NP-MRD: Showing NP-Card for (22S)-3a,22-dihydroxylanosta-8,24-diene (NP0044165)

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Record Information

Version

1.0

Created at

2021-11-12 23:53:47 UTC

Updated at

2021-11-26 17:46:09 UTC

NP-MRD ID

NP0044165

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(22S)-3a,22-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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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 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
  7 25  1  0  0  0  0
  2 26  1  6  0  0  0
 26 27  1  1  0  0  0
 26 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  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044165

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O2/c1-19(2)9-11-24(31)20(3)21-13-17-30(8)23-10-12-25-27(4,5)26(32)15-16-28(25,6)22(23)14-18-29(21,30)7/h9,20-21,24-26,31-32H,10-18H2,1-8H3/t20-,21+,24-,25-,26+,28+,29+,30-/m0/s1

> <INCHI_KEY>
KKWJCGCIAHLFNE-RXPMIZTQSA-N

> <FORMULA>
C30H50O2

> <MOLECULAR_WEIGHT>
442.728

> <EXACT_MASS>
442.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.42495865847204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R,7R,11R,14R,15R)-14-[(2S,3S)-3-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-ol

> <ALOGPS_LOGP>
6.27

> <JCHEM_LOGP>
6.397907724

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.553786825962863

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.363993805786063

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5454708400122458

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
136.13719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,7R,11R,14R,15R)-14-[(2S,3S)-3-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-ol

> <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  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       1.803   3.396   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.988   0.157   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    5   12                                             
CONECT   12   11                                                            
CONECT   13    8   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   13   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    7                                                       
CONECT   26    2   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₂

Average Mass

442.7280 Da

Monoisotopic Mass

442.38108 Da

IUPAC Name

(2S,5R,7R,11R,14R,15R)-14-[(2S,3S)-3-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-ol

Traditional Name

(2S,5R,7R,11R,14R,15R)-14-[(2S,3S)-3-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-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H50O2/c1-19(2)9-11-24(31)20(3)21-13-17-30(8)23-10-12-25-27(4,5)26(32)15-16-28(25,6)22(23)14-18-29(21,30)7/h9,20-21,24-26,31-32H,10-18H2,1-8H3/t20-,21+,24-,25-,26+,28+,29+,30-/m0/s1

InChI Key

KKWJCGCIAHLFNE-RXPMIZTQSA-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	6.27	ALOGPS
logP	6.4	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	19.36	ChemAxon
pKa (Strongest Basic)	-0.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.14 m³·mol⁻¹	ChemAxon
Polarizability	55.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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 (22S)-3a,22-dihydroxylanosta-8,24-diene (NP0044165)

MOL for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

3D MOL for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

3D SDF for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

3D-SDF for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

PDB for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

3D PDB for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

SMILES for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

INCHI for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

Structure for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)

3D Structure for NP0044165 ((22S)-3a,22-dihydroxylanosta-8,24-diene)