NP-MRD: Showing NP-Card for Toyocamycin (NP0021695)

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Record Information

Version

1.0

Created at

2021-01-06 06:58:09 UTC

Updated at

2021-07-15 17:37:02 UTC

NP-MRD ID

NP0021695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Toyocamycin

Provided By

NPAtlas

Description

Toyocamycin is also known as a-399-y4 or ahygroscopin-b. Toyocamycin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Toyocamycin is found in Streptomyces diastatochromogenes, Streptomyces toyocaensis and Tolypothrix tenuis. It was first documented in 1968 (PMID: 5634627). Based on a literature review a significant number of articles have been published on toyocamycin (PMID: 22629386) (PMID: 22852048) (PMID: 23775805) (PMID: 23900861).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 34 36  0  0  0  0            999 V2000
    4.6333   -1.1913   -2.9131 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -0.8911   -2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -0.5036   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -0.5071   -1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -0.0837   -0.5765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026    0.0246   -0.5994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2989    1.0221    0.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.8315    0.1004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4629    1.5730    1.1489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8092    1.3143    0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214   -0.6447    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5749   -1.0070   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.2051   -0.0099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4447   -2.2885   -0.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802    0.1827    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488    0.6243    1.6608 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.8171    2.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.5736    2.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.1299    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -0.1425    0.3413 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -0.0667   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781   -0.8059   -2.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    0.2070   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521    1.2907   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.6610    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265    1.2404    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9709    1.0150   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331   -1.0163    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.3485   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.4159    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213   -2.0702   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.1712    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7962    0.6385    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -1.1289    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21  3  1  0  0  0  0
 13  6  1  0  0  0  0
 21 15  1  0  0  0  0
  4 22  1  0  0  0  0
  6 23  1  6  0  0  0
  8 24  1  6  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  1  1  0  0  0
 12 29  1  0  0  0  0
 13 30  1  1  0  0  0
 14 31  1  0  0  0  0
 17 32  1  0  0  0  0
 20 33  1  0  0  0  0
 20 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    4.6333   -1.1913   -2.9131 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -0.8911   -2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -0.5036   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -0.5071   -1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -0.0837   -0.5765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026    0.0246   -0.5994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2989    1.0221    0.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.8315    0.1004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4629    1.5730    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    1.3143    0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214   -0.6447    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5749   -1.0070   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.2051   -0.0099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4447   -2.2885   -0.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802    0.1827    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488    0.6243    1.6608 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.8171    2.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.5736    2.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.1299    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -0.1425    0.3413 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -0.0667   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781   -0.8059   -2.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    0.2070   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521    1.2907   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.6610    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265    1.2404    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9709    1.0150   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331   -1.0163    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.3485   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.4159    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213   -2.0702   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.1712    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7962    0.6385    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -1.1289    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 13  6  1  0
 21 15  1  0
  4 22  1  0
  6 23  1  6
  8 24  1  6
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 13 30  1  1
 14 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
M  END


  Mrv1652306242105183D          

 34 36  0  0  0  0            999 V2000
    4.6333   -1.1913   -2.9131 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -0.8911   -2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -0.5036   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -0.5071   -1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -0.0837   -0.5765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026    0.0246   -0.5994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2989    1.0221    0.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.8315    0.1004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4629    1.5730    1.1489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8092    1.3143    0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214   -0.6447    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5749   -1.0070   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.2051   -0.0099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4447   -2.2885   -0.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802    0.1827    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488    0.6243    1.6608 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.8171    2.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.5736    2.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.1299    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -0.1425    0.3413 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -0.0667   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781   -0.8059   -2.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    0.2070   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521    1.2907   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.6610    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265    1.2404    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9709    1.0150   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331   -1.0163    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.3485   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.4159    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213   -2.0702   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.1712    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7962    0.6385    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -1.1289    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21  3  1  0  0  0  0
 13  6  1  0  0  0  0
 21 15  1  0  0  0  0
  4 22  1  0  0  0  0
  6 23  1  6  0  0  0
  8 24  1  6  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
 10 27  1  0  0  0  0
 11 28  1  1  0  0  0
 12 29  1  0  0  0  0
 13 30  1  1  0  0  0
 14 31  1  0  0  0  0
 17 32  1  0  0  0  0
 20 33  1  0  0  0  0
 20 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C([H])=C(C#N)C3=C(N=C([H])N=C23)N([H])[H])[C@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1

> <INCHI_KEY>
XOKJUSAYZUAMGJ-WOUKDFQISA-N

> <FORMULA>
C12H13N5O4

> <MOLECULAR_WEIGHT>
291.2627

> <EXACT_MASS>
291.096753929

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.765814908774292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

> <ALOGPS_LOGP>
-0.77

> <JCHEM_LOGP>
-1.4223638733333335

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.891812927040135

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.45562910172708

> <JCHEM_PKA_STRONGEST_BASIC>
4.695339199283504

> <JCHEM_POLAR_SURFACE_AREA>
150.44000000000003

> <JCHEM_REFRACTIVITY>
71.09319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    4.6333   -1.1913   -2.9131 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -0.8911   -2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -0.5036   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -0.5071   -1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -0.0837   -0.5765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026    0.0246   -0.5994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2989    1.0221    0.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.8315    0.1004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4629    1.5730    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    1.3143    0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214   -0.6447    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5749   -1.0070   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.2051   -0.0099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4447   -2.2885   -0.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802    0.1827    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488    0.6243    1.6608 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.8171    2.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.5736    2.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.1299    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -0.1425    0.3413 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -0.0667   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781   -0.8059   -2.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    0.2070   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521    1.2907   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.6610    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265    1.2404    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9709    1.0150   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331   -1.0163    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.3485   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.4159    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213   -2.0702   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.1712    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7962    0.6385    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -1.1289    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 13  6  1  0
 21 15  1  0
  4 22  1  0
  6 23  1  6
  8 24  1  6
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 13 30  1  1
 14 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  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       4.633  -1.191  -2.913  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.776  -0.891  -2.193  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.708  -0.504  -1.309  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.352  -0.507  -1.646  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.617  -0.084  -0.577  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.803   0.025  -0.599  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.299   1.022   0.235  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.676   0.832   0.100  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.463   1.573   1.149  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.809   1.314   0.922  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.921  -0.645   0.126  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.575  -1.007  -1.075  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.499  -1.205  -0.010  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.445  -2.289  -0.850  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.480   0.183   0.416  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.249   0.624   1.661  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.319   0.817   2.486  0.00  0.00           C+0
HETATM   18  N   UNK     0       3.590   0.574   2.075  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.843   0.130   0.830  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.145  -0.143   0.341  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.771  -0.067  -0.007  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.978  -0.806  -2.616  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.223   0.207  -1.602  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.952   1.291  -0.887  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.300   2.661   0.996  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.227   1.240   2.175  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.971   1.015  -0.025  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.433  -1.016   1.011  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.292  -0.349  -1.777  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.105  -1.416   1.001  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.921  -2.070  -1.684  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.204   1.171   3.501  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.796   0.639   0.125  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.452  -1.129   0.197  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   13   23                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   11   24                                             
CONECT    9    8   10   25   26                                             
CONECT   10    9   27                                                       
CONECT   11    8   12   13   28                                             
CONECT   12   11   29                                                       
CONECT   13   11   14    6   30                                             
CONECT   14   13   31                                                       
CONECT   15    5   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   33   34                                                  
CONECT   21   19    3   15                                                  
CONECT   22    4                                                            
CONECT   23    6                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   17                                                            
CONECT   33   20                                                            
CONECT   34   20                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
    4.6333   -1.1913   -2.9131 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7761   -0.8911   -2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -0.5036   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3523   -0.5071   -1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -0.0837   -0.5765 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8026    0.0246   -0.5994 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2989    1.0221    0.2349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.8315    0.1004 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4629    1.5730    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8092    1.3143    0.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214   -0.6447    0.1259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5749   -1.0070   -1.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -1.2051   -0.0099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4447   -2.2885   -0.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4802    0.1827    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488    0.6243    1.6608 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189    0.8171    2.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5900    0.5736    2.0755 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432    0.1299    0.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -0.1425    0.3413 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -0.0667   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781   -0.8059   -2.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    0.2070   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9521    1.2907   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    2.6610    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2265    1.2404    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9709    1.0150   -0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331   -1.0163    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -0.3485   -1.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1045   -1.4159    1.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9213   -2.0702   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036    1.1712    3.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7962    0.6385    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521   -1.1289    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 13  6  1  0
 21 15  1  0
  4 22  1  0
  6 23  1  6
  8 24  1  6
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  1
 12 29  1  0
 13 30  1  1
 14 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Amino-5-cyano-7-(D-ribofuranosyl)-7H-pyrrolo(2,3-D)pyrimidine	ChEBI
7-Deaza-7-cyanoadenosine	ChEBI
a-399-Y4	ChEBI
Ahygroscopin-b	ChEBI
Antibiotic 1037	ChEBI
Antibiotic a-399-y4	ChEBI
Antibiotic e212	ChEBI
Cyanotubericidin	ChEBI
e-212	ChEBI
Siromycin	ChEBI
Uramycin b	ChEBI
Vengicide	ChEBI
UNAMYCIN b	ChEMBL
Toyokamycin	MeSH
Deazacyanoadenosine	MeSH

Chemical Formula

C₁₂H₁₃N₅O₄

Average Mass

291.2627 Da

Monoisotopic Mass

291.09675 Da

IUPAC Name

4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Traditional Name

4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1C(=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C#N

InChI Identifier

InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1

InChI Key

XOKJUSAYZUAMGJ-WOUKDFQISA-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 diastatochromogenes	LOTUS Database	35616633
Streptomyces toyocaensis	NPAtlas	5634627
Tolypothrix tenuis	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Thermoactinomyces sp. A6019	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrrolopyrimidine nucleosides and nucleotides

Sub Class

Not Available

Direct Parent

Pyrrolopyrimidine nucleosides and nucleotides

Alternative Parents

Substituents

Pyrrolopyrimidine ribonucleoside
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
Pyrrolo[2,3-d]pyrimidine
Pyrrolopyrimidine
Aminopyrimidine
Monosaccharide
Pyrimidine
Imidolactam
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Tetrahydrofuran
Secondary alcohol
Carbonitrile
Nitrile
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Primary amine
Organic oxygen compound
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	-0.77	ALOGPS
logP	-1.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.09 m³·mol⁻¹	ChemAxon
Polarizability	27.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA006347

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017105

Chemspider ID

11331

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11824

PDB ID

Not Available

ChEBI ID

134606

Good Scents ID

Not Available

References

General References

Tolman RL, Robins RK, Townsend LB: Pyrrolo[2,3-d]pyrimidine nucleoside antibiotics. Total synthesis and structure of toyocamycin, unamycin B, vengicide, antibiotic E-212, and Sangivamycin (BA-90912). J Am Chem Soc. 1968 Jan 17;90(2):524-6. doi: 10.1021/ja01004a076. [PubMed:5634627 ]
Kiburu IN, LaRonde-LeBlanc N: Interaction of Rio1 kinase with toyocamycin reveals a conformational switch that controls oligomeric state and catalytic activity. PLoS One. 2012;7(5):e37371. doi: 10.1371/journal.pone.0037371. Epub 2012 May 22. [PubMed:22629386 ]
Ri M, Tashiro E, Oikawa D, Shinjo S, Tokuda M, Yokouchi Y, Narita T, Masaki A, Ito A, Ding J, Kusumoto S, Ishida T, Komatsu H, Shiotsu Y, Ueda R, Iwawaki T, Imoto M, Iida S: Identification of Toyocamycin, an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing. Blood Cancer J. 2012 Jul;2(7):e79. doi: 10.1038/bcj.2012.26. Epub 2012 Jul 20. [PubMed:22852048 ]
Ma Z, Liu J, Shentu X, Bian Y, Yu X: Optimization of electroporation conditions for toyocamycin producer Streptomyces diastatochromogenes 1628. J Basic Microbiol. 2014 Apr;54(4):278-84. doi: 10.1002/jobm.201200489. Epub 2013 Jun 17. [PubMed:23775805 ]
Ma Z, Liu J, Lin X, Shentu X, Bian Y, Yu X: Formation, regeneration, and transformation of protoplasts of Streptomyces diastatochromogenes 1628. Folia Microbiol (Praha). 2014 Mar;59(2):93-7. doi: 10.1007/s12223-013-0271-5. Epub 2013 Jul 31. [PubMed:23900861 ]

Showing NP-Card for Toyocamycin (NP0021695)

MOL for NP0021695 (Toyocamycin)

3D MOL for NP0021695 (Toyocamycin)

3D SDF for NP0021695 (Toyocamycin)

3D-SDF for NP0021695 (Toyocamycin)

PDB for NP0021695 (Toyocamycin)

3D PDB for NP0021695 (Toyocamycin)

SMILES for NP0021695 (Toyocamycin)

INCHI for NP0021695 (Toyocamycin)

Structure for NP0021695 (Toyocamycin)

3D Structure for NP0021695 (Toyocamycin)