NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	124.03
Volume:	131.672
LogP:	2.387
LogD:	2.529
LogS:	-2.368
# Rotatable Bonds:	1
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.545
Synthetic Accessibility Score:	1.704
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:	-4.43
MDCK Permeability:	1.5400160918943584e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.104

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.726
Plasma Protein Binding (PPB):	91.41570281982422%
Volume Distribution (VD):	3.828
Pgp-substrate:	7.889312744140625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.21
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.423
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	14.253
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.108
Drug-inuced Liver Injury (DILI):	0.353
AMES Toxicity:	0.191
Rat Oral Acute Toxicity:	0.81
Maximum Recommended Daily Dose:	0.12
Skin Sensitization:	0.827
Carcinogencity:	0.444
Eye Corrosion:	0.96
Eye Irritation:	0.993
Respiratory Toxicity:	0.438

Download Data

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

Natural Product: NPC45255

Natural Product ID:	NPC45255
*Common Name:**	Benzenemethanethiol
IUPAC Name:	phenylmethanethiol
Synonyms:	Benzenemethanethiol
Standard InCHIKey:	UENWRTRMUIOCKN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
SMILES:	c1ccc(cc1)CS
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224557
PubChem CID:	7509
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted 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
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	aerial parts	Yuanjiang, Yunnan Province, China	2008-APR	PMID[19438253]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19757853]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21370894]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[30730729]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[8482946]
NPO14565	Strychnos froesii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14565	Strychnos froesii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12595	Euphorbia royleana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26741	Anemarrhena asphodeloides	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14565	Strychnos froesii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1292	Rennellia elliptica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9006	Merulius lacrymans	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7842	Agave atrovirens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15177	Glycine tabacina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1162	Uvaria dependens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14071	Marmota marmota	Species	Sciuridae	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
IC50	3
Potency	8

Activity Type	# Activity
Individual Protein	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	1700.0	nM	PMID[498394]
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	13000.0	nM	PMID[498394]
NPT2	Others	Unspecified		IC50	=	9200.0	nM	PMID[498395]
NPT2	Others	Unspecified		Potency	n.a.	11287.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	62937.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	70617.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	40049.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2505.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17738.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	22331.2	nM	PubChem BioAssay data set

☑ 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 NPC45255 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	2425
0.1-0.2	8511
0.2-0.3	16193
0.3-0.4	12625
0.4-0.5	2232
0.5-0.6	486
0.6-0.7	149
0.7-0.8	59
0.8-0.85	8
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC36440
0.8793	High Similarity	NPC277704
0.8793	High Similarity	NPC149436
0.8644	High Similarity	NPC198841
0.8644	High Similarity	NPC269586
0.8615	High Similarity	NPC5324
0.8594	High Similarity	NPC52330
0.85	High Similarity	NPC300345
0.85	High Similarity	NPC212114
0.85	High Similarity	NPC120441
0.85	High Similarity	NPC65873
0.8462	Intermediate Similarity	NPC181786
0.8361	Intermediate Similarity	NPC114327
0.8361	Intermediate Similarity	NPC8235
0.8361	Intermediate Similarity	NPC36357
0.8226	Intermediate Similarity	NPC169110
0.8226	Intermediate Similarity	NPC147062
0.8095	Intermediate Similarity	NPC248705
0.8095	Intermediate Similarity	NPC135924
0.8095	Intermediate Similarity	NPC210849
0.8095	Intermediate Similarity	NPC150196
0.8095	Intermediate Similarity	NPC310758
0.8095	Intermediate Similarity	NPC54368
0.8095	Intermediate Similarity	NPC238023
0.8095	Intermediate Similarity	NPC246588
0.8065	Intermediate Similarity	NPC64270
0.7971	Intermediate Similarity	NPC212463
0.7969	Intermediate Similarity	NPC29680
0.7969	Intermediate Similarity	NPC66517
0.7969	Intermediate Similarity	NPC71009
0.7969	Intermediate Similarity	NPC200745
0.7969	Intermediate Similarity	NPC22786
0.7937	Intermediate Similarity	NPC147578
0.7846	Intermediate Similarity	NPC88566
0.7846	Intermediate Similarity	NPC21211
0.7846	Intermediate Similarity	NPC113670
0.7812	Intermediate Similarity	NPC200624
0.7727	Intermediate Similarity	NPC32312
0.7727	Intermediate Similarity	NPC291066
0.7727	Intermediate Similarity	NPC155172
0.7727	Intermediate Similarity	NPC198023
0.7619	Intermediate Similarity	NPC469807
0.7612	Intermediate Similarity	NPC178527
0.7576	Intermediate Similarity	NPC45756
0.7576	Intermediate Similarity	NPC50266
0.7544	Intermediate Similarity	NPC11150
0.75	Intermediate Similarity	NPC267443
0.75	Intermediate Similarity	NPC6107
0.7465	Intermediate Similarity	NPC244738
0.7397	Intermediate Similarity	NPC302129
0.7391	Intermediate Similarity	NPC78954
0.7391	Intermediate Similarity	NPC239931
0.7391	Intermediate Similarity	NPC311343
0.7391	Intermediate Similarity	NPC82770
0.7353	Intermediate Similarity	NPC289915
0.7353	Intermediate Similarity	NPC113837
0.7286	Intermediate Similarity	NPC16190
0.7286	Intermediate Similarity	NPC246822
0.7286	Intermediate Similarity	NPC169222
0.7286	Intermediate Similarity	NPC98880
0.7286	Intermediate Similarity	NPC213570
0.7286	Intermediate Similarity	NPC139416
0.7286	Intermediate Similarity	NPC473206
0.7286	Intermediate Similarity	NPC235059
0.7206	Intermediate Similarity	NPC264470
0.7183	Intermediate Similarity	NPC229235
0.7183	Intermediate Similarity	NPC72670
0.7183	Intermediate Similarity	NPC95289
0.7183	Intermediate Similarity	NPC219246
0.7183	Intermediate Similarity	NPC251490
0.7183	Intermediate Similarity	NPC263385
0.7123	Intermediate Similarity	NPC299134
0.7083	Intermediate Similarity	NPC1008
0.7083	Intermediate Similarity	NPC87099
0.7083	Intermediate Similarity	NPC208302
0.7083	Intermediate Similarity	NPC193578
0.7083	Intermediate Similarity	NPC135433
0.7083	Intermediate Similarity	NPC326200
0.7083	Intermediate Similarity	NPC158028
0.7083	Intermediate Similarity	NPC226999
0.7083	Intermediate Similarity	NPC280135
0.7083	Intermediate Similarity	NPC155429
0.7083	Intermediate Similarity	NPC39799
0.7083	Intermediate Similarity	NPC74458
0.7042	Intermediate Similarity	NPC200936
0.7013	Intermediate Similarity	NPC475289
0.7013	Intermediate Similarity	NPC475573
0.6986	Remote Similarity	NPC271437
0.6986	Remote Similarity	NPC54269
0.6986	Remote Similarity	NPC1901
0.6986	Remote Similarity	NPC285679
0.6901	Remote Similarity	NPC22760
0.6892	Remote Similarity	NPC113000
0.6892	Remote Similarity	NPC96835
0.6892	Remote Similarity	NPC208075
0.6892	Remote Similarity	NPC108218
0.6892	Remote Similarity	NPC258492
0.6892	Remote Similarity	NPC122327
0.6892	Remote Similarity	NPC112609
0.6849	Remote Similarity	NPC125144
0.6849	Remote Similarity	NPC121708
0.6829	Remote Similarity	NPC53492
0.6812	Remote Similarity	NPC22627
0.6806	Remote Similarity	NPC297358
0.68	Remote Similarity	NPC307195
0.68	Remote Similarity	NPC32203
0.68	Remote Similarity	NPC276699
0.68	Remote Similarity	NPC189371
0.68	Remote Similarity	NPC98976
0.68	Remote Similarity	NPC206800
0.675	Remote Similarity	NPC474088
0.6711	Remote Similarity	NPC139658
0.6711	Remote Similarity	NPC110264
0.6711	Remote Similarity	NPC175393
0.6711	Remote Similarity	NPC271642
0.6623	Remote Similarity	NPC3190
0.6623	Remote Similarity	NPC325662
0.6623	Remote Similarity	NPC179726
0.6623	Remote Similarity	NPC98269
0.6623	Remote Similarity	NPC287790
0.6623	Remote Similarity	NPC245966
0.6623	Remote Similarity	NPC329318
0.6623	Remote Similarity	NPC298023
0.6623	Remote Similarity	NPC9796
0.6623	Remote Similarity	NPC290638
0.6623	Remote Similarity	NPC66655
0.6623	Remote Similarity	NPC3672
0.6623	Remote Similarity	NPC249018
0.6588	Remote Similarity	NPC185501
0.6538	Remote Similarity	NPC137847
0.6538	Remote Similarity	NPC36342
0.6538	Remote Similarity	NPC76455
0.6538	Remote Similarity	NPC66270
0.6538	Remote Similarity	NPC224544
0.6538	Remote Similarity	NPC176228
0.6538	Remote Similarity	NPC12857
0.6538	Remote Similarity	NPC2785
0.6538	Remote Similarity	NPC50192
0.6538	Remote Similarity	NPC245896
0.6538	Remote Similarity	NPC285470
0.6538	Remote Similarity	NPC103488
0.6538	Remote Similarity	NPC255345
0.6515	Remote Similarity	NPC56072
0.6506	Remote Similarity	NPC148231
0.6494	Remote Similarity	NPC78500
0.6456	Remote Similarity	NPC272260
0.6456	Remote Similarity	NPC300205
0.6456	Remote Similarity	NPC170484
0.6456	Remote Similarity	NPC159661
0.6456	Remote Similarity	NPC167577
0.6456	Remote Similarity	NPC139901
0.6456	Remote Similarity	NPC78517
0.6456	Remote Similarity	NPC469894
0.6456	Remote Similarity	NPC151405
0.6437	Remote Similarity	NPC473661
0.6375	Remote Similarity	NPC71664
0.6375	Remote Similarity	NPC50063
0.6375	Remote Similarity	NPC95868
0.6375	Remote Similarity	NPC328178
0.6375	Remote Similarity	NPC127343
0.6375	Remote Similarity	NPC157055
0.6375	Remote Similarity	NPC164086
0.6375	Remote Similarity	NPC315216
0.6375	Remote Similarity	NPC192623
0.6375	Remote Similarity	NPC477703
0.6375	Remote Similarity	NPC121800
0.6375	Remote Similarity	NPC309279
0.6375	Remote Similarity	NPC285716
0.6375	Remote Similarity	NPC184030
0.6375	Remote Similarity	NPC164449
0.6375	Remote Similarity	NPC17408
0.6375	Remote Similarity	NPC190567
0.6296	Remote Similarity	NPC117180
0.6296	Remote Similarity	NPC133050
0.6296	Remote Similarity	NPC231986
0.6296	Remote Similarity	NPC71795
0.6296	Remote Similarity	NPC303245
0.6296	Remote Similarity	NPC242628
0.6296	Remote Similarity	NPC273033
0.6296	Remote Similarity	NPC165212
0.6296	Remote Similarity	NPC89950
0.6296	Remote Similarity	NPC12936
0.6296	Remote Similarity	NPC145053
0.6296	Remote Similarity	NPC100039
0.6232	Remote Similarity	NPC119076
0.6232	Remote Similarity	NPC18259
0.622	Remote Similarity	NPC230068
0.622	Remote Similarity	NPC103326
0.622	Remote Similarity	NPC329319
0.622	Remote Similarity	NPC106313
0.622	Remote Similarity	NPC103387
0.622	Remote Similarity	NPC99240
0.622	Remote Similarity	NPC475199
0.622	Remote Similarity	NPC283012
0.622	Remote Similarity	NPC99394
0.622	Remote Similarity	NPC121478
0.622	Remote Similarity	NPC73637
0.622	Remote Similarity	NPC14326
0.622	Remote Similarity	NPC323103
0.622	Remote Similarity	NPC87299

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 NPC45255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1034
0.1-0.2	937
0.2-0.3	3440
0.3-0.4	2607
0.4-0.5	830
0.5-0.6	236
0.6-0.7	62
0.7-0.8	4
