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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:29 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030212

Secondary Accession Numbers

HMDB30212

Metabolite Identification

Common Name

Mukonicine

Description

Mukonicine belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Based on a literature review very few articles have been published on Mukonicine.

Structure

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

HMDB0030212
     RDKit          3D
Mukonicine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5613    2.2083    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744    0.8303    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.1934    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -1.1694   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410   -1.8604   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -3.2123   -0.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -3.8763   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -1.1693   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -1.5463   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027   -0.4667   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740   -0.2866   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908    0.9214    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    2.0083    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    3.3193    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071    1.8608    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5932    0.6347    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927    0.1856    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    0.8797    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5624    1.0325    0.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3955   -0.0556   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3097   -0.3260    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    0.3415   -1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -1.3394   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966   -1.4687   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    2.4388    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971    2.8521   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    2.3552    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552   -1.6969   -0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157   -4.9765   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -3.6717    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8071   -3.4667   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -2.5053   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7799    3.2704    1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179    3.7676   -0.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    4.0127    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    2.7095    0.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0679    1.9215    0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9554   -1.1778    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9421    0.5289    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574   -0.6684    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628   -0.1396   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4466    1.4337   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7649    0.0526   -2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3062   -2.2542   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -2.4247   -0.5465 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 18  3  1  0
 17  8  1  0
 16 10  1  0
 24 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
M  END


  Mrv0541 05061305052D          

 24 27  0  0  0  0            999 V2000
   -0.7131    1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323    3.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6717    2.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5031    2.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    5.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    4.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000    4.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4816    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425    2.6415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150    3.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421    2.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758    3.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4237    3.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8526    2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209    4.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3999    3.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6876    3.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7947    2.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0710    3.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9160    4.2035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698    2.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4601    5.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6184    2.7287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  1  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  2  0  0  0  0
 17 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  7  1  0  0  0  0
 21 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22  4  1  0  0  0  0
 22 12  1  0  0  0  0
 23  5  1  0  0  0  0
 23 16  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030212

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO3/c1-11-8-14-15-9-12(22-4)10-16(23-5)18(15)21-17(14)13-6-7-20(2,3)24-19(11)13/h6-10,21H,1-5H3

> <INCHI_KEY>
APZRRMFSHXMDTQ-UHFFFAOYSA-N

> <FORMULA>
C20H21NO3

> <MOLECULAR_WEIGHT>
323.3856

> <EXACT_MASS>
323.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.95984711993749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,15-dimethoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
4.189587949333334

