NP-MRD: Showing NP-Card for 3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde (NP0248893)

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Record Information

Version

2.0

Created at

2022-09-07 11:18:37 UTC

Updated at

2022-09-07 11:18:37 UTC

NP-MRD ID

NP0248893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde

Description

Theasapogenol E, also known as camelliagenin e, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Theasapogenol E is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Theasapogenol E has been detected, but not quantified in, tea. 3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde is found in Camellia sinensis. This could make theasapogenol e a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307592D          

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M  END

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M  END


  Mrv0541 05061307592D          

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    4.0749    0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894    0.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2183    1.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6834   -2.4044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6472    1.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5026   -0.9971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9328    0.2404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6473    3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7533    1.9766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0749    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894   -0.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 15  5  2  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17  7  1  0  0  0  0
 18  6  1  0  0  0  0
 19  8  1  0  0  0  0
 20 12  1  0  0  0  0
 22 21  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 23 21  1  0  0  0  0
 24  3  1  0  0  0  0
 24  9  1  0  0  0  0
 24 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25  4  1  0  0  0  0
 25 13  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
 26 10  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 15  1  0  0  0  0
 27 26  1  0  0  0  0
 28 14  1  0  0  0  0
 28 16  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 29 13  2  0  0  0  0
 30 14  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 33 21  1  0  0  0  0
 34 22  1  0  0  0  0
 26 35  1  0  0  0  0
 27 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248893

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C=O)C5CCC4(C)C3(C)CC(O)C2(CO)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O6/c1-25(2)13-18-17-7-8-20-26(3)11-10-21(33)27(4,15-31)19(26)9-12-28(20,5)29(17,6)14-22(34)30(18,16-32)24(36)23(25)35/h7,15,18-24,32-36H,8-14,16H2,1-6H3

> <INCHI_KEY>
PADNECYMNLPKRN-UHFFFAOYSA-N

> <FORMULA>
C30H48O6

> <MOLECULAR_WEIGHT>
504.6985

> <EXACT_MASS>
504.345089268

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
57.76763292259285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carbaldehyde

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
1.774827743333333

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.129428963106776

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.291892021466374

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8299547666142804

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
138.71229999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde

> <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      12.597   7.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.618   7.018   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.939   1.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.595  -3.041   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.606   3.529   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.273   2.759   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.273  -1.861   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.272   0.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.605   1.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.606  -1.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.274   5.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.274   0.449   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.615  -3.041   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.941   1.989   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.940   2.759   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.274   3.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.939  -1.091   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.273   1.219   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.272  -1.091   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.607   1.219   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.941   5.069   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.941   3.529   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.607   5.839   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.939   0.449   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.605  -1.861   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.606   0.449   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.940   1.219   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.607   2.759   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.142  -4.488   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      14.275   2.759   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.938  -1.861   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.941   0.449   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.275   5.839   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.473   3.690   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.606   1.989   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.940  -0.321   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6   15                                                       
CONECT    6    5   18                                                       
CONECT    7   10   17                                                       
CONECT    8    9   19                                                       
CONECT    9    8   24                                                       
CONECT   10    7   26                                                       
CONECT   11   16   23                                                       
CONECT   12   20   27                                                       
CONECT   13   25   29                                                       
CONECT   14   28   30                                                       
CONECT   15    5   16   27                                                  
CONECT   16   11   15   28                                                  
CONECT   17    7   24   25                                                  
CONECT   18    6   24   26                                                  
CONECT   19    8   25   31                                                  
CONECT   20   12   28   32                                                  
CONECT   21   22   23   33                                                  
CONECT   22   21   28   34                                                  
CONECT   23    1    2   11   21                                             
CONECT   24    3    9   17   18                                             
CONECT   25    4   13   17   19                                             
CONECT   26   10   18   27   35                                             
CONECT   27   12   15   26   36                                             
CONECT   28   14   16   20   22                                             
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   22                                                            
CONECT   35   26                                                            
CONECT   36   27                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
3b,16a,21b,22a,28-Pentahydroxy-12-oleanen-23-al	HMDB
Camelliagenin e	HMDB

Chemical Formula

C₃₀H₄₈O₆

Average Mass

504.6985 Da

Monoisotopic Mass

504.34509 Da

IUPAC Name

3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carbaldehyde

Traditional Name

3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C=O)C5CCC4(C)C3(C)CC(O)C2(CO)C(O)C1O

InChI Identifier

InChI=1S/C30H48O6/c1-25(2)13-18-17-7-8-20-26(3)11-10-21(33)27(4,15-31)19(26)9-12-28(20,5)29(17,6)14-22(34)30(18,16-32)24(36)23(25)35/h7,15,18-24,32-36H,8-14,16H2,1-6H3

InChI Key

PADNECYMNLPKRN-UHFFFAOYSA-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

Species Name	Source	Reference
Camellia sinensis	LOTUS Database	35616633

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
Steroid
Cyclic alcohol
Secondary alcohol
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
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	3.02	ALOGPS
logP	1.77	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.71 m³·mol⁻¹	ChemAxon
Polarizability	57.77 Å³	ChemAxon
Number of Rings	5	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

HMDB0034518

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013019

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

12302288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde (NP0248893)

MOL for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

3D MOL for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

3D SDF for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

3D-SDF for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

PDB for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

3D PDB for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

SMILES for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

INCHI for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

Structure for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)

3D Structure for NP0248893 (3,8,9,10-tetrahydroxy-8a-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carbaldehyde)