NP-MRD: Showing NP-Card for (+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin (NP0078239)

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Record Information

Version

2.0

Created at

2022-04-28 23:20:38 UTC

Updated at

2022-04-28 23:20:38 UTC

NP-MRD ID

NP0078239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin

Description

CHEMBL4584794 belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin is found in Toona ciliata . Based on a literature review very few articles have been published on CHEMBL4584794.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201202D          

 34 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292201202D          

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M  END
> <DATABASE_ID>
NP0078239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@H]3O[C@H]4CC(=O)[C@]5(C)OC(=O)[C@H](O)[C@]5(O)[C@@]4(C)[C@@H]3[C@@](C)(O)[C@]11O[C@@H]1C[C@H]2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O9/c1-20-9-13-17(22(3,29)25(20)16(33-25)7-12(20)11-5-6-31-10-11)21(2)15(32-13)8-14(26)23(4)24(21,30)18(27)19(28)34-23/h5-6,10,12-13,15-18,27,29-30H,7-9H2,1-4H3/t12-,13+,15-,16+,17+,18-,20-,21+,22+,23-,24-,25+/m0/s1

> <INCHI_KEY>
MOYKAXYISXRXMP-UNWSPKOSSA-N

> <FORMULA>
C25H30O9

> <MOLECULAR_WEIGHT>
474.506

> <EXACT_MASS>
474.188982546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.28895053532898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,4R,7R,10S,12R,14S,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,20-trihydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0^{2,10}.0^{3,7}.0^{14,19}.0^{17,19}]icosane-5,8-dione

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
0.27637139666666605

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.748884675229782

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.338913815881188

> <JCHEM_PKA_STRONGEST_BASIC>
-2.770589091745519

> <JCHEM_POLAR_SURFACE_AREA>
138.96

> <JCHEM_REFRACTIVITY>
112.6065

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,7R,10S,12R,14S,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,20-trihydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0^{2,10}.0^{3,7}.0^{14,19}.0^{17,19}]icosane-5,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.888  -1.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.666  -0.448   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.903   0.891   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.363   0.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.586  -0.430   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.348  -1.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.081  -0.101   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.071   1.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.340   2.050   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.848   2.361   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.069  -1.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.574  -0.796   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.351  -2.125   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.327  -3.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.917  -2.657   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.673  -1.670   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.966   2.429   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.214   1.699   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.170  -0.776   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.322  -2.309   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.912  -2.927   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.726  -2.943   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.977  -2.045   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.380  -2.680   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.824  -0.513   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.421   0.122   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.591   1.652   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.099   1.964   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.734   3.367   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.862   0.626   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.453   2.689   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.092   0.899   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.286  -0.997   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.408   0.562   0.000  0.00  0.00           C+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   17   18                                             
CONECT    4    3    5    9   10                                             
CONECT    5    4    6    7   16                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9    4                                                       
CONECT   11    7   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16    5                                                            
CONECT   17    3                                                            
CONECT   18    3                                                            
CONECT   19    2   20   26   34                                             
CONECT   20   19   21   22                                                  
CONECT   21   20    1                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30   33                                             
CONECT   26   25   19   27   32                                             
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   25                                                       
CONECT   31   27                                                            
CONECT   32   26                                                            
CONECT   33   25                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₉

Average Mass

474.5060 Da

Monoisotopic Mass

474.18898 Da

IUPAC Name

(1S,2S,3R,4R,7R,10S,12R,14S,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,20-trihydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0^{2,10}.0^{3,7}.0^{14,19}.0^{17,19}]icosane-5,8-dione

Traditional Name

(1S,2S,3R,4R,7R,10S,12R,14S,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,20-trihydroxy-2,7,14,20-tetramethyl-6,11,18-trioxahexacyclo[10.8.0.0^{2,10}.0^{3,7}.0^{14,19}.0^{17,19}]icosane-5,8-dione

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@H]3O[C@H]4CC(=O)[C@]5(C)OC(=O)[C@H](O)[C@]5(O)[C@@]4(C)[C@@H]3[C@@](C)(O)[C@]11O[C@@H]1C[C@H]2C1=COC=C1

InChI Identifier

InChI=1S/C25H30O9/c1-20-9-13-17(22(3,29)25(20)16(33-25)7-12(20)11-5-6-31-10-11)21(2)15(32-13)8-14(26)23(4)24(21,30)18(27)19(28)34-23/h5-6,10,12-13,15-18,27,29-30H,7-9H2,1-4H3/t12-,13+,15-,16+,17+,18-,20-,21+,22+,23-,24-,25+/m0/s1

InChI Key

MOYKAXYISXRXMP-UNWSPKOSSA-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
Toona ciliata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Terpene lactone
Alpha-acyloxy ketone
Gamma butyrolactone
Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
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	1.13	ALOGPS
logP	0.28	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	112.61 m³·mol⁻¹	ChemAxon
Polarizability	47.29 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

54763994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin (NP0078239)

MOL for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

3D MOL for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

3D SDF for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

3D-SDF for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

PDB for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

3D PDB for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

SMILES for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

INCHI for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

Structure for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)

3D Structure for NP0078239 ((+)-5alpha,6beta,8alpha-Trihydroxy-28-norisotoonafolin)