NP-MRD: Showing NP-Card for Germanicol (NP0047996)

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Record Information

Version

2.0

Created at

2022-03-17 20:49:23 UTC

Updated at

2022-03-17 20:49:23 UTC

NP-MRD ID

NP0047996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Germanicol

Description

Germanicol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Germanicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Germanicol is found, on average, in the highest concentration within tea. Germanicol has also been detected, but not quantified in, several different foods, such as common sages, cereals and cereal products, fenugreeks, asparagus, and breadfruits. Germanicol is found in Barringtonia asiatica, Barringtonia racemosa, Camellia oleifera, Chrysolaena propinqua, Cnidoscolus urens, Cuphea wrightii, Equisetum arvense, Euphorbia balsamifera , Euphorbia maculata, Euphorbia nicaeensis, Euphorbia pulcherrima, Festuca argentina, Ixeris chinensis, Koelpinia linearis, Lactarius germanicum, Lactuca saligna, Lactuca sativa, Lactuca virosa, Lactucarium germanicum, Mangifera indica, Marsypianthes chamaedrys, Olea europaea, Phoradendron reichenbachianum, Phytolacca americana, Picris hieracioides, Pistacia lentiscus, Poinsettia pulcherrima, Salvia pratensis, Scorzonera cretica, Sonchus asper, Vernonia brasiliana, Vernonia incana and Vitis vinifera. This could make germanicol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310101704482D          

 31 35  0  0  0  0            999 V2000
   10.4246   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5061   -2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0991    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2631    0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0618   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6493   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4118    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4118   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  1  0  0  0  0
 20  9  1  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 11  1  0  0  0  0
 23 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 15  1  0  0  0  0
 25 19  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 27 17  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 13  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  7  1  0  0  0  0
 29 18  1  0  0  0  0
 29 20  1  0  0  0  0
 30  8  1  0  0  0  0
 30 14  1  0  0  0  0
 30 23  1  0  0  0  0
 30 29  1  0  0  0  0
 31 24  1  0  0  0  0
M  END


  Mrv1652310101704482D          

 31 35  0  0  0  0            999 V2000
   10.4246   -1.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5061   -2.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0991    0.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2631    0.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0618   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6493   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4118    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4118   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9368   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8243   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6368   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  1  0  0  0  0
 20  9  1  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 11  1  0  0  0  0
 23 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 15  1  0  0  0  0
 25 19  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 22  1  0  0  0  0
 26 24  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 27 17  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 13  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  7  1  0  0  0  0
 29 18  1  0  0  0  0
 29 20  1  0  0  0  0
 30  8  1  0  0  0  0
 30 14  1  0  0  0  0
 30 23  1  0  0  0  0
 30 29  1  0  0  0  0
 31 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h19-20,22-24,31H,9-18H2,1-8H3

> <INCHI_KEY>
QMUXVPRGNJLGRT-UHFFFAOYSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.22078753083731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12b,13,14,14a,14b-icosahydropicen-3-ol

> <ALOGPS_LOGP>
7.26

> <JCHEM_LOGP>
7.403140834333334

> <ALOGPS_LOGS>
-6.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489433390176508

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351218351367943

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
131.90729999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.82e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12b,13,14,14a-tetradecahydropicen-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0      19.459  -3.400   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.745  -4.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.499   1.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.785   0.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.242   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.312  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.622   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.691   1.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.392  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.852  -2.874   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.542   1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.232  -2.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.772  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   1.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.782  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.012  -0.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.702   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.162   1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.472  -2.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.162  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.702  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.772  -0.206   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.462  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.012  -2.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.232  -0.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.472  -0.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.542  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.392  -0.206   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.852  -0.206   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.922  -1.540   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8   30                                                            
CONECT    9   10   20                                                       
CONECT   10    9   23                                                       
CONECT   11   14   22                                                       
CONECT   12   13   24                                                       
CONECT   13   12   28                                                       
CONECT   14   11   30                                                       
CONECT   15   16   25                                                       
CONECT   16   15   27                                                       
CONECT   17   18   27                                                       
CONECT   18   17   29                                                       
CONECT   19   21   25                                                       
CONECT   20    9   21   29                                                  
CONECT   21   19   20   27                                                  
CONECT   22   11   26   28                                                  
CONECT   23   10   28   30                                                  
CONECT   24   12   26   31                                                  
CONECT   25    1    2   15   19                                             
CONECT   26    3    4   22   24                                             
CONECT   27    5   16   17   21                                             
CONECT   28    6   13   22   23                                             
CONECT   29    7   18   20   30                                             
CONECT   30    8   14   23   29                                             
CONECT   31   24                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7174 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12b,13,14,14a,14b-icosahydropicen-3-ol

Traditional Name

4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12b,13,14,14a-tetradecahydropicen-3-ol

CAS Registry Number

465-02-1

SMILES

CC1(C)CCC2(C)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2=C1

InChI Identifier

InChI=1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h19-20,22-24,31H,9-18H2,1-8H3

InChI Key

QMUXVPRGNJLGRT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Barringtonia asiatica	LOTUS Database	35616633
Barringtonia racemosa	LOTUS Database	35616633
Camellia oleifera	LOTUS Database	35616633
Chrysolaena propinqua	LOTUS Database	35616633
Cnidoscolus urens	LOTUS Database	35616633
Cuphea wrightii	LOTUS Database	35616633
Equisetum arvense	LOTUS Database	35616633
Euphorbia balsamifera	Plant	KNApSAcK
Euphorbia maculata	LOTUS Database	35616633
Euphorbia nicaeensis	LOTUS Database	35616633
Euphorbia pulcherrima	LOTUS Database	35616633
Festuca argentina	LOTUS Database	35616633
Ixeris chinensis	LOTUS Database	35616633
Koelpinia linearis	Plant	KNApSAcK
Lactarius germanicum	Fungi	KNApSAcK
Lactuca saligna L.	LOTUS Database	35616633
Lactuca sativa	LOTUS Database	35616633
Lactuca virosa	LOTUS Database	35616633
Lactucarium germanicum	-	KNApSAcK
Mangifera indica	LOTUS Database	35616633
Marsypianthes chamaedrys	LOTUS Database	35616633
Olea europaea	LOTUS Database	35616633
Phoradendron reichenbachianum	LOTUS Database	35616633
Phytolacca americana	LOTUS Database	35616633
Picris hieracioides	LOTUS Database	35616633
Pistacia lentiscus	LOTUS Database	35616633
Poinsettia pulcherrima	Plant	KNApSAcK
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia pratensis	LOTUS Database	35616633
Scorzonera cretica	LOTUS Database	35616633
Sonchus asper	LOTUS Database	35616633
Vernonia brasiliana	LOTUS Database	35616633
Vernonia incana	LOTUS Database	35616633
Vitellaria paradoxa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a triterpenoid (GERMANICOL )

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	7.26	ALOGPS
logP	7.4	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	131.91 m³·mol⁻¹	ChemAxon
Polarizability	54.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0175747

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013013

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

609334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Germanicol (NP0047996)

MOL for NP0047996 (Germanicol)

3D MOL for NP0047996 (Germanicol)

3D SDF for NP0047996 (Germanicol)

3D-SDF for NP0047996 (Germanicol)

PDB for NP0047996 (Germanicol)

3D PDB for NP0047996 (Germanicol)

SMILES for NP0047996 (Germanicol)

INCHI for NP0047996 (Germanicol)

Structure for NP0047996 (Germanicol)

3D Structure for NP0047996 (Germanicol)