NP-MRD: Showing NP-Card for (2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione (NP0247432)

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Record Information

Version

2.0

Created at

2022-09-07 09:17:08 UTC

Updated at

2022-09-07 09:17:08 UTC

NP-MRD ID

NP0247432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione

Description

6Alpha-Hydroxytriptocalline A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione is found in Tripterygium wilfordii. Based on a literature review very few articles have been published on 6alpha-Hydroxytriptocalline A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211172D          

 33 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072211172D          

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 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  7 26  1  0  0  0  0
 12 26  1  0  0  0  0
 26 27  1  1  0  0  0
  8 28  1  0  0  0  0
 28  3  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0247432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2[C@@](C)(CC[C@]3(C)[C@H]4C[C@H](O)C5=C(C)C(=O)[C@@H](O)C[C@H]5[C@]4(C)CC[C@@]23C)[C@H](O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O5/c1-14-11-19-26(4,24(33)22(14)31)8-10-28(6)20-13-17(29)21-15(2)23(32)18(30)12-16(21)25(20,3)7-9-27(19,28)5/h14,16-20,24,29-30,33H,7-13H2,1-6H3/t14-,16-,17+,18+,19+,20+,24-,25+,26-,27+,28-/m1/s1

> <INCHI_KEY>
OULQBFCIZRSZEA-PJHNONFPSA-N

> <FORMULA>
C28H42O5

> <MOLECULAR_WEIGHT>
458.639

> <EXACT_MASS>
458.303224452

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.62087484860081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4S,4aR,6aR,6bS,8S,11S,12aS,12bR,14aS,14bR)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-3,10-dione

> <JCHEM_LOGP>
3.5826304836666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.488691095360906

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.81145487455429

> <JCHEM_PKA_STRONGEST_BASIC>
-3.000891418604313

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
126.88139999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4S,4aR,6aR,6bS,8S,11S,12aS,12bR,14aS,14bR)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206 -11.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.644  -7.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.114  -5.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.114 -11.137   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.574 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.206  -5.803   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   10   28                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   26                                             
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    7   12   27                                             
CONECT   27   26                                                            
CONECT   28    8    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
6a-Hydroxytriptocalline a	Generator
6Α-hydroxytriptocalline a	Generator

Chemical Formula

C₂₈H₄₂O₅

Average Mass

458.6390 Da

Monoisotopic Mass

458.30322 Da

IUPAC Name

(2R,4S,4aR,6aR,6bS,8S,11S,12aS,12bR,14aS,14bR)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-3,10-dione

Traditional Name

(2R,4S,4aR,6aR,6bS,8S,11S,12aS,12bR,14aS,14bR)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2[C@@](C)(CC[C@]3(C)[C@H]4C[C@H](O)C5=C(C)C(=O)[C@@H](O)C[C@H]5[C@]4(C)CC[C@@]23C)[C@H](O)C1=O

InChI Identifier

InChI=1S/C28H42O5/c1-14-11-19-26(4,24(33)22(14)31)8-10-28(6)20-13-17(29)21-15(2)23(32)18(30)12-16(21)25(20,3)7-9-27(19,28)5/h14,16-20,24,29-30,33H,7-13H2,1-6H3/t14-,16-,17+,18+,19+,20+,24-,25+,26-,27+,28-/m1/s1

InChI Key

OULQBFCIZRSZEA-PJHNONFPSA-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 cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	3.58	ChemAxon
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	126.88 m³·mol⁻¹	ChemAxon
Polarizability	52.62 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

12043523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione (NP0247432)

MOL for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

3D MOL for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

3D SDF for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

3D-SDF for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

PDB for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

3D PDB for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

SMILES for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

INCHI for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

Structure for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)

3D Structure for NP0247432 ((2r,4s,4ar,6ar,6bs,8s,11s,12as,12br,14as,14br)-4,8,11-trihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,4,5,6,6b,7,8,11,12,12a,13,14,14b-tetradecahydropicene-3,10-dione)