NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	135.07
Volume:	147.609
LogP:	1.049
LogD:	1.004
LogS:	-0.806
# Rotatable Bonds:	2
TPSA:	29.1
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	1.192
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.531
MDCK Permeability:	4.970528243575245e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	55.36492919921875%
Volume Distribution (VD):	0.773
Pgp-substrate:	40.325401306152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.874
CYP1A2-substrate:	0.161
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.459
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.65
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	8.817
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.645
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.2
Carcinogencity:	0.035
Eye Corrosion:	0.006
Eye Irritation:	0.914
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC198747

Natural Product ID:	NPC198747
*Common Name:**	N-Methylbenzamide
IUPAC Name:	N-methylbenzamide
Synonyms:	N-Methyl-Benzamide
Standard InCHIKey:	NCCHARWOCKOHIH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H9NO/c1-9-8(10)7-5-3-2-4-6-7/h2-6H,1H3,(H,9,10)
SMILES:	CN=C(c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL275261
PubChem CID:	11954
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0000178] Benzamides

*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
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	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
LD50	1
Others	8
Potency	4

Activity Type	# Activity
Cell Line	4
Individual Protein	3
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1761	Cell Line	Erythroleukemia cell line		Concentration	=	1.0	mM	PMID[548966]
NPT1761	Cell Line	Erythroleukemia cell line		Cell growth	=	54.0	%	PMID[548966]
NPT1761	Cell Line	Erythroleukemia cell line		Cell growth	=	99.0	%	PMID[548966]
NPT1761	Cell Line	Erythroleukemia cell line		Benzidine positive cells	=	62.0	%	PMID[548966]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	446.7	nM	PMID[548968]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	4.4	nM	PubChem BioAssay data set
NPT32	Organism	Mus musculus	Mus musculus	LD10	=	450.0	mg kg-1 day-1	PMID[548967]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	650.0	mg kg-1 day-1	PMID[548967]
NPT32	Organism	Mus musculus	Mus musculus	Mean tumor volume	=	0.8	n.a.	PMID[548967]
NPT32	Organism	Mus musculus	Mus musculus	Control tumor volume	=	1.9	n.a.	PMID[548967]
NPT32	Organism	Mus musculus	Mus musculus	T/C	=	42.0	%	PMID[548967]
NPT2	Others	Unspecified		Potency	n.a.	61637.3	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 NPC198747 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	124
0.1-0.2	2706
0.2-0.3	9365
0.3-0.4	12913
0.4-0.5	12872
0.5-0.6	3677
0.6-0.7	871
0.7-0.8	157
0.8-0.85	6
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC265521
0.9036	High Similarity	NPC146703
0.8889	High Similarity	NPC3371
0.8791	High Similarity	NPC33168
0.8617	High Similarity	NPC318154
0.8235	Intermediate Similarity	NPC192623
0.8163	Intermediate Similarity	NPC211551
0.814	Intermediate Similarity	NPC133050
0.8095	Intermediate Similarity	NPC66655
0.8046	Intermediate Similarity	NPC99394
0.8046	Intermediate Similarity	NPC103326
0.8046	Intermediate Similarity	NPC329319
0.8046	Intermediate Similarity	NPC14326
0.8046	Intermediate Similarity	NPC87299
0.7955	Intermediate Similarity	NPC172984
0.7935	Intermediate Similarity	NPC258627
0.7935	Intermediate Similarity	NPC172128
0.7931	Intermediate Similarity	NPC117180
0.7921	Intermediate Similarity	NPC153690
0.7865	Intermediate Similarity	NPC304538
0.7865	Intermediate Similarity	NPC168855
0.7826	Intermediate Similarity	NPC470877
0.7802	Intermediate Similarity	NPC211237
0.7778	Intermediate Similarity	NPC178902
0.7778	Intermediate Similarity	NPC474354
0.7778	Intermediate Similarity	NPC3210
0.7742	Intermediate Similarity	NPC209764
0.7742	Intermediate Similarity	NPC78041
0.7742	Intermediate Similarity	NPC74936
0.7742	Intermediate Similarity	NPC159178
0.7742	Intermediate Similarity	NPC141139
0.7742	Intermediate Similarity	NPC121872
0.7742	Intermediate Similarity	NPC471307
0.7732	Intermediate Similarity	NPC107619
0.7732	Intermediate Similarity	NPC315921
0.7723	Intermediate Similarity	NPC231705
0.7717	Intermediate Similarity	NPC325441
0.7692	Intermediate Similarity	NPC93843
0.7692	Intermediate Similarity	NPC163674
0.7692	Intermediate Similarity	NPC227553
0.7692	Intermediate Similarity	NPC474211
0.767	Intermediate Similarity	NPC258056
0.7647	Intermediate Similarity	NPC189371
0.7647	Intermediate Similarity	NPC142297
0.7614	Intermediate Similarity	NPC328178
0.7609	Intermediate Similarity	NPC473031
0.7604	Intermediate Similarity	NPC215351
0.7604	Intermediate Similarity	NPC58674
0.7604	Intermediate Similarity	NPC20142
0.7596	Intermediate Similarity	NPC474149
0.7576	Intermediate Similarity	NPC328793
0.7576	Intermediate Similarity	NPC214200
0.7576	Intermediate Similarity	NPC228400
0.7553	Intermediate Similarity	NPC316108
0.7551	Intermediate Similarity	NPC108606
0.7551	Intermediate Similarity	NPC164514
0.7551	Intermediate Similarity	NPC303611
0.7551	Intermediate Similarity	NPC226096
0.7551	Intermediate Similarity	NPC290515
0.7529	Intermediate Similarity	NPC108218
0.7527	Intermediate Similarity	NPC407
0.7527	Intermediate Similarity	NPC23167
0.7527	Intermediate Similarity	NPC307235
0.75	Intermediate Similarity	NPC286904
0.75	Intermediate Similarity	NPC203076
0.75	Intermediate Similarity	NPC471309
0.75	Intermediate Similarity	NPC327226
0.75	Intermediate Similarity	NPC248817
0.7474	Intermediate Similarity	NPC226438
0.7447	Intermediate Similarity	NPC27974
0.7447	Intermediate Similarity	NPC25493
0.7447	Intermediate Similarity	NPC113460
0.7447	Intermediate Similarity	NPC1793
0.7423	Intermediate Similarity	NPC161972
0.7423	Intermediate Similarity	NPC303045
0.7419	Intermediate Similarity	NPC197783
0.7419	Intermediate Similarity	NPC155393
0.7419	Intermediate Similarity	NPC471638
0.7404	Intermediate Similarity	NPC24101
0.7404	Intermediate Similarity	NPC96224
0.74	Intermediate Similarity	NPC289381
0.74	Intermediate Similarity	NPC155847
0.7391	Intermediate Similarity	NPC124436
0.7391	Intermediate Similarity	NPC265146
0.7386	Intermediate Similarity	NPC224544
0.7368	Intermediate Similarity	NPC242240
0.7368	Intermediate Similarity	NPC258219
0.7368	Intermediate Similarity	NPC280347
0.7368	Intermediate Similarity	NPC318325
0.7368	Intermediate Similarity	NPC177420
0.7368	Intermediate Similarity	NPC123273
0.7353	Intermediate Similarity	NPC150254
0.7353	Intermediate Similarity	NPC226778
0.7353	Intermediate Similarity	NPC304761
0.7353	Intermediate Similarity	NPC147000
0.7347	Intermediate Similarity	NPC25565
0.734	Intermediate Similarity	NPC184169
0.734	Intermediate Similarity	NPC12429
0.7315	Intermediate Similarity	NPC118202
0.7312	Intermediate Similarity	NPC150837
0.7312	Intermediate Similarity	NPC175313
0.7308	Intermediate Similarity	NPC37584
0.7297	Intermediate Similarity	NPC43275
0.7294	Intermediate Similarity	NPC208302
0.7292	Intermediate Similarity	NPC79917
0.7292	Intermediate Similarity	NPC55561
0.7273	Intermediate Similarity	NPC473501
0.7273	Intermediate Similarity	NPC475439
0.7263	Intermediate Similarity	NPC199567
0.7253	Intermediate Similarity	NPC106313
0.7248	Intermediate Similarity	NPC317254
0.7222	Intermediate Similarity	NPC1986
0.7222	Intermediate Similarity	NPC474544
0.7216	Intermediate Similarity	NPC304541
0.7216	Intermediate Similarity	NPC306074
0.7216	Intermediate Similarity	NPC231150
0.7216	Intermediate Similarity	NPC204210
0.7207	Intermediate Similarity	NPC5932
0.7196	Intermediate Similarity	NPC166837
0.7188	Intermediate Similarity	NPC98772
0.7188	Intermediate Similarity	NPC70436
0.717	Intermediate Similarity	NPC316052
0.7168	Intermediate Similarity	NPC86966
0.7158	Intermediate Similarity	NPC262393
0.7156	Intermediate Similarity	NPC142599
0.7143	Intermediate Similarity	NPC3358
0.7143	Intermediate Similarity	NPC306884
0.7143	Intermediate Similarity	NPC138117
0.7143	Intermediate Similarity	NPC210497
0.7143	Intermediate Similarity	NPC165212
0.7143	Intermediate Similarity	NPC147284
0.7143	Intermediate Similarity	NPC55903
0.7143	Intermediate Similarity	NPC94139
0.7143	Intermediate Similarity	NPC325292
0.7143	Intermediate Similarity	NPC82770
0.7143	Intermediate Similarity	NPC239931
0.7143	Intermediate Similarity	NPC78954
0.7143	Intermediate Similarity	NPC162314
0.7129	Intermediate Similarity	NPC125732
0.7113	Intermediate Similarity	NPC300017
0.7113	Intermediate Similarity	NPC192
0.7113	Intermediate Similarity	NPC151764
0.7113	Intermediate Similarity	NPC245259
0.7105	Intermediate Similarity	NPC109151
0.71	Intermediate Similarity	NPC311242
0.7097	Intermediate Similarity	NPC95429
0.7093	Intermediate Similarity	NPC125144
0.7093	Intermediate Similarity	NPC121708
0.7091	Intermediate Similarity	NPC37302
0.7087	Intermediate Similarity	NPC68055
0.7083	Intermediate Similarity	NPC19680
0.7083	Intermediate Similarity	NPC104216
0.708	Intermediate Similarity	NPC112823
0.7075	Intermediate Similarity	NPC309982
0.7071	Intermediate Similarity	NPC289769
0.7071	Intermediate Similarity	NPC152415
0.7071	Intermediate Similarity	NPC316301
0.7071	Intermediate Similarity	NPC245187
0.7071	Intermediate Similarity	NPC27323
0.7065	Intermediate Similarity	NPC283012
0.7065	Intermediate Similarity	NPC475199
0.7059	Intermediate Similarity	NPC469457
0.7041	Intermediate Similarity	NPC128645
0.7041	Intermediate Similarity	NPC270547
0.7041	Intermediate Similarity	NPC155908
0.7041	Intermediate Similarity	NPC45040
0.7033	Intermediate Similarity	NPC309279
0.7027	Intermediate Similarity	NPC82963
0.7021	Intermediate Similarity	NPC58616
0.7018	Intermediate Similarity	NPC273830
0.7018	Intermediate Similarity	NPC284078
0.7018	Intermediate Similarity	NPC324702
0.7009	Intermediate Similarity	NPC65855
0.7009	Intermediate Similarity	NPC292758
0.7009	Intermediate Similarity	NPC71266
0.7	Intermediate Similarity	NPC26244
0.7	Intermediate Similarity	NPC313650
0.7	Intermediate Similarity	NPC8392
0.6991	Remote Similarity	NPC283760
0.697	Remote Similarity	NPC181709
0.697	Remote Similarity	NPC271440
0.697	Remote Similarity	NPC29373
0.6964	Remote Similarity	NPC311737
0.6964	Remote Similarity	NPC38458
0.6961	Remote Similarity	NPC12730
0.6939	Remote Similarity	NPC312304
0.6939	Remote Similarity	NPC300478
0.6939	Remote Similarity	NPC47950
0.6937	Remote Similarity	NPC303370
0.6931	Remote Similarity	NPC259512
0.6931	Remote Similarity	NPC253423
0.6931	Remote Similarity	NPC312132
0.6931	Remote Similarity	NPC473388
0.6923	Remote Similarity	NPC469894
0.6923	Remote Similarity	NPC471310
0.6923	Remote Similarity	NPC471317
0.6923	Remote Similarity	NPC4974
0.6916	Remote Similarity	NPC146530
0.69	Remote Similarity	NPC128062
0.69	Remote Similarity	NPC151715

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 NPC198747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	900
0.2-0.3	987
0.3-0.4	2956
0.4-0.5	2633
0.5-0.6	1232
0.6-0.7	274
0.7-0.8	41
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8602	High Similarity	NPD9712	Approved
0.8556	High Similarity	NPD159	Clinical (unspecified phase)
0.8495	Intermediate Similarity	NPD9710	Approved
0.8495	Intermediate Similarity	NPD9711	Approved
0.8438	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD9294	Approved
0.8	Intermediate Similarity	NPD9538	Approved
0.7957	Intermediate Similarity	NPD752	Approved
0.7849	Intermediate Similarity	NPD530	Approved
0.7732	Intermediate Similarity	NPD9273	Approved
0.7717	Intermediate Similarity	NPD1101	Approved
0.7684	Intermediate Similarity	NPD719	Approved
0.7684	Intermediate Similarity	NPD720	Approved
0.7579	Intermediate Similarity	NPD6690	Approved
0.7576	Intermediate Similarity	NPD9248	Phase 1
0.7551	Intermediate Similarity	NPD9611	Approved
0.7551	Intermediate Similarity	NPD9612	Approved
0.7551	Intermediate Similarity	NPD9609	Approved
0.75	Intermediate Similarity	NPD854	Approved
0.75	Intermediate Similarity	NPD855	Approved
0.75	Intermediate Similarity	NPD3123	Discovery
0.75	Intermediate Similarity	NPD4818	Approved
0.75	Intermediate Similarity	NPD4817	Approved
0.7431	Intermediate Similarity	NPD1359	Approved
0.7423	Intermediate Similarity	NPD4814	Discontinued
0.7396	Intermediate Similarity	NPD1812	Approved
0.7396	Intermediate Similarity	NPD1814	Approved
0.7391	Intermediate Similarity	NPD111	Approved
0.7353	Intermediate Similarity	NPD310	Approved
0.7353	Intermediate Similarity	NPD10	Approved
0.7353	Intermediate Similarity	NPD311	Approved
0.7353	Intermediate Similarity	NPD314	Approved
0.7353	Intermediate Similarity	NPD315	Approved
0.7353	Intermediate Similarity	NPD309	Approved
0.732	Intermediate Similarity	NPD1409	Phase 3
0.7308	Intermediate Similarity	NPD6406	Approved
0.7273	Intermediate Similarity	NPD1758	Phase 1
0.7273	Intermediate Similarity	NPD1875	Phase 1
0.7255	Intermediate Similarity	NPD4656	Approved
0.7255	Intermediate Similarity	NPD4231	Approved
0.7255	Intermediate Similarity	NPD3682	Approved
0.7255	Intermediate Similarity	NPD4229	Approved
0.7255	Intermediate Similarity	NPD3683	Approved
0.7255	Intermediate Similarity	NPD3680	Approved
0.7255	Intermediate Similarity	NPD4658	Approved
0.7255	Intermediate Similarity	NPD3681	Approved
0.7232	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1444	Approved
0.7212	Intermediate Similarity	NPD1445	Approved
0.7207	Intermediate Similarity	NPD1759	Phase 1
0.7184	Intermediate Similarity	NPD9610	Approved
0.7184	Intermediate Similarity	NPD9608	Approved
0.717	Intermediate Similarity	NPD9713	Approved
0.7157	Intermediate Similarity	NPD4119	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7071	Intermediate Similarity	NPD3772	Phase 3
0.7071	Intermediate Similarity	NPD2934	Approved
0.7071	Intermediate Similarity	NPD2933	Approved
0.7071	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD187	Approved
0.7043	Intermediate Similarity	NPD6624	Discontinued
0.7009	Intermediate Similarity	NPD1792	Phase 2
0.7	Intermediate Similarity	NPD2860	Approved
0.7	Intermediate Similarity	NPD844	Approved
0.7	Intermediate Similarity	NPD2859	Approved
0.699	Remote Similarity	NPD9722	Approved
0.699	Remote Similarity	NPD9721	Approved
0.6981	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1066	Discontinued
0.6961	Remote Similarity	NPD1067	Discontinued
0.6957	Remote Similarity	NPD804	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9250	Approved
0.6952	Remote Similarity	NPD999	Phase 2
0.6952	Remote Similarity	NPD1040	Phase 2
0.6952	Remote Similarity	NPD5717	Approved
0.6952	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4254	Approved
0.6944	Remote Similarity	NPD4253	Approved
0.6944	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD288	Approved
0.6923	Remote Similarity	NPD3098	Discontinued
0.6923	Remote Similarity	NPD3125	Approved
0.6923	Remote Similarity	NPD1542	Approved
0.6916	Remote Similarity	NPD4717	Approved
0.6916	Remote Similarity	NPD4718	Approved
0.6916	Remote Similarity	NPD4720	Approved
0.69	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2555	Approved
0.6893	Remote Similarity	NPD2558	Approved
0.6893	Remote Similarity	NPD2552	Approved
0.6893	Remote Similarity	NPD2549	Approved
0.6893	Remote Similarity	NPD2553	Approved
0.6893	Remote Similarity	NPD2550	Approved
0.6881	Remote Similarity	NPD2499	Approved
0.6881	Remote Similarity	NPD2500	Approved
0.687	Remote Similarity	NPD3421	Phase 3
0.687	Remote Similarity	NPD542	Phase 1
0.6863	Remote Similarity	NPD4117	Approved
0.6837	Remote Similarity	NPD9258	Approved
0.6837	Remote Similarity	NPD9256	Approved
0.6832	Remote Similarity	NPD1809	Phase 2
