NP-MRD: Showing NP-Card for Danshenol C (NP0140496)

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Record Information

Version

2.0

Created at

2022-06-29 21:37:15 UTC

Updated at

2022-06-29 21:37:15 UTC

NP-MRD ID

NP0140496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Danshenol C

Description

Danshenol C belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Danshenol C was first documented in 2006 (PMID: 16450305). Based on a literature review a small amount of articles have been published on Danshenol C (PMID: 26762059).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 48  0  0  0  0  0  0  0  0999 V2000
    1.7662    3.7474    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981    2.8519    0.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0027    2.8761   -0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8581    1.9718   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4781    0.8595    0.6728 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1900    1.2923    1.9484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7857    0.1158    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5113    0.4676    1.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810   -0.9333   -0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -1.7130   -0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -2.8841   -0.9919 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -2.6902   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4749   -1.3632   -0.5799 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5378   -1.6208    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1680   -1.2751   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064   -2.1788   -0.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347   -1.8587   -0.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -0.6604   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1885   -0.3090   -0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1520   -1.2994   -0.9616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6171    0.8907    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6682    1.7411    0.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3147    1.4166    0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9005    0.2202    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320   -0.0678    0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7430    3.7453    1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6032    4.7987    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269    3.5051    2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0641    2.4842   -0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2339    1.5112   -1.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2973    0.5268    2.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -2.5514   -2.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723   -3.4775   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8337   -0.6429   -1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261   -2.4748    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7583   -0.7204    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570   -1.9066   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7824   -3.1230   -1.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051   -2.5234   -1.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9103   -1.6104   -1.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -2.1924   -0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2007   -0.8822   -0.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6885    1.1380    0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747    2.6997    1.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161    2.0988    1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  5  1  0
  5  6  1  1
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 25  1  0
 25 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
  9 13  1  0
 24 25  1  0
 15 10  1  0
 24 18  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 13 34  1  6
 12 32  1  0
 12 33  1  0
  6 31  1  0
  4 29  1  0
  4 30  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 16 38  1  0
 17 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
M  END


  Mrv1652306292223372D          

 25 28  0  0  1  0            999 V2000
    5.2939    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455    2.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6603    2.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    1.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4868    3.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533    1.7861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  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  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 10 19  1  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1COC2=C1C(=O)[C@@](O)(CC(C)=O)C1=C2C=CC2=C(C)C=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O4/c1-11-5-4-6-15-14(11)7-8-16-18(15)21(24,9-13(3)22)20(23)17-12(2)10-25-19(16)17/h4-8,12,24H,9-10H2,1-3H3/t12-,21+/m0/s1

> <INCHI_KEY>
WQYKPUPMMFGHQW-LAJNKCICSA-N

> <FORMULA>
C21H20O4

> <MOLECULAR_WEIGHT>
336.387

> <EXACT_MASS>
336.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.0970612308119

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(14R,17R)-17-hydroxy-6,14-dimethyl-17-(2-oxopropyl)-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2,4,6,8,11(15)-hexaen-16-one

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.881395893333334

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.598265702489105

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.090728522502618

> <JCHEM_PKA_STRONGEST_BASIC>
-4.070765424267997

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
96.1449

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(14R,17R)-17-hydroxy-6,14-dimethyl-17-(2-oxopropyl)-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2,4,6,8,11(15)-hexaen-16-one

> <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   3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.090  -0.539   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.928   4.480   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.287  -2.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.565   4.266   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.099   4.738   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.957   3.705   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.775   6.244   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.460   3.334   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   11                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21   25                                             
CONECT   10    9   11   19                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   10                                                  
CONECT   20   15                                                            
CONECT   21    9   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₄

Average Mass

336.3870 Da

Monoisotopic Mass

336.13616 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1COC2=C1C(=O)[C@@](O)(CC(C)=O)C1=C2C=CC2=C(C)C=CC=C12

InChI Identifier

InChI=1S/C21H20O4/c1-11-5-4-6-15-14(11)7-8-16-18(15)21(24,9-13(3)22)20(23)17-12(2)10-25-19(16)17/h4-8,12,24H,9-10H2,1-3H3/t12-,21+/m0/s1

InChI Key

WQYKPUPMMFGHQW-LAJNKCICSA-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

Not Available

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
Hydroxysteroid
12-oxosteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Delta-7-steroid
15-oxasteroid
Steroid
Phenanthrol
Phenanthrene
Naphthofuran
Naphthalene
Benzenoid
Beta-hydroxy ketone
Acyloin
Tertiary alcohol
Vinylogous ester
Dihydrofuran
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Aldehyde
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

9863336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11688609

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu G, Peng LY, Lu L, Weng ZY, Zhao Y, Li XL, Zhao QS, Sun HD: Two new abietane diterpenoids from Salvia yunnanensis. Planta Med. 2006 Jan;72(1):84-6. doi: 10.1055/s-2005-873184. [PubMed:16450305 ]
Wang HQ, Yang LX, Chen XY, Yang PF, Chen RY: [Chemical Constituents from Salvia przewalskii Root]. Zhong Yao Cai. 2015 Jun;38(6):1197-201. [PubMed:26762059 ]

Showing NP-Card for Danshenol C (NP0140496)

MOL for NP0140496 (Danshenol C)

3D MOL for NP0140496 (Danshenol C)

3D SDF for NP0140496 (Danshenol C)

3D-SDF for NP0140496 (Danshenol C)

PDB for NP0140496 (Danshenol C)

3D PDB for NP0140496 (Danshenol C)

SMILES for NP0140496 (Danshenol C)

INCHI for NP0140496 (Danshenol C)

Structure for NP0140496 (Danshenol C)

3D Structure for NP0140496 (Danshenol C)