NP-MRD: Showing NP-Card for (2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid (NP0273045)

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Record Information

Version

2.0

Created at

2022-09-08 19:56:27 UTC

Updated at

2022-09-08 19:56:27 UTC

NP-MRD ID

NP0273045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid

Description

Ganodermic acid Jb, also known as ganodermate JB, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Ganodermic acid Jb is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ganodermic acid JB has been detected, but not quantified in, mushrooms. This could make ganodermic acid JB a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308232D          

 34 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308232D          

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 18  9  1  0  0  0  0
 19  2  1  0  0  0  0
 19 10  2  0  0  0  0
 20 13  2  0  0  0  0
 21 11  2  0  0  0  0
 21 20  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 12  1  0  0  0  0
 24 14  1  0  0  0  0
 25 17  1  0  0  0  0
 26 19  1  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 23  1  0  0  0  0
 27 24  1  0  0  0  0
 28  5  1  0  0  0  0
 28 15  1  0  0  0  0
 28 20  1  0  0  0  0
 28 23  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 21  1  0  0  0  0
 30 25  1  0  0  0  0
 30 29  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  1  0  0  0  0
 33 26  2  0  0  0  0
 34 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC\C=C(/C)C(O)=O)C1CC(O)C2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18(9-8-10-19(2)26(33)34)22-17-25(32)30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(22,30)6/h10-11,13,18,22-25,31-32H,8-9,12,14-17H2,1-7H3,(H,33,34)/b19-10+

> <INCHI_KEY>
VFCVARJMDQZNKD-VXLYETTFSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.6838

> <EXACT_MASS>
470.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.699848265032564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-6-{5,12-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
6.20

> <JCHEM_LOGP>
5.305632396333334

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.618794118226784

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.656697317263119

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2728561617635322

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
138.89399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-6-{5,12-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-2-methylhept-2-enoic acid

> <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       6.559   2.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.618   4.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.520  -4.434   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.382  -3.762   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.488   0.179   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.792   0.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.356  -3.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.508   1.715   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.453   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.983   1.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.026  -3.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.542  -3.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.972   0.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.520  -0.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.004  -0.092   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.456   0.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.496  -1.985   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.979   0.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.037   2.720   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.495  -0.998   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.503  -2.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.924  -0.506   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.534  -2.717   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.043  -1.811   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.771  -2.849   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.488   2.510   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.050  -2.988   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.011  -1.269   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.463  -0.456   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.987  -1.904   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      17.559  -2.082   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.821  -4.389   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.068   1.083   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.433   3.725   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   10                                                       
CONECT    9    8   18                                                       
CONECT   10    8   19                                                       
CONECT   11   12   21                                                       
CONECT   12   11   23                                                       
CONECT   13   16   20                                                       
CONECT   14   15   24                                                       
CONECT   15   14   28                                                       
CONECT   16   13   29                                                       
CONECT   17   22   25                                                       
CONECT   18    1    9   22                                                  
CONECT   19    2   10   26                                                  
CONECT   20   13   21   28                                                  
CONECT   21   11   20   30                                                  
CONECT   22   17   18   29                                                  
CONECT   23   12   27   28                                                  
CONECT   24   14   27   31                                                  
CONECT   25   17   30   32                                                  
CONECT   26   19   33   34                                                  
CONECT   27    3    4   23   24                                             
CONECT   28    5   15   20   23                                             
CONECT   29    6   16   22   30                                             
CONECT   30    7   21   25   29                                             
CONECT   31   24                                                            
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   26                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Ganodermate JB	Generator
(2E)-6-{5,12-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-2-methylhept-2-enoate	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6838 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(2E)-6-{5,12-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-2-methylhept-2-enoic acid

Traditional Name

(2E)-6-{5,12-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),9-dien-14-yl}-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CC\C=C(/C)C(O)=O)C1CC(O)C2(C)C3=CCC4C(C)(C)C(O)CCC4(C)C3=CCC12C

InChI Identifier

InChI=1S/C30H46O4/c1-18(9-8-10-19(2)26(33)34)22-17-25(32)30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(22,30)6/h10-11,13,18,22-25,31-32H,8-9,12,14-17H2,1-7H3,(H,33,34)/b19-10+

InChI Key

VFCVARJMDQZNKD-VXLYETTFSA-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

Not Available

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	6.2	ALOGPS
logP	5.31	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-0.27	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	138.89 m³·mol⁻¹	ChemAxon
Polarizability	55.7 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

HMDB0035334

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014006

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

14325145

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid (NP0273045)

MOL for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D MOL for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D SDF for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D-SDF for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

PDB for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D PDB for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

SMILES for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

INCHI for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

Structure for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)

3D Structure for NP0273045 ((2e)-6-{3,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylhept-2-enoic acid)