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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:41 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030246

Secondary Accession Numbers

HMDB30246

Metabolite Identification

Common Name

Narceine

Description

Narceine belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review a significant number of articles have been published on Narceine.

Structure

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


  Mrv0541 05061305062D          

 32 34  0  0  0  0            999 V2000
    3.4990   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 17  2  0  0  0  0
 21 19  1  0  0  0  0
 22 18  2  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24  1  1  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 25 16  2  0  0  0  0
 26 23  1  0  0  0  0
 27 23  2  0  0  0  0
 28  3  1  0  0  0  0
 28 17  1  0  0  0  0
 29  4  1  0  0  0  0
 29 20  1  0  0  0  0
 30  5  1  0  0  0  0
 30 21  1  0  0  0  0
 31 12  1  0  0  0  0
 31 18  1  0  0  0  0
 32 12  1  0  0  0  0
 32 22  1  0  0  0  0
M  END

HMDB0030246
     RDKit          3D
Narceine
 59 61  0  0  0  0  0  0  0  0999 V2000
    6.2414   -0.4587    2.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425   -0.9470    1.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3751   -0.5329    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    0.3585    1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3753    0.7689    1.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973    0.2726    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    0.7627   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857    1.5780    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067    0.4812   -1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    1.1496   -1.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5510   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.8093   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -1.0179    1.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -2.4376    1.6510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -2.8374    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6752   -2.6785    2.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167    1.3019   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946    2.5820   -0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957    3.1808   -1.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    2.4429   -1.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100    3.0353   -2.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390    2.8724   -3.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213    4.4878   -1.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    4.7765   -1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    3.5108   -1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.6158   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173   -1.2500   -1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -2.3469   -1.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -0.6417   -2.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -1.0115   -0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -1.9050   -0.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964   -3.3105   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3673   -0.5106    2.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0543   -1.0601    3.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0615    0.6311    2.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667    0.7546    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8351    1.4898    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -0.6061   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    0.9357   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -1.1243   -0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -1.5541   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2738   -0.7061    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906   -0.4762    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -2.2366    2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9064   -3.9288    2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746   -2.7819    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6335   -2.8573    2.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007   -3.5601    3.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802   -1.7763    3.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.8744   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    2.1338   -4.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.8551   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.5710   -3.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1165    5.2747   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    5.4112   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -1.0277   -3.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846   -3.5471    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966   -3.7236   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371   -3.7667   -1.4565 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 26 30  2  0
 30 31  1  0
 31 32  1  0
 30  3  1  0
 20 10  1  0
 25 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  9 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 29 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
M  END


  Mrv0541 05061305062D          

 32 34  0  0  0  0            999 V2000
    3.4990   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.5396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  9  8  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 14  2  0  0  0  0
 20 15  2  0  0  0  0
 21 17  2  0  0  0  0
 21 19  1  0  0  0  0
 22 18  2  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24  1  1  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 25 16  2  0  0  0  0
 26 23  1  0  0  0  0
 27 23  2  0  0  0  0
 28  3  1  0  0  0  0
 28 17  1  0  0  0  0
 29  4  1  0  0  0  0
 29 20  1  0  0  0  0
 30  5  1  0  0  0  0
 30 21  1  0  0  0  0
 31 12  1  0  0  0  0
 31 18  1  0  0  0  0
 32 12  1  0  0  0  0
 32 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030246

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC1=C(OC)C2=C(OCO2)C=C1CCN(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)

> <INCHI_KEY>
DEXMFYZAHXMZNM-UHFFFAOYSA-N

> <FORMULA>
C23H27NO8

> <MOLECULAR_WEIGHT>
445.4624

> <EXACT_MASS>
445.173666845

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
45.946946778849124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(2-{6-[2-(dimethylamino)ethyl]-4-methoxy-2H-1,3-benzodioxol-5-yl}acetyl)-2,3-dimethoxybenzoic acid

