NP-MRD: Showing NP-Card for 19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione (NP0328002)

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Record Information

Version

2.0

Created at

2022-09-12 11:04:37 UTC

Updated at

2022-09-12 11:04:37 UTC

NP-MRD ID

NP0328002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

Description

Isolimonexic acid, also known as isolimonexate, belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione is found in Citrus medica. Isolimonexic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502182D          

 36 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241502182D          

 36 42  0  0  0  0            999 V2000
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 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0328002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,17-19,29H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
DNNFETMOXYZICP-UHFFFAOYSA-N

> <FORMULA>
C26H30O10

> <MOLECULAR_WEIGHT>
502.516

> <EXACT_MASS>
502.183897166

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.43671710695322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
19-(5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.3982205516666644

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.354920310049774

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.779694311725011

> <JCHEM_PKA_STRONGEST_BASIC>
-3.948200103861612

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
117.74099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-(5-hydroxy-2-oxo-5H-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      13.994   7.703   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.478   7.432   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.367   8.968   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.906   5.952   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.632   5.088   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.421   3.563   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.995   2.982   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.784   1.457   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.779   3.927   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.948   5.239   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.416   6.033   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.900   5.762   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.377   4.314   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.861   4.043   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.868   5.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.345   3.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.352   4.949   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.359   6.126   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.883   7.575   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.890   8.752   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.399   7.846   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.914   8.117   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.391   6.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.907   6.940   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.796   8.476   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.430   8.388   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.438   9.565   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.946   8.659   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.939   7.482   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.829   3.501   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.693   2.226   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.748   1.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.176  -0.469   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.300   1.533   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.350   3.073   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.134   4.018   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   29                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   29                                             
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22   15   21   24                                             
CONECT   24   23   12   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    2   11                                                  
CONECT   30   17   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   30   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Value	Source
Isolimonexate	Generator

Chemical Formula

C₂₆H₃₀O₁₀

Average Mass

502.5160 Da

Monoisotopic Mass

502.18390 Da

IUPAC Name

19-(5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

Traditional Name

19-(5-hydroxy-2-oxo-5H-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

CAS Registry Number

Not Available

SMILES

CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=CC(O)OC1=O

InChI Identifier

InChI=1S/C26H30O10/c1-22(2)13-8-14(27)24(4)12(25(13)10-32-16(28)9-15(25)35-22)5-6-23(3)18(11-7-17(29)33-20(11)30)34-21(31)19-26(23,24)36-19/h7,12-13,15,17-19,29H,5-6,8-10H2,1-4H3

InChI Key

DNNFETMOXYZICP-UHFFFAOYSA-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 medica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
11-oxosteroid
Oxosteroid
2-oxosteroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta_valerolactone
1,4-dioxepane
Dioxepane
Delta valerolactone
2-furanone
Pyran
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Dihydrofuran
Ketone
Hemiacetal
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	1.83	ALOGPS
logP	1.4	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.74 m³·mol⁻¹	ChemAxon
Polarizability	49.44 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

13996851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione (NP0328002)

MOL for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

3D MOL for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

3D SDF for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

3D-SDF for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

PDB for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

3D PDB for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

SMILES for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

INCHI for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

Structure for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)

3D Structure for NP0328002 (19-(5-hydroxy-2-oxo-5h-furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione)