NPASS Compound

Structure

CID291610 OpenBabel06191716102D 21 23 0 0 0 0 0 0 0 0999 V2000 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 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 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.19
Volume:	317.686
LogP:	4.134
LogD:	3.658
LogS:	-3.309
# Rotatable Bonds:	4
TPSA:	6.48
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.841
Synthetic Accessibility Score:	1.87
Fsp3:	0.368
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:	-4.717
MDCK Permeability:	1.8741373423836194e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	88.34962463378906%
Volume Distribution (VD):	3.016
Pgp-substrate:	13.549335479736328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.219
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.17
CYP2C19-substrate:	0.972
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.991
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	13.974
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.948
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.569
Maximum Recommended Daily Dose:	0.593
Skin Sensitization:	0.917
Carcinogencity:	0.079
Eye Corrosion:	0.008
Eye Irritation:	0.039
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC291610

Natural Product ID:	NPC291610
*Common Name:**	Bamipine
IUPAC Name:	N-benzyl-1-methyl-N-phenylpiperidin-4-amine
Synonyms:	Bamipine; Piperamine
Standard InCHIKey:	VZSXTYKGYWISGQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H24N2/c1-20-14-12-19(13-15-20)21(18-10-6-3-7-11-18)16-17-8-4-2-5-9-17/h2-11,19H,12-16H2,1H3
SMILES:	CN1CCC(CC1)N(c1ccccc1)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520400
PubChem CID:	72075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000185] Phenylmethylamines [CHEMONTID:0004204] Phenylbenzamines

*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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO3795	Piper hispidum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9599264]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3795	Piper hispidum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3795	Piper hispidum	Species	Piperaceae	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
AC50	3
MIC	1
Others	9
Potency	7

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Organism	2
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	LC50	=	64.08	ug.mL-1	PMID[500644]
NPT4288	Individual Protein	Histamine H1 receptor	Cavia porcellus	pKb	=	8.55	n.a.	PMID[500644]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	29847	nM	PubChem BioAssay data set
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	29.0	%	PMID[500644]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	6.25	ug.mL-1	PMID[500644]
NPT2	Others	Unspecified		Ac50	n.a.	10.86	uM	PMID[500645]
NPT2	Others	Unspecified		AC50	n.a.	1000.0	nM	PMID[500645]
NPT2	Others	Unspecified		Ac50	n.a.	1.0	uM	PMID[500645]
NPT2	Others	Unspecified		Ac50	n.a.	7.079	uM	PMID[500645]
NPT2	Others	Unspecified		Ac50	n.a.	4.467	uM	PMID[500645]
NPT2	Others	Unspecified		Ac50	n.a.	15.34	uM	PMID[500645]
NPT2	Others	Unspecified		AC50	n.a.	7079.5	nM	PMID[500645]
NPT2	Others	Unspecified		AC50	n.a.	4466.8	nM	PMID[500645]
NPT2	Others	Unspecified		Potency	n.a.	26601.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9438.4	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	21313.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9520.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	14960.1	nM	PubChem BioAssay data set

