NP-MRD: Showing NP-Card for Sideroxylonal A (NP0139624)

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Record Information

Version

2.0

Created at

2022-06-29 20:02:54 UTC

Updated at

2022-06-29 20:02:54 UTC

NP-MRD ID

NP0139624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sideroxylonal A

Description

Sideroxylonal A belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Sideroxylonal A is found in Eucalyptus albens, Eucalyptus grandis, Eucalyptus loxophleba and Eucalyptus sideroxylon. Sideroxylonal A was first documented in 2003 (PMID: 12775149). Based on a literature review a small amount of articles have been published on sideroxylonal A (PMID: 23526981) (PMID: 22930658) (PMID: 20570611) (PMID: 18373517).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292222022D          

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M  END
> <DATABASE_ID>
NP0139624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H]1[C@@H](C(C)C)[C@@H](OC2=C(C=O)C(O)=C(C=O)C(O)=C12)C1=C(O)C(C=O)=C(O)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O10/c1-10(2)5-12-17(11(3)4)26(19-23(34)13(6-27)20(31)14(7-28)24(19)35)36-25-16(9-30)21(32)15(8-29)22(33)18(12)25/h6-12,17,26,31-35H,5H2,1-4H3/t12-,17+,26+/m0/s1

> <INCHI_KEY>
PHQDMQGEKNBIPF-FLFOAQQMSA-N

> <FORMULA>
C26H28O10

> <MOLECULAR_WEIGHT>
500.5

> <EXACT_MASS>
500.168247102

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.981868466969594

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-2-(3,5-diformyl-2,4,6-trihydroxyphenyl)-5,7-dihydroxy-4-(2-methylpropyl)-3-(propan-2-yl)-3,4-dihydro-2H-1-benzopyran-6,8-dicarbaldehyde

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
8.526190789666666

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.684977456068605

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.788411266674065

> <JCHEM_PKA_STRONGEST_BASIC>
-4.956528521100684

> <JCHEM_POLAR_SURFACE_AREA>
178.66

> <JCHEM_REFRACTIVITY>
132.87549999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S)-2-(3,5-diformyl-2,4,6-trihydroxyphenyl)-5,7-dihydroxy-3-isopropyl-4-(2-methylpropyl)-3,4-dihydro-2H-1-benzopyran-6,8-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.532  -3.241   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.905  -4.326   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   14                                                  
CONECT    6    5    7   34                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    5    9                                                  
CONECT   15   13                                                            
CONECT   16   12   17                                                       
CONECT   17   16                                                            
CONECT   18   11                                                            
CONECT   19   10   20                                                       
CONECT   20   19                                                            
CONECT   21    7   22   26                                                  
CONECT   22   21   23   33                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28                                                            
CONECT   30   24                                                            
CONECT   31   23   32                                                       
CONECT   32   31                                                            
CONECT   33   22                                                            
CONECT   34    6   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₈O₁₀

Average Mass

500.5000 Da

Monoisotopic Mass

500.16825 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H]1[C@@H](C(C)C)[C@@H](OC2=C(C=O)C(O)=C(C=O)C(O)=C12)C1=C(O)C(C=O)=C(O)C(C=O)=C1O

InChI Identifier

InChI=1S/C26H28O10/c1-10(2)5-12-17(11(3)4)26(19-23(34)13(6-27)20(31)14(7-28)24(19)35)36-25-16(9-30)21(32)15(8-29)22(33)18(12)25/h6-12,17,26,31-35H,5H2,1-4H3/t12-,17+,26+/m0/s1

InChI Key

PHQDMQGEKNBIPF-FLFOAQQMSA-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
Eucalyptus albens	LOTUS Database	35616633
Eucalyptus grandis	LOTUS Database	35616633
Eucalyptus loxophleba	LOTUS Database	35616633
Eucalyptus sideroxylon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

7-hydroxyflavonoids

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
Acylphloroglucinol derivative
Chromane
Benzopyran
1-benzopyran
Hydroxybenzaldehyde
Benzenetriol
Phloroglucinol derivative
Benzaldehyde
Benzoyl
Aryl-aldehyde
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Organic oxide
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
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

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

8566715

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10391273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

O'Reilly-Wapstra JM, Miller AM, Hamilton MG, Williams D, Glancy-Dean N, Potts BM: Chemical variation in a dominant tree species: population divergence, selection and genetic stability across environments. PLoS One. 2013;8(3):e58416. doi: 10.1371/journal.pone.0058416. Epub 2013 Mar 20. [PubMed:23526981 ]
Boulekbache-Makhlouf L, Meudec E, Mazauric JP, Madani K, Cheynier V: Qualitative and semi-quantitative analysis of phenolics in Eucalyptus globulus leaves by high-performance liquid chromatography coupled with diode array detection and electrospray ionisation mass spectrometry. Phytochem Anal. 2013 Feb;24(2):162-70. doi: 10.1002/pca.2396. Epub 2012 Aug 29. [PubMed:22930658 ]
Sidana J, Rohilla RK, Roy N, Barrow RA, Foley WJ, Singh IP: Antibacterial sideroxylonals and loxophlebal A from Eucalyptus loxophleba foliage. Fitoterapia. 2010 Oct;81(7):878-83. doi: 10.1016/j.fitote.2010.05.016. Epub 2010 May 31. [PubMed:20570611 ]
Freeman JS, O'Reilly-Wapstra JM, Vaillancourt RE, Wiggins N, Potts BM: Quantitative trait loci for key defensive compounds affecting herbivory of eucalypts in Australia. New Phytol. 2008;178(4):846-851. doi: 10.1111/j.1469-8137.2008.02417.x. Epub 2008 Mar 25. [PubMed:18373517 ]
Eyles A, Davies NW, Mohammed C: Novel detection of formylated phloroglucinol compounds (FPCs) in the wound wood of Eucalyptus globulus and E. nitens. J Chem Ecol. 2003 Apr;29(4):881-98. doi: 10.1023/a:1022979632281. [PubMed:12775149 ]

Showing NP-Card for Sideroxylonal A (NP0139624)

MOL for NP0139624 (Sideroxylonal A)

3D MOL for NP0139624 (Sideroxylonal A)

3D SDF for NP0139624 (Sideroxylonal A)

3D-SDF for NP0139624 (Sideroxylonal A)

PDB for NP0139624 (Sideroxylonal A)

3D PDB for NP0139624 (Sideroxylonal A)

SMILES for NP0139624 (Sideroxylonal A)

INCHI for NP0139624 (Sideroxylonal A)

Structure for NP0139624 (Sideroxylonal A)

3D Structure for NP0139624 (Sideroxylonal A)