NP-MRD: Showing NP-Card for 21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol (NP0332132)

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Record Information

Version

1.0

Created at

2023-11-23 12:06:44 UTC

Updated at

2024-05-11 00:25:53 UTC

NP-MRD ID

NP0332132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11232312062D          

 52 57  0  0  1  0            999 V2000
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6282    2.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 35  1  0  0  0  0
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 37 38  1  6  0  0  0
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 39 40  1  0  0  0  0
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 42 43  1  0  0  0  0
 39 44  2  0  0  0  0
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M  END


  Mrv2104 11232312062D          

 52 57  0  0  1  0            999 V2000
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
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  6  7  1  1  0  0  0
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  8  9  1  6  0  0  0
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  2 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(C)(C)[C@@H](OC(=O)C3=CC=CC=C3)[C@H](OC(=O)C(\C)=C/C)[C@]1(CO)[C@H](O)C[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C42H60O7/c1-10-25(2)35(46)49-34-33(48-36(47)26-14-12-11-13-15-26)37(3,4)22-28-27-16-17-30-39(7)20-19-31(44)38(5,6)29(39)18-21-40(30,8)41(27,9)23-32(45)42(28,34)24-43/h10-16,28-34,43-45H,17-24H2,1-9H3/b25-10-/t28-,29-,30+,31-,32+,33-,34-,39-,40+,41+,42-/m0/s1

> <INCHI_KEY>
PEQYSALXZUUNHS-IUMRZOLQSA-N

> <FORMULA>
C42H60O7

> <MOLECULAR_WEIGHT>
676.935

> <EXACT_MASS>
676.433904272

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
77.34804658922702

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-5,10-dihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-3-yl benzoate

> <JCHEM_LOGP>
7.449988479999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.159573633247202

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.362065282376792

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351210947245135

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
191.57230000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-5,10-dihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicen-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-23         0                                  
HETATM    1  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       5.954   0.770   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.023   3.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.173   4.969   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.644  -0.564   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.056  -0.564   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.516   4.771   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.746   6.105   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.056   4.771   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.826   3.437   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.516   2.104   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0      10.574   0.770   0.000  0.00  0.00           H+0
HETATM   46  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.076   3.620   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.791   2.630   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   52                                             
CONECT    3    2    4   45   46                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21   37                                             
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   12   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28   37                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   29                                                            
CONECT   37   27   18   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42                                                            
CONECT   44   39                                                            
CONECT   45    3                                                            
CONECT   46    3   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51    2                                                       
MASTER        0    0    0    0    0    0    0    0   52    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₀O₇

Average Mass

676.9350 Da

Monoisotopic Mass

676.43390 Da

IUPAC Name

(3R,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-5,10-dihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-3-yl benzoate

Traditional Name

(3R,4R,4aR,5R,6aS,6bR,8aR,10S,12aR,12bR,14bS)-5,10-dihydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicen-3-yl benzoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(C)(C)[C@@H](OC(=O)C3=CC=CC=C3)[C@H](OC(=O)C(\C)=C/C)[C@]1(CO)[C@H](O)C[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C

InChI Identifier

InChI=1S/C42H60O7/c1-10-25(2)35(46)49-34-33(48-36(47)26-14-12-11-13-15-26)37(3,4)22-28-27-16-17-30-39(7)20-19-31(44)38(5,6)29(39)18-21-40(30,8)41(27,9)23-32(45)42(28,34)24-43/h10-16,28-34,43-45H,17-24H2,1-9H3/b25-10-/t28-,29-,30+,31-,32+,33-,34-,39-,40+,41+,42-/m0/s1

InChI Key

PEQYSALXZUUNHS-IUMRZOLQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	kdyang@163.com	Guangxi University	Kedi Yang	2024-05-09	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
ptilosperma		Not Available

Chemical Taxonomy

Classification

Not classified

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	7.45	ChemAxon
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	191.57 m³·mol⁻¹	ChemAxon
Polarizability	77.35 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	Yes	ChemAxon

External Links

Not Available

References

General References

Ma S, Weng M, Yang T, Ge L, Yang K: Triterpenes and Pheophorbides from Camellia ptilosperma and Their Cytotoxicity, Photocytotoxicity, and Photodynamic Antibacterial Activity. Molecules. 2023 Oct 12;28(20):7058. doi: 10.3390/molecules28207058. [PubMed:37894536 ]

Showing NP-Card for 21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol (NP0332132)

MOL for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

3D MOL for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

3D SDF for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

3D-SDF for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

PDB for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

3D PDB for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

SMILES for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

INCHI for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

Structure for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)

3D Structure for NP0332132 (21β-benzoyloxy-22α-angeloylolean-12-ene-3β,16α,28-triol)