NPASS Compound

Structure

CID311330 OpenBabel06191716122D 25 29 0 0 1 0 0 0 0 0999 V2000 2.0217 -2.3472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0617 -2.3408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6783 1.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8629 -0.5053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3126 0.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3193 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4859 0.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4993 2.3821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8514 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3695 0.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0060 -0.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5241 0.5020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8327 1.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6660 0.9618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6726 1.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 1.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6908 -0.9623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8394 0.4916 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3755 -0.9519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8329 0.4808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5361 -1.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6847 0.0104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8333 2.4041 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 -1.4663 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 14 2 0 0 0 0 8 15 2 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 13 1 1 0 0 0 16 20 1 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 6 0 0 0 18 22 1 1 0 0 0 18 23 1 0 0 0 0 19 21 1 0 0 0 0 19 25 1 1 0 0 0 20 23 1 1 0 0 0 22 3 1 6 0 0 0 23 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	339.26
Volume:	375.459
LogP:	5.378
LogD:	4.604
LogS:	-6.155
# Rotatable Bonds:	0
TPSA:	32.26
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	4.312
Fsp3:	0.739
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:	-4.789
MDCK Permeability:	2.4615768779767677e-05
Pgp-inhibitor:	0.691
Pgp-substrate:	0.202
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.179
30% Bioavailability (F30%):	0.486

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	91.3438949584961%
Volume Distribution (VD):	1.221
Pgp-substrate:	6.687124729156494%

ADMET: Metabolism

CYP1A2-inhibitor:	0.317
CYP1A2-substrate:	0.379
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.588
CYP2C9-substrate:	0.593
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.498

ADMET: Excretion

Clearance (CL):	5.432
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.054
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.871
Carcinogencity:	0.026
Eye Corrosion:	0.113
Eye Irritation:	0.852
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC311330

Natural Product ID:	NPC311330
*Common Name:**	Polyveoline
IUPAC Name:	n.a.
Synonyms:	Polyveoline
Standard InCHIKey:	HVKUYPXKTAMIFI-SZKCUPFNSA-N
Standard InCHI:	InChI=1S/C23H33NO/c1-21(2)17-9-11-23(4)18(22(17,3)12-10-19(21)25)13-16-20(23)14-7-5-6-8-15(14)24-16/h5-8,16-20,24-25H,9-13H2,1-4H3/t16-,17-,18-,19+,20-,22-,23+/m0/s1
SMILES:	O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@H]2C[C@H]2[C@@H]1c1c(N2)cccc1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086376
PubChem CID:	46871719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001146] Indolines [CHEMONTID:0003476] 2,3-Cyclopentanoindolines

*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]
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]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16473	Araucaria bidwillii	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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[TM-MC]
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]
NPO24123	Ramalina scopulorum	Species	Ramalinaceae	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]
NPO28729	Spirostachys africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14893	Streptomyces eurocidicus	Species	Streptomycetaceae	Bacteria	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]

☑ 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
ED50	1
IC50	6
Ki	2
Others	1

Activity Type	# Activity
Individual Protein	3
Organism	1
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4419	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase	Oryctolagus cuniculus	IC50	=	620000.0	nM	PMID[521339]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	IC50	=	30000.0	nM	PMID[521339]
NPT2	Others	Unspecified		Ratio IC50	=	3.0	n.a.	PMID[521339]
NPT2	Others	Unspecified		Ki	=	50000.0	nM	PMID[521339]
NPT2	Others	Unspecified		Ki	=	18000.0	nM	PMID[521339]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	ED50	=	54.0	uM	PMID[521339]
NPT2	Others	Unspecified		IC50	=	110000.0	nM	PMID[521339]
NPT2	Others	Unspecified		IC50	=	310000.0	nM	PMID[521339]
NPT714	Individual Protein	Fructose-bisphosphate aldolase A	Oryctolagus cuniculus	IC50	=	270000.0	nM	PMID[521339]
NPT2	Others	Unspecified		IC50	=	80000.0	nM	PMID[521339]

☑ 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 NPC311330 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	253
0.1-0.2	1217
0.2-0.3	4480
0.3-0.4	18649
0.4-0.5	13793
0.5-0.6	3644
0.6-0.7	613
0.7-0.8	44
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9085	High Similarity	NPC212799
0.8243	Intermediate Similarity	NPC264589
0.8063	Intermediate Similarity	NPC97525
0.7818	Intermediate Similarity	NPC198339
0.7792	Intermediate Similarity	NPC475763
0.7665	Intermediate Similarity	NPC302191
0.7605	Intermediate Similarity	NPC300688
0.7574	Intermediate Similarity	NPC165201
0.7544	Intermediate Similarity	NPC119700
0.7516	Intermediate Similarity	NPC472103
0.7483	Intermediate Similarity	NPC243162
0.747	Intermediate Similarity	NPC475097
0.7457	Intermediate Similarity	NPC206967
0.744	Intermediate Similarity	NPC6093
0.7427	Intermediate Similarity	NPC52262
0.7397	Intermediate Similarity	NPC40488
0.7346	Intermediate Similarity	NPC472102
0.7346	Intermediate Similarity	NPC309531
0.7299	Intermediate Similarity	NPC34271
0.7278	Intermediate Similarity	NPC151939
0.7247	Intermediate Similarity	NPC231342
0.7229	Intermediate Similarity	NPC154293
0.717	Intermediate Similarity	NPC318086
0.7126	Intermediate Similarity	NPC201700
0.7091	Intermediate Similarity	NPC99632
0.7091	Intermediate Similarity	NPC282339
0.7086	Intermediate Similarity	NPC99428
0.7072	Intermediate Similarity	NPC473747
0.7059	Intermediate Similarity	NPC478140
0.7055	Intermediate Similarity	NPC477156
0.7055	Intermediate Similarity	NPC477157
0.7034	Intermediate Similarity	NPC475915
0.703	Intermediate Similarity	NPC315368
0.7025	Intermediate Similarity	NPC116519
0.7011	Intermediate Similarity	NPC19679
0.6995	Remote Similarity	NPC475489
0.6995	Remote Similarity	NPC475151
0.6981	Remote Similarity	NPC472100
0.6923	Remote Similarity	NPC313673
0.6919	Remote Similarity	NPC475223
0.6919	Remote Similarity	NPC476441
0.6901	Remote Similarity	NPC473880
0.6886	Remote Similarity	NPC286871
0.6886	Remote Similarity	NPC176983
0.6886	Remote Similarity	NPC472117
0.6886	Remote Similarity	NPC472120
0.6886	Remote Similarity	NPC472101
0.6882	Remote Similarity	NPC246983
0.6882	Remote Similarity	NPC469915
0.6882	Remote Similarity	NPC475448
0.6879	Remote Similarity	NPC186284
0.6879	Remote Similarity	NPC22082
0.6875	Remote Similarity	NPC470579
0.6867	Remote Similarity	NPC36495
0.6839	Remote Similarity	NPC218594
0.6839	Remote Similarity	NPC99043
0.6829	Remote Similarity	NPC478076
0.6828	Remote Similarity	NPC123019
0.6826	Remote Similarity	NPC68650
0.6809	Remote Similarity	NPC18661
0.6805	Remote Similarity	NPC472106
0.6805	Remote Similarity	NPC475420
0.6793	Remote Similarity	NPC477041
0.6793	Remote Similarity	NPC477044
0.6786	Remote Similarity	NPC472121
0.6786	Remote Similarity	NPC85651
0.6784	Remote Similarity	NPC472118
0.6778	Remote Similarity	NPC474059
0.6765	Remote Similarity	NPC214960
0.6765	Remote Similarity	NPC279527
0.6763	Remote Similarity	NPC329688
0.6763	Remote Similarity	NPC189812
0.6757	Remote Similarity	NPC477045
0.6755	Remote Similarity	NPC478079
0.6755	Remote Similarity	NPC145754
0.6754	Remote Similarity	NPC475165
0.6744	Remote Similarity	NPC126492
0.6739	Remote Similarity	NPC90967
0.6726	Remote Similarity	NPC248117
0.6726	Remote Similarity	NPC225319
0.6724	Remote Similarity	NPC264482
0.6724	Remote Similarity	NPC203202
0.6723	Remote Similarity	NPC477159
0.6719	Remote Similarity	NPC250129
0.6709	Remote Similarity	NPC315051
0.6707	Remote Similarity	NPC222029
0.6707	Remote Similarity	NPC104345
0.6707	Remote Similarity	NPC469428
0.6705	Remote Similarity	NPC34508
0.6687	Remote Similarity	NPC109787
0.6687	Remote Similarity	NPC114808
0.6685	Remote Similarity	NPC205403
0.6685	Remote Similarity	NPC95783
