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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:59:44 UTC

Update Date

2021-09-26 22:58:55 UTC

HMDB ID

HMDB0248571

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Arenobufagin

Description

5-{5,11,17-trihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2H-pyran-2-one belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Based on a literature review very few articles have been published on 5-{5,11,17-trihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2H-pyran-2-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). Arenobufagin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Arenobufagin 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


  Mrv0541 02241205382D          

 30 34  0  0  0  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  2  0  0  0  0
M  END

HMDB0248571
     RDKit          3D
Arenobufagin
 62 66  0  0  0  0  0  0  0  0999 V2000
    2.6704    1.7758   -1.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2013    0.6175   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7018   -0.6178   -1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1064   -1.0001   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893   -0.0380   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.5002   -0.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1170    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959    0.8917    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.2037    1.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644   -0.7540    1.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.3311    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    0.7629   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    0.3446   -1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.7334   -2.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534    0.0028   -0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    0.3064   -1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -0.6942    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698   -2.0958    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -0.7807    0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -0.4242    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.8746   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7518    1.0352   -0.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3960   -0.0279   -1.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3874    0.2015   -2.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9764   -1.2383   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9653   -1.4187   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088   -0.0429    2.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -0.1984    2.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429    0.2076    1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5526    1.5108    1.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    1.5046   -1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6668    2.7299   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549    1.8462   -2.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803   -1.5436   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863   -0.4894   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319   -1.2825   -1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754   -1.9832   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229   -0.5370    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7826    0.1447   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    1.4026    1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    2.0334   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    1.8509    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878   -1.0375    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    0.2568    2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.7280    1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9186   -0.8741    2.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718    1.1936    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006    1.9004   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    1.1672   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -0.6990   -2.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -2.4844    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -2.7322   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521   -2.2203   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.8574    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462    1.6598    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950    2.0557   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6464   -2.4593   -0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.5103    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2790    1.0285    2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688   -1.2571    2.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130    0.5130    3.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238    2.1965    1.4890 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
  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
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  2  1  0
 29 11  1  0
 12  2  1  0
 29 17  1  0
 26 20  2  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 21 55  1  0
 22 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  0
M  END


  Mrv0541 02241205382D          

 30 34  0  0  0  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    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
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248571

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12C(CCC1(O)C1CCC3CC(O)CCC3(C)C1C(O)C2=O)C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3

> <INCHI_KEY>
JGDCRWYOMWSTFC-UHFFFAOYSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.5073

> <EXACT_MASS>
416.219888756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
44.721461808418326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{5,11,17-trihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2H-pyran-2-one

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.8163659516666661

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.043869222403902

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.05728043977221

> <JCHEM_PKA_STRONGEST_BASIC>
-1.35695541029656

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
110.59709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arenobufagin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0248571
     RDKit          3D
Arenobufagin
 62 66  0  0  0  0  0  0  0  0999 V2000
    2.6704    1.7758   -1.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2013    0.6175   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7018   -0.6178   -1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1064   -1.0001   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893   -0.0380   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.5002   -0.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1170    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959    0.8917    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.2037    1.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644   -0.7540    1.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.3311    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    0.7629   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    0.3446   -1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.7334   -2.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534    0.0028   -0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    0.3064   -1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -0.6942    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698   -2.0958    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -0.7807    0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -0.4242    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.8746   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7518    1.0352   -0.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3960   -0.0279   -1.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3874    0.2015   -2.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9764   -1.2383   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9653   -1.4187   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088   -0.0429    2.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -0.1984    2.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429    0.2076    1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5526    1.5108    1.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    1.5046   -1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6668    2.7299   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549    1.8462   -2.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803   -1.5436   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863   -0.4894   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319   -1.2825   -1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754   -1.9832   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229   -0.5370    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7826    0.1447   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    1.4026    1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    2.0334   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    1.8509    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878   -1.0375    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    0.2568    2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.7280    1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9186   -0.8741    2.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718    1.1936    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006    1.9004   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    1.1672   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -0.6990   -2.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -2.4844    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -2.7322   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521   -2.2203   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.8574    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462    1.6598    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950    2.0557   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6464   -2.4593   -0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.5103    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2790    1.0285    2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688   -1.2571    2.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130    0.5130    3.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238    2.1965    1.4890 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
  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
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  2  1  0
 29 11  1  0
 12  2  1  0
 29 17  1  0
 26 20  2  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 21 55  1  0
 22 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.574  -2.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.338  -2.435   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.815  -3.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.947  -9.510   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.311  -6.868   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6   22                                             
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2   23                                                  
CONECT   23   22                                                            
CONECT   24    3   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

COMPND    HMDB0248571
HETATM    1  C1  UNL     1       2.670   1.776  -1.334  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.201   0.618  -0.430  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.702  -0.618  -1.049  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.106  -1.000  -0.776  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.989  -0.038  -0.093  1.00  0.00           C  
HETATM    6  O1  UNL     1       5.971   0.500  -0.966  1.00  0.00           O  
HETATM    7  C6  UNL     1       4.334   1.117   0.580  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.896   0.892   0.914  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.689  -0.204   1.905  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.264  -0.754   1.794  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.408   0.331   1.230  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.745   0.763  -0.175  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.152   0.345  -1.264  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.273  -0.733  -2.041  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.553   0.003  -0.884  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.486   0.306  -1.627  1.00  0.00           O  
HETATM   17  C14 UNL     1      -1.751  -0.694   0.385  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.170  -2.096   0.351  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.119  -0.781   0.952  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.239  -0.424   0.104  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.679   0.875  -0.153  1.00  0.00           C  
HETATM   22  C19 UNL     1      -5.752   1.035  -0.986  1.00  0.00           C  
HETATM   23  C20 UNL     1      -6.396  -0.028  -1.567  1.00  0.00           C  
HETATM   24  O4  UNL     1      -7.387   0.201  -2.331  1.00  0.00           O  
HETATM   25  O5  UNL     1      -5.976  -1.238  -1.319  1.00  0.00           O  
HETATM   26  C21 UNL     1      -4.965  -1.419  -0.536  1.00  0.00           C  
HETATM   27  C22 UNL     1      -3.109  -0.043   2.299  1.00  0.00           C  
HETATM   28  C23 UNL     1      -1.616  -0.198   2.660  1.00  0.00           C  
HETATM   29  C24 UNL     1      -1.043   0.208   1.365  1.00  0.00           C  
HETATM   30  O6  UNL     1      -1.553   1.511   1.111  1.00  0.00           O  
HETATM   31  H1  UNL     1       3.580   1.505  -1.866  1.00  0.00           H  
HETATM   32  H2  UNL     1       2.667   2.730  -0.814  1.00  0.00           H  
HETATM   33  H3  UNL     1       1.855   1.846  -2.114  1.00  0.00           H  
HETATM   34  H4  UNL     1       2.080  -1.544  -0.857  1.00  0.00           H  
HETATM   35  H5  UNL     1       2.586  -0.489  -2.171  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.632  -1.282  -1.745  1.00  0.00           H  
HETATM   37  H7  UNL     1       4.175  -1.983  -0.210  1.00  0.00           H  
HETATM   38  H8  UNL     1       5.623  -0.537   0.705  1.00  0.00           H  
HETATM   39  H9  UNL     1       5.783   0.145  -1.876  1.00  0.00           H  
HETATM   40  H10 UNL     1       4.846   1.403   1.547  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.423   2.033  -0.051  1.00  0.00           H  
HETATM   42  H12 UNL     1       2.486   1.851   1.289  1.00  0.00           H  
HETATM   43  H13 UNL     1       3.388  -1.038   1.844  1.00  0.00           H  
HETATM   44  H14 UNL     1       2.859   0.257   2.924  1.00  0.00           H  
HETATM   45  H15 UNL     1       1.239  -1.728   1.360  1.00  0.00           H  
HETATM   46  H16 UNL     1       0.919  -0.874   2.864  1.00  0.00           H  
HETATM   47  H17 UNL     1       0.672   1.194   1.940  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.601   1.900  -0.135  1.00  0.00           H  
HETATM   49  H19 UNL     1      -0.264   1.167  -2.040  1.00  0.00           H  
HETATM   50  H20 UNL     1      -0.018  -0.699  -2.966  1.00  0.00           H  
HETATM   51  H21 UNL     1      -1.026  -2.484   1.366  1.00  0.00           H  
HETATM   52  H22 UNL     1      -2.011  -2.732  -0.070  1.00  0.00           H  
HETATM   53  H23 UNL     1      -0.352  -2.220  -0.351  1.00  0.00           H  
HETATM   54  H24 UNL     1      -3.315  -1.857   1.284  1.00  0.00           H  
HETATM   55  H25 UNL     1      -4.146   1.660   0.323  1.00  0.00           H  
HETATM   56  H26 UNL     1      -6.095   2.056  -1.187  1.00  0.00           H  
HETATM   57  H27 UNL     1      -4.646  -2.459  -0.356  1.00  0.00           H  
HETATM   58  H28 UNL     1      -3.757  -0.510   3.036  1.00  0.00           H  
HETATM   59  H29 UNL     1      -3.279   1.028   2.184  1.00  0.00           H  
HETATM   60  H30 UNL     1      -1.469  -1.257   2.934  1.00  0.00           H  
HETATM   61  H31 UNL     1      -1.413   0.513   3.467  1.00  0.00           H  
HETATM   62  H32 UNL     1      -0.924   2.196   1.489  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    8   12
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6    7   38
CONECT    6   39
CONECT    7    8   40   41
CONECT    8    9   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   29   47
CONECT   12   13   48
CONECT   13   14   15   49
CONECT   14   50
CONECT   15   16   16   17
CONECT   17   18   19   29
CONECT   18   51   52   53
CONECT   19   20   27   54
CONECT   20   21   26   26
CONECT   21   22   22   55
CONECT   22   23   56
CONECT   23   24   24   25
CONECT   25   26
CONECT   26   57
CONECT   27   28   58   59
CONECT   28   29   60   61
CONECT   29   30
CONECT   30   62
END

HMDB0248571
     RDKit          3D
Arenobufagin
 62 66  0  0  0  0  0  0  0  0999 V2000
    2.6704    1.7758   -1.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2013    0.6175   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7018   -0.6178   -1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1064   -1.0001   -0.7765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893   -0.0380   -0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9711    0.5002   -0.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1170    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959    0.8917    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6888   -0.2037    1.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2644   -0.7540    1.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080    0.3311    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450    0.7629   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523    0.3446   -1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.7334   -2.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534    0.0028   -0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    0.3064   -1.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509   -0.6942    0.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698   -2.0958    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186   -0.7807    0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -0.4242    0.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6789    0.8746   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7518    1.0352   -0.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3960   -0.0279   -1.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3874    0.2015   -2.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9764   -1.2383   -1.3194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9653   -1.4187   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088   -0.0429    2.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -0.1984    2.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429    0.2076    1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5526    1.5108    1.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5800    1.5046   -1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6668    2.7299   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549    1.8462   -2.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803   -1.5436   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863   -0.4894   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6319   -1.2825   -1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1754   -1.9832   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6229   -0.5370    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7826    0.1447   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8460    1.4026    1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4226    2.0334   -0.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4865    1.8509    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878   -1.0375    1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8589    0.2568    2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2386   -1.7280    1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9186   -0.8741    2.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6718    1.1936    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006    1.9004   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2644    1.1672   -2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -0.6990   -2.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264   -2.4844    1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0106   -2.7322   -0.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521   -2.2203   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -1.8574    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1462    1.6598    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950    2.0557   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6464   -2.4593   -0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.5103    3.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2790    1.0285    2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688   -1.2571    2.9345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4130    0.5130    3.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9238    2.1965    1.4890 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
  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
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
  8  2  1  0
 29 11  1  0
 12  2  1  0
 29 17  1  0
 26 20  2  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  0
 14 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 21 55  1  0
 22 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Molecular Weight

416.5073

Monoisotopic Molecular Weight

416.219888756

IUPAC Name

5-{5,11,17-trihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl}-2H-pyran-2-one

Traditional Name

arenobufagin

CAS Registry Number

Not Available

SMILES

CC12C(CCC1(O)C1CCC3CC(O)CCC3(C)C1C(O)C2=O)C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3

InChI Key

JGDCRWYOMWSTFC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-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

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
12-oxosteroid
Oxosteroid
11-hydroxysteroid
Pyranone
Pyran
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Ketone
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Cytoplasm (HMDB: HMDB0248571)
extracellular (HMDB: HMDB0248571)

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	1.72	ALOGPS
logP	1.82	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	110.6 m³·mol⁻¹	ChemAxon
Polarizability	44.72 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	235.474	30932474
DeepCCS	[M+Na]+	210.702	30932474
AllCCS	[M+H]+	201.2	32859911
AllCCS	[M+H-H2O]+	199.1	32859911
AllCCS	[M+NH4]+	203.2	32859911
AllCCS	[M+Na]+	203.8	32859911
AllCCS	[M-H]-	197.2	32859911
AllCCS	[M+Na-2H]-	197.9	32859911
AllCCS	[M+HCOO]-	198.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arenobufagin	CC12C(CCC1(O)C1CCC3CC(O)CCC3(C)C1C(O)C2=O)C1=COC(=O)C=C1	3091.4	Standard polar	33892256
Arenobufagin	CC12C(CCC1(O)C1CCC3CC(O)CCC3(C)C1C(O)C2=O)C1=COC(=O)C=C1	3190.1	Standard non polar	33892256
Arenobufagin	CC12C(CCC1(O)C1CCC3CC(O)CCC3(C)C1C(O)C2=O)C1=COC(=O)C=C1	3796.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arenobufagin,4TMS,isomer #1	CC12CCC(O[Si](C)(C)C)CC1CCC1C2C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C2(C)C(C3=COC(=O)C=C3)CCC12O[Si](C)(C)C	3676.0	Semi standard non polar	33892256
Arenobufagin,4TMS,isomer #1	CC12CCC(O[Si](C)(C)C)CC1CCC1C2C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C2(C)C(C3=COC(=O)C=C3)CCC12O[Si](C)(C)C	3547.9	Standard non polar	33892256
Arenobufagin,4TMS,isomer #1	CC12CCC(O[Si](C)(C)C)CC1CCC1C2C(O[Si](C)(C)C)=C(O[Si](C)(C)C)C2(C)C(C3=COC(=O)C=C3)CCC12O[Si](C)(C)C	3742.8	Standard polar	33892256
Arenobufagin,4TBDMS,isomer #1	CC12CCC(O[Si](C)(C)C(C)(C)C)CC1CCC1C2C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2(C)C(C3=COC(=O)C=C3)CCC12O[Si](C)(C)C(C)(C)C	4433.4	Semi standard non polar	33892256
Arenobufagin,4TBDMS,isomer #1	CC12CCC(O[Si](C)(C)C(C)(C)C)CC1CCC1C2C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2(C)C(C3=COC(=O)C=C3)CCC12O[Si](C)(C)C(C)(C)C	4348.4	Standard non polar	33892256
Arenobufagin,4TBDMS,isomer #1	CC12CCC(O[Si](C)(C)C(C)(C)C)CC1CCC1C2C(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2(C)C(C3=COC(=O)C=C3)CCC12O[Si](C)(C)C(C)(C)C	3994.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-0914000000-6b19a919f97c568c2904	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arenobufagin GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-03	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 - Arenobufagin 10V, Positive-QTOF	splash10-00l2-0009200000-ec9bea7f168e7ad8d0ea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 20V, Positive-QTOF	splash10-001j-0209000000-d99e506bdb1224c9cc5d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 40V, Positive-QTOF	splash10-015c-2409000000-571414e2629a135d205b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 10V, Negative-QTOF	splash10-014i-0005900000-13d84e9eb810c8cc56f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 20V, Negative-QTOF	splash10-00kb-1009400000-e39a1d1a31283c7dd4e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 40V, Negative-QTOF	splash10-0q2c-2009000000-851242390aab2495002a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 10V, Positive-QTOF	splash10-014j-0006900000-9112f39773da4209d0b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 20V, Positive-QTOF	splash10-00l2-0109100000-74ba32d7e2de994fdb32	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 40V, Positive-QTOF	splash10-006w-3905000000-f9b793d143d1142df64d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 10V, Negative-QTOF	splash10-014i-0000900000-9a890c6be382e03ff0e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 20V, Negative-QTOF	splash10-014i-0206900000-a7500363755fd25629ef	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arenobufagin 40V, Negative-QTOF	splash10-05ow-6595100000-0fa57da16ad9cd24787a	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

Not Available

Chemspider ID

529777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

609443

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 ]

Showing metabocard for Arenobufagin (HMDB0248571)

MOL for HMDB0248571 (Arenobufagin)

3D MOL for HMDB0248571 (Arenobufagin)

3D SDF for HMDB0248571 (Arenobufagin)

3D-SDF for HMDB0248571 (Arenobufagin)

PDB for HMDB0248571 (Arenobufagin)

3D PDB for HMDB0248571 (Arenobufagin)

SMILES for HMDB0248571 (Arenobufagin)

INCHI for HMDB0248571 (Arenobufagin)

Structure for HMDB0248571 (Arenobufagin)

3D Structure for HMDB0248571 (Arenobufagin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra