NP-MRD: Showing NP-Card for (+)-Lariciresinol 9'-caffeinate (NP0078138)

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Record Information

Version

2.0

Created at

2022-04-28 23:16:00 UTC

Updated at

2022-04-28 23:16:00 UTC

NP-MRD ID

NP0078138

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Lariciresinol 9'-caffeinate

Description

[(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. (+)-Lariciresinol 9'-caffeinate is found in Larix olgensis var. koreana. Based on a literature review very few articles have been published on [(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201162D          

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M  END

     RDKit          3D

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  Mrv1652304292201162D          

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 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
  1 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 33 36  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078138

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@@H]1OC[C@@H](CC2=CC(OC)=C(O)C=C2)[C@H]1COC(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O9/c1-35-26-13-18(4-8-23(26)31)11-20-15-38-29(19-6-9-24(32)27(14-19)36-2)21(20)16-37-28(34)10-5-17-3-7-22(30)25(33)12-17/h3-10,12-14,20-21,29-33H,11,15-16H2,1-2H3/b10-5+/t20-,21-,29+/m1/s1

> <INCHI_KEY>
LVXBWQNYQALGLB-FUCYCWKWSA-N

> <FORMULA>
C29H30O9

> <MOLECULAR_WEIGHT>
522.55

> <EXACT_MASS>
522.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.76284231582609

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.732070389666667

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.834473663427417

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.099184472731853

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0375695206428155

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
140.7231

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.032  -4.795   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.477  -6.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.009  -5.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.914  -7.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.287  -8.532   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.756  -8.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.851  -7.448   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.129 -10.100   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.598 -10.261   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.193  -9.778   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.657  -3.885   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.121  -3.409   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.442  -1.903   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.266  -4.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.731  -3.963   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.875  -4.994   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.340  -4.518   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.484  -5.548   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.164  -7.055   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.699  -7.531   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.555  -6.500   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.379  -9.037   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.308  -8.085   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.469   3.735   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.803   4.505   0.000  0.00  0.00           C+0
CONECT    1    2    5   29                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1                                                       
CONECT    6    3    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    6                                                       
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29    1   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   33                                                            
CONECT   37   32   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S)-2-(4-Hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₉H₃₀O₉

Average Mass

522.5500 Da

Monoisotopic Mass

522.18898 Da

IUPAC Name

[(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S)-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@@H]1OC[C@@H](CC2=CC(OC)=C(O)C=C2)[C@H]1COC(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C29H30O9/c1-35-26-13-18(4-8-23(26)31)11-20-15-38-29(19-6-9-24(32)27(14-19)36-2)21(20)16-37-28(34)10-5-17-3-7-22(30)25(33)12-17/h3-10,12-14,20-21,29-33H,11,15-16H2,1-2H3/b10-5+/t20-,21-,29+/m1/s1

InChI Key

LVXBWQNYQALGLB-FUCYCWKWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Larix gmelinii var. olgensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Anisole
Catechol
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Oxolane
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.98	ALOGPS
logP	4.73	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	140.72 m³·mol⁻¹	ChemAxon
Polarizability	54.76 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

9672127

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11497321

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Lariciresinol 9'-caffeinate (NP0078138)

MOL for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

3D MOL for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

3D SDF for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

3D-SDF for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

PDB for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

3D PDB for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

SMILES for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

INCHI for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

Structure for NP0078138 ((+)-Lariciresinol 9'-caffeinate)

3D Structure for NP0078138 ((+)-Lariciresinol 9'-caffeinate)