NP-MRD: Showing NP-Card for 11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one (NP0230611)

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Record Information

Version

2.0

Created at

2022-09-06 11:06:50 UTC

Updated at

2022-09-06 11:06:51 UTC

NP-MRD ID

NP0230611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

Description

2-O-Caffeoylarbutin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 2-O-Caffeoylarbutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-O-Caffeoylarbutin has been detected, but not quantified in, fruits. 11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one is found in Abrus precatorius, Celastrus hypoleucus, Euonymus alatus, Plenckia populnea and Tripterygium wilfordii. This could make 2-O-caffeoylarbutin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308432D          

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M  END

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  Mrv0541 05061308432D          

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 15 14  1  0  0  0  0
 18  8  2  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20 10  1  0  0  0  0
 21  9  1  0  0  0  0
 22 11  1  0  0  0  0
 23 17  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 20  1  0  0  0  0
 25 22  1  0  0  0  0
 26  3  1  0  0  0  0
 26 16  1  0  0  0  0
 26 17  1  0  0  0  0
 26 24  1  0  0  0  0
 27  4  1  0  0  0  0
 27 14  1  0  0  0  0
 27 19  1  0  0  0  0
 27 23  1  0  0  0  0
 28  5  1  0  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
 28 21  1  0  0  0  0
 29  6  1  0  0  0  0
 29 15  1  0  0  0  0
 29 18  1  0  0  0  0
 30  7  1  0  0  0  0
 30 13  1  0  0  0  0
 30 21  1  0  0  0  0
 30 29  1  0  0  0  0
 31 22  1  0  0  0  0
 32 24  2  0  0  0  0
 33 23  1  0  0  0  0
 33 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(OC1=O)C1(C)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-25(2)20-10-13-30(7)21(28(20,5)12-11-22(25)31)9-8-18-19-16-26(3)17-23(33-24(26)32)27(19,4)14-15-29(18,30)6/h8,19-23,31H,9-17H2,1-7H3

> <INCHI_KEY>
HHQJBWYXBWOFJY-UHFFFAOYSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.6844

> <EXACT_MASS>
454.344695338

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
54.01220991387562

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

> <ALOGPS_LOGP>
6.28

> <JCHEM_LOGP>
6.028493491000001

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489433291560097

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351216522845059

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
131.64779999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.49e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

> <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      10.676   2.981   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.628   2.647   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.573   0.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.448  -2.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.489  -1.919   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.935   1.033   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.905  -1.319   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.601  -2.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.045  -2.453   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.824   2.101   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.378  -0.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.934  -1.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.380   1.567   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.046  -0.035   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.491   0.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.713  -1.011   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.416  -2.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.009   1.117   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.305  -0.935   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.638   0.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.453   1.651   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.787  -1.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.749  -0.401   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.675  -0.485   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.120   0.049   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.082   1.201   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.534  -3.384   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.223  -3.066   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   18                                                       
CONECT    9    8   21                                                       
CONECT   10   13   20                                                       
CONECT   11   12   22                                                       
CONECT   12   11   28                                                       
CONECT   13   10   30                                                       
CONECT   14   15   27                                                       
CONECT   15   14   29                                                       
CONECT   16   19   26                                                       
CONECT   17   23   26                                                       
CONECT   18    8   19   29                                                  
CONECT   19   16   18   27                                                  
CONECT   20   10   25   28                                                  
CONECT   21    9   28   30                                                  
CONECT   22   11   25   31                                                  
CONECT   23   17   27   33                                                  
CONECT   24   26   32   33                                                  
CONECT   25    1    2   20   22                                             
CONECT   26    3   16   17   24                                             
CONECT   27    4   14   19   23                                             
CONECT   28    5   12   20   21                                             
CONECT   29    6   15   18   30                                             
CONECT   30    7   13   21   29                                             
CONECT   31   22                                                            
CONECT   32   24                                                            
CONECT   33   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
3b-Hydroxy-12-oleanen-30,22b-olide	HMDB
Wilforlide a	MeSH

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6844 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

Traditional Name

11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one

CAS Registry Number

Not Available

SMILES

CC12CC(OC1=O)C1(C)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C1C2

InChI Identifier

InChI=1S/C30H46O3/c1-25(2)20-10-13-30(7)21(28(20,5)12-11-22(25)31)9-8-18-19-16-26(3)17-23(33-24(26)32)27(19,4)14-15-29(18,30)6/h8,19-23,31H,9-17H2,1-7H3

InChI Key

HHQJBWYXBWOFJY-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
Abrus precatorius	LOTUS Database	35616633
Celastrus hypoleucus	LOTUS Database	35616633
Euonymus alatus	LOTUS Database	35616633
Plenckia populnea	LOTUS Database	35616633
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
4-alkoxyphenol
Phenoxy compound
Catechol
Phenol ether
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Oxane
Fatty acyl
Monosaccharide
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	6.28	ALOGPS
logP	6.03	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.65 m³·mol⁻¹	ChemAxon
Polarizability	54.01 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031347

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003411

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

131751154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one (NP0230611)

MOL for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D MOL for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D SDF for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D-SDF for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

PDB for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D PDB for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

SMILES for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

INCHI for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

Structure for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)

3D Structure for NP0230611 (11-hydroxy-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-en-22-one)