NP-MRD: Showing NP-Card for Aloe resin A (NP0060376)

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Record Information

Version

2.0

Created at

2022-04-28 05:26:25 UTC

Updated at

2022-04-28 05:26:25 UTC

NP-MRD ID

NP0060376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aloe resin A

Description

(2S,3S,4S,5S,6S)-4,5-dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate 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. Aloe resin A is found in Aloe sp. . Based on a literature review very few articles have been published on (2S,3S,4S,5S,6S)-4,5-dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207262D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282207262D          

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 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 30 33  1  0  0  0  0
 10 34  1  0  0  0  0
  8 35  1  0  0  0  0
  1 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC1=CC(=O)C2=C(C)C=C(O)C([C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]3OC(=O)\C=C\C3=CC=C(O)C=C3)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O11/c1-13-9-18(32)23(26-22(13)19(33)11-17(37-26)10-14(2)30)27-28(25(36)24(35)20(12-29)38-27)39-21(34)8-5-15-3-6-16(31)7-4-15/h3-9,11,20,24-25,27-29,31-32,35-36H,10,12H2,1-2H3/b8-5+/t20-,24+,25-,27-,28-/m0/s1

> <INCHI_KEY>
QACRJXSXSVUOFZ-NYPJHIEPSA-N

> <FORMULA>
C28H28O11

> <MOLECULAR_WEIGHT>
540.521

> <EXACT_MASS>
540.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.27361677594395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5S,6S)-4,5-dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.7422274410000003

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.398655061493905

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.198182832317196

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979193259405119

> <JCHEM_POLAR_SURFACE_AREA>
180.04999999999998

> <JCHEM_REFRACTIVITY>
138.3827

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5S,6S)-4,5-dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    7   36                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1                                                       
CONECT    8    4    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10    3   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22   13   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   30                                                            
CONECT   34   10                                                            
CONECT   35    8                                                            
CONECT   36    1   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4S,5S,6S)-4,5-Dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₁

Average Mass

540.5210 Da

Monoisotopic Mass

540.16316 Da

IUPAC Name

(2S,3S,4S,5S,6S)-4,5-dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3S,4S,5S,6S)-4,5-dihydroxy-2-[7-hydroxy-5-methyl-4-oxo-2-(2-oxopropyl)chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)CC1=CC(=O)C2=C(C)C=C(O)C([C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]3OC(=O)\C=C\C3=CC=C(O)C=C3)=C2O1

InChI Identifier

InChI=1S/C28H28O11/c1-13-9-18(32)23(26-22(13)19(33)11-17(37-26)10-14(2)30)27-28(25(36)24(35)20(12-29)38-27)39-21(34)8-5-15-3-6-16(31)7-4-15/h3-9,11,20,24-25,27-29,31-32,35-36H,10,12H2,1-2H3/b8-5+/t20-,24+,25-,27-,28-/m0/s1

InChI Key

QACRJXSXSVUOFZ-NYPJHIEPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aloe sp.	Plant	KNApSAcK

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
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Coumaric acid or derivatives
Cinnamic acid or derivatives
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Alcohol
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	2.05	ALOGPS
logP	1.74	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	138.38 m³·mol⁻¹	ChemAxon
Polarizability	53.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162922524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Aloe resin A (NP0060376)

MOL for NP0060376 (Aloe resin A)

3D MOL for NP0060376 (Aloe resin A)

3D SDF for NP0060376 (Aloe resin A)

3D-SDF for NP0060376 (Aloe resin A)

PDB for NP0060376 (Aloe resin A)

3D PDB for NP0060376 (Aloe resin A)

SMILES for NP0060376 (Aloe resin A)

INCHI for NP0060376 (Aloe resin A)

Structure for NP0060376 (Aloe resin A)

3D Structure for NP0060376 (Aloe resin A)