NP-MRD: Showing NP-Card for Lucidadiol (NP0044179)

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Record Information

Version

2.0

Created at

2021-11-12 23:54:38 UTC

Updated at

2021-11-26 17:46:18 UTC

NP-MRD ID

NP0044179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lucidadiol

Description

LUCIDADIOL belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Lucidadiol is found in Ganoderma lucidum , Ganoderma pfeiferri and Ganoderma pfeifferi. Lucidadiol was first documented in 1999 (González, et al.). Based on a literature review very few articles have been published on LUCIDADIOL.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100542D          

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 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  2  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044179

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-19(18-31)9-8-10-20(2)21-11-16-30(7)26-22(12-15-29(21,30)6)28(5)14-13-25(33)27(3,4)24(28)17-23(26)32/h9,20-21,24-25,31,33H,8,10-18H2,1-7H3/b19-9+/t20-,21-,24+,25+,28-,29-,30+/m1/s1

> <INCHI_KEY>
AZPOACUDFJKUHJ-GPEQXWBKSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.09340852682508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R,5E)-7-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-9-one

> <ALOGPS_LOGP>
5.99

> <JCHEM_LOGP>
5.758618003

> <ALOGPS_LOGS>
-5.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.618725644141033

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.643645082036485

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785519487579803

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
137.01259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R,5E)-7-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-9-one

> <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  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.929  -1.853   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14   30                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   11   18                                             
CONECT   18   17                                                            
CONECT   19   14   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   13   31                                                  
CONECT   31   30                                                            
CONECT   32    2   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R,5E)-7-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-9-one

Traditional Name

(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R,5E)-7-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-9-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O3/c1-19(18-31)9-8-10-20(2)21-11-16-30(7)26-22(12-15-29(21,30)6)28(5)14-13-25(33)27(3,4)24(28)17-23(26)32/h9,20-21,24-25,31,33H,8,10-18H2,1-7H3/b19-9+/t20-,21-,24+,25+,28-,29-,30+/m1/s1

InChI Key

AZPOACUDFJKUHJ-GPEQXWBKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, 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

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Ganoderma lucidum	Fungi	KNApSAcK
Ganoderma pfeiferri	Fungi	KNApSAcK
Ganoderma pfeifferi	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
7-oxosteroid
Steroid
Fatty alcohol
Cyclohexenone
Fatty acyl
Cyclic alcohol
Ketone
Secondary alcohol
Primary alcohol
Organic oxygen compound
Organooxygen 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	5.99	ALOGPS
logP	5.76	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.01 m³·mol⁻¹	ChemAxon
Polarizability	56.09 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043676

Chemspider ID

8965303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10789991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Antonio G. González, Francisco León, Augusto Rivera, Claudia M. Muñoz, and Jaime Bermejo (1999). Lanostanoid Triterpenes from Ganoderma lucidum. J. Nat. Prod. 1999, 62, 12, 1700–1701. DOI: 10.1021/np990295y. J. Nat. Prod..

Showing NP-Card for Lucidadiol (NP0044179)

MOL for NP0044179 (Lucidadiol)

3D MOL for NP0044179 (Lucidadiol)

3D SDF for NP0044179 (Lucidadiol)

3D-SDF for NP0044179 (Lucidadiol)

PDB for NP0044179 (Lucidadiol)

3D PDB for NP0044179 (Lucidadiol)

SMILES for NP0044179 (Lucidadiol)

INCHI for NP0044179 (Lucidadiol)

Structure for NP0044179 (Lucidadiol)

3D Structure for NP0044179 (Lucidadiol)