(3S,4R,4aS)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one

Details

• Internal ID: 0dd193e8-0d5b-44a1-98e9-1c3eb64b1514
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3S,4R,4aS)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
• SMILES (Canonical): C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10?,11?,12?,13?,15+,16?/m1/s1
• InChI Key: VSJGJMKGNMDJCI-FGNDQDIWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₉
• Molecular Weight: 358.34 g/mol
• Exact Mass: 358.12638228 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.59
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• NSC-606404

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6190	61.90%
Caco-2	-	0.8586	85.86%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7627	76.27%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8558	85.58%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8683	86.83%
P-glycoprotein inhibitior	-	0.8876	88.76%
P-glycoprotein substrate	-	0.9186	91.86%
CYP3A4 substrate	+	0.5785	57.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8602	86.02%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.8660	86.60%
CYP2C19 inhibition	-	0.8277	82.77%
CYP2D6 inhibition	-	0.8774	87.74%
CYP1A2 inhibition	-	0.8514	85.14%
CYP2C8 inhibition	-	0.6974	69.74%
CYP inhibitory promiscuity	-	0.8641	86.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6851	68.51%
Eye corrosion	-	0.9805	98.05%
Eye irritation	-	0.9306	93.06%
Skin irritation	-	0.7821	78.21%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.6270	62.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5940	59.40%
Micronuclear	-	0.7741	77.41%
Hepatotoxicity	-	0.7341	73.41%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5602	56.02%
Acute Oral Toxicity (c)	III	0.4512	45.12%
Estrogen receptor binding	+	0.5372	53.72%
Androgen receptor binding	+	0.5640	56.40%
Thyroid receptor binding	+	0.5772	57.72%
Glucocorticoid receptor binding	-	0.5814	58.14%
Aromatase binding	-	0.5091	50.91%
PPAR gamma	+	0.6089	60.89%
Honey bee toxicity	-	0.7952	79.52%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.4064	40.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	94.95%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.24%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	88.22%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.91%	96.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	86.78%	83.57%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.38%	86.92%
CHEMBL2581	P07339	Cathepsin D	85.87%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.73%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	82.91%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.88%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.51%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.18%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.11%	89.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.00%	95.83%

Plants that contains it

• Amsonia orientalis
• Anthocleista djalonensis
• Anthocleista grandiflora
• Anthocleista nobilis
• Anthocleista vogelii
• Bhesa paniculata
• Calycophyllum spruceanum
• Carapichea ipecacuanha
• Centaurium erythraea
• Cephalaria ambrosioides
• Chelonanthus alatus
• Chimarrhis turbinata
• Chione venosa
• Chironia baccifera
• Citronella gongonha
• Curtia tenuifolia
• Cyrtophyllum fragrans
• Desfontainia spinosa
• Dipsacus asperoides
• Dipsacus laciniatus
• Eucnide bartonioides
• Fagraea gracilipes
• Gentiana algida
• Gentiana lutea
• Gentiana macrophylla
• Gentiana olivieri
• Gentiana punctata
• Gentiana scabra
• Gentiana septemfida
• Gentiana sino-ornata
• Gentiana siphonantha
• Gentiana thunbergii
• Gentiana tibetica
• Gentiana verna
• Guettarda platypoda
• Hydrangea chinensis
• Hydrangea macrophylla
• Lomelosia variifolia
• Lonicera angustifolia
• Lonicera caerulea
• Lonicera japonica
• Lonicera quinquelocularis
• Mentzelia decapetala
• Nasa trianae
• Neonauclea sessilifolia
• Nyssa ogeche
• Ophiorrhiza japonica
• Ophiorrhiza kuroiwai
• Potalia amara
• Simira williamsii
• Strychnos axillaris
• Strychnos lucida
• Strychnos spinosa
• Swertia arisanensis
• Swertia calycina
• Swertia chirata
• Swertia franchetiana
• Swertia japonica
• Tabernaemontana cymosa
• Tripterospermum japonicum
• Tripterospermum lanceolatum

Cross-Links

• PubChem: 354447
• LOTUS: LTS0114959
• wikiData: Q104667292