Barbaloin

Details

• Internal ID: f86c500f-2497-4420-afb4-cf23e516b8a2
• Taxonomy: Benzenoids > Anthracenes
• IUPAC Name: 1,8-dihydroxy-3-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• SMILES (Canonical): C1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4C(C(C(C(O4)CO)O)O)O)C=C(C=C3O)CO
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4C(C(C(C(O4)CO)O)O)O)C=C(C=C3O)CO
• InChI: InChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2
• InChI Key: AFHJQYHRLPMKHU-UHFFFAOYSA-N
• Popularity: 153 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₉
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.12638228 g/mol
• Topological Polar Surface Area (TPSA): 168.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.89
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• Barbaloin
• Aloinum
• Ugandaloin
• Cafaloin
• Jafaloin
• Socaloin
• 8015-61-0
• 20226-90-8
• NSC407305
• 1,8-dihydroxy-3-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• 73649-93-1
• Aloin-B;Isobarbaloin
• NSC227189
• Aloin [BAN]
• 1,5-anhydro-1-[4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]hexitol
• 9(10H)-Anthracenone, 10-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10R)-
• NSC374116
• NSC374117
• NSC631263
• (10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• ALOINE A
• ALOINE B
• 10-(1',5'-Anhydroglucosyl)aloe-emodin-9-anthrone
• MLS006011832
• CHEMBL123026
• Aloin-A; Barbaloin-A;Barbaloin
• SCHEMBL13990758
• DTXSID70859643
• Aloin-A; Barbaloin-A;Isobarbaloin
• (10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• 5133-19-7
• BCP13735
• BCP25762
• BBL028189
• STL146381
• AKOS005720865
• NSC-227189
• NSC-374116
• NSC-374117
• NSC-631263
• NCI60_001856
• NCI60_003874
• SMR004703497
• VS-08686
• FT-0622064
• ANTHRONE,8-DIHYDROXY-3-(HYDROXYMETHYL)
• 10-b-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone, 9CI
• 1,8-dihydroxy-3-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6888	68.88%
Caco-2	-	0.9076	90.76%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5288	52.88%
OATP2B1 inhibitior	-	0.5619	56.19%
OATP1B1 inhibitior	-	0.7739	77.39%
OATP1B3 inhibitior	+	0.9667	96.67%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8591	85.91%
P-glycoprotein inhibitior	-	0.6959	69.59%
P-glycoprotein substrate	-	0.8569	85.69%
CYP3A4 substrate	+	0.5716	57.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8245	82.45%
CYP3A4 inhibition	-	0.8490	84.90%
CYP2C9 inhibition	-	0.8905	89.05%
CYP2C19 inhibition	-	0.8846	88.46%
CYP2D6 inhibition	-	0.9333	93.33%
CYP1A2 inhibition	-	0.8005	80.05%
CYP2C8 inhibition	-	0.6545	65.45%
CYP inhibitory promiscuity	-	0.6844	68.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6709	67.09%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7660	76.60%
Skin irritation	-	0.7902	79.02%
Skin corrosion	-	0.9612	96.12%
Ames mutagenesis	+	0.7836	78.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4296	42.96%
Micronuclear	+	0.6459	64.59%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8660	86.60%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5285	52.85%
Acute Oral Toxicity (c)	IV	0.4034	40.34%
Estrogen receptor binding	+	0.6002	60.02%
Androgen receptor binding	+	0.6369	63.69%
Thyroid receptor binding	-	0.6024	60.24%
Glucocorticoid receptor binding	+	0.5634	56.34%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7705	77.05%
Honey bee toxicity	-	0.8359	83.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.7031	70.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.37%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.54%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	92.46%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.40%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.29%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.35%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.23%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.97%	94.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.45%	89.67%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.75%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.28%	95.89%

Plants that contains it

• Aloe africana
• Aloe arborescens
• Aloe castanea
• Aloe castellorum
• Aloe excelsa
• Aloe ferox
• Aloe microdonta
• Aloe rivae
• Aloe rubroviolacea
• Aloe spicata
• Aloe vera
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 313325
• NPASS: NPC84568
• LOTUS: LTS0029105
• wikiData: Q104667246