NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	209.09
Volume:	218.006
LogP:	2.944
LogD:	3.047
LogS:	-3.287
# Rotatable Bonds:	5
TPSA:	20.31
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	2.125
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.445
MDCK Permeability:	3.282125908299349e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	89.58112335205078%
Volume Distribution (VD):	0.785
Pgp-substrate:	11.881770133972168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.833
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.451
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.787
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.601

ADMET: Excretion

Clearance (CL):	10.442
Half-life (T1/2):	0.661

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.749
Carcinogencity:	0.169
Eye Corrosion:	0.263
Eye Irritation:	0.899
Respiratory Toxicity:	0.246

Download Data

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

Natural Product: NPC474088

Natural Product ID:	NPC474088
*Common Name:**	Niranin
IUPAC Name:	S-methyl N-methyl-N-(2-phenylethyl)carbamothioate
Synonyms:	niranin
Standard InCHIKey:	SFUIBAHKLMJTHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H15NOS/c1-12(11(13)14-2)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3
SMILES:	CN(CCC1=CC=CC=C1)C(=O)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460765
PubChem CID:	179703
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
NPO33498	glycosmis sp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9036182]

☑ 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
EC50	1
ED50	1
Others	2

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	ED50	=	28.0	ug ml-1	PMID[511251]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	=	0.25	umol/g	PMID[511251]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	=	0.81	umol/g	PMID[511251]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	=	0.03	umol/dm'2	PMID[511251]

