NP-MRD: Showing NP-Card for Borapetic acid B (NP0331654)

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Record Information

Version

2.0

Created at

2023-05-31 12:00:18 UTC

Updated at

2025-02-11 15:45:33 UTC

NP-MRD ID

NP0331654

Natural Product DOI

https://doi.org/10.57994/0643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Borapetic acid B

Description

Borapetic acid B, also known as borapetate b, belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Borapetic acid B was first documented in 2023 (PMID: 37200063). Based on a literature review very few articles have been published on Borapetic acid B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305312314002D          

 33 35  0  0  1  0            999 V2000
    0.0542   -0.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652   -0.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -1.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9508   -1.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -2.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -1.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -2.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -3.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -3.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -3.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017   -0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271    0.5709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4297    0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.6655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3837    1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037    1.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874   -0.0319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3297    2.4135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1091    2.1431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717    3.1643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    1.9727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6609    2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    2.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    3.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126    3.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    4.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077    3.7690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881    2.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    0.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5421    1.1527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3201    1.4272    0.0000 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  2 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  6  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 24 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 22 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END


  Mrv1652305312314002D          

 33 35  0  0  1  0            999 V2000
    0.0542   -0.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652   -0.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -1.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9508   -1.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2254   -2.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -1.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -2.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -3.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -3.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6889   -3.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017   -0.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1271    0.5709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4297    0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466    0.6655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3837    1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037    1.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874   -0.0319    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3297    2.4135    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1091    2.1431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717    3.1643    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6323    1.9727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6609    2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0328    2.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    3.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8126    3.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028    4.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077    3.7690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881    2.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782    1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    0.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5421    1.1527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3201    1.4272    0.0000 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  2 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  6  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  2  0  0  0  0
 24 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 22 32  1  0  0  0  0
 12 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0331654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]([H])(C(=O)O1)[C@@](C)(CC(O)C(=C\C(O)=O)\C(O)=O)[C@]1([H])CCC=C(C(=O)OC)[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O9/c1-20(9-13(22)10(17(25)26)7-16(23)24)12-8-15(30-19(12)28)21(2)11(18(27)29-3)5-4-6-14(20)21/h5,7,12-15,22H,4,6,8-9H2,1-3H3,(H,23,24)(H,25,26)/b10-7-/t12-,13?,14-,15-,20+,21-/m0/s1

> <INCHI_KEY>
IWNLRPDJOXSJOV-WCUMRFAYSA-N

> <FORMULA>
C21H26O9

> <MOLECULAR_WEIGHT>
422.43

> <EXACT_MASS>
422.157682417

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.27954003315982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-{1-hydroxy-2-[(1S,2R,7S,8S,9R)-3-(methoxycarbonyl)-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-en-8-yl]ethyl}but-2-enedioic acid

> <JCHEM_LOGP>
1.3228383089999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.831009579744966

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.470213356607133

> <JCHEM_PKA_STRONGEST_BASIC>
-3.125671724853807

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
102.4273

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-{1-hydroxy-2-[(1S,2R,7S,8S,9R)-3-(methoxycarbonyl)-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-en-8-yl]ethyl}but-2-enedioic 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       0.101  -1.274   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.615  -1.557   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.128  -3.009   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.641  -3.291   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.154  -4.743   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.643  -2.121   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.126  -4.179   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.639  -5.631   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.637  -6.801   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.153  -5.913   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.616  -0.387   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104   1.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.802   0.243   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.634   1.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.450   2.548   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.980   2.380   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       4.457  -0.060   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       3.466   3.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.482   4.505   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.937   4.001   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       3.120   5.907   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       1.180   3.682   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.234   5.221   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.061   4.594   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.107   6.124   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.517   6.744   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.685   8.275   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.134   7.035   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.471   3.974   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.639   2.443   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.398   1.532   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.012   2.152   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       2.464   2.664   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   14   32                                             
CONECT   13   12                                                            
CONECT   14   12   15   17   18                                             
CONECT   15   14   16   20                                                  
CONECT   16   15                                                            
CONECT   17   14                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19   15                                                       
CONECT   21   19                                                            
CONECT   22   19   23   24   32                                             
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25                                                            
CONECT   29   24   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   22   12   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
Borapetate b	Generator

Chemical Formula

C₂₁H₂₆O₉

Average Mass

422.4300 Da

Monoisotopic Mass

422.15768 Da

IUPAC Name

(2Z)-2-{1-hydroxy-2-[(1S,2R,7S,8S,9R)-3-(methoxycarbonyl)-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-en-8-yl]ethyl}but-2-enedioic acid

Traditional Name

(2Z)-2-{1-hydroxy-2-[(1S,2R,7S,8S,9R)-3-(methoxycarbonyl)-2,8-dimethyl-10-oxo-11-oxatricyclo[7.2.1.0^{2,7}]dodec-3-en-8-yl]ethyl}but-2-enedioic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]([H])(C(=O)O1)[C@@](C)(CC(O)C(=C\C(O)=O)\C(O)=O)[C@]1([H])CCC=C(C(=O)OC)[C@]21C

InChI Identifier

InChI=1S/C21H26O9/c1-20(9-13(22)10(17(25)26)7-16(23)24)12-8-15(30-19(12)28)21(2)11(18(27)29-3)5-4-6-14(20)21/h5,7,12-15,22H,4,6,8-9H2,1-3H3,(H,23,24)(H,25,26)/b10-7-/t12-,13?,14-,15-,20+,21-/m0/s1

InChI Key

IWNLRPDJOXSJOV-WCUMRFAYSA-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
Tinospora crispa		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Tetracarboxylic acid or derivatives
Caprolactone
Oxepane
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.32	ChemAxon
pKa (Strongest Acidic)	2.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.43 m³·mol⁻¹	ChemAxon
Polarizability	41.28 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	Yes	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

DOI: 10.1021/acs.jnatprod.3c00114

Showing NP-Card for Borapetic acid B (NP0331654)

MOL for NP0331654 (Borapetic acid B)

3D MOL for NP0331654 (Borapetic acid B)

3D SDF for NP0331654 (Borapetic acid B)

3D-SDF for NP0331654 (Borapetic acid B)

PDB for NP0331654 (Borapetic acid B)

3D PDB for NP0331654 (Borapetic acid B)

SMILES for NP0331654 (Borapetic acid B)

INCHI for NP0331654 (Borapetic acid B)

Structure for NP0331654 (Borapetic acid B)

3D Structure for NP0331654 (Borapetic acid B)