NP-MRD: Showing NP-Card for (20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene (NP0044164)

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Record Information

Version

1.0

Created at

2021-11-12 23:53:44 UTC

Updated at

2021-11-26 17:46:08 UTC

NP-MRD ID

NP0044164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene

Description

It was first documented in 2017 (Masahiko Isaka et al.).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100532D          

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M  END


  Mrv1652311132100532D          

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    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9660    1.8191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9452   -0.2865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9957   -2.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848   -3.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -4.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675   -3.7368    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
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  6  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
  2 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1([C@@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](OC(C)=O)C(C)(C)[C@]1([H])CC3)C(C)(O)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O4/c1-20(2)11-10-16-32(9,35)27-24(34)19-31(8)23-12-13-25-28(4,5)26(36-21(3)33)15-17-29(25,6)22(23)14-18-30(27,31)7/h11,24-27,34-35H,10,12-19H2,1-9H3/t24-,25-,26-,27-,29+,30+,31-,32?/m0/s1

> <INCHI_KEY>
ZOZVRUXJAZNBAO-KYVANANQSA-N

> <FORMULA>
C32H52O4

> <MOLECULAR_WEIGHT>
500.764

> <EXACT_MASS>
500.386560154

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
60.74152432095853

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11R,13S,14R,15R)-13-hydroxy-14-(2-hydroxy-6-methylhept-5-en-2-yl)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

> <ALOGPS_LOGP>
6.39

> <JCHEM_LOGP>
5.487428906333335

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.150685401286196

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.440745928702007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.880548106372556

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
146.94899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11R,13S,14R,15R)-13-hydroxy-14-(2-hydroxy-6-methylhept-5-en-2-yl)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  H   UNK     0      10.449   0.026   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.813   1.738   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.221   2.761   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.737   3.032   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.229   3.938   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       1.803   3.396   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.666  -2.425   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.098  -0.535   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.827  -2.696   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.247  -4.122   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.192  -5.338   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.612  -6.765   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.557  -7.980   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.086  -6.975   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12   30                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9   29                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2    6   13                                             
CONECT   13   12                                                            
CONECT   14    9   15   16   26                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   14   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    8                                                       
CONECT   30    2   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₂O₄

Average Mass

500.7640 Da

Monoisotopic Mass

500.38656 Da

IUPAC Name

(2S,5S,7R,11R,13S,14R,15R)-13-hydroxy-14-(2-hydroxy-6-methylhept-5-en-2-yl)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

Traditional Name

(2S,5S,7R,11R,13S,14R,15R)-13-hydroxy-14-(2-hydroxy-6-methylhept-5-en-2-yl)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1([C@@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](OC(C)=O)C(C)(C)[C@]1([H])CC3)C(C)(O)CCC=C(C)C

InChI Identifier

InChI=1S/C32H52O4/c1-20(2)11-10-16-32(9,35)27-24(34)19-31(8)23-12-13-25-28(4,5)26(36-21(3)33)15-17-29(25,6)22(23)14-18-30(27,31)7/h11,24-27,34-35H,10,12-19H2,1-9H3/t24-,25-,26-,27-,29+,30+,31-,32?/m0/s1

InChI Key

ZOZVRUXJAZNBAO-KYVANANQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Astraeus asiaticus

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	6.39	ALOGPS
logP	5.49	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	146.95 m³·mol⁻¹	ChemAxon
Polarizability	60.74 Å³	ChemAxon
Number of Rings	4	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

Masahiko Isaka et al. (2017). Lanostane triterpenoids from the edible mushroom Astraeus asiaticus. Tetrahedron, 73(12), 1561-1567 - March 2017. DOI: 10.1016/j.tet.2017.01.070. Tetrahedron.

Showing NP-Card for (20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene (NP0044164)

MOL for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

3D MOL for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

3D SDF for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

3D-SDF for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

PDB for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

3D PDB for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

SMILES for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

INCHI for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

Structure for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)

3D Structure for NP0044164 ((20S)-3beta-acetoxy-16b,20-dihydroxylanosta-8,24-diene)