NP-MRD: Showing NP-Card for (−)-Parairesinol (NP0350974)

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Record Information

Version

2.0

Created at

2025-04-24 04:54:49 UTC

Updated at

2025-05-12 16:32:47 UTC

NP-MRD ID

NP0350974

Natural Product DOI

https://doi.org/10.57994/3961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(−)-Parairesinol

Description

(−)-Parairesinol belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (−)-Parairesinol was first documented in 2025 (PMID: 40241524). Based on a literature review very few articles have been published on (−)-Parairesinol.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02042307212D          

 26 28  0  0  1  0            999 V2000
    0.6078    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973   -2.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9411   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
  4 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv2104 02042307212D          

 26 28  0  0  1  0            999 V2000
    0.6078    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973   -2.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9411   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
  7 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  0  0  0  0
  4 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0350974

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@@H]2[C@@H](CC3=CC(OC)=C(O)C=C3)COC2=O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-24-18-6-4-13(9-17(18)22)8-15-14(11-26-20(15)23)7-12-3-5-16(21)19(10-12)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

> <INCHI_KEY>
ARHRTBJYFHSMDL-LSDHHAIUSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.85884036060649

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_LOGP>
3.2917825110000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.225642204501723

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.622483080743304

> <JCHEM_PKA_STRONGEST_BASIC>
-4.589059530054854

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
95.6344

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-FEB-23         0                                  
HETATM    1  O   UNK     0       1.134   3.735   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.091  -2.854   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.657  -3.885   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.121  -3.409   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.266  -4.439   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.731  -3.963   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.875  -4.994   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.946  -5.946   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.090  -6.976   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.481  -6.422   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.337  -5.391   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.134  -0.885   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.199  -0.115   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.199   1.425   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.533   2.195   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.867   1.425   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   13                                                       
CONECT   22    4   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    2   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3900 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

(3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[(3-hydroxy-4-methoxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@@H]2[C@@H](CC3=CC(OC)=C(O)C=C3)COC2=O)C=C1O

InChI Identifier

InChI=1S/C20H22O6/c1-24-18-6-4-13(9-17(18)22)8-15-14(11-26-20(15)23)7-12-3-5-16(21)19(10-12)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

InChI Key

ARHRTBJYFHSMDL-LSDHHAIUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Himalaiella heteromalla		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Oxolane
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.29	ChemAxon
pKa (Strongest Acidic)	9.62	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.63 m³·mol⁻¹	ChemAxon
Polarizability	36.86 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

102042848

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh B, Thappa C, Komal, Laasya Priya P, Begum S, Nalli Y, Gopu B: Two new dibenzyl-gamma-butyrolactone lignans with cytotoxic activity from Himalaiella heteromalla, an Indian Himalayan plant. Nat Prod Res. 2025 Apr 17:1-8. doi: 10.1080/14786419.2025.2491122. [PubMed:40241524 ]
DOI: 10.1080/14786419.2025.2491122
PMID: 40241524

Showing NP-Card for (−)-Parairesinol (NP0350974)

MOL for NP0350974 ((−)-Parairesinol)

3D MOL for NP0350974 ((−)-Parairesinol)

3D SDF for NP0350974 ((−)-Parairesinol)

3D-SDF for NP0350974 ((−)-Parairesinol)

PDB for NP0350974 ((−)-Parairesinol)

3D PDB for NP0350974 ((−)-Parairesinol)

SMILES for NP0350974 ((−)-Parairesinol)

INCHI for NP0350974 ((−)-Parairesinol)

Structure for NP0350974 ((−)-Parairesinol)

3D Structure for NP0350974 ((−)-Parairesinol)