NP-MRD: Showing NP-Card for 5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde (NP0299454)

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Record Information

Version

2.0

Created at

2022-09-10 11:17:06 UTC

Updated at

2022-09-10 11:17:07 UTC

NP-MRD ID

NP0299454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

Description

Macrocarpal I belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. 5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde is found in Eucalyptus globulus. 5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde was first documented in 2021 (PMID: 33137468). Based on a literature review very few articles have been published on Macrocarpal I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102213172D          

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M  END

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M  END


  Mrv1652309102213172D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  2  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
 14 17  2  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19  5  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 25 34  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0299454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H]([C@H]1CC[C@](C)(O)[C@H]2C[C@H](CC[C@]12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O7/c1-15(2)11-17(22-24(32)18(13-29)23(31)19(14-30)25(22)33)20-8-10-28(6,35)21-12-16(26(3,4)34)7-9-27(20,21)5/h13-17,20-21,31-35H,7-12H2,1-6H3/t16-,17-,20+,21-,27+,28-/m0/s1

> <INCHI_KEY>
PXQFFMATXFLUPK-DMVNJTFYSA-N

> <FORMULA>
C28H42O7

> <MOLECULAR_WEIGHT>
490.637

> <EXACT_MASS>
490.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.17580525091742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1S)-1-[(1R,4S,4aS,6S,8aR)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-decahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

> <JCHEM_LOGP>
7.0070424849999995

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.767552066199063

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.688077014154504

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3574850426025956

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
136.9206

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S)-1-[(1R,4S,4aS,6S,8aR)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.240  -3.374   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.657   1.180   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.772  -1.334   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.232   1.334   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -3.850   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   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   27   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   25   19   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

C₂₈H₄₂O₇

Average Mass

490.6370 Da

Monoisotopic Mass

490.29305 Da

IUPAC Name

5-[(1S)-1-[(1R,4S,4aS,6S,8aR)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-decahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

Traditional Name

5-[(1S)-1-[(1R,4S,4aS,6S,8aR)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H]([C@H]1CC[C@](C)(O)[C@H]2C[C@H](CC[C@]12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O

InChI Identifier

InChI=1S/C28H42O7/c1-15(2)11-17(22-24(32)18(13-29)23(31)19(14-30)25(22)33)20-8-10-28(6,35)21-12-16(26(3,4)34)7-9-27(20,21)5/h13-17,20-21,31-35H,7-12H2,1-6H3/t16-,17-,20+,21-,27+,28-/m0/s1

InChI Key

PXQFFMATXFLUPK-DMVNJTFYSA-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 globulus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Acylphloroglucinol derivative
Hydroxybenzaldehyde
Phloroglucinol derivative
Benzenetriol
Benzoyl
Benzaldehyde
Aryl-aldehyde
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Alcohol
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	7.01	ChemAxon
pKa (Strongest Acidic)	6.69	ChemAxon
pKa (Strongest Basic)	-0.36	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.92 m³·mol⁻¹	ChemAxon
Polarizability	54.18 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

133561815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qi L, Zhang Y, Zhang W, Wang Y, Han Y, Ding Y: The inhibition of colorectal cancer growth by the natural product macrocarpal I. Free Radic Biol Med. 2021 Jan;162:383-391. doi: 10.1016/j.freeradbiomed.2020.10.317. Epub 2020 Oct 31. [PubMed:33137468 ]
LOTUS database [Link]

Showing NP-Card for 5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde (NP0299454)

MOL for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D MOL for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D SDF for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D-SDF for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

PDB for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D PDB for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

SMILES for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

INCHI for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

Structure for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)

3D Structure for NP0299454 (5-[(1s)-1-[(1r,4s,4as,6s,8ar)-4-hydroxy-6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-octahydronaphthalen-1-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde)