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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:28 UTC

Update Date

2022-03-07 02:52:31 UTC

HMDB ID

HMDB0030381

Secondary Accession Numbers

HMDB30381

Metabolite Identification

Common Name

Roquefortine

Description

Roquefortine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review a significant number of articles have been published on Roquefortine.

Structure

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


  Mrv0541 02241215412D          

 29 33  0  0  0  0            999 V2000
    1.5794   -2.0894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -2.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3821   -3.1561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551   -2.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -1.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372   -0.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -0.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    0.3603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7154    0.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574    1.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2364    1.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1527   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -0.5237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481    0.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4886   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551    0.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    1.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938   -1.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124    3.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    2.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    2.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317    1.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 24  2  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 15 28  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 25 26  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0030381
     RDKit          3D
Roquefortine
 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.9918    0.9885   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632    0.8968   -1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    1.2048   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    1.0808    1.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2665    2.6377   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.2634   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216    0.4050   -1.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.0697   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    0.7501   -2.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446    0.7535   -4.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926    0.4321   -2.7405 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    0.2043   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046   -0.0581   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -0.3077   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002    0.3086    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492   -0.2052    1.5960 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6277   -1.1221    1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221   -1.1787    0.9128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.3042   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    0.1200    0.8688 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    0.6265   -0.5122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    0.5942    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547   -0.5071    1.2988 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9925   -1.5201    0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616   -2.8200    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498   -3.6207    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134   -3.2092   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8639   -1.9431   -0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -1.1122   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8239    0.7639   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2001    1.2657    0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6172    0.6225   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    2.0414    1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416    0.2523    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1119    0.8859    1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    2.8315   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228    3.2219   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    3.0744    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    0.9947   -2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328   -0.6254   -2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648    2.1787   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.3584   -3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -0.0835   -2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811    1.0918   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924    0.0958    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072   -1.7213    2.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793    1.5586    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6435   -0.5661    2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -3.1458    2.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615   -4.6171    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7656   -3.9003   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312   -1.6141   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22  6  1  0
 29 24  1  0
 29  6  1  0
 21  8  1  0
 18 14  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
 11 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  1  0
M  END


  Mrv0541 02241215412D          

 29 33  0  0  0  0            999 V2000
    1.5794   -2.0894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5931   -2.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3821   -3.1561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8551   -2.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -1.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6008   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0372   -0.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721   -0.0109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790    0.3603    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7154    0.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9574    1.7512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2364    1.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1527   -0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8111   -0.5237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2481    0.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4886   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8551    0.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6145    1.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938   -1.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124    3.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    2.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509    2.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317    1.7334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 24  2  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 15 28  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 25 26  2  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030381

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+

> <INCHI_KEY>
SPWSUFUPTSJWNG-CXUHLZMHSA-N

> <FORMULA>
C22H23N5O2

> <MOLECULAR_WEIGHT>
389.4503

> <EXACT_MASS>
389.185175005

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.526723945848154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
1.549902113666667

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.713760150970522

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.699754210196987

> <JCHEM_PKA_STRONGEST_BASIC>
6.040133075814444

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
111.176

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030381
     RDKit          3D
Roquefortine
 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.9918    0.9885   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632    0.8968   -1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    1.2048   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    1.0808    1.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2665    2.6377   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.2634   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216    0.4050   -1.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.0697   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    0.7501   -2.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446    0.7535   -4.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926    0.4321   -2.7405 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    0.2043   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046   -0.0581   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -0.3077   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002    0.3086    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492   -0.2052    1.5960 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6277   -1.1221    1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221   -1.1787    0.9128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.3042   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    0.1200    0.8688 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    0.6265   -0.5122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    0.5942    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547   -0.5071    1.2988 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9925   -1.5201    0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616   -2.8200    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498   -3.6207    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134   -3.2092   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8639   -1.9431   -0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -1.1122   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8239    0.7639   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2001    1.2657    0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6172    0.6225   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    2.0414    1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416    0.2523    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1119    0.8859    1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    2.8315   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228    3.2219   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    3.0744    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    0.9947   -2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328   -0.6254   -2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648    2.1787   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.3584   -3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -0.0835   -2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811    1.0918   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924    0.0958    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072   -1.7213    2.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793    1.5586    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6435   -0.5661    2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -3.1458    2.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615   -4.6171    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7656   -3.9003   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312   -1.6141   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22  6  1  0
 29 24  1  0
 29  6  1  0
 21  8  1  0
 18 14  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
 11 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  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  N   UNK     0       2.948  -3.900   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.974  -5.440   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.447  -5.891   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.330  -4.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.400  -3.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.855  -1.927   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.803  -0.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.304  -1.149   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.255  -0.020   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       4.254   0.673   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.202   1.796   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.654   3.269   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.704   1.450   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.441   2.332   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.790   1.406   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.285  -0.049   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.514  -0.978   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.330   1.381   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.779  -0.092   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.280  -0.439   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.330   0.688   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.880   2.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.379   2.507   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.855  -2.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.023   5.891   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.429   5.265   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.405   3.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.588   3.736   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.046   3.236   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   13   16                                                  
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13    9   11   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18   28                                             
CONECT   16    9   15   17                                                  
CONECT   17   16   19                                                       
CONECT   18   15   19   23                                                  
CONECT   19   17   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   18   22                                                       
CONECT   24    8                                                            
CONECT   25   26                                                            
CONECT   26   25   28                                                       
CONECT   27   28                                                            
CONECT   28   15   26   27   29                                             
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

COMPND    HMDB0030381
HETATM    1  C1  UNL     1      -4.992   0.989  -0.523  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.763   0.897  -1.045  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.636   1.205  -0.121  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.037   1.081   1.336  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.267   2.638  -0.368  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.501   0.263  -0.411  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.022   0.405  -1.830  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.337   1.070  -1.773  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.214   0.750  -2.905  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.745   0.753  -4.065  1.00  0.00           O  
HETATM   11  N1  UNL     1       2.593   0.432  -2.740  1.00  0.00           N  
HETATM   12  C10 UNL     1       3.131   0.204  -1.438  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.405  -0.058  -1.295  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.044  -0.308  -0.034  1.00  0.00           C  
HETATM   15  C13 UNL     1       6.200   0.309   0.397  1.00  0.00           C  
HETATM   16  N2  UNL     1       6.549  -0.205   1.596  1.00  0.00           N  
HETATM   17  C14 UNL     1       5.628  -1.122   1.902  1.00  0.00           C  
HETATM   18  N3  UNL     1       4.722  -1.179   0.913  1.00  0.00           N  
HETATM   19  C15 UNL     1       2.245   0.304  -0.301  1.00  0.00           C  
HETATM   20  O2  UNL     1       2.658   0.120   0.869  1.00  0.00           O  
HETATM   21  N4  UNL     1       0.851   0.627  -0.512  1.00  0.00           N  
HETATM   22  C16 UNL     1      -0.275   0.594   0.400  1.00  0.00           C  
HETATM   23  N5  UNL     1      -0.055  -0.507   1.299  1.00  0.00           N  
HETATM   24  C17 UNL     1      -0.992  -1.520   0.967  1.00  0.00           C  
HETATM   25  C18 UNL     1      -1.162  -2.820   1.481  1.00  0.00           C  
HETATM   26  C19 UNL     1      -2.150  -3.621   0.994  1.00  0.00           C  
HETATM   27  C20 UNL     1      -3.013  -3.209  -0.003  1.00  0.00           C  
HETATM   28  C21 UNL     1      -2.864  -1.943  -0.518  1.00  0.00           C  
HETATM   29  C22 UNL     1      -1.850  -1.112  -0.023  1.00  0.00           C  
HETATM   30  H1  UNL     1      -5.824   0.764  -1.195  1.00  0.00           H  
HETATM   31  H2  UNL     1      -5.200   1.266   0.493  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.617   0.622  -2.068  1.00  0.00           H  
HETATM   33  H4  UNL     1      -3.448   2.041   1.722  1.00  0.00           H  
HETATM   34  H5  UNL     1      -3.742   0.252   1.463  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.112   0.886   1.949  1.00  0.00           H  
HETATM   36  H7  UNL     1      -2.025   2.832  -1.448  1.00  0.00           H  
HETATM   37  H8  UNL     1      -3.223   3.222  -0.206  1.00  0.00           H  
HETATM   38  H9  UNL     1      -1.550   3.074   0.327  1.00  0.00           H  
HETATM   39  H10 UNL     1      -1.685   0.995  -2.483  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.833  -0.625  -2.251  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.265   2.179  -1.725  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.236   0.358  -3.556  1.00  0.00           H  
HETATM   43  H14 UNL     1       5.014  -0.083  -2.235  1.00  0.00           H  
HETATM   44  H15 UNL     1       6.781   1.092  -0.108  1.00  0.00           H  
HETATM   45  H16 UNL     1       7.392   0.096   2.139  1.00  0.00           H  
HETATM   46  H17 UNL     1       5.607  -1.721   2.795  1.00  0.00           H  
HETATM   47  H18 UNL     1      -0.379   1.559   0.948  1.00  0.00           H  
HETATM   48  H19 UNL     1       0.644  -0.566   2.044  1.00  0.00           H  
HETATM   49  H20 UNL     1      -0.486  -3.146   2.263  1.00  0.00           H  
HETATM   50  H21 UNL     1      -2.261  -4.617   1.406  1.00  0.00           H  
HETATM   51  H22 UNL     1      -3.766  -3.900  -0.331  1.00  0.00           H  
HETATM   52  H23 UNL     1      -3.531  -1.614  -1.296  1.00  0.00           H  
CONECT    1    2    2   30   31
CONECT    2    3   32
CONECT    3    4    5    6
CONECT    4   33   34   35
CONECT    5   36   37   38
CONECT    6    7   22   29
CONECT    7    8   39   40
CONECT    8    9   21   41
CONECT    9   10   10   11
CONECT   11   12   42
CONECT   12   13   13   19
CONECT   13   14   43
CONECT   14   15   15   18
CONECT   15   16   44
CONECT   16   17   45
CONECT   17   18   18   46
CONECT   19   20   20   21
CONECT   21   22
CONECT   22   23   47
CONECT   23   24   48
CONECT   24   25   25   29
CONECT   25   26   49
CONECT   26   27   27   50
CONECT   27   28   51
CONECT   28   29   29   52
END

HMDB0030381
     RDKit          3D
Roquefortine
 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.9918    0.9885   -0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7632    0.8968   -1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362    1.2048   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    1.0808    1.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2665    2.6377   -0.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.2634   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216    0.4050   -1.8301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373    1.0697   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    0.7501   -2.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446    0.7535   -4.0649 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926    0.4321   -2.7405 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    0.2043   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4046   -0.0581   -1.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0442   -0.3077   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002    0.3086    0.3971 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5492   -0.2052    1.5960 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6277   -1.1221    1.9018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221   -1.1787    0.9128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.3042   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    0.1200    0.8688 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    0.6265   -0.5122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747    0.5942    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0547   -0.5071    1.2988 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9925   -1.5201    0.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616   -2.8200    1.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1498   -3.6207    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0134   -3.2092   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8639   -1.9431   -0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502   -1.1122   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8239    0.7639   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2001    1.2657    0.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6172    0.6225   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481    2.0414    1.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416    0.2523    1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1119    0.8859    1.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253    2.8315   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228    3.2219   -0.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    3.0744    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    0.9947   -2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328   -0.6254   -2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2648    2.1787   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.3584   -3.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0142   -0.0835   -2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7811    1.0918   -0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924    0.0958    2.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6072   -1.7213    2.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3793    1.5586    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6435   -0.5661    2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -3.1458    2.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615   -4.6171    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7656   -3.9003   -0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5312   -1.6141   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 12 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 22  6  1  0
 29 24  1  0
 29  6  1  0
 21  8  1  0
 18 14  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
 11 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 22 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Roquefortine C	HMDB
Roquefortin	HMDB
Isoroquefortine C	HMDB
Roquefortine	MeSH

Chemical Formula

C₂₂H₂₃N₅O₂

Average Molecular Weight

389.4503

Monoisotopic Molecular Weight

389.185175005

IUPAC Name

(4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione

Traditional Name

(4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione

CAS Registry Number

58735-64-1

SMILES

CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1

InChI Identifier

InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+

InChI Key

SPWSUFUPTSJWNG-CXUHLZMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Dioxopiperazine
2,5-dioxopiperazine
Secondary aliphatic/aromatic amine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Heteroaromatic compound
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Azole
Imidazole
Secondary carboxylic acid amide
Amino acid or derivatives
Lactam
Carboxamide group
Secondary amine
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030381)

Source

Endogenous

Endogenous (HMDB: HMDB0030381)

Animal

Animal (HMDB: HMDB0030381)

Exogenous

Food

Food (HMDB: HMDB0030381)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Exogenous (HMDB: HMDB0030381)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 - 200 °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	0.11 g/L	ALOGPS
logP	3.07	ALOGPS
logP	1.55	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	6.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.18 m³·mol⁻¹	ChemAxon
Polarizability	41.53 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	220.183	30932474
DeepCCS	[M+Na]+	195.337	30932474
AllCCS	[M+H]+	194.9	32859911
AllCCS	[M+H-H2O]+	192.2	32859911
AllCCS	[M+NH4]+	197.3	32859911
AllCCS	[M+Na]+	198.0	32859911
AllCCS	[M-H]-	195.4	32859911
AllCCS	[M+Na-2H]-	195.3	32859911
AllCCS	[M+HCOO]-	195.3	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.	5.09 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7175 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.99 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2040.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	386.1 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	518.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	947.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	395.8 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	1279.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	310.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	235.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	196.7 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Roquefortine	CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1	5154.7	Standard polar	33892256
Roquefortine	CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1	3255.9	Standard non polar	33892256
Roquefortine	CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1	3880.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Roquefortine,1TMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3493.4	Semi standard non polar	33892256
Roquefortine,1TMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3312.6	Standard non polar	33892256
Roquefortine,1TMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12	3430.2	Semi standard non polar	33892256
Roquefortine,1TMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12	3254.8	Standard non polar	33892256
Roquefortine,1TMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3687.4	Semi standard non polar	33892256
Roquefortine,1TMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3496.3	Standard non polar	33892256
Roquefortine,2TMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3323.1	Semi standard non polar	33892256
Roquefortine,2TMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3239.2	Standard non polar	33892256
Roquefortine,2TMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3551.5	Semi standard non polar	33892256
Roquefortine,2TMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3461.7	Standard non polar	33892256
Roquefortine,2TMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3545.7	Semi standard non polar	33892256
Roquefortine,2TMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3387.0	Standard non polar	33892256
Roquefortine,3TMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3442.6	Semi standard non polar	33892256
Roquefortine,3TMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12	3334.5	Standard non polar	33892256
Roquefortine,1TBDMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	3738.6	Semi standard non polar	33892256
Roquefortine,1TBDMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	3541.3	Standard non polar	33892256
Roquefortine,1TBDMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12	3635.7	Semi standard non polar	33892256
Roquefortine,1TBDMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12	3460.2	Standard non polar	33892256
Roquefortine,1TBDMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3947.4	Semi standard non polar	33892256
Roquefortine,1TBDMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3706.9	Standard non polar	33892256
Roquefortine,2TBDMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	3733.8	Semi standard non polar	33892256
Roquefortine,2TBDMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	3630.6	Standard non polar	33892256
Roquefortine,2TBDMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	4004.6	Semi standard non polar	33892256
Roquefortine,2TBDMS,isomer #2	C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	3868.4	Standard non polar	33892256
Roquefortine,2TBDMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3968.3	Semi standard non polar	33892256
Roquefortine,2TBDMS,isomer #3	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12	3775.9	Standard non polar	33892256
Roquefortine,3TBDMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	4042.1	Semi standard non polar	33892256
Roquefortine,3TBDMS,isomer #1	C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12	3905.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Roquefortine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-2913000000-176e78d8b0008c96c04c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Roquefortine 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 - Roquefortine 10V, Positive-QTOF	splash10-0006-0009000000-056dceae120713e3c6c3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 20V, Positive-QTOF	splash10-006x-0009000000-c140adabaa40d6a94087	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 40V, Positive-QTOF	splash10-056r-9561000000-6869346a9432a2cc5c17	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 10V, Negative-QTOF	splash10-000i-0009000000-222a2527c0e685c21595	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 20V, Negative-QTOF	splash10-004i-3393000000-d4461e4bae68a6cb8ef3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 40V, Negative-QTOF	splash10-0a6r-4950000000-7f095e0b11568f1f3151	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 10V, Positive-QTOF	splash10-0006-0009000000-a6b45c36b5d0ee9f2c8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 20V, Positive-QTOF	splash10-01ox-0009000000-aab292de038f44ae8430	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 40V, Positive-QTOF	splash10-0601-0379000000-67ca9aa810d1e2bec071	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 10V, Negative-QTOF	splash10-000i-0009000000-70d5e544e37f0fee62ef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 20V, Negative-QTOF	splash10-000i-0009000000-b035d02196095486523c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Roquefortine 40V, Negative-QTOF	splash10-014l-2769000000-c617e00c2c056c797475	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

FDB002232

KNApSAcK ID

C00011251

Chemspider ID

10696908

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Roquefortine C

METLIN ID

Not Available

PubChem Compound

5935070

PDB ID

Not Available

ChEBI ID

182411

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1819491

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 Roquefortine (HMDB0030381)

MOL for HMDB0030381 (Roquefortine)

3D MOL for HMDB0030381 (Roquefortine)

3D SDF for HMDB0030381 (Roquefortine)

3D-SDF for HMDB0030381 (Roquefortine)

PDB for HMDB0030381 (Roquefortine)

3D PDB for HMDB0030381 (Roquefortine)

SMILES for HMDB0030381 (Roquefortine)

INCHI for HMDB0030381 (Roquefortine)

Structure for HMDB0030381 (Roquefortine)

3D Structure for HMDB0030381 (Roquefortine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra