NP-MRD: Showing NP-Card for methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate (NP0297772)

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Record Information

Version

1.0

Created at

2022-09-10 08:25:21 UTC

Updated at

2022-09-10 08:25:21 UTC

NP-MRD ID

NP0297772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate

Description

Methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate is found in Piper aduncum. Based on a literature review very few articles have been published on methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210252D          

 37 40  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309102210252D          

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 16 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 12 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 10 37  2  0  0  0  0
  5 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC=C(O)C(=C1)C1C(OC2=C1C(OC)=CC(O)C2C(=O)CCC1=CC=CC=C1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O8/c1-29(2,34)27-23(18-14-17(28(33)36-4)11-13-19(18)30)25-22(35-3)15-21(32)24(26(25)37-27)20(31)12-10-16-8-6-5-7-9-16/h5-9,11,13-15,21,23-24,27,30,32,34H,10,12H2,1-4H3

> <INCHI_KEY>
BUYHVQYKLADDJT-UHFFFAOYSA-N

> <FORMULA>
C29H32O8

> <MOLECULAR_WEIGHT>
508.567

> <EXACT_MASS>
508.20971799

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.99146497062681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate

> <JCHEM_LOGP>
2.619238151999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.948313479816013

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.245789213209571

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1151386677654305

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
139.7443

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.215  -7.903   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.708  -7.583   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.232  -6.118   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.263  -4.974   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.726  -5.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.696  -6.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.189  -6.622   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.287  -5.158   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.793  -4.838   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.713   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.253  -1.303   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.713  -2.843   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.530   1.777   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.864   2.547   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.197   2.547   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.197   4.087   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.530   4.857   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.530   6.397   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.864   7.167   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.198   6.397   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.198   4.857   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.864   4.087   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.250  -4.334   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   37                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   34                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   13   21   31                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   20   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   12   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoic acid	Generator

Chemical Formula

C₂₉H₃₂O₈

Average Mass

508.5670 Da

Monoisotopic Mass

508.20972 Da

IUPAC Name

methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate

Traditional Name

methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C(O)C(=C1)C1C(OC2=C1C(OC)=CC(O)C2C(=O)CCC1=CC=CC=C1)C(C)(C)O

InChI Identifier

InChI=1S/C29H32O8/c1-29(2,34)27-23(18-14-17(28(33)36-4)11-13-19(18)30)25-22(35-3)15-21(32)24(26(25)37-27)20(31)12-10-16-8-6-5-7-9-16/h5-9,11,13-15,21,23-24,27,30,32,34H,10,12H2,1-4H3

InChI Key

BUYHVQYKLADDJT-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
Piper aduncum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Benzofuran
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Methyl ester
Tertiary alcohol
Dihydrofuran
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.62	ChemAxon
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.74 m³·mol⁻¹	ChemAxon
Polarizability	52.99 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

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

162820252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate (NP0297772)

MOL for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

3D MOL for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

3D SDF for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

3D-SDF for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

PDB for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

3D PDB for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

SMILES for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

INCHI for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

Structure for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)

3D Structure for NP0297772 (methyl 4-hydroxy-3-[6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3,6,7-tetrahydro-1-benzofuran-3-yl]benzoate)