NP-MRD: Showing NP-Card for 11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione (NP0168594)

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Record Information

Version

2.0

Created at

2022-09-03 04:25:55 UTC

Updated at

2022-09-03 04:25:55 UTC

NP-MRD ID

NP0168594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione

Description

11'-(Furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]Pentadecane]-3',6,13'-trione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione is found in Citrus aurantium. 11'-(Furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]Pentadecane]-3',6,13'-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520372D          

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M  END

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M  END


  Mrv1533004231520372D          

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 26 27  2  0  0  0  0
 23 27  1  0  0  0  0
 11 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168594

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CC(=O)C2(C)C(CCC3(C)C(OC(=O)C4OC234)C2=COC=C2)C11COC(=O)CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O9/c1-22(2,31)15-9-16(27)24(4)14(25(15)12-33-18(29)10-17(25)28)5-7-23(3)19(13-6-8-32-11-13)34-21(30)20-26(23,24)35-20/h6,8,11,14-15,17,19-20,28,31H,5,7,9-10,12H2,1-4H3

> <INCHI_KEY>
GNNAZOFNKOMONV-UHFFFAOYSA-N

> <FORMULA>
C26H32O9

> <MOLECULAR_WEIGHT>
488.533

> <EXACT_MASS>
488.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.18562538357021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.295487568666665

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.092003635684868

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.244968994870455

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7874983239571565

> <JCHEM_POLAR_SURFACE_AREA>
135.79999999999998

> <JCHEM_REFRACTIVITY>
118.22929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       9.813   4.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.400   3.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.012   2.416   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.788   5.243   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.986   3.218   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.750   4.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.337   3.524   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.100   4.442   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.160   1.994   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.699   3.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.397   1.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.220  -0.454   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.807  -1.066   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.570  -0.148   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.394  -1.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.157  -0.760   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.080   0.158   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.097   1.688   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.139   2.606   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.510   2.300   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.924   2.912   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.747   1.382   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.980  -2.290   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.114  -3.332   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.473  -4.732   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.056  -4.556   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.361  -3.046   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.810   1.688   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.223   2.300   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.460   1.382   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.283  -0.148   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.519  -1.066   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.870  -0.760   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.633   0.158   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.850  -1.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   22                                             
CONECT   10    9                                                            
CONECT   11    9   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21    9   14   20                                             
CONECT   23   16   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23                                                       
CONECT   28   11    5   29   34                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28   35                                                  
CONECT   35   34                                                            
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

11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione

Traditional Name

11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CC(=O)C2(C)C(CCC3(C)C(OC(=O)C4OC234)C2=COC=C2)C11COC(=O)CC1O

InChI Identifier

InChI=1S/C26H32O9/c1-22(2,31)15-9-16(27)24(4)14(25(15)12-33-18(29)10-17(25)28)5-7-23(3)19(13-6-8-32-11-13)34-21(30)20-26(23,24)35-20/h6,8,11,14-15,17,19-20,28,31H,5,7,9-10,12H2,1-4H3

InChI Key

GNNAZOFNKOMONV-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 aurantium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Naphthopyran
Naphthalene
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Dicarboxylic acid or derivatives
Pyran
Oxane
Heteroaromatic compound
Furan
Tertiary alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Lactone
Organoheterocyclic compound
Ether
Oxirane
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aldehyde
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	1.81	ALOGPS
logP	1.3	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-2.8	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	2	ChemAxon
Refractivity	118.23 m³·mol⁻¹	ChemAxon
Polarizability	49.19 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

4482268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione (NP0168594)

MOL for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

3D MOL for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

3D SDF for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

3D-SDF for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

PDB for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

3D PDB for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

SMILES for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

INCHI for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

Structure for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)

3D Structure for NP0168594 (11'-(furan-3-yl)-4-hydroxy-5'-(2-hydroxypropan-2-yl)-2',10'-dimethyl-12',15'-dioxaspiro[oxane-3,6'-tetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecane]-3',6,13'-trione)