NP-MRD: Showing NP-Card for (-)-Thannilignan (NP0050446)

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Record Information

Version

2.0

Created at

2022-04-27 21:39:43 UTC

Updated at

2022-04-27 21:39:44 UTC

NP-MRD ID

NP0050446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Thannilignan

Description

(2R)-2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (-)-Thannilignan is found in Terminalia bellerica . Based on a literature review very few articles have been published on (2R)-2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223392D          

 24 25  0  0  1  0            999 V2000
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  9  1  0  0  0  0
  1 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 11 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C[C@](O)(CO)C(=C)CC2=CC=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O5/c1-13(9-14-3-6-16(21)7-4-14)19(23,12-20)11-15-5-8-17(24-2)10-18(15)22/h3-8,10,20-23H,1,9,11-12H2,2H3/t19-/m0/s1

> <INCHI_KEY>
UICXJFXGPMLFAQ-IBGZPJMESA-N

> <FORMULA>
C19H22O5

> <MOLECULAR_WEIGHT>
330.38

> <EXACT_MASS>
330.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.45301772802618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.5761728489999998

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.822903830991784

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.2199580775406

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0993905531868933

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
92.0467

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -6.160   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.438  -5.184   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.978  -5.184   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.898  -2.516   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7                                                            
CONECT    9    2                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   14   24                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24   11                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₅

Average Mass

330.3800 Da

Monoisotopic Mass

330.14672 Da

IUPAC Name

(2R)-2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol

Traditional Name

(2R)-2-[(2-hydroxy-4-methoxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]but-3-ene-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C[C@](O)(CO)C(=C)CC2=CC=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C19H22O5/c1-13(9-14-3-6-16(21)7-4-14)19(23,12-20)11-15-5-8-17(24-2)10-18(15)22/h3-8,10,20-23H,1,9,11-12H2,2H3/t19-/m0/s1

InChI Key

UICXJFXGPMLFAQ-IBGZPJMESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Terminalia bellirica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Norlignan skeleton
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
1,2-diol
Ether
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.91	ALOGPS
logP	2.58	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.22	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	92.05 m³·mol⁻¹	ChemAxon
Polarizability	35.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163018288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Thannilignan (NP0050446)

MOL for NP0050446 ((-)-Thannilignan)

3D MOL for NP0050446 ((-)-Thannilignan)

3D SDF for NP0050446 ((-)-Thannilignan)

3D-SDF for NP0050446 ((-)-Thannilignan)

PDB for NP0050446 ((-)-Thannilignan)

3D PDB for NP0050446 ((-)-Thannilignan)

SMILES for NP0050446 ((-)-Thannilignan)

INCHI for NP0050446 ((-)-Thannilignan)

Structure for NP0050446 ((-)-Thannilignan)

3D Structure for NP0050446 ((-)-Thannilignan)