NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	160.05
Volume:	168.802
LogP:	2.727
LogD:	2.696
LogS:	-2.6
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.62
Synthetic Accessibility Score:	1.856
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:	-4.629
MDCK Permeability:	1.836604678828735e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.284
Plasma Protein Binding (PPB):	95.3080825805664%
Volume Distribution (VD):	0.669
Pgp-substrate:	3.5389204025268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.631
CYP2C19-inhibitor:	0.454
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.518
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.416
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	13.317
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.017
Drug-inuced Liver Injury (DILI):	0.248
AMES Toxicity:	0.668
Rat Oral Acute Toxicity:	0.624
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.943
Carcinogencity:	0.84
Eye Corrosion:	0.799
Eye Irritation:	0.994
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC168393

Natural Product ID:	NPC168393
*Common Name:**	Naphthalene-1,8-Diol
IUPAC Name:	naphthalene-1,8-diol
Synonyms:	Naphthalene-1,8-Diol
Standard InCHIKey:	OENHRRVNRZBNNS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6,11-12H
SMILES:	Oc1cccc2c1c(O)ccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL203537
PubChem CID:	68438
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols 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
NPO28292	Streptomyces microflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9918397]
NPO5951	Crotalaria ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5951	Crotalaria ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO839	Sorocea ilicifolia	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5951	Crotalaria ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2935	Zanthoxylum parviflorum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25519	Kleinia tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17804	Melanocarpus albomyces	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO839	Sorocea ilicifolia	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17771	Senna didymobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7740	Clitocybula oculus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5951	Crotalaria ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28292	Streptomyces microflavus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4791	Murrayella periclados	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3095	Aster conspicuus	Species	Asteraceae	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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1855	Cell Line	HFL1	Homo sapiens	ED50	=	20.0	uM	PMID[558999]
NPT550	Cell Line	T-24	Homo sapiens	ED50	=	10.0	uM	PMID[558999]
NPT25083	SINGLE PROTEIN	Arginase-1	Bos taurus	Inhibition	=	61.0	%	PMID[559000]

☑ 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 NPC168393 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	501
0.1-0.2	2302
0.2-0.3	7677
0.3-0.4	11774
0.4-0.5	5124
0.5-0.6	9519
0.6-0.7	4466
0.7-0.8	1092
0.8-0.85	195
0.85-0.9	41
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC67250
0.9579	High Similarity	NPC156313
0.9406	High Similarity	NPC202647
0.9388	High Similarity	NPC233827
0.9175	High Similarity	NPC32674
0.91	High Similarity	NPC102216
0.9062	High Similarity	NPC245187
0.8962	High Similarity	NPC249270
0.8958	High Similarity	NPC271440
0.8932	High Similarity	NPC233835
0.8911	High Similarity	NPC238696
0.89	High Similarity	NPC100340
0.89	High Similarity	NPC143659
0.89	High Similarity	NPC12221
0.8824	High Similarity	NPC292452
0.8824	High Similarity	NPC471350
0.8796	High Similarity	NPC261973
0.8788	High Similarity	NPC291789
0.8785	High Similarity	NPC107240
0.8776	High Similarity	NPC274678
0.875	High Similarity	NPC174981
0.8738	High Similarity	NPC54765
0.8738	High Similarity	NPC248904
0.8725	High Similarity	NPC30506
0.8725	High Similarity	NPC327811
0.8725	High Similarity	NPC254965
0.8725	High Similarity	NPC241891
0.8716	High Similarity	NPC470760
0.8679	High Similarity	NPC224527
0.8679	High Similarity	NPC95716
0.8673	High Similarity	NPC128062
0.8673	High Similarity	NPC76938
0.8667	High Similarity	NPC314187
0.8667	High Similarity	NPC19808
0.8667	High Similarity	NPC33728
0.8667	High Similarity	NPC58865
0.8641	High Similarity	NPC134829
0.8636	High Similarity	NPC63010
0.8627	High Similarity	NPC168829
0.8624	High Similarity	NPC115808
0.8614	High Similarity	NPC248573
0.8614	High Similarity	NPC161571
0.8614	High Similarity	NPC275053
0.8598	High Similarity	NPC46940
0.8586	High Similarity	NPC32714
0.8571	High Similarity	NPC95344
0.8558	High Similarity	NPC302681
0.8558	High Similarity	NPC39097
0.8558	High Similarity	NPC39664
0.8558	High Similarity	NPC109691
0.8558	High Similarity	NPC118286
0.8558	High Similarity	NPC470700
0.8544	High Similarity	NPC288411
0.8544	High Similarity	NPC475580
0.8544	High Similarity	NPC119860
0.8542	High Similarity	NPC27974
0.8532	High Similarity	NPC246760
0.8532	High Similarity	NPC84999
0.8526	High Similarity	NPC155393
0.8505	High Similarity	NPC225679
0.8505	High Similarity	NPC476632
0.8505	High Similarity	NPC151537
0.8505	High Similarity	NPC165770
0.8505	High Similarity	NPC4493
0.85	High Similarity	NPC312132
0.85	High Similarity	NPC259512
0.85	High Similarity	NPC202986
0.8476	Intermediate Similarity	NPC54844
0.8476	Intermediate Similarity	NPC320439
0.8469	Intermediate Similarity	NPC45040
0.8469	Intermediate Similarity	NPC231150
0.8462	Intermediate Similarity	NPC474839
0.8462	Intermediate Similarity	NPC138942
0.8462	Intermediate Similarity	NPC117115
0.8462	Intermediate Similarity	NPC246056
0.8438	Intermediate Similarity	NPC307235
0.8438	Intermediate Similarity	NPC407
0.8431	Intermediate Similarity	NPC166761
0.8431	Intermediate Similarity	NPC294741
0.8431	Intermediate Similarity	NPC72729
0.8431	Intermediate Similarity	NPC10588
0.8426	Intermediate Similarity	NPC43525
0.8426	Intermediate Similarity	NPC166995
0.8416	Intermediate Similarity	NPC88420
0.8416	Intermediate Similarity	NPC152097
0.8416	Intermediate Similarity	NPC79241
0.8416	Intermediate Similarity	NPC6597
0.8411	Intermediate Similarity	NPC224870
0.8407	Intermediate Similarity	NPC277798
0.8407	Intermediate Similarity	NPC100108
0.8396	Intermediate Similarity	NPC169450
0.8396	Intermediate Similarity	NPC11554
0.8393	Intermediate Similarity	NPC217174
0.8384	Intermediate Similarity	NPC29373
0.8384	Intermediate Similarity	NPC55903
0.8378	Intermediate Similarity	NPC50521
0.8378	Intermediate Similarity	NPC221549
0.8378	Intermediate Similarity	NPC244816
0.8367	Intermediate Similarity	NPC47950
0.8367	Intermediate Similarity	NPC192
0.8365	Intermediate Similarity	NPC227458
0.8365	Intermediate Similarity	NPC218879
0.8365	Intermediate Similarity	NPC244513
0.8365	Intermediate Similarity	NPC323810
0.8365	Intermediate Similarity	NPC272029
0.8364	Intermediate Similarity	NPC472893
0.835	Intermediate Similarity	NPC284011
0.835	Intermediate Similarity	NPC72947
0.8349	Intermediate Similarity	NPC322239
0.8349	Intermediate Similarity	NPC23804
0.8349	Intermediate Similarity	NPC117846
0.8349	Intermediate Similarity	NPC715
0.8349	Intermediate Similarity	NPC261343
0.8333	Intermediate Similarity	NPC80027
0.8333	Intermediate Similarity	NPC33675
0.8333	Intermediate Similarity	NPC92730
0.8333	Intermediate Similarity	NPC299762
0.8333	Intermediate Similarity	NPC260775
0.8319	Intermediate Similarity	NPC472071
0.8318	Intermediate Similarity	NPC186385
0.8318	Intermediate Similarity	NPC299568
0.8317	Intermediate Similarity	NPC82664
0.8317	Intermediate Similarity	NPC216520
