NP-MRD: Showing NP-Card for 2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde (NP0224159)

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Record Information

Version

2.0

Created at

2022-09-06 02:27:15 UTC

Updated at

2022-09-06 02:27:15 UTC

NP-MRD ID

NP0224159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde

Description

2,4,6-Trihydroxy-5-({5-hydroxy-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-2-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde 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. 2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde is found in Psidium guajava. 2,4,6-Trihydroxy-5-({5-hydroxy-1,1,2,5-tetramethyl-decahydro-1H-cyclopropa[e]azulen-2-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241501192D          

 36 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241501192D          

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  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 24 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 29 32  2  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  0  0  0  0
  7 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC(C)(O)C3CCC(C)(C(C4=CC=CC=C4)C4=C(O)C(C=O)=C(O)C(C=O)=C4O)C3C12

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O6/c1-28(2)19-11-13-30(4,36)20-10-12-29(3,24(20)23(19)28)22(16-8-6-5-7-9-16)21-26(34)17(14-31)25(33)18(15-32)27(21)35/h5-9,14-15,19-20,22-24,33-36H,10-13H2,1-4H3

> <INCHI_KEY>
POUWCXHIRSNTHS-UHFFFAOYSA-N

> <FORMULA>
C30H36O6

> <MOLECULAR_WEIGHT>
492.612

> <EXACT_MASS>
492.251188879

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.13599945430788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde

> <ALOGPS_LOGP>
4.82

> <JCHEM_LOGP>
7.59205397

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.594605698650087

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.517645176132079

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5137842945235448

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
139.52540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde

> <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       4.784   3.823   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.969   2.294   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.437   2.454   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.418   2.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.729   2.006   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.914   0.477   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.834  -0.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.302  -0.461   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.472   0.836   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.982   0.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.891  -1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.325  -1.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.395  -2.759   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.932  -3.140   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.446  -3.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.053  -5.033   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.567  -5.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.526  -4.353   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.133  -2.864   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.353  -2.459   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.025  -4.225   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.511  -3.821   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.904  -2.332   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.604  -4.906   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.090  -4.502   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.183  -5.586   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.211  -6.395   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.304  -7.480   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.725  -6.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.332  -8.288   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.846  -8.692   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.632  -5.714   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.146  -6.118   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.325  -1.007   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.604  -2.521   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.843  -1.262   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   14   22   32                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   21   33                                                  
CONECT   33   32                                                            
CONECT   34    7    6   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₆

Average Mass

492.6120 Da

Monoisotopic Mass

492.25119 Da

IUPAC Name

2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde

Traditional Name

2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

CC1(C)C2CCC(C)(O)C3CCC(C)(C(C4=CC=CC=C4)C4=C(O)C(C=O)=C(O)C(C=O)=C4O)C3C12

InChI Identifier

InChI=1S/C30H36O6/c1-28(2)19-11-13-30(4,36)20-10-12-29(3,24(20)23(19)28)22(16-8-6-5-7-9-16)21-26(34)17(14-31)25(33)18(15-32)27(21)35/h5-9,14-15,19-20,22-24,33-36H,10-13H2,1-4H3

InChI Key

POUWCXHIRSNTHS-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
Psidium guajava	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

5,10-cycloaromadendrane sesquiterpenoid
Guaiane sesquiterpenoid
Diphenylmethane
Acylphloroglucinol derivative
Benzenetriol
Hydroxybenzaldehyde
Phloroglucinol derivative
Benzaldehyde
Benzoyl
Aryl-aldehyde
Phenol
Benzenoid
Monocyclic benzene moiety
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Polyol
Alcohol
Organooxygen compound
Organic oxygen 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	4.82	ALOGPS
logP	7.59	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	6.52	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	5	ChemAxon
Refractivity	139.53 m³·mol⁻¹	ChemAxon
Polarizability	53.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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 2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde (NP0224159)

MOL for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

3D MOL for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

3D SDF for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

3D-SDF for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

PDB for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

3D PDB for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

SMILES for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

INCHI for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

Structure for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)

3D Structure for NP0224159 (2,4,6-trihydroxy-5-({4-hydroxy-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulen-7-yl}(phenyl)methyl)benzene-1,3-dicarbaldehyde)