NP-MRD: Showing NP-Card for Isotanshinone IIA (NP0139154)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 19:41:38 UTC

Updated at

2022-06-29 19:41:38 UTC

NP-MRD ID

NP0139154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isotanshinone IIA

Description

Isotanshinone IIA belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Isotanshinone IIA is found in Salvia glutinosa and Salvia miltiorrhiza. Isotanshinone IIA is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    5.5800   -1.8241    0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6317   -1.4095   -0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032   -1.3397   -1.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -0.9321   -2.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8441   -0.7361   -1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3232   -1.0284   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4448   -0.8895    1.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9260   -1.1682    2.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0656   -0.4444    0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -0.3364    1.9907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0238    0.0818    1.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5368    0.3857    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7692    0.2810   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5531   -0.1408   -0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4467   -0.2888   -1.5328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0049   -0.0217   -2.6799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223    0.6176   -1.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7237    1.1505   -1.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    0.4650   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9685    0.8149    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983    2.3128    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6935    0.0639    1.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9172   -2.8537    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4480   -1.1470    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1177   -1.8394    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8516   -1.5763   -2.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -0.5777    2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157    0.1589    2.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3074   -0.2503   -2.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238    1.4204   -2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7597    2.2499   -1.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2023    0.9406   -2.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -0.6255   -0.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6066    0.8354   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398    2.5489    1.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    2.7401    0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1646    2.7766    0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7567   -0.1263    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5960    0.6269    2.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1891   -0.9150    1.8098 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
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6  2  1  0
 14  9  1  0
 15  5  1  0
 20 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
 10 27  1  0
 11 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
 22 39  1  0
 22 40  1  0
M  END


  Mrv1533004201505092D          

 22 25  0  0  0  0            999 V2000
   -0.8637   -4.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -3.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -2.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -2.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596   -2.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399   -2.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -3.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0603   -3.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2495   -4.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -4.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -4.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187   -5.1604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -3.7538    0.0000 C   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  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  9 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
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
  5 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0139154

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1C(=O)C1=CC=C3C(CCCC3(C)C)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O3/c1-10-9-22-18-14(10)16(20)12-6-7-13-11(15(12)17(18)21)5-4-8-19(13,2)3/h6-7,9H,4-5,8H2,1-3H3

> <INCHI_KEY>
QHGPIJMPUOVBOL-UHFFFAOYSA-N

> <FORMULA>
C19H18O3

> <MOLECULAR_WEIGHT>
294.35

> <EXACT_MASS>
294.12559444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.72707918149201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,6,13-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1,7,9,12(16),13-pentaene-11,17-dione

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
4.531694530333333

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.029434697925783

> <JCHEM_POLAR_SURFACE_AREA>
47.28

> <JCHEM_REFRACTIVITY>
85.08899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,6,13-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1,7,9,12(16),13-pentaene-11,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -1.612  -8.173   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.667  -6.957   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.095  -5.478   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.179  -4.614   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.395  -5.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.911  -5.288   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.434  -3.839   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.904  -6.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.420  -6.194   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.943  -4.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.459  -4.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.452  -5.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.929  -7.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.446  -7.364   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.932  -8.640   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.413  -7.371   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.889  -8.820   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.374  -9.091   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.381  -7.913   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.865  -8.184   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.342  -9.633   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.872  -7.007   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   19                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈O₃

Average Mass

294.3500 Da

Monoisotopic Mass

294.12559 Da

IUPAC Name

6,6,13-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1,7,9,12(16),13-pentaene-11,17-dione

Traditional Name

6,6,13-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadeca-1,7,9,12(16),13-pentaene-11,17-dione

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(=O)C1=CC=C3C(CCCC3(C)C)=C1C2=O

InChI Identifier

InChI=1S/C19H18O3/c1-10-9-22-18-14(10)16(20)12-6-7-13-11(15(12)17(18)21)5-4-8-19(13,2)3/h6-7,9H,4-5,8H2,1-3H3

InChI Key

QHGPIJMPUOVBOL-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 glutinosa	LOTUS Database	35616633
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

Isotanshinone skeleton
Phenanthrene
Naphthofuran
Naphthalene
Tetralin
Aryl ketone
Benzenoid
Furan
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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
logP	4.11	ALOGPS
logP	4.53	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.28 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.09 m³·mol⁻¹	ChemAxon
Polarizability	32.73 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

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

626354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isotanshinone IIA (NP0139154)

MOL for NP0139154 (Isotanshinone IIA)

3D MOL for NP0139154 (Isotanshinone IIA)

3D SDF for NP0139154 (Isotanshinone IIA)

3D-SDF for NP0139154 (Isotanshinone IIA)

PDB for NP0139154 (Isotanshinone IIA)

3D PDB for NP0139154 (Isotanshinone IIA)

SMILES for NP0139154 (Isotanshinone IIA)

INCHI for NP0139154 (Isotanshinone IIA)

Structure for NP0139154 (Isotanshinone IIA)

3D Structure for NP0139154 (Isotanshinone IIA)