NP-MRD: Showing NP-Card for (1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione (NP0257042)

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Record Information

Version

2.0

Created at

2022-09-07 22:03:15 UTC

Updated at

2022-09-07 22:03:15 UTC

NP-MRD ID

NP0257042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione

Description

(1S,2R,4S,7R,8R,11R,12R,17S,19S)-19-hydroxy-7-[(5R)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]Nonadec-13-ene-5,15-dione 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. Based on a literature review very few articles have been published on (1S,2R,4S,7R,8R,11R,12R,17S,19S)-19-hydroxy-7-[(5R)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]Nonadec-13-ene-5,15-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200032D          

 34 39  0  0  1  0            999 V2000
    5.4731    1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309082200032D          

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 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 34 33  1  1  0  0  0
 32 34  1  0  0  0  0
 14 34  1  0  0  0  0
 19 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@H](O)[C@]3(C)[C@H](CC[C@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C3=C[C@H](O)OC3=O)[C@@]2(C)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-22(2)14-11-16(28)25(5)13(23(14,3)8-7-15(22)27)6-9-24(4)18(12-10-17(29)32-20(12)30)33-21(31)19-26(24,25)34-19/h7-8,10,13-14,16-19,28-29H,6,9,11H2,1-5H3/t13-,14-,16+,17-,18+,19-,23-,24-,25+,26-/m1/s1

> <INCHI_KEY>
RRFTZZWQTYRKLC-XMQMZBILSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.534

> <EXACT_MASS>
472.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.70594060543618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S,7R,8R,11R,12R,17S,19S)-19-hydroxy-7-[(5R)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15-dione

> <JCHEM_LOGP>
2.799888313333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.5266279925725

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.779031715701816

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9758430457620513

> <JCHEM_POLAR_SURFACE_AREA>
122.66000000000003

> <JCHEM_REFRACTIVITY>
118.86329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7R,8R,11R,12R,17S,19S)-19-hydroxy-7-[(5R)-5-hydroxy-2-oxo-5H-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.216   3.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.346   3.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.227   2.886   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.838  -1.849   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.206  -3.403   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.277  -4.632   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.725  -6.105   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.178  -4.128   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.148  -2.588   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.376  -1.659   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.179   0.479   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.350   2.516   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   34                                             
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   34                                             
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   21   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32   34                                                       
CONECT   34   33   32   14   19                                             
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₈

Average Mass

472.5340 Da

Monoisotopic Mass

472.20972 Da

IUPAC Name

(1S,2R,4S,7R,8R,11R,12R,17S,19S)-19-hydroxy-7-[(5R)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15-dione

Traditional Name

(1S,2R,4S,7R,8R,11R,12R,17S,19S)-19-hydroxy-7-[(5R)-5-hydroxy-2-oxo-5H-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15-dione

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@H](O)[C@]3(C)[C@H](CC[C@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C3=C[C@H](O)OC3=O)[C@@]2(C)C=CC1=O

InChI Identifier

InChI=1S/C26H32O8/c1-22(2)14-11-16(28)25(5)13(23(14,3)8-7-15(22)27)6-9-24(4)18(12-10-17(29)32-20(12)30)33-21(31)19-26(24,25)34-19/h7-8,10,13-14,16-19,28-29H,6,9,11H2,1-5H3/t13-,14-,16+,17-,18+,19-,23-,24-,25+,26-/m1/s1

InChI Key

RRFTZZWQTYRKLC-XMQMZBILSA-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

Not Available

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
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Cyclohexenone
Pyran
Oxane
2-furanone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Dihydrofuran
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Ether
Oxirane
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
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	2.8	ChemAxon
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	118.86 m³·mol⁻¹	ChemAxon
Polarizability	47.71 Å³	ChemAxon
Number of Rings	6	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

162958344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione (NP0257042)

MOL for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

3D MOL for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

3D SDF for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

3D-SDF for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

PDB for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

3D PDB for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

SMILES for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

INCHI for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

Structure for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)

3D Structure for NP0257042 ((1s,2r,4s,7r,8r,11r,12r,17s,19s)-19-hydroxy-7-[(5r)-5-hydroxy-2-oxo-5h-furan-3-yl]-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15-dione)