NPASS Compound

Structure

NPC101543 OpenBabel07101719512D 36 42 0 0 1 0 0 0 0 0999 V2000 2.5326 5.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7944 3.5696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 3.5696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9819 1.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8254 0.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4305 5.9819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2047 2.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0598 5.2047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8919 0.0844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5572 5.8254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1554 3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2711 1.7014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7014 4.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1147 0.7137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9156 4.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1213 3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 3.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 2.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1554 3.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2863 4.1147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6730 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 2.6730 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 1.4483 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 0.5573 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4427 3.1270 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9033 4.7354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8284 3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8284 3.8284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 17 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 21 2 0 0 0 0 13 30 1 0 0 0 0 14 22 1 0 0 0 0 14 31 2 0 0 0 0 15 16 1 0 0 0 0 15 26 1 6 0 0 0 16 27 1 1 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 18 25 2 0 0 0 0 19 32 1 0 0 0 0 20 25 1 0 0 0 0 20 34 1 0 0 0 0 21 23 1 0 0 0 0 21 35 1 0 0 0 0 22 24 2 0 0 0 0 22 36 1 0 0 0 0 23 28 2 0 0 0 0 24 29 1 0 0 0 0 25 33 1 0 0 0 0 26 28 1 0 0 0 0 26 30 2 0 0 0 0 27 29 2 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.2
Volume:	488.965
LogP:	5.555
LogD:	4.062
LogS:	-5.768
# Rotatable Bonds:	5
TPSA:	85.05
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	3.843
Fsp3:	0.241
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.113
MDCK Permeability:	7.600125172757544e-06
Pgp-inhibitor:	0.968
Pgp-substrate:	0.285
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	94.64962005615234%
Volume Distribution (VD):	1.232
Pgp-substrate:	5.3664045333862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.886
CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.852
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.376
CYP3A4-substrate:	0.926

ADMET: Excretion

Clearance (CL):	4.297
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.615
Human Hepatotoxicity (H-HT):	0.586
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.785
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.369
Carcinogencity:	0.716
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC101543

Natural Product ID:	NPC101543
*Common Name:**	Quassidine A
IUPAC Name:	4,8-dimethoxy-1-[(1R,2R)-2-(4-methoxy-9H-pyrido[3,4-b]indol-1-yl)cyclobutyl]-9H-pyrido[3,4-b]indole
Synonyms:
Standard InCHIKey:	MQTKEFAXTQTDJF-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C29H26N4O3/c1-34-20-10-6-8-18-24-22(36-3)14-31-27(29(24)33-25(18)20)16-12-11-15(16)26-28-23(21(35-2)13-30-26)17-7-4-5-9-19(17)32-28/h4-10,13-16,32-33H,11-12H2,1-3H3/t15-,16-/m1/s1
SMILES:	COc1cccc2c1[nH]c1c2c(OC)cnc1[C@@H]1CC[C@H]1c1ncc(c2c1[nH]c1c2cccc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087520
PubChem CID:	46184320
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
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	89390.0	nM	PMID[505128]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	88410.0	nM	PMID[505128]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[505128]

☑ 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 NPC101543 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	839
