NP-MRD: Showing NP-Card for Parvistemin C (NP0085973)

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Record Information

Version

2.0

Created at

2022-04-29 06:23:02 UTC

Updated at

2022-04-29 06:23:02 UTC

NP-MRD ID

NP0085973

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Parvistemin C

Description

4,4'-Dihydroxy-6,6'-bis[2-(2-methoxyphenyl)ethyl]-3,3'-dimethyl-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. Parvistemin C is found in Stemona parviflora. 4,4'-Dihydroxy-6,6'-bis[2-(2-methoxyphenyl)ethyl]-3,3'-dimethyl-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509252D          

 40 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251509252D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 21 38  1  0  0  0  0
 38 39  2  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC=C1CCC1=C(C(=O)C(C)=C(O)C1=O)C1=C(CCC2=CC=CC=C2OC)C(=O)C(O)=C(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O8/c1-17-27(33)25(21(31(37)29(17)35)15-13-19-9-5-7-11-23(19)39-3)26-22(32(38)30(36)18(2)28(26)34)16-14-20-10-6-8-12-24(20)40-4/h5-12,35-36H,13-16H2,1-4H3

> <INCHI_KEY>
BHWKQSAEJGSVHV-UHFFFAOYSA-N

> <FORMULA>
C32H30O8

> <MOLECULAR_WEIGHT>
542.584

> <EXACT_MASS>
542.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
56.9517601385286

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-5-{4-hydroxy-2-[2-(2-methoxyphenyl)ethyl]-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl}-6-[2-(2-methoxyphenyl)ethyl]-3-methylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
5.761892037333333

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.060974111341218

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.399203991794902

> <JCHEM_PKA_STRONGEST_BASIC>
-4.52295482205453

> <JCHEM_POLAR_SURFACE_AREA>
127.2

> <JCHEM_REFRACTIVITY>
152.65120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-5-{4-hydroxy-2-[2-(2-methoxyphenyl)ethyl]-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl}-6-[2-(2-methoxyphenyl)ethyl]-3-methylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.669   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   12   22   38                                                  
CONECT   22   21   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   22   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   21   39                                                  
CONECT   39   38                                                            
CONECT   40   35                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₈

Average Mass

542.5840 Da

Monoisotopic Mass

542.19407 Da

IUPAC Name

2-hydroxy-5-{4-hydroxy-2-[2-(2-methoxyphenyl)ethyl]-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl}-6-[2-(2-methoxyphenyl)ethyl]-3-methylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2-hydroxy-5-{4-hydroxy-2-[2-(2-methoxyphenyl)ethyl]-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl}-6-[2-(2-methoxyphenyl)ethyl]-3-methylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=CC=C1CCC1=C(C(=O)C(C)=C(O)C1=O)C1=C(CCC2=CC=CC=C2OC)C(=O)C(O)=C(C)C1=O

InChI Identifier

InChI=1S/C32H30O8/c1-17-27(33)25(21(31(37)29(17)35)15-13-19-9-5-7-11-23(19)39-3)26-22(32(38)30(36)18(2)28(26)34)16-14-20-10-6-8-12-24(20)40-4/h5-12,35-36H,13-16H2,1-4H3

InChI Key

BHWKQSAEJGSVHV-UHFFFAOYSA-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
Stemona parviflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
Phenoxy compound
Anisole
Methoxybenzene
P-benzoquinone
Phenol ether
Quinone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Cyclic ketone
Ether
Enol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.99	ALOGPS
logP	5.76	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	5.4	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	127.2 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	152.65 m³·mol⁻¹	ChemAxon
Polarizability	56.95 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Parvistemin C (NP0085973)

MOL for NP0085973 (Parvistemin C)

3D MOL for NP0085973 (Parvistemin C)

3D SDF for NP0085973 (Parvistemin C)

3D-SDF for NP0085973 (Parvistemin C)

PDB for NP0085973 (Parvistemin C)

3D PDB for NP0085973 (Parvistemin C)

SMILES for NP0085973 (Parvistemin C)

INCHI for NP0085973 (Parvistemin C)

Structure for NP0085973 (Parvistemin C)

3D Structure for NP0085973 (Parvistemin C)