MiMeDB: Showing metabocard for Preaustinoid B (MMDBc0007554)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 00:42:02 UTC

Update Date

2022-08-31 06:27:27 UTC

Metabolite ID

MMDBc0007554

Metabolite Identification

Common Name

Preaustinoid B

Description

Preaustinoid B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a small amount of articles have been published on Preaustinoid B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152102422D          

 34 37  0  0  1  0            999 V2000
    0.5696    0.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    1.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586   -0.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579   -0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1739    1.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059   -0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -0.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    1.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984    1.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586    1.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -0.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7868    0.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647    0.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8732   -0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113    0.6073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3997   -0.1503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6622    1.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973    1.0620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1604    2.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848    0.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2078   -0.0906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -1.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864    0.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5762   -1.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.6363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    0.6109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 14  1  2  0  0  0  0
 15  2  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22  5  1  6  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  6  1  6  0  0  0
 23 12  1  0  0  0  0
 23 17  1  0  0  0  0
 24  7  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 25 23  1  0  0  0  0
 26 15  1  6  0  0  0
 26 19  1  0  0  0  0
 26 24  1  0  0  0  0
 27 15  2  0  0  0  0
 28 18  2  0  0  0  0
 29 19  2  0  0  0  0
 30 20  2  0  0  0  0
 26 31  1  1  0  0  0
 32  8  1  0  0  0  0
 32 20  1  0  0  0  0
 33 16  1  0  0  0  0
 34 17  1  0  0  0  0
M  END


  Mrv1652305152102422D          

 34 37  0  0  1  0            999 V2000
    0.5696    0.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    1.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586   -0.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6579   -0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1739    1.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0682   -0.9057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0059   -0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616   -0.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8229    1.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984    1.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8371   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586    1.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691    1.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -0.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7868    0.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603    0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647    0.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8732   -0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113    0.6073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3997   -0.1503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6622    1.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9973    1.0620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1604    2.4816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848    0.6944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2078   -0.0906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -1.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864    0.9104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5762   -1.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.6363    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    0.6109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 14  1  2  0  0  0  0
 15  2  1  0  0  0  0
 16  9  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 21  3  1  0  0  0  0
 21  4  1  0  0  0  0
 21 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22  5  1  6  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23  6  1  6  0  0  0
 23 12  1  0  0  0  0
 23 17  1  0  0  0  0
 24  7  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 25 23  1  0  0  0  0
 26 15  1  6  0  0  0
 26 19  1  0  0  0  0
 26 24  1  0  0  0  0
 27 15  2  0  0  0  0
 28 18  2  0  0  0  0
 29 19  2  0  0  0  0
 30 20  2  0  0  0  0
 26 31  1  1  0  0  0
 32  8  1  0  0  0  0
 32 20  1  0  0  0  0
 33 16  1  0  0  0  0
 34 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0007554

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C12CC[C@]3(C)C([H])(CC4(C)C(=C)C3(C(=O)OC)C(=O)[C@]4(O)C(C)=O)[C@@]1(C)CCC(=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O6/c1-14-24(7)13-17-22(5)11-10-18(28)21(3,4)16(22)9-12-23(17,6)25(14,20(30)32-8)19(29)26(24,31)15(2)27/h16-17,31H,1,9-13H2,2-8H3/t16?,17?,22-,23+,24?,25?,26+/m0/s1

> <INCHI_KEY>
DXAQFFJRJPDSIQ-UFMKZKCMSA-N

> <FORMULA>
C26H36O6

> <MOLECULAR_WEIGHT>
444.568

> <EXACT_MASS>
444.251188879

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.783748590519885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R,10R,14R)-14-acetyl-14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadecane-1-carboxylate

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
3.9790581710000024

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.10403327412064

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.95582511633908

> <JCHEM_PKA_STRONGEST_BASIC>
-4.567721551953402

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
118.10669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,10R,14R)-14-acetyl-14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadecane-1-carboxylate

> <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       1.063   1.243   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.281   3.571   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.883  -1.643   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.561  -0.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.925   2.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.861  -1.691   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.820   4.408   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.011  -1.354   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.835  -1.532   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.003   2.548   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.464   2.494   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.296  -1.586   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.589   2.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.602   1.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.249   3.395   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.558  -0.172   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.202   1.079   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.819   1.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.801   0.444   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.564  -2.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.097  -0.118   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.741   1.134   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.480  -0.281   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.103   2.894   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.966  -0.563   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.862   1.982   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.166   4.632   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      11.358   1.296   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.388  -0.169   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.650  -3.141   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.348   1.699   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.075  -2.445   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       8.280   1.188   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.663   1.140   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3   21                                                            
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6   23                                                            
CONECT    7   24                                                            
CONECT    8   32                                                            
CONECT    9   12   16                                                       
CONECT   10   11   18                                                       
CONECT   11   10   22                                                       
CONECT   12    9   23                                                       
CONECT   13   17   24                                                       
CONECT   14    1   24   25                                                  
CONECT   15    2   26   27                                                  
CONECT   16    9   21   22   33                                             
CONECT   17   13   22   23   34                                             
CONECT   18   10   21   28                                                  
CONECT   19   25   26   29                                                  
CONECT   20   25   30   32                                                  
CONECT   21    3    4   16   18                                             
CONECT   22    5   11   16   17                                             
CONECT   23    6   12   17   25                                             
CONECT   24    7   13   14   26                                             
CONECT   25   14   19   20   23                                             
CONECT   26   15   19   24   31                                             
CONECT   27   15                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31   26                                                            
CONECT   32    8   20                                                       
CONECT   33   16                                                            
CONECT   34   17                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

Synonyms

Not Available

Molecular Formula

C₂₆H₃₆O₆

Average Mass

444.568

Monoisotopic Mass

444.251188879

IUPAC Name

methyl (2R,10R,14R)-14-acetyl-14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadecane-1-carboxylate

Traditional Name

methyl (2R,10R,14R)-14-acetyl-14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0^{2,11}.0^{5,10}]hexadecane-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]C12CC[C@]3(C)C([H])(CC4(C)C(=C)C3(C(=O)OC)C(=O)[C@]4(O)C(C)=O)[C@@]1(C)CCC(=O)C2(C)C

InChI Identifier

InChI=1S/C26H36O6/c1-14-24(7)13-17-22(5)11-10-18(28)21(3,4)16(22)9-12-23(17,6)25(14,20(30)32-8)19(29)26(24,31)15(2)27/h16-17,31H,1,9-13H2,2-8H3/t16?,17?,22-,23+,24?,25?,26+/m0/s1

InChI Key

DXAQFFJRJPDSIQ-UFMKZKCMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Steroid
Acyloin
Alpha-hydroxy ketone
Cyclic alcohol
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0094 g/L	ALOGPS
logP	3.49	ALOGPS
logP	3.98	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	10.96	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	118.11 m³·mol⁻¹	ChemAxon
Polarizability	47.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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

Metabolic Reactions

Not Available

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

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

8518885

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10343426

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 Preaustinoid B (MMDBc0007554)

MOL for #<Metabolite:0x00007fdb245df488>

3D MOL for #<Metabolite:0x00007fdb245df488>

3D SDF for #<Metabolite:0x00007fdb245df488>

3D-SDF for #<Metabolite:0x00007fdb245df488>

PDB for #<Metabolite:0x00007fdb245df488>

3D PDB for #<Metabolite:0x00007fdb245df488>

SMILES for #<Metabolite:0x00007fdb245df488>

INCHI for #<Metabolite:0x00007fdb245df488>

Structure for #<Metabolite:0x00007fdb245df488>

3D Structure for #<Metabolite:0x00007fdb245df488>