NPASS Compound

Structure

NPC50562 OpenBabel07101719242D 26 27 0 0 0 0 0 0 0 0999 V2000 7.7372 -5.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6032 -3.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 -2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 -3.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0052 -2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2731 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 -1.7601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.1391 0.0878 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 2.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7372 -4.4122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 -0.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 7 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 22 1 0 0 0 0 8 24 1 0 0 0 0 9 26 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 13 1 0 0 0 0 11 15 2 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 23 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.91
Volume:	401.367
LogP:	4.508
LogD:	3.963
LogS:	-5.519
# Rotatable Bonds:	10
TPSA:	57.36
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	2.669
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	1.768145739333704e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.761
Plasma Protein Binding (PPB):	89.75798797607422%
Volume Distribution (VD):	2.237
Pgp-substrate:	12.434471130371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.912
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.487
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.627
CYP2D6-inhibitor:	0.955
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.834
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	4.619
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.912
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.625
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.528
Carcinogencity:	0.162
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.671

Download Data

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

Natural Product: NPC50562

Natural Product ID:	NPC50562
*Common Name:**	Agelanesin D
IUPAC Name:	4,5-dibromo-N-[3-[4-[2-(dimethylamino)ethyl]-2-iodophenoxy]propyl]-1H-pyrrole-2-carboxamide
Synonyms:	Agelanesin D
Standard InCHIKey:	CCGQVOAULLCHMD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H22Br2IN3O2/c1-24(2)8-6-12-4-5-16(14(21)10-12)26-9-3-7-22-18(25)15-11-13(19)17(20)23-15/h4-5,10-11,23H,3,6-9H2,1-2H3,(H,22,25)
SMILES:	CN(CCc1ccc(c(c1)I)OCCCNC(=O)c1[nH]c(c(c1)Br)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598109
PubChem CID:	46232061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO33334	agelas sponges	Species	Agelasidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[20061160]

☑ 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	1
MIC	1
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	-2.3	%	PMID[496612]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	13060.0	nM	PMID[496612]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	33000.0	nM	PMID[496612]

☑ 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 NPC50562 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	436
0.1-0.2	5314
0.2-0.3	11934
0.3-0.4	8439
0.4-0.5	11763
0.5-0.6	3678
0.6-0.7	1067
0.7-0.8	60
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC67658
0.9492	High Similarity	NPC168209
0.9254	High Similarity	NPC243633
0.9254	High Similarity	NPC175150
0.7907	Intermediate Similarity	NPC323969
0.7658	Intermediate Similarity	NPC194740
0.7523	Intermediate Similarity	NPC305984
0.7409	Intermediate Similarity	NPC303658
0.7378	Intermediate Similarity	NPC118559
0.7378	Intermediate Similarity	NPC304307
0.7378	Intermediate Similarity	NPC124920
0.7378	Intermediate Similarity	NPC34580
0.7368	Intermediate Similarity	NPC284888
0.7345	Intermediate Similarity	NPC471762
0.7345	Intermediate Similarity	NPC66777
0.7345	Intermediate Similarity	NPC100547
0.7336	Intermediate Similarity	NPC245055
0.7336	Intermediate Similarity	NPC33064
0.7325	Intermediate Similarity	NPC196718
0.7318	Intermediate Similarity	NPC322064
0.7313	Intermediate Similarity	NPC95240
0.7313	Intermediate Similarity	NPC322135
0.7313	Intermediate Similarity	NPC223409
0.7301	Intermediate Similarity	NPC261251
0.7281	Intermediate Similarity	NPC14288
0.7257	Intermediate Similarity	NPC214142
0.7249	Intermediate Similarity	NPC102593
0.7249	Intermediate Similarity	NPC321592
0.7249	Intermediate Similarity	NPC54803
0.7229	Intermediate Similarity	NPC272549
0.7195	Intermediate Similarity	NPC477979
0.7189	Intermediate Similarity	NPC249583
0.717	Intermediate Similarity	NPC74153
0.7168	Intermediate Similarity	NPC122436
0.7163	Intermediate Similarity	NPC295898
0.7162	Intermediate Similarity	NPC148183
0.7162	Intermediate Similarity	NPC152768
0.7156	Intermediate Similarity	NPC198503
0.7155	Intermediate Similarity	NPC181081
0.7149	Intermediate Similarity	NPC157931
0.7149	Intermediate Similarity	NPC257851
0.711	Intermediate Similarity	NPC321428
0.711	Intermediate Similarity	NPC4687
0.711	Intermediate Similarity	NPC270918
0.7101	Intermediate Similarity	NPC295158
0.7094	Intermediate Similarity	NPC101350
0.7094	Intermediate Similarity	NPC82472
0.7089	Intermediate Similarity	NPC473814
0.7089	Intermediate Similarity	NPC78767
0.7068	Intermediate Similarity	NPC260041
0.7064	Intermediate Similarity	NPC472286
0.7064	Intermediate Similarity	NPC472287
0.7061	Intermediate Similarity	NPC21638
0.7054	Intermediate Similarity	NPC223189
0.7051	Intermediate Similarity	NPC235685
0.7051	Intermediate Similarity	NPC184680
0.7035	Intermediate Similarity	NPC472099
0.7028	Intermediate Similarity	NPC473821
0.7027	Intermediate Similarity	NPC310211
0.7027	Intermediate Similarity	NPC308137
0.7021	Intermediate Similarity	NPC470784
0.7021	Intermediate Similarity	NPC470785
0.7019	Intermediate Similarity	NPC241025
0.7009	Intermediate Similarity	NPC74969
0.7	Intermediate Similarity	NPC2414
0.6995	Remote Similarity	NPC93390
0.6986	Remote Similarity	NPC45190
0.6986	Remote Similarity	NPC82053
0.6983	Remote Similarity	NPC260434
0.6982	Remote Similarity	NPC87413
0.6982	Remote Similarity	NPC146418
0.698	Remote Similarity	NPC216369
0.6971	Remote Similarity	NPC84478
0.696	Remote Similarity	NPC150239
0.6953	Remote Similarity	NPC279189
0.6953	Remote Similarity	NPC200553
0.6951	Remote Similarity	NPC264176
0.6947	Remote Similarity	NPC473041
0.6936	Remote Similarity	NPC162002
0.6926	Remote Similarity	NPC478078
0.692	Remote Similarity	NPC477586
0.692	Remote Similarity	NPC477585
0.692	Remote Similarity	NPC477588
0.692	Remote Similarity	NPC477590
0.6909	Remote Similarity	NPC300156
0.6903	Remote Similarity	NPC169402
0.6898	Remote Similarity	NPC472284
0.6894	Remote Similarity	NPC174489
0.6889	Remote Similarity	NPC116238
0.6886	Remote Similarity	NPC225279
0.6881	Remote Similarity	NPC471944
0.6878	Remote Similarity	NPC37268
0.6872	Remote Similarity	NPC247803
0.6872	Remote Similarity	NPC46561
0.6869	Remote Similarity	NPC142688
0.6867	Remote Similarity	NPC115595
0.6857	Remote Similarity	NPC476423
0.6856	Remote Similarity	NPC280799
0.6854	Remote Similarity	NPC243716
0.6854	Remote Similarity	NPC92111
0.6842	Remote Similarity	NPC208084
0.6842	Remote Similarity	NPC288987
0.6835	Remote Similarity	NPC329747
0.6835	Remote Similarity	NPC26641
0.6835	Remote Similarity	NPC477587
0.6835	Remote Similarity	NPC477589
0.683	Remote Similarity	NPC187501
0.6829	Remote Similarity	NPC80528
0.6824	Remote Similarity	NPC311906
0.682	Remote Similarity	NPC72211
0.6812	Remote Similarity	NPC54066
0.681	Remote Similarity	NPC319232
0.681	Remote Similarity	NPC24370
0.6809	Remote Similarity	NPC473186
0.6808	Remote Similarity	NPC76748
0.6806	Remote Similarity	NPC77061
0.6798	Remote Similarity	NPC96321
0.6791	Remote Similarity	NPC307963
0.6789	Remote Similarity	NPC477004
0.6789	Remote Similarity	NPC18487
0.6786	Remote Similarity	NPC269367
0.6786	Remote Similarity	NPC471304
0.6778	Remote Similarity	NPC37152
0.6777	Remote Similarity	NPC133003
0.6771	Remote Similarity	NPC39679
0.6771	Remote Similarity	NPC475910
0.677	Remote Similarity	NPC471080
0.677	Remote Similarity	NPC469592
0.6763	Remote Similarity	NPC316224
0.6762	Remote Similarity	NPC176127
0.6761	Remote Similarity	NPC296527
0.6753	Remote Similarity	NPC144452
0.6753	Remote Similarity	NPC220851
0.6751	Remote Similarity	NPC39370
0.675	Remote Similarity	NPC27296
0.6741	Remote Similarity	NPC174758
0.6739	Remote Similarity	NPC174760
0.6739	Remote Similarity	NPC128115
0.6734	Remote Similarity	NPC474236
0.6728	Remote Similarity	NPC70259
0.6728	Remote Similarity	NPC79356
0.6728	Remote Similarity	NPC102592
0.6727	Remote Similarity	NPC232727
0.6721	Remote Similarity	NPC303374
0.6714	Remote Similarity	NPC184932
0.6714	Remote Similarity	NPC472861
0.6713	Remote Similarity	NPC19342
0.671	Remote Similarity	NPC60621
0.67	Remote Similarity	NPC206148
0.6698	Remote Similarity	NPC138370
0.6696	Remote Similarity	NPC269270
0.6696	Remote Similarity	NPC298436
0.6696	Remote Similarity	NPC39500
0.6695	Remote Similarity	NPC474688
0.6695	Remote Similarity	NPC6786
0.6695	Remote Similarity	NPC179287
0.6682	Remote Similarity	NPC205934
0.6682	Remote Similarity	NPC121772
0.6682	Remote Similarity	NPC43787
0.6681	Remote Similarity	NPC478141
0.6681	Remote Similarity	NPC475635
0.6681	Remote Similarity	NPC27041
0.668	Remote Similarity	NPC244543
0.6667	Remote Similarity	NPC258048
0.6667	Remote Similarity	NPC162484
0.6667	Remote Similarity	NPC127085
0.6667	Remote Similarity	NPC131486
0.6667	Remote Similarity	NPC474383
0.6667	Remote Similarity	NPC14686
0.6667	Remote Similarity	NPC16066
0.6667	Remote Similarity	NPC63571
0.6653	Remote Similarity	NPC91868
0.6653	Remote Similarity	NPC63971
0.6653	Remote Similarity	NPC477549
0.6652	Remote Similarity	NPC118940
0.6652	Remote Similarity	NPC174576
0.6652	Remote Similarity	NPC469717
0.6652	Remote Similarity	NPC469594
0.6652	Remote Similarity	NPC9635
0.6652	Remote Similarity	NPC472098
0.6652	Remote Similarity	NPC183777
0.6651	Remote Similarity	NPC324091
0.6651	Remote Similarity	NPC251090
0.6651	Remote Similarity	NPC13880
0.6639	Remote Similarity	NPC475816
0.6639	Remote Similarity	NPC323752
0.6639	Remote Similarity	NPC473105
0.6638	Remote Similarity	NPC187145
0.6637	Remote Similarity	NPC123839
0.6637	Remote Similarity	NPC285558
0.6636	Remote Similarity	NPC310633
0.6635	Remote Similarity	NPC243381
0.6635	Remote Similarity	NPC275292
0.6632	Remote Similarity	NPC150592
0.6626	Remote Similarity	NPC165964
0.6623	Remote Similarity	NPC236668
0.6622	Remote Similarity	NPC291535
0.6622	Remote Similarity	NPC475112
0.6622	Remote Similarity	NPC287208
0.6622	Remote Similarity	NPC475085

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 NPC50562 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	726
0.2-0.3	864
0.3-0.4	1404
0.4-0.5	2890
0.5-0.6	2492
0.6-0.7	521
0.7-0.8	19
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
0.7557	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD5632	Approved
0.7385	Intermediate Similarity	NPD3945	Discontinued
0.7352	Intermediate Similarity	NPD5293	Phase 2
0.7304	Intermediate Similarity	NPD7853	Phase 2
0.7265	Intermediate Similarity	NPD7180	Phase 3
0.726	Intermediate Similarity	NPD5866	Approved
0.7237	Intermediate Similarity	NPD5479	Discontinued
0.72	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7994	Phase 2
0.7137	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3263	Phase 3
0.7087	Intermediate Similarity	NPD1659	Phase 1
0.7078	Intermediate Similarity	NPD6376	Discontinued
0.7071	Intermediate Similarity	NPD4558	Phase 2
0.7064	Intermediate Similarity	NPD8403	Phase 1
0.7051	Intermediate Similarity	NPD5513	Phase 2
0.7035	Intermediate Similarity	NPD6242	Discontinued
0.7035	Intermediate Similarity	NPD1996	Discontinued
0.7026	Intermediate Similarity	NPD4885	Approved
0.7023	Intermediate Similarity	NPD1768	Approved
0.7017	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6209	Approved
0.6966	Remote Similarity	NPD2951	Discontinued
0.694	Remote Similarity	NPD4952	Phase 3
0.6933	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7467	Discontinued
0.6916	Remote Similarity	NPD6974	Phase 3
0.6912	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3003	Approved
0.6907	Remote Similarity	NPD4368	Phase 2
0.6907	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5482	Discontinued
0.6872	Remote Similarity	NPD6568	Discontinued
0.6867	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3825	Phase 3
0.6864	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4373	Phase 2
0.6847	Remote Similarity	NPD5658	Approved
0.684	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5601	Phase 2
0.6833	Remote Similarity	NPD4130	Phase 3
0.6825	Remote Similarity	NPD5256	Discontinued
0.6824	Remote Similarity	NPD5559	Phase 2
0.6822	Remote Similarity	NPD4372	Phase 1
0.6818	Remote Similarity	NPD6176	Phase 1
0.6812	Remote Similarity	NPD8479	Phase 2
0.681	Remote Similarity	NPD5640	Discontinued
0.6807	Remote Similarity	NPD4314	Approved
0.6807	Remote Similarity	NPD4313	Approved
0.6802	Remote Similarity	NPD1392	Approved
0.6798	Remote Similarity	NPD5948	Phase 2
0.6794	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1038	Approved
0.6791	Remote Similarity	NPD4539	Phase 1
0.6789	Remote Similarity	NPD2778	Approved
0.6787	Remote Similarity	NPD3947	Discontinued
0.6786	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3392	Approved
0.6781	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2510	Approved
0.6771	Remote Similarity	NPD2509	Approved
0.6761	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3395	Approved
0.6759	Remote Similarity	NPD3396	Approved
0.6756	Remote Similarity	NPD5066	Phase 2
0.6756	Remote Similarity	NPD5067	Phase 2
0.6756	Remote Similarity	NPD5416	Discontinued
0.6753	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5014	Discontinued
0.6747	Remote Similarity	NPD5116	Phase 1
0.6742	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7031	Phase 1
0.6736	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3569	Discontinued
0.6723	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6716	Phase 1
0.6722	Remote Similarity	NPD4322	Discontinued
0.6714	Remote Similarity	NPD4203	Approved
0.6714	Remote Similarity	NPD4204	Approved
0.6713	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4309	Approved
0.6698	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD2779	Approved
0.6682	Remote Similarity	NPD4418	Discontinued
0.668	Remote Similarity	NPD6790	Phase 1
0.6667	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5850	Phase 3
0.6667	Remote Similarity	NPD5903	Approved
0.6667	Remote Similarity	NPD5902	Approved
0.6667	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD1096	Discontinued
0.6651	Remote Similarity	NPD4072	Approved
0.6651	Remote Similarity	NPD4071	Approved
0.665	Remote Similarity	NPD5186	Approved
0.665	Remote Similarity	NPD5183	Approved
0.6638	Remote Similarity	NPD3389	Approved
0.6638	Remote Similarity	NPD5612	Discontinued
0.6638	Remote Similarity	NPD3393	Approved
0.6638	Remote Similarity	NPD3394	Approved
0.6636	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7194	Discontinued
0.6621	Remote Similarity	NPD2952	Discontinued
0.662	Remote Similarity	NPD4889	Approved
0.6605	Remote Similarity	NPD4021	Phase 2
0.6598	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4847	Phase 1
0.6594	Remote Similarity	NPD1638	Discovery
0.6594	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD772	Phase 3
0.659	Remote Similarity	NPD6569	Phase 2
0.6584	Remote Similarity	NPD7022	Phase 2
0.6583	Remote Similarity	NPD3006	Discontinued
0.6582	Remote Similarity	NPD5924	Discontinued
0.6575	Remote Similarity	NPD5512	Phase 3
0.6575	Remote Similarity	NPD5450	Discontinued
0.657	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3259	Approved
0.6567	Remote Similarity	NPD4923	Phase 1
0.6562	Remote Similarity	NPD3397	Phase 2
0.6561	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4548	Discontinued
0.6557	Remote Similarity	NPD3178	Discontinued
0.6555	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5139	Phase 1
0.6555	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1867	Approved
0.6553	Remote Similarity	NPD4890	Phase 2
0.6548	Remote Similarity	NPD7708	Approved
0.6546	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8311	Discontinued
0.6537	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3507	Phase 2
0.653	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8289	Discontinued
0.6524	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3257	Approved
0.6522	Remote Similarity	NPD4897	Phase 2
0.6522	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5149	Phase 2
0.6518	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5022	Discontinued
0.6512	Remote Similarity	NPD7689	Approved
0.651	Remote Similarity	NPD7803	Approved
0.6509	Remote Similarity	NPD7395	Discontinued
0.6509	Remote Similarity	NPD4429	Discontinued
0.6509	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6985	Discontinued
0.6507	Remote Similarity	NPD6202	Discontinued
0.6507	Remote Similarity	NPD7605	Discovery
0.6504	Remote Similarity	NPD6397	Phase 3
0.65	Remote Similarity	NPD2289	Phase 3
0.65	Remote Similarity	NPD2290	Phase 3
0.65	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD7588	Discontinued
0.6492	Remote Similarity	NPD6475	Phase 2
0.649	Remote Similarity	NPD565	Phase 2
0.6481	Remote Similarity	NPD2884	Phase 1
0.6481	Remote Similarity	NPD3258	Approved
0.6481	Remote Similarity	NPD6770	Approved
0.648	Remote Similarity	NPD8463	Approved
0.6475	Remote Similarity	NPD5273	Approved
0.6475	Remote Similarity	NPD5271	Approved
0.6473	Remote Similarity	NPD7316	Discontinued
0.6471	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1630	Approved
0.6466	Remote Similarity	NPD4989	Phase 2
0.6458	Remote Similarity	NPD7796	Approved
0.6458	Remote Similarity	NPD7797	Approved
0.6457	Remote Similarity	NPD4501	Approved
0.6457	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4500	Approved
0.6456	Remote Similarity	NPD7426	Phase 1
0.6456	Remote Similarity	NPD7603	Discontinued
0.6455	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8102	Discontinued
0.6452	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4369	Phase 2
0.6452	Remote Similarity	NPD4334	Discontinued
0.645	Remote Similarity	NPD2547	Discontinued
0.6444	Remote Similarity	NPD6991	Approved
0.6443	Remote Similarity	NPD7955	Approved
0.6443	Remote Similarity	NPD7956	Approved
0.6438	Remote Similarity	NPD4376	Phase 3

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