NPASS Compound

Structure

NPC197045 OpenBabel07101719142D 23 23 0 0 0 0 0 0 0 0999 V2000 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 3 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.07
Volume:	326.963
LogP:	0.707
LogD:	-0.069
LogS:	-2.596
# Rotatable Bonds:	10
TPSA:	143.82
# H-Bond Aceptor:	8
# H-Bond Donor:	7
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	2.71
Fsp3:	0.357
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:	-5.741
MDCK Permeability:	9.270904229197185e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.576
20% Bioavailability (F20%):	0.264
30% Bioavailability (F30%):	0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.656
Plasma Protein Binding (PPB):	69.7739028930664%
Volume Distribution (VD):	0.874
Pgp-substrate:	38.7872428894043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.058
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.126
CYP2D6-substrate:	0.347
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	4.531
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.211
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.302
AMES Toxicity:	0.17
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.236
Carcinogencity:	0.224
Eye Corrosion:	0.003
Eye Irritation:	0.009
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: NPC197045

Natural Product ID:	NPC197045
*Common Name:**	Clavatadine E
IUPAC Name:	(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[4-(diaminomethylideneamino)butyl]-2-hydroxyiminopropanamide
Synonyms:	Clavatadine E
Standard InCHIKey:	FHRJNEDPVPOFPW-RGVLZGJSSA-N
Standard InCHI:	InChI=1S/C14H20BrN5O3/c15-10-7-9(3-4-12(10)21)8-11(20-23)13(22)18-5-1-2-6-19-14(16)17/h3-4,7,21,23H,1-2,5-6,8H2,(H,18,22)(H4,16,17,19)/b20-11+
SMILES:	C(CCNC(=N)N)CN=C(/C(=N/O)/Cc1ccc(c(c1)Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL557486
PubChem CID:	44139373
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0002320] Halophenols [CHEMONTID:0002764] Bromophenols [CHEMONTID:0002768] O-bromophenols

*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
NPO13261	Suberea clavata	Species	Aplysinellidae	Eukaryota	n.a.	Australian	n.a.	PMID[19379003]
NPO13261	Suberea clavata	Species	Aplysinellidae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4197	Individual Protein	Coagulation factor XI	Homo sapiens	Inhibition	=	37.0	%	PMID[486344]
NPT4655	Individual Protein	Coagulation factor IX	Homo sapiens	Inhibition	<	5.0	%	PMID[486344]

☑ 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 NPC197045 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	279
0.1-0.2	3318
0.2-0.3	13693
0.3-0.4	9781
0.4-0.5	12771
0.5-0.6	2442
0.6-0.7	355
0.7-0.8	49
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8321	Intermediate Similarity	NPC474091
0.8175	Intermediate Similarity	NPC202776
0.8163	Intermediate Similarity	NPC20755
0.8129	Intermediate Similarity	NPC475735
0.8085	Intermediate Similarity	NPC120114
0.8085	Intermediate Similarity	NPC71888
0.8071	Intermediate Similarity	NPC166624
0.8014	Intermediate Similarity	NPC163810
0.7972	Intermediate Similarity	NPC309667
0.7943	Intermediate Similarity	NPC474753
0.7887	Intermediate Similarity	NPC184465
0.7887	Intermediate Similarity	NPC267237
0.7863	Intermediate Similarity	NPC59387
0.7755	Intermediate Similarity	NPC474128
0.7727	Intermediate Similarity	NPC156311
0.7724	Intermediate Similarity	NPC474587
0.7724	Intermediate Similarity	NPC475132
0.7687	Intermediate Similarity	NPC168861
0.7676	Intermediate Similarity	NPC474087
0.7671	Intermediate Similarity	NPC475293
0.7671	Intermediate Similarity	NPC48202
0.7671	Intermediate Similarity	NPC214988
