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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015130

Secondary Accession Numbers

HMDB15130

Metabolite Identification

Common Name

Auranofin

Description

Auranofin is only found in individuals that have used or taken this drug. It is a organogold compound classified by the World Health Organization as an antirheumatic agent. Auranofin appears to induce heme oxygenase 1 (HO-1) mRNA. Heme oxygenase 1 is an inducible heme-degrading enzyme with anti-inflammatory properties.Exactly how auranofin works is not well understood. It may act as an inhibitor of kappab kinase and thioredoxin reductase which would lead to a decreased immune response and decreased free radical production, respectively. In patients with inflammatory arthritis, such as adult and juvenile rheumatoid arthritis, gold salts can decrease the inflammation of the joint lining. This effect can prevent destruction of bone and cartilage.

Structure

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


  Mrv1652307031705452D          

 32 32  0  0  1  0            999 V2000
    6.6365  -13.5279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3499  -13.1128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9196  -13.1128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3499  -12.2863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0634  -13.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9196  -12.2863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2062  -13.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6365  -11.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0600  -11.8746    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028  -11.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6374  -14.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042  -11.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899  -10.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899   -9.8156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753  -11.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904  -13.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773  -13.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904  -12.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9234  -14.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090  -14.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9234  -15.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7779  -13.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4924  -13.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7779  -12.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689  -10.6008    0.0000 P   0  3  0  0  0  0  0  0  0  0  0  0
    7.3602   -9.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6589  -11.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501  -10.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0702   -9.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6414   -9.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0353  -10.9932    0.0000 Au  0  5  0  0  0  0  0  0  0  0  0  0
    5.9390  -10.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  6  0  0  0
  3  6  1  0  0  0  0
  3  7  1  6  0  0  0
  4  8  1  0  0  0  0
  4  9  1  1  0  0  0
  6 10  1  1  0  0  0
  6  8  1  0  0  0  0
  1 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
  9 31  1  0  0  0  0
 27 32  1  0  0  0  0
M  CHG  2  25   1  31  -1
M  END

HMDB0015130
     RDKit          3D
Auranofin
 66 66  0  0  0  0  0  0  0  0999 V2000
    5.3714    0.1023   -2.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886    0.3501   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088   -0.1871    0.3074 P   0  0  0  0  0  4  0  0  0  0  0  0
    4.0024   -1.9681    0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -2.6313    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.6699    1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6967   -0.0135    2.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.4723   -0.8861 Au  0  0  0  0  0  2  0  0  0  0  0  0
    1.3794    1.3803   -1.0561 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    1.6107   -0.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6833    1.6225    0.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    1.8639    0.7324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3090    2.0719    2.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215    0.9278    2.9181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341    0.8226    4.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6085   -0.4124    4.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    1.7974    4.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943    0.6998    0.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1291    0.5954    0.5492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825   -0.4959    1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133   -0.5709    1.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -1.4395    1.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    0.7543   -1.3451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4335   -0.1367   -2.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862    0.2741   -2.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2528   -0.6887   -3.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484    1.5157   -3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    0.5166   -1.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7656    0.4962   -2.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.5937   -3.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.6308   -4.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -1.5980   -2.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975    0.1723   -2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125    0.8629   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7146   -0.9285   -2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998    1.4407   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.1333   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856   -2.3821   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5090   -2.2910    1.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -2.6957    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075   -3.6725    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0487   -2.1499   -0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290    0.5754    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220    1.7212    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2722    0.3697    3.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662   -1.0971    2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7823    0.2030    2.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.5831   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978    2.7821    0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970    3.0109    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.1590    2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700   -0.3862    6.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -0.5440    5.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -1.2946    4.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -0.2415    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4974   -1.6120    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6836   -0.0241    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3274   -0.1454    2.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838    1.8297   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1663   -0.1400   -4.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839   -1.5242   -3.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7611   -1.1115   -4.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288   -0.4462   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2092   -1.2082   -5.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    0.3702   -5.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -1.2290   -5.4572 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
  3  6  1  0
  6  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  7 47  1  0
 10 48  1  6
 12 49  1  6
 13 50  1  0
 13 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 18 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  6
 26 60  1  0
 26 61  1  0
 26 62  1  0
 28 63  1  1
 31 64  1  0
 31 65  1  0
 31 66  1  0
M  CHG  2   3   1   8  -1
M  END


  Mrv1652307031705452D          

 32 32  0  0  1  0            999 V2000
    6.6365  -13.5279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3499  -13.1128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9196  -13.1128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3499  -12.2863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0634  -13.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9196  -12.2863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2062  -13.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6365  -11.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0600  -11.8746    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2028  -11.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6374  -14.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042  -11.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899  -10.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4899   -9.8156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7753  -11.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904  -13.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7773  -13.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904  -12.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9234  -14.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2090  -14.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9234  -15.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7779  -13.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4924  -13.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7779  -12.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3689  -10.6008    0.0000 P   0  3  0  0  0  0  0  0  0  0  0  0
    7.3602   -9.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6589  -11.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6501  -10.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0702   -9.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6414   -9.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0353  -10.9932    0.0000 Au  0  5  0  0  0  0  0  0  0  0  0  0
    5.9390  -10.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  6  0  0  0
  3  6  1  0  0  0  0
  3  7  1  6  0  0  0
  4  8  1  0  0  0  0
  4  9  1  1  0  0  0
  6 10  1  1  0  0  0
  6  8  1  0  0  0  0
  1 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
  9 31  1  0  0  0  0
 27 32  1  0  0  0  0
M  CHG  2  25   1  31  -1
M  END
> <DATABASE_ID>
HMDB0015130

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[P+](CC)(CC)[Au-]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1

> <INCHI_KEY>
AUJRCFUBUPVWSZ-XTZHGVARSA-M

> <FORMULA>
C20H34AuO9PS

> <MOLECULAR_WEIGHT>
678.48

> <EXACT_MASS>
678.132685

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.82389447493229

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-lambda5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
-1.0202999999999993

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.267856439255475

> <JCHEM_POLAR_SURFACE_AREA>
114.43

> <JCHEM_REFRACTIVITY>
114.88500000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-lambda5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015130
     RDKit          3D
Auranofin
 66 66  0  0  0  0  0  0  0  0999 V2000
    5.3714    0.1023   -2.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886    0.3501   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088   -0.1871    0.3074 P   0  0  0  0  0  4  0  0  0  0  0  0
    4.0024   -1.9681    0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -2.6313    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.6699    1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6967   -0.0135    2.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.4723   -0.8861 Au  0  0  0  0  0  2  0  0  0  0  0  0
    1.3794    1.3803   -1.0561 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    1.6107   -0.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6833    1.6225    0.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    1.8639    0.7324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3090    2.0719    2.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215    0.9278    2.9181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341    0.8226    4.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6085   -0.4124    4.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    1.7974    4.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943    0.6998    0.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1291    0.5954    0.5492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825   -0.4959    1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133   -0.5709    1.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -1.4395    1.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    0.7543   -1.3451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4335   -0.1367   -2.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862    0.2741   -2.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2528   -0.6887   -3.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484    1.5157   -3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    0.5166   -1.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7656    0.4962   -2.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.5937   -3.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.6308   -4.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -1.5980   -2.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975    0.1723   -2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125    0.8629   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7146   -0.9285   -2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998    1.4407   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.1333   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856   -2.3821   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5090   -2.2910    1.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -2.6957    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075   -3.6725    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0487   -2.1499   -0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290    0.5754    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220    1.7212    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2722    0.3697    3.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662   -1.0971    2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7823    0.2030    2.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.5831   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978    2.7821    0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970    3.0109    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.1590    2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700   -0.3862    6.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -0.5440    5.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -1.2946    4.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -0.2415    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4974   -1.6120    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6836   -0.0241    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3274   -0.1454    2.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838    1.8297   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1663   -0.1400   -4.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839   -1.5242   -3.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7611   -1.1115   -4.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288   -0.4462   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2092   -1.2082   -5.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    0.3702   -5.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -1.2290   -5.4572 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
  3  6  1  0
  6  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  7 47  1  0
 10 48  1  6
 12 49  1  6
 13 50  1  0
 13 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 18 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  6
 26 60  1  0
 26 61  1  0
 26 62  1  0
 28 63  1  1
 31 64  1  0
 31 65  1  0
 31 66  1  0
M  CHG  2   3   1   8  -1
M  END

HEADER    PROTEIN                                 03-JUL-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUL-17         0                                  
HETATM    1  C   UNK     0      12.388 -25.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.720 -24.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.050 -24.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.720 -22.934   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.052 -25.252   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.050 -22.934   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.718 -25.252   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.388 -22.172   0.000  0.00  0.00           O+0
HETATM    9  S   UNK     0      15.045 -22.166   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0       9.712 -22.172   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.390 -26.792   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.715 -20.632   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.381 -19.862   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.381 -18.322   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.047 -20.632   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.382 -24.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.051 -25.261   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.382 -22.946   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.057 -27.563   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.723 -26.793   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.057 -29.103   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.385 -24.482   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.719 -25.252   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.385 -22.942   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      13.755 -19.788   0.000  0.00  0.00           P+1
HETATM   26  C   UNK     0      13.739 -18.248   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.430 -20.572   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.414 -19.032   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.064 -17.464   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.397 -17.493   0.000  0.00  0.00           C+0
HETATM   31 Au   UNK     0      14.999 -20.521   0.000  0.00  0.00          Au-1
HETATM   32  C   UNK     0      11.086 -19.827   0.000  0.00  0.00           C+0
CONECT    1    2    3   11                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7                                                  
CONECT    4    2    8    9                                                  
CONECT    5    2   22                                                       
CONECT    6    3   10    8                                                  
CONECT    7    3   16                                                       
CONECT    8    4    6                                                       
CONECT    9    4   31                                                       
CONECT   10    6   12                                                       
CONECT   11    1   19                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    7   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    5   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   26   27   28   31                                             
CONECT   26   25   29                                                       
CONECT   27   25   32                                                       
CONECT   28   25   30                                                       
CONECT   29   26                                                            
CONECT   30   28                                                            
CONECT   31   25    9                                                       
CONECT   32   27                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

COMPND    HMDB0015130
HETATM    1  C1  UNL     1       5.371   0.102  -2.077  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.589   0.350  -0.579  1.00  0.00           C  
HETATM    3  P1  UNL     1       4.109  -0.187   0.307  1.00  0.00           P1+
HETATM    4  C3  UNL     1       4.002  -1.968   0.483  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.364  -2.631   0.443  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.915   0.670   1.891  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.697  -0.014   2.990  1.00  0.00           C  
HETATM    8 AU1  UNL     1       2.492   0.472  -0.886  1.00  0.00          AU1-
HETATM    9  S1  UNL     1       1.379   1.380  -1.056  1.00  0.00           S  
HETATM   10  C7  UNL     1      -0.397   1.611  -0.836  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.683   1.623   0.513  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.059   1.864   0.732  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.309   2.072   2.205  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.922   0.928   2.918  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.034   0.823   4.295  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.608  -0.412   4.998  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.507   1.797   4.951  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.794   0.700   0.167  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.129   0.595   0.549  1.00  0.00           O  
HETATM   20  C13 UNL     1      -4.682  -0.496   1.210  1.00  0.00           C  
HETATM   21  C14 UNL     1      -6.113  -0.571   1.602  1.00  0.00           C  
HETATM   22  O5  UNL     1      -3.878  -1.440   1.463  1.00  0.00           O  
HETATM   23  C15 UNL     1      -2.614   0.754  -1.345  1.00  0.00           C  
HETATM   24  O6  UNL     1      -3.433  -0.137  -2.027  1.00  0.00           O  
HETATM   25  C16 UNL     1      -4.386   0.274  -2.980  1.00  0.00           C  
HETATM   26  C17 UNL     1      -5.253  -0.689  -3.699  1.00  0.00           C  
HETATM   27  O7  UNL     1      -4.448   1.516  -3.176  1.00  0.00           O  
HETATM   28  C18 UNL     1      -1.128   0.517  -1.579  1.00  0.00           C  
HETATM   29  O8  UNL     1      -0.766   0.496  -2.920  1.00  0.00           O  
HETATM   30  C19 UNL     1      -0.135  -0.594  -3.498  1.00  0.00           C  
HETATM   31  C20 UNL     1       0.255  -0.631  -4.919  1.00  0.00           C  
HETATM   32  O9  UNL     1       0.119  -1.598  -2.786  1.00  0.00           O  
HETATM   33  H1  UNL     1       4.297   0.172  -2.335  1.00  0.00           H  
HETATM   34  H2  UNL     1       5.912   0.863  -2.682  1.00  0.00           H  
HETATM   35  H3  UNL     1       5.715  -0.929  -2.327  1.00  0.00           H  
HETATM   36  H4  UNL     1       5.700   1.441  -0.446  1.00  0.00           H  
HETATM   37  H5  UNL     1       6.508  -0.133  -0.236  1.00  0.00           H  
HETATM   38  H6  UNL     1       3.386  -2.382  -0.348  1.00  0.00           H  
HETATM   39  H7  UNL     1       3.509  -2.291   1.435  1.00  0.00           H  
HETATM   40  H8  UNL     1       5.800  -2.696   1.450  1.00  0.00           H  
HETATM   41  H9  UNL     1       5.207  -3.673   0.067  1.00  0.00           H  
HETATM   42  H10 UNL     1       6.049  -2.150  -0.273  1.00  0.00           H  
HETATM   43  H11 UNL     1       2.829   0.575   2.171  1.00  0.00           H  
HETATM   44  H12 UNL     1       4.222   1.721   1.804  1.00  0.00           H  
HETATM   45  H13 UNL     1       4.272   0.370   3.959  1.00  0.00           H  
HETATM   46  H14 UNL     1       4.566  -1.097   2.980  1.00  0.00           H  
HETATM   47  H15 UNL     1       5.782   0.203   2.928  1.00  0.00           H  
HETATM   48  H16 UNL     1      -0.682   2.583  -1.323  1.00  0.00           H  
HETATM   49  H17 UNL     1      -2.298   2.782   0.156  1.00  0.00           H  
HETATM   50  H18 UNL     1      -1.897   3.011   2.580  1.00  0.00           H  
HETATM   51  H19 UNL     1      -3.430   2.159   2.314  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.970  -0.386   6.043  1.00  0.00           H  
HETATM   53  H21 UNL     1      -0.523  -0.544   5.006  1.00  0.00           H  
HETATM   54  H22 UNL     1      -2.122  -1.295   4.526  1.00  0.00           H  
HETATM   55  H23 UNL     1      -2.273  -0.242   0.489  1.00  0.00           H  
HETATM   56  H24 UNL     1      -6.497  -1.612   1.585  1.00  0.00           H  
HETATM   57  H25 UNL     1      -6.684  -0.024   0.800  1.00  0.00           H  
HETATM   58  H26 UNL     1      -6.327  -0.145   2.583  1.00  0.00           H  
HETATM   59  H27 UNL     1      -2.784   1.830  -1.626  1.00  0.00           H  
HETATM   60  H28 UNL     1      -6.166  -0.140  -4.009  1.00  0.00           H  
HETATM   61  H29 UNL     1      -5.584  -1.524  -3.070  1.00  0.00           H  
HETATM   62  H30 UNL     1      -4.761  -1.112  -4.596  1.00  0.00           H  
HETATM   63  H31 UNL     1      -0.829  -0.446  -1.104  1.00  0.00           H  
HETATM   64  H32 UNL     1       1.209  -1.208  -5.044  1.00  0.00           H  
HETATM   65  H33 UNL     1       0.377   0.370  -5.357  1.00  0.00           H  
HETATM   66  H34 UNL     1      -0.525  -1.229  -5.457  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4    6    8
CONECT    4    5   38   39
CONECT    5   40   41   42
CONECT    6    7   43   44
CONECT    7   45   46   47
CONECT    8    9
CONECT    9   10
CONECT   10   11   28   48
CONECT   11   12
CONECT   12   13   18   49
CONECT   13   14   50   51
CONECT   14   15
CONECT   15   16   17   17
CONECT   16   52   53   54
CONECT   18   19   23   55
CONECT   19   20
CONECT   20   21   22   22
CONECT   21   56   57   58
CONECT   23   24   28   59
CONECT   24   25
CONECT   25   26   27   27
CONECT   26   60   61   62
CONECT   28   29   63
CONECT   29   30
CONECT   30   31   32   32
CONECT   31   64   65   66
END

HMDB0015130
     RDKit          3D
Auranofin
 66 66  0  0  0  0  0  0  0  0999 V2000
    5.3714    0.1023   -2.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5886    0.3501   -0.5795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088   -0.1871    0.3074 P   0  0  0  0  0  4  0  0  0  0  0  0
    4.0024   -1.9681    0.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3638   -2.6313    0.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9147    0.6699    1.8909 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6967   -0.0135    2.9904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.4723   -0.8861 Au  0  0  0  0  0  2  0  0  0  0  0  0
    1.3794    1.3803   -1.0561 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3972    1.6107   -0.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6833    1.6225    0.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0586    1.8639    0.7324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3090    2.0719    2.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9215    0.9278    2.9181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341    0.8226    4.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6085   -0.4124    4.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5072    1.7974    4.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943    0.6998    0.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1291    0.5954    0.5492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825   -0.4959    1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1133   -0.5709    1.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -1.4395    1.4633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6140    0.7543   -1.3451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4335   -0.1367   -2.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862    0.2741   -2.9797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2528   -0.6887   -3.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4484    1.5157   -3.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1275    0.5166   -1.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7656    0.4962   -2.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.5937   -3.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.6308   -4.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -1.5980   -2.7859 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2975    0.1723   -2.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125    0.8629   -2.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7146   -0.9285   -2.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998    1.4407   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5083   -0.1333   -0.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856   -2.3821   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5090   -2.2910    1.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -2.6957    1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075   -3.6725    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0487   -2.1499   -0.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8290    0.5754    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2220    1.7212    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2722    0.3697    3.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662   -1.0971    2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7823    0.2030    2.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.5831   -1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978    2.7821    0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970    3.0109    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.1590    2.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700   -0.3862    6.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5228   -0.5440    5.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1220   -1.2946    4.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2732   -0.2415    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4974   -1.6120    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6836   -0.0241    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3274   -0.1454    2.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7838    1.8297   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1663   -0.1400   -4.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5839   -1.5242   -3.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7611   -1.1115   -4.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288   -0.4462   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2092   -1.2082   -5.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3771    0.3702   -5.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5254   -1.2290   -5.4572 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
  3  6  1  0
  6  7  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28 10  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  7 47  1  0
 10 48  1  6
 12 49  1  6
 13 50  1  0
 13 51  1  0
 16 52  1  0
 16 53  1  0
 16 54  1  0
 18 55  1  1
 21 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  6
 26 60  1  0
 26 61  1  0
 26 62  1  0
 28 63  1  1
 31 64  1  0
 31 65  1  0
 31 66  1  0
M  CHG  2   3   1   8  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate	ChEBI
2,3,4,6-Tetra-O-acetyl-1-thio-beta-D-glucopyranosato-S (triethylphosphine)gold	ChEBI
Auranofina	ChEBI
Auranofine	ChEBI
Auranofinum	ChEBI
Ridaura	ChEBI
Triethylphosphine gold	ChEBI
(1-Thio-b-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate	Generator
(1-Thio-b-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetic acid	Generator
(1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetic acid	Generator
(1-Thio-β-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate	Generator
(1-Thio-β-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetic acid	Generator
2,3,4,6-Tetra-O-acetyl-1-thio-b-D-glucopyranosato-S (triethylphosphine)gold	Generator
2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranosato-S (triethylphosphine)gold	Generator
Auroafen	HMDB
Auranofin yamanouchi brand	HMDB
Crisinor	HMDB
SmithKline beecham brand OF auranofin	HMDB
Auranofin recordati brand	HMDB
Yamanouchi brand OF auranofin	HMDB
Recordati brand OF auranofin	HMDB
Ridauran	HMDB
Rubio brand OF auranofin	HMDB
SK And F D 39162	HMDB
SK And F-39162	HMDB
Auranofin robapharm brand	HMDB
Robapharm brand OF auranofin	HMDB
SK And F 39162	HMDB
Auranofin rubio brand	HMDB
SK And F39162	HMDB

Chemical Formula

C₂₀H₃₄AuO₉PS

Average Molecular Weight

678.48

Monoisotopic Molecular Weight

678.132685

IUPAC Name

[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-lambda5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

Traditional Name

[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-lambda5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

CAS Registry Number

34031-32-8

SMILES

CC[P+](CC)(CC)[Au-]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1

InChI Key

AUJRCFUBUPVWSZ-XTZHGVARSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Monosaccharide
Oxane
Carboxylic acid ester
Sulfenyl compound
Organoheterocyclic compound
Organic transition metal salt
Organic metal salt
Oxacycle
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organophosphorus compound
Organic salt
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

gold coordination entity (CHEBI:2922 )
S-glycosyl compound (CHEBI:2922 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015130)
Extracellular (HMDB: HMDB0015130)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.15 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.99	ALOGPS
logP	-1	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	114.43 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	114.88 m³·mol⁻¹	ChemAxon
Polarizability	50.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	224.9	32859911
AllCCS	[M+H-H2O]+	223.9	32859911
AllCCS	[M+NH4]+	225.9	32859911
AllCCS	[M+Na]+	226.1	32859911
AllCCS	[M-H]-	211.7	32859911
AllCCS	[M+Na-2H]-	214.0	32859911
AllCCS	[M+HCOO]-	216.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Auranofin	CC[P+](CC)(CC)[Au-]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O	3809.7	Standard polar	33892256
Auranofin	CC[P+](CC)(CC)[Au-]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O	2405.4	Standard non polar	33892256
Auranofin	CC[P+](CC)(CC)[Au-]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O	3067.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Auranofin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2112019000-4559e7286bc64db87381	2017-09-01	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 - Auranofin 10V, Positive-QTOF	splash10-00p0-1001049000-6850c6deb49e5a0a2eac	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranofin 20V, Positive-QTOF	splash10-0pi0-1203059000-fd2208a9502429fce004	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranofin 40V, Positive-QTOF	splash10-004i-3100192000-14a6acbb9c48a5b4658a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranofin 10V, Negative-QTOF	splash10-004i-4101009000-cdd4553c6e6132fb5962	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranofin 20V, Negative-QTOF	splash10-0a4i-9400001000-40e619ee51f9255dc7b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Auranofin 40V, Negative-QTOF	splash10-0a4i-9000000000-45f3856100c55f4417ca	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00995	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00995	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00995

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293650

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Auranofin

METLIN ID

Not Available

PubChem Compound

6918453

PDB ID

Not Available

ChEBI ID

2922

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

Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. [PubMed:12754408 ]
Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. [PubMed:15191400 ]
Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. [PubMed:16036347 ]
Kim IS, Jin JY, Lee IH, Park SJ: Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. Br J Pharmacol. 2004 Jun;142(4):749-55. Epub 2004 May 24. [PubMed:15159275 ]
Hafejee A, Winhoven S, Coulson IH: Jessner's lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. [PubMed:15370403 ]

Enzymes

Enzyme Details

1. Inhibitor of nuclear factor kappa-B kinase subunit beta

General function:: Involved in protein kinase activity
Specific function:: Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. Also phosphorylates NCOA3
Gene Name:: IKBKB
Uniprot ID:: O14920
Molecular weight:: 86563.2

References

Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. [PubMed:12754408 ]
Youn HS, Lee JY, Saitoh SI, Miyake K, Hwang DH: Auranofin, as an anti-rheumatic gold compound, suppresses LPS-induced homodimerization of TLR4. Biochem Biophys Res Commun. 2006 Dec 1;350(4):866-71. Epub 2006 Sep 28. [PubMed:17034761 ]

Enzyme Details

2. Peroxiredoxin-5, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Reduces hydrogen peroxide and alkyl hydroperoxides with reducing equivalents provided through the thioredoxin system. Involved in intracellular redox signaling.
Gene Name:: PRDX5
Uniprot ID:: P30044
Molecular weight:: 22026.205

References

Rigobello MP, Scutari G, Boscolo R, Bindoli A: Induction of mitochondrial permeability transition by auranofin, a gold(I)-phosphine derivative. Br J Pharmacol. 2002 Aug;136(8):1162-8. [PubMed:12163349 ]
Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. [PubMed:15191400 ]
Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. [PubMed:16036347 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gundimeda U, Schiffman JE, Gottlieb SN, Roth BI, Gopalakrishna R: Negation of the cancer-preventive actions of selenium by over-expression of protein kinase Cepsilon and selenoprotein thioredoxin reductase. Carcinogenesis. 2009 Sep;30(9):1553-61. doi: 10.1093/carcin/bgp164. Epub 2009 Jul 3. [PubMed:19578042 ]

Showing metabocard for Auranofin (HMDB0015130)

MOL for HMDB0015130 (Auranofin)

3D MOL for HMDB0015130 (Auranofin)

3D SDF for HMDB0015130 (Auranofin)

3D-SDF for HMDB0015130 (Auranofin)

PDB for HMDB0015130 (Auranofin)

3D PDB for HMDB0015130 (Auranofin)

SMILES for HMDB0015130 (Auranofin)

INCHI for HMDB0015130 (Auranofin)

Structure for HMDB0015130 (Auranofin)

3D Structure for HMDB0015130 (Auranofin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References