(3S,6R,8R,18Z)-15-[(2R,4R,5R,6R)-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]-6,8,12,14-tetrahydroxy-3-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-18-indol-3-ylidene-6-methyl-20-oxapentacyclo[11.7.1.02,11.03,8.017,21]henicosa-1(21),2(11),9,12,14,16-hexaene-4,19-dione

Details

• Internal ID: af89a281-2afe-48c7-85ea-3a21f7b00dc7
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (3S,6R,8R,18Z)-15-[(2R,4R,5R,6R)-4-[(2S,5S,6S)-5-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]-6,8,12,14-tetrahydroxy-3-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-18-indol-3-ylidene-6-methyl-20-oxapentacyclo[11.7.1.02,11.03,8.017,21]henicosa-1(21),2(11),9,12,14,16-hexaene-4,19-dione
• InChI: InChI=1S/C53H61NO18/c1-22-32(55)10-12-39(66-22)72-53-37(57)19-51(5,63)21-52(53,64)15-14-27-44(53)49-42-29(41(50(62)71-49)30-20-54-31-9-7-6-8-26(30)31)16-28(48(61)43(42)47(27)60)35-18-36(46(59)25(4)65-35)70-38-13-11-34(23(2)67-38)69-40-17-33(56)45(58)24(3)68-40/h6-9,14-16,20,22-25,32-36,38-40,45-46,55-56,58-61,63-64H,10-13,17-19,21H2,1-5H3/b41-30+/t22-,23-,24+,25+,32-,33+,34-,35+,36+,38-,39-,40-,45+,46+,51-,52-,53-/m0/s1
• InChI Key: MDUVTHQZLSWVBH-ZLGDECBESA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₆₁NO₁₈
• Molecular Weight: 1000.00 g/mol
• Exact Mass: 999.38886410 g/mol
• Topological Polar Surface Area (TPSA): 282.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.32
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9210	92.10%
Caco-2	-	0.8653	86.53%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5211	52.11%
OATP2B1 inhibitior	-	0.8655	86.55%
OATP1B1 inhibitior	+	0.8359	83.59%
OATP1B3 inhibitior	+	0.9019	90.19%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8571	85.71%
BSEP inhibitior	+	0.9926	99.26%
P-glycoprotein inhibitior	+	0.7433	74.33%
P-glycoprotein substrate	+	0.8214	82.14%
CYP3A4 substrate	+	0.7541	75.41%
CYP2C9 substrate	-	0.8014	80.14%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.7159	71.59%
CYP2C19 inhibition	-	0.7190	71.90%
CYP2D6 inhibition	-	0.8844	88.44%
CYP1A2 inhibition	-	0.6310	63.10%
CYP2C8 inhibition	+	0.8197	81.97%
CYP inhibitory promiscuity	-	0.7441	74.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4597	45.97%
Eye corrosion	-	0.9862	98.62%
Eye irritation	-	0.9022	90.22%
Skin irritation	-	0.7318	73.18%
Skin corrosion	-	0.9184	91.84%
Ames mutagenesis	+	0.5646	56.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7551	75.51%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8108	81.08%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7264	72.64%
Acute Oral Toxicity (c)	III	0.3525	35.25%
Estrogen receptor binding	+	0.8114	81.14%
Androgen receptor binding	+	0.7704	77.04%
Thyroid receptor binding	+	0.6440	64.40%
Glucocorticoid receptor binding	+	0.7889	78.89%
Aromatase binding	+	0.5955	59.55%
PPAR gamma	+	0.8277	82.77%
Honey bee toxicity	-	0.6557	65.57%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9910	99.10%

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	99.84%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.49%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.87%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	97.37%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.34%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	97.30%	91.49%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	94.72%	97.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.54%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.23%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.08%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.87%	95.89%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	92.17%	96.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.92%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.70%	95.83%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.23%	96.21%
CHEMBL2535	P11166	Glucose transporter	89.86%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.26%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.56%	90.71%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	87.22%	83.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.12%	100.00%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	86.73%	96.39%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.70%	93.10%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.25%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.18%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.67%	96.77%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	85.63%	85.11%
CHEMBL2637	P53779	c-Jun N-terminal kinase 3	84.68%	92.75%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.65%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.64%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.87%	97.14%
CHEMBL3401	O75469	Pregnane X receptor	81.57%	94.73%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.11%	100.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	80.01%	95.71%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135867538
• LOTUS: LTS0252908
• wikiData: Q105161982