NP-MRD: Showing NP-Card for 4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione (NP0230654)

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Record Information

Version

2.0

Created at

2022-09-06 11:10:41 UTC

Updated at

2022-09-06 11:10:41 UTC

NP-MRD ID

NP0230654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione

Description

4,11-Dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-3,8-dione belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione is found in Tripterygium wilfordii. 4,11-Dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-3,8-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161504312D          

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M  END

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M  END


  Mrv1533004161504312D          

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  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 12 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
  8 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(C(=O)C=C3C2(C)CCC2(C)C4CC(C)C(=O)C(O)C4(C)CCC32C)=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O6/c1-15-11-20-27(3,25(34)23(15)33)8-10-29(5)21-13-18(31)22-16(14-30)24(35-6)19(32)12-17(22)26(21,2)7-9-28(20,29)4/h12-13,15,20,25,30,32,34H,7-11,14H2,1-6H3

> <INCHI_KEY>
IZDJSAJVSZKIGM-UHFFFAOYSA-N

> <FORMULA>
C29H38O6

> <MOLECULAR_WEIGHT>
482.617

> <EXACT_MASS>
482.266838944

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.14829138131584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-3,8-dione

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
3.853851410999999

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.94861928197528

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.158115367329444

> <JCHEM_PKA_STRONGEST_BASIC>
-3.094948133662852

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
134.35889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      14.424   2.104   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.804   4.771   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.114   3.437   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.654   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   33                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   31                                             
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   12   17   32                                             
CONECT   32   31                                                            
CONECT   33    8    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₆

Average Mass

482.6170 Da

Monoisotopic Mass

482.26684 Da

IUPAC Name

4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-3,8-dione

Traditional Name

4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(C(=O)C=C3C2(C)CCC2(C)C4CC(C)C(=O)C(O)C4(C)CCC32C)=C1CO

InChI Identifier

InChI=1S/C29H38O6/c1-15-11-20-27(3,25(34)23(15)33)8-10-29(5)21-13-18(31)22-16(14-30)24(35-6)19(32)12-17(22)26(21,2)7-9-28(20,29)4/h12-13,15,20,25,30,32,34H,7-11,14H2,1-6H3

InChI Key

IZDJSAJVSZKIGM-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
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthalene
Anisole
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Ether
Aromatic alcohol
Primary alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
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	4.21	ALOGPS
logP	3.85	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.36 m³·mol⁻¹	ChemAxon
Polarizability	54.15 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

75069647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione (NP0230654)

MOL for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

3D MOL for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

3D SDF for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

3D-SDF for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

PDB for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

3D PDB for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

SMILES for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

INCHI for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

Structure for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)

3D Structure for NP0230654 (4,11-dihydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-1,2,4,5,6,13,14,14b-octahydropicene-3,8-dione)