NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	275.99
Volume:	224.688
LogP:	3.554
LogD:	3.186
LogS:	-4.528
# Rotatable Bonds:	0
TPSA:	38.05
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	2.676
Fsp3:	0.083
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:	-4.665
MDCK Permeability:	2.25064668484265e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.759
Plasma Protein Binding (PPB):	84.27658081054688%
Volume Distribution (VD):	1.397
Pgp-substrate:	16.275754928588867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.312
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.198
CYP2C9-substrate:	0.429
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.597
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	5.894
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.829
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.272
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.181
Carcinogencity:	0.754
Eye Corrosion:	0.005
Eye Irritation:	0.536
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC476121

Natural Product ID:	NPC476121
*Common Name:**	2-Methyleudistomin J
IUPAC Name:	7-bromo-2-methyl-9H-pyrido[3,4-b]indol-2-ium-6-ol;chloride
Synonyms:	2-Methyleudistomin J
Standard InCHIKey:	HFVUCSGBOVBUCM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H9BrN2O.ClH/c1-15-3-2-7-8-4-12(16)9(13)5-10(8)14-11(7)6-15;/h2-6,16H,1H3;1H
SMILES:	Cn1ccc2c(c1)nc1c2cc(c(c1)Br)O.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL538117
PubChem CID:	45266441
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO32719	eudistoma gilboverde	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720532]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[565952]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	15.1	ug.mL-1	PMID[565952]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	17.5	ug.mL-1	PMID[565952]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15.1	ug.mL-1	PMID[565952]

☑ 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 NPC476121 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	913
0.1-0.2	10859
0.2-0.3	8100
0.3-0.4	15182
0.4-0.5	4190
0.5-0.6	2390
0.6-0.7	950
0.7-0.8	107
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC476124
0.8818	High Similarity	NPC60006
0.8768	High Similarity	NPC245348
0.8586	High Similarity	NPC222018
0.8513	High Similarity	NPC211813
0.8458	Intermediate Similarity	NPC477610
0.8436	Intermediate Similarity	NPC97902
0.8426	Intermediate Similarity	NPC475070
0.8204	Intermediate Similarity	NPC477609
0.8173	Intermediate Similarity	NPC476167
0.8122	Intermediate Similarity	NPC192315
0.8073	Intermediate Similarity	NPC171171
0.8063	Intermediate Similarity	NPC204717
0.804	Intermediate Similarity	NPC176538
0.8039	Intermediate Similarity	NPC5145
0.8021	Intermediate Similarity	NPC314002
0.801	Intermediate Similarity	NPC220765
0.801	Intermediate Similarity	NPC200836
0.801	Intermediate Similarity	NPC53144
0.8	Intermediate Similarity	NPC246518
0.799	Intermediate Similarity	NPC292958
0.7981	Intermediate Similarity	NPC304926
0.7981	Intermediate Similarity	NPC476041
0.7944	Intermediate Similarity	NPC477608
0.7944	Intermediate Similarity	NPC477607
0.7941	Intermediate Similarity	NPC82548
0.7877	Intermediate Similarity	NPC470501
0.7874	Intermediate Similarity	NPC128084
0.7868	Intermediate Similarity	NPC324149
0.7868	Intermediate Similarity	NPC99666
0.783	Intermediate Similarity	NPC470502
0.782	Intermediate Similarity	NPC255110
0.7801	Intermediate Similarity	NPC184964
0.7783	Intermediate Similarity	NPC473761
0.7778	Intermediate Similarity	NPC85273
0.7762	Intermediate Similarity	NPC142901
0.7757	Intermediate Similarity	NPC470503
0.7711	Intermediate Similarity	NPC77555
0.7656	Intermediate Similarity	NPC121903
0.765	Intermediate Similarity	NPC329541
0.7621	Intermediate Similarity	NPC470505
0.7576	Intermediate Similarity	NPC46580
0.7573	Intermediate Similarity	NPC476138
0.7573	Intermediate Similarity	NPC245816
0.7569	Intermediate Similarity	NPC6215
0.7561	Intermediate Similarity	NPC232727
0.756	Intermediate Similarity	NPC80596
0.7545	Intermediate Similarity	NPC37152
0.7539	Intermediate Similarity	NPC314940
0.7539	Intermediate Similarity	NPC473764
0.7537	Intermediate Similarity	NPC156704
0.7536	Intermediate Similarity	NPC470500
0.7512	Intermediate Similarity	NPC470799
0.7512	Intermediate Similarity	NPC8022
0.7512	Intermediate Similarity	NPC249040
0.7511	Intermediate Similarity	NPC200553
0.75	Intermediate Similarity	NPC475841
0.75	Intermediate Similarity	NPC25899
0.75	Intermediate Similarity	NPC82331
0.75	Intermediate Similarity	NPC474145
0.7488	Intermediate Similarity	NPC213530
0.7488	Intermediate Similarity	NPC251090
0.7488	Intermediate Similarity	NPC223427
0.7488	Intermediate Similarity	NPC193267
0.7487	Intermediate Similarity	NPC88363
0.7476	Intermediate Similarity	NPC174758
0.7476	Intermediate Similarity	NPC174672
0.7475	Intermediate Similarity	NPC307963
0.7474	Intermediate Similarity	NPC274229
0.7464	Intermediate Similarity	NPC53344
0.7463	Intermediate Similarity	NPC92111
0.7462	Intermediate Similarity	NPC48938
0.7451	Intermediate Similarity	NPC267928
0.745	Intermediate Similarity	NPC32771
0.745	Intermediate Similarity	NPC296527
0.7427	Intermediate Similarity	NPC303820
0.7427	Intermediate Similarity	NPC315491
0.7427	Intermediate Similarity	NPC23420
0.7427	Intermediate Similarity	NPC45459
0.7427	Intermediate Similarity	NPC106771
0.7427	Intermediate Similarity	NPC213308
0.7427	Intermediate Similarity	NPC205254
0.7415	Intermediate Similarity	NPC212213
0.7413	Intermediate Similarity	NPC76748
0.7411	Intermediate Similarity	NPC162002
0.7411	Intermediate Similarity	NPC295228
0.7404	Intermediate Similarity	NPC475774
0.7393	Intermediate Similarity	NPC476116
0.7391	Intermediate Similarity	NPC475935
0.7391	Intermediate Similarity	NPC94211
0.7391	Intermediate Similarity	NPC52909
0.7368	Intermediate Similarity	NPC48192
0.7366	Intermediate Similarity	NPC174489
0.7364	Intermediate Similarity	NPC214980
0.7356	Intermediate Similarity	NPC57398
0.7356	Intermediate Similarity	NPC470678
0.7354	Intermediate Similarity	NPC279189
0.7354	Intermediate Similarity	NPC207686
0.7353	Intermediate Similarity	NPC326634
0.7343	Intermediate Similarity	NPC315957
0.7343	Intermediate Similarity	NPC19872
0.7333	Intermediate Similarity	NPC472111
0.7325	Intermediate Similarity	NPC39092
0.7321	Intermediate Similarity	NPC476098
0.732	Intermediate Similarity	NPC252590
0.7317	Intermediate Similarity	NPC242209
0.7311	Intermediate Similarity	NPC185782
0.7309	Intermediate Similarity	NPC476451
0.7301	Intermediate Similarity	NPC26641
0.7296	Intermediate Similarity	NPC474958
0.7285	Intermediate Similarity	NPC103687
0.7285	Intermediate Similarity	NPC132631
0.7277	Intermediate Similarity	NPC167860
0.7277	Intermediate Similarity	NPC123976
0.7273	Intermediate Similarity	NPC211416
0.7269	Intermediate Similarity	NPC41679
0.7269	Intermediate Similarity	NPC274982
0.7264	Intermediate Similarity	NPC287208
0.7264	Intermediate Similarity	NPC477111
0.7261	Intermediate Similarity	NPC470504
0.726	Intermediate Similarity	NPC310118
0.726	Intermediate Similarity	NPC60621
0.7259	Intermediate Similarity	NPC96890
0.7256	Intermediate Similarity	NPC476287
0.7256	Intermediate Similarity	NPC266931
0.7251	Intermediate Similarity	NPC477113
0.7246	Intermediate Similarity	NPC239954
0.7243	Intermediate Similarity	NPC208284
0.724	Intermediate Similarity	NPC97367
0.7222	Intermediate Similarity	NPC72980
0.722	Intermediate Similarity	NPC198673
0.7217	Intermediate Similarity	NPC88008
0.7211	Intermediate Similarity	NPC129721
0.7209	Intermediate Similarity	NPC26679
0.7205	Intermediate Similarity	NPC81175
0.7204	Intermediate Similarity	NPC47059
0.7204	Intermediate Similarity	NPC165349
0.7204	Intermediate Similarity	NPC329708
0.7204	Intermediate Similarity	NPC472259
0.7204	Intermediate Similarity	NPC264166
0.7204	Intermediate Similarity	NPC274291
0.7204	Intermediate Similarity	NPC118832
0.7202	Intermediate Similarity	NPC471178
0.7198	Intermediate Similarity	NPC474188
0.7192	Intermediate Similarity	NPC246700
0.7192	Intermediate Similarity	NPC128751
0.7181	Intermediate Similarity	NPC477549
0.7164	Intermediate Similarity	NPC108011
0.7164	Intermediate Similarity	NPC284678
0.7157	Intermediate Similarity	NPC469497
0.7157	Intermediate Similarity	NPC106833
0.7143	Intermediate Similarity	NPC216369
0.7136	Intermediate Similarity	NPC106937
0.7136	Intermediate Similarity	NPC270918
0.7135	Intermediate Similarity	NPC131718
0.713	Intermediate Similarity	NPC316981
0.7129	Intermediate Similarity	NPC287437
0.712	Intermediate Similarity	NPC60553
0.7117	Intermediate Similarity	NPC130570
0.7115	Intermediate Similarity	NPC90229
0.7114	Intermediate Similarity	NPC176127
0.711	Intermediate Similarity	NPC477110
0.7107	Intermediate Similarity	NPC474409
0.7107	Intermediate Similarity	NPC471294
0.7101	Intermediate Similarity	NPC276517
0.71	Intermediate Similarity	NPC295452
0.71	Intermediate Similarity	NPC171393
0.7098	Intermediate Similarity	NPC110151
0.7098	Intermediate Similarity	NPC124542
0.7098	Intermediate Similarity	NPC471177
0.7098	Intermediate Similarity	NPC59779
0.7095	Intermediate Similarity	NPC234197
0.7087	Intermediate Similarity	NPC473342
0.7087	Intermediate Similarity	NPC304187
0.7087	Intermediate Similarity	NPC477167
0.7087	Intermediate Similarity	NPC477861
0.7087	Intermediate Similarity	NPC477166
0.7081	Intermediate Similarity	NPC168911
0.7081	Intermediate Similarity	NPC474916
0.7078	Intermediate Similarity	NPC27041
0.7078	Intermediate Similarity	NPC469727
0.7065	Intermediate Similarity	NPC307191
0.7065	Intermediate Similarity	NPC314394
0.7061	Intermediate Similarity	NPC245055
0.7059	Intermediate Similarity	NPC276657
0.7056	Intermediate Similarity	NPC158129
0.7051	Intermediate Similarity	NPC112206
0.7051	Intermediate Similarity	NPC202605
0.7051	Intermediate Similarity	NPC207020
0.7051	Intermediate Similarity	NPC219087
0.7051	Intermediate Similarity	NPC471603
0.7042	Intermediate Similarity	NPC285558
0.704	Intermediate Similarity	NPC167908
0.7037	Intermediate Similarity	NPC309845
0.7035	Intermediate Similarity	NPC150048
0.7035	Intermediate Similarity	NPC203754
0.7026	Intermediate Similarity	NPC473312
0.7024	Intermediate Similarity	NPC472289
0.7023	Intermediate Similarity	NPC171787
0.7021	Intermediate Similarity	NPC470111

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 NPC476121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	480
0.1-0.2	882
0.2-0.3	630
0.3-0.4	2385
0.4-0.5	2737
0.5-0.6	1691
0.6-0.7	331
0.7-0.8	14
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
0.7927	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD7112	Discontinued
0.7475	Intermediate Similarity	NPD1038	Approved
0.7452	Intermediate Similarity	NPD4795	Phase 2
0.7427	Intermediate Similarity	NPD484	Approved
0.7389	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD925	Approved
0.7382	Intermediate Similarity	NPD926	Approved
0.7381	Intermediate Similarity	NPD7222	Phase 2
0.7349	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD425	Approved
0.7344	Intermediate Similarity	NPD424	Approved
0.7343	Intermediate Similarity	NPD1739	Approved
0.7343	Intermediate Similarity	NPD1740	Approved
0.7333	Intermediate Similarity	NPD9690	Approved
0.7321	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD9705	Discontinued
0.7316	Intermediate Similarity	NPD112	Approved
0.7282	Intermediate Similarity	NPD7948	Phase 1
0.722	Intermediate Similarity	NPD9695	Approved
0.7217	Intermediate Similarity	NPD7452	Approved
0.7217	Intermediate Similarity	NPD1197	Approved
0.7217	Intermediate Similarity	NPD7453	Approved
0.7204	Intermediate Similarity	NPD4035	Approved
0.7204	Intermediate Similarity	NPD32	Approved
0.7204	Intermediate Similarity	NPD4033	Approved
0.7204	Intermediate Similarity	NPD31	Approved
0.7204	Intermediate Similarity	NPD4122	Approved
0.7204	Intermediate Similarity	NPD4037	Approved
0.7204	Intermediate Similarity	NPD4036	Approved
0.7204	Intermediate Similarity	NPD4034	Approved
0.7204	Intermediate Similarity	NPD4039	Approved
0.7204	Intermediate Similarity	NPD4038	Approved
0.72	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5065	Approved
0.7156	Intermediate Similarity	NPD6991	Approved
0.7156	Intermediate Similarity	NPD4886	Phase 2
0.7143	Intermediate Similarity	NPD2383	Phase 1
0.7143	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD802	Phase 2
0.711	Intermediate Similarity	NPD5612	Discontinued
0.7109	Intermediate Similarity	NPD6975	Discontinued
0.7101	Intermediate Similarity	NPD4418	Discontinued
0.7089	Intermediate Similarity	NPD5530	Phase 1
0.7065	Intermediate Similarity	NPD4203	Approved
0.7065	Intermediate Similarity	NPD4204	Approved
0.7028	Intermediate Similarity	NPD3931	Approved
0.7028	Intermediate Similarity	NPD3928	Approved
0.7023	Intermediate Similarity	NPD7672	Approved
0.7023	Intermediate Similarity	NPD7671	Approved
0.7	Intermediate Similarity	NPD2882	Phase 1
0.7	Intermediate Similarity	NPD6159	Phase 2
0.6995	Remote Similarity	NPD5255	Approved
0.6978	Remote Similarity	NPD7603	Discontinued
0.6968	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2762	Phase 2
0.6954	Remote Similarity	NPD2781	Approved
0.695	Remote Similarity	NPD5100	Phase 3
0.695	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4845	Discontinued
0.6944	Remote Similarity	NPD5658	Approved
0.6939	Remote Similarity	NPD2780	Approved
0.6939	Remote Similarity	NPD2782	Approved
0.693	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3923	Approved
0.6923	Remote Similarity	NPD3921	Approved
0.6923	Remote Similarity	NPD3924	Approved
0.6923	Remote Similarity	NPD3922	Approved
0.6923	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6158	Phase 2
0.6911	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3354	Phase 2
0.6888	Remote Similarity	NPD5050	Approved
0.6887	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6999	Discontinued
0.6866	Remote Similarity	NPD2187	Approved
0.6866	Remote Similarity	NPD2189	Approved
0.6858	Remote Similarity	NPD4890	Phase 2
0.6857	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD1856	Discontinued
0.6842	Remote Similarity	NPD9689	Approved
0.6833	Remote Similarity	NPD4897	Phase 2
0.683	Remote Similarity	NPD6856	Discontinued
0.6828	Remote Similarity	NPD2070	Approved
0.6828	Remote Similarity	NPD2071	Approved
0.6828	Remote Similarity	NPD2069	Approved
0.6828	Remote Similarity	NPD2068	Approved
0.6822	Remote Similarity	NPD4511	Phase 1
0.682	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3816	Phase 1
0.6818	Remote Similarity	NPD3330	Phase 1
0.6818	Remote Similarity	NPD3815	Phase 1
0.6814	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD2175	Phase 3
0.6808	Remote Similarity	NPD2176	Approved
0.6808	Remote Similarity	NPD3825	Phase 3
0.6808	Remote Similarity	NPD2177	Approved
0.6806	Remote Similarity	NPD1183	Approved
0.68	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7666	Phase 3
0.6789	Remote Similarity	NPD7665	Phase 2
0.6787	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5601	Phase 2
0.6772	Remote Similarity	NPD3813	Approved
0.6769	Remote Similarity	NPD5559	Phase 2
0.6769	Remote Similarity	NPD7555	Discontinued
0.6762	Remote Similarity	NPD6569	Phase 2
0.6762	Remote Similarity	NPD3404	Approved
0.6759	Remote Similarity	NPD4044	Discontinued
0.6758	Remote Similarity	NPD4520	Approved
0.6756	Remote Similarity	NPD6242	Discontinued
0.6754	Remote Similarity	NPD1661	Suspended
0.6754	Remote Similarity	NPD4703	Approved
0.6754	Remote Similarity	NPD4702	Approved
0.6751	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1325	Approved
0.675	Remote Similarity	NPD1326	Approved
0.6749	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6281	Approved
0.6733	Remote Similarity	NPD6492	Phase 2
0.673	Remote Similarity	NPD4551	Phase 2
0.6715	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1229	Phase 2
0.6714	Remote Similarity	NPD1622	Discontinued
0.6712	Remote Similarity	NPD2916	Discontinued
0.6709	Remote Similarity	NPD7068	Approved
0.6709	Remote Similarity	NPD7067	Approved
0.67	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD750	Phase 2
0.6683	Remote Similarity	NPD706	Phase 1
0.6682	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1213	Phase 3
0.6667	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5051	Phase 1
0.6667	Remote Similarity	NPD5891	Approved
0.6667	Remote Similarity	NPD2021	Discontinued
0.6667	Remote Similarity	NPD5045	Phase 2
0.6667	Remote Similarity	NPD7567	Approved
0.6667	Remote Similarity	NPD1684	Approved
0.6667	Remote Similarity	NPD1685	Approved
0.6652	Remote Similarity	NPD5507	Approved
0.6652	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6494	Phase 2
0.6652	Remote Similarity	NPD5506	Approved
0.6651	Remote Similarity	NPD9687	Approved
0.6651	Remote Similarity	NPD3397	Phase 2
0.6651	Remote Similarity	NPD5425	Phase 1
0.6651	Remote Similarity	NPD9688	Approved
0.665	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8101	Phase 3
0.6637	Remote Similarity	NPD2615	Phase 3
0.6637	Remote Similarity	NPD2616	Phase 3
0.6636	Remote Similarity	NPD4612	Discontinued
0.6636	Remote Similarity	NPD5495	Phase 2
0.6634	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2757	Phase 2
0.6622	Remote Similarity	NPD5939	Approved
0.6622	Remote Similarity	NPD3939	Suspended
0.6622	Remote Similarity	NPD949	Phase 1
0.6622	Remote Similarity	NPD5936	Approved
0.6621	Remote Similarity	NPD7001	Phase 3
0.6616	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3962	Phase 2
0.6611	Remote Similarity	NPD3959	Phase 2
0.6605	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6595	Phase 3
0.6602	Remote Similarity	NPD6452	Discontinued
0.6599	Remote Similarity	NPD2581	Approved
0.6599	Remote Similarity	NPD9382	Approved
0.6599	Remote Similarity	NPD9383	Approved
0.6599	Remote Similarity	NPD2582	Approved
0.6595	Remote Similarity	NPD8512	Phase 3
0.6595	Remote Similarity	NPD1995	Approved
0.6595	Remote Similarity	NPD1993	Approved
0.6595	Remote Similarity	NPD1994	Approved
0.6592	Remote Similarity	NPD5097	Phase 2
0.6591	Remote Similarity	NPD1392	Approved
0.6591	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3477	Phase 2
0.6589	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3321	Discontinued
0.6587	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7558	Phase 2
0.658	Remote Similarity	NPD4547	Phase 3
0.6578	Remote Similarity	NPD6957	Approved
0.6578	Remote Similarity	NPD6958	Approved
0.6578	Remote Similarity	NPD5287	Discontinued
0.6578	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8395	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