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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:03:35 UTC

Update Date

2021-09-26 23:10:11 UTC

HMDB ID

HMDB0255424

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nafoxidine

Description

Nafoxidine belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group. It was developed at around the same time as tamoxifen and clomifene, which are also triphenylethylene derivatives. Nafoxidine is a very strong basic compound (based on its pKa). However, it produced side effects including ichthyosis, partial hair loss, and phototoxicity of the skin in almost all patients, and this resulted in the discontinuation of its development. Nafoxidine was assessed in clinical trials in the treatment of breast cancer and was found to be effective. The drug was originally synthesized by the fertility control program at Upjohn as a postcoital contraceptive, but was subsequently repurposed for the treatment of breast cancer. Nafoxidine (INN; developmental code names U-11,000A, NSC-70735) or nafoxidine hydrochloride (USAN) is a nonsteroidal selective estrogen receptor modulator (SERM) or partial antiestrogen of the triphenylethylene group that was developed for the treatment of advanced breast cancer by Upjohn in the 1970s but was never marketed. Nafoxidine is a long-acting estrogen receptor ligand, with a nuclear retention in the range of 24 to 48 hours or more. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nafoxidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nafoxidine 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


  Mrv1652306031606162D          

 32 36  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    7.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    6.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282    7.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392    5.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  5  1  0  0  0  0
 18  6  1  0  0  0  0
 20 19  1  0  0  0  0
 22  7  2  0  0  0  0
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 24 21  2  0  0  0  0
 25 12  2  0  0  0  0
 25 13  1  0  0  0  0
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 27 15  1  0  0  0  0
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 30 17  1  0  0  0  0
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 30 19  1  0  0  0  0
 31  1  1  0  0  0  0
 31 26  1  0  0  0  0
 32 20  1  0  0  0  0
 32 25  1  0  0  0  0
M  END

HMDB0255424
     RDKit          3D
Nafoxidine
 63 67  0  0  0  0  0  0  0  0999 V2000
   -7.1575    4.4439    1.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    4.2503    2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1089    3.1718    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8249    3.0490    2.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0197    2.0095    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    1.1115    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216    1.2381    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6182    2.2757    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.2720   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180   -0.6783   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -0.7678   -0.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722   -1.8364   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -2.0478   -2.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -3.0785   -3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -3.8909   -2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -3.6996   -0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973   -2.6689   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    0.0418    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187   -0.0971    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -0.2106    1.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.2867    2.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.2506    1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888   -0.3203    1.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.2760    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.3445    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1900   -0.3056    0.2494 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449    0.8257   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0219    0.5943   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1620   -0.9032   -0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7332   -1.4208   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.1374   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368   -0.0620   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6142    5.2660    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2215    4.7140    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9306    0.8971   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2719   -0.2327   -0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3436   -0.3278   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9633   -1.6987   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.4301   -3.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -3.1972   -4.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081   -4.7078   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -4.3673   -0.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6694   -2.5838    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -0.2592    2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302   -0.3764    3.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -1.2042   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6013    0.6217   -0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -1.2835    1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1219    0.4879    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3944    1.8111   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0457    0.8449   -1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741    0.9665   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6753    1.0783   -0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5611   -1.3391   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7906   -1.1778    0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107   -1.6108   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8070   -2.3228    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567   -0.1073   -0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.0338   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  6  7  1  0
  7  8  2  0
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 11 18  2  0
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 29 30  1  0
 22 31  1  0
 31 32  2  0
  8  3  1  0
 17 12  1  0
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 18  6  1  0
 30 26  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
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 31 62  1  0
 32 63  1  0
M  END


  Mrv1652306031606162D          

 32 36  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    7.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5912    6.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282    7.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392    5.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  5  1  0  0  0  0
 18  6  1  0  0  0  0
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 22  7  2  0  0  0  0
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 23  9  2  0  0  0  0
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 25 12  2  0  0  0  0
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 26 14  2  0  0  0  0
 26 21  1  0  0  0  0
 27 15  1  0  0  0  0
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 28 16  2  0  0  0  0
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 31  1  1  0  0  0  0
 31 26  1  0  0  0  0
 32 20  1  0  0  0  0
 32 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255424

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(CCC(C3=CC=CC=C3)=C2C2=CC=C(OCCN3CCCC3)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3

> <INCHI_KEY>
JEYWNNAZDLFBFF-UHFFFAOYSA-N

> <FORMULA>
C29H31NO2

> <MOLECULAR_WEIGHT>
425.572

> <EXACT_MASS>
425.235479242

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.19019251758988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine

> <ALOGPS_LOGP>
6.36

> <JCHEM_LOGP>
6.204474978333333

> <ALOGPS_LOGS>
-5.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.954718096281882

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
141.07299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nafoxidine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0255424
     RDKit          3D
Nafoxidine
 63 67  0  0  0  0  0  0  0  0999 V2000
   -7.1575    4.4439    1.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    4.2503    2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1089    3.1718    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8249    3.0490    2.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0197    2.0095    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    1.1115    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216    1.2381    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6182    2.2757    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.2720   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180   -0.6783   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -0.7678   -0.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722   -1.8364   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -2.0478   -2.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -3.0785   -3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -3.8909   -2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -3.6996   -0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973   -2.6689   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    0.0418    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187   -0.0971    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -0.2106    1.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.2867    2.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.2506    1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888   -0.3203    1.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.2760    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.3445    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1900   -0.3056    0.2494 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449    0.8257   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0219    0.5943   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1620   -0.9032   -0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7332   -1.4208   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.1374   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368   -0.0620   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7056    3.5003    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6142    5.2660    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2215    4.7140    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716    3.7247    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    1.8800    1.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6353    2.3995    0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    0.8971   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2719   -0.2327   -0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3436   -0.3278   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9633   -1.6987   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.4301   -3.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -3.1972   -4.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081   -4.7078   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -4.3673   -0.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6694   -2.5838    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -0.2592    2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302   -0.3764    3.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -1.2042   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6013    0.6217   -0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -1.2835    1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1219    0.4879    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3944    1.8111   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0457    0.8449   -1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741    0.9665   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6753    1.0783   -0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5611   -1.3391   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7906   -1.1778    0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107   -1.6108   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8070   -2.3228    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567   -0.1073   -0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.0338   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 22 31  1  0
 31 32  2  0
  8  3  1  0
 17 12  1  0
 32 19  1  0
 18  6  1  0
 30 26  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 20 48  1  0
 21 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.334  13.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.104  12.068   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   6.160   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.173  13.082   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.073  10.924   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   1.540   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  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.334  11.550   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
CONECT    1   31                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6   17                                                       
CONECT    6    5   18                                                       
CONECT    7    3   22                                                       
CONECT    8    4   22                                                       
CONECT    9   12   23                                                       
CONECT   10   13   23                                                       
CONECT   11   15   24                                                       
CONECT   12    9   25                                                       
CONECT   13   10   25                                                       
CONECT   14   16   26                                                       
CONECT   15   11   27                                                       
CONECT   16   14   28                                                       
CONECT   17    5   30                                                       
CONECT   18    6   30                                                       
CONECT   19   20   30                                                       
CONECT   20   19   32                                                       
CONECT   21   24   26                                                       
CONECT   22    7    8   27                                                  
CONECT   23    9   10   29                                                  
CONECT   24   11   21   28                                                  
CONECT   25   12   13   32                                                  
CONECT   26   14   21   31                                                  
CONECT   27   15   22   29                                                  
CONECT   28   16   24   29                                                  
CONECT   29   23   27   28                                                  
CONECT   30   17   18   19                                                  
CONECT   31    1   26                                                       
CONECT   32   20   25                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

COMPND    HMDB0255424
HETATM    1  C1  UNL     1      -7.157   4.444   1.678  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.845   4.250   2.119  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.109   3.172   1.621  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.825   3.049   2.101  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.020   2.009   1.660  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.545   1.112   0.735  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.822   1.238   0.265  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.618   2.276   0.705  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.404   0.272  -0.669  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.518  -0.678  -1.341  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.156  -0.768  -0.764  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.272  -1.836  -1.230  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.126  -2.048  -2.582  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.313  -3.079  -3.060  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.653  -3.891  -2.200  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.784  -3.700  -0.844  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.597  -2.669  -0.378  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.688   0.042   0.182  1.00  0.00           C  
HETATM   19  C18 UNL     1      -1.319  -0.097   0.639  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.880  -0.211   1.918  1.00  0.00           C  
HETATM   21  C20 UNL     1       0.478  -0.287   2.220  1.00  0.00           C  
HETATM   22  C21 UNL     1       1.433  -0.251   1.230  1.00  0.00           C  
HETATM   23  O2  UNL     1       2.789  -0.320   1.477  1.00  0.00           O  
HETATM   24  C22 UNL     1       3.732  -0.276   0.414  1.00  0.00           C  
HETATM   25  C23 UNL     1       5.092  -0.344   1.076  1.00  0.00           C  
HETATM   26  N1  UNL     1       6.190  -0.306   0.249  1.00  0.00           N  
HETATM   27  C24 UNL     1       6.545   0.826  -0.493  1.00  0.00           C  
HETATM   28  C25 UNL     1       8.022   0.594  -0.816  1.00  0.00           C  
HETATM   29  C26 UNL     1       8.162  -0.903  -0.695  1.00  0.00           C  
HETATM   30  C27 UNL     1       6.733  -1.421  -0.396  1.00  0.00           C  
HETATM   31  C28 UNL     1       1.007  -0.137  -0.069  1.00  0.00           C  
HETATM   32  C29 UNL     1      -0.337  -0.062  -0.359  1.00  0.00           C  
HETATM   33  H1  UNL     1      -7.706   3.500   1.783  1.00  0.00           H  
HETATM   34  H2  UNL     1      -7.614   5.266   2.301  1.00  0.00           H  
HETATM   35  H3  UNL     1      -7.222   4.714   0.590  1.00  0.00           H  
HETATM   36  H4  UNL     1      -3.372   3.725   2.825  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.020   1.880   1.986  1.00  0.00           H  
HETATM   38  H6  UNL     1      -6.635   2.399   0.345  1.00  0.00           H  
HETATM   39  H7  UNL     1      -5.931   0.897  -1.461  1.00  0.00           H  
HETATM   40  H8  UNL     1      -6.272  -0.233  -0.149  1.00  0.00           H  
HETATM   41  H9  UNL     1      -4.344  -0.328  -2.405  1.00  0.00           H  
HETATM   42  H10 UNL     1      -4.963  -1.699  -1.492  1.00  0.00           H  
HETATM   43  H11 UNL     1      -2.628  -1.430  -3.303  1.00  0.00           H  
HETATM   44  H12 UNL     1      -1.236  -3.197  -4.131  1.00  0.00           H  
HETATM   45  H13 UNL     1      -0.008  -4.708  -2.541  1.00  0.00           H  
HETATM   46  H14 UNL     1      -0.243  -4.367  -0.180  1.00  0.00           H  
HETATM   47  H15 UNL     1      -1.669  -2.584   0.686  1.00  0.00           H  
HETATM   48  H16 UNL     1      -1.580  -0.259   2.716  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.830  -0.376   3.237  1.00  0.00           H  
HETATM   50  H18 UNL     1       3.590  -1.204  -0.188  1.00  0.00           H  
HETATM   51  H19 UNL     1       3.601   0.622  -0.212  1.00  0.00           H  
HETATM   52  H20 UNL     1       5.079  -1.283   1.682  1.00  0.00           H  
HETATM   53  H21 UNL     1       5.122   0.488   1.819  1.00  0.00           H  
HETATM   54  H22 UNL     1       6.394   1.811  -0.011  1.00  0.00           H  
HETATM   55  H23 UNL     1       6.046   0.845  -1.509  1.00  0.00           H  
HETATM   56  H24 UNL     1       8.274   0.966  -1.835  1.00  0.00           H  
HETATM   57  H25 UNL     1       8.675   1.078  -0.055  1.00  0.00           H  
HETATM   58  H26 UNL     1       8.561  -1.339  -1.624  1.00  0.00           H  
HETATM   59  H27 UNL     1       8.791  -1.178   0.199  1.00  0.00           H  
HETATM   60  H28 UNL     1       6.311  -1.611  -1.414  1.00  0.00           H  
HETATM   61  H29 UNL     1       6.807  -2.323   0.204  1.00  0.00           H  
HETATM   62  H30 UNL     1       1.757  -0.107  -0.866  1.00  0.00           H  
HETATM   63  H31 UNL     1      -0.589   0.034  -1.394  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   36
CONECT    5    6    6   37
CONECT    6    7   18
CONECT    7    8    8    9
CONECT    8   38
CONECT    9   10   39   40
CONECT   10   11   41   42
CONECT   11   12   18   18
CONECT   12   13   13   17
CONECT   13   14   43
CONECT   14   15   15   44
CONECT   15   16   45
CONECT   16   17   17   46
CONECT   17   47
CONECT   18   19
CONECT   19   20   20   32
CONECT   20   21   48
CONECT   21   22   22   49
CONECT   22   23   31
CONECT   23   24
CONECT   24   25   50   51
CONECT   25   26   52   53
CONECT   26   27   30
CONECT   27   28   54   55
CONECT   28   29   56   57
CONECT   29   30   58   59
CONECT   30   60   61
CONECT   31   32   32   62
CONECT   32   63
END

