NP-MRD: Showing NP-Card for Sparsomycin (NP0004825)

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Record Information

Version

2.0

Created at

2020-12-09 02:14:12 UTC

Updated at

2021-07-15 16:50:16 UTC

NP-MRD ID

NP0004825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sparsomycin

Provided By

NPAtlas

Description

Sparsomycin is found in Unknown-fungus sp. Sparsomycin was first documented in 1963 (PMID: 14015652). Based on a literature review a small amount of articles have been published on Sparsomycin (PMID: 29111481) (PMID: 26046698) (PMID: 23249745).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 42 42  0  0  0  0            999 V2000
    6.5470   -0.8529    2.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    0.3566    2.6040 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483    0.9369    1.0369 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5620   -0.4370    0.3106 S   0  0  2  0  0  4  0  0  0  0  0  0
    4.6819   -1.4074   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.0386   -1.1944 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7353    1.0540   -1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0055    2.4300   -0.8077 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    2.7256    0.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.6267   -0.9875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5718    0.5264   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    0.8269   -3.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9628    0.1155   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2076   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809   -0.6369   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -0.9269    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365   -0.7960    2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -1.3271    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2969   -1.4688    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4523   -1.8512    0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0603   -1.2017   -0.8965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207   -0.7965   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652   -0.5630   -2.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -1.7974    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1160   -0.4254    1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546   -0.9904    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.7562    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3168    1.2613    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.9482   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.2619   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    1.2178   -2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    3.2000   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    2.7209   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.7949    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    0.4081    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6177    0.0744   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.1379    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -0.7828    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6007    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    0.2240    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5386   -1.5489    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8239   -1.3039   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  2  0  0  0  0
  4  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
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 15  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  6  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 21 42  1  0  0  0  0
M  END

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    6.5470   -0.8529    2.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    0.3566    2.6040 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483    0.9369    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620   -0.4370    0.3106 S   0  0  0  0  0  4  0  0  0  0  0  0
    4.6819   -1.4074   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.0386   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353    1.0540   -1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0055    2.4300   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    2.7256    0.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.6267   -0.9875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5718    0.5264   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    0.8269   -3.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9628    0.1155   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2076   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809   -0.6369   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -0.9269    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365   -0.7960    2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -1.3271    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2969   -1.4688    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4523   -1.8512    0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0603   -1.2017   -0.8965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207   -0.7965   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652   -0.5630   -2.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -1.7974    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1160   -0.4254    1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546   -0.9904    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.7562    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3168    1.2613    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.9482   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.2619   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    1.2178   -2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    3.2000   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    2.7209   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.7949    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    0.4081    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6177    0.0744   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.1379    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -0.7828    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6007    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    0.2240    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5386   -1.5489    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8239   -1.3039   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
M  END


  Mrv1652306242121113D          

 42 42  0  0  0  0            999 V2000
    6.5470   -0.8529    2.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    0.3566    2.6040 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483    0.9369    1.0369 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5620   -0.4370    0.3106 S   0  0  2  0  0  4  0  0  0  0  0  0
    4.6819   -1.4074   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.0386   -1.1944 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7353    1.0540   -1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0055    2.4300   -0.8077 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    2.7256    0.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.6267   -0.9875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5718    0.5264   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    0.8269   -3.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9628    0.1155   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2076   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809   -0.6369   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -0.9269    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365   -0.7960    2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -1.3271    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2969   -1.4688    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4523   -1.8512    0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0603   -1.2017   -0.8965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207   -0.7965   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652   -0.5630   -2.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -1.7974    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1160   -0.4254    1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546   -0.9904    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.7562    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3168    1.2613    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.9482   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.2619   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    1.2178   -2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    3.2000   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    2.7209   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.7949    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    0.4081    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6177    0.0744   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.1379    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -0.7828    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6007    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    0.2240    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5386   -1.5489    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8239   -1.3039   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  2  0  0  0  0
  4  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
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 15  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  6  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 13 36  1  0  0  0  0
 14 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 21 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]([H])(N([H])C(=O)C(\[H])=C(/[H])C1=C(N([H])C(=O)N([H])C1=O)C([H])([H])[H])C([H])([H])[S@@](=O)C([H])([H])SC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+/m0/s1

> <INCHI_KEY>
XKLZIVIOZDNKEQ-CLQLPEFOSA-N

> <FORMULA>
C13H19N3O5S2

> <MOLECULAR_WEIGHT>
361.437

> <EXACT_MASS>
361.076612113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.01032306577814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-{1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl}-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide

> <ALOGPS_LOGP>
-1.32

> <JCHEM_LOGP>
-2.4821507096666666

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.709261699758851

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.973405601030635

> <JCHEM_PKA_STRONGEST_BASIC>
-0.33858718655731523

> <JCHEM_POLAR_SURFACE_AREA>
124.6

> <JCHEM_REFRACTIVITY>
91.66539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-{1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl}-3-(4-methyl-2,6-dioxo-1,3-dihydropyrimidin-5-yl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    6.5470   -0.8529    2.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    0.3566    2.6040 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483    0.9369    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620   -0.4370    0.3106 S   0  0  0  0  0  4  0  0  0  0  0  0
    4.6819   -1.4074   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.0386   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353    1.0540   -1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0055    2.4300   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    2.7256    0.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.6267   -0.9875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5718    0.5264   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    0.8269   -3.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9628    0.1155   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2076   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809   -0.6369   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -0.9269    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365   -0.7960    2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -1.3271    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2969   -1.4688    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4523   -1.8512    0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0603   -1.2017   -0.8965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207   -0.7965   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652   -0.5630   -2.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -1.7974    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1160   -0.4254    1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546   -0.9904    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.7562    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3168    1.2613    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.9482   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.2619   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    1.2178   -2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    3.2000   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    2.7209   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.7949    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    0.4081    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6177    0.0744   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.1379    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -0.7828    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6007    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    0.2240    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5386   -1.5489    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8239   -1.3039   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  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  C   UNK     0       6.547  -0.853   2.153  0.00  0.00           C+0
HETATM    2  S   UNK     0       5.271   0.357   2.604  0.00  0.00           S+0
HETATM    3  C   UNK     0       4.448   0.937   1.037  0.00  0.00           C+0
HETATM    4  S   UNK     0       3.562  -0.437   0.311  0.00  0.00           S+0
HETATM    5  O   UNK     0       4.682  -1.407  -0.128  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.773   0.039  -1.194  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.735   1.054  -1.257  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.006   2.430  -0.808  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.733   2.726   0.506  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.372   0.627  -0.988  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.572   0.526  -2.006  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.182   0.827  -3.188  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.963   0.116  -1.877  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.438  -0.208  -0.701  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.781  -0.637  -0.377  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.071  -0.927   0.963  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.037  -0.796   2.018  0.00  0.00           C+0
HETATM   18  N   UNK     0      -5.308  -1.327   1.284  0.00  0.00           N+0
HETATM   19  C   UNK     0      -6.297  -1.469   0.393  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.452  -1.851   0.751  0.00  0.00           O+0
HETATM   21  N   UNK     0      -6.060  -1.202  -0.897  0.00  0.00           N+0
HETATM   22  C   UNK     0      -4.821  -0.797  -1.246  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.665  -0.563  -2.467  0.00  0.00           O+0
HETATM   24  H   UNK     0       6.106  -1.797   1.782  0.00  0.00           H+0
HETATM   25  H   UNK     0       7.116  -0.425   1.291  0.00  0.00           H+0
HETATM   26  H   UNK     0       7.255  -0.990   2.978  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.822   1.756   1.368  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.317   1.261   0.421  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.321  -0.948  -1.606  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.621   0.262  -1.954  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.651   1.218  -2.452  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.427   3.200  -1.410  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.077   2.721  -1.038  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.792   2.795   0.728  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.185   0.408   0.038  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.618   0.074  -2.754  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.716  -0.138   0.122  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.559  -0.783   3.001  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.305  -1.601   2.038  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.611   0.224   1.907  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.539  -1.549   2.288  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.824  -1.304  -1.631  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   27   28                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   29   30                                             
CONECT    7    6    8   10   31                                             
CONECT    8    7    9   32   33                                             
CONECT    9    8   34                                                       
CONECT   10    7   11   35                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   36                                                  
CONECT   14   13   15   37                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   38   39   40                                             
CONECT   18   16   19   41                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   42                                                  
CONECT   22   21   23   15                                                  
CONECT   23   22                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   21                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   84    0
END

RDKit          3D

42 42  0  0  0  0  0  0  0  0999 V2000
    6.5470   -0.8529    2.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708    0.3566    2.6040 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4483    0.9369    1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620   -0.4370    0.3106 S   0  0  0  0  0  4  0  0  0  0  0  0
    4.6819   -1.4074   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727    0.0386   -1.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353    1.0540   -1.2573 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0055    2.4300   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    2.7256    0.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718    0.6267   -0.9875 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5718    0.5264   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1822    0.8269   -3.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9628    0.1155   -1.8773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4376   -0.2076   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7809   -0.6369   -0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -0.9269    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365   -0.7960    2.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3082   -1.3271    1.2839 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2969   -1.4688    0.3934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4523   -1.8512    0.7507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0603   -1.2017   -0.8965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207   -0.7965   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652   -0.5630   -2.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055   -1.7974    1.7821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1160   -0.4254    1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2546   -0.9904    2.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224    1.7562    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3168    1.2613    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -0.9482   -1.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6208    0.2619   -1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6507    1.2178   -2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265    3.2000   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    2.7209   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    2.7949    0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854    0.4081    0.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6177    0.0744   -2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -0.1379    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -0.7828    3.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -1.6007    2.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109    0.2240    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5386   -1.5489    2.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8239   -1.3039   -1.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  6
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 14 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 21 42  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E)-3-(2,4-Dihydroxy-6-methylpyrimidin-5-yl)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl]prop-2-enimidate	Generator
(2E)-3-(2,4-Dihydroxy-6-methylpyrimidin-5-yl)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulphanyl)methanesulphinyl]propan-2-yl]prop-2-enimidate	Generator
(2E)-3-(2,4-Dihydroxy-6-methylpyrimidin-5-yl)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulphanyl)methanesulphinyl]propan-2-yl]prop-2-enimidic acid	Generator

Chemical Formula

C₁₃H₁₉N₃O₅S₂

Average Mass

361.4370 Da

Monoisotopic Mass

361.07661 Da

IUPAC Name

(2E)-N-{1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl}-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide

Traditional Name

(2E)-N-{1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl}-3-(4-methyl-2,6-dioxo-1,3-dihydropyrimidin-5-yl)prop-2-enamide

CAS Registry Number

Not Available

SMILES

CSC[S@](=O)C[C@H](CO)NC(=O)\C=C\C1=C(C)NC(=O)NC1=O

InChI Identifier

InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+/m0/s1

InChI Key

XKLZIVIOZDNKEQ-CLQLPEFOSA-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
Unknown-fungus sp.	NPAtlas	14015652

Species Where Detected

Species Name	Source	Reference
Streptomyces cuspidosporus	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

Alternative Parents

Substituents

Pyrimidone
Hydropyrimidine
Vinylogous amide
Heteroaromatic compound
Carboxamide group
Lactam
Secondary carboxylic acid amide
Sulfoxide
Urea
Sulfenyl compound
Sulfinyl compound
Carboxylic acid derivative
Thioether
Azacycle
Dialkylthioether
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-1.3	ALOGPS
logP	-2.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.97	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	91.67 m³·mol⁻¹	ChemAxon
Polarizability	36.01 Å³	ChemAxon
Number of Rings	1	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

NPA014239

HMDB ID

Not Available

DrugBank ID

DB04222

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000748

Chemspider ID

7822406

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sparsomycin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

BRODASKY TF: Quantitative spectrophotometric papergram assays. II. Sparsomycin, a new antitumor antibiotic. J Pharm Sci. 1963 Mar;52:233-5. doi: 10.1002/jps.2600520309. [PubMed:14015652 ]
Zhang H, Zhou Q, Lou T, Wang S, Ruan H: Draft genome sequence of broad-spectrum antibiotic sparsomycin-producing Streptomyces sparsogenes ATCC 25498 from the American Type Culture Collection. J Glob Antimicrob Resist. 2017 Dec;11:159-160. doi: 10.1016/j.jgar.2017.10.011. Epub 2017 Oct 27. [PubMed:29111481 ]
Rui Z, Huang W, Xu F, Han M, Liu X, Lin S, Zhang W: Sparsomycin Biosynthesis Highlights Unusual Module Architecture and Processing Mechanism in Non-ribosomal Peptide Synthetase. ACS Chem Biol. 2015 Aug 21;10(8):1765-9. doi: 10.1021/acschembio.5b00284. Epub 2015 Jun 9. [PubMed:26046698 ]
Ermolenko DN, Cornish PV, Ha T, Noller HF: Antibiotics that bind to the A site of the large ribosomal subunit can induce mRNA translocation. RNA. 2013 Feb;19(2):158-66. doi: 10.1261/rna.035964.112. Epub 2012 Dec 17. [PubMed:23249745 ]

Showing NP-Card for Sparsomycin (NP0004825)

MOL for NP0004825 (Sparsomycin)

3D MOL for NP0004825 (Sparsomycin)

3D SDF for NP0004825 (Sparsomycin)

3D-SDF for NP0004825 (Sparsomycin)

PDB for NP0004825 (Sparsomycin)

3D PDB for NP0004825 (Sparsomycin)

SMILES for NP0004825 (Sparsomycin)

INCHI for NP0004825 (Sparsomycin)

Structure for NP0004825 (Sparsomycin)

3D Structure for NP0004825 (Sparsomycin)