☑ 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 NPC291610 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	769
0.1-0.2	8348
0.2-0.3	14992
0.3-0.4	12076
0.4-0.5	4834
0.5-0.6	1361
0.6-0.7	285
0.7-0.8	27
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8081	Intermediate Similarity	NPC470926
0.8	Intermediate Similarity	NPC475915
0.7965	Intermediate Similarity	NPC313449
0.7928	Intermediate Similarity	NPC187036
0.7928	Intermediate Similarity	NPC296163
0.7807	Intermediate Similarity	NPC192209
0.7798	Intermediate Similarity	NPC302790
0.7788	Intermediate Similarity	NPC288232
0.7667	Intermediate Similarity	NPC252794
0.7623	Intermediate Similarity	NPC473417
0.7586	Intermediate Similarity	NPC264580
0.7545	Intermediate Similarity	NPC79618
0.7545	Intermediate Similarity	NPC434
0.75	Intermediate Similarity	NPC329430
0.7475	Intermediate Similarity	NPC229477
0.7449	Intermediate Similarity	NPC104070
0.7447	Intermediate Similarity	NPC271642
0.7407	Intermediate Similarity	NPC239854
0.7373	Intermediate Similarity	NPC226143
0.734	Intermediate Similarity	NPC98976
0.7321	Intermediate Similarity	NPC164802
0.7317	Intermediate Similarity	NPC476950
0.7282	Intermediate Similarity	NPC191444
0.7273	Intermediate Similarity	NPC134825
0.725	Intermediate Similarity	NPC257490
0.72	Intermediate Similarity	NPC169016
0.7184	Intermediate Similarity	NPC176858
0.7177	Intermediate Similarity	NPC145754
0.7157	Intermediate Similarity	NPC262295
0.7119	Intermediate Similarity	NPC313673
0.7083	Intermediate Similarity	NPC291962
0.7083	Intermediate Similarity	NPC177684
0.7063	Intermediate Similarity	NPC9856
0.704	Intermediate Similarity	NPC478079
0.7025	Intermediate Similarity	NPC161956
0.7025	Intermediate Similarity	NPC112373
0.7025	Intermediate Similarity	NPC258531
0.7023	Intermediate Similarity	NPC251722
0.7023	Intermediate Similarity	NPC314102
0.7	Intermediate Similarity	NPC81561
0.6981	Remote Similarity	NPC108800
0.6977	Remote Similarity	NPC313352
0.697	Remote Similarity	NPC130251
0.6952	Remote Similarity	NPC78154
0.6942	Remote Similarity	NPC54102
0.6942	Remote Similarity	NPC162689
0.6939	Remote Similarity	NPC12857
0.6931	Remote Similarity	NPC119677
0.6923	Remote Similarity	NPC30445
0.6923	Remote Similarity	NPC111233
0.6917	Remote Similarity	NPC186284
0.6917	Remote Similarity	NPC22082
0.6917	Remote Similarity	NPC148140
0.6912	Remote Similarity	NPC469735
0.6911	Remote Similarity	NPC182570
0.6911	Remote Similarity	NPC48564
0.6911	Remote Similarity	NPC265605
0.6903	Remote Similarity	NPC474695
0.69	Remote Similarity	NPC231986
0.6893	Remote Similarity	NPC258046
0.688	Remote Similarity	NPC122718
0.6875	Remote Similarity	NPC474430
0.687	Remote Similarity	NPC471123
0.6864	Remote Similarity	NPC57051
0.6861	Remote Similarity	NPC469740
0.6857	Remote Similarity	NPC173991
0.6822	Remote Similarity	NPC53044
0.6815	Remote Similarity	NPC63157
0.6815	Remote Similarity	NPC473868
0.6814	Remote Similarity	NPC328877
0.6794	Remote Similarity	NPC300299
0.6788	Remote Similarity	NPC264589
0.6774	Remote Similarity	NPC268534
0.6767	Remote Similarity	NPC469560
0.6765	Remote Similarity	NPC20144
0.6759	Remote Similarity	NPC322040
0.6757	Remote Similarity	NPC75496
0.6754	Remote Similarity	NPC473418
0.6748	Remote Similarity	NPC316582
0.6746	Remote Similarity	NPC476322
0.6741	Remote Similarity	NPC59084
0.6723	Remote Similarity	NPC314141
0.6721	Remote Similarity	NPC240136
0.6721	Remote Similarity	NPC228515
0.6721	Remote Similarity	NPC297486
0.6721	Remote Similarity	NPC471402
0.6718	Remote Similarity	NPC184437
0.6714	Remote Similarity	NPC206592
0.6696	Remote Similarity	NPC326792
0.6694	Remote Similarity	NPC215519
0.6691	Remote Similarity	NPC109787
0.6691	Remote Similarity	NPC21605
0.6667	Remote Similarity	NPC301760
0.6667	Remote Similarity	NPC46358
0.6667	Remote Similarity	NPC91958
0.6667	Remote Similarity	NPC98269
0.6667	Remote Similarity	NPC325662
0.6667	Remote Similarity	NPC88097
0.6667	Remote Similarity	NPC104483
0.6639	Remote Similarity	NPC476566
0.6638	Remote Similarity	NPC20322
0.6618	Remote Similarity	NPC2949
0.6617	Remote Similarity	NPC198988
0.6617	Remote Similarity	NPC325599
0.6615	Remote Similarity	NPC476131
0.6613	Remote Similarity	NPC179605
0.6613	Remote Similarity	NPC279385
0.6612	Remote Similarity	NPC218710
0.6609	Remote Similarity	NPC313362
0.6596	Remote Similarity	NPC33421
0.6596	Remote Similarity	NPC40070
0.6591	Remote Similarity	NPC316104
0.6591	Remote Similarity	NPC162417
0.6569	Remote Similarity	NPC469537
0.6567	Remote Similarity	NPC325252
0.6565	Remote Similarity	NPC69914
0.6565	Remote Similarity	NPC282398
0.6562	Remote Similarity	NPC245244
0.6562	Remote Similarity	NPC166424
0.6562	Remote Similarity	NPC146373
0.656	Remote Similarity	NPC103292
0.6555	Remote Similarity	NPC27802
0.6549	Remote Similarity	NPC117032
0.6545	Remote Similarity	NPC108339
0.6544	Remote Similarity	NPC316811
0.6544	Remote Similarity	NPC32002
0.6544	Remote Similarity	NPC315348
0.6535	Remote Similarity	NPC290094
0.6535	Remote Similarity	NPC192533
0.6532	Remote Similarity	NPC143603
0.6519	Remote Similarity	NPC83214
0.6509	Remote Similarity	NPC17497
0.6509	Remote Similarity	NPC305602
0.6508	Remote Similarity	NPC39818
0.6484	Remote Similarity	NPC27740
0.6484	Remote Similarity	NPC472244
0.6484	Remote Similarity	NPC470343
0.6479	Remote Similarity	NPC154602
0.6479	Remote Similarity	NPC243756
0.6479	Remote Similarity	NPC66936
0.6471	Remote Similarity	NPC243162
0.6466	Remote Similarity	NPC167336
0.6465	Remote Similarity	NPC301874
0.6462	Remote Similarity	NPC150863
0.646	Remote Similarity	NPC323726
0.6457	Remote Similarity	NPC329825
0.6457	Remote Similarity	NPC328683
0.6457	Remote Similarity	NPC283130
0.6449	Remote Similarity	NPC297532
0.6439	Remote Similarity	NPC476685
0.6439	Remote Similarity	NPC476687
0.6439	Remote Similarity	NPC476689
0.6434	Remote Similarity	NPC250476
0.6423	Remote Similarity	NPC125416
0.6423	Remote Similarity	NPC471574
0.6412	Remote Similarity	NPC472245
0.6412	Remote Similarity	NPC280807
0.6412	Remote Similarity	NPC314431
0.6408	Remote Similarity	NPC307456
0.6404	Remote Similarity	NPC474582
0.64	Remote Similarity	NPC139658
0.6397	Remote Similarity	NPC150259
0.6392	Remote Similarity	NPC271732
0.6392	Remote Similarity	NPC219246
0.6391	Remote Similarity	NPC101165
0.6385	Remote Similarity	NPC469949
0.6385	Remote Similarity	NPC476140
0.6385	Remote Similarity	NPC202957
0.6385	Remote Similarity	NPC169625
0.637	Remote Similarity	NPC267508
0.6364	Remote Similarity	NPC66775
0.6364	Remote Similarity	NPC299134
0.6364	Remote Similarity	NPC475763
0.6364	Remote Similarity	NPC113000
0.6364	Remote Similarity	NPC112609
0.6364	Remote Similarity	NPC122327
0.6364	Remote Similarity	NPC231382
0.6351	Remote Similarity	NPC469741
0.635	Remote Similarity	NPC169433
0.6345	Remote Similarity	NPC476219
0.6341	Remote Similarity	NPC143156
0.6339	Remote Similarity	NPC471320
0.6339	Remote Similarity	NPC471319
0.6336	Remote Similarity	NPC471313
0.6336	Remote Similarity	NPC471311
0.6336	Remote Similarity	NPC328590
0.6336	Remote Similarity	NPC209389
0.6327	Remote Similarity	NPC475990
0.6327	Remote Similarity	NPC56765
0.6327	Remote Similarity	NPC221786
0.6327	Remote Similarity	NPC276085
0.6327	Remote Similarity	NPC6436
0.6327	Remote Similarity	NPC474880
0.6319	Remote Similarity	NPC470233
0.6316	Remote Similarity	NPC213774
0.6316	Remote Similarity	NPC22079
0.6312	Remote Similarity	NPC469525
0.6306	Remote Similarity	NPC469330
0.6304	Remote Similarity	NPC470301
0.6304	Remote Similarity	NPC2823

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 NPC291610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	805
0.2-0.3	1111
0.3-0.4	1692
0.4-0.5	3120
0.5-0.6	1552
0.6-0.7	421
0.7-0.8	118
0.8-0.85	12
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9307	High Similarity	NPD7633	Discontinued
0.9118	High Similarity	NPD4116	Approved
0.8952	High Similarity	NPD5179	Approved
0.8952	High Similarity	NPD5180	Approved
0.8952	High Similarity	NPD5181	Approved
0.8922	High Similarity	NPD5253	Approved
0.8824	High Similarity	NPD3545	Approved
0.8824	High Similarity	NPD3546	Approved
0.8774	High Similarity	NPD2913	Approved
0.8774	High Similarity	NPD2914	Approved
0.8738	High Similarity	NPD4114	Approved
0.8738	High Similarity	NPD4115	Approved
0.8519	High Similarity	NPD5629	Discontinued
0.8431	Intermediate Similarity	NPD4734	Approved
0.8431	Intermediate Similarity	NPD4735	Approved
0.8411	Intermediate Similarity	NPD2038	Approved
0.8411	Intermediate Similarity	NPD2999	Approved
0.8411	Intermediate Similarity	NPD2039	Approved
0.8411	Intermediate Similarity	NPD3001	Approved
0.8381	Intermediate Similarity	NPD6299	Approved
0.8381	Intermediate Similarity	NPD6300	Approved
0.8265	Intermediate Similarity	NPD2997	Approved
0.8265	Intermediate Similarity	NPD2998	Approved
0.8265	Intermediate Similarity	NPD3000	Approved
0.8214	Intermediate Similarity	NPD5657	Phase 3
0.8131	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2539	Approved
0.8105	Intermediate Similarity	NPD2538	Approved
0.8036	Intermediate Similarity	NPD6070	Approved
0.8036	Intermediate Similarity	NPD6069	Approved
0.8034	Intermediate Similarity	NPD5136	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD5631	Phase 3
0.7965	Intermediate Similarity	NPD7480	Approved
0.7965	Intermediate Similarity	NPD7481	Approved
0.7949	Intermediate Similarity	NPD2871	Approved
0.7949	Intermediate Similarity	NPD2870	Approved
0.7938	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6548	Approved
0.7921	Intermediate Similarity	NPD6549	Approved
0.7909	Intermediate Similarity	NPD3009	Approved
0.7909	Intermediate Similarity	NPD3010	Approved
0.789	Intermediate Similarity	NPD3548	Approved
0.789	Intermediate Similarity	NPD2520	Approved
0.789	Intermediate Similarity	NPD2522	Approved
0.7876	Intermediate Similarity	NPD3484	Approved
0.7876	Intermediate Similarity	NPD3483	Approved
0.7826	Intermediate Similarity	NPD3499	Approved
0.7826	Intermediate Similarity	NPD3498	Approved
0.7815	Intermediate Similarity	NPD3438	Approved
0.7797	Intermediate Similarity	NPD2940	Approved
0.7797	Intermediate Similarity	NPD2938	Approved
0.7788	Intermediate Similarity	NPD2924	Approved
0.7788	Intermediate Similarity	NPD2925	Approved
0.7778	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1064	Approved
0.7778	Intermediate Similarity	NPD1065	Approved
0.7769	Intermediate Similarity	NPD5131	Approved
0.775	Intermediate Similarity	NPD5993	Phase 1
0.7748	Intermediate Similarity	NPD3036	Approved
0.7748	Intermediate Similarity	NPD2521	Approved
0.7748	Intermediate Similarity	NPD2518	Approved
0.7748	Intermediate Similarity	NPD2519	Approved
0.7748	Intermediate Similarity	NPD3565	Approved
0.7748	Intermediate Similarity	NPD3566	Approved
0.7719	Intermediate Similarity	NPD2464	Approved
0.7719	Intermediate Similarity	NPD2467	Approved
0.7719	Intermediate Similarity	NPD2463	Approved
0.7712	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6489	Phase 3
0.7692	Intermediate Similarity	NPD4546	Discontinued
0.7623	Intermediate Similarity	NPD3424	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD4489	Approved
0.7623	Intermediate Similarity	NPD4490	Approved
0.7619	Intermediate Similarity	NPD6498	Approved
0.7619	Intermediate Similarity	NPD6499	Approved
0.7607	Intermediate Similarity	NPD3956	Phase 3
0.7607	Intermediate Similarity	NPD3955	Approved
0.7607	Intermediate Similarity	NPD3957	Phase 2
0.7604	Intermediate Similarity	NPD4026	Approved
0.7604	Intermediate Similarity	NPD4027	Approved
0.7586	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD4985	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD603	Approved
0.7544	Intermediate Similarity	NPD4085	Approved
0.7541	Intermediate Similarity	NPD3008	Approved
0.7541	Intermediate Similarity	NPD3011	Approved
0.7541	Intermediate Similarity	NPD3012	Approved
0.7525	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2840	Approved
0.7521	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3005	Phase 3
0.75	Intermediate Similarity	NPD5372	Approved
0.75	Intermediate Similarity	NPD5371	Approved
0.748	Intermediate Similarity	NPD4019	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD1723	Phase 2
0.7478	Intermediate Similarity	NPD1720	Phase 2
0.7458	Intermediate Similarity	NPD2340	Discontinued
0.7456	Intermediate Similarity	NPD2587	Approved
0.7436	Intermediate Similarity	NPD3954	Approved
0.7431	Intermediate Similarity	NPD2937	Phase 1
0.7431	Intermediate Similarity	NPD2939	Approved
0.7429	Intermediate Similarity	NPD2005	Discontinued
0.7414	Intermediate Similarity	NPD6660	Discontinued
0.7411	Intermediate Similarity	NPD1539	Approved
0.74	Intermediate Similarity	NPD4636	Approved
0.7395	Intermediate Similarity	NPD4610	Approved
0.7395	Intermediate Similarity	NPD4611	Approved
0.7374	Intermediate Similarity	NPD5178	Approved
0.7368	Intermediate Similarity	NPD4147	Approved
0.7368	Intermediate Similarity	NPD4144	Approved
0.7347	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4169	Approved
0.7347	Intermediate Similarity	NPD4170	Approved
0.7344	Intermediate Similarity	NPD6358	Phase 2
0.7339	Intermediate Similarity	NPD8263	Discontinued
0.7339	Intermediate Similarity	NPD4365	Phase 2
0.7333	Intermediate Similarity	NPD5554	Approved
0.7323	Intermediate Similarity	NPD3385	Approved
0.7323	Intermediate Similarity	NPD6318	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD477	Phase 1
0.7308	Intermediate Similarity	NPD4407	Approved
0.7308	Intermediate Similarity	NPD4408	Approved
0.7308	Intermediate Similarity	NPD4405	Approved
0.7304	Intermediate Similarity	NPD2659	Approved
0.7304	Intermediate Similarity	NPD3148	Approved
0.7304	Intermediate Similarity	NPD3149	Approved
0.7304	Intermediate Similarity	NPD2658	Approved
0.7304	Intermediate Similarity	NPD3150	Approved
0.7304	Intermediate Similarity	NPD3147	Approved