HMDB0255424
     RDKit          3D
Nafoxidine
 63 67  0  0  0  0  0  0  0  0999 V2000
   -7.1575    4.4439    1.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    4.2503    2.1190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1089    3.1718    1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8249    3.0490    2.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0197    2.0095    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    1.1115    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8216    1.2381    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6182    2.2757    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4043    0.2720   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5180   -0.6783   -1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564   -0.7678   -0.7638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722   -1.8364   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -2.0478   -2.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131   -3.0785   -3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -3.8909   -2.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7840   -3.6996   -0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973   -2.6689   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    0.0418    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187   -0.0971    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8799   -0.2106    1.9184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4776   -0.2867    2.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -0.2506    1.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7888   -0.3203    1.4774 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -0.2760    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.3445    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1900   -0.3056    0.2494 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449    0.8257   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0219    0.5943   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1620   -0.9032   -0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7332   -1.4208   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071   -0.1374   -0.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3368   -0.0620   -0.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7056    3.5003    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6142    5.2660    2.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2215    4.7140    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716    3.7247    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    1.8800    1.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6353    2.3995    0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    0.8971   -1.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2719   -0.2327   -0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3436   -0.3278   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9633   -1.6987   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6280   -1.4301   -3.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -3.1972   -4.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0081   -4.7078   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -4.3673   -0.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6694   -2.5838    0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803   -0.2592    2.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302   -0.3764    3.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -1.2042   -0.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6013    0.6217   -0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -1.2835    1.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1219    0.4879    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3944    1.8111   -0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0457    0.8449   -1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2741    0.9665   -1.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6753    1.0783   -0.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5611   -1.3391   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7906   -1.1778    0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107   -1.6108   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8070   -2.3228    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567   -0.1073   -0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.0338   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 11 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 22 31  1  0
 31 32  2  0
  8  3  1  0
 17 12  1  0
 32 19  1  0
 18  6  1  0
 30 26  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
 20 48  1  0
 21 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hydrochloride, nafoxidine	MeSH
Nafoxidine hydrochloride	MeSH
U-11000a	ChEMBL

Chemical Formula

C₂₉H₃₁NO₂

Average Molecular Weight

425.572

Monoisotopic Molecular Weight

425.235479242

IUPAC Name

1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine

Traditional Name

nafoxidine

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(CCC(C3=CC=CC=C3)=C2C2=CC=C(OCCN3CCCC3)C=C2)=C1

InChI Identifier

InChI=1S/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3

InChI Key

JEYWNNAZDLFBFF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylnaphthalenes. Phenylnaphthalenes are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenylnaphthalene
Stilbene
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ring assembly (CHEBI:34881 )
naphthalenes (CHEBI:34881 )
benzenes (CHEBI:34881 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.36	ALOGPS
logP	6.2	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.07 m³·mol⁻¹	ChemAxon
Polarizability	50.19 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	205.981	30932474
DeepCCS	[M-H]-	203.623	30932474
DeepCCS	[M-2H]-	236.507	30932474
DeepCCS	[M+Na]+	212.074	30932474
AllCCS	[M+H]+	209.2	32859911
AllCCS	[M+H-H2O]+	206.8	32859911
AllCCS	[M+NH4]+	211.3	32859911
AllCCS	[M+Na]+	211.9	32859911
AllCCS	[M-H]-	206.6	32859911
AllCCS	[M+Na-2H]-	206.9	32859911
AllCCS	[M+HCOO]-	207.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nafoxidine	COC1=CC=C2C(CCC(C3=CC=CC=C3)=C2C2=CC=C(OCCN3CCCC3)C=C2)=C1	4844.4	Standard polar	33892256
Nafoxidine	COC1=CC=C2C(CCC(C3=CC=CC=C3)=C2C2=CC=C(OCCN3CCCC3)C=C2)=C1	3433.7	Standard non polar	33892256
Nafoxidine	COC1=CC=C2C(CCC(C3=CC=CC=C3)=C2C2=CC=C(OCCN3CCCC3)C=C2)=C1	3681.9	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 - Nafoxidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9005100000-bf42a00371c7c92f6d61	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nafoxidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nafoxidine 10V, Positive-QTOF	splash10-004i-2103900000-20d62335a037a2cecbb4	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nafoxidine 20V, Positive-QTOF	splash10-0002-9323100000-41f3b5ce93ea16447ea1	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nafoxidine 40V, Positive-QTOF	splash10-0002-9212000000-56de5f6b718fb9c79afd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nafoxidine 10V, Negative-QTOF	splash10-00di-0002900000-f87c247d1b57adee23b0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nafoxidine 20V, Negative-QTOF	splash10-00fr-3029600000-2a34647b9a72227ebc9b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nafoxidine 40V, Negative-QTOF	splash10-0201-5069000000-d8cb7647eeef6cefb87a	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14212

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nafoxidine

METLIN ID

Not Available

PubChem Compound

4416

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 Nafoxidine (HMDB0255424)

MOL for HMDB0255424 (Nafoxidine)

3D MOL for HMDB0255424 (Nafoxidine)

3D SDF for HMDB0255424 (Nafoxidine)

3D-SDF for HMDB0255424 (Nafoxidine)

PDB for HMDB0255424 (Nafoxidine)

3D PDB for HMDB0255424 (Nafoxidine)

SMILES for HMDB0255424 (Nafoxidine)

INCHI for HMDB0255424 (Nafoxidine)

Structure for HMDB0255424 (Nafoxidine)

3D Structure for HMDB0255424 (Nafoxidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra