NP-MRD: Showing NP-Card for Panduratin B (NP0054826)

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Record Information

Version

2.0

Created at

2022-04-28 01:03:16 UTC

Updated at

2022-04-28 01:03:16 UTC

NP-MRD ID

NP0054826

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Panduratin B

Description

[(2S)-7-Hydroxy-5-methoxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-8-yl][(1R,2S,6R)-3-methyl-2-(3-methyl-2-butenyl)-6-phenyl-3-cyclohexenyl]methanone belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Panduratin B is found in Boesenbergia pandurata and Boesenbergia rotunda. Based on a literature review very few articles have been published on [(2S)-7-Hydroxy-5-methoxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-8-yl][(1R,2S,6R)-3-methyl-2-(3-methyl-2-butenyl)-6-phenyl-3-cyclohexenyl]methanone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203032D          

 40 43  0  0  1  0            999 V2000
   -0.7240    1.1126    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  1  0  0  0
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 38 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282203032D          

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   -0.6432   -3.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5103   -0.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7401    1.9375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4625    2.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688    1.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526    1.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302    0.6862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4141   -0.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6916   -0.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6755   -1.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3817   -1.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042   -1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203   -0.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4787    3.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    2.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500    3.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6562    3.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401    4.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3787    3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  6  0  0  0
 11 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 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
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 23  1  0  0  0  0
  1 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  1  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  6  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
 25 35  1  0  0  0  0
 24 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054826

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)[C@@H]2[C@H](CC=C(C)C)C(C)=CC[C@H]2C2=CC=CC=C2)C2=C1C=C[C@](C)(CCC=C(C)C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C36H44O4/c1-23(2)12-11-20-36(6)21-19-29-31(39-7)22-30(37)33(35(29)40-36)34(38)32-27(17-15-24(3)4)25(5)16-18-28(32)26-13-9-8-10-14-26/h8-10,12-16,19,21-22,27-28,32,37H,11,17-18,20H2,1-7H3/t27-,28+,32-,36+/m1/s1

> <INCHI_KEY>
TVOAGJMMOUCDTK-XIERRQFNSA-N

> <FORMULA>
C36H44O4

> <MOLECULAR_WEIGHT>
540.744

> <EXACT_MASS>
540.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.21629239851771

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-5-methoxy-2-methyl-8-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]-2-(4-methylpent-3-en-1-yl)-2H-chromen-7-ol

> <ALOGPS_LOGP>
7.64

> <JCHEM_LOGP>
9.275877762333337

> <ALOGPS_LOGS>
-6.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.995219803120925

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30734196863999

> <JCHEM_PKA_STRONGEST_BASIC>
-4.619550445557085

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
168.0185

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.06e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-methoxy-2-methyl-8-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]-2-(4-methylpent-3-en-1-yl)chromen-7-ol

> <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      -1.351   2.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.003   1.333   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.315   2.129   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.027  -0.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.925  -0.846   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.895  -2.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.088  -3.286   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.406  -2.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.376  -0.950   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.694  -0.154   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.043  -0.898   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.073  -2.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.754  -3.234   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.833   0.424   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.580  -0.814   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.422  -2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.960  -2.020   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.801  -3.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.339  -3.226   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.105  -4.683   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.118  -4.826   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.201  -5.622   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.819  -1.193   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.382   3.617   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.730   4.360   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.048   3.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.018   2.025   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.670   1.281   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.640  -0.259   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.291  -1.003   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.261  -2.542   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.579  -3.338   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.928  -2.594   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.958  -1.055   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.760   5.900   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.063   4.413   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.093   5.952   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.225   6.748   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.195   8.288   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.573   6.005   0.000  0.00  0.00           C+0
CONECT    1    2   24   28                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14   15                                             
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    7   22                                                       
CONECT   22   21                                                            
CONECT   23    5                                                            
CONECT   24    1   25   36                                                  
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    1   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   25                                                            
CONECT   36   24   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₄O₄

Average Mass

540.7440 Da

Monoisotopic Mass

540.32396 Da

IUPAC Name

(2S)-5-methoxy-2-methyl-8-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]-2-(4-methylpent-3-en-1-yl)-2H-chromen-7-ol

Traditional Name

(2S)-5-methoxy-2-methyl-8-[(1R,2S,6R)-3-methyl-2-(3-methylbut-2-en-1-yl)-6-phenylcyclohex-3-ene-1-carbonyl]-2-(4-methylpent-3-en-1-yl)chromen-7-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)[C@@H]2[C@H](CC=C(C)C)C(C)=CC[C@H]2C2=CC=CC=C2)C2=C1C=C[C@](C)(CCC=C(C)C)O2

InChI Identifier

InChI=1S/C36H44O4/c1-23(2)12-11-20-36(6)21-19-29-31(39-7)22-30(37)33(35(29)40-36)34(38)32-27(17-15-24(3)4)25(5)16-18-28(32)26-13-9-8-10-14-26/h8-10,12-16,19,21-22,27-28,32,37H,11,17-18,20H2,1-7H3/t27-,28+,32-,36+/m1/s1

InChI Key

TVOAGJMMOUCDTK-XIERRQFNSA-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
Boesenbergia pandurata	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
1-benzopyran
Anisole
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	7.64	ALOGPS
logP	9.28	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	168.02 m³·mol⁻¹	ChemAxon
Polarizability	62.22 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

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

101855694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Panduratin B (NP0054826)

MOL for NP0054826 (Panduratin B)

3D MOL for NP0054826 (Panduratin B)

3D SDF for NP0054826 (Panduratin B)

3D-SDF for NP0054826 (Panduratin B)

PDB for NP0054826 (Panduratin B)

3D PDB for NP0054826 (Panduratin B)

SMILES for NP0054826 (Panduratin B)

INCHI for NP0054826 (Panduratin B)

Structure for NP0054826 (Panduratin B)

3D Structure for NP0054826 (Panduratin B)