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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:13:56 UTC

Update Date

2022-03-07 02:55:08 UTC

HMDB ID

HMDB0036988

Secondary Accession Numbers

HMDB36988

Metabolite Identification

Common Name

N-Methoxycarbonyl-N-nornuciferine

Description

N-Methoxycarbonyl-N-nornuciferine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. N-Methoxycarbonyl-N-nornuciferine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, N-methoxycarbonyl-N-nornuciferine has been detected, but not quantified in, alcoholic beverages and fruits. This could make N-methoxycarbonyl-N-nornuciferine a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 02241208032D          

 25 28  0  0  0  0            999 V2000
    1.9202    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9202    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    1.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -1.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -2.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    2.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844    2.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    2.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669    2.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -2.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748   -2.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  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  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 24  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END

HMDB0036988
     RDKit          3D
N-Methoxycarbonyl-N-nornuciferine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.7199   -1.7213   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5302   -1.7743   -0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749   -0.7470   -0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    0.1726   -1.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -0.7496    0.3179 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -1.8552    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -2.5609    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901   -1.5651    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4803   -2.0659    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593   -1.2515    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.7471    0.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518   -3.1031    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.1005    0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133    0.8390   -0.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    1.3804    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0885    0.5682   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146   -0.2615    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4112    0.2755    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    1.3267   -0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    2.2626   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532    3.5605   -1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417    4.4777   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5132    4.0816   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    2.7903   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    1.9002   -0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2975   -0.8090   -0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961   -2.6395   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -1.7977   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -2.5854    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058   -1.4324    2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -3.2112   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -3.1885    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -3.1064    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -3.3293    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064   -3.7516    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763   -3.3369    1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251    1.8717    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179    0.5099    1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    2.1310    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561    0.8145    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398    1.9400   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757    0.9406   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    3.8458   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    5.4872   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    4.7565   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    2.5573   -0.6120 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17  8  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END


  Mrv0541 02241208032D          

 25 28  0  0  0  0            999 V2000
    1.9202    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9202    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    1.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241    1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    0.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -1.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -1.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -2.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    2.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844    2.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    2.6102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669    2.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -2.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0748   -2.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  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  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 24  1  0  0  0  0
 19 25  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036988

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC1=C3C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO4/c1-23-16-11-13-8-9-21(20(22)25-3)15-10-12-6-4-5-7-14(12)18(17(13)15)19(16)24-2/h4-7,11,15H,8-10H2,1-3H3

> <INCHI_KEY>
NZPPZYPCWOGFIQ-UHFFFAOYSA-N

> <FORMULA>
C20H21NO4

> <MOLECULAR_WEIGHT>
339.385

> <EXACT_MASS>
339.147058165

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.10765614089712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 15,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.2322549699999996

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.605722828485088

> <JCHEM_POLAR_SURFACE_AREA>
48

> <JCHEM_REFRACTIVITY>
94.8475

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 15,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036988
     RDKit          3D
N-Methoxycarbonyl-N-nornuciferine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.7199   -1.7213   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5302   -1.7743   -0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749   -0.7470   -0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    0.1726   -1.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -0.7496    0.3179 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -1.8552    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -2.5609    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901   -1.5651    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4803   -2.0659    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593   -1.2515    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.7471    0.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518   -3.1031    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.1005    0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133    0.8390   -0.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    1.3804    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0885    0.5682   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146   -0.2615    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4112    0.2755    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    1.3267   -0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    2.2626   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532    3.5605   -1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417    4.4777   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5132    4.0816   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    2.7903   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    1.9002   -0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2975   -0.8090   -0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961   -2.6395   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -1.7977   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -2.5854    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058   -1.4324    2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -3.2112   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -3.1885    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -3.1064    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -3.3293    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064   -3.7516    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763   -3.3369    1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251    1.8717    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179    0.5099    1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    2.1310    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561    0.8145    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398    1.9400   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757    0.9406   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    3.8458   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    5.4872   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    4.7565   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    2.5573   -0.6120 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17  8  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.584   0.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.584   1.923   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.200   2.692   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.969   1.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.415   2.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.801   1.923   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.032   2.692   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.418   1.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.418   0.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.032  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.801   0.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.415  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.969   0.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.200  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.200  -1.923   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.969  -2.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.415  -1.923   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.801  -2.693   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.969  -4.232   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.200   4.232   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.091   4.872   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.309   4.872   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.418   4.232   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.801  -3.972   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.140  -4.872   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13    4   12   14                                                  
CONECT   14    1   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   12   16   18                                                  
CONECT   18   17   24                                                       
CONECT   19   16   25                                                       
CONECT   20    3   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036988
HETATM    1  C1  UNL     1       5.720  -1.721  -1.135  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.530  -1.774  -0.342  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.575  -0.747  -0.437  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.844   0.173  -1.237  1.00  0.00           O  
HETATM    5  N1  UNL     1       2.391  -0.750   0.318  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.174  -1.855   1.225  1.00  0.00           C  
HETATM    7  C4  UNL     1       0.893  -2.561   0.842  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.190  -1.565   0.564  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.480  -2.066   0.682  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.559  -1.251   0.458  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.852  -1.747   0.577  1.00  0.00           O  
HETATM   12  C8  UNL     1      -4.052  -3.103   0.933  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.364   0.100   0.103  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.513   0.839  -0.091  1.00  0.00           O  
HETATM   15  C10 UNL     1      -4.215   1.380   1.059  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.089   0.568  -0.014  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.015  -0.261   0.222  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.411   0.276   0.238  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.664   1.327  -0.753  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.519   2.263  -0.825  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.753   3.560  -1.284  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.242   4.478  -1.488  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.513   4.082  -1.224  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.815   2.790  -0.759  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.798   1.900  -0.563  1.00  0.00           C  
HETATM   26  H1  UNL     1       6.298  -0.809  -0.939  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.296  -2.640  -0.914  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.395  -1.798  -2.195  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.992  -2.585   1.223  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.106  -1.432   2.257  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.054  -3.211  -0.020  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.595  -3.189   1.706  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.673  -3.106   0.953  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.122  -3.329   1.110  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.606  -3.752   0.133  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.476  -3.337   1.876  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.425   1.872   1.662  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.618   0.510   1.614  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.944   2.131   0.769  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.456   0.815   1.265  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.540   1.940  -0.463  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.776   0.941  -1.800  1.00  0.00           H  
HETATM   43  H18 UNL     1       1.777   3.846  -1.485  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.056   5.487  -1.845  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.349   4.756  -1.365  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.822   2.557  -0.612  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   18
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9    9   17
CONECT    9   10   33
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   34   35   36
CONECT   13   14   16
CONECT   14   15
CONECT   15   37   38   39
CONECT   16   17   17   25
CONECT   17   18
CONECT   18   19   40
CONECT   19   20   41   42
CONECT   20   21   21   25
CONECT   21   22   43
CONECT   22   23   23   44
CONECT   23   24   45
CONECT   24   25   25   46
END

HMDB0036988
     RDKit          3D
N-Methoxycarbonyl-N-nornuciferine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.7199   -1.7213   -1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5302   -1.7743   -0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5749   -0.7470   -0.4370 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    0.1726   -1.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -0.7496    0.3179 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -1.8552    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -2.5609    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901   -1.5651    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4803   -2.0659    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5593   -1.2515    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.7471    0.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518   -3.1031    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    0.1005    0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5133    0.8390   -0.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2151    1.3804    1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0885    0.5682   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0146   -0.2615    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4112    0.2755    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    1.3267   -0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    2.2626   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532    3.5605   -1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417    4.4777   -1.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5132    4.0816   -1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    2.7903   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    1.9002   -0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2975   -0.8090   -0.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2961   -2.6395   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -1.7977   -2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922   -2.5854    1.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058   -1.4324    2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0545   -3.2112   -0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -3.1885    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6725   -3.1064    0.9529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1219   -3.3293    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064   -3.7516    0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4763   -3.3369    1.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251    1.8717    1.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179    0.5099    1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9441    2.1310    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561    0.8145    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398    1.9400   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757    0.9406   -1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7766    3.8458   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    5.4872   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3487    4.7565   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8222    2.5573   -0.6120 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17  8  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 15,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,13,15-hexaene-10-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₁NO₄

Average Molecular Weight

339.385

Monoisotopic Molecular Weight

339.147058165

IUPAC Name

methyl 15,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

Traditional Name

methyl 15,16-dimethoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

CAS Registry Number

356042-11-0

SMILES

COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC1=C3C=CC=C1

InChI Identifier

InChI=1S/C20H21NO4/c1-23-16-11-13-8-9-21(20(22)25-3)15-10-12-6-4-5-7-14(12)18(17(13)15)19(16)24-2/h4-7,11,15H,8-10H2,1-3H3

InChI Key

NZPPZYPCWOGFIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036988)

Cellular substructure

Membrane (HMDB: HMDB0036988)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036988)

Source

Exogenous

Food

Food (HMDB: HMDB0036988)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0036988)

Not Available

Nutrient (HMDB: HMDB0036988)

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
Water Solubility	0.038 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.23	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.85 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.417	31661259
DarkChem	[M-H]-	179.957	31661259
DeepCCS	[M+H]+	182.508	30932474
DeepCCS	[M-H]-	180.15	30932474
DeepCCS	[M-2H]-	214.374	30932474
DeepCCS	[M+Na]+	189.629	30932474
AllCCS	[M+H]+	180.9	32859911
AllCCS	[M+H-H2O]+	177.8	32859911
AllCCS	[M+NH4]+	183.8	32859911
AllCCS	[M+Na]+	184.7	32859911
AllCCS	[M-H]-	187.4	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methoxycarbonyl-N-nornuciferine	COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC1=C3C=CC=C1	4104.3	Standard polar	33892256
N-Methoxycarbonyl-N-nornuciferine	COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC1=C3C=CC=C1	2735.0	Standard non polar	33892256
N-Methoxycarbonyl-N-nornuciferine	COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC1=C3C=CC=C1	2810.8	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 - N-Methoxycarbonyl-N-nornuciferine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fs-0097000000-c12733638f25eb403ac4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 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 - N-Methoxycarbonyl-N-nornuciferine 10V, Positive-QTOF	splash10-0006-0009000000-cb12295438802236dba9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 20V, Positive-QTOF	splash10-0a4i-0049000000-ed8266d7f9e13220b9f9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 40V, Positive-QTOF	splash10-0w31-0090000000-5ad8eb4999ef7e930177	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 10V, Negative-QTOF	splash10-052r-0009000000-c1adee188acf310e0a31	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 20V, Negative-QTOF	splash10-0a4r-0029000000-dd516280bc3bdb803276	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 40V, Negative-QTOF	splash10-0006-2091000000-0dd8e55c6abce960749d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 10V, Positive-QTOF	splash10-0006-0009000000-4c7e5f46ba97112cd9e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 20V, Positive-QTOF	splash10-0a5c-0069000000-0158739503e9df15d1e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 40V, Positive-QTOF	splash10-0gc9-0090000000-254938ec3dd61cc2a7d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 10V, Negative-QTOF	splash10-000i-0009000000-a9f00908271fb71883c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 20V, Negative-QTOF	splash10-03di-0090000000-0bf709ba3c6dafe76608	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxycarbonyl-N-nornuciferine 40V, Negative-QTOF	splash10-03dl-3090000000-f25436377e20f8128057	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB015960

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49840374

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for N-Methoxycarbonyl-N-nornuciferine (HMDB0036988)

MOL for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

3D MOL for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

3D SDF for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

3D-SDF for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

PDB for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

3D PDB for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

SMILES for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

INCHI for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

Structure for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

3D Structure for HMDB0036988 (N-Methoxycarbonyl-N-nornuciferine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra