NP-MRD: Showing NP-Card for 16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione (NP0249388)

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Record Information

Version

2.0

Created at

2022-09-07 11:55:51 UTC

Updated at

2022-09-07 11:55:51 UTC

NP-MRD ID

NP0249388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione

Description

16-(Furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]Nonadec-3-ene-5,10-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. 16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione is found in Toona sureni. 16-(Furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]Nonadec-3-ene-5,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518232D          

 32 37  0  0  0  0            999 V2000
    5.0297    1.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0071    2.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1476    0.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0217   -0.1694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6605   -0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8404   -0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996    0.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717   -0.4536    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


  Mrv1533004191518232D          

 32 37  0  0  0  0            999 V2000
    5.0297    1.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0249388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4C(O)C(=O)C3(C)C11OC1CC2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O6/c1-22(2)20-19(28)21(29)25(5)16(23(20,3)9-7-18(27)32-22)6-10-24(4)15(14-8-11-30-13-14)12-17-26(24,25)31-17/h7-9,11,13,15-17,19-20,28H,6,10,12H2,1-5H3

> <INCHI_KEY>
KXIBKDPQXSWDJM-UHFFFAOYSA-N

> <FORMULA>
C26H32O6

> <MOLECULAR_WEIGHT>
440.536

> <EXACT_MASS>
440.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.579533812408215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.6465561313333335

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.025618225743834

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7873017597531673

> <JCHEM_POLAR_SURFACE_AREA>
89.27

> <JCHEM_REFRACTIVITY>
116.36779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       9.389   3.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.303   2.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.480   3.836   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.609   1.718   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.786   0.188   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.240  -0.316   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.700  -0.903   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.169  -0.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.346   0.566   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.734  -0.847   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.834   0.276   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.329  -1.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.816  -1.469   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.809  -0.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.155  -1.699   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.269  -0.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.178   1.199   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.086   2.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.505   2.678   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.313   1.150   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.826   1.441   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.227   2.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.330   2.896   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.323   4.060   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.843   3.186   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.348   4.641   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.851   2.021   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.661  -1.502   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.214  -2.976   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.477  -3.856   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.705  -2.927   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.200  -1.472   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   27                                             
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   27                                             
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   20                                             
CONECT   15   14                                                            
CONECT   16   14   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14   18   21                                             
CONECT   21   20   11   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2    9                                                  
CONECT   28   16   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₆

Average Mass

440.5360 Da

Monoisotopic Mass

440.21989 Da

IUPAC Name

16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione

Traditional Name

16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione

CAS Registry Number

Not Available

SMILES

CC12CCC3C4(C)C=CC(=O)OC(C)(C)C4C(O)C(=O)C3(C)C11OC1CC2C1=COC=C1

InChI Identifier

InChI=1S/C26H32O6/c1-22(2)20-19(28)21(29)25(5)16(23(20,3)9-7-18(27)32-22)6-10-24(4)15(14-8-11-30-13-14)12-17-26(24,25)31-17/h7-9,11,13,15-17,19-20,28H,6,10,12H2,1-5H3

InChI Key

KXIBKDPQXSWDJM-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
Toona sureni	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
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	3.88	ALOGPS
logP	3.65	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.27 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.37 m³·mol⁻¹	ChemAxon
Polarizability	46.58 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

3501312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione (NP0249388)

MOL for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

3D MOL for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

3D SDF for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

3D-SDF for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

PDB for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

3D PDB for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

SMILES for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

INCHI for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

Structure for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)

3D Structure for NP0249388 (16-(furan-3-yl)-9-hydroxy-2,7,7,11,17-pentamethyl-6,13-dioxapentacyclo[9.8.0.0²,⁸.0¹²,¹⁴.0¹²,¹⁷]nonadec-3-ene-5,10-dione)