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Lotusine D

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

Canonical Smiles	CN[C@H](C(=O)N1CC[C@H]2C1C(=O)N[C@@H](C(CC)C)C(=O)N/C=C\c1ccc(O2)cc1)Cc1ccccc1
InChI	InChI=1S/C29H36N4O4/c1-4-19(2)25-27(34)31-16-14-20-10-12-22(13-11-20)37-24-15-17-33(26(24)28(35)32-25)29(36)23(30-3)18-21-8-6-5-7-9-21/h5-14,16,19,23-26,30H,4,15,17-18H2,1-3H3,(H,31,34)(H,32,35)/b16-14-/t19?,23-,24-,25-,26?/m0/s1
InChIKey	OLALXNPCMVWJPU-JFUAQMBZSA-N
Formula	C₂₉H₃₆N₄O₄
HBA	5
HBD	3
MW	504.63
Rotatable Bonds	6
TPSA	99.77
LogP	2.5
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	504.27
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: 101229398

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 504.63 g/mol

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

Level: 0

Mol. Weight: 504.63 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 504.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.74
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.78
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.13
Plasma Protein Binding: 81.61
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: 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: 14.99
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): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.51
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.14
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: -1364.67
Rat (Acute): 2.93
Rat (Chronic Oral): 1.45
Fathead Minnow: 7.22
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: 487.07
Hydration Free Energy: -2.88
Log(D) at pH=7.4: 3.18
Log(P): 2.84
Log S: -3.44
Log(Vapor Pressure): -10.6
Melting Point: 211.1
pKa Acid: 8.3
pKa Basic: 7.02

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	0.9541
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.9541
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8828
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8828
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8603
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8603
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8595
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8595
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.8329
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.8329
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8073
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8073
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7764
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7764
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7758
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7758
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7615
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7615
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7507
Polymerase acidic protein	P03433	PA_I34A1	Influenza A virus	2	0.7507
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7481
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7481
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7443
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7443
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7431
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7431
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7429
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7429
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7377
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7377
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7364
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7364
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7364
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7364
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7268
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7268
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7208
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7208
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7171
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7171
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7131
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7131
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7116
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7116
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7083
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7083
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7077
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7077
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7065
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7065
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7053
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7053
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7017
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7017

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