NP-MRD: Showing NP-Card for (2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid (NP0295839)

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Record Information

Version

2.0

Created at

2022-09-10 05:03:42 UTC

Updated at

2022-09-10 05:03:42 UTC

NP-MRD ID

NP0295839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid

Description

Triptohypol A 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. Triptohypol A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid is found in Tripterygium hypoglaucum. Based on a literature review very few articles have been published on triptohypol A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102207032D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102207032D          

 36 40  0  0  1  0            999 V2000
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    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2388   -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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  0  0  0  0
 30 29  1  1  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 15 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0295839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(C(=O)C=C3[C@@]2(C)CC[C@@]2(C)[C@@H]4C[C@@](C)(CC[C@]4(C)CC[C@]32C)C(O)=O)=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O6/c1-26-7-8-27(2,25(34)35)15-22(26)30(5)12-10-28(3)18-13-20(33)24(36-6)17(16-31)23(18)19(32)14-21(28)29(30,4)11-9-26/h13-14,22,31,33H,7-12,15-16H2,1-6H3,(H,34,35)/t22-,26-,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
QWODMBKBVGCKFL-NLVUKCNFSA-N

> <FORMULA>
C30H40O6

> <MOLECULAR_WEIGHT>
496.644

> <EXACT_MASS>
496.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.44626728032754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aS,6aS,12bR,14aS,14bR)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

> <JCHEM_LOGP>
4.984000134000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.158208630021244

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.456779969426996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0949481335774083

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
138.5457

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aS,6aS,12bR,14aS,14bR)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.486  -5.184   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.256  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.796  -6.517   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.796  -1.183   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.256  -1.183   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.106   0.151   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.576  -1.183   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.793  -5.710   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.078  -6.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      20.258  -7.690   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      17.631  -7.227   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.646  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17   18   31                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   30                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   29                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30                                                       
CONECT   30   29   20   31                                                  
CONECT   31   30   16   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   15    7   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₆

Average Mass

496.6440 Da

Monoisotopic Mass

496.28249 Da

IUPAC Name

(2R,4aS,6aS,12bR,14aS,14bR)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Traditional Name

(2R,4aS,6aS,12bR,14aS,14bR)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(C(=O)C=C3[C@@]2(C)CC[C@@]2(C)[C@@H]4C[C@@](C)(CC[C@]4(C)CC[C@]32C)C(O)=O)=C1CO

InChI Identifier

InChI=1S/C30H40O6/c1-26-7-8-27(2,25(34)35)15-22(26)30(5)12-10-28(3)18-13-20(33)24(36-6)17(16-31)23(18)19(32)14-21(28)29(30,4)11-9-26/h13-14,22,31,33H,7-12,15-16H2,1-6H3,(H,34,35)/t22-,26-,27-,28+,29-,30+/m1/s1

InChI Key

QWODMBKBVGCKFL-NLVUKCNFSA-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 hypoglaucum	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
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Ketone
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
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	4.98	ChemAxon
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	138.55 m³·mol⁻¹	ChemAxon
Polarizability	55.45 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

58827393

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101936043

PDB ID

Not Available

ChEBI ID

132315

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid (NP0295839)

MOL for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

3D MOL for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

3D SDF for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

3D-SDF for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

PDB for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

3D PDB for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

SMILES for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

INCHI for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

Structure for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)

3D Structure for NP0295839 ((2r,4as,6as,12br,14as,14br)-11-hydroxy-9-(hydroxymethyl)-10-methoxy-2,4a,6a,12b,14a-pentamethyl-8-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid)