NP-MRD: Showing NP-Card for 5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde (NP0222375)

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Record Information

Version

2.0

Created at

2022-09-06 00:11:47 UTC

Updated at

2022-09-06 00:11:47 UTC

NP-MRD ID

NP0222375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

Description

Euvimal 1 belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. 5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde is found in Eucalyptus viminalis. Based on a literature review very few articles have been published on Euvimal 1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202112D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062202112D          

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 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  6  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  1  0  0  0
 26 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H](C1=C(O)C(C=O)=C(O)C(C=O)=C1O)[C@]1(C)CC[C@@H]2[C@H]1[C@H]1[C@@H](CC[C@@]2(C)O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19-,21-,22+,27+,28-/m1/s1

> <INCHI_KEY>
IBLPTYJTKWQCDX-XOQZPGFESA-N

> <FORMULA>
C28H40O6

> <MOLECULAR_WEIGHT>
472.622

> <EXACT_MASS>
472.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.36981232378743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1S)-1-[(1aR,1bR,2R,4aR,5R,7aR)-5-hydroxy-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-2-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

> <JCHEM_LOGP>
7.634406423666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.756828707589799

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.677256865580053

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5137813161268133

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
133.18099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S)-1-[(1aR,1bR,2R,4aR,5R,7aR)-5-hydroxy-1,1,2,5-tetramethyl-octahydrocyclopropa[e]azulen-2-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.200  -2.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.031  -1.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.322  -0.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.569  -1.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.399  -0.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.937  -0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.767   0.960   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.059   2.327   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.306   0.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.136   2.186   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.674   2.116   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.014  -0.478   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.553  -0.548   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.184  -1.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.892  -3.143   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.062  -4.440   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.646  -1.705   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.816  -3.002   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.691   1.100   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.405   0.253   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.125   1.662   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.034   3.199   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.543   3.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.713   2.290   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.182   2.130   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.102   3.228   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.287   4.757   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.597   5.566   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.047   5.045   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.535   6.506   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.515   5.509   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.309   1.744   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.828   1.489   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.589   0.230   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    6   18                                                  
CONECT   18   17                                                            
CONECT   19    5   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   25   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₆

Average Mass

472.6220 Da

Monoisotopic Mass

472.28249 Da

IUPAC Name

5-[(1S)-1-[(1aR,1bR,2R,4aR,5R,7aR)-5-hydroxy-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-2-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

Traditional Name

5-[(1S)-1-[(1aR,1bR,2R,4aR,5R,7aR)-5-hydroxy-1,1,2,5-tetramethyl-octahydrocyclopropa[e]azulen-2-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H](C1=C(O)C(C=O)=C(O)C(C=O)=C1O)[C@]1(C)CC[C@@H]2[C@H]1[C@H]1[C@@H](CC[C@@]2(C)O)C1(C)C

InChI Identifier

InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19-,21-,22+,27+,28-/m1/s1

InChI Key

IBLPTYJTKWQCDX-XOQZPGFESA-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
Eucalyptus viminalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

Guaiane sesquiterpenoid
5,10-cycloaromadendrane sesquiterpenoid
Acylphloroglucinol derivative
Benzenetriol
Hydroxybenzaldehyde
Phloroglucinol derivative
Benzaldehyde
Benzoyl
Phenol
Aryl-aldehyde
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Polyol
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	7.63	ChemAxon
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	-0.51	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.18 m³·mol⁻¹	ChemAxon
Polarizability	52.37 Å³	ChemAxon
Number of Rings	4	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

101619916

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde (NP0222375)

MOL for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D MOL for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D SDF for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D-SDF for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

PDB for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D PDB for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

SMILES for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

INCHI for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

Structure for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D Structure for NP0222375 (5-[(1s)-1-[(1ar,4r,4ar,7r,7ar,7br)-4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)