0.6827	Remote Similarity	NPD4189	Approved
0.6827	Remote Similarity	NPD1540	Approved
0.6827	Remote Similarity	NPD4188	Approved
0.6818	Remote Similarity	NPD821	Approved
0.6809	Remote Similarity	NPD9491	Approved
0.6804	Remote Similarity	NPD531	Approved
0.68	Remote Similarity	NPD1080	Approved
0.6796	Remote Similarity	NPD3020	Approved
0.6789	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2229	Approved
0.6757	Remote Similarity	NPD2234	Approved
0.6757	Remote Similarity	NPD2228	Approved
0.6731	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1616	Discontinued
0.6724	Remote Similarity	NPD3143	Discontinued
0.67	Remote Similarity	NPD9251	Approved
0.6699	Remote Similarity	NPD9495	Approved
0.6698	Remote Similarity	NPD3047	Approved
0.6698	Remote Similarity	NPD3048	Approved
0.6698	Remote Similarity	NPD3046	Approved
0.6697	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD475	Phase 2
0.6696	Remote Similarity	NPD1793	Approved
0.6696	Remote Similarity	NPD1791	Approved
0.6667	Remote Similarity	NPD846	Approved
0.6667	Remote Similarity	NPD9532	Phase 3
0.6667	Remote Similarity	NPD940	Approved
0.6667	Remote Similarity	NPD4480	Approved
0.6667	Remote Similarity	NPD5716	Approved
0.6667	Remote Similarity	NPD4719	Phase 2
0.6667	Remote Similarity	NPD9716	Approved
0.6636	Remote Similarity	NPD2583	Phase 2
0.6636	Remote Similarity	NPD1018	Approved
0.6629	Remote Similarity	NPD9728	Phase 1
0.661	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.661	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1415	Approved
0.6604	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD226	Approved
0.6585	Remote Similarity	NPD1048	Approved
0.6581	Remote Similarity	NPD1980	Approved
0.6581	Remote Similarity	NPD1981	Approved
0.6581	Remote Similarity	NPD1983	Approved
0.6579	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD9508	Approved
0.6574	Remote Similarity	NPD2551	Approved
0.6574	Remote Similarity	NPD2559	Approved
0.6574	Remote Similarity	NPD3524	Approved
0.6574	Remote Similarity	NPD3526	Approved
0.6574	Remote Similarity	NPD810	Approved
0.6574	Remote Similarity	NPD811	Approved
0.6574	Remote Similarity	NPD812	Approved
0.6571	Remote Similarity	NPD1275	Phase 2
0.6566	Remote Similarity	NPD800	Approved
0.6557	Remote Similarity	NPD4698	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD9087	Approved
0.6555	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD9614	Approved
0.6549	Remote Similarity	NPD9618	Approved
0.6529	Remote Similarity	NPD7451	Discontinued
0.6522	Remote Similarity	NPD16	Approved
0.6522	Remote Similarity	NPD9247	Phase 3
0.6522	Remote Similarity	NPD9613	Approved
0.6522	Remote Similarity	NPD317	Approved
0.6522	Remote Similarity	NPD9615	Approved
0.6522	Remote Similarity	NPD828	Approved
0.6522	Remote Similarity	NPD9616	Approved
0.6522	Remote Similarity	NPD318	Approved
0.6522	Remote Similarity	NPD856	Approved
0.6518	Remote Similarity	NPD9377	Approved
0.6518	Remote Similarity	NPD9379	Approved
0.6509	Remote Similarity	NPD1735	Approved
0.6509	Remote Similarity	NPD1736	Approved
0.6509	Remote Similarity	NPD1737	Approved
0.6504	Remote Similarity	NPD2372	Approved
0.65	Remote Similarity	NPD1086	Approved
0.65	Remote Similarity	NPD1090	Approved
0.65	Remote Similarity	NPD1089	Approved
0.6491	Remote Similarity	NPD709	Approved
0.6486	Remote Similarity	NPD3643	Approved
0.6486	Remote Similarity	NPD3642	Approved
0.6486	Remote Similarity	NPD3644	Approved
0.648	Remote Similarity	NPD1106	Discontinued
0.6471	Remote Similarity	NPD3070	Discontinued
0.6471	Remote Similarity	NPD3719	Approved
0.6471	Remote Similarity	NPD964	Approved
0.6471	Remote Similarity	NPD3718	Approved
0.6466	Remote Similarity	NPD5304	Approved
0.6466	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5303	Approved
0.6466	Remote Similarity	NPD316	Approved
0.6452	Remote Similarity	NPD1330	Phase 2
0.6452	Remote Similarity	NPD1329	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