NP-MRD: Showing NP-Card for Sequoiatone A (NP0003916)

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Record Information

Version

2.0

Created at

2020-12-09 01:27:48 UTC

Updated at

2021-07-15 16:47:44 UTC

NP-MRD ID

NP0003916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sequoiatone A

Provided By

NPAtlas

Description

Methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0²,⁶]Dodeca-5,7,9-triene-7-carboxylate belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Sequoiatone A is found in Aegiceras corniculatum and Aspergillus parasiticus. Based on a literature review very few articles have been published on methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0²,⁶]Dodeca-5,7,9-triene-7-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 59 61  0  0  0  0            999 V2000
    8.5940   -0.1695    0.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1407    0.2536    0.6939 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6869   -0.1152   -0.6921 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2548    0.2560   -0.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2885   -0.4286   -0.0096 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8940    0.0273   -0.3884 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8444   -0.5978    0.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8974   -2.1098    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -0.1592    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4642    0.5685   -0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973   -0.5836    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079   -0.2677    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    0.4052   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.5480   -1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6984    0.1302   -2.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5973    1.2807   -2.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    1.4950   -4.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    0.8037    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1236    1.5064   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    1.6435    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3553    2.3717    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9070    1.0949    1.9827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735   -0.0434    2.0927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7387    0.2880    1.5491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8668   -0.9354    1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5739   -2.0338    0.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781   -1.3641    2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -1.3040    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525   -1.7633    2.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9950   -0.5980   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7199   -0.9461    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2333    0.6997    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0897    1.3456    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -0.2111    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3119    0.4234   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8140   -1.2015   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562    1.3513   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -0.1236   -1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -1.5180   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6431   -0.2226   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2002    2.5163   -4.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3898   -2.4934    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
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 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
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 13 18  2  0  0  0  0
 18 19  1  0  0  0  0
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 22 23  1  0  0  0  0
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 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
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 28 11  1  0  0  0  0
 25 12  1  0  0  0  0
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  1 30  1  0  0  0  0
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M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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    4.2885   -0.4286   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8940    0.0273   -0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8444   -0.5978    0.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8974   -2.1098    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -0.1592    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8272    0.4052   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.5480   -1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0
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M  END


  Mrv1652306242117513D          

 59 61  0  0  0  0            999 V2000
    8.5940   -0.1695    0.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1407    0.2536    0.6939 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6869   -0.1152   -0.6921 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2548    0.2560   -0.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2885   -0.4286   -0.0096 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.5044   -0.1592    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7387    0.2880    1.5491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8668   -0.9354    1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5739   -2.0338    0.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781   -1.3641    2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -1.3040    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525   -1.7633    2.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9950   -0.5980   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7199   -0.9461    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2333    0.6997    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0897    1.3456    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -0.2111    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3119    0.4234   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8140   -1.2015   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562    1.3513   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -0.1236   -1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -1.5180   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5527   -0.1015    1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -0.2226   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.1301   -0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318   -0.2436    1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9029   -2.5388    0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -2.5979    1.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.3829   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2002    2.5163   -4.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8638    0.7226   -4.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5400    1.3097   -4.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2281    1.9221   -1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1419    3.2953   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7696    2.7240    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0805    1.7235   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5343   -0.8332    1.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -0.3834    3.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2085    0.9853    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346   -1.7173   -0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170   -2.8328    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -2.4934    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 11  1  0  0  0  0
 25 12  1  0  0  0  0
 24 18  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  5 39  1  0  0  0  0
  5 40  1  0  0  0  0
  6 41  1  0  0  0  0
  6 42  1  0  0  0  0
  7 43  1  1  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
  8 46  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 19 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 23 54  1  0  0  0  0
 23 55  1  0  0  0  0
 24 56  1  1  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 26 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(OC([H])([H])[C@]2([H])C1=C(C(=O)OC([H])([H])[H])C1=C(C(=O)[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C(=O)O[C@@]21C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O6/c1-6-7-8-9-10-13(2)20(24)18-19-17(21(25)27-5)15-11-14(3)28-12-16(15)23(19,4)29-22(18)26/h11,13,16H,6-10,12H2,1-5H3/t13-,16+,23-/m0/s1

> <INCHI_KEY>
UMDDQZKJZQPILY-LZDDTZTRSA-N

> <FORMULA>
C23H30O6

> <MOLECULAR_WEIGHT>
402.487

> <EXACT_MASS>
402.204238686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.699760401895375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0^{2,6}]dodeca-5,7,9-triene-7-carboxylate

