NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	158.01
Volume:	145.954
LogP:	2.43
LogD:	2.173
LogS:	-1.095
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	2.237
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.529
MDCK Permeability:	2.4417195163550787e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	91.93460083007812%
Volume Distribution (VD):	0.574
Pgp-substrate:	7.315788269042969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.942
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.202
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.806
CYP2D6-inhibitor:	0.388
CYP2D6-substrate:	0.632
CYP3A4-inhibitor:	0.128
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	13.493
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.922
Carcinogencity:	0.262
Eye Corrosion:	0.961
Eye Irritation:	0.985
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC187958

Natural Product ID:	NPC187958
*Common Name:**	4-Chloro-3,5-Dihydroxytoluene
IUPAC Name:	2-chloro-5-methylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	HLQYXRVJOUOMFF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H7ClO2/c1-4-2-5(9)7(8)6(10)3-4/h2-3,9-10H,1H3
SMILES:	Cc1cc(c(c(c1)O)Cl)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448814
PubChem CID:	5324741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	diseased bulbs	n.a.	n.a.	PMID[9677274]
NPO18110	Lilium maximowiczii	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5063	Organism	Bipolaris leersiae	Bipolaris leersiae	Inhibition	=	80.0	%	PMID[457239]

☑ 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 NPC187958 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	529
0.1-0.2	3612
0.2-0.3	13407
0.3-0.4	7157
0.4-0.5	8433
0.5-0.6	7842
0.6-0.7	1485
0.7-0.8	213
0.8-0.85	8
0.85-0.9	3
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC43411
0.8515	High Similarity	NPC295295
0.8037	Intermediate Similarity	NPC166761
0.8019	Intermediate Similarity	NPC291789
0.8018	Intermediate Similarity	NPC146096
0.7963	Intermediate Similarity	NPC166313
0.7963	Intermediate Similarity	NPC11280
0.7963	Intermediate Similarity	NPC147310
0.7963	Intermediate Similarity	NPC294186
0.7963	Intermediate Similarity	NPC24407
0.7963	Intermediate Similarity	NPC137415
0.7963	Intermediate Similarity	NPC192032
0.789	Intermediate Similarity	NPC146798
0.789	Intermediate Similarity	NPC106396
0.789	Intermediate Similarity	NPC94351
0.789	Intermediate Similarity	NPC222522
0.789	Intermediate Similarity	NPC168303
0.789	Intermediate Similarity	NPC242342
0.789	Intermediate Similarity	NPC302219
0.789	Intermediate Similarity	NPC313030
0.789	Intermediate Similarity	NPC249828
0.789	Intermediate Similarity	NPC24404
0.789	Intermediate Similarity	NPC85479
0.789	Intermediate Similarity	NPC53051
0.789	Intermediate Similarity	NPC71002
0.787	Intermediate Similarity	NPC275053
0.787	Intermediate Similarity	NPC161571
0.787	Intermediate Similarity	NPC10588
0.787	Intermediate Similarity	NPC248573
0.7826	Intermediate Similarity	NPC91452
0.7818	Intermediate Similarity	NPC227458
0.7818	Intermediate Similarity	NPC244513
0.7818	Intermediate Similarity	NPC218879
0.7815	Intermediate Similarity	NPC67791
0.7798	Intermediate Similarity	NPC284011
0.7798	Intermediate Similarity	NPC72947
0.7798	Intermediate Similarity	NPC143659
0.7798	Intermediate Similarity	NPC100340
0.7797	Intermediate Similarity	NPC15350
0.7748	Intermediate Similarity	NPC37802
0.7692	Intermediate Similarity	NPC244403
0.7679	Intermediate Similarity	NPC164576
0.7679	Intermediate Similarity	NPC12640
0.7679	Intermediate Similarity	NPC99836
0.7679	Intermediate Similarity	NPC201662
