NP-MRD: Showing NP-Card for (4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid (NP0155786)

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Record Information

Version

2.0

Created at

2022-09-02 12:54:38 UTC

Updated at

2022-09-02 12:54:38 UTC

NP-MRD ID

NP0155786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid

Description

(4E,6S,8E,10E,12E,14E,16E,18E,20R,21S)-6,20-dihydroxy-4,18-dimethyl-21-[(2S,4R,8S,10Z,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. (4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid is found in Sorangium cellulosum. Based on a literature review very few articles have been published on (4E,6S,8E,10E,12E,14E,16E,18E,20R,21S)-6,20-dihydroxy-4,18-dimethyl-21-[(2S,4R,8S,10Z,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214542D          

 60 60  0  0  1  0            999 V2000
    3.3326    3.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8627    3.0488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    2.3029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6850    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    2.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    2.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3897    1.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7421    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2722    0.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -0.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4468   -0.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1548   -1.3591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3326   -1.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072   -2.1051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3294   -2.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373   -2.7832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3897   -3.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -2.7154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8627   -1.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -3.3935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0977   -4.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9231   -3.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5707   -2.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7485   -2.5119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0405   -1.9016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882   -1.1557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8660   -1.0878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5136   -0.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5435   -3.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -2.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8927   -1.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2451   -0.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0673   -0.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2419    0.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4165    0.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    1.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5910    1.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.7656    2.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1180    3.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6482    3.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9402    3.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4100    2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.5846    3.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1580   -0.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2755    0.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3929    2.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 26 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  6  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
  3 60  1  0  0  0  0
M  END

     RDKit          3D

136136  0  0  0  0  0  0  0  0999 V2000
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   -7.3205   -2.4585   -2.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.0845   -0.9652   -3.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.2792    0.9304   -2.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7419    1.8595   -1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.6415    1.2535    0.6342 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -9.2748    0.7595    3.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8759    1.1814    0.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1999    1.5551    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8072    1.0700    1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1708    1.4359    2.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7045    0.8187    3.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8850   -0.2276    3.4671 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0436   -0.0948    4.3271 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022214542D          

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  8  9  1  0  0  0  0
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 58 59  1  0  0  0  0
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  3 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155786

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C49H76O11/c1-34(22-17-13-11-9-8-10-12-14-19-24-40(50)30-35(2)28-29-46(54)55)31-43(52)37(4)45-32-41(51)25-21-27-42(59-7)26-20-16-15-18-23-36(3)48(57)39(6)49(58)38(5)44(53)33-47(56)60-45/h8-20,22,30-31,36-45,48-53,57-58H,21,23-29,32-33H2,1-7H3,(H,54,55)/b9-8+,12-10+,13-11+,18-15+,19-14+,20-16-,22-17+,34-31+,35-30+/t36-,37-,38+,39-,40-,41+,42+,43+,44+,45-,48+,49-/m0/s1

> <INCHI_KEY>
VHPBIOVAVQXSJO-OCTBXXSZSA-N

> <FORMULA>
C49H76O11

> <MOLECULAR_WEIGHT>
841.136

> <EXACT_MASS>
840.538763267

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
136

> <JCHEM_AVERAGE_POLARIZABILITY>
99.53111837988844

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E,6S,8E,10E,12E,14E,16E,18E,20R,21S)-6,20-dihydroxy-4,18-dimethyl-21-[(2S,4R,8S,10Z,12E,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid

> <ALOGPS_LOGP>
5.62

> <JCHEM_LOGP>
5.917893208666666

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.935500173474619

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.711317525646426

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4931656424603097

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
248.68780000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E,6S,8E,10E,12E,14E,16E,18E,20R,21S)-6,20-dihydroxy-4,18-dimethyl-21-[(2S,4R,8S,10Z,12E,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.221   6.957   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.344   5.691   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.002   4.299   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.879   5.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.413   5.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.071   4.046   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.194   2.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.852   1.387   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.975   0.121   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.633  -1.271   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.167  -1.398   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.756  -2.537   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.221  -2.410   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.413  -3.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.948  -4.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.536  -5.195   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.194  -6.588   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.002  -5.069   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.344  -3.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.125  -6.335   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.782  -7.727   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.590  -6.208   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.932  -4.816   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.397  -4.689   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.809  -3.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.151  -2.157   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.616  -2.031   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.959  -0.638   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.739  -3.297   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.453  -4.810   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.795  -3.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.672  -4.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.015  -5.828   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.207  -4.309   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.865  -2.917   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.400  -2.790   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.057  -1.398   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.592  -1.271   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.250   0.121   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.785   0.248   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -10.443   1.640   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -11.977   1.767   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -12.635   3.159   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -14.170   3.286   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -14.828   4.678   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -13.951   5.944   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0     -16.363   4.805   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -17.020   6.198   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -16.143   7.463   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -18.555   6.324   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -19.432   5.058   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -20.967   5.185   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -21.625   6.577   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0     -21.844   3.919   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       4.028  -0.891   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       3.370   0.501   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       1.836   0.628   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       4.248   1.767   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       3.590   3.159   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       4.467   4.425   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   60                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   55                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   26   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59    3                                                       
MASTER        0    0    0    0    0    0    0    0   60    0  120    0
END

View in JSmol

Synonyms

Value	Source
(4E,6S,8E,10E,12E,14E,16E,18E,20R,21S)-6,20-Dihydroxy-4,18-dimethyl-21-[(2S,4R,8S,10Z,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoate	Generator

Chemical Formula

C₄₉H₇₆O₁₁

Average Mass

841.1360 Da

Monoisotopic Mass

840.53876 Da

IUPAC Name

(4E,6S,8E,10E,12E,14E,16E,18E,20R,21S)-6,20-dihydroxy-4,18-dimethyl-21-[(2S,4R,8S,10Z,12E,15S,16R,17S,18S,19R,20R)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1CCC[C@@H](O)C[C@H](OC(=O)C[C@@H](O)[C@@H](C)[C@H](O)[C@@H](C)[C@H](O)[C@@H](C)C\C=C\C=C/C1)[C@@H](C)[C@H](O)\C=C(/C)\C=C\C=C\C=C\C=C\C=C\C[C@H](O)\C=C(/C)CCC(O)=O

InChI Identifier

InChI=1S/C49H76O11/c1-34(22-17-13-11-9-8-10-12-14-19-24-40(50)30-35(2)28-29-46(54)55)31-43(52)37(4)45-32-41(51)25-21-27-42(59-7)26-20-16-15-18-23-36(3)48(57)39(6)49(58)38(5)44(53)33-47(56)60-45/h8-20,22,30-31,36-45,48-53,57-58H,21,23-29,32-33H2,1-7H3,(H,54,55)/b9-8+,12-10+,13-11+,18-15+,19-14+,20-16-,22-17+,34-31+,35-30+/t36-,37-,38+,39-,40-,41+,42+,43+,44+,45-,48+,49-/m0/s1

InChI Key

VHPBIOVAVQXSJO-OCTBXXSZSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sorangium cellulosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Very long-chain fatty acids

Alternative Parents

Substituents

Very long-chain fatty acid
Macrolide
Methyl-branched fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	5.62	ALOGPS
logP	5.92	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	248.69 m³·mol⁻¹	ChemAxon
Polarizability	99.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162945850

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid (NP0155786)

MOL for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

3D MOL for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

3D SDF for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

3D-SDF for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

PDB for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

3D PDB for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

SMILES for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

INCHI for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

Structure for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)

3D Structure for NP0155786 ((4e,6s,8e,10e,12e,14e,16e,18e,20r,21s)-6,20-dihydroxy-4,18-dimethyl-21-[(2s,4r,8s,10z,12e,15s,16r,17s,18s,19r,20r)-4,16,18,20-tetrahydroxy-8-methoxy-15,17,19-trimethyl-22-oxo-1-oxacyclodocosa-10,12-dien-2-yl]docosa-4,8,10,12,14,16,18-heptaenoic acid)