NPASS Compound

Structure

CID193471 OpenBabel06191715582D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.4680 -3.6433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4969 -1.5313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7881 0.1326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3550 -3.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2349 -0.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2430 -3.1107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1398 -0.5329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 -2.5993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2058 -2.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7397 -0.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3798 -1.5382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7148 -2.8247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3509 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3381 -2.5883 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3445 -1.5549 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0191 -3.0934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6989 -0.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1969 -0.8153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1334 -1.5660 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.1606 -4.2015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3278 0.6631 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3134 -0.8533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7217 -3.0081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 1 0 0 0 0 4 12 2 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 1 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 6 1 1 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 1 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.17
Volume:	338.617
LogP:	1.307
LogD:	1.835
LogS:	-2.357
# Rotatable Bonds:	0
TPSA:	76.07
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	5.044
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.628
MDCK Permeability:	3.661806840682402e-05
Pgp-inhibitor:	0.867
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.697
30% Bioavailability (F30%):	0.699

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.784
Plasma Protein Binding (PPB):	56.095909118652344%
Volume Distribution (VD):	2.097
Pgp-substrate:	47.598388671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.717
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	6.418
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.816
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.598
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.363
Carcinogencity:	0.931
Eye Corrosion:	0.004
Eye Irritation:	0.067
Respiratory Toxicity:	0.701

Download Data

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

Natural Product: NPC193471

Natural Product ID:	NPC193471
*Common Name:**	Senecionine
IUPAC Name:	n.a.
Synonyms:	Senecionine
Standard InCHIKey:	HKODIGSRFALUTA-JTLQZVBZSA-N
Standard InCHI:	InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1
SMILES:	C/C=C1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL362153
PubChem CID:	5280906
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543912]
NPO30852	Senecio	Genus	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21710732]
NPO33066	senecio anonymus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3210016]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32881525]
NPO2029	Didemnum rubeum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358648]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22458	Fordia cauliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24092	Glaucium pulchrum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7677	Rhodomyrtus macrocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24092	Glaucium pulchrum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22458	Fordia cauliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7677	Rhodomyrtus macrocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11260	Agave toumeyana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10521	Phacelia ixodes	Species	Hydrophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8064	Baccharis petiolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9610	Ageratum myriadenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2029	Didemnum rubeum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2561	Capnella erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20004	Corydalis tenuis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28452	Rhododendron linearifolium	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17735	Acinetobacter genospecies	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24177	Sagotia racemosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18149	Linum paniculatum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2824	Senecio pampeanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23012	Schizogyne glaberrima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20407	Pityrogramma sulphurea	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7677	Rhodomyrtus macrocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20642	Iphiona fragrans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19694	Senecio scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11374	Pycnanthemum muticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22036	Magnolia compressa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25257	Menispermum fenestratum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20767	Hydnum imbricatum	Species	Hydnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24828	Pteraster tesselatus	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22458	Fordia cauliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25564	Ficus erecta	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5639	Carlina corymbosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24092	Glaucium pulchrum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO523	Tussilago farfara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25503	Anticarsia gemmatalis	Species	0ctuidae	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

Activity Type	# Activity
EC50	4
IC50	2
Others	8
Potency	7

Activity Type	# Activity
Cell Line	2
Individual Protein	10
Organism	7
Others	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Log 1/Km	=	-2.477	n.a.	PMID[474022]
NPT2319	Cell Line	A204	Homo sapiens	IC50	=	150.0	ug.mL-1	PMID[474023]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[474024]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	28183.8	nM	PMID[474025]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[474025]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	7.46	%	PMID[474026]
NPT1161	Cell Line	CHO	Cricetulus griseus	EC50	>	100.0	ug.mL-1	PMID[474027]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[474025]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[474025]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	25118.9	nM	PMID[474025]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[474025]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[474025]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	19.16	%	PMID[474026]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	<	50.0	%	PMID[474027]
NPT27	Others	Unspecified		EC50	>	100.0	ug.mL-1	PMID[474027]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	84.0	%	PMID[474027]
NPT2528	Organism	Rhopalosiphum padi	Rhopalosiphum padi	Activity	=	40.0	%	PMID[474027]
NPT348	Organism	Myzus persicae	Myzus persicae	Activity	=	40.0	%	PMID[474027]
NPT1275	Organism	Leptinotarsa decemlineata	Leptinotarsa decemlineata	EC50	=	1.3	microg/cm2	PMID[474027]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	>	50.0	microg/cm2	PMID[474027]

☑ 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 NPC193471 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	108
0.1-0.2	716
0.2-0.3	4361
0.3-0.4	19271
0.4-0.5	12296
0.5-0.6	5074
0.6-0.7	838
0.7-0.8	12
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC130124
0.963	High Similarity	NPC284656
0.963	High Similarity	NPC201889
0.963	High Similarity	NPC106791
0.9619	High Similarity	NPC181510
0.9619	High Similarity	NPC168758
0.9619	High Similarity	NPC47857
0.8929	High Similarity	NPC235625
0.8899	High Similarity	NPC30911
0.8899	High Similarity	NPC316984
0.886	High Similarity	NPC23963
0.8519	High Similarity	NPC64168
0.8426	Intermediate Similarity	NPC279833
0.8426	Intermediate Similarity	NPC80439
0.8426	Intermediate Similarity	NPC6271
0.8426	Intermediate Similarity	NPC173690
0.8304	Intermediate Similarity	NPC196073
0.8304	Intermediate Similarity	NPC195435
0.8158	Intermediate Similarity	NPC275100
0.8158	Intermediate Similarity	NPC474497
0.7815	Intermediate Similarity	NPC156336
0.7815	Intermediate Similarity	NPC120599
0.7815	Intermediate Similarity	NPC200412
0.7398	Intermediate Similarity	NPC230849
0.7203	Intermediate Similarity	NPC474099
0.7155	Intermediate Similarity	NPC474827
0.7155	Intermediate Similarity	NPC68001
0.7155	Intermediate Similarity	NPC199831
0.7155	Intermediate Similarity	NPC474828
0.7049	Intermediate Similarity	NPC469597
0.7045	Intermediate Similarity	NPC133089
0.7023	Intermediate Similarity	NPC477988
0.7018	Intermediate Similarity	NPC476344
0.6991	Remote Similarity	NPC150041
0.6977	Remote Similarity	NPC329401
0.6977	Remote Similarity	NPC477987
0.6975	Remote Similarity	NPC271562
0.6964	Remote Similarity	NPC81419
0.6964	Remote Similarity	NPC179746
0.6957	Remote Similarity	NPC471144
0.6942	Remote Similarity	NPC469603
0.6937	Remote Similarity	NPC51004
0.6935	Remote Similarity	NPC30196
0.6923	Remote Similarity	NPC473289
0.6923	Remote Similarity	NPC474244
0.6899	Remote Similarity	NPC326386
0.6899	Remote Similarity	NPC477985
0.6899	Remote Similarity	NPC471087
0.6885	Remote Similarity	NPC474431
0.6885	Remote Similarity	NPC474411
0.6881	Remote Similarity	NPC469860
0.6881	Remote Similarity	NPC130436
0.6881	Remote Similarity	NPC469861
0.688	Remote Similarity	NPC6531
0.688	Remote Similarity	NPC65045
0.6875	Remote Similarity	NPC208886
0.6875	Remote Similarity	NPC30515
0.6875	Remote Similarity	NPC12172
0.687	Remote Similarity	NPC52820
0.6864	Remote Similarity	NPC475945
0.6864	Remote Similarity	NPC475871
0.685	Remote Similarity	NPC11379
0.6847	Remote Similarity	NPC307411
0.6842	Remote Similarity	NPC316401
0.6838	Remote Similarity	NPC474742
0.6829	Remote Similarity	NPC60432
0.6829	Remote Similarity	NPC261750
0.6829	Remote Similarity	NPC1111
0.6825	Remote Similarity	NPC174463
0.6822	Remote Similarity	NPC111162
0.6822	Remote Similarity	NPC477990
0.6822	Remote Similarity	NPC318445
0.6822	Remote Similarity	NPC316133
0.6822	Remote Similarity	NPC477989
0.6822	Remote Similarity	NPC293550
0.6822	Remote Similarity	NPC323168
0.6814	Remote Similarity	NPC476300
0.6814	Remote Similarity	NPC475912
0.681	Remote Similarity	NPC473326
0.6807	Remote Similarity	NPC474741
0.6786	Remote Similarity	NPC473619
0.6786	Remote Similarity	NPC474761
0.6786	Remote Similarity	NPC476004
0.678	Remote Similarity	NPC149371
0.678	Remote Similarity	NPC474747
0.6767	Remote Similarity	NPC307165
0.6757	Remote Similarity	NPC202672
0.6754	Remote Similarity	NPC474035
0.6754	Remote Similarity	NPC81386
0.6748	Remote Similarity	NPC58281
0.6742	Remote Similarity	NPC471086
0.6726	Remote Similarity	NPC184463
0.6726	Remote Similarity	NPC473321
0.6721	Remote Similarity	NPC38154
0.6718	Remote Similarity	NPC474371
0.6696	Remote Similarity	NPC295312
0.6696	Remote Similarity	NPC270013
0.6696	Remote Similarity	NPC14961
0.6696	Remote Similarity	NPC36954
0.6695	Remote Similarity	NPC47880
0.6695	Remote Similarity	NPC476270
0.6694	Remote Similarity	NPC43648
0.6667	Remote Similarity	NPC476951
0.6667	Remote Similarity	NPC212486
0.6667	Remote Similarity	NPC470000
0.6667	Remote Similarity	NPC204556
0.6667	Remote Similarity	NPC469604
0.6667	Remote Similarity	NPC160138
0.6667	Remote Similarity	NPC314282
0.6642	Remote Similarity	NPC215507
0.6641	Remote Similarity	NPC138534
0.6641	Remote Similarity	NPC477986
0.6636	Remote Similarity	NPC21469
0.6618	Remote Similarity	NPC120420
0.6617	Remote Similarity	NPC173173
0.6612	Remote Similarity	NPC223450
0.6612	Remote Similarity	NPC243998
0.6612	Remote Similarity	NPC93179
0.661	Remote Similarity	NPC475949
0.6609	Remote Similarity	NPC473316
0.6609	Remote Similarity	NPC473330
0.6593	Remote Similarity	NPC120335
0.6587	Remote Similarity	NPC103391
0.6587	Remote Similarity	NPC472536
0.6583	Remote Similarity	NPC472755
0.6583	Remote Similarity	NPC475873
0.6577	Remote Similarity	NPC112685
0.6577	Remote Similarity	NPC284902
0.6569	Remote Similarity	NPC471256
0.6569	Remote Similarity	NPC99864
