NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	139.03
Volume:	130.598
LogP:	0.37
LogD:	-0.219
LogS:	-1.542
# Rotatable Bonds:	1
TPSA:	70.16
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	2.138
Fsp3:	0.0
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:	-5.583
MDCK Permeability:	6.974338248255663e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.484
Plasma Protein Binding (PPB):	16.62738800048828%
Volume Distribution (VD):	0.2
Pgp-substrate:	72.11234283447266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	4.067
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.227
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.313
Carcinogencity:	0.045
Eye Corrosion:	0.004
Eye Irritation:	0.923
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC113812

Natural Product ID:	NPC113812
*Common Name:**	6-Oxo-1H-Pyridine-3-Carboxylic Acid
IUPAC Name:	6-oxo-1H-pyridine-3-carboxylic acid
Synonyms:	6-Hydroxy-Nicotinic Acid
Standard InCHIKey:	BLHCMGRVFXRYRN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H5NO3/c8-5-2-1-4(3-7-5)6(9)10/h1-3H,(H,7,8)(H,9,10)
SMILES:	Oc1ccc(cn1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL95293
PubChem CID:	72924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001322] Pyridinecarboxylic acids and derivatives [CHEMONTID:0002414] Pyridinecarboxylic acids

*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

☑ 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	1
Others	2
Potency	2

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	30106.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	42.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Activity	=	94.0	%	PMID[497216]
NPT2	Others	Unspecified		Ac50	n.a.	0.5623	uM	PMID[497217]
NPT2	Others	Unspecified		AC50	n.a.	562.3	nM	PMID[497217]

☑ 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 NPC113812 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	608
0.1-0.2	7142
0.2-0.3	10300
0.3-0.4	13794
0.4-0.5	7542
0.5-0.6	2455
0.6-0.7	770
0.7-0.8	68
0.8-0.85	10
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC167400
0.8859	High Similarity	NPC159630
0.8859	High Similarity	NPC230085
0.8712	High Similarity	NPC164340
0.8701	High Similarity	NPC312860
0.8684	High Similarity	NPC112741
0.8645	High Similarity	NPC263455
0.8462	Intermediate Similarity	NPC107287
0.8456	Intermediate Similarity	NPC114310
0.8304	Intermediate Similarity	NPC44354
0.8293	Intermediate Similarity	NPC273532
0.8146	Intermediate Similarity	NPC29702
0.8107	Intermediate Similarity	NPC317010
0.8082	Intermediate Similarity	NPC151489
0.8068	Intermediate Similarity	NPC146724
0.8036	Intermediate Similarity	NPC476419
0.7852	Intermediate Similarity	NPC212125
0.7852	Intermediate Similarity	NPC306397
0.7852	Intermediate Similarity	NPC165370
0.7829	Intermediate Similarity	NPC322488
0.78	Intermediate Similarity	NPC471589
0.7799	Intermediate Similarity	NPC302159
0.7778	Intermediate Similarity	NPC90229
0.7751	Intermediate Similarity	NPC249614
0.7679	Intermediate Similarity	NPC41717
0.7647	Intermediate Similarity	NPC253810
0.7556	Intermediate Similarity	NPC56170
0.7514	Intermediate Similarity	NPC295158
0.7484	Intermediate Similarity	NPC318935
0.7474	Intermediate Similarity	NPC309845
0.7458	Intermediate Similarity	NPC207851
0.7419	Intermediate Similarity	NPC174421
0.7391	Intermediate Similarity	NPC329024
0.7368	Intermediate Similarity	NPC108469
0.7356	Intermediate Similarity	NPC303225
0.7353	Intermediate Similarity	NPC473057
0.7351	Intermediate Similarity	NPC317672
0.7351	Intermediate Similarity	NPC59033
