NP-MRD: Showing NP-Card for {5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate (NP0154241)

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Record Information

Version

2.0

Created at

2022-09-02 11:01:35 UTC

Updated at

2022-09-02 11:01:35 UTC

NP-MRD ID

NP0154241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

Description

Quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside has been detected, but not quantified in, pulses. {5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate is found in Annona cherimola. This could make quercetin 3-(6''''-feruloylglucosyl)-(1->2)-galactosyl-(1->2)-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307062D          

 29 32  0  0  0  0            999 V2000
    6.9375    2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061307062D          

 29 32  0  0  0  0            999 V2000
    6.9375    2.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0154241

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/c1-16(25)28-14-21(3)9-5-10-22(4)19(21)8-11-23-12-18(6-7-20(22)23)24(27,13-23)15-29-17(2)26/h18-20,27H,5-15H2,1-4H3

> <INCHI_KEY>
OQDCKOUFTOKDOD-UHFFFAOYSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.5555

> <EXACT_MASS>
406.271924326

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
46.288258053043684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.203146448666666

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.752230216807543

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3445745031683813

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
109.17239999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.950   4.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.778   4.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.062   5.474   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.109   0.827   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.130   1.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.723   0.398   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.099   4.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.629   2.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.619   1.124   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.935   4.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.745   3.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.602   4.885   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.266   4.643   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.616   4.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.934   3.167   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.263   2.607   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.572   6.425   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.762   6.098   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.000   1.725   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.283   4.089   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.258   3.479   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    9   10                                                       
CONECT    6    7   18                                                       
CONECT    7    6   20                                                       
CONECT    8   11   19                                                       
CONECT    9    5   21                                                       
CONECT   10    5   22                                                       
CONECT   11    8   23                                                       
CONECT   12   18   23                                                       
CONECT   13   23   24                                                       
CONECT   14   21   28                                                       
CONECT   15   24   29                                                       
CONECT   16    1   25   28                                                  
CONECT   17    2   26   29                                                  
CONECT   18    6   12   24                                                  
CONECT   19    8   21   22                                                  
CONECT   20    7   22   23                                                  
CONECT   21    3    9   14   19                                             
CONECT   22    4   10   19   20                                             
CONECT   23   11   12   13   20                                             
CONECT   24   13   15   18   27                                             
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   24                                                            
CONECT   28   14   16                                                       
CONECT   29   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
3-[[O-6-O-[(2E)-3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranosyl-(1->2)-O-beta-D-galactopyranosyl-(1->2)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	HMDB
{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₈O₅

Average Mass

406.5555 Da

Monoisotopic Mass

406.27192 Da

IUPAC Name

{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

Traditional Name

{5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1(O)CC23CC1CCC2C1(C)CCCC(C)(COC(C)=O)C1CC3

InChI Identifier

InChI=1S/C24H38O5/c1-16(25)28-14-21(3)9-5-10-22(4)19(21)8-11-23-12-18(6-7-20(22)23)24(27,13-23)15-29-17(2)26/h18-20,27H,5-15H2,1-4H3

InChI Key

OQDCKOUFTOKDOD-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

Species Name	Source	Reference
Annona cherimola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Oligosaccharide
Flavonoid-3-o-glycoside
Flavone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Cinnamic acid ester
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Methoxyphenol
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
Catechol
Styrene
Alkyl aryl ether
Fatty acid ester
Pyranone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Oxane
Pyran
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Primary alcohol
Organic oxygen compound
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	3.54	ALOGPS
logP	3.2	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.17 m³·mol⁻¹	ChemAxon
Polarizability	46.29 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0030415

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017106

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

131751014

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate (NP0154241)

MOL for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D MOL for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D SDF for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D-SDF for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

PDB for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D PDB for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

SMILES for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

INCHI for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

Structure for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D Structure for NP0154241 ({5-[(acetyloxy)methyl]-14-hydroxy-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)