NP-MRD: Showing NP-Card for 2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid (NP0165120)

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Record Information

Version

2.0

Created at

2022-09-03 00:09:05 UTC

Updated at

2022-09-03 00:09:05 UTC

NP-MRD ID

NP0165120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid

Description

Bryononic acid, also known as bryononate, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Bryononic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Bryononic acid has been detected, but not quantified in, fruits. 2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid is found in Lagenaria siceraria, Sandoricum indicum and Sandoricum koetjape. This could make bryononic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308342D          

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M  END

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  Mrv0541 05061308342D          

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 25 21  1  0  0  0  0
 25 23  1  0  0  0  0
 26  3  1  0  0  0  0
 26 14  1  0  0  0  0
 26 16  1  0  0  0  0
 26 22  1  0  0  0  0
 27  4  1  0  0  0  0
 27 15  1  0  0  0  0
 27 18  1  0  0  0  0
 27 24  1  0  0  0  0
 28  5  1  0  0  0  0
 28 12  1  0  0  0  0
 28 19  1  0  0  0  0
 28 21  1  0  0  0  0
 29  6  1  0  0  0  0
 29 17  1  0  0  0  0
 29 20  1  0  0  0  0
 30  7  1  0  0  0  0
 30 13  1  0  0  0  0
 30 22  1  0  0  0  0
 30 29  1  0  0  0  0
 31 23  2  0  0  0  0
 32 24  2  0  0  0  0
 33 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC3=C(CCC4(C)C5CC(C)(CCC5(C)CCC34C)C(O)=O)C2(C)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-22H,8-18H2,1-7H3,(H,32,33)

> <INCHI_KEY>
XKLPFWHBIRYSNP-UHFFFAOYSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.6844

> <EXACT_MASS>
454.344695338

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
54.579652974207605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid

> <ALOGPS_LOGP>
6.60

> <JCHEM_LOGP>
7.114703314333335

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.69285621740435

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615564205719523

> <JCHEM_PKA_STRONGEST_BASIC>
-7.471290151345441

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
132.53559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1H-picene-2-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       9.743   0.230   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.457   1.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.413   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.503   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   4.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620   0.413   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.310   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.160   0.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.700   0.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.010   4.414   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.470   4.414   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.540   0.413   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   0.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.470   1.746   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.780   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.217   4.940   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.010   1.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.770   1.746   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.700   3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.320   3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.397   3.950   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.485   6.457   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   30                                                            
CONECT    8    9   20                                                       
CONECT    9    8   21                                                       
CONECT   10   13   19                                                       
CONECT   11   12   23                                                       
CONECT   12   11   28                                                       
CONECT   13   10   30                                                       
CONECT   14   15   26                                                       
CONECT   15   14   27                                                       
CONECT   16   17   26                                                       
CONECT   17   16   29                                                       
CONECT   18   22   27                                                       
CONECT   19   10   20   28                                                  
CONECT   20    8   19   29                                                  
CONECT   21    9   25   28                                                  
CONECT   22   18   26   30                                                  
CONECT   23   11   25   31                                                  
CONECT   24   27   32   33                                                  
CONECT   25    1    2   21   23                                             
CONECT   26    3   14   16   22                                             
CONECT   27    4   15   18   24                                             
CONECT   28    5   12   19   21                                             
CONECT   29    6   17   20   30                                             
CONECT   30    7   13   22   29                                             
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   24                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Bryononate	Generator
3-oxo-8-Multifloren-29-Oic acid	HMDB
2,4a,6a,9,9,12a,14a-Heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylate	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6844 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid

Traditional Name

2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1H-picene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)C2CCC3=C(CCC4(C)C5CC(C)(CCC5(C)CCC34C)C(O)=O)C2(C)CCC1=O

InChI Identifier

InChI=1S/C30H46O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-22H,8-18H2,1-7H3,(H,32,33)

InChI Key

XKLPFWHBIRYSNP-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
Lagenaria siceraria	LOTUS Database	35616633
Sandoricum indicum	LOTUS Database	35616633
Sandoricum koetjape	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	6.6	ALOGPS
logP	7.11	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.54 m³·mol⁻¹	ChemAxon
Polarizability	54.58 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

HMDB0035594

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014286

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

131751810

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid (NP0165120)

MOL for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

3D MOL for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

3D SDF for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

3D-SDF for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

PDB for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

3D PDB for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

SMILES for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

INCHI for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

Structure for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)

3D Structure for NP0165120 (2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,13,14,14b-dodecahydro-1h-picene-2-carboxylic acid)