NP-MRD: Showing NP-Card for brazilein (NP0199965)

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Record Information

Version

2.0

Created at

2022-09-04 18:42:23 UTC

Updated at

2022-09-04 18:42:23 UTC

NP-MRD ID

NP0199965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

brazilein

Description

Brazilein belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Brazilein is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. brazilein was first documented in 2022 (PMID: 36037115). Based on a literature review a small amount of articles have been published on brazilein (PMID: 35969994) (PMID: 35818043) (PMID: 35773064) (PMID: 35225488).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -5.2513    0.5511   -1.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0180    0.4504   -0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4066   -0.8721   -0.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1338   -1.0466   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946   -2.2703   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -1.7751    0.2627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4005   -1.6864    1.6603 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944   -2.4984    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.7253    0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3685   -0.3927    0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6016    0.2203    0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7731    1.5262    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0337    2.1065    0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    2.2075   -0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    1.6137   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2960    0.3145   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095   -0.3218   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464    0.1210   -0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    1.4404   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1649    1.6104   -0.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7005    2.8932   -0.7688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0759   -1.7263   -0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227   -3.0968    0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1189   -2.6016   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9326   -2.4886    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5158   -2.6878   -0.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1517   -3.4588    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553   -0.3071    0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362    2.5844    1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7800    3.2251   -0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973    2.1577   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089    2.3434   -0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644    3.5896   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 16  1  0
  6 17  1  0
  4 18  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
 21 33  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
M  END


  Mrv1652309042220422D          

 21 24  0  0  1  0            999 V2000
    2.1552   -0.5001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9519   -0.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1645    0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612    0.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350    1.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1499    1.3331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9356    2.1297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7905    1.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5611    1.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6910    0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4615    0.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5914   -0.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3619   -0.6610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9508   -0.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1803   -0.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0504    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2799    0.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5452    0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3325   -0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5358   -0.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3231   -1.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C3=C4C=C(O)C(=O)C=C4C[C@@]3(O)COC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,17,19-20H,6-7H2/t16-/m1/s1

> <INCHI_KEY>
MLWIYODOURBGPI-MRXNPFEDSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.29443128590782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10S)-5,10,15-trihydroxy-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(17),2,4,6,12,15-hexaen-14-one

> <JCHEM_LOGP>
0.6469219053333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.002620310148718

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.732302746377147

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5974672792120295

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
77.13799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10S)-5,10,15-trihydroxy-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(17),2,4,6,12,15-hexaen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       4.023  -0.933   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.510  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.907   0.955   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.394   1.355   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.092   2.728   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.613   2.488   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.213   3.975   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.809   3.459   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.247   2.908   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.490   1.388   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.928   0.837   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.171  -0.684   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      15.609  -1.234   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.975  -1.654   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.537  -1.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.294   0.417   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.856   0.968   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.484   0.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.087  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.600  -1.621   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.203  -3.109   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16    6   18                                                  
CONECT   18   17    4   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

(10S)-5,10,15-trihydroxy-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(17),2,4,6,12,15-hexaen-14-one

Traditional Name

(10S)-5,10,15-trihydroxy-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-1(17),2,4,6,12,15-hexaen-14-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C3=C4C=C(O)C(=O)C=C4C[C@@]3(O)COC2=C1

InChI Identifier

InChI=1S/C16H12O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,17,19-20H,6-7H2/t16-/m1/s1

InChI Key

MLWIYODOURBGPI-MRXNPFEDSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Ketone
Cyclic ketone
Enol
Ether
Polyol
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	0.65	ChemAxon
pKa (Strongest Acidic)	8.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.14 m³·mol⁻¹	ChemAxon
Polarizability	28.29 Å³	ChemAxon
Number of Rings	4	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

21111715

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Brazilin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

69196

Good Scents ID

Not Available

References

General References

Handayani S, Susidarti RA, Utomo RY, Meiyanto E, Jenie RII: Synergistic Cytotoxic and Antimigratory Effect of Brazilein and Doxorubicin on HER2-Overexpressing Cells. Asian Pac J Cancer Prev. 2022 Aug 1;23(8):2623-2632. doi: 10.31557/APJCP.2022.23.8.2623. [PubMed:36037115 ]
Ngamwonglumlert L, Devahastin S: Brazilein as an alternative pigment: Isolation, characterization, stability enhancement and food applications. Food Chem. 2023 Jan 1;398:133898. doi: 10.1016/j.foodchem.2022.133898. Epub 2022 Aug 9. [PubMed:35969994 ]
Duran-Izquierdo M, Taboada-Alquerque M, Sierra-Marquez L, Alvarez-Ortega N, Stashenko E, Olivero-Verbel J: Hydroalcoholic extract of Haematoxylum brasiletto protects Caenorhabditis elegans from cadmium-induced toxicity. BMC Complement Med Ther. 2022 Jul 11;22(1):184. doi: 10.1186/s12906-022-03654-6. [PubMed:35818043 ]
Mou Z, Wang Y, Li Y: Retraction notice to "Brazilein induces apoptosis and G1/G0 phase cell cycle arrest by up-regulation of miR-133a in human vestibular schwannoma cells" [Experimental and Molecular Pathology 107 (2019) 95-101]. Exp Mol Pathol. 2022 Aug;127:104782. doi: 10.1016/j.yexmp.2022.104782. Epub 2022 Jun 27. [PubMed:35773064 ]
Haryanti S, Zulfin UM, Salsabila IA, Wulandari F, Meiyanto E: The Cytotoxic and Anti-Migratory Properties of Caesalpinia sappan and Ficus septica, in Combination with Doxorubicin on 4T1 TNBC Cells with Nephroprotective Potential. Asian Pac J Cancer Prev. 2022 Feb 1;23(2):743-752. doi: 10.31557/APJCP.2022.23.2.743. [PubMed:35225488 ]
LOTUS database [Link]

Showing NP-Card for brazilein (NP0199965)

MOL for NP0199965 (brazilein)

3D MOL for NP0199965 (brazilein)

3D SDF for NP0199965 (brazilein)

3D-SDF for NP0199965 (brazilein)

PDB for NP0199965 (brazilein)

3D PDB for NP0199965 (brazilein)

SMILES for NP0199965 (brazilein)

INCHI for NP0199965 (brazilein)

Structure for NP0199965 (brazilein)

3D Structure for NP0199965 (brazilein)