Lotusine E - Compound Card

Lotusine E

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Lotusine E

Structure
Zoomed Structure
  • 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)Oc2cc(/C=C\NC1=O)c(O)cc2)C
InChI InChI=1S/C36H49N5O6/c1-7-23(4)31-34(44)37-17-15-25-21-26(13-14-29(25)42)47-30-16-18-41(32(30)35(45)39-31)36(46)27(20-24-11-9-8-10-12-24)38-33(43)28(40(5)6)19-22(2)3/h8-15,17,21-23,27-28,30-32,42H,7,16,18-20H2,1-6H3,(H,37,44)(H,38,43)(H,39,45)/b17-15-/t23?,27-,28-,30?,31-,32-/m0/s1
InChIKey DXPDHISZCSUSCO-RKNDUAPSSA-N
Formula C36H49N5O6
HBA 7
HBD 4
MW 647.82
Rotatable Bonds 10
TPSA 140.31
LogP 3.08
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 47
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 647.37
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: 101917047

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCC(=O)N(CC2)C(C23)C(=O)NCC(=O)NC=Cc4cc(O3)ccc4

Level: 1

Mol. Weight: 647.82 g/mol

Structure

SMILES: C1CNC(C12)C(=O)NCC(=O)NC=Cc3cc(O2)ccc3

Level: 0

Mol. Weight: 647.82 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 647.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.89
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
52.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.95
Plasma Protein Binding
88.16
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
Inhibitor

Excretion

Clearance
12.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.27
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.5
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
-95646.41
Rat (Acute)
3.14
Rat (Chronic Oral)
1.7
Fathead Minnow
133.58
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
5430.5
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.66
Log(P)
3.55
Log S
-3.87
Log(Vapor Pressure)
-202.79
Melting Point
217.47
pKa Acid
6.09
pKa Basic
7.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8361
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8361
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8212
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8212
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8005
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8005
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7821
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7821
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7666
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7666
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.7662
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.7662
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7650
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7650
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7490
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7490
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7477
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7477
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7424
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7424
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7315
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7315
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7243
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7243
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7220
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7220
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7218
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7218
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7211
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7211
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7172
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7172
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7161
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7161
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7116
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7116
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7101
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7101
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7098
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7098
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7063
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7063
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7053
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7053
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7014
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7014
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7002
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7002

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