Clivimine

Details

• Internal ID: 68f4cb85-3e77-46d8-85c6-6e02e194d601
• Taxonomy: Alkaloids and derivatives > Amaryllidaceae alkaloids > Homolycorine-type amaryllidaceae alkaloids
• IUPAC Name: bis[(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.02,10.03,7.015,19]icosa-1(20),13,15(19)-trien-9-yl] 2,6-dimethylpyridine-3,5-dicarboxylate
• SMILES (Canonical): CC1=C(C=C(C(=N1)C)C(=O)OC2CC3CCN(C3C4C2OC(=O)C5=CC6=C(C=C45)OCO6)C)C(=O)OC7CC8CCN(C8C9C7OC(=O)C1=CC2=C(C=C91)OCO2)C
• SMILES (Isomeric): CC1=C(C=C(C(=N1)C)C(=O)O[C@H]2C[C@H]3CCN([C@H]3[C@H]4[C@H]2OC(=O)C5=CC6=C(C=C45)OCO6)C)C(=O)O[C@H]7C[C@H]8CCN([C@H]8[C@H]9[C@H]7OC(=O)C1=CC2=C(C=C91)OCO2)C
• InChI: InChI=1S/C43H43N3O12/c1-18-22(40(47)55-32-9-20-5-7-45(3)36(20)34-24-12-28-30(53-16-51-28)14-26(24)42(49)57-38(32)34)11-23(19(2)44-18)41(48)56-33-10-21-6-8-46(4)37(21)35-25-13-29-31(54-17-52-29)15-27(25)43(50)58-39(33)35/h11-15,20-21,32-39H,5-10,16-17H2,1-4H3/t20-,21-,32+,33+,34+,35+,36-,37-,38+,39+/m1/s1
• InChI Key: CJYOGPFDNAEALZ-BVORSCEZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₃N₃O₁₂
• Molecular Weight: 793.80 g/mol
• Exact Mass: 793.28467382 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.30
• H-Bond Acceptor: 15
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 7096-85-7
• 3,5-Pyridinedicarboxylic acid, 2,6-dimethyl-, bis((3aR,5S,5aR,12bS,12cR)-1,2,3,3a,4,5,5a,7,12b,12c-decahydro-1-methyl-7-oxo(1,3)dioxolo(6,7)(2)benzopyrano(3,4-g)indol-5-yl) ester
• 3-(2R,3S,7R,9S,10R)-4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo(11.7.0.0,.0,.0,)icosa-1(20),13,15(19)-trien-9-yl 5-(2S,3S,7S,9R,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo(11.7.0.0,.0,.0,)icosa-1(20),13,15(19)-trien-9-yl 2,6-dimethylpyridine-3,5-dicarboxylic acid
• 3-(2R,3S,7R,9S,10R)-4-Methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),13,15(19)-trien-9-yl 5-(2S,3S,7S,9R,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.0,.0,.0,]icosa-1(20),13,15(19)-trien-9-yl 2,6-dimethylpyridine-3,5-dicarboxylic acid
• bis((2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo(11.7.0.02,10.03,7.015,19)icosa-1(20),13,15(19)-trien-9-yl) 2,6-dimethylpyridine-3,5-dicarboxylate
• bis[(2S,3R,7R,9S,10R)-4-methyl-12-oxo-11,16,18-trioxa-4-azapentacyclo[11.7.0.02,10.03,7.015,19]icosa-1(20),13,15(19)-trien-9-yl] 2,6-dimethylpyridine-3,5-dicarboxylate
• RefChem:127000
• CHEMBL451626

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9084	90.84%
Caco-2	-	0.8380	83.80%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5050	50.50%
OATP2B1 inhibitior	+	0.5809	58.09%
OATP1B1 inhibitior	+	0.8963	89.63%
OATP1B3 inhibitior	+	0.9023	90.23%
MATE1 inhibitior	-	0.8409	84.09%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9790	97.90%
P-glycoprotein inhibitior	+	0.8218	82.18%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.6916	69.16%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.7883	78.83%
CYP3A4 inhibition	-	0.5126	51.26%
CYP2C9 inhibition	-	0.9117	91.17%
CYP2C19 inhibition	+	0.5563	55.63%
CYP2D6 inhibition	-	0.7133	71.33%
CYP1A2 inhibition	-	0.7649	76.49%
CYP2C8 inhibition	-	0.5967	59.67%
CYP inhibitory promiscuity	-	0.6092	60.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5531	55.31%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.8193	81.93%
Skin corrosion	-	0.9544	95.44%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7498	74.98%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6176	61.76%
skin sensitisation	-	0.8886	88.86%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5856	58.56%
Acute Oral Toxicity (c)	III	0.7425	74.25%
Estrogen receptor binding	+	0.8256	82.56%
Androgen receptor binding	+	0.7651	76.51%
Thyroid receptor binding	+	0.5842	58.42%
Glucocorticoid receptor binding	+	0.7792	77.92%
Aromatase binding	+	0.6487	64.87%
PPAR gamma	+	0.7299	72.99%
Honey bee toxicity	-	0.7929	79.29%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9190	91.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.55%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.17%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.31%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.59%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.47%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.30%	85.14%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	88.52%	93.65%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.63%	94.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.98%	94.42%
CHEMBL2581	P07339	Cathepsin D	86.49%	98.95%
CHEMBL4530	P00488	Coagulation factor XIII	85.07%	96.00%
CHEMBL4302	P08183	P-glycoprotein 1	85.05%	92.98%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.80%	90.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.19%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.02%	92.62%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	82.57%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.48%	95.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.77%	93.40%

Plants that contains it

• Clivia miniata

Cross-Links

• PubChem: 44559309
• LOTUS: LTS0032844
• wikiData: Q104394882