☑ 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 NPC474088 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	178
0.1-0.2	4795
0.2-0.3	15120
0.3-0.4	16950
0.4-0.5	4414
0.5-0.6	966
0.6-0.7	244
0.7-0.8	25
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8875	High Similarity	NPC475289
0.8875	High Similarity	NPC475573
0.8736	High Similarity	NPC473661
0.8636	High Similarity	NPC71140
0.8025	Intermediate Similarity	NPC98976
0.8	Intermediate Similarity	NPC244738
0.7955	Intermediate Similarity	NPC53492
0.7927	Intermediate Similarity	NPC271642
0.7927	Intermediate Similarity	NPC139658
0.7753	Intermediate Similarity	NPC305602
0.7753	Intermediate Similarity	NPC17497
0.7531	Intermediate Similarity	NPC229235
0.7529	Intermediate Similarity	NPC12857
0.75	Intermediate Similarity	NPC104070
0.7471	Intermediate Similarity	NPC231986
0.747	Intermediate Similarity	NPC122327
0.747	Intermediate Similarity	NPC112609
0.747	Intermediate Similarity	NPC113000
0.747	Intermediate Similarity	NPC299134
0.7381	Intermediate Similarity	NPC276699
0.7368	Intermediate Similarity	NPC256452
0.7263	Intermediate Similarity	NPC474974
0.7216	Intermediate Similarity	NPC472258
0.7209	Intermediate Similarity	NPC98269
0.7209	Intermediate Similarity	NPC325662
0.7209	Intermediate Similarity	NPC290638
0.7108	Intermediate Similarity	NPC219246
0.71	Intermediate Similarity	NPC329375
0.7059	Intermediate Similarity	NPC473418
0.7033	Intermediate Similarity	NPC169016
0.7013	Intermediate Similarity	NPC65873
0.7013	Intermediate Similarity	NPC120441
0.7013	Intermediate Similarity	NPC300345
0.7013	Intermediate Similarity	NPC212114
0.6989	Remote Similarity	NPC473031
0.697	Remote Similarity	NPC322598
0.6951	Remote Similarity	NPC52330
0.6915	Remote Similarity	NPC12429
0.6883	Remote Similarity	NPC198841
0.6883	Remote Similarity	NPC269586
0.6882	Remote Similarity	NPC258046
0.6882	Remote Similarity	NPC203076
0.6875	Remote Similarity	NPC470926
0.6842	Remote Similarity	NPC470877
0.6827	Remote Similarity	NPC45033
0.6822	Remote Similarity	NPC475013
0.6813	Remote Similarity	NPC14326
0.6809	Remote Similarity	NPC471638
0.6796	Remote Similarity	NPC469974
0.679	Remote Similarity	NPC50266
0.6771	Remote Similarity	NPC74936
0.6771	Remote Similarity	NPC159178
0.6771	Remote Similarity	NPC78041
0.6771	Remote Similarity	NPC471307
0.6771	Remote Similarity	NPC209764
0.6771	Remote Similarity	NPC141139
0.6771	Remote Similarity	NPC121872
0.6768	Remote Similarity	NPC471320
0.6768	Remote Similarity	NPC471319
0.6753	Remote Similarity	NPC277704
0.6753	Remote Similarity	NPC149436
0.675	Remote Similarity	NPC135924
0.675	Remote Similarity	NPC310758
0.675	Remote Similarity	NPC45255
0.675	Remote Similarity	NPC210849
0.675	Remote Similarity	NPC54368
0.675	Remote Similarity	NPC238023
0.675	Remote Similarity	NPC150196
0.675	Remote Similarity	NPC248705
0.6726	Remote Similarity	NPC302169
0.6709	Remote Similarity	NPC8235
0.6701	Remote Similarity	NPC245259
0.6697	Remote Similarity	NPC476048
0.6667	Remote Similarity	NPC155847
0.6667	Remote Similarity	NPC29680
0.6667	Remote Similarity	NPC311343
0.6667	Remote Similarity	NPC289381
0.6667	Remote Similarity	NPC269340
0.6667	Remote Similarity	NPC133162
0.6667	Remote Similarity	NPC214200
0.6667	Remote Similarity	NPC228400
0.6635	Remote Similarity	NPC275467
0.6628	Remote Similarity	NPC74458
0.6627	Remote Similarity	NPC36440
0.6625	Remote Similarity	NPC147062
0.6625	Remote Similarity	NPC169110
0.6604	Remote Similarity	NPC55529
0.6598	Remote Similarity	NPC316108
0.6596	Remote Similarity	NPC3210
0.6588	Remote Similarity	NPC5324
0.6588	Remote Similarity	NPC98880
0.6588	Remote Similarity	NPC200936
0.6585	Remote Similarity	NPC88566
0.6571	Remote Similarity	NPC476198
0.6571	Remote Similarity	NPC143516
0.6566	Remote Similarity	NPC291070
0.6566	Remote Similarity	NPC322040
0.6566	Remote Similarity	NPC246757
0.6566	Remote Similarity	NPC471309
0.6559	Remote Similarity	NPC119677
0.6552	Remote Similarity	NPC285679
0.6545	Remote Similarity	NPC35850
0.6545	Remote Similarity	NPC276949
0.6543	Remote Similarity	NPC246588
0.6531	Remote Similarity	NPC226438
0.6512	Remote Similarity	NPC95289
0.6509	Remote Similarity	NPC471447
0.6509	Remote Similarity	NPC474804
0.6509	Remote Similarity	NPC474973
0.6509	Remote Similarity	NPC130898
0.6506	Remote Similarity	NPC198023
0.6506	Remote Similarity	NPC155172
0.6506	Remote Similarity	NPC32312
0.65	Remote Similarity	NPC161972
0.65	Remote Similarity	NPC114327
0.65	Remote Similarity	NPC36357
0.65	Remote Similarity	NPC108339
0.65	Remote Similarity	NPC303045
0.65	Remote Similarity	NPC58674
0.65	Remote Similarity	NPC64270
0.6486	Remote Similarity	NPC33742
0.6463	Remote Similarity	NPC66517
0.6463	Remote Similarity	NPC71009
0.6463	Remote Similarity	NPC22786
0.6442	Remote Similarity	NPC327226
0.6437	Remote Similarity	NPC326200
0.6437	Remote Similarity	NPC125144
0.6437	Remote Similarity	NPC121708
0.6436	Remote Similarity	NPC25565
0.6429	Remote Similarity	NPC178527
0.6415	Remote Similarity	NPC167336
0.6415	Remote Similarity	NPC67043
0.6408	Remote Similarity	NPC12730
0.64	Remote Similarity	NPC7067
0.64	Remote Similarity	NPC469330
0.6395	Remote Similarity	NPC16190
0.6395	Remote Similarity	NPC235059
0.6395	Remote Similarity	NPC169222
0.6392	Remote Similarity	NPC325441
0.6389	Remote Similarity	NPC473676
0.6386	Remote Similarity	NPC113670
0.6386	Remote Similarity	NPC45756
0.6386	Remote Similarity	NPC21211
0.6373	Remote Similarity	NPC473501
0.6373	Remote Similarity	NPC475439
0.6372	Remote Similarity	NPC470544
0.6364	Remote Similarity	NPC271437
0.6364	Remote Similarity	NPC212463
0.6353	Remote Similarity	NPC267443
0.6353	Remote Similarity	NPC6107
0.6339	Remote Similarity	NPC246904
0.6337	Remote Similarity	NPC329430
0.6333	Remote Similarity	NPC110264
0.6321	Remote Similarity	NPC226778
0.6321	Remote Similarity	NPC147000
0.6321	Remote Similarity	NPC150254
0.6321	Remote Similarity	NPC304761
0.6316	Remote Similarity	NPC470545
0.631	Remote Similarity	NPC291066
0.6292	Remote Similarity	NPC208075
0.6289	Remote Similarity	NPC60408
0.6286	Remote Similarity	NPC239854
0.6283	Remote Similarity	NPC473573
0.6279	Remote Similarity	NPC82770
0.6279	Remote Similarity	NPC239931
0.6279	Remote Similarity	NPC181786
0.6279	Remote Similarity	NPC78954
0.6275	Remote Similarity	NPC317400
0.6265	Remote Similarity	NPC200745
0.6264	Remote Similarity	NPC298023
0.6263	Remote Similarity	NPC172128
0.6263	Remote Similarity	NPC258627
0.6263	Remote Similarity	NPC78154
0.6261	Remote Similarity	NPC470546
0.6261	Remote Similarity	NPC220698
0.625	Remote Similarity	NPC208302
0.625	Remote Similarity	NPC155429
0.6237	Remote Similarity	NPC192623
0.6235	Remote Similarity	NPC113837
0.6235	Remote Similarity	NPC289915
0.623	Remote Similarity	NPC300315
0.6228	Remote Similarity	NPC285926
0.6228	Remote Similarity	NPC14672
0.6228	Remote Similarity	NPC315276
0.6226	Remote Similarity	NPC471317
0.6226	Remote Similarity	NPC202613
0.6222	Remote Similarity	NPC189371
0.6216	Remote Similarity	NPC181390
0.6214	Remote Similarity	NPC311242
0.6214	Remote Similarity	NPC122493
0.6214	Remote Similarity	NPC10781
0.6214	Remote Similarity	NPC293628
0.6207	Remote Similarity	NPC213570
0.6207	Remote Similarity	NPC246822
0.6207	Remote Similarity	NPC139416
0.6204	Remote Similarity	NPC473498
0.6196	Remote Similarity	NPC2785
0.6196	Remote Similarity	NPC76455
0.6196	Remote Similarity	NPC36342
0.6196	Remote Similarity	NPC103488

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 NPC474088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	946
0.2-0.3	1411
0.3-0.4	3284
0.4-0.5	2137
0.5-0.6	934
0.6-0.7	246
0.7-0.8	50
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
0.8	Intermediate Similarity	NPD9728	Phase 1
0.7857	Intermediate Similarity	NPD1052	Approved
0.7857	Intermediate Similarity	NPD1051	Approved
0.7857	Intermediate Similarity	NPD1053	Approved
0.7849	Intermediate Similarity	NPD157	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4144	Approved
0.7831	Intermediate Similarity	NPD603	Approved
0.7831	Intermediate Similarity	NPD4147	Approved
0.7765	Intermediate Similarity	NPD5371	Approved
0.7765	Intermediate Similarity	NPD5372	Approved
0.7738	Intermediate Similarity	NPD293	Approved
0.7738	Intermediate Similarity	NPD296	Approved
0.7738	Intermediate Similarity	NPD295	Approved
0.7647	Intermediate Similarity	NPD507	Approved
0.7647	Intermediate Similarity	NPD508	Approved
0.7471	Intermediate Similarity	NPD3035	Approved
0.7471	Intermediate Similarity	NPD4027	Approved
0.7471	Intermediate Similarity	NPD4026	Approved
0.747	Intermediate Similarity	NPD9593	Approved
0.747	Intermediate Similarity	NPD9588	Approved
0.747	Intermediate Similarity	NPD9592	Approved
0.747	Intermediate Similarity	NPD9589	Approved
0.747	Intermediate Similarity	NPD9594	Approved
0.747	Intermediate Similarity	NPD80	Approved
0.747	Intermediate Similarity	NPD9590	Approved
0.747	Intermediate Similarity	NPD9591	Approved
0.7442	Intermediate Similarity	NPD590	Approved
0.7442	Intermediate Similarity	NPD589	Approved
0.7416	Intermediate Similarity	NPD2538	Approved
0.7416	Intermediate Similarity	NPD2539	Approved
0.7386	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4170	Approved
0.7386	Intermediate Similarity	NPD4169	Approved
0.732	Intermediate Similarity	NPD466	Approved
0.7303	Intermediate Similarity	NPD4635	Approved
0.7303	Intermediate Similarity	NPD830	Approved
0.7303	Intermediate Similarity	NPD831	Approved
0.7273	Intermediate Similarity	NPD4803	Discontinued
0.7253	Intermediate Similarity	NPD5252	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD742	Approved
0.7229	Intermediate Similarity	NPD292	Approved
0.7229	Intermediate Similarity	NPD294	Approved
0.7222	Intermediate Similarity	NPD5178	Approved
0.7222	Intermediate Similarity	NPD785	Approved
0.7172	Intermediate Similarity	NPD1795	Discontinued
0.7159	Intermediate Similarity	NPD3979	Approved
0.7159	Intermediate Similarity	NPD3903	Approved
0.7159	Intermediate Similarity	NPD3981	Approved
0.7159	Intermediate Similarity	NPD3904	Approved
0.7143	Intermediate Similarity	NPD2205	Approved
0.7143	Intermediate Similarity	NPD2208	Approved
0.7111	Intermediate Similarity	NPD1800	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD813	Approved
0.7097	Intermediate Similarity	NPD3345	Approved
0.7097	Intermediate Similarity	NPD5675	Discontinued
0.7079	Intermediate Similarity	NPD472	Approved
0.7071	Intermediate Similarity	NPD1796	Phase 3
0.7071	Intermediate Similarity	NPD787	Suspended
0.7065	Intermediate Similarity	NPD4406	Approved
0.7065	Intermediate Similarity	NPD4636	Approved
0.7065	Intermediate Similarity	NPD4409	Approved
0.7059	Intermediate Similarity	NPD1765	Approved
0.7059	Intermediate Similarity	NPD1763	Approved
0.7059	Intermediate Similarity	NPD1767	Approved
0.7059	Intermediate Similarity	NPD1766	Approved
0.7059	Intermediate Similarity	NPD1761	Approved
0.7059	Intermediate Similarity	NPD505	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1099	Approved
0.7041	Intermediate Similarity	NPD1100	Approved
0.7021	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4094	Approved
0.7	Intermediate Similarity	NPD5630	Phase 1
0.699	Remote Similarity	NPD7130	Phase 3
0.6989	Remote Similarity	NPD783	Approved
0.6989	Remote Similarity	NPD780	Approved
0.6989	Remote Similarity	NPD781	Approved
0.6989	Remote Similarity	NPD782	Approved
0.6966	Remote Similarity	NPD260	Discontinued
0.6957	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5916	Discontinued
0.6947	Remote Similarity	NPD4728	Approved
0.6932	Remote Similarity	NPD9563	Approved
0.6932	Remote Similarity	NPD9564	Approved
0.6932	Remote Similarity	NPD9397	Approved
0.6932	Remote Similarity	NPD79	Approved
0.6932	Remote Similarity	NPD9393	Approved
0.6931	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD588	Approved
0.6915	Remote Similarity	NPD587	Approved
0.6914	Remote Similarity	NPD173	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD1576	Approved
0.6893	Remote Similarity	NPD959	Discontinued
0.6882	Remote Similarity	NPD305	Approved
0.6882	Remote Similarity	NPD3099	Discontinued
0.6882	Remote Similarity	NPD304	Approved
0.6875	Remote Similarity	NPD2997	Approved
0.6875	Remote Similarity	NPD3000	Approved
0.6875	Remote Similarity	NPD2998	Approved
0.6869	Remote Similarity	NPD4657	Approved
0.6869	Remote Similarity	NPD4655	Approved
0.6863	Remote Similarity	NPD1387	Phase 1
0.6852	Remote Similarity	NPD5063	Approved
0.6852	Remote Similarity	NPD5064	Approved
0.6848	Remote Similarity	NPD4544	Approved
0.6847	Remote Similarity	NPD474	Approved
0.6842	Remote Similarity	NPD771	Phase 3
0.6827	Remote Similarity	NPD1064	Approved
0.6827	Remote Similarity	NPD1065	Approved
0.6809	Remote Similarity	NPD2002	Discontinued
0.6809	Remote Similarity	NPD3426	Approved
0.6809	Remote Similarity	NPD3428	Approved
0.6809	Remote Similarity	NPD4145	Approved
0.6809	Remote Similarity	NPD4146	Approved
0.6804	Remote Similarity	NPD4408	Approved
0.6804	Remote Similarity	NPD4407	Approved
0.6804	Remote Similarity	NPD4405	Approved
0.6796	Remote Similarity	NPD488	Approved
0.6796	Remote Similarity	NPD489	Approved
0.6771	Remote Similarity	NPD3344	Approved
0.6771	Remote Similarity	NPD3346	Approved
0.6771	Remote Similarity	NPD5915	Approved
0.6768	Remote Similarity	NPD3457	Approved
0.6768	Remote Similarity	NPD3456	Approved
0.6768	Remote Similarity	NPD3458	Approved
0.6765	Remote Similarity	NPD1386	Phase 1
0.6739	Remote Similarity	NPD4000	Phase 3
0.6735	Remote Similarity	NPD4545	Approved
0.6735	Remote Similarity	NPD4542	Approved
0.6733	Remote Similarity	NPD4007	Approved
0.6733	Remote Similarity	NPD4008	Approved
0.6667	Remote Similarity	NPD2656	Approved
0.6667	Remote Similarity	NPD9395	Approved
0.6667	Remote Similarity	NPD3427	Approved
0.6667	Remote Similarity	NPD297	Approved
0.6667	Remote Similarity	NPD9	Approved
0.6667	Remote Similarity	NPD3429	Approved
0.6667	Remote Similarity	NPD2655	Approved
0.6636	Remote Similarity	NPD3581	Discontinued
0.6636	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4813	Approved
0.6634	Remote Similarity	NPD4117	Approved
0.6634	Remote Similarity	NPD4263	Approved
0.6634	Remote Similarity	NPD1724	Approved
0.6633	Remote Similarity	NPD1814	Approved
0.6633	Remote Similarity	NPD6690	Approved
0.6633	Remote Similarity	NPD1812	Approved
0.6632	Remote Similarity	NPD187	Approved
0.6609	Remote Similarity	NPD4478	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD480	Approved
0.6602	Remote Similarity	NPD854	Approved
0.6602	Remote Similarity	NPD855	Approved
0.6602	Remote Similarity	NPD2648	Phase 3
0.6602	Remote Similarity	NPD2171	Approved
0.6602	Remote Similarity	NPD2196	Discontinued
0.6602	Remote Similarity	NPD2193	Phase 2
0.6602	Remote Similarity	NPD6024	Approved
0.6602	Remote Similarity	NPD6027	Approved
0.6593	Remote Similarity	NPD1617	Discontinued
0.6574	Remote Similarity	NPD2583	Phase 2
0.6571	Remote Similarity	NPD2197	Approved
0.6571	Remote Similarity	NPD2192	Approved
0.6566	Remote Similarity	NPD2878	Approved
0.6566	Remote Similarity	NPD8	Approved
0.6566	Remote Similarity	NPD243	Approved
0.6566	Remote Similarity	NPD6548	Approved
0.6566	Remote Similarity	NPD6549	Approved
0.6559	Remote Similarity	NPD2001	Discontinued
0.6545	Remote Similarity	NPD5180	Approved
0.6545	Remote Similarity	NPD5179	Approved
0.6545	Remote Similarity	NPD5181	Approved
0.6538	Remote Similarity	NPD3357	Discontinued
0.6535	Remote Similarity	NPD5598	Approved
0.6535	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5597	Approved
0.6531	Remote Similarity	NPD4543	Discontinued
0.6531	Remote Similarity	NPD7160	Approved
0.6531	Remote Similarity	NPD517	Discontinued
0.6522	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD2124	Approved
0.6509	Remote Similarity	NPD3459	Approved
0.65	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5554	Approved
0.6495	Remote Similarity	NPD9350	Approved
0.6495	Remote Similarity	NPD9348	Approved
0.6495	Remote Similarity	NPD9351	Phase 3
0.6495	Remote Similarity	NPD9349	Approved
0.6486	Remote Similarity	NPD2543	Discontinued
0.6486	Remote Similarity	NPD2508	Discontinued
0.6442	Remote Similarity	NPD4818	Approved
0.6442	Remote Similarity	NPD5716	Approved
0.6442	Remote Similarity	NPD4817	Approved
0.6442	Remote Similarity	NPD4119	Approved
0.6442	Remote Similarity	NPD4719	Phase 2
0.6436	Remote Similarity	NPD5964	Phase 2
0.6436	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1738	Approved
0.6436	Remote Similarity	NPD2005	Discontinued
0.6436	Remote Similarity	NPD6472	Discontinued
0.6436	Remote Similarity	NPD2895	Discontinued
0.6436	Remote Similarity	NPD5963	Phase 2

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