   -2.0102   -0.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    4.0552   -2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522    4.6331   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9981   -1.5457    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182    1.4020   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5669    1.4233    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6860   -0.5657    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3819   -2.5811    1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -2.6220    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    2.5716   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1274   -0.4649   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927   -1.0531   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741   -0.4319    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4124   -1.5543    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1230    0.6015    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6140   -2.6713   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -3.1283    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -0.7850    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -2.7924   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14  2  1  0
 25 18  1  0
 11  6  1  0
 17 13  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       5.489  -8.901   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.719  -7.567   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.750  -6.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.996  -8.580   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.157  -7.049   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.430  -4.916   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       8.140  -9.611   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.979 -11.142   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       9.386 -11.769   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      10.416 -10.624   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.646  -9.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.957 -10.624   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      12.726  -9.291   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      11.957  -7.957   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      10.416  -7.957   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      12.726  -6.623   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      14.266  -6.623   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.036  -5.290   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.576  -5.290   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.346  -6.623   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.576  -7.957   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.036  -7.957   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      12.726 -11.958   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       4.863 -10.307   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.188  -7.406   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.965  -4.440   0.000  0.00  0.00           O+0
CONECT    1    2    4   24                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    5    6                                                  
CONECT    4    1    5    7                                                  
CONECT    5    4    3                                                       
CONECT    6    3   26                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    7   15                                                  
CONECT   12   10   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   11                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   12                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0001069
HETATM    1  N1  UNL     1       1.735   3.880  -1.424  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.265   2.591  -1.081  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.022   1.626  -0.603  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.662   0.385  -0.254  1.00  0.00           C  
HETATM    5  N3  UNL     1       2.499  -0.615   0.252  1.00  0.00           N  
HETATM    6  C3  UNL     1       3.856  -0.591   0.516  1.00  0.00           C  
HETATM    7  C4  UNL     1       4.644   0.500   0.303  1.00  0.00           C  
HETATM    8  C5  UNL     1       6.009   0.519   0.570  1.00  0.00           C  
HETATM    9  C6  UNL     1       6.614  -0.595   1.069  1.00  0.00           C  
HETATM   10  C7  UNL     1       5.861  -1.733   1.304  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.512  -1.722   1.030  1.00  0.00           C  
HETATM   12  N4  UNL     1       0.323   0.140  -0.439  1.00  0.00           N  
HETATM   13  C9  UNL     1      -0.525   1.059  -0.920  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.074   2.314  -1.255  1.00  0.00           C  
HETATM   15  N5  UNL     1      -1.106   3.029  -1.704  1.00  0.00           N  
HETATM   16  C11 UNL     1      -2.210   2.227  -1.653  1.00  0.00           C  
HETATM   17  N6  UNL     1      -1.830   1.034  -1.172  1.00  0.00           N  
HETATM   18  C12 UNL     1      -2.718  -0.074  -0.974  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.803   0.312  -0.188  1.00  0.00           O  
HETATM   20  C13 UNL     1      -4.386  -0.830   0.308  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.881  -0.653   1.730  1.00  0.00           C  
HETATM   22  O2  UNL     1      -5.832   0.379   1.732  1.00  0.00           O  
HETATM   23  C15 UNL     1      -3.381  -1.935   0.267  1.00  0.00           C  
HETATM   24  O3  UNL     1      -3.186  -2.540   1.507  1.00  0.00           O  
HETATM   25  C16 UNL     1      -2.116  -1.188  -0.172  1.00  0.00           C  
HETATM   26  O4  UNL     1      -1.277  -2.010  -0.909  1.00  0.00           O  
HETATM   27  H1  UNL     1       2.059   4.055  -2.385  1.00  0.00           H  
HETATM   28  H2  UNL     1       1.752   4.633  -0.724  1.00  0.00           H  
HETATM   29  H3  UNL     1       1.998  -1.546   0.468  1.00  0.00           H  
HETATM   30  H4  UNL     1       4.218   1.402  -0.088  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.567   1.423   0.375  1.00  0.00           H  
HETATM   32  H6  UNL     1       7.686  -0.566   1.273  1.00  0.00           H  
HETATM   33  H7  UNL     1       6.382  -2.581   1.695  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.938  -2.622   1.221  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.186   2.572  -1.965  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.127  -0.465  -1.945  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.293  -1.053  -0.314  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.074  -0.432   2.438  1.00  0.00           H  
HETATM   39  H13 UNL     1      -5.412  -1.554   2.084  1.00  0.00           H  
HETATM   40  H14 UNL     1      -6.123   0.602   2.649  1.00  0.00           H  
HETATM   41  H15 UNL     1      -3.614  -2.671  -0.524  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.971  -3.128   1.653  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.660  -0.785   0.738  1.00  0.00           H  
HETATM   44  H18 UNL     1      -1.817  -2.792  -1.202  1.00  0.00           H  
CONECT    1    2   27   28
CONECT    2    3    3   14
CONECT    3    4
CONECT    4    5   12   12
CONECT    5    6   29
CONECT    6    7    7   11
CONECT    7    8   30
CONECT    8    9    9   31
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   34
CONECT   12   13
CONECT   13   14   14   17
CONECT   14   15
CONECT   15   16   16
CONECT   16   17   35
CONECT   17   18
CONECT   18   19   25   36
CONECT   19   20
CONECT   20   21   23   37
CONECT   21   22   38   39
CONECT   22   40
CONECT   23   24   25   41
CONECT   24   42
CONECT   25   26   43
CONECT   26   44
END

HMDB0001069
     RDKit          3D
2-Phenylaminoadenosine
 44 47  0  0  0  0  0  0  0  0999 V2000
    1.7346    3.8800   -1.4241 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2648    2.5914   -1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    1.6259   -0.6026 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.3849   -0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990   -0.6154    0.2524 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565   -0.5912    0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437    0.4998    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0088    0.5194    0.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -0.5953    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8610   -1.7327    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5117   -1.7223    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    0.1404   -0.4390 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    1.0586   -0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0744    2.3142   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1063    3.0293   -1.7040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2099    2.2273   -1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8296    1.0341   -1.1725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7178   -0.0744   -0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8026    0.3115   -0.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.8302    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8810   -0.6529    1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8319    0.3794    1.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3811   -1.9347    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.5398    1.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1159   -1.1882   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768   -2.0102   -0.9095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0595    4.0552   -2.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7522    4.6331   -0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9981   -1.5457    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182    1.4020   -0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5669    1.4233    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6860   -0.5657    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3819   -2.5811    1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -2.6220    1.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    2.5716   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1274   -0.4649   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2927   -1.0531   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741   -0.4319    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4124   -1.5543    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1230    0.6015    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6140   -2.6713   -0.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711   -3.1283    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -0.7850    0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8167   -2.7924   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  4 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14  2  1  0
 25 18  1  0
 11  6  1  0
 17 13  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 18 36  1  0
 20 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
 25 43  1  0
 26 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
6-Amino-2-phenylamino-9-b-D-ribofuranosyl-9H-purine	HMDB
6-Amino-2-phenylamino-9-beta-delta-ribofuranosyl-9H-purine	HMDB
2-Phenylaminoadenosine	MeSH

Chemical Formula

C₁₆H₁₈N₆O₄

Average Mass

358.3519 Da

Monoisotopic Mass

358.13895 Da

IUPAC Name

2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Traditional Name

2-[6-amino-2-(phenylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

CAS Registry Number

53296-10-9

SMILES

NC1=C2N=CN(C3OC(CO)C(O)C3O)C2=NC(NC2=CC=CC=C2)=N1

InChI Identifier

InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)

InChI Key

SCNILGOVBBRMBK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	¹³C NMR Spectrum (1D, 252 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	¹³C NMR Spectrum (1D, 75 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	¹³C NMR Spectrum (1D, 126 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	¹³C NMR Spectrum (1D, 176 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	¹³C NMR Spectrum (1D, 226 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
N-substituted imidazole
Monosaccharide
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Imidazole
Azole
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Primary amine
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

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
Water Solubility	3.93 g/L	ALOGPS
logP	0.22	ALOGPS
logP	0.028	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	3.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	151.57 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.63 m³·mol⁻¹	ChemAxon
Polarizability	36.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001069

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022408

KNApSAcK ID

Not Available

Chemspider ID

1528

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5981

PubChem Compound

1585

PDB ID

Not Available

ChEBI ID

91804

Good Scents ID

Not Available

References

General References

Dionisotti S, Ongini E, Zocchi C, Kull B, Arslan G, Fredholm BB: Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261. Br J Pharmacol. 1997 Jun;121(3):353-60. [PubMed:9179373 ]
Wilson CN, Batra VK: Lipopolysaccharide binds to and activates A(1) adenosine receptors on human pulmonary artery endothelial cells. J Endotoxin Res. 2002;8(4):263-71. [PubMed:12230916 ]
Kull B, Arslan G, Nilsson C, Owman C, Lorenzen A, Schwabe U, Fredholm BB: Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors. Biochem Pharmacol. 1999 Jan 1;57(1):65-75. [PubMed:9920286 ]
Zhang H, Zhang S, Wang W, Wang Q, Kuang H, Wang Q: Characterizing metabolites and potential metabolic pathways changes to understanding the mechanism of medicinal plant Phellodendri Amurensis cortex against doxorubicin-induced nephritis rats using UPLC-Q/TOF-MS metabolomics. J Pharm Biomed Anal. 2020 Sep 5;188:113336. doi: 10.1016/j.jpba.2020.113336. Epub 2020 May 22. [PubMed:32653762 ]
Bader A, Bintig W, Begandt D, Klett A, Siller IG, Gregor C, Schaarschmidt F, Weksler B, Romero I, Couraud PO, Hell SW, Ngezahayo A: Adenosine receptors regulate gap junction coupling of the human cerebral microvascular endothelial cells hCMEC/D3 by Ca(2+) influx through cyclic nucleotide-gated channels. J Physiol. 2017 Apr 15;595(8):2497-2517. doi: 10.1113/JP273150. Epub 2017 Feb 14. [PubMed:28075020 ]

Showing NP-Card for 2-Phenylaminoadenosine (NP0000737)

MOL for NP0000737 (2-Phenylaminoadenosine)

3D MOL for NP0000737 (2-Phenylaminoadenosine)

3D SDF for NP0000737 (2-Phenylaminoadenosine)

3D-SDF for NP0000737 (2-Phenylaminoadenosine)

PDB for NP0000737 (2-Phenylaminoadenosine)

3D PDB for NP0000737 (2-Phenylaminoadenosine)

SMILES for NP0000737 (2-Phenylaminoadenosine)

INCHI for NP0000737 (2-Phenylaminoadenosine)

Structure for NP0000737 (2-Phenylaminoadenosine)

3D Structure for NP0000737 (2-Phenylaminoadenosine)