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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:56:54 UTC

Update Date

2021-09-26 23:00:20 UTC

HMDB ID

HMDB0249437

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bulbocapnine

Description

17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol 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. Based on a literature review very few articles have been published on 17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bulbocapnine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bulbocapnine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249437
     RDKit          3D
Bulbocapnine
 43 47  0  0  0  0  0  0  0  0999 V2000
    5.6110   -1.5190   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -0.5593   -0.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749   -0.8851   -0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804   -2.1669   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5690   -2.4459    0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -1.4315    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -0.1466   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    0.1566   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987    1.4017   -0.7106 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    0.9011   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154    2.1979   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    3.1320   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    2.7770   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822    1.4781    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    0.5240    0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314   -0.8124    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -1.8786    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -1.1973    0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -2.4742    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374   -0.2823    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604    1.0893    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    4.3758   -0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    4.2517   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    2.8945   -0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -2.2234    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -1.0416   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5126   -2.1161   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270   -2.9478   -0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3150   -3.4693    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543    1.5899   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    3.5472   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090   -0.7189    1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -2.6446   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -2.4985    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534   -2.5361    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -2.4922    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8743   -3.3396    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7822   -0.6839    0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5621   -0.1963   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3462    1.8453    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499    1.1838    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    4.8781   -1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4315    4.4828    0.6306 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
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 15 10  1  0
 17  6  1  0
 24 11  1  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
M  END


  Mrv1533004191514102D          

 24 28  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
 13 21  1  0  0  0  0
 20 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  2  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249437

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2CC3N(C)CCC4=CC5=C(OCO5)C(=C34)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO4/c1-20-6-5-11-8-14-19(24-9-23-14)17-15(11)12(20)7-10-3-4-13(22-2)18(21)16(10)17/h3-4,8,12,21H,5-7,9H2,1-2H3

> <INCHI_KEY>
LODGIKWNLDQZBM-UHFFFAOYSA-N

> <FORMULA>
C19H19NO4

> <MOLECULAR_WEIGHT>
325.364

> <EXACT_MASS>
325.131408096

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.12190203971437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-18-ol

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.863408908

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.489696991885099

> <JCHEM_PKA_STRONGEST_BASIC>
6.838596921866727

> <JCHEM_POLAR_SURFACE_AREA>
51.160000000000004

> <JCHEM_REFRACTIVITY>
90.23729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bulbocapnine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249437
     RDKit          3D
Bulbocapnine
 43 47  0  0  0  0  0  0  0  0999 V2000
    5.6110   -1.5190   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -0.5593   -0.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749   -0.8851   -0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804   -2.1669   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5690   -2.4459    0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -1.4315    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -0.1466   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    0.1566   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987    1.4017   -0.7106 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    0.9011   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154    2.1979   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    3.1320   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    2.7770   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822    1.4781    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    0.5240    0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314   -0.8124    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -1.8786    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -1.1973    0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -2.4742    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374   -0.2823    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604    1.0893    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    4.3758   -0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    4.2517   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    2.8945   -0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -2.2234    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -1.0416   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5126   -2.1161   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270   -2.9478   -0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3150   -3.4693    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543    1.5899   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    3.5472   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090   -0.7189    1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -2.6446   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -2.4985    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534   -2.5361    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -2.4922    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8743   -3.3396    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7822   -0.6839    0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5621   -0.1963   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3462    1.8453    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499    1.1838    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    4.8781   -1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4315    4.4828    0.6306 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
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 15 10  1  0
 17  6  1  0
 24 11  1  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20    8   13                                                  
CONECT   22   20    6   23                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0249437
HETATM    1  C1  UNL     1       5.611  -1.519  -0.719  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.579  -0.559  -0.696  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.275  -0.885  -0.386  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.880  -2.167  -0.077  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.569  -2.446   0.225  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.631  -1.432   0.220  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.032  -0.147  -0.090  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.332   0.157  -0.395  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.799   1.402  -0.711  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.016   0.901  -0.063  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.315   2.198  -0.389  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.723   3.132  -0.367  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.009   2.777  -0.033  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.282   1.478   0.287  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.274   0.524   0.277  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.731  -0.812   0.670  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.732  -1.879   0.545  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.954  -1.197   0.023  1.00  0.00           N  
HETATM   19  C16 UNL     1      -3.349  -2.474   0.592  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.037  -0.282   0.193  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.660   1.089   0.641  1.00  0.00           C  
HETATM   22  O3  UNL     1      -0.166   4.376  -0.733  1.00  0.00           O  
HETATM   23  C19 UNL     1       1.235   4.252  -0.418  1.00  0.00           C  
HETATM   24  O4  UNL     1       1.412   2.895  -0.755  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.518  -2.223   0.157  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.610  -1.042  -0.730  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.513  -2.116  -1.656  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.627  -2.948  -0.078  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.315  -3.469   0.461  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.754   1.590  -0.928  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.766   3.547  -0.037  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.009  -0.719   1.767  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.993  -2.645  -0.245  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.648  -2.498   1.486  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.453  -2.536   0.496  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.149  -2.492   1.701  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.874  -3.340   0.087  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.782  -0.684   0.911  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.562  -0.196  -0.783  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.346   1.845   0.208  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.750   1.184   1.749  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.797   4.878  -1.136  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.431   4.483   0.631  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   17
CONECT    7    8    8   10
CONECT    8    9
CONECT    9   30
CONECT   10   11   11   15
CONECT   11   12   24
CONECT   12   13   13   22
CONECT   13   14   31
CONECT   14   15   15   21
CONECT   15   16
CONECT   16   17   18   32
CONECT   17   33   34
CONECT   18   19   20
CONECT   19   35   36   37
CONECT   20   21   38   39
CONECT   21   40   41
CONECT   22   23
CONECT   23   24   42   43
END

HMDB0249437
     RDKit          3D
Bulbocapnine
 43 47  0  0  0  0  0  0  0  0999 V2000
    5.6110   -1.5190   -0.7192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -0.5593   -0.6960 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2749   -0.8851   -0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8804   -2.1669   -0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5690   -2.4459    0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315   -1.4315    0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317   -0.1466   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    0.1566   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7987    1.4017   -0.7106 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0156    0.9011   -0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3154    2.1979   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7226    3.1320   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0094    2.7770   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822    1.4781    0.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    0.5240    0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7314   -0.8124    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -1.8786    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9535   -1.1973    0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3493   -2.4742    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374   -0.2823    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6604    1.0893    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    4.3758   -0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2346    4.2517   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    2.8945   -0.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -2.2234    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -1.0416   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5126   -2.1161   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6270   -2.9478   -0.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3150   -3.4693    0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543    1.5899   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7664    3.5472   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090   -0.7189    1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9933   -2.6446   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -2.4985    1.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534   -2.5361    0.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490   -2.4922    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8743   -3.3396    0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7822   -0.6839    0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5621   -0.1963   -0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3462    1.8453    0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499    1.1838    1.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7969    4.8781   -1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4315    4.4828    0.6306 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
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 15 10  1  0
 17  6  1  0
 24 11  1  0
 21 14  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  9 30  1  0
 13 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₁₉NO₄

Average Molecular Weight

325.364

Monoisotopic Molecular Weight

325.131408096

IUPAC Name

17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-18-ol

Traditional Name

bulbocapnine

CAS Registry Number

Not Available

SMILES

COC1=CC=C2CC3N(C)CCC4=CC5=C(OCO5)C(=C34)C2=C1O

InChI Identifier

InChI=1S/C19H19NO4/c1-20-6-5-11-8-14-19(24-9-23-14)17-15(11)12(20)7-10-3-4-13(22-2)18(21)16(10)17/h3-4,8,12,21H,5-7,9H2,1-2H3

InChI Key

LODGIKWNLDQZBM-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

Substituents

Aporphine
Benzoquinoline
Phenanthrene
1-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Oxacycle
Azacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.28	ALOGPS
logP	2.86	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	6.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.24 m³·mol⁻¹	ChemAxon
Polarizability	35.12 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
DeepCCS	[M-2H]-	215.813	30932474
DeepCCS	[M+Na]+	191.461	30932474
AllCCS	[M+H]+	177.3	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.0	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	177.1	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bulbocapnine	COC1=CC=C2CC3N(C)CCC4=CC5=C(OCO5)C(=C34)C2=C1O	4105.6	Standard polar	33892256
Bulbocapnine	COC1=CC=C2CC3N(C)CCC4=CC5=C(OCO5)C(=C34)C2=C1O	2667.1	Standard non polar	33892256
Bulbocapnine	COC1=CC=C2CC3N(C)CCC4=CC5=C(OCO5)C(=C34)C2=C1O	3032.7	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 - Bulbocapnine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-0193000000-074eceb76d42e79c6585	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bulbocapnine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bulbocapnine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bulbocapnine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - Bulbocapnine 10V, Positive-QTOF	splash10-004i-0009000000-8258216b4e41e9caadf2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bulbocapnine 20V, Positive-QTOF	splash10-004i-0009000000-3ff82eadc5ec478a997c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bulbocapnine 40V, Positive-QTOF	splash10-00sj-0092000000-da3d7d8d951014bd294b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bulbocapnine 10V, Negative-QTOF	splash10-00di-0009000000-fd8a579508e412fbe114	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bulbocapnine 20V, Negative-QTOF	splash10-00di-0049000000-65b9ed369c387d7fe2d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bulbocapnine 40V, Negative-QTOF	splash10-00di-0095000000-89e553e67f18c2470cfe	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8919

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Bulbocapnine (HMDB0249437)

MOL for HMDB0249437 (Bulbocapnine)

3D MOL for HMDB0249437 (Bulbocapnine)

3D SDF for HMDB0249437 (Bulbocapnine)

3D-SDF for HMDB0249437 (Bulbocapnine)

PDB for HMDB0249437 (Bulbocapnine)

3D PDB for HMDB0249437 (Bulbocapnine)

SMILES for HMDB0249437 (Bulbocapnine)

INCHI for HMDB0249437 (Bulbocapnine)

Structure for HMDB0249437 (Bulbocapnine)

3D Structure for HMDB0249437 (Bulbocapnine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra