NPASS Compound

Structure

CID103687 OpenBabel06191715452D 27 31 0 0 0 0 0 0 0 0999 V2000 -0.1478 4.5766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0535 3.6040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3182 -1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3183 -0.4459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5453 -1.7844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5455 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -2.6764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7728 -3.1227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3894 3.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3181 -0.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5454 0.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1721 3.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5452 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7726 -1.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.7842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7727 -0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3179 -1.3382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 0.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0696 2.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7726 -1.3379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5456 -1.7842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7726 -0.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5453 -2.6764 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6311 1.5233 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 3.1152 -1.7986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8118 2.0773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 23 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 24 2 3 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.13
Volume:	367.856
LogP:	4.85
LogD:	4.078
LogS:	-6.763
# Rotatable Bonds:	3
TPSA:	66.63
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	2.962
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.915
MDCK Permeability:	1.2787588275386952e-05
Pgp-inhibitor:	0.517
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.76

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	97.43770599365234%
Volume Distribution (VD):	0.434
Pgp-substrate:	1.7521893978118896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.506
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.789
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	2.381
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.322
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.896
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.828
Carcinogencity:	0.934
Eye Corrosion:	0.004
Eye Irritation:	0.866
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC103687

Natural Product ID:	NPC103687
*Common Name:**	IWIBKNRYVHDQHU-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IWIBKNRYVHDQHU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H17N3O2/c1-12(2)9-19(27)24-18-11-13-10-17(26)21-20-15(7-8-23-21)14-5-3-4-6-16(14)25(18)22(13)20/h3-11,26H,1-2H3,(H,24,27)
SMILES:	CC(=CC(=Nc1cc2c3n1c1ccccc1c1c3c(c(c2)O)ncc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419311
PubChem CID:	73346121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO14024	Cystodytes violatinctus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23961991]
NPO8019	Pentaceras australe	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13848	Amomum daniellii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14024	Cystodytes violatinctus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO394	Psilostrophe villosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15255	Piptadenia contorta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9122	Pycnanthemum lanceolatum	Species	Lamiaceae	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
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	6000.0	nM	PMID[468428]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	8480.0	nM	PMID[468428]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	4320.0	nM	PMID[468428]

☑ 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 NPC103687 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	700
0.1-0.2	5549
0.2-0.3	12194
0.3-0.4	16000
0.4-0.5	4253
0.5-0.6	2574
0.6-0.7	1295
0.7-0.8	128
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC132631
0.8824	High Similarity	NPC477111
0.8634	High Similarity	NPC477113
0.8443	Intermediate Similarity	NPC477110
0.8221	Intermediate Similarity	NPC470678
0.8091	Intermediate Similarity	NPC130570
0.784	Intermediate Similarity	NPC475774
0.7804	Intermediate Similarity	NPC475070
0.7797	Intermediate Similarity	NPC477112
0.7736	Intermediate Similarity	NPC476167
0.7719	Intermediate Similarity	NPC476451
0.7706	Intermediate Similarity	NPC5145
0.7689	Intermediate Similarity	NPC192315
0.7658	Intermediate Similarity	NPC304926
0.7658	Intermediate Similarity	NPC476041
0.765	Intermediate Similarity	NPC314940
0.765	Intermediate Similarity	NPC473764
0.7621	Intermediate Similarity	NPC214980
0.7621	Intermediate Similarity	NPC2497
0.7619	Intermediate Similarity	NPC99666
0.7583	Intermediate Similarity	NPC329541
0.7564	Intermediate Similarity	NPC477861
0.7561	Intermediate Similarity	NPC478032
0.756	Intermediate Similarity	NPC472289
0.7548	Intermediate Similarity	NPC171171
0.7546	Intermediate Similarity	NPC211813
0.7525	Intermediate Similarity	NPC252590
0.7511	Intermediate Similarity	NPC6215
0.75	Intermediate Similarity	NPC314002
0.7478	Intermediate Similarity	NPC132642
0.7477	Intermediate Similarity	NPC77555
0.7455	Intermediate Similarity	NPC476161
0.7452	Intermediate Similarity	NPC204717
0.7426	Intermediate Similarity	NPC473312
0.7411	Intermediate Similarity	NPC237740
0.7404	Intermediate Similarity	NPC220765
0.7399	Intermediate Similarity	NPC94157
0.7397	Intermediate Similarity	NPC329708
0.7397	Intermediate Similarity	NPC118832
0.7397	Intermediate Similarity	NPC274291
0.7397	Intermediate Similarity	NPC264166
0.7397	Intermediate Similarity	NPC47059
0.7397	Intermediate Similarity	NPC165349
0.7393	Intermediate Similarity	NPC230805
0.7373	Intermediate Similarity	NPC30540
0.7359	Intermediate Similarity	NPC473185
0.7354	Intermediate Similarity	NPC208284
0.7353	Intermediate Similarity	NPC39092
0.7319	Intermediate Similarity	NPC24802
0.7303	Intermediate Similarity	NPC471891
0.7297	Intermediate Similarity	NPC476157
0.7294	Intermediate Similarity	NPC249040
0.7285	Intermediate Similarity	NPC476121
0.7285	Intermediate Similarity	NPC476124
0.726	Intermediate Similarity	NPC88363
0.7244	Intermediate Similarity	NPC471603
0.7243	Intermediate Similarity	NPC472031
0.7243	Intermediate Similarity	NPC472066
0.7243	Intermediate Similarity	NPC472067
0.7241	Intermediate Similarity	NPC471178
0.724	Intermediate Similarity	NPC470500
0.7234	Intermediate Similarity	NPC469554
0.7227	Intermediate Similarity	NPC41679
0.7225	Intermediate Similarity	NPC470799
0.7225	Intermediate Similarity	NPC8022
0.722	Intermediate Similarity	NPC18348
0.7212	Intermediate Similarity	NPC184964
0.7209	Intermediate Similarity	NPC324149
0.7208	Intermediate Similarity	NPC295452
0.7208	Intermediate Similarity	NPC171393
0.7205	Intermediate Similarity	NPC213530
0.7205	Intermediate Similarity	NPC193267
0.7192	Intermediate Similarity	NPC97367
0.7188	Intermediate Similarity	NPC476116
0.7179	Intermediate Similarity	NPC314954
0.7167	Intermediate Similarity	NPC81175
0.7163	Intermediate Similarity	NPC203754
0.7163	Intermediate Similarity	NPC150048
0.7161	Intermediate Similarity	NPC101543
0.7156	Intermediate Similarity	NPC156704
0.715	Intermediate Similarity	NPC246700
0.7143	Intermediate Similarity	NPC295228
0.7137	Intermediate Similarity	NPC477610
0.7131	Intermediate Similarity	NPC180504
0.713	Intermediate Similarity	NPC472111
0.713	Intermediate Similarity	NPC475841
0.713	Intermediate Similarity	NPC474145
0.7118	Intermediate Similarity	NPC469727
0.7117	Intermediate Similarity	NPC200836
0.7117	Intermediate Similarity	NPC245816
0.7117	Intermediate Similarity	NPC476138
0.7117	Intermediate Similarity	NPC53144
0.7116	Intermediate Similarity	NPC3715
0.7113	Intermediate Similarity	NPC473183
0.7097	Intermediate Similarity	NPC307963
0.7093	Intermediate Similarity	NPC112206
