NP-MRD: Showing NP-Card for 14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate (NP0299522)

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Record Information

Version

2.0

Created at

2022-09-10 11:23:31 UTC

Updated at

2022-09-10 11:23:32 UTC

NP-MRD ID

NP0299522

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate

Description

14-(Acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]Nonadecan-19-yl acetate belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. 14-(Acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]Nonadecan-19-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171523412D          

 35 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171523412D          

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 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  5 34  1  0  0  0  0
 15 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299522

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2OCC2(OC(C)=O)C2C(O)C3CC(O)C4(C)OCC3(C)C4(O)C(O)C(=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O11/c1-10(25)34-14-7-15-23(9-32-15,35-11(2)26)17-16(28)12-6-13(27)22(5)24(31,20(12,3)8-33-22)19(30)18(29)21(14,17)4/h12-17,19,27-28,30-31H,6-9H2,1-5H3

> <INCHI_KEY>
RFSLPOAJKCLJFP-UHFFFAOYSA-N

> <FORMULA>
C24H34O11

> <MOLECULAR_WEIGHT>
498.525

> <EXACT_MASS>
498.210111915

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.4084596049855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-2.0529994779999994

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.37557854765289

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.700247046088538

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0064834737694843

> <JCHEM_POLAR_SURFACE_AREA>
169.04999999999998

> <JCHEM_REFRACTIVITY>
114.62549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.534  -5.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.773  -3.954   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.210  -3.400   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.575  -2.987   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.813  -1.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.250  -0.911   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.489   0.610   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.456   1.808   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.258   2.776   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.291   1.577   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.384   2.822   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.008   4.230   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.101   5.474   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.539   4.393   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.854   1.023   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.651   2.090   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.881   3.612   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.978   1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.036  -0.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.503  -0.735   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.552  -1.947   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.373   0.681   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.108   0.258   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.697   2.026   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.870   3.004   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.171   2.164   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.148   3.355   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.230   0.587   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.736   0.909   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.907  -1.092   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.905  -2.262   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.423  -1.444   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.761  -2.947   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.615  -0.498   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.609  -2.038   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    7   11   15                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   34                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    5   15   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
14-(Acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0,.0,.0,]nonadecan-19-yl acetic acid	Generator
14-(Acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₄O₁₁

Average Mass

498.5250 Da

Monoisotopic Mass

498.21011 Da

IUPAC Name

14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate

Traditional Name

14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2OCC2(OC(C)=O)C2C(O)C3CC(O)C4(C)OCC3(C)C4(O)C(O)C(=O)C12C

InChI Identifier

InChI=1S/C24H34O11/c1-10(25)34-14-7-15-23(9-32-15,35-11(2)26)17-16(28)12-6-13(27)22(5)24(31,20(12,3)8-33-22)19(30)18(29)21(14,17)4/h12-17,19,27-28,30-31H,6-9H2,1-5H3

InChI Key

RFSLPOAJKCLJFP-UHFFFAOYSA-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 oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Oxetane
Ketone
Carboxylic acid ester
Polyol
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	-0.89	ALOGPS
logP	-2.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.7	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.63 m³·mol⁻¹	ChemAxon
Polarizability	48.41 Å³	ChemAxon
Number of Rings	5	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

14866183

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate (NP0299522)

MOL for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

3D MOL for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

3D SDF for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

3D-SDF for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

PDB for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

3D PDB for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

SMILES for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

INCHI for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

Structure for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)

3D Structure for NP0299522 (14-(acetyloxy)-2,5,10,11-tetrahydroxy-6,9,13-trimethyl-12-oxo-7,17-dioxapentacyclo[11.6.0.0³,⁹.0⁶,¹⁰.0¹⁶,¹⁹]nonadecan-19-yl acetate)