NP-MRD: Showing NP-Card for Multiorthoquinone (NP0074747)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 20:03:59 UTC

Updated at

2022-04-28 20:03:59 UTC

NP-MRD ID

NP0074747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Multiorthoquinone

Description

Multiorthoquinone belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Multiorthoquinone is found in Salvia blepharochaena Hedge and Hub.Mor., Salvia blepharochlaena and Salvia multicaulis. Multiorthoquinone was first documented in 1997 (PMID: 9428161). Multiorthoquinone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -3.8249   -2.8521   -0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2766   -1.5662   -0.3171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3500   -0.5629   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9759   -0.8724   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376    0.1000    0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3138   -0.2079   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2596    0.8067    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.0761    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5038    2.3874    0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4398    1.4025    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7859    1.7113    0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    3.0916    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107    0.7213    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1454    1.0266    0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6603    0.4785    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1680   -0.6986   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6146   -0.9884   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -1.6117   -1.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4690    0.1962   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2082   -1.7747   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6554   -2.9137   -0.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7675   -1.5447   -0.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0388   -2.5156   -0.6620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -2.8126   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369   -3.2018    0.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6635   -3.5530   -0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114   -1.8708   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741    2.8503    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8604    3.3874    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    3.1565    0.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208    3.8342    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    3.3216    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4714    1.1666    1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4374    1.9410   -0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7776    0.2092   -0.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3682    1.2893    0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8425   -1.7578    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -2.7021   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0867   -1.4292   -1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4869   -1.1529   -2.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4516    0.8832   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5295   -0.1565   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2412    0.7081    0.8107 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 13  2  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6 22  1  0
 22 23  2  0
 22 20  1  0
 20 21  2  0
 20 16  1  0
 16 15  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 10  1  0
 15  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
  9 29  1  0
  8 28  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
  4 27  1  0
M  END


  Mrv1533004201500442D          

 23 25  0  0  0  0            999 V2000
   -0.9355   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  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
 12 13  1  0  0  0  0
  6 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
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  3 19  2  0  0  0  0
 19 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(C)=C2C=CC3=C(C(=O)C(=O)C(=C3)C(C)C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O3/c1-10(2)15-8-13-6-7-14-11(3)12(4)17(23-5)9-16(14)18(13)20(22)19(15)21/h6-10H,1-5H3

> <INCHI_KEY>
YJIHLYMLQOIPEU-UHFFFAOYSA-N

> <FORMULA>
C20H20O3

> <MOLECULAR_WEIGHT>
308.377

> <EXACT_MASS>
308.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.02285497883425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methoxy-7,8-dimethyl-2-(propan-2-yl)-3,4-dihydrophenanthrene-3,4-dione

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
5.192085681

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.826232751802123

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
92.6675

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.63e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-6-methoxy-7,8-dimethylphenanthrene-3,4-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      -1.746  -1.183   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.206  -1.183   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.414  -1.183   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.494  -1.183   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206  -6.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.804  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3   20                                                  
CONECT   20   19                                                            
CONECT   21   11   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
2-Methoxy-11,12-dioxoabieta-1,3,5(10),6,8,13-hexaene	ChEBI

Chemical Formula

C₂₀H₂₀O₃

Average Mass

308.3770 Da

Monoisotopic Mass

308.14124 Da

IUPAC Name

6-methoxy-7,8-dimethyl-2-(propan-2-yl)-3,4-dihydrophenanthrene-3,4-dione

Traditional Name

2-isopropyl-6-methoxy-7,8-dimethylphenanthrene-3,4-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(C)=C2C=CC3=C(C(=O)C(=O)C(=C3)C(C)C)C2=C1

InChI Identifier

InChI=1S/C20H20O3/c1-10(2)15-8-13-6-7-14-11(3)12(4)17(23-5)9-16(14)18(13)20(22)19(15)21/h6-10H,1-5H3

InChI Key

YJIHLYMLQOIPEU-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 blepharochaena Hedge and Hub.Mor.	Plant	KNApSAcK
Salvia blepharochlaena	Plant	KNApSAcK
Salvia multicaulis	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
Hydrophenanthrene
Phenanthrene
Naphthoquinone
Naphthalene
Anisole
Aryl ketone
Quinone
Alkyl aryl ether
Benzenoid
Cyclic ketone
Ketone
Ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ether (CHEBI:66409 )
quinone (CHEBI:66409 )
diterpenoid (CHEBI:66409 )
phenanthrenes (CHEBI:66409 )

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	4.07	ALOGPS
logP	5.19	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.67 m³·mol⁻¹	ChemAxon
Polarizability	35.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

467784

PDB ID

Not Available

ChEBI ID

66409

Good Scents ID

Not Available

References

General References

Ulubelen A, Topcu G, Johansson CB: Norditerpenoids and diterpenoids from Salvia multicaulis with antituberculous activity. J Nat Prod. 1997 Dec;60(12):1275-80. doi: 10.1021/np9700681. [PubMed:9428161 ]

Showing NP-Card for Multiorthoquinone (NP0074747)

MOL for NP0074747 (Multiorthoquinone)

3D MOL for NP0074747 (Multiorthoquinone)

3D SDF for NP0074747 (Multiorthoquinone)

3D-SDF for NP0074747 (Multiorthoquinone)

PDB for NP0074747 (Multiorthoquinone)

3D PDB for NP0074747 (Multiorthoquinone)

SMILES for NP0074747 (Multiorthoquinone)

INCHI for NP0074747 (Multiorthoquinone)

Structure for NP0074747 (Multiorthoquinone)

3D Structure for NP0074747 (Multiorthoquinone)