NP-MRD: Showing NP-Card for Borapetic acid C (NP0331655)

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Record Information

Version

2.0

Created at

2023-05-31 12:00:27 UTC

Updated at

2024-09-03 04:16:23 UTC

NP-MRD ID

NP0331655

Natural Product DOI

https://doi.org/10.57994/0644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Borapetic acid C

Description

Borapetic acid C, also known as borapetate C, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Borapetic acid C was first documented in 2023 (PMID: 37200063). Based on a literature review very few articles have been published on Borapetic acid C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305312314002D          

 25 27  0  0  1  0            999 V2000
    0.5315   -3.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -2.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9802   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0978   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697   -0.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -1.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -1.4972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051   -0.3412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0732   -0.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180   -2.7626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 10  1  6  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  6  0  0  0
  2 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@]([H])(C(O)=O)[C@@](C)(CC(O)=O)[C@]3([H])CCC=C(C(=O)O1)[C@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O6/c1-15(7-12(17)18)9(13(19)20)6-11-16(2)8(14(21)22-11)4-3-5-10(15)16/h4,9-11H,3,5-7H2,1-2H3,(H,17,18)(H,19,20)/t9-,10+,11-,15-,16+/m1/s1

> <INCHI_KEY>
OLRSMLXTUXLIHS-FELLMWIQSA-N

> <FORMULA>
C16H20O6

> <MOLECULAR_WEIGHT>
308.33

> <EXACT_MASS>
308.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.16203899609183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,9S,10S,12R)-9-(carboxymethyl)-9,12-dimethyl-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-10-carboxylic acid

> <JCHEM_LOGP>
1.6411719646666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.54480307597035

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8631393654676396

> <JCHEM_PKA_STRONGEST_BASIC>
-6.885415106599268

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
75.24719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9S,10S,12R)-9-(carboxymethyl)-9,12-dimethyl-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-10-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-23         0                                  
HETATM    1  O   UNK     0       0.992  -5.802   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.100  -4.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.727  -3.238   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.696  -3.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.182  -1.890   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.063  -0.984   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.021  -3.421   0.000  0.00  0.00           O+0
HETATM   10  H   UNK     0       1.428  -2.795   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.996  -0.637   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.737  -0.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.078   3.605   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       4.297  -3.081   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       3.580  -5.157   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   23                                             
CONECT    5    4                                                            
CONECT    6    4    7   10   11                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12   18                                                       
CONECT   14   12                                                            
CONECT   15   12   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15    4   24                                             
CONECT   24   23                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Borapetate C	Generator

Chemical Formula

C₁₆H₂₀O₆

Average Mass

308.3300 Da

Monoisotopic Mass

308.12599 Da

IUPAC Name

(1R,8S,9S,10S,12R)-9-(carboxymethyl)-9,12-dimethyl-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-10-carboxylic acid

Traditional Name

(1R,8S,9S,10S,12R)-9-(carboxymethyl)-9,12-dimethyl-3-oxo-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-ene-10-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@]([H])(C(O)=O)[C@@](C)(CC(O)=O)[C@]3([H])CCC=C(C(=O)O1)[C@]23C

InChI Identifier

InChI=1S/C16H20O6/c1-15(7-12(17)18)9(13(19)20)6-11-16(2)8(14(21)22-11)4-3-5-10(15)16/h4,9-11H,3,5-7H2,1-2H3,(H,17,18)(H,19,20)/t9-,10+,11-,15-,16+/m1/s1

InChI Key

OLRSMLXTUXLIHS-FELLMWIQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400, CD₃OD, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
crispa		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.64	ChemAxon
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.25 m³·mol⁻¹	ChemAxon
Polarizability	30.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Borapetic acid C (NP0331655)

MOL for NP0331655 (Borapetic acid C)

3D MOL for NP0331655 (Borapetic acid C)

3D SDF for NP0331655 (Borapetic acid C)

3D-SDF for NP0331655 (Borapetic acid C)

PDB for NP0331655 (Borapetic acid C)

3D PDB for NP0331655 (Borapetic acid C)

SMILES for NP0331655 (Borapetic acid C)

INCHI for NP0331655 (Borapetic acid C)

Structure for NP0331655 (Borapetic acid C)

3D Structure for NP0331655 (Borapetic acid C)