nigrumnin II

Details

• Internal ID: b063215c-167a-4f46-aeb7-75204e283eab
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (1R,2S,4S,5'R,6R,7S,8S,9S,12S,13S,16S,18S)-8-hydroxy-16-[(2R,3R,4S,5R,6R)-4-hydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-10-one
• SMILES (Canonical): CC1CCC2(C(C3(C(O2)CC4C3(C(=O)CC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)O)O)O)OC2C(C(C(CO2)O)O)O)O)OC2C(C(C(C(O2)C)O)O)O)C)C)O)C)OC1
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@H]([C@]3([C@@H](O2)C[C@@H]4[C@@]3(C(=O)C[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@H](CO2)O)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C)O)O)O)C)C)O)C)OC1
• InChI: InChI=1S/C55H88O27/c1-20-8-11-54(73-17-20)22(3)55(70)33(82-54)14-27-25-7-6-23-12-24(9-10-52(23,4)26(25)13-32(60)53(27,55)5)75-50-45(80-49-41(68)38(65)34(61)21(2)74-49)42(69)43(31(16-57)77-50)78-51-46(81-48-40(67)36(63)29(59)19-72-48)44(37(64)30(15-56)76-51)79-47-39(66)35(62)28(58)18-71-47/h20-31,33-51,56-59,61-70H,6-19H2,1-5H3/t20-,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31-,33+,34+,35+,36+,37-,38-,39-,40-,41-,42+,43+,44+,45-,46-,47+,48+,49+,50-,51+,52+,53-,54-,55-/m1/s1
• InChI Key: MVNPCFRHJXMCMA-MENRLZMASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₈O₂₇
• Molecular Weight: 1181.30 g/mol
• Exact Mass: 1180.55129753 g/mol
• Topological Polar Surface Area (TPSA): 411.00 Ų
• XlogP: -4.10
• Atomic LogP (AlogP): -4.49
• H-Bond Acceptor: 27
• H-Bond Donor: 14
• Rotatable Bonds: 12

Synonyms

• RefChem:165897
• (25R)-3beta,17alpha-Dihydroxy-5alpha-spirostan-1 2-one 3-O-beta-D-xylopyranosyl-(1-->3)-(alpha-L-arabinopyranosyl-(1--> 2))-beta-D-glucopyranosyl-(1-->4)-(alpha-L-rhamnopyra-nosyl-(1-->2))L-beta-D-galactopyranoside
• 289698-36-8
• (1R,2S,4S,5'R,6R,7S,8S,9S,12S,13S,16S,18S)-8-hydroxy-16-((2R,3R,4S,5R,6R)-4-hydroxy-5-((2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxy-3-((2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl)oxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl)oxy-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-oxane)-10-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5734	57.34%
Caco-2	-	0.8801	88.01%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7299	72.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8465	84.65%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8202	82.02%
P-glycoprotein inhibitior	+	0.7438	74.38%
P-glycoprotein substrate	+	0.6530	65.30%
CYP3A4 substrate	+	0.7511	75.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9265	92.65%
CYP2C9 inhibition	-	0.9261	92.61%
CYP2C19 inhibition	-	0.9124	91.24%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.9264	92.64%
CYP2C8 inhibition	+	0.6885	68.85%
CYP inhibitory promiscuity	-	0.9693	96.93%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6417	64.17%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.9024	90.24%
Skin irritation	-	0.6168	61.68%
Skin corrosion	-	0.9490	94.90%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7834	78.34%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.9422	94.22%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7627	76.27%
Acute Oral Toxicity (c)	I	0.7641	76.41%
Estrogen receptor binding	+	0.8580	85.80%
Androgen receptor binding	+	0.7643	76.43%
Thyroid receptor binding	+	0.5513	55.13%
Glucocorticoid receptor binding	+	0.6988	69.88%
Aromatase binding	+	0.6400	64.00%
PPAR gamma	+	0.8011	80.11%
Honey bee toxicity	-	0.5770	57.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8173	81.73%

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	98.87%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.96%	97.09%
CHEMBL325	Q13547	Histone deacetylase 1	95.62%	95.92%
CHEMBL1937	Q92769	Histone deacetylase 2	94.60%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	94.32%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.06%	97.25%
CHEMBL1951	P21397	Monoamine oxidase A	92.82%	91.49%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.63%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.90%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.88%	89.00%
CHEMBL1914	P06276	Butyrylcholinesterase	89.61%	95.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.94%	96.61%
CHEMBL5255	O00206	Toll-like receptor 4	88.73%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.33%	91.24%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	87.14%	95.83%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.45%	93.04%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	86.10%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.72%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.69%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	85.36%	90.08%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.55%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.98%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.42%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.85%	95.56%
CHEMBL233	P35372	Mu opioid receptor	82.69%	97.93%
CHEMBL4302	P08183	P-glycoprotein 1	82.43%	92.98%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.38%	97.36%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.26%	82.69%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.48%	95.50%
CHEMBL237	P41145	Kappa opioid receptor	81.47%	98.10%
CHEMBL3524	P56524	Histone deacetylase 4	81.34%	92.97%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	81.31%	92.86%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.22%	91.71%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.19%	97.29%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.75%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.09%	92.62%

Plants that contains it

• Achillea millefolium
• Alcea nudiflora
• Alocasia macrorrhizos
• Anaphalis margaritacea
• Angelica sinensis
• Boronia lanceolata
• Campanula pendula
• Carissa spinarum
• Chloranthus holostegius
• Clerodendrum infortunatum
• Corydalis crystallina
• Eucalyptus campanulata
• Euphorbia cattimandoo
• Hemiphragma heterophyllum
• Lasianthus attenuatus var. attenuatus
• Lomandra hastilis
• Mercurialis leiocarpa
• Morisonia scabrida
• Neolitsea sericea
• Ochradenus baccatus
• Plantago ovata
• Podocarpus sellowii
• Podophyllum pleianthum
• Primula denticulata
• Rubus niveus
• Solanum nigrum
• Spinacia oleracea
• Teucrium cossonii
• Thujopsis dolabrata
• Turnera ulmifolia

Cross-Links

• PubChem: 10630134
• NPASS: NPC77184
• LOTUS: LTS0200377
• wikiData: Q105173175