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.889434870061898

> <JCHEM_PKA_STRONGEST_BASIC>
-4.397399623469927

> <JCHEM_POLAR_SURFACE_AREA>
43.480000000000004

> <JCHEM_REFRACTIVITY>
95.83320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,15-dimethoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030212
     RDKit          3D
Mukonicine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5613    2.2083    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744    0.8303    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.1934    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -1.1694   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410   -1.8604   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -3.2123   -0.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -3.8763   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -1.1693   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -1.5463   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027   -0.4667   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740   -0.2866   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908    0.9214    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    2.0083    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    3.3193    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071    1.8608    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5932    0.6347    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927    0.1856    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    0.8797    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5624    1.0325    0.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3955   -0.0556   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3097   -0.3260    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    0.3415   -1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -1.3394   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966   -1.4687   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    2.4388    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971    2.8521   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    2.3552    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552   -1.6969   -0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157   -4.9765   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -3.6717    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8071   -3.4667   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -2.5053   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7799    3.2704    1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179    3.7676   -0.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    4.0127    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    2.7095    0.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0679    1.9215    0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9554   -1.1778    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9421    0.5289    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574   -0.6684    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628   -0.1396   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4466    1.4337   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7649    0.0526   -2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3062   -2.2542   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -2.4247   -0.5465 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 18  3  1  0
 17  8  1  0
 16 10  1  0
 24 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  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      -1.331   2.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.100   7.302   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.987   5.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.406   5.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.297  10.378   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.636   7.845   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.173   7.757   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.899   3.982   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.373   4.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.815   7.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.639   3.894   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.741   5.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.791   6.557   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.592   5.358   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.077   5.763   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.519   8.007   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.746   6.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.150   7.302   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.483   5.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.866   6.381   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.710   7.847   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       7.037   4.804   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.592   9.546   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.021   5.094   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   22                                                            
CONECT    5   23                                                            
CONECT    6    7   13                                                       
CONECT    7    6   20                                                       
CONECT    8   11   14                                                       
CONECT    9   12   15                                                       
CONECT   10   12   16                                                       
CONECT   11    1    8   19                                                  
CONECT   12    9   10   22                                                  
CONECT   13    6   17   19                                                  
CONECT   14    8   15   17                                                  
CONECT   15    9   14   18                                                  
CONECT   16   10   18   23                                                  
CONECT   17   13   14   21                                                  
CONECT   18   15   16   21                                                  
CONECT   19   11   13   24                                                  
CONECT   20    2    3    7   24                                             
CONECT   21   17   18                                                       
CONECT   22    4   12                                                       
CONECT   23    5   16                                                       
CONECT   24   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0030212
HETATM    1  C1  UNL     1       5.561   2.208   0.478  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.474   0.830   0.185  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.248   0.193   0.043  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.220  -1.169  -0.247  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.041  -1.860  -0.400  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.066  -3.212  -0.687  1.00  0.00           O  
HETATM    7  C5  UNL     1       4.307  -3.876  -0.821  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.871  -1.169  -0.259  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.590  -1.546  -0.346  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.203  -0.467  -0.121  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.574  -0.287  -0.090  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.191   0.921   0.163  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.360   2.008   0.398  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.996   3.319   0.673  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.007   1.861   0.374  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.593   0.635   0.117  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.893   0.186   0.028  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.066   0.880   0.182  1.00  0.00           C  
HETATM   19  O3  UNL     1      -3.562   1.032   0.179  1.00  0.00           O  
HETATM   20  C16 UNL     1      -4.395  -0.056  -0.056  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.310  -0.326   1.152  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.275   0.342  -1.252  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.710  -1.339  -0.326  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.397  -1.469  -0.346  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.632   2.439   0.646  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.097   2.852  -0.272  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.015   2.355   1.445  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.155  -1.697  -0.354  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.116  -4.976  -0.938  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.903  -3.672   0.092  1.00  0.00           H  
HETATM   31  H7  UNL     1       4.807  -3.467  -1.738  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.220  -2.505  -0.552  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.780   3.270   1.436  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.418   3.768  -0.272  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.202   4.013   1.015  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.678   2.709   0.558  1.00  0.00           H  
HETATM   37  H13 UNL     1       3.068   1.921   0.404  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.955  -1.178   0.847  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.942   0.529   1.384  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.657  -0.668   1.972  1.00  0.00           H  
HETATM   41  H17 UNL     1      -6.263  -0.140  -1.110  1.00  0.00           H  
HETATM   42  H18 UNL     1      -5.447   1.434  -1.264  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.765   0.053  -2.178  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.306  -2.254  -0.523  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.919  -2.425  -0.546  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   28
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   29   30   31
CONECT    8    9   17
CONECT    9   10   32
CONECT   10   11   11   16
CONECT   11   12   24
CONECT   12   13   13   19
CONECT   13   14   15
CONECT   14   33   34   35
CONECT   15   16   16   36
CONECT   16   17
CONECT   17   18   18
CONECT   18   37
CONECT   19   20
CONECT   20   21   22   23
CONECT   21   38   39   40
CONECT   22   41   42   43
CONECT   23   24   24   44
CONECT   24   45
END

HMDB0030212
     RDKit          3D
Mukonicine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5613    2.2083    0.4779 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744    0.8303    0.1847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2477    0.1934    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -1.1694   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410   -1.8604   -0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658   -3.2123   -0.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -3.8763   -0.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -1.1693   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5899   -1.5463   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2027   -0.4667   -0.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740   -0.2866   -0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908    0.9214    0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    2.0083    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    3.3193    0.6733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071    1.8608    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5932    0.6347    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927    0.1856    0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    0.8797    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5624    1.0325    0.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3955   -0.0556   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3097   -0.3260    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2747    0.3415   -1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7098   -1.3394   -0.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3966   -1.4687   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6316    2.4388    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971    2.8521   -0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0152    2.3552    1.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552   -1.6969   -0.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157   -4.9765   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9033   -3.6717    0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8071   -3.4667   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -2.5053   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7799    3.2704    1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4179    3.7676   -0.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    4.0127    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    2.7095    0.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0679    1.9215    0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9554   -1.1778    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9421    0.5289    1.3838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574   -0.6684    1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2628   -0.1396   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4466    1.4337   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7649    0.0526   -2.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3062   -2.2542   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -2.4247   -0.5465 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  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 18  3  1  0
 17  8  1  0
 16 10  1  0
 24 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 18 37  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,11-Dihydro-8,10-dimethoxy-3,3,5-trimethylpyrano[3,2-a]carbazole, 9ci	HMDB

