NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate (NP0293720)

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Record Information

Version

2.0

Created at

2022-09-10 01:52:28 UTC

Updated at

2022-09-10 01:52:28 UTC

NP-MRD ID

NP0293720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate

Description

(2S,3R,4S,5S,6R,7R,8S)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate is found in Botrytis cinerea. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R,7R,8S)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102203522D          

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M  END

     RDKit          3D

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  Mrv1652309102203522D          

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 30 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0293720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC[C@@H](O)\C=C\C(=O)O[C@H]1[C@H](C)OC(=O)[C@@H](C)[C@@H](OC(C)=O)[C@](C)(O)[C@@H](O)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O9/c1-7-8-9-10-11-18(26)12-13-19(27)33-20-14(2)21(28)24(6,30)22(32-17(5)25)15(3)23(29)31-16(20)4/h12-16,18,20-22,26,28,30H,7-11H2,1-6H3/b13-12+/t14-,15+,16+,18-,20-,21+,22-,24-/m1/s1

> <INCHI_KEY>
RNADGXHRZMPKTC-SSDSDTPGSA-N

> <FORMULA>
C24H40O9

> <MOLECULAR_WEIGHT>
472.575

> <EXACT_MASS>
472.267232868

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.48774154563487

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R,7R,8S)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoate

> <JCHEM_LOGP>
2.8140846809999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.352391113275019

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.949912382207156

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8715618167844488

> <JCHEM_POLAR_SURFACE_AREA>
139.59000000000003

> <JCHEM_REFRACTIVITY>
120.06209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R,7R,8S)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.687  -7.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.354  -7.078   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.020  -7.848   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.686  -7.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.353  -7.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.019  -7.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.685  -7.848   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.685  -9.388   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.352  -7.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.018  -7.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.316  -7.078   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.316  -5.538   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.649  -7.848   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.983  -7.078   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.716  -5.562   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.199  -5.294   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.486  -4.228   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.933  -3.701   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.933  -2.161   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.380  -4.228   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.370  -3.048   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.150  -5.562   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.666  -5.294   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.656  -6.474   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.173  -6.206   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.130  -7.921   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.882  -7.078   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.412  -6.899   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.492  -8.492   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.703  -8.068   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.229  -9.515   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.163  -8.068   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.636  -9.515   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   14   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5S,6R,7R,8S)-7-(Acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoic acid	Generator

Chemical Formula

C₂₄H₄₀O₉

Average Mass

472.5750 Da

Monoisotopic Mass

472.26723 Da

IUPAC Name

(2S,3R,4S,5S,6R,7R,8S)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoate

Traditional Name

(2S,3R,4S,5S,6R,7R,8S)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E,4R)-4-hydroxydec-2-enoate

CAS Registry Number

Not Available

SMILES

CCCCCC[C@@H](O)\C=C\C(=O)O[C@H]1[C@H](C)OC(=O)[C@@H](C)[C@@H](OC(C)=O)[C@](C)(O)[C@@H](O)[C@@H]1C

InChI Identifier

InChI=1S/C24H40O9/c1-7-8-9-10-11-18(26)12-13-19(27)33-20-14(2)21(28)24(6,30)22(32-17(5)25)15(3)23(29)31-16(20)4/h12-16,18,20-22,26,28,30H,7-11H2,1-6H3/b13-12+/t14-,15+,16+,18-,20-,21+,22-,24-/m1/s1

InChI Key

RNADGXHRZMPKTC-SSDSDTPGSA-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
Botrytis cinerea	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

Fatty alcohol
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.81	ChemAxon
pKa (Strongest Acidic)	12.95	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.06 m³·mol⁻¹	ChemAxon
Polarizability	51.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

163193429

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate (NP0293720)

MOL for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

3D MOL for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

3D SDF for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

3D-SDF for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

PDB for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

3D PDB for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

SMILES for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

INCHI for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

Structure for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)

3D Structure for NP0293720 ((2s,3r,4s,5s,6r,7r,8s)-7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2e,4r)-4-hydroxydec-2-enoate)