NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	181.04
Volume:	171.343
LogP:	-1.967
LogD:	-1.866
LogS:	-0.422
# Rotatable Bonds:	3
TPSA:	81.31
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	3.264
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:	-5.967
MDCK Permeability:	0.00036135001573711634
Pgp-inhibitor:	0.0
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.858
20% Bioavailability (F20%):	0.218
30% Bioavailability (F30%):	0.505

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.443
Plasma Protein Binding (PPB):	9.068021774291992%
Volume Distribution (VD):	0.265
Pgp-substrate:	91.85982513427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.065
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	2.744
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.475
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.292
Carcinogencity:	0.071
Eye Corrosion:	0.083
Eye Irritation:	0.986
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC312860

Natural Product ID:	NPC312860
*Common Name:**	1-Carboxymethylnicotinic Acid
IUPAC Name:	2-(3-carboxypyridin-1-ium-1-yl)acetate
Synonyms:	1-Carboxymethylnicotinic Acid
Standard InCHIKey:	CABOJBWCHSEHQK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NO4/c10-7(11)5-9-3-1-2-6(4-9)8(12)13/h1-4H,5H2,(H-,10,11,12,13)
SMILES:	c1cc(c[n+](c1)CC(=O)O)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479228
PubChem CID:	44575449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO32788	anthosigmella cf. raromicrosclera	Species	Clionaidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599275]

☑ 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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT201	Individual Protein	Papain	Carica papaya	IC50	=	80.0	ug.mL-1	PMID[452421]

☑ 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 NPC312860 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	475
0.1-0.2	6508
0.2-0.3	12427
0.3-0.4	16154
0.4-0.5	3738
0.5-0.6	2516
0.6-0.7	772
0.7-0.8	89
0.8-0.85	8
0.85-0.9	5
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9521	High Similarity	NPC263455
0.9371	High Similarity	NPC159630
0.9371	High Similarity	NPC230085
0.9306	High Similarity	NPC167400
0.8919	High Similarity	NPC112741
0.8854	High Similarity	NPC273532
0.8808	High Similarity	NPC107287
0.8701	High Similarity	NPC113812
0.8642	High Similarity	NPC317010
0.8493	Intermediate Similarity	NPC29702
0.8457	Intermediate Similarity	NPC476419
0.8435	Intermediate Similarity	NPC114310
0.8235	Intermediate Similarity	NPC302159
0.8199	Intermediate Similarity	NPC41717
0.8014	Intermediate Similarity	NPC471589
0.7941	Intermediate Similarity	NPC207851
0.7939	Intermediate Similarity	NPC249614
0.7919	Intermediate Similarity	NPC322488
0.7823	Intermediate Similarity	NPC165370
0.7823	Intermediate Similarity	NPC212125
0.7823	Intermediate Similarity	NPC306397
0.7811	Intermediate Similarity	NPC164340
0.7702	Intermediate Similarity	NPC33229
0.7647	Intermediate Similarity	NPC328029
0.7611	Intermediate Similarity	NPC59033
0.7607	Intermediate Similarity	NPC213914
0.7593	Intermediate Similarity	NPC209362
0.7569	Intermediate Similarity	NPC103361
0.7554	Intermediate Similarity	NPC25442
0.7554	Intermediate Similarity	NPC12944
0.7542	Intermediate Similarity	NPC135950
0.7527	Intermediate Similarity	NPC79223
0.75	Intermediate Similarity	NPC105811
0.75	Intermediate Similarity	NPC85443
0.7484	Intermediate Similarity	NPC467188
0.7473	Intermediate Similarity	NPC156044
0.7459	Intermediate Similarity	NPC329024
0.7458	Intermediate Similarity	NPC44354
0.7446	Intermediate Similarity	NPC57398
0.7421	Intermediate Similarity	NPC471323
0.7418	Intermediate Similarity	NPC324245
0.7418	Intermediate Similarity	NPC320748
0.7418	Intermediate Similarity	NPC317672
0.7416	Intermediate Similarity	NPC469489
0.7403	Intermediate Similarity	NPC109922
0.7394	Intermediate Similarity	NPC138018
0.7322	Intermediate Similarity	NPC474916
0.731	Intermediate Similarity	NPC253810
0.7305	Intermediate Similarity	NPC322644
0.7303	Intermediate Similarity	NPC278434
0.7297	Intermediate Similarity	NPC328559
0.7297	Intermediate Similarity	NPC32451
0.7294	Intermediate Similarity	NPC470894
0.7288	Intermediate Similarity	NPC311282
0.7288	Intermediate Similarity	NPC295158
0.7283	Intermediate Similarity	NPC123395
0.7278	Intermediate Similarity	NPC114974
0.7277	Intermediate Similarity	NPC111732
0.7273	Intermediate Similarity	NPC229055
0.7256	Intermediate Similarity	NPC70406
0.7253	Intermediate Similarity	NPC146724
0.7234	Intermediate Similarity	NPC309498
0.7229	Intermediate Similarity	NPC74357
0.7212	Intermediate Similarity	NPC251391
0.7209	Intermediate Similarity	NPC302647
0.7195	Intermediate Similarity	NPC313889
0.7191	Intermediate Similarity	NPC282103
0.719	Intermediate Similarity	NPC313823
0.7174	Intermediate Similarity	NPC90229
0.7158	Intermediate Similarity	NPC63041
0.7152	Intermediate Similarity	NPC472260
0.7152	Intermediate Similarity	NPC109158
0.7152	Intermediate Similarity	NPC472288
0.7127	Intermediate Similarity	NPC83111
0.712	Intermediate Similarity	NPC48042
0.712	Intermediate Similarity	NPC472752
0.712	Intermediate Similarity	NPC472550
0.712	Intermediate Similarity	NPC304179
0.7115	Intermediate Similarity	NPC330326
0.7105	Intermediate Similarity	NPC151489
0.7097	Intermediate Similarity	NPC315320
0.7095	Intermediate Similarity	NPC318020
0.7093	Intermediate Similarity	NPC319456
0.709	Intermediate Similarity	NPC472259
0.709	Intermediate Similarity	NPC289086
0.7072	Intermediate Similarity	NPC75544
0.7032	Intermediate Similarity	NPC71236
0.703	Intermediate Similarity	NPC123906
0.701	Intermediate Similarity	NPC476467
0.701	Intermediate Similarity	NPC472553
0.7006	Intermediate Similarity	NPC194541
0.7	Intermediate Similarity	NPC241025
0.6995	Remote Similarity	NPC138370
0.6994	Remote Similarity	NPC70949
0.6983	Remote Similarity	NPC327373
0.6983	Remote Similarity	NPC325093
0.6979	Remote Similarity	NPC470190
0.6978	Remote Similarity	NPC182814
0.6977	Remote Similarity	NPC477975
0.697	Remote Similarity	NPC477974
0.6957	Remote Similarity	NPC56170
0.6952	Remote Similarity	NPC248782
0.6939	Remote Similarity	NPC319128
0.6939	Remote Similarity	NPC228331
0.6935	Remote Similarity	NPC77061
0.6923	Remote Similarity	NPC76540
0.6915	Remote Similarity	NPC474767
0.691	Remote Similarity	NPC256268
0.6907	Remote Similarity	NPC309845
0.6904	Remote Similarity	NPC470306
0.6904	Remote Similarity	NPC477909
0.6904	Remote Similarity	NPC477907
0.6904	Remote Similarity	NPC477910
0.6904	Remote Similarity	NPC42678
0.6903	Remote Similarity	NPC471313
0.6903	Remote Similarity	NPC471311
0.6902	Remote Similarity	NPC127647
0.6891	Remote Similarity	NPC266249
0.6882	Remote Similarity	NPC202812
0.6875	Remote Similarity	NPC477976
0.6872	Remote Similarity	NPC40919
0.6872	Remote Similarity	NPC61011
0.6872	Remote Similarity	NPC470189
0.6872	Remote Similarity	NPC325705
0.6872	Remote Similarity	NPC52831
0.6869	Remote Similarity	NPC6981
0.6869	Remote Similarity	NPC475408
0.6869	Remote Similarity	NPC471016
0.6869	Remote Similarity	NPC471014
0.6869	Remote Similarity	NPC206343
0.6869	Remote Similarity	NPC477908
0.6864	Remote Similarity	NPC298288
0.6854	Remote Similarity	NPC219848
0.6851	Remote Similarity	NPC46895
0.6851	Remote Similarity	NPC285923
0.6845	Remote Similarity	NPC470679
0.6845	Remote Similarity	NPC217021
0.6842	Remote Similarity	NPC80681
0.6837	Remote Similarity	NPC280473
0.6837	Remote Similarity	NPC323551
0.6836	Remote Similarity	NPC469938
0.6835	Remote Similarity	NPC174421
0.6834	Remote Similarity	NPC294579
0.6834	Remote Similarity	NPC62367
0.6834	Remote Similarity	NPC144779
0.6832	Remote Similarity	NPC229893
0.6831	Remote Similarity	NPC328798
0.6821	Remote Similarity	NPC265100
0.6821	Remote Similarity	NPC123839
0.6816	Remote Similarity	NPC283219
0.681	Remote Similarity	NPC318935
0.6802	Remote Similarity	NPC165837
0.6802	Remote Similarity	NPC41724
0.6802	Remote Similarity	NPC51008
0.68	Remote Similarity	NPC471402
0.68	Remote Similarity	NPC216428
0.68	Remote Similarity	NPC472555
0.68	Remote Similarity	NPC297486
0.68	Remote Similarity	NPC301368
0.68	Remote Similarity	NPC240136
0.68	Remote Similarity	NPC84815
0.6796	Remote Similarity	NPC322043
0.6786	Remote Similarity	NPC82370
0.6782	Remote Similarity	NPC471178
0.6781	Remote Similarity	NPC27802
0.678	Remote Similarity	NPC191310
0.6778	Remote Similarity	NPC73994
0.6776	Remote Similarity	NPC118084
0.6772	Remote Similarity	NPC472284
0.6768	Remote Similarity	NPC4421
0.6768	Remote Similarity	NPC264674
0.6766	Remote Similarity	NPC54066
0.676	Remote Similarity	NPC83774
0.6754	Remote Similarity	NPC98864
0.6751	Remote Similarity	NPC118940
0.6748	Remote Similarity	NPC43477
0.6743	Remote Similarity	NPC114637
0.6739	Remote Similarity	NPC36498
0.6738	Remote Similarity	NPC103230
0.6734	Remote Similarity	NPC62844
0.6734	Remote Similarity	NPC207531
0.6734	Remote Similarity	NPC193361
0.6733	Remote Similarity	NPC477912
0.673	Remote Similarity	NPC324611
0.673	Remote Similarity	NPC256893
0.6728	Remote Similarity	NPC65408
0.6722	Remote Similarity	NPC248041
0.6722	Remote Similarity	NPC126709
0.6705	Remote Similarity	NPC473706
0.6703	Remote Similarity	NPC243058
0.6702	Remote Similarity	NPC93390
0.67	Remote Similarity	NPC127026
0.67	Remote Similarity	NPC477911
0.67	Remote Similarity	NPC127720
0.67	Remote Similarity	NPC472285
0.6686	Remote Similarity	NPC473878
0.6685	Remote Similarity	NPC471997
0.6684	Remote Similarity	NPC143325
0.6667	Remote Similarity	NPC473115
0.6667	Remote Similarity	NPC318299

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 NPC312860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	716
0.2-0.3	884
0.3-0.4	2064
0.4-0.5	3086
0.5-0.6	1716
0.6-0.7	406
0.7-0.8	46
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9306	High Similarity	NPD9075	Approved
0.9306	High Similarity	NPD9074	Approved
0.9296	High Similarity	NPD107	Approved
0.8919	High Similarity	NPD9271	Approved
0.8636	High Similarity	NPD820	Phase 3
0.8378	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD272	Approved
0.7829	Intermediate Similarity	NPD9506	Approved
0.7823	Intermediate Similarity	NPD9284	Approved
0.7823	Intermediate Similarity	NPD9080	Approved
0.7725	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1096	Discontinued
0.7616	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1173	Approved
0.7578	Intermediate Similarity	NPD510	Phase 1
0.7542	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1649	Discontinued
0.7436	Intermediate Similarity	NPD2896	Discontinued
0.743	Intermediate Similarity	NPD981	Phase 2
0.7421	Intermediate Similarity	NPD1352	Discontinued
0.7414	Intermediate Similarity	NPD3178	Discontinued
