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Lotusine C

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

Canonical Smiles	CCC([C@@H]1NC(=O)[C@@H]2C(CCN2C(=O)[C@@H](N(C(=O)[C@H](C(C)C)NC)C)Cc2ccccc2)Oc2ccc(/C=C\NC1=O)cc2)C
InChI	InChI=1S/C35H47N5O5/c1-7-23(4)30-32(41)37-19-17-24-13-15-26(16-14-24)45-28-18-20-40(31(28)33(42)38-30)34(43)27(21-25-11-9-8-10-12-25)39(6)35(44)29(36-5)22(2)3/h8-17,19,22-23,27-31,36H,7,18,20-21H2,1-6H3,(H,37,41)(H,38,42)/b19-17-/t23?,27-,28?,29-,30-,31-/m0/s1
InChIKey	HNXSZBLOFKQSRI-HRIDFCPCSA-N
Formula	C₃₅H₄₇N₅O₅
HBA	6
HBD	3
MW	617.79
Rotatable Bonds	9
TPSA	120.08
LogP	2.98
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.49
Exact Mass	617.36
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

Ghedira K, Chemli R, et al. (1995). Four cyclopeptide alkaloids from Zizyphus lotus. Phytochemistry, 1995, 38(3), 767-772. [View]
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: 101917048

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 419.48 g/mol

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

Level: 0

Mol. Weight: 287.32 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.92
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 25.66

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.02
Plasma Protein Binding: 87.27
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: 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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.86
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.07
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.83
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.67
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: -45721.49
Rat (Acute): 3.02
Rat (Chronic Oral): 1.27
Fathead Minnow: 71.58
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: 961.75
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.36
Log(P): 3.45
Log S: -3.57
Log(Vapor Pressure): -45.82
Melting Point: 202.45
pKa Acid: 6.2
pKa Basic: 7.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.9204
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.9204
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8818
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8818
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8711
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8711
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8380
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8380
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8352
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8352
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8316
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8316
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8127
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8127
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8112
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8112
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8052
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8052
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8002
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8002
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7967
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7967
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7919
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7919
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7909
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7909
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7874
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7874
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7796
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7796
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7787
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7787
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7702
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7702
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7681
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7681
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7676
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7676
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7664
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7664
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7613
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7613
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7603
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7603
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7571
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7571
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7560
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7560
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7549
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7549
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7469
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7469
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7451
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7451
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7364
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7364
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7363
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7363
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7341
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7341
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7315
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7315
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7311
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7311
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7309
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7309
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7280
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7280
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7225
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7225
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7205
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7205
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7204
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7204
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7193
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7193
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7173
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7173
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7166
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	2	0.7166
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7154
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7154
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7145
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7145
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7145
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7145
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7136
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7136
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7132
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7132
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7129
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7129
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7121
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7121
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7119
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7119
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7106
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7106
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7058
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7058
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7055
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7055
6-phosphogluconate dehydrogenase, decarboxylating	P96789	6PGD_LACLM	Lactococcus lactis subsp. cremoris	3	0.7035
6-phosphogluconate dehydrogenase, decarboxylating	P96789	6PGD_LACLM	Lactococcus lactis subsp. cremoris	3	0.7035
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7007
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7007

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