NP-MRD: Showing NP-Card for Griseolic acid (NP0018294)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 02:57:00 UTC

Updated at

2021-07-15 17:27:49 UTC

NP-MRD ID

NP0018294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Griseolic acid

Provided By

NPAtlas

Description

(2R,5R,6R,6aR)-5-(6-amino-9H-purin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-2H,5H,6H,6aH-furo[3,2-b]furan-2-carboxylic acid belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Griseolic acid is found in Streptomyces, Streptomyces griseoaurantiacus and Streptomyces griseoaurantiacus SANK 63479. Griseolic acid was first documented in 1985 (PMID: 2993219). Based on a literature review very few articles have been published on (2R,5R,6R,6aR)-5-(6-amino-9H-purin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-2H,5H,6H,6aH-furo[3,2-b]furan-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104323D          

 40 43  0  0  0  0            999 V2000
    6.8155   -0.9710   -0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5893   -0.6224    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4684   -0.6774    1.7931 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -0.3536    2.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.0395    1.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983    0.1206    0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837   -0.2166   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0686   -1.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.3520   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271    0.4669   -0.5980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    0.8805   -0.3900 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5351    0.4824    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.2624    0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.1600    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0130    0.2121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6771    1.3181    0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776    1.5939    1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    2.2676   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0329   -1.0985    0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8512   -0.9212   -0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -1.0280    1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -1.1562    2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2085   -0.8129    1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.0811   -0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.7090   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1099    0.2603   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2439    0.8024   -2.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3177   -1.8342    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983   -0.3248   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.4014    3.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    0.5523   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    1.9806   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -0.5434    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496    2.0455   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679   -2.0917    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086   -0.0514   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -1.5082    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    1.7859   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.8310   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    0.0582   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7  2  1  0  0  0  0
 26 11  1  0  0  0  0
 10  6  1  0  0  0  0
 25 13  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 30  1  0  0  0  0
  9 31  1  0  0  0  0
 11 32  1  1  0  0  0
 14 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
 20 36  1  0  0  0  0
 23 37  1  0  0  0  0
 25 38  1  1  0  0  0
 26 39  1  6  0  0  0
 27 40  1  0  0  0  0
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    6.8155   -0.9710   -0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5893   -0.6224    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4684   -0.6774    1.7931 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -0.3536    2.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.0395    1.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983    0.1206    0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837   -0.2166   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0686   -1.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.3520   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271    0.4669   -0.5980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    0.8805   -0.3900 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5351    0.4824    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.2624    0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.1600    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0130    0.2121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6771    1.3181    0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776    1.5939    1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    2.2676   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0329   -1.0985    0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8512   -0.9212   -0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -1.0280    1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -1.1562    2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2085   -0.8129    1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.0811   -0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.7090   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1099    0.2603   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2439    0.8024   -2.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3177   -1.8342    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983   -0.3248   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.4014    3.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    0.5523   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    1.9806   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -0.5434    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496    2.0455   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679   -2.0917    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086   -0.0514   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -1.5082    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    1.7859   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.8310   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    0.0582   -3.3052 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  7  2  1  0
 26 11  1  0
 10  6  1  0
 25 13  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 11 32  1  1
 14 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 23 37  1  0
 25 38  1  1
 26 39  1  6
 27 40  1  0
M  END


  Mrv1652306242104323D          

 40 43  0  0  0  0            999 V2000
    6.8155   -0.9710   -0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5893   -0.6224    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4684   -0.6774    1.7931 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -0.3536    2.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.0395    1.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983    0.1206    0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837   -0.2166   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0686   -1.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.3520   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271    0.4669   -0.5980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    0.8805   -0.3900 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5351    0.4824    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.2624    0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.1600    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0130    0.2121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6771    1.3181    0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776    1.5939    1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    2.2676   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0329   -1.0985    0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8512   -0.9212   -0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -1.0280    1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -1.1562    2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2085   -0.8129    1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.0811   -0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.7090   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1099    0.2603   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2439    0.8024   -2.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3177   -1.8342    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983   -0.3248   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.4014    3.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    0.5523   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    1.9806   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -0.5434    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496    2.0455   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679   -2.0917    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086   -0.0514   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -1.5082    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    1.7859   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.8310   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    0.0582   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7  2  1  0  0  0  0
 26 11  1  0  0  0  0
 10  6  1  0  0  0  0
 25 13  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 30  1  0  0  0  0
  9 31  1  0  0  0  0
 11 32  1  1  0  0  0
 14 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  6  0  0  0
 20 36  1  0  0  0  0
 23 37  1  0  0  0  0
 25 38  1  1  0  0  0
 26 39  1  6  0  0  0
 27 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0018294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(O[H])[C@@]1(O[C@@]2([H])C(O[C@@]([H])(N3C([H])=NC4=C3N=C([H])N=C4N([H])[H])[C@]2([H])O[H])=C1[H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H13N5O8/c15-9-5-10(17-2-16-9)19(3-18-5)11-6(20)7-4(26-11)1-14(27-7,13(24)25)8(21)12(22)23/h1-3,6-8,11,20-21H,(H,22,23)(H,24,25)(H2,15,16,17)/t6-,7+,8-,11-,14-/m1/s1

