NP-MRD: Showing NP-Card for withaphysalin N (NP0027324)

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Record Information

Version

1.0

Created at

2021-06-19 18:58:50 UTC

Updated at

2021-06-29 23:53:22 UTC

NP-MRD ID

NP0027324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

withaphysalin N

Provided By

JEOL Database JEOL Logo

Description

withaphysalin N is found in Acnistus arborescens. It was first documented in 2004 (PMID: 15104512). Based on a literature review very few articles have been published on withaphysalin N (PMID: 33840171).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120583D          

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M  END

     RDKit          3D

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  1 36  1  0
  1 37  1  0
  1 38  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
M  END


  Mrv1652306192120583D          

 71 77  0  0  0  0            999 V2000
    0.8339    1.8904    7.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    1.8645    6.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6973    1.7081    7.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    1.4707    8.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    1.8309    6.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0537    1.9661    7.2569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9127    1.8257    5.3197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7127    1.3392    4.6729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8365    1.5350    3.1299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2359    2.9923    2.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978    0.6871    2.6494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6310    0.2145    1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289   -0.4508    0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.6180    0.9489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2722    1.6264   -0.1970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7230    0.9630   -1.5090 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8957   -0.2904   -1.9221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7833   -1.2885   -0.7309 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2086   -2.4089   -1.0664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0863   -3.0800   -2.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4636   -3.3589   -2.5822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -2.3841   -3.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7217   -2.9441   -4.8705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0022   -3.3692   -5.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1525   -1.9338   -5.8528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9709   -0.6567   -5.8429 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9124   -0.0659   -4.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    1.0861   -4.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045   -0.9535   -3.2767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9467   -0.9878   -3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -0.5348    0.5217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1147   -1.3138    1.8069 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1266   -0.1897    2.8141 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6252    1.0752    2.2949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5069    2.0519    5.2833 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3938    2.7692    7.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937    1.9461    8.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004    0.9949    7.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540    1.1530    9.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313    2.3809    9.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6046    0.6727    9.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6941    0.2649    4.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0693    3.3256    3.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6056    3.1152    1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996    3.6813    2.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    2.0735   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9597    2.4500    0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788    0.6963   -1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859    1.7223   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    0.0667   -2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7649   -1.7384   -0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288   -2.0084   -1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011   -3.1650   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -3.8517   -2.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0764   -3.8304   -4.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763   -3.9115   -4.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -2.3508   -6.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8878   -1.7089   -5.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -0.8216   -6.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    0.0614   -6.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077   -1.5542   -4.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -1.4563   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3715    0.0168   -3.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -0.1035    0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -1.9987    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069   -1.8923    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.0398    2.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349   -0.5209    3.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.8866    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    1.6487    4.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    3.1283    5.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
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 19 18  1  0  0  0  0
 17 18  1  0  0  0  0
 23 22  1  0  0  0  0
 29 27  1  0  0  0  0
 29 22  1  0  0  0  0
 34  9  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 14 12  1  1  0  0  0
 27 28  2  0  0  0  0
 17 16  1  0  0  0  0
 22 21  1  1  0  0  0
 20 21  1  0  0  0  0
  8  7  1  0  0  0  0
 18 31  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 26 25  1  0  0  0  0
 23 24  1  0  0  0  0
 26 27  1  0  0  0  0
  8 35  1  0  0  0  0
  7  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2 35  1  0  0  0  0
  9  8  1  0  0  0  0
 29 30  1  1  0  0  0
 18 51  1  1  0  0  0
 25 23  1  0  0  0  0
  3  4  1  0  0  0  0
 31 64  1  6  0  0  0
  5  6  2  0  0  0  0
 14 31  1  0  0  0  0
  2  1  1  0  0  0  0
 29 17  1  0  0  0  0
 12 13  2  0  0  0  0
 22 20  1  0  0  0  0
  8 42  1  6  0  0  0
 20 19  1  0  0  0  0
  9 10  1  1  0  0  0
 31 32  1  0  0  0  0
 17 50  1  6  0  0  0
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 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
 10 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])C(=O)[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]45C(=O)O[C@](C([H])([H])[H])([C@@]4([H])C([H])([H])C([H])([H])[C@@]5([H])[C@]3([H])C([H])([H])[C@@]3([H])O[C@@]123)[C@]1([H])OC(=O)C(=C(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O7/c1-13-11-21(33-23(31)14(13)2)26(4)18-6-5-17-15-12-22-28(34-22)20(30)8-7-19(29)25(28,3)16(15)9-10-27(17,18)24(32)35-26/h15-18,20-22,30H,5-12H2,1-4H3/t15-,16+,17+,18-,20+,21-,22-,25+,26-,27-,28-/m1/s1

> <INCHI_KEY>
PGJRQHKPPYIVQE-BGDMQGTOSA-N

> <FORMULA>
C28H36O7

> <MOLECULAR_WEIGHT>
484.589

> <EXACT_MASS>
484.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.70826685606198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6R,9R,12S,13R,17S,18R,20R)-6-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-17-hydroxy-6,13-dimethyl-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicosane-8,14-dione

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
3.483832009999998

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.70677934435169

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.862331738890035

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2962723374126597

> <JCHEM_POLAR_SURFACE_AREA>
102.43

> <JCHEM_REFRACTIVITY>
124.15679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6R,9R,12S,13R,17S,18R,20R)-6-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-17-hydroxy-6,13-dimethyl-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicosane-8,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
    0.8339    1.8904    7.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2359    2.9923    2.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3938    2.7692    7.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2288   -2.0084   -1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2011   -3.1650   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8878   -1.7089   -5.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -0.8216   -6.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5449    0.0614   -6.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3077   -1.5542   -4.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769   -1.4563   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3715    0.0168   -3.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -0.1035    0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7375   -1.9987    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069   -1.8923    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.0398    2.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349   -0.5209    3.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.8866    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    1.6487    4.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    3.1283    5.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 33  1  0
 33 34  1  0
 14 34  1  0
 19 18  1  0
 17 18  1  0
 23 22  1  0
 29 27  1  0
 29 22  1  0
 34  9  1  0
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 11 12  1  0
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 27 28  2  0
 17 16  1  0
 22 21  1  1
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  8  7  1  0
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 15 14  1  0
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 26 25  1  0
 23 24  1  0
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  8 35  1  0
  7  5  1  0
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  2 35  1  0
  9  8  1  0
 29 30  1  1
 18 51  1  1
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  3  4  1  0
 31 64  1  6
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 14 31  1  0
  2  1  1  0
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 22 20  1  0
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 10 43  1  0
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 10 45  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       0.834   1.890   7.429  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.521   1.865   6.779  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.697   1.708   7.423  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.874   1.471   8.896  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.985   1.831   6.673  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.054   1.966   7.257  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.913   1.826   5.320  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.713   1.339   4.673  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.837   1.535   3.130  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.236   2.992   2.816  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.898   0.687   2.649  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.631   0.215   1.396  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.429  -0.451   0.756  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.226   0.618   0.949  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.272   1.626  -0.197  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.723   0.963  -1.509  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.896  -0.290  -1.922  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.783  -1.289  -0.731  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.209  -2.409  -1.066  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.086  -3.080  -2.356  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.464  -3.359  -2.582  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.845  -2.384  -3.466  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.722  -2.944  -4.870  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.002  -3.369  -5.326  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.153  -1.934  -5.853  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.971  -0.657  -5.843  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.912  -0.066  -4.455  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.500   1.086  -4.306  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.405  -0.954  -3.277  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.947  -0.988  -3.348  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.309  -0.535   0.522  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.115  -1.314   1.807  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.127  -0.190   2.814  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.625   1.075   2.295  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.507   2.052   5.283  0.00  0.00           C+0
HETATM   36  H   UNK     0       1.394   2.769   7.091  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.794   1.946   8.519  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.400   0.995   7.154  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.954   1.153   9.392  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.231   2.381   9.388  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.605   0.673   9.070  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.694   0.265   4.894  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.069   3.326   3.444  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.606   3.115   1.798  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.400   3.681   2.968  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.281   2.074  -0.344  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.960   2.450   0.005  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.779   0.696  -1.400  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.686   1.722  -2.297  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.130   0.067  -2.107  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.765  -1.738  -0.545  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.229  -2.008  -1.113  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.201  -3.165  -0.273  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.634  -3.852  -2.596  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.076  -3.830  -4.874  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.376  -3.912  -4.604  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.159  -2.351  -6.867  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.888  -1.709  -5.587  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.014  -0.822  -6.128  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.545   0.061  -6.552  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.308  -1.554  -4.211  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.377  -1.456  -2.456  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.372   0.017  -3.451  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.675  -0.104   0.271  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.738  -1.999   1.768  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.007  -1.892   2.071  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.200   0.040   2.837  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.135  -0.521   3.819  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.103   1.887   2.178  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.421   1.649   4.865  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.526   3.128   5.078  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3   35    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   39   40   41                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    7   35    9   42                                             
CONECT    9   34   11    8   10                                             
CONECT   10    9   43   44   45                                             
CONECT   11    9   12                                                       
CONECT   12   11   14   13                                                  
CONECT   13   12                                                            
CONECT   14   34   12   15   31                                             
CONECT   15   14   16   46   47                                             
CONECT   16   17   15   48   49                                             
CONECT   17   18   16   29   50                                             
CONECT   18   19   17   31   51                                             
CONECT   19   18   20   52   53                                             
CONECT   20   21   22   19   54                                             
CONECT   21   22   20                                                       
CONECT   22   23   29   21   20                                             
CONECT   23   22   24   25   55                                             
CONECT   24   23   56                                                       
CONECT   25   26   23   57   58                                             
CONECT   26   25   27   59   60                                             
CONECT   27   29   28   26                                                  
CONECT   28   27                                                            
CONECT   29   27   22   30   17                                             
CONECT   30   29   61   62   63                                             
CONECT   31   18   64   14   32                                             
CONECT   32   33   31   65   66                                             
CONECT   33   32   34   67   68                                             
CONECT   34   33   14    9   69                                             
CONECT   35    8    2   70   71                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    8                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   32                                                            
CONECT   67   33                                                            
CONECT   68   33                                                            
CONECT   69   34                                                            
CONECT   70   35                                                            
CONECT   71   35                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  154    0
END

RDKit          3D

71 77  0  0  0  0  0  0  0  0999 V2000
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   -1.7127    1.3392    4.6729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8365    1.5350    3.1299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2359    2.9923    2.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978    0.6871    2.6494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6310    0.2145    1.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289   -0.4508    0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    0.6180    0.9489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2722    1.6264   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0863   -3.0800   -2.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.9467   -0.9878   -3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3093   -0.5348    0.5217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1147   -1.3138    1.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1266   -0.1897    2.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6252    1.0752    2.2949 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5069    2.0519    5.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938    2.7692    7.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937    1.9461    8.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004    0.9949    7.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540    1.1530    9.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2313    2.3809    9.3883 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0693    3.3256    3.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3996    3.6813    2.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9597    2.4500    0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7649   -1.7384   -0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288   -2.0084   -1.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8878   -1.7089   -5.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7375   -1.9987    1.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069   -1.8923    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002    0.0398    2.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1349   -0.5209    3.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.8866    2.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    1.6487    4.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    3.1283    5.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 33  1  0
 33 34  1  0
 14 34  1  0
 19 18  1  0
 17 18  1  0
 23 22  1  0
 29 27  1  0
 29 22  1  0
 34  9  1  0
  9 11  1  0
 11 12  1  0
 14 12  1  1
 27 28  2  0
 17 16  1  0
 22 21  1  1
 20 21  1  0
  8  7  1  0
 18 31  1  0
 15 14  1  0
 15 16  1  0
 26 25  1  0
 23 24  1  0
 26 27  1  0
  8 35  1  0
  7  5  1  0
  5  3  1  0
  3  2  2  0
  2 35  1  0
  9  8  1  0
 29 30  1  1
 18 51  1  1
 25 23  1  0
  3  4  1  0
 31 64  1  6
  5  6  2  0
 14 31  1  0
  2  1  1  0
 29 17  1  0
 12 13  2  0
 22 20  1  0
  8 42  1  6
 20 19  1  0
  9 10  1  1
 31 32  1  0
 17 50  1  6
 26 59  1  0
 26 60  1  0
 25 57  1  0
 25 58  1  0
 23 55  1  1
 20 54  1  6
 19 52  1  0
 19 53  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 24 56  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  6
 35 70  1  0
 35 71  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 10 43  1  0
 10 44  1  0
 10 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
Rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-24-enolide	MeSH

