MiMeDB: Showing metabocard for Paspaline (MMDBc0008860)

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:33:58 UTC

Update Date

2025-10-07 16:05:31 UTC

Metabolite ID

MMDBc0008860

Metabolite Identification

Common Name

Paspaline

Description

Paspaline is a member of the indole diterpenoid chemical class, characterized by its complex structure and biological activity. It is primarily produced by various fungi, such as those from the genus Penicillium, and is notable for its role in the biosynthesis of tetrahydropyran-ring-containing structures, which are conserved across different species (PMID:40308950 ). Paspaline and its derivatives have been isolated from marine-derived fungi, demonstrating a rich diversity of related compounds (PMID:38387395 ). In biological contexts, paspaline exhibits significant pharmacological properties, including potent inhibition of ferroptosis, a form of regulated cell death, with an EC50 value of 0.21 µM (PMID:40106372 ). Additionally, paspaline-derived indole diterpenes are recognized for their tremorgenic activity, which can induce ataxia and staggers in livestock, highlighting their toxicological relevance (PMID:34822583 ). The structural complexity of paspaline and its derivatives has prompted synthetic studies aimed at understanding their biosynthetic pathways and potential applications (PMID:34784090 ). Overall, paspaline serves as an important metabolite with implications in both pharmacology and toxicology.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08291401162D          

 35 40  0  0  1  0            999 V2000
   10.8055   -3.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2195   -1.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1267   -4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1189   -2.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -2.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545   -3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6377   -2.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3901   -2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -4.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3743   -4.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6315   -3.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6238   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8791   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8714   -2.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463   -4.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9526   -4.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9762   -3.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311   -3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -2.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -3.6144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7147   -2.5993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2930   -2.4553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2809   -3.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4671   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2099   -3.2761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7882   -3.1320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0358   -3.4704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8657   -2.4247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1287   -1.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454   -2.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7050   -3.9528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5406   -2.7936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7978   -1.7785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9623   -2.9377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18  8  2  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  2  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24 19  2  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 22 25  1  6  0  0  0
 26  3  1  6  0  0  0
 26 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27  4  1  6  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 28  5  1  1  0  0  0
 28 17  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 29 20  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31 22  1  0  0  0  0
 31 23  1  0  0  0  0
 17 32  1  6  0  0  0
 21 33  1  1  0  0  0
 22 34  1  1  0  0  0
 23 35  1  1  0  0  0
M  END


  Mrv0541 08291401162D          

 35 40  0  0  1  0            999 V2000
   10.8055   -3.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2195   -1.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1267   -4.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1189   -2.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -2.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545   -3.2761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6377   -2.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3901   -2.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -4.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3743   -4.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6315   -3.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6238   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8791   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8714   -2.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1463   -4.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9526   -4.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9762   -3.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7311   -3.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -2.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -3.6144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7147   -2.5993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2930   -2.4553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2809   -3.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4671   -2.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2099   -3.2761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7882   -3.1320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0358   -3.4704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8657   -2.4247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1287   -1.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0454   -2.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7050   -3.9528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5406   -2.7936    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7978   -1.7785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9623   -2.9377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18  8  2  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  2  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24 19  2  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 22 25  1  6  0  0  0
 26  3  1  6  0  0  0
 26 14  1  0  0  0  0
 26 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27  4  1  6  0  0  0
 27 15  1  0  0  0  0
 27 21  1  0  0  0  0
 28  5  1  1  0  0  0
 28 17  1  0  0  0  0
 28 24  1  0  0  0  0
 28 27  1  0  0  0  0
 29 20  1  0  0  0  0
 29 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31 22  1  0  0  0  0
 31 23  1  0  0  0  0
 17 32  1  6  0  0  0
 21 33  1  1  0  0  0
 22 34  1  1  0  0  0
 23 35  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008860

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@]([H])(CC[C@@]3(C)[C@]1([H])CC2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1

> <INCHI_KEY>
WLAIEIMDXUAGPY-HSECPPETSA-N

> <FORMULA>
C28H39NO2

> <MOLECULAR_WEIGHT>
421.6148

> <EXACT_MASS>
421.298079497

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.52545461834933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
5.6359221396666666

> <ALOGPS_LOGS>
-7.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.860463551856473

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.324846174098045

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0935564409641225

> <JCHEM_POLAR_SURFACE_AREA>
45.25

> <JCHEM_REFRACTIVITY>
125.02669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      20.170  -5.625   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.943  -3.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.170  -7.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.422  -4.946   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.785  -5.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.768  -6.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -4.583   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.018  -7.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.328  -3.952   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.361  -8.911   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.765  -8.279   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.979  -6.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.231  -3.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.574  -7.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.827  -4.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.606  -8.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.112  -8.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.422  -6.384   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.831  -7.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.577  -4.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.921  -6.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.134  -4.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.480  -4.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.858  -5.857   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.539  -4.220   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.325  -6.115   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.671  -5.846   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.267  -6.478   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       9.083  -4.526   0.000  0.00  0.00           N+0
HETATM   30  O   UNK     0      18.907  -2.816   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      16.885  -3.952   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      12.516  -7.379   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      14.076  -5.215   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      18.289  -3.320   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      16.730  -5.484   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    6   18                                                       
CONECT    9    7   20                                                       
CONECT   10   11   17                                                       
CONECT   11   10   21                                                       
CONECT   12   14   22                                                       
CONECT   13   15   23                                                       
CONECT   14   12   26                                                       
CONECT   15   13   27                                                       
CONECT   16   17   19                                                       
CONECT   17   10   16   28   32                                             
CONECT   18    8   19   20                                                  
CONECT   19   16   18   24                                                  
CONECT   20    9   18   29                                                  
CONECT   21   11   26   27   33                                             
CONECT   22   12   25   31   34                                             
CONECT   23   13   26   31   35                                             
CONECT   24   19   28   29                                                  
CONECT   25    1    2   22   30                                             
CONECT   26    3   14   21   23                                             
CONECT   27    4   15   21   28                                             
CONECT   28    5   17   24   27                                             
CONECT   29   20   24                                                       
CONECT   30   25                                                            
CONECT   31   22   23                                                       
CONECT   32   17                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₃₉NO₂

Average Mass

421.6148

Monoisotopic Mass

421.298079497

IUPAC Name

2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

Traditional Name

2-[(1S,2S,5S,7S,10S,11R,14S)-1,2,10-trimethyl-6-oxa-23-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁶,²⁴.0¹⁷,²²]tetracosa-16(24),17,19,21-tetraen-7-yl]propan-2-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@]([H])(CC[C@@]3(C)[C@]1([H])CC2)C(C)(C)O

InChI Identifier

InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1

InChI Key

WLAIEIMDXUAGPY-HSECPPETSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
3-alkylindole
Indole
Indole or derivatives
Oxane
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Ether
Dialkyl ether
Azacycle
Oxacycle
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
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	2.0e-05 g/L	ALOGPS
logP	6.3	ALOGPS
logP	5.64	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	45.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125.03 m³·mol⁻¹	ChemAxon
Polarizability	51.53 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0003900000-ce5ced2a3e9c7be017b8	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-0119100000-9b6ffa195d91e2eab6e5	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02a9-5389000000-d97c710f5a8a01a8bea5	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0001900000-091f4a2324c7c12bddb1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2208900000-1c08cf6c909ff015af93	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00si-1109000000-465cb760412ff872e51b	2016-08-03	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 (eluted)	2025-10-23	144.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	36.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	663.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	999.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1081.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	534.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3405.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	85.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	294.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	793.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	540.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	205.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	257.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	289.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	601.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	508.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1872.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1630.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Paspaline_TMS_1	CC(C)(O[Si](C)(C)C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1	standard non polar	2025-10-23	1748.72
Gas Chromatography	Paspaline_TMS_2	CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1	standard non polar	2025-10-23	2061.56
Gas Chromatography	Paspaline_TMS_3	CC(C)(O[Si](C)(C)C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1	standard non polar	2025-10-23	2122.14
Gas Chromatography	Paspaline_TMS_1	CC(C)(O[Si](C)(C)C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C([NH]C5=CC=CC=C45)[C@@]23C)O1	standard polar	2025-10-23	2288.88
Gas Chromatography	Paspaline_TMS_2	CC(C)(O)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1	standard polar	2025-10-23	1068.73
Gas Chromatography	Paspaline_TMS_3	CC(C)(O[Si](C)(C)C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(N([Si](C)(C)C)C5=CC=CC=C45)[C@@]23C)O1	standard polar	2025-10-23	1864.54

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	8	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20530

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115028

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 Paspaline (MMDBc0008860)

MOL for #<Metabolite:0x00007f9ad02bc038>

3D MOL for #<Metabolite:0x00007f9ad02bc038>

3D SDF for #<Metabolite:0x00007f9ad02bc038>

3D-SDF for #<Metabolite:0x00007f9ad02bc038>

PDB for #<Metabolite:0x00007f9ad02bc038>

3D PDB for #<Metabolite:0x00007f9ad02bc038>

SMILES for #<Metabolite:0x00007f9ad02bc038>

INCHI for #<Metabolite:0x00007f9ad02bc038>

Structure for #<Metabolite:0x00007f9ad02bc038>

3D Structure for #<Metabolite:0x00007f9ad02bc038>