0.7297	Intermediate Similarity	NPD993	Approved
0.7297	Intermediate Similarity	NPD990	Approved
0.7295	Intermediate Similarity	NPD8128	Discontinued
0.7248	Intermediate Similarity	NPD708	Approved
0.7245	Intermediate Similarity	NPD3035	Approved
0.7244	Intermediate Similarity	NPD7200	Approved
0.7241	Intermediate Similarity	NPD1813	Discontinued
0.7228	Intermediate Similarity	NPD4409	Approved
0.7228	Intermediate Similarity	NPD4406	Approved
0.7222	Intermediate Similarity	NPD1946	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1762	Approved
0.7217	Intermediate Similarity	NPD1764	Approved
0.7216	Intermediate Similarity	NPD507	Approved
0.7216	Intermediate Similarity	NPD508	Approved
0.7182	Intermediate Similarity	NPD2244	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2679	Approved
0.7168	Intermediate Similarity	NPD2678	Approved
0.7165	Intermediate Similarity	NPD3137	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1377	Approved
0.7155	Intermediate Similarity	NPD1378	Approved
0.7154	Intermediate Similarity	NPD4609	Approved
0.7154	Intermediate Similarity	NPD6320	Approved
0.7154	Intermediate Similarity	NPD1937	Approved
0.7154	Intermediate Similarity	NPD4608	Approved
0.7143	Intermediate Similarity	NPD5782	Phase 3
0.713	Intermediate Similarity	NPD3865	Approved
0.712	Intermediate Similarity	NPD2118	Approved
0.712	Intermediate Similarity	NPD2119	Approved
0.712	Intermediate Similarity	NPD2036	Approved
0.712	Intermediate Similarity	NPD4549	Discontinued
0.7117	Intermediate Similarity	NPD1728	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5431	Phase 2
0.7107	Intermediate Similarity	NPD3582	Approved
0.7105	Intermediate Similarity	NPD6235	Approved
0.7105	Intermediate Similarity	NPD6236	Approved
0.7105	Intermediate Similarity	NPD1108	Approved
0.7105	Intermediate Similarity	NPD1107	Approved
0.7103	Intermediate Similarity	NPD5963	Phase 2
0.7103	Intermediate Similarity	NPD5964	Phase 2
0.7099	Intermediate Similarity	NPD6606	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6900	Discontinued
0.7097	Intermediate Similarity	NPD1949	Approved
0.7097	Intermediate Similarity	NPD572	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1950	Approved
0.7091	Intermediate Similarity	NPD1419	Approved
0.7091	Intermediate Similarity	NPD1417	Approved
0.7087	Intermediate Similarity	NPD6822	Approved
0.7087	Intermediate Similarity	NPD6820	Approved
0.7087	Intermediate Similarity	NPD3345	Approved
0.708	Intermediate Similarity	NPD2243	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1111	Phase 3
0.708	Intermediate Similarity	NPD1112	Phase 3
0.7075	Intermediate Similarity	NPD4545	Approved
0.7075	Intermediate Similarity	NPD4542	Approved
0.7059	Intermediate Similarity	NPD299	Phase 3
0.7054	Intermediate Similarity	NPD233	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2448	Approved
0.7049	Intermediate Similarity	NPD2449	Approved
0.7049	Intermediate Similarity	NPD2439	Approved
0.7049	Intermediate Similarity	NPD4176	Approved
0.7049	Intermediate Similarity	NPD5233	Approved
0.7049	Intermediate Similarity	NPD4178	Approved
0.7049	Intermediate Similarity	NPD5231	Approved
0.7049	Intermediate Similarity	NPD5232	Approved
0.7041	Intermediate Similarity	NPD1051	Approved
0.7041	Intermediate Similarity	NPD1052	Approved
0.7041	Intermediate Similarity	NPD1053	Approved
0.7037	Intermediate Similarity	NPD5598	Approved
0.7037	Intermediate Similarity	NPD5597	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