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
0.7846	Intermediate Similarity	NPD675	Discontinued
0.7727	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9728	Phase 1
0.7286	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD294	Approved
0.7083	Intermediate Similarity	NPD292	Approved
0.6892	Remote Similarity	NPD9593	Approved
0.6892	Remote Similarity	NPD9591	Approved
0.6892	Remote Similarity	NPD9592	Approved
0.6892	Remote Similarity	NPD9588	Approved
0.6892	Remote Similarity	NPD80	Approved
0.6892	Remote Similarity	NPD9594	Approved
0.6892	Remote Similarity	NPD9589	Approved
0.6892	Remote Similarity	NPD9590	Approved
0.6892	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD1673	Approved
0.68	Remote Similarity	NPD9716	Approved
0.6667	Remote Similarity	NPD1628	Approved
0.6667	Remote Similarity	NPD1629	Approved
0.6623	Remote Similarity	NPD603	Approved
0.6623	Remote Similarity	NPD4144	Approved
0.6623	Remote Similarity	NPD4147	Approved
0.6623	Remote Similarity	NPD9294	Approved
0.6588	Remote Similarity	NPD4728	Approved
0.6543	Remote Similarity	NPD423	Phase 3
0.6538	Remote Similarity	NPD79	Approved
0.6538	Remote Similarity	NPD225	Approved
0.6538	Remote Similarity	NPD9563	Approved
0.6538	Remote Similarity	NPD9564	Approved
0.6538	Remote Similarity	NPD9397	Approved
0.6538	Remote Similarity	NPD227	Approved
0.6538	Remote Similarity	NPD296	Approved
0.6538	Remote Similarity	NPD293	Approved
0.6538	Remote Similarity	NPD9393	Approved
0.6538	Remote Similarity	NPD295	Approved
0.6508	Remote Similarity	NPD9072	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1053	Approved
0.6456	Remote Similarity	NPD1052	Approved
0.6456	Remote Similarity	NPD507	Approved
0.6456	Remote Similarity	NPD589	Approved
0.6456	Remote Similarity	NPD508	Approved
0.6456	Remote Similarity	NPD590	Approved
0.6456	Remote Similarity	NPD1051	Approved
0.6456	Remote Similarity	NPD1475	Approved
0.6395	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD3981	Approved
0.6375	Remote Similarity	NPD3904	Approved
0.6375	Remote Similarity	NPD1617	Discontinued
0.6375	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5372	Approved
0.6375	Remote Similarity	NPD260	Discontinued
0.6375	Remote Similarity	NPD3903	Approved
0.6375	Remote Similarity	NPD5371	Approved
0.6375	Remote Similarity	NPD3979	Approved
0.6353	Remote Similarity	NPD9184	Approved
0.6353	Remote Similarity	NPD9186	Approved
0.6322	Remote Similarity	NPD1007	Discontinued
0.6296	Remote Similarity	NPD3035	Approved
0.6296	Remote Similarity	NPD4026	Approved
0.6296	Remote Similarity	NPD226	Approved
0.6296	Remote Similarity	NPD4027	Approved
0.6296	Remote Similarity	NPD472	Approved
0.6296	Remote Similarity	NPD942	Approved
0.625	Remote Similarity	NPD9490	Approved
0.6222	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3458	Approved
0.6222	Remote Similarity	NPD3457	Approved
0.6222	Remote Similarity	NPD3456	Approved
0.622	Remote Similarity	NPD4170	Approved
0.622	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4169	Approved
0.6196	Remote Similarity	NPD1067	Discontinued
0.6173	Remote Similarity	NPD914	Suspended
0.6145	Remote Similarity	NPD4635	Approved
0.6145	Remote Similarity	NPD830	Approved
0.6145	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD9491	Approved
0.6145	Remote Similarity	NPD3971	Phase 1
0.6145	Remote Similarity	NPD262	Approved
0.6145	Remote Similarity	NPD1185	Approved
0.6145	Remote Similarity	NPD2001	Discontinued
0.6145	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD263	Approved
0.6145	Remote Similarity	NPD831	Approved
0.6118	Remote Similarity	NPD1697	Approved
0.6098	Remote Similarity	NPD9250	Approved
0.6071	Remote Similarity	NPD2538	Approved
0.6071	Remote Similarity	NPD3429	Approved
0.6071	Remote Similarity	NPD4544	Approved
0.6071	Remote Similarity	NPD9395	Approved
0.6071	Remote Similarity	NPD5178	Approved
0.6071	Remote Similarity	NPD2539	Approved
0.6071	Remote Similarity	NPD3427	Approved
0.6071	Remote Similarity	NPD785	Approved
0.6044	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4737	Phase 2
0.6	Remote Similarity	NPD2208	Approved
0.6	Remote Similarity	NPD837	Approved
0.6	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2205	Approved
0.6	Remote Similarity	NPD111	Approved
0.6	Remote Similarity	NPD5916	Discontinued
0.6	Remote Similarity	NPD1409	Phase 3
0.5957	Remote Similarity	NPD6354	Discontinued
0.593	Remote Similarity	NPD304	Approved
0.593	Remote Similarity	NPD4406	Approved
0.593	Remote Similarity	NPD4409	Approved
0.593	Remote Similarity	NPD4636	Approved
0.593	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.593	Remote Similarity	NPD305	Approved
0.587	Remote Similarity	NPD838	Approved
0.587	Remote Similarity	NPD3093	Approved
0.5862	Remote Similarity	NPD187	Approved
0.5862	Remote Similarity	NPD781	Approved
0.5862	Remote Similarity	NPD3428	Approved
0.5862	Remote Similarity	NPD783	Approved
0.5862	Remote Similarity	NPD9538	Approved
0.5862	Remote Similarity	NPD650	Approved
0.5862	Remote Similarity	NPD782	Approved
0.5862	Remote Similarity	NPD1087	Approved
0.5862	Remote Similarity	NPD2002	Discontinued
0.5862	Remote Similarity	NPD3426	Approved
0.5862	Remote Similarity	NPD4793	Discontinued
0.5862	Remote Similarity	NPD1282	Approved
0.5862	Remote Similarity	NPD4146	Approved
0.5862	Remote Similarity	NPD4145	Approved
0.5862	Remote Similarity	NPD780	Approved
0.5862	Remote Similarity	NPD506	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD1796	Phase 3
0.5833	Remote Similarity	NPD744	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3345	Approved
0.5795	Remote Similarity	NPD588	Approved
0.5795	Remote Similarity	NPD1101	Approved
0.5795	Remote Similarity	NPD5675	Discontinued
0.5795	Remote Similarity	NPD531	Approved
0.5795	Remote Similarity	NPD587	Approved
0.5789	Remote Similarity	NPD1795	Discontinued
0.5773	Remote Similarity	NPD488	Approved
0.5773	Remote Similarity	NPD489	Approved
0.5765	Remote Similarity	NPD4000	Phase 3
0.5761	Remote Similarity	NPD9260	Approved
0.5747	Remote Similarity	NPD3099	Discontinued
0.5747	Remote Similarity	NPD9259	Approved
0.5747	Remote Similarity	NPD9257	Approved
0.573	Remote Similarity	NPD5346	Phase 2
0.573	Remote Similarity	NPD5347	Phase 2
0.573	Remote Similarity	NPD9348	Approved
0.573	Remote Similarity	NPD800	Approved
0.573	Remote Similarity	NPD771	Phase 3
0.573	Remote Similarity	NPD9350	Approved
0.573	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.573	Remote Similarity	NPD689	Discontinued
0.573	Remote Similarity	NPD9349	Approved
0.573	Remote Similarity	NPD9	Approved
0.573	Remote Similarity	NPD9351	Phase 3
0.573	Remote Similarity	NPD297	Approved
0.5699	Remote Similarity	NPD157	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD4008	Approved
0.5684	Remote Similarity	NPD4007	Approved
0.567	Remote Similarity	NPD1387	Phase 1
0.5667	Remote Similarity	NPD5915	Approved
0.5667	Remote Similarity	NPD3346	Approved
0.5667	Remote Similarity	NPD1089	Approved
0.5667	Remote Similarity	NPD3673	Approved
0.5667	Remote Similarity	NPD3344	Approved
0.5667	Remote Similarity	NPD1086	Approved
0.5667	Remote Similarity	NPD3672	Approved
0.5667	Remote Similarity	NPD1090	Approved
0.5657	Remote Similarity	NPD3459	Approved
0.5604	Remote Similarity	NPD7160	Approved
0.5604	Remote Similarity	NPD4543	Discontinued
0.5604	Remote Similarity	NPD7609	Phase 3
0.5604	Remote Similarity	NPD2997	Approved
0.5604	Remote Similarity	NPD3000	Approved
0.5604	Remote Similarity	NPD530	Approved
0.5604	Remote Similarity	NPD517	Discontinued
0.5604	Remote Similarity	NPD1239	Approved
0.5604	Remote Similarity	NPD2998	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