NP-MRD: Showing NP-Card for 20-acetoxy-clavulone i (NP0168954)

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Record Information

Version

2.0

Created at

2022-09-03 04:49:42 UTC

Updated at

2022-09-03 04:49:42 UTC

NP-MRD ID

NP0168954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-acetoxy-clavulone i

Description

20-Acetoxy-clavulone i belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids. Thus, 20-acetoxy-clavulone I is considered to be an eicosanoid. 20-acetoxy-clavulone i is found in Clavularia viridis. Based on a literature review very few articles have been published on 20-acetoxy-clavulone i.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032206492D          

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M  END

     RDKit          3D

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 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0168954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@@H](OC(C)=O)\C=C/C=C1/C(=O)C=C[C@]1(C\C=C/CCCCCOC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O9/c1-20(28)34-19-10-8-6-5-7-9-17-27(36-22(3)30)18-16-25(31)24(27)13-11-12-23(35-21(2)29)14-15-26(32)33-4/h7,9,11-13,16,18,23H,5-6,8,10,14-15,17,19H2,1-4H3/b9-7-,12-11-,24-13-/t23-,27-/m0/s1

> <INCHI_KEY>
LHIPZWGSDUHLAW-GLZYZVBFSA-N

> <FORMULA>
C27H36O9

> <MOLECULAR_WEIGHT>
504.576

> <EXACT_MASS>
504.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.98774251749779

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4R,5Z)-4-(acetyloxy)-7-[(1E,2S)-2-(acetyloxy)-2-[(2Z)-8-(acetyloxy)oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
3.255538029666668

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.37965567772995

> <JCHEM_POLAR_SURFACE_AREA>
122.27000000000001

> <JCHEM_REFRACTIVITY>
135.49219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.35e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-acetoxy-clavulone I

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.243 -10.088   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.783 -10.088   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.553 -11.422   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.783 -12.755   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.093 -11.422   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.863 -12.755   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.403 -12.755   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.173 -14.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.713 -14.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.483 -12.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.023 -12.755   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.928 -11.509   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.452 -10.045   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.393 -11.985   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.393 -13.525   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.928 -14.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.233 -15.511   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.692 -16.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.847 -14.984   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.543 -13.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.698 -12.456   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.158 -12.947   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.313 -11.928   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.773 -12.419   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.928 -11.401   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      22.387 -11.892   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.542 -10.874   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      22.692 -13.402   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.795 -15.044   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.131 -16.546   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.600 -17.007   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.997 -17.589   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.173 -11.422   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.403 -10.088   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.863 -10.088   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.173  -8.754   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17   29                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    7   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₉

Average Mass

504.5760 Da

Monoisotopic Mass

504.23593 Da

IUPAC Name

methyl (4R,5Z)-4-(acetyloxy)-7-[(1E,2S)-2-(acetyloxy)-2-[(2Z)-8-(acetyloxy)oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

Traditional Name

20-acetoxy-clavulone I

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@@H](OC(C)=O)\C=C/C=C1/C(=O)C=C[C@]1(C\C=C/CCCCCOC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C27H36O9/c1-20(28)34-19-10-8-6-5-7-9-17-27(36-22(3)30)18-16-25(31)24(27)13-11-12-23(35-21(2)29)14-15-26(32)33-4/h7,9,11-13,16,18,23H,5-6,8,10,14-15,17,19H2,1-4H3/b9-7-,12-11-,24-13-/t23-,27-/m0/s1

InChI Key

LHIPZWGSDUHLAW-GLZYZVBFSA-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
Clavularia viridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Clavulones and derivatives

Alternative Parents

Substituents

Clavulone
Clavulone-skeleton
Tetracarboxylic acid or derivatives
Fatty alcohol ester
Fatty acid ester
Fatty acid methyl ester
Methyl ester
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Clavulones and derivatives (LMFA03120005 )

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	4.12	ALOGPS
logP	3.26	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	122.27 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	135.49 m³·mol⁻¹	ChemAxon
Polarizability	53.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

4446340

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283219

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 20-acetoxy-clavulone i (NP0168954)

MOL for NP0168954 (20-acetoxy-clavulone i)

3D MOL for NP0168954 (20-acetoxy-clavulone i)

3D SDF for NP0168954 (20-acetoxy-clavulone i)

3D-SDF for NP0168954 (20-acetoxy-clavulone i)

PDB for NP0168954 (20-acetoxy-clavulone i)

3D PDB for NP0168954 (20-acetoxy-clavulone i)

SMILES for NP0168954 (20-acetoxy-clavulone i)

INCHI for NP0168954 (20-acetoxy-clavulone i)

Structure for NP0168954 (20-acetoxy-clavulone i)

3D Structure for NP0168954 (20-acetoxy-clavulone i)