NP-MRD: Showing NP-Card for methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate (NP0222935)

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Record Information

Version

1.0

Created at

2022-09-06 00:53:53 UTC

Updated at

2022-09-06 00:53:54 UTC

NP-MRD ID

NP0222935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Piperaduncine B 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-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate is found in Piper longicaudatum. It was first documented in 2022 (PMID: 36075636). Based on a literature review a significant number of articles have been published on piperaduncine B (PMID: 36075614) (PMID: 36075610) (PMID: 36075538) (PMID: 36075481).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202532D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062202532D          

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 24 29  1  0  0  0  0
 19 30  2  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 10 37  2  0  0  0  0
  5 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC=C(O)C(=C1)[C@H]1[C@@H](OC2=C(C(=O)CCC3=CC=CC=C3)C(O)=CC(OC)=C12)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O8/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/h5-9,11,13-15,23,27,30,32,34H,10,12H2,1-4H3/t23-,27-/m1/s1

> <INCHI_KEY>
KGNWKZGVYSTAOX-YIXXDRMTSA-N

> <FORMULA>
C29H30O8

> <MOLECULAR_WEIGHT>
506.551

> <EXACT_MASS>
506.194067926

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.568705358688064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.146287665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.272865987212358

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.154399418408756

> <JCHEM_PKA_STRONGEST_BASIC>
-3.115495395639014

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
137.59290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.821   5.297   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.315   4.977   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.869   2.368   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.698   4.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.187   2.232   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.258  -5.153   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.590  -5.153   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -6.693   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.860  -1.303   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.320   0.237   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.320  -2.843   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.143   1.728   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   32                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   19   12   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   11   33                                                  
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   10    5                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₀O₈

Average Mass

506.5510 Da

Monoisotopic Mass

506.19407 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC=C(O)C(=C1)[C@H]1[C@@H](OC2=C(C(=O)CCC3=CC=CC=C3)C(O)=CC(OC)=C12)C(C)(C)O

InChI Identifier

InChI=1S/C29H30O8/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/h5-9,11,13-15,23,27,30,32,34H,10,12H2,1-4H3/t23-,27-/m1/s1

InChI Key

KGNWKZGVYSTAOX-YIXXDRMTSA-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 longicaudatum	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
2'-hydroxy-dihydrochalcone
1-phenylcoumaran
P-hydroxybenzoic acid ester
Butyrophenone
P-hydroxybenzoic acid alkyl ester
Benzoate ester
Coumaran
Benzoic acid or derivatives
Anisole
Phenol ether
Benzoyl
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	5.15	ChemAxon
pKa (Strongest Acidic)	8.15	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	137.59 m³·mol⁻¹	ChemAxon
Polarizability	53.57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

24705767

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44575763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pugliese NR, Balletti A, Armenia S, De Biase N, Faita F, Mengozzi A, Paneni F, Ruschitzka F, Virdis A, Ghiadoni L, Taddei S, Williams B, Antonini-Canterin F, Masi S: Ventricular-Arterial Coupling Derived From Proximal Aortic Stiffness and Aerobic Capacity Across the Heart Failure Spectrum. JACC Cardiovasc Imaging. 2022 Sep;15(9):1545-1559. doi: 10.1016/j.jcmg.2022.03.024. Epub 2022 May 11. [PubMed:36075614 ]
Cerutti A, Filipska M, Fa XM, Tacho-Pinot R: Impact of the mucosal milieu on antibody responses to allergens. J Allergy Clin Immunol. 2022 Sep;150(3):503-512. doi: 10.1016/j.jaci.2022.07.007. [PubMed:36075636 ]
Qi B, Hariri A, Nezhad R, Fu L, Li Y, Jin Z, Yim W, He T, Cheng Y, Zhou J, Jokerst JV: A miniaturized ultrasound transducer for monitoring full-mouth oral health: a preliminary study. Dentomaxillofac Radiol. 2022 Sep 8:20220220. doi: 10.1259/dmfr.20220220. [PubMed:36075610 ]
Gronbeck C, Grant-Kels JM, Lu J, Feng H: Increased Utilization of Teledermatology Among Medicare Part B Beneficiaries During the Covid-19 Pandemic. Clin Dermatol. 2022 Sep 5. pii: S0738-081X(22)00120-1. doi: 10.1016/j.clindermatol.2022.09.004. [PubMed:36075538 ]
Murray J, Bauer A, Loret de Mola C, Martins RC, Blumenberg C, Esposti MD, Stein A, Barros FC, Hallal PC, Silveira MF, Bertoldi AD, Domingues MR: Child and Maternal Mental Health Before and During the COVID-19 Pandemic: Longitudinal Social Inequalities in a Brazilian Birth Cohort. J Am Acad Child Adolesc Psychiatry. 2022 Sep 1. pii: S0890-8567(22)01323-5. doi: 10.1016/j.jaac.2022.07.832. [PubMed:36075481 ]
LOTUS database [Link]

Showing NP-Card for methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate (NP0222935)

MOL for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

3D MOL for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

3D SDF for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

3D-SDF for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

PDB for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

3D PDB for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

SMILES for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

INCHI for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

Structure for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)

3D Structure for NP0222935 (methyl 4-hydroxy-3-[(2r,3r)-6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-7-(3-phenylpropanoyl)-2,3-dihydro-1-benzofuran-3-yl]benzoate)