NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	169.04
Volume:	156.684
LogP:	1.78
LogD:	1.4
LogS:	-1.747
# Rotatable Bonds:	1
TPSA:	83.6
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	2.168
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.445
MDCK Permeability:	0.00013523503730539232
Pgp-inhibitor:	0.0
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):	0.241
Plasma Protein Binding (PPB):	87.69422149658203%
Volume Distribution (VD):	0.297
Pgp-substrate:	10.214577674865723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.804
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.163
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.185
CYP2D6-substrate:	0.458
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	16.132
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.666
Drug-inuced Liver Injury (DILI):	0.609
AMES Toxicity:	0.334
Rat Oral Acute Toxicity:	0.586
Maximum Recommended Daily Dose:	0.79
Skin Sensitization:	0.935
Carcinogencity:	0.846
Eye Corrosion:	0.904
Eye Irritation:	0.966
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC317872

Natural Product ID:	NPC317872
*Common Name:**	4-Methyl-5-Nitrobenzene-1,2-Diol
IUPAC Name:	4-methyl-5-nitrobenzene-1,2-diol
Synonyms:
Standard InCHIKey:	WLLRAKCRHPMKNA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H7NO4/c1-4-2-6(9)7(10)3-5(4)8(11)12/h2-3,9-10H,1H3
SMILES:	CC1=CC(=C(C=C1[N+](=O)[O-])O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL288833
PubChem CID:	4660280
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000141] Nitrophenols

*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
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11976110]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12930985]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16347440]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2013566]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22609920]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25912724]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28335605]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28478925]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8195105]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031664]
NPO30084	Pseudomonas sp.	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9157190]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT269	Individual Protein	Nitric-oxide synthase, brain	Rattus norvegicus	Inhibition	=	35.0	%	PMID[509032]

☑ 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 NPC317872 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	454
0.1-0.2	4374
0.2-0.3	13703
0.3-0.4	6810
0.4-0.5	13079
0.5-0.6	3963
0.6-0.7	304
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7717	Intermediate Similarity	NPC44836
0.7481	Intermediate Similarity	NPC280382
0.7174	Intermediate Similarity	NPC321869
0.7162	Intermediate Similarity	NPC126637
0.7143	Intermediate Similarity	NPC329358
0.7134	Intermediate Similarity	NPC477185
0.7132	Intermediate Similarity	NPC222982
0.7125	Intermediate Similarity	NPC72291
0.7077	Intermediate Similarity	NPC256838
0.7015	Intermediate Similarity	NPC9336
0.7006	Intermediate Similarity	NPC477187
0.6985	Remote Similarity	NPC322735
0.6934	Remote Similarity	NPC329190
0.6867	Remote Similarity	NPC310894
0.6846	Remote Similarity	NPC70201
0.6821	Remote Similarity	NPC166667
0.6812	Remote Similarity	NPC142599
0.6797	Remote Similarity	NPC107522
0.6791	Remote Similarity	NPC76327
0.6788	Remote Similarity	NPC146422
0.6748	Remote Similarity	NPC235628
0.6743	Remote Similarity	NPC477186
0.6687	Remote Similarity	NPC184161
0.6667	Remote Similarity	NPC300020
