NP-MRD: Showing NP-Card for Przewaquinone C (NP0139155)

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Record Information

Version

2.0

Created at

2022-06-29 19:41:40 UTC

Updated at

2022-06-29 19:41:40 UTC

NP-MRD ID

NP0139155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Przewaquinone C

Description

Tanshinol B, also known as przewaquinone C, belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Przewaquinone C is found in Salvia miltiorrhiza. Przewaquinone C was first documented in 2017 (PMID: 29031618). Based on a literature review a small amount of articles have been published on Tanshinol B (PMID: 33289608) (PMID: 34989310) (PMID: 29670981).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    5.8005    0.1770   -0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -0.1684    0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4907   -0.7168    1.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2378   -0.8781    1.9490 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4605   -0.4656    0.9758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581   -0.0020   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7004    0.5292   -1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4338    0.9488   -2.2037 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410    0.5795   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    1.0315   -2.5083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    0.0854   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0091   -0.4077    0.7812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457   -0.8767    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208   -0.8398    1.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -0.3520    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9876    0.1226   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837    0.6595   -1.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    0.6053   -1.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978   -0.5852   -0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2081   -0.3580    0.4899 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8051    0.9159    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -1.4380    1.2184 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5773    0.4928   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3595    0.9812    0.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4779   -0.7189   -0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2914   -1.0020    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7230   -1.2683    2.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7102   -1.2172    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3255    1.7269   -1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945    0.0746   -2.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224    0.5096   -2.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5500    1.5175   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6829   -0.6490   -1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0714   -1.4919   -1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7086    1.1641    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.7488    1.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1581    0.7390    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0495   -1.1736    2.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  1
  6  2  1  0
 16 11  1  0
 12  5  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
 13 27  1  0
 14 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 21 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv1652306292221412D          

 22 25  0  0  0  0            999 V2000
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    2.0051    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O4/c1-9-8-22-17-11-5-6-12-10(4-3-7-18(12,2)21)14(11)16(20)15(19)13(9)17/h5-6,8,21H,3-4,7H2,1-2H3

> <INCHI_KEY>
JVRKHBLVECIWMZ-UHFFFAOYSA-N

> <FORMULA>
C18H16O4

> <MOLECULAR_WEIGHT>
296.322

> <EXACT_MASS>
296.104858995

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.657608738963432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-6,14-dimethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.9943939153333323

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.13095186502261

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9566854064758217

> <JCHEM_POLAR_SURFACE_AREA>
67.51

> <JCHEM_REFRACTIVITY>
82.21900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-6,14-dimethyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.928  -2.940   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.896  -2.398   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.332   3.252   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.028   3.743   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
Przewaquinone C	MeSH

Chemical Formula

C₁₈H₁₆O₄

Average Mass

296.3220 Da

Monoisotopic Mass

296.10486 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CCCC2(C)O

InChI Identifier

InChI=1S/C18H16O4/c1-9-8-22-17-11-5-6-12-10(4-3-7-18(12,2)21)14(11)16(20)15(19)13(9)17/h5-6,8,21H,3-4,7H2,1-2H3

InChI Key

JVRKHBLVECIWMZ-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, 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
Salvia miltiorrhiza	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tanshinones, isotanshinones, and derivatives

Alternative Parents

Substituents

Tanshinone skeleton
Phenanthrol
Phenanthrene
Naphthofuran
Naphthalene
Tetralin
Aryl ketone
Quinone
O-quinone
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Furan
Ketone
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
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

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

112093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126071

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim DH, Paudel P, Yu T, Ngo TM, Kim JA, Jung HA, Yokozawa T, Choi JS: Characterization of the inhibitory activity of natural tanshinones from Salvia miltiorrhiza roots on protein tyrosine phosphatase 1B. Chem Biol Interact. 2017 Dec 25;278:65-73. doi: 10.1016/j.cbi.2017.10.013. Epub 2017 Oct 12. [PubMed:29031618 ]
Rafi MO, Al-Khafaji K, Tok TT, Rahman MS: Computer-based identification of potential compounds from Salviae miltiorrhizae against Neirisaral adhesion A regulatory protein. J Biomol Struct Dyn. 2022 Jul;40(10):4301-4313. doi: 10.1080/07391102.2020.1856189. Epub 2020 Dec 8. [PubMed:33289608 ]
Alvarez MRS, Grijaldo SJB, Nacario RC, Rabajante JF, Heralde FM 3rd, Lebrilla CB, Completo GC: In silico screening-based discovery of inhibitors against glycosylation proteins dysregulated in cancer. J Biomol Struct Dyn. 2023 Mar;41(5):1540-1552. doi: 10.1080/07391102.2021.2022534. Epub 2022 Jan 6. [PubMed:34989310 ]
Wang F, Yang H, Yu S, Xue Y, Fan Z, Liang G, Geng M, Zhang A, Ding C: Total synthesis of (+/-)-tanshinol B, tanshinone I, and (+/-)-tanshindiol B and C. Org Biomol Chem. 2018 May 9;16(18):3376-3381. doi: 10.1039/c8ob00567b. [PubMed:29670981 ]

Showing NP-Card for Przewaquinone C (NP0139155)

MOL for NP0139155 (Przewaquinone C)

3D MOL for NP0139155 (Przewaquinone C)

3D SDF for NP0139155 (Przewaquinone C)

3D-SDF for NP0139155 (Przewaquinone C)

PDB for NP0139155 (Przewaquinone C)

3D PDB for NP0139155 (Przewaquinone C)

SMILES for NP0139155 (Przewaquinone C)

INCHI for NP0139155 (Przewaquinone C)

Structure for NP0139155 (Przewaquinone C)

3D Structure for NP0139155 (Przewaquinone C)