NP-MRD: Showing NP-Card for (1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one (NP0272850)

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Record Information

Version

2.0

Created at

2022-09-08 19:39:38 UTC

Updated at

2022-09-08 19:39:38 UTC

NP-MRD ID

NP0272850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one

Description

Maduropeptin belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. (1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one is found in Actinomadura madurae. (1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one was first documented in 2010 (PMID: 20718468). Based on a literature review a small amount of articles have been published on Maduropeptin (PMID: 26484067) (PMID: 23360970) (PMID: 29341603) (PMID: 23034235).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082221392D          

 32 36  0  0  1  0            999 V2000
    7.4216    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2317    3.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4415    3.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412    3.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0509    3.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8610    2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614    2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    1.2295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2516    2.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    1.5789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1130    0.7732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3474    1.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634    0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442   -0.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8585   -1.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3321   -0.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0474   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6593   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3222    0.1335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7332    0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019    0.0456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8876    0.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922   -0.6525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2754   -0.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -0.0034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056    0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.8088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149    2.2461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6056    2.8951    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  3  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  3  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 18 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 15 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    1.9133    4.8731   -0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1129    3.8403   -0.0458 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6157    2.5421    0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9413    2.3907   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384    1.1362    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6762    0.0336    0.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357    0.2363    0.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -0.9756    1.9432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7962    1.4819    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5459    1.9198    0.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627    1.4862   -0.0994 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0833    0.6541   -1.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5877   -0.0451   -1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0632   -1.1478   -2.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -2.2141   -1.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3194   -1.7979   -0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -1.3112   -0.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0396   -0.5405    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3128   -0.8466    0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.3384    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1209    1.4625    0.5285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4774    1.7729   -0.7484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    0.8586    0.6647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3909    0.8213    2.0412 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4012   -3.4912   -1.4995 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2433   -4.4038   -0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138   -3.6755   -0.2204 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858   -3.1654    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769   -3.4255    1.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -2.2616   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5408   -1.1686    0.6152 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0070   -1.8060    1.6957 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008    4.5639   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2812    5.7657   -0.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994    5.0878    0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    3.2050   -0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5249    1.0344   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9865    2.4329   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5175   -0.9043   -3.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8473   -1.7726    0.3742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0024    0.4317    0.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7864    0.3053    2.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1706    2.3154    1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3668    2.7598   -0.8687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506    1.4767    2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395   -4.1779   -2.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426   -5.4776   -0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515   -3.9792    0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9580   -2.7747   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897   -1.7302   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5231   -0.8680    0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3964   -1.2658    2.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 31  1  0
 31 32  1  0
 31 30  1  0
 30 28  1  0
 28 29  2  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  3  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
 11 23  1  0
 23 24  1  1
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  3  0
  9  3  1  0
 18 23  1  0
  7  6  1  0
 25 27  1  0
 16 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
 31 51  1  6
 32 52  1  0
 30 49  1  0
 30 50  1  0
 26 47  1  0
 26 48  1  0
 25 46  1  6
 14 39  1  0
 11 38  1  6
 24 45  1  0
 21 43  1  1
 22 44  1  0
 20 41  1  0
 20 42  1  0
 19 40  1  0
M  END


  Mrv1652309082221392D          

 32 36  0  0  1  0            999 V2000
    7.4216    4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2317    3.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4415    3.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8412    3.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0509    3.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8610    2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614    2.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715    1.2295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2516    2.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9358    1.5789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1130    0.7732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3474    1.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5634    0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442   -0.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8585   -1.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830   -1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3321   -0.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0474   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6593   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3222    0.1335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7332    0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5019    0.0456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8876    0.7748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922   -0.6525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2754   -0.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829   -0.0034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056    0.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.8088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5955    1.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149    2.2461    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6056    2.8951    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  3  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  3  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 18 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 15 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0272850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2[C@@H](O)CC(=O)N3C[C@H]3C3=CC#C[C@H](OC1=C2Cl)[C@@]1(O)[C@@H](O)CC=C1C#C3

> <INCHI_IDENTIFIER>
InChI=1S/C24H20ClNO6/c1-31-18-9-8-15-17(27)11-21(29)26-12-16(26)13-3-2-4-20(32-23(18)22(15)25)24(30)14(6-5-13)7-10-19(24)28/h3,7-9,16-17,19-20,27-28,30H,10-12H2,1H3/b13-3+/t16-,17-,19-,20-,24-,26?/m0/s1

> <INCHI_KEY>
RUCAXECSYVMPPH-QFIHHIJXSA-N

> <FORMULA>
C24H20ClNO6

> <MOLECULAR_WEIGHT>
453.88

> <EXACT_MASS>
453.0979151

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.1703430317594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,2R,7S,14S,15S,16S)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1^{8,12}.0^{2,4}.0^{15,19}]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one

> <JCHEM_LOGP>
0.6024688173333337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.885193399218107

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.67055679459152

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1321915672864615

> <JCHEM_POLAR_SURFACE_AREA>
99.23

> <JCHEM_REFRACTIVITY>
118.00169999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1E,2R,7S,14S,15S,16S)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1^{8,12}.0^{2,4}.0^{15,19}]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      13.854   7.676   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.499   6.177   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.024   5.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.903   6.791   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.428   6.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.074   4.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.195   3.794   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       9.840   2.295   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0      11.670   4.236   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.947   2.947   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.278   1.443   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.849   2.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.385   1.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.572   0.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.789  -1.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.936  -2.322   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.475  -2.373   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.686  -1.422   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.022  -2.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.164  -1.156   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.535   0.249   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.302   1.585   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.003   0.085   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.724   1.446   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.639  -1.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.114  -1.436   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.688  -0.006   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       6.357   1.498   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.817   1.510   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.712   2.996   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.681   4.193   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.731   5.404   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   18   11   24                                             
CONECT   24   23                                                            
CONECT   25   15   26   27                                                  
CONECT   26   25   27                                                       
CONECT   27   26   25   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    6   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₀ClNO₆

Average Mass

453.8800 Da

Monoisotopic Mass

453.09792 Da

IUPAC Name

(1E,2R,7S,14S,15S,16S)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1^{8,12}.0^{2,4}.0^{15,19}]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one

Traditional Name

(1E,2R,7S,14S,15S,16S)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1^{8,12}.0^{2,4}.0^{15,19}]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2[C@@H](O)CC(=O)N3C[C@H]3C3=CC#C[C@H](OC1=C2Cl)[C@@]1(O)[C@@H](O)CC=C1C#C3

InChI Identifier

InChI=1S/C24H20ClNO6/c1-31-18-9-8-15-17(27)11-21(29)26-12-16(26)13-3-2-4-20(32-23(18)22(15)25)24(30)14(6-5-13)7-10-19(24)28/h3,7-9,16-17,19-20,27-28,30H,10-12H2,1H3/b13-3+/t16-,17-,19-,20-,24-,26?/m0/s1

InChI Key

RUCAXECSYVMPPH-QFIHHIJXSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Actinomadura madurae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
Anisole
Alkyl aryl ether
Benzenoid
Aryl halide
Aryl chloride
Vinylaziridine
Tertiary carboxylic acid amide
Tertiary alcohol
Secondary alcohol
Lactam
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Aziridine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.6	ChemAxon
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118 m³·mol⁻¹	ChemAxon
Polarizability	43.17 Å³	ChemAxon
Number of Rings	5	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Maduropeptin

METLIN ID

Not Available

PubChem Compound

102505401

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Khatri I, Subramanian S, Mayilraj S: Genome sequencing and annotation of Amycolatopsis azurea DSM 43854(T). Genom Data. 2014 Mar 12;2:44-5. doi: 10.1016/j.gdata.2013.12.003. eCollection 2014 Dec. [PubMed:26484067 ]
Lohman JR, Huang SX, Horsman GP, Dilfer PE, Huang T, Chen Y, Wendt-Pienkowski E, Shen B: Cloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics. Mol Biosyst. 2013 Mar;9(3):478-91. doi: 10.1039/c3mb25523a. Epub 2013 Jan 29. [PubMed:23360970 ]
Guo X, Crnovcic I, Chang CY, Luo J, Lohman JR, Papinski M, Bechthold A, Horsman GP, Shen B: PokMT1 from the Polyketomycin Biosynthetic Machinery of Streptomyces diastatochromogenes Tu6028 Belongs to the Emerging Family of C-Methyltransferases That Act on CoA-Activated Aromatic Substrates. Biochemistry. 2018 Feb 13;57(6):1003-1011. doi: 10.1021/acs.biochem.7b01219. Epub 2018 Jan 30. [PubMed:29341603 ]
Lohman JR, Shen B: 4-methylideneimidazole-5-one-containing aminomutases in enediyne biosynthesis. Methods Enzymol. 2012;516:299-319. doi: 10.1016/B978-0-12-394291-3.00007-1. [PubMed:23034235 ]
Ling J, Horsman GP, Huang SX, Luo Y, Lin S, Shen B: Enediyne antitumor antibiotic maduropeptin biosynthesis featuring a C-methyltransferase that acts on a CoA-tethered aromatic substrate. J Am Chem Soc. 2010 Sep 15;132(36):12534-6. doi: 10.1021/ja1050814. [PubMed:20718468 ]
LOTUS database [Link]

Showing NP-Card for (1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one (NP0272850)

MOL for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

3D MOL for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

3D SDF for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

3D-SDF for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

PDB for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

3D PDB for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

SMILES for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

INCHI for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

Structure for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)

3D Structure for NP0272850 ((1e,2r,7s,14s,15s,16s)-25-chloro-7,15,16-trihydroxy-11-methoxy-13-oxa-4-azapentacyclo[12.7.3.1⁸,¹².0²,⁴.0¹⁵,¹⁹]pentacosa-1(22),8,10,12(25),18-pentaen-20,23-diyn-5-one)