MiMeDB: Showing metabocard for Asterrelenin (MMDBc0004575)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:31:00 UTC

Update Date

2025-10-07 16:04:53 UTC

Metabolite ID

MMDBc0004575

Metabolite Identification

Common Name

Asterrelenin

Description

Asterrelenin is a novel alkaloid belonging to the chemical class of meroterpenoids. It was isolated from the thermophilic fungus Aspergillus terreus TM8, alongside other metabolites such as terretonin M and terrelumamide A (PMID:16124769 ). This compound exhibits a complex tetracyclic structure and is part of a broader group of bioactive secondary metabolites produced by fungi, which often possess significant pharmacological properties. The biosynthetic pathways leading to the formation of asterrelenin and its related compounds highlight the intricate chemistry involved in fungal metabolism. Asterrelenin's potential biological activities and interactions within biological systems are of interest, particularly in the context of its isolation from a thermophilic organism, which may suggest unique adaptive features that enhance its stability or efficacy in various environments. Further research into asterrelenin could elucidate its role in the ecology of Aspergillus terreus and its potential applications in medicine, particularly in the development of new therapeutic agents derived from fungal metabolites (PMID:16124769 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100312D          

 33 37  0  0  1  0            999 V2000
    4.0607   -3.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3521    0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412   -2.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3941   -2.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896   -0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -1.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455   -0.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310   -0.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -0.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9200   -1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4788   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375   -2.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    0.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996   -0.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044   -1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437   -1.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2021   -0.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -2.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337   -0.8214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9073   -2.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -1.4874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1521   -1.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7037   -2.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.1526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -1.0785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    1.2460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6847    0.2389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944   -3.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017   -2.7148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4469   -0.1553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 15  2  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 23  3  1  0  0  0  0
 23  4  1  0  0  0  0
 23  5  1  0  0  0  0
 24 14  1  0  0  0  0
 24 17  1  0  0  0  0
 24 22  1  0  0  0  0
 24 23  1  1  0  0  0
 25 14  1  0  0  0  0
 25 21  1  0  0  0  0
 26 18  1  0  0  0  0
 26 21  2  0  0  0  0
 27 15  1  0  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 15  2  0  0  0  0
 30 20  2  0  0  0  0
 31 21  1  0  0  0  0
 25 32  1  1  0  0  0
 22 33  1  1  0  0  0
M  END


  Mrv1652305152100312D          

 33 37  0  0  1  0            999 V2000
    4.0607   -3.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3521    0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2412   -2.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3941   -2.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896   -0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6333   -1.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455   -0.8798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6310   -0.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -0.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9200   -1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4788   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9154    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375   -2.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    0.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996   -0.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2044   -1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3437   -1.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2021   -0.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -2.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337   -0.8214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9073   -2.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -1.4874    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1521   -1.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7037   -2.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.1526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1498   -1.0785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    1.2460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6847    0.2389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6944   -3.2235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017   -2.7148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4469   -0.1553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 15  2  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 18 16  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 23  3  1  0  0  0  0
 23  4  1  0  0  0  0
 23  5  1  0  0  0  0
 24 14  1  0  0  0  0
 24 17  1  0  0  0  0
 24 22  1  0  0  0  0
 24 23  1  1  0  0  0
 25 14  1  0  0  0  0
 25 21  1  0  0  0  0
 26 18  1  0  0  0  0
 26 21  2  0  0  0  0
 27 15  1  0  0  0  0
 27 19  1  0  0  0  0
 27 22  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 15  2  0  0  0  0
 30 20  2  0  0  0  0
 31 21  1  0  0  0  0
 25 32  1  1  0  0  0
 22 33  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004575

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12N(C(C)=O)C3=CC=CC=C3[C@@]1(C[C@@]1(O)N2C(=O)C2=CC=CC=C2N=C1O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H25N3O4/c1-5-23(3,4)24-14-25(32)21(31)26-18-12-8-6-10-16(18)20(30)28(25)22(24)27(15(2)29)19-13-9-7-11-17(19)24/h5-13,22,32H,1,14H2,2-4H3,(H,26,31)/t22-,24+,25-/m0/s1

> <INCHI_KEY>
VQSXFZXCXRKORH-CAOCKLPOSA-N

> <FORMULA>
C25H25N3O4

> <MOLECULAR_WEIGHT>
431.492

> <EXACT_MASS>
431.184506297

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.19271137457869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,10R,12S)-3-acetyl-12,13-dihydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaen-21-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
3.594414538333333

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.276046144732915

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.181369369865658

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7847873037664589

> <JCHEM_POLAR_SURFACE_AREA>
93.44

> <JCHEM_REFRACTIVITY>
120.90989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,10R,12S)-3-acetyl-12,13-dihydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaen-21-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       7.580  -6.672   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.391   1.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.537  -3.111   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.050  -4.929   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.202  -5.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.101  -0.253   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.516  -2.289   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.765  -1.642   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.511  -0.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.435  -0.133   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.184  -3.063   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.894  -2.912   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.175   0.017   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.483  -4.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.898   1.178   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.306  -1.403   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.848  -2.297   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.642  -2.793   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.844  -0.757   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.806  -1.056   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.816  -4.517   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.476  -1.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.294  -4.020   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.385  -2.777   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.017  -3.553   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.314  -4.178   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       6.378  -0.285   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       4.013  -2.013   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0       6.925   2.326   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.145   0.446   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.163  -6.017   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.297  -5.068   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       4.568  -0.290   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   15                                                            
CONECT    3   23                                                            
CONECT    4   23                                                            
CONECT    5    1   23                                                       
CONECT    6    8   10                                                       
CONECT    7    9   11                                                       
CONECT    8    6   12                                                       
CONECT    9    7   13                                                       
CONECT   10    6   16                                                       
CONECT   11    7   17                                                       
CONECT   12    8   18                                                       
CONECT   13    9   19                                                       
CONECT   14   24   25                                                       
CONECT   15    2   27   29                                                  
CONECT   16   10   18   20                                                  
CONECT   17   11   19   24                                                  
CONECT   18   12   16   26                                                  
CONECT   19   13   17   27                                                  
CONECT   20   16   28   30                                                  
CONECT   21   25   26   31                                                  
CONECT   22   24   27   28   33                                             
CONECT   23    3    4    5   24                                             
CONECT   24   14   17   22   23                                             
CONECT   25   14   21   28   32                                             
CONECT   26   18   21                                                       
CONECT   27   15   19   22                                                  
CONECT   28   20   22   25                                                  
CONECT   29   15                                                            
CONECT   30   20                                                            
CONECT   31   21                                                            
CONECT   32   25                                                            
CONECT   33   22                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₂₅N₃O₄

Average Mass

431.492

Monoisotopic Mass

431.184506297

IUPAC Name

(2S,10R,12S)-3-acetyl-12,13-dihydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaen-21-one

Traditional Name

(2S,10R,12S)-3-acetyl-12,13-dihydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaen-21-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12N(C(C)=O)C3=CC=CC=C3[C@@]1(C[C@@]1(O)N2C(=O)C2=CC=CC=C2N=C1O)C(C)(C)C=C

InChI Identifier

InChI=1S/C25H25N3O4/c1-5-23(3,4)24-14-25(32)21(31)26-18-12-8-6-10-16(18)20(30)28(25)22(24)27(15(2)29)19-13-9-7-11-17(19)24/h5-13,22,32H,1,14H2,2-4H3,(H,26,31)/t22-,24+,25-/m0/s1

InChI Key

VQSXFZXCXRKORH-CAOCKLPOSA-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
Benzodiazepine
1,4-benzodiazepine
Alpha-amino acid or derivatives
Indole
Benzenoid
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous amide
Acetamide
Lactam
Carboxamide group
Secondary carboxylic acid amide
Alkanolamine
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	2.37	ALOGPS
logP	3.59	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	2.18	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	120.91 m³·mol⁻¹	ChemAxon
Polarizability	45.19 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	19.9
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	28.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	546.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	762.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	541.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	237.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2902.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	90.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	420.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	446.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	86.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	167.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	168.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	9.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	279.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	94.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	452.0
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1723.1
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1166.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Asterrelenin_TMS_1	C=CC(C)(C)[C@@]12C[C@]3(O[Si](C)(C)C)C(O)=NC4=CC=CC=C4C(=O)N3[C@@H]1N(C(C)=O)C1=CC=CC=C12	standard non polar	2025-10-23	1764.99
Gas Chromatography	Asterrelenin_TMS_2	C=CC(C)(C)[C@@]12C[C@]3(O)C(O[Si](C)(C)C)=NC4=CC=CC=C4C(=O)N3[C@@H]1N(C(C)=O)C1=CC=CC=C12	standard non polar	2025-10-23	1305.53
Gas Chromatography	Asterrelenin_TMS_3	C=CC(C)(C)[C@@]12C[C@]3(O[Si](C)(C)C)C(O[Si](C)(C)C)=NC4=CC=CC=C4C(=O)N3[C@@H]1N(C(C)=O)C1=CC=CC=C12	standard non polar	2025-10-23	1271.11
Gas Chromatography	Asterrelenin_TMS_1	C=CC(C)(C)[C@@]12C[C@]3(O[Si](C)(C)C)C(O)=NC4=CC=CC=C4C(=O)N3[C@@H]1N(C(C)=O)C1=CC=CC=C12	standard polar	2025-10-23	2373.07
Gas Chromatography	Asterrelenin_TMS_2	C=CC(C)(C)[C@@]12C[C@]3(O)C(O[Si](C)(C)C)=NC4=CC=CC=C4C(=O)N3[C@@H]1N(C(C)=O)C1=CC=CC=C12	standard polar	2025-10-23	2806.23
Gas Chromatography	Asterrelenin_TMS_3	C=CC(C)(C)[C@@]12C[C@]3(O[Si](C)(C)C)C(O[Si](C)(C)C)=NC4=CC=CC=C4C(=O)N3[C@@H]1N(C(C)=O)C1=CC=CC=C12	standard polar	2025-10-23	2876.83

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00042249

Chemspider ID

9872428

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11697703

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Asterrelenin (MMDBc0004575)

MOL for #<Metabolite:0x00007f9a9fcfcb28>

3D MOL for #<Metabolite:0x00007f9a9fcfcb28>

3D SDF for #<Metabolite:0x00007f9a9fcfcb28>

3D-SDF for #<Metabolite:0x00007f9a9fcfcb28>

PDB for #<Metabolite:0x00007f9a9fcfcb28>

3D PDB for #<Metabolite:0x00007f9a9fcfcb28>

SMILES for #<Metabolite:0x00007f9a9fcfcb28>

INCHI for #<Metabolite:0x00007f9a9fcfcb28>

Structure for #<Metabolite:0x00007f9a9fcfcb28>

3D Structure for #<Metabolite:0x00007f9a9fcfcb28>