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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 18:15:44 UTC

Update Date

2022-09-22 18:34:25 UTC

HMDB ID

HMDB0033524

Secondary Accession Numbers

HMDB33524

Metabolite Identification

Common Name

Lambertine

Description

Lambertine belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. Lambertine has been detected, but not quantified in, several different foods, such as black tea, teas (Camellia sinensis), red tea, herbal tea, and green tea. This could make lambertine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lambertine.

Structure

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

  Mrv0541 05061307102D          

 25 29  0  0  0  0            999 V2000
    2.2354   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 12  3  2  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  2  0  0  0  0
 16 14  1  0  0  0  0
 17  4  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  2  0  0  0  0
 20 17  1  0  0  0  0
 21  6  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
 22  1  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 20  1  0  0  0  0
 24 11  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 25 19  1  0  0  0  0
M  END

HMDB0033524
     RDKit          3D
Lambertine
 44 48  0  0  0  0  0  0  0  0999 V2000
   -6.0801    2.0167    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458    0.8285    0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    0.8995    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    2.1060    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    2.1431    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    0.9946    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8520   -0.1758   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453   -0.2579   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9215   -1.4231   -0.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -1.8899   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -1.3902   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202   -1.2809   -0.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -2.5400    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038   -2.4658   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.1727    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169   -1.1503    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1737    0.0263    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4737    1.1930    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976    1.2105    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429    0.0229    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680   -0.0299    0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    1.0808    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232    2.1962    0.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6639    1.7014    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5294    0.3157    0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8558    2.3511    1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1546    1.8962    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7279    2.8307   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9074    2.9945    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105    3.0726    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -2.9930   -1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244   -1.8262   -1.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.3532   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.2253    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2520   -1.6742   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161   -3.2310   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389   -2.9262    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753   -2.8133   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990   -3.2216    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766   -2.0819    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070    2.1488    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    2.0337    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4713    2.1589    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7175    1.9007   -0.8818 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
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 21 12  1  0
 22  6  1  0
 20 15  1  0
 25 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 19 41  1  0
 22 42  1  0
 24 43  1  0
 24 44  1  0
M  END

  Mrv0541 05061307102D          

 25 29  0  0  0  0            999 V2000
    2.2354   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -1.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2066    1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3817    1.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -0.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5864   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1335    0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127   -1.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1849   -0.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7101   -0.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3600   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4619   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8347   -0.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4113   -0.8877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.5787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6370   -0.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837    0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6389   -0.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9540   -1.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
 12  3  2  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  2  0  0  0  0
 16 14  1  0  0  0  0
 17  4  2  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  2  0  0  0  0
 20 17  1  0  0  0  0
 21  6  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
 22  1  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 20  1  0  0  0  0
 24 11  1  0  0  0  0
 24 18  1  0  0  0  0
 25 11  1  0  0  0  0
 25 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033524

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3

> <INCHI_KEY>
FZAGOOYMTPGPGF-UHFFFAOYSA-N

> <FORMULA>
C20H19NO4

> <MOLECULAR_WEIGHT>
337.3692

> <EXACT_MASS>
337.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.113005530353306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.836994116333334

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.02031869254873

> <JCHEM_POLAR_SURFACE_AREA>
40.160000000000004

> <JCHEM_REFRACTIVITY>
95.68939999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033524
     RDKit          3D
Lambertine
 44 48  0  0  0  0  0  0  0  0999 V2000
   -6.0801    2.0167    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458    0.8285    0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    0.8995    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    2.1060    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    2.1431    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    0.9946    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8520   -0.1758   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453   -0.2579   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9215   -1.4231   -0.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -1.8899   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -1.3902   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202   -1.2809   -0.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -2.5400    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038   -2.4658   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.1727    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169   -1.1503    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1737    0.0263    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4737    1.1930    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976    1.2105    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429    0.0229    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680   -0.0299    0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    1.0808    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232    2.1962    0.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6639    1.7014    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5294    0.3157    0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8558    2.3511    1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1546    1.8962    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7279    2.8307   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9074    2.9945    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105    3.0726    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -2.9930   -1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244   -1.8262   -1.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.3532   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.2253    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2520   -1.6742   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161   -3.2310   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389   -2.9262    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753   -2.8133   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990   -3.2216    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766   -2.0819    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070    2.1488    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    2.0337    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4713    2.1589    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7175    1.9007   -0.8818 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
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 21 12  1  0
 22  6  1  0
 20 15  1  0
 25 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 19 41  1  0
 22 42  1  0
 24 43  1  0
 24 44  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       4.173  -0.148   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.963   1.174   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.752  -2.885   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.212  -2.862   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.452   2.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.913   2.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082  -1.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.742   1.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.161  -1.634   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.583   1.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.130  -2.212   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.542  -1.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.202   1.033   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.412  -0.288   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.792  -0.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.872  -0.265   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.462  -1.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.491  -0.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.701  -1.657   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.252  -0.195   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      11.122   1.080   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       4.922  -1.493   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.503   1.150   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      17.993  -0.678   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      16.714  -2.817   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3    4   12                                                       
CONECT    4    3   17                                                       
CONECT    5    6   13                                                       
CONECT    6    5   21                                                       
CONECT    7   12   16                                                       
CONECT    8   13   18                                                       
CONECT    9   14   19                                                       
CONECT   10   15   21                                                       
CONECT   11   24   25                                                       
CONECT   12    3    7   15                                                  
CONECT   13    5    8   14                                                  
CONECT   14    9   13   16                                                  
CONECT   15   10   12   20                                                  
CONECT   16    7   14   21                                                  
CONECT   17    4   20   22                                                  
CONECT   18    8   19   24                                                  
CONECT   19    9   18   25                                                  
CONECT   20   15   17   23                                                  
CONECT   21    6   10   16                                                  
CONECT   22    1   17                                                       
CONECT   23    2   20                                                       
CONECT   24   11   18                                                       
CONECT   25   11   19                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0033524
HETATM    1  C1  UNL     1      -6.080   2.017   0.364  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.346   0.828   0.128  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.959   0.899   0.159  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.302   2.106   0.414  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.924   2.143   0.438  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.196   0.995   0.211  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.852  -0.176  -0.038  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.245  -0.258  -0.071  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.922  -1.423  -0.317  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.313  -1.890  -1.582  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.101  -1.390  -0.330  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.320  -1.281  -0.058  1.00  0.00           N  
HETATM   13  C10 UNL     1       1.050  -2.540   0.039  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.504  -2.466  -0.159  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.137  -1.173   0.075  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.517  -1.150   0.153  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.174   0.026   0.353  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.474   1.193   0.478  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.098   1.210   0.406  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.443   0.023   0.204  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.968  -0.030   0.134  1.00  0.00           C  
HETATM   22  C19 UNL     1       0.267   1.081   0.297  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.423   2.196   0.669  1.00  0.00           O  
HETATM   24  C20 UNL     1       6.664   1.701   0.204  1.00  0.00           C  
HETATM   25  O4  UNL     1       6.529   0.316   0.467  1.00  0.00           O  
HETATM   26  H1  UNL     1      -5.856   2.351   1.387  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.155   1.896   0.171  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.728   2.831  -0.317  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.907   2.994   0.588  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.410   3.073   0.634  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.089  -2.993  -1.605  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.424  -1.826  -1.624  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.835  -1.353  -2.424  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.495  -2.225   0.281  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.252  -1.674  -1.392  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.616  -3.231  -0.723  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.839  -2.926   1.070  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.775  -2.813  -1.194  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.999  -3.222   0.525  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.077  -2.082   0.053  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.607   2.149   0.508  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.722   2.034   0.491  1.00  0.00           H  
HETATM   43  H18 UNL     1       7.471   2.159   0.789  1.00  0.00           H  
HETATM   44  H19 UNL     1       6.717   1.901  -0.882  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   29
CONECT    5    6    6   30
CONECT    6    7   22
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   31   32   33
CONECT   11   12   34   35
CONECT   12   13   21
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   16   20
CONECT   16   17   40
CONECT   17   18   18   25
CONECT   18   19   23
CONECT   19   20   20   41
CONECT   20   21
CONECT   21   22   22
CONECT   22   42
CONECT   23   24
CONECT   24   25   43   44
END

