NP-MRD: Showing NP-Card for Tanshindiol B (NP0139161)

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Record Information

Version

2.0

Created at

2022-06-29 19:41:56 UTC

Updated at

2022-06-29 19:41:56 UTC

NP-MRD ID

NP0139161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tanshindiol B

Description

Tanshindiol B belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Tanshindiol B is found in Salvia miltiorrhiza. Tanshindiol B was first documented in 2014 (PMID: 24767850). Based on a literature review a small amount of articles have been published on Tanshindiol B (PMID: 29670981) (PMID: 33600944).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    5.7911    0.5155    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6576   -0.1485    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6910   -1.1961   -0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4600   -1.4855   -0.8309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139   -0.6984   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113    0.1703    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561    1.1731    1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3419    1.9323    2.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1812    1.2219    1.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5817    2.0704    2.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667    0.2891    0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546   -0.6472   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -1.5497   -1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8675   -1.5181   -1.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774   -0.6056   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9403    0.2787    0.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6243    1.3010    1.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041    1.1661    1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6136   -0.1635    0.7413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3057   -1.1580    1.6682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0657   -0.5597   -0.5794 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4263    0.4622   -1.6559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6007   -1.7963   -0.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5702    1.6053    1.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833    0.0912    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7186    0.3719    0.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5901   -1.6838   -0.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0825   -2.2579   -1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139   -2.1956   -1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3219    1.0624    2.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585    2.3275    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5371    1.9416    0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5518    1.3718    2.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7195   -0.1250    0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9128   -1.9315    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5235    1.0143   -1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8778   -0.0369   -2.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777    1.1770   -1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7224   -1.7863   -1.9240 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
 19 21  1  0
 21 22  1  0
 21 23  1  6
  6  2  1  0
 16 11  1  0
 12  5  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  6
 20 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
M  END


  Mrv1652306292221412D          

 23 26  0  0  1  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  1  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  1  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
   -0.9098    0.7029    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  1  0  0  0
 20 22  1  6  0  0  0
 19 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0139161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CC[C@H](O)[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-8-7-23-17-10-3-5-11-9(4-6-12(19)18(11,2)22)14(10)16(21)15(20)13(8)17/h3,5,7,12,19,22H,4,6H2,1-2H3/t12-,18+/m0/s1

> <INCHI_KEY>
RTKDBIDPGKCZJS-KPZWWZAWSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.56216018453729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R)-5,6-dihydroxy-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>
2.11

> <JCHEM_LOGP>
1.9194903083333323

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.751401114123006

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.106514908648645

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9567032192675278

> <JCHEM_POLAR_SURFACE_AREA>
87.74000000000001

> <JCHEM_REFRACTIVITY>
83.5805

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R)-5,6-dihydroxy-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
HETATM   23  O   UNK     0      -1.698   1.312   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   23                                                  
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1CC[C@H](O)[C@]2(C)O

InChI Identifier

InChI=1S/C18H16O5/c1-8-7-23-17-10-3-5-11-9(4-6-12(19)18(11,2)22)14(10)16(21)15(20)13(8)17/h3,5,7,12,19,22H,4,6H2,1-2H3/t12-,18+/m0/s1

InChI Key

RTKDBIDPGKCZJS-KPZWWZAWSA-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
O-quinone
Aryl ketone
Quinone
Benzenoid
Furan
Heteroaromatic compound
Tertiary alcohol
1,2-diol
Ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Organooxygen 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

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

4479300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321620

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
Zhong B, Yu J, Hou Y, Ai N, Ge W, Lu JJ, Chen X: A novel strategy for glioblastoma treatment by induction of noptosis, an NQO1-dependent necrosis. Free Radic Biol Med. 2021 Apr;166:104-115. doi: 10.1016/j.freeradbiomed.2021.02.014. Epub 2021 Feb 15. [PubMed:33600944 ]
Woo J, Kim HY, Byun BJ, Chae CH, Lee JY, Ryu SY, Park WK, Cho H, Choi G: Biological evaluation of tanshindiols as EZH2 histone methyltransferase inhibitors. Bioorg Med Chem Lett. 2014 Jun 1;24(11):2486-92. doi: 10.1016/j.bmcl.2014.04.010. Epub 2014 Apr 13. [PubMed:24767850 ]

Showing NP-Card for Tanshindiol B (NP0139161)

MOL for NP0139161 (Tanshindiol B)

3D MOL for NP0139161 (Tanshindiol B)

3D SDF for NP0139161 (Tanshindiol B)

3D-SDF for NP0139161 (Tanshindiol B)

PDB for NP0139161 (Tanshindiol B)

3D PDB for NP0139161 (Tanshindiol B)

SMILES for NP0139161 (Tanshindiol B)

INCHI for NP0139161 (Tanshindiol B)

Structure for NP0139161 (Tanshindiol B)

3D Structure for NP0139161 (Tanshindiol B)