NP-MRD: Showing NP-Card for 7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione (NP0299449)

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Record Information

Version

2.0

Created at

2022-09-10 11:16:43 UTC

Updated at

2022-09-10 11:16:43 UTC

NP-MRD ID

NP0299449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione

Description

7-(Furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icosane-5,15,19-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. 7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione is found in Citrus reticulata. 7-(Furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icosane-5,15,19-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512582D          

 35 40  0  0  0  0            999 V2000
    5.2964    1.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004171512582D          

 35 40  0  0  0  0            999 V2000
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 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  2 30  1  0  0  0  0
 10 30  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 31 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C4(C)C(C(=O)C(O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-22(2)17-16(29)18(30)25(5)13(24(17,4)14(27)10-15(28)34-22)6-8-23(3)19(12-7-9-32-11-12)33-21(31)20-26(23,25)35-20/h7,9,11,13-14,17-20,27,30H,6,8,10H2,1-5H3

> <INCHI_KEY>
BMCRLPQAFRMIIT-UHFFFAOYSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.533

> <EXACT_MASS>
488.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.2666270374607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.6830868126666656

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.40741538646899

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.844561649620516

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8726928081501684

> <JCHEM_POLAR_SURFACE_AREA>
135.8

> <JCHEM_REFRACTIVITY>
117.68989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         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  O   UNK     0       6.921  -2.063   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.882   0.545   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.287  -0.876   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.373   0.236   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.886  -1.225   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.378  -1.534   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.356  -0.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.869  -1.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.847  -0.691   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.175   0.461   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.312   1.922   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.710   3.074   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.820   2.231   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.329   2.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.842   1.079   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.351   1.388   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.201   2.921   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.838   2.849   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.816   4.001   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.346   3.158   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.833   4.619   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.368   2.006   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.360  -2.152   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.256  -3.405   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.342  -4.644   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.119  -4.157   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.108  -2.617   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   30                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   30                                             
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18   31                                                  
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   30                                                  
CONECT   29   28                                                            
CONECT   30   28    2   10                                                  
CONECT   31   17   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₉

Average Mass

488.5330 Da

Monoisotopic Mass

488.20463 Da

IUPAC Name

7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione

Traditional Name

7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione

CAS Registry Number

Not Available

SMILES

CC12CCC3C4(C)C(C(=O)C(O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O

InChI Identifier

InChI=1S/C26H32O9/c1-22(2)17-16(29)18(30)25(5)13(24(17,4)14(27)10-15(28)34-22)6-8-23(3)19(12-7-9-32-11-12)33-21(31)20-26(23,25)35-20/h7,9,11,13-14,17-20,27,30H,6,8,10H2,1-5H3

InChI Key

BMCRLPQAFRMIIT-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 reticulata	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
Caprolactone
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Oxepane
Oxane
Pyran
Dicarboxylic acid or derivatives
Heteroaromatic compound
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Carboxylic acid derivative
Dialkyl ether
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.22	ALOGPS
logP	1.68	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.84	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.69 m³·mol⁻¹	ChemAxon
Polarizability	49.27 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

13857956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione (NP0299449)

MOL for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

3D MOL for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

3D SDF for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

3D-SDF for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

PDB for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

3D PDB for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

SMILES for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

INCHI for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

Structure for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)

3D Structure for NP0299449 (7-(furan-3-yl)-13,20-dihydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,19-trione)