0.8317	Intermediate Similarity	NPC132271
0.8317	Intermediate Similarity	NPC292730
0.8302	Intermediate Similarity	NPC204901
0.8302	Intermediate Similarity	NPC158253
0.8302	Intermediate Similarity	NPC66834
0.8302	Intermediate Similarity	NPC151477
0.8302	Intermediate Similarity	NPC232523
0.83	Intermediate Similarity	NPC151715
0.83	Intermediate Similarity	NPC152415
0.8286	Intermediate Similarity	NPC239291
0.8286	Intermediate Similarity	NPC37802
0.8283	Intermediate Similarity	NPC306074
0.8273	Intermediate Similarity	NPC195922
0.8273	Intermediate Similarity	NPC470837
0.8269	Intermediate Similarity	NPC302219
0.8269	Intermediate Similarity	NPC249828
0.8269	Intermediate Similarity	NPC71002
0.8269	Intermediate Similarity	NPC242342
0.8269	Intermediate Similarity	NPC313030
0.8269	Intermediate Similarity	NPC146798
0.8269	Intermediate Similarity	NPC53051
0.8269	Intermediate Similarity	NPC85479
0.8269	Intermediate Similarity	NPC24404
0.8269	Intermediate Similarity	NPC106396
0.8269	Intermediate Similarity	NPC168303
0.8269	Intermediate Similarity	NPC222522
0.8269	Intermediate Similarity	NPC94351
0.8257	Intermediate Similarity	NPC302371
0.8257	Intermediate Similarity	NPC473521
0.8252	Intermediate Similarity	NPC130103
0.8252	Intermediate Similarity	NPC174911
0.8252	Intermediate Similarity	NPC70677
0.8252	Intermediate Similarity	NPC248396
0.8252	Intermediate Similarity	NPC130756
0.8252	Intermediate Similarity	NPC12931
0.8252	Intermediate Similarity	NPC129373
0.8252	Intermediate Similarity	NPC48730
0.8246	Intermediate Similarity	NPC102639
0.8241	Intermediate Similarity	NPC132720
0.8241	Intermediate Similarity	NPC13482
0.8235	Intermediate Similarity	NPC475078
0.8235	Intermediate Similarity	NPC225464
0.823	Intermediate Similarity	NPC151197
0.8229	Intermediate Similarity	NPC286904
0.8229	Intermediate Similarity	NPC150837
0.8224	Intermediate Similarity	NPC63698
0.8224	Intermediate Similarity	NPC61885
0.8224	Intermediate Similarity	NPC262365
0.8218	Intermediate Similarity	NPC26244
0.8214	Intermediate Similarity	NPC299180
0.8208	Intermediate Similarity	NPC201662
0.8208	Intermediate Similarity	NPC21594
0.8208	Intermediate Similarity	NPC99836
0.8208	Intermediate Similarity	NPC12640
0.8208	Intermediate Similarity	NPC155072
0.82	Intermediate Similarity	NPC306884
0.82	Intermediate Similarity	NPC147284
0.82	Intermediate Similarity	NPC94139
0.82	Intermediate Similarity	NPC162314
0.82	Intermediate Similarity	NPC3358
0.82	Intermediate Similarity	NPC295295
0.82	Intermediate Similarity	NPC210497
0.8198	Intermediate Similarity	NPC808
0.8198	Intermediate Similarity	NPC167934
0.819	Intermediate Similarity	NPC475225
0.819	Intermediate Similarity	NPC130817
0.819	Intermediate Similarity	NPC471511
0.8182	Intermediate Similarity	NPC312304
0.8182	Intermediate Similarity	NPC263753
0.8174	Intermediate Similarity	NPC39029
0.8174	Intermediate Similarity	NPC237667
0.8173	Intermediate Similarity	NPC11280
0.8173	Intermediate Similarity	NPC147310
0.8173	Intermediate Similarity	NPC192032
0.8173	Intermediate Similarity	NPC24407
0.8173	Intermediate Similarity	NPC294186
0.8173	Intermediate Similarity	NPC252105

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 NPC168393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	464
0.1-0.2	1049
0.2-0.3	1390
0.3-0.4	3018
0.4-0.5	1757
0.5-0.6	1072
0.6-0.7	340
0.7-0.8	46
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD2342	Discontinued
0.8614	High Similarity	NPD1242	Phase 1
0.85	High Similarity	NPD288	Approved
0.8431	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8426	Intermediate Similarity	NPD7635	Approved
0.84	Intermediate Similarity	NPD844	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.8318	Intermediate Similarity	NPD4750	Phase 3
0.83	Intermediate Similarity	NPD2934	Approved
0.83	Intermediate Similarity	NPD2933	Approved
0.8218	Intermediate Similarity	NPD2859	Approved
0.8218	Intermediate Similarity	NPD2860	Approved
0.8173	Intermediate Similarity	NPD846	Approved
0.8173	Intermediate Similarity	NPD940	Approved
0.802	Intermediate Similarity	NPD845	Approved
0.7982	Intermediate Similarity	NPD3021	Approved
0.7982	Intermediate Similarity	NPD3022	Approved
0.7941	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD709	Approved
0.7818	Intermediate Similarity	NPD1792	Phase 2
0.7788	Intermediate Similarity	NPD497	Approved
0.7787	Intermediate Similarity	NPD4625	Phase 3
0.7755	Intermediate Similarity	NPD111	Approved
0.7714	Intermediate Similarity	NPD9273	Approved
0.7712	Intermediate Similarity	NPD1201	Approved
0.7699	Intermediate Similarity	NPD495	Approved
0.7699	Intermediate Similarity	NPD498	Approved
0.7699	Intermediate Similarity	NPD496	Approved
0.7692	Intermediate Similarity	NPD1809	Phase 2
0.7692	Intermediate Similarity	NPD2286	Discontinued
0.7672	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD1610	Phase 2
0.7545	Intermediate Similarity	NPD1445	Approved
0.7545	Intermediate Similarity	NPD1444	Approved
0.7521	Intermediate Similarity	NPD3091	Approved
0.7521	Intermediate Similarity	NPD1548	Phase 1
0.7478	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD1470	Approved
0.7458	Intermediate Similarity	NPD4093	Discontinued
0.7414	Intermediate Similarity	NPD6671	Approved
0.7395	Intermediate Similarity	NPD2932	Approved
0.7395	Intermediate Similarity	NPD4059	Approved
0.7395	Intermediate Similarity	NPD3019	Approved
0.7387	Intermediate Similarity	NPD968	Approved
0.735	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1164	Approved
0.7295	Intermediate Similarity	NPD4749	Approved
0.728	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9089	Approved
0.7273	Intermediate Similarity	NPD3092	Approved
0.725	Intermediate Similarity	NPD1751	Approved
0.7248	Intermediate Similarity	NPD3028	Approved
0.7241	Intermediate Similarity	NPD2234	Approved
0.7241	Intermediate Similarity	NPD2229	Approved
0.7241	Intermediate Similarity	NPD2228	Approved
0.7217	Intermediate Similarity	NPD228	Approved
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3094	Phase 2
0.7172	Intermediate Similarity	NPD9093	Approved
0.7158	Intermediate Similarity	NPD9087	Approved
0.7155	Intermediate Similarity	NPD9379	Approved
0.7155	Intermediate Similarity	NPD9377	Approved
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7131	Intermediate Similarity	NPD1611	Approved
0.712	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9500	Approved
0.7117	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4589	Approved
0.7107	Intermediate Similarity	NPD4626	Approved
0.7107	Intermediate Similarity	NPD3095	Discontinued
0.7105	Intermediate Similarity	NPD74	Approved
0.7105	Intermediate Similarity	NPD9266	Approved
0.7099	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD5304	Approved
0.7083	Intermediate Similarity	NPD5303	Approved
0.7073	Intermediate Similarity	NPD2230	Approved
0.7073	Intermediate Similarity	NPD2233	Approved
0.7073	Intermediate Similarity	NPD2232	Approved
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7054	Intermediate Similarity	NPD9608	Approved
0.7054	Intermediate Similarity	NPD9610	Approved
0.7054	Intermediate Similarity	NPD943	Approved
0.7054	Intermediate Similarity	NPD4060	Phase 1
0.7054	Intermediate Similarity	NPD1613	Approved
0.7054	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1980	Approved
0.7049	Intermediate Similarity	NPD1981	Approved
0.7049	Intermediate Similarity	NPD1983	Approved
0.7045	Intermediate Similarity	NPD5406	Approved
0.7045	Intermediate Similarity	NPD5404	Approved
0.7045	Intermediate Similarity	NPD5405	Approved
0.7045	Intermediate Similarity	NPD5408	Approved
0.7041	Intermediate Similarity	NPD9088	Approved
0.7034	Intermediate Similarity	NPD1793	Approved
0.7034	Intermediate Similarity	NPD9618	Approved
0.7034	Intermediate Similarity	NPD1791	Approved
0.7034	Intermediate Similarity	NPD9614	Approved
0.7031	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1651	Approved
0.7018	Intermediate Similarity	NPD9267	Approved
0.7018	Intermediate Similarity	NPD9263	Approved
0.7018	Intermediate Similarity	NPD9264	Approved
0.7018	Intermediate Similarity	NPD290	Approved
0.7016	Intermediate Similarity	NPD1669	Approved
0.6992	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD422	Phase 1
0.6992	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3027	Phase 3
0.6949	Remote Similarity	NPD5283	Phase 1
0.6949	Remote Similarity	NPD1398	Phase 1
0.6949	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4097	Suspended
0.6942	Remote Similarity	NPD7330	Discontinued
0.6942	Remote Similarity	NPD1759	Phase 1
0.6939	Remote Similarity	NPD9294	Approved
0.6937	Remote Similarity	NPD1616	Discontinued
0.6929	Remote Similarity	NPD5736	Approved
0.6923	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9493	Approved
0.6905	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9615	Approved
0.686	Remote Similarity	NPD1758	Phase 1
0.686	Remote Similarity	NPD9613	Approved
0.686	Remote Similarity	NPD9616	Approved
0.6857	Remote Similarity	NPD9094	Approved
0.6855	Remote Similarity	NPD1281	Approved
0.685	Remote Similarity	NPD2194	Approved
0.685	Remote Similarity	NPD2195	Approved
0.6842	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5311	Approved
0.6825	Remote Similarity	NPD5310	Approved
0.6825	Remote Similarity	NPD6696	Suspended
0.6822	Remote Similarity	NPD5155	Approved
0.6822	Remote Similarity	NPD5156	Approved
0.6812	Remote Similarity	NPD7390	Discontinued
0.6807	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD316	Approved
0.68	Remote Similarity	NPD1840	Phase 2
0.68	Remote Similarity	NPD1608	Approved
0.6797	Remote Similarity	NPD3637	Approved
0.6797	Remote Similarity	NPD3636	Approved
0.6797	Remote Similarity	NPD3635	Approved
0.6791	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6099	Approved
0.6791	Remote Similarity	NPD6100	Approved
0.6789	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7340	Approved
0.6774	Remote Similarity	NPD3023	Approved
0.6774	Remote Similarity	NPD3026	Approved
0.6772	Remote Similarity	NPD3053	Approved
0.6772	Remote Similarity	NPD1203	Approved
0.6772	Remote Similarity	NPD3055	Approved
0.6748	Remote Similarity	NPD3443	Approved
0.6748	Remote Similarity	NPD5691	Approved
0.6748	Remote Similarity	NPD3025	Approved
0.6748	Remote Similarity	NPD3444	Approved
0.6748	Remote Similarity	NPD3024	Approved
0.6748	Remote Similarity	NPD3445	Approved
0.6746	Remote Similarity	NPD1755	Approved
0.6744	Remote Similarity	NPD2606	Approved
0.6744	Remote Similarity	NPD3594	Approved
0.6744	Remote Similarity	NPD2605	Approved
0.6744	Remote Similarity	NPD3595	Approved
0.6741	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4624	Approved
0.6719	Remote Similarity	NPD6584	Phase 3
0.6718	Remote Similarity	NPD6405	Approved
0.6718	Remote Similarity	NPD6663	Approved
0.6718	Remote Similarity	NPD6407	Approved
0.6715	Remote Similarity	NPD3892	Phase 2
0.6715	Remote Similarity	NPD3750	Approved
0.6694	Remote Similarity	NPD9381	Approved
0.6694	Remote Similarity	NPD9384	Approved
0.6694	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3225	Approved
0.6692	Remote Similarity	NPD1024	Discontinued
0.6692	Remote Similarity	NPD2568	Approved
0.6691	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1712	Approved
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2231	Phase 2
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD2235	Phase 2
0.6667	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9261	Approved
0.6642	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3268	Approved
0.6641	Remote Similarity	NPD3764	Approved
0.664	Remote Similarity	NPD3496	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