NP-MRD: Showing NP-Card for Epoxyquinomicin C (NP0023722)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 08:46:30 UTC

Updated at

2021-07-15 17:42:31 UTC

NP-MRD ID

NP0023722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epoxyquinomicin C

Provided By

NPAtlas

Description

Epoxyquinomicin C is found in Amycolatopsis sulphurea. Epoxyquinomicin C was first documented in 2006 (PMID: 16865289). Based on a literature review very few articles have been published on Epoxyquinomicin C (PMID: 32377746) (PMID: 32179183) (PMID: 29510517) (PMID: 28418286) (PMID: 25519802) (PMID: 20337659).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120443D          

 34 36  0  0  0  0            999 V2000
   -0.9135   -1.6193   -0.6894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.4479   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.5542   -0.2378 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    0.2483   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.7661   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828    0.3831   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.3690   -1.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.0069    0.9664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8141    0.7663    1.5629 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0172    0.1854    1.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.3384    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260   -0.3963    1.7716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2592   -0.7152    1.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2282   -0.7153    1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -0.1826   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.1028   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520    1.3877   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267    0.4051   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -0.8744   -1.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926   -1.1810   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -2.4910   -1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    1.5298   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6822    1.4771   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935    0.6982    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.8438    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.9081    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -0.3187    2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -1.7228    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -0.8928    2.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.9509   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9979    2.3951   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    0.5827   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7423   -1.6782   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -2.9869   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13  4  1  0  0  0  0
 20 15  1  0  0  0  0
 12  8  1  0  0  0  0
  3 22  1  0  0  0  0
  5 23  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
 14 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 21 34  1  0  0  0  0
M  END

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.9135   -1.6193   -0.6894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.4479   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.5542   -0.2378 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    0.2483   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.7661   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828    0.3831   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.3690   -1.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.0069    0.9664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8141    0.7663    1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0172    0.1854    1.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.3384    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260   -0.3963    1.7716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2592   -0.7152    1.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2282   -0.7153    1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -0.1826   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.1028   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520    1.3877   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267    0.4051   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -0.8744   -1.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926   -1.1810   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -2.4910   -1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    1.5298   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6822    1.4771   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935    0.6982    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.8438    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.9081    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -0.3187    2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -1.7228    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -0.8928    2.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.9509   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9979    2.3951   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    0.5827   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7423   -1.6782   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -2.9869   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 13  4  1  0
 20 15  1  0
 12  8  1  0
  3 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  1
 13 28  1  6
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
M  END


  Mrv1652306242120443D          

 34 36  0  0  0  0            999 V2000
   -0.9135   -1.6193   -0.6894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.4479   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.5542   -0.2378 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    0.2483   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.7661   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828    0.3831   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.3690   -1.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.0069    0.9664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8141    0.7663    1.5629 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0172    0.1854    1.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.3384    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260   -0.3963    1.7716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2592   -0.7152    1.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2282   -0.7153    1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -0.1826   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.1028   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520    1.3877   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267    0.4051   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -0.8744   -1.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926   -1.1810   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -2.4910   -1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    1.5298   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6822    1.4771   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935    0.6982    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.8438    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.9081    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -0.3187    2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -1.7228    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -0.8928    2.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.9509   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9979    2.3951   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    0.5827   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7423   -1.6782   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -2.9869   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13  4  1  0  0  0  0
 20 15  1  0  0  0  0
 12  8  1  0  0  0  0
  3 22  1  0  0  0  0
  5 23  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  0  0  0  0
 10 26  1  0  0  0  0
 12 27  1  1  0  0  0
 13 28  1  6  0  0  0
 14 29  1  0  0  0  0
 16 30  1  0  0  0  0
 17 31  1  0  0  0  0
 18 32  1  0  0  0  0
 19 33  1  0  0  0  0
 21 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C([H])=C1C(=O)N([H])C1=C([H])C(=O)[C@@]2(O[C@]2([H])[C@@]1([H])O[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H13NO6/c16-6-14-10(18)5-8(11(19)12(14)21-14)15-13(20)7-3-1-2-4-9(7)17/h1-5,11-12,16-17,19H,6H2,(H,15,20)/t11-,12+,14-/m0/s1

> <INCHI_KEY>
JNDISHBDOZQLTR-SCRDCRAPSA-N

> <FORMULA>
C14H13NO6

> <MOLECULAR_WEIGHT>
291.259

> <EXACT_MASS>
291.074287143

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.98477307501046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
-0.11996051899999992

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.092932673819462

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.740067555298875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.188735095748453

> <JCHEM_POLAR_SURFACE_AREA>
119.39000000000001

> <JCHEM_REFRACTIVITY>
71.7938

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.9135   -1.6193   -0.6894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.4479   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.5542   -0.2378 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    0.2483   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.7661   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828    0.3831   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.3690   -1.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.0069    0.9664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8141    0.7663    1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0172    0.1854    1.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.3384    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260   -0.3963    1.7716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2592   -0.7152    1.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2282   -0.7153    1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -0.1826   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.1028   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520    1.3877   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267    0.4051   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -0.8744   -1.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926   -1.1810   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -2.4910   -1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    1.5298   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6822    1.4771   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935    0.6982    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.8438    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.9081    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -0.3187    2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -1.7228    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -0.8928    2.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.9509   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9979    2.3951   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    0.5827   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7423   -1.6782   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -2.9869   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 13  4  1  0
 20 15  1  0
 12  8  1  0
  3 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  1
 13 28  1  6
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -0.914  -1.619  -0.689  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.417  -0.448  -0.592  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.458   0.554  -0.238  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.915   0.248  -0.021  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.912   0.766  -0.716  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.283   0.383  -0.410  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.163   0.369  -1.299  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.639   0.007   0.966  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.814   0.766   1.563  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.017   0.185   1.135  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.624  -1.338   1.347  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.526  -0.396   1.772  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.259  -0.715   1.051  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.228  -0.715   1.987  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.819  -0.183  -0.821  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.295   1.103  -0.699  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.652   1.388  -0.916  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.527   0.405  -1.251  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.053  -0.874  -1.372  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.693  -1.181  -1.158  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.363  -2.491  -1.312  0.00  0.00           O+0
HETATM   22  H   UNK     0      -0.792   1.530  -0.140  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.682   1.477  -1.513  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.793   0.698   2.675  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.757   1.844   1.309  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.532   0.908   0.697  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.510  -0.319   2.887  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.280  -1.723   0.562  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.562  -0.893   2.906  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.668   1.951  -0.436  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.998   2.395  -0.816  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.574   0.583  -1.425  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.742  -1.678  -1.640  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.532  -2.987  -1.233  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11   12                                             
CONECT    9    8   10   24   25                                             
CONECT   10    9   26                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13    8   27                                             
CONECT   13   12   14    4   28                                             
CONECT   14   13   29                                                       
CONECT   15    2   16   20                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   32                                                  
CONECT   19   18   20   33                                                  
CONECT   20   19   21   15                                                  
CONECT   21   20   34                                                       
CONECT   22    3                                                            
CONECT   23    5                                                            
CONECT   24    9                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
CONECT   33   19                                                            
CONECT   34   21                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
   -0.9135   -1.6193   -0.6894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167   -0.4479   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577    0.5542   -0.2378 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    0.2483   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.7661   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2828    0.3831   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1626    0.3690   -1.2988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    0.0069    0.9664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8141    0.7663    1.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0172    0.1854    1.1354 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6240   -1.3384    1.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5260   -0.3963    1.7716 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2592   -0.7152    1.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2282   -0.7153    1.9867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -0.1826   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2946    1.1028   -0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6520    1.3877   -0.9163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5267    0.4051   -1.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -0.8744   -1.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926   -1.1810   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3634   -2.4910   -1.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923    1.5298   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6822    1.4771   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7935    0.6982    2.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7570    1.8438    1.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320    0.9081    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097   -0.3187    2.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -1.7228    0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5618   -0.8928    2.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6676    1.9509   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9979    2.3951   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    0.5827   -1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7423   -1.6782   -1.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5316   -2.9869   -1.2328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  1
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 13  4  1  0
 20 15  1  0
 12  8  1  0
  3 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  1
 13 28  1  6
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 21 34  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₄H₁₃NO₆

Average Mass

291.2590 Da

Monoisotopic Mass

291.07429 Da

IUPAC Name

2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide

Traditional Name

2-hydroxy-N-[(1R,2S,6R)-2-hydroxy-6-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide

CAS Registry Number

Not Available

SMILES

OC[C@@]12O[C@@H]1[C@@H](O)C(NC(=O)C1=CC=CC=C1O)=CC2=O

InChI Identifier

InChI=1S/C14H13NO6/c16-6-14-10(18)5-8(11(19)12(14)21-14)15-13(20)7-3-1-2-4-9(7)17/h1-5,11-12,16-17,19H,6H2,(H,15,20)/t11-,12+,14-/m0/s1

InChI Key

JNDISHBDOZQLTR-SCRDCRAPSA-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
Amycolatopsis sulphurea	NPAtlas	9592560

Species Where Detected

Species Name	Source	Reference
Amycolatopsis sp. MK299-95F4	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.19	ALOGPS
logP	-0.12	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	119.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.79 m³·mol⁻¹	ChemAxon
Polarizability	27.98 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

NPA014158

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016391

Chemspider ID

2334387

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3075748

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ando Y, Sato Y, Kudo A, Watanabe T, Hirakata A, Okada AA, Umezawa K, Keino H: Antiinflammatory effects of the NFkappaB inhibitor dehydroxymethylepoxyquinomicin on ARPE19 cells. Mol Med Rep. 2020 Jul;22(1):582-590. doi: 10.3892/mmr.2020.11115. Epub 2020 May 4. [PubMed:32377746 ]
Umezawa K, Lin Y: Inhibition of matrix metalloproteinase expression and cellular invasion by NF-kappaB inhibitors of microbial origin. Biochim Biophys Acta Proteins Proteom. 2020 Jun;1868(6):140412. doi: 10.1016/j.bbapap.2020.140412. Epub 2020 Mar 14. [PubMed:32179183 ]
Lin Y, Ukaji T, Koide N, Umezawa K: Inhibition of Late and Early Phases of Cancer Metastasis by the NF-kappaB Inhibitor DHMEQ Derived from Microbial Bioactive Metabolite Epoxyquinomicin: A Review. Int J Mol Sci. 2018 Mar 3;19(3). pii: ijms19030729. doi: 10.3390/ijms19030729. [PubMed:29510517 ]
Jiang X, Lan Y, Wei B, Dai C, Gu Y, Ma J, Liu X, Umezawa K, Zhang Y: External application of NF-kappaB inhibitor DHMEQ suppresses development of atopic dermatitis-like lesions induced with DNCB/OX in BALB/c mice. Immunopharmacol Immunotoxicol. 2017 Jun;39(3):157-164. doi: 10.1080/08923973.2017.1312436. [PubMed:28418286 ]
Inokawa S, Watanabe T, Keino H, Sato Y, Hirakata A, Okada AA, Fukuda K, Fukushima A, Umezawa K: Dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, reduces chemokines and adhesion molecule expression induced by IL-1beta in human corneal fibroblasts. Graefes Arch Clin Exp Ophthalmol. 2015 Apr;253(4):557-63. doi: 10.1007/s00417-014-2879-9. Epub 2014 Dec 18. [PubMed:25519802 ]
Cardile V, Libra M, Caggia S, Frasca G, Umezawa K, Stivala F, Mazzarino MC, Bevelacqua Y, Coco M, Malaponte G: Dehydroxymethylepoxyquinomicin, a novel nuclear factor-kappaB inhibitor, prevents inflammatory injury induced by interferon-gamma and histamine in NCTC 2544 keratinocytes. Clin Exp Pharmacol Physiol. 2010 Jul;37(7):679-83. doi: 10.1111/j.1440-1681.2010.05375.x. Epub 2010 Mar 12. [PubMed:20337659 ]
Cardile V, Frasca G, Libra M, Caggia S, Umezawa K, Panico A, Malaponte G: Dehydroxymethylepoxyquinomicin inhibits expression and production of inflammatory mediators in interleukin-1beta-induced human chondrocytes. Cell Physiol Biochem. 2010;25(4-5):543-50. doi: 10.1159/000303058. Epub 2010 Mar 23. [PubMed:20332635 ]
Nishimura D, Ishikawa H, Matsumoto K, Shibata H, Motoyoshi Y, Fukuta M, Kawashimo H, Goto T, Taura N, Ichikawa T, Hamasaki K, Nakao K, Umezawa K, Eguchi K: DHMEQ, a novel NF-kappaB inhibitor, induces apoptosis and cell-cycle arrest in human hepatoma cells. Int J Oncol. 2006 Sep;29(3):713-9. [PubMed:16865289 ]

Showing NP-Card for Epoxyquinomicin C (NP0023722)

MOL for NP0023722 (Epoxyquinomicin C)

3D MOL for NP0023722 (Epoxyquinomicin C)

3D SDF for NP0023722 (Epoxyquinomicin C)

3D-SDF for NP0023722 (Epoxyquinomicin C)

PDB for NP0023722 (Epoxyquinomicin C)

3D PDB for NP0023722 (Epoxyquinomicin C)

SMILES for NP0023722 (Epoxyquinomicin C)

INCHI for NP0023722 (Epoxyquinomicin C)

Structure for NP0023722 (Epoxyquinomicin C)

3D Structure for NP0023722 (Epoxyquinomicin C)