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
-0.3271650888108926

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.130543534734954

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5022229441902315

> <JCHEM_PKA_STRONGEST_BASIC>
8.331468661716835

> <JCHEM_POLAR_SURFACE_AREA>
103.76000000000002

> <JCHEM_REFRACTIVITY>
116.89309999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
narceine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030246
     RDKit          3D
Narceine
 59 61  0  0  0  0  0  0  0  0999 V2000
    6.2414   -0.4587    2.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425   -0.9470    1.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3751   -0.5329    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    0.3585    1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3753    0.7689    1.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973    0.2726    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    0.7627   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857    1.5780    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067    0.4812   -1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    1.1496   -1.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5510   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.8093   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -1.0179    1.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -2.4376    1.6510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -2.8374    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6752   -2.6785    2.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167    1.3019   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946    2.5820   -0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957    3.1808   -1.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    2.4429   -1.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100    3.0353   -2.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390    2.8724   -3.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213    4.4878   -1.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    4.7765   -1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    3.5108   -1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.6158   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173   -1.2500   -1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -2.3469   -1.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -0.6417   -2.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -1.0115   -0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -1.9050   -0.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964   -3.3105   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3673   -0.5106    2.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0543   -1.0601    3.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0615    0.6311    2.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667    0.7546    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8351    1.4898    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -0.6061   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    0.9357   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -1.1243   -0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -1.5541   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2738   -0.7061    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906   -0.4762    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -2.2366    2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9064   -3.9288    2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746   -2.7819    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6335   -2.8573    2.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007   -3.5601    3.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802   -1.7763    3.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.8744   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    2.1338   -4.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.8551   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.5710   -3.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1165    5.2747   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    5.4112   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -1.0277   -3.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846   -3.5471    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966   -3.7236   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371   -3.7667   -1.4565 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 26 30  2  0
 30 31  1  0
 31 32  1  0
 30  3  1  0
 20 10  1  0
 25 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  9 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 29 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.531  -2.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865  -0.237   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.866   8.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.532   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.865   9.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198  -0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.531   6.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.199   8.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.199   6.693   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       6.531  -1.007   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       3.864   6.693   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.199   3.613   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.531   3.613   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.532   9.003   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.532   5.923   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   24                                                            
CONECT    2   24                                                            
CONECT    3   28                                                            
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6    7   14                                                       
CONECT    7    6   17                                                       
CONECT    8    9   13                                                       
CONECT    9    8   24                                                       
CONECT   10   13   18                                                       
CONECT   11   15   16                                                       
CONECT   12   31   32                                                       
CONECT   13    8   10   15                                                  
