(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-10,16-diol

Details

• Internal ID: c633be9d-7177-41b5-a4bc-4beef60b7922
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Spirosolanes and derivatives
• IUPAC Name: (1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-5'-(hydroxymethyl)-7,9,13-trimethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-10,16-diol
• SMILES (Canonical): CC1C2C(CC3C2(C(CC4C3CC=C5C4(CCC(C5)O)C)O)C)OC16CCC(CN6)CO
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2([C@@H](C[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)O)C)O[C@]16CC[C@H](CN6)CO
• InChI: InChI=1S/C27H43NO4/c1-15-24-22(32-27(15)9-6-16(14-29)13-28-27)11-21-19-5-4-17-10-18(30)7-8-25(17,2)20(19)12-23(31)26(21,24)3/h4,15-16,18-24,28-31H,5-14H2,1-3H3/t15-,16+,18-,19+,20-,21-,22-,23+,24-,25-,26+,27+/m0/s1
• InChI Key: RFENQHCDYDELRG-FSSGBPHASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₃NO₄
• Molecular Weight: 445.60 g/mol
• Exact Mass: 445.31920885 g/mol
• Topological Polar Surface Area (TPSA): 82.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9602	96.02%
Caco-2	-	0.6945	69.45%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5653	56.53%
OATP2B1 inhibitior	-	0.5642	56.42%
OATP1B1 inhibitior	+	0.8898	88.98%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5730	57.30%
BSEP inhibitior	+	0.6270	62.70%
P-glycoprotein inhibitior	-	0.6534	65.34%
P-glycoprotein substrate	+	0.6596	65.96%
CYP3A4 substrate	+	0.6949	69.49%
CYP2C9 substrate	-	0.8076	80.76%
CYP2D6 substrate	-	0.7375	73.75%
CYP3A4 inhibition	-	0.8978	89.78%
CYP2C9 inhibition	-	0.9066	90.66%
CYP2C19 inhibition	-	0.8976	89.76%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.9131	91.31%
CYP2C8 inhibition	+	0.6750	67.50%
CYP inhibitory promiscuity	-	0.8239	82.39%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4910	49.10%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.9782	97.82%
Skin irritation	-	0.7169	71.69%
Skin corrosion	-	0.9136	91.36%
Ames mutagenesis	-	0.7959	79.59%
Human Ether-a-go-go-Related Gene inhibition	-	0.3772	37.72%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8403	84.03%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.7089	70.89%
Acute Oral Toxicity (c)	III	0.6847	68.47%
Estrogen receptor binding	+	0.6613	66.13%
Androgen receptor binding	+	0.5706	57.06%
Thyroid receptor binding	+	0.7307	73.07%
Glucocorticoid receptor binding	+	0.7916	79.16%
Aromatase binding	+	0.6943	69.43%
PPAR gamma	+	0.5680	56.80%
Honey bee toxicity	-	0.7600	76.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	-	0.3799	37.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.52%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.54%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.86%	95.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.18%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	90.99%	89.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.95%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	90.64%	97.79%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.75%	97.25%
CHEMBL4072	P07858	Cathepsin B	88.45%	93.67%
CHEMBL3045	P05771	Protein kinase C beta	85.93%	97.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.65%	86.33%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.35%	92.88%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.29%	96.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.80%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.72%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.68%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.12%	92.94%
CHEMBL2581	P07339	Cathepsin D	82.64%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.33%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.51%	97.28%

Plants that contains it

• Achillea millefolium
• Alcea nudiflora
• Alocasia macrorrhizos
• Anaphalis margaritacea
• Angelica sinensis
• Antirrhinum majus
• 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: 21573757
• NPASS: NPC129253
• LOTUS: LTS0183379
• wikiData: Q82450605