NP-MRD: Showing NP-Card for Digoxigenin (NP0002884)

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Record Information

Version

2.0

Created at

2020-11-23 19:42:47 UTC

Updated at

2021-08-12 19:52:25 UTC

NP-MRD ID

NP0002884

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Digoxigenin

Provided By

BMRB

Description

Digoxigenin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Digoxigenin is found in Asclepias syriaca and Digitalis purpurea. Digoxigenin was first documented in 1994 (PMID: 8080093). Based on a literature review a small amount of articles have been published on Digoxigenin (PMID: 23344238) (PMID: 23383657).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

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M  END

NP0002884
     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
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M  END


     RDKit          2D

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   -2.5024    2.5990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3908    1.8540    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7573    2.8789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7782   -0.9383    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2387    0.4244    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9178   -2.7024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2579   -1.7676    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -2.4739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2574   -3.8855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7838   -3.3028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291   -3.4411    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2790   -3.8496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -2.4639    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343    1.6583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2604    3.0440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103    2.6355    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.4972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8309    4.0856    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    2.4242    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9113    0.7511    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028    2.8327    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7684    1.5122    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1274    2.7935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3919   -2.3875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -1.8377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -1.3976    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0344   -2.8089    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9689   -3.3309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7360   -3.4955    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -3.6592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
  8  2  1  0
 27 11  1  0
  2 12  1  6
 16 27  1  1
 24 19  1  0
  1 29  1  1
  1 30  1  0
  1 31  1  0
  3 32  1  1
  3 33  1  0
  4 34  1  6
  4 35  1  0
  5 36  1  6
  6 37  1  0
  7 38  1  1
  7 39  1  0
  8 40  1  1
  9 41  1  1
  9 42  1  0
 10 43  1  6
 10 44  1  0
 11 45  1  1
 12 46  1  6
 13 47  1  1
 13 48  1  0
 14 49  1  6
 15 50  1  0
 17 51  1  6
 17 52  1  0
 17 53  1  0
 18 54  1  6
 20 55  1  0
 24 56  1  1
 24 57  1  0
 25 58  1  1
 25 59  1  0
 26 60  1  1
 26 61  1  0
 28 62  1  0
M  END
> <DATABASE_ID>
NP0002884

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18+,19-,21+,22+,23+/m1/s1

> <INCHI_KEY>
SHIBSTMRCDJXLN-KCZCNTNESA-N

> <FORMULA>
C23H34O5

> <MOLECULAR_WEIGHT>
390.5131

> <EXACT_MASS>
390.240624198

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.40186413163667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.8365435200000007

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.971828180929794

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1511163990866295

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569547719289878

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
105.15609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
digoxigenin

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002884
     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
   -2.3451   -1.9048   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2259   -0.6168    0.0852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7809   -1.0533    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054   -1.5278    1.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0573   -0.2954    1.0174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0338   -0.5852    0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895    0.8529    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498    0.3958   -0.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5510    1.6322   -1.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    2.0495   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3247    0.8554   -0.6304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8118   -0.2166    0.2989 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1615   -1.3502    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027   -1.1949   -0.6609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9847   -1.4280   -1.9859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    0.1113   -0.5691 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7782    0.3277   -1.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    0.1312    0.6595 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2120   -0.4134    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800    0.3244    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4647   -0.4681    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6700   -0.0999    0.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0711   -1.7161    0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -1.7426    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349    1.5716    1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399    1.8882    0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723    1.2808   -0.3925 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3547    2.2964   -1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4004   -1.8975   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945   -1.8987   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -2.8091   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -0.2079    2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1147   -1.8386    1.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474   -2.3295    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4827   -1.9503    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5774    0.0042    1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9163   -0.0920   -0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8532    1.5641    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7374    1.4160    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971   -0.0447   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2535    2.5084   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    1.5248   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3735    2.2236    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947    2.9475   -0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443    0.5548   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    0.2451    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -1.5400    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -2.3420    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -1.9926   -0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103   -2.3541   -2.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.6156   -2.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309    0.9156   -2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    0.9443   -1.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490   -0.4675    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3821    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3795   -1.9847   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -2.5528    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.6389    2.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484    2.2311    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876    2.9938    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8379    1.4254    1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054    2.3026   -2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  8  2  1  0
 27 11  1  0
 12  2  1  0
 27 16  1  0
 24 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  6
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  6
 12 46  1  1
 13 47  1  0
 13 48  1  0
 14 49  1  1
 15 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  1
 20 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 28 62  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4   14                                                       
CONECT    4    3   17                                                       
CONECT    5    7   15                                                       
CONECT    6    8   16                                                       
CONECT    7    5   21                                                       
CONECT    8    6   23                                                       
CONECT    9   13   20                                                       
CONECT   10   14   15                                                       
CONECT   11   18   19                                                       
CONECT   12   13   28                                                       
CONECT   13    9   12   16                                                  
CONECT   14    3   10   21   29                                             
CONECT   15    5   10   24   30                                             
CONECT   16    6   13   22   31                                             
CONECT   17    4   18   23   32                                             
CONECT   18   11   17   21   33                                             
CONECT   19   11   22   25   34                                             
CONECT   20    9   26   28                                                  
CONECT   21    1    7   14   18                                             
CONECT   22    2   16   19   23                                             
CONECT   23    8   17   22   27                                             
CONECT   24   15                                                            
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27   23                                                            
CONECT   28   12   20                                                       
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   18                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

