NP-MRD: Showing NP-Card for Leutinacin (NP0021613)

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Record Information

Version

2.0

Created at

2021-01-06 06:53:45 UTC

Updated at

2021-07-15 17:36:48 UTC

NP-MRD ID

NP0021613

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leutinacin

Provided By

NPAtlas

Description

Leutinacin is found in Lentinus and Lentinula edodes. Leutinacin was first documented in 2002 (PMID: 11741948). Based on a literature review very few articles have been published on D-Eritadenine (PMID: 20412798) (PMID: 17559404) (PMID: 17214973).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242105173D          

 29 30  0  0  0  0            999 V2000
    5.1269   -0.6994    0.7462 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -0.2651    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398    0.0251   -1.2992 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    0.4391   -2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5809   -1.4052 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.3032   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -0.1179    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223   -0.3083    1.8819 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.0119    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.3669    0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8058    0.7615    0.3982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6286   -0.4049   -0.0266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7373   -1.3950    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    0.0606   -0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6869   -1.0414   -1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    0.6384    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.6572    1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0625    0.0445    0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146   -1.6451    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -0.1380    1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.6638   -3.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -0.0728    2.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    1.2071    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521    1.5366   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.8874   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -2.1018    0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022    0.8077   -1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.6795   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    0.6760    0.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  7  2  1  0  0  0  0
 10  6  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  4 21  1  0  0  0  0
  9 22  1  0  0  0  0
 11 23  1  0  0  0  0
 11 24  1  0  0  0  0
 12 25  1  6  0  0  0
 13 26  1  0  0  0  0
 14 27  1  6  0  0  0
 15 28  1  0  0  0  0
 18 29  1  0  0  0  0
M  END

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.1269   -0.6994    0.7462 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -0.2651    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398    0.0251   -1.2992 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    0.4391   -2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5809   -1.4052 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.3032   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -0.1179    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223   -0.3083    1.8819 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.0119    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.3669    0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8058    0.7615    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.4049   -0.0266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7373   -1.3950    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    0.0606   -0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6869   -1.0414   -1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    0.6384    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.6572    1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0625    0.0445    0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146   -1.6451    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -0.1380    1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.6638   -3.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -0.0728    2.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    1.2071    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521    1.5366   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.8874   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -2.1018    0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022    0.8077   -1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.6795   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    0.6760    0.8141 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
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  7  2  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  9 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  6
 13 26  1  0
 14 27  1  6
 15 28  1  0
 18 29  1  0
M  END

  Mrv1652306242105173D          

 29 30  0  0  0  0            999 V2000
    5.1269   -0.6994    0.7462 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -0.2651    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398    0.0251   -1.2992 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    0.4391   -2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5809   -1.4052 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.3032   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -0.1179    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223   -0.3083    1.8819 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.0119    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.3669    0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8058    0.7615    0.3982 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6286   -0.4049   -0.0266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7373   -1.3950    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    0.0606   -0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6869   -1.0414   -1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    0.6384    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.6572    1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0625    0.0445    0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146   -1.6451    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -0.1380    1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.6638   -3.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -0.0728    2.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8521    1.5366   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9022    0.8077   -1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.6795   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    0.6760    0.8141 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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  7  2  1  0  0  0  0
 10  6  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  4 21  1  0  0  0  0
  9 22  1  0  0  0  0
 11 23  1  0  0  0  0
 11 24  1  0  0  0  0
 12 25  1  6  0  0  0
 13 26  1  0  0  0  0
 14 27  1  6  0  0  0
 15 28  1  0  0  0  0
 18 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021613

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])N1C([H])=NC2=C1N=C([H])N=C2N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1

> <INCHI_KEY>
LIEMBEWXEZJEEZ-INEUFUBQSA-N

> <FORMULA>
C9H11N5O4

> <MOLECULAR_WEIGHT>
253.2147

> <EXACT_MASS>
253.081103865

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.320635922485792

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-4-(6-amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-3.0890856023954716

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.12248293727627

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2115093556507706

> <JCHEM_PKA_STRONGEST_BASIC>
4.185881205504833

> <JCHEM_POLAR_SURFACE_AREA>
147.38

> <JCHEM_REFRACTIVITY>
59.58070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-4-(6-aminopurin-9-yl)-2,3-dihydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    5.1269   -0.6994    0.7462 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -0.2651    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398    0.0251   -1.2992 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    0.4391   -2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5809   -1.4052 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.3032   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -0.1179    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223   -0.3083    1.8819 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.0119    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.3669    0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8058    0.7615    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.4049   -0.0266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7373   -1.3950    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    0.0606   -0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6869   -1.0414   -1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    0.6384    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.6572    1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0625    0.0445    0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146   -1.6451    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -0.1380    1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.6638   -3.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -0.0728    2.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    1.2071    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521    1.5366   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.8874   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -2.1018    0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022    0.8077   -1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.6795   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    0.6760    0.8141 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
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  7  2  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  9 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  6
 13 26  1  0
 14 27  1  6
 15 28  1  0
 18 29  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       5.127  -0.699   0.746  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.987  -0.265   0.014  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.040   0.025  -1.299  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.955   0.439  -2.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.757   0.581  -1.405  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.643   0.303  -0.085  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.748  -0.118   0.626  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.322  -0.308   1.882  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.990  -0.012   1.940  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.570   0.367   0.722  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.806   0.762   0.398  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.629  -0.405  -0.027  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.737  -1.395   0.946  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.989   0.061  -0.497  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.687  -1.041  -1.065  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.828   0.638   0.558  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.526   1.657   1.232  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.063   0.045   0.870  0.00  0.00           O+0
HETATM   19  H   UNK     0       5.515  -1.645   0.542  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.604  -0.138   1.476  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.047   0.664  -3.068  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.374  -0.073   2.827  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.289   1.207   1.317  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.852   1.537  -0.379  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.145  -0.887  -0.934  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.043  -2.102   0.799  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.902   0.808  -1.310  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.320  -0.680  -1.728  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.864   0.676   0.814  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11    6                                                  
CONECT   11   10   12   23   24                                             
CONECT   12   11   13   14   25                                             
CONECT   13   12   26                                                       
CONECT   14   12   15   16   27                                             
CONECT   15   14   28                                                       
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   29                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    4                                                            
CONECT   22    9                                                            
CONECT   23   11                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   15                                                            
CONECT   29   18                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

RDKit          3D

29 30  0  0  0  0  0  0  0  0999 V2000
    5.1269   -0.6994    0.7462 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868   -0.2651    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0398    0.0251   -1.2992 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    0.4391   -2.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5809   -1.4052 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6426    0.3032   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484   -0.1179    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223   -0.3083    1.8819 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904   -0.0119    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.3669    0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8058    0.7615    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286   -0.4049   -0.0266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7373   -1.3950    0.9458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9891    0.0606   -0.4969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6869   -1.0414   -1.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275    0.6384    0.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5257    1.6572    1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0625    0.0445    0.8703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146   -1.6451    0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6045   -0.1380    1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0470    0.6638   -3.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -0.0728    2.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2889    1.2071    1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8521    1.5366   -0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.8874   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0432   -2.1018    0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022    0.8077   -1.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3198   -0.6795   -1.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8639    0.6760    0.8141 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
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  7  2  1  0
 10  6  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  9 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  6
 13 26  1  0
 14 27  1  6
 15 28  1  0
 18 29  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Eritadenine, (S-(r,r))-isomer	MeSH
Eritadenine, monosodium salt, (R-(r,r))-isomer	MeSH
6-amino-alpha,beta-Dihydroxy-9H-purine-9-butanoic acid	MeSH
Eritadenine, (S-(r,s))-isomer	MeSH
Eritadenine	MeSH
Eritadenine, monosodium salt, (S-(r,r))-isomer	MeSH
Eritadenine, (R-(r,s))-isomer	MeSH
(2R,3R)-4-(6-Amino-9H-purin-9-yl)-2,3-dihydroxybutanoate	Generator

Chemical Formula

C₉H₁₁N₅O₄

Average Mass

253.2147 Da

Monoisotopic Mass

253.08110 Da

IUPAC Name

(2R,3R)-4-(6-amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid

Traditional Name

(2R,3R)-4-(6-aminopurin-9-yl)-2,3-dihydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2C[C@@H](O)[C@@H](O)C(O)=O

InChI Identifier

InChI=1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)/t4-,6-/m1/s1

InChI Key

LIEMBEWXEZJEEZ-INEUFUBQSA-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
Lentinus	NPAtlas	5391883
Lentinus edodes	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound 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
Aminopyrimidine
Beta-hydroxy acid
Sugar acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Heteroaromatic compound
Azole
Imidazole
Secondary alcohol
Amino acid
Amino acid or derivatives
1,2-diol
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
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	-1.7	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	4.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	147.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.58 m³·mol⁻¹	ChemAxon
Polarizability	23.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016035

HMDB ID

Not Available

DrugBank ID

DB03769

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

140628

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Eritadenine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ctrnacta V, Fritzler JM, Surinova M, Hrdy I, Zhu G, Stejskal F: Efficacy of S-adenosylhomocysteine hydrolase inhibitors, D-eritadenine and (S)-DHPA, against the growth of Cryptosporidium parvum in vitro. Exp Parasitol. 2010 Oct;126(2):113-6. doi: 10.1016/j.exppara.2010.04.007. Epub 2010 Apr 20. [PubMed:20412798 ]
Ctrnacta V, Stejskal F, Keithly JS, Hrdy I: Characterization of S-adenosylhomocysteine hydrolase from Cryptosporidium parvum. FEMS Microbiol Lett. 2007 Aug;273(1):87-95. doi: 10.1111/j.1574-6968.2007.00795.x. Epub 2007 Jun 7. [PubMed:17559404 ]
Yamada T, Komoto J, Lou K, Ueki A, Hua DH, Sugiyama K, Takata Y, Ogawa H, Takusagawa F: Structure and function of eritadenine and its 3-deaza analogues: potent inhibitors of S-adenosylhomocysteine hydrolase and hypocholesterolemic agents. Biochem Pharmacol. 2007 Apr 1;73(7):981-9. doi: 10.1016/j.bcp.2006.12.014. Epub 2006 Dec 14. [PubMed:17214973 ]
Huang Y, Komoto J, Takata Y, Powell DR, Gomi T, Ogawa H, Fujioka M, Takusagawa F: Inhibition of S-adenosylhomocysteine hydrolase by acyclic sugar adenosine analogue D-eritadenine. Crystal structure of S-adenosylhomocysteine hydrolase complexed with D-eritadenine. J Biol Chem. 2002 Mar 1;277(9):7477-82. doi: 10.1074/jbc.M109187200. Epub 2001 Dec 10. [PubMed:11741948 ]

Showing NP-Card for Leutinacin (NP0021613)

MOL for NP0021613 (Leutinacin)

3D MOL for NP0021613 (Leutinacin)

3D SDF for NP0021613 (Leutinacin)

3D-SDF for NP0021613 (Leutinacin)

PDB for NP0021613 (Leutinacin)

3D PDB for NP0021613 (Leutinacin)

SMILES for NP0021613 (Leutinacin)

INCHI for NP0021613 (Leutinacin)

Structure for NP0021613 (Leutinacin)

3D Structure for NP0021613 (Leutinacin)