NP-MRD: Showing NP-Card for Hydroxytanshinone IIA (NP0139163)

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Record Information

Version

2.0

Created at

2022-06-29 19:42:01 UTC

Updated at

2022-06-29 19:42:01 UTC

NP-MRD ID

NP0139163

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxytanshinone IIA

Description

Hydroxytanshinone belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Hydroxytanshinone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, hydroxytanshinone has been detected, but not quantified in, a few different foods, such as alcoholic beverages, herbs and spices, and tea. Hydroxytanshinone IIA is found in Salvia przewalskii and Salvia sclarea. It was first documented in 2000 (PMID: 11413487). This could make hydroxytanshinone a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    6.0392   -0.6322   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8393    0.2173   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7403    1.5310   -0.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4768    1.8730   -0.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7023    0.8819   -0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144   -0.1890   -0.1050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9431   -1.4540    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6714   -2.4259    0.5767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4697   -1.5415    0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9365   -2.6117    0.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6334   -0.3784    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329    0.8097   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946    1.9497   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580    1.8526   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131    0.6896   -0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -0.4130    0.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482   -1.7212    0.5703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2130   -2.6788   -0.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8800   -1.6474    0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639   -0.7031   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895    0.6822   -0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4795    1.1220    1.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5839    1.6346   -1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9296    0.0020    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2446   -1.2821   -0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9275   -1.2943    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113    2.1357   -0.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0243    2.8441   -0.9239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634    2.7161   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -2.0673    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5011   -3.5499   -0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3503   -2.6326    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843   -1.3035    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1073   -1.0273   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507   -0.8258   -0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7343    2.2013    1.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315    0.5779    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7444    0.9511    2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0866    1.6255   -2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    2.6622   -0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716    1.4196   -1.1299 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
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  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  1
 18 31  1  0
 19 32  1  0
 19 33  1  0
 20 34  1  0
 20 35  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
M  END


  Mrv0541 05061309152D          

 23 26  0  0  0  0            999 V2000
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    0.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551    3.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  2  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23  8  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139163

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O4/c1-9-8-23-18-10-4-5-11-15(12(20)6-7-19(11,2)3)14(10)17(22)16(21)13(9)18/h4-5,8,12,20H,6-7H2,1-3H3

> <INCHI_KEY>
UPCWCCRFMPIOAP-UHFFFAOYSA-N

> <FORMULA>
C19H18O4

> <MOLECULAR_WEIGHT>
310.3438

> <EXACT_MASS>
310.120509064

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.46542280542824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.3008834633333333

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.115854840667883

> <JCHEM_PKA_STRONGEST_BASIC>
-3.185525092691867

> <JCHEM_POLAR_SURFACE_AREA>
67.50999999999999

> <JCHEM_REFRACTIVITY>
86.60449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.791   0.621   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.929  -0.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.943   1.665   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.890   5.740   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.342   6.553   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.373   6.011   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.180   1.533   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   19                                                       
CONECT    8    9   23                                                       
CONECT    9    1    8   13                                                  
CONECT   10    4   14   18                                                  
CONECT   11    5   15   19                                                  
CONECT   12    6   15   20                                                  
CONECT   13    9   16   18                                                  
CONECT   14   10   15   17                                                  
CONECT   15   11   12   14                                                  
CONECT   16   13   17   21                                                  
CONECT   17   14   16   22                                                  
CONECT   18   10   13   23                                                  
CONECT   19    2    3    7   11                                             
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23    8   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
1-Hydroxy-14,16-epoxy-20-nor-5(10),6,8,13,15-abietapentaene-11,12-dione	HMDB

Chemical Formula

C₁₉H₁₈O₄

Average Mass

310.3438 Da

Monoisotopic Mass

310.12051 Da

IUPAC Name

3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

Traditional Name

3-hydroxy-6,6,14-trimethyl-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-16,17-dione

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(=O)C(=O)C1=C2C=CC2=C1C(O)CCC2(C)C

InChI Identifier

InChI=1S/C19H18O4/c1-9-8-23-18-10-4-5-11-15(12(20)6-7-19(11,2)3)14(10)17(22)16(21)13(9)18/h4-5,8,12,20H,6-7H2,1-3H3

InChI Key

UPCWCCRFMPIOAP-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 przewalskii	LOTUS Database	35616633
Salvia sclarea	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

Not Available

Substituents

Not Available

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
logP	3.14	ALOGPS
logP	3.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.6 m³·mol⁻¹	ChemAxon
Polarizability	33.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036635

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015555

KNApSAcK ID

Not Available

Chemspider ID

4476947

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318349

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Hydroxytanshinone IIA (NP0139163)

MOL for NP0139163 (Hydroxytanshinone IIA)

3D MOL for NP0139163 (Hydroxytanshinone IIA)

3D SDF for NP0139163 (Hydroxytanshinone IIA)

3D-SDF for NP0139163 (Hydroxytanshinone IIA)

PDB for NP0139163 (Hydroxytanshinone IIA)

3D PDB for NP0139163 (Hydroxytanshinone IIA)

SMILES for NP0139163 (Hydroxytanshinone IIA)

INCHI for NP0139163 (Hydroxytanshinone IIA)

Structure for NP0139163 (Hydroxytanshinone IIA)

3D Structure for NP0139163 (Hydroxytanshinone IIA)