HMDB0033524
     RDKit          3D
Lambertine
 44 48  0  0  0  0  0  0  0  0999 V2000
   -6.0801    2.0167    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3458    0.8285    0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    0.8995    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    2.1060    0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241    2.1431    0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959    0.9946    0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8520   -0.1758   -0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2453   -0.2579   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9215   -1.4231   -0.3174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -1.8899   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009   -1.3902   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3202   -1.2809   -0.0584 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0497   -2.5400    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038   -2.4658   -0.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366   -1.1727    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169   -1.1503    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1737    0.0263    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4737    1.1930    0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976    1.2105    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429    0.0229    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9680   -0.0299    0.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    1.0808    0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232    2.1962    0.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6639    1.7014    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5294    0.3157    0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8558    2.3511    1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1546    1.8962    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7279    2.8307   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9074    2.9945    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105    3.0726    0.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -2.9930   -1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4244   -1.8262   -1.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8349   -1.3532   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948   -2.2253    0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2520   -1.6742   -1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6161   -3.2310   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8389   -2.9262    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7753   -2.8133   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990   -3.2216    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766   -2.0819    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070    2.1488    0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    2.0337    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4713    2.1589    0.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7175    1.9007   -0.8818 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
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
  8  3  1  0
 21 12  1  0
 22  6  1  0
 20 15  1  0
 25 17  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 19 41  1  0
 22 42  1  0
 24 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dihydroberberine hydrochloride	MeSH
Dihydroberberine	HMDB

Chemical Formula

C₂₀H₁₉NO₄

Average Molecular Weight

337.3692

Monoisotopic Molecular Weight

337.131408101

IUPAC Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene

Traditional Name

16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),2,4(8),9,15,17,19-heptaene

CAS Registry Number

120834-89-1

SMILES

COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC

InChI Identifier

InChI=1S/C20H19NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-9H,5-6,10-11H2,1-2H3

InChI Key

FZAGOOYMTPGPGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroisoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Acetal
Organoheterocyclic compound
Oxacycle
Azacycle
Enamine
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033524)
Cell membrane (HMDB: HMDB0033524)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033524)

Source

Exogenous

Exogenous (HMDB: HMDB0033524)

Food

Food (HMDB: HMDB0033524)

Tea

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033524)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033524)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 - 164 °C	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	0.073 g/L	ALOGPS
logP	3.36	ALOGPS
logP	2.84	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	4.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.69 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	5	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]+	179.332	31661259
DarkChem	[M-H]-	179.842	31661259
DeepCCS	[M-2H]-	221.465	30932474
DeepCCS	[M+Na]+	196.692	30932474
AllCCS	[M+H]+	180.7	32859911
AllCCS	[M+H-H2O]+	177.5	32859911
AllCCS	[M+NH4]+	183.7	32859911
AllCCS	[M+Na]+	184.6	32859911
AllCCS	[M-H]-	187.1	32859911
AllCCS	[M+Na-2H]-	186.5	32859911
AllCCS	[M+HCOO]-	185.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lambertine	COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC	4761.9	Standard polar	33892256
Lambertine	COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC	2786.6	Standard non polar	33892256
Lambertine	COC1=CC=C2C=C3N(CCC4=CC5=C(OCO5)C=C34)CC2=C1OC	3170.6	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 - Lambertine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0937000000-0c51681a533aea1542e8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lambertine 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 - Lambertine 10V, Positive-QTOF	splash10-000i-0009000000-71e9dc30e119186620ae	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 20V, Positive-QTOF	splash10-000i-0109000000-811a0237d57b2724db6b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 40V, Positive-QTOF	splash10-002g-0891000000-70473923c1a156f45883	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 10V, Negative-QTOF	splash10-000i-0009000000-a4fa7b371323f46c26ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 20V, Negative-QTOF	splash10-000i-0019000000-f71cc29f31c9f8419066	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 40V, Negative-QTOF	splash10-0fdo-0092000000-a15fa22a545766a000f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 10V, Negative-QTOF	splash10-000i-0009000000-e425d548b88b81358192	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 20V, Negative-QTOF	splash10-000i-0009000000-875cb50d577bc475b166	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 40V, Negative-QTOF	splash10-0076-0093000000-545328ff2003bc0bf8bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 10V, Positive-QTOF	splash10-000i-0009000000-195152c9499dc2b0f3dd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 20V, Positive-QTOF	splash10-000i-0009000000-177debf6280ad456cbfd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lambertine 40V, Positive-QTOF	splash10-000i-0369000000-0a5b23cfa362b926caa0	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB011580

KNApSAcK ID

C00028445

Chemspider ID

9800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10217

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 Lambertine (HMDB0033524)

MOL for HMDB0033524 (Lambertine)

3D MOL for HMDB0033524 (Lambertine)

3D SDF for HMDB0033524 (Lambertine)

3D-SDF for HMDB0033524 (Lambertine)

PDB for HMDB0033524 (Lambertine)

3D PDB for HMDB0033524 (Lambertine)

SMILES for HMDB0033524 (Lambertine)

INCHI for HMDB0033524 (Lambertine)

Structure for HMDB0033524 (Lambertine)

3D Structure for HMDB0033524 (Lambertine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra