NPASS Compound

Structure

NPC60006 OpenBabel07101719242D 22 24 0 0 1 0 0 0 0 0999 V2000 -0.3621 -3.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2202 -2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7579 -2.3225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.7045 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 -1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6722 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 -0.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 0.9819 0.0000 Br 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 1.9890 -1.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2257 -2.6361 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5382 -0.0181 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7634 -2.4271 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 9 2 0 0 0 0 7 18 2 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 8 1 6 0 0 0 11 16 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 17 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.38
Volume:	534.525
LogP:	5.887
LogD:	5.202
LogS:	-4.514
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	4.927
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.748
MDCK Permeability:	4.2880925320787355e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.749
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.421
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	97.00154876708984%
Volume Distribution (VD):	1.001
Pgp-substrate:	1.6092289686203003%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.254
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	5.096
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.394
Human Hepatotoxicity (H-HT):	0.711
Drug-inuced Liver Injury (DILI):	0.409
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.966
Carcinogencity:	0.048
Eye Corrosion:	0.96
Eye Irritation:	0.695
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC60006

Natural Product ID:	NPC60006
*Common Name:**	14-Methyleudistomidin C
IUPAC Name:	5-bromo-1-[(1S)-1-(dimethylamino)-2-methylsulfanylethyl]-9H-pyrido[3,4-b]indol-6-ol
Synonyms:	14-Methyleudistomidin C
Standard InCHIKey:	UXXSAQIRPRDAQT-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C16H18BrN3OS/c1-20(2)11(8-22-3)16-15-9(6-7-18-16)13-10(19-15)4-5-12(21)14(13)17/h4-7,11,19,21H,8H2,1-3H3/t11-/m1/s1
SMILES:	CSC[C@H](c1nccc2c1[nH]c1c2c(Br)c(cc1)O)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504090
PubChem CID:	10045316
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
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	=	0.98	ug.mL-1	PMID[552627]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	0.42	ug.mL-1	PMID[552627]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	0.57	ug.mL-1	PMID[552627]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.41	ug.mL-1	PMID[552627]

☑ 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 NPC60006 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	9989
0.2-0.3	9473
0.3-0.4	15507
0.4-0.5	3467
0.5-0.6	2170
0.6-0.7	1215
0.7-0.8	160
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC245348
0.9005	High Similarity	NPC476124
0.8852	High Similarity	NPC255110
0.8818	High Similarity	NPC476121
0.8676	High Similarity	NPC475070
0.85	High Similarity	NPC97902
0.8436	Intermediate Similarity	NPC477610
0.8284	Intermediate Similarity	NPC222018
0.8148	Intermediate Similarity	NPC476041
0.8148	Intermediate Similarity	NPC304926
0.8122	Intermediate Similarity	NPC5145
0.8111	Intermediate Similarity	NPC477609
0.8069	Intermediate Similarity	NPC171171
0.7991	Intermediate Similarity	NPC292958
0.799	Intermediate Similarity	NPC476167
0.797	Intermediate Similarity	NPC204717
0.7961	Intermediate Similarity	NPC99666
0.7957	Intermediate Similarity	NPC39092
0.7952	Intermediate Similarity	NPC176538
0.7946	Intermediate Similarity	NPC477608
0.7946	Intermediate Similarity	NPC477607
0.7943	Intermediate Similarity	NPC192315
0.7931	Intermediate Similarity	NPC314002
0.7921	Intermediate Similarity	NPC220765
0.7883	Intermediate Similarity	NPC470501
0.7874	Intermediate Similarity	NPC324149
0.7838	Intermediate Similarity	NPC470502
0.7822	Intermediate Similarity	NPC6215
0.781	Intermediate Similarity	NPC77555
0.7768	Intermediate Similarity	NPC470503
0.7752	Intermediate Similarity	NPC246518
0.7723	Intermediate Similarity	NPC184964
0.771	Intermediate Similarity	NPC211813
0.77	Intermediate Similarity	NPC249040
0.7639	Intermediate Similarity	NPC470505
0.7636	Intermediate Similarity	NPC128084
0.7593	Intermediate Similarity	NPC223427
0.7586	Intermediate Similarity	NPC295228
0.7585	Intermediate Similarity	NPC470504
0.758	Intermediate Similarity	NPC476116
0.7559	Intermediate Similarity	NPC156704
0.7558	Intermediate Similarity	NPC470500
0.7546	Intermediate Similarity	NPC473761
0.7535	Intermediate Similarity	NPC303820
0.7535	Intermediate Similarity	NPC205254
0.7535	Intermediate Similarity	NPC23420
0.7535	Intermediate Similarity	NPC106771
0.7534	Intermediate Similarity	NPC142901
0.7532	Intermediate Similarity	NPC200553
0.7521	Intermediate Similarity	NPC41679
0.7512	Intermediate Similarity	NPC46580
0.7511	Intermediate Similarity	NPC213530
0.7511	Intermediate Similarity	NPC193267
0.75	Intermediate Similarity	NPC94211
0.75	Intermediate Similarity	NPC475935
0.75	Intermediate Similarity	NPC307963
0.75	Intermediate Similarity	NPC232727
0.75	Intermediate Similarity	NPC52909
0.7489	Intermediate Similarity	NPC476451
0.7488	Intermediate Similarity	NPC92111
0.7476	Intermediate Similarity	NPC32771
0.7458	Intermediate Similarity	NPC81175
0.7454	Intermediate Similarity	NPC315491
0.7454	Intermediate Similarity	NPC45459
0.7441	Intermediate Similarity	NPC76748
0.7438	Intermediate Similarity	NPC82331
0.7436	Intermediate Similarity	NPC162002
0.7431	Intermediate Similarity	NPC476138
0.7431	Intermediate Similarity	NPC245816
0.743	Intermediate Similarity	NPC251090
0.7427	Intermediate Similarity	NPC88363
0.7421	Intermediate Similarity	NPC80596
0.7415	Intermediate Similarity	NPC37152
0.7415	Intermediate Similarity	NPC474958
0.7404	Intermediate Similarity	NPC48938
0.7393	Intermediate Similarity	NPC174489
0.7393	Intermediate Similarity	NPC296527
0.7382	Intermediate Similarity	NPC207686
0.7382	Intermediate Similarity	NPC279189
0.7378	Intermediate Similarity	NPC470799
0.7378	Intermediate Similarity	NPC8022
0.7373	Intermediate Similarity	NPC213308
0.7368	Intermediate Similarity	NPC310118
0.7366	Intermediate Similarity	NPC266931
0.7362	Intermediate Similarity	NPC477549
0.7354	Intermediate Similarity	NPC208284
0.7353	Intermediate Similarity	NPC171393
0.7353	Intermediate Similarity	NPC295452
0.7352	Intermediate Similarity	NPC476098
0.7331	Intermediate Similarity	NPC26641
0.7311	Intermediate Similarity	NPC128751
0.7311	Intermediate Similarity	NPC246700
0.7309	Intermediate Similarity	NPC167860
0.7309	Intermediate Similarity	NPC123976
0.7304	Intermediate Similarity	NPC167908
0.7302	Intermediate Similarity	NPC326634
0.7294	Intermediate Similarity	NPC19872
0.7277	Intermediate Similarity	NPC106833
0.7277	Intermediate Similarity	NPC469497
0.7273	Intermediate Similarity	NPC200836
0.7273	Intermediate Similarity	NPC53144
0.7269	Intermediate Similarity	NPC242209
0.7269	Intermediate Similarity	NPC477861
0.7244	Intermediate Similarity	NPC26679
0.7241	Intermediate Similarity	NPC274229
0.7229	Intermediate Similarity	NPC211416
0.7229	Intermediate Similarity	NPC130570
0.722	Intermediate Similarity	NPC82548
0.722	Intermediate Similarity	NPC477111
0.7217	Intermediate Similarity	NPC60621
0.7215	Intermediate Similarity	NPC315957
0.7215	Intermediate Similarity	NPC329793
0.7212	Intermediate Similarity	NPC96890
0.7212	Intermediate Similarity	NPC248454
0.721	Intermediate Similarity	NPC110151
0.7208	Intermediate Similarity	NPC473312
0.7188	Intermediate Similarity	NPC185782
0.7177	Intermediate Similarity	NPC72980
0.7176	Intermediate Similarity	NPC106937
0.7175	Intermediate Similarity	NPC88008
0.7168	Intermediate Similarity	NPC316981
0.7162	Intermediate Similarity	NPC285558
0.716	Intermediate Similarity	NPC471891
0.7149	Intermediate Similarity	NPC469928
0.7137	Intermediate Similarity	NPC476287
0.7136	Intermediate Similarity	NPC121772
0.713	Intermediate Similarity	NPC473342
0.713	Intermediate Similarity	NPC477166
0.713	Intermediate Similarity	NPC304187
0.713	Intermediate Similarity	NPC477167
0.713	Intermediate Similarity	NPC477113
0.7123	Intermediate Similarity	NPC284678
0.7123	Intermediate Similarity	NPC265576
0.7119	Intermediate Similarity	NPC178858
0.7118	Intermediate Similarity	NPC27041
0.7113	Intermediate Similarity	NPC184225
0.7112	Intermediate Similarity	NPC280272
0.7108	Intermediate Similarity	NPC216369
0.7106	Intermediate Similarity	NPC253580
0.7106	Intermediate Similarity	NPC314954
0.7101	Intermediate Similarity	NPC33064
0.7101	Intermediate Similarity	NPC245055
0.71	Intermediate Similarity	NPC276657
0.7098	Intermediate Similarity	NPC473362
0.7098	Intermediate Similarity	NPC166492
0.7098	Intermediate Similarity	NPC270918
0.7097	Intermediate Similarity	NPC329541
0.7094	Intermediate Similarity	NPC214142
0.7094	Intermediate Similarity	NPC131718
0.7093	Intermediate Similarity	NPC207020
0.7089	Intermediate Similarity	NPC15102
0.708	Intermediate Similarity	NPC85273
0.7078	Intermediate Similarity	NPC153042
0.7075	Intermediate Similarity	NPC163055
0.7075	Intermediate Similarity	NPC176127
0.7074	Intermediate Similarity	NPC74969
0.7067	Intermediate Similarity	NPC474409
0.7064	Intermediate Similarity	NPC34580
0.7064	Intermediate Similarity	NPC261251
0.7064	Intermediate Similarity	NPC470126
0.7064	Intermediate Similarity	NPC124920
0.7064	Intermediate Similarity	NPC276517
0.7064	Intermediate Similarity	NPC304307
0.7064	Intermediate Similarity	NPC118559
0.7054	Intermediate Similarity	NPC474145
0.7054	Intermediate Similarity	NPC475841
0.7045	Intermediate Similarity	NPC153400
0.7037	Intermediate Similarity	NPC231536
0.7034	Intermediate Similarity	NPC100547
0.7028	Intermediate Similarity	NPC307191
0.7028	Intermediate Similarity	NPC314394
0.7022	Intermediate Similarity	NPC53344
0.7021	Intermediate Similarity	NPC319232
0.7021	Intermediate Similarity	NPC24370
0.7018	Intermediate Similarity	NPC219087
0.7018	Intermediate Similarity	NPC471603
0.7017	Intermediate Similarity	NPC469554
0.7012	Intermediate Similarity	NPC82472
0.7009	Intermediate Similarity	NPC94943
0.7004	Intermediate Similarity	NPC322135
0.7004	Intermediate Similarity	NPC223409
0.7004	Intermediate Similarity	NPC95240
0.7	Intermediate Similarity	NPC475746
0.7	Intermediate Similarity	NPC121903
0.7	Intermediate Similarity	NPC183407
0.7	Intermediate Similarity	NPC272549
0.7	Intermediate Similarity	NPC477110
0.6991	Remote Similarity	NPC171787
0.6991	Remote Similarity	NPC476465
0.6987	Remote Similarity	NPC478074
0.6977	Remote Similarity	NPC62749
0.6975	Remote Similarity	NPC14288
0.6971	Remote Similarity	NPC97343
0.697	Remote Similarity	NPC469727
0.6963	Remote Similarity	NPC190007
0.6959	Remote Similarity	NPC95783
0.6957	Remote Similarity	NPC474561
0.6957	Remote Similarity	NPC49954
0.6949	Remote Similarity	NPC214980
0.6946	Remote Similarity	NPC54803

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 NPC60006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	799
0.2-0.3	745
0.3-0.4	2194
0.4-0.5	2634
0.5-0.6	1921
0.6-0.7	491
0.7-0.8	23
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
0.801	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1038	Approved
0.7477	Intermediate Similarity	NPD7948	Phase 1
0.7455	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD484	Approved
0.7451	Intermediate Similarity	NPD5065	Approved
0.7418	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7112	Discontinued
0.7333	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4795	Phase 2
0.7301	Intermediate Similarity	NPD5612	Discontinued
0.7248	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1739	Approved
0.7215	Intermediate Similarity	NPD1740	Approved
0.7188	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD802	Phase 2
0.7167	Intermediate Similarity	NPD7603	Discontinued
0.7162	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5658	Approved
0.704	Intermediate Similarity	NPD4044	Discontinued
0.7027	Intermediate Similarity	NPD4511	Phase 1
0.7018	Intermediate Similarity	NPD3330	Phase 1
0.7009	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD3928	Approved
0.6996	Remote Similarity	NPD3931	Approved
0.6991	Remote Similarity	NPD2189	Approved
0.6991	Remote Similarity	NPD2187	Approved
0.6986	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4886	Phase 2
0.6957	Remote Similarity	NPD425	Approved
0.6957	Remote Similarity	NPD424	Approved
0.694	Remote Similarity	NPD2021	Discontinued
0.6937	Remote Similarity	NPD3825	Phase 3
0.6917	Remote Similarity	NPD2471	Approved
0.6917	Remote Similarity	NPD2472	Approved
0.6907	Remote Similarity	NPD1258	Discontinued
0.6903	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5559	Phase 2
0.689	Remote Similarity	NPD1326	Approved
0.689	Remote Similarity	NPD1325	Approved
0.688	Remote Similarity	NPD6242	Discontinued
0.6872	Remote Similarity	NPD7222	Phase 2
0.6872	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5050	Approved
0.6861	Remote Similarity	NPD3814	Phase 1
0.6858	Remote Similarity	NPD4034	Approved
0.6858	Remote Similarity	NPD4038	Approved
0.6858	Remote Similarity	NPD32	Approved
0.6858	Remote Similarity	NPD4037	Approved
0.6858	Remote Similarity	NPD4122	Approved
0.6858	Remote Similarity	NPD4039	Approved
0.6858	Remote Similarity	NPD4035	Approved
0.6858	Remote Similarity	NPD4036	Approved
0.6858	Remote Similarity	NPD4033	Approved
0.6858	Remote Similarity	NPD31	Approved
0.6844	Remote Similarity	NPD8073	Approved
0.684	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6595	Phase 3
0.681	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6492	Phase 2
0.6792	Remote Similarity	NPD8512	Phase 3
0.6789	Remote Similarity	NPD2383	Phase 1
0.6786	Remote Similarity	NPD8396	Approved
0.6786	Remote Similarity	NPD2175	Phase 3
0.6786	Remote Similarity	NPD2176	Approved
0.6786	Remote Similarity	NPD2177	Approved
0.6786	Remote Similarity	NPD8395	Approved
0.6784	Remote Similarity	NPD8272	Phase 2
0.6777	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8284	Discontinued
0.6765	Remote Similarity	NPD4890	Phase 2
0.6759	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5530	Phase 1
0.6747	Remote Similarity	NPD6276	Discontinued
0.6746	Remote Similarity	NPD926	Approved
0.6746	Remote Similarity	NPD925	Approved
0.6742	Remote Similarity	NPD3404	Approved
0.674	Remote Similarity	NPD8072	Approved
0.674	Remote Similarity	NPD6991	Approved
0.6726	Remote Similarity	NPD3127	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4865	Approved
0.6725	Remote Similarity	NPD7453	Approved
0.6725	Remote Similarity	NPD1392	Approved
0.6725	Remote Similarity	NPD7452	Approved
0.6723	Remote Similarity	NPD3354	Phase 2
0.6714	Remote Similarity	NPD9690	Approved
0.6712	Remote Similarity	NPD9695	Approved
0.6708	Remote Similarity	NPD7558	Phase 2
0.6707	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3610	Approved
0.6698	Remote Similarity	NPD3609	Approved
0.6697	Remote Similarity	NPD2762	Phase 2
0.6683	Remote Similarity	NPD112	Approved
0.6683	Remote Similarity	NPD9705	Discontinued
0.6682	Remote Similarity	NPD3396	Approved
0.6682	Remote Similarity	NPD3395	Approved
0.6667	Remote Similarity	NPD706	Phase 1
0.6653	Remote Similarity	NPD4558	Phase 2
0.6651	Remote Similarity	NPD6159	Phase 2
0.6651	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1661	Suspended
0.6639	Remote Similarity	NPD4845	Discontinued
0.6638	Remote Similarity	NPD5901	Discontinued
0.6636	Remote Similarity	NPD4203	Approved
0.6636	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4204	Approved
0.6635	Remote Similarity	NPD704	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5255	Approved
0.6635	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7068	Approved
0.6627	Remote Similarity	NPD8101	Phase 3
0.6627	Remote Similarity	NPD7067	Approved
0.6624	Remote Similarity	NPD2616	Phase 3
0.6624	Remote Similarity	NPD2615	Phase 3
0.6623	Remote Similarity	NPD7671	Approved
0.6623	Remote Similarity	NPD7672	Approved
0.6623	Remote Similarity	NPD6975	Discontinued
0.6619	Remote Similarity	NPD5138	Approved
0.6619	Remote Similarity	NPD5140	Approved
0.6609	Remote Similarity	NPD949	Phase 1
0.6609	Remote Similarity	NPD3003	Approved
0.6609	Remote Similarity	NPD5936	Approved
0.6609	Remote Similarity	NPD5067	Phase 2
0.6609	Remote Similarity	NPD5939	Approved
0.6609	Remote Similarity	NPD5066	Phase 2
0.6607	Remote Similarity	NPD4418	Discontinued
0.6605	Remote Similarity	NPD5100	Phase 3
0.6598	Remote Similarity	NPD7711	Discontinued
0.6595	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8442	Discontinued
0.6584	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.658	Remote Similarity	NPD1197	Approved
0.6571	Remote Similarity	NPD4850	Phase 1
0.6569	Remote Similarity	NPD4703	Approved
0.6569	Remote Similarity	NPD4702	Approved
0.6567	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3013	Phase 3
0.6565	Remote Similarity	NPD5426	Phase 3
0.6565	Remote Similarity	NPD3255	Phase 1
0.6565	Remote Similarity	NPD3254	Phase 1
0.6561	Remote Similarity	NPD8431	Approved
0.6561	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8106	Phase 2
0.6557	Remote Similarity	NPD2062	Phase 2
0.6556	Remote Similarity	NPD4403	Phase 3
0.6556	Remote Similarity	NPD4401	Phase 2
0.6553	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD2882	Phase 1
0.6553	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD6158	Phase 2
0.6552	Remote Similarity	NPD2916	Discontinued
0.6545	Remote Similarity	NPD3082	Discontinued
0.6543	Remote Similarity	NPD7555	Discontinued
0.6534	Remote Similarity	NPD3959	Phase 2
0.6534	Remote Similarity	NPD3962	Phase 2
0.653	Remote Similarity	NPD2094	Phase 2
0.653	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.653	Remote Similarity	NPD2095	Phase 2
0.653	Remote Similarity	NPD2092	Phase 2
0.6528	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2781	Approved
0.6526	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2641	Approved
0.6526	Remote Similarity	NPD2640	Approved
0.6525	Remote Similarity	NPD4897	Phase 2
0.6522	Remote Similarity	NPD2837	Discontinued
0.652	Remote Similarity	NPD5051	Phase 1
0.6518	Remote Similarity	NPD3922	Approved
0.6518	Remote Similarity	NPD3921	Approved
0.6518	Remote Similarity	NPD1259	Discontinued
0.6518	Remote Similarity	NPD3923	Approved
0.6518	Remote Similarity	NPD3924	Approved
0.6511	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2780	Approved
0.6509	Remote Similarity	NPD2782	Approved
0.6508	Remote Similarity	NPD8100	Phase 3
0.6504	Remote Similarity	NPD6494	Phase 2
0.65	Remote Similarity	NPD2096	Phase 2
0.65	Remote Similarity	NPD2091	Phase 2
0.6498	Remote Similarity	NPD6957	Approved
0.6498	Remote Similarity	NPD6958	Approved
0.6496	Remote Similarity	NPD5482	Discontinued
0.6494	Remote Similarity	NPD3397	Phase 2
0.6493	Remote Similarity	NPD1685	Approved
0.6493	Remote Similarity	NPD1684	Approved
0.6488	Remote Similarity	NPD6246	Approved
0.6485	Remote Similarity	NPD3402	Phase 1
0.6485	Remote Similarity	NPD7194	Discontinued
0.6481	Remote Similarity	NPD482	Approved
0.6481	Remote Similarity	NPD4612	Discontinued
0.6481	Remote Similarity	NPD7666	Phase 3
0.6481	Remote Similarity	NPD7665	Phase 2
0.6478	Remote Similarity	NPD5669	Clinical (unspecified phase)

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