(7R)-2-[(2S,3R,4R)-3,4-dihydroxyoxolan-2-yl]-4,7-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-6-one

Details

• Internal ID: f72540c4-5ba6-45da-80b6-ae641573457b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: (7R)-2-[(2S,3R,4R)-3,4-dihydroxyoxolan-2-yl]-4,7-dihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-6-one
• SMILES (Canonical): C1C(C(C(O1)C2=CC3=C(N2)C(C(=O)C(=C3O)C(=O)C=CC4=CC=C(C=C4)O)(C5C(C(C(C(O5)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@H]([C@@H](O1)C2=CC3=C(N2)[C@](C(=O)C(=C3O)C(=O)/C=C/C4=CC=C(C=C4)O)([C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O
• InChI: InChI=1S/C27H29NO13/c29-8-16-20(35)21(36)22(37)26(41-16)27(39)24-12(7-13(28-24)23-19(34)15(32)9-40-23)18(33)17(25(27)38)14(31)6-3-10-1-4-11(30)5-2-10/h1-7,15-16,19-23,26,28-30,32-37,39H,8-9H2/b6-3+/t15-,16-,19-,20-,21+,22-,23+,26-,27+/m1/s1
• InChI Key: DDYOBOBXPBUGTA-OOQHCORPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₉NO₁₃
• Molecular Weight: 575.50 g/mol
• Exact Mass: 575.16388998 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.32
• H-Bond Acceptor: 13
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9058	90.58%
Caco-2	-	0.9141	91.41%
Blood Brain Barrier	-	0.6023	60.23%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Nucleus	0.4332	43.32%
OATP2B1 inhibitior	-	0.5644	56.44%
OATP1B1 inhibitior	+	0.8161	81.61%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7600	76.00%
P-glycoprotein inhibitior	-	0.4733	47.33%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.6717	67.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.9289	92.89%
CYP2C9 inhibition	-	0.7669	76.69%
CYP2C19 inhibition	-	0.7807	78.07%
CYP2D6 inhibition	-	0.8895	88.95%
CYP1A2 inhibition	-	0.5746	57.46%
CYP2C8 inhibition	+	0.6670	66.70%
CYP inhibitory promiscuity	-	0.6572	65.72%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5824	58.24%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9135	91.35%
Skin irritation	-	0.8026	80.26%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3676	36.76%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.7973	79.73%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8866	88.66%
Acute Oral Toxicity (c)	III	0.5131	51.31%
Estrogen receptor binding	+	0.7457	74.57%
Androgen receptor binding	+	0.6799	67.99%
Thyroid receptor binding	-	0.5663	56.63%
Glucocorticoid receptor binding	-	0.5910	59.10%
Aromatase binding	+	0.5984	59.84%
PPAR gamma	+	0.6375	63.75%
Honey bee toxicity	-	0.7717	77.17%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5296	52.96%
Fish aquatic toxicity	-	0.4248	42.48%

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	99.24%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.91%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.23%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.72%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	96.67%	95.93%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	95.91%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.55%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.28%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.08%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.02%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.44%	89.67%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.18%	97.28%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.99%	85.31%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.50%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.87%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.84%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.49%	90.71%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.31%	95.83%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.07%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	82.84%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	81.96%	94.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.56%	93.40%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.82%	90.24%

Plants that contains it

• Carthamus tinctorius

Cross-Links

• PubChem: 101020171
• NPASS: NPC284120