Pulmatin

Details

• Internal ID: 9ac725ff-fe8a-4600-8a8a-5ba2d04747fc
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/m1/s1
• InChI Key: WMMOMSNMMDMSRB-JNHRPPPUSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₉
• Molecular Weight: 416.40 g/mol
• Exact Mass: 416.11073221 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): -0.35
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• Chrysophanol 8-O-glucoside
• Pulmatin
• 1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• 5D9G301STW
• 9,10-Anthracenedione, 8-(beta-D-glucopyranosyloxy)-1-hydroxy-3-methyl-
• Chrysophanol-8-O-glucoside
• Chrysophanol-8-beta-D-glucoside
• DTXSID60157529
• Chrysophanol 8-O-beta-D-glucopyranoside
• CHRYSOPHANOL-8-.BETA.-D-GLUCOSIDE
• CHRYSOPHANOL-8-O-.BETA.-D-GLUCOSIDE
• O-.BETA.-D-GLUCOPYRANOSYLCHRYSOPHANOL
• CHRYSOPHANOL-8-MONO-.BETA.-D-GLUCOSIDE
• CHRYSOPHANOL 8-O-.BETA.-D-GLUCOPYRANOSIDE
• ANTHRAQUINONE, 8-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-METHYL-
• 9,10-ANTHRACENEDIONE, 8-(.BETA.-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-METHYL-
• 1-hydroxy-3-methyl-8-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyanthracene-9,10-dione
• CP-8-O-glc
• RefChem:870312
• DTXCID6080020
• Chrysophanol-8-O-beta-D-glucoside
• O-BETA-D-GLUCOPYRANOSYLCHRYSOPHANOL
• CHRYSOPHANOL-8-MONO-BETA-D-GLUCOSIDE
• ANTHRAQUINONE, 8-(BETA-D-GLUCOPYRANOSYLOXY)-1-HYDROXY-3-METHYL-
• Chrysophanol 8-glucoside
• Chrysophanol 8-O-beta-D-glucoside
• Chrysophanol-8-glucoside
• MFCD20260508
• Chrysophanol-8-O-|A-D-glucopyranoside
• Chrysophanol-8-O-beta-D-glucopyranoside
• CHEBI:3688
• 1-Hydroxy-3-methyl-8-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)anthracene-9,10-dione
• UNII-5D9G301STW
• Chrysophanol8-O-glucoside
• AC1L9DB8
• CHEMBL443804
• orb1303427
• SCHEMBL25257975
• HY-N2395R
• HY-N2395
• NAA24128
• LMPK13040007
• AKOS032948547
• Chrysophanol 8-O-glucoside (Standard)
• 8-hydroxy-6-methyl-9,10-dioxo-9,10-dihydroanthracen-1-yl beta-D-glucopyranoside
• 4CN-1718
• DA-51886
• MS-27238
• CS-0022597
• NS00094742
• F17668
• Q27106165
• GLUCOPYRANOSIDE, 8-HYDROXY-6-METHYL-1-ANTHRAQUINONYL
• 8-(beta-D-glucopyranosyloxy)-1-hydroxy-3-methyl-9,10-anthraquinone
• 9,10-Anthracenedione, 8-(|A-D-glucopyranosyloxy)-1-hydroxy-3-methyl-
• GLUCOPYRANOSIDE, 8-HYDROXY-6-METHYL-1-ANTHRAQUINONYL, .BETA.-D-
• 1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-anthracene-9,10-dione
• 1-hydroxy-3-methyl-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• Chrysophanol 8-O-glucoside; 9,10-Anthracenedione, 8-(ss-D-glucopyranosyloxy)-1-hydroxy-3-methyl- (9CI, ACI); 8-(ss-D-Glucopyranosyloxy)-1-hydroxy-3-methyl-9,10-anthracenedione (ACI); Anthraquinone, 8-(ss-D-glucopyranosyloxy)-1-hydroxy-3-methyl- (8CI); Glucopyranoside, 8-hydroxy-6-methy

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5944	59.44%
Caco-2	-	0.8864	88.64%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5632	56.32%
OATP2B1 inhibitior	-	0.5592	55.92%
OATP1B1 inhibitior	+	0.9109	91.09%
OATP1B3 inhibitior	+	0.9621	96.21%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5355	53.55%
P-glycoprotein inhibitior	-	0.7511	75.11%
P-glycoprotein substrate	-	0.8666	86.66%
CYP3A4 substrate	+	0.6006	60.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8589	85.89%
CYP3A4 inhibition	-	0.9206	92.06%
CYP2C9 inhibition	-	0.9028	90.28%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9616	96.16%
CYP1A2 inhibition	-	0.8334	83.34%
CYP2C8 inhibition	-	0.6603	66.03%
CYP inhibitory promiscuity	-	0.8549	85.49%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7207	72.07%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.8712	87.12%
Skin irritation	-	0.8348	83.48%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	+	0.7936	79.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.4227	42.27%
Micronuclear	+	0.6133	61.33%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.9172	91.72%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7455	74.55%
Acute Oral Toxicity (c)	III	0.5952	59.52%
Estrogen receptor binding	+	0.7578	75.78%
Androgen receptor binding	-	0.5165	51.65%
Thyroid receptor binding	-	0.6477	64.77%
Glucocorticoid receptor binding	+	0.6224	62.24%
Aromatase binding	-	0.5279	52.79%
PPAR gamma	+	0.5825	58.25%
Honey bee toxicity	-	0.8412	84.12%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6550	65.50%
Fish aquatic toxicity	+	0.8720	87.20%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.60%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.65%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.44%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.81%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.43%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.65%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.63%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.18%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.47%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.75%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.38%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	90.07%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.65%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.70%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.28%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.28%	96.95%

Plants that contains it

• Albizia myriophylla
• Aloe castellorum
• Amphorogyne spicata
• Anaphalis lactea
• Anchusa azurea
• Balanophora laxiflora
• Benincasa hispida
• Carduus tenuiflorus
• Cassia fistula
• Chaiturus marrubiastrum
• Cryptochilus strictus
• Degenia velebitica
• Delphinium nuttallianum
• Delphinium virgatum
• Dillenia indica
• Dipsacus dipsacoides
• Erythrophleum ivorense
• Etlingera elatior
• Grangea maderaspatana
• Helichrysum chionosphaerum
• Jacquemontia paniculata
• Kniphofia foliosa
• Leptocereus quadricostatus
• Lespedeza tomentosa
• Lupinus argenteus subsp. argenteus
• Mandragora officinarum
• Metrodorea nigra
• Nepeta granatensis
• Onobrychis arenaria
• Petunia inflata
• Phedimus selskanianus
• Photinia serratifolia
• Picramnia latifolia
• Quercus rubra
• Reynoutria japonica
• Rheum australe
• Rheum officinale
• Rheum palmatum
• Rheum rhabarbarum
• Rheum tanguticum
• Rosa villosa
• Rumex crispus
• Rumex nepalensis
• Rumex patientia
• Salvia greggii
• Selaginella delicatula
• Senecio behnii
• Senecio praecox
• Senna tora
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Verbascum densiflorum

Cross-Links

• PubChem: 442731
• NPASS: NPC278329
• LOTUS: LTS0237838
• wikiData: Q27106165