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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:13:59 UTC

Update Date

2022-03-07 02:55:08 UTC

HMDB ID

HMDB0036989

Secondary Accession Numbers

HMDB36989

Metabolite Identification

Common Name

Romucosine B

Description

Romucosine B 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. Romucosine B has been detected, but not quantified in, alcoholic beverages and fruits. This could make romucosine b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Romucosine B.

Structure

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

HMDB0036989
     RDKit          3D
Romucosine B
 43 46  0  0  0  0  0  0  0  0999 V2000
    5.0389   -1.3188   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682   -0.9882   -0.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5419    0.2449    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5552    1.0261    0.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    0.7119    0.5864 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    2.0747    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721    2.8652    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764    2.1779    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453    2.9403   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    4.6687   -0.5019 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    2.3855   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    3.1486   -0.8830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443    0.9992   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329    0.5199   -0.6066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5707    0.6321    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2847    0.2202   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    0.8305    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992    0.0057    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099   -1.4030    0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -1.9723    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -3.3466    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022   -4.0058   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369   -3.2553   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023   -1.8617   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984   -1.2429   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -0.8995   -0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -2.4441   -1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481   -0.9815   -2.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434    2.4672    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874    1.9905    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    3.9094    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484    2.9051   -0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1389    2.7247   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4172   -0.1583    1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5850    0.5772    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4741    1.6144    1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -0.0054    1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7276   -2.0404    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645   -1.4698   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -3.9608    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -5.0861   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5585   -3.8004   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.3987   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17  8  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
M  END


  Mrv0541 02241209412D          

 25 28  0  0  0  0            999 V2000
    1.9202    0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9202    0.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    1.2711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    0.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222    1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    0.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241    1.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    0.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3669    0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6241   -0.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -0.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -0.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785   -1.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -1.6140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -1.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -1.6140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193   -2.4388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844    2.4388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    2.4388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3669    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -2.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784   -1.5340    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 24  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036989

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H18ClNO4/c1-24-18-15-11-6-4-3-5-10(11)9-13-14(15)12(16(20)17(18)22)7-8-21(13)19(23)25-2/h3-6,13,22H,7-9H2,1-2H3

> <INCHI_KEY>
FFSNCZHOAOMPLR-UHFFFAOYSA-N

> <FORMULA>
C19H18ClNO4

> <MOLECULAR_WEIGHT>
359.804

> <EXACT_MASS>
359.092435776

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.23151688094644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 14-chloro-15-hydroxy-16-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
3.6904055903333326

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.298245083259227

> <JCHEM_PKA_STRONGEST_BASIC>
-4.922667637550812

> <JCHEM_POLAR_SURFACE_AREA>
59

> <JCHEM_REFRACTIVITY>
95.16999999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 14-chloro-15-hydroxy-16-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036989
     RDKit          3D
Romucosine B
 43 46  0  0  0  0  0  0  0  0999 V2000
    5.0389   -1.3188   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682   -0.9882   -0.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5419    0.2449    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5552    1.0261    0.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    0.7119    0.5864 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    2.0747    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721    2.8652    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764    2.1779    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453    2.9403   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    4.6687   -0.5019 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    2.3855   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    3.1486   -0.8830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443    0.9992   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329    0.5199   -0.6066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5707    0.6321    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2847    0.2202   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    0.8305    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992    0.0057    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099   -1.4030    0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -1.9723    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -3.3466    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022   -4.0058   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369   -3.2553   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023   -1.8617   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984   -1.2429   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -0.8995   -0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -2.4441   -1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481   -0.9815   -2.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434    2.4672    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874    1.9905    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    3.9094    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484    2.9051   -0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1389    2.7247   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4172   -0.1583    1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5850    0.5772    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4741    1.6144    1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -0.0054    1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7276   -2.0404    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645   -1.4698   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -3.9608    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -5.0861   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5585   -3.8004   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.3987   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17  8  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.584   0.063   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.584   1.603   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.200   2.373   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.969   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.415   2.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.801   1.603   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.032   2.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.418   1.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.418   0.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.032  -0.705   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.801   0.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.415  -0.705   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.969   0.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.200  -0.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.200  -2.243   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.969  -3.013   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.415  -2.243   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.801  -3.013   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.969  -4.552   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.200   3.913   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.091   4.552   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.309   4.552   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.418   3.913   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.801  -4.292   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       3.320  -2.863   0.000  0.00  0.00          Cl+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13    4   12   14                                                  
CONECT   14    1   13   15                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   19                                                  
CONECT   17   12   16   18                                                  
CONECT   18   17   24                                                       
CONECT   19   16                                                            
CONECT   20    3   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   18                                                            
CONECT   25   15                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036989
HETATM    1  C1  UNL     1       5.039  -1.319  -1.044  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.768  -0.988  -0.531  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.542   0.245   0.039  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.555   1.026   0.055  1.00  0.00           O  
HETATM    5  N1  UNL     1       2.344   0.712   0.586  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.322   2.075   1.159  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.472   2.865   0.210  1.00  0.00           C  
HETATM    8  C5  UNL     1       0.176   2.178   0.027  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.945   2.940  -0.330  1.00  0.00           C  
HETATM   10 CL1  UNL     1      -0.703   4.669  -0.502  1.00  0.00          CL  
HETATM   11  C7  UNL     1      -2.163   2.386  -0.535  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.249   3.149  -0.883  1.00  0.00           O  
HETATM   13  C8  UNL     1      -2.344   0.999  -0.396  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.633   0.520  -0.607  1.00  0.00           O  
HETATM   15  C9  UNL     1      -4.571   0.632   0.517  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.285   0.220  -0.062  1.00  0.00           C  
HETATM   17  C11 UNL     1      -0.015   0.830   0.157  1.00  0.00           C  
HETATM   18  C12 UNL     1       1.099   0.006   0.669  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.110  -1.403   0.263  1.00  0.00           C  
HETATM   20  C14 UNL     1      -0.249  -1.972   0.099  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.305  -3.347   0.074  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.502  -4.006  -0.143  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.637  -3.255  -0.334  1.00  0.00           C  
HETATM   24  C18 UNL     1      -2.602  -1.862  -0.312  1.00  0.00           C  
HETATM   25  C19 UNL     1      -1.398  -1.243  -0.092  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.855  -0.900  -0.424  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.092  -2.444  -1.052  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.148  -0.982  -2.090  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.343   2.467   1.267  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.787   1.990   2.121  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.304   3.909   0.553  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.048   2.905  -0.765  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.139   2.725  -1.045  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.417  -0.158   1.246  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.585   0.577   0.082  1.00  0.00           H  
HETATM   36  H11 UNL     1      -4.474   1.614   1.007  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.892  -0.005   1.814  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.728  -2.040   0.916  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.565  -1.470  -0.767  1.00  0.00           H  
HETATM   40  H15 UNL     1       0.600  -3.961   0.225  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.504  -5.086  -0.154  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.559  -3.800  -0.502  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.512  -1.399  -0.513  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   18
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9    9   17
CONECT    9   10   11
CONECT   11   12   13   13
CONECT   12   33
CONECT   13   14   16
CONECT   14   15
CONECT   15   34   35   36
CONECT   16   17   17   25
CONECT   17   18
CONECT   18   19   37
CONECT   19   20   38   39
CONECT   20   21   21   25
CONECT   21   22   40
CONECT   22   23   23   41
CONECT   23   24   42
CONECT   24   25   25   43
END

HMDB0036989
     RDKit          3D
Romucosine B
 43 46  0  0  0  0  0  0  0  0999 V2000
    5.0389   -1.3188   -1.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7682   -0.9882   -0.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5419    0.2449    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5552    1.0261    0.0553 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3443    0.7119    0.5864 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    2.0747    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4721    2.8652    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1764    2.1779    0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9453    2.9403   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7027    4.6687   -0.5019 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    2.3855   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    3.1486   -0.8830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3443    0.9992   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6329    0.5199   -0.6066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5707    0.6321    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2847    0.2202   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146    0.8305    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0992    0.0057    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1099   -1.4030    0.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -1.9723    0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049   -3.3466    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5022   -4.0058   -0.1429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369   -3.2553   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023   -1.8617   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3984   -1.2429   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549   -0.8995   -0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -2.4441   -1.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1481   -0.9815   -2.0901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3434    2.4672    1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874    1.9905    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3041    3.9094    0.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484    2.9051   -0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1389    2.7247   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4172   -0.1583    1.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5850    0.5772    0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4741    1.6144    1.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -0.0054    1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7276   -2.0404    0.9165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5645   -1.4698   -0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -3.9608    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -5.0861   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5585   -3.8004   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117   -1.3987   -0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  5  1  0
 25 20  1  0
 17  8  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 14-chloro-15-hydroxy-16-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaene-10-carboxylic acid	HMDB

Chemical Formula

C₁₉H₁₈ClNO₄

Average Molecular Weight

359.804

Monoisotopic Molecular Weight

359.092435776

IUPAC Name

methyl 14-chloro-15-hydroxy-16-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

Traditional Name

methyl 14-chloro-15-hydroxy-16-methoxy-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2(7),3,5,13,15-hexaene-10-carboxylate