Chemical Formula

C₂₈H₃₆O₇

Average Mass

484.5890 Da

Monoisotopic Mass

484.24610 Da

IUPAC Name

(1R,2S,5S,6R,9R,12S,13R,17S,18R,20R)-6-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-17-hydroxy-6,13-dimethyl-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicosane-8,14-dione

Traditional Name

(1R,2S,5S,6R,9R,12S,13R,17S,18R,20R)-6-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-17-hydroxy-6,13-dimethyl-7,19-dioxahexacyclo[10.9.0.0^{2,9}.0^{5,9}.0^{13,18}.0^{18,20}]henicosane-8,14-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])C(=O)[C@]2(C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])[C@]45C(=O)O[C@](C([H])([H])[H])([C@@]4([H])C([H])([H])C([H])([H])[C@@]5([H])[C@]3([H])C([H])([H])[C@@]3([H])O[C@@]123)[C@]1([H])OC(=O)C(=C(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C28H36O7/c1-13-11-21(33-23(31)14(13)2)26(4)18-6-5-17-15-12-22-28(34-22)20(30)8-7-19(29)25(28,3)16(15)9-10-27(17,18)24(32)35-26/h15-18,20-22,30H,5-12H2,1-4H3/t15-,16+,17+,18-,20+,21-,22-,25+,26-,27-,28-/m1/s1

InChI Key

PGJRQHKPPYIVQE-BGDMQGTOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Acnistus arborescens	JEOL database	Veras, M. L., et al, J. Nat. Prod. 67, 710 (2004)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
Dihydropyranone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	2.66	ALOGPS
logP	3.48	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	124.16 m³·mol⁻¹	ChemAxon
Polarizability	52.71 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

9926767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11752064

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Veras ML, Bezerra MZ, Lemos TL, Uchoa DE, Braz-Filho R, Chai HB, Cordell GA, Pessoa OD: Cytotoxic withaphysalins from the leaves of Acnistus arborescens. J Nat Prod. 2004 Apr;67(4):710-3. doi: 10.1021/np0340347. [PubMed:15104512 ]
Rath SN, Jena L, Bhuyan R, Mahanandia NC, Patri M: In silico discovery and evaluation of phytochemicals binding mechanism against human catechol-O-methyltransferase as a putative bioenhancer of L-DOPA therapy in Parkinson disease. Genomics Inform. 2021 Mar;19(1):e7. doi: 10.5808/gi.20061. Epub 2021 Feb 26. [PubMed:33840171 ]
Veras, M. L., et al. (2004). Veras, M. L., et al, J. Nat. Prod. 67, 710 (2004). J. Nat. Prod..

Showing NP-Card for withaphysalin N (NP0027324)

MOL for NP0027324 (withaphysalin N)

3D MOL for NP0027324 (withaphysalin N)

3D SDF for NP0027324 (withaphysalin N)

3D-SDF for NP0027324 (withaphysalin N)

PDB for NP0027324 (withaphysalin N)

3D PDB for NP0027324 (withaphysalin N)

SMILES for NP0027324 (withaphysalin N)

INCHI for NP0027324 (withaphysalin N)

Structure for NP0027324 (withaphysalin N)

3D Structure for NP0027324 (withaphysalin N)