0.7093	Intermediate Similarity	NPC202605
0.7091	Intermediate Similarity	NPC287437
0.709	Intermediate Similarity	NPC472068
0.7087	Intermediate Similarity	NPC173080
0.7071	Intermediate Similarity	NPC477549
0.707	Intermediate Similarity	NPC32771
0.7067	Intermediate Similarity	NPC471294
0.7067	Intermediate Similarity	NPC82548
0.7061	Intermediate Similarity	NPC266931
0.7059	Intermediate Similarity	NPC471177
0.7059	Intermediate Similarity	NPC59779
0.7059	Intermediate Similarity	NPC124542
0.7059	Intermediate Similarity	NPC315491
0.7059	Intermediate Similarity	NPC45459
0.7056	Intermediate Similarity	NPC473179
0.7042	Intermediate Similarity	NPC184225
0.7029	Intermediate Similarity	NPC473184
0.7028	Intermediate Similarity	NPC144114
0.7028	Intermediate Similarity	NPC477891
0.7023	Intermediate Similarity	NPC254762
0.7023	Intermediate Similarity	NPC46580
0.7018	Intermediate Similarity	NPC26679
0.7014	Intermediate Similarity	NPC476582
0.7014	Intermediate Similarity	NPC4071
0.7014	Intermediate Similarity	NPC128823
0.7014	Intermediate Similarity	NPC476578
0.7009	Intermediate Similarity	NPC472259
0.7005	Intermediate Similarity	NPC92111
0.7005	Intermediate Similarity	NPC44161
0.7	Intermediate Similarity	NPC267928
0.7	Intermediate Similarity	NPC153042
0.6996	Remote Similarity	NPC72905
0.6991	Remote Similarity	NPC128751
0.6991	Remote Similarity	NPC314957
0.6986	Remote Similarity	NPC133366
0.6982	Remote Similarity	NPC329793
0.6982	Remote Similarity	NPC176538
0.6978	Remote Similarity	NPC470164
0.6978	Remote Similarity	NPC323345
0.6974	Remote Similarity	NPC294375
0.6972	Remote Similarity	NPC74619
0.6966	Remote Similarity	NPC162748
0.6966	Remote Similarity	NPC216612
0.6964	Remote Similarity	NPC223427
0.6962	Remote Similarity	NPC253580
0.696	Remote Similarity	NPC185782
0.6959	Remote Similarity	NPC469497
0.6959	Remote Similarity	NPC76748
0.6959	Remote Similarity	NPC106833
0.6955	Remote Similarity	NPC242209
0.6955	Remote Similarity	NPC251090
0.6947	Remote Similarity	NPC53344
0.6947	Remote Similarity	NPC313189
0.6941	Remote Similarity	NPC474177
0.694	Remote Similarity	NPC477609
0.6938	Remote Similarity	NPC158129
0.6933	Remote Similarity	NPC36229
0.6933	Remote Similarity	NPC16452
0.6933	Remote Similarity	NPC476581
0.6933	Remote Similarity	NPC285558
0.693	Remote Similarity	NPC85273
0.693	Remote Similarity	NPC167860
0.693	Remote Similarity	NPC309845
0.693	Remote Similarity	NPC123976
0.6926	Remote Similarity	NPC469928
0.692	Remote Similarity	NPC328596
0.692	Remote Similarity	NPC328318
0.692	Remote Similarity	NPC470126
0.6916	Remote Similarity	NPC470931
0.6916	Remote Similarity	NPC287208
0.6913	Remote Similarity	NPC476287
0.6912	Remote Similarity	NPC296527
0.6906	Remote Similarity	NPC213308
0.6905	Remote Similarity	NPC208060
0.6904	Remote Similarity	NPC475253
0.6901	Remote Similarity	NPC28945
0.6901	Remote Similarity	NPC15801
0.6901	Remote Similarity	NPC285343
0.6898	Remote Similarity	NPC314573
0.6898	Remote Similarity	NPC474707
0.6898	Remote Similarity	NPC142385
0.6892	Remote Similarity	NPC212213
0.6891	Remote Similarity	NPC477608
0.6891	Remote Similarity	NPC477607
0.689	Remote Similarity	NPC164664
0.6886	Remote Similarity	NPC209769
0.6886	Remote Similarity	NPC469589
0.688	Remote Similarity	NPC276657
0.6878	Remote Similarity	NPC60006
0.6878	Remote Similarity	NPC472193
0.6875	Remote Similarity	NPC207686
0.687	Remote Similarity	NPC296482
0.687	Remote Similarity	NPC208522
0.687	Remote Similarity	NPC202768
0.687	Remote Similarity	NPC53069
0.6867	Remote Similarity	NPC137353
0.6867	Remote Similarity	NPC204446
0.6866	Remote Similarity	NPC204565
0.6865	Remote Similarity	NPC475746
0.6864	Remote Similarity	NPC167908
0.6856	Remote Similarity	NPC290689
0.6856	Remote Similarity	NPC199667
0.6854	Remote Similarity	NPC232340
0.6852	Remote Similarity	NPC94943

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 NPC103687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	669
0.2-0.3	874
0.3-0.4	1814
0.4-0.5	2489
0.5-0.6	1891
0.6-0.7	993
0.7-0.8	81
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8531	High Similarity	NPD7112	Discontinued
0.7837	Intermediate Similarity	NPD9695	Approved
