NP-MRD: Showing NP-Card for Haematoxylin (NP0051723)

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Record Information

Version

2.0

Created at

2022-04-27 22:58:55 UTC

Updated at

2022-04-27 22:58:55 UTC

NP-MRD ID

NP0051723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Haematoxylin

Description

(+)-Haematoxylin, also known as hydroxybrasilin or natural black 1, 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. Thus, (+)-haematoxylin is considered to be a flavonoid. Haematoxylin is found in Haematoxylon compechianum and Haematoxylum campechianum . Haematoxylin was first documented in 2021 (PMID: 35464804). Based on a literature review a small amount of articles have been published on (+)-haematoxylin (PMID: 35470982) (PMID: 35466619) (PMID: 35452797) (PMID: 35449128).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -4.6668    1.6705   -1.3233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    1.1734   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067   -0.0505   -1.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8840   -0.5598   -0.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631    0.1618    0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8059    1.3589    0.9093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9346    1.8928    0.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4313    3.1202    0.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -0.6019    1.0659 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2049   -0.0926    0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5832    1.1981    0.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7850    1.7406    0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468    1.0063   -0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8461    1.5398   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2922   -0.2832   -0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -1.0612   -1.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877   -0.8217   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584   -2.1303   -0.5550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8887   -2.8033    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644   -2.0143    0.6003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1362   -2.7035    1.5278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573   -1.8363   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549    2.5513   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5039   -0.6030   -1.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3773    1.9759    1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    3.6337    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -0.6081    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9805    1.8686    1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0534    2.7555    0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0756    2.4918   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045   -0.6982   -1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201   -3.7648   -0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007   -2.9547    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -2.0575    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856   -2.6800   -0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -1.8144   -1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
 10 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 17 15  1  0
 15 16  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 11  2  0
  7  2  1  0
 20  9  1  0
 22  4  1  0
 11 10  1  0
  1 23  1  0
  3 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  1
 19 32  1  0
 19 33  1  0
 21 34  1  0
 22 35  1  0
 22 36  1  0
 16 31  1  0
 14 30  1  0
 12 29  1  0
 11 28  1  0
M  END


  Mrv1652304282200582D          

 22 25  0  0  1  0            999 V2000
    2.2458    1.0022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1159    1.8169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7565    2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5270    2.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6569    1.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463   -0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9168   -0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5574    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274    0.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0680    1.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3279   -0.1772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    1.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111    0.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984   -0.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5018   -0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0822    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1305    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8789   -0.0162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2891   -1.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    2.6136    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  1 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
  2 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1O)[C@@H]1C3=C(OC[C@]1(O)C2)C(O)=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13-,16+/m0/s1

> <INCHI_KEY>
WZUVPPKBWHMQCE-XJKSGUPXSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.74960137642278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10S)-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-2(7),3,5,12(17),13,15-hexaene-5,6,10,14,15-pentol

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
1.4733008469999997

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.803180137708011

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.166513725707375

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4933525532403973

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
77.48270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S)-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-2(7),3,5,12(17),13,15-hexaene-5,6,10,14,15-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.192   1.871   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.950   3.392   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.145   4.362   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.584   3.812   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.826   2.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.630   1.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.873  -0.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.311  -0.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.507   0.220   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.265   1.740   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.460   2.711   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.945  -0.331   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.428   3.631   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.731   2.258   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.821   1.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.424  -0.318   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.937  -0.718   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.153   0.370   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.244   1.858   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.641  -0.030   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.540  -2.206   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.550   4.879   0.000  0.00  0.00           O+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3   13   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    1   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
(+)-Hematoxylin	ChEBI
(6AS,11BR)-7,11b-dihydrobenz[b]indeno[1,2-D]pyran-3,4,6a,9,10(6H)-pentol	ChEBI
cis-(+)-7,11b-Dihydrobenz[b]indeno[1,2-D]pyran-3,4,6a,9,10(6H)-pentol	ChEBI
Haematoxylin	ChEBI
Hydroxybrasilin	ChEBI
Hydroxybrazilin	ChEBI
Natural black 1	Kegg
C.I. 75290	Kegg

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2820 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

(1R,10S)-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-2(7),3,5,12(17),13,15-hexaene-5,6,10,14,15-pentol

Traditional Name

(1R,10S)-8-oxatetracyclo[8.7.0.0^{2,7}.0^{12,17}]heptadeca-2(7),3,5,12(17),13,15-hexaene-5,6,10,14,15-pentol

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C=C1O)[C@@H]1C3=C(OC[C@]1(O)C2)C(O)=C(O)C=C3

InChI Identifier

InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13-,16+/m0/s1

InChI Key

WZUVPPKBWHMQCE-XJKSGUPXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Haematoxylon compechianum	-	KNApSAcK
Haematoxylum campechianum	Plant	KNApSAcK

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
Indane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tertiary alcohol
Oxacycle
Polyol
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

haematoxylin (CHEBI:5601 )
Neoflavonoids (C09931 )
Neoflavonoids (LMPK12100063 )

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	0.94	ALOGPS
logP	1.47	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.48 m³·mol⁻¹	ChemAxon
Polarizability	29.75 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

C00002993

Chemspider ID

390940

KEGG Compound ID

C09931

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442514

PDB ID

Not Available

ChEBI ID

5601

Good Scents ID

rw1249171

References

General References

Secker TJ, Harling CC, Hand C, Voegeli D, Keevil CW, Leighton TG: A proof-of-concept study of the removal of early and late phase biofilm from skin wound models using a liquid acoustic stream. Int Wound J. 2022 Apr 26. doi: 10.1111/iwj.13818. [PubMed:35470982 ]
Shamsi FB, Anwar A, Lail RA, Bukhari MH, Naseem N, Nagi AH: Immunohistochemical Expression Of Matrix Metalloproteinase-1 (MMP-1) in Different Types Of Breast Carcinoma And Its Comparison With ER/PER and HER2/neu. J Ayub Med Coll Abbottabad. 2022 Jan-Mar;34(1):12-16. doi: 10.55519/JAMC-01-8189. [PubMed:35466619 ]
Lei X, Cheng L, Yang Y, Pang M, Dong Y, Zhu X, Chen C, Yao Z, Wu G, Cheng B, Forouzanfar T: Co-administration of platelet-rich plasma and small intestinal submucosa is more beneficial than their individual use in promoting acute skin wound healing. Burns Trauma. 2021 Nov 30;9:tkab033. doi: 10.1093/burnst/tkab033. eCollection 2021. [PubMed:35464804 ]
Ungari LP, Netherlands EC, Santos ALQ, de Alcantara EP, Emmerich E, da Silva RJ, O'Dwyer LH: Diversity of haemogregarine parasites infecting Brazilian snakes from the Midwest and Southeast regions with a description of two new species of Hepatozoon (Apicomplexa: Adeleorina: Hepatozoidae). Parasitol Int. 2022 Apr 20;89:102587. doi: 10.1016/j.parint.2022.102587. [PubMed:35452797 ]
Pi L, Fang B, Meng X, Qian L: LncRNA XIST accelerates burn wound healing by promoting M2 macrophage polarization through targeting IL-33 via miR-19b. Cell Death Discov. 2022 Apr 21;8(1):220. doi: 10.1038/s41420-022-00990-x. [PubMed:35449128 ]

Showing NP-Card for Haematoxylin (NP0051723)

MOL for NP0051723 (Haematoxylin)

3D MOL for NP0051723 (Haematoxylin)

3D SDF for NP0051723 (Haematoxylin)

3D-SDF for NP0051723 (Haematoxylin)

PDB for NP0051723 (Haematoxylin)

3D PDB for NP0051723 (Haematoxylin)

SMILES for NP0051723 (Haematoxylin)

INCHI for NP0051723 (Haematoxylin)

Structure for NP0051723 (Haematoxylin)

3D Structure for NP0051723 (Haematoxylin)