Chemical Formula

C₂₀H₂₁NO₃

Average Molecular Weight

323.3856

Monoisotopic Molecular Weight

323.152143543

IUPAC Name

13,15-dimethoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

Traditional Name

13,15-dimethoxy-5,5,8-trimethyl-6-oxa-17-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1,3,7,9,11(16),12,14-heptaene

CAS Registry Number

88607-43-6

SMILES

COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C(OC)=C1

InChI Identifier

InChI=1S/C20H21NO3/c1-11-8-14-15-9-12(22-4)10-16(23-5)18(15)21-17(14)13-6-7-20(2,3)24-19(11)13/h6-10,21H,1-5H3

InChI Key

APZRRMFSHXMDTQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Indole
Anisole
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Oxacycle
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
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: HMDB0030212)
Cell membrane (HMDB: HMDB0030212)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030212)

Source

Endogenous

Endogenous (HMDB: HMDB0030212)

Plant

Plant (HMDB: HMDB0030212)

Exogenous

Food

Food (HMDB: HMDB0030212)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030212)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	233 - 234 °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	0.0012 g/L	ALOGPS
logP	5.19	ALOGPS
logP	4.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.83 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	177.517	31661259
DarkChem	[M-H]-	180.537	31661259
DeepCCS	[M-2H]-	221.591	30932474
DeepCCS	[M+Na]+	197.697	30932474
AllCCS	[M+H]+	177.0	32859911
AllCCS	[M+H-H2O]+	173.6	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.1	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	183.7	32859911
AllCCS	[M+HCOO]-	183.1	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.	6.8 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9322 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2356.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	137.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	743.9 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	547.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1222.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	538.4 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	1349.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	485.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	425.0 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mukonicine	COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C(OC)=C1	3717.2	Standard polar	33892256
Mukonicine	COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C(OC)=C1	2940.8	Standard non polar	33892256
Mukonicine	COC1=CC2=C(NC3=C4C=CC(C)(C)OC4=C(C)C=C23)C(OC)=C1	3039.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mukonicine,1TMS,isomer #1	COC1=CC(OC)=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C	3082.8	Semi standard non polar	33892256
Mukonicine,1TMS,isomer #1	COC1=CC(OC)=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C	2632.8	Standard non polar	33892256
Mukonicine,1TBDMS,isomer #1	COC1=CC(OC)=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C(C)(C)C	3188.6	Semi standard non polar	33892256
Mukonicine,1TBDMS,isomer #1	COC1=CC(OC)=C2C(=C1)C1=CC(C)=C3OC(C)(C)C=CC3=C1N2[Si](C)(C)C(C)(C)C	2851.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mukonicine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0195000000-9b75b81b5b887d58bbc9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mukonicine 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 - Mukonicine 10V, Positive-QTOF	splash10-00di-0029000000-faa0e8b156be4bed3136	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 20V, Positive-QTOF	splash10-00dl-0094000000-108076fccbe922aee48c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 40V, Positive-QTOF	splash10-02ti-1090000000-5298a73c514a8baa764e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 10V, Negative-QTOF	splash10-00di-0019000000-79eeb72624074c61f300	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 20V, Negative-QTOF	splash10-00di-0069000000-cf51bd943f39bc12ab2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 40V, Negative-QTOF	splash10-0ka9-0090000000-5ecdc6574c8f9965c7af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 10V, Negative-QTOF	splash10-00di-0009000000-b8817382b3fde66270d6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 20V, Negative-QTOF	splash10-00di-0009000000-131076375e7afba8b6f7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 40V, Negative-QTOF	splash10-004i-0090000000-ca9c359741560905f30f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 10V, Positive-QTOF	splash10-00di-0009000000-7684723ce4870da7ab11	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 20V, Positive-QTOF	splash10-00di-0039000000-0037c5d1d594a7363929	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mukonicine 40V, Positive-QTOF	splash10-014i-1091000000-cc3acc7caaa6f321b9fc	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

FDB002031

KNApSAcK ID

C00024719

Chemspider ID

30776819

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86242003

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 Mukonicine (HMDB0030212)

MOL for HMDB0030212 (Mukonicine)

3D MOL for HMDB0030212 (Mukonicine)

3D SDF for HMDB0030212 (Mukonicine)

3D-SDF for HMDB0030212 (Mukonicine)

PDB for HMDB0030212 (Mukonicine)

3D PDB for HMDB0030212 (Mukonicine)

SMILES for HMDB0030212 (Mukonicine)

INCHI for HMDB0030212 (Mukonicine)

Structure for HMDB0030212 (Mukonicine)

3D Structure for HMDB0030212 (Mukonicine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra