NP-MRD: Showing NP-Card for Sangivamycin (NP0021733)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 07:00:30 UTC

Updated at

2021-07-15 17:37:07 UTC

NP-MRD ID

NP0021733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sangivamycin

Provided By

NPAtlas

Description

Sangivamycin 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. Sangivamycin is found in Streptomyces sp. Sangivamycin was first documented in 1968 (PMID: 5748694). Based on a literature review very few articles have been published on sangivamycin (PMID: 3338987).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 37 39  0  0  0  0            999 V2000
   -4.8292   -1.6023    0.2725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.9454    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.2081    0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552   -1.0731   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -1.4911   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323   -0.4370   -0.4577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.4964   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8301   -1.1933    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1643   -0.8616    0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7440   -0.7297    1.7017 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0882   -0.3953    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    0.4471   -0.3997 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8304    0.1910   -1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    0.8623   -0.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6786    1.6060   -1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.6603   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    1.9535   -0.4925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    2.9341   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    2.6192   -0.1991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    1.3123   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5777    1.0408    0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.2988   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5354   -1.5016   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.4343    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -2.5343   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -0.9085   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -1.6746   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768   -1.7030    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.0451    2.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5594   -1.0376    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    1.2003    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886   -0.7642   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.4363    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    2.5451   -1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168    3.9547   -0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    0.9814    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.9032   -0.7062 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
  2  4  1  0  0  0  0
  4  5  2  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
 10 11  1  0  0  0  0
  9 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
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22  4  1  0  0  0  0
 14  7  1  0  0  0  0
 22 16  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  7 26  1  6  0  0  0
  9 27  1  6  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  1  0  0  0
 13 32  1  0  0  0  0
 14 33  1  1  0  0  0
 15 34  1  0  0  0  0
 18 35  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.8292   -1.6023    0.2725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.9454    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.2081    0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552   -1.0731   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -1.4911   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323   -0.4370   -0.4577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.4964   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8301   -1.1933    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1643   -0.8616    0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7440   -0.7297    1.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0882   -0.3953    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    0.4471   -0.3997 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8304    0.1910   -1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    0.8623   -0.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6786    1.6060   -1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.6603   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    1.9535   -0.4925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    2.9341   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    2.6192   -0.1991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    1.3123   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5777    1.0408    0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.2988   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5354   -1.5016   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.4343    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -2.5343   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -0.9085   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -1.6746   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768   -1.7030    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.0451    2.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5594   -1.0376    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    1.2003    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886   -0.7642   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.4363    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    2.5451   -1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168    3.9547   -0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    0.9814    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.9032   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  4  1  0
 14  7  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  6
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 14 33  1  1
 15 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
M  END


  Mrv1652306242105183D          

 37 39  0  0  0  0            999 V2000
   -4.8292   -1.6023    0.2725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.9454    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.2081    0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552   -1.0731   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -1.4911   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323   -0.4370   -0.4577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.4964   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8301   -1.1933    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1643   -0.8616    0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7440   -0.7297    1.7017 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0882   -0.3953    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    0.4471   -0.3997 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8304    0.1910   -1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    0.8623   -0.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6786    1.6060   -1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.6603   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    1.9535   -0.4925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    2.9341   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    2.6192   -0.1991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    1.3123   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5777    1.0408    0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.2988   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5354   -1.5016   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.4343    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -2.5343   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -0.9085   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -1.6746   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768   -1.7030    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.0451    2.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5594   -1.0376    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    1.2003    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886   -0.7642   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.4363    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    2.5451   -1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168    3.9547   -0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    0.9814    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.9032   -0.7062 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
  2  4  1  0  0  0  0
  4  5  2  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
 10 11  1  0  0  0  0
  9 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
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22  4  1  0  0  0  0
 14  7  1  0  0  0  0
 22 16  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  7 26  1  6  0  0  0
  9 27  1  6  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  1  0  0  0
 13 32  1  0  0  0  0
 14 33  1  1  0  0  0
 15 34  1  0  0  0  0
 18 35  1  0  0  0  0
 21 36  1  0  0  0  0
 21 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021733

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1

> <INCHI_KEY>
OBZJZDHRXBKKTJ-JTFADIMSSA-N

> <FORMULA>
C12H15N5O5

> <MOLECULAR_WEIGHT>
309.278

> <EXACT_MASS>
309.107318615

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.36418289880128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <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-carboxamide

> <ALOGPS_LOGP>
-1.45

> <JCHEM_LOGP>
-2.4278197673333333

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.75193413705691

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.449251645778105

> <JCHEM_PKA_STRONGEST_BASIC>
5.699891985585614

> <JCHEM_POLAR_SURFACE_AREA>
169.74000000000004

> <JCHEM_REFRACTIVITY>
74.44999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+01 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-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -4.8292   -1.6023    0.2725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.9454    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.2081    0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552   -1.0731   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -1.4911   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323   -0.4370   -0.4577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.4964   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8301   -1.1933    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1643   -0.8616    0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7440   -0.7297    1.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0882   -0.3953    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    0.4471   -0.3997 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8304    0.1910   -1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    0.8623   -0.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6786    1.6060   -1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.6603   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    1.9535   -0.4925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    2.9341   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    2.6192   -0.1991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    1.3123   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5777    1.0408    0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.2988   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5354   -1.5016   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.4343    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -2.5343   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -0.9085   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -1.6746   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768   -1.7030    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.0451    2.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5594   -1.0376    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    1.2003    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886   -0.7642   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.4363    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    2.5451   -1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168    3.9547   -0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    0.9814    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.9032   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  4  1  0
 14  7  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  6
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 14 33  1  1
 15 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  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      -4.829  -1.602   0.273  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.489  -1.945   0.089  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.256  -3.208   0.108  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.355  -1.073  -0.116  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.024  -1.491  -0.296  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.232  -0.437  -0.458  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.186  -0.496  -0.665  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.830  -1.193   0.352  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.164  -0.862   0.304  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.744  -0.730   1.702  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.088  -0.395   1.626  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.302   0.447  -0.400  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.830   0.191  -1.678  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.842   0.862  -0.570  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.679   1.606  -1.731  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.985   0.660  -0.393  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.680   1.954  -0.493  0.00  0.00           N+0
HETATM   18  C   UNK     0      -1.571   2.934  -0.402  0.00  0.00           C+0
HETATM   19  N   UNK     0      -2.852   2.619  -0.199  0.00  0.00           N+0
HETATM   20  C   UNK     0      -3.218   1.312  -0.090  0.00  0.00           C+0
HETATM   21  N   UNK     0      -4.578   1.041   0.124  0.00  0.00           N+0
HETATM   22  C   UNK     0      -2.301   0.299  -0.182  0.00  0.00           C+0
HETATM   23  H   UNK     0      -5.535  -1.502  -0.490  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.150  -1.434   1.269  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.682  -2.534  -0.302  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.450  -0.909  -1.661  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.741  -1.675  -0.194  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.577  -1.703   2.210  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.214   0.045   2.300  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.559  -1.038   1.025  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.881   1.200   0.153  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.689  -0.764  -1.932  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.504   1.436   0.319  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.889   2.545  -1.502  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.217   3.955  -0.498  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.021   0.981   1.065  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.193   0.903  -0.706  0.00  0.00           H+0
CONECT    1    2   23   24                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6   25                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   14   26                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   12   27                                             
CONECT   10    9   11   28   29                                             
CONECT   11   10   30                                                       
CONECT   12    9   13   14   31                                             
CONECT   13   12   32                                                       
CONECT   14   12   15    7   33                                             
CONECT   15   14   34                                                       
CONECT   16    6   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   36   37                                                  
CONECT   22   20    4   16                                                  
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    5                                                            
CONECT   26    7                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   18                                                            
CONECT   36   21                                                            
CONECT   37   21                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
   -4.8292   -1.6023    0.2725 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -1.9454    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2559   -3.2081    0.1076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552   -1.0731   -0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0245   -1.4911   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2323   -0.4370   -0.4577 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862   -0.4964   -0.6653 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8301   -1.1933    0.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1643   -0.8616    0.3044 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7440   -0.7297    1.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0882   -0.3953    1.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023    0.4471   -0.3997 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8304    0.1910   -1.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    0.8623   -0.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6786    1.6060   -1.7308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852    0.6603   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803    1.9535   -0.4925 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5712    2.9341   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8515    2.6192   -0.1991 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2176    1.3123   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5777    1.0408    0.1235 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3011    0.2988   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5354   -1.5016   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.4343    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822   -2.5343   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -0.9085   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -1.6746   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768   -1.7030    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.0451    2.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5594   -1.0376    1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8813    1.2003    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6886   -0.7642   -1.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5039    1.4363    0.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892    2.5451   -1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168    3.9547   -0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0215    0.9814    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1932    0.9032   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  6 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  4  1  0
 14  7  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  6
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 14 33  1  1
 15 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
7-Deaza-7-carbamoyladenosine	ChEBI
7-Deazaadenosine-7-carboxamide	ChEBI
4-amino-5-carboxamido-7-(D-Ribofuranosyl)-pyrrolo-(2,3-D)pyrimidine	MeSH
Sangivamycin monohydrochloride	MeSH

Chemical Formula

C₁₂H₁₅N₅O₅

Average Mass

309.2780 Da

Monoisotopic Mass

309.10732 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-carboxamide

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(N)=NC=N2

InChI Identifier

InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1

InChI Key

OBZJZDHRXBKKTJ-JTFADIMSSA-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 sp.	NPAtlas	5748694

Chemical Taxonomy

Description

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
Pyrimidinecarboxamide
Pyrrolopyrimidine
Pyrrole-3-carboxamide
Pyrrole-3-carboxylic acid or derivatives
Aminopyrimidine
Monosaccharide
Pyrimidine
Substituted pyrrole
Imidolactam
Vinylogous amide
Pyrrole
Tetrahydrofuran
Heteroaromatic compound
Amino acid or derivatives
Secondary alcohol
Carboxamide group
Primary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organic oxide
Primary alcohol
Primary amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleoside analogue (CHEBI:85997 )

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	-1.4	ALOGPS
logP	-2.4	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	169.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.45 m³·mol⁻¹	ChemAxon
Polarizability	29.36 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

NPA005297

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sangivamycin

METLIN ID

Not Available

PubChem Compound

14978

PDB ID

Not Available

ChEBI ID

85997

Good Scents ID

Not Available

References

General References

Rao KV: Structure of sangivamycin. J Med Chem. 1968 Sep;11(5):939-41. doi: 10.1021/jm00311a005. [PubMed:5748694 ]
Loomis CR, Bell RM: Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C. J Biol Chem. 1988 Feb 5;263(4):1682-92. [PubMed:3338987 ]

Showing NP-Card for Sangivamycin (NP0021733)

MOL for NP0021733 (Sangivamycin)

3D MOL for NP0021733 (Sangivamycin)

3D SDF for NP0021733 (Sangivamycin)

3D-SDF for NP0021733 (Sangivamycin)

PDB for NP0021733 (Sangivamycin)

3D PDB for NP0021733 (Sangivamycin)

SMILES for NP0021733 (Sangivamycin)

INCHI for NP0021733 (Sangivamycin)

Structure for NP0021733 (Sangivamycin)

3D Structure for NP0021733 (Sangivamycin)