NP-MRD: Showing NP-Card for 6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one (NP0305121)

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Record Information

Version

2.0

Created at

2022-09-10 20:40:49 UTC

Updated at

2022-09-10 20:40:49 UTC

NP-MRD ID

NP0305121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one

Description

6-(Furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-3-one 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. 6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one is found in Pterorhachis zenkeri. 6-(Furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523092D          

 34 40  0  0  0  0            999 V2000
    5.3430    2.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1708   -1.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495   -0.1288    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


  Mrv1533004191523092D          

 34 40  0  0  0  0            999 V2000
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 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 23 29  1  0  0  0  0
 27 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 30 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC(=O)C3C(C)(C(O)CC4C5(C)C(O)CC(O)C34COC5O)C11OC1CC2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-22-9-14(27)20-24(3,26(22)19(34-26)6-13(22)12-4-5-32-10-12)17(29)7-15-23(2)16(28)8-18(30)25(15,20)11-33-21(23)31/h4-5,10,13,15-21,28-31H,6-9,11H2,1-3H3

> <INCHI_KEY>
HSCJAFPISVISEW-UHFFFAOYSA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.55

> <EXACT_MASS>
474.225368055

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.22606145307765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
-0.09966442199999938

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.712339694132684

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.795077930286755

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858839052887518

> <JCHEM_POLAR_SURFACE_AREA>
132.89

> <JCHEM_REFRACTIVITY>
117.56689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one

> <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       9.974   3.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.944   2.751   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.607   1.362   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.145   1.443   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.094  -0.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.704  -0.754   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.786  -2.292   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.252  -0.241   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.589   1.149   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.754   2.863   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.492   3.265   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.411   4.803   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.224   1.592   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.156   2.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.617   2.370   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.800   3.675   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.896   1.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.522   2.503   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.713  -0.296   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.992  -1.656   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.809  -2.962   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.453  -1.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.635  -0.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.776  -1.684   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.118  -0.141   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.098   1.384   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.286   2.060   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.780   2.435   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.357   0.954   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.988  -1.212   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.772  -2.737   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.156  -3.413   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.227  -2.307   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.505  -0.946   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11   13                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13   19                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
CONECT   13    8    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   17   23   27                                             
CONECT   30   25   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₈

Average Mass

474.5500 Da

Monoisotopic Mass

474.22537 Da

IUPAC Name

6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one

Traditional Name

6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one

CAS Registry Number

Not Available

SMILES

CC12CC(=O)C3C(C)(C(O)CC4C5(C)C(O)CC(O)C34COC5O)C11OC1CC2C1=COC=C1

InChI Identifier

InChI=1S/C26H34O8/c1-22-9-14(27)20-24(3,26(22)19(34-26)6-13(22)12-4-5-32-10-12)17(29)7-15-23(2)16(28)8-18(30)25(15,20)11-33-21(23)31/h4-5,10,13,15-21,28-31H,6-9,11H2,1-3H3

InChI Key

HSCJAFPISVISEW-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
Pterorhachis zenkeri	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
17-furanylsteroid skeleton
Naphthopyran
Naphthalene
Pyran
Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Hemiacetal
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	0.85	ALOGPS
logP	-0.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	117.57 m³·mol⁻¹	ChemAxon
Polarizability	49.23 Å³	ChemAxon
Number of Rings	7	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one (NP0305121)

MOL for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

3D MOL for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

3D SDF for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

3D-SDF for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

PDB for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

3D PDB for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

SMILES for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

INCHI for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

Structure for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)

3D Structure for NP0305121 (6-(furan-3-yl)-12,16,19,21-tetrahydroxy-5,11,15-trimethyl-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-3-one)