NP-MRD: Showing NP-Card for (5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one (NP0266548)

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Record Information

Version

2.0

Created at

2022-09-08 10:55:31 UTC

Updated at

2022-09-08 10:55:31 UTC

NP-MRD ID

NP0266548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one

Description

Palodesangren B belongs to the class of organic compounds known as 3-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 3-position. (5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one is found in Brosimum rubescens. (5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one was first documented in 2019 (PMID: 31409069). Based on a literature review very few articles have been published on Palodesangren B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082212552D          

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M  END

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M  END


  Mrv1652309082212552D          

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 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 37 28  1  1  0  0  0
 15 37  1  0  0  0  0
 10 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC=C1[C@@H]1CC(C)=C[C@@H]2[C@H]1[C@H](OC1=C2C=C2C=CC(=O)OC2=C1)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O7/c1-15-9-21(19-6-5-18(31)13-26(19)35-2)29-22(10-15)20-11-16-4-8-28(34)36-25(16)14-27(20)37-30(29)17-3-7-23(32)24(33)12-17/h3-8,10-14,21-22,29-33H,9H2,1-2H3/t21-,22-,29-,30+/m0/s1

> <INCHI_KEY>
VKFBYVPUKNMLSC-XVIYFPLKSA-N

> <FORMULA>
C30H26O7

> <MOLECULAR_WEIGHT>
498.531

> <EXACT_MASS>
498.167853177

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.50077711609826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5bR,9R,9aS,10S)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-2,5b,8,9,9a,10-hexahydro-1,11-dioxatetraphen-2-one

> <JCHEM_LOGP>
5.205684511666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.869608444932041

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.104711076178129

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5659240003881125

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
139.0733

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5bR,9R,9aS,10S)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bH-1,11-dioxatetraphen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       3.667 -12.069   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.052 -10.657   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.521 -10.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.513 -11.649   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.999 -11.358   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.373 -11.981   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.869  -9.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.861  -8.197   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.651  -8.488   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.659  -3.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.692  -6.742   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.749  -6.742   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.229  -7.615   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.196  -8.197   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.188  -9.361   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.676  -9.070   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667 -10.234   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.171 -11.690   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.163 -12.854   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.651 -12.563   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.357 -13.727   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.147 -11.108   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.365 -10.817   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.155  -9.943   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   37                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   16   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29                                                       
CONECT   37   28   15   10                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₇

Average Mass

498.5310 Da

Monoisotopic Mass

498.16785 Da

IUPAC Name

(5bR,9R,9aS,10S)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-2,5b,8,9,9a,10-hexahydro-1,11-dioxatetraphen-2-one

Traditional Name

(5bR,9R,9aS,10S)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bH-1,11-dioxatetraphen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC=C1[C@@H]1CC(C)=C[C@@H]2[C@H]1[C@H](OC1=C2C=C2C=CC(=O)OC2=C1)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H26O7/c1-15-9-21(19-6-5-18(31)13-26(19)35-2)29-22(10-15)20-11-16-4-8-28(34)36-25(16)14-27(20)37-30(29)17-3-7-23(32)24(33)12-17/h3-8,10-14,21-22,29-33H,9H2,1-2H3/t21-,22-,29-,30+/m0/s1

InChI Key

VKFBYVPUKNMLSC-XVIYFPLKSA-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
Brosimum rubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

3-prenylated flavans

Alternative Parents

Substituents

Pyranoflavonoid
3-prenylated flavan
Linear 1,7-diphenylheptane skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
Pyranocoumarin
Linear pyranocoumarin
Pyranochromene
Coumarin
Benzopyran
Chromane
Methoxyphenol
1-benzopyran
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	5.21	ChemAxon
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	139.07 m³·mol⁻¹	ChemAxon
Polarizability	52.5 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00014556

Chemspider ID

8824346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10648988

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tangdenpaisal K, Songthammawat P, Akkarasereenon K, Chuayboonsong K, Ruchirawat S, Ploypradith P: Total Synthesis of Palodesangren B Trimethyl Ether and D Dimethyl Ether via a Late-Stage Formation of 2H-Pyran-2-one of the Tetrahydrobenzo[c]pyranochromenone Core. J Org Chem. 2019 Nov 1;84(21):13410-13429. doi: 10.1021/acs.joc.9b01596. Epub 2019 Aug 27. [PubMed:31409069 ]
LOTUS database [Link]

Showing NP-Card for (5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one (NP0266548)

MOL for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

3D MOL for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

3D SDF for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

3D-SDF for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

PDB for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

3D PDB for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

SMILES for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

INCHI for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

Structure for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)

3D Structure for NP0266548 ((5br,9r,9as,10s)-10-(3,4-dihydroxyphenyl)-9-(4-hydroxy-2-methoxyphenyl)-7-methyl-8,9,9a,10-tetrahydro-5bh-1,11-dioxatetraphen-2-one)