NP-MRD: Showing NP-Card for khayseneganin D (NP0043266)

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Record Information

Version

1.0

Created at

2021-06-21 00:43:25 UTC

Updated at

2021-06-30 00:18:51 UTC

NP-MRD ID

NP0043266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

khayseneganin D

Provided By

JEOL Database JEOL Logo

Description

Rel-Khayseneganin D belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. khayseneganin D is found in Khaya senegalensis. It was first documented in 2021 (PMID: 34130369). Based on a literature review a significant number of articles have been published on Rel-Khayseneganin D (PMID: 34130276) (PMID: 34130326) (PMID: 34130315) (PMID: 34130243).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102433D          

 70 74  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 34 66  1  0
 34 67  1  0
M  END


  Mrv1652306212102433D          

 70 74  0  0  0  0            999 V2000
    1.5510   -3.7449    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -2.7370   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.3151   -0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4785   -0.9468   -0.3918 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0621   -1.1479   -1.7976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7321   -2.5400   -2.4101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5925   -3.6277   -1.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9860   -2.5364   -3.9457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4125   -2.2545   -4.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968   -0.9817   -4.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -1.2139   -4.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -2.5425   -4.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -3.1674   -4.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5614   -3.7759   -4.5483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806   -4.2456   -4.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680   -4.9302   -5.1456 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -4.0895   -2.9186 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7905   -2.8033   -2.2220 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4622   -1.7043   -2.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -1.1662   -2.2196 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4753   -0.4575   -3.2316 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7440    0.5422   -4.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.4168   -5.2744 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2170    1.6044   -3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344    2.0656   -2.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7331    3.4488   -2.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9165    2.3954   -1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6847    1.1112   -1.0586 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4588    1.7617    0.3535 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6710    2.3415    0.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    2.7336    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.6188   -0.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114    3.7190    1.3229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446    4.6738    1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -0.4155   -0.9071 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4027   -0.5114    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617   -4.7651   -0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880   -3.5778    1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -1.3009    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.5733    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793    0.0715   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886   -0.3555   -2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.0023   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533   -3.7337   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -4.6114   -2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586   -3.3813   -1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870   -1.7505   -4.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5147   -0.0141   -4.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1391   -0.5766   -5.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4811   -4.2464   -4.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -4.9801   -2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -4.1204   -2.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -2.0287   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916   -0.0478   -2.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210   -1.2178   -3.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    4.0393   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    3.3390   -2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    4.0436   -2.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3476    2.8580   -2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625    3.0970   -1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5367    1.5315   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6986    1.0193   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898    0.9954    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    2.8998    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.4254    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    4.1893    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7260    5.1745    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849   -0.1410    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691    0.0302   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228   -1.5521    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
 14  8  1  0  0  0  0
  2  1  2  3  0  0  0
  3 35  1  0  0  0  0
 28 29  1  0  0  0  0
  6  7  1  1  0  0  0
 35 28  1  0  0  0  0
  3  4  1  0  0  0  0
 28 25  1  0  0  0  0
  8  9  1  0  0  0  0
 35 20  1  0  0  0  0
  9 13  2  0  0  0  0
 25 24  1  0  0  0  0
  2 18  1  0  0  0  0
 20 21  1  0  0  0  0
  6  5  1  0  0  0  0
 24 22  1  0  0  0  0
 21 22  1  0  0  0  0
  5  4  1  0  0  0  0
 22 23  2  0  0  0  0
  6 18  1  0  0  0  0
 25 26  1  6  0  0  0
 13 12  1  0  0  0  0
  3 39  1  1  0  0  0
 12 11  1  0  0  0  0
 35 36  1  1  0  0  0
 11 10  2  0  0  0  0
 25 27  1  0  0  0  0
 10  9  1  0  0  0  0
 29 30  1  0  0  0  0
  6  8  1  0  0  0  0
 29 31  1  0  0  0  0
 15 16  2  0  0  0  0
 31 32  2  0  0  0  0
  2  3  1  0  0  0  0
 31 33  1  0  0  0  0
 18 17  1  0  0  0  0
 33 34  1  0  0  0  0
 17 15  1  0  0  0  0
 20 19  1  0  0  0  0
 18 19  1  6  0  0  0
  5 42  1  0  0  0  0
  5 43  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
 17 51  1  0  0  0  0
 17 52  1  0  0  0  0
  8 47  1  6  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
  7 46  1  0  0  0  0
 13 50  1  0  0  0  0
 11 49  1  0  0  0  0
 10 48  1  0  0  0  0
 29 63  1  1  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
 28 62  1  6  0  0  0
 20 53  1  1  0  0  0
 21 54  1  0  0  0  0
 21 55  1  0  0  0  0
 26 56  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 36 68  1  0  0  0  0
 36 69  1  0  0  0  0
 36 70  1  0  0  0  0
 27 59  1  0  0  0  0
 27 60  1  0  0  0  0
 27 61  1  0  0  0  0
 30 64  1  0  0  0  0
 34 65  1  0  0  0  0
 34 66  1  0  0  0  0
 34 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043266

