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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:25 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030202

Secondary Accession Numbers

HMDB30202

Metabolite Identification

Common Name

Fumigaclavine A

Description

Fumigaclavine A belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. Fumigaclavine A is an antibacterial ergoline alkaloid produced by endophytic Aspergillus. Fumigaclavine A is a very strong basic compound (based on its pKa).

Structure

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

HMDB0030202
     RDKit          3D
Fumigaclavine A
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.2759   -3.4333   -0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -2.6131    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -3.0854    1.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.3459   -0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -0.5092    0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    0.6097    1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    0.6230    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175    1.9787    0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706    2.0950   -0.3913 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    3.4861   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    1.3216   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    1.5015   -1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512    0.8435   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    1.0647   -1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102    0.1166   -0.6098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.6913    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8242   -1.7934    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586   -2.3807    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -1.9021    1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979   -0.8017    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768   -0.2455   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -0.1584   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938   -3.4214   -1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3295   -3.1075   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579   -4.4961   -0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -1.1092    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    0.4550    2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1989    0.0863    0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.0572   -0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    1.6404    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024    2.7287    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    2.0924    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    3.7568   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558    3.8760    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915    4.0439   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893    1.6164    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    2.5759   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.9866   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3056    1.8477   -1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362   -0.0045   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088   -2.1836    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520   -3.2490    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423   -2.3832    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759   -0.4895   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 11  1  0
 21 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  0
M  END


  Mrv0541 05061305042D          

 22 25  0  0  0  0            999 V2000
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2989   -3.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5849   -3.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301   -3.8687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5859   -2.6321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  9  1  0  0  0  0
 11  2  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 15  7  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  2  0  0  0  0
 22 11  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030202

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CN(C)C2CC3=CNC4=CC=CC(C2C1OC(C)=O)=C34

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2O2/c1-10-9-20(3)15-7-12-8-19-14-6-4-5-13(16(12)14)17(15)18(10)22-11(2)21/h4-6,8,10,15,17-19H,7,9H2,1-3H3

> <INCHI_KEY>
GJSSYQDXZLZOLR-UHFFFAOYSA-N

> <FORMULA>
C18H22N2O2

> <MOLECULAR_WEIGHT>
298.3795

> <EXACT_MASS>
298.168127958

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.777943449907234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.2402231293333337

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.053048852645148

> <JCHEM_PKA_STRONGEST_BASIC>
8.495710975765837

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
85.858

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030202
     RDKit          3D
Fumigaclavine A
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.2759   -3.4333   -0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -2.6131    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -3.0854    1.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.3459   -0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -0.5092    0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    0.6097    1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    0.6230    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175    1.9787    0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706    2.0950   -0.3913 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    3.4861   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    1.3216   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    1.5015   -1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512    0.8435   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    1.0647   -1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102    0.1166   -0.6098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.6913    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8242   -1.7934    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586   -2.3807    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -1.9021    1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979   -0.8017    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768   -0.2455   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -0.1584   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938   -3.4214   -1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3295   -3.1075   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579   -4.4961   -0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -1.1092    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    0.4550    2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1989    0.0863    0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.0572   -0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    1.6404    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024    2.7287    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    2.0924    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    3.7568   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558    3.8760    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915    4.0439   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893    1.6164    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    2.5759   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.9866   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3056    1.8477   -1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362   -0.0045   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088   -2.1836    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520   -3.2490    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423   -2.3832    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759   -0.4895   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 11  1  0
 21 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.425  -7.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.237  -1.827   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.574  -4.910   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.092  -6.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.239  -4.142   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -2.905  -2.598   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -0.243  -7.222   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.094  -4.913   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   20                                                            
CONECT    4    5    6                                                       
CONECT    5    4   13                                                       
CONECT    6    4   14                                                       
CONECT    7   12   15                                                       
CONECT    8   12   19                                                       
CONECT    9   10   20                                                       
CONECT   10    1    9   18                                                  
CONECT   11    2   21   22                                                  
CONECT   12    7    8   16                                                  
CONECT   13    5   16   17                                                  
CONECT   14    6   16   19                                                  
CONECT   15    7   17   20                                                  
CONECT   16   12   13   14                                                  
CONECT   17   13   15   18                                                  
CONECT   18   10   17   22                                                  
CONECT   19    8   14                                                       
CONECT   20    3    9   15                                                  
CONECT   21   11                                                            
CONECT   22   11   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0030202
HETATM    1  C1  UNL     1       3.276  -3.433  -0.783  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.419  -2.613   0.111  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.053  -3.085   1.210  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.012  -1.346  -0.229  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.181  -0.509   0.593  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.083   0.610   1.035  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.399   0.623   0.244  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.517   1.979   0.929  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.871   2.095  -0.391  1.00  0.00           N  
HETATM   10  C7  UNL     1       0.630   3.486  -0.600  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.312   1.322  -0.271  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.262   1.502  -1.449  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.551   0.843  -1.036  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.891   1.065  -1.283  1.00  0.00           C  
HETATM   15  N2  UNL     1      -4.610   0.117  -0.610  1.00  0.00           N  
HETATM   16  C12 UNL     1      -3.730  -0.691   0.052  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.824  -1.793   0.877  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.659  -2.381   1.388  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.400  -1.902   1.101  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.298  -0.802   0.278  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.477  -0.245  -0.210  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.029  -0.158  -0.143  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.894  -3.421  -1.812  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.330  -3.107  -0.763  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.258  -4.496  -0.449  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.937  -1.109   1.491  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.399   0.455   2.088  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.199   0.086   0.781  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.242   0.057  -0.717  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.735   1.640   0.022  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.302   2.729   0.994  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.721   2.092   1.693  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.267   3.757  -1.596  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.056   3.876   0.204  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.591   4.044  -0.439  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.889   1.616   0.638  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.436   2.576  -1.555  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.923   0.987  -2.345  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.306   1.848  -1.899  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.636  -0.004  -0.579  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.809  -2.184   1.114  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.752  -3.249   2.037  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.542  -2.383   1.509  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.076  -0.489  -1.230  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   26
CONECT    6    7    8   27
CONECT    7   28   29   30
CONECT    8    9   31   32
CONECT    9   10   11
CONECT   10   33   34   35
CONECT   11   12   22   36
CONECT   12   13   37   38
CONECT   13   14   14   21
CONECT   14   15   39
CONECT   15   16   40
CONECT   16   17   17   21
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21   22
CONECT   22   44
END

HMDB0030202
     RDKit          3D
Fumigaclavine A
 44 47  0  0  0  0  0  0  0  0999 V2000
    3.2759   -3.4333   -0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4188   -2.6131    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -3.0854    1.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0119   -1.3459   -0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1814   -0.5092    0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    0.6097    1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    0.6230    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5175    1.9787    0.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706    2.0950   -0.3913 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    3.4861   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3118    1.3216   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    1.5015   -1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512    0.8435   -1.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911    1.0647   -1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6102    0.1166   -0.6098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7300   -0.6913    0.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8242   -1.7934    0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586   -2.3807    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -1.9021    1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979   -0.8017    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4768   -0.2455   -0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292   -0.1584   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938   -3.4214   -1.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3295   -3.1075   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2579   -4.4961   -0.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -1.1092    1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    0.4550    2.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1989    0.0863    0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417    0.0572   -0.7174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    1.6404    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024    2.7287    0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209    2.0924    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    3.7568   -1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558    3.8760    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915    4.0439   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8893    1.6164    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4357    2.5759   -1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.9866   -2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3056    1.8477   -1.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362   -0.0045   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8088   -2.1836    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520   -3.2490    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423   -2.3832    1.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0759   -0.4895   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  5  1  0
 22 11  1  0
 21 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isofumigaclavine a	HMDB
4,6-Dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-yl acetic acid	Generator
Isofumigaclavine a, (8alpha,9beta)-isomer	MeSH
9-Acetoxy-6,8-dimethylergoline	MeSH

Chemical Formula

C₁₈H₂₂N₂O₂

Average Molecular Weight

298.3795

Monoisotopic Molecular Weight

298.168127958

IUPAC Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

Traditional Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-3-yl acetate

CAS Registry Number

6879-59-0

SMILES

CC1CN(C)C2CC3=CNC4=CC=CC(C2C1OC(C)=O)=C34

InChI Identifier

InChI=1S/C18H22N2O2/c1-10-9-20(3)15-7-12-8-19-14-6-4-5-13(16(12)14)17(15)18(10)22-11(2)21/h4-6,8,10,15,17-19H,7,9H2,1-3H3

InChI Key

GJSSYQDXZLZOLR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Clavines and derivatives

Direct Parent

Clavines and derivatives

Alternative Parents

Substituents

Clavine skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030202)

Membrane (HMDB: HMDB0030202)
Cell membrane (HMDB: HMDB0030202)

Source

Endogenous

Endogenous (HMDB: HMDB0030202)

Exogenous

Food

Food (HMDB: HMDB0030202)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	84 - 85 °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	0.17 g/L	ALOGPS
logP	3	ALOGPS
logP	2.24	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	17.05	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.86 m³·mol⁻¹	ChemAxon
Polarizability	32.78 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]+	171.047	31661259
DarkChem	[M-H]-	171.431	31661259
DeepCCS	[M-2H]-	200.535	30932474
DeepCCS	[M+Na]+	175.838	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.3	32859911
AllCCS	[M-H]-	178.4	32859911
AllCCS	[M+Na-2H]-	178.1	32859911
AllCCS	[M+HCOO]-	178.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fumigaclavine A	CC1CN(C)C2CC3=CNC4=CC=CC(C2C1OC(C)=O)=C34	3621.5	Standard polar	33892256
Fumigaclavine A	CC1CN(C)C2CC3=CNC4=CC=CC(C2C1OC(C)=O)=C34	2514.3	Standard non polar	33892256
Fumigaclavine A	CC1CN(C)C2CC3=CNC4=CC=CC(C2C1OC(C)=O)=C34	2681.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fumigaclavine A,1TMS,isomer #1	CC(=O)OC1C(C)CN(C)C2CC3=CN([Si](C)(C)C)C4=CC=CC(=C34)C12	2529.6	Semi standard non polar	33892256
Fumigaclavine A,1TMS,isomer #1	CC(=O)OC1C(C)CN(C)C2CC3=CN([Si](C)(C)C)C4=CC=CC(=C34)C12	2520.6	Standard non polar	33892256
Fumigaclavine A,1TBDMS,isomer #1	CC(=O)OC1C(C)CN(C)C2CC3=CN([Si](C)(C)C(C)(C)C)C4=CC=CC(=C34)C12	2741.3	Semi standard non polar	33892256
Fumigaclavine A,1TBDMS,isomer #1	CC(=O)OC1C(C)CN(C)C2CC3=CN([Si](C)(C)C(C)(C)C)C4=CC=CC(=C34)C12	2742.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fumigaclavine A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2910000000-346f654859d73bbc8f91	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumigaclavine A 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 - Fumigaclavine A 10V, Positive-QTOF	splash10-0002-0090000000-b715403218c40e676043	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 20V, Positive-QTOF	splash10-052r-0290000000-24c9fb2ef862ffc27093	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 40V, Positive-QTOF	splash10-0udj-1910000000-3dc6ab6c6f35de210795	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 10V, Negative-QTOF	splash10-052b-1090000000-53f5b8043f56a590e046	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 20V, Negative-QTOF	splash10-0a4i-3090000000-a25338e53c4a3846217e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 40V, Negative-QTOF	splash10-0pbl-9450000000-f4d9132368c12c68e42e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 10V, Negative-QTOF	splash10-0a4i-1090000000-b5f0630f6481fb38021c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 20V, Negative-QTOF	splash10-0a4j-5090000000-d8c0ad054a355a6fd1e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 40V, Negative-QTOF	splash10-056r-2590000000-73c94c935ea3f9a7260e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 10V, Positive-QTOF	splash10-000i-0090000000-e68cbcd9fc6ab3f36905	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 20V, Positive-QTOF	splash10-000j-0090000000-9aa67a1aee54fe1adca0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumigaclavine A 40V, Positive-QTOF	splash10-0fki-1930000000-6d5d1720775ae299602c	2021-09-22	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

FDB002020

KNApSAcK ID

C00011246

Chemspider ID

28581575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fumigaclavine A

METLIN ID

Not Available

PubChem Compound

12309935

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 Fumigaclavine A (HMDB0030202)

MOL for HMDB0030202 (Fumigaclavine A)

3D MOL for HMDB0030202 (Fumigaclavine A)

3D SDF for HMDB0030202 (Fumigaclavine A)

3D-SDF for HMDB0030202 (Fumigaclavine A)

PDB for HMDB0030202 (Fumigaclavine A)

3D PDB for HMDB0030202 (Fumigaclavine A)

SMILES for HMDB0030202 (Fumigaclavine A)

INCHI for HMDB0030202 (Fumigaclavine A)

Structure for HMDB0030202 (Fumigaclavine A)

3D Structure for HMDB0030202 (Fumigaclavine A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra