NP-MRD: Showing NP-Card for trigohowilol C (NP0037052)

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Record Information

Version

2.0

Created at

2021-06-20 20:04:03 UTC

Updated at

2021-06-30 00:09:02 UTC

NP-MRD ID

NP0037052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trigohowilol C

Provided By

JEOL Database JEOL Logo

Description

Trigohowilol C belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. trigohowilol C is found in Trigonostemon howii. trigohowilol C was first documented in 2012 (Tang, G. -H., et al.). Based on a literature review very few articles have been published on Trigohowilol C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122043D          

 67 72  0  0  0  0            999 V2000
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    2.0869    0.4394    2.6636 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122043D          

 67 72  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0037052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C([H])=C(C3=C4C(=C([H])C(=O)C5=C4C([H])=C(O[H])C(=C5[H])C([H])([H])[H])C(C3=O)(C([H])([H])[H])C([H])([H])[H])C(=O)C2(C([H])([H])[H])C([H])([H])[H])C2=C1C([H])=C(C(O[H])=C2[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C33H28O6/c1-14-7-18-16(10-24(14)34)17-9-21(30(38)32(3,4)22(17)12-26(18)36)29-28-20-11-25(35)15(2)8-19(20)27(37)13-23(28)33(5,6)31(29)39/h7-13,34-36H,1-6H3

> <INCHI_KEY>
DFDVUOJRRAVNNF-UHFFFAOYSA-N

> <FORMULA>
C33H28O6

> <MOLECULAR_WEIGHT>
520.581

> <EXACT_MASS>
520.188588622

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
57.124625069050126

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(6,9-dihydroxy-1,1,7-trimethyl-2-oxo-1,2-dihydrophenanthren-3-yl)-8-hydroxy-3,3,7-trimethyl-2H,3H,5H-cyclopenta[a]naphthalene-2,5-dione

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
6.772520824666668

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.322420111895624

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.560129469359218

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2615205872907715

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999998

> <JCHEM_REFRACTIVITY>
152.12869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(6,9-dihydroxy-1,1,7-trimethyl-2-oxophenanthren-3-yl)-8-hydroxy-3,3,7-trimethylcyclopenta[a]naphthalene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 72  0  0  0  0  0  0  0  0999 V2000
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 24 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 28 60  1  0
 23 53  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 17 48  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       4.292   1.073   3.714  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.387   0.090   3.030  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.819  -1.215   2.778  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.971  -2.138   2.146  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.675  -1.771   1.729  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.235  -0.475   2.034  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.087   0.439   2.664  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.652   1.705   2.942  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.855  -2.794   1.033  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.304  -2.651   0.364  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.127  -1.515   0.048  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.735  -0.520  -0.762  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.582   0.640  -1.104  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.979   0.523  -0.908  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.809   1.565  -1.348  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.264   2.713  -1.918  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.106   3.715  -2.331  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.878   2.875  -2.074  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.337   4.056  -2.634  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.040   4.251  -2.795  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.544   5.530  -3.396  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.887   3.232  -2.376  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.247   3.309  -2.468  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.378   2.055  -1.824  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.013   1.832  -1.663  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.575  -0.735  -0.258  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.071  -1.693  -1.355  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.752  -0.401   0.686  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.519  -1.478   0.576  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.773  -2.066   1.629  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.696  -4.010  -0.097  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.684  -4.214  -0.793  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.271  -5.078   0.370  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.415  -5.982   1.393  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.795  -5.870  -0.828  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.310  -4.181   0.998  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.527  -4.541   1.423  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.464  -3.531   1.965  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.605  -3.861   2.264  0.00  0.00           O+0
HETATM   40  H   UNK     0       4.369   1.994   3.128  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.907   1.309   4.712  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.305   0.673   3.829  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.818  -1.525   3.084  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.222  -0.162   1.814  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.756   1.827   2.587  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.251  -0.571  -1.212  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.887   1.483  -1.255  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.026   3.449  -2.174  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.020   4.845  -2.950  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.168   6.067  -2.674  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.127   5.321  -4.298  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.278   6.194  -3.683  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.498   4.167  -2.844  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.108   1.317  -1.506  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.268  -1.963  -2.052  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.878  -1.245  -1.945  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.449  -2.627  -0.922  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.613   0.015   0.152  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.118  -1.295   1.205  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.450   0.322   1.453  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.285  -6.717   1.807  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.247  -6.530   0.937  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.830  -5.407   2.229  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.263  -5.213  -1.571  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.536  -6.617  -0.524  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.020  -6.399  -1.337  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.896  -5.559   1.377  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3    7                                                  
CONECT    3    4    2   43                                                  
CONECT    4   38    5    3                                                  
CONECT    5    9    4    6                                                  
CONECT    6    7    5   44                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7   45                                                       
CONECT    9    5   36   10                                                  
CONECT   10    9   31   11                                                  
CONECT   11   29   12   10                                                  
CONECT   12   11   13   46                                                  
CONECT   13   12   14   25                                                  
CONECT   14   26   13   15                                                  
CONECT   15   14   16   47                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   48                                                       
CONECT   18   16   25   19                                                  
CONECT   19   18   20   49                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20   50   51   52                                             
CONECT   22   20   24   23                                                  
CONECT   23   22   53                                                       
CONECT   24   25   22   54                                                  
CONECT   25   13   18   24                                                  
CONECT   26   29   14   27   28                                             
CONECT   27   26   55   56   57                                             
CONECT   28   26   58   59   60                                             
CONECT   29   11   26   30                                                  
CONECT   30   29                                                            
CONECT   31   10   33   32                                                  
CONECT   32   31                                                            
CONECT   33   31   36   34   35                                             
CONECT   34   33   61   62   63                                             
CONECT   35   33   64   65   66                                             
CONECT   36    9   37   33                                                  
CONECT   37   36   38   67                                                  
CONECT   38   39   37    4                                                  
CONECT   39   38                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    3                                                            
CONECT   44    6                                                            
CONECT   45    8                                                            
CONECT   46   12                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   34                                                            
CONECT   62   34                                                            
CONECT   63   34                                                            
CONECT   64   35                                                            
CONECT   65   35                                                            
CONECT   66   35                                                            
CONECT   67   37                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  144    0
END

RDKit          3D

67 72  0  0  0  0  0  0  0  0999 V2000
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 17 48  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₈O₆

Average Mass

520.5810 Da

Monoisotopic Mass

520.18859 Da

IUPAC Name

1-(6,9-dihydroxy-1,1,7-trimethyl-2-oxo-1,2-dihydrophenanthren-3-yl)-8-hydroxy-3,3,7-trimethyl-2H,3H,5H-cyclopenta[a]naphthalene-2,5-dione

Traditional Name

1-(6,9-dihydroxy-1,1,7-trimethyl-2-oxophenanthren-3-yl)-8-hydroxy-3,3,7-trimethylcyclopenta[a]naphthalene-2,5-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C([H])=C(C3=C4C(=C([H])C(=O)C5=C4C([H])=C(O[H])C(=C5[H])C([H])([H])[H])C(C3=O)(C([H])([H])[H])C([H])([H])[H])C(=O)C2(C([H])([H])[H])C([H])([H])[H])C2=C1C([H])=C(C(O[H])=C2[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C33H28O6/c1-14-7-18-16(10-24(14)34)17-9-21(30(38)32(3,4)22(17)12-26(18)36)29-28-20-11-25(35)15(2)8-19(20)27(37)13-23(28)33(5,6)31(29)39/h7-13,34-36H,1-6H3

InChI Key

DFDVUOJRRAVNNF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trigonostemon howii	JEOL database	Tang, G. -H., et al, J. Nat. Prod. 75, 1962 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
Hydrophenanthrene
2-naphthol
1-naphthol
Naphthalene
Aryl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Cyclic ketone
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.5	ALOGPS
logP	6.77	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	152.13 m³·mol⁻¹	ChemAxon
Polarizability	57.12 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

28641495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71460597

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tang, G. -H., et al. (2012). Tang, G. -H., et al, J. Nat. Prod. 75, 1962 (2012). J. Nat. Prod..

Showing NP-Card for trigohowilol C (NP0037052)

MOL for NP0037052 (trigohowilol C)

3D MOL for NP0037052 (trigohowilol C)

3D SDF for NP0037052 (trigohowilol C)

3D-SDF for NP0037052 (trigohowilol C)

PDB for NP0037052 (trigohowilol C)

3D PDB for NP0037052 (trigohowilol C)

SMILES for NP0037052 (trigohowilol C)

INCHI for NP0037052 (trigohowilol C)

Structure for NP0037052 (trigohowilol C)

3D Structure for NP0037052 (trigohowilol C)