0.6562	Remote Similarity	NPC9714
0.6557	Remote Similarity	NPC477513
0.6557	Remote Similarity	NPC26617
0.6555	Remote Similarity	NPC110443
0.6555	Remote Similarity	NPC185141
0.6555	Remote Similarity	NPC472753
0.6555	Remote Similarity	NPC164598
0.6555	Remote Similarity	NPC474339
0.6555	Remote Similarity	NPC15993
0.6555	Remote Similarity	NPC46998
0.6555	Remote Similarity	NPC128733
0.6555	Remote Similarity	NPC133907
0.6552	Remote Similarity	NPC471142
0.6549	Remote Similarity	NPC477011
0.6532	Remote Similarity	NPC5103
0.6532	Remote Similarity	NPC113012
0.6532	Remote Similarity	NPC122926
0.6529	Remote Similarity	NPC203659
0.6529	Remote Similarity	NPC44514
0.6529	Remote Similarity	NPC100487
0.6525	Remote Similarity	NPC187268
0.6522	Remote Similarity	NPC288240
0.6522	Remote Similarity	NPC162205
0.6522	Remote Similarity	NPC243902
0.6522	Remote Similarity	NPC295204
0.6522	Remote Similarity	NPC273579
0.6522	Remote Similarity	NPC135776
0.6518	Remote Similarity	NPC231889
0.6518	Remote Similarity	NPC186148
0.6518	Remote Similarity	NPC475703
0.6515	Remote Similarity	NPC313342
0.6515	Remote Similarity	NPC313333
0.6515	Remote Similarity	NPC314451
0.6515	Remote Similarity	NPC314512
0.6515	Remote Similarity	NPC469999
0.6512	Remote Similarity	NPC471261
0.6504	Remote Similarity	NPC70235
0.65	Remote Similarity	NPC86077
0.65	Remote Similarity	NPC320019
0.65	Remote Similarity	NPC324017
0.65	Remote Similarity	NPC472754
0.6496	Remote Similarity	NPC476315
0.6496	Remote Similarity	NPC17585
0.6496	Remote Similarity	NPC477921
0.6491	Remote Similarity	NPC473448
0.6486	Remote Similarity	NPC100921
0.6486	Remote Similarity	NPC215364
0.6486	Remote Similarity	NPC477018
0.6484	Remote Similarity	NPC469997
0.648	Remote Similarity	NPC179798
0.648	Remote Similarity	NPC304180
0.6471	Remote Similarity	NPC189393
0.6471	Remote Similarity	NPC90814
0.6471	Remote Similarity	NPC26597
0.6471	Remote Similarity	NPC288876
0.6466	Remote Similarity	NPC477131
0.646	Remote Similarity	NPC58219
0.646	Remote Similarity	NPC153805
0.646	Remote Similarity	NPC177629
0.646	Remote Similarity	NPC89001
0.646	Remote Similarity	NPC473715
0.6446	Remote Similarity	NPC110989
0.6446	Remote Similarity	NPC472747
0.6446	Remote Similarity	NPC472750
0.6444	Remote Similarity	NPC316205
0.6444	Remote Similarity	NPC470539
0.6444	Remote Similarity	NPC315387
0.6439	Remote Similarity	NPC314629
0.6435	Remote Similarity	NPC118844
0.6435	Remote Similarity	NPC299808

