NP-MRD: Showing NP-Card for Protetrone (NP0021722)

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Record Information

Version

2.0

Created at

2021-01-06 06:59:58 UTC

Updated at

2021-07-15 17:37:06 UTC

NP-MRD ID

NP0021722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Protetrone

Provided By

NPAtlas

Description

Protetrone is found in Kitasatospora aureofaciens and Streptomyces. Protetrone was first documented in 1968 (PMID: 5688362). Based on a literature review very few articles have been published on Protetrone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

 41 43  0  0  0  0            999 V2000
    4.3211   -2.4009    2.1252 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6351    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -2.2474    0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.2026    1.2658 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9721    0.5083    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254    1.1809   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    0.5246   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    1.2522   -1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    2.0963   -2.2245 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4195    3.3245   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    3.5916   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    4.2584   -2.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    1.2496   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5240   -1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.2344    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -0.2355    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -0.9570    1.5082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.0048    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.6893    1.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564   -1.0062    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -1.7507    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -2.5110    2.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.6878    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.9412   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.2217   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4404   -0.2488   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950    0.5370   -1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    1.2204   -2.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7143   -3.3719    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -2.0558    3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.0163    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6047    0.2279    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4714   -2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    2.4272   -3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1988    5.2173   -1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    1.8222   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.5160    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.6970    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0304   -2.2647    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7432   -0.9087   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536    0.3712   -1.8372 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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 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
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 16  7  1  0  0  0  0
 26 20  1  0  0  0  0
 27 14  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  0  0  0  0
 17 37  1  0  0  0  0
 22 38  1  0  0  0  0
 23 39  1  0  0  0  0
 24 40  1  0  0  0  0
 25 41  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    4.3211   -2.4009    2.1252 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6351    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -2.2474    0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.2026    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    0.5083    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254    1.1809   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    0.5246   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    1.2522   -1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    2.0963   -2.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    3.3245   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    3.5916   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    4.2584   -2.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    1.2496   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5240   -1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.2344    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -0.2355    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -0.9570    1.5082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.0048    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.6893    1.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564   -1.0062    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -1.7507    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -2.5110    2.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.6878    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.9412   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.2217   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4404   -0.2488   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950    0.5370   -1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    1.2204   -2.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7143   -3.3719    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -2.0558    3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.0163    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6047    0.2279    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4714   -2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    2.4272   -3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1988    5.2173   -1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    1.8222   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.5160    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.6970    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0304   -2.2647    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7432   -0.9087   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536    0.3712   -1.8372 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 16  7  1  0
 26 20  1  0
 27 14  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
 12 35  1  0
 13 36  1  0
 17 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
 25 41  1  0
M  END


  Mrv1652306242105183D          

 41 43  0  0  0  0            999 V2000
    4.3211   -2.4009    2.1252 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6351    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -2.2474    0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.2026    1.2658 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9721    0.5083    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254    1.1809   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    0.5246   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    1.2522   -1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    2.0963   -2.2245 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4195    3.3245   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    3.5916   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    4.2584   -2.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    1.2496   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5240   -1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.2344    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -0.2355    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -0.9570    1.5082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.0048    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.6893    1.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564   -1.0062    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -1.7507    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -2.5110    2.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.6878    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.9412   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.2217   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4404   -0.2488   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950    0.5370   -1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    1.2204   -2.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7143   -3.3719    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -2.0558    3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.0163    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6047    0.2279    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4714   -2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    2.4272   -3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1988    5.2173   -1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    1.8222   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.5160    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.6970    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0304   -2.2647    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7432   -0.9087   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536    0.3712   -1.8372 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  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 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
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 16  7  1  0  0  0  0
 26 20  1  0  0  0  0
 27 14  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
 12 35  1  0  0  0  0
 13 36  1  0  0  0  0
 17 37  1  0  0  0  0
 22 38  1  0  0  0  0
 23 39  1  0  0  0  0
 24 40  1  0  0  0  0
 25 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C1=C(C(=O)C([H])([H])C(=O)N([H])[H])C(O[H])=C2C(=O)C3=C(O[H])C([H])=C([H])C([H])=C3C(=O)C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H13NO8/c20-12(23)6-11(22)14-7(5-13(24)25)4-9-16(18(14)27)19(28)15-8(17(9)26)2-1-3-10(15)21/h1-4,21,27H,5-6H2,(H2,20,23)(H,24,25)

> <INCHI_KEY>
PIXFQUMLCLXSMP-UHFFFAOYSA-N

> <FORMULA>
C19H13NO8

> <MOLECULAR_WEIGHT>
383.312

> <EXACT_MASS>
383.064116383

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
36.411358273064955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-(2-carbamoylacetyl)-4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl]acetic acid

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
2.5422570716666666

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.5043764522044265

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9362564769760016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.632481443037405

> <JCHEM_POLAR_SURFACE_AREA>
172.06

> <JCHEM_REFRACTIVITY>
94.9895

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3-(2-carbamoylacetyl)-4,5-dihydroxy-9,10-dioxoanthracen-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    4.3211   -2.4009    2.1252 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6351    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -2.2474    0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.2026    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    0.5083    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254    1.1809   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    0.5246   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    1.2522   -1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    2.0963   -2.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    3.3245   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    3.5916   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    4.2584   -2.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    1.2496   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5240   -1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.2344    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -0.2355    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -0.9570    1.5082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.0048    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.6893    1.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564   -1.0062    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -1.7507    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -2.5110    2.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.6878    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.9412   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.2217   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4404   -0.2488   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950    0.5370   -1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    1.2204   -2.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7143   -3.3719    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -2.0558    3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.0163    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6047    0.2279    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4714   -2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    2.4272   -3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1988    5.2173   -1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    1.8222   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.5160    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.6970    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0304   -2.2647    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7432   -0.9087   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536    0.3712   -1.8372 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
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 16 17  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
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 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 16  7  1  0
 26 20  1  0
 27 14  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  4 32  1  0
  9 33  1  0
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 12 35  1  0
 13 36  1  0
 17 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
 25 41  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       4.321  -2.401   2.125  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.770  -1.635   1.065  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.485  -2.247   0.001  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.567  -0.203   1.266  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.972   0.508   0.116  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.825   1.181  -0.566  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.605   0.525  -0.297  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.185   1.252  -1.359  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.097   2.096  -2.224  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.420   3.325  -1.469  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.966   3.592  -0.312  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.274   4.258  -2.049  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.162   1.250  -1.709  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.087   0.524  -1.003  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.673  -0.234   0.097  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.682  -0.236   0.454  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.123  -0.957   1.508  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.638  -1.005   0.852  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.299  -1.689   1.835  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.056  -1.006   0.483  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.955  -1.751   1.223  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.659  -2.511   2.294  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.308  -1.688   0.788  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.690  -0.941  -0.288  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.769  -0.222  -0.989  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.440  -0.249  -0.607  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.495   0.537  -1.388  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.869   1.220  -2.379  0.00  0.00           O+0
HETATM   29  H   UNK     0       4.714  -3.372   1.978  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.372  -2.056   3.111  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.972  -0.016   2.170  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.605   0.228   1.483  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.936   1.471  -2.525  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.497   2.427  -3.122  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.199   5.217  -1.802  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.539   1.822  -2.557  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.721  -1.516   2.133  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.843  -2.697   2.750  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.030  -2.265   1.355  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.743  -0.909  -0.606  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.054   0.371  -1.837  0.00  0.00           H+0
CONECT    1    2   29   30                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31   32                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   33   34                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   35                                                       
CONECT   13    8   14   36                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17    7                                                  
CONECT   17   16   37                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   38                                                       
CONECT   23   21   24   39                                                  
CONECT   24   23   25   40                                                  
CONECT   25   24   26   41                                                  
CONECT   26   25   27   20                                                  
CONECT   27   26   28   14                                                  
CONECT   28   27                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   17                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
CONECT   41   25                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    4.3211   -2.4009    2.1252 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.6351    1.0652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4853   -2.2474    0.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -0.2026    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    0.5083    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8254    1.1809   -0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055    0.5246   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    1.2522   -1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    2.0963   -2.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    3.3245   -1.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656    3.5916   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737    4.2584   -2.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1616    1.2496   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869    0.5240   -1.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -0.2344    0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817   -0.2355    0.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1230   -0.9570    1.5082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -1.0048    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.6893    1.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564   -1.0062    0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -1.7507    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -2.5110    2.2943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.6878    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.9412   -0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -0.2217   -0.9888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4404   -0.2488   -0.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4950    0.5370   -1.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    1.2204   -2.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7143   -3.3719    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720   -2.0558    3.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.0163    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6047    0.2279    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9362    1.4714   -2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974    2.4272   -3.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1988    5.2173   -1.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    1.8222   -2.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.5160    2.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8426   -2.6970    2.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0304   -2.2647    1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7432   -0.9087   -0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0536    0.3712   -1.8372 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 16  7  1  0
 26 20  1  0
 27 14  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  4 32  1  0
  9 33  1  0
  9 34  1  0
 12 35  1  0
 13 36  1  0
 17 37  1  0
 22 38  1  0
 23 39  1  0
 24 40  1  0
 25 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-{4,5-dihydroxy-3-[2-(C-hydroxycarbonimidoyl)acetyl]-9,10-dioxo-9,10-dihydroanthracen-2-yl}acetate	Generator

Chemical Formula

C₁₉H₁₃NO₈

Average Mass

383.3120 Da

Monoisotopic Mass

383.06412 Da

IUPAC Name

2-[3-(2-carbamoylacetyl)-4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl]acetic acid

Traditional Name

[3-(2-carbamoylacetyl)-4,5-dihydroxy-9,10-dioxoanthracen-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

NC(=O)CC(=O)C1=C(CC(O)=O)C=C2C(=O)C3=C(C(O)=CC=C3)C(=O)C2=C1O

InChI Identifier

InChI=1S/C19H13NO8/c20-12(23)6-11(22)14-7(5-13(24)25)4-9-16(18(14)27)19(28)15-8(17(9)26)2-1-3-10(15)21/h1-4,21,27H,5-6H2,(H2,20,23)(H,24,25)

InChI Key

PIXFQUMLCLXSMP-UHFFFAOYSA-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
Kitasatospora aureofaciens	LOTUS Database	35616633
Streptomyces	NPAtlas	5688362

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty amide
Fatty acyl
1,3-dicarbonyl compound
Vinylogous acid
Carboxamide group
Ketone
Primary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.43	ALOGPS
logP	2.54	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	172.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.99 m³·mol⁻¹	ChemAxon
Polarizability	36.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019112

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435377

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314612

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McCormick JR, Jensen ER: Biosynthesis of tetracyclines. X. Protetrone. J Am Chem Soc. 1968 Dec 4;90(25):7126-7. doi: 10.1021/ja01027a045. [PubMed:5688362 ]

Showing NP-Card for Protetrone (NP0021722)

MOL for NP0021722 (Protetrone)

3D MOL for NP0021722 (Protetrone)

3D SDF for NP0021722 (Protetrone)

3D-SDF for NP0021722 (Protetrone)

PDB for NP0021722 (Protetrone)

3D PDB for NP0021722 (Protetrone)

SMILES for NP0021722 (Protetrone)

INCHI for NP0021722 (Protetrone)

Structure for NP0021722 (Protetrone)

3D Structure for NP0021722 (Protetrone)