NP-MRD: Showing NP-Card for (2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one (NP0317138)

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Record Information

Version

2.0

Created at

2022-09-11 16:48:52 UTC

Updated at

2022-09-11 16:48:52 UTC

NP-MRD ID

NP0317138

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one

Description

Kamalachalcone C belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. (2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one is found in Mallotus philippensis. Based on a literature review very few articles have been published on Kamalachalcone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218482D          

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 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
  9 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 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
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 24 35  2  0  0  0  0
 17 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 14 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317138

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(O)C(C)=C2O[C@@H]3[C@H](CC2=C1O)C(C)(C)OC1=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C(C)C(O)=C31

> <INCHI_IDENTIFIER>
InChI=1S/C31H30O8/c1-14-24(34)22(20(33)12-11-17-9-7-6-8-10-17)30-23(25(14)35)29-19(31(4,5)39-30)13-18-27(37)21(16(3)32)26(36)15(2)28(18)38-29/h6-12,19,29,34-37H,13H2,1-5H3/b12-11+/t19-,29+/m0/s1

> <INCHI_KEY>
MVVFHQOKTKNFCX-HEYBQQLDSA-N

> <FORMULA>
C31H30O8

> <MOLECULAR_WEIGHT>
530.573

> <EXACT_MASS>
530.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.706211771804576

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-1-[(5aR,11aS)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one

> <JCHEM_LOGP>
7.349488845333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.679300491716786

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.434661747983936

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5924458598050295

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
147.50279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-[(5aR,11aS)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5aH-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.424   0.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.415   1.352   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.919   2.807   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.407  -1.558   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.399   3.680   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.366   0.188   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.350  -1.558   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.691   0.188   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.683   3.098   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.195   2.807   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.179   4.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.187   5.718   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.683   7.173   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.691   8.337   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.187   9.792   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.326  10.083   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   8.919   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.830   7.464   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.342   3.680   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.616   5.493   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.982   5.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   37                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15    9                                                       
CONECT   17   15   18   35                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   35                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   24   17   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   14   38   39                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₀O₈

Average Mass

530.5730 Da

Monoisotopic Mass

530.19407 Da

IUPAC Name

(2E)-1-[(5aR,11aS)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-5a,11,11a,12-tetrahydro-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one

Traditional Name

(2E)-1-[(5aR,11aS)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5aH-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(O)C(C)=C2O[C@@H]3[C@H](CC2=C1O)C(C)(C)OC1=C(C(=O)\C=C\C2=CC=CC=C2)C(O)=C(C)C(O)=C31

InChI Identifier

InChI=1S/C31H30O8/c1-14-24(34)22(20(33)12-11-17-9-7-6-8-10-17)30-23(25(14)35)29-19(31(4,5)39-30)13-18-27(37)21(16(3)32)26(36)15(2)28(18)38-29/h6-12,19,29,34-37H,13H2,1-5H3/b12-11+/t19-,29+/m0/s1

InChI Key

MVVFHQOKTKNFCX-HEYBQQLDSA-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
Mallotus philippensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamic acid or derivatives
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Acetophenone
Styrene
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Vinylogous acid
Acryloyl-group
Enone
Ketone
Organoheterocyclic compound
Polyol
Oxacycle
Ether
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	7.35	ChemAxon
pKa (Strongest Acidic)	7.43	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	147.5 m³·mol⁻¹	ChemAxon
Polarizability	57.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

101721039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one (NP0317138)

MOL for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

3D MOL for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

3D SDF for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

3D-SDF for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

PDB for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

3D PDB for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

SMILES for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

INCHI for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

Structure for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)

3D Structure for NP0317138 ((2e)-1-[(5ar,11as)-2-acetyl-1,3,6,8-tetrahydroxy-4,7,11,11-tetramethyl-11a,12-dihydro-5ah-5,10-dioxatetraphen-9-yl]-3-phenylprop-2-en-1-one)