0.6667	Remote Similarity	NPC302171
0.6667	Remote Similarity	NPC33338
0.6643	Remote Similarity	NPC252817
0.662	Remote Similarity	NPC85276
0.6599	Remote Similarity	NPC318965
0.6591	Remote Similarity	NPC223393
0.6567	Remote Similarity	NPC52087
0.6565	Remote Similarity	NPC109955
0.6554	Remote Similarity	NPC321561
0.6522	Remote Similarity	NPC40209
0.6515	Remote Similarity	NPC131587
0.6503	Remote Similarity	NPC122009
0.6493	Remote Similarity	NPC477801
0.6493	Remote Similarity	NPC477802
0.6493	Remote Similarity	NPC196479
0.649	Remote Similarity	NPC308885
0.649	Remote Similarity	NPC255550
0.649	Remote Similarity	NPC313466
0.6486	Remote Similarity	NPC314278
0.6485	Remote Similarity	NPC291359
0.6481	Remote Similarity	NPC219383
0.6478	Remote Similarity	NPC146370
0.6466	Remote Similarity	NPC29601
0.6463	Remote Similarity	NPC10730
0.6463	Remote Similarity	NPC10875
0.6458	Remote Similarity	NPC268572
0.6455	Remote Similarity	NPC471561
0.6449	Remote Similarity	NPC71266
0.6447	Remote Similarity	NPC130595
0.6447	Remote Similarity	NPC93882
0.6444	Remote Similarity	NPC120719
0.6444	Remote Similarity	NPC79672
0.6444	Remote Similarity	NPC471511
0.6437	Remote Similarity	NPC98416
0.6434	Remote Similarity	NPC283468
0.6418	Remote Similarity	NPC110764
0.6414	Remote Similarity	NPC115627
0.6414	Remote Similarity	NPC118522
0.6414	Remote Similarity	NPC169207
0.6405	Remote Similarity	NPC313737
0.6405	Remote Similarity	NPC6854
0.6405	Remote Similarity	NPC285078
0.64	Remote Similarity	NPC16031
0.64	Remote Similarity	NPC145888
0.64	Remote Similarity	NPC161593
0.6374	Remote Similarity	NPC326634
0.637	Remote Similarity	NPC311660
0.637	Remote Similarity	NPC284078
0.6369	Remote Similarity	NPC323123
0.6364	Remote Similarity	NPC218530
0.6358	Remote Similarity	NPC168153
0.6351	Remote Similarity	NPC318777
0.6351	Remote Similarity	NPC140359
0.6351	Remote Similarity	NPC13020
0.635	Remote Similarity	NPC1786
0.635	Remote Similarity	NPC1075
0.635	Remote Similarity	NPC294902
0.635	Remote Similarity	NPC477814
0.634	Remote Similarity	NPC88667
0.6331	Remote Similarity	NPC228343
0.6331	Remote Similarity	NPC254833
0.6331	Remote Similarity	NPC255721
0.6329	Remote Similarity	NPC470090
0.6329	Remote Similarity	NPC301702
0.6324	Remote Similarity	NPC12278
0.6316	Remote Similarity	NPC257354
0.6306	Remote Similarity	NPC170170
0.6306	Remote Similarity	NPC219233
0.6306	Remote Similarity	NPC211468
0.6304	Remote Similarity	NPC37584
0.6294	Remote Similarity	NPC19555
0.6292	Remote Similarity	NPC28425
0.6286	Remote Similarity	NPC226914
0.6283	Remote Similarity	NPC477825
0.6282	Remote Similarity	NPC159722
0.6282	Remote Similarity	NPC43218
0.6282	Remote Similarity	NPC301050
0.6282	Remote Similarity	NPC131204
0.6277	Remote Similarity	NPC239291
0.6271	Remote Similarity	NPC311936
0.6266	Remote Similarity	NPC314113
0.6259	Remote Similarity	NPC105727
0.6259	Remote Similarity	NPC34864
0.6259	Remote Similarity	NPC114392
0.6259	Remote Similarity	NPC58427
0.6241	Remote Similarity	NPC226250
0.6236	Remote Similarity	NPC119579
0.6235	Remote Similarity	NPC315829
0.6232	Remote Similarity	NPC19149
0.6225	Remote Similarity	NPC236347
0.6225	Remote Similarity	NPC323775
0.6223	Remote Similarity	NPC135887
0.6223	Remote Similarity	NPC199277
0.6218	Remote Similarity	NPC159589
0.6214	Remote Similarity	NPC246358
0.6214	Remote Similarity	NPC7097
0.6214	Remote Similarity	NPC233731
0.6214	Remote Similarity	NPC172046
0.6214	Remote Similarity	NPC36108
0.6211	Remote Similarity	NPC294249
0.6205	Remote Similarity	NPC37272
0.6188	Remote Similarity	NPC320088
0.6187	Remote Similarity	NPC176527
0.6186	Remote Similarity	NPC477827