COMPND    NP0002884
HETATM    1  C1  UNL     1      -2.345  -1.905  -0.748  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.226  -0.617   0.085  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.781  -1.053   1.456  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.205  -1.528   1.335  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.057  -0.295   1.017  1.00  0.00           C  
HETATM    6  O1  UNL     1      -6.034  -0.585   0.070  1.00  0.00           O  
HETATM    7  C6  UNL     1      -4.190   0.853   0.588  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.150   0.396  -0.450  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.551   1.632  -1.022  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.263   2.049  -0.395  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.325   0.855  -0.630  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.812  -0.217   0.299  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.161  -1.350   0.290  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.303  -1.195  -0.661  1.00  0.00           C  
HETATM   15  O2  UNL     1       0.985  -1.428  -1.986  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.017   0.111  -0.569  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.778   0.328  -1.843  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.851   0.131   0.660  1.00  0.00           C  
HETATM   19  C17 UNL     1       4.212  -0.413   0.501  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.280   0.324   0.748  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.465  -0.468   0.509  1.00  0.00           C  
HETATM   22  O3  UNL     1       7.670  -0.100   0.639  1.00  0.00           O  
HETATM   23  O4  UNL     1       6.071  -1.716   0.106  1.00  0.00           O  
HETATM   24  C20 UNL     1       4.667  -1.743   0.082  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.835   1.572   1.120  1.00  0.00           C  
HETATM   26  C22 UNL     1       1.340   1.888   0.949  1.00  0.00           C  
HETATM   27  C23 UNL     1       1.072   1.281  -0.393  1.00  0.00           C  
HETATM   28  O5  UNL     1       1.355   2.296  -1.341  1.00  0.00           O  
HETATM   29  H1  UNL     1      -3.400  -1.898  -1.156  1.00  0.00           H  
HETATM   30  H2  UNL     1      -1.695  -1.899  -1.618  1.00  0.00           H  
HETATM   31  H3  UNL     1      -2.292  -2.809  -0.127  1.00  0.00           H  
HETATM   32  H4  UNL     1      -2.772  -0.208   2.171  1.00  0.00           H  
HETATM   33  H5  UNL     1      -2.115  -1.839   1.903  1.00  0.00           H  
HETATM   34  H6  UNL     1      -4.347  -2.330   0.598  1.00  0.00           H  
HETATM   35  H7  UNL     1      -4.483  -1.950   2.322  1.00  0.00           H  
HETATM   36  H8  UNL     1      -5.577   0.004   1.950  1.00  0.00           H  
HETATM   37  H9  UNL     1      -5.916  -0.092  -0.779  1.00  0.00           H  
HETATM   38  H10 UNL     1      -4.853   1.564   0.023  1.00  0.00           H  
HETATM   39  H11 UNL     1      -3.737   1.416   1.402  1.00  0.00           H  
HETATM   40  H12 UNL     1      -3.797  -0.045  -1.268  1.00  0.00           H  
HETATM   41  H13 UNL     1      -3.254   2.508  -0.935  1.00  0.00           H  
HETATM   42  H14 UNL     1      -2.369   1.525  -2.118  1.00  0.00           H  
HETATM   43  H15 UNL     1      -1.374   2.224   0.705  1.00  0.00           H  
HETATM   44  H16 UNL     1      -0.895   2.948  -0.905  1.00  0.00           H  
HETATM   45  H17 UNL     1      -0.444   0.555  -1.674  1.00  0.00           H  
HETATM   46  H18 UNL     1      -0.754   0.245   1.331  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.619  -1.540   1.307  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.320  -2.342   0.041  1.00  0.00           H  
HETATM   49  H21 UNL     1       2.055  -1.993  -0.383  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.110  -2.354  -2.271  1.00  0.00           H  
HETATM   51  H23 UNL     1       3.002  -0.616  -2.382  1.00  0.00           H  
HETATM   52  H24 UNL     1       2.131   0.916  -2.528  1.00  0.00           H  
HETATM   53  H25 UNL     1       3.666   0.944  -1.635  1.00  0.00           H  
HETATM   54  H26 UNL     1       2.349  -0.467   1.448  1.00  0.00           H  
HETATM   55  H27 UNL     1       5.291   1.382   1.086  1.00  0.00           H  
HETATM   56  H28 UNL     1       4.379  -1.985  -0.975  1.00  0.00           H  
HETATM   57  H29 UNL     1       4.351  -2.553   0.776  1.00  0.00           H  
HETATM   58  H30 UNL     1       3.136   1.639   2.170  1.00  0.00           H  
HETATM   59  H31 UNL     1       3.448   2.231   0.469  1.00  0.00           H  
HETATM   60  H32 UNL     1       1.188   2.994   0.912  1.00  0.00           H  
HETATM   61  H33 UNL     1       0.838   1.425   1.792  1.00  0.00           H  
HETATM   62  H34 UNL     1       0.705   2.303  -2.068  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    8   12
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6    7   36
CONECT    6   37
CONECT    7    8   38   39
CONECT    8    9   40
CONECT    9   10   41   42
CONECT   10   11   43   44
CONECT   11   12   27   45
CONECT   12   13   46
CONECT   13   14   47   48
CONECT   14   15   16   49
CONECT   15   50
CONECT   16   17   18   27
CONECT   17   51   52   53
CONECT   18   19   25   54
CONECT   19   20   20   24
CONECT   20   21   55
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   56   57
CONECT   25   26   58   59
CONECT   26   27   60   61
CONECT   27   28
CONECT   28   62
END

NP0002884
     RDKit          3D

62 66  0  0  0  0  0  0  0  0999 V2000
   -2.3451   -1.9048   -0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2259   -0.6168    0.0852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7809   -1.0533    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2054   -1.5278    1.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0573   -0.2954    1.0174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0338   -0.5852    0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895    0.8529    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1498    0.3958   -0.4499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5510    1.6322   -1.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    2.0495   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3247    0.8554   -0.6304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8118   -0.2166    0.2989 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1615   -1.3502    0.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027   -1.1949   -0.6609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9847   -1.4280   -1.9859 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    0.1113   -0.5691 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7782    0.3277   -1.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    0.1312    0.6595 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2120   -0.4134    0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2800    0.3244    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4647   -0.4681    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6700   -0.0999    0.6394 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0711   -1.7161    0.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -1.7426    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349    1.5716    1.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399    1.8882    0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0723    1.2808   -0.3925 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3547    2.2964   -1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4004   -1.8975   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6945   -1.8987   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2922   -2.8091   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -0.2079    2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1147   -1.8386    1.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474   -2.3295    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4827   -1.9503    2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5774    0.0042    1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9163   -0.0920   -0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8532    1.5641    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7374    1.4160    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971   -0.0447   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2535    2.5084   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687    1.5248   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3735    2.2236    0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947    2.9475   -0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4443    0.5548   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    0.2451    1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -1.5400    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -2.3420    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0548   -1.9926   -0.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103   -2.3541   -2.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023   -0.6156   -2.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309    0.9156   -2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    0.9443   -1.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490   -0.4675    1.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3821    1.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3795   -1.9847   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -2.5528    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    1.6389    2.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4484    2.2311    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1876    2.9938    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8379    1.4254    1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7054    2.3026   -2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 18 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
  8  2  1  0
 27 11  1  0
 12  2  1  0
 27 16  1  0
 24 19  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  6
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  6
 12 46  1  1
 13 47  1  0
 13 48  1  0
 14 49  1  1
 15 50  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  1
 20 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 28 62  1  0
M  END

View in JSmol

Synonyms

Value	Source
Lanadigenin	MeSH

Chemical Formula

C₂₃H₃₄O₅

Average Mass

390.5131 Da

Monoisotopic Mass

390.24062 Da

IUPAC Name

4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one

Traditional Name

digoxigenin

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18+,19-,21+,22+,23+/m1/s1

InChI Key

SHIBSTMRCDJXLN-KCZCNTNESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, methanol, experimental)	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
Asclepias syriaca	LOTUS Database	35616633
Digitalis purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
3-hydroxysteroid
3-beta-hydroxysteroid
12-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:42098 )
3beta-sterol (CHEBI:42098 )
14beta-hydroxy steroid (CHEBI:42098 )
12beta-hydroxy steroid (CHEBI:42098 )
Cardanolides and derivatives (LMST01120008 )

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	1.6	ALOGPS
logP	1.84	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	105.16 m³·mol⁻¹	ChemAxon
Polarizability	43.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB03671

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14728

KEGG Compound ID

Not Available

BioCyc ID

CPD-22579

BiGG ID

Not Available

Wikipedia Link

Digoxigenin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

42098

Good Scents ID

Not Available

References

General References

Schneider B, Grote M, John M, Haas A, Bramlage B, Ickenstein LM, Jahn-Hofmann K, Bauss F, Cheng W, Croasdale R, Daub K, Dill S, Hoffmann E, Lau W, Burtscher H, Ludtke JL, Metz S, Mundigl O, Neal ZC, Scheuer W, Stracke J, Herweijer H, Brinkmann U: Targeted siRNA Delivery and mRNA Knockdown Mediated by Bispecific Digoxigenin-binding Antibodies. Mol Ther Nucleic Acids. 2012 Sep 18;1:e46. doi: 10.1038/mtna.2012.39. [PubMed:23344238 ]
Li G, Li K, Lea AS, Li NL, Abdulla NE, Eltorky MA, Ferguson MR: In situ hybridization for the detection of hepatitis C virus RNA in human liver tissue. J Viral Hepat. 2013 Mar;20(3):183-92. doi: 10.1111/j.1365-2893.2012.01642.x. Epub 2012 Jul 30. [PubMed:23383657 ]
Gleizes PE, Noaillac-Depeyre J, Gas N: Labeling of basic fibroblast growth factor with digoxigenin: a nonradioactive probe for biochemical and cytological applications. Anal Biochem. 1994 Jun;219(2):360-7. doi: 10.1006/abio.1994.1277. [PubMed:8080093 ]

Showing NP-Card for Digoxigenin (NP0002884)

MOL for NP0002884 (Digoxigenin)

3D MOL for NP0002884 (Digoxigenin)

3D SDF for NP0002884 (Digoxigenin)

3D-SDF for NP0002884 (Digoxigenin)

PDB for NP0002884 (Digoxigenin)

3D PDB for NP0002884 (Digoxigenin)

SMILES for NP0002884 (Digoxigenin)

INCHI for NP0002884 (Digoxigenin)

Structure for NP0002884 (Digoxigenin)

3D Structure for NP0002884 (Digoxigenin)