NPASS Compound

Structure

CID245348 OpenBabel06191716042D 21 23 0 0 1 0 0 0 0 0999 V2000 2.0796 -2.5692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1585 -3.8038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1845 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0212 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8369 1.4496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1898 -2.1672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6739 0.9664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3475 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8363 -1.4493 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0214 0.9657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3477 0.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1849 1.4489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8365 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1852 2.4489 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.7813 -1.6504 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 2.5108 -0.4836 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8876 1.4655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4881 -3.0860 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 8 2 0 0 0 0 6 18 2 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 7 1 6 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 13 16 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	365.02
Volume:	306.081
LogP:	3.199
LogD:	2.816
LogS:	-4.338
# Rotatable Bonds:	4
TPSA:	60.94
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.541
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957
MDCK Permeability:	1.141648226621328e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.854
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.541
Plasma Protein Binding (PPB):	73.18658447265625%
Volume Distribution (VD):	2.017
Pgp-substrate:	27.89931869506836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.785
CYP2D6-inhibitor:	0.624
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.472
CYP3A4-substrate:	0.753

ADMET: Excretion

Clearance (CL):	5.223
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.605
Human Hepatotoxicity (H-HT):	0.825
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.454
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.393
Carcinogencity:	0.487
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC245348

Natural Product ID:	NPC245348
*Common Name:**	Eudistomidin C
IUPAC Name:	5-bromo-1-[(1S)-1-(methylamino)-2-methylsulfanylethyl]-9H-pyrido[3,4-b]indol-6-ol
Synonyms:	Eudistomidin C
Standard InCHIKey:	RGJZFVKMTLBCJY-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C15H16BrN3OS/c1-17-10(7-21-2)15-14-8(5-6-18-15)12-9(19-14)3-4-11(20)13(12)16/h3-6,10,17,19-20H,7H2,1-2H3/t10-/m1/s1
SMILES:	CSC[C@H](c1nccc2c1[nH]c1c2c(Br)c(cc1)O)NC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1800684
PubChem CID:	23426231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO4412	Vepris stolzii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7903	Ascochyta fabae	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3258	Parmelia glabra	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8196	Leucanthemum aligulatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2552	Shorea acuminata	Species	Dipterocarpaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	0.36	ug.mL-1	PMID[487575]

☑ 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 NPC245348 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	702
0.1-0.2	9991
0.2-0.3	9479
0.3-0.4	15550
0.4-0.5	3443
0.5-0.6	2180
0.6-0.7	1183
0.7-0.8	154
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC60006
0.8986	High Similarity	NPC255110
0.8955	High Similarity	NPC476124
0.8768	High Similarity	NPC476121
0.8539	High Similarity	NPC97902
0.8537	High Similarity	NPC475070
0.8476	Intermediate Similarity	NPC477610
0.8416	Intermediate Similarity	NPC222018
0.8148	Intermediate Similarity	NPC477609
0.8109	Intermediate Similarity	NPC171171
0.81	Intermediate Similarity	NPC204717
0.8075	Intermediate Similarity	NPC5145
0.806	Intermediate Similarity	NPC314002
0.805	Intermediate Similarity	NPC220765
0.8029	Intermediate Similarity	NPC476167
0.8028	Intermediate Similarity	NPC292958
0.8018	Intermediate Similarity	NPC476041
0.8018	Intermediate Similarity	NPC304926
0.8	Intermediate Similarity	NPC99666
0.799	Intermediate Similarity	NPC176538
0.7982	Intermediate Similarity	NPC477607
0.7982	Intermediate Similarity	NPC477608
0.7981	Intermediate Similarity	NPC192315
0.7913	Intermediate Similarity	NPC39092
0.7913	Intermediate Similarity	NPC324149
0.787	Intermediate Similarity	NPC246518
0.785	Intermediate Similarity	NPC184964
0.7847	Intermediate Similarity	NPC77555
0.7838	Intermediate Similarity	NPC470501
0.7793	Intermediate Similarity	NPC470502
0.7752	Intermediate Similarity	NPC128084
0.7723	Intermediate Similarity	NPC470503
0.7699	Intermediate Similarity	NPC6215
0.7678	Intermediate Similarity	NPC156704
0.7664	Intermediate Similarity	NPC211813
0.7647	Intermediate Similarity	NPC142901
0.7633	Intermediate Similarity	NPC46580
0.7619	Intermediate Similarity	NPC307963
0.7593	Intermediate Similarity	NPC470505
0.7581	Intermediate Similarity	NPC473761
0.757	Intermediate Similarity	NPC315491
0.757	Intermediate Similarity	NPC45459
0.757	Intermediate Similarity	NPC249040
0.757	Intermediate Similarity	NPC205254
0.757	Intermediate Similarity	NPC23420
0.757	Intermediate Similarity	NPC106771
0.757	Intermediate Similarity	NPC303820
0.756	Intermediate Similarity	NPC76748
0.7547	Intermediate Similarity	NPC251090
0.7546	Intermediate Similarity	NPC223427
0.7542	Intermediate Similarity	NPC470504
0.7535	Intermediate Similarity	NPC232727
0.7535	Intermediate Similarity	NPC475935
0.7535	Intermediate Similarity	NPC94211
0.7535	Intermediate Similarity	NPC52909
0.7534	Intermediate Similarity	NPC80596
0.7534	Intermediate Similarity	NPC476116
0.7524	Intermediate Similarity	NPC92111
0.7512	Intermediate Similarity	NPC470500
0.7512	Intermediate Similarity	NPC296527
0.7512	Intermediate Similarity	NPC32771
0.7489	Intermediate Similarity	NPC200553
0.7488	Intermediate Similarity	NPC213308
0.7468	Intermediate Similarity	NPC295228
0.7467	Intermediate Similarity	NPC213530
0.7467	Intermediate Similarity	NPC193267
0.7465	Intermediate Similarity	NPC245816
0.7465	Intermediate Similarity	NPC476138
0.7465	Intermediate Similarity	NPC476098
0.7463	Intermediate Similarity	NPC88363
0.7451	Intermediate Similarity	NPC474958
0.744	Intermediate Similarity	NPC48938
0.7418	Intermediate Similarity	NPC326634
0.7414	Intermediate Similarity	NPC207686
0.7411	Intermediate Similarity	NPC470799
0.7411	Intermediate Similarity	NPC8022
0.7404	Intermediate Similarity	NPC41679
0.7399	Intermediate Similarity	NPC266931
0.7393	Intermediate Similarity	NPC162002
0.7389	Intermediate Similarity	NPC82331
0.7384	Intermediate Similarity	NPC171393
0.7384	Intermediate Similarity	NPC295452
0.7383	Intermediate Similarity	NPC242209
0.7373	Intermediate Similarity	NPC37152
0.7371	Intermediate Similarity	NPC476451
0.735	Intermediate Similarity	NPC174489
0.7342	Intermediate Similarity	NPC81175
0.7339	Intermediate Similarity	NPC279189
0.7336	Intermediate Similarity	NPC167908
0.733	Intermediate Similarity	NPC96890
0.7327	Intermediate Similarity	NPC315957
0.7327	Intermediate Similarity	NPC19872
0.7325	Intermediate Similarity	NPC310118
0.7309	Intermediate Similarity	NPC208284
0.7288	Intermediate Similarity	NPC26641
0.7285	Intermediate Similarity	NPC88008
0.7277	Intermediate Similarity	NPC316981
0.7277	Intermediate Similarity	NPC274229
0.7265	Intermediate Similarity	NPC167860
0.7265	Intermediate Similarity	NPC123976
0.7264	Intermediate Similarity	NPC128751
0.7264	Intermediate Similarity	NPC246700
0.7261	Intermediate Similarity	NPC130570
0.7249	Intermediate Similarity	NPC60621
0.7248	Intermediate Similarity	NPC121772
0.7246	Intermediate Similarity	NPC477549
0.7246	Intermediate Similarity	NPC248454
0.723	Intermediate Similarity	NPC469497
0.723	Intermediate Similarity	NPC106833
0.7227	Intermediate Similarity	NPC200836
0.7227	Intermediate Similarity	NPC53144
0.722	Intermediate Similarity	NPC185782
0.7214	Intermediate Similarity	NPC131718
0.7212	Intermediate Similarity	NPC72980
0.7209	Intermediate Similarity	NPC106937
0.7207	Intermediate Similarity	NPC270918
0.72	Intermediate Similarity	NPC26679
0.7186	Intermediate Similarity	NPC211416
0.7175	Intermediate Similarity	NPC477111
0.7175	Intermediate Similarity	NPC82548
0.7168	Intermediate Similarity	NPC476287
0.7167	Intermediate Similarity	NPC110151
0.7163	Intermediate Similarity	NPC477166
0.7163	Intermediate Similarity	NPC473342
0.7163	Intermediate Similarity	NPC304187
0.7163	Intermediate Similarity	NPC477167
0.7162	Intermediate Similarity	NPC477113
0.7156	Intermediate Similarity	NPC284678
0.7155	Intermediate Similarity	NPC477861
0.7149	Intermediate Similarity	NPC178858
0.7137	Intermediate Similarity	NPC216369
0.713	Intermediate Similarity	NPC329541
0.713	Intermediate Similarity	NPC276657
0.7124	Intermediate Similarity	NPC207020
0.7124	Intermediate Similarity	NPC219087
0.7123	Intermediate Similarity	NPC15102
0.7119	Intermediate Similarity	NPC471891
0.7117	Intermediate Similarity	NPC285558
0.7109	Intermediate Similarity	NPC163055
0.7109	Intermediate Similarity	NPC176127
0.7101	Intermediate Similarity	NPC474409
0.7098	Intermediate Similarity	NPC171787
0.7097	Intermediate Similarity	NPC276517
0.7095	Intermediate Similarity	NPC473312
0.7091	Intermediate Similarity	NPC329793
0.7078	Intermediate Similarity	NPC265576
0.7074	Intermediate Similarity	NPC27041
0.7071	Intermediate Similarity	NPC184225
0.7069	Intermediate Similarity	NPC280272
0.7062	Intermediate Similarity	NPC307191
0.7062	Intermediate Similarity	NPC314394
0.7059	Intermediate Similarity	NPC102423
0.7035	Intermediate Similarity	NPC85273
0.7032	Intermediate Similarity	NPC153042
0.7031	Intermediate Similarity	NPC477110
0.7031	Intermediate Similarity	NPC469928
0.7031	Intermediate Similarity	NPC74969
0.7028	Intermediate Similarity	NPC475746
0.7022	Intermediate Similarity	NPC476465
0.7019	Intermediate Similarity	NPC313791
0.701	Intermediate Similarity	NPC282231
0.7009	Intermediate Similarity	NPC62749
0.7005	Intermediate Similarity	NPC97343
0.7004	Intermediate Similarity	NPC153400
0.7	Intermediate Similarity	NPC469727
0.6995	Remote Similarity	NPC230869
0.6992	Remote Similarity	NPC253580
0.6992	Remote Similarity	NPC156003
0.6992	Remote Similarity	NPC314954
0.699	Remote Similarity	NPC49954
0.699	Remote Similarity	NPC474561
0.6987	Remote Similarity	NPC245055
0.6987	Remote Similarity	NPC33064
0.6986	Remote Similarity	NPC13880
0.6979	Remote Similarity	NPC319232
0.6979	Remote Similarity	NPC214142
0.6979	Remote Similarity	NPC24370
0.6978	Remote Similarity	NPC166492
0.6978	Remote Similarity	NPC473362
0.6975	Remote Similarity	NPC469554
0.6974	Remote Similarity	NPC471603
0.697	Remote Similarity	NPC264285
0.6963	Remote Similarity	NPC94943
0.6961	Remote Similarity	NPC279918
0.696	Remote Similarity	NPC11464
0.6957	Remote Similarity	NPC63751
0.6957	Remote Similarity	NPC183407
0.6949	Remote Similarity	NPC304307
0.6949	Remote Similarity	NPC118559
0.6949	Remote Similarity	NPC261251
0.6949	Remote Similarity	NPC34580
0.6949	Remote Similarity	NPC124920
0.6949	Remote Similarity	NPC470126
0.6948	Remote Similarity	NPC212535
0.694	Remote Similarity	NPC74360
0.6933	Remote Similarity	NPC474145
0.6933	Remote Similarity	NPC475841
0.6929	Remote Similarity	NPC15801
0.6926	Remote Similarity	NPC477114
0.6923	Remote Similarity	NPC473764

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 NPC245348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	797
0.2-0.3	739
0.3-0.4	2255
0.4-0.5	2622
0.5-0.6	1896
0.6-0.7	469
0.7-0.8	24
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
0.7961	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1038	Approved
0.757	Intermediate Similarity	NPD484	Approved
0.7536	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD7948	Phase 1
0.7411	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5065	Approved
0.7333	Intermediate Similarity	NPD5612	Discontinued
0.7327	Intermediate Similarity	NPD1739	Approved
0.7327	Intermediate Similarity	NPD1740	Approved
0.7273	Intermediate Similarity	NPD4795	Phase 2
0.7264	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7112	Discontinued
0.7209	Intermediate Similarity	NPD802	Phase 2
0.7204	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7603	Discontinued
0.7123	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2189	Approved
0.7022	Intermediate Similarity	NPD2187	Approved
0.7018	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1326	Approved
0.7005	Intermediate Similarity	NPD1325	Approved
0.699	Remote Similarity	NPD425	Approved
0.699	Remote Similarity	NPD424	Approved
0.6982	Remote Similarity	NPD4511	Phase 1
0.6968	Remote Similarity	NPD3825	Phase 3
0.6963	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5658	Approved
0.6943	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1258	Discontinued
0.6926	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4044	Discontinued
0.692	Remote Similarity	NPD4886	Phase 2
0.69	Remote Similarity	NPD3330	Phase 1
0.6897	Remote Similarity	NPD2021	Discontinued
0.6892	Remote Similarity	NPD3814	Phase 1
0.6875	Remote Similarity	NPD8073	Approved
0.6875	Remote Similarity	NPD3931	Approved
0.6875	Remote Similarity	NPD2472	Approved
0.6875	Remote Similarity	NPD3928	Approved
0.6875	Remote Similarity	NPD2471	Approved
0.6854	Remote Similarity	NPD6595	Phase 3
0.6853	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5559	Phase 2
0.6842	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6242	Discontinued
0.6829	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1392	Approved
0.6828	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2177	Approved
0.6816	Remote Similarity	NPD2175	Phase 3
0.6816	Remote Similarity	NPD2176	Approved
0.6784	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD925	Approved
0.6779	Remote Similarity	NPD926	Approved
0.6774	Remote Similarity	NPD706	Phase 1
0.6773	Remote Similarity	NPD3404	Approved
0.677	Remote Similarity	NPD8072	Approved
0.6759	Remote Similarity	NPD5050	Approved
0.6757	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7222	Phase 2
0.675	Remote Similarity	NPD8512	Phase 3
0.6748	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6492	Phase 2
0.6745	Remote Similarity	NPD9690	Approved
0.6742	Remote Similarity	NPD9695	Approved
0.6741	Remote Similarity	NPD8396	Approved
0.6741	Remote Similarity	NPD8395	Approved
0.674	Remote Similarity	NPD31	Approved
0.674	Remote Similarity	NPD4038	Approved
0.674	Remote Similarity	NPD4036	Approved
0.674	Remote Similarity	NPD4033	Approved
0.674	Remote Similarity	NPD4034	Approved
0.674	Remote Similarity	NPD4037	Approved
0.674	Remote Similarity	NPD8272	Phase 2
0.674	Remote Similarity	NPD4122	Approved
0.674	Remote Similarity	NPD32	Approved
0.674	Remote Similarity	NPD4039	Approved
0.674	Remote Similarity	NPD4035	Approved
0.6736	Remote Similarity	NPD7558	Phase 2
0.6732	Remote Similarity	NPD8284	Discontinued
0.6723	Remote Similarity	NPD4890	Phase 2
0.6715	Remote Similarity	NPD9705	Discontinued
0.6715	Remote Similarity	NPD112	Approved
0.671	Remote Similarity	NPD949	Phase 1
0.6683	Remote Similarity	NPD1661	Suspended
0.6681	Remote Similarity	NPD4865	Approved
0.6681	Remote Similarity	NPD3354	Phase 2
0.6667	Remote Similarity	NPD2383	Phase 1
0.6667	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3609	Approved
0.6651	Remote Similarity	NPD2762	Phase 2
0.6651	Remote Similarity	NPD3610	Approved
0.6651	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6276	Discontinued
0.6638	Remote Similarity	NPD5067	Phase 2
0.6638	Remote Similarity	NPD5530	Phase 1
0.6638	Remote Similarity	NPD5936	Approved
0.6638	Remote Similarity	NPD5066	Phase 2
0.6638	Remote Similarity	NPD3003	Approved
0.6638	Remote Similarity	NPD5939	Approved
0.6637	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD3395	Approved
0.6637	Remote Similarity	NPD3396	Approved
0.6636	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6991	Approved
0.6614	Remote Similarity	NPD8442	Discontinued
0.6614	Remote Similarity	NPD4558	Phase 2
0.6609	Remote Similarity	NPD7452	Approved
0.6609	Remote Similarity	NPD7453	Approved
0.6605	Remote Similarity	NPD6159	Phase 2
0.6605	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4845	Discontinued
0.6598	Remote Similarity	NPD4850	Phase 1
0.6595	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3013	Phase 3
0.6594	Remote Similarity	NPD5901	Discontinued
0.6591	Remote Similarity	NPD8431	Approved
0.6591	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD482	Approved
0.6587	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2615	Phase 3
0.6581	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2616	Phase 3
0.6578	Remote Similarity	NPD1218	Approved
0.6578	Remote Similarity	NPD1219	Approved
0.6577	Remote Similarity	NPD459	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2094	Phase 2
0.656	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2092	Phase 2
0.656	Remote Similarity	NPD2095	Phase 2
0.6558	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5100	Phase 3
0.6556	Remote Similarity	NPD7711	Discontinued
0.6552	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1259	Discontinued
0.6543	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD1197	Approved
0.653	Remote Similarity	NPD2096	Phase 2
0.653	Remote Similarity	NPD2091	Phase 2
0.6527	Remote Similarity	NPD3254	Phase 1
0.6527	Remote Similarity	NPD3255	Phase 1
0.6524	Remote Similarity	NPD1685	Approved
0.6524	Remote Similarity	NPD1684	Approved
0.6522	Remote Similarity	NPD8101	Phase 3
0.6522	Remote Similarity	NPD5426	Phase 3
0.652	Remote Similarity	NPD7068	Approved
0.652	Remote Similarity	NPD7067	Approved
0.652	Remote Similarity	NPD1768	Approved
0.6517	Remote Similarity	NPD1722	Approved
0.6516	Remote Similarity	NPD2062	Phase 2
0.6516	Remote Similarity	NPD8106	Phase 2
0.6514	Remote Similarity	NPD4203	Approved
0.6514	Remote Similarity	NPD4204	Approved
0.6509	Remote Similarity	NPD2916	Discontinued
0.6509	Remote Similarity	NPD7672	Approved
0.6509	Remote Similarity	NPD7671	Approved
0.6507	Remote Similarity	NPD5255	Approved
0.6507	Remote Similarity	NPD6975	Discontinued
0.6505	Remote Similarity	NPD6158	Phase 2
0.6505	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.65	Remote Similarity	NPD786	Approved
0.6496	Remote Similarity	NPD4502	Phase 2
0.6494	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3962	Phase 2
0.6494	Remote Similarity	NPD3959	Phase 2
0.6493	Remote Similarity	NPD5140	Approved
0.6493	Remote Similarity	NPD5138	Approved
0.6489	Remote Similarity	NPD4418	Discontinued
0.6485	Remote Similarity	NPD5930	Phase 3
0.6479	Remote Similarity	NPD2640	Approved
0.6479	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2641	Approved
0.6479	Remote Similarity	NPD2781	Approved
0.6473	Remote Similarity	NPD3924	Approved
0.6473	Remote Similarity	NPD3923	Approved
0.6473	Remote Similarity	NPD994	Phase 2
0.6473	Remote Similarity	NPD3921	Approved
0.6473	Remote Similarity	NPD996	Phase 2
0.6473	Remote Similarity	NPD3922	Approved
0.6466	Remote Similarity	NPD6290	Phase 2
0.6463	Remote Similarity	NPD6494	Phase 2
0.6462	Remote Similarity	NPD2782	Approved
0.6462	Remote Similarity	NPD2780	Approved
0.6457	Remote Similarity	NPD5482	Discontinued
0.6446	Remote Similarity	NPD4403	Phase 3
0.6446	Remote Similarity	NPD4401	Phase 2
0.6444	Remote Similarity	NPD3402	Phase 1
0.6444	Remote Similarity	NPD534	Phase 2
0.6444	Remote Similarity	NPD537	Phase 2
0.6441	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4703	Approved
0.6439	Remote Similarity	NPD4702	Approved
0.6438	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4612	Discontinued

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