NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.07
Volume:	228.854
LogP:	3.134
LogD:	2.47
LogS:	-3.346
# Rotatable Bonds:	1
TPSA:	55.12
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	2.156
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.24
MDCK Permeability:	1.5205730960587971e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	87.56755065917969%
Volume Distribution (VD):	0.75
Pgp-substrate:	8.671821594238281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.18
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	4.283
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.76
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.584
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.042
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.115
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC57398

Natural Product ID:	NPC57398
*Common Name:**	2-Methylpyrido[3,4-B]Indole-3-Carboxylic Acid
IUPAC Name:	2-methylpyrido[3,4-b]indole-3-carboxylic acid
Synonyms:
Standard InCHIKey:	SBBAFANGKJSOIR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10N2O2/c1-15-7-11-9(6-12(15)13(16)17)8-4-2-3-5-10(8)14-11/h2-7H,1H3,(H,16,17)
SMILES:	OC(=O)c1cc2c(cn1C)nc1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451124
PubChem CID:	10656832
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO33504	lignopsis spongiosum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10346963]
NPO40819	Cnemidocarpa irene	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[33030894]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	11.0	mm	PMID[455009]

☑ 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 NPC57398 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	407
0.1-0.2	3305
0.2-0.3	12882
0.3-0.4	15739
0.4-0.5	5693
0.5-0.6	2217
0.6-0.7	1989
0.7-0.8	438
0.8-0.85	21
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8978	High Similarity	NPC141454
0.8918	High Similarity	NPC118940
0.883	High Similarity	NPC474916
0.8756	High Similarity	NPC229893
0.8698	High Similarity	NPC165599
0.852	High Similarity	NPC266249
0.8486	Intermediate Similarity	NPC207851
0.8485	Intermediate Similarity	NPC82370
0.8469	Intermediate Similarity	NPC244741
0.8436	Intermediate Similarity	NPC41717
0.8434	Intermediate Similarity	NPC123839
0.8367	Intermediate Similarity	NPC472259
0.8308	Intermediate Similarity	NPC89508
0.8298	Intermediate Similarity	NPC62749
0.8274	Intermediate Similarity	NPC132539
0.8212	Intermediate Similarity	NPC322644
0.8205	Intermediate Similarity	NPC81535
0.8186	Intermediate Similarity	NPC312645
0.8168	Intermediate Similarity	NPC83111
0.8154	Intermediate Similarity	NPC212213
0.8098	Intermediate Similarity	NPC472285
0.8049	Intermediate Similarity	NPC36405
0.8	Intermediate Similarity	NPC477979
0.799	Intermediate Similarity	NPC211813
0.799	Intermediate Similarity	NPC328596
0.799	Intermediate Similarity	NPC328318
0.7981	Intermediate Similarity	NPC260434
0.7979	Intermediate Similarity	NPC248041
0.7979	Intermediate Similarity	NPC126709
0.7979	Intermediate Similarity	NPC219336
0.797	Intermediate Similarity	NPC239954
0.7953	Intermediate Similarity	NPC182222
0.795	Intermediate Similarity	NPC53144
0.7949	Intermediate Similarity	NPC198673
0.7947	Intermediate Similarity	NPC48938
0.7947	Intermediate Similarity	NPC159125
0.794	Intermediate Similarity	NPC471944
0.7929	Intermediate Similarity	NPC123395
0.7926	Intermediate Similarity	NPC217372
0.7926	Intermediate Similarity	NPC15573
0.7926	Intermediate Similarity	NPC183662
0.7923	Intermediate Similarity	NPC27041
0.7884	Intermediate Similarity	NPC283219
0.7876	Intermediate Similarity	NPC278434
