NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	440.94
Volume:	296.23
LogP:	-0.849
LogD:	0.219
LogS:	0.383
# Rotatable Bonds:	5
TPSA:	49.36
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	3.81
Fsp3:	0.462
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:	-5.25
MDCK Permeability:	3.506217763060704e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.731
20% Bioavailability (F20%):	0.915
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.278
Plasma Protein Binding (PPB):	14.473283767700195%
Volume Distribution (VD):	0.733
Pgp-substrate:	79.9073486328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.401
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.51
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	2.383
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.633
Drug-inuced Liver Injury (DILI):	0.021
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.017
Carcinogencity:	0.057
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC40321

Natural Product ID:	NPC40321
*Common Name:**	Purpuroine H
IUPAC Name:	(2R)-3-(3-bromo-5-iodo-4-methoxyphenyl)-2-(trimethylazaniumyl)propanoate
Synonyms:	Purpuroine H
Standard InCHIKey:	YVFRPWMJWCFFSL-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C13H17BrINO3/c1-16(2,3)11(13(17)18)7-8-5-9(14)12(19-4)10(15)6-8/h5-6,11H,7H2,1-4H3/t11-/m1/s1
SMILES:	C[N+](C)(C)[C@H](Cc1cc(c(c(c1)I)OC)Br)C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204072
PubChem CID:	71459442
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:0004321] Phenylalanine 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	3

Activity Type	# Activity
Individual Protein	3

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[541691]
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	7.91	ug.mL-1	PMID[541691]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	=	7.54	ug.mL-1	PMID[541691]

☑ 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 NPC40321 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	231
0.1-0.2	2095
0.2-0.3	9638
0.3-0.4	9122
0.4-0.5	12845
0.5-0.6	8172
0.6-0.7	532
0.7-0.8	57
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8931	High Similarity	NPC124776
0.8913	High Similarity	NPC470709
0.8889	High Similarity	NPC243404
0.7883	Intermediate Similarity	NPC116562
0.7868	Intermediate Similarity	NPC56634
0.7842	Intermediate Similarity	NPC110131
0.7817	Intermediate Similarity	NPC70485
0.7606	Intermediate Similarity	NPC280736
0.7517	Intermediate Similarity	NPC470392
0.75	Intermediate Similarity	NPC195902
0.7417	Intermediate Similarity	NPC308571
0.7273	Intermediate Similarity	NPC272463
0.7261	Intermediate Similarity	NPC47672
0.7233	Intermediate Similarity	NPC233926
0.7226	Intermediate Similarity	NPC71629
0.7226	Intermediate Similarity	NPC296085
0.7219	Intermediate Similarity	NPC128877
0.72	Intermediate Similarity	NPC470248
0.72	Intermediate Similarity	NPC470249
0.7184	Intermediate Similarity	NPC248822
0.7163	Intermediate Similarity	NPC180207
0.7143	Intermediate Similarity	NPC1065
0.7143	Intermediate Similarity	NPC317784
0.7143	Intermediate Similarity	NPC142638
0.7143	Intermediate Similarity	NPC135349
0.7124	Intermediate Similarity	NPC474128
0.7105	Intermediate Similarity	NPC470250
0.7105	Intermediate Similarity	NPC326860
0.7105	Intermediate Similarity	NPC259800
0.7105	Intermediate Similarity	NPC282087
0.7105	Intermediate Similarity	NPC197239
0.7105	Intermediate Similarity	NPC317741
0.7105	Intermediate Similarity	NPC328137
0.7105	Intermediate Similarity	NPC318984
0.7105	Intermediate Similarity	NPC318028
0.7105	Intermediate Similarity	NPC241086
0.7092	Intermediate Similarity	NPC239697
0.7089	Intermediate Similarity	NPC258222
0.707	Intermediate Similarity	NPC324081
0.7063	Intermediate Similarity	NPC142577
0.7039	Intermediate Similarity	NPC474673
0.702	Intermediate Similarity	NPC470471
0.7007	Intermediate Similarity	NPC122359
0.7007	Intermediate Similarity	NPC159987
0.7007	Intermediate Similarity	NPC78061
0.7006	Intermediate Similarity	NPC477255
0.6985	Remote Similarity	NPC234639
0.6972	Remote Similarity	NPC319950
0.6943	Remote Similarity	NPC9373
0.6941	Remote Similarity	NPC143450
0.6939	Remote Similarity	NPC476353
0.6937	Remote Similarity	NPC469711
0.6933	Remote Similarity	NPC474753
0.6928	Remote Similarity	NPC470470
0.6923	Remote Similarity	NPC184632
0.6918	Remote Similarity	NPC214239
0.6918	Remote Similarity	NPC76412
0.6917	Remote Similarity	NPC298224
0.6913	Remote Similarity	NPC135173
0.6912	Remote Similarity	NPC97811
0.6908	Remote Similarity	NPC235633
0.6903	Remote Similarity	NPC66518
0.6892	Remote Similarity	NPC296712
0.6887	Remote Similarity	NPC266425
0.6879	Remote Similarity	NPC188867
0.6879	Remote Similarity	NPC281686
0.6879	Remote Similarity	NPC106551
0.6875	Remote Similarity	NPC109968
0.687	Remote Similarity	NPC322598
0.6868	Remote Similarity	NPC473450
0.6867	Remote Similarity	NPC45191
0.6867	Remote Similarity	NPC11449
0.6866	Remote Similarity	NPC38209
0.6861	Remote Similarity	NPC259554
0.6835	Remote Similarity	NPC189908
0.6815	Remote Similarity	NPC78530
0.681	Remote Similarity	NPC156311
0.6806	Remote Similarity	NPC321133
0.68	Remote Similarity	NPC474087
0.6795	Remote Similarity	NPC204546
0.6786	Remote Similarity	NPC109241
0.6786	Remote Similarity	NPC26524
0.6768	Remote Similarity	NPC319320
0.6768	Remote Similarity	NPC287757
0.6743	Remote Similarity	NPC477254
0.6733	Remote Similarity	NPC283079
0.6732	Remote Similarity	NPC303993
0.6726	Remote Similarity	NPC473502
0.6712	Remote Similarity	NPC27581
0.6709	Remote Similarity	NPC142803
0.6709	Remote Similarity	NPC81026
0.6709	Remote Similarity	NPC470472
0.6707	Remote Similarity	NPC472923
0.6691	Remote Similarity	NPC473855
0.6691	Remote Similarity	NPC42383
0.6691	Remote Similarity	NPC476198
0.6688	Remote Similarity	NPC196708
0.6687	Remote Similarity	NPC235033
0.6687	Remote Similarity	NPC73132
0.6687	Remote Similarity	NPC471235
0.6667	Remote Similarity	NPC293424
0.6667	Remote Similarity	NPC59387
0.6647	Remote Similarity	NPC196091
0.6646	Remote Similarity	NPC266741
0.6646	Remote Similarity	NPC470247
0.6644	Remote Similarity	NPC326079
0.6624	Remote Similarity	NPC81137
0.6623	Remote Similarity	NPC478147
0.662	Remote Similarity	NPC115803
0.6606	Remote Similarity	NPC56635
0.6603	Remote Similarity	NPC225745
0.6603	Remote Similarity	NPC213471
0.6603	Remote Similarity	NPC194359
0.6603	Remote Similarity	NPC471237
0.6603	Remote Similarity	NPC28641
0.6603	Remote Similarity	NPC177967
0.6601	Remote Similarity	NPC259017
0.66	Remote Similarity	NPC218323
0.6599	Remote Similarity	NPC474862
0.6599	Remote Similarity	NPC7830
0.6593	Remote Similarity	NPC475843
0.6588	Remote Similarity	NPC186617
0.6585	Remote Similarity	NPC470710
0.6584	Remote Similarity	NPC132771
0.6573	Remote Similarity	NPC220540
0.6573	Remote Similarity	NPC8093
0.6573	Remote Similarity	NPC51345
0.6573	Remote Similarity	NPC121571
0.6571	Remote Similarity	NPC475120
0.6569	Remote Similarity	NPC238115
0.6564	Remote Similarity	NPC470088
0.6561	Remote Similarity	NPC197766
0.6561	Remote Similarity	NPC471236
0.6554	Remote Similarity	NPC298486
0.6554	Remote Similarity	NPC296202
0.6552	Remote Similarity	NPC205502
0.655	Remote Similarity	NPC473693
0.655	Remote Similarity	NPC471568
0.6541	Remote Similarity	NPC138438
0.6541	Remote Similarity	NPC908
0.6538	Remote Similarity	NPC471338
0.6538	Remote Similarity	NPC474678
0.6536	Remote Similarity	NPC257390
0.6536	Remote Similarity	NPC80337
0.6533	Remote Similarity	NPC320242
0.6525	Remote Similarity	NPC269340
0.6525	Remote Similarity	NPC23332
0.6525	Remote Similarity	NPC21890
0.6524	Remote Similarity	NPC39431
0.6522	Remote Similarity	NPC17760
0.6514	Remote Similarity	NPC475421
0.6513	Remote Similarity	NPC325651
0.651	Remote Similarity	NPC105999
0.6509	Remote Similarity	NPC158900
0.6507	Remote Similarity	NPC43275
0.6503	Remote Similarity	NPC178097
0.6494	Remote Similarity	NPC88667
0.6494	Remote Similarity	NPC118419
0.6494	Remote Similarity	NPC244866
0.6491	Remote Similarity	NPC469505
0.6486	Remote Similarity	NPC26285
0.648	Remote Similarity	NPC259071
0.648	Remote Similarity	NPC77435
0.6475	Remote Similarity	NPC186469
0.6474	Remote Similarity	NPC109580
0.6474	Remote Similarity	NPC180647
0.6471	Remote Similarity	NPC474091
0.6471	Remote Similarity	NPC307425
0.6467	Remote Similarity	NPC213414
0.6464	Remote Similarity	NPC230539
0.6463	Remote Similarity	NPC469540
0.6463	Remote Similarity	NPC469539
0.6458	Remote Similarity	NPC322358
0.6457	Remote Similarity	NPC475976
0.6454	Remote Similarity	NPC183648
0.6454	Remote Similarity	NPC473809
0.6453	Remote Similarity	NPC474858
0.6452	Remote Similarity	NPC132308
0.6452	Remote Similarity	NPC163810
0.6448	Remote Similarity	NPC65714
0.6448	Remote Similarity	NPC473941
0.6437	Remote Similarity	NPC475688
0.6433	Remote Similarity	NPC307682
0.6433	Remote Similarity	NPC106606
0.6429	Remote Similarity	NPC473724
0.6423	Remote Similarity	NPC179686
0.642	Remote Similarity	NPC469978
0.6415	Remote Similarity	NPC189724
0.6415	Remote Similarity	NPC212850
0.6415	Remote Similarity	NPC83289
0.6414	Remote Similarity	NPC470860
0.6414	Remote Similarity	NPC19290
0.6408	Remote Similarity	NPC166837
0.6408	Remote Similarity	NPC233238
0.6404	Remote Similarity	NPC470903
0.6404	Remote Similarity	NPC167763
0.6404	Remote Similarity	NPC470112
0.6403	Remote Similarity	NPC176971
0.6403	Remote Similarity	NPC326447
0.64	Remote Similarity	NPC211218

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 NPC40321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	777
0.2-0.3	1371
0.3-0.4	2399
0.4-0.5	2633
0.5-0.6	1528
0.6-0.7	265
0.7-0.8	15
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
0.7746	Intermediate Similarity	NPD9718	Approved
0.7622	Intermediate Similarity	NPD5746	Approved
0.7518	Intermediate Similarity	NPD196	Phase 1
0.7517	Intermediate Similarity	NPD5745	Approved
0.7211	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1536	Approved
0.72	Intermediate Similarity	NPD1521	Approved
0.72	Intermediate Similarity	NPD1520	Approved
0.7197	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1537	Approved
0.7105	Intermediate Similarity	NPD1522	Approved
0.7105	Intermediate Similarity	NPD1538	Phase 1
0.7105	Intermediate Similarity	NPD2239	Approved
0.7105	Intermediate Similarity	NPD1519	Approved
0.7105	Intermediate Similarity	NPD1523	Approved
0.7105	Intermediate Similarity	NPD2240	Approved
0.702	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5688	Approved
0.6974	Remote Similarity	NPD5689	Approved
0.6968	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3140	Approved
0.6887	Remote Similarity	NPD3142	Approved
0.6879	Remote Similarity	NPD9568	Approved
0.6875	Remote Similarity	NPD7131	Phase 3
0.6857	Remote Similarity	NPD595	Approved
0.6857	Remote Similarity	NPD593	Approved
0.6849	Remote Similarity	NPD1420	Approved
0.6849	Remote Similarity	NPD1421	Approved
0.6842	Remote Similarity	NPD4618	Approved
0.6842	Remote Similarity	NPD4622	Approved
0.6839	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6390	Discontinued
0.6806	Remote Similarity	NPD2667	Approved
0.6806	Remote Similarity	NPD2668	Approved
0.6795	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1894	Discontinued
0.6774	Remote Similarity	NPD4477	Approved
0.6774	Remote Similarity	NPD4476	Approved
0.677	Remote Similarity	NPD1670	Discontinued
0.6768	Remote Similarity	NPD5355	Approved
0.6768	Remote Similarity	NPD5356	Approved
0.6733	Remote Similarity	NPD2614	Approved
0.6711	Remote Similarity	NPD7018	Phase 2
0.6708	Remote Similarity	NPD2184	Approved
0.6708	Remote Similarity	NPD2183	Approved
0.6707	Remote Similarity	NPD6385	Approved
0.6707	Remote Similarity	NPD6386	Approved
0.669	Remote Similarity	NPD256	Approved
0.669	Remote Similarity	NPD255	Approved
0.6646	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3847	Discontinued
0.6643	Remote Similarity	NPD3596	Phase 2
0.6622	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2897	Discontinued
0.6581	Remote Similarity	NPD2653	Approved
0.6579	Remote Similarity	NPD5163	Phase 2
0.6579	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3640	Phase 3
0.6564	Remote Similarity	NPD3639	Approved
0.6564	Remote Similarity	NPD3641	Approved
0.6556	Remote Similarity	NPD2237	Approved
0.6552	Remote Similarity	NPD6581	Approved
0.6552	Remote Similarity	NPD6580	Approved
0.655	Remote Similarity	NPD7608	Discontinued
0.6543	Remote Similarity	NPD3146	Approved
0.6543	Remote Similarity	NPD3536	Discontinued
0.6543	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2654	Approved
0.6538	Remote Similarity	NPD743	Approved
0.6533	Remote Similarity	NPD1819	Approved
0.6533	Remote Similarity	NPD1820	Approved
0.6533	Remote Similarity	NPD1818	Approved
0.6533	Remote Similarity	NPD1817	Approved
0.6533	Remote Similarity	NPD1318	Phase 2
0.6527	Remote Similarity	NPD7972	Discontinued
0.6522	Remote Similarity	NPD6666	Approved
0.6522	Remote Similarity	NPD6667	Approved
0.6507	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD2595	Approved
0.6507	Remote Similarity	NPD2594	Approved
0.6506	Remote Similarity	NPD6873	Phase 2
0.6506	Remote Similarity	NPD6677	Suspended
0.6494	Remote Similarity	NPD2245	Discovery
0.6494	Remote Similarity	NPD259	Phase 1
0.6486	Remote Similarity	NPD1535	Discovery
0.6479	Remote Similarity	NPD2497	Approved
0.6479	Remote Similarity	NPD2496	Approved
0.6478	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6297	Approved
0.6474	Remote Similarity	NPD3054	Approved
0.6474	Remote Similarity	NPD3052	Approved
0.6471	Remote Similarity	NPD3136	Phase 2
0.6467	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2198	Approved
0.6467	Remote Similarity	NPD2199	Approved
0.6463	Remote Similarity	NPD1914	Approved
0.6463	Remote Similarity	NPD7427	Discontinued
0.6458	Remote Similarity	NPD2557	Approved
0.6456	Remote Similarity	NPD6032	Approved
0.6443	Remote Similarity	NPD1481	Phase 2
0.6441	Remote Similarity	NPD1298	Discontinued
0.6438	Remote Similarity	NPD2486	Discontinued
0.6434	Remote Similarity	NPD1241	Discontinued
0.6429	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.641	Remote Similarity	NPD555	Phase 2
0.6407	Remote Similarity	NPD5890	Approved
0.6407	Remote Similarity	NPD5889	Approved
0.6405	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD810	Approved
0.6403	Remote Similarity	NPD812	Approved
0.6403	Remote Similarity	NPD3134	Approved
0.6403	Remote Similarity	NPD811	Approved
0.6402	Remote Similarity	NPD2186	Approved
0.64	Remote Similarity	NPD6582	Phase 2
0.64	Remote Similarity	NPD6583	Phase 3
0.6393	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5236	Approved
0.6383	Remote Similarity	NPD5239	Approved
0.6383	Remote Similarity	NPD5237	Approved
0.6383	Remote Similarity	NPD5235	Approved
0.6383	Remote Similarity	NPD5240	Approved
0.6382	Remote Similarity	NPD2987	Approved
0.6382	Remote Similarity	NPD2990	Approved
0.6376	Remote Similarity	NPD1281	Approved
0.6364	Remote Similarity	NPD3165	Approved
0.6364	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3166	Approved
0.6364	Remote Similarity	NPD3167	Approved
0.6364	Remote Similarity	NPD3164	Approved
0.6357	Remote Similarity	NPD5373	Approved
0.6357	Remote Similarity	NPD1358	Approved
0.6357	Remote Similarity	NPD5374	Approved
0.6352	Remote Similarity	NPD1725	Approved
0.6347	Remote Similarity	NPD6585	Discontinued
0.6346	Remote Similarity	NPD3109	Approved
0.6346	Remote Similarity	NPD3110	Approved
0.6346	Remote Similarity	NPD2203	Discontinued
0.634	Remote Similarity	NPD9569	Approved
0.6338	Remote Similarity	NPD2201	Approved
0.6333	Remote Similarity	NPD2233	Approved
0.6333	Remote Similarity	NPD6853	Approved
0.6333	Remote Similarity	NPD2232	Approved
0.6333	Remote Similarity	NPD2230	Approved
0.6333	Remote Similarity	NPD6851	Approved
0.6331	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD2200	Suspended
0.6325	Remote Similarity	NPD3686	Approved
0.6325	Remote Similarity	NPD3687	Approved
0.6323	Remote Similarity	NPD5718	Phase 2
0.6322	Remote Similarity	NPD5242	Approved
0.6316	Remote Similarity	NPD1794	Approved
0.631	Remote Similarity	NPD4424	Discontinued
0.631	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3294	Phase 2
0.6303	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2249	Approved
0.6301	Remote Similarity	NPD2247	Approved
0.6301	Remote Similarity	NPD6107	Approved
0.6296	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5967	Approved
0.6291	Remote Similarity	NPD1669	Approved
0.6291	Remote Similarity	NPD6540	Phase 3
0.6291	Remote Similarity	NPD6539	Approved
0.6291	Remote Similarity	NPD2429	Approved
0.6291	Remote Similarity	NPD2428	Approved
0.6291	Remote Similarity	NPD6542	Approved
0.6291	Remote Similarity	NPD6543	Approved
0.6287	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1651	Approved
0.6284	Remote Similarity	NPD6382	Discontinued
0.6282	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4870	Approved
0.6282	Remote Similarity	NPD1423	Approved
0.6275	Remote Similarity	NPD6584	Phase 3
0.6275	Remote Similarity	NPD7905	Discontinued
0.6272	Remote Similarity	NPD6280	Approved
0.6272	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6279	Approved
0.6272	Remote Similarity	NPD7317	Phase 3
0.6266	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6808	Phase 2
0.6264	Remote Similarity	NPD4010	Discontinued
0.6259	Remote Similarity	NPD318	Approved
0.6259	Remote Similarity	NPD317	Approved
0.6259	Remote Similarity	NPD1758	Phase 1
0.6258	Remote Similarity	NPD3179	Approved
0.6258	Remote Similarity	NPD3180	Approved
0.6258	Remote Similarity	NPD9537	Phase 1
0.6258	Remote Similarity	NPD9536	Phase 1
0.6258	Remote Similarity	NPD5241	Discontinued
0.625	Remote Similarity	NPD6541	Approved
0.625	Remote Similarity	NPD2607	Approved
0.625	Remote Similarity	NPD6538	Approved
0.625	Remote Similarity	NPD1283	Approved
0.625	Remote Similarity	NPD6875	Approved
0.625	Remote Similarity	NPD5667	Approved
0.625	Remote Similarity	NPD6876	Approved
0.625	Remote Similarity	NPD3175	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