NP-MRD: Showing NP-Card for (+)-Glaucarubinone (NP0139549)

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Record Information

Version

2.0

Created at

2022-06-29 19:59:32 UTC

Updated at

2022-06-29 19:59:32 UTC

NP-MRD ID

NP0139549

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Glaucarubinone

Description

Glaucarubinone belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. (+)-Glaucarubinone is found in Ailanthus altissima, Ailanthus excelsa, Hannoa undulata, Perriera madagascariensis, Simarouba amara and Simarouba versicolor. (+)-Glaucarubinone was first documented in 1984 (PMID: 17340307). Based on a literature review a small amount of articles have been published on glaucarubinone (PMID: 12560029) (PMID: 19199792) (PMID: 19501276) (PMID: 21264793).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221592D          

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M  END

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 12 32  1  1  0  0  0
 11 33  1  6  0  0  0
 10 34  1  6  0  0  0
  3 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0139549

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@](C)(O)C(=O)O[C@@H]1[C@H]2[C@@H](C)[C@@H](O)[C@]3(O)OC[C@@]22[C@H]3[C@@]3(C)[C@H](O)C(=O)C=C(C)[C@@H]3C[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-12,14-18,20,27-28,31-32H,6,8-9H2,1-5H3/t11-,12+,14-,15-,16-,17-,18-,20-,22+,23-,24+,25+/m1/s1

> <INCHI_KEY>
WRBGCYVAJRRQKP-STDAJNJZSA-N

> <FORMULA>
C25H34O10

> <MOLECULAR_WEIGHT>
494.537

> <EXACT_MASS>
494.215197295

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.20234605450907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-14-en-8-yl (2S)-2-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
0.3712398596666653

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.426739362741941

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.884471825007157

> <JCHEM_PKA_STRONGEST_BASIC>
-3.655986878952845

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
118.95619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,6R,7S,8R,11R,13S,17S,18S,19R)-4,5,17-trihydroxy-6,14,18-trimethyl-9,16-dioxo-3,10-dioxapentacyclo[9.8.0.0^{1,7}.0^{4,19}.0^{13,18}]nonadec-14-en-8-yl (2S)-2-hydroxy-2-methylbutanoate

> <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      -9.328  -0.808   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.991  -1.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.661  -0.795   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.884  -2.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.331  -0.019   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.338   1.521   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -3.994  -0.783   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.664  -0.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.481  -0.617   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.319  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.019  -3.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.349  -2.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.341  -0.757   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.004   0.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.136  -1.029   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.503  -2.433   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.004   1.547   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.326   2.323   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.664   1.559   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.671   0.019   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.008  -0.744   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.338   0.032   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.676  -0.732   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.331   1.572   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.994   2.336   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.986   3.876   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.016  -2.284   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.678  -1.521   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.341   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.671   1.534   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.008   2.297   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.888  -2.317   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.026  -4.613   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.649  -3.086   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -7.437   0.535   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   35                                             
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   34                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13   16   32                                             
CONECT   13   12   14   20                                                  
CONECT   14   13    9   15   17                                             
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   14   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   13   21   28                                             
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25                                                            
CONECT   27   21                                                            
CONECT   28   20                                                            
CONECT   29   17   30                                                       
CONECT   30   29    8   31                                                  
CONECT   31   30                                                            
CONECT   32   12                                                            
CONECT   33   11                                                            
CONECT   34   10                                                            
CONECT   35    3                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(+)-Glaucarubinone	ChEBI

Chemical Formula

C₂₅H₃₄O₁₀

Average Mass

494.5370 Da

Monoisotopic Mass

494.21520 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@](C)(O)C(=O)O[C@@H]1[C@H]2[C@@H](C)[C@@H](O)[C@]3(O)OC[C@@]22[C@H]3[C@@]3(C)[C@H](O)C(=O)C=C(C)[C@@H]3C[C@H]2OC1=O

InChI Identifier

InChI=1S/C25H34O10/c1-6-22(4,31)21(30)35-16-15-11(3)17(27)25(32)20-23(5)12(10(2)7-13(26)18(23)28)8-14(34-19(16)29)24(15,20)9-33-25/h7,11-12,14-18,20,27-28,31-32H,6,8-9H2,1-5H3/t11-,12+,14-,15-,16-,17-,18-,20-,22+,23-,24+,25+/m1/s1

InChI Key

WRBGCYVAJRRQKP-STDAJNJZSA-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
Ailanthus altissima	LOTUS Database	35616633
Ailanthus excelsa	LOTUS Database	35616633
Hannoa undulata	LOTUS Database	35616633
Perriera madagascariensis	LOTUS Database	35616633
Simarouba amara	LOTUS Database	35616633
Simarouba versicolor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Triterpenoid
Polycyclic triterpenoid
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Cyclohexenone
Pyran
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Tertiary alcohol
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Hemiacetal
Lactone
Ketone
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid (CHEBI:5371 )
Dammarenes (C08763 )

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

C00003711

Chemspider ID

390388

KEGG Compound ID

C08763

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441796

PDB ID

Not Available

ChEBI ID

5371

Good Scents ID

Not Available

References

General References

Joshi BC, Pandey A, Sharma RP, Khare A: Quassinoids from Ailanthus excelsa. Phytochemistry. 2003 Feb;62(4):579-84. doi: 10.1016/s0031-9422(02)00493-4. [PubMed:12560029 ]
Waterman PG, Ampofo SA: Cytotoxic Quassinoids from Odyendyea gabonensis Stem Bark: Isolation and High-Field NMR. Planta Med. 1984 Jun;50(3):261-3. doi: 10.1055/s-2007-969694. [PubMed:17340307 ]
Beutler JA, Kang MI, Robert F, Clement JA, Pelletier J, Colburn NH, McKee TC, Goncharova E, McMahon JB, Henrich CJ: Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition. J Nat Prod. 2009 Mar 27;72(3):503-6. doi: 10.1021/np800732n. [PubMed:19199792 ]
de Mesquita ML, de Paula JE, Pessoa C, de Moraes MO, Costa-Lotufo LV, Grougnet R, Michel S, Tillequin F, Espindola LS: Cytotoxic activity of Brazilian Cerrado plants used in traditional medicine against cancer cell lines. J Ethnopharmacol. 2009 Jun 25;123(3):439-45. doi: 10.1016/j.jep.2009.03.018. Epub 2009 Mar 26. [PubMed:19501276 ]
Zarse K, Bossecker A, Muller-Kuhrt L, Siems K, Hernandez MA, Berendsohn WG, Birringer M, Ristow M: The phytochemical glaucarubinone promotes mitochondrial metabolism, reduces body fat, and extends lifespan of Caenorhabditis elegans. Horm Metab Res. 2011 Apr;43(4):241-3. doi: 10.1055/s-0030-1270524. Epub 2011 Jan 24. [PubMed:21264793 ]

Showing NP-Card for (+)-Glaucarubinone (NP0139549)

MOL for NP0139549 ((+)-Glaucarubinone)

3D MOL for NP0139549 ((+)-Glaucarubinone)

3D SDF for NP0139549 ((+)-Glaucarubinone)

3D-SDF for NP0139549 ((+)-Glaucarubinone)

PDB for NP0139549 ((+)-Glaucarubinone)

3D PDB for NP0139549 ((+)-Glaucarubinone)

SMILES for NP0139549 ((+)-Glaucarubinone)

INCHI for NP0139549 ((+)-Glaucarubinone)

Structure for NP0139549 ((+)-Glaucarubinone)

3D Structure for NP0139549 ((+)-Glaucarubinone)