NP-MRD: Showing NP-Card for 3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al (NP0048235)

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Record Information

Version

2.0

Created at

2022-03-17 20:53:16 UTC

Updated at

2022-03-17 20:53:16 UTC

NP-MRD ID

NP0048235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al

Description

3Beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al, also known as ganoderic aldehyde a, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3Beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3beta-3-hydroxy-11-oxolanosta-8,24-dien-26-al has been detected, but not quantified in, mushrooms. 3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al is found in Ganoderma lucidum . This could make 3beta-3-hydroxy-11-oxolanosta-8,24-dien-26-al a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308252D          

 33 36  0  0  0  0            999 V2000
   -4.3282   -0.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119    3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    2.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -1.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7064   -2.1749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  2  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 11  1  0  0  0  0
 23 17  1  0  0  0  0
 24 12  1  0  0  0  0
 25 14  1  0  0  0  0
 26 22  2  0  0  0  0
 26 23  1  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28  5  1  0  0  0  0
 28 15  1  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29  6  1  0  0  0  0
 29 16  1  0  0  0  0
 29 22  1  0  0  0  0
 30  7  1  0  0  0  0
 30 17  1  0  0  0  0
 30 21  1  0  0  0  0
 30 29  1  0  0  0  0
 31 18  2  0  0  0  0
 32 23  2  0  0  0  0
 33 25  1  0  0  0  0
M  END


  Mrv0541 05061308252D          

 33 36  0  0  0  0            999 V2000
   -4.3282   -0.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119    3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    2.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000   -1.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -0.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7064   -2.1749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  2  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 21 20  1  0  0  0  0
 22 11  1  0  0  0  0
 23 17  1  0  0  0  0
 24 12  1  0  0  0  0
 25 14  1  0  0  0  0
 26 22  2  0  0  0  0
 26 23  1  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 24  1  0  0  0  0
 27 25  1  0  0  0  0
 28  5  1  0  0  0  0
 28 15  1  0  0  0  0
 28 24  1  0  0  0  0
 28 26  1  0  0  0  0
 29  6  1  0  0  0  0
 29 16  1  0  0  0  0
 29 22  1  0  0  0  0
 30  7  1  0  0  0  0
 30 17  1  0  0  0  0
 30 21  1  0  0  0  0
 30 29  1  0  0  0  0
 31 18  2  0  0  0  0
 32 23  2  0  0  0  0
 33 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC\C=C(\C)C=O)C1CCC2(C)C3=C(C(=O)CC12C)C1(C)CCC(O)C(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-19(18-31)9-8-10-20(2)21-13-16-29(6)22-11-12-24-27(3,4)25(33)14-15-28(24,5)26(22)23(32)17-30(21,29)7/h9,18,20-21,24-25,33H,8,10-17H2,1-7H3/b19-9-

> <INCHI_KEY>
CFBBUWFXWSYJHB-OCKHKDLRSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.6844

> <EXACT_MASS>
454.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
54.69921024505504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enal

> <ALOGPS_LOGP>
6.14

> <JCHEM_LOGP>
6.072465506333334

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.553772310569403

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8067624496954889

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
136.02969999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.079  -1.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.032  -0.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.929   5.737   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.791   5.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.897   1.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.764   4.702   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.200   0.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.083  -0.412   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.609  -0.202   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.138   0.803   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.434   4.926   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.950   5.198   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.095   3.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.929   1.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.413   1.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.180   4.152   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.865   0.581   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.973  -2.844   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.554  -1.418   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.612   0.593   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.667   1.809   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.911   3.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.381   0.852   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.943   4.020   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.452   3.114   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.904   2.301   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.459   4.291   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.420   2.572   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.395   3.207   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.872   1.759   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.919  -4.060   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.373  -0.325   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.968   3.385   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   10                                                       
CONECT    9    8   19                                                       
CONECT   10    8   20                                                       
CONECT   11   12   22                                                       
CONECT   12   11   24                                                       
CONECT   13   16   21                                                       
CONECT   14   15   25                                                       
CONECT   15   14   28                                                       
CONECT   16   13   29                                                       
CONECT   17   23   30                                                       
CONECT   18   19   31                                                       
CONECT   19    1    9   18                                                  
CONECT   20    2   10   21                                                  
CONECT   21   13   20   30                                                  
CONECT   22   11   26   29                                                  
CONECT   23   17   26   32                                                  
CONECT   24   12   27   28                                                  
CONECT   25   14   27   33                                                  
CONECT   26   22   23   28                                                  
CONECT   27    3    4   24   25                                             
CONECT   28    5   15   24   26                                             
CONECT   29    6   16   22   30                                             
CONECT   30    7   17   21   29                                             
CONECT   31   18                                                            
CONECT   32   23                                                            
CONECT   33   25                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
3b-3-Hydroxy-11-oxolanosta-8,24-dien-26-al	Generator
3Β-3-hydroxy-11-oxolanosta-8,24-dien-26-al	Generator
(+)-Ganoderic aldehyde a	HMDB
Ganoderic aldehyde a	HMDB

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6844 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enal

Traditional Name

(2Z)-6-{5-hydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enal

CAS Registry Number

126313-85-7

SMILES

CC(CC\C=C(\C)C=O)C1CCC2(C)C3=C(C(=O)CC12C)C1(C)CCC(O)C(C)(C)C1CC3

InChI Identifier

InChI=1S/C30H46O3/c1-19(18-31)9-8-10-20(2)21-13-16-29(6)22-11-12-24-27(3,4)25(33)14-15-28(24,5)26(22)23(32)17-30(21,29)7/h9,18,20-21,24-25,33H,8,10-17H2,1-7H3/b19-9-

InChI Key

CFBBUWFXWSYJHB-OCKHKDLRSA-N

Experimental Spectra

Not Available

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
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

Not Available

Substituents

Not Available

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	6.14	ALOGPS
logP	6.07	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.03 m³·mol⁻¹	ChemAxon
Polarizability	54.7 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

HMDB0035406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014081

KNApSAcK ID

C00033852

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

131751740

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al (NP0048235)

MOL for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

3D MOL for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

3D SDF for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

3D-SDF for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

PDB for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

3D PDB for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

SMILES for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

INCHI for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

Structure for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)

3D Structure for NP0048235 (3beta-3-Hydroxy-11-oxolanosta-8,24-dien-26-al)