0.7375	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6665	Discontinued
0.7321	Intermediate Similarity	NPD5088	Discontinued
0.7284	Intermediate Similarity	NPD1270	Approved
0.7273	Intermediate Similarity	NPD7396	Approved
0.7235	Intermediate Similarity	NPD4174	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1631	Approved
0.7205	Intermediate Similarity	NPD3813	Approved
0.7205	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3371	Approved
0.7188	Intermediate Similarity	NPD4805	Approved
0.7182	Intermediate Similarity	NPD2336	Approved
0.7181	Intermediate Similarity	NPD944	Approved
0.7179	Intermediate Similarity	NPD1623	Approved
0.7151	Intermediate Similarity	NPD1573	Approved
0.7151	Intermediate Similarity	NPD1575	Approved
0.7143	Intermediate Similarity	NPD1630	Approved
0.7115	Intermediate Similarity	NPD9100	Approved
0.7097	Intermediate Similarity	NPD9207	Approved
0.7097	Intermediate Similarity	NPD9206	Approved
0.709	Intermediate Similarity	NPD2831	Approved
0.7063	Intermediate Similarity	NPD4804	Approved
0.7049	Intermediate Similarity	NPD4376	Phase 3
0.7037	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2307	Discontinued
0.7006	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3947	Discontinued
0.6977	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1643	Phase 3
0.6964	Remote Similarity	NPD2061	Approved
0.6923	Remote Similarity	NPD4948	Discontinued
0.6914	Remote Similarity	NPD9599	Approved
0.6904	Remote Similarity	NPD5490	Discontinued
0.6901	Remote Similarity	NPD2511	Approved
0.6878	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD750	Phase 2
0.6872	Remote Similarity	NPD9510	Approved
0.6864	Remote Similarity	NPD2809	Approved
0.6852	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD721	Approved
0.6833	Remote Similarity	NPD9362	Approved
0.6816	Remote Similarity	NPD1587	Approved
0.6813	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1380	Discovery
0.6786	Remote Similarity	NPD4417	Approved
0.6786	Remote Similarity	NPD5475	Discontinued
0.6772	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5255	Approved
0.6742	Remote Similarity	NPD1586	Approved
0.6739	Remote Similarity	NPD9363	Approved
0.6739	Remote Similarity	NPD9364	Phase 2
0.6736	Remote Similarity	NPD4905	Approved
0.6736	Remote Similarity	NPD4903	Approved
0.6736	Remote Similarity	NPD6987	Phase 1
0.6736	Remote Similarity	NPD4906	Approved
0.6736	Remote Similarity	NPD5901	Discontinued
0.6728	Remote Similarity	NPD200	Phase 2
0.6728	Remote Similarity	NPD201	Phase 2
0.672	Remote Similarity	NPD1977	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2510	Approved
0.6718	Remote Similarity	NPD2509	Approved
0.6717	Remote Similarity	NPD3795	Approved
0.6717	Remote Similarity	NPD3794	Approved
0.6701	Remote Similarity	NPD4904	Approved
0.6687	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1618	Phase 2
0.6684	Remote Similarity	NPD3288	Approved
0.6684	Remote Similarity	NPD3406	Suspended
0.6667	Remote Similarity	NPD5017	Discontinued
0.6667	Remote Similarity	NPD2290	Phase 3
0.6667	Remote Similarity	NPD1383	Phase 3
0.6667	Remote Similarity	NPD5020	Approved
0.6667	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3569	Discontinued
0.6667	Remote Similarity	NPD6173	Approved
0.6667	Remote Similarity	NPD1382	Phase 2
0.6667	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2289	Phase 3
0.665	Remote Similarity	NPD3393	Approved
0.665	Remote Similarity	NPD3389	Approved
0.665	Remote Similarity	NPD3394	Approved
0.6649	Remote Similarity	NPD4526	Approved
0.6649	Remote Similarity	NPD4528	Approved
0.6649	Remote Similarity	NPD4529	Approved
0.6649	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4883	Approved
0.6648	Remote Similarity	NPD482	Approved
0.6647	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD9595	Approved
0.6647	Remote Similarity	NPD9596	Approved
0.6627	Remote Similarity	NPD1427	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5228	Phase 3
0.6611	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6529	Discontinued
0.6593	Remote Similarity	NPD6452	Discontinued
0.659	Remote Similarity	NPD2582	Approved
0.659	Remote Similarity	NPD2581	Approved
0.6578	Remote Similarity	NPD3321	Discontinued
0.6569	Remote Similarity	NPD4301	Approved
0.6568	Remote Similarity	NPD4703	Approved
0.6568	Remote Similarity	NPD4702	Approved
0.6564	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4988	Discontinued
0.6557	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD158	Discontinued
0.6556	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5611	Phase 2
0.6552	Remote Similarity	NPD7404	Approved
0.655	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3717	Discontinued
0.6522	Remote Similarity	NPD9726	Discontinued
0.6522	Remote Similarity	NPD2092	Phase 2
0.6522	Remote Similarity	NPD2094	Phase 2
0.6522	Remote Similarity	NPD2095	Phase 2
0.652	Remote Similarity	NPD3280	Approved
0.6517	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1343	Approved
0.6516	Remote Similarity	NPD268	Approved
0.6516	Remote Similarity	NPD271	Approved
0.6516	Remote Similarity	NPD270	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6752	Phase 1
0.6505	Remote Similarity	NPD3315	Phase 3
0.6505	Remote Similarity	NPD6753	Phase 1
0.65	Remote Similarity	NPD1599	Approved
0.6494	Remote Similarity	NPD9382	Approved
0.6494	Remote Similarity	NPD9383	Approved
0.6486	Remote Similarity	NPD2417	Approved
0.6486	Remote Similarity	NPD2096	Phase 2
0.6486	Remote Similarity	NPD2416	Approved
0.6486	Remote Similarity	NPD2091	Phase 2
0.648	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6999	Discontinued
0.6467	Remote Similarity	NPD4823	Approved
0.6467	Remote Similarity	NPD4824	Approved
0.6461	Remote Similarity	NPD424	Approved
0.6461	Remote Similarity	NPD425	Approved
0.6453	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7010	Phase 3
0.6443	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD484	Approved
0.6439	Remote Similarity	NPD1996	Discontinued
0.6438	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5583	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5891	Approved
0.6429	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5100	Phase 3
0.6422	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5505	Discontinued
0.6421	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.642	Remote Similarity	NPD112	Approved
0.642	Remote Similarity	NPD1527	Phase 2
0.642	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.642	Remote Similarity	NPD9705	Discontinued
0.6417	Remote Similarity	NPD5809	Phase 3
0.6414	Remote Similarity	NPD6135	Phase 1
0.6413	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD2481	Approved
0.6413	Remote Similarity	NPD2479	Phase 3
0.6406	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6226	Phase 3
0.6404	Remote Similarity	NPD926	Approved
0.6404	Remote Similarity	NPD925	Approved
0.6402	Remote Similarity	NPD8063	Discontinued
0.6402	Remote Similarity	NPD2544	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD460	Discontinued
0.6384	Remote Similarity	NPD5400	Approved
0.6382	Remote Similarity	NPD1367	Phase 2

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