NP-MRD: Showing NP-Card for (1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione (NP0292251)

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Record Information

Version

2.0

Created at

2022-09-09 23:41:58 UTC

Updated at

2022-09-09 23:41:58 UTC

NP-MRD ID

NP0292251

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

Description

(1R,2R,4S,7R,8S,11S,12R,18S)-7-[(2S)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icos-13-ene-5,15,20-trione 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. (1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione is found in Citrus natsudaidai and Phellodendron amurense. Based on a literature review very few articles have been published on (1R,2R,4S,7R,8S,11S,12R,18S)-7-[(2S)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icos-13-ene-5,15,20-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102201412D          

 35 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102201412D          

 35 40  0  0  1  0            999 V2000
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 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 22 30  1  0  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  1  1  0  0  0
 35 34  1  1  0  0  0
 33 35  1  0  0  0  0
 20 35  1  0  0  0  0
 15 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292251

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O9/c1-22(2)14-11-15(27)25(5)13(23(14,3)8-7-16(28)34-22)6-9-24(4)18(12-10-17(29)32-20(12)30)33-21(31)19-26(24,25)35-19/h7-8,10,13-14,18-20,30H,6,9,11H2,1-5H3/t13-,14+,18-,19+,20-,23+,24-,25-,26+/m0/s1

> <INCHI_KEY>
DZWMSKKYNYZQTC-KFPFEIEJSA-N

> <FORMULA>
C26H30O9

> <MOLECULAR_WEIGHT>
486.517

> <EXACT_MASS>
486.188982546

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.35703695813551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,7R,8S,11S,12R,18S)-7-[(2S)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-ene-5,15,20-trione

> <JCHEM_LOGP>
2.6711593483333322

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.730228716668416

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.303217278766658

> <JCHEM_PKA_STRONGEST_BASIC>
-4.303772014294933

> <JCHEM_POLAR_SURFACE_AREA>
128.73000000000002

> <JCHEM_REFRACTIVITY>
119.13309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,7R,8S,11S,12R,18S)-7-[(2S)-2-hydroxy-5-oxo-2H-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-ene-5,15,20-trione

> <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       9.887   3.641   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.814   2.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.975   3.828   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.130   1.737   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.326   0.209   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.787  -0.278   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.253  -0.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.720  -0.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.882   0.545   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.287  -0.876   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.368   2.006   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.346   3.158   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.838   2.849   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.816   4.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.351   1.388   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.201   2.921   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.373   0.236   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.886  -1.225   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.378  -1.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.356  -0.382   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.869  -1.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.847  -0.691   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.360  -2.152   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.256  -3.405   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.342  -4.644   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.807  -6.112   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.119  -4.157   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.108  -2.617   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.347  -1.703   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.175   0.461   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.312   1.922   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.710   3.074   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.820   2.231   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.329   2.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.842   1.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   11                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   35                                             
CONECT   16   15                                                            
CONECT   17   15    9   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   35                                             
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
CONECT   30   22   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33   35                                                       
CONECT   35   34   33   20   15                                             
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₉

Average Mass

486.5170 Da

Monoisotopic Mass

486.18898 Da

IUPAC Name

(1R,2R,4S,7R,8S,11S,12R,18S)-7-[(2S)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-ene-5,15,20-trione

Traditional Name

(1R,2R,4S,7R,8S,11S,12R,18S)-7-[(2S)-2-hydroxy-5-oxo-2H-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-ene-5,15,20-trione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H30O9/c1-22(2)14-11-15(27)25(5)13(23(14,3)8-7-16(28)34-22)6-9-24(4)18(12-10-17(29)32-20(12)30)33-21(31)19-26(24,25)35-19/h7-8,10,13-14,18-20,30H,6,9,11H2,1-5H3/t13-,14+,18-,19+,20-,23+,24-,25-,26+/m0/s1

InChI Key

DZWMSKKYNYZQTC-KFPFEIEJSA-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
Citrus natsudaidai	LOTUS Database	35616633
Phellodendron amurense	LOTUS Database	35616633

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
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
2-furanone
Pyran
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Ether
Oxirane
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.67	ChemAxon
pKa (Strongest Acidic)	5.3	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	128.73 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	119.13 m³·mol⁻¹	ChemAxon
Polarizability	48.36 Å³	ChemAxon
Number of Rings	6	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

162912722

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione (NP0292251)

MOL for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

3D MOL for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

3D SDF for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

3D-SDF for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

PDB for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

3D PDB for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

SMILES for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

INCHI for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

Structure for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)

3D Structure for NP0292251 ((1r,2r,4s,7r,8s,11s,12r,18s)-7-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione)