NP-MRD: Showing NP-Card for Haliclamide (NP0025375)

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Record Information

Version

2.0

Created at

2021-06-19 17:30:47 UTC

Updated at

2021-06-29 23:50:17 UTC

NP-MRD ID

NP0025375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haliclamide

Provided By

JEOL Database JEOL Logo

Description

Haliclamide is found in Haliclona sp. Haliclamide was first documented in 2001 (Randazzo, A., et al.). Based on a literature review very few articles have been published on (3S,6R,10R,16R)-3-benzyl-12-hydroxy-10-(hydroxymethyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-11-ene-2,5-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119303D          

 73 74  0  0  0  0            999 V2000
   -2.6035   -3.2171   -3.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.1259   -3.4181 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744   -2.7073   -3.2644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8945   -1.6301   -3.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3312   -2.1900   -3.0616 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6351   -3.4221   -2.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5892   -3.1511   -0.6999 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9750   -4.3842    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -4.6267    0.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061   -5.2651    0.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -5.1729    0.2613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0598   -6.5807    0.2568 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4951   -7.3517   -0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -4.2532    1.3094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4638   -3.7424    0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0264   -2.6272    1.7650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6580   -1.1975    1.2999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5480   -0.1864    2.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4761    0.0189    0.7317 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    0.1777    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2585    2.3150   -0.2842 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1540    4.6017   -2.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274    4.9814   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342    4.5060    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    3.6491    0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1599    0.8620   -2.8092 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6636   -0.9914   -1.7529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3637   -3.7469   -4.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8384   -0.8986   -3.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6040   -2.8030   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3654   -6.0082    1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1412   -7.1078    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1720   -4.7745    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770   -3.4073    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4327   -3.4009   -0.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1651   -4.5852    0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1207   -2.7157    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367   -2.7948    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6017   -0.3409    1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885    0.8441    1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -0.2824    3.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392   -0.6964    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    1.0540    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    0.3084   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290    0.7516   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040    2.5300   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    2.5690    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    3.4595   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3035    4.9709   -3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571    5.6489   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    4.8050    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304    3.2929    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 19  1  0  0  0  0
  2  1  1  0  0  0  0
 19 21  1  0  0  0  0
  6  5  1  0  0  0  0
 19 20  2  0  0  0  0
  8 10  1  0  0  0  0
 21 23  1  0  0  0  0
  8  7  1  0  0  0  0
 23 31  1  0  0  0  0
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 31 33  1  0  0  0  0
  5  4  1  0  0  0  0
 31 32  2  0  0  0  0
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 11 14  1  0  0  0  0
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  9  8  2  0  0  0  0
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  4  3  1  0  0  0  0
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 25 26  2  0  0  0  0
  7  6  1  0  0  0  0
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 16 17  1  0  0  0  0
 27 28  2  0  0  0  0
  3  2  1  0  0  0  0
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 30 25  1  0  0  0  0
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  7 46  1  0  0  0  0
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  6 44  1  0  0  0  0
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  5 42  1  0  0  0  0
  5 43  1  0  0  0  0
  4 41  1  6  0  0  0
  3 39  1  0  0  0  0
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  2 37  1  0  0  0  0
  2 38  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
 10 48  1  0  0  0  0
 11 49  1  6  0  0  0
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 16 58  1  0  0  0  0
 17 59  1  6  0  0  0
 18 60  1  0  0  0  0
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 18 62  1  0  0  0  0
 23 66  1  1  0  0  0
 12 50  1  0  0  0  0
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 13 52  1  0  0  0  0
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 30 73  1  0  0  0  0
 22 63  1  0  0  0  0
 22 64  1  0  0  0  0
 22 65  1  0  0  0  0
M  END

     RDKit          3D

 73 74  0  0  0  0  0  0  0  0999 V2000
   -2.6035   -3.2171   -3.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.1259   -3.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -2.7073   -3.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.6301   -3.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3312   -2.1900   -3.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5892   -3.1511   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -4.3842    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -4.6267    0.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6580   -1.1975    1.2999 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4761    0.0189    0.7317 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    0.1777    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450    0.8229   -0.3632 C   0  0  1  0  0  0  0  0  0  0  0  0
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  2  1  1  0
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  6  5  1  0
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  2 38  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 10 48  1  0
 11 49  1  6
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  6
 18 60  1  0
 18 61  1  0
 18 62  1  0
 23 66  1  1
 12 50  1  0
 12 51  1  0
 13 52  1  0
 24 67  1  0
 24 68  1  0
 26 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
M  END


  Mrv1652306192119303D          

 73 74  0  0  0  0            999 V2000
   -2.6035   -3.2171   -3.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.1259   -3.4181 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1744   -2.7073   -3.2644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8945   -1.6301   -3.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3312   -2.1900   -3.0616 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6351   -3.4221   -2.1981 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5892   -3.1511   -0.6999 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9750   -4.3842    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -4.6267    0.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0061   -5.2651    0.4784 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5571   -5.1729    0.2613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0598   -6.5807    0.2568 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4951   -7.3517   -0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -4.2532    1.3094 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4638   -3.7424    0.8695 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0264   -2.6272    1.7650 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4761    0.0189    0.7317 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    0.1777    0.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450    0.8229   -0.3632 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2585    2.3150   -0.2842 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8837    3.2591   -0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865    3.7457   -1.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540    4.6017   -2.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0274    4.9814   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1294    0.2653   -1.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6636   -0.9914   -1.7529 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1412   -7.1078    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1420   -6.5437    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1720   -4.7745    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770   -3.4073    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4207    0.3084   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0  0  0  0
 19 21  1  0  0  0  0
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 19 20  2  0  0  0  0
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 21 23  1  0  0  0  0
  8  7  1  0  0  0  0
 23 31  1  0  0  0  0
 10 11  1  0  0  0  0
 31 33  1  0  0  0  0
  5  4  1  0  0  0  0
 31 32  2  0  0  0  0
 33  4  1  0  0  0  0
 11 14  1  0  0  0  0
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  4  3  1  0  0  0  0
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 25 26  2  0  0  0  0
  7  6  1  0  0  0  0
 26 27  1  0  0  0  0
 16 17  1  0  0  0  0
 27 28  2  0  0  0  0
  3  2  1  0  0  0  0
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  5 42  1  0  0  0  0
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  4 41  1  6  0  0  0
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 30 73  1  0  0  0  0
 22 63  1  0  0  0  0
 22 64  1  0  0  0  0
 22 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025375

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H40N2O5/c1-4-10-22-15-9-16-24(30)27-21(18-29)14-8-11-19(2)25(31)28(3)23(26(32)33-22)17-20-12-6-5-7-13-20/h5-7,12-13,19,21-23,29H,4,8-11,14-18H2,1-3H3,(H,27,30)/t19-,21-,22-,23+/m1/s1

> <INCHI_KEY>
SGJNUKUCBPFPJZ-ADHNFCLRSA-N

> <FORMULA>
C26H40N2O5

> <MOLECULAR_WEIGHT>
460.615

> <EXACT_MASS>
460.293722396

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.927286146255376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R,10R,16R)-3-benzyl-10-(hydroxymethyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadecane-2,5,12-trione

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.543448859333332

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.151463650535678

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.353155628260222

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6079610434413695

> <JCHEM_POLAR_SURFACE_AREA>
95.94000000000001

> <JCHEM_REFRACTIVITY>
127.2629

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R,10R,16R)-3-benzyl-10-(hydroxymethyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadecane-2,5,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 74  0  0  0  0  0  0  0  0999 V2000
   -2.6035   -3.2171   -3.7026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827   -2.1259   -3.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -2.7073   -3.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.6301   -3.0279 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3312   -2.1900   -3.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351   -3.4221   -2.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892   -3.1511   -0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -4.3842    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1478   -4.6267    0.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7367   -2.7948    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513   -1.1421    0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017   -0.3409    1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885    0.8441    1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -0.2824    3.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392   -0.6964    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    1.0540    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    0.3084   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290    0.7516   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040    2.5300   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    2.5690    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    3.4595   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3035    4.9709   -3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571    5.6489   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    4.8050    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304    3.2929    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 19  1  0
  2  1  1  0
 19 21  1  0
  6  5  1  0
 19 20  2  0
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  8  7  1  0
 23 31  1  0
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  5  4  1  0
 31 32  2  0
 33  4  1  0
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  9  8  2  0
 12 13  1  0
 14 15  1  0
 23 24  1  0
  4  3  1  0
 24 25  1  0
 15 16  1  0
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  7  6  1  0
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 16 17  1  0
 27 28  2  0
  3  2  1  0
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 17 18  1  0
 29 30  2  0
 30 25  1  0
 21 22  1  0
  7 46  1  0
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  6 44  1  0
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  4 41  1  6
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 22 63  1  0
 22 64  1  0
 22 65  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.603  -3.217  -3.703  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.583  -2.126  -3.418  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.174  -2.707  -3.264  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.895  -1.630  -3.028  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.331  -2.190  -3.062  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.635  -3.422  -2.198  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.589  -3.151  -0.700  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.975  -4.384   0.092  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.148  -4.627   0.374  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.006  -5.265   0.478  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.557  -5.173   0.261  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.060  -6.581   0.257  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.495  -7.352  -0.809  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.088  -4.253   1.309  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.464  -3.742   0.870  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.026  -2.627   1.765  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.658  -1.198   1.300  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.548  -0.186   2.030  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.200  -0.839   1.594  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.351  -1.287   2.604  0.00  0.00           O+0
HETATM   21  N   UNK     0       0.476   0.019   0.732  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.912   0.178   0.946  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.145   0.823  -0.363  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.259   2.315  -0.284  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.884   3.259  -0.592  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.087   3.746  -1.889  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.154   4.602  -2.166  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.027   4.981  -1.149  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.834   4.506   0.146  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.768   3.649   0.424  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.129   0.265  -1.779  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.160   0.862  -2.809  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.664  -0.991  -1.753  0.00  0.00           O+0
HETATM   34  H   UNK     0      -2.364  -3.747  -4.630  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.603  -2.783  -3.808  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.634  -3.947  -2.887  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.879  -1.601  -2.503  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.598  -1.397  -4.236  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.194  -3.403  -2.420  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.080  -3.281  -4.163  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.838  -0.899  -3.844  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.562  -2.458  -4.101  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.027  -1.390  -2.781  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.644  -3.771  -2.455  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.968  -4.250  -2.463  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.297  -2.356  -0.438  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.604  -2.803  -0.392  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.365  -6.008   1.068  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.425  -4.746  -0.736  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.141  -7.108   1.196  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.142  -6.544   0.105  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.457  -7.194  -0.803  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.172  -4.774   2.271  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.577  -3.407   1.488  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.433  -3.401  -0.171  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.165  -4.585   0.899  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.121  -2.716   1.732  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.737  -2.795   2.809  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.851  -1.142   0.225  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.602  -0.341   1.775  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.289   0.844   1.772  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.444  -0.282   3.116  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.339  -0.696   1.446  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.082   1.054   1.577  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.421   0.308  -0.013  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.229   0.752  -0.252  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.104   2.530  -0.951  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.608   2.569   0.725  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.419   3.459  -2.700  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.304   4.971  -3.177  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.857   5.649  -1.366  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.513   4.805   0.941  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.630   3.293   1.443  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3   37   38                                             
CONECT    3    4    2   39   40                                             
CONECT    4    5   33    3   41                                             
CONECT    5    6    4   42   43                                             
CONECT    6    5    7   44   45                                             
CONECT    7    8    6   46   47                                             
CONECT    8   10    7    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   48                                                  
CONECT   11   10   14   12   49                                             
CONECT   12   11   13   50   51                                             
CONECT   13   12   52                                                       
CONECT   14   11   15   53   54                                             
CONECT   15   14   16   55   56                                             
CONECT   16   15   17   57   58                                             
CONECT   17   19   16   18   59                                             
CONECT   18   17   60   61   62                                             
CONECT   19   17   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   23   22                                                  
CONECT   22   21   63   64   65                                             
CONECT   23   21   31   24   66                                             
CONECT   24   23   25   67   68                                             
CONECT   25   24   26   30                                                  
CONECT   26   25   27   69                                                  
CONECT   27   26   28   70                                                  
CONECT   28   27   29   71                                                  
CONECT   29   28   30   72                                                  
CONECT   30   29   25   73                                                  
CONECT   31   23   33   32                                                  
CONECT   32   31                                                            
CONECT   33   31    4                                                       
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    5                                                            
CONECT   44    6                                                            
CONECT   45    6                                                            
CONECT   46    7                                                            
CONECT   47    7                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   16                                                            
CONECT   58   16                                                            
CONECT   59   17                                                            
CONECT   60   18                                                            
CONECT   61   18                                                            
CONECT   62   18                                                            
CONECT   63   22                                                            
CONECT   64   22                                                            
CONECT   65   22                                                            
CONECT   66   23                                                            
CONECT   67   24                                                            
CONECT   68   24                                                            
CONECT   69   26                                                            
CONECT   70   27                                                            
CONECT   71   28                                                            
CONECT   72   29                                                            
CONECT   73   30                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  148    0
END

RDKit          3D

73 74  0  0  0  0  0  0  0  0999 V2000
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    4.1478   -4.6267    0.3740 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5571   -5.1729    0.2613 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.2885    0.8441    1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -0.2824    3.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3392   -0.6964    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    1.0540    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207    0.3084   -0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290    0.7516   -0.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1040    2.5300   -0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    2.5690    0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4187    3.4595   -2.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3035    4.9709   -3.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571    5.6489   -1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5129    4.8050    0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304    3.2929    1.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 19  1  0
  2  1  1  0
 19 21  1  0
  6  5  1  0
 19 20  2  0
  8 10  1  0
 21 23  1  0
  8  7  1  0
 23 31  1  0
 10 11  1  0
 31 33  1  0
  5  4  1  0
 31 32  2  0
 33  4  1  0
 11 14  1  0
 11 12  1  0
  9  8  2  0
 12 13  1  0
 14 15  1  0
 23 24  1  0
  4  3  1  0
 24 25  1  0
 15 16  1  0
 25 26  2  0
  7  6  1  0
 26 27  1  0
 16 17  1  0
 27 28  2  0
  3  2  1  0
 28 29  1  0
 17 18  1  0
 29 30  2  0
 30 25  1  0
 21 22  1  0
  7 46  1  0
  7 47  1  0
  6 44  1  0
  6 45  1  0
  5 42  1  0
  5 43  1  0
  4 41  1  6
  3 39  1  0
  3 40  1  0
  2 37  1  0
  2 38  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 10 48  1  0
 11 49  1  6
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 16 57  1  0
 16 58  1  0
 17 59  1  6
 18 60  1  0
 18 61  1  0
 18 62  1  0
 23 66  1  1
 12 50  1  0
 12 51  1  0
 13 52  1  0
 24 67  1  0
 24 68  1  0
 26 69  1  0
 27 70  1  0
 28 71  1  0
 29 72  1  0
 30 73  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀N₂O₅

Average Mass

460.6150 Da

Monoisotopic Mass

460.29372 Da

IUPAC Name

(3S,6R,10R,16R)-3-benzyl-10-(hydroxymethyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadecane-2,5,12-trione

Traditional Name

(3S,6R,10R,16R)-3-benzyl-10-(hydroxymethyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadecane-2,5,12-trione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]1([H])N([H])C(=O)C([H])([H])C([H])([H])C([H])([H])[C@]([H])(OC(=O)[C@@]([H])(N(C(=O)[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C1([H])[H])C([H])([H])[H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H40N2O5/c1-4-10-22-15-9-16-24(30)27-21(18-29)14-8-11-19(2)25(31)28(3)23(26(32)33-22)17-20-12-6-5-7-13-20/h5-7,12-13,19,21-23,29H,4,8-11,14-18H2,1-3H3,(H,27,30)/t19-,21-,22-,23+/m1/s1

InChI Key

SGJNUKUCBPFPJZ-ADHNFCLRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Haliclona sp.	JEOL database	Randazzo, A., et al, Tetrahedron 57, 4443 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolide lactams

Sub Class

Not Available

Direct Parent

Macrolide lactams

Alternative Parents

Substituents

Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	3.19	ALOGPS
logP	3.54	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.26 m³·mol⁻¹	ChemAxon
Polarizability	50.93 Å³	ChemAxon
Number of Rings	2	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

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

71615018

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Randazzo, A., et al. (2001). Randazzo, A., et al, Tetrahedron 57, 4443 (2001). Tetrahedron.

Showing NP-Card for Haliclamide (NP0025375)

MOL for NP0025375 (Haliclamide)

3D MOL for NP0025375 (Haliclamide)

3D SDF for NP0025375 (Haliclamide)

3D-SDF for NP0025375 (Haliclamide)

PDB for NP0025375 (Haliclamide)

3D PDB for NP0025375 (Haliclamide)

SMILES for NP0025375 (Haliclamide)

INCHI for NP0025375 (Haliclamide)

Structure for NP0025375 (Haliclamide)

3D Structure for NP0025375 (Haliclamide)