NP-MRD: Showing NP-Card for Aureoglanduloside A (NP0331563)

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Record Information

Version

2.0

Created at

2023-03-20 08:00:26 UTC

Updated at

2025-02-11 15:45:44 UTC

NP-MRD ID

NP0331563

Natural Product DOI

https://doi.org/10.57994/0540

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aureoglanduloside A

Description

Aureoglanduloside A belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. Aureoglanduloside A was first documented in 2023 (PMID: 36907662). Based on a literature review very few articles have been published on Aureoglanduloside A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303202309002D          

 69 75  0  0  1  0            999 V2000
   14.3881   -4.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6253   -4.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4649   -2.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652303202309002D          

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   13.6253   -4.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 61 62  1  0  0  0  0
 60 63  2  0  0  0  0
 53 63  1  0  0  0  0
 39 64  2  0  0  0  0
  8 65  2  0  0  0  0
  5 66  1  0  0  0  0
 66 67  2  0  0  0  0
  2 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331563

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@@H]2[C@H]3CO[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4OC(=O)\C(=C\C4=CC(OC)=C(O)C(OC)=C4)C4=CC(O)=C(O)C=C4CCO[C@H](O3)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C46H54O23/c1-19-34(52)37(55)38(56)45(65-19)69-41-39(57)44-62-10-9-22-15-26(48)27(49)16-23(22)24(11-21-13-30(60-3)36(54)31(14-21)61-4)43(58)68-42-35(53)28(50)17-63-46(42)64-18-32(66-44)40(41)67-33(51)8-6-20-5-7-25(47)29(12-20)59-2/h5-8,11-16,19,28,32,34-35,37-42,44-50,52-57H,9-10,17-18H2,1-4H3/b8-6+,24-11+/t19-,28+,32+,34-,35-,37+,38+,39+,40+,41+,42+,44+,45-,46-/m0/s1

> <INCHI_KEY>
QASUTJBCLFFVRO-ZPXVZAGKSA-N

> <FORMULA>
C46H54O23

> <MOLECULAR_WEIGHT>
974.915

> <EXACT_MASS>
974.305587999

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
95.84601741535116

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,7R,8S,9R,12E,22R,23R,24R,25R)-7,8,15,16,23-pentahydroxy-12-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-11-oxo-24-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,10,21,26-pentaoxatetracyclo[20.3.1.0^{4,9}.0^{13,18}]hexacosa-13,15,17-trien-25-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
1.9346435569999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.328629527680217

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.758048124644628

> <JCHEM_PKA_STRONGEST_BASIC>
-3.676505497283866

> <JCHEM_POLAR_SURFACE_AREA>
337.96999999999997

> <JCHEM_REFRACTIVITY>
232.2053

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,7R,8S,9R,12E,22R,23R,24R,25R)-7,8,15,16,23-pentahydroxy-12-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-11-oxo-24-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,10,21,26-pentaoxatetracyclo[20.3.1.0^{4,9}.0^{13,18}]hexacosa-13,15,17-trien-25-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-23         0                                  
HETATM    1  O   UNK     0      26.858  -8.943   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      25.434  -8.357   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.214  -9.296   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.790  -8.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.586  -7.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.162  -6.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.958  -5.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.534  -4.484   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      19.331  -2.957   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      17.907  -2.370   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.772  -0.836   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      19.032   0.048   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      18.897   1.582   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.501   2.232   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.366   3.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.970   4.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.627   4.650   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.492   6.184   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      20.158   2.466   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.554   1.816   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.023   4.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.284   4.884   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.375  -0.186   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.306   1.352   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.102  -0.926   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.250  -2.605   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.330  -3.702   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.620  -5.069   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.101  -4.816   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.642  -5.660   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.711  -7.198   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.413  -8.027   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.046  -7.317   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.748  -8.145   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.496  -5.337   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.129  -4.627   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.276  -4.950   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.978  -5.778   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.611  -5.068   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.025  -3.971   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.841  -2.701   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.543  -3.530   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.694  -2.379   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.878  -3.649   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       6.625  -0.841   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.259  -0.131   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.924  -0.012   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.772  -1.163   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.070  -0.334   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      12.437  -1.044   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      13.735  -0.216   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       7.176  -2.820   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.108  -1.282   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.741  -0.572   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.672   0.967   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       4.306   1.677   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       3.008   0.848   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       6.971   1.795   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.902   3.334   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       8.337   1.085   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       9.635   1.914   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      11.002   1.204   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       8.406  -0.453   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       7.313  -5.897   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      18.315  -5.423   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      23.806  -6.243   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      25.230  -6.830   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      26.450  -5.890   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      27.874  -6.477   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   67                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   66                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   65                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   21                                                  
CONECT   18   17                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   17   22                                                  
CONECT   22   21                                                            
CONECT   23   11   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   51                                                  
CONECT   26   25   27                                                       
CONECT   27   26   10   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   30   35   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   64                                                  
CONECT   40   39   41   52                                                  
CONECT   41   40   42   48                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   41   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   25                                                       
CONECT   52   40   53                                                       
CONECT   53   52   54   63                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   58                                                  
CONECT   56   55   57                                                       
CONECT   57   56                                                            
CONECT   58   55   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   63                                                  
CONECT   61   60   62                                                       
CONECT   62   61                                                            
CONECT   63   60   53                                                       
CONECT   64   39                                                            
CONECT   65    8                                                            
CONECT   66    5   67                                                       
CONECT   67   66    2   68                                                  
CONECT   68   67   69                                                       
CONECT   69   68                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  150    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₅₄O₂₃

Average Mass

974.9150 Da

Monoisotopic Mass

974.30559 Da

IUPAC Name

(1R,4S,7R,8S,9R,12E,22R,23R,24R,25R)-7,8,15,16,23-pentahydroxy-12-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-11-oxo-24-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,10,21,26-pentaoxatetracyclo[20.3.1.0^{4,9}.0^{13,18}]hexacosa-13,15,17-trien-25-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@@H]2[C@H]3CO[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4OC(=O)\C(=C\C4=CC(OC)=C(O)C(OC)=C4)C4=CC(O)=C(O)C=C4CCO[C@H](O3)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C46H54O23/c1-19-34(52)37(55)38(56)45(65-19)69-41-39(57)44-62-10-9-22-15-26(48)27(49)16-23(22)24(11-21-13-30(60-3)36(54)31(14-21)61-4)43(58)68-42-35(53)28(50)17-63-46(42)64-18-32(66-44)40(41)67-33(51)8-6-20-5-7-25(47)29(12-20)59-2/h5-8,11-16,19,28,32,34-35,37-42,44-50,52-57H,9-10,17-18H2,1-4H3/b8-6+,24-11+/t19-,28+,32+,34-,35-,37+,38+,39+,40+,41+,42+,44+,45-,46-/m0/s1

InChI Key

QASUTJBCLFFVRO-ZPXVZAGKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	xht8710@163.com	Not Available	Not Available	2023-03-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.13, CD₃OD, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Caryopteris aureoglandulosa		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as saccharolipids. These are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Alkyl glycoside
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.93	ChemAxon
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	337.97 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	232.21 m³·mol⁻¹	ChemAxon
Polarizability	95.85 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1002/cbdv.202201037

Showing NP-Card for Aureoglanduloside A (NP0331563)

MOL for NP0331563 (Aureoglanduloside A)

3D MOL for NP0331563 (Aureoglanduloside A)

3D SDF for NP0331563 (Aureoglanduloside A)

3D-SDF for NP0331563 (Aureoglanduloside A)

PDB for NP0331563 (Aureoglanduloside A)

3D PDB for NP0331563 (Aureoglanduloside A)

SMILES for NP0331563 (Aureoglanduloside A)

INCHI for NP0331563 (Aureoglanduloside A)

Structure for NP0331563 (Aureoglanduloside A)

3D Structure for NP0331563 (Aureoglanduloside A)