CAS Registry Number

356048-24-3

SMILES

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

InChI Identifier

InChI=1S/C19H18ClNO4/c1-24-18-15-11-6-4-3-5-10(11)9-13-14(15)12(16(20)17(18)22)7-8-21(13)19(23)25-2/h3-6,13,22H,7-9H2,1-2H3

InChI Key

FFSNCZHOAOMPLR-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
2-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aryl chloride
Aryl halide
Benzenoid
Methylcarbamate
Carbamic acid ester
Carbonic acid derivative
Azacycle
Ether
Organoheterocyclic compound
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen 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: HMDB0036989)
Cell membrane (HMDB: HMDB0036989)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036989)

Source

Exogenous

Exogenous (HMDB: HMDB0036989)

Food

Food (HMDB: HMDB0036989)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0036989)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036989)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	3.61	ALOGPS
logP	3.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.17 m³·mol⁻¹	ChemAxon
Polarizability	37.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	183.81	30932474
DeepCCS	[M-H]-	181.452	30932474
DeepCCS	[M-2H]-	215.739	30932474
DeepCCS	[M+Na]+	190.966	30932474
AllCCS	[M+H]+	181.6	32859911
AllCCS	[M+H-H2O]+	178.6	32859911
AllCCS	[M+NH4]+	184.4	32859911
AllCCS	[M+Na]+	185.2	32859911
AllCCS	[M-H]-	185.2	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	184.1	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.	7.75 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1877 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.44 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2334.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	391.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	210.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	683.6 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	769.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1377.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	547.4 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	1546.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	466.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	396.3 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	11.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Romucosine B	COC(=O)N1CCC2=C(Cl)C(O)=C(OC)C3=C2C1CC1=C3C=CC=C1	4425.9	Standard polar	33892256
Romucosine B	COC(=O)N1CCC2=C(Cl)C(O)=C(OC)C3=C2C1CC1=C3C=CC=C1	2790.7	Standard non polar	33892256
Romucosine B	COC(=O)N1CCC2=C(Cl)C(O)=C(OC)C3=C2C1CC1=C3C=CC=C1	3048.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Romucosine B,1TMS,isomer #1	COC(=O)N1CCC2=C(Cl)C(O[Si](C)(C)C)=C(OC)C3=C2C1CC1=CC=CC=C13	2868.1	Semi standard non polar	33892256
Romucosine B,1TBDMS,isomer #1	COC(=O)N1CCC2=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C(OC)C3=C2C1CC1=CC=CC=C13	3052.6	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 - Romucosine B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ki6-0049000000-cf070fd8de19450f5f29	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Romucosine B GC-MS (1 TMS) - 70eV, Positive	splash10-01b9-3039700000-daf6d27a1891a942c4aa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Romucosine B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Romucosine B 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 - Romucosine B 10V, Positive-QTOF	splash10-03di-0009000000-97061ac59979e46ac9c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 20V, Positive-QTOF	splash10-004i-0029000000-199871f3674bbab60876	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 40V, Positive-QTOF	splash10-0h9r-0093000000-4e3c3ad770a7e6effaef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 10V, Negative-QTOF	splash10-0a6r-0009000000-cbb022e0a7a1bce43f25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 20V, Negative-QTOF	splash10-004i-0019000000-34f9de78dba434e47ace	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 40V, Negative-QTOF	splash10-03fv-6089000000-7eef01e627aaf8964a52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 10V, Positive-QTOF	splash10-03di-0009000000-bb2aab7c1751997fc29c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 20V, Positive-QTOF	splash10-01t9-0019000000-2cf80cea9255ca28b485	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 40V, Positive-QTOF	splash10-0f79-0095000000-d5fa6e228e88702a07ed	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 10V, Negative-QTOF	splash10-0a4i-0009000000-3015c6e703dedfb321a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 20V, Negative-QTOF	splash10-0fai-2059000000-2f872dabd0c81e022b8a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Romucosine B 40V, Negative-QTOF	splash10-0536-9041000000-8e311376007b19e92a22	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015961

KNApSAcK ID

Not Available

Chemspider ID

35014342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85152934

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 Romucosine B (HMDB0036989)

MOL for HMDB0036989 (Romucosine B)

3D MOL for HMDB0036989 (Romucosine B)

3D SDF for HMDB0036989 (Romucosine B)

3D-SDF for HMDB0036989 (Romucosine B)

PDB for HMDB0036989 (Romucosine B)

3D PDB for HMDB0036989 (Romucosine B)

SMILES for HMDB0036989 (Romucosine B)

INCHI for HMDB0036989 (Romucosine B)

Structure for HMDB0036989 (Romucosine B)

3D Structure for HMDB0036989 (Romucosine B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra