NP-MRD: Showing NP-Card for michaolide c (NP0201649)

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Record Information

Version

2.0

Created at

2022-09-04 20:44:01 UTC

Updated at

2022-09-04 20:44:01 UTC

NP-MRD ID

NP0201649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

michaolide c

Description

Michaolide C belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Michaolide C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on michaolide C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042222442D          

 32 34  0  0  1  0            999 V2000
   -0.1498   -2.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1075   -2.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -1.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -0.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.0336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2558   -0.2915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1353    0.5247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024    0.2209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9666    1.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7073    0.4020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7098    1.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110    0.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666   -0.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -1.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -0.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075   -1.8699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3112   -2.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5520   -2.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3557   -3.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9889   -3.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472   -2.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -2.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -4.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8920   -3.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -2.6030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6020   -3.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224   -3.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -4.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -4.4440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8929   -1.8586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32  2  1  1  0  0  0
  6 32  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    4.9815   -0.5981   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0922    0.2558    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4341    1.6677    0.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5757    2.1826    0.6855 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218    2.3898    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2952    1.6040   -0.0410 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8899    1.9756    0.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5327    2.7737   -1.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4240    3.3049    0.2370 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2946    4.5012    0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676    3.3694    0.5779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3983    2.4847    1.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518    3.2429   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968    2.4837   -0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4295    1.2010   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9053    0.7985   -0.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5134    0.0543   -0.3759 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2456   -1.1923   -0.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787   -2.0707    0.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6947   -3.3627    0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -1.8055    1.6060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -0.1350   -1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1323   -1.5319   -1.5664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1340   -1.8429   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4655   -3.3345   -1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2967   -0.9157   -1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570   -0.9108    0.0319 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4697   -2.0869    0.4626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -2.9575    1.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760   -4.1956    1.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.6946    1.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480    0.2358    0.4895 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7010   -1.6387   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0208   -0.3705   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7118    1.6085   -1.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172    1.1668    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553    4.4438    1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    5.3848    0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188    4.7258   -0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    4.3921    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6080    2.2031    2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884    4.2980   -1.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3078    2.8691   -1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0981    3.1665   -0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2983    0.4519   -1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9798   -0.0313    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4817    1.6409    0.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259    0.0096    0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788   -4.1155    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9612   -3.7653   -0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5971   -3.1751    1.5258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    0.6156   -1.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4194   -0.1622   -2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8664   -2.3794   -1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5387   -3.5027   -1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0372   -3.8480   -2.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0084   -3.7036   -0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162    0.0780   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437   -1.1066   -2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9184   -0.8783    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5243   -5.0322    1.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -4.5377    2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787   -4.0548    1.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5651    0.3566    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 31  2  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 24  1  0
 24 25  1  0
 24 23  2  0
 23 22  1  0
 22 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 17 15  1  0
 15 16  1  0
 15 14  2  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  6
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 32  1  0
 32 27  1  0
  7  9  1  0
 32  6  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
 27 60  1  1
 26 58  1  0
 26 59  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
 23 54  1  0
 22 52  1  0
 22 53  1  0
 17 48  1  1
 20 49  1  0
 20 50  1  0
 20 51  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 14 44  1  0
 13 42  1  0
 13 43  1  0
 11 40  1  1
 12 41  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
  7 36  1  1
  6 35  1  6
  1 33  1  0
  1 34  1  0
 32 64  1  1
M  END


  Mrv1652309042222442D          

 32 34  0  0  1  0            999 V2000
   -0.1498   -2.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1075   -2.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -1.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2003   -1.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1117   -0.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -1.0336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2558   -0.2915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1353    0.5247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024    0.2209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9666    1.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7073    0.4020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7098    1.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110    0.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666   -0.5285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100   -1.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2545   -0.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075   -1.8699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3112   -2.0559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5520   -2.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3557   -3.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9889   -3.4481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472   -2.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -2.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -4.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8920   -3.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2486   -2.6030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6020   -3.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224   -3.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894   -4.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0758   -4.4440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8929   -1.8586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 27 32  1  0  0  0  0
 32  2  1  1  0  0  0
  6 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C\C(C)=C\C[C@H](OC(C)=O)\C(C)=C\C[C@@H](O)[C@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-12-7-9-17(29-15(4)25)13(2)8-10-19(27)24(6)22(32-24)21-20(14(3)23(28)31-21)18(11-12)30-16(5)26/h7-8,17-22,27H,3,9-11H2,1-2,4-6H3/b12-7+,13-8+/t17-,18+,19+,20+,21-,22-,24-/m0/s1

> <INCHI_KEY>
DQOVBYCKEDMWMR-NZVYTFDISA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.294160131651154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5R,7E,9S,11E,14R,15R)-14-(acetyloxy)-5-hydroxy-4,8,12-trimethyl-16-methylidene-17-oxo-3,18-dioxatricyclo[13.3.0.0^{2,4}]octadeca-7,11-dien-9-yl acetate

> <JCHEM_LOGP>
1.9623812200000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.853858207191685

> <JCHEM_PKA_STRONGEST_BASIC>
-3.300122420174354

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000003

> <JCHEM_REFRACTIVITY>
115.1062

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,7E,9S,11E,14R,15R)-14-(acetyloxy)-5-hydroxy-4,8,12-trimethyl-16-methylidene-17-oxo-3,18-dioxatricyclo[13.3.0.0^{2,4}]octadeca-7,11-dien-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.280  -5.404   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.201  -3.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.701  -2.692   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.241  -2.687   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.208  -1.449   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.672  -1.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.344  -0.544   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.119   0.979   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.551   0.412   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.671   1.948   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   0.750   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.058   2.290   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.554   0.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.218  -0.987   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.419  -1.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.808  -1.287   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.414  -3.490   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.914  -3.838   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.364  -5.311   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.864  -5.658   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.313  -6.436   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.741  -4.876   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.239  -5.214   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.032  -6.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.370  -7.673   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.532  -5.823   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.331  -4.859   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.124  -5.815   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.348  -7.339   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.780  -7.906   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.141  -8.295   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.667  -3.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(1S,2S,4S,5R,7E,9S,11E,14R,15R)-14-(acetyloxy)-5-hydroxy-4,8,12-trimethyl-16-methylidene-17-oxo-3,18-dioxatricyclo[13.3.0.0^{2,4}]octadeca-7,11-dien-9-yl acetate

Traditional Name

(1S,2S,4S,5R,7E,9S,11E,14R,15R)-14-(acetyloxy)-5-hydroxy-4,8,12-trimethyl-16-methylidene-17-oxo-3,18-dioxatricyclo[13.3.0.0^{2,4}]octadeca-7,11-dien-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C\C(C)=C\C[C@H](OC(C)=O)\C(C)=C\C[C@@H](O)[C@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C24H32O8/c1-12-7-9-17(29-15(4)25)13(2)8-10-19(27)24(6)22(32-24)21-20(14(3)23(28)31-21)18(11-12)30-16(5)26/h7-8,17-22,27H,3,9-11H2,1-2,4-6H3/b12-7+,13-8+/t17-,18+,19+,20+,21-,22-,24-/m0/s1

InChI Key

DQOVBYCKEDMWMR-NZVYTFDISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Tricarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:66376 )
epoxide (CHEBI:66376 )
acetate ester (CHEBI:66376 )
cembrane diterpenoid (CHEBI:66376 )
gamma-lactone (CHEBI:66376 )
macrocycle (CHEBI:66376 )

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	1.96	ChemAxon
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.11 m³·mol⁻¹	ChemAxon
Polarizability	46.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17627116

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16723565

PDB ID

Not Available

ChEBI ID

66376

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for michaolide c (NP0201649)

MOL for NP0201649 (michaolide c)

3D MOL for NP0201649 (michaolide c)

3D SDF for NP0201649 (michaolide c)

3D-SDF for NP0201649 (michaolide c)

PDB for NP0201649 (michaolide c)

3D PDB for NP0201649 (michaolide c)

SMILES for NP0201649 (michaolide c)

INCHI for NP0201649 (michaolide c)

Structure for NP0201649 (michaolide c)

3D Structure for NP0201649 (michaolide c)