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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:44:51 UTC

Update Date

2021-09-26 23:05:31 UTC

HMDB ID

HMDB0252732

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Givinostat

Description

Givinostat belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids. Givinostat inhibits class I and class II histone deacetylases (HDACs) and several pro-inflammatory cytokines. Givinostat is a very strong basic compound (based on its pKa). In patients with polycythaemia, the reduction of mutant JAK2 concentrations by givinostat is believed to slow down the abnormal growth of erythrocytes and ameliorate the symptoms of the disease. One-fifth of patients experienced prolongation of the QT interval, a measure of electrical conduction in the heart, severe enough to warrant temporary suspension of treatment. In clinical trials of givinostat as a salvage therapy for advanced Hodgkin's lymphoma, the most common adverse reactions were fatigue (seen in 50% of participants), mild diarrhea or abdominal pain (40% of participants), moderate thrombocytopenia (decreased platelet counts, seen in one third of patients), and mild leukopenia (a decrease in white blood cell levels, seen in 30% of patients). Givinostat is in numerous phase II clinical trials (including for relapsed leukemias and myelomas), and has been granted orphan drug designation in the European Union for the treatment of systemic juvenile idiopathic arthritis, polycythaemia vera. This reduces expression of tumour necrosis factor (TNF), interleukin 1α and β, and interleukin 6. A preclinical study produced early results suggesting the molecule might help with diastolic dysfunction. It is a hydroxamate used in the form of its hydrochloride. ITF2357 was discovered at Italfarmaco of Milan, Italy. It was patented in 1997 and first described in the scientific literature in 2005. Givinostat (INN) or gavinostat (originally ITF2357) is a histone deacetylase inhibitor with potential anti-inflammatory, anti-angiogenic, and antineoplastic activities. It also has activity against cells expressing JAK2(V617F), a mutated form of the janus kinase 2 (JAK2) enzyme that is implicated in the pathophysiology of many myeloproliferative diseases, including polycythaemia vera. This compound has been identified in human blood as reported by (PMID: 31557052 ). Givinostat is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Givinostat 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


  Mrv1652310211601242D          

 31 33  0  0  0  0            999 V2000
   -7.8592    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

HMDB0252732
     RDKit          3D
Givinostat
 58 60  0  0  0  0  0  0  0  0999 V2000
   -6.8836    1.2874    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6550   -0.1854    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4484   -0.4829   -1.1041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808   -0.3109   -1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6286   -1.3330   -1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.6667   -1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257   -1.4602   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -2.5532   -0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255   -2.3488    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -1.0735    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.8396    0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0740    0.4517    1.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.6341    1.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.4771    0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6150    0.6095    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488    0.8620    2.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5921    0.4576    0.0289 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9842    0.5659    0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5913    0.9426    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9825    1.0206    1.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7957    0.7139    0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333    0.7985    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7302    1.1925    1.6766 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1142    0.4473   -0.4506 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4663    0.5326   -0.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1748    0.3333   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8159    0.2548   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166    1.5252    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    1.3200    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    0.0496   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7893   -0.2058   -0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9732    1.5190    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4676    1.5442    1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3494    1.8842   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7647   -0.5033    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5092   -0.7364    0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9405    0.7316   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2713   -0.4310   -3.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6215   -0.8511   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7371   -2.0600   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3515   -1.8820   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2130   -2.5249   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6098   -1.9522   -2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -3.5571   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152   -3.1917    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -1.6975    1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.6376    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105   -0.1790    2.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263    0.2413   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866    1.1951    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812    1.3221    2.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8003    0.1101   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9047    0.7526   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8265    0.0884   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3959   -0.0534   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.5445    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    2.1561   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    0.6277   -0.8850 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  7  1  0
 30 10  1  0
 27 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 13 47  1  0
 13 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
M  END


  Mrv1652310211601242D          

 31 33  0  0  0  0            999 V2000
   -7.8592    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
  7 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252732

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C=C3)C(=O)NO)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H27N3O4/c1-3-27(4-2)15-17-5-7-21-14-18(6-8-20(21)13-17)16-31-24(29)25-22-11-9-19(10-12-22)23(28)26-30/h5-14,30H,3-4,15-16H2,1-2H3,(H,25,29)(H,26,28)

> <INCHI_KEY>
YALNUENQHAQXEA-UHFFFAOYSA-N

> <FORMULA>
C24H27N3O4

> <MOLECULAR_WEIGHT>
421.497

> <EXACT_MASS>
421.200156361

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
47.58959374474196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{6-[(diethylamino)methyl]naphthalen-2-yl}methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
3.5119122360959274

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.056962292847402

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.988585994549252

> <JCHEM_PKA_STRONGEST_BASIC>
9.350867215805634

> <JCHEM_POLAR_SURFACE_AREA>
90.9

> <JCHEM_REFRACTIVITY>
122.49029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
givinostat

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252732
     RDKit          3D
Givinostat
 58 60  0  0  0  0  0  0  0  0999 V2000
   -6.8836    1.2874    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6550   -0.1854    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4484   -0.4829   -1.1041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808   -0.3109   -1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6286   -1.3330   -1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.6667   -1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257   -1.4602   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -2.5532   -0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255   -2.3488    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -1.0735    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.8396    0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0740    0.4517    1.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.6341    1.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.4771    0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6150    0.6095    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488    0.8620    2.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5921    0.4576    0.0289 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9842    0.5659    0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5913    0.9426    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9825    1.0206    1.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7957    0.7139    0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333    0.7985    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7302    1.1925    1.6766 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1142    0.4473   -0.4506 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4663    0.5326   -0.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1748    0.3333   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8159    0.2548   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166    1.5252    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    1.3200    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    0.0496   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7893   -0.2058   -0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9732    1.5190    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4676    1.5442    1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3494    1.8842   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7647   -0.5033    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5092   -0.7364    0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9405    0.7316   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2713   -0.4310   -3.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6215   -0.8511   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7371   -2.0600   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3515   -1.8820   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2130   -2.5249   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6098   -1.9522   -2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -3.5571   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152   -3.1917    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -1.6975    1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.6376    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105   -0.1790    2.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263    0.2413   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866    1.1951    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812    1.3221    2.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8003    0.1101   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9047    0.7526   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8265    0.0884   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3959   -0.0534   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.5445    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    2.1561   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    0.6277   -0.8850 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  7  1  0
 30 10  1  0
 27 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 13 47  1  0
 13 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
M  END

HEADER    PROTEIN                                 21-OCT-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-OCT-16         0                                  
HETATM    1  C   UNK     0     -14.670   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0     -12.003   5.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   30  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    7                                                       
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0252732
HETATM    1  C1  UNL     1      -6.884   1.287   0.491  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.655  -0.185   0.271  1.00  0.00           C  
HETATM    3  N1  UNL     1      -6.448  -0.483  -1.104  1.00  0.00           N  
HETATM    4  C3  UNL     1      -7.581  -0.311  -1.949  1.00  0.00           C  
HETATM    5  C4  UNL     1      -8.629  -1.333  -1.637  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.686  -1.667  -1.334  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.326  -1.460  -0.721  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.572  -2.553  -0.311  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.326  -2.349   0.243  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.818  -1.073   0.395  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.577  -0.840   0.945  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.074   0.452   1.095  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.271   0.634   1.699  1.00  0.00           C  
HETATM   14  O1  UNL     1       2.237   0.477   0.679  1.00  0.00           O  
HETATM   15  C13 UNL     1       3.615   0.610   1.017  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.849   0.862   2.223  1.00  0.00           O  
HETATM   17  N2  UNL     1       4.592   0.458   0.029  1.00  0.00           N  
HETATM   18  C14 UNL     1       5.984   0.566   0.229  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.591   0.943   1.398  1.00  0.00           C  
HETATM   20  C16 UNL     1       7.983   1.021   1.527  1.00  0.00           C  
HETATM   21  C17 UNL     1       8.796   0.714   0.457  1.00  0.00           C  
HETATM   22  C18 UNL     1      10.233   0.799   0.599  1.00  0.00           C  
HETATM   23  O3  UNL     1      10.730   1.193   1.677  1.00  0.00           O  
HETATM   24  N3  UNL     1      11.114   0.447  -0.451  1.00  0.00           N  
HETATM   25  O4  UNL     1      12.466   0.533  -0.302  1.00  0.00           O  
HETATM   26  C19 UNL     1       8.175   0.333  -0.724  1.00  0.00           C  
HETATM   27  C20 UNL     1       6.816   0.255  -0.857  1.00  0.00           C  
HETATM   28  C21 UNL     1      -0.817   1.525   0.691  1.00  0.00           C  
HETATM   29  C22 UNL     1      -2.051   1.320   0.142  1.00  0.00           C  
HETATM   30  C23 UNL     1      -2.549   0.050  -0.006  1.00  0.00           C  
HETATM   31  C24 UNL     1      -3.789  -0.206  -0.554  1.00  0.00           C  
HETATM   32  H1  UNL     1      -7.973   1.519   0.534  1.00  0.00           H  
HETATM   33  H2  UNL     1      -6.468   1.544   1.488  1.00  0.00           H  
HETATM   34  H3  UNL     1      -6.349   1.884  -0.256  1.00  0.00           H  
HETATM   35  H4  UNL     1      -5.765  -0.503   0.848  1.00  0.00           H  
HETATM   36  H5  UNL     1      -7.509  -0.736   0.724  1.00  0.00           H  
HETATM   37  H6  UNL     1      -7.940   0.732  -1.836  1.00  0.00           H  
HETATM   38  H7  UNL     1      -7.271  -0.431  -3.009  1.00  0.00           H  
HETATM   39  H8  UNL     1      -9.621  -0.851  -1.506  1.00  0.00           H  
HETATM   40  H9  UNL     1      -8.737  -2.060  -2.495  1.00  0.00           H  
HETATM   41  H10 UNL     1      -8.351  -1.882  -0.736  1.00  0.00           H  
HETATM   42  H11 UNL     1      -6.213  -2.525  -0.835  1.00  0.00           H  
HETATM   43  H12 UNL     1      -5.610  -1.952  -2.392  1.00  0.00           H  
HETATM   44  H13 UNL     1      -3.975  -3.557  -0.434  1.00  0.00           H  
HETATM   45  H14 UNL     1      -1.715  -3.192   0.572  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.006  -1.698   1.263  1.00  0.00           H  
HETATM   47  H16 UNL     1       1.349   1.638   2.186  1.00  0.00           H  
HETATM   48  H17 UNL     1       1.411  -0.179   2.464  1.00  0.00           H  
HETATM   49  H18 UNL     1       4.226   0.241  -0.961  1.00  0.00           H  
HETATM   50  H19 UNL     1       5.987   1.195   2.257  1.00  0.00           H  
HETATM   51  H20 UNL     1       8.381   1.322   2.467  1.00  0.00           H  
HETATM   52  H21 UNL     1      10.800   0.110  -1.378  1.00  0.00           H  
HETATM   53  H22 UNL     1      12.905   0.753  -1.168  1.00  0.00           H  
HETATM   54  H23 UNL     1       8.826   0.088  -1.580  1.00  0.00           H  
HETATM   55  H24 UNL     1       6.396  -0.053  -1.819  1.00  0.00           H  
HETATM   56  H25 UNL     1      -0.418   2.545   0.810  1.00  0.00           H  
HETATM   57  H26 UNL     1      -2.636   2.156  -0.177  1.00  0.00           H  
HETATM   58  H27 UNL     1      -4.406   0.628  -0.885  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4    6
CONECT    4    5   37   38
CONECT    5   39   40   41
CONECT    6    7   42   43
CONECT    7    8    8   31
CONECT    8    9   44
CONECT    9   10   10   45
CONECT   10   11   30
CONECT   11   12   12   46
CONECT   12   13   28
CONECT   13   14   47   48
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   49
CONECT   18   19   19   27
CONECT   19   20   50
CONECT   20   21   21   51
CONECT   21   22   26
CONECT   22   23   23   24
CONECT   24   25   52
CONECT   25   53
CONECT   26   27   27   54
CONECT   27   55
CONECT   28   29   29   56
CONECT   29   30   57
CONECT   30   31   31
CONECT   31   58
END

HMDB0252732
     RDKit          3D
Givinostat
 58 60  0  0  0  0  0  0  0  0999 V2000
   -6.8836    1.2874    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6550   -0.1854    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4484   -0.4829   -1.1041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5808   -0.3109   -1.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6286   -1.3330   -1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6858   -1.6667   -1.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3257   -1.4602   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -2.5532   -0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3255   -2.3488    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178   -1.0735    0.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.8396    0.9451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0740    0.4517    1.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.6341    1.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2370    0.4771    0.6789 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6150    0.6095    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8488    0.8620    2.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5921    0.4576    0.0289 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9842    0.5659    0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5913    0.9426    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9825    1.0206    1.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7957    0.7139    0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2333    0.7985    0.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7302    1.1925    1.6766 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1142    0.4473   -0.4506 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4663    0.5326   -0.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1748    0.3333   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8159    0.2548   -0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8166    1.5252    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0511    1.3200    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489    0.0496   -0.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7893   -0.2058   -0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9732    1.5190    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4676    1.5442    1.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3494    1.8842   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7647   -0.5033    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5092   -0.7364    0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9405    0.7316   -1.8364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2713   -0.4310   -3.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6215   -0.8511   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7371   -2.0600   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3515   -1.8820   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2130   -2.5249   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6098   -1.9522   -2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751   -3.5571   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152   -3.1917    0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0057   -1.6975    1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    1.6376    2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4105   -0.1790    2.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263    0.2413   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866    1.1951    2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3812    1.3221    2.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8003    0.1101   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9047    0.7526   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8265    0.0884   -1.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3959   -0.0534   -1.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4176    2.5445    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    2.1561   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4058    0.6277   -0.8850 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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  2  0
 12 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31  7  1  0
 30 10  1  0
 27 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
  8 44  1  0
  9 45  1  0
 11 46  1  0
 13 47  1  0
 13 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
 31 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₄H₂₇N₃O₄

Average Molecular Weight

421.497

Monoisotopic Molecular Weight

421.200156361

IUPAC Name

{6-[(diethylamino)methyl]naphthalen-2-yl}methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate

Traditional Name

givinostat

CAS Registry Number

Not Available

SMILES

CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C=C3)C(=O)NO)C=CC2=C1

InChI Identifier

InChI=1S/C24H27N3O4/c1-3-27(4-2)15-17-5-7-21-14-18(6-8-20(21)13-17)16-31-24(29)25-22-11-9-19(10-12-22)23(28)26-30/h5-14,30H,3-4,15-16H2,1-2H3,(H,25,29)(H,26,28)

InChI Key

YALNUENQHAQXEA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylcarbamic acid esters

Direct Parent

Phenylcarbamic acid esters

Alternative Parents

Substituents

Phenylcarbamic acid ester
Naphthalene
Benzoic acid or derivatives
Benzoyl
Aralkylamine
Carbamic acid ester
Amino acid or derivatives
Hydroxamic acid
Tertiary aliphatic amine
Tertiary amine
Carbonic acid derivative
Carboxylic acid derivative
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0252732)

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	4.18	ALOGPS
logP	3.51	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	9.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	122.49 m³·mol⁻¹	ChemAxon
Polarizability	47.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	206.066	30932474
DeepCCS	[M-H]-	203.708	30932474
DeepCCS	[M-2H]-	237.962	30932474
DeepCCS	[M+Na]+	213.909	30932474
AllCCS	[M+H]+	204.3	32859911
AllCCS	[M+H-H2O]+	201.9	32859911
AllCCS	[M+NH4]+	206.5	32859911
AllCCS	[M+Na]+	207.1	32859911
AllCCS	[M-H]-	201.6	32859911
AllCCS	[M+Na-2H]-	202.1	32859911
AllCCS	[M+HCOO]-	202.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.233 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.53 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1510.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	178.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	341.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	413.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	252.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	646.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	403.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1260.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	274.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	60.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Givinostat	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C=C3)C(=O)NO)C=CC2=C1	4926.9	Standard polar	33892256
Givinostat	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C=C3)C(=O)NO)C=CC2=C1	3597.6	Standard non polar	33892256
Givinostat	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C=C3)C(=O)NO)C=CC2=C1	4088.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Givinostat,1TMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)NO)C=C3)[Si](C)(C)C)C=CC2=C1	3926.4	Semi standard non polar	33892256
Givinostat,1TMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)NO)C=C3)[Si](C)(C)C)C=CC2=C1	3717.2	Standard non polar	33892256
Givinostat,1TMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)NO)C=C3)[Si](C)(C)C)C=CC2=C1	4822.3	Standard polar	33892256
Givinostat,1TMS,isomer #2	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C(=O)N(O)[Si](C)(C)C)C=C3)C=CC2=C1	3979.0	Semi standard non polar	33892256
Givinostat,1TMS,isomer #2	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C(=O)N(O)[Si](C)(C)C)C=C3)C=CC2=C1	3749.3	Standard non polar	33892256
Givinostat,1TMS,isomer #2	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C(=O)N(O)[Si](C)(C)C)C=C3)C=CC2=C1	5009.8	Standard polar	33892256
Givinostat,2TMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)N(O)[Si](C)(C)C)C=C3)[Si](C)(C)C)C=CC2=C1	3749.8	Semi standard non polar	33892256
Givinostat,2TMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)N(O)[Si](C)(C)C)C=C3)[Si](C)(C)C)C=CC2=C1	3546.0	Standard non polar	33892256
Givinostat,2TMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)N(O)[Si](C)(C)C)C=C3)[Si](C)(C)C)C=CC2=C1	4581.5	Standard polar	33892256
Givinostat,1TBDMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)NO)C=C3)[Si](C)(C)C(C)(C)C)C=CC2=C1	4189.6	Semi standard non polar	33892256
Givinostat,1TBDMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)NO)C=C3)[Si](C)(C)C(C)(C)C)C=CC2=C1	3897.9	Standard non polar	33892256
Givinostat,1TBDMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)NO)C=C3)[Si](C)(C)C(C)(C)C)C=CC2=C1	4797.1	Standard polar	33892256
Givinostat,1TBDMS,isomer #2	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C(=O)N(O)[Si](C)(C)C(C)(C)C)C=C3)C=CC2=C1	4240.4	Semi standard non polar	33892256
Givinostat,1TBDMS,isomer #2	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C(=O)N(O)[Si](C)(C)C(C)(C)C)C=C3)C=CC2=C1	3920.9	Standard non polar	33892256
Givinostat,1TBDMS,isomer #2	CCN(CC)CC1=CC=C2C=C(COC(=O)NC3=CC=C(C(=O)N(O)[Si](C)(C)C(C)(C)C)C=C3)C=CC2=C1	4983.0	Standard polar	33892256
Givinostat,2TBDMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)N(O)[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C=CC2=C1	4253.9	Semi standard non polar	33892256
Givinostat,2TBDMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)N(O)[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C=CC2=C1	3885.1	Standard non polar	33892256
Givinostat,2TBDMS,isomer #1	CCN(CC)CC1=CC=C2C=C(COC(=O)N(C3=CC=C(C(=O)N(O)[Si](C)(C)C(C)(C)C)C=C3)[Si](C)(C)C(C)(C)C)C=CC2=C1	4624.9	Standard polar	33892256

Spectra

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

DB12645

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Givinostat

METLIN ID

Not Available

PubChem Compound

9804992

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 Givinostat (HMDB0252732)

MOL for HMDB0252732 (Givinostat)

3D MOL for HMDB0252732 (Givinostat)

3D SDF for HMDB0252732 (Givinostat)

3D-SDF for HMDB0252732 (Givinostat)

PDB for HMDB0252732 (Givinostat)

3D PDB for HMDB0252732 (Givinostat)

SMILES for HMDB0252732 (Givinostat)

INCHI for HMDB0252732 (Givinostat)

Structure for HMDB0252732 (Givinostat)

3D Structure for HMDB0252732 (Givinostat)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized