NP-MRD: Showing NP-Card for heptemerone B (NP0028576)

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Record Information

Version

2.0

Created at

2021-06-19 20:25:42 UTC

Updated at

2021-06-29 23:55:27 UTC

NP-MRD ID

NP0028576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

heptemerone B

Provided By

JEOL Database JEOL Logo

Description

heptemerone B is found in Coprinus heptemerus. heptemerone B was first documented in 2005 (Valdivia, C., et al.). Based on a literature review very few articles have been published on (1R,2S,4R,5R,6R,9R,12S)-4-(acetyloxy)-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0²,⁶.0¹³,¹⁶]Hexadec-13(16)-en-12-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122253D          

 64 67  0  0  0  0            999 V2000
    6.2973   -1.6221    2.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447   -0.3031    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619    0.4771    1.6062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8461   -0.1143    1.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593    1.1232    0.7891 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8693    0.9972   -0.7138 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7705    0.2310   -1.4700 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3498    0.8716   -1.3300 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2741    2.1180   -2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154   -0.1971   -1.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1640    0.2161   -1.7101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8978   -0.0345   -0.3625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2706   -1.5349   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388    0.3513    0.8857 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1058    0.5810    1.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9300    0.3966    3.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    0.9557    1.3183 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.2057    1.4231    3.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1873    2.1511    2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469    1.7886    2.3130 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1105    1.3904    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    1.2941    0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817   -1.6397    3.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3430   -1.7610    2.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119   -2.4313    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    1.9422    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    1.9979   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225    0.4785   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.7992   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460    0.1586   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794    1.8409   -3.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664    2.8387   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    2.6584   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.1229   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -0.4595   -2.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799    1.2595   -2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634   -0.3653   -2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8095   -1.7761    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -2.1652   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9007   -1.8470   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5672   -0.5009    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    1.9776    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -1.7033    3.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0495    2.6603    2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    0.9660    3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 14  1  0  0  0  0
 11 12  1  0  0  0  0
 26 30  1  0  0  0  0
  8  7  1  0  0  0  0
 14 15  1  0  0  0  0
 17 22  1  0  0  0  0
 22 12  1  0  0  0  0
  7  6  1  0  0  0  0
  4  2  1  0  0  0  0
  5 29  1  0  0  0  0
  2  1  1  0  0  0  0
 30  8  1  0  0  0  0
  2  3  2  0  0  0  0
  8  9  1  6  0  0  0
 30 29  2  0  0  0  0
 22 23  1  0  0  0  0
 29 28  1  0  0  0  0
 23 24  1  0  0  0  0
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  8 10  1  0  0  0  0
 26 62  1  6  0  0  0
  5  4  1  0  0  0  0
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 20 51  1  0  0  0  0
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 20 53  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    6.2973   -1.6221    2.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447   -0.3031    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619    0.4771    1.6062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8461   -0.1143    1.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593    1.1232    0.7891 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8693    0.9972   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3498    0.8716   -1.3300 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2741    2.1180   -2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192122253D          

 64 67  0  0  0  0            999 V2000
    6.2973   -1.6221    2.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447   -0.3031    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8461   -0.1143    1.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593    1.1232    0.7891 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8693    0.9972   -0.7138 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7705    0.2310   -1.4700 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3498    0.8716   -1.3300 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.0664    2.8387   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4613   -1.1229   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -0.4595   -2.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6634   -0.3653   -2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8565    1.9026   -0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8577   -0.4078   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3015    2.4075    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495    2.6603    2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    0.9660    3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  1  0  0  0  0
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  2  1  1  0  0  0  0
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  8  9  1  6  0  0  0
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 20 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028576

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C(=O)O[C@@]1([H])C(=O)[C@]2([H])[C@@]3([H])OC([H])([H])C4=C3[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])[C@]4([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]1([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O6/c1-12(2)17-22(30-14(4)26)20(27)19-21-18-15(11-28-21)16(29-13(3)25)7-8-23(18,5)9-10-24(17,19)6/h12,16-17,19,21-22H,7-11H2,1-6H3/t16-,17-,19+,21-,22+,23-,24+/m0/s1

> <INCHI_KEY>
WMVJIPZZKUYCOU-DREMNZCRSA-N

> <FORMULA>
C24H34O6

> <MOLECULAR_WEIGHT>
418.53

> <EXACT_MASS>
418.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.06920654035083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R,5R,6R,9R,12S)-4-(acetyloxy)-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-en-12-yl acetate

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.863899946333332

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.193331296892698

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2078514619650935

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
109.90749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,6R,9R,12S)-4-(acetyloxy)-5-isopropyl-6,9-dimethyl-3-oxo-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-en-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    6.2973   -1.6221    2.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2741    2.1180   -2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154   -0.1971   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640    0.2161   -1.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8978   -0.0345   -0.3625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2706   -1.5349   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4574    0.5621   -1.0308 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5468    1.6188   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401    0.4887   -2.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    1.6084    0.7255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1873    2.1511    2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1105    1.3904    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    1.2941    0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8225    0.4785   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.7992   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460    0.1586   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794    1.8409   -3.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664    2.8387   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    2.6584   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.1229   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3015    2.4075    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495    2.6603    2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    0.9660    3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 14  1  0
 11 12  1  0
 26 30  1  0
  8  7  1  0
 14 15  1  0
 17 22  1  0
 22 12  1  0
  7  6  1  0
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  5 29  1  0
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 30  8  1  0
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  8  9  1  6
 30 29  2  0
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  5  4  1  0
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 15 16  2  0
 12 13  1  1
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 20 52  1  0
 20 53  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       6.297  -1.622   2.510  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.145  -0.303   1.817  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.062   0.477   1.606  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.846  -0.114   1.461  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.559   1.123   0.789  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.869   0.997  -0.714  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.771   0.231  -1.470  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.350   0.872  -1.330  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.274   2.118  -2.238  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.315  -0.197  -1.773  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.164   0.216  -1.710  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.898  -0.035  -0.363  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.271  -1.535  -0.271  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.039   0.351   0.886  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.106   0.581   1.929  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.930   0.397   3.130  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.439   0.956   1.318  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.384  -0.031   1.739  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.158   0.318   2.803  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.990  -0.853   3.231  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.206   1.423   3.321  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.171   0.891  -0.212  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.457   0.562  -1.031  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.547   1.619  -0.772  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.240   0.489  -2.544  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.824   1.608   0.726  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.187   2.151   2.014  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.547   1.789   2.313  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.111   1.390   1.007  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.140   1.294   0.094  0.00  0.00           C+0
HETATM   31  H   UNK     0       5.682  -1.640   3.413  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.343  -1.761   2.799  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.012  -2.431   1.833  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.147   1.942   1.222  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.979   1.998  -1.147  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.822   0.479  -0.867  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.755  -0.799  -1.088  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.046   0.159  -2.530  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.379   1.841  -3.293  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.066   2.839  -2.008  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.328   2.658  -2.129  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.461  -1.123  -1.202  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.537  -0.460  -2.817  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.280   1.260  -2.017  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.663  -0.365  -2.492  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.810  -1.776   0.650  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.375  -2.165  -0.288  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.901  -1.847  -1.109  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.567  -0.501   1.221  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.710   1.978   1.605  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.343  -1.703   3.461  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.698  -1.111   2.440  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.548  -0.591   4.134  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.857   1.903  -0.510  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.858  -0.408  -0.711  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.455   1.389  -1.339  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.206   2.616  -1.071  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.836   1.664   0.281  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.675   1.351  -2.911  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.197   0.467  -3.078  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.719  -0.428  -2.827  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.302   2.408   0.191  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.050   2.660   2.740  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.550   0.966   3.034  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5   29    4    6   34                                             
CONECT    6    7    5   35   36                                             
CONECT    7    8    6   37   38                                             
CONECT    8    7   30    9   10                                             
CONECT    9    8   39   40   41                                             
CONECT   10    8   11   42   43                                             
CONECT   11   12   10   44   45                                             
CONECT   12   11   22   13   14                                             
CONECT   13   12   46   47   48                                             
CONECT   14   26   15   49   12                                             
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   22   15   18   50                                             
CONECT   18   17   19                                                       
CONECT   19   18   21   20                                                  
CONECT   20   19   51   52   53                                             
CONECT   21   19                                                            
CONECT   22   17   12   23   54                                             
CONECT   23   22   24   25   55                                             
CONECT   24   23   56   57   58                                             
CONECT   25   23   59   60   61                                             
CONECT   26   14   30   27   62                                             
CONECT   27   28   26                                                       
CONECT   28   29   27   63   64                                             
CONECT   29    5   30   28                                                  
CONECT   30   26    8   29                                                  
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   17                                                            
CONECT   51   20                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  134    0
END

RDKit          3D

64 67  0  0  0  0  0  0  0  0999 V2000
    6.2973   -1.6221    2.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447   -0.3031    1.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0619    0.4771    1.6062 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8461   -0.1143    1.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5593    1.1232    0.7891 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8693    0.9972   -0.7138 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7705    0.2310   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498    0.8716   -1.3300 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2741    2.1180   -2.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3154   -0.1971   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1640    0.2161   -1.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8978   -0.0345   -0.3625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2706   -1.5349   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388    0.3513    0.8857 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1058    0.5810    1.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9300    0.3966    3.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    0.9557    1.3183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3842   -0.0309    1.7391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1584    0.3175    2.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9899   -0.8528    3.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2057    1.4231    3.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1710    0.8907   -0.2122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4574    0.5621   -1.0308 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5468    1.6188   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401    0.4887   -2.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    1.6084    0.7255 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1873    2.1511    2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469    1.7886    2.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    1.3904    1.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1397    1.2941    0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6817   -1.6397    3.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3430   -1.7610    2.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119   -2.4313    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470    1.9422    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    1.9979   -1.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225    0.4785   -0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.7992   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0460    0.1586   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3794    1.8409   -3.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664    2.8387   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    2.6584   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.1229   -1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -0.4595   -2.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799    1.2595   -2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634   -0.3653   -2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8095   -1.7761    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750   -2.1652   -0.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9007   -1.8470   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5672   -0.5009    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101    1.9776    1.6054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431   -1.7033    3.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6984   -1.1110    2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5481   -0.5905    4.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.9026   -0.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8577   -0.4078   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4551    1.3886   -1.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2062    2.6159   -1.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8358    1.6638    0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6751    1.3513   -2.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1970    0.4666   -3.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7191   -0.4279   -2.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3015    2.4075    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495    2.6603    2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    0.9660    3.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 14  1  0
 11 12  1  0
 26 30  1  0
  8  7  1  0
 14 15  1  0
 17 22  1  0
 22 12  1  0
  7  6  1  0
  4  2  1  0
  5 29  1  0
  2  1  1  0
 30  8  1  0
  2  3  2  0
  8  9  1  6
 30 29  2  0
 22 23  1  0
 29 28  1  0
 23 24  1  0
 28 27  1  0
 23 25  1  0
 17 15  1  0
 27 26  1  0
 17 18  1  0
  8 10  1  0
 26 62  1  6
  5  4  1  0
 14 49  1  1
  5  6  1  0
 15 16  2  0
 12 13  1  1
 18 19  1  0
 12 14  1  0
 19 21  2  0
 10 11  1  0
 19 20  1  0
  5 34  1  1
  7 37  1  0
  7 38  1  0
  6 35  1  0
  6 36  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 28 63  1  0
 28 64  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 17 50  1  1
 22 54  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
 23 55  1  1
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 20 51  1  0
 20 52  1  0
 20 53  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1R,2S,4R,5R,6R,9R,12S)-4-(Acetyloxy)-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0,.0,]hexadec-13(16)-en-12-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₄O₆

Average Mass

418.5300 Da

Monoisotopic Mass

418.23554 Da

IUPAC Name

(1R,2S,4R,5R,6R,9R,12S)-4-(acetyloxy)-6,9-dimethyl-3-oxo-5-(propan-2-yl)-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-en-12-yl acetate

Traditional Name

(1R,2S,4R,5R,6R,9R,12S)-4-(acetyloxy)-5-isopropyl-6,9-dimethyl-3-oxo-15-oxatetracyclo[7.6.1.0^{2,6}.0^{13,16}]hexadec-13(16)-en-12-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])C(=O)O[C@@]1([H])C(=O)[C@]2([H])[C@@]3([H])OC([H])([H])C4=C3[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])[C@]4([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]1([H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H34O6/c1-12(2)17-22(30-14(4)26)20(27)19-21-18-15(11-28-21)16(29-13(3)25)7-8-23(18,5)9-10-24(17,19)6/h12,16-17,19,21-22H,7-11H2,1-6H3/t16-,17-,19+,21-,22+,23-,24+/m0/s1

InChI Key

WMVJIPZZKUYCOU-DREMNZCRSA-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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Coprinellus heptemerus	JEOL database	Valdivia, C., et al, Tetrahedron 61, 9527 (2005)

Chemical Taxonomy

Classification

Not classified

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	3.05	ALOGPS
logP	2.86	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.19	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.91 m³·mol⁻¹	ChemAxon
Polarizability	46.07 Å³	ChemAxon
Number of Rings	4	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

9410505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11235458

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Valdivia, C., et al. (2005). Valdivia, C., et al, Tetrahedron 61, 9527 (2005). Tetrahedron.

Showing NP-Card for heptemerone B (NP0028576)

MOL for NP0028576 (heptemerone B)

3D MOL for NP0028576 (heptemerone B)

3D SDF for NP0028576 (heptemerone B)

3D-SDF for NP0028576 (heptemerone B)

PDB for NP0028576 (heptemerone B)

3D PDB for NP0028576 (heptemerone B)

SMILES for NP0028576 (heptemerone B)

INCHI for NP0028576 (heptemerone B)

Structure for NP0028576 (heptemerone B)

3D Structure for NP0028576 (heptemerone B)