ANPDB

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Lotusine B

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

Canonical Smiles	CCC([C@@H]1NC(=O)[C@@H]2C(CCN2C(=O)[C@@H](NC(=O)[C@@H](N(C)C)CC(C)C)Cc2ccccc2)Oc2ccc(/C=C\NC1=O)cc2)C
InChI	InChI=1S/C36H49N5O5/c1-7-24(4)31-34(43)37-19-17-25-13-15-27(16-14-25)46-30-18-20-41(32(30)35(44)39-31)36(45)28(22-26-11-9-8-10-12-26)38-33(42)29(40(5)6)21-23(2)3/h8-17,19,23-24,28-32H,7,18,20-22H2,1-6H3,(H,37,43)(H,38,42)(H,39,44)/b19-17-/t24?,28-,29-,30?,31-,32-/m0/s1
InChIKey	QIIAHRYZRXDYGH-ZRIDXQSGSA-N
Formula	C₃₆H₄₉N₅O₅
HBA	6
HBD	3
MW	631.82
Rotatable Bonds	10
TPSA	120.08
LogP	3.37
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	631.37
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: 101917049

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 631.82 g/mol

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

Level: 0

Mol. Weight: 631.82 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 631.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.39
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.83
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 36.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.11
Plasma Protein Binding: 90.54
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Inhibitor

Excretion

Clearance: 13.0
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.44
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.43
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.75
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: -66150.08
Rat (Acute): 3.21
Rat (Chronic Oral): 1.42
Fathead Minnow: 96.26
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 2757.6
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 4.04
Log(P): 3.98
Log S: -3.83
Log(Vapor Pressure): -110.37
Melting Point: 219.23
pKa Acid: 6.75
pKa Basic: 6.81

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8792
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8792
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8638
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8638
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.8012
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.8012
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7931
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7931
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7913
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7913
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7791
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7791
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7693
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7693
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7691
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7691
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7647
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7647
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7607
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7607
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7588
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7588
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7585
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7585
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7513
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7513
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7483
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7483
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7466
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7466
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7446
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7446
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7385
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7385
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7372
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7372
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7355
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7355
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7327
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7327
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7326
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7326
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7278
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7278
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7242
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7242
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7199
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7199
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7198
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7198
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7175
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7175
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7163
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7163
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7116
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7116
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7106
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7106
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7104
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7104
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7092
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7092
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7081
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7081
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7071
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7071
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7068
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7068
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7049
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7049
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7023
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7023

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