NP-MRD: Showing NP-Card for (-)-Cipadesin E (NP0071036)

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Record Information

Version

2.0

Created at

2022-04-28 16:26:23 UTC

Updated at

2022-04-28 16:26:23 UTC

NP-MRD ID

NP0071036

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cipadesin E

Description

Methyl 2-[(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]Heptadeca-1,3-dien-12-yl]acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (-)-Cipadesin E is found in Cipadessa cinerascens. Based on a literature review very few articles have been published on methyl 2-[(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]Heptadeca-1,3-dien-12-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218262D          

 38 42  0  0  1  0            999 V2000
    5.1571   -0.1327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 34 35  1  0  0  0  0
 20 36  1  1  0  0  0
 13 37  1  1  0  0  0
  6 38  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282218262D          

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    1.9562   -0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936   -0.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 29  1  0  0  0  0
 22 30  1  0  0  0  0
 21 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 20 36  1  1  0  0  0
 13 37  1  1  0  0  0
  6 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1[C@]2(C)[C@H](C[C@@H](OC(C)=O)C1(C)C)OC1=C(C)C3=CC(=O)O[C@@H](C4=COC=C4)[C@]3(C)[C@@H](O)[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-14-17-10-22(32)38-26(16-8-9-35-13-16)28(17,5)25(33)23-24(14)37-20-12-19(36-15(2)30)27(3,4)18(29(20,23)6)11-21(31)34-7/h8-10,13,18-20,23,25-26,33H,11-12H2,1-7H3/t18-,19+,20-,23+,25-,26-,28-,29+/m0/s1

> <INCHI_KEY>
QPOFDJPNBLTBIL-OCKZNKFTSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.538292957963534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3-dien-12-yl]acetate

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
1.9759475896666665

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.15693057580447

> <JCHEM_PKA_STRONGEST_BASIC>
-2.883672682412032

> <JCHEM_POLAR_SURFACE_AREA>
121.5

> <JCHEM_REFRACTIVITY>
135.54539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3-dien-12-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       9.627  -0.248   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.390   1.754   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.864  -2.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.907  -3.383   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.152  -4.725   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.642  -4.421   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.464  -2.891   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.463   4.315   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.358   3.069   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.733   1.058   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.375   2.458   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.908   2.602   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.483   3.714   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.245  -2.013   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.934  -1.176   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.617  -2.030   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.726  -3.286   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.193  -3.141   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.368  -4.685   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.476  -5.941   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.652  -0.699   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.249  -1.724   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.708  -1.232   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   13   38                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    6   14   37                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    5   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   14   21   36                                             
CONECT   21   20   22   31                                                  
CONECT   22   21   23   29   30                                             
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   22                                                            
CONECT   30   22                                                            
CONECT   31   21   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   20                                                            
CONECT   37   13                                                            
CONECT   38    6                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0,.0,]heptadeca-1,3-dien-12-yl]acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

methyl 2-[(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3-dien-12-yl]acetate

Traditional Name

methyl [(7R,8S,9S,10S,11S,12S,14R,16S)-14-(acetyloxy)-7-(furan-3-yl)-9-hydroxy-2,8,11,13,13-pentamethyl-5-oxo-6,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1,3-dien-12-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1[C@]2(C)[C@H](C[C@@H](OC(C)=O)C1(C)C)OC1=C(C)C3=CC(=O)O[C@@H](C4=COC=C4)[C@]3(C)[C@@H](O)[C@H]21

InChI Identifier

InChI=1S/C29H36O9/c1-14-17-10-22(32)38-26(16-8-9-35-13-16)28(17,5)25(33)23-24(14)37-20-12-19(36-15(2)30)27(3,4)18(29(20,23)6)11-21(31)34-7/h8-10,13,18-20,23,25-26,33H,11-12H2,1-7H3/t18-,19+,20-,23+,25-,26-,28-,29+/m0/s1

InChI Key

QPOFDJPNBLTBIL-OCKZNKFTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cipadessa cinerascens	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Dihydropyranone
Pyran
Furan
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.77	ALOGPS
logP	1.98	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	121.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.55 m³·mol⁻¹	ChemAxon
Polarizability	54.54 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163031366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Cipadesin E (NP0071036)

MOL for NP0071036 ((-)-Cipadesin E)

3D MOL for NP0071036 ((-)-Cipadesin E)

3D SDF for NP0071036 ((-)-Cipadesin E)

3D-SDF for NP0071036 ((-)-Cipadesin E)

PDB for NP0071036 ((-)-Cipadesin E)

3D PDB for NP0071036 ((-)-Cipadesin E)

SMILES for NP0071036 ((-)-Cipadesin E)

INCHI for NP0071036 ((-)-Cipadesin E)

Structure for NP0071036 ((-)-Cipadesin E)

3D Structure for NP0071036 ((-)-Cipadesin E)