NP-MRD: Showing NP-Card for 3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde (NP0202759)

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Record Information

Version

2.0

Created at

2022-09-04 22:02:29 UTC

Updated at

2022-09-04 22:02:29 UTC

NP-MRD ID

NP0202759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde

Description

3-(2-{2-Ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]Octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-(2-{2-Ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]Octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508182D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241508182D          

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 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 22 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 31 34  2  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC11C(O)CC(OC1O)C(CC(C)C)C(=O)C1=CC(C(OC)C(C)C)=C(O)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O9/c1-7-20-26(35-20)19(28)10-18(34-25(26)32)14(8-12(2)3)21(29)15-9-16(24(33-6)13(4)5)23(31)17(11-27)22(15)30/h9,11-14,18-20,24-25,28,30-32H,7-8,10H2,1-6H3

> <INCHI_KEY>
BBNGNPNFMQLQLU-UHFFFAOYSA-N

> <FORMULA>
C26H38O9

> <MOLECULAR_WEIGHT>
494.581

> <EXACT_MASS>
494.251582804

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.60412100847146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
5.205921650666667

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.662497873951251

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.476294549992647

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3808524199399237

> <JCHEM_POLAR_SURFACE_AREA>
146.04999999999998

> <JCHEM_REFRACTIVITY>
128.60209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde

> <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       0.921  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.413  -1.953   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.746  -1.183   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.286  -1.183   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.516   0.151   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.850   0.921   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.184   0.151   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.850   2.461   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.516   3.231   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.183   2.461   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.183   0.921   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.151   0.151   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.850   5.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.184   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.184   3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.517   5.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.183   5.541   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.151   4.771   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.183   7.081   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.516   7.851   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.516   9.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.850  10.161   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.850  11.701   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.184  12.471   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.184   9.391   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.517  10.161   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.184   7.851   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.183  10.161   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.183  11.701   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.151   9.391   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.485  10.161   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.818   9.391   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.151   7.851   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.485   7.081   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6   11                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   22   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   20   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₉

Average Mass

494.5810 Da

Monoisotopic Mass

494.25158 Da

IUPAC Name

3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde

Traditional Name

3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde

CAS Registry Number

Not Available

SMILES

CCC1OC11C(O)CC(OC1O)C(CC(C)C)C(=O)C1=CC(C(OC)C(C)C)=C(O)C(C=O)=C1O

InChI Identifier

InChI=1S/C26H38O9/c1-7-20-26(35-20)19(28)10-18(34-25(26)32)14(8-12(2)3)21(29)15-9-16(24(33-6)13(4)5)23(31)17(11-27)22(15)30/h9,11-14,18-20,24-25,28,30-32H,7-8,10H2,1-6H3

InChI Key

BBNGNPNFMQLQLU-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Alkyl-phenylketone
Butyrophenone
Phenylpropane
Phenylketone
Benzylether
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
Resorcinol
Aryl alkyl ketone
Aryl ketone
Phenol
Aryl-aldehyde
Monocyclic benzene moiety
Benzenoid
Oxane
Vinylogous acid
Ketone
Hemiacetal
Secondary alcohol
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	2.88	ALOGPS
logP	5.21	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.48	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.6 m³·mol⁻¹	ChemAxon
Polarizability	53.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9913673

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde (NP0202759)

MOL for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

3D MOL for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

3D SDF for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

3D-SDF for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

PDB for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

3D PDB for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

SMILES for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

INCHI for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

Structure for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)

3D Structure for NP0202759 (3-(2-{2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl}-4-methylpentanoyl)-2,6-dihydroxy-5-(1-methoxy-2-methylpropyl)benzaldehyde)