Hematoxylin

Details

• Internal ID: 70a5bb1f-3614-4196-b944-2db6e1ebbcec
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans
• IUPAC Name: (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
• SMILES (Canonical): C1C2=CC(=C(C=C2C3C1(COC4=C3C=CC(=C4O)O)O)O)O
• SMILES (Isomeric): C1C2=CC(=C(C=C2[C@H]3[C@@]1(COC4=C3C=CC(=C4O)O)O)O)O
• InChI: 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
• Popularity: 6,256 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.28 g/mol
• Exact Mass: 302.07903816 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.32
• H-Bond Acceptor: 6
• H-Bond Donor: 5
• Rotatable Bonds: 0

Synonyms

• Haematoxylin
• Hematoxyline
• Hydroxybrazilin
• 517-28-2
• Hydroxybrasilin
• Natural Black 1
• Hematoxylin hydrate
• (+)-Hematoxylin
• hematoxiline
• (+)-haematoxylin
• Hydroxylrasilin
• CCRIS 5916
• 1412-19-7
• HSDB 4174
• EINECS 208-237-3
• UNII-YKM8PY2Z55
• NSC 270085
• YKM8PY2Z55
• CHEBI:5601
• CHEMBL477197
• (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
• Benz(b)indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, cis-(+)-
• NCI-C55889
• (6aS,11bR)-6,6a,7,11b-tetrahydroindeno[2,1-c]chromene-3,4,6a,9,10-pentaol
• (6aS,11bR)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol
• hematoxilina
• (6aS,11bR)-7,11b-dihydroindeno[2,1-c]chromene-3,4,6a,9,10(6H)-pentol
• Benz(b)indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro- (VAN)
• cis-(+)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol
• Benz(b)indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, (6aS,11bR)-
• C.I. 75290
• 1621-46-1
• cid_10603
• DTXSID8020678
• Ematossilina
• cis-(+)-7,11b-dihydrobenz[b]indeno(1,2-d)pyran-3,4,6a,9,10(6H)-pentol
• Natural Black I
• NSC-270085
• Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, (6aS,11bR)-
• Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, cis-(+)-
• rel-(6aS,11bR)-6,6a,7,11b-Tetrahydroindeno[2,1-c]chromene-3,4,6a,9,10-pentaol
• CI 75290
• Hematoxylin n-Hydrate
• Hematoxylin, certified
• OC12COc3c(O)c(O)ccc3C1c4cc(O)c(O)cc4C2
• Hematoxylin n-Hyd rate
• HEMATOXYLIN [MI]
• C.I. Natural Black 1
• HEMATOXYLIN [HSDB]
• SCHEMBL19654
• Hematoxylin (Hydroxybrazilin)
• Natural Black 1;Haematoxylin
• (6aS,11bR)-7,11b-Dihydro-benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol
• Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-, cis-(++)-
• WZUVPPKBWHMQCE-XJKSGUPXSA-N
• HMS3656K13
• HY-N0116
• BDBM50263183
• LMPK12100063
• LS-168
• s2384
• AKOS016843524
• CCG-267488
• CS-5341
• FS-4071
• Benz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, 7,11b-dihydro-,(6aS,11bR)-
• NCGC00160144-01
• AC-34747
• Hematoxylin monohydrate, SAJ special grade
• C.I.75290
• SW219095-1
• C09931
• Q1146112
• Hematoxylin, certified by the Biological Stain Commission
• Hematoxylin, for microscopy (Hist.), indicator (pH 5.0-6.0)
• 7,11b-Dihydrobenz[ss]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol
• (6aS)-7,11b-dihydroindeno[2,1-c]chromene-3,4,6a,9,10(6H)-pentol
• 7,11bbeta-Dihydrobenz[b]indeno[1,2-d]pyran-3,4,6abeta,9,10(6H)-pentol
• (6aS,11bR)-7,11b-dihydroindeno[2,1-c]chromene-3,4,6a,9,10(6H)-pentaol
• 8005-33-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9069	90.69%
Caco-2	-	0.7838	78.38%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5926	59.26%
OATP2B1 inhibitior	-	0.5636	56.36%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9821	98.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8800	88.00%
P-glycoprotein inhibitior	-	0.9274	92.74%
P-glycoprotein substrate	-	0.8087	80.87%
CYP3A4 substrate	+	0.5195	51.95%
CYP2C9 substrate	+	0.6000	60.00%
CYP2D6 substrate	+	0.4194	41.94%
CYP3A4 inhibition	-	0.9112	91.12%
CYP2C9 inhibition	-	0.6159	61.59%
CYP2C19 inhibition	+	0.5296	52.96%
CYP2D6 inhibition	-	0.5902	59.02%
CYP1A2 inhibition	+	0.6714	67.14%
CYP2C8 inhibition	-	0.6151	61.51%
CYP inhibitory promiscuity	-	0.8353	83.53%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Warning	0.5244	52.44%
Eye corrosion	-	0.9927	99.27%
Eye irritation	+	0.9629	96.29%
Skin irritation	-	0.6918	69.18%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7514	75.14%
Micronuclear	+	0.7159	71.59%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7931	79.31%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6889	68.89%
Acute Oral Toxicity (c)	III	0.4369	43.69%
Estrogen receptor binding	+	0.8136	81.36%
Androgen receptor binding	+	0.7319	73.19%
Thyroid receptor binding	+	0.7518	75.18%
Glucocorticoid receptor binding	+	0.8555	85.55%
Aromatase binding	+	0.6428	64.28%
PPAR gamma	+	0.5682	56.82%
Honey bee toxicity	-	0.7667	76.67%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6950	69.50%
Fish aquatic toxicity	+	0.6950	69.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	11220.2 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	12589.3 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	63.1 nM	Potency	via Super-PRED
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	3400 nM	IC50	PMID: 18610999
CHEMBL3650	P11362	Fibroblast growth factor receptor 1	320 nM	IC50	PMID: 18610999
CHEMBL3717	P08581	Hepatocyte growth factor receptor	400 nM	IC50	PMID: 18610999
CHEMBL1287622	Q9Y468	Lethal(3)malignant brain tumor-like protein 1	125.9 nM	Potency	via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	14125.4 nM; 707.9 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	12589.3 nM; 14125.4 nM; 15848.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1824	P04626	Receptor protein-tyrosine kinase erbB-2	960 nM	IC50	PMID: 18610999
CHEMBL1936	P10721	Stem cell growth factor receptor	2700 nM	IC50	PMID: 18610999
CHEMBL267	P12931	Tyrosine-protein kinase SRC	440 nM	IC50	PMID: 18610999
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	251.2 nM; 316.2 nM; 1584.9 nM	Potency; Potency; Potency	via Super-PRED; via Super-PRED; via CMAUP
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	2900 nM	IC50	PMID: 18610999
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	2100 nM	IC50	PMID: 18610999

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.75%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.01%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.49%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	87.61%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.23%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.77%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.36%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.57%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.67%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.59%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.20%	92.94%

Plants that contains it

• Biancaea sappan
• Haematoxylum campechianum

Cross-Links

• PubChem: 442514
• NPASS: NPC44530
• ChEMBL: CHEMBL477197
• LOTUS: LTS0120586
• wikiData: Q1146112