NP-MRD: Showing NP-Card for Palodesangren C (NP0060742)

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Record Information

Version

2.0

Created at

2022-04-28 05:44:21 UTC

Updated at

2022-04-28 05:44:21 UTC

NP-MRD ID

NP0060742

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Palodesangren C

Description

(5BS,9R,9aS,10S)-10-(4-hydroxy-2-methoxyphenyl)-9-(4-hydroxyphenyl)-7-methyl-2,5b,8,9,9a,10-hexahydro-1,11-dioxatetraphen-2-one 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. Palodesangren C is found in Brosimum rubescens . Based on a literature review very few articles have been published on (5bS,9R,9aS,10S)-10-(4-hydroxy-2-methoxyphenyl)-9-(4-hydroxyphenyl)-7-methyl-2,5b,8,9,9a,10-hexahydro-1,11-dioxatetraphen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207442D          

 36 41  0  0  1  0            999 V2000
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7651    1.1921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    0.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6048    1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282207442D          

 36 41  0  0  1  0            999 V2000
    5.0352   -0.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0060742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CC(O)=C1)[C@H]1OC2=C(C=C3C=CC(=O)OC3=C2)[C@H]2C=C(C)C[C@H]([C@H]12)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O6/c1-16-11-22(17-3-6-19(31)7-4-17)29-24(12-16)23-13-18-5-10-28(33)35-25(18)15-27(23)36-30(29)21-9-8-20(32)14-26(21)34-2/h3-10,12-15,22,24,29-32H,11H2,1-2H3/t22-,24+,29-,30+/m0/s1

> <INCHI_KEY>
PRFNZHGCOFIZAC-VBVMOUJJSA-N

> <FORMULA>
C30H26O6

> <MOLECULAR_WEIGHT>
482.532

> <EXACT_MASS>
482.172938557

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
51.56424027828608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
5.509249833333334

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.277409816240407

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.36116853536684

> <JCHEM_PKA_STRONGEST_BASIC>
-4.575172311726537

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
137.0924

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.76e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.895   2.225   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.683   3.098   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.195   2.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.203   3.971   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.699   5.427   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.775   5.432   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.766   4.268   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.477   6.755   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   4.844   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.838   6.300   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.830   7.464   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.683   7.173   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.187   5.718   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.179   4.553   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.691   8.337   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.350   6.591   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.854   8.046   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14    9   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   23                                                            
CONECT   27   17                                                            
CONECT   28   13   29   33                                                  
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31                                                            
CONECT   35   29   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₆

Average Mass

482.5320 Da

Monoisotopic Mass

482.17294 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(C=CC(O)=C1)[C@H]1OC2=C(C=C3C=CC(=O)OC3=C2)[C@H]2C=C(C)C[C@H]([C@H]12)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C30H26O6/c1-16-11-22(17-3-6-19(31)7-4-17)29-24(12-16)23-13-18-5-10-28(33)35-25(18)15-27(23)36-30(29)21-9-8-20(32)14-26(21)34-2/h3-10,12-15,22,24,29-32H,11H2,1-2H3/t22-,24+,29-,30+/m0/s1

InChI Key

PRFNZHGCOFIZAC-VBVMOUJJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

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

3-prenylated flavan
Pyranoflavonoid
Linear 1,7-diphenylheptane skeleton
2p-methoxyflavonoid-skeleton
Monohydroxyflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
Linear pyranocoumarin
Pyranocoumarin
Pyranochromene
Coumarin
1-benzopyran
Methoxyphenol
Benzopyran
Chromane
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	5.16	ALOGPS
logP	5.51	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	9.36	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	3	ChemAxon
Refractivity	137.09 m³·mol⁻¹	ChemAxon
Polarizability	51.56 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

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

162926157

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Palodesangren C (NP0060742)

MOL for NP0060742 (Palodesangren C)

3D MOL for NP0060742 (Palodesangren C)

3D SDF for NP0060742 (Palodesangren C)

3D-SDF for NP0060742 (Palodesangren C)

PDB for NP0060742 (Palodesangren C)

3D PDB for NP0060742 (Palodesangren C)

SMILES for NP0060742 (Palodesangren C)

INCHI for NP0060742 (Palodesangren C)

Structure for NP0060742 (Palodesangren C)

3D Structure for NP0060742 (Palodesangren C)