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C(=O)OC([H])([H])[H])[C@]1([H])[C@]2(C([H])([H])[H])[C@@]([H])(O[C@@]34C(=C([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC(=O)C4([H])[H])C2=C([H])OC([H])=C2[H])C([H])([H])C(=O)OC1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O9/c1-14-16-7-9-25(4)22(15-8-10-33-13-15)34-19(29)12-27(14,25)35-17-11-18(28)36-24(2,3)21(26(16,17)5)20(30)23(31)32-6/h8,10,13,16-17,20-22,30H,1,7,9,11-12H2,2-6H3/t16-,17-,20+,21-,22-,25-,26-,27-/m0/s1

> <INCHI_KEY>
WZMQOORLOIIGRA-KFHOXVFPSA-N

> <FORMULA>
C27H34O9

> <MOLECULAR_WEIGHT>
502.56

> <EXACT_MASS>
502.220282675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.1783419307981

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-[(1S,3S,8S,9R,10R,13S,14R)-14-(furan-3-yl)-7,7,9,13-tetramethyl-18-methylidene-5,16-dioxo-2,6,15-trioxatetracyclo[8.7.1.0^{1,13}.0^{3,9}]octadecan-8-yl]-2-hydroxyacetate

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.2154452813333325

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.36086585733101

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8695934753499217

> <JCHEM_POLAR_SURFACE_AREA>
121.50000000000001

> <JCHEM_REFRACTIVITY>
123.95669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-(methyl [(1S,3S,8S,9R,10R,13S,14R)-14-(furan-3-yl)-7,7,9,13-tetramethyl-18-methylidene-5,16-dioxo-2,6,15-trioxatetracyclo[8.7.1.0^{1,13}.0^{3,9}]octadecan-8-yl](hydroxy)acetate)

