(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1S,12S)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol

Details

• Internal ID: 4e245479-a2bc-4b2f-a2c4-d2e3116dbccd
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(1S,12S)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol
• SMILES (Canonical): C1C2C(C3=C(O1)C=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6
• SMILES (Isomeric): C1[C@H]2[C@@H](C3=C(O1)C=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC5=CC6=C(C=C25)OCO6
• InChI: InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17-,18-,19+,20-,21-,22-/m1/s1
• InChI Key: VGSYCWGXBYZLLE-WFFYVNQPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.20
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5863	58.63%
Caco-2	-	0.8618	86.18%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5300	53.00%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9134	91.34%
OATP1B3 inhibitior	+	0.9590	95.90%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6963	69.63%
P-glycoprotein inhibitior	-	0.6328	63.28%
P-glycoprotein substrate	-	0.8422	84.22%
CYP3A4 substrate	+	0.5803	58.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7727	77.27%
CYP3A4 inhibition	-	0.7256	72.56%
CYP2C9 inhibition	-	0.8922	89.22%
CYP2C19 inhibition	-	0.6642	66.42%
CYP2D6 inhibition	-	0.7229	72.29%
CYP1A2 inhibition	-	0.8626	86.26%
CYP2C8 inhibition	+	0.4659	46.59%
CYP inhibitory promiscuity	-	0.5097	50.97%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5121	51.21%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9128	91.28%
Skin irritation	-	0.8012	80.12%
Skin corrosion	-	0.9534	95.34%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3666	36.66%
Micronuclear	+	0.6059	60.59%
Hepatotoxicity	-	0.8302	83.02%
skin sensitisation	-	0.8555	85.55%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7316	73.16%
Acute Oral Toxicity (c)	III	0.5505	55.05%
Estrogen receptor binding	+	0.6592	65.92%
Androgen receptor binding	+	0.5600	56.00%
Thyroid receptor binding	+	0.5339	53.39%
Glucocorticoid receptor binding	-	0.6121	61.21%
Aromatase binding	+	0.5332	53.32%
PPAR gamma	+	0.7878	78.78%
Honey bee toxicity	-	0.7831	78.31%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7293	72.93%

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	98.91%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.52%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	96.42%	95.93%
CHEMBL2039	P27338	Monoamine oxidase B	95.00%	92.51%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.30%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.65%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.78%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.13%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.00%	92.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.99%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.40%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.67%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.56%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.44%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	83.22%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.03%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.45%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.92%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.52%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.47%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.28%	96.00%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Ononis vaginalis
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 6326060
• NPASS: NPC260197
• LOTUS: LTS0100539
• wikiData: Q105286031