NP-MRD: Showing NP-Card for acetyldigitoxin (NP0149655)

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Record Information

Version

2.0

Created at

2022-09-02 05:34:13 UTC

Updated at

2022-09-02 05:34:13 UTC

NP-MRD ID

NP0149655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

acetyldigitoxin

Description

Acetyldigitoxin, also known as acylanid or acedoxin, belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. A cardenolide glycoside compound consisting of digitoxin having an acetyl substituent at the 3-position on the D-ribo-hexopyranosyl residue at the non-reducing end. Acetyldigitoxin is a drug which is used for fast digitalization in congestive heart failure. acetyldigitoxin is found in Digitalis grandiflora and Digitalis lanata. acetyldigitoxin was first documented in 1999 (PMID: 10202961). Acetyldigitoxin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212132D          

 61 68  0  0  0  0            999 V2000
   -1.5313    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112    0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2457   -0.8500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8168   -0.8500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8168   -1.6750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168   -0.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8168    0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023    0.3875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1023   -0.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266    0.3875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3266   -0.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3266    1.2125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3266    2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1158    2.4986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8575    2.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248    2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1374    3.3233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598    3.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0838    4.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112    1.4675    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9081    1.6810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121   -0.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6121    0.8000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5961    0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9602   -1.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6747   -0.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6747   -0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3891   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3891    0.3875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3891    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1036   -0.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8181   -1.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1036   -0.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8181    0.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2470    0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2470   -1.2625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2470   -2.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9615   -0.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6759    0.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9615   -0.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6759   -1.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3904   -0.8500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.1049   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3904   -0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1049    0.3875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1049    1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8193   -0.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.5338    0.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8193   -0.8500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.5338   -1.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2483   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9627   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2483   -0.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  8  1  0  0  0  0
  8  3  1  0  0  0  0
  3  9  1  0  0  0  0
 13 11  1  0  0  0  0
 11  9  1  0  0  0  0
  9  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 28  1  0  0  0  0
 28 15  1  0  0  0  0
 13 28  1  0  0  0  0
  6 13  1  0  0  0  0
 17  6  1  0  0  0  0
 17 18  1  0  0  0  0
 26 18  1  0  0  0  0
 18 15  1  0  0  0  0
 15  7  1  0  0  0  0
 26 30  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  1  0  0  0
  9 10  1  1  0  0  0
 11 12  1  1  0  0  0
 13 14  1  6  0  0  0
 15 16  1  1  0  0  0
 18 19  1  1  0  0  0
 26 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 21  1  0  0  0  0
 21 22  2  0  0  0  0
 24 25  2  0  0  0  0
 26 27  1  6  0  0  0
 28 29  1  1  0  0  0
 32 31  1  1  0  0  0
 34 32  1  0  0  0  0
 32 33  1  0  0  0  0
 35 39  1  0  0  0  0
 35 33  1  0  0  0  0
 39 37  1  0  0  0  0
 37 34  1  0  0  0  0
 35 36  1  1  0  0  0
 37 38  1  6  0  0  0
 39 40  1  6  0  0  0
 41 40  1  6  0  0  0
 43 41  1  0  0  0  0
 42 41  1  0  0  0  0
 42 46  1  0  0  0  0
 46 48  1  0  0  0  0
 48 44  1  0  0  0  0
 44 43  1  0  0  0  0
 44 45  1  6  0  0  0
 46 47  1  1  0  0  0
 48 49  1  1  0  0  0
 50 49  1  1  0  0  0
 51 50  1  0  0  0  0
 50 52  1  0  0  0  0
 53 55  1  0  0  0  0
 53 52  1  0  0  0  0
 55 57  1  0  0  0  0
 57 51  1  0  0  0  0
 53 54  1  1  0  0  0
 55 56  1  6  0  0  0
 57 58  1  6  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  2  0  0  0  0
M  END

     RDKit          3D

123130  0  0  0  0  0  0  0  0999 V2000
   13.2438    2.0050    0.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8623    1.4581    0.7438 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8750    1.9059    1.3690 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6364    0.4076   -0.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3655   -0.1493   -0.3108 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8248    0.0236   -1.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5643   -0.8466   -1.7902 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7289   -0.6497   -0.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4628   -0.2069   -1.0607 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3649   -1.0899   -0.5716 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6328   -2.4375   -0.6599 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -0.6434    0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2672    0.7077    0.6164 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0076    0.4082    0.1298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619    0.8108    0.9305 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9921    1.6041    0.0574 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4656    2.8565   -0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    0.7479   -1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0600   -0.5066   -0.7251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2147   -0.1402   -0.2868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009   -0.7512   -1.0801 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0673   -1.5730   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581   -0.7156    1.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5897    0.1131    0.1823 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -9.6792    1.1725    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.3436   -1.3158   -0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1949   -2.0142    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5051   -1.9518   -0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5806   -2.4995    0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3822   -1.1850   -1.2568 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0515   -0.7776   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0623   -1.6498   -1.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6192   -0.4264   -1.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7151    0.7302   -0.8525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3776    1.8133   -1.4683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3805    1.2593   -0.3898 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.3023    2.4199   -0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4799    1.2458   -0.5422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0577    0.3473   -1.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -1.1706    0.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102   -0.4602    1.3096 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.9183   -2.1937   -1.8210 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4201   -2.0305    0.7417 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6639    2.1866   -0.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2117    2.9930    1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6574    0.4200    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5748   -0.2987   -2.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1019   -0.6212   -2.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361   -0.0801   -2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1588    1.2301    1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.8299    1.9220   -0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.9433   -2.5473    1.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6710   -1.1764   -2.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 04191212132D          

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 17  6  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0149655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](OC(C)=O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1

> <INCHI_KEY>
HPMZBILYSWLILX-UMDUKNJSSA-N

> <FORMULA>
C43H66O14

> <MOLECULAR_WEIGHT>
806.9757

> <EXACT_MASS>
806.44525682

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
87.94543079481707

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,6S)-3-hydroxy-6-{[(2R,3S,4S,6S)-4-hydroxy-6-{[(2R,3S,4S,6R)-4-hydroxy-6-{[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl acetate

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
4.0386171493333345

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.05997602246958

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182635647025093

> <JCHEM_PKA_STRONGEST_BASIC>
0.24222921557030686

> <JCHEM_POLAR_SURFACE_AREA>
188.89999999999998

> <JCHEM_REFRACTIVITY>
200.86880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetyldigitoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -2.858   0.723   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.192  -0.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.858  -2.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.191  -2.357   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.143  -1.587   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.191   2.263   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.941   0.248   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.192  -1.587   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.525  -1.587   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -1.525  -3.127   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -1.525  -0.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.525   1.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.191   0.723   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      -0.191  -0.817   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       2.476   0.723   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.476  -0.817   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.143   3.033   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.476   2.263   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.476   3.803   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.816   4.664   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.467   5.496   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.340   4.227   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.856   6.203   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.405   6.718   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.890   8.147   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.941   2.739   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       5.428   3.138   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       1.143  -0.047   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.143   1.493   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       4.846   1.493   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.526  -2.357   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.859  -1.587   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.859  -0.047   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.193  -2.357   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.193   0.723   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.193   2.263   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.527  -1.587   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -10.860  -2.357   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -9.527  -0.047   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -10.860   0.723   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0     -12.194  -0.047   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -13.528   0.723   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -12.194  -1.587   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0     -13.528  -2.357   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -13.528  -3.897   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -14.861  -0.047   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -16.195   0.723   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0     -14.861  -1.587   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0     -16.195  -2.357   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0     -17.529  -1.587   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -18.862  -2.357   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -17.529  -0.047   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0     -18.862   0.723   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -18.862   2.263   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -20.196  -0.047   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -21.530   0.723   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -20.196  -1.587   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -21.530  -2.357   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0     -22.863  -1.587   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -24.197  -2.357   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -22.863  -0.047   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    8                                                       
CONECT    3    8    9                                                       
CONECT    4    9    5                                                       
CONECT    5    4   28                                                       
CONECT    6   13   17                                                       
CONECT    7   15   30                                                       
CONECT    8    2    3   31                                                  
CONECT    9    3   11    4   10                                             
CONECT   10    9                                                            
CONECT   11    1   13    9   12                                             
CONECT   12   11                                                            
CONECT   13   11   28    6   14                                             
CONECT   14   13                                                            
CONECT   15   28   18    7   16                                             
CONECT   16   15                                                            
CONECT   17    6   18                                                       
CONECT   18   17   26   15   19                                             
CONECT   19   18                                                            
CONECT   20   23   22                                                       
CONECT   21   24   22                                                       
CONECT   22   26   20   21                                                  
CONECT   23   20   24                                                       
CONECT   24   23   21   25                                                  
CONECT   25   24                                                            
CONECT   26   18   30   22   27                                             
CONECT   27   26                                                            
CONECT   28    5   15   13   29                                             
CONECT   29   28                                                            
CONECT   30   26    7                                                       
CONECT   31    8   32                                                       
CONECT   32   31   34   33                                                  
CONECT   33   32   35                                                       
CONECT   34   32   37                                                       
CONECT   35   39   33   36                                                  
CONECT   36   35                                                            
CONECT   37   39   34   38                                                  
CONECT   38   37                                                            
CONECT   39   35   37   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   43   42                                                  
CONECT   42   41   46                                                       
CONECT   43   41   44                                                       
CONECT   44   48   43   45                                                  
CONECT   45   44                                                            
CONECT   46   42   48   47                                                  
CONECT   47   46                                                            
CONECT   48   46   44   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50   57                                                       
CONECT   52   50   53                                                       
CONECT   53   55   52   54                                                  
CONECT   54   53                                                            
CONECT   55   53   57   56                                                  
CONECT   56   55                                                            
CONECT   57   55   51   58                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  136    0
END

View in JSmol

Synonyms

Value	Source
Acetildigitoxina	ChEBI
Acetyl-digitoxin-alpha	ChEBI
Acetyldiginatin	ChEBI
Acetyldigitoxinum	ChEBI
Acetylgitaloxin	ChEBI
Acetylgitoxin	ChEBI
alpha-Acetyldigitoxin	ChEBI
alpha-Acetylgitaloxin	ChEBI
alpha-Monoacetyldigitoxin	ChEBI
Desglucolanatoside a	ChEBI
Digitoxin 3'''-acetate	ChEBI
Acylanid	Kegg
Acetyl-digitoxin-a	Generator
Acetyl-digitoxin-α	Generator
a-Acetyldigitoxin	Generator
Α-acetyldigitoxin	Generator
a-Acetylgitaloxin	Generator
Α-acetylgitaloxin	Generator
a-Monoacetyldigitoxin	Generator
Α-monoacetyldigitoxin	Generator
Digitoxin 3'''-acetic acid	Generator
3'''-O-acetyldigitoxin	HMDB
Acedoxin	HMDB
Digitoxin monoacetate	HMDB
Desglucolanatosides a	HMDB
Acetyldigitoxins	HMDB
Monoacetate, digitoxin	HMDB
alpha Acetyldigitoxin	HMDB
Adicin	HMDB
Acetyldigitoxin	ChEBI

Chemical Formula

C₄₃H₆₆O₁₄

Average Mass

806.9757 Da

Monoisotopic Mass

806.44526 Da

IUPAC Name

(2R,3R,4S,6S)-3-hydroxy-6-{[(2R,3S,4S,6S)-4-hydroxy-6-{[(2R,3S,4S,6R)-4-hydroxy-6-{[(1S,2S,5S,7R,10R,11S,14R,15R)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl acetate

Traditional Name

acetyldigitoxin

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@H]3C[C@H](OC(C)=O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1

InChI Key

HPMZBILYSWLILX-UMDUKNJSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Digitalis grandiflora	LOTUS Database	35616633
Digitalis lanata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
Oligosaccharide
14-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
2-furanone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cardenolide glycoside (CHEBI:53773 )

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	2.87	ALOGPS
logP	4.04	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	188.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	200.87 m³·mol⁻¹	ChemAxon
Polarizability	87.95 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0014652

DrugBank ID

DB00511

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetyldigitoxin

METLIN ID

Not Available

PubChem Compound

5284512

PDB ID

Not Available

ChEBI ID

53773

Good Scents ID

Not Available

References

General References

Hage DS, Sengupta A: Characterisation of the binding of digitoxin and acetyldigitoxin to human serum albumin by high-performance affinity chromatography. J Chromatogr B Biomed Sci Appl. 1999 Mar 5;724(1):91-100. doi: 10.1016/s0378-4347(98)00589-1. [PubMed:10202961 ]
LOTUS database [Link]

Showing NP-Card for acetyldigitoxin (NP0149655)

MOL for NP0149655 (acetyldigitoxin)

3D MOL for NP0149655 (acetyldigitoxin)

3D SDF for NP0149655 (acetyldigitoxin)

3D-SDF for NP0149655 (acetyldigitoxin)

PDB for NP0149655 (acetyldigitoxin)

3D PDB for NP0149655 (acetyldigitoxin)

SMILES for NP0149655 (acetyldigitoxin)

INCHI for NP0149655 (acetyldigitoxin)

Structure for NP0149655 (acetyldigitoxin)

3D Structure for NP0149655 (acetyldigitoxin)