0.6685	Remote Similarity	NPC97584
0.6667	Remote Similarity	NPC181928
0.6667	Remote Similarity	NPC193410
0.663	Remote Similarity	NPC85066
0.663	Remote Similarity	NPC181502
0.663	Remote Similarity	NPC221687
0.6629	Remote Similarity	NPC256288
0.6627	Remote Similarity	NPC477158
0.6625	Remote Similarity	NPC477155
0.6615	Remote Similarity	NPC471284
0.6609	Remote Similarity	NPC285622
0.6609	Remote Similarity	NPC473743
0.6609	Remote Similarity	NPC476425
0.6607	Remote Similarity	NPC123241
0.6607	Remote Similarity	NPC61013
0.6606	Remote Similarity	NPC206592
0.6604	Remote Similarity	NPC130251
0.6603	Remote Similarity	NPC132847
0.6599	Remote Similarity	NPC264580
0.6598	Remote Similarity	NPC235900
0.6595	Remote Similarity	NPC97100
0.6595	Remote Similarity	NPC473375
0.6593	Remote Similarity	NPC473298
0.6593	Remote Similarity	NPC22689
0.6593	Remote Similarity	NPC105055
0.6592	Remote Similarity	NPC2933
0.6588	Remote Similarity	NPC293458
0.6588	Remote Similarity	NPC469741
0.6581	Remote Similarity	NPC476685
0.6581	Remote Similarity	NPC476687
0.6581	Remote Similarity	NPC476689
0.6579	Remote Similarity	NPC477043
0.6573	Remote Similarity	NPC476428
0.6562	Remote Similarity	NPC301760
0.6556	Remote Similarity	NPC476319
0.6556	Remote Similarity	NPC476095
0.6556	Remote Similarity	NPC259626
0.6554	Remote Similarity	NPC270009
0.655	Remote Similarity	NPC311276
0.655	Remote Similarity	NPC40779
0.6548	Remote Similarity	NPC469785
0.6548	Remote Similarity	NPC29285
0.6548	Remote Similarity	NPC285469
0.6547	Remote Similarity	NPC56168
0.6545	Remote Similarity	NPC187456
0.6541	Remote Similarity	NPC198205
0.6541	Remote Similarity	NPC21483
0.6536	Remote Similarity	NPC472109
0.6536	Remote Similarity	NPC472110
0.6532	Remote Similarity	NPC167724
0.6532	Remote Similarity	NPC224970
0.6532	Remote Similarity	NPC473484
0.6532	Remote Similarity	NPC469462
0.6532	Remote Similarity	NPC223595
0.6525	Remote Similarity	NPC79618
0.6524	Remote Similarity	NPC311054
0.6524	Remote Similarity	NPC112752
0.6519	Remote Similarity	NPC473615
0.6514	Remote Similarity	NPC96901
0.6514	Remote Similarity	NPC472123
0.6514	Remote Similarity	NPC251212
0.6514	Remote Similarity	NPC139085
0.6514	Remote Similarity	NPC214626
0.6512	Remote Similarity	NPC470508
0.6509	Remote Similarity	NPC113946
0.6509	Remote Similarity	NPC469762
0.6507	Remote Similarity	NPC101139
0.6506	Remote Similarity	NPC66936
0.65	Remote Similarity	NPC472294
0.65	Remote Similarity	NPC474695
0.6497	Remote Similarity	NPC186669
0.6494	Remote Similarity	NPC280548
0.6491	Remote Similarity	NPC16667
0.6489	Remote Similarity	NPC107828
0.6489	Remote Similarity	NPC90358
0.6484	Remote Similarity	NPC229484
0.6484	Remote Similarity	NPC285841
0.648	Remote Similarity	NPC192270
0.648	Remote Similarity	NPC473547
0.6477	Remote Similarity	NPC87755
0.6477	Remote Similarity	NPC472586
0.6471	Remote Similarity	NPC198390
0.6471	Remote Similarity	NPC252794
0.6465	Remote Similarity	NPC96131
0.6464	Remote Similarity	NPC307396
0.6461	Remote Similarity	NPC213468
0.6461	Remote Similarity	NPC6974
0.6455	Remote Similarity	NPC49196
0.6455	Remote Similarity	NPC79129
0.6455	Remote Similarity	NPC81654
0.6455	Remote Similarity	NPC249150
0.6455	Remote Similarity	NPC195461
0.6455	Remote Similarity	NPC313985
0.6452	Remote Similarity	NPC34717
0.6448	Remote Similarity	NPC292675
0.6448	Remote Similarity	NPC284706
0.6447	Remote Similarity	NPC97388
0.6444	Remote Similarity	NPC472108
0.6444	Remote Similarity	NPC139291
0.6441	Remote Similarity	NPC320147
0.6437	Remote Similarity	NPC317430
0.6436	Remote Similarity	NPC50503
0.6433	Remote Similarity	NPC201424
0.6433	Remote Similarity	NPC149379
0.6429	Remote Similarity	NPC469763
0.6429	Remote Similarity	NPC73952
0.6429	Remote Similarity	NPC469765

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 NPC311330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	549
0.2-0.3	725
0.3-0.4	1361
0.4-0.5	3977
0.5-0.6	2162
0.6-0.7	208
0.7-0.8	10
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
0.7643	Intermediate Similarity	NPD5743	Approved
0.7643	Intermediate Similarity	NPD5741	Approved
0.7643	Intermediate Similarity	NPD5742	Approved
0.758	Intermediate Similarity	NPD4121	Phase 3
0.758	Intermediate Similarity	NPD4120	Approved
0.7355	Intermediate Similarity	NPD7295	Approved
0.7179	Intermediate Similarity	NPD7487	Discontinued
0.7124	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7082	Approved
0.707	Intermediate Similarity	NPD7259	Approved
0.7027	Intermediate Similarity	NPD6900	Discontinued
0.7011	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8131	Suspended
0.6914	Remote Similarity	NPD7962	Phase 2
0.6909	Remote Similarity	NPD6694	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6789	Approved
0.6855	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6026	Approved
0.6824	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3638	Discontinued
0.679	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5253	Approved
0.6743	Remote Similarity	NPD7479	Phase 2
0.6726	Remote Similarity	NPD5989	Phase 1
0.6712	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7606	Phase 3
0.6706	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6069	Approved
0.669	Remote Similarity	NPD6070	Approved
0.669	Remote Similarity	NPD2999	Approved
0.669	Remote Similarity	NPD3001	Approved
0.6687	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8401	Approved
0.6667	Remote Similarity	NPD8402	Approved
0.6667	Remote Similarity	NPD8400	Approved
0.6667	Remote Similarity	NPD4116	Approved
0.6626	Remote Similarity	NPD7478	Approved
0.6623	Remote Similarity	NPD6320	Approved
0.6621	Remote Similarity	NPD4031	Approved
0.6621	Remote Similarity	NPD1723	Phase 2
0.6621	Remote Similarity	NPD4032	Approved
0.6621	Remote Similarity	NPD1720	Phase 2
0.6605	Remote Similarity	NPD5060	Phase 1
0.6605	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7582	Discontinued
0.6596	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6301	Phase 2
0.6573	Remote Similarity	NPD2039	Approved
0.6573	Remote Similarity	NPD2038	Approved
0.6566	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1710	Approved
0.6552	Remote Similarity	NPD1813	Discontinued
0.6552	Remote Similarity	NPD5629	Discontinued
0.6549	Remote Similarity	NPD7633	Discontinued
0.6549	Remote Similarity	NPD1108	Approved
0.6549	Remote Similarity	NPD1107	Approved
0.6514	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6892	Discontinued
0.6509	Remote Similarity	NPD8630	Approved
0.6507	Remote Similarity	NPD2622	Approved
0.6486	Remote Similarity	NPD5657	Phase 3
0.6486	Remote Similarity	NPD5511	Discontinued
0.6485	Remote Similarity	NPD5941	Approved
0.6485	Remote Similarity	NPD3645	Discontinued
0.6485	Remote Similarity	NPD5942	Approved
0.6483	Remote Similarity	NPD2913	Approved
0.6483	Remote Similarity	NPD2914	Approved
0.6481	Remote Similarity	NPD5024	Approved
0.6474	Remote Similarity	NPD865	Approved
0.6474	Remote Similarity	NPD864	Approved
0.6471	Remote Similarity	NPD1950	Approved
0.6471	Remote Similarity	NPD7599	Phase 2
0.6471	Remote Similarity	NPD1949	Approved
0.6467	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.646	Remote Similarity	NPD3625	Discontinued
0.6456	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4600	Approved
0.6455	Remote Similarity	NPD4601	Approved
0.6452	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7105	Phase 1
0.6446	Remote Similarity	NPD1405	Approved
0.6443	Remote Similarity	NPD2212	Approved
0.6443	Remote Similarity	NPD1922	Discontinued
0.6443	Remote Similarity	NPD2210	Approved
0.6437	Remote Similarity	NPD5021	Discontinued
0.6433	Remote Similarity	NPD7600	Phase 2
0.6433	Remote Similarity	NPD1595	Approved
0.6433	Remote Similarity	NPD1594	Phase 3
0.6429	Remote Similarity	NPD5086	Approved
0.6424	Remote Similarity	NPD6378	Approved
0.6415	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3720	Discontinued
0.641	Remote Similarity	NPD1068	Approved
0.641	Remote Similarity	NPD4275	Approved
0.641	Remote Similarity	NPD4274	Approved
0.6408	Remote Similarity	NPD4115	Approved
0.6408	Remote Similarity	NPD4114	Approved
0.6403	Remote Similarity	NPD4735	Approved
0.6403	Remote Similarity	NPD4734	Approved
0.6403	Remote Similarity	NPD4719	Phase 2
0.6398	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1738	Approved
0.6393	Remote Similarity	NPD8431	Approved
0.638	Remote Similarity	NPD2820	Phase 3
0.6375	Remote Similarity	NPD6342	Discontinued
0.6374	Remote Similarity	NPD6283	Phase 2
0.637	Remote Similarity	NPD3148	Approved
0.637	Remote Similarity	NPD3147	Approved
0.637	Remote Similarity	NPD2658	Approved
0.637	Remote Similarity	NPD2659	Approved
0.637	Remote Similarity	NPD3149	Approved
0.637	Remote Similarity	NPD3150	Approved
0.6369	Remote Similarity	NPD4079	Approved
0.6369	Remote Similarity	NPD4076	Approved
0.6358	Remote Similarity	NPD6635	Approved
0.6354	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD2381	Approved
0.6348	Remote Similarity	NPD2382	Approved
0.6348	Remote Similarity	NPD2380	Approved
0.634	Remote Similarity	NPD2938	Approved
0.634	Remote Similarity	NPD2940	Approved
0.6338	Remote Similarity	NPD3545	Approved
0.6338	Remote Similarity	NPD3546	Approved
0.6333	Remote Similarity	NPD6595	Phase 3
0.6333	Remote Similarity	NPD6879	Phase 2
0.6333	Remote Similarity	NPD6878	Phase 2
0.6333	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD8118	Discontinued
0.6327	Remote Similarity	NPD5631	Phase 3
0.6325	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5554	Approved
0.6319	Remote Similarity	NPD2365	Approved
0.6313	Remote Similarity	NPD3505	Approved
0.6313	Remote Similarity	NPD3506	Approved
0.6309	Remote Similarity	NPD7522	Discontinued
0.6307	Remote Similarity	NPD1325	Approved
0.6307	Remote Similarity	NPD1326	Approved
0.6307	Remote Similarity	NPD7474	Suspended
0.6301	Remote Similarity	NPD1764	Approved
0.6301	Remote Similarity	NPD1762	Approved
0.6296	Remote Similarity	NPD4707	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5185	Approved
0.6289	Remote Similarity	NPD5184	Approved
0.6289	Remote Similarity	NPD5182	Approved
0.6289	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7957	Phase 1
0.6284	Remote Similarity	NPD7508	Discontinued
0.6282	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2036	Approved
0.628	Remote Similarity	NPD4430	Phase 2
0.6278	Remote Similarity	NPD8386	Phase 2
0.6275	Remote Similarity	NPD519	Approved
0.6273	Remote Similarity	NPD5318	Discontinued
0.6273	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6636	Phase 3
0.6273	Remote Similarity	NPD4411	Phase 1
0.6268	Remote Similarity	NPD564	Approved
0.6268	Remote Similarity	NPD563	Approved
0.6267	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD3141	Discontinued
0.6264	Remote Similarity	NPD3790	Phase 2
0.6259	Remote Similarity	NPD5179	Approved
0.6259	Remote Similarity	NPD5180	Approved
0.6259	Remote Similarity	NPD5181	Approved
0.6259	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD1953	Discontinued
0.6257	Remote Similarity	NPD6619	Phase 3
0.6257	Remote Similarity	NPD2789	Approved
0.625	Remote Similarity	NPD2679	Approved
0.625	Remote Similarity	NPD2678	Approved
0.6243	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD5599	Discontinued
0.6242	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD8263	Discontinued
0.6242	Remote Similarity	NPD5162	Approved
0.6242	Remote Similarity	NPD6660	Discontinued
0.6236	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD5430	Discontinued
0.6226	Remote Similarity	NPD1316	Discontinued
0.6224	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5498	Phase 2
0.6221	Remote Similarity	NPD6886	Approved
0.6221	Remote Similarity	NPD6885	Approved
0.622	Remote Similarity	NPD1908	Phase 2
0.6215	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD4463	Approved
0.6213	Remote Similarity	NPD4462	Approved
0.6212	Remote Similarity	NPD5939	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