NPASS Compound

Structure

CID200743 OpenBabel06191715592D 25 29 0 0 1 0 0 0 0 0999 V2000 -3.8416 -2.8129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7975 -2.8129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4929 0.5671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0263 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5318 1.4520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5309 0.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6848 -0.0121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6664 -1.9087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1461 -0.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3195 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 -1.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0138 1.9306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6655 0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8258 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8395 0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4929 -1.4315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6664 0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1461 -1.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3195 -1.9087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4929 -0.4770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8398 -0.4770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0503 -1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 17 2 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 16 2 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 16 24 1 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 1 0 0 0 19 22 1 6 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 22 3 1 1 0 0 0 23 4 1 1 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.22
Volume:	370.187
LogP:	5.06
LogD:	4.208
LogS:	-5.139
# Rotatable Bonds:	0
TPSA:	22.0
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.637
Synthetic Accessibility Score:	4.201
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	1.8992810510098934e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.808
Plasma Protein Binding (PPB):	93.92264556884766%
Volume Distribution (VD):	0.755
Pgp-substrate:	6.245326042175293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.629
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.709
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.373
CYP2D6-substrate:	0.416
CYP3A4-inhibitor:	0.729
CYP3A4-substrate:	0.652

ADMET: Excretion

Clearance (CL):	10.696
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.158
Carcinogencity:	0.199
Eye Corrosion:	0.003
Eye Irritation:	0.074
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC200743

Natural Product ID:	NPC200743
*Common Name:**	Polysin
IUPAC Name:	n.a.
Synonyms:	Polysin
Standard InCHIKey:	NEPLKJAINOWIJL-DHNNRRLOSA-N
Standard InCHI:	InChI=1S/C23H29NO/c1-21(2)18-9-12-23(4)19(22(18,3)11-10-20(21)25)14-16-13-15-7-5-6-8-17(15)24(16)23/h5-8,13,18-19H,9-12,14H2,1-4H3/t18-,19-,22-,23+/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@@H](Cc4cc5ccccc5n34)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1083627
PubChem CID:	46871703
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620236]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28729	Spirostachys africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24723	Ophiorrhiza bracteata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24342	Lupinus albus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21816	Calea jamaicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25164	Polyalthia suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24593	Campanula pyramidalis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24561	Sesuvium portulacastrum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25009	Cystoseira myrica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4501	Caragana intermedia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24939	Veronica officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13718	Poria tenuis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12599.1	Pinus leiophylla var. chihuahuana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24123	Ramalina scopulorum	Species	Ramalinaceae	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
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Ki	=	9000.0	nM	PMID[512849]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Ki/Km	=	0.05	n.a.	PMID[512849]

☑ 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 NPC200743 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	530
0.1-0.2	2241
0.2-0.3	10717
0.3-0.4	21497
0.4-0.5	3815
0.5-0.6	2416
0.6-0.7	1254
0.7-0.8	223
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC126492
0.7901	Intermediate Similarity	NPC194881
0.7853	Intermediate Similarity	NPC21174
0.7853	Intermediate Similarity	NPC271797
0.7849	Intermediate Similarity	NPC99428
0.7848	Intermediate Similarity	NPC33421
0.7834	Intermediate Similarity	NPC477134
0.7831	Intermediate Similarity	NPC6982
0.7805	Intermediate Similarity	NPC71132
0.7727	Intermediate Similarity	NPC104483
0.7727	Intermediate Similarity	NPC471386
0.7654	Intermediate Similarity	NPC51054
0.7619	Intermediate Similarity	NPC122718
0.7616	Intermediate Similarity	NPC475450
0.7613	Intermediate Similarity	NPC312092
0.7576	Intermediate Similarity	NPC214106
0.7574	Intermediate Similarity	NPC161861
0.7566	Intermediate Similarity	NPC473930
0.7561	Intermediate Similarity	NPC6436
0.756	Intermediate Similarity	NPC471943
0.755	Intermediate Similarity	NPC475428
0.7542	Intermediate Similarity	NPC181502
0.7542	Intermediate Similarity	NPC85066
0.7531	Intermediate Similarity	NPC281094
0.75	Intermediate Similarity	NPC76982
0.75	Intermediate Similarity	NPC179365
0.75	Intermediate Similarity	NPC213468
0.75	Intermediate Similarity	NPC81561
0.75	Intermediate Similarity	NPC154293
0.7485	Intermediate Similarity	NPC115232
0.7483	Intermediate Similarity	NPC473587
0.7471	Intermediate Similarity	NPC117027
0.7471	Intermediate Similarity	NPC97525
0.7468	Intermediate Similarity	NPC20144
0.7466	Intermediate Similarity	NPC215519
0.7458	Intermediate Similarity	NPC473666
0.7457	Intermediate Similarity	NPC15840
0.7455	Intermediate Similarity	NPC41257
0.7453	Intermediate Similarity	NPC124005
0.7452	Intermediate Similarity	NPC238499
0.7448	Intermediate Similarity	NPC54102
0.7448	Intermediate Similarity	NPC162689
0.7442	Intermediate Similarity	NPC64436
0.7439	Intermediate Similarity	NPC184476
0.7438	Intermediate Similarity	NPC478186
0.7431	Intermediate Similarity	NPC148140
0.743	Intermediate Similarity	NPC47190
0.7421	Intermediate Similarity	NPC242556
0.7417	Intermediate Similarity	NPC473762
0.7405	Intermediate Similarity	NPC277157
0.74	Intermediate Similarity	NPC250361
0.7399	Intermediate Similarity	NPC6093
0.7394	Intermediate Similarity	NPC286427
0.7371	Intermediate Similarity	NPC470205
0.7349	Intermediate Similarity	NPC56765
0.7349	Intermediate Similarity	NPC206819
0.7349	Intermediate Similarity	NPC318065
0.7342	Intermediate Similarity	NPC2949
0.7341	Intermediate Similarity	NPC284775
0.733	Intermediate Similarity	NPC472119
0.733	Intermediate Similarity	NPC258480
0.7329	Intermediate Similarity	NPC129042
0.7318	Intermediate Similarity	NPC329858
0.7284	Intermediate Similarity	NPC21605
0.7273	Intermediate Similarity	NPC38736
0.7273	Intermediate Similarity	NPC19679
0.7267	Intermediate Similarity	NPC470440
0.7261	Intermediate Similarity	NPC314102
0.7261	Intermediate Similarity	NPC150259
0.7261	Intermediate Similarity	NPC251722
0.7257	Intermediate Similarity	NPC198339
0.7257	Intermediate Similarity	NPC91179
0.7253	Intermediate Similarity	NPC157828
0.7253	Intermediate Similarity	NPC195239
0.7251	Intermediate Similarity	NPC194411
0.7248	Intermediate Similarity	NPC41174
0.7241	Intermediate Similarity	NPC234987
0.7239	Intermediate Similarity	NPC187951
0.7239	Intermediate Similarity	NPC37548
0.7235	Intermediate Similarity	NPC56233
0.7233	Intermediate Similarity	NPC59084
0.7222	Intermediate Similarity	NPC206967
0.7219	Intermediate Similarity	NPC472587
0.7219	Intermediate Similarity	NPC162799
0.7219	Intermediate Similarity	NPC271734
0.7216	Intermediate Similarity	NPC302191
0.7213	Intermediate Similarity	NPC11445
0.7211	Intermediate Similarity	NPC284102
0.7208	Intermediate Similarity	NPC22079
0.7207	Intermediate Similarity	NPC472323
0.7202	Intermediate Similarity	NPC255229
0.7202	Intermediate Similarity	NPC473320
0.7202	Intermediate Similarity	NPC81229
0.72	Intermediate Similarity	NPC248462
0.7198	Intermediate Similarity	NPC304203
0.7195	Intermediate Similarity	NPC53947
0.7193	Intermediate Similarity	NPC70949
0.7191	Intermediate Similarity	NPC472107
0.7191	Intermediate Similarity	NPC79062
0.7191	Intermediate Similarity	NPC476319
0.7188	Intermediate Similarity	NPC63157
0.7188	Intermediate Similarity	NPC473868
0.7186	Intermediate Similarity	NPC299594
0.7182	Intermediate Similarity	NPC472097
0.7175	Intermediate Similarity	NPC143533
0.7169	Intermediate Similarity	NPC471458
0.7166	Intermediate Similarity	NPC162730
0.7159	Intermediate Similarity	NPC300688
0.7159	Intermediate Similarity	NPC477042
0.7151	Intermediate Similarity	NPC66210
0.7151	Intermediate Similarity	NPC65080
0.7151	Intermediate Similarity	NPC478077
0.7143	Intermediate Similarity	NPC474880
0.7143	Intermediate Similarity	NPC475990
0.7143	Intermediate Similarity	NPC237188
0.7143	Intermediate Similarity	NPC221786
0.7143	Intermediate Similarity	NPC151939
0.7135	Intermediate Similarity	NPC114637
0.7135	Intermediate Similarity	NPC165201
0.7134	Intermediate Similarity	NPC198988
0.7127	Intermediate Similarity	NPC314333
0.7126	Intermediate Similarity	NPC37423
0.7126	Intermediate Similarity	NPC275305
0.7119	Intermediate Similarity	NPC113626
0.7118	Intermediate Similarity	NPC8104
0.7118	Intermediate Similarity	NPC478182
0.7107	Intermediate Similarity	NPC169433
0.7105	Intermediate Similarity	NPC477065
0.7102	Intermediate Similarity	NPC215795
0.7102	Intermediate Similarity	NPC176199
0.7101	Intermediate Similarity	NPC229173
0.7095	Intermediate Similarity	NPC99939
0.7095	Intermediate Similarity	NPC308931
0.7093	Intermediate Similarity	NPC201700
0.7086	Intermediate Similarity	NPC56618
0.7083	Intermediate Similarity	NPC129721
0.7083	Intermediate Similarity	NPC216643
0.7079	Intermediate Similarity	NPC159125
0.7074	Intermediate Similarity	NPC474116
0.7073	Intermediate Similarity	NPC477974
0.7069	Intermediate Similarity	NPC252572
0.7069	Intermediate Similarity	NPC477976
0.7066	Intermediate Similarity	NPC470507
0.7063	Intermediate Similarity	NPC88097
0.7059	Intermediate Similarity	NPC16667
0.7059	Intermediate Similarity	NPC242116
0.7059	Intermediate Similarity	NPC252338
0.7053	Intermediate Similarity	NPC18661
0.7052	Intermediate Similarity	NPC280548
0.7045	Intermediate Similarity	NPC68354
0.7045	Intermediate Similarity	NPC157583
0.7043	Intermediate Similarity	NPC473747
0.7043	Intermediate Similarity	NPC34837
0.7041	Intermediate Similarity	NPC92796
0.7041	Intermediate Similarity	NPC135141
0.7033	Intermediate Similarity	NPC472112
0.7029	Intermediate Similarity	NPC469938
0.7029	Intermediate Similarity	NPC329688
0.7029	Intermediate Similarity	NPC189812
0.7024	Intermediate Similarity	NPC285469
0.7021	Intermediate Similarity	NPC300183
0.7018	Intermediate Similarity	NPC265100
0.7018	Intermediate Similarity	NPC90723
0.7017	Intermediate Similarity	NPC119700
0.7012	Intermediate Similarity	NPC288838
0.7	Intermediate Similarity	NPC133003
0.7	Intermediate Similarity	NPC215584
0.7	Intermediate Similarity	NPC44773
0.6995	Remote Similarity	NPC476460
0.6989	Remote Similarity	NPC151635
0.6989	Remote Similarity	NPC227582
0.6988	Remote Similarity	NPC40070
0.6984	Remote Similarity	NPC123019
0.6984	Remote Similarity	NPC137589
0.6984	Remote Similarity	NPC260900
0.6981	Remote Similarity	NPC325252
0.6978	Remote Similarity	NPC34271
0.6973	Remote Similarity	NPC289299
0.6973	Remote Similarity	NPC57994
0.6968	Remote Similarity	NPC475151
0.6964	Remote Similarity	NPC207726
0.6961	Remote Similarity	NPC135601
0.6961	Remote Similarity	NPC141612
0.6961	Remote Similarity	NPC17273
0.6959	Remote Similarity	NPC204303
0.6957	Remote Similarity	NPC316018
0.6957	Remote Similarity	NPC73767
0.6957	Remote Similarity	NPC314058
0.6951	Remote Similarity	NPC314372
0.6947	Remote Similarity	NPC98715
0.6944	Remote Similarity	NPC228835
0.6944	Remote Similarity	NPC472294
0.6941	Remote Similarity	NPC67056
0.6941	Remote Similarity	NPC293487
0.6941	Remote Similarity	NPC80681
0.694	Remote Similarity	NPC324091
0.6935	Remote Similarity	NPC472116
0.6933	Remote Similarity	NPC190296
0.6932	Remote Similarity	NPC293216
0.6932	Remote Similarity	NPC469529

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 NPC200743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	594
0.2-0.3	735
0.3-0.4	2176
0.4-0.5	2653
0.5-0.6	1997
0.6-0.7	610
0.7-0.8	53
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7748	Intermediate Similarity	NPD3385	Approved
0.7697	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5473	Discontinued
0.76	Intermediate Similarity	NPD3654	Approved
0.7532	Intermediate Similarity	NPD5254	Discontinued
0.7529	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5021	Discontinued
0.7484	Intermediate Similarity	NPD6554	Approved
0.7484	Intermediate Similarity	NPD45	Approved
0.7438	Intermediate Similarity	NPD1683	Approved
0.741	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4640	Approved
0.7396	Intermediate Similarity	NPD4639	Approved
0.7396	Intermediate Similarity	NPD4638	Approved
0.7394	Intermediate Similarity	NPD4326	Phase 2
0.7384	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4075	Phase 2
0.7377	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5315	Discontinued
0.7358	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4880	Discontinued
0.7342	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3323	Discontinued
0.7314	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2172	Phase 1
0.7294	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4547	Phase 3
0.7247	Intermediate Similarity	NPD5809	Phase 3
0.7209	Intermediate Similarity	NPD5472	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4462	Approved
0.7195	Intermediate Similarity	NPD4463	Approved
0.7184	Intermediate Similarity	NPD5501	Discontinued
0.7181	Intermediate Similarity	NPD6987	Phase 1
0.7176	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD3320	Approved
0.7175	Intermediate Similarity	NPD3318	Approved
0.7175	Intermediate Similarity	NPD3319	Phase 1
0.7174	Intermediate Similarity	NPD6664	Approved
0.7166	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD2879	Approved
0.7166	Intermediate Similarity	NPD2881	Approved
0.7161	Intermediate Similarity	NPD1251	Discontinued
0.7159	Intermediate Similarity	NPD5897	Approved
0.7159	Intermediate Similarity	NPD5899	Approved
0.7159	Intermediate Similarity	NPD5898	Approved
0.7152	Intermediate Similarity	NPD1262	Discovery
0.7151	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4300	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD4499	Approved
0.7105	Intermediate Similarity	NPD3905	Phase 3
0.7091	Intermediate Similarity	NPD3835	Phase 3
0.7091	Intermediate Similarity	NPD3833	Phase 3
0.7089	Intermediate Similarity	NPD1255	Approved
0.7089	Intermediate Similarity	NPD1256	Approved
0.7089	Intermediate Similarity	NPD1253	Approved
0.7089	Intermediate Similarity	NPD1254	Approved
0.7088	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5471	Phase 3
0.7081	Intermediate Similarity	NPD5020	Approved
0.7079	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2915	Discontinued
0.7072	Intermediate Similarity	NPD7233	Approved
0.7072	Intermediate Similarity	NPD7234	Approved
0.7045	Intermediate Similarity	NPD3505	Approved
0.7045	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4398	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4181	Approved
0.7045	Intermediate Similarity	NPD3506	Approved
0.7043	Intermediate Similarity	NPD6846	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1630	Approved
0.7037	Intermediate Similarity	NPD4047	Discontinued
0.7035	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD947	Approved
0.703	Intermediate Similarity	NPD3100	Discontinued
0.7024	Intermediate Similarity	NPD2580	Discontinued
0.7018	Intermediate Similarity	NPD3583	Phase 2
0.7017	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3610	Approved
0.7011	Intermediate Similarity	NPD3609	Approved
0.701	Intermediate Similarity	NPD7455	Approved
0.701	Intermediate Similarity	NPD7454	Approved
0.7006	Intermediate Similarity	NPD4079	Approved
0.7006	Intermediate Similarity	NPD4076	Approved
0.7005	Intermediate Similarity	NPD6999	Discontinued
0.7005	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4918	Discontinued
0.6994	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4509	Discontinued
0.6989	Remote Similarity	NPD5104	Approved
0.6987	Remote Similarity	NPD3475	Approved
0.6987	Remote Similarity	NPD3476	Approved
0.6973	Remote Similarity	NPD7618	Phase 3
0.6973	Remote Similarity	NPD7619	Phase 3
0.6973	Remote Similarity	NPD7944	Discontinued
0.6973	Remote Similarity	NPD4602	Approved
0.6971	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD750	Phase 2
0.6971	Remote Similarity	NPD43	Approved
0.6971	Remote Similarity	NPD6182	Approved
0.6954	Remote Similarity	NPD1573	Approved
0.6954	Remote Similarity	NPD1575	Approved
0.6946	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6158	Phase 2
0.6946	Remote Similarity	NPD2882	Phase 1
0.6944	Remote Similarity	NPD7564	Discontinued
0.694	Remote Similarity	NPD6281	Approved
0.6936	Remote Similarity	NPD6446	Discontinued
0.6936	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4128	Approved
0.6932	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4399	Phase 2
0.6923	Remote Similarity	NPD3961	Discontinued
0.6919	Remote Similarity	NPD1631	Approved
0.6914	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2118	Approved
0.6903	Remote Similarity	NPD2119	Approved
0.6898	Remote Similarity	NPD2880	Discontinued
0.6893	Remote Similarity	NPD3238	Discontinued
0.6893	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2916	Discontinued
0.689	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5904	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4601	Approved
0.6878	Remote Similarity	NPD4600	Approved
0.6871	Remote Similarity	NPD1722	Approved
0.6868	Remote Similarity	NPD6217	Discontinued
0.6864	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4030	Approved
0.6855	Remote Similarity	NPD4028	Approved
0.6855	Remote Similarity	NPD4029	Approved
0.6854	Remote Similarity	NPD2753	Discontinued
0.6852	Remote Similarity	NPD786	Approved
0.6845	Remote Similarity	NPD4848	Phase 1
0.6839	Remote Similarity	NPD2639	Approved
0.6839	Remote Similarity	NPD2642	Approved
0.6837	Remote Similarity	NPD2411	Approved
0.6833	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6507	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2150	Discontinued
0.6823	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD5426	Phase 3
0.6813	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1343	Approved
0.68	Remote Similarity	NPD2844	Phase 3
0.6798	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD1534	Approved
0.6792	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6995	Phase 1
0.6778	Remote Similarity	NPD2479	Phase 3
0.6778	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD2481	Approved
0.6772	Remote Similarity	NPD53	Approved
0.6772	Remote Similarity	NPD7778	Approved
0.6772	Remote Similarity	NPD7777	Approved
0.677	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6285	Phase 2
0.6763	Remote Similarity	NPD5400	Approved
0.6761	Remote Similarity	NPD1325	Approved
0.6761	Remote Similarity	NPD1326	Approved
0.675	Remote Similarity	NPD3944	Approved
0.675	Remote Similarity	NPD3942	Approved
0.6739	Remote Similarity	NPD4948	Discontinued
0.6739	Remote Similarity	NPD4988	Discontinued
0.6739	Remote Similarity	NPD7394	Phase 2
0.6728	Remote Similarity	NPD200	Phase 2
0.6728	Remote Similarity	NPD201	Phase 2
0.6727	Remote Similarity	NPD2006	Phase 2
0.6726	Remote Similarity	NPD2430	Phase 2
0.6722	Remote Similarity	NPD6448	Phase 1
0.6721	Remote Similarity	NPD5075	Discontinued
0.6721	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5003	Discontinued
0.6707	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2837	Discontinued
0.6705	Remote Similarity	NPD2641	Approved
0.6705	Remote Similarity	NPD2640	Approved
0.6705	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7001	Phase 3
0.6687	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6595	Phase 3
0.6685	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6452	Discontinued
0.6685	Remote Similarity	NPD4524	Discontinued
0.6684	Remote Similarity	NPD4397	Phase 1
0.6684	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD972	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