NP-MRD: Showing NP-Card for 10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid (NP0165794)

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Record Information

Version

2.0

Created at

2022-09-03 01:01:47 UTC

Updated at

2022-09-03 01:01:47 UTC

NP-MRD ID

NP0165794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

Description

Queretaroic acid, also known as queretaroate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Queretaroic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Queretaroic acid has been detected, but not quantified in, cereals and cereal products and fruits. 10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid is found in Akebia quinata, Drypetes inaequalis, Oxyceros horridus, Stauntonia hexaphylla, Stauntonia obovatifoliola, Stenocereus eruca and Tripterygium hypoglaucum. This could make queretaroic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307522D          

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M  END

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M  END


  Mrv0541 05061307522D          

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    6.2804    1.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285    4.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646   -1.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9949    0.1148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7093    1.3523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 19  7  2  0  0  0  0
 20 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21  9  1  0  0  0  0
 22  8  1  0  0  0  0
 23 10  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 21  1  0  0  0  0
 25 23  1  0  0  0  0
 26  3  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
 26 18  1  0  0  0  0
 27  4  1  0  0  0  0
 27 11  1  0  0  0  0
 27 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28  5  1  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29  6  1  0  0  0  0
 29 12  1  0  0  0  0
 29 22  1  0  0  0  0
 29 28  1  0  0  0  0
 30 15  1  0  0  0  0
 30 16  1  0  0  0  0
 30 20  1  0  0  0  0
 30 24  1  0  0  0  0
 31 18  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  2  0  0  0  0
 34 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(O)CCC2(C)C1CCC1(C)C2CC=C2C3CC(C)(CO)CCC3(CCC12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-25(2)21-9-12-29(6)22(27(21,4)11-10-23(25)32)8-7-19-20-17-26(3,18-31)13-15-30(20,24(33)34)16-14-28(19,29)5/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)

> <INCHI_KEY>
CZWBKSDPBWNHGO-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.6997

> <EXACT_MASS>
472.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.84547846214383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
5.98

> <JCHEM_LOGP>
5.314062276666666

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.285194899054087

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.644878908319913

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7220666805556876

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
135.39919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic 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       4.711  -3.275   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.731  -3.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.734   6.784   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.055   1.754   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.056  -0.556   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.744   1.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.722   3.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.389   2.524   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.389  -2.096   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.388   0.214   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.721   0.984   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.722  -1.326   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.057   4.834   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.390   0.214   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.057   3.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.723   0.984   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.390   4.834   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.713   6.784   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.056   2.524   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.390   3.294   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.055  -1.326   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.389   0.984   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.388  -1.326   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.057   1.754   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.721  -2.096   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.723   5.604   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.055   0.214   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.056   0.984   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.722   0.214   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.723   2.524   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.187   8.231   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.054  -2.096   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.057   0.214   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.391   2.524   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7    8   19                                                       
CONECT    8    7   22                                                       
CONECT    9   12   21                                                       
CONECT   10   11   23                                                       
CONECT   11   10   27                                                       
CONECT   12    9   29                                                       
CONECT   13   15   26                                                       
CONECT   14   16   28                                                       
CONECT   15   13   30                                                       
CONECT   16   14   30                                                       
CONECT   17   20   26                                                       
CONECT   18   26   31                                                       
CONECT   19    7   20   28                                                  
CONECT   20   17   19   30                                                  
CONECT   21    9   25   27                                                  
CONECT   22    8   27   29                                                  
CONECT   23   10   25   32                                                  
CONECT   24   30   33   34                                                  
CONECT   25    1    2   21   23                                             
CONECT   26    3   13   17   18                                             
CONECT   27    4   11   21   22                                             
CONECT   28    5   14   19   29                                             
CONECT   29    6   12   22   28                                             
CONECT   30   15   16   20   24                                             
CONECT   31   18                                                            
CONECT   32   23                                                            
CONECT   33   24                                                            
CONECT   34   24                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Queretaroate	Generator
10-Hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.6997 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)C(O)CCC2(C)C1CCC1(C)C2CC=C2C3CC(C)(CO)CCC3(CCC12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O4/c1-25(2)21-9-12-29(6)22(27(21,4)11-10-23(25)32)8-7-19-20-17-26(3,18-31)13-15-30(20,24(33)34)16-14-28(19,29)5/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)

InChI Key

CZWBKSDPBWNHGO-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
Akebia quinata	LOTUS Database	35616633
Drypetes inaequalis	LOTUS Database	35616633
Oxyceros horridus	LOTUS Database	35616633
Stauntonia hexaphylla	LOTUS Database	35616633
Stauntonia obovatifoliola	LOTUS Database	35616633
Stenocereus eruca	LOTUS Database	35616633
Tripterygium hypoglaucum	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
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
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	5.98	ALOGPS
logP	5.31	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-0.72	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	2	ChemAxon
Refractivity	135.4 m³·mol⁻¹	ChemAxon
Polarizability	55.85 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

HMDB0034523

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013024

KNApSAcK ID

C00031116

Chemspider ID

4477681

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319375

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid (NP0165794)

MOL for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D MOL for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D SDF for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D-SDF for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

PDB for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D PDB for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

SMILES for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

INCHI for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

Structure for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)

3D Structure for NP0165794 (10-hydroxy-2-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid)