O-Deacetylgerminaline

Details

• Internal ID: 59dc49fb-f7c7-4eae-8fa3-2310447a7b43
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Cerveratrum-type alkaloids
• IUPAC Name: [(6S,9S,10S,12R,14S,16R,19S,22S,23S,25R)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-22-(2-methylbutanoyloxy)-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-13-yl] 2-hydroxy-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CCC2(C3C1(OC24CC5C6CN7CC(CCC7C(C6C(C(C5(C4C(C3)O)O)OC(=O)C(C)(CC)O)O)(C)O)C)O)C
• SMILES (Isomeric): CCC(C)C(=O)O[C@H]1CC[C@]2(C3[C@@]1(O[C@@]24CC5C6CN7C[C@H](CC[C@H]7[C@@](C6[C@H](C([C@]5(C4[C@@H](C3)O)O)OC(=O)C(C)(CC)O)O)(C)O)C)O)C
• InChI: InChI=1S/C37H59NO11/c1-8-19(4)30(41)47-25-12-13-32(5)23-14-22(39)28-35(32,49-37(23,25)46)15-21-20-17-38-16-18(3)10-11-24(38)34(7,44)26(20)27(40)29(36(21,28)45)48-31(42)33(6,43)9-2/h18-29,39-40,43-46H,8-17H2,1-7H3/t18-,19?,20?,21?,22+,23?,24-,25-,26?,27+,28?,29?,32-,33?,34+,35+,36-,37-/m0/s1
• InChI Key: SGYGAUUUPXBOSA-PTSVTHRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₉NO₁₁
• Molecular Weight: 693.90 g/mol
• Exact Mass: 693.40881170 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.49
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• Germerin [German]
• O-Deacetylgerminaline
• Germerin
• 63951-45-1
• Cevane-3-beta,4-beta,7-alpha,14,15-alpha,16-beta,20-heptol, 4,9-epoxy-, 15-((+)-2-hydroxy-2-methylbutyrate) 3-((-)-2-methylbutyrate)
• C37-H59-N-O11
• DTXSID40981329
• Cevane-3,4,7,14,15,16,20-heptol, 4,9-epoxy-, 15-(2-hydroxy-2-methylbutanoate) 3-(2-methylbutanoate), [3.beta.(R),4.alpha.,7.alpha.,15.alpha.(S),16.beta.]-
• LS-52859
• 4,7,14,16,20-Pentahydroxy-3-[(2-methylbutanoyl)oxy]-4,9-epoxycevan-15-yl 2-hydroxy-2-methylbutanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6715	67.15%
Caco-2	-	0.8464	84.64%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Lysosomes	0.6149	61.49%
OATP2B1 inhibitior	-	0.7237	72.37%
OATP1B1 inhibitior	+	0.8960	89.60%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5744	57.44%
P-glycoprotein inhibitior	+	0.7193	71.93%
P-glycoprotein substrate	+	0.6869	68.69%
CYP3A4 substrate	+	0.7457	74.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7867	78.67%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9078	90.78%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9308	93.08%
CYP1A2 inhibition	-	0.9425	94.25%
CYP2C8 inhibition	+	0.7194	71.94%
CYP inhibitory promiscuity	-	0.9613	96.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5302	53.02%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9175	91.75%
Skin irritation	-	0.7598	75.98%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.6037	60.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5204	52.04%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	+	0.5166	51.66%
skin sensitisation	-	0.8817	88.17%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	+	0.5107	51.07%
Acute Oral Toxicity (c)	I	0.8149	81.49%
Estrogen receptor binding	+	0.6593	65.93%
Androgen receptor binding	+	0.7648	76.48%
Thyroid receptor binding	-	0.5817	58.17%
Glucocorticoid receptor binding	+	0.6399	63.99%
Aromatase binding	+	0.6720	67.20%
PPAR gamma	+	0.6669	66.69%
Honey bee toxicity	-	0.6865	68.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7302	73.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.96%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.28%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.56%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	97.37%	89.05%
CHEMBL1914	P06276	Butyrylcholinesterase	96.22%	95.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.75%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	93.87%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.99%	97.14%
CHEMBL299	P17252	Protein kinase C alpha	92.97%	98.03%
CHEMBL2581	P07339	Cathepsin D	92.78%	98.95%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	92.22%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.15%	82.69%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	90.92%	95.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.70%	97.09%
CHEMBL204	P00734	Thrombin	89.90%	96.01%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.77%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.75%	96.47%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.41%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.46%	93.56%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.36%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.17%	86.33%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.84%	98.05%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	87.57%	82.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.46%	91.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.91%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.89%	92.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.77%	97.28%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	86.40%	99.17%
CHEMBL1871	P10275	Androgen Receptor	86.32%	96.43%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.08%	89.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.92%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.86%	96.61%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	85.66%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.54%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	85.45%	96.90%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.41%	97.31%
CHEMBL4660	P28907	Lymphocyte differentiation antigen CD38	84.40%	95.27%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.97%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.97%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.32%	89.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.19%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.78%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.36%	94.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.26%	95.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.15%	95.17%
CHEMBL2007625	O75874	Isocitrate dehydrogenase [NADP] cytoplasmic	80.90%	99.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.08%	95.71%

Plants that contains it

• Veratrum nigrum

Cross-Links

• PubChem: 45690
• NPASS: NPC152665