0.6186	Remote Similarity	NPC477826
0.6184	Remote Similarity	NPC153990
0.6184	Remote Similarity	NPC259098
0.6184	Remote Similarity	NPC251571
0.6184	Remote Similarity	NPC197680
0.618	Remote Similarity	NPC215747
0.618	Remote Similarity	NPC192939
0.6178	Remote Similarity	NPC316574
0.6173	Remote Similarity	NPC471531
0.617	Remote Similarity	NPC174096
0.617	Remote Similarity	NPC222084
0.617	Remote Similarity	NPC120982
0.617	Remote Similarity	NPC226401
0.617	Remote Similarity	NPC147634
0.617	Remote Similarity	NPC79793
0.6167	Remote Similarity	NPC276674
0.6167	Remote Similarity	NPC33902
0.6159	Remote Similarity	NPC428
0.6159	Remote Similarity	NPC24233
0.6159	Remote Similarity	NPC476571
0.6159	Remote Similarity	NPC246587
0.6159	Remote Similarity	NPC147390
0.6159	Remote Similarity	NPC135538
0.6154	Remote Similarity	NPC95381
0.6154	Remote Similarity	NPC475326
0.6154	Remote Similarity	NPC264782
0.6154	Remote Similarity	NPC148969
0.6154	Remote Similarity	NPC264558
0.6149	Remote Similarity	NPC225381
0.6149	Remote Similarity	NPC323798
0.6143	Remote Similarity	NPC233835
0.6142	Remote Similarity	NPC477828
0.6131	Remote Similarity	NPC178902
0.6131	Remote Similarity	NPC469428
0.6131	Remote Similarity	NPC68055
0.6129	Remote Similarity	NPC214869
0.6129	Remote Similarity	NPC474188
0.6127	Remote Similarity	NPC173746
0.6127	Remote Similarity	NPC257124
0.6127	Remote Similarity	NPC187583
0.6127	Remote Similarity	NPC156840
0.6127	Remote Similarity	NPC179002
0.6127	Remote Similarity	NPC257430
0.6127	Remote Similarity	NPC8547
0.6127	Remote Similarity	NPC139617
0.6127	Remote Similarity	NPC297657
0.6127	Remote Similarity	NPC78918
0.6127	Remote Similarity	NPC268032
0.6124	Remote Similarity	NPC260118
0.6115	Remote Similarity	NPC6913
0.6111	Remote Similarity	NPC33749
0.6111	Remote Similarity	NPC125852
0.6111	Remote Similarity	NPC328593
0.6111	Remote Similarity	NPC261453
0.6104	Remote Similarity	NPC195749
0.6104	Remote Similarity	NPC35961
0.6104	Remote Similarity	NPC52029
0.6103	Remote Similarity	NPC155847
0.6103	Remote Similarity	NPC289381
0.6103	Remote Similarity	NPC91234
0.6101	Remote Similarity	NPC314252
0.6099	Remote Similarity	NPC55617
0.6099	Remote Similarity	NPC62258
0.6099	Remote Similarity	NPC22928
0.6098	Remote Similarity	NPC191376
0.6098	Remote Similarity	NPC321505
0.6098	Remote Similarity	NPC179825
0.6094	Remote Similarity	NPC150837
0.6084	Remote Similarity	NPC97221
0.6084	Remote Similarity	NPC192768
0.6084	Remote Similarity	NPC51698
0.6084	Remote Similarity	NPC151895

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 NPC317872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	1059
0.2-0.3	1064
0.3-0.4	3024
0.4-0.5	2850
0.5-0.6	749
0.6-0.7	87
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD711	Discontinued
0.7658	Intermediate Similarity	NPD1293	Approved
0.7453	Intermediate Similarity	NPD1220	Phase 1
0.7423	Intermediate Similarity	NPD1221	Approved
0.6934	Remote Similarity	NPD286	Approved
0.6791	Remote Similarity	NPD9507	Approved
0.6788	Remote Similarity	NPD9379	Approved
0.6788	Remote Similarity	NPD9377	Approved
0.6765	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9247	Phase 3
0.6575	Remote Similarity	NPD9622	Approved
0.6573	Remote Similarity	NPD5641	Discontinued
0.6554	Remote Similarity	NPD258	Approved
0.6554	Remote Similarity	NPD257	Approved
0.6549	Remote Similarity	NPD313	Approved
0.6522	Remote Similarity	NPD9376	Approved
0.6507	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3296	Phase 1
0.649	Remote Similarity	NPD3144	Approved
0.649	Remote Similarity	NPD3145	Approved
0.6452	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2674	Phase 3
0.6419	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD9384	Approved
0.6414	Remote Similarity	NPD9381	Approved
0.6402	Remote Similarity	NPD5617	Suspended
0.64	Remote Similarity	NPD9569	Approved
0.6376	Remote Similarity	NPD3055	Approved
0.6376	Remote Similarity	NPD3053	Approved
0.6352	Remote Similarity	NPD5819	Phase 2
0.634	Remote Similarity	NPD259	Phase 1
0.6331	Remote Similarity	NPD3022	Approved
0.6331	Remote Similarity	NPD3021	Approved
0.6329	Remote Similarity	NPD75	Approved
0.6329	Remote Similarity	NPD9277	Approved
0.6316	Remote Similarity	NPD9536	Phase 1
0.6316	Remote Similarity	NPD9537	Phase 1
0.6306	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD825	Approved
0.6299	Remote Similarity	NPD826	Approved
0.629	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD9278	Suspended
0.6266	Remote Similarity	NPD9275	Approved
0.6266	Remote Similarity	NPD9276	Approved
0.6266	Remote Similarity	NPD9274	Approved
0.6266	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2672	Discontinued
0.6264	Remote Similarity	NPD3634	Approved
0.6264	Remote Similarity	NPD3633	Approved
0.6258	Remote Similarity	NPD275	Approved
0.6258	Remote Similarity	NPD555	Phase 2
0.6258	Remote Similarity	NPD274	Approved
0.6257	Remote Similarity	NPD3511	Discontinued
0.6257	Remote Similarity	NPD2821	Approved
0.625	Remote Similarity	NPD3241	Phase 2
0.6242	Remote Similarity	NPD1162	Approved
0.6241	Remote Similarity	NPD308	Approved
0.6234	Remote Similarity	NPD1136	Approved
0.6234	Remote Similarity	NPD1132	Approved
0.6234	Remote Similarity	NPD1130	Approved
0.6225	Remote Similarity	NPD9621	Approved
0.6225	Remote Similarity	NPD9620	Approved
0.6225	Remote Similarity	NPD9619	Approved
0.6218	Remote Similarity	NPD471	Approved
0.6211	Remote Similarity	NPD302	Approved
0.6207	Remote Similarity	NPD457	Approved
0.62	Remote Similarity	NPD5310	Approved
0.62	Remote Similarity	NPD5311	Approved
0.6182	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD9342	Approved
0.6178	Remote Similarity	NPD6296	Discontinued
0.6178	Remote Similarity	NPD9279	Approved
0.6178	Remote Similarity	NPD6636	Phase 3
0.6169	Remote Similarity	NPD597	Approved
0.6169	Remote Similarity	NPD601	Approved
0.6169	Remote Similarity	NPD598	Approved
0.6149	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD2420	Approved
0.6135	Remote Similarity	NPD2421	Approved
0.6127	Remote Similarity	NPD228	Approved
0.6111	Remote Similarity	NPD9618	Approved
0.6111	Remote Similarity	NPD9614	Approved
0.6102	Remote Similarity	NPD7479	Phase 2
0.6099	Remote Similarity	NPD3398	Discontinued
0.6092	Remote Similarity	NPD4083	Discontinued
0.6087	Remote Similarity	NPD9608	Approved
0.6087	Remote Similarity	NPD965	Approved
0.6087	Remote Similarity	NPD4740	Approved
0.6087	Remote Similarity	NPD9610	Approved
0.6082	Remote Similarity	NPD3453	Discontinued
0.6074	Remote Similarity	NPD3845	Phase 1
0.6074	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2789	Approved
0.6054	Remote Similarity	NPD7125	Discontinued
0.6049	Remote Similarity	NPD1196	Approved
0.6016	Remote Similarity	NPD111	Approved
0.6013	Remote Similarity	NPD817	Approved
0.6013	Remote Similarity	NPD823	Approved
0.6	Remote Similarity	NPD935	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9570	Approved
0.5988	Remote Similarity	NPD1195	Approved
0.5988	Remote Similarity	NPD814	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD3059	Approved
0.5987	Remote Similarity	NPD3061	Approved
0.5987	Remote Similarity	NPD3062	Approved
0.5986	Remote Similarity	NPD254	Approved
0.5978	Remote Similarity	NPD2843	Phase 2
0.5978	Remote Similarity	NPD2845	Phase 2
0.5976	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD956	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5599	Discontinued
0.5964	Remote Similarity	NPD1405	Approved
0.5962	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5811	Approved
0.5952	Remote Similarity	NPD3229	Phase 2
0.5944	Remote Similarity	NPD5637	Discontinued
0.5939	Remote Similarity	NPD1543	Discontinued
0.5931	Remote Similarity	NPD2234	Approved
0.5931	Remote Similarity	NPD2228	Approved
0.5931	Remote Similarity	NPD2229	Approved
0.5931	Remote Similarity	NPD456	Approved
0.592	Remote Similarity	NPD3251	Approved
0.5917	Remote Similarity	NPD3684	Discontinued
0.5917	Remote Similarity	NPD1557	Discontinued
0.5912	Remote Similarity	NPD5314	Approved
0.5909	Remote Similarity	NPD9723	Approved
0.5893	Remote Similarity	NPD9715	Phase 2
0.5893	Remote Similarity	NPD2883	Discontinued
0.5892	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD7628	Phase 3
0.5892	Remote Similarity	NPD7630	Phase 3
0.5887	Remote Similarity	NPD1445	Approved
0.5887	Remote Similarity	NPD1444	Approved
0.5886	Remote Similarity	NPD756	Suspended
0.5882	Remote Similarity	NPD2468	Approved
0.5882	Remote Similarity	NPD2469	Approved
0.5882	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3778	Approved
0.5882	Remote Similarity	NPD9695	Approved
0.5879	Remote Similarity	NPD3141	Discontinued
0.5879	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4951	Discontinued
0.5868	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3252	Approved
0.586	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD19	Approved
0.5838	Remote Similarity	NPD1742	Approved
0.5838	Remote Similarity	NPD1743	Approved
0.5829	Remote Similarity	NPD2341	Discontinued
0.5819	Remote Similarity	NPD2216	Approved
0.5819	Remote Similarity	NPD2215	Approved
0.5806	Remote Similarity	NPD2195	Approved
0.5806	Remote Similarity	NPD2194	Approved
0.5802	Remote Similarity	NPD3391	Approved
0.5799	Remote Similarity	NPD4003	Phase 3
0.5798	Remote Similarity	NPD3631	Phase 3
0.5789	Remote Similarity	NPD1440	Discontinued
0.5789	Remote Similarity	NPD4604	Approved
0.5789	Remote Similarity	NPD4605	Approved
0.5789	Remote Similarity	NPD1622	Discontinued
0.5787	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD1793	Approved
0.5782	Remote Similarity	NPD1791	Approved
0.5772	Remote Similarity	NPD9616	Approved
0.5772	Remote Similarity	NPD9615	Approved
0.5772	Remote Similarity	NPD9613	Approved
0.5771	Remote Similarity	NPD4796	Discontinued
0.5767	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD824	Approved
0.5764	Remote Similarity	NPD1792	Phase 2
0.5764	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.5762	Remote Similarity	NPD9272	Approved
0.5761	Remote Similarity	NPD6045	Phase 3
0.5755	Remote Similarity	NPD1242	Phase 1
0.5754	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD522	Approved
0.5743	Remote Similarity	NPD255	Approved
0.5743	Remote Similarity	NPD256	Approved
0.5741	Remote Similarity	NPD1169	Approved
0.5739	Remote Similarity	NPD7129	Suspended
0.5735	Remote Similarity	NPD2934	Approved
0.5735	Remote Similarity	NPD2933	Approved
0.5735	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD316	Approved
0.5733	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD7153	Discontinued
0.5732	Remote Similarity	NPD1908	Phase 2
0.5732	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.573	Remote Similarity	NPD3975	Discontinued
0.5724	Remote Similarity	NPD1981	Approved
0.5724	Remote Similarity	NPD1980	Approved
0.5724	Remote Similarity	NPD1983	Approved
0.5714	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5610	Approved
0.5714	Remote Similarity	NPD955	Approved
0.5714	Remote Similarity	NPD6184	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