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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:56:35 UTC

Update Date

2021-09-26 23:00:19 UTC

HMDB ID

HMDB0249432

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bufotalin

Description

Bufotaline 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 Bufotaline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bufotalin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bufotalin 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


  Mrv1533004161502222D          

 32 36  0  0  0  0            999 V2000
    1.1419   -0.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   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
    4.4247   -3.1470    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
    3.5330   -3.2587    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
    2.5619   -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 O   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 C   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  2  0  0  0  0
  2  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
  7  8  1  0  0  0  0
  7  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
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END

HMDB0249432
     RDKit          3D
Bufotalin
 68 72  0  0  0  0  0  0  0  0999 V2000
    5.3193    3.4554    1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    2.7349    1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    2.7741    2.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4242    2.0252    0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1936    1.3403    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1308    1.8506   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2249    0.6687   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    0.9173   -1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    0.3442    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    1.4801    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    1.6843    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    0.4117   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815    0.5559    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378   -0.6893    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7585   -0.5771   -0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9001   -1.9540   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4207   -1.9869   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881   -0.7911    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464   -0.8637    2.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -0.9267    0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -1.7318   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6658   -1.8069   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -0.4412   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655   -0.4587   -2.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095   -0.1161    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660   -0.5197   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529   -1.5384    0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -1.8814    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2444   -1.2093   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4295   -1.5058   -1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -0.2535   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3538    0.1024   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    3.3838    0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0035    3.0639    2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    4.5385    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    1.5056    1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    2.0541   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423    2.7707   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    1.7303   -2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    0.2601    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    1.2298    2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8925    2.4364    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3095    2.3794    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394    2.2174   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815    0.1876   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9042    1.2624    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886    1.1524   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8678   -0.7332    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2420   -1.4224   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -2.7597    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3005   -2.3081   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -2.9224    0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -1.9749   -1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -1.0021    2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8828   -1.7758    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094    0.0163    2.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205   -1.5907    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -2.7903   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -1.3294   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -2.0513    0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1075   -2.5965   -1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -1.0017   -2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529   -1.0735   -2.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875    0.5403   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559   -0.6910    1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8276   -2.0424    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561   -2.6716    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    0.9147   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
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 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 25  5  1  0
 32 26  2  0
 23  7  1  0
 20  9  1  0
 18 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
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 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 27 66  1  0
 28 67  1  0
 32 68  1  0
M  END


  Mrv1533004161502222D          

 32 36  0  0  0  0            999 V2000
    1.1419   -0.3243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5485   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   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
    4.4247   -3.1470    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
    3.5330   -3.2587    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
    2.5619   -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 O   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 C   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  2  0  0  0  0
  2  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249432

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3

> <INCHI_KEY>
VOZHMAYHYHEWBW-UHFFFAOYSA-N

> <FORMULA>
C26H36O6

> <MOLECULAR_WEIGHT>
444.568

> <EXACT_MASS>
444.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.177400312813866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,11-dihydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.3363281110000003

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.296396316662538

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.073322232765726

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569540766803594

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
119.18909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bufotalin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249432
     RDKit          3D
Bufotalin
 68 72  0  0  0  0  0  0  0  0999 V2000
    5.3193    3.4554    1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    2.7349    1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    2.7741    2.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4242    2.0252    0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1936    1.3403    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1308    1.8506   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2249    0.6687   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    0.9173   -1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    0.3442    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    1.4801    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    1.6843    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    0.4117   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815    0.5559    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378   -0.6893    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7585   -0.5771   -0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9001   -1.9540   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4207   -1.9869   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881   -0.7911    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464   -0.8637    2.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -0.9267    0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -1.7318   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6658   -1.8069   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -0.4412   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655   -0.4587   -2.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095   -0.1161    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660   -0.5197   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529   -1.5384    0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -1.8814    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2444   -1.2093   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4295   -1.5058   -1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -0.2535   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3538    0.1024   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    3.3838    0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0035    3.0639    2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    4.5385    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    1.5056    1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    2.0541   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423    2.7707   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    1.7303   -2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    0.2601    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    1.2298    2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8925    2.4364    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3095    2.3794    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394    2.2174   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815    0.1876   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9042    1.2624    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886    1.1524   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8678   -0.7332    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2420   -1.4224   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -2.7597    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3005   -2.3081   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -2.9224    0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -1.9749   -1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -1.0021    2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8828   -1.7758    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094    0.0163    2.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205   -1.5907    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -2.7903   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -1.3294   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -2.0513    0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1075   -2.5965   -1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -1.0017   -2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529   -1.0735   -2.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875    0.5403   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559   -0.6910    1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8276   -2.0424    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561   -2.6716    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    0.9147   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  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  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 25  5  1  0
 32 26  2  0
 23  7  1  0
 20  9  1  0
 18 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 27 66  1  0
 28 67  1  0
 32 68  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.132  -0.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.580  -1.129   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.757  -0.136   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.947  -9.510   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    9   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    7   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    5   26                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0249432
HETATM    1  C1  UNL     1       5.319   3.455   1.244  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.029   2.735   1.390  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.456   2.774   2.506  1.00  0.00           O  
HETATM    4  O2  UNL     1       3.424   2.025   0.371  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.194   1.340   0.517  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.131   1.851  -0.392  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.225   0.669  -0.594  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.575   0.917  -1.677  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.538   0.344   0.673  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.424   1.480   1.108  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.619   1.684   0.240  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.316   0.412  -0.096  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.782   0.556   0.135  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.538  -0.689   0.338  1.00  0.00           C  
HETATM   15  O4  UNL     1      -6.759  -0.577  -0.374  1.00  0.00           O  
HETATM   16  C12 UNL     1      -4.900  -1.954  -0.061  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.421  -1.987  -0.090  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.788  -0.791   0.636  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.246  -0.864   2.070  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.301  -0.927   0.592  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.829  -1.732  -0.628  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.666  -1.807  -0.528  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.242  -0.441  -0.836  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.665  -0.459  -2.269  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.309  -0.116   0.151  1.00  0.00           C  
HETATM   26  C22 UNL     1       3.666  -0.520  -0.217  1.00  0.00           C  
HETATM   27  C23 UNL     1       4.353  -1.538   0.432  1.00  0.00           C  
HETATM   28  C24 UNL     1       5.631  -1.881   0.057  1.00  0.00           C  
HETATM   29  C25 UNL     1       6.244  -1.209  -0.976  1.00  0.00           C  
HETATM   30  O5  UNL     1       7.429  -1.506  -1.345  1.00  0.00           O  
HETATM   31  O6  UNL     1       5.571  -0.253  -1.568  1.00  0.00           O  
HETATM   32  C26 UNL     1       4.354   0.102  -1.241  1.00  0.00           C  
HETATM   33  H1  UNL     1       5.735   3.384   0.232  1.00  0.00           H  
HETATM   34  H2  UNL     1       6.004   3.064   2.025  1.00  0.00           H  
HETATM   35  H3  UNL     1       5.161   4.538   1.514  1.00  0.00           H  
HETATM   36  H4  UNL     1       1.870   1.506   1.565  1.00  0.00           H  
HETATM   37  H5  UNL     1       1.616   2.054  -1.386  1.00  0.00           H  
HETATM   38  H6  UNL     1       0.642   2.771  -0.095  1.00  0.00           H  
HETATM   39  H7  UNL     1      -0.338   1.730  -2.191  1.00  0.00           H  
HETATM   40  H8  UNL     1       0.259   0.260   1.473  1.00  0.00           H  
HETATM   41  H9  UNL     1      -1.755   1.230   2.159  1.00  0.00           H  
HETATM   42  H10 UNL     1      -0.892   2.436   1.199  1.00  0.00           H  
HETATM   43  H11 UNL     1      -3.310   2.379   0.783  1.00  0.00           H  
HETATM   44  H12 UNL     1      -2.339   2.217  -0.691  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.181   0.188  -1.196  1.00  0.00           H  
HETATM   46  H14 UNL     1      -4.904   1.262   1.009  1.00  0.00           H  
HETATM   47  H15 UNL     1      -5.189   1.152  -0.735  1.00  0.00           H  
HETATM   48  H16 UNL     1      -5.868  -0.733   1.418  1.00  0.00           H  
HETATM   49  H17 UNL     1      -7.242  -1.422  -0.189  1.00  0.00           H  
HETATM   50  H18 UNL     1      -5.243  -2.760   0.654  1.00  0.00           H  
HETATM   51  H19 UNL     1      -5.301  -2.308  -1.057  1.00  0.00           H  
HETATM   52  H20 UNL     1      -3.008  -2.922   0.385  1.00  0.00           H  
HETATM   53  H21 UNL     1      -3.072  -1.975  -1.121  1.00  0.00           H  
HETATM   54  H22 UNL     1      -2.375  -1.002   2.778  1.00  0.00           H  
HETATM   55  H23 UNL     1      -3.883  -1.776   2.271  1.00  0.00           H  
HETATM   56  H24 UNL     1      -3.809   0.016   2.397  1.00  0.00           H  
HETATM   57  H25 UNL     1      -1.020  -1.591   1.465  1.00  0.00           H  
HETATM   58  H26 UNL     1      -1.207  -2.790  -0.562  1.00  0.00           H  
HETATM   59  H27 UNL     1      -1.194  -1.329  -1.569  1.00  0.00           H  
HETATM   60  H28 UNL     1       0.909  -2.051   0.540  1.00  0.00           H  
HETATM   61  H29 UNL     1       1.108  -2.597  -1.194  1.00  0.00           H  
HETATM   62  H30 UNL     1       0.840  -1.002  -2.824  1.00  0.00           H  
HETATM   63  H31 UNL     1       2.553  -1.073  -2.417  1.00  0.00           H  
HETATM   64  H32 UNL     1       1.687   0.540  -2.751  1.00  0.00           H  
HETATM   65  H33 UNL     1       2.056  -0.691   1.094  1.00  0.00           H  
HETATM   66  H34 UNL     1       3.828  -2.042   1.243  1.00  0.00           H  
HETATM   67  H35 UNL     1       6.156  -2.672   0.565  1.00  0.00           H  
HETATM   68  H36 UNL     1       3.834   0.915  -1.774  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   25   36
CONECT    6    7   37   38
CONECT    7    8    9   23
CONECT    8   39
CONECT    9   10   20   40
CONECT   10   11   41   42
CONECT   11   12   43   44
CONECT   12   13   18   45
CONECT   13   14   46   47
CONECT   14   15   16   48
CONECT   15   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   20
CONECT   19   54   55   56
CONECT   20   21   57
CONECT   21   22   58   59
CONECT   22   23   60   61
CONECT   23   24   25
CONECT   24   62   63   64
CONECT   25   26   65
CONECT   26   27   32   32
CONECT   27   28   28   66
CONECT   28   29   67
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   68
END