0.7326	Intermediate Similarity	NPC155792
0.731	Intermediate Similarity	NPC471178
0.7305	Intermediate Similarity	NPC33229
0.7258	Intermediate Similarity	NPC320748
0.7258	Intermediate Similarity	NPC324245
0.7251	Intermediate Similarity	NPC97367
0.7243	Intermediate Similarity	NPC109922
0.7238	Intermediate Similarity	NPC278434
0.7233	Intermediate Similarity	NPC328029
0.7213	Intermediate Similarity	NPC114974
0.7191	Intermediate Similarity	NPC325705
0.7191	Intermediate Similarity	NPC52831
0.7181	Intermediate Similarity	NPC79223
0.7172	Intermediate Similarity	NPC74360
0.7152	Intermediate Similarity	NPC220523
0.7143	Intermediate Similarity	NPC328559
0.7143	Intermediate Similarity	NPC32451
0.7135	Intermediate Similarity	NPC183777
0.7135	Intermediate Similarity	NPC193238
0.7134	Intermediate Similarity	NPC471323
0.712	Intermediate Similarity	NPC472259
0.712	Intermediate Similarity	NPC25442
0.712	Intermediate Similarity	NPC12944
0.7098	Intermediate Similarity	NPC171787
0.7093	Intermediate Similarity	NPC59779
0.7093	Intermediate Similarity	NPC471177
0.7093	Intermediate Similarity	NPC124542
0.7083	Intermediate Similarity	NPC309498
0.7074	Intermediate Similarity	NPC474916
0.7065	Intermediate Similarity	NPC83111
0.7062	Intermediate Similarity	NPC472752
0.7049	Intermediate Similarity	NPC206186
0.7048	Intermediate Similarity	NPC161292
0.7047	Intermediate Similarity	NPC156044
0.7044	Intermediate Similarity	NPC194541
0.7033	Intermediate Similarity	NPC241025
0.701	Intermediate Similarity	NPC63041
0.7006	Intermediate Similarity	NPC105811
0.7005	Intermediate Similarity	NPC135950
0.7	Intermediate Similarity	NPC209362
0.6995	Remote Similarity	NPC194040
0.6994	Remote Similarity	NPC85443
0.6988	Remote Similarity	NPC467188
0.6974	Remote Similarity	NPC472550
0.6974	Remote Similarity	NPC304179
0.6974	Remote Similarity	NPC48042
0.6957	Remote Similarity	NPC36498
0.6954	Remote Similarity	NPC219087
0.6952	Remote Similarity	NPC473821
0.6947	Remote Similarity	NPC103361
0.694	Remote Similarity	NPC282103
0.6937	Remote Similarity	NPC330326
0.6919	Remote Similarity	NPC138018
0.6919	Remote Similarity	NPC213914
0.6919	Remote Similarity	NPC183805
0.6918	Remote Similarity	NPC315320
0.6915	Remote Similarity	NPC93390
0.6911	Remote Similarity	NPC213308
0.6901	Remote Similarity	NPC63562
0.6882	Remote Similarity	NPC153769
0.6882	Remote Similarity	NPC70406
0.6869	Remote Similarity	NPC111732
0.6869	Remote Similarity	NPC476467
0.6869	Remote Similarity	NPC472553
0.6856	Remote Similarity	NPC289086
0.685	Remote Similarity	NPC477910
0.6842	Remote Similarity	NPC74153
0.6842	Remote Similarity	NPC473814
0.6842	Remote Similarity	NPC78767
0.6839	Remote Similarity	NPC57398
0.6839	Remote Similarity	NPC322644
0.6837	Remote Similarity	NPC470190
0.6831	Remote Similarity	NPC327373
0.6825	Remote Similarity	NPC202812
0.6824	Remote Similarity	NPC313889
0.6823	Remote Similarity	NPC45459
0.6823	Remote Similarity	NPC315491
0.6821	Remote Similarity	NPC269919
0.6821	Remote Similarity	NPC116573
0.6821	Remote Similarity	NPC132680
0.6816	Remote Similarity	NPC27041
0.6807	Remote Similarity	NPC60553
0.6804	Remote Similarity	NPC317572
0.6802	Remote Similarity	NPC229055
0.68	Remote Similarity	NPC319128
0.68	Remote Similarity	NPC228331
0.6798	Remote Similarity	NPC314940
0.6798	Remote Similarity	NPC276657
0.6798	Remote Similarity	NPC473764
0.6796	Remote Similarity	NPC219848
0.6792	Remote Similarity	NPC313823
0.6791	Remote Similarity	NPC144381
0.6791	Remote Similarity	NPC469489
0.6772	Remote Similarity	NPC45850
0.6771	Remote Similarity	NPC280714
0.6766	Remote Similarity	NPC470306
0.6766	Remote Similarity	NPC477909
0.6766	Remote Similarity	NPC477907
0.6766	Remote Similarity	NPC42678
0.6763	Remote Similarity	NPC74357
0.676	Remote Similarity	NPC302647
0.6758	Remote Similarity	NPC256268
0.6757	Remote Similarity	NPC311282
0.6755	Remote Similarity	NPC138370
0.6754	Remote Similarity	NPC156704
0.6749	Remote Similarity	NPC216428
0.6744	Remote Similarity	NPC251391
0.6743	Remote Similarity	NPC25899
0.6743	Remote Similarity	NPC63338
0.6743	Remote Similarity	NPC322976
0.6743	Remote Similarity	NPC324203
0.6735	Remote Similarity	NPC76540
0.6734	Remote Similarity	NPC40919
0.6734	Remote Similarity	NPC470189
0.6733	Remote Similarity	NPC475408
0.6733	Remote Similarity	NPC477908
0.6733	Remote Similarity	NPC6981
0.6733	Remote Similarity	NPC206343
0.6733	Remote Similarity	NPC471016
0.6733	Remote Similarity	NPC471014
0.673	Remote Similarity	NPC471313
0.673	Remote Similarity	NPC471311
0.6719	Remote Similarity	NPC472284
0.6716	Remote Similarity	NPC237740
0.6716	Remote Similarity	NPC54066
0.6705	Remote Similarity	NPC48192
0.6703	Remote Similarity	NPC285923
0.6703	Remote Similarity	NPC96890
0.67	Remote Similarity	NPC144779
0.67	Remote Similarity	NPC62367
0.67	Remote Similarity	NPC294579
0.6686	Remote Similarity	NPC84508
0.6683	Remote Similarity	NPC477912
0.6667	Remote Similarity	NPC472555
0.6667	Remote Similarity	NPC84815
0.6667	Remote Similarity	NPC263439
0.6667	Remote Similarity	NPC211187
0.6667	Remote Similarity	NPC252590
0.6667	Remote Similarity	NPC301368
0.6651	Remote Similarity	NPC246381
0.6651	Remote Similarity	NPC182222
0.665	Remote Similarity	NPC477911
0.6649	Remote Similarity	NPC322043
0.6649	Remote Similarity	NPC325093
0.6649	Remote Similarity	NPC243058
0.6648	Remote Similarity	NPC319456
0.6633	Remote Similarity	NPC53144
0.6633	Remote Similarity	NPC200836
0.663	Remote Similarity	NPC191310
0.663	Remote Similarity	NPC471997
0.663	Remote Similarity	NPC271792
0.662	Remote Similarity	NPC477549
0.6617	Remote Similarity	NPC280473
0.6617	Remote Similarity	NPC323551
0.6616	Remote Similarity	NPC88008
0.6613	Remote Similarity	NPC203635
0.6612	Remote Similarity	NPC184964
0.6602	Remote Similarity	NPC253314
0.6601	Remote Similarity	NPC207531
0.6601	Remote Similarity	NPC62844
0.6601	Remote Similarity	NPC193361
0.66	Remote Similarity	NPC27802

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 NPC113812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	784
0.2-0.3	816
0.3-0.4	2024
0.4-0.5	3209
0.5-0.6	1671
0.6-0.7	324
0.7-0.8	29
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9315	High Similarity	NPD9075	Approved
0.9315	High Similarity	NPD9074	Approved
0.9041	High Similarity	NPD107	Approved
0.8684	High Similarity	NPD9271	Approved
0.8302	Intermediate Similarity	NPD820	Phase 3
0.8278	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9284	Approved
0.7852	Intermediate Similarity	NPD9080	Approved
0.7751	Intermediate Similarity	NPD485	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD9506	Approved
0.7514	Intermediate Similarity	NPD1173	Approved
0.75	Intermediate Similarity	NPD272	Approved
0.7473	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1649	Discontinued
0.7345	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2831	Approved
0.7251	Intermediate Similarity	NPD5088	Discontinued
0.725	Intermediate Similarity	NPD2896	Discontinued
0.7239	Intermediate Similarity	NPD1352	Discontinued
0.7191	Intermediate Similarity	NPD9510	Approved
0.7186	Intermediate Similarity	NPD510	Phase 1
0.7181	Intermediate Similarity	NPD4491	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1096	Discontinued
0.7134	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8823	Approved
0.7134	Intermediate Similarity	NPD3813	Approved
0.712	Intermediate Similarity	NPD7396	Approved
0.712	Intermediate Similarity	NPD944	Approved
0.7091	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2336	Approved
0.7011	Intermediate Similarity	NPD926	Approved
0.7011	Intermediate Similarity	NPD925	Approved
0.7006	Intermediate Similarity	NPD1270	Approved
0.6982	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD424	Approved
0.6971	Remote Similarity	NPD425	Approved
0.6961	Remote Similarity	NPD3178	Discontinued
0.6957	Remote Similarity	NPD9364	Phase 2
0.6957	Remote Similarity	NPD9363	Approved
0.6937	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD9100	Approved
0.6918	Remote Similarity	NPD9206	Approved
0.6918	Remote Similarity	NPD9207	Approved
0.6901	Remote Similarity	NPD2809	Approved
0.6898	Remote Similarity	NPD981	Phase 2
0.6889	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2307	Discontinued
0.6872	Remote Similarity	NPD158	Discontinued
0.6829	Remote Similarity	NPD852	Discontinued
0.6823	Remote Similarity	NPD484	Approved
0.6821	Remote Similarity	NPD9382	Approved
0.6821	Remote Similarity	NPD9383	Approved
0.6818	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4376	Phase 3
0.6809	Remote Similarity	NPD6665	Discontinued
0.6802	Remote Similarity	NPD2061	Approved
0.6776	Remote Similarity	NPD9362	Approved
0.6766	Remote Similarity	NPD5490	Discontinued
0.6743	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5228	Phase 3
0.6703	Remote Similarity	NPD3569	Discontinued
0.6703	Remote Similarity	NPD721	Approved
0.6701	Remote Similarity	NPD3371	Approved
0.6685	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4948	Discontinued
0.6667	Remote Similarity	NPD1631	Approved
0.6667	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4021	Phase 2
0.6648	Remote Similarity	NPD2511	Approved
0.6647	Remote Similarity	NPD9599	Approved
0.662	Remote Similarity	NPD1483	Discontinued
0.6611	Remote Similarity	NPD1575	Approved
0.6611	Remote Similarity	NPD1573	Approved
0.6603	Remote Similarity	NPD4845	Discontinued
0.66	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5901	Discontinued
0.6593	Remote Similarity	NPD9690	Approved
0.6591	Remote Similarity	NPD604	Clinical (unspecified phase)
0.659	Remote Similarity	NPD9595	Approved
0.659	Remote Similarity	NPD9596	Approved
0.6578	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4989	Phase 2
0.6567	Remote Similarity	NPD4417	Approved
0.6556	Remote Similarity	NPD2781	Approved
0.6554	Remote Similarity	NPD112	Approved
0.6554	Remote Similarity	NPD9705	Discontinued
0.6552	Remote Similarity	NPD180	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6529	Discontinued
0.6548	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5513	Phase 2
0.6545	Remote Similarity	NPD3406	Suspended
0.6541	Remote Similarity	NPD1643	Phase 3
0.654	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2782	Approved
0.6536	Remote Similarity	NPD2780	Approved
0.6527	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD1213	Phase 3
0.6515	Remote Similarity	NPD3947	Discontinued
0.651	Remote Similarity	NPD4551	Phase 2
0.6509	Remote Similarity	NPD4805	Approved
0.6505	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4883	Approved
0.6502	Remote Similarity	NPD3794	Approved
0.6502	Remote Similarity	NPD3243	Approved
0.6502	Remote Similarity	NPD3795	Approved
0.6497	Remote Similarity	NPD1630	Approved
0.6489	Remote Similarity	NPD4889	Approved
0.6455	Remote Similarity	NPD4375	Approved
0.6444	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6987	Phase 1
0.6429	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2509	Approved
0.6418	Remote Similarity	NPD2510	Approved
0.6415	Remote Similarity	NPD2761	Approved
0.6412	Remote Similarity	NPD5020	Approved
0.641	Remote Similarity	NPD2952	Discontinued
0.6409	Remote Similarity	NPD5611	Phase 2
0.6409	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5255	Approved
0.6396	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD8479	Phase 2
0.6391	Remote Similarity	NPD4804	Approved
0.6391	Remote Similarity	NPD569	Clinical (unspecified phase)
0.639	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD269	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5100	Phase 3
0.6378	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD1623	Approved
0.6377	Remote Similarity	NPD2011	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD201	Phase 2
0.6369	Remote Similarity	NPD200	Phase 2
0.6364	Remote Similarity	NPD1618	Phase 2
0.6359	Remote Similarity	NPD750	Phase 2
0.6359	Remote Similarity	NPD1599	Approved
0.6344	Remote Similarity	NPD4071	Approved
0.6344	Remote Similarity	NPD4072	Approved
0.634	Remote Similarity	NPD6361	Phase 2
0.6337	Remote Similarity	NPD7467	Discontinued
0.6333	Remote Similarity	NPD8356	Approved
0.6327	Remote Similarity	NPD1622	Discontinued
0.6324	Remote Similarity	NPD482	Approved
0.6324	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5416	Discontinued
0.6324	Remote Similarity	NPD5475	Discontinued
0.6322	Remote Similarity	NPD4703	Approved
0.6322	Remote Similarity	NPD4702	Approved
0.6321	Remote Similarity	NPD5640	Discontinued
0.6316	Remote Similarity	NPD3280	Approved
0.631	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1587	Approved
0.6304	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD2803	Discontinued
0.6298	Remote Similarity	NPD4429	Discontinued
0.6298	Remote Similarity	NPD1926	Approved
0.6296	Remote Similarity	NPD2095	Phase 2
0.6296	Remote Similarity	NPD2094	Phase 2
0.6296	Remote Similarity	NPD2092	Phase 2
0.6293	Remote Similarity	NPD7069	Discontinued
0.6292	Remote Similarity	NPD276	Clinical (unspecified phase)
0.629	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6135	Phase 1
0.6286	Remote Similarity	NPD4301	Approved
0.6286	Remote Similarity	NPD4923	Phase 1
0.6284	Remote Similarity	NPD1343	Approved
0.6283	Remote Similarity	NPD3039	Clinical (unspecified phase)
0.628	Remote Similarity	NPD1095	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3717	Discontinued
0.6277	Remote Similarity	NPD2600	Approved
0.6277	Remote Similarity	NPD2599	Approved
0.6277	Remote Similarity	NPD2601	Approved
0.6269	Remote Similarity	NPD3321	Discontinued
0.6269	Remote Similarity	NPD5316	Approved
0.6268	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD2096	Phase 2
0.6263	Remote Similarity	NPD6999	Discontinued
0.6263	Remote Similarity	NPD2091	Phase 2
0.6257	Remote Similarity	NPD1032	Phase 2
0.6256	Remote Similarity	NPD9695	Approved
0.6256	Remote Similarity	NPD4528	Approved
0.6256	Remote Similarity	NPD4529	Approved
0.6256	Remote Similarity	NPD4526	Approved
0.625	Remote Similarity	NPD6791	Phase 2
0.625	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD3386	Phase 2
0.6243	Remote Similarity	NPD1684	Approved
0.6243	Remote Similarity	NPD1685	Approved
0.6238	Remote Similarity	NPD2317	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4559	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7010	Phase 3

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