NP-MRD: Showing NP-Card for Aureoverticillactam (NP0005481)

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Record Information

Version

2.0

Created at

2020-12-09 02:42:32 UTC

Updated at

2021-07-15 16:52:07 UTC

NP-MRD ID

NP0005481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aureoverticillactam

Provided By

NPAtlas

Description

(3Z,5Z,7Z,13Z,15Z,17Z,19Z)-22-[(2E)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol 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. Aureoverticillactam is found in Streptomyces and Streptomyces aureoverticilatus NPS001583. Aureoverticillactam was first documented in 2004 (PMID: 15332863). Based on a literature review very few articles have been published on (3Z,5Z,7Z,13Z,15Z,17Z,19Z)-22-[(2E)-hex-2-en-1-yl]-17-methyl-1-azacyclodocosa-1,3,5,7,13,15,17,19-octaene-2,9,10,12-tetrol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242118193D          

 72 72  0  0  0  0            999 V2000
    6.8074    0.0885    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0925    0.7407    0.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2446    0.0527   -0.9704 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7886    0.1928   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.7793   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    0.9981   -1.2678 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8238    0.4706   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8596   -1.0256    0.0259 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0938   -1.6918   -1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.8746   -1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9735   -0.7350   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0410    1.6097    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.2691   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    1.3697   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    3.2784    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2 37  1  0  0  0  0
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 27 68  1  0  0  0  0
 28 69  1  0  0  0  0
 29 70  1  0  0  0  0
 30 71  1  0  0  0  0
 33 72  1  0  0  0  0
M  END

     RDKit          3D

 72 72  0  0  0  0  0  0  0  0999 V2000
    6.8074    0.0885    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0925    0.7407    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2446    0.0527   -0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7886    0.1928   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.7793   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    0.9981   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238    0.4706   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4248   -2.9021   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3193   -1.7707    1.4006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9811   -2.0632    2.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1968    1.5155    1.8704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120    1.5615   -0.1292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7969    1.3078   -0.7401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1819    3.0346    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  1
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  1
 22 63  1  0
 23 64  1  6
 24 65  1  0
 25 66  1  0
 26 67  1  0
 27 68  1  0
 28 69  1  0
 29 70  1  0
 30 71  1  0
 33 72  1  0
M  END

  Mrv1652306242118193D          

 72 72  0  0  0  0            999 V2000
    6.8074    0.0885    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0925    0.7407    0.0734 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2446    0.0527   -0.9704 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7886    0.1928   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.7793   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    0.9981   -1.2678 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8238    0.4706   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8596   -1.0256    0.0259 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0938   -1.6918   -1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.8746   -1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -3.8201   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -3.8684   -0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -5.0561    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4248   -2.9021   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -1.8451   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456   -1.3715    0.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9320   -1.3261    1.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9811   -2.0632    2.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -0.5521    0.6904 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3052    0.7429    1.0822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1968    1.5155    1.8704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0120    1.5615   -0.1292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7969    1.3078   -0.7401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1819    3.0346    0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    3.9563   -0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4616    3.7877   -1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1405    3.8820   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3536    4.1830   -0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0969    3.3968    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    1.9551    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8969    1.6028    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534    0.9417    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.9737    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7050    0.1244    2.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9378    0.6174    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8725    1.8063    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1579    0.5499   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883    0.4581   -1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4989   -0.2114    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059    1.1678   -2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417    0.6636   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085    2.1472   -1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6446   -1.3640    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096   -1.4536    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934   -1.1616   -2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -3.1614   -2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192   -4.6908   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2226   -5.9124   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984   -4.9093    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946   -5.5028   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3045   -2.6043    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0314   -0.5057    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
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 29 30  2  0  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33  7  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  2 37  1  0  0  0  0
  2 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  4 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  0  0  0  0
  6 44  1  0  0  0  0
  7 45  1  1  0  0  0
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 27 68  1  0  0  0  0
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 29 70  1  0  0  0  0
 30 71  1  0  0  0  0
 33 72  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])\C([H])=C(\[H])/C(/[H])=C(/[H])\C(=C(\[H])/C(/[H])=C([H])\C([H])([H])[C@]([H])(N([H])C(=O)\C([H])=C(\[H])/C(/[H])=C(/[H])\C(\[H])=C([H])/[C@@]([H])(O[H])[C@@]([H])(O[H])C1([H])[H])C([H])([H])C(\[H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO4/c1-3-4-5-8-17-24-18-13-11-15-23(2)16-12-14-19-25(30)22-27(32)26(31)20-9-6-7-10-21-28(33)29-24/h5-16,19-21,24-27,30-32H,3-4,17-18,22H2,1-2H3,(H,29,33)/b7-6-,8-5+,13-11-,16-12-,19-14-,20-9-,21-10-,23-15-/t24-,25-,26-,27+/m1/s1

> <INCHI_KEY>
VMKRIAILWBEBLR-KTVVYJSFSA-N

> <FORMULA>
C28H39NO4

> <MOLECULAR_WEIGHT>
453.623

> <EXACT_MASS>
453.28790874

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.35640479356715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3Z,5Z,7Z,9R,10S,12S,13Z,15Z,17Z,19Z,22R)-22-[(2E)-hex-2-en-1-yl]-9,10,12-trihydroxy-17-methyl-1-azacyclodocosa-3,5,7,13,15,17,19-heptaen-2-one

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
3.793843503999999

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.656084333321242

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.5924611621869

> <JCHEM_PKA_STRONGEST_BASIC>
-0.11414803077232893

> <JCHEM_POLAR_SURFACE_AREA>
89.78999999999999

> <JCHEM_REFRACTIVITY>
145.36210000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5Z,7Z,9R,10S,12S,13Z,15Z,17Z,19Z,22R)-22-[(2E)-hex-2-en-1-yl]-9,10,12-trihydroxy-17-methyl-1-azacyclodocosa-3,5,7,13,15,17,19-heptaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 72  0  0  0  0  0  0  0  0999 V2000
    6.8074    0.0885    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0925    0.7407    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2446    0.0527   -0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7886    0.1928   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.7793   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    0.9981   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238    0.4706   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8596   -1.0256    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938   -1.6918   -1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.8746   -1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -3.8201   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -3.8684   -0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -5.0561    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0374   -1.8451   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9320   -1.3261    1.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9920   -3.1614   -2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5774   -1.2586   -1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0340   -0.9176    1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7035   -0.9484    2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045   -2.6043    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1161   -3.0465    2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.5057    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735   -0.7350   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122    0.6359    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0410    1.6097    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.2691   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    1.3697   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    3.2784    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8652    4.9867   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127    3.6391   -2.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758    3.7358   -2.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032    5.2646   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    3.8978    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    0.4207   -0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  1
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  1
 22 63  1  0
 23 64  1  6
 24 65  1  0
 25 66  1  0
 26 67  1  0
 27 68  1  0
 28 69  1  0
 29 70  1  0
 30 71  1  0
 33 72  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.807   0.089   1.403  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.093   0.741   0.073  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.245   0.053  -0.970  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.789   0.193  -0.636  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.951   0.779  -1.434  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.518   0.998  -1.268  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.824   0.471  -0.077  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.860  -1.026   0.026  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.094  -1.692  -1.283  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.631  -2.875  -1.579  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.851  -3.820  -0.877  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.496  -3.868  -0.661  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.968  -5.056   0.128  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.425  -2.902  -1.158  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.037  -1.845  -0.604  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.946  -1.371   0.732  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.932  -1.326   1.653  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.319  -1.771   1.401  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.981  -2.063   2.558  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.980  -0.552   0.690  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.305   0.743   1.082  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.197   1.516   1.870  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.012   1.562  -0.129  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.797   1.308  -0.740  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.182   3.035   0.076  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.481   3.956  -0.572  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.462   3.788  -1.546  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.141   3.882  -1.407  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.354   4.183  -0.255  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.097   3.397   0.692  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.100   1.955   0.803  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.897   1.603   1.773  0.00  0.00           O+0
HETATM   33  N   UNK     0       0.453   0.942   0.013  0.00  0.00           N+0
HETATM   34  H   UNK     0       6.511  -0.974   1.310  0.00  0.00           H+0
HETATM   35  H   UNK     0       7.705   0.124   2.048  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.938   0.617   1.846  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.872   1.806   0.053  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.158   0.550  -0.158  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.388   0.458  -1.975  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.454  -1.044  -1.007  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.499  -0.211   0.317  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.406   1.168  -2.381  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.942   0.664  -2.168  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.409   2.147  -1.236  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.451   0.812   0.813  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.645  -1.364   0.775  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.910  -1.454   0.472  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.693  -1.162  -2.064  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.992  -3.161  -2.646  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.419  -4.691  -0.441  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.223  -5.912  -0.015  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.998  -4.909   1.201  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.895  -5.503  -0.323  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.861  -3.076  -2.214  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.577  -1.259  -1.417  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.034  -0.918   1.152  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.704  -0.948   2.672  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.305  -2.604   0.676  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.116  -3.046   2.645  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.031  -0.506   1.022  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.973  -0.735  -0.402  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.412   0.636   1.686  0.00  0.00           H+0
HETATM   63  H   UNK     0      -6.041   1.610   1.345  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.793   1.269  -0.922  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.878   1.370  -1.709  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.950   3.278   0.831  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.865   4.987  -0.287  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.813   3.639  -2.625  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.576   3.736  -2.373  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.003   5.265  -0.105  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.681   3.898   1.524  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.231   0.421  -0.630  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3   37   38                                             
CONECT    3    2    4   39   40                                             
CONECT    4    3    5   41                                                  
CONECT    5    4    6   42                                                  
CONECT    6    5    7   43   44                                             
CONECT    7    6    8   33   45                                             
CONECT    8    7    9   46   47                                             
CONECT    9    8   10   48                                                  
CONECT   10    9   11   49                                                  
CONECT   11   10   12   50                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   51   52   53                                             
CONECT   14   12   15   54                                                  
CONECT   15   14   16   55                                                  
CONECT   16   15   17   56                                                  
CONECT   17   16   18   57                                                  
CONECT   18   17   19   20   58                                             
CONECT   19   18   59                                                       
CONECT   20   18   21   60   61                                             
CONECT   21   20   22   23   62                                             
CONECT   22   21   63                                                       
CONECT   23   21   24   25   64                                             
CONECT   24   23   65                                                       
CONECT   25   23   26   66                                                  
CONECT   26   25   27   67                                                  
CONECT   27   26   28   68                                                  
CONECT   28   27   29   69                                                  
CONECT   29   28   30   70                                                  
CONECT   30   29   31   71                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    7   72                                                  
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    2                                                            
CONECT   38    2                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    7                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   13                                                            
CONECT   52   13                                                            
CONECT   53   13                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   18                                                            
CONECT   59   19                                                            
CONECT   60   20                                                            
CONECT   61   20                                                            
CONECT   62   21                                                            
CONECT   63   22                                                            
CONECT   64   23                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   26                                                            
CONECT   68   27                                                            
CONECT   69   28                                                            
CONECT   70   29                                                            
CONECT   71   30                                                            
CONECT   72   33                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  144    0
END

RDKit          3D

72 72  0  0  0  0  0  0  0  0999 V2000
    6.8074    0.0885    1.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0925    0.7407    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2446    0.0527   -0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7886    0.1928   -0.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513    0.7793   -1.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175    0.9981   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8238    0.4706   -0.0768 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8596   -1.0256    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0938   -1.6918   -1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6308   -2.8746   -1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -3.8201   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -3.8684   -0.6606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680   -5.0561    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4248   -2.9021   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -1.8451   -0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3193   -1.7707    1.4006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9811   -2.0632    2.5576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -0.5521    0.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1968    1.5155    1.8704 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4616    3.7877   -1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0969    3.3968    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0996    1.9551    0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8969    1.6028    1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4534    0.9417    0.0132 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5107   -0.9737    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7050    0.1244    2.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9378    0.6174    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8725    1.8063    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1579    0.5499   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883    0.4581   -1.9748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4541   -1.0441   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4989   -0.2114    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059    1.1678   -2.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417    0.6636   -2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4085    2.1472   -1.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510    0.8123    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446   -1.3640    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9096   -1.4536    0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934   -1.1616   -2.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9920   -3.1614   -2.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4192   -4.6908   -0.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2226   -5.9124   -0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9984   -4.9093    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946   -5.5028   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611   -3.0763   -2.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7035   -0.9484    2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045   -2.6043    0.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1161   -3.0465    2.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0314   -0.5057    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735   -0.7350   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4122    0.6359    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0410    1.6097    1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.2691   -0.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8782    1.3697   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500    3.2784    0.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8652    4.9867   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127    3.6391   -2.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5758    3.7358   -2.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032    5.2646   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    3.8978    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    0.4207   -0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33  7  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  2 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  1
  8 46  1  0
  8 47  1  0
  9 48  1  0
 10 49  1  0
 11 50  1  0
 13 51  1  0
 13 52  1  0
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 15 55  1  0
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 17 57  1  0
 18 58  1  6
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 30 71  1  0
 33 72  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₉NO₄

Average Mass

453.6230 Da

Monoisotopic Mass

453.28791 Da

IUPAC Name

(3Z,5Z,7Z,9R,10S,12S,13Z,15Z,17Z,19Z,22R)-22-[(2E)-hex-2-en-1-yl]-9,10,12-trihydroxy-17-methyl-1-azacyclodocosa-3,5,7,13,15,17,19-heptaen-2-one

Traditional Name

(3Z,5Z,7Z,9R,10S,12S,13Z,15Z,17Z,19Z,22R)-22-[(2E)-hex-2-en-1-yl]-9,10,12-trihydroxy-17-methyl-1-azacyclodocosa-3,5,7,13,15,17,19-heptaen-2-one

CAS Registry Number

Not Available

SMILES

CCC\C=C\CC1C\C=C/C=C(/C)\C=C/C=C\C(O)CC(O)C(O)\C=C/C=C\C=C/C(=O)N1

InChI Identifier

InChI=1S/C28H39NO4/c1-3-4-5-8-17-24-18-13-11-15-23(2)16-12-14-19-25(30)22-27(32)26(31)20-9-6-7-10-21-28(33)29-24/h5-16,19-21,24-27,30-32H,3-4,17-18,22H2,1-2H3,(H,29,33)/b7-6-,8-5+,13-11-,16-12-,19-14-,20-9-,21-10-,23-15-

InChI Key

VMKRIAILWBEBLR-KTVVYJSFSA-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
Streptomyces	NPAtlas	15332863
Streptomyces aureoverticilatus NPS001583	Bacteria	KNApSAcK

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
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Polyol
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.65	ALOGPS
logP	3.79	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	-0.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.36 m³·mol⁻¹	ChemAxon
Polarizability	52.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011274

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

Not Available

METLIN ID

Not Available

PubChem Compound

101348436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mitchell SS, Nicholson B, Teisan S, Lam KS, Potts BC: Aureoverticillactam, a novel 22-atom macrocyclic lactam from the marine actinomycete Streptomyces aureoverticillatus. J Nat Prod. 2004 Aug;67(8):1400-2. doi: 10.1021/np049970g. [PubMed:15332863 ]

Showing NP-Card for Aureoverticillactam (NP0005481)

MOL for NP0005481 (Aureoverticillactam)

3D MOL for NP0005481 (Aureoverticillactam)

3D SDF for NP0005481 (Aureoverticillactam)

3D-SDF for NP0005481 (Aureoverticillactam)

PDB for NP0005481 (Aureoverticillactam)

3D PDB for NP0005481 (Aureoverticillactam)

SMILES for NP0005481 (Aureoverticillactam)

INCHI for NP0005481 (Aureoverticillactam)

Structure for NP0005481 (Aureoverticillactam)

3D Structure for NP0005481 (Aureoverticillactam)