NP-MRD: Showing NP-Card for (1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate (NP0284012)

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Record Information

Version

2.0

Created at

2022-09-09 11:31:40 UTC

Updated at

2022-09-09 11:31:40 UTC

NP-MRD ID

NP0284012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate

Description

Michaolide G belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Michaolide G is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on michaolide G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213312D          

 36 39  0  0  1  0            999 V2000
    5.5712    2.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1676    1.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9793    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3372    2.5853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3702    1.1155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3145   -0.1258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1028   -0.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092213312D          

 36 39  0  0  1  0            999 V2000
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 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
 36  2  1  1  0  0  0
  6 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@]2(C)O[C@H]2C[C@H](OC(C)=O)\C(C)=C\C[C@@H](OC(C)=O)[C@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-12-8-9-19(33-16(5)29)26(7)23(36-26)22-21(13(2)24(30)34-22)18(32-15(4)28)11-25(6)20(35-25)10-17(12)31-14(3)27/h8,17-23H,2,9-11H2,1,3-7H3/b12-8+/t17-,18+,19+,20-,21+,22-,23-,25-,26-/m0/s1

> <INCHI_KEY>
MDAGMBAVURBMPE-LNFGTXBMSA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.548

> <EXACT_MASS>
506.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.16067444273526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,7E,9S,11S,13S,15R,16R)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0^{2,4}.0^{11,13}]nonadec-7-en-5-yl acetate

> <JCHEM_LOGP>
1.3571371100000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9413919537262116

> <JCHEM_POLAR_SURFACE_AREA>
130.26000000000002

> <JCHEM_REFRACTIVITY>
122.93100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,7E,9S,11S,13S,15R,16R)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0^{2,4}.0^{11,13}]nonadec-7-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.400   4.228   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.513   3.163   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.028   3.438   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.696   4.826   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.758   2.082   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.694   0.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.654  -0.235   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.125  -0.689   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.996  -1.736   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.330  -2.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.654  -3.238   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.041  -3.906   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.314  -3.038   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.199  -1.503   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.701  -3.706   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.694  -4.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.154  -4.442   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.766  -5.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.766  -6.650   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.379  -4.442   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.418  -5.646   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.896  -5.416   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.935  -6.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.333  -3.983   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.418  -3.238   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.076  -1.736   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.947  -0.689   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.418  -0.235   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.551   1.038   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.379   0.969   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.766   1.637   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.423   3.139   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.952   3.593   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.823   2.545   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.609   5.094   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.306   1.637   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   28                                                       
CONECT   28   27   26   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₀

Average Mass

506.5480 Da

Monoisotopic Mass

506.21520 Da

IUPAC Name

(1S,2S,4S,5R,7E,9S,11S,13S,15R,16R)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0^{2,4}.0^{11,13}]nonadec-7-en-5-yl acetate

Traditional Name

(1S,2S,4S,5R,7E,9S,11S,13S,15R,16R)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0^{2,4}.0^{11,13}]nonadec-7-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@]2(C)O[C@H]2C[C@H](OC(C)=O)\C(C)=C\C[C@@H](OC(C)=O)[C@]2(C)O[C@H]2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C26H34O10/c1-12-8-9-19(33-16(5)29)26(7)23(36-26)22-21(13(2)24(30)34-22)18(32-15(4)28)11-25(6)20(35-25)10-17(12)31-14(3)27/h8,17-23H,2,9-11H2,1,3-7H3/b12-8+/t17-,18+,19+,20-,21+,22-,23-,25-,26-/m0/s1

InChI Key

MDAGMBAVURBMPE-LNFGTXBMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:66380 )
acetate ester (CHEBI:66380 )
cembrane diterpenoid (CHEBI:66380 )
gamma-lactone (CHEBI:66380 )
macrocycle (CHEBI:66380 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.36	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	130.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.93 m³·mol⁻¹	ChemAxon
Polarizability	51.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28638995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16723569

PDB ID

Not Available

ChEBI ID

66380

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate (NP0284012)

MOL for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

3D MOL for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

3D SDF for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

3D-SDF for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

PDB for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

3D PDB for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

SMILES for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

INCHI for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

Structure for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)

3D Structure for NP0284012 ((1s,2s,4s,5r,7e,9s,11s,13s,15r,16r)-9,15-bis(acetyloxy)-4,8,13-trimethyl-17-methylidene-18-oxo-3,12,19-trioxatetracyclo[14.3.0.0²,⁴.0¹¹,¹³]nonadec-7-en-5-yl acetate)