NP-MRD: Showing NP-Card for {3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate (NP0173125)

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Record Information

Version

1.0

Created at

2022-09-03 10:12:54 UTC

Updated at

2022-09-03 10:12:54 UTC

NP-MRD ID

NP0173125

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate

Description

{3-[(Acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. {3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate is found in Araucaria angustifolia. It was first documented in 2022 (PMID: 36057450). Based on a literature review a significant number of articles have been published on {3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate (PMID: 36057449) (PMID: 36057448) (PMID: 36057447) (PMID: 36057446).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032212122D          

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M  END

     RDKit          3D

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  Mrv1652309032212122D          

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M  END
> <DATABASE_ID>
NP0173125

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C1C(COC(C)=O)C(COC(C)=O)CC2=CC(OC)=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-15(27)33-13-19-9-18-11-24(31-5)25(32-6)12-20(18)26(21(19)14-34-16(2)28)17-7-8-22(29-3)23(10-17)30-4/h7-8,10-12,19,21,26H,9,13-14H2,1-6H3

> <INCHI_KEY>
CUOAFOYIZBYIOI-UHFFFAOYSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.534

> <EXACT_MASS>
472.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.00837336957876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
2.954477268333335

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.290315615453145

> <JCHEM_POLAR_SURFACE_AREA>
89.52

> <JCHEM_REFRACTIVITY>
125.1402

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    6   32                                                       
CONECT   32   31    3   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
{3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₂O₈

Average Mass

472.5340 Da

Monoisotopic Mass

472.20972 Da

IUPAC Name

{3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate

Traditional Name

{3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C1C(COC(C)=O)C(COC(C)=O)CC2=CC(OC)=C(OC)C=C12

InChI Identifier

InChI=1S/C26H32O8/c1-15(27)33-13-19-9-18-11-24(31-5)25(32-6)12-20(18)26(21(19)14-34-16(2)28)17-7-8-22(29-3)23(10-17)30-4/h7-8,10-12,19,21,26H,9,13-14H2,1-6H3

InChI Key

CUOAFOYIZBYIOI-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
Araucaria angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
O-dimethoxybenzene
Dimethoxybenzene
Tetralin
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.12	ALOGPS
logP	2.95	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	125.14 m³·mol⁻¹	ChemAxon
Polarizability	51.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

73830454

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
Park JI, Kim SJ, Kim YJ, Lee SJ: Protective role of Caesalpinia sappan extract and its main component brazilin against blue light-induced damage in human fibroblasts. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15354. [PubMed:36057446 ]
LOTUS database [Link]

Showing NP-Card for {3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate (NP0173125)

MOL for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

3D MOL for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

3D SDF for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

3D-SDF for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

PDB for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

3D PDB for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

SMILES for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

INCHI for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

Structure for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)

3D Structure for NP0173125 ({3-[(acetyloxy)methyl]-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl}methyl acetate)