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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:22:22 UTC

Update Date

2021-10-01 19:45:54 UTC

HMDB ID

HMDB0249669

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cardenolide

Description

Cardenolide 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. Based on a literature review a significant number of articles have been published on Cardenolide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cardenolide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cardenolide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652309112108222D          

 25 29  0  0  0  0            999 V2000
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 14 25  1  0  0  0  0
M  END

HMDB0249669
     RDKit          3D
Cardenolide
 59 63  0  0  0  0  0  0  0  0999 V2000
    2.6745   -0.9911    1.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582   -0.7301    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735   -1.8963   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445   -1.5564   -1.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165   -0.9080   -1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.3835   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.4980   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.7474    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293    1.8267    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969    0.9232   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -0.5410   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1045   -1.2518    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3212   -0.6619    1.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    0.5602    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.6734    2.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    0.5705    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931   -0.5637   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034   -1.7031   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111   -2.4831   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840   -3.6229   -1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746   -1.7662   -1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345   -0.5849   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978    1.8576   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515    2.1832   -0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    0.9527   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7953   -0.8473    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449   -2.0500    1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.3556    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -2.2799   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -2.7664   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -2.5092   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804   -0.9549   -2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6270   -0.7629   -1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868   -1.6249   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199    0.5986    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796    1.2234   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6681   -1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443    1.7222    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    2.6339   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.8711    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699    1.5838    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    1.2593   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872   -1.0003   -1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -2.3201    0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -1.4351    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -0.4940    2.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492   -1.4386    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.2161    3.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266    2.5302    1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    2.0203    2.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    0.8116    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -2.0708   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084    0.3300   -1.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8979   -0.4219    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710    1.5603   -1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341    2.6767    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5872    3.1079   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    2.4325   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.1701   -0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
  7  2  1  0
 25 10  1  0
 11  2  1  0
 25 14  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 18 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
M  END


  Mrv1652309112108222D          

 25 29  0  0  0  0            999 V2000
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249669

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4CCCCC34C)C1CCC2C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O2/c1-22-11-4-3-5-16(22)6-7-17-19-9-8-18(15-13-21(24)25-14-15)23(19,2)12-10-20(17)22/h13,16-20H,3-12,14H2,1-2H3

> <INCHI_KEY>
JIUWTCXNUNHEGP-UHFFFAOYSA-N

> <FORMULA>
C23H34O2

> <MOLECULAR_WEIGHT>
342.523

> <EXACT_MASS>
342.255880335

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.696612267437814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
5.535419149000002

> <ALOGPS_LOGS>
-6.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.215211024196978

> <JCHEM_PKA_STRONGEST_BASIC>
-6.823907973984927

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
100.51999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0249669
     RDKit          3D
Cardenolide
 59 63  0  0  0  0  0  0  0  0999 V2000
    2.6745   -0.9911    1.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582   -0.7301    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735   -1.8963   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445   -1.5564   -1.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165   -0.9080   -1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.3835   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.4980   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.7474    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293    1.8267    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969    0.9232   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -0.5410   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1045   -1.2518    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3212   -0.6619    1.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    0.5602    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.6734    2.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    0.5705    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931   -0.5637   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034   -1.7031   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111   -2.4831   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840   -3.6229   -1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746   -1.7662   -1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345   -0.5849   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978    1.8576   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515    2.1832   -0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    0.9527   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7953   -0.8473    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449   -2.0500    1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.3556    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -2.2799   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -2.7664   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -2.5092   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804   -0.9549   -2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6270   -0.7629   -1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868   -1.6249   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199    0.5986    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796    1.2234   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6681   -1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443    1.7222    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    2.6339   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.8711    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699    1.5838    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    1.2593   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872   -1.0003   -1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -2.3201    0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -1.4351    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -0.4940    2.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492   -1.4386    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.2161    3.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266    2.5302    1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    2.0203    2.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    0.8116    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -2.0708   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084    0.3300   -1.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8979   -0.4219    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710    1.5603   -1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341    2.6767    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5872    3.1079   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    2.4325   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.1701   -0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
  7  2  1  0
 25 10  1  0
 11  2  1  0
 25 14  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 18 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   25                                             
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19                                                       
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0249669
HETATM    1  C1  UNL     1       2.675  -0.991   1.448  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.158  -0.730   0.066  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.574  -1.896  -0.799  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.645  -1.556  -1.783  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.817  -0.908  -1.086  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.349   0.383  -0.487  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.826   0.498  -0.460  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.512   1.747   0.327  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.029   1.827   0.718  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.297   0.923  -0.202  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.674  -0.541  -0.011  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.105  -1.252   1.018  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.321  -0.662   1.586  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.893   0.560   1.035  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.818   1.673   2.083  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.268   0.570   0.480  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.793  -0.564  -0.253  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.303  -1.703  -0.666  1.00  0.00           C  
HETATM   19  C19 UNL     1      -4.311  -2.483  -1.373  1.00  0.00           C  
HETATM   20  O1  UNL     1      -4.184  -3.623  -1.901  1.00  0.00           O  
HETATM   21  O2  UNL     1      -5.475  -1.766  -1.382  1.00  0.00           O  
HETATM   22  C20 UNL     1      -5.234  -0.585  -0.721  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.298   1.858  -0.381  1.00  0.00           C  
HETATM   24  C22 UNL     1      -1.851   2.183  -0.650  1.00  0.00           C  
HETATM   25  C23 UNL     1      -1.167   0.953  -0.223  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.795  -0.847   1.463  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.545  -2.050   1.754  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.294  -0.356   2.237  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.692  -2.280  -1.391  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.909  -2.766  -0.186  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.020  -2.509  -2.215  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.280  -0.955  -2.640  1.00  0.00           H  
HETATM   33  H8  UNL     1       5.627  -0.763  -1.834  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.187  -1.625  -0.325  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.820   0.599   0.476  1.00  0.00           H  
HETATM   36  H11 UNL     1       4.680   1.223  -1.167  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.521   0.668  -1.505  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.144   1.722   1.238  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.842   2.634  -0.246  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.735   2.871   0.472  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.970   1.584   1.772  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.608   1.259  -1.245  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.387  -1.000  -1.008  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.326  -2.320   0.708  1.00  0.00           H  
HETATM   45  H20 UNL     1       0.617  -1.435   1.877  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.192  -0.494   2.725  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.149  -1.439   1.638  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.483   1.216   3.061  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.227   2.530   1.797  1.00  0.00           H  
HETATM   50  H25 UNL     1      -2.847   2.020   2.293  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.995   0.812   1.313  1.00  0.00           H  
HETATM   52  H27 UNL     1      -2.317  -2.071  -0.556  1.00  0.00           H  
HETATM   53  H28 UNL     1      -5.408   0.330  -1.360  1.00  0.00           H  
HETATM   54  H29 UNL     1      -5.898  -0.422   0.167  1.00  0.00           H  
HETATM   55  H30 UNL     1      -3.771   1.560  -1.341  1.00  0.00           H  
HETATM   56  H31 UNL     1      -3.834   2.677   0.124  1.00  0.00           H  
HETATM   57  H32 UNL     1      -1.587   3.108  -0.098  1.00  0.00           H  
HETATM   58  H33 UNL     1      -1.698   2.433  -1.732  1.00  0.00           H  
HETATM   59  H34 UNL     1      -1.473   0.170  -0.988  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    7   11
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   40   41
CONECT   10   11   25   42
CONECT   11   12   43
CONECT   12   13   44   45
CONECT   13   14   46   47
CONECT   14   15   16   25
CONECT   15   48   49   50
CONECT   16   17   23   51
CONECT   17   18   18   22
CONECT   18   19   52
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   53   54
CONECT   23   24   55   56
CONECT   24   25   57   58
CONECT   25   59
END

HMDB0249669
     RDKit          3D
Cardenolide
 59 63  0  0  0  0  0  0  0  0999 V2000
    2.6745   -0.9911    1.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582   -0.7301    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5735   -1.8963   -0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6445   -1.5564   -1.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165   -0.9080   -1.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.3835   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    0.4980   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121    1.7474    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0293    1.8267    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2969    0.9232   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -0.5410   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1045   -1.2518    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3212   -0.6619    1.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    0.5602    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.6734    2.0834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    0.5705    0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931   -0.5637   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3034   -1.7031   -0.6663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3111   -2.4831   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1840   -3.6229   -1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4746   -1.7662   -1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345   -0.5849   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2978    1.8576   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8515    2.1832   -0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1668    0.9527   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7953   -0.8473    1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449   -2.0500    1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2936   -0.3556    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -2.2799   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -2.7664   -0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -2.5092   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804   -0.9549   -2.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6270   -0.7629   -1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1868   -1.6249   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199    0.5986    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796    1.2234   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6681   -1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443    1.7222    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    2.6339   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7347    2.8711    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9699    1.5838    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6082    1.2593   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872   -1.0003   -1.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -2.3201    0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -1.4351    1.8773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -0.4940    2.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1492   -1.4386    1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    1.2161    3.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2266    2.5302    1.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8475    2.0203    2.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951    0.8116    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -2.0708   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4084    0.3300   -1.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8979   -0.4219    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7710    1.5603   -1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8341    2.6767    0.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5872    3.1079   -0.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    2.4325   -1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4733    0.1701   -0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  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
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 16 23  1  0
 23 24  1  0
 24 25  1  0
  7  2  1  0
 25 10  1  0
 11  2  1  0
 25 14  1  0
 22 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 18 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cardenolides	MeSH

