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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:58:28 UTC

Update Date

2022-03-07 02:55:51 UTC

HMDB ID

HMDB0038642

Secondary Accession Numbers

HMDB38642

Metabolite Identification

Common Name

Fumitremorgin C

Description

Fumitremorgin C, also known as tryptoquivaline, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Based on a literature review a significant number of articles have been published on Fumitremorgin C.

Structure

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


  Mrv0541 02241221442D          

 28 32  0  0  1  0            999 V2000
    5.5187   -3.1036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5186   -3.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2330   -4.3410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2330   -5.1661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5185   -5.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -6.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -5.1659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895   -5.5784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3751   -5.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -4.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -4.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2551   -3.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -3.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -3.8269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -3.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852   -4.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1056   -4.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5904   -5.4207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897   -3.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -4.3409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0895   -6.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -6.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6606   -6.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749   -7.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0176   -5.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5026   -4.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0177   -4.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21  2  1  1  0  0  0
  8 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  4 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END

HMDB0038642
     RDKit          3D
Fumitremorgin C
 53 57  0  0  0  0  0  0  0  0999 V2000
    7.1825   -1.0528    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1783   -0.0880    1.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9700   -0.1952    0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7322   -1.2243   -0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360   -1.3310   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5479   -0.3949   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768   -0.2498   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    0.8837   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    1.4000    0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959    0.6415    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9944    0.7520    1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    1.2579   -0.8329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0770    2.3466    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521    3.4020   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    3.6592   -1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265    4.4112    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4142    0.0677   -0.7588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    0.0023    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501    0.9420    0.8710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626   -1.2430   -0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2848   -1.4440    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1271   -2.8876    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469   -3.4303    0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186   -2.3505   -0.0075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815   -2.2776   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2900   -3.1624   -0.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -1.0598   -1.5748 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4375   -0.9833   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547   -1.1320    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -1.9994    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0945   -0.6860    1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5169   -1.9516   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3537   -2.1487   -1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5326    2.2589    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769    1.5668    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5778    1.6013   -1.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032    2.2297    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    2.7336   -2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283    4.0564   -1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    4.4492   -2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760    5.1357    0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2353    5.0184    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849    3.9354    1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8804   -1.2144   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3240   -1.2421    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053   -0.7392    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9763   -2.9048    2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128   -3.4994    1.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -3.7694    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858   -4.3224    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6124   -1.1388   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572   -0.5854   -3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.0434   -2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 11  3  1  0
 27 17  1  0
 10  6  1  0
 24 20  1  0
 28  7  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  6
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 20 44  1  6
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 27 51  1  6
 28 52  1  0
 28 53  1  0
M  END


  Mrv0541 02241221442D          

 28 32  0  0  1  0            999 V2000
    5.5187   -3.1036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5186   -3.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2330   -4.3410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2330   -5.1661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5185   -5.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184   -6.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -5.1659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0895   -5.5784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3751   -5.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3752   -4.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5906   -4.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2551   -3.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346   -3.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -3.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -3.8269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -3.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2852   -4.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1056   -4.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5904   -5.4207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0897   -3.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -4.3409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0895   -6.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750   -6.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6606   -6.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3749   -7.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0176   -5.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5026   -4.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0177   -4.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21  2  1  1  0  0  0
  8 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  4 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038642

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1

> <INCHI_KEY>
DBEYVIGIPJSTOR-FHWLQOOXSA-N

> <FORMULA>
C22H25N3O3

> <MOLECULAR_WEIGHT>
379.4522

> <EXACT_MASS>
379.189591681

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
42.52010047530972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4,6,8-tetraene-14,20-dione

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
2.1129623283333334

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.79052044285027

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.106837658497426

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6415973374064436

> <JCHEM_POLAR_SURFACE_AREA>
65.64000000000001

> <JCHEM_REFRACTIVITY>
106.56979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4,6,8-tetraene-14,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038642
     RDKit          3D
Fumitremorgin C
 53 57  0  0  0  0  0  0  0  0999 V2000
    7.1825   -1.0528    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1783   -0.0880    1.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9700   -0.1952    0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7322   -1.2243   -0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360   -1.3310   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5479   -0.3949   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768   -0.2498   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    0.8837   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    1.4000    0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959    0.6415    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9944    0.7520    1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    1.2579   -0.8329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0770    2.3466    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521    3.4020   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    3.6592   -1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265    4.4112    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4142    0.0677   -0.7588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    0.0023    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501    0.9420    0.8710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626   -1.2430   -0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2848   -1.4440    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1271   -2.8876    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469   -3.4303    0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186   -2.3505   -0.0075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815   -2.2776   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2900   -3.1624   -0.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -1.0598   -1.5748 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4375   -0.9833   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547   -1.1320    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -1.9994    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0945   -0.6860    1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5169   -1.9516   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3537   -2.1487   -1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5326    2.2589    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769    1.5668    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5778    1.6013   -1.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032    2.2297    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    2.7336   -2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283    4.0564   -1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    4.4492   -2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760    5.1357    0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2353    5.0184    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849    3.9354    1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8804   -1.2144   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3240   -1.2421    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053   -0.7392    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9763   -2.9048    2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128   -3.4994    1.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -3.7694    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858   -4.3224    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6124   -1.1388   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572   -0.5854   -3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.0434   -2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 11  3  1  0
 27 17  1  0
 10  6  1  0
 24 20  1  0
 28  7  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  6
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 20 44  1  6
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 27 51  1  6
 28 52  1  0
 28 53  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  O   UNK     0      10.302  -5.793   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.301  -7.333   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      11.635  -8.103   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      11.635  -9.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.301 -10.413   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.301 -11.953   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       8.968  -9.643   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.634 -10.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.300  -9.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.300  -8.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.836  -7.627   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.210  -6.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.678  -6.059   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.773  -7.305   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.241  -7.144   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.385  -5.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.399  -8.712   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.930  -8.873   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.835 -10.119   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       7.634  -7.333   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.968  -8.103   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.634 -11.953   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.300 -12.723   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.966 -11.953   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.300 -14.263   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.100 -10.119   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.005  -8.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.100  -7.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   21                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18    9                                                       
CONECT   20   10   21                                                       
CONECT   21   20    7    2                                                  
CONECT   22    8   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    4   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    3                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0038642
HETATM    1  C1  UNL     1       7.182  -1.053   1.272  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.178  -0.088   1.501  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.970  -0.195   0.828  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.732  -1.224  -0.058  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.536  -1.331  -0.725  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.548  -0.395  -0.510  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.277  -0.250  -1.025  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.768   0.884  -0.427  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.681   1.400   0.407  1.00  0.00           N  
HETATM   10  C8  UNL     1       2.796   0.642   0.387  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.994   0.752   1.057  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.630   1.258  -0.833  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.077   2.347   0.055  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.752   3.402  -0.304  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.178   3.659  -1.708  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.126   4.411   0.719  1.00  0.00           C  
HETATM   17  N2  UNL     1      -1.414   0.068  -0.759  1.00  0.00           N  
HETATM   18  C15 UNL     1      -2.558   0.002   0.086  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.850   0.942   0.871  1.00  0.00           O  
HETATM   20  C16 UNL     1      -3.363  -1.243  -0.036  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.285  -1.444   1.134  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.127  -2.888   1.538  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.947  -3.430   0.796  1.00  0.00           C  
HETATM   24  N3  UNL     1      -2.419  -2.350  -0.007  1.00  0.00           N  
HETATM   25  C20 UNL     1      -1.182  -2.278  -0.705  1.00  0.00           C  
HETATM   26  O3  UNL     1      -0.290  -3.162  -0.615  1.00  0.00           O  
HETATM   27  C21 UNL     1      -0.995  -1.060  -1.575  1.00  0.00           C  
HETATM   28  C22 UNL     1       0.437  -0.983  -1.985  1.00  0.00           C  
HETATM   29  H1  UNL     1       7.355  -1.132   0.197  1.00  0.00           H  
HETATM   30  H2  UNL     1       6.832  -1.999   1.732  1.00  0.00           H  
HETATM   31  H3  UNL     1       8.095  -0.686   1.827  1.00  0.00           H  
HETATM   32  H4  UNL     1       5.517  -1.952  -0.217  1.00  0.00           H  
HETATM   33  H5  UNL     1       3.354  -2.149  -1.425  1.00  0.00           H  
HETATM   34  H6  UNL     1       1.533   2.259   0.976  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.177   1.567   1.755  1.00  0.00           H  
HETATM   36  H8  UNL     1      -0.578   1.601  -1.886  1.00  0.00           H  
HETATM   37  H9  UNL     1      -0.803   2.230   1.098  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.219   2.734  -2.317  1.00  0.00           H  
HETATM   39  H11 UNL     1      -3.228   4.056  -1.703  1.00  0.00           H  
HETATM   40  H12 UNL     1      -1.551   4.449  -2.156  1.00  0.00           H  
HETATM   41  H13 UNL     1      -2.876   5.136   0.343  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.235   5.018   1.010  1.00  0.00           H  
HETATM   43  H15 UNL     1      -2.485   3.935   1.670  1.00  0.00           H  
HETATM   44  H16 UNL     1      -3.880  -1.214  -1.002  1.00  0.00           H  
HETATM   45  H17 UNL     1      -5.324  -1.242   0.840  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.005  -0.739   1.940  1.00  0.00           H  
HETATM   47  H19 UNL     1      -3.976  -2.905   2.649  1.00  0.00           H  
HETATM   48  H20 UNL     1      -5.013  -3.499   1.243  1.00  0.00           H  
HETATM   49  H21 UNL     1      -2.173  -3.769   1.542  1.00  0.00           H  
HETATM   50  H22 UNL     1      -3.186  -4.322   0.194  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.612  -1.139  -2.499  1.00  0.00           H  
HETATM   52  H24 UNL     1       0.557  -0.585  -3.031  1.00  0.00           H  
HETATM   53  H25 UNL     1       0.820  -2.043  -2.037  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   32
CONECT    5    6    6   33
CONECT    6    7   10
CONECT    7    8    8   28
CONECT    8    9   12
CONECT    9   10   34
CONECT   10   11   11
CONECT   11   35
CONECT   12   13   17   36
CONECT   13   14   14   37
CONECT   14   15   16
CONECT   15   38   39   40
CONECT   16   41   42   43
CONECT   17   18   27
CONECT   18   19   19   20
CONECT   20   21   24   44
CONECT   21   22   45   46
CONECT   22   23   47   48
CONECT   23   24   49   50
CONECT   24   25
CONECT   25   26   26   27
CONECT   27   28   51
CONECT   28   52   53
END

