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Lotusine A

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

Canonical Smiles	CCC([C@@H]1NC(=O)C2[C@H](CCN2C(=O)[C@@H](N(C)C)Cc2ccccc2)Oc2ccc(/C=C\NC1=O)cc2)C
InChI	InChI=1S/C30H38N4O4/c1-5-20(2)26-28(35)31-17-15-21-11-13-23(14-12-21)38-25-16-18-34(27(25)29(36)32-26)30(37)24(33(3)4)19-22-9-7-6-8-10-22/h6-15,17,20,24-27H,5,16,18-19H2,1-4H3,(H,31,35)(H,32,36)/b17-15-/t20?,24-,25-,26-,27?/m0/s1
InChIKey	NHZHWPDWUVLKIB-OFSZBOEISA-N
Formula	C₃₀H₃₈N₄O₄
HBA	5
HBD	2
MW	518.66
Rotatable Bonds	6
TPSA	90.98
LogP	2.84
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	518.29
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zizyphus lotus	Rhamnaceae	Plantae	3867
2	Ziziphus lotus	Rhamnaceae	Plantae	345809

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]
Ghedira K, Chemli R, et al. (1993). Two cyclopeptide alkaloids from Zizyphus lotus. Phytochemistry, 1993, 32(6), 1591-1594. [View]

Pubchem: 101229399

No compound-protein relationship available.

SMILES: c1ccccc1CCC(=O)N(CC2)C(C23)C(=O)NCC(=O)NC=Cc4ccc(O3)cc4

Level: 1

Mol. Weight: 518.66 g/mol

SMILES: C1CNC(C12)C(=O)NCC(=O)NC=Cc3ccc(O2)cc3

Level: 0

Mol. Weight: 518.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 518.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.49
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.79
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.66

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.14
Plasma Protein Binding: 81.93
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: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 15.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.3
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.26
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.58
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: -1914.14
Rat (Acute): 2.99
Rat (Chronic Oral): 1.47
Fathead Minnow: 9.49
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 476.91
Hydration Free Energy: -2.87
Log(D) at pH=7.4: 3.42
Log(P): 3.41
Log S: -3.43
Log(Vapor Pressure): -10.12
Melting Point: 203.89
pKa Acid: 8.13
pKa Basic: 7.13

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.9208
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.9208
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8616
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8616
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8554
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8554
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8542
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8542
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8500
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8500
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8455
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8455
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8058
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8058
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8022
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8022
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.8003
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.8003
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7916
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7916
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7849
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7849
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7829
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7829
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7800
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7800
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7771
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7771
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7751
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7751
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7730
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7730
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7727
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7727
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.7716
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.7716
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7713
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7713
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7708
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7708
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7638
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7638
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7590
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7590
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7578
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7578
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7532
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7532
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7518
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7518
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7458
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7458
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7374
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7374
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7353
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7353
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7342
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7342
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7331
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7331
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7301
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7301
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7265
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7265
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7253
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7253
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7246
Snake venom metalloproteinase atrolysin-D	P15167	VM1AD_CROAT	Crotalus atrox	2	0.7246
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7217
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7217
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7215
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7215
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7212
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7212
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7201
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7201
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7171
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7171
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7168
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7168
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7157
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7157
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7148
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7148
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7124
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7124
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7109
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7109
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7077
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7077
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7072
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7072
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7069
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7069
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7065
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7065
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7054
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7054
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7048
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7048
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7038
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7038
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7028
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7028
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7027
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7027
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7008
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7008

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