Brazilein | C16H12O5 - PubChem

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NIH

http://pubchem.ncbi.nlm.nih.gov/compound/6453902#section=Top

U.S. National Library of Medicine

National Center for Biotechnology Information

Compound Summary for CID 6453902

Brazilein
Vendors

Literature

Patents

Bioactivities

Cite this Record

PubChem CID: 6453902
Chemical Names: Brazilein; CHEBI:69196; 600-76-0; Benz(b)indeno(1,2-d)pyran-9(6H)-one,
6a,7-dihydro-3,6a,10-trihydroxy-; Benz[b]indeno[1,2-d]pyran-9(6H)-one, 6a,7-dihydro-3,6a,10trihydroxy-; AGN-PC-0OD1IO; More...
Molecular Formula: C16H12O5
Molecular Weight: 284.26348 g/mol
InChI Key: PGERTGWKXFAEFR-UHFFFAOYSA-N
Create Date: 2006-04-29

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Contents

http://pubchem.ncbi.nlm.nih.gov/compound/6453902#section=Top

1 2D Structure
2 3D Conformer
3 Identification
4 Chemical and Physical Properties
5 Related Records
6 Chemical Vendors
7 Literature
8 Patents
9 Biological Test Results
10 Classification
11 Information Sources

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1 2D Structure
Search

Download

Get Image

Magnify

from PubChem [1]

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2 3D Conformer
Search

Download

Get Image

Magnify

Show Hydrogens

Show Atoms

Animate
from PubChem [1]

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3 Identification
3.1 Computed Descriptors
3.1.1 IUPAC Name
6a,9,10-trihydroxy-6,7-dihydroindeno[2,1-c]chromen-3-one

from PubChem [1]

3.1.2 InChI
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/h1-5,18-20H,6-7H2
from PubChem [1]

3.1.3 InChI Key

PGERTGWKXFAEFR-UHFFFAOYSA-N

from PubChem [1]

3.1.4 Canonical SMILES

C1C2=CC(=C(C=C2C3=C4C=CC(=O)C=C4OCC31O)O)O

from PubChem [1]

3.2 Synonyms
3.2.1 MeSH Synonyms
brazilein

from MeSH [2] http://www.ncbi.nlm.nih.gov/mesh/67050295

3.2.2 Depositor-Supplied Synonyms

1. Brazilein

11. SCHEMBL12162549

2. CHEBI:69196

12. 6a,9,10-trihydroxy-6,7-dihydroindeno[2,1-c]chrome

3. 600-76-0

13. (6aR)-6a,9,10-trihydroxy-6,7-dihydroindeno[2,1-c]c

4. Benz(b)indeno(1,2-d)pyran-9(6H)-one, 6a,7-dihydro-3,6a,10-trihydroxy5. Benz[b]indeno[1,2-d]pyran-9(6H)-one, 6a,7-dihydro-3,6a,10-trihydroxy6. AGN-PC-0OD1IO

7. AC1O58BF
8. AGN-PC-015ICO
9. CHEMBL598750
10. SCHEMBL12162547
from PubChem [1]

3.3 Create Date

2006-04-29

from PubChem [1]

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4 Chemical and Physical Properties

4.1 Computed Properties
Molecular Weight

284.26348 g/mol

Molecular Formula

C16H12O5

XLogP3

0.1

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Exact Mass

284.068473 g/mol

Monoisotopic Mass

284.068473 g/mol

Topological Polar Surface Area

87 A^2

Heavy Atom Count

21

Formal Charge

Complexity

602

Isotope Atom Count

Defined Atom Stereocenter Count

Undefined Atom Stereocenter Count

Defined Bond Stereocenter Count

Undefined Bond Stereocenter Count

Covalently-Bonded Unit Count

1
from PubChem [1]

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5 Related Records
5.1 Related Compounds with Annotation
Download

Literature (3)

Bioactivities (6)

Hematoxylin

Patents (2)

brazilin

brazilin

from PubChem [1]

5.2 Related Compounds

Same Tautomer

Same Connectivity

Same Parent, Tautomer

Same Parent, Connectivity

Similar Compounds

Similar Conformers

22
from PubChem [1]

5.3 Related Substances

Same

16
from PubChem [1]

5.4 Entrez Crosslinks

PubMed

Taxonomy

OMIM

Gene

6
from PubChem [1]

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6 Chemical Vendors
Refine/Analyze

Vendor/Supplier

Download

Purchasable Chemical

PubChem SID

AGN-PC-015ICO

174252102

AGN-PC-0OD1IO

222598883

AC1O58BF

114533598

Angene Chemical
ABI Chem

from PubChem [1]

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7 Literature
7.1 Depositor Provided PubMed Citations
Depositor Provided PubMed Citation Count (2)

from PubChem [1]

7.2 NLM Curated PubMed Citations

All NLM Curated PubMed Citations

from PubChem [1]

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8 Patents
8.1 Depositor-Supplied Patent Identifiers
Refine/Analyze

1 to 1 of 1

Download

Relevance

Patent

Submitted

Granted

COMPOSITION COMPRISING A DERIVATIVE OF HEMATOXYLIN, OF HEMATEIN, OF

BRAZILIN OR OF BRAZILEIN, METAL SALT, HYDROGEN PEROXIDE, AND
(BI)CARBONATE AND HAIR DYEING METHOD THEREWITH [US7833290]

2010-06-17

2010-11-16

from PubChem [1]

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9 Biological Test Results

9.1 BioAssay Results
Refine/Analyze

Download

1 to 10 of 21

Relevance

Activity

Substance

BioAssay

unspecified

103725887

Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an

equimolar substrate-inhibitor concentration of 10 uM [AID: 977599]

unspecified

103725887

Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an

equimolar substrate-inhibitor concentration of 10 uM [AID: 977602]

active
IC50: 14.2M

103725887

Antiinflammatory activity in human neutrophils assessed as inhibition of

fMLP/cytochalasin B-induced elastase release [AID: 459779]

unspecified

103725887

Cytotoxicity against human MDA-MB-231 cells [AID: 459770]

unspecified
IC50

103725887

Cytotoxicity against human A549 cells [AID: 459772]

unspecified

103725887

Cytotoxicity against human MCF7 cells [AID: 459771]

active
IC50: 4M

103725887

Antiinflammatory activity in human neutrophils assessed as inhibition of

fMLP/cytochalasin B-induced superoxide anion generation [AID: 459777]

unspecified

103725887

Cytotoxicity against human HepG2 cells [AID: 459768]

unspecified

103725887

Cytotoxicity against human Hep3B cells [AID: 459769]

unspecified

103725887

Cytotoxicity against human Ca9-22 cells [AID: 459773]

from PubChem [1]

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10 Classification
10.1 Ontologies
10.1.1 MeSH Tree
Refine/Analyze

1 to 1 of 1

List View

Download

Tree View

brazilein
from MeSH [3] http://www.nlm.nih.gov/mesh/meshhome.html

10.1.2 ChEBI Ontology

Refine/Analyze

1 to 1 of 1

List View

Download

Tree View

brazilein
from ChEBI [4] http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology

10.1.3 WIPO IPC

Refine/Analyze

1 to 2 of 2

List View

Download

Tree View

A61Q5/10 - Preparations for permanently dyeing the hair

C07D311/00 - Heterocyclic compounds containing six-membered rings having one oxygen atom a...
from WIPO [5] http://www.wipo.int/classifications/ipc/

10.2 Substance Categorization Classification

Download

Biological Properties (5)

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Chemical Reactions (2)

Patents (5)
Physical Properties (2)
Substance Vendors (3)
Theoretical Properties (2)
Toxicology (1)

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11 Information Sources
1. PubChem http://pubchem.ncbi.nlm.nih.gov
Data deposited in or computed by PubChem
2. brazilein from MeSH 67050295 http://www.ncbi.nlm.nih.gov/mesh/67050295
3. MeSH Tree from MeSH DescTree http://www.nlm.nih.gov/mesh/meshhome.html
MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for
PubMed.
4. ChEBI Ontology from ChEBI OBO http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
The ChEBI Ontology is a structured classification of the entities contained within ChEBI.
5. International Patent Classification 2015 from WIPO IPC http://www.wipo.int/classifications/ipc/
The World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a
hierarchical system of language independent symbols for the classification of patents and utility models according to
the different areas of technology to which they pertain.

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