NP-MRD: Showing NP-Card for Phomacin B (NP0003903)

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Record Information

Version

2.0

Created at

2020-12-09 01:27:10 UTC

Updated at

2021-07-15 16:47:41 UTC

NP-MRD ID

NP0003903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phomacin B

Provided By

NPAtlas

Description

(5S,7S,13S,13aS,14S,16aS,16bS)-5,16-dihydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,16bH-oxacyclododeca[3,2-e]isoindol-2-one belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Phomacin B is found in Phoma sp. Based on a literature review very few articles have been published on (5S,7S,13S,13aS,14S,16aS,16bS)-5,16-dihydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,16bH-oxacyclododeca[3,2-e]isoindol-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 68 70  0  0  0  0            999 V2000
    0.1169    3.8919    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914    2.5551    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515    2.1611   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652    0.8419   -1.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2427    0.3298   -2.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514    0.3669   -2.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.2382   -3.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160    1.0084   -0.9037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0258    0.0199   -0.2679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4670    0.5274    1.0676 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1001    1.7893    0.9086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -1.3117   -0.3706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0521   -2.0877    0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1672   -2.9152    1.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -1.4482    2.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3935   -1.1423    2.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2673   -1.4091    1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -2.2078    1.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5551   -0.1496   -0.6764 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3062   -1.1068   -1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.4130   -2.7235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102   -1.4938   -0.7520 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -0.4141    0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1289    0.1818   -0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2756   -0.7435    0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3206   -1.9244   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3867   -1.2802    1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532    0.6276   -0.2089 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.2389    1.3798    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    3.9965    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6661    1.1209   -2.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.1848   -3.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    0.3911   -4.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0349   -1.2260   -3.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2677    1.0485   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5184    0.8175    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -0.0926    1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4645   -3.3000    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870   -1.1907    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -0.6486    3.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350   -2.4343   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1601    0.5613   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3181    1.0533    0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2077   -0.1255   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8768   -0.5880    2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -1.3953    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -2.2678    1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    1.1058   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930    2.4134    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245    1.3270    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    2.2502    2.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    0.4446    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
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 13 15  1  0  0  0  0
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 30  2  1  0  0  0  0
 20  4  1  0  0  0  0
 29 20  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  6  0  0  0
  5 37  1  0  0  0  0
  7 38  1  0  0  0  0
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 14 50  1  0  0  0  0
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 16 52  1  0  0  0  0
 23 53  1  0  0  0  0
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 30 65  1  1  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 31 68  1  0  0  0  0
M  END

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
    0.1169    3.8919    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914    2.5551    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6821    0.4446    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
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 30 65  1  1
 31 66  1  0
 31 67  1  0
 31 68  1  0
M  END


  Mrv1652306242117513D          

 68 70  0  0  0  0            999 V2000
    0.1169    3.8919    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914    2.5551    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515    2.1611   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7698   -0.4141    0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1289    0.1818   -0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2756   -0.7435    0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3206   -1.9244   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3130   -2.8831    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4645   -3.3000    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870   -1.1907    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8350   -2.4343   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -0.7104    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601    0.5613   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3181    1.0533    0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0767   -2.8799   -0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4165   -2.0827   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8768   -0.5880    2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -1.3953    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -2.2678    1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    1.1058   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930    2.4134    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245    1.3270    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    2.2502    2.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    0.4446    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
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  9 12  1  0  0  0  0
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 30  2  1  0  0  0  0
 20  4  1  0  0  0  0
 29 20  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  6  0  0  0
  5 37  1  0  0  0  0
  7 38  1  0  0  0  0
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 31 67  1  0  0  0  0
 31 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003903

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])C([H])([H])\C(=C([H])/[C@@]2([H])C([H])=C(C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@@]3([H])[C@@]([H])(N([H])C(=O)[C@]23OC(=O)\C([H])=C([H])/[C@@]([H])(O[H])C1([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO5/c1-14(2)8-21-23-17(5)16(4)11-19-10-15(3)9-18(13-27)12-20(28)6-7-22(29)31-25(19,23)24(30)26-21/h6-7,10-11,14,17-21,23,27-28H,8-9,12-13H2,1-5H3,(H,26,30)/b7-6-,15-10-/t17-,18+,19+,20-,21+,23+,25+/m1/s1

> <INCHI_KEY>
IXONDWQZWWLZDF-LWCQKGSWSA-N

> <FORMULA>
C25H37NO5

> <MOLECULAR_WEIGHT>
431.573

> <EXACT_MASS>
431.267173295

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.65618130786439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,7S,13S,13aS,14S,16aS,16bS)-5-hydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,15H,16H,16bH-oxacyclododeca[3,2-e]isoindole-2,16-dione

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.806960356666666

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.787112988043518

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.893948940937609

> <JCHEM_PKA_STRONGEST_BASIC>
-2.599331730027969

> <JCHEM_POLAR_SURFACE_AREA>
95.86000000000001

> <JCHEM_REFRACTIVITY>
122.05909999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,7S,13S,13aS,14S,16aS,16bS)-5-hydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-5H,6H,7H,8H,13H,13aH,14H,15H,16bH-oxacyclododeca[3,2-e]isoindole-2,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
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    5.3206   -1.9244   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
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  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 20 19  1  1
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 30  2  1  0
 20  4  1  0
 29 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  6
 10 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  6
 14 50  1  0
 15 51  1  0
 16 52  1  0
 23 53  1  0
 24 54  1  1
 25 55  1  0
 25 56  1  0
 26 57  1  6
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  6
 30 65  1  1
 31 66  1  0
 31 67  1  0
 31 68  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       0.117   3.892   0.715  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.391   2.555   0.125  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.352   2.161  -0.901  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.165   0.842  -1.570  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.243   0.330  -2.365  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.551   0.367  -2.141  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.472  -0.238  -3.128  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.016   1.008  -0.904  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.026   0.020  -0.268  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.467   0.527   1.068  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.100   1.789   0.909  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.456  -1.312  -0.371  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.052  -2.088   0.802  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.167  -2.915   1.153  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.642  -1.448   2.020  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.393  -1.142   2.293  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.267  -1.409   1.399  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.620  -2.208   1.958  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.171  -0.892   0.170  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.555  -0.150  -0.676  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.306  -1.107  -1.585  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.981  -1.413  -2.724  0.00  0.00           O+0
HETATM   23  N   UNK     0       2.410  -1.494  -0.752  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.770  -0.414   0.122  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.129   0.182  -0.131  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.276  -0.744   0.012  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.321  -1.924  -0.894  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.387  -1.280   1.441  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.753   0.628  -0.209  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.499   1.719   0.722  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.239   1.380   2.138  0.00  0.00           C+0
HETATM   32  H   UNK     0       0.492   3.997   1.742  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.716   4.627   0.101  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.944   4.199   0.594  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.140   2.785  -1.309  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.666   1.121  -2.322  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.976  -0.185  -3.317  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.439   0.391  -4.060  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.479  -0.445  -2.793  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.035  -1.226  -3.459  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.268   1.048  -0.085  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.473   1.994  -1.046  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.933   0.137  -0.935  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.518   0.818   1.610  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.149  -0.093   1.626  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.366   2.043   1.834  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.567  -1.315  -1.083  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.194  -1.957  -0.958  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.313  -2.883   0.445  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.465  -3.300   0.277  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.387  -1.191   2.797  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.172  -0.649   3.286  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.835  -2.434  -0.812  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.764  -0.710   1.194  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.160   0.561  -1.202  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.318   1.053   0.539  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.208  -0.126  -0.164  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.077  -2.880  -0.353  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.417  -2.083  -1.159  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.827  -1.812  -1.863  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.877  -0.588   2.120  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.446  -1.395   1.705  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.897  -2.268   1.523  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.159   1.106  -1.161  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.393   2.413   0.709  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.125   1.327   2.280  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.546   2.250   2.791  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.682   0.445   2.480  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   30                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   20   36                                             
CONECT    5    4    6   37                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   38   39   40                                             
CONECT    8    6    9   41   42                                             
CONECT    9    8   10   12   43                                             
CONECT   10    9   11   44   45                                             
CONECT   11   10   46                                                       
CONECT   12    9   13   47   48                                             
CONECT   13   12   14   15   49                                             
CONECT   14   13   50                                                       
CONECT   15   13   16   51                                                  
CONECT   16   15   17   52                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21    4   29                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   53                                                  
CONECT   24   23   25   29   54                                             
CONECT   25   24   26   55   56                                             
CONECT   26   25   27   28   57                                             
CONECT   27   26   58   59   60                                             
CONECT   28   26   61   62   63                                             
CONECT   29   24   30   20   64                                             
CONECT   30   29   31    2   65                                             
CONECT   31   30   66   67   68                                             
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   31                                                            
CONECT   68   31                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  140    0
END

RDKit          3D

68 70  0  0  0  0  0  0  0  0999 V2000
    0.1169    3.8919    0.7151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3914    2.5551    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3515    2.1611   -0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652    0.8419   -1.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2427    0.3298   -2.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5514    0.3669   -2.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.2382   -3.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0160    1.0084   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258    0.0199   -0.2679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4670    0.5274    1.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1001    1.7893    0.9086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -1.3117   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521   -2.0877    0.8019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1672   -2.9152    1.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415   -1.4482    2.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3935   -1.1423    2.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2673   -1.4091    1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6195   -2.2078    1.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707   -0.8916    0.1695 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5551   -0.1496   -0.6764 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3062   -1.1068   -1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.4130   -2.7235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102   -1.4938   -0.7520 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7698   -0.4141    0.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1289    0.1818   -0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2756   -0.7435    0.0115 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3206   -1.9244   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3867   -1.2802    1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532    0.6276   -0.2089 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4987    1.7192    0.7215 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2389    1.3798    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    3.9965    1.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7157    4.6272    0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9443    4.1987    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399    2.7846   -1.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6661    1.1209   -2.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759   -0.1848   -3.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4395    0.3911   -4.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4788   -0.4446   -2.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0349   -1.2260   -3.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2677    1.0485   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4727    1.9943   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9330    0.1374   -0.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5184    0.8175    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -0.0926    1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3657    2.0434    1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -1.3153   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943   -1.9567   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3130   -2.8831    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4645   -3.3000    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3870   -1.1907    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -0.6486    3.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350   -2.4343   -0.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -0.7104    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601    0.5613   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3181    1.0533    0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2077   -0.1255   -0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0767   -2.8799   -0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4165   -2.0827   -1.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8272   -1.8123   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768   -0.5880    2.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4455   -1.3953    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -2.2678    1.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595    1.1058   -1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3930    2.4134    0.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245    1.3270    2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5461    2.2502    2.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    0.4446    2.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 20 19  1  1
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 24 29  1  0
 29 30  1  0
 30 31  1  0
 30  2  1  0
 20  4  1  0
 29 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  6
 10 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  6
 14 50  1  0
 15 51  1  0
 16 52  1  0
 23 53  1  0
 24 54  1  1
 25 55  1  0
 25 56  1  0
 26 57  1  6
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  6
 30 65  1  1
 31 66  1  0
 31 67  1  0
 31 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₃₇NO₅

Average Mass

431.5730 Da

Monoisotopic Mass

431.26717 Da

IUPAC Name

(5S,7S,13S,13aS,14S,16aS,16bS)-5-hydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-2H,5H,6H,7H,8H,13H,13aH,14H,15H,16H,16bH-oxacyclododeca[3,2-e]isoindole-2,16-dione

Traditional Name

(5S,7S,13S,13aS,14S,16aS,16bS)-5-hydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-5H,6H,7H,8H,13H,13aH,14H,15H,16bH-oxacyclododeca[3,2-e]isoindole-2,16-dione

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]1NC(=O)[C@@]23OC(=O)\C=C/[C@@H](O)C[C@@H](CO)C\C(C)=C/[C@H]2C=C(C)[C@@H](C)[C@@H]13

InChI Identifier

InChI=1S/C25H37NO5/c1-14(2)8-21-23-17(5)16(4)11-19-10-15(3)9-18(13-27)12-20(28)6-7-22(29)31-25(19,23)24(30)26-21/h6-7,10-11,14,17-21,23,27-28H,8-9,12-13H2,1-5H3,(H,26,30)/b7-6-,15-10-/t17-,18+,19+,20-,21+,23+,25+/m1/s1

InChI Key

IXONDWQZWWLZDF-LWCQKGSWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phoma sp.	NPAtlas	11671521

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrroline
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.5	ALOGPS
logP	2.81	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	122.06 m³·mol⁻¹	ChemAxon
Polarizability	47.66 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

NPAtlas ID

NPA008051

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437211

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585348

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phomacin B (NP0003903)

MOL for NP0003903 (Phomacin B)

3D MOL for NP0003903 (Phomacin B)

3D SDF for NP0003903 (Phomacin B)

3D-SDF for NP0003903 (Phomacin B)

PDB for NP0003903 (Phomacin B)

3D PDB for NP0003903 (Phomacin B)

SMILES for NP0003903 (Phomacin B)

INCHI for NP0003903 (Phomacin B)

Structure for NP0003903 (Phomacin B)

3D Structure for NP0003903 (Phomacin B)