HMDB0038642
     RDKit          3D
Fumitremorgin C
 53 57  0  0  0  0  0  0  0  0999 V2000
    7.1825   -1.0528    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1783   -0.0880    1.5006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9700   -0.1952    0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7322   -1.2243   -0.0580 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5360   -1.3310   -0.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5479   -0.3949   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2768   -0.2498   -1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    0.8837   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6813    1.4000    0.4066 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959    0.6415    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9944    0.7520    1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301    1.2579   -0.8329 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0770    2.3466    0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7521    3.4020   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1777    3.6592   -1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265    4.4112    0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4142    0.0677   -0.7588 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5584    0.0023    0.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501    0.9420    0.8710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626   -1.2430   -0.0356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2848   -1.4440    1.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1271   -2.8876    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9469   -3.4303    0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186   -2.3505   -0.0075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815   -2.2776   -0.7054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2900   -3.1624   -0.6148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -1.0598   -1.5748 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4375   -0.9833   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547   -1.1320    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8317   -1.9994    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0945   -0.6860    1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5169   -1.9516   -0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3537   -2.1487   -1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5326    2.2589    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1769    1.5668    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5778    1.6013   -1.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032    2.2297    1.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    2.7336   -2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283    4.0564   -1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    4.4492   -2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8760    5.1357    0.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2353    5.0184    1.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4849    3.9354    1.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8804   -1.2144   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3240   -1.2421    0.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053   -0.7392    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9763   -2.9048    2.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128   -3.4994    1.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1729   -3.7694    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1858   -4.3224    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6124   -1.1388   -2.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5572   -0.5854   -3.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8197   -2.0434   -2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 11  3  1  0
 27 17  1  0
 10  6  1  0
 24 20  1  0
 28  7  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  5 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  6
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 20 44  1  6
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 27 51  1  6
 28 52  1  0
 28 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tryptoquivaline	ChEBI
Tryproquivaline D (2's-(2'alpha,9'alpha(4R(s)),9'abeta))-isomer	MeSH
Tryproquivaline L (9'r-(9'alpha(r*),9'abeta))-isomer	MeSH
Tryproquivaline L (9'r-(9'alpha(s*),9'abeta))-isomer	MeSH
Tryproquivaline m (2's-(2'alpha,9'alpha(4R(s)),9'abeta))-isomer	MeSH
Tryproquivaline m (2's-(2'alpha,9'alpha(4S(s)),9'abeta))-isomer	MeSH
Tryproquivaline N (2's-(2'alpha,9'alpha(r*),9'abeta))-isomer	MeSH
SM-Q	HMDB

Chemical Formula

C₂₂H₂₅N₃O₃

Average Molecular Weight

379.4522

Monoisotopic Molecular Weight

379.189591681

IUPAC Name

(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4,6,8-tetraene-14,20-dione

Traditional Name

(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4,6,8-tetraene-14,20-dione

CAS Registry Number

118974-02-0

SMILES

COC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C1

InChI Identifier

InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1

InChI Key

DBEYVIGIPJSTOR-FHWLQOOXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Anisole
Dioxopiperazine
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Lactam
Azacycle
Ether
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:72763 )
organic heteropentacyclic compound (CHEBI:72763 )
indole alkaloid (CHEBI:72763 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0038642)

Food

Food (HMDB: HMDB0038642)

Process

Not Available

Role

Biological role

Mycotoxin (HMDB: HMDB0038642)
Nutrient (HMDB: HMDB0038642)

Modulator

Inhibitor

Breast cancer resistance protein inhibitor (HMDB: HMDB0038642)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	259.5 - 260.5 °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	0.39 g/L	ALOGPS
logP	2.2	ALOGPS
logP	2.11	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	15.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.64 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.57 m³·mol⁻¹	ChemAxon
Polarizability	42.52 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	187.488	31661259
DarkChem	[M-H]-	188.414	31661259
DeepCCS	[M+H]+	198.009	30932474
DeepCCS	[M-H]-	195.614	30932474
DeepCCS	[M-2H]-	228.498	30932474
DeepCCS	[M+Na]+	203.942	30932474
AllCCS	[M+H]+	192.8	32859911
AllCCS	[M+H-H2O]+	190.2	32859911
AllCCS	[M+NH4]+	195.3	32859911
AllCCS	[M+Na]+	196.0	32859911
AllCCS	[M-H]-	196.5	32859911
AllCCS	[M+Na-2H]-	196.6	32859911
AllCCS	[M+HCOO]-	196.9	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.	6.35 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5681 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2437.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	223.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	140.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	482.0 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	450.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	997.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	482.3 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	1311.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	208.1 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	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fumitremorgin C	COC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C1	4824.4	Standard polar	33892256
Fumitremorgin C	COC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C1	3606.5	Standard non polar	33892256
Fumitremorgin C	COC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C1	3638.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fumitremorgin C,1TMS,isomer #1	COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C)C2=C1	3394.4	Semi standard non polar	33892256
Fumitremorgin C,1TMS,isomer #1	COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C)C2=C1	3295.6	Standard non polar	33892256
Fumitremorgin C,1TBDMS,isomer #1	COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C(C)(C)C)C2=C1	3520.7	Semi standard non polar	33892256
Fumitremorgin C,1TBDMS,isomer #1	COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C(C)(C)C)C2=C1	3531.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w2a-8095000000-7194759fc8623292bdeb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin C GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumitremorgin C 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 - Fumitremorgin C 10V, Positive-QTOF	splash10-001i-0009000000-0f0c39953390b4eda991	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Positive-QTOF	splash10-001i-2119000000-673774e3d3fbffa8e334	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Positive-QTOF	splash10-05fu-9130000000-21de2d5497bc35a45a63	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 10V, Negative-QTOF	splash10-004i-0009000000-36a2fe9ac638e57b2fc2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Negative-QTOF	splash10-004i-7079000000-092c074c39d9e22324d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Negative-QTOF	splash10-0gb9-9080000000-e123deaf8b2815821b01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 10V, Positive-QTOF	splash10-001i-0009000000-bd5ffa7b6ba5e943ad00	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Positive-QTOF	splash10-001i-0009000000-5642131e191c150db5b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Positive-QTOF	splash10-00bi-3139000000-f79890b4f8399c58e00e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 10V, Negative-QTOF	splash10-004i-0009000000-478cc77e0dbfe3e7b7cb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Negative-QTOF	splash10-004i-0009000000-16ac16601dba9cca9075	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Negative-QTOF	splash10-004i-1229000000-742943f1d35328892cb7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018037

KNApSAcK ID

C00011298

Chemspider ID

357779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

403923

PDB ID

Not Available

ChEBI ID

72763

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 Fumitremorgin C (HMDB0038642)

MOL for HMDB0038642 (Fumitremorgin C)

3D MOL for HMDB0038642 (Fumitremorgin C)

3D SDF for HMDB0038642 (Fumitremorgin C)

3D-SDF for HMDB0038642 (Fumitremorgin C)

PDB for HMDB0038642 (Fumitremorgin C)

3D PDB for HMDB0038642 (Fumitremorgin C)

SMILES for HMDB0038642 (Fumitremorgin C)

INCHI for HMDB0038642 (Fumitremorgin C)

Structure for HMDB0038642 (Fumitremorgin C)

3D Structure for HMDB0038642 (Fumitremorgin C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra