NP-MRD: Showing NP-Card for Paucinone I (NP0085980)

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Record Information

Version

2.0

Created at

2022-04-29 06:23:19 UTC

Updated at

2022-04-29 06:23:19 UTC

NP-MRD ID

NP0085980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paucinone I

Description

Paucinone I is found in Garcinia paucinervis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208232D          

 33 34  0  0  1  0            999 V2000
    2.4815   -1.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -1.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899    0.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748    0.8370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393    1.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4417    4.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0217    4.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    5.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0068    6.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4118    7.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918    7.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3968    8.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    9.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218    8.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6317    4.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068    4.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4018    4.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8217    5.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4232    4.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3188    1.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953    0.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -0.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
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  9 14  1  0  0  0  0
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  6 32  1  0  0  0  0
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  2 33  1  0  0  0  0
M  END

     RDKit          3D

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    5.3096    2.0991    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5099    2.6835    0.8450 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3361   -0.3092   -1.2820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878    0.2065    0.6378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0984    1.6031    0.9067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055    2.0537    1.9986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8326    2.6098    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1284    2.6401   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7637    3.6972   -1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1202    4.7857   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7581    5.8439   -1.5861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488    4.8200    0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1964    5.9169    1.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292208232D          

 33 34  0  0  1  0            999 V2000
    2.4815   -1.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -1.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9341    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9918    7.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9769    9.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2218    8.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6309   -0.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 27 29  1  0  0  0  0
 13 30  2  0  0  0  0
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  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\C[C@]1(CC=C(C)C)C(=O)C(O)=C(C(=O)C2=CC(O)=C(O)C=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O6/c1-16(2)7-6-8-18(5)12-14-27(13-11-17(3)4)25(32)22(24(31)26(27)33)23(30)19-9-10-20(28)21(29)15-19/h7,9-12,15,28-29,31H,6,8,13-14H2,1-5H3/b18-12+/t27-/m0/s1

> <INCHI_KEY>
JABJSHMLHVMIMA-UMGXQCJCSA-N

> <FORMULA>
C27H32O6

> <MOLECULAR_WEIGHT>
452.547

> <EXACT_MASS>
452.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.50244485941395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-4-(3,4-dihydroxybenzoyl)-2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-2-(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
6.138610762333332

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.972982012495728

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7945940380242167

> <JCHEM_PKA_STRONGEST_BASIC>
-6.505900280117587

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
132.51149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-(3,4-dihydroxybenzoyl)-2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-2-(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       4.632  -2.658   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.006  -1.251   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.474  -1.090   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.569  -2.336   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.848   0.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.753   1.562   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.127   2.969   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.032   4.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.556   5.680   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.091   6.156   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.572   4.215   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.477   2.969   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.048   5.680   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.558   7.927   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.774   9.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.530  10.594   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.070  10.610   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.746  11.919   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.502  13.261   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.718  14.587   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.474  15.928   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.690  17.254   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.014  15.944   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.046   7.927   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.506   7.943   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.750   9.284   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.534  10.610   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.790   9.301   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.512   6.156   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.595   3.130   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.285   1.401   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.911  -0.005   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   31                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   30                                                  
CONECT   14   13    9   15   25                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   13                                                            
CONECT   31    7                                                            
CONECT   32    6   33                                                       
CONECT   33   32    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₆

Average Mass

452.5470 Da

Monoisotopic Mass

452.21989 Da

IUPAC Name

(2S)-4-(3,4-dihydroxybenzoyl)-2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-2-(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

Traditional Name

(2S)-4-(3,4-dihydroxybenzoyl)-2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-hydroxy-2-(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\C[C@]1(CC=C(C)C)C(=O)C(O)=C(C(=O)C2=CC(O)=C(O)C=C2)C1=O

InChI Identifier

InChI=1S/C27H32O6/c1-16(2)7-6-8-18(5)12-14-27(13-11-17(3)4)25(32)22(24(31)26(27)33)23(30)19-9-10-20(28)21(29)15-19/h7,9-12,15,28-29,31H,6,8,13-14H2,1-5H3/b18-12+/t27-/m0/s1

InChI Key

JABJSHMLHVMIMA-UMGXQCJCSA-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
Garcinia paucinervis	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	4.27	ALOGPS
logP	6.14	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.51 m³·mol⁻¹	ChemAxon
Polarizability	49.5 Å³	ChemAxon
Number of Rings	2	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

Not Available

References

General References

Not Available

Showing NP-Card for Paucinone I (NP0085980)

MOL for NP0085980 (Paucinone I)

3D MOL for NP0085980 (Paucinone I)

3D SDF for NP0085980 (Paucinone I)

3D-SDF for NP0085980 (Paucinone I)

PDB for NP0085980 (Paucinone I)

3D PDB for NP0085980 (Paucinone I)

SMILES for NP0085980 (Paucinone I)

INCHI for NP0085980 (Paucinone I)

Structure for NP0085980 (Paucinone I)

3D Structure for NP0085980 (Paucinone I)