> <INCHI_KEY>
IAPZXUKYTCQQFE-FTRAOVNNSA-N

> <FORMULA>
C14H13N5O8

> <MOLECULAR_WEIGHT>
379.285

> <EXACT_MASS>
379.076412399

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.87234963590681

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R,6R,6aR)-5-(6-amino-9H-purin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-2H,5H,6H,6aH-furo[3,2-b]furan-2-carboxylic acid

> <ALOGPS_LOGP>
-1.16

> <JCHEM_LOGP>
-3.4919252834996244

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.660813941253341

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.827693648771934

> <JCHEM_PKA_STRONGEST_BASIC>
3.8683299002154854

> <JCHEM_POLAR_SURFACE_AREA>
203.13999999999996

> <JCHEM_REFRACTIVITY>
83.85069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R,6R,6aR)-5-(6-aminopurin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-5H,6H,6aH-furo[3,2-b]furan-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    6.8155   -0.9710   -0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5893   -0.6224    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4684   -0.6774    1.7931 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -0.3536    2.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.0395    1.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983    0.1206    0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837   -0.2166   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0686   -1.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.3520   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271    0.4669   -0.5980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    0.8805   -0.3900 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5351    0.4824    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.2624    0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.1600    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0130    0.2121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6771    1.3181    0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776    1.5939    1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    2.2676   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0329   -1.0985    0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8512   -0.9212   -0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -1.0280    1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -1.1562    2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2085   -0.8129    1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.0811   -0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.7090   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1099    0.2603   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2439    0.8024   -2.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3177   -1.8342    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983   -0.3248   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.4014    3.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    0.5523   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    1.9806   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -0.5434    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496    2.0455   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679   -2.0917    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086   -0.0514   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -1.5082    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    1.7859   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.8310   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    0.0582   -3.3052 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  7  2  1  0
 26 11  1  0
 10  6  1  0
 25 13  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 11 32  1  1
 14 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 23 37  1  0
 25 38  1  1
 26 39  1  6
 27 40  1  0
M  END

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  N   UNK     0       6.816  -0.971  -0.180  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.589  -0.622   0.459  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.468  -0.677   1.793  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.321  -0.354   2.424  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.252   0.040   1.712  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.298   0.121   0.350  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.484  -0.217  -0.265  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.309  -0.069  -1.571  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.043   0.352  -1.775  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.427   0.467  -0.598  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.093   0.881  -0.390  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.535   0.482   0.833  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.830   0.262   0.699  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.956  -0.160   1.238  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.000   0.013   0.212  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.677   1.318   0.278  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.378   1.594   1.281  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.581   2.268  -0.721  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.033  -1.099   0.252  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.851  -0.921  -0.861  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.844  -1.028   1.460  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.354  -1.156   2.610  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.208  -0.813   1.375  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.263  -0.081  -0.968  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.189   0.709  -0.699  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.110   0.260  -1.390  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.244   0.802  -2.642  0.00  0.00           O+0
HETATM   28  H   UNK     0       7.318  -1.834   0.049  0.00  0.00           H+0
HETATM   29  H   UNK     0       7.198  -0.325  -0.894  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.234  -0.401   3.501  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.639   0.552  -2.780  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.989   1.981  -0.502  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.005  -0.543   2.248  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.550   2.046  -1.707  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.568  -2.092   0.152  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.309  -0.051  -0.734  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.893  -1.508   1.155  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.318   1.786  -0.754  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.114  -0.831  -1.348  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.325   0.058  -3.305  0.00  0.00           H+0
CONECT    1    2   28   29                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10   12   26   32                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16   19   24                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   34                                                       
CONECT   19   15   20   21   35                                             
CONECT   20   19   36                                                       
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   37                                                       
CONECT   24   15   25                                                       
CONECT   25   24   26   13   38                                             
CONECT   26   25   27   11   39                                             
CONECT   27   26   40                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   14                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   23                                                            
CONECT   38   25                                                            
CONECT   39   26                                                            
CONECT   40   27                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