0.7658	Intermediate Similarity	NPC241891
0.7658	Intermediate Similarity	NPC102216
0.7658	Intermediate Similarity	NPC30506
0.7647	Intermediate Similarity	NPC150837
0.7619	Intermediate Similarity	NPC185313
0.7615	Intermediate Similarity	NPC80027
0.7611	Intermediate Similarity	NPC305603
0.7611	Intermediate Similarity	NPC158253
0.7611	Intermediate Similarity	NPC61033
0.7611	Intermediate Similarity	NPC204901
0.7611	Intermediate Similarity	NPC232523
0.7589	Intermediate Similarity	NPC292452
0.7589	Intermediate Similarity	NPC134829
0.7589	Intermediate Similarity	NPC246056
0.7544	Intermediate Similarity	NPC174981
0.7541	Intermediate Similarity	NPC42644
0.7522	Intermediate Similarity	NPC118286
0.7522	Intermediate Similarity	NPC470700
0.7522	Intermediate Similarity	NPC302681
0.7522	Intermediate Similarity	NPC39097
0.7522	Intermediate Similarity	NPC109691
0.7522	Intermediate Similarity	NPC39664
0.75	Intermediate Similarity	NPC4154
0.7478	Intermediate Similarity	NPC299568
0.7478	Intermediate Similarity	NPC186385
0.7478	Intermediate Similarity	NPC19808
0.7478	Intermediate Similarity	NPC33728
0.746	Intermediate Similarity	NPC26576
0.7456	Intermediate Similarity	NPC54844
0.7456	Intermediate Similarity	NPC176527
0.7429	Intermediate Similarity	NPC19680
0.7429	Intermediate Similarity	NPC27974
0.7426	Intermediate Similarity	NPC270094
0.7414	Intermediate Similarity	NPC224870
0.7414	Intermediate Similarity	NPC94045
0.7414	Intermediate Similarity	NPC242178
0.7414	Intermediate Similarity	NPC168657
0.7391	Intermediate Similarity	NPC114392
0.7391	Intermediate Similarity	NPC105727
0.7391	Intermediate Similarity	NPC34864
0.7391	Intermediate Similarity	NPC58427
0.7383	Intermediate Similarity	NPC174048
0.7383	Intermediate Similarity	NPC322888
0.736	Intermediate Similarity	NPC33402
0.735	Intermediate Similarity	NPC225679
0.735	Intermediate Similarity	NPC255068
0.735	Intermediate Similarity	NPC296920
0.735	Intermediate Similarity	NPC90520
0.735	Intermediate Similarity	NPC4493
0.735	Intermediate Similarity	NPC165770
0.735	Intermediate Similarity	NPC476632
0.735	Intermediate Similarity	NPC224527
0.7339	Intermediate Similarity	NPC122175
0.7328	Intermediate Similarity	NPC202647
0.7315	Intermediate Similarity	NPC29373
0.729	Intermediate Similarity	NPC312304
0.7288	Intermediate Similarity	NPC43525
0.7288	Intermediate Similarity	NPC166995
0.7288	Intermediate Similarity	NPC280606
0.7288	Intermediate Similarity	NPC473521
0.7281	Intermediate Similarity	NPC471350
0.7227	Intermediate Similarity	NPC117846
0.7227	Intermediate Similarity	NPC23804
0.7227	Intermediate Similarity	NPC162113
0.7227	Intermediate Similarity	NPC319803
0.7227	Intermediate Similarity	NPC62546
0.7227	Intermediate Similarity	NPC263753
0.7222	Intermediate Similarity	NPC174729
0.7222	Intermediate Similarity	NPC231150
0.7217	Intermediate Similarity	NPC248904
0.7212	Intermediate Similarity	NPC38459
0.7212	Intermediate Similarity	NPC33756
0.7212	Intermediate Similarity	NPC124436
0.7207	Intermediate Similarity	NPC88420
0.7203	Intermediate Similarity	NPC268032
0.7193	Intermediate Similarity	NPC119860
0.7182	Intermediate Similarity	NPC107522
0.7167	Intermediate Similarity	NPC107240
0.7167	Intermediate Similarity	NPC180508
0.7167	Intermediate Similarity	NPC22610
0.7167	Intermediate Similarity	NPC276737
0.7167	Intermediate Similarity	NPC228287
0.7156	Intermediate Similarity	NPC94139
0.7156	Intermediate Similarity	NPC162314
0.7156	Intermediate Similarity	NPC306884
0.7156	Intermediate Similarity	NPC3358
0.7156	Intermediate Similarity	NPC210497
0.7156	Intermediate Similarity	NPC147284
0.7156	Intermediate Similarity	NPC55903
0.7143	Intermediate Similarity	NPC248817
0.7143	Intermediate Similarity	NPC286904
0.713	Intermediate Similarity	NPC192
0.713	Intermediate Similarity	NPC474839
0.713	Intermediate Similarity	NPC300478
0.713	Intermediate Similarity	NPC47950
0.7109	Intermediate Similarity	NPC91204
0.7109	Intermediate Similarity	NPC111723
0.7109	Intermediate Similarity	NPC8058
0.7109	Intermediate Similarity	NPC237517
0.7107	Intermediate Similarity	NPC53906
0.7107	Intermediate Similarity	NPC84999
0.7107	Intermediate Similarity	NPC808
0.7107	Intermediate Similarity	NPC472893
0.7107	Intermediate Similarity	NPC246760
0.7107	Intermediate Similarity	NPC167934
0.7105	Intermediate Similarity	NPC315022
0.7105	Intermediate Similarity	NPC168393
0.7094	Intermediate Similarity	NPC63698
0.7094	Intermediate Similarity	NPC61885
0.7091	Intermediate Similarity	NPC245187
0.7083	Intermediate Similarity	NPC261343
0.7083	Intermediate Similarity	NPC98543
0.708	Intermediate Similarity	NPC130103
0.7075	Intermediate Similarity	NPC197783
0.7054	Intermediate Similarity	NPC32715
0.7054	Intermediate Similarity	NPC474073
0.7054	Intermediate Similarity	NPC152097
0.7054	Intermediate Similarity	NPC98200
0.7054	Intermediate Similarity	NPC475078
0.7049	Intermediate Similarity	NPC123559
0.7049	Intermediate Similarity	NPC203113
0.7049	Intermediate Similarity	NPC193067
0.7049	Intermediate Similarity	NPC141090
0.7049	Intermediate Similarity	NPC114064
0.7049	Intermediate Similarity	NPC150624
0.7048	Intermediate Similarity	NPC265146
0.7045	Intermediate Similarity	NPC139335
0.7043	Intermediate Similarity	NPC130817
0.7043	Intermediate Similarity	NPC315936
0.7027	Intermediate Similarity	NPC257182
0.7027	Intermediate Similarity	NPC313650
0.7027	Intermediate Similarity	NPC222146
0.7027	Intermediate Similarity	NPC274678
0.7009	Intermediate Similarity	NPC307235
0.7009	Intermediate Similarity	NPC407
0.7009	Intermediate Similarity	NPC23167
0.7009	Intermediate Similarity	NPC280254
0.7009	Intermediate Similarity	NPC184169
0.6992	Remote Similarity	NPC15860
0.6992	Remote Similarity	NPC33270
0.6992	Remote Similarity	NPC221549
0.6992	Remote Similarity	NPC195466
0.6992	Remote Similarity	NPC219070
0.6992	Remote Similarity	NPC277588
0.6992	Remote Similarity	NPC259638
0.6992	Remote Similarity	NPC470759
0.6992	Remote Similarity	NPC127894
0.6992	Remote Similarity	NPC244816
0.6992	Remote Similarity	NPC50521
0.6992	Remote Similarity	NPC474933
0.6992	Remote Similarity	NPC69261
0.6991	Remote Similarity	NPC260775
0.6981	Remote Similarity	NPC175313
0.697	Remote Similarity	NPC193334
0.6964	Remote Similarity	NPC312132

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 NPC187958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	462
0.1-0.2	1172
0.2-0.3	2383
0.3-0.4	2861
0.4-0.5	1618
0.5-0.6	554
0.6-0.7	91
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.789	Intermediate Similarity	NPD9500	Approved
0.787	Intermediate Similarity	NPD1242	Phase 1
0.75	Intermediate Similarity	NPD9093	Approved
0.7478	Intermediate Similarity	NPD4750	Phase 3
0.7477	Intermediate Similarity	NPD940	Approved
0.7477	Intermediate Similarity	NPD846	Approved
0.7426	Intermediate Similarity	NPD9089	Approved
0.7212	Intermediate Similarity	NPD111	Approved
0.7212	Intermediate Similarity	NPD9073	Approved
0.7027	Intermediate Similarity	NPD844	Approved
0.7025	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9094	Approved
0.6964	Remote Similarity	NPD288	Approved
0.693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4589	Approved
0.6797	Remote Similarity	NPD1157	Approved
0.6791	Remote Similarity	NPD1555	Discontinued
0.6786	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2933	Approved
0.6786	Remote Similarity	NPD2934	Approved
0.6757	Remote Similarity	NPD9251	Approved
0.6754	Remote Similarity	NPD9273	Approved
0.6726	Remote Similarity	NPD2859	Approved
0.6726	Remote Similarity	NPD2860	Approved
0.6696	Remote Similarity	NPD3020	Approved
0.6634	Remote Similarity	NPD9087	Approved
0.6615	Remote Similarity	NPD4749	Approved
0.6557	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD845	Approved
0.6538	Remote Similarity	NPD9269	Phase 2
0.6538	Remote Similarity	NPD9088	Approved
0.65	Remote Similarity	NPD1444	Approved
0.65	Remote Similarity	NPD1445	Approved
0.6496	Remote Similarity	NPD1616	Discontinued
0.6484	Remote Similarity	NPD9268	Approved
0.6475	Remote Similarity	NPD3021	Approved
0.6475	Remote Similarity	NPD3022	Approved
0.6466	Remote Similarity	NPD858	Approved
0.6466	Remote Similarity	NPD602	Approved
0.6466	Remote Similarity	NPD599	Approved
0.6466	Remote Similarity	NPD859	Approved
0.6435	Remote Similarity	NPD1809	Phase 2
0.6406	Remote Similarity	NPD1548	Phase 1
0.6371	Remote Similarity	NPD228	Approved
0.6343	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1792	Phase 2
0.6339	Remote Similarity	NPD9249	Phase 1
0.6336	Remote Similarity	NPD1610	Phase 2
0.6336	Remote Similarity	NPD422	Phase 1
0.6333	Remote Similarity	NPD9244	Approved
0.6324	Remote Similarity	NPD4625	Phase 3
0.6324	Remote Similarity	NPD3027	Phase 3
0.6311	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD454	Approved
0.6296	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1416	Approved
0.6286	Remote Similarity	NPD4538	Approved
0.6286	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4536	Approved
0.6277	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.626	Remote Similarity	NPD9266	Approved
0.626	Remote Similarity	NPD74	Approved
0.6259	Remote Similarity	NPD3364	Phase 3
0.625	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD829	Discontinued
0.622	Remote Similarity	NPD911	Approved
0.622	Remote Similarity	NPD9618	Approved
0.622	Remote Similarity	NPD9614	Approved
0.621	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD2372	Approved
0.62	Remote Similarity	NPD1714	Approved
0.62	Remote Similarity	NPD1715	Phase 1
0.6198	Remote Similarity	NPD9608	Approved
0.6198	Remote Similarity	NPD9610	Approved
0.619	Remote Similarity	NPD9377	Approved
0.619	Remote Similarity	NPD7635	Approved
0.619	Remote Similarity	NPD9379	Approved
0.6179	Remote Similarity	NPD9263	Approved
0.6179	Remote Similarity	NPD2342	Discontinued
0.6179	Remote Similarity	NPD9264	Approved
0.6179	Remote Similarity	NPD9267	Approved
0.6172	Remote Similarity	NPD6671	Approved
0.617	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD230	Phase 1
0.6132	Remote Similarity	NPD9294	Approved
0.6131	Remote Similarity	NPD4908	Phase 1
0.6127	Remote Similarity	NPD5588	Approved
0.6127	Remote Similarity	NPD5960	Phase 3
0.6119	Remote Similarity	NPD2982	Phase 2
0.6119	Remote Similarity	NPD2983	Phase 2
0.6099	Remote Similarity	NPD2568	Approved
0.6098	Remote Similarity	NPD968	Approved
0.6094	Remote Similarity	NPD1793	Approved
0.6094	Remote Similarity	NPD1791	Approved
0.608	Remote Similarity	NPD5451	Approved
0.6077	Remote Similarity	NPD9616	Approved
0.6077	Remote Similarity	NPD9613	Approved
0.6077	Remote Similarity	NPD9615	Approved
0.6071	Remote Similarity	NPD943	Approved
0.6071	Remote Similarity	NPD1613	Approved
0.6071	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD9381	Approved
0.6061	Remote Similarity	NPD9384	Approved
0.6053	Remote Similarity	NPD9295	Approved
0.6048	Remote Similarity	NPD9532	Phase 3
0.6048	Remote Similarity	NPD9552	Approved
0.6048	Remote Similarity	NPD290	Approved
0.6045	Remote Similarity	NPD2981	Phase 2
0.6043	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.604	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD316	Approved
0.6031	Remote Similarity	NPD3091	Approved
0.6028	Remote Similarity	NPD1184	Approved
0.6016	Remote Similarity	NPD2229	Approved
0.6016	Remote Similarity	NPD2228	Approved
0.6016	Remote Similarity	NPD2234	Approved
0.6015	Remote Similarity	NPD915	Approved
0.6014	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9493	Approved
0.6	Remote Similarity	NPD9622	Approved
0.5972	Remote Similarity	NPD6100	Approved
0.5972	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6099	Approved
0.597	Remote Similarity	NPD1201	Approved
0.597	Remote Similarity	NPD3092	Approved
0.596	Remote Similarity	NPD1973	Approved
0.596	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1972	Approved
0.5954	Remote Similarity	NPD856	Approved
0.5954	Remote Similarity	NPD317	Approved
0.5954	Remote Similarity	NPD16	Approved
0.5954	Remote Similarity	NPD318	Approved
0.595	Remote Similarity	NPD3028	Approved
0.5946	Remote Similarity	NPD5058	Phase 3
0.5946	Remote Similarity	NPD6815	Approved
0.5942	Remote Similarity	NPD3018	Phase 2
0.594	Remote Similarity	NPD2932	Approved
0.594	Remote Similarity	NPD4059	Approved
0.594	Remote Similarity	NPD3019	Approved
0.5935	Remote Similarity	NPD9501	Approved
0.5912	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD3094	Phase 2
0.5909	Remote Similarity	NPD9545	Approved
0.5909	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7041	Phase 2
0.5903	Remote Similarity	NPD651	Clinical (unspecified phase)
0.589	Remote Similarity	NPD970	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD3365	Discontinued
0.587	Remote Similarity	NPD9621	Approved
0.587	Remote Similarity	NPD9620	Approved
0.587	Remote Similarity	NPD9619	Approved
0.5865	Remote Similarity	NPD1357	Approved
0.5865	Remote Similarity	NPD4093	Discontinued
0.5859	Remote Similarity	NPD2500	Approved
0.5859	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD2499	Approved
0.5854	Remote Similarity	NPD1415	Approved
0.5854	Remote Similarity	NPD9261	Approved
0.5852	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD9281	Approved
0.5845	Remote Similarity	NPD468	Phase 1
0.5845	Remote Similarity	NPD1240	Approved
0.5839	Remote Similarity	NPD6696	Suspended
0.5828	Remote Similarity	NPD1159	Approved
0.5827	Remote Similarity	NPD910	Approved
0.5821	Remote Similarity	NPD2286	Discontinued
0.5821	Remote Similarity	NPD1751	Approved
0.5821	Remote Similarity	NPD1778	Approved
0.5821	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD1718	Discontinued
0.5811	Remote Similarity	NPD4535	Phase 3
0.5811	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD1608	Approved
0.5802	Remote Similarity	NPD256	Approved
0.5802	Remote Similarity	NPD709	Approved
0.5802	Remote Similarity	NPD255	Approved
0.5798	Remote Similarity	NPD9296	Approved
0.5797	Remote Similarity	NPD987	Approved
0.5797	Remote Similarity	NPD1133	Approved
0.5797	Remote Similarity	NPD1135	Approved
0.5797	Remote Similarity	NPD1131	Approved
0.5797	Remote Similarity	NPD1134	Approved
0.5797	Remote Similarity	NPD1470	Approved
0.5797	Remote Similarity	NPD1129	Approved
0.5789	Remote Similarity	NPD1759	Phase 1
0.5782	Remote Similarity	NPD4534	Discontinued
0.5769	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD1755	Approved
0.5766	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD1607	Approved
0.5762	Remote Similarity	NPD1578	Phase 2
0.5748	Remote Similarity	NPD2684	Approved
0.5738	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD1091	Approved

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