NP-MRD: Showing NP-Card for bruceanol f (NP0296022)

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Record Information

Version

2.0

Created at

2022-09-10 05:21:40 UTC

Updated at

2022-09-10 05:21:41 UTC

NP-MRD ID

NP0296022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bruceanol f

Description

Bruceanol F 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. bruceanol f is found in Brucea antidysenterica. bruceanol f was first documented in 2022 (PMID: 35895695). Based on a literature review very few articles have been published on bruceanol F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102207212D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102207212D          

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   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 29 39  1  0  0  0  0
 39  5  1  1  0  0  0
  8 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(=O)\C=C(/C)C(C)C)C(=O)O[C@@H]3C[C@H]1[C@H](C)C=C(O)C(=O)[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h7-8,11,13-14,16,18-21,23,29,31,33H,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,23+,26+,27-,28+/m1/s1

> <INCHI_KEY>
PCKQDAAUYVCTJJ-XYGKKIDYSA-N

> <FORMULA>
C28H36O11

> <MOLECULAR_WEIGHT>
548.585

> <EXACT_MASS>
548.225761979

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4087207029231

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,3R,6R,8S,9S,13S,14S,15R,16S,17S)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,12-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-10-ene-17-carboxylate

> <JCHEM_LOGP>
1.5254782999999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.743561456277277

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.714303298723959

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3289825724715705

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
134.3853

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3R,6R,8S,9S,13S,14S,15R,16S,17S)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,12-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-10-ene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.918   5.952   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.265   4.452   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.139   3.401   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.557   2.800   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.185   3.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.391   2.683   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12   39                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25   39                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    8   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   29    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
(11beta,12alpha,15beta(e))-15-((3,4-Dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-picras-2-en-21-Oic acid methyl ester	ChEBI
(11b,12a,15b(e))-15-((3,4-Dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-picras-2-en-21-Oate methyl ester	Generator
(11b,12a,15b(e))-15-((3,4-Dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-picras-2-en-21-Oic acid methyl ester	Generator
(11beta,12alpha,15beta(e))-15-((3,4-Dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-picras-2-en-21-Oate methyl ester	Generator
(11Β,12α,15β(e))-15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-picras-2-en-21-Oate methyl ester	Generator
(11Β,12α,15β(e))-15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-2,11,12-trihydroxy-1,16-dioxo-picras-2-en-21-Oic acid methyl ester	Generator

Chemical Formula

C₂₈H₃₆O₁₁

Average Mass

548.5850 Da

Monoisotopic Mass

548.22576 Da

IUPAC Name

methyl (1R,2S,3R,6R,8S,9S,13S,14S,15R,16S,17S)-3-{[(2E)-3,4-dimethylpent-2-enoyl]oxy}-11,15,16-trihydroxy-9,13-dimethyl-4,12-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-10-ene-17-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12OC[C@@]34[C@H]1[C@@H](OC(=O)\C=C(/C)C(C)C)C(=O)O[C@@H]3C[C@H]1[C@H](C)C=C(O)C(=O)[C@]1(C)[C@H]4[C@@H](O)[C@@H]2O

InChI Identifier

InChI=1S/C28H36O11/c1-11(2)12(3)8-17(30)39-19-21-27-10-37-28(21,25(35)36-6)23(33)18(31)20(27)26(5)14(9-16(27)38-24(19)34)13(4)7-15(29)22(26)32/h7-8,11,13-14,16,18-21,23,29,31,33H,9-10H2,1-6H3/b12-8+/t13-,14+,16-,18-,19-,20-,21-,23+,26+,27-,28+/m1/s1

InChI Key

PCKQDAAUYVCTJJ-XYGKKIDYSA-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
Brucea antidysenterica	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
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Furopyran
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Cyclohexenone
Fatty acid ester
Oxepane
Delta valerolactone
Delta_valerolactone
Pyran
Oxane
Fatty acyl
Hydroxy acid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Methyl ester
Tetrahydrofuran
Ketone
1,2-diol
Lactone
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Enol
Ether
Polyol
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:65528 )
methyl ester (CHEBI:65528 )
delta-lactone (CHEBI:65528 )
triol (CHEBI:65528 )
cyclic ether (CHEBI:65528 )
enoate ester (CHEBI:65528 )
enol (CHEBI:65528 )
pentacyclic triterpenoid (CHEBI:65528 )
quassinoid (CHEBI:65528 )

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	1.53	ChemAxon
pKa (Strongest Acidic)	8.71	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.39 m³·mol⁻¹	ChemAxon
Polarizability	55.41 Å³	ChemAxon
Number of Rings	5	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

4943354

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bruceanol F

METLIN ID

Not Available

PubChem Compound

6438914

PDB ID

Not Available

ChEBI ID

65528

Good Scents ID

Not Available

References

General References

Bultum LE, Tolossa GB, Lee D: Combining empirical knowledge, in silico molecular docking and ADMET profiling to identify therapeutic phytochemicals from Brucea antidysentrica for acute myeloid leukemia. PLoS One. 2022 Jul 27;17(7):e0270050. doi: 10.1371/journal.pone.0270050. eCollection 2022. [PubMed:35895695 ]
LOTUS database [Link]

Showing NP-Card for bruceanol f (NP0296022)

MOL for NP0296022 (bruceanol f)

3D MOL for NP0296022 (bruceanol f)

3D SDF for NP0296022 (bruceanol f)

3D-SDF for NP0296022 (bruceanol f)

PDB for NP0296022 (bruceanol f)

3D PDB for NP0296022 (bruceanol f)

SMILES for NP0296022 (bruceanol f)

INCHI for NP0296022 (bruceanol f)

Structure for NP0296022 (bruceanol f)

3D Structure for NP0296022 (bruceanol f)