RDKit          3D

40 43  0  0  0  0  0  0  0  0999 V2000
    6.8155   -0.9710   -0.1800 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5893   -0.6224    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4684   -0.6774    1.7931 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3213   -0.3536    2.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2525    0.0395    1.7123 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983    0.1206    0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4837   -0.2166   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087   -0.0686   -1.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0430    0.3520   -1.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4271    0.4669   -0.5980 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    0.8805   -0.3900 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5351    0.4824    0.8332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    0.2624    0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.1600    1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0130    0.2121 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6771    1.3181    0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776    1.5939    1.2805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    2.2676   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0329   -1.0985    0.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8512   -0.9212   -0.8607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8438   -1.0280    1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3538   -1.1562    2.6102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2085   -0.8129    1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2631   -0.0811   -0.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.7090   -0.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1099    0.2603   -1.3901 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2439    0.8024   -2.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3177   -1.8342    0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1983   -0.3248   -0.8937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -0.4014    3.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    0.5523   -2.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9886    1.9806   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -0.5434    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496    2.0455   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679   -2.0917    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3086   -0.0514   -0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8929   -1.5082    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    1.7859   -0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1141   -0.8310   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    0.0582   -3.3052 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  7  2  1  0
 26 11  1  0
 10  6  1  0
 25 13  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 11 32  1  1
 14 33  1  0
 18 34  1  0
 19 35  1  6
 20 36  1  0
 23 37  1  0
 25 38  1  1
 26 39  1  6
 27 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,5R,6R,6AR)-5-(6-amino-9H-purin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-2H,5H,6H,6ah-furo[3,2-b]furan-2-carboxylate	Generator
Griseolate	Generator

Chemical Formula

C₁₄H₁₃N₅O₈

Average Mass

379.2850 Da

Monoisotopic Mass

379.07641 Da

IUPAC Name

(2R,5R,6R,6aR)-5-(6-amino-9H-purin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-2H,5H,6H,6aH-furo[3,2-b]furan-2-carboxylic acid

Traditional Name

(2R,5R,6R,6aR)-5-(6-aminopurin-9-yl)-2-[(S)-carboxy(hydroxy)methyl]-6-hydroxy-5H,6H,6aH-furo[3,2-b]furan-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1OC2=C[C@@](O[C@@H]2[C@H]1O)([C@H](O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C14H13N5O8/c15-9-5-10(17-2-16-9)19(3-18-5)11-6(20)7-4(26-11)1-14(27-7,13(24)25)8(21)12(22)23/h1-3,6-8,11,20-21H,(H,22,23)(H,24,25)(H2,15,16,17)/t6-,7+,8-,11-,14-/m1/s1

InChI Key

IAPZXUKYTCQQFE-FTRAOVNNSA-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
Streptomyces	NPAtlas	2993219
Streptomyces griseoaurantiacus	LOTUS Database	35616633
Streptomyces griseoaurantiacus SANK 63479	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Beta-hydroxy acid
Aminopyrimidine
Imidolactam
Pyrimidine
N-substituted imidazole
Hydroxy acid
Dicarboxylic acid or derivatives
Alpha-hydroxy acid
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Dihydrofuran
Azole
Amino acid
Secondary alcohol
Amino acid or derivatives
Oxacycle
Azacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-1.2	ALOGPS
logP	-3.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.83	ChemAxon
pKa (Strongest Basic)	3.87	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	203.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.85 m³·mol⁻¹	ChemAxon
Polarizability	32.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020881

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78443024

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13745497

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takahashi S, Nakagawa F, Kawazoe K, Furukawa Y, Sato S, Tamura C, Naito A: Griseolic acid, an inhibitor of cyclic adenosine 3',5'-monophosphate phosphodiesterase. II. The structure of griseolic acid. J Antibiot (Tokyo). 1985 Jul;38(7):830-4. doi: 10.7164/antibiotics.38.830. [PubMed:2993219 ]

Showing NP-Card for Griseolic acid (NP0018294)

MOL for NP0018294 (Griseolic acid)

3D MOL for NP0018294 (Griseolic acid)

3D SDF for NP0018294 (Griseolic acid)

3D-SDF for NP0018294 (Griseolic acid)

PDB for NP0018294 (Griseolic acid)

3D PDB for NP0018294 (Griseolic acid)

SMILES for NP0018294 (Griseolic acid)

INCHI for NP0018294 (Griseolic acid)

Structure for NP0018294 (Griseolic acid)

3D Structure for NP0018294 (Griseolic acid)