NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	426.93
Volume:	278.934
LogP:	-1.272
LogD:	0.023
LogS:	0.273
# Rotatable Bonds:	4
TPSA:	60.36
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	3.923
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.448
MDCK Permeability:	3.79965640604496e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.877
20% Bioavailability (F20%):	0.855
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.29
Plasma Protein Binding (PPB):	17.966840744018555%
Volume Distribution (VD):	0.731
Pgp-substrate:	80.53732299804688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.272
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	2.079
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.704
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.542
Skin Sensitization:	0.019
Carcinogencity:	0.057
Eye Corrosion:	0.005
Eye Irritation:	0.029
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC243404

Natural Product ID:	NPC243404
*Common Name:**	Purpuroine I
IUPAC Name:	(2R)-3-(3-bromo-4-hydroxy-5-iodophenyl)-2-(trimethylazaniumyl)propanoate
Synonyms:	Purpuroine I
Standard InCHIKey:	JRMILWBTUZMVEQ-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C12H15BrINO3/c1-15(2,3)10(12(17)18)6-7-4-8(13)11(16)9(14)5-7/h4-5,10H,6H2,1-3H3,(H-,16,17,18)/t10-/m1/s1
SMILES:	C[N+](C)(C)[C@H](Cc1cc(c(c(c1)I)O)Br)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204073
PubChem CID:	71454037
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 [CHEMONTID:0004319] Tyrosine 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
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924179]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23131412]
NPO9305	Iotrochota purpurea	Species	Iotrochotidae	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	4

Activity Type	# Activity
Individual Protein	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[568314]
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[568314]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[568314]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	=	18.06	ug.mL-1	PMID[568314]

☑ 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 NPC243404 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	196
0.1-0.2	1718
0.2-0.3	8659
0.3-0.4	10774
0.4-0.5	14611
0.5-0.6	6002
0.6-0.7	688
0.7-0.8	45
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC40321
0.8889	High Similarity	NPC56634
0.8077	Intermediate Similarity	NPC317784
0.8077	Intermediate Similarity	NPC142638
0.8015	Intermediate Similarity	NPC239697
0.7902	Intermediate Similarity	NPC470709
0.7879	Intermediate Similarity	NPC319950
0.7868	Intermediate Similarity	NPC124776
0.782	Intermediate Similarity	NPC180207
0.7786	Intermediate Similarity	NPC106551
0.7786	Intermediate Similarity	NPC281686
0.7786	Intermediate Similarity	NPC188867
0.7704	Intermediate Similarity	NPC142577
0.7643	Intermediate Similarity	NPC474087
0.7574	Intermediate Similarity	NPC27581
0.7557	Intermediate Similarity	NPC59387
0.7535	Intermediate Similarity	NPC474753
0.75	Intermediate Similarity	NPC115803
0.7429	Intermediate Similarity	NPC476353
0.7391	Intermediate Similarity	NPC116562
0.7376	Intermediate Similarity	NPC296712
0.7324	Intermediate Similarity	NPC478147
0.726	Intermediate Similarity	NPC109580
0.7246	Intermediate Similarity	NPC326079
0.7222	Intermediate Similarity	NPC45191
0.7222	Intermediate Similarity	NPC257390
0.7203	Intermediate Similarity	NPC325651
0.7194	Intermediate Similarity	NPC474862
0.7172	Intermediate Similarity	NPC244866
0.7172	Intermediate Similarity	NPC259017
0.7165	Intermediate Similarity	NPC155847
0.7165	Intermediate Similarity	NPC289381
0.7153	Intermediate Similarity	NPC474091
0.7152	Intermediate Similarity	NPC81026
0.7134	Intermediate Similarity	NPC475688
0.7133	Intermediate Similarity	NPC161593
0.7133	Intermediate Similarity	NPC16031
0.7133	Intermediate Similarity	NPC145888
0.7103	Intermediate Similarity	NPC475735
0.7087	Intermediate Similarity	NPC245561
0.7086	Intermediate Similarity	NPC266741
0.7066	Intermediate Similarity	NPC475120
0.7063	Intermediate Similarity	NPC305717
0.7055	Intermediate Similarity	NPC88667
0.7045	Intermediate Similarity	NPC471495
0.7031	Intermediate Similarity	NPC52472
0.7008	Intermediate Similarity	NPC322598
0.7	Intermediate Similarity	NPC317741
0.7	Intermediate Similarity	NPC197239
0.7	Intermediate Similarity	NPC282087
0.7	Intermediate Similarity	NPC241086
0.7	Intermediate Similarity	NPC328137
0.7	Intermediate Similarity	NPC318984
0.7	Intermediate Similarity	NPC259800
0.7	Intermediate Similarity	NPC326860
0.7	Intermediate Similarity	NPC318028
0.6992	Remote Similarity	NPC54543
0.6986	Remote Similarity	NPC326966
0.6986	Remote Similarity	NPC48909
0.6986	Remote Similarity	NPC473724
0.698	Remote Similarity	NPC313694
0.698	Remote Similarity	NPC242159
0.6959	Remote Similarity	NPC471328
0.695	Remote Similarity	NPC7830
0.6947	Remote Similarity	NPC67043
0.6947	Remote Similarity	NPC476198
0.6944	Remote Similarity	NPC321561
0.6943	Remote Similarity	NPC39431
0.694	Remote Similarity	NPC473358
0.6939	Remote Similarity	NPC470392
0.6933	Remote Similarity	NPC177967
0.6933	Remote Similarity	NPC471237
0.6913	Remote Similarity	NPC6913
0.6912	Remote Similarity	NPC309808
0.6901	Remote Similarity	NPC296202
0.6897	Remote Similarity	NPC202776
0.6892	Remote Similarity	NPC163810
0.6887	Remote Similarity	NPC471236
0.6887	Remote Similarity	NPC197766
0.6875	Remote Similarity	NPC260000
0.6875	Remote Similarity	NPC110131
0.6871	Remote Similarity	NPC70485
0.6857	Remote Similarity	NPC100395
0.6853	Remote Similarity	NPC105999
0.6842	Remote Similarity	NPC81137
0.6842	Remote Similarity	NPC251439
0.6822	Remote Similarity	NPC280869
0.6821	Remote Similarity	NPC48202
0.6821	Remote Similarity	NPC238412
0.6821	Remote Similarity	NPC197045
0.6818	Remote Similarity	NPC473941
0.6818	Remote Similarity	NPC65714
0.6818	Remote Similarity	NPC13495
0.6812	Remote Similarity	NPC10286
0.6812	Remote Similarity	NPC213
0.6806	Remote Similarity	NPC171372
0.6806	Remote Similarity	NPC213414
0.68	Remote Similarity	NPC6570
0.6797	Remote Similarity	NPC474128
0.6794	Remote Similarity	NPC178902
0.6792	Remote Similarity	NPC473580
0.6791	Remote Similarity	NPC31274
0.6781	Remote Similarity	NPC122359
0.6781	Remote Similarity	NPC159987
0.6781	Remote Similarity	NPC78061
0.6779	Remote Similarity	NPC184465
0.6774	Remote Similarity	NPC16188
0.6739	Remote Similarity	NPC118202
0.6736	Remote Similarity	NPC307020
0.673	Remote Similarity	NPC47672
0.6728	Remote Similarity	NPC469243
0.6711	Remote Similarity	NPC328070
0.6711	Remote Similarity	NPC166624
0.671	Remote Similarity	NPC184632
0.6709	Remote Similarity	NPC233702
0.6708	Remote Similarity	NPC233926
0.6705	Remote Similarity	NPC248822
0.6704	Remote Similarity	NPC471592
0.6692	Remote Similarity	NPC12730
0.6691	Remote Similarity	NPC317254
0.6688	Remote Similarity	NPC66518
0.6667	Remote Similarity	NPC280736
0.6667	Remote Similarity	NPC13426
0.6646	Remote Similarity	NPC20755
0.6645	Remote Similarity	NPC473052
0.6645	Remote Similarity	NPC473055
0.6644	Remote Similarity	NPC11449
0.6642	Remote Similarity	NPC231705
0.6641	Remote Similarity	NPC214200
0.6641	Remote Similarity	NPC228400
0.6626	Remote Similarity	NPC475544
0.6625	Remote Similarity	NPC469711
0.6623	Remote Similarity	NPC71888
0.6623	Remote Similarity	NPC91953
0.6623	Remote Similarity	NPC120114
0.662	Remote Similarity	NPC117759
0.6618	Remote Similarity	NPC258056
0.6618	Remote Similarity	NPC326187
0.6606	Remote Similarity	NPC223207
0.6603	Remote Similarity	NPC135349
0.6603	Remote Similarity	NPC147137
0.6601	Remote Similarity	NPC322526
0.6601	Remote Similarity	NPC474673
0.6597	Remote Similarity	NPC268348
0.6594	Remote Similarity	NPC48525
0.6594	Remote Similarity	NPC17693
0.6593	Remote Similarity	NPC142297
0.6581	Remote Similarity	NPC13696
0.6577	Remote Similarity	NPC99280
0.6577	Remote Similarity	NPC195902
0.6577	Remote Similarity	NPC478071
0.6577	Remote Similarity	NPC120251
0.6569	Remote Similarity	NPC222084
0.6569	Remote Similarity	NPC474149
0.6566	Remote Similarity	NPC471771
0.6566	Remote Similarity	NPC304074
0.6566	Remote Similarity	NPC290755
0.6565	Remote Similarity	NPC125732
0.6562	Remote Similarity	NPC258222
0.6562	Remote Similarity	NPC202198
0.6558	Remote Similarity	NPC197921
0.6558	Remote Similarity	NPC150712
0.6547	Remote Similarity	NPC148969
0.6547	Remote Similarity	NPC471488
0.6544	Remote Similarity	NPC153690
0.6541	Remote Similarity	NPC324081
0.6538	Remote Similarity	NPC308571
0.6538	Remote Similarity	NPC122493
0.6538	Remote Similarity	NPC293628
0.6538	Remote Similarity	NPC10781
0.6536	Remote Similarity	NPC470248
0.6536	Remote Similarity	NPC470249
0.6536	Remote Similarity	NPC309667
0.6534	Remote Similarity	NPC96275
0.6529	Remote Similarity	NPC288747
0.6525	Remote Similarity	NPC82963
0.6522	Remote Similarity	NPC227553
0.6522	Remote Similarity	NPC163674
0.6519	Remote Similarity	NPC317592
0.6519	Remote Similarity	NPC122599
0.6519	Remote Similarity	NPC270848
0.6519	Remote Similarity	NPC272868
0.6516	Remote Similarity	NPC469360
0.6513	Remote Similarity	NPC473360
0.6513	Remote Similarity	NPC470441
0.6509	Remote Similarity	NPC191557
0.6506	Remote Similarity	NPC63931
0.6503	Remote Similarity	NPC38483
0.6503	Remote Similarity	NPC283760
0.6497	Remote Similarity	NPC246591
0.6496	Remote Similarity	NPC145638
0.6496	Remote Similarity	NPC290566
0.6496	Remote Similarity	NPC234639
0.6496	Remote Similarity	NPC473372
0.6494	Remote Similarity	NPC471201
0.6493	Remote Similarity	NPC261573
0.6493	Remote Similarity	NPC120693
0.6493	Remote Similarity	NPC8931
0.6479	Remote Similarity	NPC38458
0.6479	Remote Similarity	NPC311737

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 NPC243404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	627
0.2-0.3	1326
0.3-0.4	2556
0.4-0.5	2809
0.5-0.6	1445
0.6-0.7	236
0.7-0.8	5
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8712	High Similarity	NPD9718	Approved
0.7786	Intermediate Similarity	NPD9568	Approved
0.7576	Intermediate Similarity	NPD255	Approved
0.7576	Intermediate Similarity	NPD256	Approved
0.7133	Intermediate Similarity	NPD9569	Approved
0.7055	Intermediate Similarity	NPD259	Phase 1
0.7042	Intermediate Similarity	NPD196	Phase 1
0.7034	Intermediate Similarity	NPD3136	Phase 2
0.7034	Intermediate Similarity	NPD9537	Phase 1
0.7034	Intermediate Similarity	NPD9536	Phase 1
0.7	Intermediate Similarity	NPD1519	Approved
0.7	Intermediate Similarity	NPD1523	Approved
0.7	Intermediate Similarity	NPD1538	Phase 1
0.7	Intermediate Similarity	NPD1522	Approved
0.7	Intermediate Similarity	NPD1537	Approved
0.6959	Remote Similarity	NPD555	Phase 2
0.6957	Remote Similarity	NPD318	Approved
0.6957	Remote Similarity	NPD317	Approved
0.6944	Remote Similarity	NPD257	Approved
0.6944	Remote Similarity	NPD258	Approved
0.6906	Remote Similarity	NPD1759	Phase 1
0.687	Remote Similarity	NPD9608	Approved
0.687	Remote Similarity	NPD9610	Approved
0.6867	Remote Similarity	NPD1521	Approved
0.6867	Remote Similarity	NPD1536	Approved
0.6867	Remote Similarity	NPD1520	Approved
0.6835	Remote Similarity	NPD1758	Phase 1
0.6824	Remote Similarity	NPD5745	Approved
0.6824	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2228	Approved
0.6788	Remote Similarity	NPD2229	Approved
0.6788	Remote Similarity	NPD2234	Approved
0.6736	Remote Similarity	NPD4659	Approved
0.6736	Remote Similarity	NPD1755	Approved
0.6714	Remote Similarity	NPD856	Approved
0.6714	Remote Similarity	NPD16	Approved
0.6689	Remote Similarity	NPD5746	Approved
0.6667	Remote Similarity	NPD7495	Discontinued
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD7523	Phase 3
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD2562	Approved
0.6667	Remote Similarity	NPD2561	Approved
0.6667	Remote Similarity	NPD9570	Approved
0.6644	Remote Similarity	NPD4103	Phase 2
0.6644	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1445	Approved
0.6642	Remote Similarity	NPD1444	Approved
0.6623	Remote Similarity	NPD275	Approved
0.6623	Remote Similarity	NPD274	Approved
0.6603	Remote Similarity	NPD3400	Discontinued
0.6601	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD855	Approved
0.6591	Remote Similarity	NPD854	Approved
0.6582	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7450	Phase 2
0.6549	Remote Similarity	NPD5303	Approved
0.6549	Remote Similarity	NPD5304	Approved
0.6538	Remote Similarity	NPD9566	Approved
0.6538	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7978	Discontinued
0.651	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD4102	Approved
0.6503	Remote Similarity	NPD4105	Approved
0.6496	Remote Similarity	NPD1792	Phase 2
0.6496	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD9613	Approved
0.6479	Remote Similarity	NPD9616	Approved
0.6479	Remote Similarity	NPD9615	Approved
0.6463	Remote Similarity	NPD8019	Approved
0.646	Remote Similarity	NPD7131	Phase 3
0.6452	Remote Similarity	NPD2239	Approved
0.6452	Remote Similarity	NPD2240	Approved
0.6447	Remote Similarity	NPD4445	Approved
0.6439	Remote Similarity	NPD9712	Approved
0.6434	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD316	Approved
0.6424	Remote Similarity	NPD4619	Approved
0.6424	Remote Similarity	NPD4621	Approved
0.6419	Remote Similarity	NPD2627	Approved
0.6419	Remote Similarity	NPD2159	Approved
0.6419	Remote Similarity	NPD1129	Approved
0.6419	Remote Similarity	NPD2628	Approved
0.6419	Remote Similarity	NPD1135	Approved
0.6419	Remote Similarity	NPD2625	Approved
0.6419	Remote Similarity	NPD1131	Approved
0.6419	Remote Similarity	NPD2626	Approved
0.6419	Remote Similarity	NPD1133	Approved
0.6419	Remote Similarity	NPD1134	Approved
0.6419	Remote Similarity	NPD2160	Approved
0.6389	Remote Similarity	NPD4093	Discontinued
0.6383	Remote Similarity	NPD9618	Approved
0.6383	Remote Similarity	NPD9614	Approved
0.6383	Remote Similarity	NPD1791	Approved
0.6383	Remote Similarity	NPD1793	Approved
0.637	Remote Similarity	NPD311	Approved
0.637	Remote Similarity	NPD10	Approved
0.637	Remote Similarity	NPD315	Approved
0.637	Remote Similarity	NPD1535	Discovery
0.637	Remote Similarity	NPD314	Approved
0.637	Remote Similarity	NPD310	Approved
0.637	Remote Similarity	NPD309	Approved
0.6364	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD9711	Approved
0.6364	Remote Similarity	NPD9710	Approved
0.6358	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.635	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6346	Approved
0.6327	Remote Similarity	NPD1481	Phase 2
0.6319	Remote Similarity	NPD1894	Discontinued
0.6316	Remote Similarity	NPD597	Approved
0.6316	Remote Similarity	NPD598	Approved
0.6316	Remote Similarity	NPD601	Approved
0.6316	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2098	Approved
0.6309	Remote Similarity	NPD3053	Approved
0.6309	Remote Similarity	NPD3055	Approved
0.6301	Remote Similarity	NPD4135	Approved
0.6301	Remote Similarity	NPD4106	Approved
0.6301	Remote Similarity	NPD4136	Approved
0.6296	Remote Similarity	NPD6390	Discontinued
0.6296	Remote Similarity	NPD2183	Approved
0.6296	Remote Similarity	NPD2184	Approved
0.6291	Remote Similarity	NPD4620	Approved
0.6291	Remote Similarity	NPD2614	Approved
0.6291	Remote Similarity	NPD5201	Approved
0.6291	Remote Similarity	NPD5203	Approved
0.6291	Remote Similarity	NPD4617	Approved
0.6284	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD1169	Approved
0.628	Remote Similarity	NPD3455	Phase 2
0.6275	Remote Similarity	NPD1132	Approved
0.6275	Remote Similarity	NPD1130	Approved
0.6275	Remote Similarity	NPD1136	Approved
0.6275	Remote Similarity	NPD520	Approved
0.6272	Remote Similarity	NPD8303	Discontinued
0.6268	Remote Similarity	NPD747	Discontinued
0.6267	Remote Similarity	NPD602	Approved
0.6267	Remote Similarity	NPD9619	Approved
0.6267	Remote Similarity	NPD599	Approved
0.6267	Remote Similarity	NPD9621	Approved
0.6267	Remote Similarity	NPD9620	Approved
0.6266	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD5356	Approved
0.6265	Remote Similarity	NPD5355	Approved
0.6259	Remote Similarity	NPD4807	Approved
0.6259	Remote Similarity	NPD4806	Approved
0.6258	Remote Similarity	NPD1670	Discontinued
0.6258	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4476	Approved
0.6242	Remote Similarity	NPD4477	Approved
0.6241	Remote Similarity	NPD9377	Approved
0.6241	Remote Similarity	NPD9379	Approved
0.6235	Remote Similarity	NPD3536	Discontinued
0.6233	Remote Similarity	NPD1751	Approved
0.6233	Remote Similarity	NPD2667	Approved
0.6233	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD2668	Approved
0.6225	Remote Similarity	NPD3664	Approved
0.6225	Remote Similarity	NPD3636	Approved
0.6225	Remote Similarity	NPD5204	Approved
0.6225	Remote Similarity	NPD3663	Approved
0.6225	Remote Similarity	NPD3661	Approved
0.6225	Remote Similarity	NPD3637	Approved
0.6225	Remote Similarity	NPD3662	Phase 3
0.6225	Remote Similarity	NPD3635	Approved
0.6214	Remote Similarity	NPD3644	Approved
0.6214	Remote Similarity	NPD3642	Approved
0.6214	Remote Similarity	NPD3643	Approved
0.6211	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD9545	Approved
0.6203	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2097	Approved
0.619	Remote Similarity	NPD3421	Phase 3
0.619	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4207	Discontinued
0.6184	Remote Similarity	NPD2606	Approved
0.6184	Remote Similarity	NPD2605	Approved
0.6181	Remote Similarity	NPD3123	Discovery
0.6178	Remote Similarity	NPD1753	Discontinued
0.6174	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5157	Phase 1
0.6174	Remote Similarity	NPD9622	Approved
0.6174	Remote Similarity	NPD5159	Phase 2
0.617	Remote Similarity	NPD9508	Approved
0.6169	Remote Similarity	NPD829	Discontinued
0.6164	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD1161	Approved
0.6163	Remote Similarity	NPD4652	Approved
0.6159	Remote Similarity	NPD7451	Discontinued
0.6159	Remote Similarity	NPD859	Approved
0.6159	Remote Similarity	NPD858	Approved
0.6154	Remote Similarity	NPD3052	Approved
0.6154	Remote Similarity	NPD3054	Approved
0.6154	Remote Similarity	NPD2568	Approved
0.6149	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5156	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