NP-MRD: Showing NP-Card for methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate (NP0255464)

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Record Information

Version

2.0

Created at

2022-09-07 19:58:43 UTC

Updated at

2022-09-07 19:58:43 UTC

NP-MRD ID

NP0255464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate

Description

Methyl 2-[(1Z,4bS,6aR,7S,9R,10aS,10bS,12aR)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-1,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-1-ylidene]acetate belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton. methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate is found in Tripterygium wilfordii. Based on a literature review very few articles have been published on methyl 2-[(1Z,4bS,6aR,7S,9R,10aS,10bS,12aR)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-1,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-1-ylidene]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221582D          

 33 36  0  0  1  0            999 V2000
    1.1420   -4.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -4.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2221   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -3.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -3.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521   -2.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8424   -3.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309072221582D          

 33 36  0  0  1  0            999 V2000
    1.1420   -4.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 27 26  1  1  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 13 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C1/C(=CC=C2[C@@]1(C)CC[C@@]1(C)[C@@H]3C[C@@H](C)C(=O)[C@@H](O)[C@]3(C)CC[C@]21C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O5/c1-16-14-21-26(4,24(32)23(16)31)11-13-27(5)20-9-8-18(17(2)29)19(15-22(30)33-7)25(20,3)10-12-28(21,27)6/h8-9,15-16,21,24,32H,10-14H2,1-7H3/b19-15+/t16-,21-,24-,25+,26-,27-,28+/m1/s1

> <INCHI_KEY>
AXTDWQFUQQFNPB-HPSZYYLOSA-N

> <FORMULA>
C28H38O5

> <MOLECULAR_WEIGHT>
454.607

> <EXACT_MASS>
454.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.66001040715581

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1Z,4bS,6aR,7S,9R,10aS,10bS,12aR)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-1,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-1-ylidene]acetate

> <JCHEM_LOGP>
4.256476728333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.872800915600312

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.959211030211954

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6914402292139146

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
129.47920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1Z,4bS,6aR,7S,9R,10aS,10bS,12aR)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate

> <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       2.132  -8.798   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.644  -8.507   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.148  -7.051   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.140  -5.887   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.660  -6.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -4.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.636  -3.268   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.381  -5.313   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.685  -2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.221  -1.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.734  -0.940   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.750  -3.268   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.742  -6.178   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.709  -5.596   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.197  -5.887   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.172  -6.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   16   28                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   18   28                                                  
CONECT   28   27   14   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13    6   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1Z,4BS,6ar,7S,9R,10as,10BS,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-1,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-1-ylidene]acetic acid	Generator

Chemical Formula

C₂₈H₃₈O₅

Average Mass

454.6070 Da

Monoisotopic Mass

454.27192 Da

IUPAC Name

methyl 2-[(1Z,4bS,6aR,7S,9R,10aS,10bS,12aR)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-1,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysen-1-ylidene]acetate

Traditional Name

methyl [(1Z,4bS,6aR,7S,9R,10aS,10bS,12aR)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C1/C(=CC=C2[C@@]1(C)CC[C@@]1(C)[C@@H]3C[C@@H](C)C(=O)[C@@H](O)[C@]3(C)CC[C@]21C)C(C)=O

InChI Identifier

InChI=1S/C28H38O5/c1-16-14-21-26(4,24(32)23(16)31)11-13-27(5)20-9-8-18(17(2)29)19(15-22(30)33-7)25(20,3)10-12-28(21,27)6/h8-9,15-16,21,24,32H,10-14H2,1-7H3/b19-15+/t16-,21-,24-,25+,26-,27-,28+/m1/s1

InChI Key

AXTDWQFUQQFNPB-HPSZYYLOSA-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 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

16-oxosteroids

Alternative Parents

Substituents

16-oxosteroid
17-oxosteroid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	4.26	ChemAxon
pKa (Strongest Acidic)	12.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.48 m³·mol⁻¹	ChemAxon
Polarizability	51.66 Å³	ChemAxon
Number of Rings	4	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

163034322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate (NP0255464)

MOL for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

3D MOL for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

3D SDF for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

3D-SDF for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

PDB for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

3D PDB for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

SMILES for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

INCHI for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

Structure for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)

3D Structure for NP0255464 (methyl 2-[(1z,4bs,6ar,7s,9r,10as,10bs,12ar)-2-acetyl-7-hydroxy-4b,6a,9,10b,12a-pentamethyl-8-oxo-5,6,7,9,10,10a,11,12-octahydrochrysen-1-ylidene]acetate)