0.7872	Intermediate Similarity	NPC267885
0.7871	Intermediate Similarity	NPC238457
0.7871	Intermediate Similarity	NPC317373
0.7864	Intermediate Similarity	NPC317752
0.7861	Intermediate Similarity	NPC200836
0.7831	Intermediate Similarity	NPC111275
0.7831	Intermediate Similarity	NPC84827
0.7831	Intermediate Similarity	NPC14113
0.7831	Intermediate Similarity	NPC145885
0.7822	Intermediate Similarity	NPC327592
0.7819	Intermediate Similarity	NPC110500
0.7819	Intermediate Similarity	NPC149155
0.7819	Intermediate Similarity	NPC469938
0.7819	Intermediate Similarity	NPC203468
0.7817	Intermediate Similarity	NPC202812
0.7816	Intermediate Similarity	NPC318299
0.7807	Intermediate Similarity	NPC273532
0.7801	Intermediate Similarity	NPC191415
0.7789	Intermediate Similarity	NPC248462
0.7789	Intermediate Similarity	NPC168911
0.7778	Intermediate Similarity	NPC472116
0.7778	Intermediate Similarity	NPC207686
0.7773	Intermediate Similarity	NPC60621
0.7772	Intermediate Similarity	NPC476098
0.7772	Intermediate Similarity	NPC282103
0.776	Intermediate Similarity	NPC143533
0.7749	Intermediate Similarity	NPC24864
0.7742	Intermediate Similarity	NPC56233
0.7718	Intermediate Similarity	NPC85273
0.7717	Intermediate Similarity	NPC15801
0.7708	Intermediate Similarity	NPC113626
0.7701	Intermediate Similarity	NPC78020
0.77	Intermediate Similarity	NPC131887
0.77	Intermediate Similarity	NPC122436
0.7686	Intermediate Similarity	NPC74619
0.7668	Intermediate Similarity	NPC102755
0.7668	Intermediate Similarity	NPC243058
0.7665	Intermediate Similarity	NPC117244
0.7665	Intermediate Similarity	NPC473763
0.7662	Intermediate Similarity	NPC476167
0.7659	Intermediate Similarity	NPC270918
0.7656	Intermediate Similarity	NPC469896
0.7654	Intermediate Similarity	NPC302159
0.7653	Intermediate Similarity	NPC321708
0.7647	Intermediate Similarity	NPC314648
0.7644	Intermediate Similarity	NPC219848
0.7633	Intermediate Similarity	NPC309845
0.7629	Intermediate Similarity	NPC284678
0.7626	Intermediate Similarity	NPC316411
0.7626	Intermediate Similarity	NPC97902
0.7624	Intermediate Similarity	NPC315491
0.7624	Intermediate Similarity	NPC45459
0.7624	Intermediate Similarity	NPC213308
0.7619	Intermediate Similarity	NPC158129
0.7612	Intermediate Similarity	NPC192315
0.7612	Intermediate Similarity	NPC67288
0.7608	Intermediate Similarity	NPC234078
0.7608	Intermediate Similarity	NPC221100
0.7604	Intermediate Similarity	NPC55772
0.7604	Intermediate Similarity	NPC256268
0.7602	Intermediate Similarity	NPC472323
0.7591	Intermediate Similarity	NPC57453
0.759	Intermediate Similarity	NPC241025
0.7576	Intermediate Similarity	NPC138370
0.7573	Intermediate Similarity	NPC53344
0.7571	Intermediate Similarity	NPC237740
0.7569	Intermediate Similarity	NPC315062
0.7569	Intermediate Similarity	NPC267853
0.7568	Intermediate Similarity	NPC293487
0.7565	Intermediate Similarity	NPC15840
0.7562	Intermediate Similarity	NPC90229
0.7562	Intermediate Similarity	NPC106824
0.7552	Intermediate Similarity	NPC234987
0.7551	Intermediate Similarity	NPC160381
0.7551	Intermediate Similarity	NPC235684
0.7551	Intermediate Similarity	NPC90415
0.755	Intermediate Similarity	NPC289299
0.755	Intermediate Similarity	NPC57994
0.754	Intermediate Similarity	NPC478182
0.7539	Intermediate Similarity	NPC303225
0.7538	Intermediate Similarity	NPC203635
0.7536	Intermediate Similarity	NPC82548
0.7536	Intermediate Similarity	NPC322064
0.7534	Intermediate Similarity	NPC244897
0.7524	Intermediate Similarity	NPC472064
0.7524	Intermediate Similarity	NPC472065
0.7512	Intermediate Similarity	NPC192712
0.7512	Intermediate Similarity	NPC245916
0.7512	Intermediate Similarity	NPC102592
0.7512	Intermediate Similarity	NPC179701
0.7512	Intermediate Similarity	NPC79356
0.75	Intermediate Similarity	NPC174758
0.75	Intermediate Similarity	NPC295452
0.75	Intermediate Similarity	NPC171393
0.75	Intermediate Similarity	NPC84347
0.7489	Intermediate Similarity	NPC258048
0.7488	Intermediate Similarity	NPC284338
0.7488	Intermediate Similarity	NPC314297
0.7488	Intermediate Similarity	NPC315545
0.7488	Intermediate Similarity	NPC193238
0.7478	Intermediate Similarity	NPC178858
0.7475	Intermediate Similarity	NPC262898
0.7475	Intermediate Similarity	NPC221873
0.7475	Intermediate Similarity	NPC227582
0.7462	Intermediate Similarity	NPC315555
0.7461	Intermediate Similarity	NPC157583
0.7455	Intermediate Similarity	NPC200553
0.7455	Intermediate Similarity	NPC279189
0.7455	Intermediate Similarity	NPC148889
0.7452	Intermediate Similarity	NPC287208
0.7449	Intermediate Similarity	NPC472119
0.7446	Intermediate Similarity	NPC312860
0.744	Intermediate Similarity	NPC313796
0.744	Intermediate Similarity	NPC314855
0.744	Intermediate Similarity	NPC313345
0.744	Intermediate Similarity	NPC315638
0.7437	Intermediate Similarity	NPC154339
0.7437	Intermediate Similarity	NPC469489
0.7436	Intermediate Similarity	NPC314394
0.7431	Intermediate Similarity	NPC476491
0.7427	Intermediate Similarity	NPC317701
0.7423	Intermediate Similarity	NPC164340
0.7423	Intermediate Similarity	NPC12649
0.7419	Intermediate Similarity	NPC129721
0.7416	Intermediate Similarity	NPC174672
0.7416	Intermediate Similarity	NPC472070
0.7413	Intermediate Similarity	NPC230403
0.7413	Intermediate Similarity	NPC472295
0.7413	Intermediate Similarity	NPC269886
0.7413	Intermediate Similarity	NPC267343
0.7413	Intermediate Similarity	NPC81802
0.7413	Intermediate Similarity	NPC472210
0.7413	Intermediate Similarity	NPC326422
0.7413	Intermediate Similarity	NPC247735
0.7411	Intermediate Similarity	NPC295158
0.7409	Intermediate Similarity	NPC134586
0.7409	Intermediate Similarity	NPC151635
0.7404	Intermediate Similarity	NPC321428
0.7399	Intermediate Similarity	NPC235685
0.7395	Intermediate Similarity	NPC276657
0.7394	Intermediate Similarity	NPC478185
0.7393	Intermediate Similarity	NPC471194
0.7393	Intermediate Similarity	NPC471193
0.7391	Intermediate Similarity	NPC475070
0.7387	Intermediate Similarity	NPC174489
0.7385	Intermediate Similarity	NPC73994
0.7385	Intermediate Similarity	NPC319232
0.7385	Intermediate Similarity	NPC24370
0.7382	Intermediate Similarity	NPC32534
0.7381	Intermediate Similarity	NPC314834
0.7381	Intermediate Similarity	NPC5145
0.7379	Intermediate Similarity	NPC472063
0.7379	Intermediate Similarity	NPC472062
0.7379	Intermediate Similarity	NPC472069
0.7374	Intermediate Similarity	NPC478077
0.7374	Intermediate Similarity	NPC94752

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 NPC57398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	615
0.2-0.3	865
0.3-0.4	1604
0.4-0.5	2675
0.5-0.6	2061
0.6-0.7	942
0.7-0.8	131
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8274	Intermediate Similarity	NPD5901	Discontinued
0.8152	Intermediate Similarity	NPD750	Phase 2
0.8112	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD6999	Discontinued
0.803	Intermediate Similarity	NPD5017	Discontinued
0.7989	Intermediate Similarity	NPD3178	Discontinued
0.797	Intermediate Similarity	NPD7665	Phase 2
0.797	Intermediate Similarity	NPD7666	Phase 3
0.7969	Intermediate Similarity	NPD4948	Discontinued
0.7895	Intermediate Similarity	NPD5827	Discontinued
0.789	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7001	Phase 3
0.7846	Intermediate Similarity	NPD2336	Approved
