Catalpol

Details

• Internal ID: ff0d6390-8925-4412-af70-f1f9a02b439c
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=COC(C2C1C(C3C2(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=CO[C@H]([C@H]2[C@@H]1[C@@H]([C@H]3[C@@]2(O3)CO)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/m1/s1
• InChI Key: LHDWRKICQLTVDL-PZYDOOQISA-N
• Popularity: 344 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.33 g/mol
• Exact Mass: 362.12129689 g/mol
• Topological Polar Surface Area (TPSA): 162.00 Ų
• XlogP: -3.20
• Atomic LogP (AlogP): -3.59
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• Catalpinoside
• 2415-24-9
• De(p-hydroxybenzoyl)catalposide
• Catalposide, des-p-hydroxybenzoyl-
• EINECS 219-324-0
• UNII-JCX5L7JIC2
• JCX5L7JIC2
• Catapol
• CHEMBL513223
• CHEBI:69797
• DTXSID60178850
• beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl, (1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-
• (1AS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha))-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl-beta-D-glucopyranoside
• beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy- 1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl, (1aS-(1a-alpha,1b-beta,2-beta,5a-beta,6-beta,6a-alpha))-
• [1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6aalpha)]-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-beta-D-glucopyranoside
• Digitalis purpurea L
• SCHEMBL420515
• Catalpol, >=96% (HPLC)
• DTXCID20101341
• HY-N0820
• BDBM50259972
• AKOS024264429
• AC-8052
• AM84820
• CCG-208299
• LMPR0102070007
• NCGC00163523-01
• AS-75213
• LS-71485
• SR-05000002315
• Q1050267
• SR-05000002315-2
• (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl beta-D-glucopyranoside
• (1S,5R,6R)-2-[(1S,1bS,2S,5aR,6S)-6-hydroxy-1a-((S)-hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydro-1,3-dioxa-cyclopropa[a]inden-2-yloxy]-6-((S)-hydroxymethyl)-tetrahydro-pyran-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-(((1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-[[(1S,2S,4S,5S,6R,10S)-5-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-10-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-{[(1S,2S,4S,5S,6R,10S)-5-HYDROXY-2-(HYDROXYMETHYL)-3,9-DIOXATRICYCLO[4.4.0.0(2),?]DEC-7-EN-10-YL]OXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
• .beta.-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl
• beta-D-Glucopyranoside, 1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl, (1aS-(1a-alpha,1b-beta,2-beta,5a-beta,6-beta,6a-alpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7320	73.20%
Caco-2	-	0.8738	87.38%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5544	55.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8600	86.00%
OATP1B3 inhibitior	+	0.9582	95.82%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9666	96.66%
P-glycoprotein inhibitior	-	0.8766	87.66%
P-glycoprotein substrate	-	0.8884	88.84%
CYP3A4 substrate	+	0.5795	57.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8339	83.39%
CYP3A4 inhibition	-	0.9510	95.10%
CYP2C9 inhibition	-	0.9133	91.33%
CYP2C19 inhibition	-	0.7795	77.95%
CYP2D6 inhibition	-	0.9021	90.21%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	-	0.7147	71.47%
CYP inhibitory promiscuity	-	0.8277	82.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5906	59.06%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9665	96.65%
Skin irritation	-	0.7993	79.93%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5334	53.34%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.9282	92.82%
skin sensitisation	-	0.8502	85.02%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.4674	46.74%
Acute Oral Toxicity (c)	III	0.3217	32.17%
Estrogen receptor binding	-	0.7021	70.21%
Androgen receptor binding	-	0.6204	62.04%
Thyroid receptor binding	-	0.5068	50.68%
Glucocorticoid receptor binding	-	0.6802	68.02%
Aromatase binding	+	0.7285	72.85%
PPAR gamma	+	0.6908	69.08%
Honey bee toxicity	-	0.7599	75.99%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.6525	65.25%

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	95.93%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.04%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.47%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.06%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	83.54%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.52%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.65%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.50%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.91%	92.94%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.28%	92.32%

Plants that contains it

• Aragoa cundinamarcensis
• Argylia radiata
• Asystasia gangetica subsp. micrantha
• Aureolaria flava
• Buddleja cordobensis
• Buddleja davidii
• Buddleja globosa
• Castilleja hispida
• Castilleja integra
• Castilleja miniata
• Castilleja rhexifolia
• Catalpa bignonioides
• Chelone obliqua
• Dimorphotheca fruticosa
• Eremophila maculata
• Eucommia ulmoides
• Garcinia subelliptica
• Glinus oppositifolius
• Globularia alypum
• Globularia bisnagarica
• Globularia dumulosa
• Globularia orientalis
• Globularia trichosantha
• Gmelina philippensis
• Holmskioldia sanguinea
• Hypericum reflexum
• Juncus effusus
• Kandelia candel
• Lagotis brevituba
• Lagotis stolonifera
• Linaria macroura
• Littorella uniflora
• Mackaya bella
• Markhamia stipulata
• Monochasma savateri
• Myroxylon peruiferum
• Nicotiana alata
• Odontites vernus
• Paulownia tomentosa
• Penstemon albidus
• Penstemon ambiguus
• Penstemon auriberbis
• Penstemon barbatus
• Penstemon centranthifolius
• Penstemon newberryi
• Penstemon parryi
• Penstemon secundiflorus
• Penstemon whippleanus
• Pinguicula moranensis
• Pinguicula vulgaris
• Plantago argentea
• Plantago asiatica
• Plantago depressa
• Plantago hookeriana
• Plantago lagopus
• Plantago lanceolata
• Plantago major
• Plantago patagonica
• Platycodon grandiflorus
• Rehmannia glutinosa
• Scrophularia scorodonia
• Scutellaria albida
• Scutellaria albida subsp. albida
• Scutellaria galericulata
• Scutellaria grossa
• Senecio sandersonii
• Sideritis soluta
• Sideritis trojana
• Sidneya tenuifolia
• Triaenophora rupestris
• Verbascum cheiranthifolium
• Verbascum georgicum
• Verbascum lychnitis
• Verbascum phlomoides
• Verbascum pyroliforme subsp. dudleyanum
• Verbascum sinuatum
• Verbascum spinosum
• Verbascum thapsus
• Verbascum wiedemannianum
• Veronica alpina
• Veronica anagallis-aquatica
• Veronica austriaca
• Veronica cymbalaria
• Veronica fuhsii
• Veronica ligustrifolia
• Veronica liwanensis
• Veronica longifolia
• Veronica officinalis
• Veronica pulvinaris
• Veronica turrilliana
• Vinca minor
• Zaluzianskya capensis

Cross-Links

• PubChem: 91520
• NPASS: NPC258501
• ChEMBL: CHEMBL513223
• LOTUS: LTS0114481
• wikiData: Q1050267