NP-MRD: Showing NP-Card for lupan-3β,20-diol (NP0324850)

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Record Information

Version

2.0

Created at

2022-09-12 05:10:31 UTC

Updated at

2022-09-12 05:10:31 UTC

NP-MRD ID

NP0324850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lupan-3β,20-diol

Description

lupan-3β,20-diol is found in Betula ermanii, Betula maximowicziana, Betula pendula, Camellia japonica, Ceriops decandra, Englerophytum magalismontanum, Maclura pomifera, Relhania calycina, Pleurostylia opposita, Salacia chinensis and Salvia montbretii.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303082008142D          

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M  END

     RDKit          3D

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M  END


  Mrv1652303082008142D          

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    2.7139    1.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1979   -1.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0141   -1.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -0.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0021   -1.2597    0.0000 O   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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  6  0  0  0
  3 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@@H](CC[C@]1(C)CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O2/c1-25(2)21-12-16-30(8)22(28(21,6)15-13-23(25)31)10-9-20-24-19(26(3,4)32)11-14-27(24,5)17-18-29(20,30)7/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21+,22-,23+,24-,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
YDNYDUBBAZTLTQ-LIVJDELJSA-N

> <FORMULA>
C30H52O2

> <MOLECULAR_WEIGHT>
444.744

> <EXACT_MASS>
444.396730914

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
55.47665605468959

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,8R,9S,10R,13R,14R,17S,19R)-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol

> <ALOGPS_LOGP>
5.75

> <JCHEM_LOGP>
6.402531336999999

> <ALOGPS_LOGS>
-6.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.48943339017772

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.48015959804241

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5361152819791056

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
132.8899

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.39e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,8R,9S,10R,13R,14R,17S,19R)-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  H   UNK     0       8.283   1.998   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       9.033   0.653   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.046  -0.507   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.462   0.098   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.324   1.632   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.823   1.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.747   3.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.073   3.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.533   3.343   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.743   2.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.994   3.367   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.493   0.676   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       8.243  -0.669   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       6.703  -0.645   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.163  -0.622   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.413   0.723   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       3.664   2.068   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       2.874   0.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.623  -0.599   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.083  -0.575   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.544  -0.552   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.206   0.793   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.746   0.817   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.584   2.115   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.855   2.664   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.875   3.628   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.124   2.092   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       1.374   3.437   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       2.914   3.414   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.454   3.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.204   2.045   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.066   3.579   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.703  -2.008   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.360  -3.510   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.201  -1.665   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.204  -2.351   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6   12                                             
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   31                                             
CONECT   11   10                                                            
CONECT   12   10    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   31                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   18   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   10   16   32                                             
CONECT   32   31                                                            
CONECT   33    3   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₂O₂

Average Mass

444.7440 Da

Monoisotopic Mass

444.39673 Da

IUPAC Name

(1R,2R,5R,8R,9S,10R,13R,14R,17S,19R)-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol

Traditional Name

(1R,2R,5R,8R,9S,10R,13R,14R,17S,19R)-8-(2-hydroxypropan-2-yl)-1,2,5,14,18,18-hexamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@@H](CC[C@]1(C)CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(C)(C)O

InChI Identifier

InChI=1S/C30H52O2/c1-25(2)21-12-16-30(8)22(28(21,6)15-13-23(25)31)10-9-20-24-19(26(3,4)32)11-14-27(24,5)17-18-29(20,30)7/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21+,22-,23+,24-,27-,28+,29-,30-/m1/s1

InChI Key

YDNYDUBBAZTLTQ-LIVJDELJSA-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
Betula ermanii	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Camellia japonica	LOTUS Database	35616633
Ceriops decandra	LOTUS Database	35616633
Englerophytum magalismontanum	LOTUS Database	35616633
Maclura pomifera	LOTUS Database	35616633
Oedera calycina	LOTUS Database	35616633
Pleurostylia opposita	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633
Salvia montbretii	LOTUS Database	35616633

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	5.75	ALOGPS
logP	6.4	ChemAxon
logS	-6.9	ALOGPS
pKa (Strongest Acidic)	19.48	ChemAxon
pKa (Strongest Basic)	-0.54	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	1	ChemAxon
Refractivity	132.89 m³·mol⁻¹	ChemAxon
Polarizability	55.48 Å³	ChemAxon
Number of Rings	5	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

LOTUS database [Link]

Showing NP-Card for lupan-3β,20-diol (NP0324850)

MOL for NP0324850 (lupan-3β,20-diol)

3D MOL for NP0324850 (lupan-3β,20-diol)

3D SDF for NP0324850 (lupan-3β,20-diol)

3D-SDF for NP0324850 (lupan-3β,20-diol)

PDB for NP0324850 (lupan-3β,20-diol)

3D PDB for NP0324850 (lupan-3β,20-diol)

SMILES for NP0324850 (lupan-3β,20-diol)

INCHI for NP0324850 (lupan-3β,20-diol)

Structure for NP0324850 (lupan-3β,20-diol)

3D Structure for NP0324850 (lupan-3β,20-diol)