0.1-0.2	4761
0.2-0.3	12592
0.3-0.4	14613
0.4-0.5	5481
0.5-0.6	2522
0.6-0.7	1581
0.7-0.8	272
0.8-0.85	21
0.85-0.9	8
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9712	High Similarity	NPC469554
0.9108	High Similarity	NPC314954
0.9078	High Similarity	NPC26679
0.9024	High Similarity	NPC185782
0.8899	High Similarity	NPC53534
0.878	High Similarity	NPC476138
0.878	High Similarity	NPC245816
0.8768	High Similarity	NPC470799
0.8768	High Similarity	NPC8022
0.8761	High Similarity	NPC26543
0.867	High Similarity	NPC152620
0.8634	High Similarity	NPC19872
0.8619	High Similarity	NPC167860
0.8619	High Similarity	NPC123976
0.8472	Intermediate Similarity	NPC193267
0.8472	Intermediate Similarity	NPC213530
0.8411	Intermediate Similarity	NPC476287
0.8365	Intermediate Similarity	NPC176538
0.8364	Intermediate Similarity	NPC94157
0.8246	Intermediate Similarity	NPC475774
0.8238	Intermediate Similarity	NPC232727
0.8227	Intermediate Similarity	NPC310118
0.8221	Intermediate Similarity	NPC267928
0.8211	Intermediate Similarity	NPC476041
0.8211	Intermediate Similarity	NPC304926
0.8208	Intermediate Similarity	NPC285558
0.8136	Intermediate Similarity	NPC292958
0.8102	Intermediate Similarity	NPC5145
0.81	Intermediate Similarity	NPC132642
0.8082	Intermediate Similarity	NPC170114
0.8057	Intermediate Similarity	NPC476167
0.8052	Intermediate Similarity	NPC148889
0.8044	Intermediate Similarity	NPC473185
0.8044	Intermediate Similarity	NPC110151
0.8037	Intermediate Similarity	NPC470549
0.8035	Intermediate Similarity	NPC295228
0.8034	Intermediate Similarity	NPC471891
0.8018	Intermediate Similarity	NPC199667
0.8018	Intermediate Similarity	NPC476451
0.8009	Intermediate Similarity	NPC192315
0.799	Intermediate Similarity	NPC84853
0.7982	Intermediate Similarity	NPC208284
0.7972	Intermediate Similarity	NPC473181
0.7972	Intermediate Similarity	NPC187558
0.7953	Intermediate Similarity	NPC470500
0.7948	Intermediate Similarity	NPC180504
0.7948	Intermediate Similarity	NPC141053
0.7945	Intermediate Similarity	NPC473180
0.7939	Intermediate Similarity	NPC475253
0.7931	Intermediate Similarity	NPC477861
0.7926	Intermediate Similarity	NPC287208
0.7907	Intermediate Similarity	NPC223427
0.7892	Intermediate Similarity	NPC473179
0.7888	Intermediate Similarity	NPC101350
0.787	Intermediate Similarity	NPC475070
0.7864	Intermediate Similarity	NPC284678
0.7848	Intermediate Similarity	NPC469594
0.7847	Intermediate Similarity	NPC76748
0.7845	Intermediate Similarity	NPC235685
0.7828	Intermediate Similarity	NPC471080
0.7828	Intermediate Similarity	NPC469592
0.7821	Intermediate Similarity	NPC81175
0.782	Intermediate Similarity	NPC307963
0.781	Intermediate Similarity	NPC92111
0.7807	Intermediate Similarity	NPC6215
0.7799	Intermediate Similarity	NPC296527
0.7799	Intermediate Similarity	NPC242928
0.7768	Intermediate Similarity	NPC473183
0.7749	Intermediate Similarity	NPC473186
0.7743	Intermediate Similarity	NPC60621
0.7721	Intermediate Similarity	NPC18487
0.7712	Intermediate Similarity	NPC473312
0.7706	Intermediate Similarity	NPC165349
0.7706	Intermediate Similarity	NPC274291
0.7706	Intermediate Similarity	NPC264166
0.7706	Intermediate Similarity	NPC47059
0.7706	Intermediate Similarity	NPC260434
0.7706	Intermediate Similarity	NPC118832
0.7706	Intermediate Similarity	NPC329708
0.7685	Intermediate Similarity	NPC329793
0.7685	Intermediate Similarity	NPC315957
0.7682	Intermediate Similarity	NPC82548
0.7682	Intermediate Similarity	NPC473184
0.7682	Intermediate Similarity	NPC39370
0.7681	Intermediate Similarity	NPC474798
0.7664	Intermediate Similarity	NPC251090
0.7625	Intermediate Similarity	NPC91868
0.7625	Intermediate Similarity	NPC63971
0.7623	Intermediate Similarity	NPC258048
0.7607	Intermediate Similarity	NPC182222
0.7606	Intermediate Similarity	NPC324149
0.7604	Intermediate Similarity	NPC121772
0.7598	Intermediate Similarity	NPC122436
0.7591	Intermediate Similarity	NPC472111
0.7581	Intermediate Similarity	NPC13880
0.7568	Intermediate Similarity	NPC174672
0.7568	Intermediate Similarity	NPC174758
0.7558	Intermediate Similarity	NPC128823
0.7523	Intermediate Similarity	NPC477111
0.7523	Intermediate Similarity	NPC329747
0.7511	Intermediate Similarity	NPC41679
0.7511	Intermediate Similarity	NPC11408
0.7511	Intermediate Similarity	NPC266931
0.75	Intermediate Similarity	NPC472434
0.7489	Intermediate Similarity	NPC305984
0.7489	Intermediate Similarity	NPC476116
0.7489	Intermediate Similarity	NPC469589
0.7489	Intermediate Similarity	NPC473182
0.7478	Intermediate Similarity	NPC280272
0.7476	Intermediate Similarity	NPC176127
0.7466	Intermediate Similarity	NPC36229
0.7466	Intermediate Similarity	NPC16452
0.7466	Intermediate Similarity	NPC476581
0.7466	Intermediate Similarity	NPC470930
0.7457	Intermediate Similarity	NPC227908
0.7455	Intermediate Similarity	NPC11464
0.7448	Intermediate Similarity	NPC217554
0.7445	Intermediate Similarity	NPC288349
0.7444	Intermediate Similarity	NPC476465
0.7444	Intermediate Similarity	NPC475910
0.7443	Intermediate Similarity	NPC249040
0.7434	Intermediate Similarity	NPC473757
0.7434	Intermediate Similarity	NPC162530
0.7429	Intermediate Similarity	NPC161887
0.7414	Intermediate Similarity	NPC21638
0.7407	Intermediate Similarity	NPC226202
0.7407	Intermediate Similarity	NPC198673
0.7407	Intermediate Similarity	NPC475190
0.7406	Intermediate Similarity	NPC20249
0.7403	Intermediate Similarity	NPC470501
0.7397	Intermediate Similarity	NPC287437
0.7397	Intermediate Similarity	NPC4071
0.7397	Intermediate Similarity	NPC476578
0.7397	Intermediate Similarity	NPC476582
0.7395	Intermediate Similarity	NPC15801
0.7393	Intermediate Similarity	NPC48938
0.7391	Intermediate Similarity	NPC86078
0.7389	Intermediate Similarity	NPC171409
0.7389	Intermediate Similarity	NPC202768
0.7389	Intermediate Similarity	NPC296482
0.7389	Intermediate Similarity	NPC316981
0.7389	Intermediate Similarity	NPC53069
0.7389	Intermediate Similarity	NPC96405
0.7384	Intermediate Similarity	NPC24802
0.7378	Intermediate Similarity	NPC471304
0.7375	Intermediate Similarity	NPC477066
0.7368	Intermediate Similarity	NPC472027
0.7368	Intermediate Similarity	NPC274982
0.7368	Intermediate Similarity	NPC148183
0.7368	Intermediate Similarity	NPC477110
0.7368	Intermediate Similarity	NPC251936
0.7368	Intermediate Similarity	NPC152768
0.7364	Intermediate Similarity	NPC30540
0.7361	Intermediate Similarity	NPC99666
0.7359	Intermediate Similarity	NPC471506
0.7359	Intermediate Similarity	NPC470502
0.7358	Intermediate Similarity	NPC84478
0.7357	Intermediate Similarity	NPC478074
0.7357	Intermediate Similarity	NPC234078
0.7357	Intermediate Similarity	NPC221100
0.7355	Intermediate Similarity	NPC284141
0.7354	Intermediate Similarity	NPC477113
0.7352	Intermediate Similarity	NPC168911
0.7344	Intermediate Similarity	NPC478081
0.7344	Intermediate Similarity	NPC478082
0.7344	Intermediate Similarity	NPC477067
0.733	Intermediate Similarity	NPC31930
0.7321	Intermediate Similarity	NPC313189
0.7321	Intermediate Similarity	NPC135549
0.7319	Intermediate Similarity	NPC253580
0.7316	Intermediate Similarity	NPC477533
0.7316	Intermediate Similarity	NPC472099
0.7313	Intermediate Similarity	NPC472098
0.7308	Intermediate Similarity	NPC202503
0.73	Intermediate Similarity	NPC196718
0.73	Intermediate Similarity	NPC102593
0.73	Intermediate Similarity	NPC207686
0.7296	Intermediate Similarity	NPC470503
0.7295	Intermediate Similarity	NPC476518
0.7294	Intermediate Similarity	NPC131017
0.7288	Intermediate Similarity	NPC326363
0.7285	Intermediate Similarity	NPC234197
0.7281	Intermediate Similarity	NPC195268
0.7281	Intermediate Similarity	NPC477610
0.7281	Intermediate Similarity	NPC133140
0.7277	Intermediate Similarity	NPC470126
0.7277	Intermediate Similarity	NPC323345
0.7277	Intermediate Similarity	NPC476492
0.7277	Intermediate Similarity	NPC470164
0.7273	Intermediate Similarity	NPC239954
0.7268	Intermediate Similarity	NPC118511
0.7265	Intermediate Similarity	NPC162484
0.7264	Intermediate Similarity	NPC219963
0.7264	Intermediate Similarity	NPC266551
0.726	Intermediate Similarity	NPC14651
0.726	Intermediate Similarity	NPC121658
0.725	Intermediate Similarity	NPC184680
0.7244	Intermediate Similarity	NPC166492
0.7244	Intermediate Similarity	NPC473362
0.7243	Intermediate Similarity	NPC15102

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 NPC101543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	656
0.2-0.3	865
0.3-0.4	2028
0.4-0.5	2484
0.5-0.6	1876
0.6-0.7	750
0.7-0.8	101
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
0.7964	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD5482	Discontinued
0.7872	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1038	Approved
0.782	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD7558	Phase 2
0.7788	Intermediate Similarity	NPD1856	Discontinued
0.7788	Intermediate Similarity	NPD4795	Phase 2
0.7763	Intermediate Similarity	NPD5658	Approved
0.7727	Intermediate Similarity	NPD6961	Discontinued
0.7725	Intermediate Similarity	NPD3006	Discontinued
0.7706	Intermediate Similarity	NPD32	Approved
0.7706	Intermediate Similarity	NPD4033	Approved
0.7706	Intermediate Similarity	NPD4036	Approved
0.7706	Intermediate Similarity	NPD4037	Approved
0.7706	Intermediate Similarity	NPD4039	Approved
0.7706	Intermediate Similarity	NPD4122	Approved
0.7706	Intermediate Similarity	NPD4038	Approved
0.7706	Intermediate Similarity	NPD4034	Approved
0.7706	Intermediate Similarity	NPD4035	Approved
0.7706	Intermediate Similarity	NPD31	Approved
0.7702	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD5559	Phase 2
0.7685	Intermediate Similarity	NPD1740	Approved
0.7685	Intermediate Similarity	NPD1739	Approved
0.7655	Intermediate Similarity	NPD3402	Phase 1
0.7652	Intermediate Similarity	NPD3343	Phase 3
0.7639	Intermediate Similarity	NPD3825	Phase 3
0.7639	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7603	Discontinued
0.76	Intermediate Similarity	NPD5612	Discontinued
0.7581	Intermediate Similarity	NPD3477	Phase 2
0.7581	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4548	Discontinued
0.755	Intermediate Similarity	NPD4442	Phase 2
0.7533	Intermediate Similarity	NPD4429	Discontinued
0.7531	Intermediate Similarity	NPD7067	Approved
0.7531	Intermediate Similarity	NPD7068	Approved
0.751	Intermediate Similarity	NPD5450	Discontinued
0.75	Intermediate Similarity	NPD4502	Phase 2
0.747	Intermediate Similarity	NPD5018	Phase 3
0.7454	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2189	Approved
0.7444	Intermediate Similarity	NPD2187	Approved
0.7442	Intermediate Similarity	NPD6569	Phase 2
0.7436	Intermediate Similarity	NPD6968	Phase 2
0.7436	Intermediate Similarity	NPD6969	Phase 2
0.7424	Intermediate Similarity	NPD7194	Discontinued
0.7422	Intermediate Similarity	NPD4131	Phase 3
0.7422	Intermediate Similarity	NPD5067	Phase 2
0.7422	Intermediate Similarity	NPD5066	Phase 2
0.7415	Intermediate Similarity	NPD6494	Phase 2
0.7399	Intermediate Similarity	NPD7222	Phase 2
0.7399	Intermediate Similarity	NPD1392	Approved
0.7398	Intermediate Similarity	NPD8442	Discontinued
0.7391	Intermediate Similarity	NPD6242	Discontinued
0.7389	Intermediate Similarity	NPD3816	Phase 1
0.7389	Intermediate Similarity	NPD3815	Phase 1
0.7359	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD5530	Phase 1
0.7354	Intermediate Similarity	NPD3003	Approved
0.7354	Intermediate Similarity	NPD8403	Phase 1
0.7336	Intermediate Similarity	NPD5644	Phase 1
0.7333	Intermediate Similarity	NPD4858	Phase 2
0.7331	Intermediate Similarity	NPD6131	Phase 1
0.7327	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5903	Approved
0.7325	Intermediate Similarity	NPD5902	Approved
0.7322	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5999	Phase 2
0.7316	Intermediate Similarity	NPD5930	Phase 3
0.7313	Intermediate Similarity	NPD3330	Phase 1
0.7306	Intermediate Similarity	NPD7948	Phase 1
0.7306	Intermediate Similarity	NPD6243	Phase 3
0.7306	Intermediate Similarity	NPD6244	Phase 3
0.73	Intermediate Similarity	NPD4885	Approved
0.7296	Intermediate Similarity	NPD6306	Phase 2
0.7293	Intermediate Similarity	NPD6643	Discontinued
0.7289	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD3924	Approved
0.7281	Intermediate Similarity	NPD4372	Phase 1
0.7281	Intermediate Similarity	NPD3922	Approved
0.7281	Intermediate Similarity	NPD3923	Approved
0.7281	Intermediate Similarity	NPD3921	Approved
0.7273	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4558	Phase 2
0.7256	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1034	Phase 3
0.7253	Intermediate Similarity	NPD7221	Approved
0.7253	Intermediate Similarity	NPD7219	Approved
0.725	Intermediate Similarity	NPD4343	Phase 1
0.725	Intermediate Similarity	NPD4344	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7659	Discontinued
0.7229	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD8358	Approved
0.7215	Intermediate Similarity	NPD5022	Discontinued
0.7215	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5256	Discontinued
0.7208	Intermediate Similarity	NPD4454	Phase 2
0.7205	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8100	Phase 3
0.7179	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7859	Phase 2
0.7172	Intermediate Similarity	NPD5802	Phase 2
0.7171	Intermediate Similarity	NPD112	Approved
0.7171	Intermediate Similarity	NPD9705	Discontinued
0.7168	Intermediate Similarity	NPD7453	Approved
0.7168	Intermediate Similarity	NPD7452	Approved
0.7167	Intermediate Similarity	NPD6964	Approved
0.7167	Intermediate Similarity	NPD6963	Approved
0.7165	Intermediate Similarity	NPD8284	Discontinued
0.7161	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7674	Phase 3
0.7161	Intermediate Similarity	NPD7675	Phase 3
0.7161	Intermediate Similarity	NPD7426	Phase 1
0.716	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6985	Discontinued
0.7149	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8512	Phase 3
0.7137	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3875	Discontinued
0.7124	Intermediate Similarity	NPD3763	Approved
0.7118	Intermediate Similarity	NPD949	Phase 1
0.7118	Intermediate Similarity	NPD3939	Suspended
0.7111	Intermediate Similarity	NPD4886	Phase 2
0.7105	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6573	Phase 3
0.7102	Intermediate Similarity	NPD6572	Phase 2
0.7097	Intermediate Similarity	NPD8101	Phase 3
0.7091	Intermediate Similarity	NPD802	Phase 2
0.7085	Intermediate Similarity	NPD2177	Approved
0.7085	Intermediate Similarity	NPD2175	Phase 3
0.7085	Intermediate Similarity	NPD1768	Approved
0.7085	Intermediate Similarity	NPD2176	Approved
0.7082	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6750	Phase 2
0.7078	Intermediate Similarity	NPD5913	Phase 3
0.7071	Intermediate Similarity	NPD5479	Discontinued
0.7061	Intermediate Similarity	NPD6473	Phase 1
0.7056	Intermediate Similarity	NPD6595	Phase 3
0.7054	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD8247	Approved
0.7052	Intermediate Similarity	NPD8246	Approved
0.7051	Intermediate Similarity	NPD4919	Phase 3
0.7051	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4921	Phase 3
0.7048	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5939	Approved
0.7043	Intermediate Similarity	NPD5936	Approved
0.7037	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8063	Discontinued
0.7031	Intermediate Similarity	NPD4437	Phase 3
0.703	Intermediate Similarity	NPD8525	Approved
0.7028	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6550	Discontinued
0.7021	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6856	Discontinued
0.7018	Intermediate Similarity	NPD6290	Phase 2
0.7009	Intermediate Similarity	NPD5948	Phase 2
0.7008	Intermediate Similarity	NPD6531	Approved
0.7008	Intermediate Similarity	NPD6530	Approved
0.7005	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4889	Approved
0.7004	Intermediate Similarity	NPD6230	Discontinued
0.7	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5529	Phase 1
0.6982	Remote Similarity	NPD4418	Discontinued
0.6977	Remote Similarity	NPD7924	Phase 2
0.6977	Remote Similarity	NPD7925	Phase 2
0.6975	Remote Similarity	NPD3938	Phase 1
0.6975	Remote Similarity	NPD4890	Phase 2
0.6974	Remote Similarity	NPD5601	Phase 2
0.6972	Remote Similarity	NPD4375	Approved
0.6971	Remote Similarity	NPD2062	Phase 2
0.697	Remote Similarity	NPD7470	Discontinued
0.697	Remote Similarity	NPD6220	Phase 3
0.697	Remote Similarity	NPD3570	Phase 2
0.6969	Remote Similarity	NPD7955	Approved
0.6969	Remote Similarity	NPD7956	Approved
0.6967	Remote Similarity	NPD565	Phase 2
0.6966	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1032	Phase 2
0.6957	Remote Similarity	NPD8244	Phase 2
0.6957	Remote Similarity	NPD8049	Phase 2
0.6955	Remote Similarity	NPD2757	Phase 2
0.6948	Remote Similarity	NPD5065	Approved
0.6946	Remote Similarity	NPD7051	Phase 3
0.6946	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2311	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