NP-MRD: Showing NP-Card for 3-acetylganodermadiol (NP0044162)

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Record Information

Version

2.0

Created at

2021-11-12 23:53:38 UTC

Updated at

2021-11-26 17:46:07 UTC

NP-MRD ID

NP0044162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-acetylganodermadiol

Description

3-Acetyl-ganodermadiol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-acetylganodermadiol was first documented in 2019 (Liefeng Ma et al.). Based on a literature review very few articles have been published on 3-acetyl-ganodermadiol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100532D          

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M  END

     RDKit          3D

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M  END


  Mrv1652311132100532D          

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    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6773   -5.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1710   -5.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537   -5.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4819   -6.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9755   -7.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  1  0  0  0
 15 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  2 29  1  1  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(C)C3=CC[C@@]4([H])C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O)[C@H](C)CC\C=C(/C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O3/c1-21(20-33)10-9-11-22(2)24-14-18-32(8)26-12-13-27-29(4,5)28(35-23(3)34)16-17-30(27,6)25(26)15-19-31(24,32)7/h10,12,15,22,24,27-28,33H,9,11,13-14,16-20H2,1-8H3/b21-10+/t22-,24-,27+,28+,30-,31-,32+/m1/s1

> <INCHI_KEY>
XZPGUQWQPJEACY-UIAQYYJJSA-N

> <FORMULA>
C32H50O3

> <MOLECULAR_WEIGHT>
482.749

> <EXACT_MASS>
482.37599547

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
60.00661809958683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11R,14R,15R)-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}]heptadeca-1(17),9-dien-5-yl acetate

> <ALOGPS_LOGP>
8.30

> <JCHEM_LOGP>
6.505105118

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.64402356141891

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797040942353693

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
146.58749999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11R,14R,15R)-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}]heptadeca-1(17),9-dien-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       4.215  -4.357   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0      13.330  -3.613   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.527 -10.937   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.633 -12.574   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.688 -13.790   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23   29                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   23                                             
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    2    5   24                                             
CONECT   24   23                                                            
CONECT   25   15   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₀O₃

Average Mass

482.7490 Da

Monoisotopic Mass

482.37600 Da

IUPAC Name

(2S,5S,7R,11R,14R,15R)-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}]heptadeca-1(17),9-dien-5-yl acetate

Traditional Name

(2S,5S,7R,11R,14R,15R)-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}]heptadeca-1(17),9-dien-5-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(C)C3=CC[C@@]4([H])C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O)[C@H](C)CC\C=C(/C)CO

InChI Identifier

InChI=1S/C32H50O3/c1-21(20-33)10-9-11-22(2)24-14-18-32(8)26-12-13-27-29(4,5)28(35-23(3)34)16-17-30(27,6)25(26)15-19-31(24,32)7/h10,12,15,22,24,27-28,33H,9,11,13-14,16-20H2,1-8H3/b21-10+/t22-,24-,27+,28+,30-,31-,32+/m1/s1

InChI Key

XZPGUQWQPJEACY-UIAQYYJJSA-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

Ganoderma hainanense

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
Cholane-skeleton
Monohydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
14-alpha-methylsteroid
Steroid
Delta-7-steroid
Fatty alcohol
Fatty acyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	8.3	ALOGPS
logP	6.51	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.59 m³·mol⁻¹	ChemAxon
Polarizability	60.01 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liefeng Ma et al. (2019). Bioassay-guided isolation of lanostane-type triterpenoids as α-glucosidase inhibitors from Ganoderma hainanense. Phytochemistry Letters 29:154-159, February 2019. DOI: 10.1016/j.phytol.2018.12.007. Phytochemistry Letters.

Showing NP-Card for 3-acetylganodermadiol (NP0044162)

MOL for NP0044162 (3-acetylganodermadiol)

3D MOL for NP0044162 (3-acetylganodermadiol)

3D SDF for NP0044162 (3-acetylganodermadiol)

3D-SDF for NP0044162 (3-acetylganodermadiol)

PDB for NP0044162 (3-acetylganodermadiol)

3D PDB for NP0044162 (3-acetylganodermadiol)

SMILES for NP0044162 (3-acetylganodermadiol)

INCHI for NP0044162 (3-acetylganodermadiol)

Structure for NP0044162 (3-acetylganodermadiol)

3D Structure for NP0044162 (3-acetylganodermadiol)