NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.05
Volume:	209.304
LogP:	1.377
LogD:	1.154
LogS:	-1.803
# Rotatable Bonds:	2
TPSA:	79.37
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	3.027
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.881
MDCK Permeability:	2.229225901828613e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.194
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	44.10438919067383%
Volume Distribution (VD):	1.292
Pgp-substrate:	58.35808563232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.222
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.548
CYP3A4-inhibitor:	0.318
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	7.724
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.408
AMES Toxicity:	0.372
Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.081
Carcinogencity:	0.045
Eye Corrosion:	0.005
Eye Irritation:	0.065
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC324702

Natural Product ID:	NPC324702
*Common Name:**	Pulicatins G
IUPAC Name:	n.a.
Synonyms:	Pulicatins G
Standard InCHIKey:	CMXJVCRUSKHTHR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H10N2O2S/c11-9(14)7-5-15-10(12-7)6-3-1-2-4-8(6)13/h1-4,7,13H,5H2,(H2,11,14)
SMILES:	OC(=N)C1CSC(=N1)c1ccccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651092
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids 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
NPO30976	Streptomyces sp. cp32	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]

☑ 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
Ki	11
Others	2

Activity Type	# Activity
Individual Protein	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	1260.0	nM	PMID[548072]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Activity	=	3708.0	nM	PMID[548072]
NPT251	Individual Protein	Histamine H1 receptor	Homo sapiens	Activity	=	678.0	nM	PMID[548072]
NPT291	Individual Protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	1300.0	nM	PMID[548073]
NPT2776	Individual Protein	Serotonin 1e (5-HT1e) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT290	Individual Protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT292	Individual Protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT425	Individual Protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT1784	Individual Protein	Serotonin 5a (5-HT5a) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT294	Individual Protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT973	Individual Protein	Serotonin 1b (5-HT1b) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]
NPT974	Individual Protein	Serotonin 1d (5-HT1d) receptor	Homo sapiens	Ki	>	10000.0	nM	PMID[548073]

☑ 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 NPC324702 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	218
0.1-0.2	2980
0.2-0.3	13291
0.3-0.4	7495
0.4-0.5	14137
0.5-0.6	3955
0.6-0.7	578
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9397	High Similarity	NPC112823
0.9316	High Similarity	NPC86966
0.7984	Intermediate Similarity	NPC5932
0.7971	Intermediate Similarity	NPC128237
0.7971	Intermediate Similarity	NPC83790
0.7739	Intermediate Similarity	NPC315921
0.7705	Intermediate Similarity	NPC227553
0.7586	Intermediate Similarity	NPC107619
0.752	Intermediate Similarity	NPC118202
0.75	Intermediate Similarity	NPC283760
0.746	Intermediate Similarity	NPC317254
0.7459	Intermediate Similarity	NPC153690
0.7419	Intermediate Similarity	NPC163674
0.7402	Intermediate Similarity	NPC82963
0.7388	Intermediate Similarity	NPC202776
0.7373	Intermediate Similarity	NPC275104
0.7344	Intermediate Similarity	NPC311737
0.7344	Intermediate Similarity	NPC38458
0.7333	Intermediate Similarity	NPC178902
0.7295	Intermediate Similarity	NPC231705
0.7258	Intermediate Similarity	NPC258056
0.7236	Intermediate Similarity	NPC142297
0.72	Intermediate Similarity	NPC474149
0.7197	Intermediate Similarity	NPC27581
0.7177	Intermediate Similarity	NPC24101
0.7177	Intermediate Similarity	NPC96224
0.7155	Intermediate Similarity	NPC265521
0.7132	Intermediate Similarity	NPC477839
0.7122	Intermediate Similarity	NPC184465
0.712	Intermediate Similarity	NPC316052
0.7059	Intermediate Similarity	NPC33168
0.705	Intermediate Similarity	NPC166624
0.7018	Intermediate Similarity	NPC198747
0.7018	Intermediate Similarity	NPC155393
0.6975	Remote Similarity	NPC3371
0.697	Remote Similarity	NPC319950
0.6957	Remote Similarity	NPC325651
0.6957	Remote Similarity	NPC407
0.6957	Remote Similarity	NPC307235
0.6942	Remote Similarity	NPC125732
0.694	Remote Similarity	NPC474862
0.693	Remote Similarity	NPC286904
0.6911	Remote Similarity	NPC68055
0.6879	Remote Similarity	NPC163810
0.6857	Remote Similarity	NPC326966
0.685	Remote Similarity	NPC71266
0.685	Remote Similarity	NPC145638
0.685	Remote Similarity	NPC290566
0.6846	Remote Similarity	NPC142599
0.6831	Remote Similarity	NPC71888
0.6831	Remote Similarity	NPC120114
0.6814	Remote Similarity	NPC146703
0.68	Remote Similarity	NPC211551
0.678	Remote Similarity	NPC47950
0.6761	Remote Similarity	NPC267237
0.675	Remote Similarity	NPC128062
0.6748	Remote Similarity	NPC29601
0.6748	Remote Similarity	NPC289381
0.6748	Remote Similarity	NPC155847
0.6744	Remote Similarity	NPC166837
0.6742	Remote Similarity	NPC188867
0.6742	Remote Similarity	NPC106551
0.6742	Remote Similarity	NPC281686
0.6741	Remote Similarity	NPC473050
0.6741	Remote Similarity	NPC284078
0.6741	Remote Similarity	NPC473051
0.6739	Remote Similarity	NPC476249
0.6736	Remote Similarity	NPC309667
0.6723	Remote Similarity	NPC306074
0.6723	Remote Similarity	NPC204210
0.6723	Remote Similarity	NPC231150
0.6716	Remote Similarity	NPC268572
0.6716	Remote Similarity	NPC43275
0.6714	Remote Similarity	NPC478147
0.6696	Remote Similarity	NPC265146
0.6694	Remote Similarity	NPC318154
0.6694	Remote Similarity	NPC246679
0.6692	Remote Similarity	NPC283468
0.669	Remote Similarity	NPC328070
0.6667	Remote Similarity	NPC23167
0.6667	Remote Similarity	NPC271440
0.6667	Remote Similarity	NPC64205
0.6667	Remote Similarity	NPC29373
0.6667	Remote Similarity	NPC37302
0.6667	Remote Similarity	NPC213
0.6667	Remote Similarity	NPC10286
0.6667	Remote Similarity	NPC326241
0.6643	Remote Similarity	NPC296712
0.6642	Remote Similarity	NPC122009
0.6641	Remote Similarity	NPC309808
0.6639	Remote Similarity	NPC283711
0.6639	Remote Similarity	NPC300017
0.6638	Remote Similarity	NPC248817
0.6638	Remote Similarity	NPC175313
0.6621	Remote Similarity	NPC473052
0.6621	Remote Similarity	NPC473055
0.6613	Remote Similarity	NPC328793
0.6612	Remote Similarity	NPC152415
0.6612	Remote Similarity	NPC245187
0.661	Remote Similarity	NPC113460
0.661	Remote Similarity	NPC104216
0.661	Remote Similarity	NPC25493
0.661	Remote Similarity	NPC27974
0.6599	Remote Similarity	NPC477837
0.6599	Remote Similarity	NPC477838
0.6596	Remote Similarity	NPC271808
0.6593	Remote Similarity	NPC239697
0.6585	Remote Similarity	NPC475078
0.6585	Remote Similarity	NPC152097
0.6583	Remote Similarity	NPC45040
0.6581	Remote Similarity	NPC197783
0.6581	Remote Similarity	NPC326349
0.6581	Remote Similarity	NPC323336
0.6575	Remote Similarity	NPC322526
0.6575	Remote Similarity	NPC471201
0.6575	Remote Similarity	NPC214988
0.6575	Remote Similarity	NPC48202
0.6573	Remote Similarity	NPC244866
0.6571	Remote Similarity	NPC476353
0.6569	Remote Similarity	NPC142577
0.6567	Remote Similarity	NPC137096
0.6565	Remote Similarity	NPC146422
0.6562	Remote Similarity	NPC315388
0.6558	Remote Similarity	NPC123011
0.6558	Remote Similarity	NPC256689
0.6557	Remote Similarity	NPC8392
0.6555	Remote Similarity	NPC123273
0.6555	Remote Similarity	NPC318325
0.6555	Remote Similarity	NPC280347
0.6555	Remote Similarity	NPC242240
0.6555	Remote Similarity	NPC70436
0.6555	Remote Similarity	NPC258219
0.6555	Remote Similarity	NPC177420
0.6555	Remote Similarity	NPC316108
0.6552	Remote Similarity	NPC124436
0.6547	Remote Similarity	NPC171372
0.6545	Remote Similarity	NPC249662
0.6541	Remote Similarity	NPC303370
0.6532	Remote Similarity	NPC80027
0.6532	Remote Similarity	NPC260775
0.6532	Remote Similarity	NPC128723
0.6531	Remote Similarity	NPC197921
0.6529	Remote Similarity	NPC325292
0.6529	Remote Similarity	NPC138117
0.6528	Remote Similarity	NPC105541
0.6525	Remote Similarity	NPC184169
0.6513	Remote Similarity	NPC20755
0.6512	Remote Similarity	NPC309982
0.651	Remote Similarity	NPC106183
0.6507	Remote Similarity	NPC474587
0.6507	Remote Similarity	NPC166667
0.6507	Remote Similarity	NPC475132
0.6507	Remote Similarity	NPC313694
0.6507	Remote Similarity	NPC242159
0.6504	Remote Similarity	NPC259512
0.6504	Remote Similarity	NPC312132
0.65	Remote Similarity	NPC55561
0.65	Remote Similarity	NPC192
0.65	Remote Similarity	NPC29477
0.65	Remote Similarity	NPC300478
0.65	Remote Similarity	NPC312304
0.65	Remote Similarity	NPC151764
0.65	Remote Similarity	NPC226438
0.6496	Remote Similarity	NPC150837
0.6493	Remote Similarity	NPC258992
0.6486	Remote Similarity	NPC168861
0.6486	Remote Similarity	NPC469360
0.6486	Remote Similarity	NPC91953
0.648	Remote Similarity	NPC248396
0.648	Remote Similarity	NPC129373
0.648	Remote Similarity	NPC174911
0.648	Remote Similarity	NPC130103
0.648	Remote Similarity	NPC130756
0.648	Remote Similarity	NPC48730
0.648	Remote Similarity	NPC70677
0.648	Remote Similarity	NPC72729
0.648	Remote Similarity	NPC12931
0.6475	Remote Similarity	NPC151715
0.6475	Remote Similarity	NPC289769
0.6463	Remote Similarity	NPC475293
0.6462	Remote Similarity	NPC172046
0.6458	Remote Similarity	NPC307123
0.6458	Remote Similarity	NPC471953
0.6458	Remote Similarity	NPC247018
0.6458	Remote Similarity	NPC97870
0.6452	Remote Similarity	NPC226096
0.6452	Remote Similarity	NPC156313
0.6452	Remote Similarity	NPC290515
0.6452	Remote Similarity	NPC303611
0.6452	Remote Similarity	NPC6597
0.6452	Remote Similarity	NPC79241
0.6452	Remote Similarity	NPC164514
0.6452	Remote Similarity	NPC108606
0.6452	Remote Similarity	NPC88420
0.6452	Remote Similarity	NPC77492
0.6446	Remote Similarity	NPC270547
0.6446	Remote Similarity	NPC304541
0.6438	Remote Similarity	NPC6570
0.6434	Remote Similarity	NPC474091
0.6429	Remote Similarity	NPC95733

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 NPC324702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	692
0.2-0.3	1131
0.3-0.4	2518
0.4-0.5	3200
0.5-0.6	1239
0.6-0.7	226
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.803	Intermediate Similarity	NPD468	Phase 1
0.7937	Intermediate Similarity	NPD3143	Discontinued
0.7739	Intermediate Similarity	NPD9273	Approved
0.7538	Intermediate Similarity	NPD3070	Discontinued
0.7536	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1759	Phase 1
0.7153	Intermediate Similarity	NPD2372	Approved
0.7131	Intermediate Similarity	NPD9608	Approved
0.7131	Intermediate Similarity	NPD9610	Approved
0.7114	Intermediate Similarity	NPD3111	Phase 1
0.7105	Intermediate Similarity	NPD7494	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD682	Discontinued
0.7077	Intermediate Similarity	NPD1758	Phase 1
0.7059	Intermediate Similarity	NPD7451	Discontinued
0.7027	Intermediate Similarity	NPD7303	Discontinued
0.6993	Remote Similarity	NPD7737	Approved
0.6993	Remote Similarity	NPD7738	Approved
0.6992	Remote Similarity	NPD3421	Phase 3
0.6944	Remote Similarity	NPD1803	Phase 3
0.6929	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3136	Phase 2
0.6853	Remote Similarity	NPD3555	Approved
0.6853	Remote Similarity	NPD3553	Approved
0.6853	Remote Similarity	NPD3552	Approved
0.6853	Remote Similarity	NPD3554	Approved
0.685	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9618	Approved
0.6846	Remote Similarity	NPD9614	Approved
0.6824	Remote Similarity	NPD6106	Discontinued
0.6822	Remote Similarity	NPD1105	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD318	Approved
0.6818	Remote Similarity	NPD317	Approved
0.6815	Remote Similarity	NPD7133	Discontinued
0.6803	Remote Similarity	NPD9712	Approved
0.68	Remote Similarity	NPD6390	Discontinued
0.6795	Remote Similarity	NPD2098	Approved
0.6742	Remote Similarity	NPD9568	Approved
0.6741	Remote Similarity	NPD1981	Approved
0.6741	Remote Similarity	NPD1983	Approved
0.6741	Remote Similarity	NPD1980	Approved
0.6723	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD9710	Approved
0.6721	Remote Similarity	NPD9711	Approved
0.6715	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1786	Approved
0.6667	Remote Similarity	NPD1785	Approved
0.6667	Remote Similarity	NPD1787	Approved
0.6667	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2097	Approved
0.6642	Remote Similarity	NPD6093	Discontinued
0.6625	Remote Similarity	NPD4652	Approved
0.6623	Remote Similarity	NPD4739	Approved
0.6622	Remote Similarity	NPD3599	Approved
0.6618	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1444	Approved
0.6614	Remote Similarity	NPD1445	Approved
0.6613	Remote Similarity	NPD9248	Phase 1
0.6603	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD475	Phase 2
0.6589	Remote Similarity	NPD9713	Approved
0.6581	Remote Similarity	NPD9538	Approved
0.6573	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD839	Approved
0.6573	Remote Similarity	NPD840	Approved
0.6569	Remote Similarity	NPD804	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4480	Approved
0.6567	Remote Similarity	NPD16	Approved
0.6567	Remote Similarity	NPD9613	Approved
0.6567	Remote Similarity	NPD9615	Approved
0.6567	Remote Similarity	NPD856	Approved
0.6567	Remote Similarity	NPD9616	Approved
0.6565	Remote Similarity	NPD9377	Approved
0.6565	Remote Similarity	NPD9379	Approved
0.6562	Remote Similarity	NPD2889	Approved
0.6562	Remote Similarity	NPD2017	Approved
0.6562	Remote Similarity	NPD2888	Approved
0.6562	Remote Similarity	NPD2890	Approved
0.6557	Remote Similarity	NPD844	Approved
0.6552	Remote Similarity	NPD111	Approved
0.6538	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7450	Phase 2
0.6529	Remote Similarity	NPD845	Approved
0.6525	Remote Similarity	NPD4212	Discontinued
0.6522	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2561	Approved
0.6522	Remote Similarity	NPD2517	Approved
0.6522	Remote Similarity	NPD2562	Approved
0.6522	Remote Similarity	NPD4273	Approved
0.6519	Remote Similarity	NPD5304	Approved
0.6519	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5303	Approved
0.6519	Remote Similarity	NPD316	Approved
0.651	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD288	Approved
0.6503	Remote Similarity	NPD1048	Approved
0.65	Remote Similarity	NPD1135	Approved
0.65	Remote Similarity	NPD1129	Approved
0.65	Remote Similarity	NPD1131	Approved
0.65	Remote Similarity	NPD1133	Approved
0.65	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1134	Approved
0.6496	Remote Similarity	NPD542	Phase 1
0.6486	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7978	Discontinued
0.648	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2933	Approved
0.6475	Remote Similarity	NPD2934	Approved
0.6462	Remote Similarity	NPD1792	Phase 2
0.646	Remote Similarity	NPD2516	Approved
0.6458	Remote Similarity	NPD1423	Approved
0.6452	Remote Similarity	NPD9611	Approved
0.6452	Remote Similarity	NPD9612	Approved
0.6452	Remote Similarity	NPD9609	Approved
0.6446	Remote Similarity	NPD1814	Approved
0.6446	Remote Similarity	NPD1812	Approved
0.6444	Remote Similarity	NPD6360	Discontinued
0.6443	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD846	Approved
0.6429	Remote Similarity	NPD940	Approved
0.6423	Remote Similarity	NPD2860	Approved
0.6423	Remote Similarity	NPD2859	Approved
0.6418	Remote Similarity	NPD256	Approved
0.6418	Remote Similarity	NPD255	Approved
0.6408	Remote Similarity	NPD1712	Approved
0.6408	Remote Similarity	NPD767	Phase 1
0.6406	Remote Similarity	NPD1040	Phase 2
0.6403	Remote Similarity	NPD6624	Discontinued
0.6392	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5929	Approved
0.6391	Remote Similarity	NPD2234	Approved
0.6391	Remote Similarity	NPD2229	Approved
0.6391	Remote Similarity	NPD2228	Approved
0.6389	Remote Similarity	NPD5299	Approved
0.6386	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.637	Remote Similarity	NPD654	Phase 3
0.637	Remote Similarity	NPD3123	Discovery
0.637	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD530	Approved
0.6358	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD9622	Approved
0.6351	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7477	Discontinued
0.6343	Remote Similarity	NPD595	Approved
0.6343	Remote Similarity	NPD593	Approved
0.6341	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD309	Approved
0.6328	Remote Similarity	NPD10	Approved
0.6328	Remote Similarity	NPD311	Approved
0.6328	Remote Similarity	NPD314	Approved
0.6328	Remote Similarity	NPD310	Approved
0.6328	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD315	Approved
0.6327	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3692	Discontinued
0.6316	Remote Similarity	NPD821	Approved
0.6316	Remote Similarity	NPD302	Approved
0.6312	Remote Similarity	NPD2922	Phase 1
0.6304	Remote Similarity	NPD9381	Approved
0.6304	Remote Similarity	NPD9384	Approved
0.6301	Remote Similarity	NPD5323	Approved
0.6301	Remote Similarity	NPD6346	Approved
0.6301	Remote Similarity	NPD1555	Discontinued
0.6299	Remote Similarity	NPD2504	Approved
0.6299	Remote Similarity	NPD2505	Approved
0.6291	Remote Similarity	NPD2211	Approved
0.6291	Remote Similarity	NPD2209	Approved
0.629	Remote Similarity	NPD1809	Phase 2
0.6286	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD696	Discontinued
0.628	Remote Similarity	NPD6332	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7330	Discontinued
0.627	Remote Similarity	NPD3020	Approved
0.627	Remote Similarity	NPD1067	Discontinued
0.6269	Remote Similarity	NPD592	Approved
0.6269	Remote Similarity	NPD594	Approved
0.6268	Remote Similarity	NPD1794	Approved
0.6268	Remote Similarity	NPD3053	Approved
0.6268	Remote Similarity	NPD3055	Approved
0.6258	Remote Similarity	NPD4319	Phase 2
0.625	Remote Similarity	NPD600	Approved
0.625	Remote Similarity	NPD596	Approved
0.6241	Remote Similarity	NPD4659	Approved
0.6241	Remote Similarity	NPD4991	Discontinued
0.6232	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD602	Approved
0.6224	Remote Similarity	NPD599	Approved
0.6222	Remote Similarity	NPD1791	Approved
0.6222	Remote Similarity	NPD1793	Approved
0.622	Remote Similarity	NPD1275	Phase 2
0.6214	Remote Similarity	NPD3151	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2046	Approved
0.6207	Remote Similarity	NPD2045	Approved
0.6207	Remote Similarity	NPD21	Approved
0.6207	Remote Similarity	NPD2048	Approved
0.6207	Remote Similarity	NPD2049	Clinical (unspecified phase)

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