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
3.8386429609999997

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.32857136180186

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.628276108742323

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7637958242884775

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
110.54019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0^{2,6}]dodeca-5,7,9-triene-7-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
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    1.8444   -0.5978    0.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8974   -2.1098    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -0.1592    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6973   -0.5836    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079   -0.2677    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    0.4052   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9118    0.8037    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1236    1.5064   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    1.6435    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3553    2.3717    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9070    1.0949    1.9827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735   -0.0434    2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.2880    1.5491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8668   -0.9354    1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5739   -2.0338    0.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781   -1.3641    2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -1.3040    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525   -1.7633    2.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9950   -0.5980   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7199   -0.9461    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2333    0.6997    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0897    1.3456    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -0.2111    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3119    0.4234   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8140   -1.2015   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562    1.3513   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -0.1236   -1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -1.5180   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5527   -0.1015    1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -0.2226   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.1301   -0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318   -0.2436    1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9029   -2.5388    0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -2.5979    1.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.3829   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2002    2.5163   -4.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8638    0.7226   -4.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5400    1.3097   -4.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2281    1.9221   -1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1419    3.2953   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7696    2.7240    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0805    1.7235   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5343   -0.8332    1.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -0.3834    3.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2085    0.9853    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346   -1.7173   -0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170   -2.8328    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -2.4934    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 13 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 11  1  0
 25 12  1  0
 24 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 26 57  1  0
 26 58  1  0
 26 59  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       8.594  -0.170   0.841  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.141   0.254   0.694  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.687  -0.115  -0.692  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.255   0.256  -0.962  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.289  -0.429  -0.010  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.894   0.027  -0.388  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.844  -0.598   0.502  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.897  -2.110   0.381  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.504  -0.159   0.036  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.464   0.569  -0.956  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.697  -0.584   0.735  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.908  -0.268   0.357  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.827   0.405  -0.554  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.618   0.548  -1.957  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.698   0.130  -2.671  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.597   1.281  -2.679  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.507   1.495  -4.067  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.912   0.804   0.133  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.124   1.506  -0.204  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.080   1.644   0.694  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.355   2.372   0.378  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.907   1.095   1.983  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.074  -0.043   2.093  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.739   0.288   1.549  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.867  -0.935   1.330  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.574  -2.034   0.590  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.078  -1.364   2.372  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.713  -1.304   2.030  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.253  -1.763   2.690  0.00  0.00           O+0
HETATM   30  H   UNK     0       8.995  -0.598  -0.105  0.00  0.00           H+0
HETATM   31  H   UNK     0       8.720  -0.946   1.618  0.00  0.00           H+0
HETATM   32  H   UNK     0       9.233   0.700   1.128  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.090   1.346   0.845  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.532  -0.211   1.482  0.00  0.00           H+0
HETATM   35  H   UNK     0       7.312   0.423  -1.431  0.00  0.00           H+0
HETATM   36  H   UNK     0       6.814  -1.202  -0.857  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.156   1.351  -0.927  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.003  -0.124  -1.978  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.414  -1.518  -0.076  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.553  -0.102   1.013  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.643  -0.223  -1.431  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.869   1.130  -0.238  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.032  -0.244   1.538  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.903  -2.539   0.145  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.415  -2.598   1.230  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.529  -2.383  -0.517  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.200   2.516  -4.335  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.864   0.723  -4.574  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.540   1.310  -4.484  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.228   1.922  -1.217  0.00  0.00           H+0
HETATM   51  H   UNK     0      -7.142   3.295  -0.210  0.00  0.00           H+0
HETATM   52  H   UNK     0      -7.770   2.724   1.346  0.00  0.00           H+0
HETATM   53  H   UNK     0      -8.081   1.724  -0.128  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.534  -0.833   1.438  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.052  -0.383   3.155  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.208   0.985   2.186  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.935  -1.717  -0.407  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.817  -2.833   0.403  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.390  -2.493   1.141  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   33   34                                             
CONECT    3    2    4   35   36                                             
CONECT    4    3    5   37   38                                             
CONECT    5    4    6   39   40                                             
CONECT    6    5    7   41   42                                             
CONECT    7    6    8    9   43                                             
CONECT    8    7   44   45   46                                             
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   47   48   49                                             
CONECT   18   13   19   24                                                  
CONECT   19   18   20   50                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   51   52   53                                             
CONECT   22   20   23                                                       
CONECT   23   22   24   54   55                                             
CONECT   24   23   25   18   56                                             
CONECT   25   24   26   27   12                                             
CONECT   26   25   57   58   59                                             
CONECT   27   25   28                                                       
CONECT   28   27   29   11                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   19                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  122    0
END

RDKit          3D

59 61  0  0  0  0  0  0  0  0999 V2000
    8.5940   -0.1695    0.8412 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1407    0.2536    0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6869   -0.1152   -0.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    0.2560   -0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2885   -0.4286   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8940    0.0273   -0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8444   -0.5978    0.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8974   -2.1098    0.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5044   -0.1592    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4642    0.5685   -0.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6973   -0.5836    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079   -0.2677    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272    0.4052   -0.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.5480   -1.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6984    0.1302   -2.6714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5973    1.2807   -2.6792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5071    1.4950   -4.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118    0.8037    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1236    1.5064   -0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0795    1.6435    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3553    2.3717    0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9070    1.0949    1.9827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0735   -0.0434    2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7387    0.2880    1.5491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8668   -0.9354    1.3304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5739   -2.0338    0.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781   -1.3641    2.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -1.3040    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525   -1.7633    2.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9950   -0.5980   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7199   -0.9461    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2333    0.6997    1.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0897    1.3456    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -0.2111    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3119    0.4234   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8140   -1.2015   -0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1562    1.3513   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -0.1236   -1.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -1.5180   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5527   -0.1015    1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6431   -0.2226   -1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.1301   -0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318   -0.2436    1.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9029   -2.5388    0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -2.5979    1.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.3829   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2002    2.5163   -4.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8638    0.7226   -4.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5400    1.3097   -4.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2281    1.9221   -1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1419    3.2953   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7696    2.7240    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0805    1.7235   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5343   -0.8332    1.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0518   -0.3834    3.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2085    0.9853    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346   -1.7173   -0.4070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8170   -2.8328    0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -2.4934    1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 13 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 11  1  0
 25 12  1  0
 24 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 19 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 26 57  1  0
 26 58  1  0
 26 59  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0,]dodeca-5,7,9-triene-7-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₀O₆

Average Mass

402.4870 Da

Monoisotopic Mass

402.20424 Da

IUPAC Name

methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0^{2,6}]dodeca-5,7,9-triene-7-carboxylate

Traditional Name

methyl (1S,2S)-2,10-dimethyl-5-[(2S)-2-methyloctanoyl]-4-oxo-3,11-dioxatricyclo[6.4.0.0^{2,6}]dodeca-5,7,9-triene-7-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCC[C@H](C)C(=O)C1=C2C(C(=O)OC)=C3C=C(C)OC[C@H]3[C@]2(C)OC1=O

InChI Identifier

InChI=1S/C23H30O6/c1-6-7-8-9-10-13(2)20(24)18-19-17(21(25)27-5)15-11-14(3)28-12-16(15)23(19,4)29-22(18)26/h11,13,16H,6-10,12H2,1-5H3/t13-,16+,23-/m0/s1

InChI Key

UMDDQZKJZQPILY-LZDDTZTRSA-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
Aegiceras corniculatum	LOTUS Database	35616633
Aspergillus parasiticus	NPAtlas	11674610

Species Where Detected

Species Name	Source	Reference
Aspergillus parasiticus RDWD1-2	KNApSAcK Database	22123792
Penicillium sp. JP-1	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
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	4.3	ALOGPS
logP	3.84	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.54 m³·mol⁻¹	ChemAxon
Polarizability	44.7 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	Yes	ChemAxon

External Links

NPAtlas ID

NPA015412

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8154056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9978464

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Sequoiatone A (NP0003916)

MOL for NP0003916 (Sequoiatone A)

3D MOL for NP0003916 (Sequoiatone A)

3D SDF for NP0003916 (Sequoiatone A)

3D-SDF for NP0003916 (Sequoiatone A)

PDB for NP0003916 (Sequoiatone A)

3D PDB for NP0003916 (Sequoiatone A)

SMILES for NP0003916 (Sequoiatone A)

INCHI for NP0003916 (Sequoiatone A)

Structure for NP0003916 (Sequoiatone A)

3D Structure for NP0003916 (Sequoiatone A)