0.7723	Intermediate Similarity	NPD4945	Discontinued
0.7692	Intermediate Similarity	NPD7067	Approved
0.7692	Intermediate Similarity	NPD7068	Approved
0.7672	Intermediate Similarity	NPD6750	Phase 2
0.7667	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5428	Discontinued
0.7578	Intermediate Similarity	NPD7423	Phase 2
0.7549	Intermediate Similarity	NPD6159	Phase 2
0.7547	Intermediate Similarity	NPD4998	Phase 3
0.7547	Intermediate Similarity	NPD4999	Phase 3
0.7546	Intermediate Similarity	NPD6132	Phase 1
0.749	Intermediate Similarity	NPD5644	Phase 1
0.7489	Intermediate Similarity	NPD7222	Phase 2
0.7477	Intermediate Similarity	NPD3330	Phase 1
0.7468	Intermediate Similarity	NPD2757	Phase 2
0.7458	Intermediate Similarity	NPD3809	Discontinued
0.7455	Intermediate Similarity	NPD6957	Approved
0.7455	Intermediate Similarity	NPD6958	Approved
0.7451	Intermediate Similarity	NPD9690	Approved
0.7404	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD31	Approved
0.7397	Intermediate Similarity	NPD32	Approved
0.7397	Intermediate Similarity	NPD4037	Approved
0.7397	Intermediate Similarity	NPD4039	Approved
0.7397	Intermediate Similarity	NPD4036	Approved
0.7397	Intermediate Similarity	NPD4035	Approved
0.7397	Intermediate Similarity	NPD4034	Approved
0.7397	Intermediate Similarity	NPD4038	Approved
0.7397	Intermediate Similarity	NPD4033	Approved
0.7397	Intermediate Similarity	NPD4122	Approved
0.7393	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7603	Discontinued
0.738	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6711	Approved
0.7368	Intermediate Similarity	NPD7726	Phase 1
0.735	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD9705	Discontinued
0.735	Intermediate Similarity	NPD112	Approved
0.7339	Intermediate Similarity	NPD4511	Phase 1
0.733	Intermediate Similarity	NPD1197	Approved
0.7315	Intermediate Similarity	NPD7948	Phase 1
0.7309	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD3013	Phase 3
0.7306	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6500	Approved
0.7281	Intermediate Similarity	NPD6501	Approved
0.7273	Intermediate Similarity	NPD4886	Phase 2
0.7257	Intermediate Similarity	NPD5413	Phase 2
0.7257	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7452	Approved
0.7252	Intermediate Similarity	NPD7453	Approved
0.7238	Intermediate Similarity	NPD3872	Phase 3
0.7229	Intermediate Similarity	NPD5045	Phase 2
0.7227	Intermediate Similarity	NPD6975	Discontinued
0.7225	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5936	Approved
0.72	Intermediate Similarity	NPD5939	Approved
0.7174	Intermediate Similarity	NPD6856	Discontinued
0.7169	Intermediate Similarity	NPD3814	Phase 1
0.7169	Intermediate Similarity	NPD5828	Phase 2
0.7167	Intermediate Similarity	NPD7050	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7051	Phase 3
0.7154	Intermediate Similarity	NPD7405	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6968	Phase 2
0.7149	Intermediate Similarity	NPD3962	Phase 2
0.7149	Intermediate Similarity	NPD3959	Phase 2
0.7149	Intermediate Similarity	NPD6969	Phase 2
0.713	Intermediate Similarity	NPD3404	Approved
0.713	Intermediate Similarity	NPD4615	Phase 2
0.7129	Intermediate Similarity	NPD5255	Approved
0.7124	Intermediate Similarity	NPD4401	Phase 2
0.7124	Intermediate Similarity	NPD4403	Phase 3
0.7124	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD1954	Phase 1
0.711	Intermediate Similarity	NPD7935	Phase 2
0.7104	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1038	Approved
0.7091	Intermediate Similarity	NPD2175	Phase 3
0.7091	Intermediate Similarity	NPD2176	Approved
0.7091	Intermediate Similarity	NPD2177	Approved
0.7089	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2414	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5612	Discontinued
0.7072	Intermediate Similarity	NPD3928	Approved
0.7072	Intermediate Similarity	NPD3931	Approved
0.707	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4612	Discontinued
0.7059	Intermediate Similarity	NPD484	Approved
0.7059	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4858	Phase 2
0.7054	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6569	Phase 2
0.7048	Intermediate Similarity	NPD7111	Discontinued
0.7037	Intermediate Similarity	NPD2410	Phase 2
0.7033	Intermediate Similarity	NPD5065	Approved
0.7033	Intermediate Similarity	NPD8101	Phase 3
0.7031	Intermediate Similarity	NPD7188	Phase 3
0.7021	Intermediate Similarity	NPD6352	Phase 2
0.7014	Intermediate Similarity	NPD5999	Phase 2
0.7012	Intermediate Similarity	NPD7923	Phase 2
0.7004	Intermediate Similarity	NPD8321	Discontinued
0.6992	Remote Similarity	NPD6327	Phase 1
0.6992	Remote Similarity	NPD6326	Phase 2
0.6992	Remote Similarity	NPD6165	Phase 2
0.6992	Remote Similarity	NPD6164	Phase 2
0.6991	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5529	Phase 1
0.6987	Remote Similarity	NPD2616	Phase 3
0.6987	Remote Similarity	NPD2615	Phase 3
0.6983	Remote Similarity	NPD7117	Phase 2
0.6983	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5270	Discontinued
0.6979	Remote Similarity	NPD4890	Phase 2
0.6978	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD9689	Approved
0.697	Remote Similarity	NPD4893	Phase 3
0.6968	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5885	Approved
0.6967	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3234	Phase 3
0.6966	Remote Similarity	NPD3233	Phase 2
0.6966	Remote Similarity	NPD1856	Discontinued
0.6962	Remote Similarity	NPD7555	Discontinued
0.6959	Remote Similarity	NPD6281	Approved
0.6958	Remote Similarity	NPD6970	Phase 2
0.6957	Remote Similarity	NPD6528	Phase 1
0.6955	Remote Similarity	NPD3477	Phase 2
0.6955	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6290	Phase 2
0.6947	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2383	Phase 1
0.6941	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5044	Phase 2
0.6938	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5425	Phase 1
0.693	Remote Similarity	NPD2762	Phase 2
0.6927	Remote Similarity	NPD4148	Approved
0.6926	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7857	Phase 3
0.6926	Remote Similarity	NPD7856	Phase 2
0.6919	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7666	Phase 3
0.6916	Remote Similarity	NPD7665	Phase 2
0.6911	Remote Similarity	NPD8100	Phase 3
0.691	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3875	Discontinued
0.691	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD925	Approved
0.6908	Remote Similarity	NPD7659	Discontinued
0.6908	Remote Similarity	NPD926	Approved
0.6906	Remote Similarity	NPD1838	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4547	Phase 3
0.69	Remote Similarity	NPD4502	Phase 2
0.6898	Remote Similarity	NPD6572	Phase 2
0.6898	Remote Similarity	NPD6573	Phase 3
0.6898	Remote Similarity	NPD7592	Phase 2
0.6897	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6961	Discontinued
0.6889	Remote Similarity	NPD4044	Discontinued
0.6881	Remote Similarity	NPD3262	Approved
0.6881	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6158	Phase 2
0.6881	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1603	Discontinued
0.6875	Remote Similarity	NPD425	Approved
0.6875	Remote Similarity	NPD4442	Phase 2
0.6875	Remote Similarity	NPD424	Approved
0.6875	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3815	Phase 1
0.687	Remote Similarity	NPD3816	Phase 1
0.6869	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4429	Discontinued
0.6861	Remote Similarity	NPD8396	Approved
0.6861	Remote Similarity	NPD8395	Approved
0.6857	Remote Similarity	NPD6490	Phase 2
0.6855	Remote Similarity	NPD4558	Phase 2
0.6853	Remote Similarity	NPD6643	Discontinued
0.6849	Remote Similarity	NPD8430	Approved
0.6846	Remote Similarity	NPD4306	Phase 1
0.6846	Remote Similarity	NPD6494	Phase 2
0.6842	Remote Similarity	NPD5862	Discovery
0.6842	Remote Similarity	NPD2187	Approved
0.6842	Remote Similarity	NPD2189	Approved
0.684	Remote Similarity	NPD5945	Phase 1
0.684	Remote Similarity	NPD5944	Phase 1
0.6835	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4418	Discontinued
0.6833	Remote Similarity	NPD1912	Approved
0.6828	Remote Similarity	NPD5530	Phase 1
0.6827	Remote Similarity	NPD6482	Phase 1
0.6825	Remote Similarity	NPD6458	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