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 NPC193471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	616
0.2-0.3	3108
0.3-0.4	3789
0.4-0.5	1244
0.5-0.6	282
0.6-0.7	21
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8899	High Similarity	NPD2204	Approved
0.6822	Remote Similarity	NPD7642	Approved
0.6744	Remote Similarity	NPD8080	Discontinued
0.6718	Remote Similarity	NPD8451	Approved
0.6693	Remote Similarity	NPD7641	Discontinued
0.6667	Remote Similarity	NPD8448	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8415	Approved
0.6557	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD8390	Approved
0.6519	Remote Similarity	NPD8391	Approved
0.6519	Remote Similarity	NPD8392	Approved
0.6515	Remote Similarity	NPD8341	Approved
0.6515	Remote Similarity	NPD8299	Approved
0.6515	Remote Similarity	NPD8340	Approved
0.6515	Remote Similarity	NPD8342	Approved
0.6471	Remote Similarity	NPD7260	Phase 2
0.6343	Remote Similarity	NPD8273	Phase 1
0.6194	Remote Similarity	NPD7830	Approved
0.6194	Remote Similarity	NPD7829	Approved
0.619	Remote Similarity	NPD2575	Approved
0.6181	Remote Similarity	NPD8384	Approved
0.6142	Remote Similarity	NPD6421	Discontinued
0.6124	Remote Similarity	NPD1376	Discontinued
0.6115	Remote Similarity	NPD3663	Approved
0.6115	Remote Similarity	NPD3664	Approved
0.6115	Remote Similarity	NPD3661	Approved
0.6115	Remote Similarity	NPD3662	Phase 3
0.6068	Remote Similarity	NPD6698	Approved
0.6068	Remote Similarity	NPD46	Approved
0.6014	Remote Similarity	NPD8336	Approved
0.6014	Remote Similarity	NPD8337	Approved
0.5974	Remote Similarity	NPD8414	Discontinued
0.5952	Remote Similarity	NPD4211	Phase 1
0.5932	Remote Similarity	NPD7838	Discovery
0.5926	Remote Similarity	NPD6909	Approved
0.5926	Remote Similarity	NPD8444	Approved
0.5926	Remote Similarity	NPD6908	Approved
0.5913	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6371	Approved
0.5887	Remote Similarity	NPD5204	Approved
0.5874	Remote Similarity	NPD4621	Approved
0.5874	Remote Similarity	NPD4619	Approved
0.5872	Remote Similarity	NPD1452	Discontinued
0.5868	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6686	Approved
0.5845	Remote Similarity	NPD8338	Approved
0.5845	Remote Similarity	NPD2613	Approved
0.5833	Remote Similarity	NPD3089	Approved
0.5833	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3616	Approved
0.5833	Remote Similarity	NPD3615	Approved
0.5833	Remote Similarity	NPD3088	Approved
0.5833	Remote Similarity	NPD2571	Approved
0.5833	Remote Similarity	NPD4746	Phase 3
0.5833	Remote Similarity	NPD2574	Discontinued
0.5833	Remote Similarity	NPD3090	Approved
0.5833	Remote Similarity	NPD3614	Approved
0.5833	Remote Similarity	NPD2573	Approved
0.5833	Remote Similarity	NPD3087	Approved
0.5833	Remote Similarity	NPD2570	Approved
0.5833	Remote Similarity	NPD4745	Approved
0.5833	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2566	Approved
0.582	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD6921	Approved
0.5769	Remote Similarity	NPD6420	Discontinued
0.5753	Remote Similarity	NPD4685	Phase 3
0.5753	Remote Similarity	NPD4686	Approved
0.5753	Remote Similarity	NPD6333	Approved
0.5753	Remote Similarity	NPD6334	Approved
0.5753	Remote Similarity	NPD4684	Phase 3
0.575	Remote Similarity	NPD7983	Approved
0.5745	Remote Similarity	NPD2627	Approved
0.5745	Remote Similarity	NPD2159	Approved
0.5745	Remote Similarity	NPD2625	Approved
0.5745	Remote Similarity	NPD2628	Approved
0.5745	Remote Similarity	NPD2160	Approved
0.5745	Remote Similarity	NPD2626	Approved
0.5739	Remote Similarity	NPD6110	Phase 1
0.5725	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1695	Approved
0.5704	Remote Similarity	NPD1773	Discontinued
0.5704	Remote Similarity	NPD6914	Discontinued
0.5693	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD4228	Discovery
0.5685	Remote Similarity	NPD6311	Approved
0.5685	Remote Similarity	NPD6309	Approved
0.5685	Remote Similarity	NPD6310	Approved
0.5682	Remote Similarity	NPD6053	Discontinued
0.5669	Remote Similarity	NPD8276	Approved
0.5669	Remote Similarity	NPD2259	Approved
0.5669	Remote Similarity	NPD1407	Approved
0.5669	Remote Similarity	NPD8275	Approved
0.5669	Remote Similarity	NPD2258	Approved
0.5664	Remote Similarity	NPD2101	Approved
0.5659	Remote Similarity	NPD8140	Approved
0.5656	Remote Similarity	NPD5282	Discontinued
0.5652	Remote Similarity	NPD7623	Phase 3
0.5652	Remote Similarity	NPD882	Phase 2
0.5652	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD883	Phase 2
0.5635	Remote Similarity	NPD5344	Discontinued
0.563	Remote Similarity	NPD7505	Discontinued
0.5625	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.562	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7122	Discontinued
0.5603	Remote Similarity	NPD8074	Phase 3
0.56	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4225	Approved

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