0.7822	Intermediate Similarity	NPD6987	Phase 1
0.7819	Intermediate Similarity	NPD482	Approved
0.7817	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7749	Intermediate Similarity	NPD6452	Discontinued
0.7748	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1631	Approved
0.7688	Intermediate Similarity	NPD2307	Discontinued
0.7685	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6665	Discontinued
0.7624	Intermediate Similarity	NPD484	Approved
0.7611	Intermediate Similarity	NPD5482	Discontinued
0.761	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7470	Discontinued
0.7577	Intermediate Similarity	NPD2095	Phase 2
0.7577	Intermediate Similarity	NPD2094	Phase 2
0.7577	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD2092	Phase 2
0.7568	Intermediate Similarity	NPD1630	Approved
0.7566	Intermediate Similarity	NPD1575	Approved
0.7566	Intermediate Similarity	NPD1573	Approved
0.7563	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4602	Approved
0.7538	Intermediate Similarity	NPD2096	Phase 2
0.7538	Intermediate Similarity	NPD2091	Phase 2
0.7525	Intermediate Similarity	NPD4397	Phase 1
0.7524	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1996	Discontinued
0.7476	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD4852	Phase 2
0.7476	Intermediate Similarity	NPD5426	Phase 3
0.7476	Intermediate Similarity	NPD3947	Discontinued
0.7463	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7944	Discontinued
0.746	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD6752	Phase 1
0.7454	Intermediate Similarity	NPD6753	Phase 1
0.7452	Intermediate Similarity	NPD2509	Approved
0.7452	Intermediate Similarity	NPD2510	Approved
0.7449	Intermediate Similarity	NPD1096	Discontinued
0.7448	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5475	Discontinued
0.7423	Intermediate Similarity	NPD1587	Approved
0.7407	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1571	Phase 2
0.7374	Intermediate Similarity	NPD5809	Phase 3
0.7373	Intermediate Similarity	NPD6173	Approved
0.7371	Intermediate Similarity	NPD3393	Approved
0.7371	Intermediate Similarity	NPD3389	Approved
0.7371	Intermediate Similarity	NPD3394	Approved
0.7364	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6178	Phase 3
0.7358	Intermediate Similarity	NPD3243	Approved
0.7358	Intermediate Similarity	NPD5065	Approved
0.7352	Intermediate Similarity	NPD4845	Discontinued
0.735	Intermediate Similarity	NPD3321	Discontinued
0.7347	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4886	Phase 2
0.7336	Intermediate Similarity	NPD6710	Phase 3
0.7326	Intermediate Similarity	NPD4326	Phase 2
0.7317	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD2915	Discontinued
0.7308	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7603	Discontinued
0.7302	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1572	Phase 2
0.7287	Intermediate Similarity	NPD5255	Approved
0.7277	Intermediate Similarity	NPD5891	Approved
0.7277	Intermediate Similarity	NPD5505	Discontinued
0.7273	Intermediate Similarity	NPD7568	Phase 1
0.7273	Intermediate Similarity	NPD6165	Phase 2
0.7273	Intermediate Similarity	NPD6164	Phase 2
0.7268	Intermediate Similarity	NPD1586	Approved
0.7264	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2813	Phase 3
0.7256	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD2844	Phase 3
0.7231	Intermediate Similarity	NPD5100	Phase 3
0.7227	Intermediate Similarity	NPD5450	Discontinued
0.7227	Intermediate Similarity	NPD8289	Discontinued
0.7213	Intermediate Similarity	NPD9074	Approved
0.7213	Intermediate Similarity	NPD9075	Approved
0.7204	Intermediate Similarity	NPD2882	Phase 1
0.7198	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7777	Approved
0.7184	Intermediate Similarity	NPD7778	Approved
0.7184	Intermediate Similarity	NPD53	Approved
0.7183	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7767	Approved
0.715	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8093	Discontinued
0.715	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD5003	Discontinued
0.7136	Intermediate Similarity	NPD3222	Phase 2
0.713	Intermediate Similarity	NPD6733	Discontinued
0.7128	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3259	Approved
0.7117	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD3794	Approved
0.7116	Intermediate Similarity	NPD3795	Approved
0.7116	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2305	Discontinued
0.7114	Intermediate Similarity	NPD706	Phase 1
0.7112	Intermediate Similarity	NPD4558	Phase 2
0.711	Intermediate Similarity	NPD7404	Approved
0.7108	Intermediate Similarity	NPD4376	Phase 3
0.7101	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD424	Approved
0.7098	Intermediate Similarity	NPD425	Approved
0.7097	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4310	Phase 3
0.7094	Intermediate Similarity	NPD6281	Approved
0.7091	Intermediate Similarity	NPD8356	Approved
0.7089	Intermediate Similarity	NPD4520	Approved
0.7083	Intermediate Similarity	NPD5088	Discontinued
0.7077	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3905	Phase 3
0.7074	Intermediate Similarity	NPD6790	Phase 1
0.7072	Intermediate Similarity	NPD2896	Discontinued
0.7072	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5866	Approved
0.7064	Intermediate Similarity	NPD1623	Approved
0.7059	Intermediate Similarity	NPD1658	Discontinued
0.7056	Intermediate Similarity	NPD7921	Approved
0.7056	Intermediate Similarity	NPD5104	Approved
0.7056	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5020	Approved
0.7048	Intermediate Similarity	NPD2879	Approved
0.7048	Intermediate Similarity	NPD2881	Approved
0.7047	Intermediate Similarity	NPD926	Approved
0.7047	Intermediate Similarity	NPD925	Approved
0.7042	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8430	Approved
0.7039	Intermediate Similarity	NPD7619	Phase 3
0.7039	Intermediate Similarity	NPD7618	Phase 3
0.7035	Intermediate Similarity	NPD5897	Approved
0.7035	Intermediate Similarity	NPD5899	Approved
0.7035	Intermediate Similarity	NPD5898	Approved
0.7033	Intermediate Similarity	NPD4600	Approved
0.7033	Intermediate Similarity	NPD4601	Approved
0.7032	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7168	Phase 3
0.703	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3315	Phase 3
0.7028	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7688	Phase 1
0.7021	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6158	Phase 2
0.7015	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2564	Approved
0.701	Intermediate Similarity	NPD4499	Approved
0.701	Intermediate Similarity	NPD2565	Phase 2
0.7009	Intermediate Similarity	NPD1600	Suspended
0.7004	Intermediate Similarity	NPD2951	Discontinued
0.7	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1233	Suspended
0.7	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6242	Discontinued
0.6995	Remote Similarity	NPD107	Approved
0.6995	Remote Similarity	NPD6791	Phase 2
0.6995	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD8463	Approved
0.6991	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1173	Approved
0.6987	Remote Similarity	NPD4938	Phase 2
0.6986	Remote Similarity	NPD3354	Phase 2
0.6986	Remote Similarity	NPD7878	Phase 2
0.6986	Remote Similarity	NPD4429	Discontinued

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