NP-MRD: Showing NP-Card for [(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol (NP0195762)

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Record Information

Version

2.0

Created at

2022-09-04 13:41:28 UTC

Updated at

2022-09-04 13:41:28 UTC

NP-MRD ID

NP0195762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol

Description

[(2S,3S,4R)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position. [(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol is found in Ulmus thomasii. Based on a literature review very few articles have been published on [(2S,3S,4R)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215412D          

 32 34  0  0  1  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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   -0.3416    2.1329   -0.9056 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042215412D          

 32 34  0  0  1  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0195762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C([C@H]([C@H](CO)[C@@H](CO)C2)C2=CC(OC)=C(OC)C(OC)=C2)C(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-27-17-9-14(10-18(28-2)22(17)30-4)20-16(12-26)15(11-25)7-13-8-19(29-3)23(31-5)24(32-6)21(13)20/h8-10,15-16,20,25-26H,7,11-12H2,1-6H3/t15-,16-,20+/m1/s1

> <INCHI_KEY>
GZDNLIQJLPCMPD-QINHECLXSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.512

> <EXACT_MASS>
448.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.525933242276324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S,3S,4R)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol

> <JCHEM_LOGP>
1.7568839163333347

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.743646408817597

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.135354837720964

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6036881189846026

> <JCHEM_POLAR_SURFACE_AREA>
95.84000000000002

> <JCHEM_REFRACTIVITY>
119.7636

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4R)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -6.930   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      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   19                                                  
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    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26    5   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27    3   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5120 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

[(2S,3S,4R)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol

Traditional Name

[(2S,3S,4R)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C([C@H]([C@H](CO)[C@@H](CO)C2)C2=CC(OC)=C(OC)C(OC)=C2)C(OC)=C1OC

InChI Identifier

InChI=1S/C24H32O8/c1-27-17-9-14(10-18(28-2)22(17)30-4)20-16(12-26)15(11-25)7-13-8-19(29-3)23(31-5)24(32-6)21(13)20/h8-10,15-16,20,25-26H,7,11-12H2,1-6H3/t15-,16-,20+/m1/s1

InChI Key

GZDNLIQJLPCMPD-QINHECLXSA-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
Ulmus thomasii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9p-dihydroxyaryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9'- position.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

9,9p-dihydroxyaryltetralin lignans

Direct Parent

9,9p-dihydroxyaryltetralin lignans

Alternative Parents

Substituents

9,9p-dihydroxyaryltetralin lignan
Tetralin
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary 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	1.76	ChemAxon
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.84 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	119.76 m³·mol⁻¹	ChemAxon
Polarizability	47.53 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

163190193

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol (NP0195762)

MOL for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

3D MOL for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

3D SDF for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

3D-SDF for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

PDB for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

3D PDB for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

SMILES for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

INCHI for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

Structure for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)

3D Structure for NP0195762 ([(2s,3s,4r)-3-(hydroxymethyl)-5,6,7-trimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol)