Structure

Physi-Chem Properties

Molecular Weight:  190.11
Volume:  196.017
LogP:  0.414
LogD:  0.769
LogS:  0.561
# Rotatable Bonds:  0
TPSA:  34.03
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.648
Synthetic Accessibility Score:  4.046
Fsp3:  0.545
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.911
MDCK Permeability:  4.542742317426018e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.186
30% Bioavailability (F30%):  0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.93
Plasma Protein Binding (PPB):  13.363560676574707%
Volume Distribution (VD):  2.001
Pgp-substrate:  81.003173828125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.119
CYP1A2-substrate:  0.225
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.634
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.098
CYP2D6-inhibitor:  0.604
CYP2D6-substrate:  0.641
CYP3A4-inhibitor:  0.063
CYP3A4-substrate:  0.275

ADMET: Excretion

Clearance (CL):  7.069
Half-life (T1/2):  0.359

ADMET: Toxicity

hERG Blockers:  0.161
Human Hepatotoxicity (H-HT):  0.592
Drug-inuced Liver Injury (DILI):  0.038
AMES Toxicity:  0.891
Rat Oral Acute Toxicity:  0.793
Maximum Recommended Daily Dose:  0.963
Skin Sensitization:  0.349
Carcinogencity:  0.677
Eye Corrosion:  0.004
Eye Irritation:  0.039
Respiratory Toxicity:  0.852

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC77890

Natural Product ID:  NPC77890
Common Name*:   Cytisine
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  ANJTVLIZGCUXLD-DTWKUNHWSA-N
Standard InCHI:  InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/p+1/t8-,9+/m0/s1
SMILES:  c1cc2[C@@H]3C[C@@H](C[NH2+]C3)Cn2c(=O)c1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL497939
PubChem CID:   10235
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002719] Lupin alkaloids
        • [CHEMONTID:0002722] Cytisine and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO6692 Pleurostylia opposita Species Celastraceae Eukaryota Stem bark University of Colombo Campus, Sri Lanka 2005-JUL PMID[17190474]
NPO24639 Streptomyces filamentosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17284073]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO30682 Fabaceae Genus Fabaceae Eukaryota n.a. n.a. n.a. PMID[22978215]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23022271]
NPO546 Candida albicans Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. PMID[23902158]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. Database[FooDB]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5725 Stephania dinklagei Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5725 Stephania dinklagei Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18975 Melilotus messanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6692 Pleurostylia opposita Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3877 Chaenorhinum minus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2915 Carya pecan Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1990 Cirsium eriophorum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26656 Heliotropium hirsutissimum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2992 Calonectria nivalis Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO546 Candida albicans Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2610 Chionodoxa gigantea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7011 Chamomilla recutita n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO11127 Inulanthera calva Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5725 Stephania dinklagei Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12152 Nicotiana raimondii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1468 Crassostrea virginica Species Ostreidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9830 Arum maximum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6679 Tephrosia watsoniana Species Geometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2419 Macrocentrus cingulum Species Braconidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13564 Leucospermum reflexum Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1077 Piper dilatatum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1051 Lathyrus cicer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18510 Dendrobium cariniferum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24639 Streptomyces filamentosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4061 Trollius europaeus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO791 Laburnum anagyroides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6060 Amaranthus spinosus Species Amaranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18441 Solanum tequilense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7795 Calonectria kyotensis Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4780 Sophora griffithii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18975 Melilotus messanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15875 Scolopia chinensis Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens EC50 = 71000.0 nM PMID[572241]
NPT408 Individual Protein Acetylcholine receptor protein delta chain Torpedo californica EC50 = 100000.0 nM PMID[572241]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 0.9 nM PMID[572244]
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens Ki = 4200.0 nM PMID[572249]
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens EC50 = 71000.0 nM PMID[572250]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Rmax = 90.0 % PMID[572250]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Rmax = 105.0 % PMID[572250]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 4200.0 nM PMID[572251]
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens Ki = 1420.0 nM PMID[572252]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 5820.0 nM PMID[572255]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 331.0 nM PMID[572256]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 300.0 nM PMID[572259]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 1000.0 nM PMID[572260]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 63.1 nM PMID[572263]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 22387.2 nM PMID[572262]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 14125.4 nM PMID[572263]
NPT583 Individual Protein Inositol monophosphatase 1 Rattus norvegicus Potency = 3162.3 nM PMID[572262]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 44668.4 nM PMID[572265]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 31622.8 nM PMID[572262]
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 17782.8 nM PMID[572265]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 31622.78 nM PMID[572262]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 31622.78 nM PMID[572262]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 39810.7 nM PMID[572263]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[572266]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 2.17 % PMID[572267]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 8000.0 nM PMID[572268]
NPT1304 Individual Protein Nicotinic acetylcholine receptor alpha 5 subunit Musca domestica Ki = 1230.0 nM PMID[572269]
NPT3925 Individual Protein Acetylcholine receptor protein alpha chain Torpedo californica IC50 = 3530.0 nM PMID[572270]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 230.0 nM PMID[572272]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 261.0 nM PMID[572274]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 250.0 nM PMID[572275]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 158489.3 nM PMID[572264]
NPT410 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Homo sapiens Ki = 5890.0 nM PMID[572276]
NPT616 Cell Line MDCK Canis lupus familiaris CC50 > 80000.0 nM PMID[572277]
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus Ki = 1700.0 nM PMID[572287]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens EC50 = 38000.0 nM PMID[572241]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens EC50 = 26000.0 nM PMID[572241]
NPT413 Protein Complex Neuronal acetylcholine receptor Rattus norvegicus EC50 = 10000.0 nM PMID[572241]
NPT29 Organism Rattus norvegicus Rattus norvegicus EC50 = 60.0 nM PMID[572241]
NPT27 Others Unspecified Binding energy = 12.1 kCal mol-1 PMID[572242]
NPT415 Protein Complex Neuronal acetylcholine receptor; alpha2/beta2 Rattus norvegicus Ki = 1.4 nM PMID[572243]
NPT2 Others Unspecified Ki = 5.5 nM PMID[572243]
NPT416 Protein Complex Neuronal acetylcholine receptor; alpha3/beta2 Rattus norvegicus Ki = 37.0 nM PMID[572243]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus Ki = 210.0 nM PMID[572243]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1.5 nM PMID[572243]
NPT418 Protein Complex Neuronal acetylcholine receptor; alpha4/beta4 Rattus norvegicus Ki = 2.2 nM PMID[572243]
NPT413 Protein Complex Neuronal acetylcholine receptor Rattus norvegicus Ki = 2.5 nM PMID[572243]
NPT2 Others Unspecified Ratio = 4.0 n.a. PMID[572243]
NPT2 Others Unspecified Ratio = 6.0 n.a. PMID[572243]
NPT2 Others Unspecified Ratio = 1.0 n.a. PMID[572243]
NPT2 Others Unspecified Ratio = 84.0 n.a. PMID[572243]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 2.78 nM PMID[572244]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 4.2 nM PMID[572245]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus EC50 = 8.8 nM PMID[572245]
NPT29 Organism Rattus norvegicus Rattus norvegicus Biodistribution = 0.2 % PMID[572246]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.123 nM PMID[572247]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus Affinity = 220.0 nM PMID[572248]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus EC50 = 25.0 nM PMID[572248]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus Efficacy = 62.0 % PMID[572248]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Affinity = 0.124 nM PMID[572248]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens EC50 = 0.42 nM PMID[572248]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Efficacy = 59.0 % PMID[572248]
NPT3919 Protein Complex Acetylcholine receptor; alpha1/beta1/delta/gamma Homo sapiens EC50 = 11.0 nM PMID[572248]
NPT3919 Protein Complex Acetylcholine receptor; alpha1/beta1/delta/gamma Homo sapiens Efficacy = 55.0 % PMID[572248]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Ki = 0.23 nM PMID[572249]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.17 nM PMID[572249]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 840.0 nM PMID[572249]
NPT2 Others Unspecified Ki = 250.0 nM PMID[572249]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Response = 56.0 % PMID[572249]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Inhibition = 30.0 % PMID[572249]
NPT423 Protein Complex Neuronal acetylcholine receptor; alpha3/beta2 Homo sapiens EC50 = 67000.0 nM PMID[572250]
NPT2 Others Unspecified EC50 = 72000.0 nM PMID[572250]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Rmax = 89.0 % PMID[572250]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Rmax = 56.0 % PMID[572250]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Rmax = 77.0 % PMID[572250]
NPT2 Others Unspecified EC50 = 900.0 nM PMID[572250]
NPT3920 Protein Complex Neuronal acetylcholine receptor; alpha4/beta4 Homo sapiens Rmax = 51.0 % PMID[572250]
NPT3920 Protein Complex Neuronal acetylcholine receptor; alpha4/beta4 Homo sapiens Rmax = 70.0 % PMID[572250]
NPT3920 Protein Complex Neuronal acetylcholine receptor; alpha4/beta4 Homo sapiens Rmax = 90.0 % PMID[572250]
NPT423 Protein Complex Neuronal acetylcholine receptor; alpha3/beta2 Homo sapiens Rmax = 55.0 % PMID[572250]
NPT423 Protein Complex Neuronal acetylcholine receptor; alpha3/beta2 Homo sapiens Rmax = 23.0 uM PMID[572250]
NPT2 Others Unspecified EC50 = 2700.0 nM PMID[572250]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Rmax = 42.0 % PMID[572250]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Rmax = 11.0 % PMID[572250]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Rmax = 2.0 % PMID[572250]
NPT2 Others Unspecified EC50 = 39000.0 nM PMID[572250]
NPT3921 Protein Complex Neuronal acetylcholine receptor; alpha2/beta4 Homo sapiens Rmax = 58.0 % PMID[572250]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.17 nM PMID[572251]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 840.0 nM PMID[572251]
NPT3922 Protein Complex Acetylcholine receptor Torpedo californica Ki = 250.0 nM PMID[572251]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Response = 56.0 % PMID[572251]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Inhibition = 30.0 % PMID[572251]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Ki = 0.23 nM PMID[572252]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 840.0 nM PMID[572252]
NPT3919 Protein Complex Acetylcholine receptor; alpha1/beta1/delta/gamma Homo sapiens Ki = 250.0 nM PMID[572252]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Efficacy = 56.0 % PMID[572252]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Inhibition = 30.0 % PMID[572252]
NPT415 Protein Complex Neuronal acetylcholine receptor; alpha2/beta2 Rattus norvegicus Ki = 1.07 nM PMID[572253]
NPT3923 Protein Complex Neuronal acetylcholine receptor; alpha2/beta4 Rattus norvegicus Ki = 5.41 nM PMID[572253]
NPT416 Protein Complex Neuronal acetylcholine receptor; alpha3/beta2 Rattus norvegicus Ki = 37.2 nM PMID[572253]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus Ki = 217.0 nM PMID[572253]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1.51 nM PMID[572253]
NPT418 Protein Complex Neuronal acetylcholine receptor; alpha4/beta4 Rattus norvegicus Ki = 2.1 nM PMID[572253]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1.92 nM PMID[572253]
NPT2 Others Unspecified Ki = 144.0 nM PMID[572253]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Ki = 2.59 nM PMID[572254]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 525.0 nM PMID[572254]
NPT2 Others Unspecified Ratio Ki = 203.0 n.a. PMID[572254]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.43 nM PMID[572255]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 1560.0 nM PMID[572255]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.48 nM PMID[572256]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.34 nM PMID[572256]
NPT2 Others Unspecified IC50 = 140.0 nM PMID[572257]
NPT2 Others Unspecified IC50 = 400000.0 nM PMID[572257]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus IC50 = 69.18 nM PMID[572258]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.4 nM PMID[572259]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1.06 nM PMID[572260]
NPT417 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Rattus norvegicus Ki = 203.0 nM PMID[572261]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1.53 nM PMID[572261]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[572262]
NPT2 Others Unspecified Potency = 206.0 nM PMID[572264]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -3.85 % PMID[572267]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 1.0 nM PMID[572268]
NPT2 Others Unspecified Ki = 650.0 nM PMID[572269]
NPT2 Others Unspecified Inhibition = 12.6 % PMID[572271]
NPT2 Others Unspecified IC50 = 267.0 nM PMID[572271]
NPT2 Others Unspecified IC50 > 1000000.0 nM PMID[572271]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 280.0 nM PMID[572272]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 2.1 nM PMID[572272]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 99.71 % PMID[572273]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 106.19 % PMID[572273]
NPT2 Others Unspecified Ki = 1300.0 nM PMID[572274]
NPT2 Others Unspecified Ki = 18.0 nM PMID[572274]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.122 nM PMID[572274]
NPT2 Others Unspecified Ki = 1300.0 nM PMID[572275]
NPT2 Others Unspecified Ki = 19.0 nM PMID[572275]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.122 nM PMID[572275]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens IC50 = 50.0 nM PMID[572276]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens IC50 = 28000.0 nM PMID[572276]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens EC50 = 2000.0 nM PMID[572276]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Efficacy = 6.5 % PMID[572276]
NPT411 Protein Complex Neuronal acetylcholine receptor; alpha3/beta4 Homo sapiens Ki = 480.0 nM PMID[572276]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Ki = 2.0 nM PMID[572276]
NPT1453 Organism Influenza A virus (A/PR/8/34(H1N1)) Influenza A virus (A/Puerto Rico/8/1934(H1N1)) EC50 > 80000.0 nM PMID[572277]
NPT32 Organism Mus musculus Mus musculus LD50 = 1.73 mg.kg-1 PMID[572278]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 5.71 % PMID[572279]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 20.97 % PMID[572280]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 14.59 % PMID[572281]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -2.316 % PMID[572282]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.12 % PMID[572283]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.04 % PMID[572284]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.12 % PMID[572285]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[572286]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[572286]
NPT409 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Homo sapiens Ki = 0.28 nM PMID[572287]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 0.4 nM PMID[572287]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 60.0 % PMID[572287]
NPT2 Others Unspecified Ki > 400000.0 nM PMID[572287]
NPT2 Others Unspecified Ki = 0.16 nM PMID[572287]
NPT2 Others Unspecified Bmax = 99.1 fmol/mg PMID[572287]
NPT2 Others Unspecified Kd = 0.145 nM PMID[572287]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC77890 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC132858
1.0 High Similarity NPC267203
0.9189 High Similarity NPC63284
0.9067 High Similarity NPC320667
0.9067 High Similarity NPC214125
0.8947 High Similarity NPC244256
0.8947 High Similarity NPC86452
0.8193 Intermediate Similarity NPC143344
0.8193 Intermediate Similarity NPC135639
0.8193 Intermediate Similarity NPC234822
0.8193 Intermediate Similarity NPC78058
0.8193 Intermediate Similarity NPC61321
0.8 Intermediate Similarity NPC25513
0.759 Intermediate Similarity NPC120699
0.759 Intermediate Similarity NPC127430
0.7159 Intermediate Similarity NPC207048
0.7143 Intermediate Similarity NPC308050
0.6753 Remote Similarity NPC42477
0.6667 Remote Similarity NPC477460
0.6667 Remote Similarity NPC76869
0.6632 Remote Similarity NPC145707
0.6591 Remote Similarity NPC268580
0.6538 Remote Similarity NPC470738
0.65 Remote Similarity NPC206660
0.63 Remote Similarity NPC91036
0.6237 Remote Similarity NPC116881
0.6237 Remote Similarity NPC57163
0.6222 Remote Similarity NPC472194
0.6117 Remote Similarity NPC100810
0.6117 Remote Similarity NPC144714
0.6111 Remote Similarity NPC28529
0.6105 Remote Similarity NPC476141
0.6076 Remote Similarity NPC385
0.6049 Remote Similarity NPC477461
0.6049 Remote Similarity NPC477459
0.6 Remote Similarity NPC133923
0.5888 Remote Similarity NPC472856
0.5854 Remote Similarity NPC252684
0.5851 Remote Similarity NPC255430
0.5778 Remote Similarity NPC34672
0.5766 Remote Similarity NPC143173
0.5714 Remote Similarity NPC17497
0.5714 Remote Similarity NPC476559
0.5714 Remote Similarity NPC305602

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC77890 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD529 Approved
0.6353 Remote Similarity NPD816 Approved
0.6353 Remote Similarity NPD815 Approved
0.5849 Remote Similarity NPD2905 Discontinued
0.5818 Remote Similarity NPD4063 Clinical (unspecified phase)
0.5726 Remote Similarity NPD1306 Clinical (unspecified phase)
0.57 Remote Similarity NPD1691 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data