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Lotusine G

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Cyclopeptide Alkaloid

Canonical Smiles	CCC(C1NC(=O)C2C(CCN2C#[O+])Oc2ccc(CCNC1=O)cc2)C
InChI	InChI=1S/C20H25N3O4/c1-3-13(2)17-19(25)21-10-8-14-4-6-15(7-5-14)27-16-9-11-23(12-24)18(16)20(26)22-17/h4-7,13,16-18H,3,8-11H2,1-2H3,(H-,21,22,25,26)/p+1
InChIKey	GACFEVHXTFYRKG-UHFFFAOYSA-O
Formula	C₂₀H₂₆N₃O₄+
HBA	4
HBD	2
MW	372.45
Rotatable Bonds	2
TPSA	90.57
LogP	1.06
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	27
Formal Charge	1
Fraction CSP3	0.55
Exact Mass	372.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zizyphus lotus	Rhamnaceae	Plantae	3867

Showing of synonyms

Le Crouéour G, Thépenier P, et al. (2002). Lotusine G: a new cyclopeptide alkaloid from Zizyphus lotus. Fitoterapia,2002,73(1),63-68. [View] [PubMed]

Pubchem: 163187633

Nmrshiftdb2: 70031113

No compound-protein relationship available.

SMILES: C1CNC(C12)C(=O)NCC(=O)NCCc3ccc(O2)cc3

Level: 0

Mol. Weight: 372.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -3.75
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.67
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.05

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.93
Plasma Protein Binding: 10.23
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.5
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.0
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.46
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.65
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -3.8
Rat (Acute): 2.15
Rat (Chronic Oral): 1.12
Fathead Minnow: 3.96
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 443.51
Hydration Free Energy: -3.48
Log(D) at pH=7.4: 0.52
Log(P): 0.6
Log S: -2.97
Log(Vapor Pressure): -8.95
Melting Point: 213.08
pKa Acid: 5.36
pKa Basic: 10.9

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8821
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8821
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8620
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8620
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8460
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8460
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8157
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8157
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8055
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8055
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7718
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7718
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7717
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7717
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7685
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7685
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7651
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7651
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7574
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7574
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7564
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7564
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7561
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7561
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7561
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7561
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7556
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7556
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7493
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7493
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7490
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7490
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7438
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7438
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7398
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7398
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7387
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7387
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7358
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7358
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7294
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7294
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7205
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7205
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7176
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7176
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7113
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7113
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7068
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7068

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