NP-MRD: Showing NP-Card for (+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin (NP0078238)

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Record Information

Version

2.0

Created at

2022-04-28 23:20:35 UTC

Updated at

2022-04-28 23:20:35 UTC

NP-MRD ID

NP0078238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin

Description

CHEMBL4442748 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,12alpha-Tetrahydroxy-28-norisotoonafolin is found in Toona ciliata . Based on a literature review very few articles have been published on CHEMBL4442748.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201202D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292201202D          

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M  END
> <DATABASE_ID>
NP0078238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12OC(=O)[C@H](O)[C@]1(O)[C@]1(C)[C@H](CC2=O)O[C@H]2[C@H]1[C@@](C)(O)[C@@]13O[C@@H]1C[C@@H](C1=COC=C1)[C@]3(C)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O10/c1-20-11(10-5-6-32-9-10)7-14-25(20,34-14)22(3,30)16-15(17(20)27)33-13-8-12(26)23(4)24(31,21(13,16)2)18(28)19(29)35-23/h5-6,9,11,13-18,27-28,30-31H,7-8H2,1-4H3/t11-,13-,14+,15-,16+,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1

> <INCHI_KEY>
OMQBBQBLEKPHLY-CJXASKDKSA-N

> <FORMULA>
C25H30O10

> <MOLECULAR_WEIGHT>
490.505

> <EXACT_MASS>
490.183897166

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.9856546207424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-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>
0.52

> <JCHEM_LOGP>
-0.642624750333334

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.67736142645057

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.335266168996544

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7733145661087115

> <JCHEM_POLAR_SURFACE_AREA>
159.19

> <JCHEM_REFRACTIVITY>
113.81399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-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  O   UNK     0       1.570  -3.097   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.081  -0.101   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.071   1.432   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.340   2.050   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.848   2.361   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.069  -1.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.574  -0.796   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.351  -2.125   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.327  -3.275   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.917  -2.657   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.673  -1.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.966   2.429   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.214   1.699   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.170  -0.776   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.322  -2.309   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.912  -2.927   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.726  -2.943   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.977  -2.045   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.380  -2.680   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.824  -0.513   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.421   0.122   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.591   1.652   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.099   1.964   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.734   3.367   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.862   0.626   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.453   2.689   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.092   0.899   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.286  -0.997   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.408   0.562   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4   18   19                                             
CONECT    4    3    5   10   11                                             
CONECT    5    4    6    8   17                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10    4                                                       
CONECT   12    8   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17    5                                                            
CONECT   18    3                                                            
CONECT   19    3                                                            
CONECT   20    2   21   27   35                                             
CONECT   21   20   22   23                                                  
CONECT   22   21    1                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31   34                                             
CONECT   27   26   20   28   33                                             
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   26                                                       
CONECT   32   28                                                            
CONECT   33   27                                                            
CONECT   34   26                                                            
CONECT   35   20                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₁₀

Average Mass

490.5050 Da

Monoisotopic Mass

490.18390 Da

IUPAC Name

(1S,2S,3R,4R,7R,10S,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-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,12S,13R,14R,15R,17R,19S,20R)-15-(furan-3-yl)-3,4,13,20-tetrahydroxy-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@@]12OC(=O)[C@H](O)[C@]1(O)[C@]1(C)[C@H](CC2=O)O[C@H]2[C@H]1[C@@](C)(O)[C@@]13O[C@@H]1C[C@@H](C1=COC=C1)[C@]3(C)[C@H]2O

InChI Identifier

InChI=1S/C25H30O10/c1-20-11(10-5-6-32-9-10)7-14-25(20,34-14)22(3,30)16-15(17(20)27)33-13-8-12(26)23(4)24(31,21(13,16)2)18(28)19(29)35-23/h5-6,9,11,13-18,27-28,30-31H,7-8H2,1-4H3/t11-,13-,14+,15-,16+,17-,18-,20+,21+,22+,23-,24-,25+/m0/s1

InChI Key

OMQBBQBLEKPHLY-CJXASKDKSA-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	0.52	ALOGPS
logP	-0.64	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	113.81 m³·mol⁻¹	ChemAxon
Polarizability	47.99 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

155516010

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,12alpha-Tetrahydroxy-28-norisotoonafolin (NP0078238)

MOL for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

3D MOL for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

3D SDF for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

3D-SDF for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

PDB for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

3D PDB for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

SMILES for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

INCHI for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

Structure for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)

3D Structure for NP0078238 ((+)-5alpha,6beta,8alpha,12alpha-Tetrahydroxy-28-norisotoonafolin)