0.7622	Intermediate Similarity	NPC473724
0.7551	Intermediate Similarity	NPC470470
0.7537	Intermediate Similarity	NPC115803
0.7534	Intermediate Similarity	NPC470471
0.7517	Intermediate Similarity	NPC326241
0.7456	Intermediate Similarity	NPC96275
0.7419	Intermediate Similarity	NPC475432
0.7391	Intermediate Similarity	NPC283760
0.7355	Intermediate Similarity	NPC258222
0.7308	Intermediate Similarity	NPC47672
0.7303	Intermediate Similarity	NPC470472
0.7278	Intermediate Similarity	NPC233926
0.7233	Intermediate Similarity	NPC473738
0.7209	Intermediate Similarity	NPC246591
0.7134	Intermediate Similarity	NPC109968
0.7123	Intermediate Similarity	NPC271808
0.7101	Intermediate Similarity	NPC317254
0.709	Intermediate Similarity	NPC471495
0.7078	Intermediate Similarity	NPC78530
0.707	Intermediate Similarity	NPC76412
0.7068	Intermediate Similarity	NPC231705
0.7054	Intermediate Similarity	NPC107619
0.7037	Intermediate Similarity	NPC258056
0.7037	Intermediate Similarity	NPC123848
0.7029	Intermediate Similarity	NPC118202
0.7006	Intermediate Similarity	NPC80514
0.6985	Remote Similarity	NPC474149
0.6985	Remote Similarity	NPC473358
0.697	Remote Similarity	NPC178902
0.6959	Remote Similarity	NPC99280
0.6929	Remote Similarity	NPC82963
0.6889	Remote Similarity	NPC142297
0.6887	Remote Similarity	NPC303993
0.6879	Remote Similarity	NPC311737
0.6879	Remote Similarity	NPC38458
0.6879	Remote Similarity	NPC477254
0.687	Remote Similarity	NPC125732
0.6857	Remote Similarity	NPC10286
0.6857	Remote Similarity	NPC213
0.6842	Remote Similarity	NPC237227
0.6838	Remote Similarity	NPC153690
0.6838	Remote Similarity	NPC96224
0.6838	Remote Similarity	NPC24101
0.6821	Remote Similarity	NPC243404
0.68	Remote Similarity	NPC326966
0.6788	Remote Similarity	NPC54543
0.6784	Remote Similarity	NPC143450
0.6779	Remote Similarity	NPC325651
0.6759	Remote Similarity	NPC27581
0.6755	Remote Similarity	NPC113369
0.6753	Remote Similarity	NPC474673
0.6753	Remote Similarity	NPC213471
0.6752	Remote Similarity	NPC135349
0.6728	Remote Similarity	NPC473580
0.6726	Remote Similarity	NPC280022
0.6725	Remote Similarity	NPC225130
0.6714	Remote Similarity	NPC309808
0.6713	Remote Similarity	NPC85276
0.6692	Remote Similarity	NPC155847
0.6692	Remote Similarity	NPC289381
0.6687	Remote Similarity	NPC22014
0.6686	Remote Similarity	NPC469979
0.6667	Remote Similarity	NPC145638
0.6667	Remote Similarity	NPC290566
0.6667	Remote Similarity	NPC81845
0.6647	Remote Similarity	NPC110454
0.6647	Remote Similarity	NPC126128
0.6647	Remote Similarity	NPC473462
0.6647	Remote Similarity	NPC191557
0.6647	Remote Similarity	NPC207819
0.6647	Remote Similarity	NPC298981
0.6627	Remote Similarity	NPC129486
0.6622	Remote Similarity	NPC272463
0.6609	Remote Similarity	NPC290534
0.6593	Remote Similarity	NPC68055
0.659	Remote Similarity	NPC226001
0.6588	Remote Similarity	NPC276506
0.6588	Remote Similarity	NPC198254
0.6588	Remote Similarity	NPC274198
0.6566	Remote Similarity	NPC469243
0.6566	Remote Similarity	NPC475544
0.6564	Remote Similarity	NPC469711
0.6552	Remote Similarity	NPC268572
0.6549	Remote Similarity	NPC142599
0.6547	Remote Similarity	NPC473372
0.6541	Remote Similarity	NPC473450
0.6536	Remote Similarity	NPC307123
0.6536	Remote Similarity	NPC247018
0.6536	Remote Similarity	NPC97870
0.6534	Remote Similarity	NPC74618
0.6534	Remote Similarity	NPC301941
0.6534	Remote Similarity	NPC214188
0.6528	Remote Similarity	NPC137096
0.6525	Remote Similarity	NPC146422
0.6516	Remote Similarity	NPC64205
0.6512	Remote Similarity	NPC475532
0.65	Remote Similarity	NPC471487
0.6497	Remote Similarity	NPC128877
0.6492	Remote Similarity	NPC295795
0.6478	Remote Similarity	NPC308571
0.6474	Remote Similarity	NPC165285
0.6474	Remote Similarity	NPC17698
0.6467	Remote Similarity	NPC110131
0.6467	Remote Similarity	NPC476249
0.6463	Remote Similarity	NPC273830
0.6461	Remote Similarity	NPC129885
0.6458	Remote Similarity	NPC106551
0.6458	Remote Similarity	NPC281686
0.6458	Remote Similarity	NPC188867
0.6457	Remote Similarity	NPC119652
0.6457	Remote Similarity	NPC97526
0.6453	Remote Similarity	NPC477255
0.645	Remote Similarity	NPC223207
0.6444	Remote Similarity	NPC29601
0.6441	Remote Similarity	NPC152205
0.6441	Remote Similarity	NPC475283
0.6438	Remote Similarity	NPC38483
0.6438	Remote Similarity	NPC319950
0.6437	Remote Similarity	NPC196243
0.6434	Remote Similarity	NPC94217
0.6433	Remote Similarity	NPC66490
0.6429	Remote Similarity	NPC158078
0.6425	Remote Similarity	NPC49172
0.6425	Remote Similarity	NPC8093
0.6425	Remote Similarity	NPC77435
0.6425	Remote Similarity	NPC259071
0.6425	Remote Similarity	NPC121571
0.6419	Remote Similarity	NPC7830
0.6419	Remote Similarity	NPC474862
0.6414	Remote Similarity	NPC283468
0.6412	Remote Similarity	NPC304074
0.6412	Remote Similarity	NPC290755
0.6412	Remote Similarity	NPC471771
0.64	Remote Similarity	NPC473546
0.6398	Remote Similarity	NPC119569
0.6393	Remote Similarity	NPC474678
0.6393	Remote Similarity	NPC471338
0.6393	Remote Similarity	NPC227953
0.6389	Remote Similarity	NPC144823
0.6384	Remote Similarity	NPC475396
0.6376	Remote Similarity	NPC296202
0.637	Remote Similarity	NPC122009
0.6364	Remote Similarity	NPC471488
0.6364	Remote Similarity	NPC76400
0.6359	Remote Similarity	NPC475843
0.6358	Remote Similarity	NPC318965
0.6354	Remote Similarity	NPC470951
0.6354	Remote Similarity	NPC82741
0.6354	Remote Similarity	NPC473409
0.6354	Remote Similarity	NPC141405
0.6351	Remote Similarity	NPC324702
0.634	Remote Similarity	NPC471306
0.634	Remote Similarity	NPC471321
0.6338	Remote Similarity	NPC166837
0.6335	Remote Similarity	NPC473804
0.6328	Remote Similarity	NPC475409
0.6328	Remote Similarity	NPC170302
0.6328	Remote Similarity	NPC153554
0.6328	Remote Similarity	NPC475564
0.6327	Remote Similarity	NPC239697
0.6327	Remote Similarity	NPC117759
0.6327	Remote Similarity	NPC43275
0.6316	Remote Similarity	NPC236347
0.6316	Remote Similarity	NPC323775
0.6309	Remote Similarity	NPC136543
0.6308	Remote Similarity	NPC25493
0.6308	Remote Similarity	NPC113460
0.6306	Remote Similarity	NPC6570
0.6298	Remote Similarity	NPC475658
0.6298	Remote Similarity	NPC471591
0.6298	Remote Similarity	NPC473892
0.6296	Remote Similarity	NPC315921
0.6292	Remote Similarity	NPC473404
0.6291	Remote Similarity	NPC213414
0.6289	Remote Similarity	NPC476989
0.6289	Remote Similarity	NPC197921
0.6284	Remote Similarity	NPC248822
0.6284	Remote Similarity	NPC180207

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 NPC197045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	642
0.2-0.3	1200
0.3-0.4	2617
0.4-0.5	3507
0.5-0.6	895
0.6-0.7	125
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7568	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7523	Phase 3
0.7075	Intermediate Similarity	NPD9718	Approved
0.7075	Intermediate Similarity	NPD1223	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7451	Discontinued
0.6917	Remote Similarity	NPD9608	Approved
0.6917	Remote Similarity	NPD9610	Approved
0.6914	Remote Similarity	NPD7495	Discontinued
0.6914	Remote Similarity	NPD8019	Approved
0.6879	Remote Similarity	NPD16	Approved
0.6879	Remote Similarity	NPD317	Approved
0.6879	Remote Similarity	NPD856	Approved
0.6879	Remote Similarity	NPD318	Approved
0.6806	Remote Similarity	NPD3421	Phase 3
0.679	Remote Similarity	NPD1009	Approved
0.6733	Remote Similarity	NPD3136	Phase 2
0.6712	Remote Similarity	NPD2561	Approved
0.6712	Remote Similarity	NPD2562	Approved
0.6707	Remote Similarity	NPD8303	Discontinued
0.6689	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5310	Approved
0.6622	Remote Similarity	NPD5311	Approved
0.6582	Remote Similarity	NPD2209	Approved
0.6582	Remote Similarity	NPD2211	Approved
0.6581	Remote Similarity	NPD3553	Approved
0.6581	Remote Similarity	NPD3555	Approved
0.6581	Remote Similarity	NPD3554	Approved
0.6581	Remote Similarity	NPD3552	Approved
0.6579	Remote Similarity	NPD1039	Discontinued
0.6577	Remote Similarity	NPD1131	Approved
0.6577	Remote Similarity	NPD3053	Approved
0.6577	Remote Similarity	NPD1133	Approved
0.6577	Remote Similarity	NPD1129	Approved
0.6577	Remote Similarity	NPD1134	Approved
0.6577	Remote Similarity	NPD1135	Approved
0.6577	Remote Similarity	NPD3055	Approved
0.6554	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2184	Approved
0.6543	Remote Similarity	NPD2183	Approved
0.6538	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1423	Approved
0.6528	Remote Similarity	NPD9613	Approved
0.6528	Remote Similarity	NPD9615	Approved
0.6528	Remote Similarity	NPD9616	Approved
0.6525	Remote Similarity	NPD9377	Approved
0.6525	Remote Similarity	NPD9379	Approved
0.6519	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7450	Phase 2
0.6483	Remote Similarity	NPD316	Approved
0.6479	Remote Similarity	NPD2229	Approved
0.6479	Remote Similarity	NPD2228	Approved
0.6479	Remote Similarity	NPD2234	Approved
0.6458	Remote Similarity	NPD9568	Approved
0.6456	Remote Similarity	NPD7978	Discontinued
0.6449	Remote Similarity	NPD1444	Approved
0.6449	Remote Similarity	NPD1445	Approved
0.6438	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1169	Approved
0.6405	Remote Similarity	NPD2372	Approved
0.64	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD598	Approved
0.6364	Remote Similarity	NPD601	Approved
0.6364	Remote Similarity	NPD597	Approved
0.6351	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7303	Discontinued
0.6329	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD829	Discontinued
0.6323	Remote Similarity	NPD1136	Approved
0.6323	Remote Similarity	NPD1132	Approved
0.6323	Remote Similarity	NPD1130	Approved
0.6319	Remote Similarity	NPD9618	Approved
0.6319	Remote Similarity	NPD9614	Approved
0.6316	Remote Similarity	NPD9619	Approved
0.6316	Remote Similarity	NPD9620	Approved
0.6316	Remote Similarity	NPD9621	Approved
0.6312	Remote Similarity	NPD1792	Phase 2
0.6296	Remote Similarity	NPD9273	Approved
0.6294	Remote Similarity	NPD821	Approved
0.6279	Remote Similarity	NPD9538	Approved
0.6267	Remote Similarity	NPD3070	Discontinued
0.6265	Remote Similarity	NPD5267	Discontinued
0.6259	Remote Similarity	NPD5303	Approved
0.6259	Remote Similarity	NPD5304	Approved
0.6259	Remote Similarity	NPD1759	Phase 1
0.6258	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1983	Approved
0.6242	Remote Similarity	NPD1980	Approved
0.6242	Remote Similarity	NPD1981	Approved
0.623	Remote Similarity	NPD7617	Discontinued
0.6226	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6407	Approved
0.6218	Remote Similarity	NPD6405	Approved
0.6209	Remote Similarity	NPD858	Approved
0.6209	Remote Similarity	NPD859	Approved
0.6209	Remote Similarity	NPD602	Approved
0.6209	Remote Similarity	NPD599	Approved
0.6207	Remote Similarity	NPD593	Approved
0.6207	Remote Similarity	NPD595	Approved
0.6203	Remote Similarity	NPD2568	Approved
0.6203	Remote Similarity	NPD5314	Approved
0.6203	Remote Similarity	NPD817	Approved
0.6203	Remote Similarity	NPD823	Approved
0.6203	Remote Similarity	NPD3052	Approved
0.6203	Remote Similarity	NPD3054	Approved
0.6194	Remote Similarity	NPD2934	Approved
0.6194	Remote Similarity	NPD2933	Approved
0.6193	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1758	Phase 1
0.6187	Remote Similarity	NPD311	Approved
0.6187	Remote Similarity	NPD10	Approved
0.6187	Remote Similarity	NPD310	Approved
0.6187	Remote Similarity	NPD309	Approved
0.6187	Remote Similarity	NPD314	Approved
0.6187	Remote Similarity	NPD315	Approved
0.6182	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD3985	Discontinued
0.6182	Remote Similarity	NPD6419	Discontinued
0.6178	Remote Similarity	NPD3061	Approved
0.6178	Remote Similarity	NPD3059	Approved
0.6178	Remote Similarity	NPD3062	Approved
0.6174	Remote Similarity	NPD9381	Approved
0.6174	Remote Similarity	NPD9384	Approved
0.6174	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD2458	Approved
0.6173	Remote Similarity	NPD2459	Approved
0.6173	Remote Similarity	NPD2460	Phase 3
0.6169	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD256	Approved
0.6164	Remote Similarity	NPD255	Approved
0.6154	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1035	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD2860	Approved
0.6148	Remote Similarity	NPD2859	Approved
0.6145	Remote Similarity	NPD1350	Approved
0.6145	Remote Similarity	NPD1349	Approved
0.6145	Remote Similarity	NPD1351	Approved
0.6144	Remote Similarity	NPD1818	Approved
0.6144	Remote Similarity	NPD1820	Approved
0.6144	Remote Similarity	NPD1817	Approved
0.6144	Remote Similarity	NPD1819	Approved
0.6118	Remote Similarity	NPD4659	Approved
0.6118	Remote Similarity	NPD9622	Approved
0.6107	Remote Similarity	NPD4093	Discontinued
0.6101	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD1791	Approved
0.6096	Remote Similarity	NPD1793	Approved
0.609	Remote Similarity	NPD530	Approved
0.6084	Remote Similarity	NPD9713	Approved
0.6084	Remote Similarity	NPD2874	Phase 2
0.6076	Remote Similarity	NPD6346	Approved
0.6074	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD7342	Discontinued
0.6067	Remote Similarity	NPD1751	Approved
0.6061	Remote Similarity	NPD7554	Discontinued
0.6053	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD1812	Approved
0.6045	Remote Similarity	NPD1814	Approved
0.6042	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.604	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD4103	Phase 2
0.6028	Remote Similarity	NPD414	Discontinued
0.6026	Remote Similarity	NPD3143	Discontinued
0.6024	Remote Similarity	NPD6087	Phase 1
0.6014	Remote Similarity	NPD3020	Approved
0.6013	Remote Similarity	NPD839	Approved
0.6013	Remote Similarity	NPD840	Approved
0.6013	Remote Similarity	NPD2674	Phase 3
0.6012	Remote Similarity	NPD7153	Discontinued
0.6	Remote Similarity	NPD2195	Approved
0.6	Remote Similarity	NPD2194	Approved
0.6	Remote Similarity	NPD111	Approved
0.6	Remote Similarity	NPD1411	Approved
0.6	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5287	Discontinued
0.6	Remote Similarity	NPD8131	Suspended
0.5988	Remote Similarity	NPD3156	Discontinued
0.5987	Remote Similarity	NPD5163	Phase 2
0.5987	Remote Similarity	NPD3164	Approved
0.5987	Remote Similarity	NPD3165	Approved
0.5987	Remote Similarity	NPD3167	Approved
0.5987	Remote Similarity	NPD3166	Approved
0.5976	Remote Similarity	NPD3638	Discontinued
0.5965	Remote Similarity	NPD2469	Approved
0.5965	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD2468	Approved
0.5962	Remote Similarity	NPD9569	Approved
0.596	Remote Similarity	NPD2668	Approved
0.596	Remote Similarity	NPD2667	Approved
0.5952	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD2186	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