NP-MRD: Showing NP-Card for Brevipolide G (NP0331381)

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Record Information

Version

1.0

Created at

2022-12-23 08:24:59 UTC

Updated at

2024-04-19 09:39:21 UTC

NP-MRD ID

NP0331381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brevipolide G

Description

Brevipolide G belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. It was first documented in 2022 (PMID: 36057450). Based on a literature review a significant number of articles have been published on Brevipolide G (PMID: 36057449) (PMID: 36057448) (PMID: 36057447) (PMID: 36057446).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032217332D          

 28 30  0  0  1  0            999 V2000
   -0.4125   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1270   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138   -6.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -4.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -4.4270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  1  0  0  0
 22 20  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
M  END


  Mrv1652309032217332D          

 28 30  0  0  1  0            999 V2000
   -0.4125   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -4.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1270   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -6.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138   -6.9020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6993   -5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -4.0145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -4.4270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559   -5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.0145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  1  0  0  0
 22 20  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](OC(=O)\C=C\C1=CC=C(O)C=C1)C(=O)[C@H]1C[C@@H]1[C@H](O)[C@H]1CC=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O7/c1-12(27-19(24)10-7-13-5-8-14(22)9-6-13)20(25)15-11-16(15)21(26)17-3-2-4-18(23)28-17/h2,4-10,12,15-17,21-22,26H,3,11H2,1H3/b10-7+/t12-,15-,16-,17+,21-/m0/s1

> <INCHI_KEY>
BJDMHAYLPGRUFH-HIELJHRRSA-N

> <FORMULA>
C21H22O7

> <MOLECULAR_WEIGHT>
386.4

> <EXACT_MASS>
386.136553048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.56225653034925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(1S,2S)-2-[(S)-hydroxy[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
3.069497823666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.884265030253449

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.398533204470173

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2823129983168586

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
101.11280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(1S,2S)-2-[(S)-hydroxy[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.770  -5.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -7.494   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.104  -8.264   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.437  -7.494   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.437  -5.954   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.771  -8.264   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.771  -9.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.105 -10.574   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.105 -12.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.438 -12.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.772 -12.114   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -10.106 -12.884   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -8.772 -10.574   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.438  -9.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564  -8.264   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.564  -9.804   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.897  -7.494   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.437  -7.494   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.771  -8.264   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.771  -9.804   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.105  -7.494   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.438  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.772  -5.954   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.772  -7.494   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.106  -8.264   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.438  -8.264   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   19                                                       
CONECT   19   18   17   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₇

Average Mass

386.4000 Da

Monoisotopic Mass

386.13655 Da

IUPAC Name

(2S)-1-[(1S,2S)-2-[(S)-hydroxy[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S)-1-[(1S,2S)-2-[(S)-hydroxy[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]cyclopropyl]-1-oxopropan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H](OC(=O)\C=C\C1=CC=C(O)C=C1)C(=O)[C@H]1C[C@@H]1[C@H](O)[C@H]1CC=CC(=O)O1

InChI Identifier

InChI=1S/C21H22O7/c1-12(27-19(24)10-7-13-5-8-14(22)9-6-13)20(25)15-11-16(15)21(26)17-3-2-4-18(23)28-17/h2,4-10,12,15-17,21-22,26H,3,11H2,1H3/b10-7+/t12-,15-,16-,17+,21-/m0/s1

InChI Key

BJDMHAYLPGRUFH-HIELJHRRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Dihydropyranone
Fatty acid ester
Phenol
Alpha-acyloxy ketone
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.07	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	101.11 m³·mol⁻¹	ChemAxon
Polarizability	38.56 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

29414929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71522010

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
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Showing NP-Card for Brevipolide G (NP0331381)

MOL for NP0331381 (Brevipolide G)

3D MOL for NP0331381 (Brevipolide G)

3D SDF for NP0331381 (Brevipolide G)

3D-SDF for NP0331381 (Brevipolide G)

PDB for NP0331381 (Brevipolide G)

3D PDB for NP0331381 (Brevipolide G)

SMILES for NP0331381 (Brevipolide G)

INCHI for NP0331381 (Brevipolide G)

Structure for NP0331381 (Brevipolide G)

3D Structure for NP0331381 (Brevipolide G)