HMDB0249432
     RDKit          3D
Bufotalin
 68 72  0  0  0  0  0  0  0  0999 V2000
    5.3193    3.4554    1.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    2.7349    1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    2.7741    2.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4242    2.0252    0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1936    1.3403    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1308    1.8506   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2249    0.6687   -0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    0.9173   -1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5381    0.3442    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    1.4801    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6194    1.6843    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    0.4117   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7815    0.5559    0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5378   -0.6893    0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7585   -0.5771   -0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9001   -1.9540   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4207   -1.9869   -0.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881   -0.7911    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2464   -0.8637    2.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3007   -0.9267    0.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8291   -1.7318   -0.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6658   -1.8069   -0.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -0.4412   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6655   -0.4587   -2.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3095   -0.1161    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6660   -0.5197   -0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3529   -1.5384    0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6305   -1.8814    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2444   -1.2093   -0.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4295   -1.5058   -1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -0.2535   -1.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3538    0.1024   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7350    3.3838    0.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0035    3.0639    2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    4.5385    1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8699    1.5056    1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160    2.0541   -1.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6423    2.7707   -0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3382    1.7303   -2.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2588    0.2601    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546    1.2298    2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8925    2.4364    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3095    2.3794    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394    2.2174   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815    0.1876   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9042    1.2624    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1886    1.1524   -0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8678   -0.7332    1.4182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2420   -1.4224   -0.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426   -2.7597    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3005   -2.3081   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -2.9224    0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0723   -1.9749   -1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3752   -1.0021    2.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8828   -1.7758    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094    0.0163    2.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205   -1.5907    1.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -2.7903   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -1.3294   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -2.0513    0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1075   -2.5965   -1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398   -1.0017   -2.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529   -1.0735   -2.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875    0.5403   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0559   -0.6910    1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8276   -2.0424    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1561   -2.6716    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8335    0.9147   -1.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  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  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 25  5  1  0
 32 26  2  0
 23  7  1  0
 20  9  1  0
 18 12  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 27 66  1  0
 28 67  1  0
 32 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,11-Dihydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetic acid	Generator
5,11-Dihydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0,.0,]heptadecan-13-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₆O₆

Average Molecular Weight

444.568

Monoisotopic Molecular Weight

444.251188879

IUPAC Name

5,11-dihydroxy-2,15-dimethyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate

Traditional Name

bufotalin

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3

InChI Key

VOZHMAYHYHEWBW-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
Steroid ester
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Pyranone
Pyran
Heteroaromatic compound
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
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)

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	2.84	ALOGPS
logP	2.34	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	119.19 m³·mol⁻¹	ChemAxon
Polarizability	49.18 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+H]+	208.301	30932474
DeepCCS	[M-H]-	205.943	30932474
DeepCCS	[M-2H]-	239.762	30932474
DeepCCS	[M+Na]+	214.99	30932474
AllCCS	[M+H]+	208.3	32859911
AllCCS	[M+H-H2O]+	206.3	32859911
AllCCS	[M+NH4]+	210.0	32859911
AllCCS	[M+Na]+	210.5	32859911
AllCCS	[M-H]-	201.8	32859911
AllCCS	[M+Na-2H]-	202.9	32859911
AllCCS	[M+HCOO]-	204.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bufotalin,1TMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3813.6	Semi standard non polar	33892256
Bufotalin,1TMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3553.7	Standard non polar	33892256
Bufotalin,1TMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4194.9	Standard polar	33892256
Bufotalin,1TMS,isomer #2	CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3799.8	Semi standard non polar	33892256
Bufotalin,1TMS,isomer #2	CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3579.2	Standard non polar	33892256
Bufotalin,1TMS,isomer #2	CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4239.9	Standard polar	33892256
Bufotalin,2TMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3803.6	Semi standard non polar	33892256
Bufotalin,2TMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3573.4	Standard non polar	33892256
Bufotalin,2TMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4138.2	Standard polar	33892256
Bufotalin,1TBDMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4041.1	Semi standard non polar	33892256
Bufotalin,1TBDMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3805.4	Standard non polar	33892256
Bufotalin,1TBDMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4317.0	Standard polar	33892256
Bufotalin,1TBDMS,isomer #2	CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4031.5	Semi standard non polar	33892256
Bufotalin,1TBDMS,isomer #2	CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	3829.4	Standard non polar	33892256
Bufotalin,1TBDMS,isomer #2	CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4368.5	Standard polar	33892256
Bufotalin,2TBDMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4242.6	Semi standard non polar	33892256
Bufotalin,2TBDMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4020.9	Standard non polar	33892256
Bufotalin,2TBDMS,isomer #1	CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=COC(=O)C=C1	4310.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotalin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-1349400000-1c804536bc582ccb4bc6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotalin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bufotalin 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 - Bufotalin 10V, Positive-QTOF	splash10-00kr-0009400000-ed497de159fdb9b9f1be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotalin 20V, Positive-QTOF	splash10-014r-0009200000-b0b98b6dfdc1f9437997	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotalin 40V, Positive-QTOF	splash10-066s-3905000000-725704e52c7f48a9822f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotalin 10V, Negative-QTOF	splash10-0006-1002900000-11f1a2f033ba8d5b31e9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotalin 20V, Negative-QTOF	splash10-0a4i-9002000000-0cd6ec75a5289d04d009	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bufotalin 40V, Negative-QTOF	splash10-0a4j-9242100000-c5158818168e9c3beded	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

227826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

259578

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 Bufotalin (HMDB0249432)

MOL for HMDB0249432 (Bufotalin)

3D MOL for HMDB0249432 (Bufotalin)

3D SDF for HMDB0249432 (Bufotalin)

3D-SDF for HMDB0249432 (Bufotalin)

PDB for HMDB0249432 (Bufotalin)

3D PDB for HMDB0249432 (Bufotalin)

SMILES for HMDB0249432 (Bufotalin)

INCHI for HMDB0249432 (Bufotalin)

Structure for HMDB0249432 (Bufotalin)

3D Structure for HMDB0249432 (Bufotalin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra