NPASS Compound

Structure

NPC98685 OpenBabel07101718292D 21 22 0 0 0 0 0 0 0 0999 V2000 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 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 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 19 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	481.88
Volume:	320.466
LogP:	4.549
LogD:	3.759
LogS:	-5.941
# Rotatable Bonds:	5
TPSA:	26.63
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	3.295
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.675
MDCK Permeability:	1.524449726275634e-05
Pgp-inhibitor:	0.77
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.598
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	95.35033416748047%
Volume Distribution (VD):	1.91
Pgp-substrate:	4.872100353240967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.965
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.903
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	2.252
Half-life (T1/2):	0.217

ADMET: Toxicity

hERG Blockers:	0.825
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.631
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.926
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.314
Carcinogencity:	0.635
Eye Corrosion:	0.009
Eye Irritation:	0.019
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC98685

Natural Product ID:	NPC98685
*Common Name:**	Convolutindole A
IUPAC Name:	N,N-dimethyl-2-(2,4,6-tribromo-1,7-dimethoxyindol-3-yl)ethanamine
Synonyms:
Standard InCHIKey:	KPTXBOJWIDAMOS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H17Br3N2O2/c1-18(2)6-5-8-11-9(15)7-10(16)13(20-3)12(11)19(21-4)14(8)17/h7H,5-6H2,1-4H3
SMILES:	CN(C)CCc1c2c(cc(c(c2n(c1Br)OC)OC)Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447385
PubChem CID:	5324072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines 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
NPO5804	Amathia convoluta	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088445]
NPO5804	Amathia convoluta	Species	Vesiculariidae	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
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6229	Organism	Heteropogon contortus	Heteropogon contortus	LD99	=	0.39	ug ml-1	PMID[538428]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	LD99	=	50.0	ug ml-1	PMID[538428]

☑ 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 NPC98685 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	692
0.1-0.2	7936
0.2-0.3	10043
0.3-0.4	15190
0.4-0.5	5825
0.5-0.6	2595
0.6-0.7	403
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7885	Intermediate Similarity	NPC292958
0.7474	Intermediate Similarity	NPC474798
0.7394	Intermediate Similarity	NPC118511
0.7379	Intermediate Similarity	NPC475774
0.725	Intermediate Similarity	NPC242928
0.7171	Intermediate Similarity	NPC267928
0.7129	Intermediate Similarity	NPC476138
0.7129	Intermediate Similarity	NPC245816
0.7108	Intermediate Similarity	NPC475190
0.7103	Intermediate Similarity	NPC94157
0.7042	Intermediate Similarity	NPC185782
0.7023	Intermediate Similarity	NPC26679
0.7019	Intermediate Similarity	NPC128823
0.7015	Intermediate Similarity	NPC42591
0.701	Intermediate Similarity	NPC92111
0.7	Intermediate Similarity	NPC176127
0.6981	Remote Similarity	NPC476124
0.6981	Remote Similarity	NPC476121
0.6961	Remote Similarity	NPC76748
0.6942	Remote Similarity	NPC307963
0.6934	Remote Similarity	NPC470930
0.6923	Remote Similarity	NPC470250
0.6912	Remote Similarity	NPC296527
0.6909	Remote Similarity	NPC255110
0.6891	Remote Similarity	NPC177404
0.6878	Remote Similarity	NPC132642
0.6852	Remote Similarity	NPC199667
0.6849	Remote Similarity	NPC8022
0.6849	Remote Similarity	NPC470799
0.6849	Remote Similarity	NPC142901
0.6842	Remote Similarity	NPC26872
0.6835	Remote Similarity	NPC476287
0.6818	Remote Similarity	NPC247980
0.6806	Remote Similarity	NPC473181
0.6798	Remote Similarity	NPC84478
0.6794	Remote Similarity	NPC222018
0.6789	Remote Similarity	NPC473180
0.6786	Remote Similarity	NPC167908
0.6766	Remote Similarity	NPC472168
0.6745	Remote Similarity	NPC19872
0.6745	Remote Similarity	NPC329793
0.6714	Remote Similarity	NPC251090
0.6712	Remote Similarity	NPC174576
0.67	Remote Similarity	NPC312872
0.6696	Remote Similarity	NPC473185
0.6682	Remote Similarity	NPC66815
0.6682	Remote Similarity	NPC287208
0.6682	Remote Similarity	NPC473761
0.6667	Remote Similarity	NPC187501
0.6667	Remote Similarity	NPC134586
0.6667	Remote Similarity	NPC223189
0.6667	Remote Similarity	NPC472111
0.6651	Remote Similarity	NPC209769
0.6649	Remote Similarity	NPC26850
0.6634	Remote Similarity	NPC211997
0.663	Remote Similarity	NPC470248
0.6621	Remote Similarity	NPC219664
0.6609	Remote Similarity	NPC475253
0.6607	Remote Similarity	NPC473179
0.6606	Remote Similarity	NPC39500
0.6605	Remote Similarity	NPC470678
0.6589	Remote Similarity	NPC176538
0.6589	Remote Similarity	NPC329747
0.658	Remote Similarity	NPC473186
0.6575	Remote Similarity	NPC469589
0.657	Remote Similarity	NPC204385
0.6567	Remote Similarity	NPC288074
0.6561	Remote Similarity	NPC203168
0.6552	Remote Similarity	NPC329631
0.6545	Remote Similarity	NPC471304
0.6544	Remote Similarity	NPC329708
0.6544	Remote Similarity	NPC264166
0.6544	Remote Similarity	NPC274291
0.6544	Remote Similarity	NPC165349
0.6544	Remote Similarity	NPC118832
0.6544	Remote Similarity	NPC47059
0.6537	Remote Similarity	NPC206201
0.6533	Remote Similarity	NPC288987
0.6532	Remote Similarity	NPC477610
0.653	Remote Similarity	NPC82548
0.6528	Remote Similarity	NPC295898
0.6524	Remote Similarity	NPC245055
0.6524	Remote Similarity	NPC39370
0.6524	Remote Similarity	NPC473184
0.6517	Remote Similarity	NPC252590
0.6509	Remote Similarity	NPC131017
0.6509	Remote Similarity	NPC101543
0.6509	Remote Similarity	NPC469554
0.6507	Remote Similarity	NPC60006
0.6504	Remote Similarity	NPC225279
0.6502	Remote Similarity	NPC121903
0.65	Remote Similarity	NPC44161
0.6489	Remote Similarity	NPC184408
0.6488	Remote Similarity	NPC168486
0.6488	Remote Similarity	NPC222592
0.6486	Remote Similarity	NPC235633
0.6486	Remote Similarity	NPC472098
0.6486	Remote Similarity	NPC474428
0.6485	Remote Similarity	NPC64055
0.6479	Remote Similarity	NPC13880
0.6476	Remote Similarity	NPC470502
0.6473	Remote Similarity	NPC67658
0.6471	Remote Similarity	NPC283152
0.6468	Remote Similarity	NPC473764
0.6468	Remote Similarity	NPC473183
0.6468	Remote Similarity	NPC314940
0.6465	Remote Similarity	NPC476167
0.6463	Remote Similarity	NPC245348
0.646	Remote Similarity	NPC208084
0.6457	Remote Similarity	NPC469592
0.6457	Remote Similarity	NPC471080
0.6457	Remote Similarity	NPC478074
0.6455	Remote Similarity	NPC470247
0.6455	Remote Similarity	NPC476465
0.6455	Remote Similarity	NPC475910
0.6452	Remote Similarity	NPC470249
0.6447	Remote Similarity	NPC144452
0.6441	Remote Similarity	NPC246518
0.6438	Remote Similarity	NPC304183
0.6435	Remote Similarity	NPC234197
0.6422	Remote Similarity	NPC223427
0.6419	Remote Similarity	NPC192315
0.6419	Remote Similarity	NPC470503
0.6416	Remote Similarity	NPC477609
0.6413	Remote Similarity	NPC316981
0.6411	Remote Similarity	NPC171171
0.6408	Remote Similarity	NPC478032
0.6406	Remote Similarity	NPC232727
0.6393	Remote Similarity	NPC285558
0.6389	Remote Similarity	NPC476582
0.6389	Remote Similarity	NPC4071
0.6389	Remote Similarity	NPC476578
0.6389	Remote Similarity	NPC18487
0.6385	Remote Similarity	NPC230403
0.6385	Remote Similarity	NPC198673
0.6384	Remote Similarity	NPC162530
0.6384	Remote Similarity	NPC266931
0.6383	Remote Similarity	NPC33064
0.6381	Remote Similarity	NPC66083
0.6372	Remote Similarity	NPC243834
0.6372	Remote Similarity	NPC70956
0.6368	Remote Similarity	NPC208284
0.6368	Remote Similarity	NPC146418
0.6364	Remote Similarity	NPC323345
0.6364	Remote Similarity	NPC470164
0.6364	Remote Similarity	NPC202503
0.6364	Remote Similarity	NPC314002
0.6356	Remote Similarity	NPC50562
0.6356	Remote Similarity	NPC272549
0.6355	Remote Similarity	NPC158129
0.6351	Remote Similarity	NPC174758
0.6347	Remote Similarity	NPC162484
0.6344	Remote Similarity	NPC131885
0.6344	Remote Similarity	NPC96321
0.6344	Remote Similarity	NPC303658
0.6344	Remote Similarity	NPC469594
0.6343	Remote Similarity	NPC72211
0.6341	Remote Similarity	NPC288943
0.6341	Remote Similarity	NPC56618
0.634	Remote Similarity	NPC141053
0.6339	Remote Similarity	NPC264176
0.6338	Remote Similarity	NPC133140
0.6338	Remote Similarity	NPC195268
0.6335	Remote Similarity	NPC313189
0.633	Remote Similarity	NPC31930
0.6327	Remote Similarity	NPC274982
0.6327	Remote Similarity	NPC74969
0.6323	Remote Similarity	NPC11464
0.6318	Remote Similarity	NPC148889
0.6316	Remote Similarity	NPC204717
0.6313	Remote Similarity	NPC287437
0.6311	Remote Similarity	NPC149471
0.6311	Remote Similarity	NPC324361
0.6311	Remote Similarity	NPC271215
0.6309	Remote Similarity	NPC314954
0.6309	Remote Similarity	NPC274640
0.6308	Remote Similarity	NPC279401
0.6308	Remote Similarity	NPC79293
0.6304	Remote Similarity	NPC135173
0.6304	Remote Similarity	NPC470501
0.6301	Remote Similarity	NPC135887
0.6301	Remote Similarity	NPC199277
0.63	Remote Similarity	NPC473513
0.6298	Remote Similarity	NPC470474
0.629	Remote Similarity	NPC474145
0.629	Remote Similarity	NPC82053
0.629	Remote Similarity	NPC216369
0.629	Remote Similarity	NPC475841
0.6288	Remote Similarity	NPC472099
0.6287	Remote Similarity	NPC109447
0.6284	Remote Similarity	NPC11017
0.6284	Remote Similarity	NPC477019
0.6284	Remote Similarity	NPC315957
0.6281	Remote Similarity	NPC6436
0.628	Remote Similarity	NPC233050
0.628	Remote Similarity	NPC276540
0.6279	Remote Similarity	NPC43787
0.6279	Remote Similarity	NPC205934
0.6278	Remote Similarity	NPC174672
0.6272	Remote Similarity	NPC173080

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 NPC98685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	887
0.2-0.3	903
0.3-0.4	2154
0.4-0.5	3448
0.5-0.6	1277
0.6-0.7	142
0.7-0.8	0
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
0.7059	Intermediate Similarity	NPD4890	Phase 2
0.698	Remote Similarity	NPD5256	Discontinued
0.6967	Remote Similarity	NPD6991	Approved
0.6942	Remote Similarity	NPD1038	Approved
0.6869	Remote Similarity	NPD7452	Approved
0.6869	Remote Similarity	NPD7222	Phase 2
0.6869	Remote Similarity	NPD7453	Approved
0.686	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7671	Approved
0.6837	Remote Similarity	NPD7672	Approved
0.6827	Remote Similarity	NPD4418	Discontinued
0.6798	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4204	Approved
0.67	Remote Similarity	NPD4203	Approved
0.6667	Remote Similarity	NPD9705	Discontinued
0.6667	Remote Similarity	NPD4502	Phase 2
0.6667	Remote Similarity	NPD112	Approved
0.6635	Remote Similarity	NPD3477	Phase 2
0.6635	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5658	Approved
0.6593	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6550	Discontinued
0.6552	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4038	Approved
0.6544	Remote Similarity	NPD4039	Approved
0.6544	Remote Similarity	NPD4035	Approved
0.6544	Remote Similarity	NPD4033	Approved
0.6544	Remote Similarity	NPD4036	Approved
0.6544	Remote Similarity	NPD31	Approved
0.6544	Remote Similarity	NPD4034	Approved
0.6544	Remote Similarity	NPD4037	Approved
0.6544	Remote Similarity	NPD32	Approved
0.6544	Remote Similarity	NPD4122	Approved
0.6542	Remote Similarity	NPD1768	Approved
0.6522	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3003	Approved
0.6509	Remote Similarity	NPD6590	Discontinued
0.6496	Remote Similarity	NPD3006	Discontinued
0.6489	Remote Similarity	NPD4429	Discontinued
0.6473	Remote Similarity	NPD6643	Discontinued
0.6471	Remote Similarity	NPD6159	Phase 2
0.6465	Remote Similarity	NPD2177	Approved
0.6465	Remote Similarity	NPD2175	Phase 3
0.6465	Remote Similarity	NPD2176	Approved
0.6465	Remote Similarity	NPD3825	Phase 3
0.646	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD1034	Phase 3
0.6455	Remote Similarity	NPD2189	Approved
0.6455	Remote Similarity	NPD2187	Approved
0.6444	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3920	Phase 2
0.6436	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD4454	Phase 2
0.6415	Remote Similarity	NPD6569	Phase 2
0.6411	Remote Similarity	NPD2444	Phase 2
0.6402	Remote Similarity	NPD5512	Phase 3
0.64	Remote Similarity	NPD5612	Discontinued
0.6393	Remote Similarity	NPD4795	Phase 2
0.6388	Remote Similarity	NPD3875	Discontinued
0.6384	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD2383	Phase 1
0.6376	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD9690	Approved
0.6368	Remote Similarity	NPD2984	Phase 2
0.6364	Remote Similarity	NPD5530	Phase 1
0.636	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5903	Approved
0.6356	Remote Similarity	NPD5902	Approved
0.6338	Remote Similarity	NPD3922	Approved
0.6338	Remote Similarity	NPD3924	Approved
0.6338	Remote Similarity	NPD3923	Approved
0.6338	Remote Similarity	NPD3921	Approved
0.6335	Remote Similarity	NPD1392	Approved
0.6323	Remote Similarity	NPD3392	Approved
0.6313	Remote Similarity	NPD4548	Discontinued
0.6313	Remote Similarity	NPD2581	Approved
0.6313	Remote Similarity	NPD2582	Approved
0.6313	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD9695	Approved
0.6304	Remote Similarity	NPD1856	Discontinued
0.6301	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD6220	Phase 3
0.6295	Remote Similarity	NPD5066	Phase 2
0.6295	Remote Similarity	NPD5067	Phase 2
0.6291	Remote Similarity	NPD5913	Phase 3
0.6291	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8403	Phase 1
0.6288	Remote Similarity	NPD6242	Discontinued
0.6284	Remote Similarity	NPD1739	Approved
0.6284	Remote Similarity	NPD1740	Approved
0.6281	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5429	Discontinued
0.6256	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5050	Approved
0.625	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD3397	Phase 2
0.6244	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3945	Discontinued
0.6239	Remote Similarity	NPD5559	Phase 2
0.6239	Remote Similarity	NPD5999	Phase 2
0.6232	Remote Similarity	NPD3504	Approved
0.6232	Remote Similarity	NPD1032	Phase 2
0.6232	Remote Similarity	NPD3503	Approved
0.6228	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5164	Discontinued
0.6224	Remote Similarity	NPD5051	Phase 1
0.6222	Remote Similarity	NPD3939	Suspended
0.6222	Remote Similarity	NPD5939	Approved
0.6222	Remote Similarity	NPD5936	Approved
0.6221	Remote Similarity	NPD6988	Phase 1
0.6217	Remote Similarity	NPD1996	Discontinued
0.6216	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD5022	Discontinued
0.6201	Remote Similarity	NPD3354	Phase 2
0.6201	Remote Similarity	NPD6985	Discontinued
0.6195	Remote Similarity	NPD3816	Phase 1
0.6195	Remote Similarity	NPD3815	Phase 1
0.619	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6290	Phase 2
0.618	Remote Similarity	NPD7719	Discontinued
0.6157	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.615	Remote Similarity	NPD1769	Discontinued
0.615	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.615	Remote Similarity	NPD2749	Discontinued
0.6147	Remote Similarity	NPD1229	Phase 2
0.6147	Remote Similarity	NPD5850	Phase 3
0.6147	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD565	Phase 2
0.6146	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD19	Approved
0.6139	Remote Similarity	NPD1742	Approved
0.6139	Remote Similarity	NPD1743	Approved
0.6133	Remote Similarity	NPD4520	Approved
0.6132	Remote Similarity	NPD4889	Approved
0.613	Remote Similarity	NPD5632	Approved
0.613	Remote Similarity	NPD7395	Discontinued
0.6129	Remote Similarity	NPD6251	Discontinued
0.6128	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD4927	Discontinued
0.6123	Remote Similarity	NPD6202	Discontinued
0.6121	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5287	Discontinued
0.6111	Remote Similarity	NPD4372	Phase 1
0.6111	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD2951	Discontinued
0.6104	Remote Similarity	NPD3763	Approved
0.6104	Remote Similarity	NPD7194	Discontinued
0.6103	Remote Similarity	NPD2917	Approved
0.6102	Remote Similarity	NPD7555	Discontinued
0.6099	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3983	Phase 3
0.6098	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD2564	Approved
0.6093	Remote Similarity	NPD2410	Phase 2
0.6093	Remote Similarity	NPD2565	Phase 2
0.6091	Remote Similarity	NPD2778	Approved
0.6089	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD3853	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD802	Phase 2
0.6083	Remote Similarity	NPD5891	Approved
0.6081	Remote Similarity	NPD1897	Discontinued
0.608	Remote Similarity	NPD6961	Discontinued
0.6078	Remote Similarity	NPD4796	Discontinued
0.6076	Remote Similarity	NPD7567	Approved
0.6076	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3507	Phase 2
0.6071	Remote Similarity	NPD6150	Discontinued
0.607	Remote Similarity	NPD3257	Approved
0.607	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD3386	Phase 2
0.6066	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD3259	Approved
0.6055	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD6324	Phase 1
0.6045	Remote Similarity	NPD2953	Discontinued
0.6039	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD3258	Approved
0.6034	Remote Similarity	NPD3402	Phase 1
0.6028	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD4919	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