CONECT   14    6   16   19                                                  
CONECT   15   11   13   20                                                  
CONECT   16   11   14   25                                                  
CONECT   17    7   21   28                                                  
CONECT   18   10   22   31                                                  
CONECT   19   14   21   23                                                  
CONECT   20   15   22   29                                                  
CONECT   21   17   19   30                                                  
CONECT   22   18   20   32                                                  
CONECT   23   19   26   27                                                  
CONECT   24    1    2    9                                                  
CONECT   25   16                                                            
CONECT   26   23                                                            
CONECT   27   23                                                            
CONECT   28    3   17                                                       
CONECT   29    4   20                                                       
CONECT   30    5   21                                                       
CONECT   31   12   18                                                       
CONECT   32   12   22                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0030246
HETATM    1  C1  UNL     1       6.241  -0.459   2.688  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.642  -0.947   1.518  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.375  -0.533   1.151  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.632   0.359   1.886  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.375   0.769   1.517  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.797   0.273   0.343  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.504   0.763  -0.012  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.086   1.578   0.805  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.307   0.481  -1.217  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.644   1.150  -1.142  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.726   0.551  -0.580  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.801  -0.809  -0.070  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.306  -1.018   1.311  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.473  -2.438   1.651  1.00  0.00           N  
HETATM   15  C12 UNL     1      -3.834  -2.837   1.807  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.675  -2.679   2.836  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.917   1.302  -0.515  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.995   2.582  -0.993  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.896   3.181  -1.561  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.739   2.443  -1.622  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.610   3.035  -2.198  1.00  0.00           O  
HETATM   22  C18 UNL     1      -0.439   2.872  -3.592  1.00  0.00           C  
HETATM   23  O4  UNL     1      -3.221   4.488  -1.976  1.00  0.00           O  
HETATM   24  C19 UNL     1      -4.492   4.777  -1.421  1.00  0.00           C  
HETATM   25  O5  UNL     1      -5.003   3.511  -1.051  1.00  0.00           O  
HETATM   26  C20 UNL     1       2.493  -0.616  -0.420  1.00  0.00           C  
HETATM   27  C21 UNL     1       2.017  -1.250  -1.637  1.00  0.00           C  
HETATM   28  O6  UNL     1       1.432  -2.347  -1.566  1.00  0.00           O  
HETATM   29  O7  UNL     1       2.217  -0.642  -2.850  1.00  0.00           O  
HETATM   30  C22 UNL     1       3.776  -1.012  -0.012  1.00  0.00           C  
HETATM   31  O8  UNL     1       4.521  -1.905  -0.747  1.00  0.00           O  
HETATM   32  C23 UNL     1       4.496  -3.310  -0.558  1.00  0.00           C  
HETATM   33  H1  UNL     1       7.367  -0.511   2.525  1.00  0.00           H  
HETATM   34  H2  UNL     1       6.054  -1.060   3.598  1.00  0.00           H  
HETATM   35  H3  UNL     1       6.062   0.631   2.825  1.00  0.00           H  
HETATM   36  H4  UNL     1       4.067   0.755   2.810  1.00  0.00           H  
HETATM   37  H5  UNL     1       1.835   1.490   2.157  1.00  0.00           H  
HETATM   38  H6  UNL     1      -0.448  -0.606  -1.291  1.00  0.00           H  
HETATM   39  H7  UNL     1       0.188   0.936  -2.096  1.00  0.00           H  
HETATM   40  H8  UNL     1      -3.888  -1.124  -0.083  1.00  0.00           H  
HETATM   41  H9  UNL     1      -2.345  -1.554  -0.795  1.00  0.00           H  
HETATM   42  H10 UNL     1      -1.274  -0.706   1.488  1.00  0.00           H  
HETATM   43  H11 UNL     1      -2.991  -0.476   2.016  1.00  0.00           H  
HETATM   44  H12 UNL     1      -4.363  -2.237   2.587  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.906  -3.929   2.104  1.00  0.00           H  
HETATM   46  H14 UNL     1      -4.375  -2.782   0.852  1.00  0.00           H  
HETATM   47  H15 UNL     1      -0.634  -2.857   2.479  1.00  0.00           H  
HETATM   48  H16 UNL     1      -2.001  -3.560   3.402  1.00  0.00           H  
HETATM   49  H17 UNL     1      -1.680  -1.776   3.481  1.00  0.00           H  
HETATM   50  H18 UNL     1      -4.815   0.874  -0.075  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.133   2.134  -4.009  1.00  0.00           H  
HETATM   52  H20 UNL     1      -0.651   3.855  -4.107  1.00  0.00           H  
HETATM   53  H21 UNL     1       0.616   2.571  -3.804  1.00  0.00           H  
HETATM   54  H22 UNL     1      -5.116   5.275  -2.181  1.00  0.00           H  
HETATM   55  H23 UNL     1      -4.401   5.411  -0.526  1.00  0.00           H  
HETATM   56  H24 UNL     1       2.856  -1.028  -3.557  1.00  0.00           H  
HETATM   57  H25 UNL     1       5.185  -3.547   0.285  1.00  0.00           H  
HETATM   58  H26 UNL     1       3.497  -3.724  -0.400  1.00  0.00           H  
HETATM   59  H27 UNL     1       4.937  -3.767  -1.456  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   30
CONECT    4    5   36
CONECT    5    6    6   37
CONECT    6    7   26
CONECT    7    8    8    9
CONECT    9   10   38   39
CONECT   10   11   11   20
CONECT   11   12   17
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   16
CONECT   15   44   45   46
CONECT   16   47   48   49
CONECT   17   18   18   50
CONECT   18   19   25
CONECT   19   20   20   23
CONECT   20   21
CONECT   21   22
CONECT   22   51   52   53
CONECT   23   24
CONECT   24   25   54   55
CONECT   26   27   30   30
CONECT   27   28   28   29
CONECT   29   56
CONECT   30   31
CONECT   31   32
CONECT   32   57   58   59
END

HMDB0030246
     RDKit          3D
Narceine
 59 61  0  0  0  0  0  0  0  0999 V2000
    6.2414   -0.4587    2.6879 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6425   -0.9470    1.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3751   -0.5329    1.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323    0.3585    1.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3753    0.7689    1.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973    0.2726    0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    0.7627   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857    1.5780    0.8049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067    0.4812   -1.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6438    1.1496   -1.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7258    0.5510   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014   -0.8093   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -1.0179    1.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -2.4376    1.6510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342   -2.8374    1.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6752   -2.6785    2.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167    1.3019   -0.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9946    2.5820   -0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957    3.1808   -1.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    2.4429   -1.6217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100    3.0353   -2.1982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4390    2.8724   -3.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213    4.4878   -1.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    4.7765   -1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0033    3.5108   -1.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4928   -0.6158   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173   -1.2500   -1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -2.3469   -1.5657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174   -0.6417   -2.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762   -1.0115   -0.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -1.9050   -0.7467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4964   -3.3105   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3673   -0.5106    2.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0543   -1.0601    3.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0615    0.6311    2.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667    0.7546    2.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8351    1.4898    2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4477   -0.6061   -1.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883    0.9357   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878   -1.1243   -0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3454   -1.5541   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2738   -0.7061    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906   -0.4762    2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -2.2366    2.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9064   -3.9288    2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3746   -2.7819    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6335   -2.8573    2.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007   -3.5601    3.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6802   -1.7763    3.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.8744   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1334    2.1338   -4.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6509    3.8551   -4.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.5710   -3.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1165    5.2747   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    5.4112   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -1.0277   -3.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846   -3.5471    0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966   -3.7236   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9371   -3.7667   -1.4565 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 26 30  2  0
 30 31  1  0
 31 32  1  0
 30  3  1  0
 20 10  1  0
 25 18  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  9 38  1  0
  9 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 29 56  1  0
 32 57  1  0
 32 58  1  0
 32 59  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-[[6-[2-(Dimethylamino)ethyl]-4-methoxy-1,3-benzodioxol-5-yl]acetyl]-2,3-dimethoxybenzoic acid, 9ci	HMDB
Narcein	HMDB

Chemical Formula

C₂₃H₂₇NO₈

Average Molecular Weight

445.4624

Monoisotopic Molecular Weight

445.173666845

IUPAC Name

6-(2-{6-[2-(dimethylamino)ethyl]-4-methoxy-2H-1,3-benzodioxol-5-yl}acetyl)-2,3-dimethoxybenzoic acid

Traditional Name

narceine

CAS Registry Number

131-28-2

SMILES

COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC1=C(OC)C2=C(OCO2)C=C1CCN(C)C

InChI Identifier

InChI=1S/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)

InChI Key

DEXMFYZAHXMZNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Alkyl-phenylketone
M-methoxybenzoic acid or derivatives
O-methoxybenzoic acid or derivatives
Dimethoxybenzene
O-dimethoxybenzene
Benzodioxole
Benzoic acid or derivatives
Benzoic acid
Phenylketone
Phenethylamine
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Aralkylamine
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Amino acid
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

stilbenoid (CHEBI:7480 )
Isoquinoline alkaloids (C09591 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030246)
Cytoplasm (HMDB: HMDB0030246)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030246)

Source

Endogenous

Endogenous (HMDB: HMDB0030246)

Plant

Plant (HMDB: HMDB0030246)

Exogenous

Food

Food (HMDB: HMDB0030246)

Herb and spice

Spice

Opium poppy (FooDB: FOOD00438)

Exogenous (HMDB: HMDB0030246)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 °C	Not Available
Boiling Point	374.48 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.78 mg/mL at 13 °C	Not Available
LogP	7.957 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.06	ALOGPS
logP	-0.33	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	8.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	116.89 m³·mol⁻¹	ChemAxon
Polarizability	45.95 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
DarkChem	[M+H]+	203.688	31661259
DarkChem	[M-H]-	200.036	31661259
DeepCCS	[M+H]+	201.551	30932474
DeepCCS	[M-H]-	199.156	30932474
DeepCCS	[M-2H]-	232.272	30932474
DeepCCS	[M+Na]+	207.464	30932474
AllCCS	[M+H]+	204.2	32859911
AllCCS	[M+H-H2O]+	201.8	32859911
AllCCS	[M+NH4]+	206.4	32859911
AllCCS	[M+Na]+	207.0	32859911
AllCCS	[M-H]-	209.6	32859911
AllCCS	[M+Na-2H]-	210.4	32859911
AllCCS	[M+HCOO]-	211.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.14 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7867 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.78 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	71.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1320.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	314.3 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	424.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	646.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	835.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	331.5 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	1324.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	309.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	405.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	399.6 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	39.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Narceine	COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC1=C(OC)C2=C(OCO2)C=C1CCN(C)C	4674.6	Standard polar	33892256
Narceine	COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC1=C(OC)C2=C(OCO2)C=C1CCN(C)C	3208.1	Standard non polar	33892256
Narceine	COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC1=C(OC)C2=C(OCO2)C=C1CCN(C)C	3345.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Narceine,1TMS,isomer #1	COC1=CC=C(C(=O)CC2=C(CCN(C)C)C=C3OCOC3=C2OC)C(C(=O)O[Si](C)(C)C)=C1OC	3289.4	Semi standard non polar	33892256
Narceine,1TBDMS,isomer #1	COC1=CC=C(C(=O)CC2=C(CCN(C)C)C=C3OCOC3=C2OC)C(C(=O)O[Si](C)(C)C(C)(C)C)=C1OC	3483.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Narceine EI-B (Non-derivatized)	splash10-0a4i-9210000000-c6c3c934ee19f8db8182	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Narceine EI-B (Non-derivatized)	splash10-0a4i-9210000000-c6c3c934ee19f8db8182	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Narceine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9541400000-7d48e466a1cce6c33aac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Narceine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9130320000-183831bca24f6c6d5f01	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Narceine 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 - Narceine 10V, Positive-QTOF	splash10-0fba-0001900000-10183188673951773c03	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 20V, Positive-QTOF	splash10-0ug0-0234900000-389e5ae29d869375d246	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 40V, Positive-QTOF	splash10-052f-0988000000-9637b882287fce432f36	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 10V, Negative-QTOF	splash10-0f6x-0001900000-ddb55e74e09433b0f01d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 20V, Negative-QTOF	splash10-0fai-0119700000-0afc1dc554a44d8ee2c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 40V, Negative-QTOF	splash10-003r-1209000000-5a110b49ba3963712d0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 10V, Negative-QTOF	splash10-0fuu-0009700000-a74fbffdc5d6b47026f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 20V, Negative-QTOF	splash10-0296-0106900000-3b73e4f6478d5b3b32b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 40V, Negative-QTOF	splash10-0f7x-1309300000-b33d2114685b42841488	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 10V, Positive-QTOF	splash10-0002-0000900000-8b5e9ec8441b6548b288	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 20V, Positive-QTOF	splash10-05c7-0629300000-cf4fc333bb19fc4e96e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Narceine 40V, Positive-QTOF	splash10-0a4i-9625200000-3cdfebf9e86291b9088a	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Narceine

METLIN ID

Not Available

PubChem Compound

8564

PDB ID

Not Available

ChEBI ID

623301

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1354911

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 Narceine (HMDB0030246)

MOL for HMDB0030246 (Narceine)

3D MOL for HMDB0030246 (Narceine)

3D SDF for HMDB0030246 (Narceine)

3D-SDF for HMDB0030246 (Narceine)

PDB for HMDB0030246 (Narceine)

3D PDB for HMDB0030246 (Narceine)

SMILES for HMDB0030246 (Narceine)

INCHI for HMDB0030246 (Narceine)

Structure for HMDB0030246 (Narceine)

3D Structure for HMDB0030246 (Narceine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra