NP-MRD: Showing NP-Card for (7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone (NP0310330)

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Record Information

Version

2.0

Created at

2022-09-11 05:34:10 UTC

Updated at

2024-09-12 20:29:50 UTC

NP-MRD ID

NP0310330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone

Description

Naphthomycin A 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. (7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone was first documented in 2013 (PMID: 23420111). Based on a literature review a small amount of articles have been published on Naphthomycin A (PMID: 28406643) (PMID: 38694805).

Structure

MOL SDF PDB SMILES InChI

NP0022672
  Mrv2104 05272322193D          

 97 99  0  0  0  0            999 V2000
   -1.3960    6.2753   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    4.9289   -0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472    4.2417   -1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211    2.9379   -1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    2.0829   -2.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225    2.2042   -1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5733    1.1825   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0545    1.1585   -1.5746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7895    2.3152   -2.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4236    1.1084   -0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7534    0.5896    0.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    0.3212    0.8569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2700   -1.1252    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9930   -1.7006   -0.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1170   -1.8403    1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0069   -3.4123   -0.3351 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8005   -6.0317   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5653    2.3371   -3.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4599    2.1358    0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7383   -0.3147   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5149    0.8238    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9252    0.2994    1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5753   -0.6511    2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1163   -6.4165    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004   -4.2003    1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3246   -5.9661   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0661   -4.9700   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074   -4.5292   -0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9926   -2.4625   -1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1211   -1.1603    2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952   -2.6881    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7056   -1.1819    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2373    1.2887   -0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8301    2.9335    0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9776    5.2663    0.7780 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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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M  END

NP0022672
  Mrv2104 05272322193D          

 97 99  0  0  0  0            999 V2000
   -1.3960    6.2753   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    4.9289   -0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472    4.2417   -1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3211    2.9379   -1.7907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3270    2.0829   -2.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225    2.2042   -1.6732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5733    1.1825   -1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0545    1.1585   -1.5746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7895    2.3152   -2.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4236    1.1084   -0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7534    0.5896    0.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    0.3212    0.8569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2700   -1.1252    0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6439    3.6907    0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575    3.1350    0.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1815    1.7734    0.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8491    1.2073    0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7362    0.0580    1.0930 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6904    2.0976    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1598    1.3030    0.3346 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    3.4285    0.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937    4.3307    0.4148 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.0926    4.3314   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    3.8566   -1.8158 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1754    4.0020    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2853    5.1656    1.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3939    6.7033   -0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6802    6.9719   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035    6.2183    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3324    4.6891   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4450    0.2477   -2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5139    3.2880   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8741    2.2050   -2.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4599    2.1358    0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7383   -0.3147   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5149    0.8238    0.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9252    0.2994    1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5753   -0.6511    2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9481   -1.7464    3.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3123   -2.3854    3.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900   -2.7142   -0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3988   -4.3692    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6889   -2.8685    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0780   -2.5376   -0.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120   -5.3414   -0.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3943   -2.4547    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140   -5.3075   -0.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7823   -5.0749    1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2280   -2.8158    2.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506   -2.9656    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9297   -2.1254    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4497   -4.1977   -1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1163   -6.4165    0.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004   -4.2003    1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3246   -5.9661   -0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0661   -4.9700   -1.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3074   -4.5292   -0.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9926   -2.4625   -1.4577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1211   -1.1603    2.2386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952   -2.6881    1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7056   -1.1819    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2373    1.2887   -0.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8301    2.9335    0.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1077    4.5340    0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4568    3.5909   -0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7744    4.7580    0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9776    5.2663    0.7780 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
  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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
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 41 42  1  0  0  0  0
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 42 44  1  0  0  0  0
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 44 46  2  0  0  0  0
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 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 46 50  1  0  0  0  0
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 48  2  1  0  0  0  0
 41 34  1  0  0  0  0
 50 40  1  0  0  0  0
  1 52  1  0  0  0  0
  1 53  1  0  0  0  0
  1 54  1  0  0  0  0
  3 55  1  0  0  0  0
  4 56  1  0  0  0  0
  5 57  1  0  0  0  0
  6 58  1  0  0  0  0
  7 59  1  0  0  0  0
  8 60  1  6  0  0  0
  9 61  1  0  0  0  0
  9 62  1  0  0  0  0
  9 63  1  0  0  0  0
 10 64  1  1  0  0  0
 11 65  1  0  0  0  0
 12 66  1  0  0  0  0
 12 67  1  0  0  0  0
 16 68  1  0  0  0  0
 16 69  1  0  0  0  0
 16 70  1  0  0  0  0
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 19 74  1  6  0  0  0
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 25 82  1  6  0  0  0
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 27 84  1  1  0  0  0
 28 85  1  0  0  0  0
 28 86  1  0  0  0  0
 28 87  1  0  0  0  0
 29 88  1  0  0  0  0
 31 89  1  0  0  0  0
 31 90  1  0  0  0  0
 31 91  1  0  0  0  0
 36 92  1  0  0  0  0
 38 93  1  0  0  0  0
 38 94  1  0  0  0  0
 38 95  1  0  0  0  0
 39 96  1  0  0  0  0
 47 97  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0310330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C3=C(C([H])=C1C([H])([H])[H])C(=O)C(N([H])C(=O)\C(=C(\[H])/C(/[H])=C(/[H])\C(\[H])=C([H])\[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C(=O)\C(=C([H])\C([H])([H])[C@]([H])(O[H])\C([H])=C([H])\[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@]([H])(\C([H])=C(\C2=O)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])=C(Cl)C3=O

> <INCHI_IDENTIFIER>
InChI=1/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9+,16-14+,21-13+,23-12-,25-17+/t20-,22-,24-,27-,29-,35-/s2

> <INCHI_KEY>
AXEGRHYJHHPVDH-DTSHVWKONA-N

> <FORMULA>
C40H46ClNO9

> <MOLECULAR_WEIGHT>
720.26

> <EXACT_MASS>
719.2861098

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
78.17443923387654

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7E,9S,10S,11S,12E,14S,16E,20S,21S,22E,24Z,26Z)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0^{5,33}]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone

> <JCHEM_LOGP>
5.620512020333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.481507425550049

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.446116819193321

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7501853812930337

> <JCHEM_POLAR_SURFACE_AREA>
178.3

> <JCHEM_REFRACTIVITY>
205.5944000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(7E,9S,10S,11S,12E,14S,16E,20S,21S,22E,24Z,26Z)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0^{5,33}]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0022672                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.396   6.275  -0.056  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.276   4.929  -0.694  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.347   4.242  -1.153  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.321   2.938  -1.791  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.327   2.083  -2.020  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.723   2.204  -1.673  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.573   1.183  -1.875  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.054   1.159  -1.575  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.790   2.315  -2.269  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.424   1.108  -0.067  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.753   0.590   0.083  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.488   0.321   0.857  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.270  -1.125   0.444  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.993  -1.701  -0.367  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.117  -1.840   1.097  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.974  -1.645   2.576  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.340  -2.612   0.311  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.099  -3.353   0.759  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.007  -3.412  -0.335  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.213  -4.558  -1.158  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.621  -3.405   0.267  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.324  -4.365   0.245  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.734  -4.273   0.846  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.980  -2.968   1.595  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.799  -4.595  -0.260  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.801  -6.032  -0.426  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.266  -4.091  -0.019  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.296  -4.936  -0.787  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.437  -2.651  -0.476  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.041  -1.615   0.148  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.723  -1.665   1.476  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.988  -0.309  -0.596  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.665  -0.220  -1.782  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.264   0.971   0.084  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.543   1.537  -0.001  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.579   0.745  -0.412  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.753   2.891   0.321  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.118   3.522   0.258  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.644   3.691   0.654  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.357   3.135   0.706  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.181   1.773   0.471  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.849   1.207   0.687  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.736   0.058   1.093  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.690   2.098   0.495  0.00  0.00           C+0
HETATM   45 Cl   UNK     0       0.160   1.303   0.335  0.00  0.00          Cl+0
HETATM   46  C   UNK     0       1.837   3.429   0.586  0.00  0.00           C+0
HETATM   47  N   UNK     0       0.794   4.331   0.415  0.00  0.00           N+0
HETATM   48  C   UNK     0       0.093   4.331  -0.779  0.00  0.00           C+0
HETATM   49  O   UNK     0       0.545   3.857  -1.816  0.00  0.00           O+0
HETATM   50  C   UNK     0       3.175   4.002   0.925  0.00  0.00           C+0
HETATM   51  O   UNK     0       3.285   5.166   1.297  0.00  0.00           O+0
HETATM   52  H   UNK     0      -2.394   6.703  -0.190  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.680   6.972  -0.501  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.204   6.218   1.020  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.332   4.689  -1.039  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.349   2.593  -2.142  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.051   1.155  -2.526  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.074   3.133  -1.239  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.197   0.253  -2.304  0.00  0.00           H+0
HETATM   60  H   UNK     0      -7.445   0.248  -2.052  0.00  0.00           H+0
HETATM   61  H   UNK     0      -7.514   3.288  -1.844  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.565   2.337  -3.342  0.00  0.00           H+0
HETATM   63  H   UNK     0      -8.874   2.205  -2.166  0.00  0.00           H+0
HETATM   64  H   UNK     0      -7.460   2.136   0.317  0.00  0.00           H+0
HETATM   65  H   UNK     0      -8.738  -0.315  -0.299  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.515   0.824   0.914  0.00  0.00           H+0
HETATM   67  H   UNK     0      -6.925   0.299   1.861  0.00  0.00           H+0
HETATM   68  H   UNK     0      -4.575  -0.651   2.798  0.00  0.00           H+0
HETATM   69  H   UNK     0      -5.948  -1.746   3.068  0.00  0.00           H+0
HETATM   70  H   UNK     0      -4.312  -2.385   3.032  0.00  0.00           H+0
HETATM   71  H   UNK     0      -4.590  -2.714  -0.747  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.399  -4.369   1.040  0.00  0.00           H+0
HETATM   73  H   UNK     0      -2.689  -2.869   1.650  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.078  -2.538  -0.992  0.00  0.00           H+0
HETATM   75  H   UNK     0      -2.112  -5.341  -0.593  0.00  0.00           H+0
HETATM   76  H   UNK     0      -0.394  -2.455   0.752  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.114  -5.308  -0.260  0.00  0.00           H+0
HETATM   78  H   UNK     0       1.782  -5.075   1.599  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.228  -2.816   2.380  0.00  0.00           H+0
HETATM   80  H   UNK     0       2.951  -2.966   2.097  0.00  0.00           H+0
HETATM   81  H   UNK     0       1.930  -2.125   0.903  0.00  0.00           H+0
HETATM   82  H   UNK     0       2.450  -4.198  -1.223  0.00  0.00           H+0
HETATM   83  H   UNK     0       3.116  -6.417   0.411  0.00  0.00           H+0
HETATM   84  H   UNK     0       4.500  -4.200   1.044  0.00  0.00           H+0
HETATM   85  H   UNK     0       5.325  -5.966  -0.411  0.00  0.00           H+0
HETATM   86  H   UNK     0       5.066  -4.970  -1.859  0.00  0.00           H+0
HETATM   87  H   UNK     0       6.307  -4.529  -0.670  0.00  0.00           H+0
HETATM   88  H   UNK     0       3.993  -2.462  -1.458  0.00  0.00           H+0
HETATM   89  H   UNK     0       5.121  -1.160   2.239  0.00  0.00           H+0
HETATM   90  H   UNK     0       5.895  -2.688   1.813  0.00  0.00           H+0
HETATM   91  H   UNK     0       6.706  -1.182   1.432  0.00  0.00           H+0
HETATM   92  H   UNK     0       8.237   1.289  -0.883  0.00  0.00           H+0
HETATM   93  H   UNK     0       8.830   2.934   0.845  0.00  0.00           H+0
HETATM   94  H   UNK     0       8.108   4.534   0.675  0.00  0.00           H+0
HETATM   95  H   UNK     0       8.457   3.591  -0.782  0.00  0.00           H+0
HETATM   96  H   UNK     0       5.774   4.758   0.850  0.00  0.00           H+0
HETATM   97  H   UNK     0       0.978   5.266   0.778  0.00  0.00           H+0
CONECT    1    2   52   53   54                                             
CONECT    2    1    3   48                                                  
CONECT    3    2    4   55                                                  
CONECT    4    3    5   56                                                  
CONECT    5    4    6   57                                                  
CONECT    6    5    7   58                                                  
CONECT    7    6    8   59                                                  
CONECT    8    7    9   10   60                                             
CONECT    9    8   61   62   63                                             
CONECT   10    8   11   12   64                                             
CONECT   11   10   65                                                       
CONECT   12   10   13   66   67                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   68   69   70                                             
CONECT   17   15   18   71                                                  
CONECT   18   17   19   72   73                                             
CONECT   19   18   20   21   74                                             
CONECT   20   19   75                                                       
CONECT   21   19   22   76                                                  
CONECT   22   21   23   77                                                  
CONECT   23   22   24   25   78                                             
CONECT   24   23   79   80   81                                             
CONECT   25   23   26   27   82                                             
CONECT   26   25   83                                                       
CONECT   27   25   28   29   84                                             
CONECT   28   27   85   86   87                                             
CONECT   29   27   30   88                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   89   90   91                                             
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   41                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   92                                                       
CONECT   37   35   38   39                                                  
CONECT   38   37   93   94   95                                             
CONECT   39   37   40   96                                                  
CONECT   40   39   41   50                                                  
CONECT   41   40   42   34                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   50                                                  
CONECT   47   46   48   97                                                  
CONECT   48   47   49    2                                                  
CONECT   49   48                                                            
CONECT   50   46   51   40                                                  
CONECT   51   50                                                            
CONECT   52    1                                                            
CONECT   53    1                                                            
CONECT   54    1                                                            
CONECT   55    3                                                            
CONECT   56    4                                                            
CONECT   57    5                                                            
CONECT   58    6                                                            
CONECT   59    7                                                            
CONECT   60    8                                                            
CONECT   61    9                                                            
CONECT   62    9                                                            
CONECT   63    9                                                            
CONECT   64   10                                                            
CONECT   65   11                                                            
CONECT   66   12                                                            
CONECT   67   12                                                            
CONECT   68   16                                                            
CONECT   69   16                                                            
CONECT   70   16                                                            
CONECT   71   17                                                            
CONECT   72   18                                                            
CONECT   73   18                                                            
CONECT   74   19                                                            
CONECT   75   20                                                            
CONECT   76   21                                                            
CONECT   77   22                                                            
CONECT   78   23                                                            
CONECT   79   24                                                            
CONECT   80   24                                                            
CONECT   81   24                                                            
CONECT   82   25                                                            
CONECT   83   26                                                            
CONECT   84   27                                                            
CONECT   85   28                                                            
CONECT   86   28                                                            
CONECT   87   28                                                            
CONECT   88   29                                                            
CONECT   89   31                                                            
CONECT   90   31                                                            
CONECT   91   31                                                            
CONECT   92   36                                                            
CONECT   93   38                                                            
CONECT   94   38                                                            
CONECT   95   38                                                            
CONECT   96   39                                                            
CONECT   97   47                                                            
MASTER        0    0    0    0    0    0    0    0   97    0  198    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₄₆ClNO₉

Average Mass

720.2600 Da

Monoisotopic Mass

719.28611 Da

IUPAC Name

(7E,9S,10S,11S,12E,14S,16E,20S,21S,22E,24Z,26Z)-31-chloro-4,10,14,20-tetrahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0^{5,33}]tetratriaconta-1(33),2,4,7,12,16,22,24,26,30-decaene-6,18,28,32,34-pentone

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C3=C(C([H])=C1C([H])([H])[H])C(=O)C(N([H])C(=O)\C(=C(\[H])/C(/[H])=C(/[H])\C(\[H])=C([H])\[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C(=O)\C(=C([H])\C([H])([H])[C@]([H])(O[H])\C([H])=C([H])\[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@]([H])(\C([H])=C(\C2=O)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])=C(Cl)C3=O

InChI Identifier

InChI=1/C40H46ClNO9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19H2,1-7H3,(H,42,51)/b10-8-,11-9+,16-14+,21-13+,23-12-,25-17+/t20-,22-,24-,27-,29-,35-/s2

InChI Key

AXEGRHYJHHPVDH-DTSHVWKONA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Naphthoquinone
Naphthalene
Quinone
Aryl ketone
Phenol
Benzenoid
Alpha-haloketone
Alpha-chloroketone
Vinylogous halide
Vinylogous amide
Vinylogous acid
Carboxamide group
Ketone
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Cyclic ketone
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Polyol
Haloalkene
Chloroalkene
Vinyl halide
Vinyl chloride
Alcohol
Organohalogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organochloride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
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	5.62	ChemAxon
pKa (Strongest Acidic)	5.45	ChemAxon
pKa (Strongest Basic)	-0.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	178.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	205.59 m³·mol⁻¹	ChemAxon
Polarizability	78.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Naphthomycin A

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Son S, Ko SK, Jang M, Lee JK, Kwon MC, Kang DH, Ryoo IJ, Lee JS, Hong YS, Kim BY, Jang JH, Ahn JS: Polyketides and Anthranilic Acid Possessing 6-Deoxy-alpha-l-talopyranose from a Streptomyces Species. J Nat Prod. 2017 May 26;80(5):1378-1386. doi: 10.1021/acs.jnatprod.6b01059. Epub 2017 Apr 13. [PubMed:28406643 ]
Kaewkla O, Perkins M, Thamchaipenet A, Saijuntha W, Sukpanoa S, Suriyachadkun C, Chamroensaksri N, Chumroenphat T, Franco CMM: Description of Streptomyces naphthomycinicus sp. nov., an endophytic actinobacterium producing naphthomycin A and its genome insight for discovering bioactive compounds. Front Microbiol. 2024 Apr 17;15:1353511. doi: 10.3389/fmicb.2024.1353511. eCollection 2024. [PubMed:38694805 ]
Liu H, Xiao L, Wei J, Schmitz JC, Liu M, Wang C, Cheng L, Wu N, Chen L, Zhang Y, Lin X: Identification of Streptomyces sp. nov. WH26 producing cytotoxic compounds isolated from marine solar saltern in China. World J Microbiol Biotechnol. 2013 Jul;29(7):1271-8. doi: 10.1007/s11274-013-1290-8. Epub 2013 Feb 19. [PubMed:23420111 ]
LOTUS database [Link]

Showing NP-Card for (7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone (NP0310330)

MOL for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

3D MOL for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

3D SDF for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

3D-SDF for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

PDB for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

3D PDB for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

SMILES for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

INCHI for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

Structure for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)

3D Structure for NP0310330 ((7e,9s,10s,11s,12e,14s,16e,20s,21s,22e,24z,26z)-31-chloro-4,10,14,20,28-pentahydroxy-3,7,9,11,17,21,27-heptamethyl-29-azatricyclo[28.3.1.0⁵,³³]tetratriaconta-1(33),2,4,7,12,16,22,24,26,28,30-undecaene-6,18,32,34-tetrone)