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
    1.5510   -3.7449    0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -2.7370   -0.7310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -1.3151   -0.2179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4785   -0.9468   -0.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621   -1.1479   -1.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7321   -2.5400   -2.4101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5925   -3.6277   -1.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9860   -2.5364   -3.9457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4125   -2.2545   -4.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968   -0.9817   -4.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -1.2139   -4.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -2.5425   -4.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4277   -3.1674   -4.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5614   -3.7759   -4.5483 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806   -4.2456   -4.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680   -4.9302   -5.1456 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -4.0895   -2.9186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7905   -2.8033   -2.2220 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4622   -1.7043   -2.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -1.1662   -2.2196 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4753   -0.4575   -3.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7440    0.5422   -4.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343    0.4168   -5.2744 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2170    1.6044   -3.4366 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4344    2.0656   -2.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7331    3.4488   -2.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9165    2.3954   -1.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6847    1.1112   -1.0586 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4588    1.7617    0.3535 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6710    2.3415    0.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2574    2.7336    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.6188   -0.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114    3.7190    1.3229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5446    4.6738    1.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -0.4155   -0.9071 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4027   -0.5114    0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617   -4.7651   -0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880   -3.5778    1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1910   -1.3009    0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -1.5733    0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6793    0.0715   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886   -0.3555   -2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -1.0023   -1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533   -3.7337   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4631   -4.6114   -2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586   -3.3813   -1.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870   -1.7505   -4.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5147   -0.0141   -4.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1391   -0.5766   -5.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4811   -4.2464   -4.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905   -4.9801   -2.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -4.1204   -2.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2198   -2.0287   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916   -0.0478   -2.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210   -1.2178   -3.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594    4.0393   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    3.3390   -2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406    4.0436   -2.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3476    2.8580   -2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625    3.0970   -1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5367    1.5315   -1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6986    1.0193   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898    0.9954    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4323    2.8998    1.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347    5.4254    2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    4.1893    1.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7260    5.1745    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849   -0.1410    1.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691    0.0302   -0.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228   -1.5521    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14  8  1  0
  2  1  2  3
  3 35  1  0
 28 29  1  0
  6  7  1  1
 35 28  1  0
  3  4  1  0
 28 25  1  0
  8  9  1  0
 35 20  1  0
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  2 18  1  0
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 22 23  2  0
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 13 12  1  0
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 10  9  1  0
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  6  8  1  0
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 31 32  2  0
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 34 66  1  0
 34 67  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.551  -3.745   0.060  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.145  -2.737  -0.731  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.017  -1.315  -0.218  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.479  -0.947  -0.392  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.062  -1.148  -1.798  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.732  -2.540  -2.410  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.593  -3.628  -1.715  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.986  -2.536  -3.946  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.413  -2.255  -4.341  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.997  -0.982  -4.615  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.311  -1.214  -4.942  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.580  -2.543  -4.903  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.428  -3.167  -4.556  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.561  -3.776  -4.548  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.681  -4.246  -4.312  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.268  -4.930  -5.146  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.220  -4.090  -2.919  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.791  -2.803  -2.222  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.462  -1.704  -2.894  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.600  -1.166  -2.220  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.475  -0.458  -3.232  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.744   0.542  -4.058  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.634   0.417  -5.274  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.217   1.604  -3.437  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.434   2.066  -2.069  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.733   3.449  -2.143  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.917   2.395  -1.837  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.685   1.111  -1.059  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.459   1.762   0.354  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.671   2.341   0.825  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.257   2.734   0.408  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.780   2.619  -0.228  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.511   3.719   1.323  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.545   4.674   1.450  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.166  -0.416  -0.907  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.403  -0.511   0.045  0.00  0.00           C+0
HETATM   37  H   UNK     0       1.662  -4.765  -0.292  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.788  -3.578   1.108  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.191  -1.301   0.867  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.060  -1.573   0.300  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.679   0.072  -0.057  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.689  -0.356  -2.456  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.148  -1.002  -1.743  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.353  -3.734  -0.653  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.463  -4.611  -2.177  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.659  -3.381  -1.765  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.387  -1.751  -4.427  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.515  -0.014  -4.577  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.139  -0.577  -5.220  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.481  -4.246  -4.503  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.891  -4.980  -2.372  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.314  -4.120  -2.995  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.220  -2.029  -1.930  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.392  -0.048  -2.813  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.821  -1.218  -3.949  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.859   4.039  -1.232  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.665   3.339  -2.361  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.141   4.044  -2.971  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.348   2.858  -2.734  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.063   3.097  -1.011  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.537   1.532  -1.625  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.699   1.019  -1.524  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.190   0.995   1.088  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.432   2.900   1.591  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.235   5.425   2.181  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.456   4.189   1.815  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.726   5.175   0.494  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.185  -0.141   1.051  0.00  0.00           H+0
HETATM   69  H   UNK     0       4.269   0.030  -0.330  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.723  -1.552   0.177  0.00  0.00           H+0
CONECT    1    2   37   38                                                  
CONECT    2    1   18    3                                                  
CONECT    3   35    4   39    2                                             
CONECT    4    3    5   40   41                                             
CONECT    5    6    4   42   43                                             
CONECT    6    7    5   18    8                                             
CONECT    7    6   44   45   46                                             
CONECT    8   14    9    6   47                                             
CONECT    9    8   13   10                                                  
CONECT   10   11    9   48                                                  
CONECT   11   12   10   49                                                  
CONECT   12   13   11                                                       
CONECT   13    9   12   50                                                  
CONECT   14   15    8                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   18   15   51   52                                             
CONECT   18    2    6   17   19                                             
CONECT   19   20   18                                                       
CONECT   20   35   21   19   53                                             
CONECT   21   20   22   54   55                                             
CONECT   22   24   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25   22                                                       
CONECT   25   28   24   26   27                                             
CONECT   26   25   56   57   58                                             
CONECT   27   25   59   60   61                                             
CONECT   28   29   35   25   62                                             
CONECT   29   28   30   31   63                                             
CONECT   30   29   64                                                       
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   65   66   67                                             
CONECT   35    3   28   20   36                                             
CONECT   36   35   68   69   70                                             
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    5                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    7                                                            
CONECT   47    8                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   17                                                            
CONECT   52   17                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
CONECT   63   29                                                            
CONECT   64   30                                                            
CONECT   65   34                                                            
CONECT   66   34                                                            
CONECT   67   34                                                            
CONECT   68   36                                                            
CONECT   69   36                                                            
CONECT   70   36                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  148    0
END

RDKit          3D

70 74  0  0  0  0  0  0  0  0999 V2000
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   -2.4125   -2.2545   -4.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5802   -2.5425   -4.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
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 14  8  1  0
  2  1  2  3
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  6  7  1  1
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  3  4  1  0
 28 25  1  0
  8  9  1  0
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  9 13  2  0
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  3 39  1  1
 12 11  1  0
 35 36  1  1
 11 10  2  0
 25 27  1  0
 10  9  1  0
 29 30  1  0
  6  8  1  0
 29 31  1  0
 15 16  2  0
 31 32  2  0
  2  3  1  0
 31 33  1  0
 18 17  1  0
 33 34  1  0
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 18 19  1  6
  5 42  1  0
  5 43  1  0
  4 40  1  0
  4 41  1  0
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 17 52  1  0
  8 47  1  6
  7 44  1  0
  7 45  1  0
  7 46  1  0
 13 50  1  0
 11 49  1  0
 10 48  1  0
 29 63  1  1
  1 37  1  0
  1 38  1  0
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 21 54  1  0
 21 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
 36 68  1  0
 36 69  1  0
 36 70  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 30 64  1  0
 34 65  1  0
 34 66  1  0
 34 67  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₉

Average Mass

502.5600 Da

Monoisotopic Mass

502.22028 Da

IUPAC Name

methyl (2R)-2-[(1S,3S,8S,9R,10R,13S,14R)-14-(furan-3-yl)-7,7,9,13-tetramethyl-18-methylidene-5,16-dioxo-2,6,15-trioxatetracyclo[8.7.1.0^{1,13}.0^{3,9}]octadecan-8-yl]-2-hydroxyacetate

Traditional Name

(R)-(methyl [(1S,3S,8S,9R,10R,13S,14R)-14-(furan-3-yl)-7,7,9,13-tetramethyl-18-methylidene-5,16-dioxo-2,6,15-trioxatetracyclo[8.7.1.0^{1,13}.0^{3,9}]octadecan-8-yl](hydroxy)acetate)

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C(=O)OC([H])([H])[H])[C@]1([H])[C@]2(C([H])([H])[H])[C@@]([H])(O[C@@]34C(=C([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(OC(=O)C4([H])[H])C2=C([H])OC([H])=C2[H])C([H])([H])C(=O)OC1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H34O9/c1-14-16-7-9-25(4)22(15-8-10-33-13-15)34-19(29)12-27(14,25)35-17-11-18(28)36-24(2,3)21(26(16,17)5)20(30)23(31)32-6/h8,10,13,16-17,20-22,30H,1,7,9,11-12H2,2-6H3/t16-,17-,20+,21-,22-,25-,26-,27-/m0/s1

InChI Key

WZMQOORLOIIGRA-KFHOXVFPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Khaya senegalensis	JEOL database	Yuan, C. -M., et al, J. Nat. Prod. 76, 327 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Caprolactone
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Furan
Heteroaromatic compound
Methyl ester
Lactone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.02	ALOGPS
logP	2.22	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.36	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	121.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.96 m³·mol⁻¹	ChemAxon
Polarizability	51.18 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29419147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71658779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Malho Guedes A, Marques R, Domingos AT, Silva AP, Bernardo I, Neves PL, Rodrigues A, Krediet RT: Overhydration May Be the Missing Link between Peritoneal Protein Clearance and Mortality. Nephron. 2021 Jun 15:1-7. doi: 10.1159/000516531. [PubMed:34130276 ]
Nepal S, Jarusriwanna A, Unnanuntana A: Stress Fracture of the Femoral Shaft in Paget's Disease of Bone: A Case Report. J Bone Metab. 2021 May;28(2):171-178. doi: 10.11005/jbm.2021.28.2.171. Epub 2021 May 31. [PubMed:34130369 ]
Lindner LH: [Deep vein thrombosis - diagnostics and clarification]. Dtsch Med Wochenschr. 2021 Jun;146(12):832-836. doi: 10.1055/a-1226-5288. Epub 2021 Jun 15. [PubMed:34130326 ]
Hekimian G, Masi P, Lejeune M, Lebreton G, Chommeloux J, Desnos C, Pineton De Chambrun M, Martin-Toutain I, Nieszkowska A, Brechot N, Schmidt M, Leprince P, Luyt CE, Combes A, Frere C: Extracorporeal Membrane Oxygenation Induces Early Alterations in Coagulation and Fibrinolysis Profiles in COVID-19 Patients with Acute Respiratory Distress Syndrome. Thromb Haemost. 2021 Aug;121(8):1031-1042. doi: 10.1055/a-1529-2257. Epub 2021 Jun 15. [PubMed:34130315 ]
Cole J, Selby B, Ismail Z, McGirr A: D-cycloserine normalizes long-term motor plasticity after transcranial magnetic intermittent theta-burst stimulation in major depressive disorder. Clin Neurophysiol. 2021 Aug;132(8):1770-1776. doi: 10.1016/j.clinph.2021.04.002. Epub 2021 Apr 21. [PubMed:34130243 ]
Yuan, C. -M., et al. (2013). Yuan, C. -M., et al, J. Nat. Prod. 76, 327 (2013). J. Nat. Prod..

Showing NP-Card for khayseneganin D (NP0043266)

MOL for NP0043266 (khayseneganin D)

3D MOL for NP0043266 (khayseneganin D)

3D SDF for NP0043266 (khayseneganin D)

3D-SDF for NP0043266 (khayseneganin D)

PDB for NP0043266 (khayseneganin D)

3D PDB for NP0043266 (khayseneganin D)

SMILES for NP0043266 (khayseneganin D)

INCHI for NP0043266 (khayseneganin D)

Structure for NP0043266 (khayseneganin D)

3D Structure for NP0043266 (khayseneganin D)