NP-MRD: Showing NP-Card for Mansonone E (NP0063330)

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Record Information

Version

2.0

Created at

2022-04-28 07:46:04 UTC

Updated at

2022-04-28 07:46:04 UTC

NP-MRD ID

NP0063330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mansonone E

Description

(4R)-4,8,12-trimethyl-2-oxatricyclo[7.3.1.0⁵,¹³]Trideca-1(12),5(13),6,8-tetraene-10,11-dione belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Mansonone E is found in Alangium chinense, Helicteres angustifolia , Hibiscus taiwanensis, Mansonia altissima, Talipariti tiliaceum, Thespesia garckeana, Thespesia populnea, Thespesia populnea L. Soland. Ex Coor , Ulmus americana, Ulmus glabra, Ulmus davidiana, Ulmus laciniata, Ulmus parviflora, Ulmus parvifolia and Ulmus pumila. Based on a literature review very few articles have been published on (4R)-4,8,12-trimethyl-2-oxatricyclo[7.3.1.0⁵,¹³]Trideca-1(12),5(13),6,8-tetraene-10,11-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.1196   -3.1405    0.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7640   -1.6886   -0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5016   -1.3351   -0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4933   -2.2818   -0.1392 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -2.0834   -0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -0.6791   -0.3951 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2273   -0.5289    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305    0.3322   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087    1.6607   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    2.6748   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6614    2.4160   -0.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039    3.4678   -0.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377    1.0982   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1002    0.0662   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4340    0.7027   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3136    1.5841   -0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312   -0.6961   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0419   -1.0169    0.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0196   -3.2633    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749   -3.5817   -0.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610   -3.6468    0.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -2.7247    0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783   -2.4887   -1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578   -0.4354   -1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1041    0.1229    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5999   -1.5158    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6669   -0.0164    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6448    1.9218   -0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    3.6918   -0.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3813    3.4196   -1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    3.5114    0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1602    4.4531   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 17  1  0
 17 18  2  0
 17 15  1  0
 15 16  2  0
 15 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8 14  1  0
  8  6  1  0
 14  3  1  0
 14 13  2  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  6 24  1  6
  5 22  1  0
  5 23  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 10 29  1  0
  9 28  1  0
M  END


  Mrv1652304282209462D          

 18 20  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  1  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1COC2=C(C)C(=O)C(=O)C3=C(C)C=CC1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-7-4-5-10-8(2)6-18-15-9(3)13(16)14(17)11(7)12(10)15/h4-5,8H,6H2,1-3H3/t8-/m0/s1

> <INCHI_KEY>
SYWTYRLIJCHSLJ-QMMMGPOBSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.752192025739493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4,8,12-trimethyl-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.879412862333334

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.859006179475167

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
69.98800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4,8,12-trimethyl-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15                                                  
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17    7                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

(4R)-4,8,12-trimethyl-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

Traditional Name

(4R)-4,8,12-trimethyl-2-oxatricyclo[7.3.1.0^{5,13}]trideca-1(12),5(13),6,8-tetraene-10,11-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1COC2=C(C)C(=O)C(=O)C3=C(C)C=CC1=C23

InChI Identifier

InChI=1S/C15H14O3/c1-7-4-5-10-8(2)6-18-15-9(3)13(16)14(17)11(7)12(10)15/h4-5,8H,6H2,1-3H3/t8-/m0/s1

InChI Key

SYWTYRLIJCHSLJ-QMMMGPOBSA-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
Alangium chinense	LOTUS Database	35616633
Helicteres angustifolia	Plant	KNApSAcK
Hibiscus taiwanensis	Plant	KNApSAcK
Mansonia altissima	Plant	KNApSAcK
Talipariti tiliaceum	LOTUS Database	35616633
Thespesia garckeana	LOTUS Database	35616633
Thespesia populnea	LOTUS Database	35616633
Thespesia populnea L. Soland. Ex Coor	Plant	KNApSAcK
Ulmus americana	LOTUS Database	35616633
Ulmus campestris	LOTUS Database	35616633
Ulmus davidiana	Plant	KNApSAcK
Ulmus laciniata	Plant	KNApSAcK
Ulmus parviflora	Plant	KNApSAcK
Ulmus parvifolia	Plant	KNApSAcK
Ulmus pumila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Benzopyran
Isochromane
2-benzopyran
Quinone
Aryl ketone
Vinylogous ester
Ketone
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	2.77	ALOGPS
logP	2.88	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.9	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	0	ChemAxon
Refractivity	69.99 m³·mol⁻¹	ChemAxon
Polarizability	25.75 Å³	ChemAxon
Number of Rings	3	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

24737446

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139071911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Mansonone E (NP0063330)

MOL for NP0063330 (Mansonone E)

3D MOL for NP0063330 (Mansonone E)

3D SDF for NP0063330 (Mansonone E)

3D-SDF for NP0063330 (Mansonone E)

PDB for NP0063330 (Mansonone E)

3D PDB for NP0063330 (Mansonone E)

SMILES for NP0063330 (Mansonone E)

INCHI for NP0063330 (Mansonone E)

Structure for NP0063330 (Mansonone E)

3D Structure for NP0063330 (Mansonone E)