Chemical Formula

C₂₃H₃₄O₂

Average Molecular Weight

342.523

Monoisotopic Molecular Weight

342.255880335

IUPAC Name

4-{2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-2,5-dihydrofuran-2-one

Traditional Name

4-{2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4CCCCC34C)C1CCC2C1=CC(=O)OC1

InChI Identifier

InChI=1S/C23H34O2/c1-22-11-4-3-5-16(22)6-7-17-19-9-8-18(15-13-21(24)25-14-15)23(19,2)12-10-20(17)22/h13,16-20H,3-12,14H2,1-2H3

InChI Key

JIUWTCXNUNHEGP-UHFFFAOYSA-N

Chemical Taxonomy

Description

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
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.02	ALOGPS
logP	5.54	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	7.22	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.52 m³·mol⁻¹	ChemAxon
Polarizability	40.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	216.651	30932474
DeepCCS	[M+Na]+	192.581	30932474
AllCCS	[M+H]+	189.1	32859911
AllCCS	[M+H-H2O]+	186.4	32859911
AllCCS	[M+NH4]+	191.6	32859911
AllCCS	[M+Na]+	192.4	32859911
AllCCS	[M-H]-	193.2	32859911
AllCCS	[M+Na-2H]-	193.7	32859911
AllCCS	[M+HCOO]-	194.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	24.1389 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.72 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3413.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	748.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	286.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	345.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	693.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	994.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1106.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1967.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	616.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2000.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	693.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	578.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	546.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	630.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cardenolide	CC12CCC3C(CCC4CCCCC34C)C1CCC2C1=CC(=O)OC1	3261.3	Standard polar	33892256
Cardenolide	CC12CCC3C(CCC4CCCCC34C)C1CCC2C1=CC(=O)OC1	2903.5	Standard non polar	33892256
Cardenolide	CC12CCC3C(CCC4CCCCC34C)C1CCC2C1=CC(=O)OC1	3232.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cardenolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-0359000000-5fdd1305126eb87bb6e2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cardenolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cardenolide 10V, Positive-QTOF	splash10-0006-0029000000-03316286812b180617a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cardenolide 20V, Positive-QTOF	splash10-0a4i-1795000000-c711e9396a34d3da2066	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cardenolide 40V, Positive-QTOF	splash10-052g-7931000000-6b988d13d633443d787a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cardenolide 10V, Negative-QTOF	splash10-0006-0009000000-65bfa238e8534a918ff3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cardenolide 20V, Negative-QTOF	splash10-0006-0019000000-e883943a7795f00e8551	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cardenolide 40V, Negative-QTOF	splash10-000l-0029000000-738f7538e52648df5c54	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00038702

Chemspider ID

11358678

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cardenolide

METLIN ID

Not Available

PubChem Compound

22340795

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Digoxin reductase

General function:: Not Available
Specific function:: Involved in the inactivation of the cardiac medication and plant natural product digoxin, thus decreasing drug efficacy and toxicity. Catalyzes the reduction of the alpha,beta-unsaturated butyrolactone ring of digoxin to the inactive metabolite dihydrodigoxin. Likely uses the cytochrome Cgr1 as the physiological electron donor, encoded by the adjacent gene in the locus. Only reduces digoxin and other cardenolide toxins, such as digitoxin, digoxigenin, ouabain and ouabagenin. Therefore is a specialized enzyme present in some gut bacteria E.lenta that protects their human host against ingested plant toxins.
Gene Name:: CGR2
Uniprot ID:: C8WLM1
Molecular weight:: 59160.825

Showing metabocard for Cardenolide (HMDB0249669)

MOL for HMDB0249669 (Cardenolide)

3D MOL for HMDB0249669 (Cardenolide)

3D SDF for HMDB0249669 (Cardenolide)

3D-SDF for HMDB0249669 (Cardenolide)

PDB for HMDB0249669 (Cardenolide)

3D PDB for HMDB0249669 (Cardenolide)

SMILES for HMDB0249669 (Cardenolide)

INCHI for HMDB0249669 (Cardenolide)

Structure for HMDB0249669 (Cardenolide)

3D Structure for HMDB0249669 (Cardenolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes