NP-MRD: Showing NP-Card for [(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate (NP0161920)

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Record Information

Version

2.0

Created at

2022-09-02 20:13:45 UTC

Updated at

2022-09-02 20:13:45 UTC

NP-MRD ID

NP0161920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate

Description

CHEMBL373139 belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. [(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate is found in Zinowiewia costaricensis. Based on a literature review very few articles have been published on CHEMBL373139.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022222132D          

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M  END

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 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0161920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(COC(C)=O)[C@H](OC(C)=O)C(=O)[C@@H]3[C@@H](OC(C)=O)[C@]12OC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O12/c1-11-9-17(33-13(3)27)20(34-14(4)28)24(10-32-12(2)26)22(36-16(6)30)19(31)18-21(35-15(5)29)25(11,24)37-23(18,7)8/h11,17-18,20-22H,9-10H2,1-8H3/t11-,17+,18-,20+,21-,22-,24+,25-/m1/s1

> <INCHI_KEY>
YLPWIVXPAOTLTE-MDUHTVMBSA-N

> <FORMULA>
C25H34O12

> <MOLECULAR_WEIGHT>
526.535

> <EXACT_MASS>
526.205026535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.60412196381242

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,4S,5R,6S,7S,9R,12R)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
0.09942106633333093

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.78616173061432

> <JCHEM_PKA_STRONGEST_BASIC>
-4.23450921382632

> <JCHEM_POLAR_SURFACE_AREA>
157.79999999999998

> <JCHEM_REFRACTIVITY>
120.07020000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4S,5R,6S,7S,9R,12R)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.745  -3.035   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.487  -1.435   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.036  -0.874   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.258  -0.394   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.621  -0.935   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.277   0.223   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.501  -1.201   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.378  -3.077   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.066  -4.806   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.912  -6.236   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.861  -5.920   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.064  -0.977   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.509  -1.979   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.147   0.302   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.378   0.933   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.766  -0.381   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.045  -1.033   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.363  -0.772   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.513  -2.660   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.508   1.680   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.187   2.716   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.788   1.877   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.163   1.765   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.998   3.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.522   2.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.380   4.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.074   2.762   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.714   1.353   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.182   2.309   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.540   3.309   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.157   3.099   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.369   4.874   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.829   0.086   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.075  -1.568   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.783  -2.650   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.428  -2.854   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.262  -4.272   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20   33                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15    6   21   25                                             
CONECT   21   20   22                                                       
CONECT   22   21   14   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28    6   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₄O₁₂

Average Mass

526.5350 Da

Monoisotopic Mass

526.20503 Da

IUPAC Name

[(1S,2R,4S,5R,6S,7S,9R,12R)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

Traditional Name

[(1S,2R,4S,5R,6S,7S,9R,12R)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-6-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(COC(C)=O)[C@H](OC(C)=O)C(=O)[C@@H]3[C@@H](OC(C)=O)[C@]12OC3(C)C

InChI Identifier

InChI=1S/C25H34O12/c1-11-9-17(33-13(3)27)20(34-14(4)28)24(10-32-12(2)26)22(36-16(6)30)19(31)18-21(35-15(5)29)25(11,24)37-23(18,7)8/h11,17-18,20-22H,9-10H2,1-8H3/t11-,17+,18-,20+,21-,22-,24+,25-/m1/s1

InChI Key

YLPWIVXPAOTLTE-MDUHTVMBSA-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

Species Name	Source	Reference
Zinowiewia costaricensis	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Agarofuran
Sesquiterpenoid
Oxepane
Alpha-acyloxy ketone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.91	ALOGPS
logP	0.099	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	157.8 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.07 m³·mol⁻¹	ChemAxon
Polarizability	51.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

9378358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11203290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate (NP0161920)

MOL for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D MOL for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D SDF for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D-SDF for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

PDB for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D PDB for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

SMILES for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

INCHI for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

Structure for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)

3D Structure for NP0161920 ([(1s,2r,4s,5r,6s,7s,9r,12r)-4,5,7,12-tetrakis(acetyloxy)-2,10,10-trimethyl-8-oxo-11-oxatricyclo[7.2.1.0¹,⁶]dodecan-6-yl]methyl acetate)