NPASS Compound

Structure

CID7560 OpenBabel06191715332D 26 28 0 0 0 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 -1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 21 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 7 13 2 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 12 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.14
Volume:	362.663
LogP:	4.073
LogD:	2.277
LogS:	-3.538
# Rotatable Bonds:	3
TPSA:	91.92
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.495
Synthetic Accessibility Score:	3.007
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.916
MDCK Permeability:	1.1962020835198928e-05
Pgp-inhibitor:	0.099
Pgp-substrate:	0.082
Human Intestinal Absorption (HIA):	0.178
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	91.46141815185547%
Volume Distribution (VD):	0.609
Pgp-substrate:	7.289137840270996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.76
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.433
CYP2C19-substrate:	0.199
CYP2C9-inhibitor:	0.798
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.633
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	3.296
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.691
Rat Oral Acute Toxicity:	0.451
Maximum Recommended Daily Dose:	0.61
Skin Sensitization:	0.834
Carcinogencity:	0.607
Eye Corrosion:	0.003
Eye Irritation:	0.897
Respiratory Toxicity:	0.414

Download Data

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

Natural Product: NPC7560

Natural Product ID:	NPC7560
*Common Name:**	Glycocitrine-Iv
IUPAC Name:	1,3,5-trihydroxy-4-methoxy-10-methyl-2-(3-methylbut-2-enyl)acridin-9-one
Synonyms:	Glycocitrine-Iv
Standard InCHIKey:	GKBPFZFFEMNSRA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H21NO5/c1-10(2)8-9-12-18(24)14-16(20(26-4)19(12)25)21(3)15-11(17(14)23)6-5-7-13(15)22/h5-8,22,24-25H,9H2,1-4H3
SMILES:	CC(=CCc1c(c2c(c(c1O)OC)n(C)c1c(cccc1O)c2=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463652
PubChem CID:	9998312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7221	Korolkowia sewerzowi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2786	Clematis flammula	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5476	Hortia arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10647	Gentiana lactea	Species	Gentianaceae	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
ED50	2
IC50	5
Ki	1
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	2
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	0.71	uM	PMID[450890]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	5.3	uM	PMID[450890]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	2200.0	nM	PMID[450891]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	Ki	=	1100.0	nM	PMID[450891]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2500.0	nM	PMID[450890]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2000.0	nM	PMID[450890]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2300.0	nM	PMID[450890]
NPT2	Others	Unspecified		Ratio	=	0.3	n.a.	PMID[450890]
NPT2	Others	Unspecified		Ratio	=	2.1	n.a.	PMID[450890]

☑ 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 NPC7560 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	547
0.1-0.2	3200
0.2-0.3	12041
0.3-0.4	5193
0.4-0.5	8667
0.5-0.6	10443
0.6-0.7	2336
0.7-0.8	219
0.8-0.85	20
0.85-0.9	15
0.9-0.95	8
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC285254
0.9694	High Similarity	NPC2905
0.9643	High Similarity	NPC114468
0.96	High Similarity	NPC76478
0.9594	High Similarity	NPC148391
0.9557	High Similarity	NPC13249
0.9548	High Similarity	NPC134702
0.9406	High Similarity	NPC118189
0.9257	High Similarity	NPC182853
0.9239	High Similarity	NPC212123
0.9059	High Similarity	NPC268223
0.9005	High Similarity	NPC474366
0.8966	High Similarity	NPC30749
0.896	High Similarity	NPC295479
0.896	High Similarity	NPC220241
0.8916	High Similarity	NPC305542
0.8827	High Similarity	NPC170333
0.8738	High Similarity	NPC176113
0.8708	High Similarity	NPC118154
0.8708	High Similarity	NPC157983
0.8612	High Similarity	NPC87560
0.8612	High Similarity	NPC195120
0.8592	High Similarity	NPC218303
0.8571	High Similarity	NPC133156
0.8462	Intermediate Similarity	NPC116178
0.8421	Intermediate Similarity	NPC217903
0.8392	Intermediate Similarity	NPC206109
0.8392	Intermediate Similarity	NPC114039
0.8333	Intermediate Similarity	NPC321166
0.8309	Intermediate Similarity	NPC198160
0.8293	Intermediate Similarity	NPC15987
0.8148	Intermediate Similarity	NPC329830
0.8098	Intermediate Similarity	NPC234933
0.8038	Intermediate Similarity	NPC301292
0.8038	Intermediate Similarity	NPC313112
0.798	Intermediate Similarity	NPC1820
0.798	Intermediate Similarity	NPC298320
0.7943	Intermediate Similarity	NPC288759
0.7799	Intermediate Similarity	NPC241263
0.7667	Intermediate Similarity	NPC17677
0.7624	Intermediate Similarity	NPC98416
0.7615	Intermediate Similarity	NPC470481
0.7615	Intermediate Similarity	NPC470482
0.7512	Intermediate Similarity	NPC100573
0.7512	Intermediate Similarity	NPC207873
0.75	Intermediate Similarity	NPC83019
0.7477	Intermediate Similarity	NPC471489
0.7477	Intermediate Similarity	NPC477825
0.7476	Intermediate Similarity	NPC78284
0.7455	Intermediate Similarity	NPC477826
0.7455	Intermediate Similarity	NPC477827
0.7453	Intermediate Similarity	NPC204580
0.7424	Intermediate Similarity	NPC204867
0.7399	Intermediate Similarity	NPC477828
0.7387	Intermediate Similarity	NPC298449
0.7352	Intermediate Similarity	NPC90185
0.7331	Intermediate Similarity	NPC477395
0.733	Intermediate Similarity	NPC327005
0.7313	Intermediate Similarity	NPC251071
0.7311	Intermediate Similarity	NPC107123
0.7306	Intermediate Similarity	NPC308943
0.7304	Intermediate Similarity	NPC315914
0.73	Intermediate Similarity	NPC299582
0.7294	Intermediate Similarity	NPC163829
0.7292	Intermediate Similarity	NPC134637
0.729	Intermediate Similarity	NPC161804
0.7285	Intermediate Similarity	NPC25961
0.7281	Intermediate Similarity	NPC94842
0.7273	Intermediate Similarity	NPC262725
0.7261	Intermediate Similarity	NPC470480
0.7261	Intermediate Similarity	NPC302807
0.726	Intermediate Similarity	NPC158551
0.725	Intermediate Similarity	NPC78225
0.725	Intermediate Similarity	NPC262286
0.725	Intermediate Similarity	NPC36852
0.7247	Intermediate Similarity	NPC132385
0.7246	Intermediate Similarity	NPC476258
0.7246	Intermediate Similarity	NPC304837
0.7236	Intermediate Similarity	NPC39184
0.7236	Intermediate Similarity	NPC134287
0.7236	Intermediate Similarity	NPC130589
0.722	Intermediate Similarity	NPC203373
0.7204	Intermediate Similarity	NPC320088
0.72	Intermediate Similarity	NPC68093
0.72	Intermediate Similarity	NPC191146
0.72	Intermediate Similarity	NPC138243
0.7198	Intermediate Similarity	NPC85613
0.7192	Intermediate Similarity	NPC83922
0.7192	Intermediate Similarity	NPC472448
0.719	Intermediate Similarity	NPC473188
0.7186	Intermediate Similarity	NPC124714
0.7185	Intermediate Similarity	NPC113455
0.7179	Intermediate Similarity	NPC185031
0.7178	Intermediate Similarity	NPC476980
0.7178	Intermediate Similarity	NPC270515
0.717	Intermediate Similarity	NPC208890
0.7164	Intermediate Similarity	NPC78103
0.7162	Intermediate Similarity	NPC46990
0.7157	Intermediate Similarity	NPC92722
0.7157	Intermediate Similarity	NPC102003
0.7155	Intermediate Similarity	NPC160100
0.7155	Intermediate Similarity	NPC15406
0.715	Intermediate Similarity	NPC117992
0.715	Intermediate Similarity	NPC152951
0.715	Intermediate Similarity	NPC113906
0.715	Intermediate Similarity	NPC57674
0.715	Intermediate Similarity	NPC230149
0.715	Intermediate Similarity	NPC168247
0.7143	Intermediate Similarity	NPC258331
0.7143	Intermediate Similarity	NPC200888
0.7143	Intermediate Similarity	NPC266314
0.7143	Intermediate Similarity	NPC29876
0.7143	Intermediate Similarity	NPC167678
0.7137	Intermediate Similarity	NPC82056
0.7137	Intermediate Similarity	NPC209981
0.7136	Intermediate Similarity	NPC181209
0.7136	Intermediate Similarity	NPC121522
0.7136	Intermediate Similarity	NPC100971
0.7136	Intermediate Similarity	NPC291802
0.7136	Intermediate Similarity	NPC269451
0.7136	Intermediate Similarity	NPC209487
0.7136	Intermediate Similarity	NPC216769
0.7136	Intermediate Similarity	NPC131266
0.7136	Intermediate Similarity	NPC245382
0.7136	Intermediate Similarity	NPC35763
0.7136	Intermediate Similarity	NPC100263
0.7129	Intermediate Similarity	NPC250214
0.7129	Intermediate Similarity	NPC95936
0.7123	Intermediate Similarity	NPC2173
0.7123	Intermediate Similarity	NPC328700
0.7123	Intermediate Similarity	NPC119818
0.7123	Intermediate Similarity	NPC202771
0.7123	Intermediate Similarity	NPC286135
0.7122	Intermediate Similarity	NPC73280
0.7121	Intermediate Similarity	NPC472279
0.7115	Intermediate Similarity	NPC5167
0.7114	Intermediate Similarity	NPC472916
0.7109	Intermediate Similarity	NPC276674
0.7109	Intermediate Similarity	NPC33902
0.7107	Intermediate Similarity	NPC183655
0.7107	Intermediate Similarity	NPC287395
0.7107	Intermediate Similarity	NPC15329
0.7107	Intermediate Similarity	NPC131451
0.7106	Intermediate Similarity	NPC316292
0.71	Intermediate Similarity	NPC70433
0.71	Intermediate Similarity	NPC273462
0.71	Intermediate Similarity	NPC88645
0.71	Intermediate Similarity	NPC227337
0.71	Intermediate Similarity	NPC206238
0.71	Intermediate Similarity	NPC292214
0.71	Intermediate Similarity	NPC250557
0.71	Intermediate Similarity	NPC271779
0.71	Intermediate Similarity	NPC49402
0.71	Intermediate Similarity	NPC33051
0.71	Intermediate Similarity	NPC19175
0.71	Intermediate Similarity	NPC167091
0.7097	Intermediate Similarity	NPC23080
0.7097	Intermediate Similarity	NPC193906
0.7097	Intermediate Similarity	NPC282346
0.7095	Intermediate Similarity	NPC120239
0.7094	Intermediate Similarity	NPC56085
0.7094	Intermediate Similarity	NPC14353
0.7094	Intermediate Similarity	NPC204290
0.7094	Intermediate Similarity	NPC227033
0.7094	Intermediate Similarity	NPC211215
0.7094	Intermediate Similarity	NPC228785
0.7087	Intermediate Similarity	NPC148124
0.7085	Intermediate Similarity	NPC262623
0.7085	Intermediate Similarity	NPC19980
0.7085	Intermediate Similarity	NPC256406
0.7085	Intermediate Similarity	NPC45291
0.708	Intermediate Similarity	NPC55470
0.7079	Intermediate Similarity	NPC222814
0.7079	Intermediate Similarity	NPC474208
0.7079	Intermediate Similarity	NPC162869
0.7079	Intermediate Similarity	NPC99597
0.7079	Intermediate Similarity	NPC472913
0.7079	Intermediate Similarity	NPC474836
0.7079	Intermediate Similarity	NPC476981
0.7079	Intermediate Similarity	NPC210084
0.7079	Intermediate Similarity	NPC475267
0.7079	Intermediate Similarity	NPC472914
0.7079	Intermediate Similarity	NPC96167
0.7079	Intermediate Similarity	NPC472910
0.7079	Intermediate Similarity	NPC472911
0.7079	Intermediate Similarity	NPC223787
0.7079	Intermediate Similarity	NPC291508
0.7079	Intermediate Similarity	NPC156057
0.7079	Intermediate Similarity	NPC245758
0.7079	Intermediate Similarity	NPC48208
0.7078	Intermediate Similarity	NPC317567
0.7076	Intermediate Similarity	NPC476220
0.7076	Intermediate Similarity	NPC160113
0.7075	Intermediate Similarity	NPC18306
0.7073	Intermediate Similarity	NPC220313
0.7072	Intermediate Similarity	NPC222561
0.7072	Intermediate Similarity	NPC16249
0.7067	Intermediate Similarity	NPC474815
0.7066	Intermediate Similarity	NPC477396
0.7065	Intermediate Similarity	NPC256612

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 NPC7560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	711
0.2-0.3	1155
0.3-0.4	1974
0.4-0.5	2682
0.5-0.6	1812
0.6-0.7	435
0.7-0.8	44
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD2899	Discontinued
0.7478	Intermediate Similarity	NPD6625	Approved
0.7454	Intermediate Similarity	NPD3298	Approved
0.743	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7922	Phase 1
0.7378	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5860	Discontinued
0.7281	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5496	Approved
0.7222	Intermediate Similarity	NPD3297	Approved
0.7185	Intermediate Similarity	NPD1483	Discontinued
0.7168	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5242	Approved
0.7156	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7263	Phase 2
0.7123	Intermediate Similarity	NPD5006	Approved
0.7123	Intermediate Similarity	NPD5005	Approved
0.7114	Intermediate Similarity	NPD8461	Discontinued
0.7094	Intermediate Similarity	NPD8067	Phase 3
0.7089	Intermediate Similarity	NPD4846	Phase 2
0.7078	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8367	Approved
0.7059	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4082	Approved
0.7033	Intermediate Similarity	NPD8492	Approved
0.7015	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4596	Phase 1
0.6986	Remote Similarity	NPD6874	Approved
0.6982	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7907	Approved
0.6968	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2906	Approved
0.6964	Remote Similarity	NPD3472	Approved
0.6964	Remote Similarity	NPD2907	Approved
0.6964	Remote Similarity	NPD4022	Approved
0.6947	Remote Similarity	NPD1945	Phase 1
0.6944	Remote Similarity	NPD5937	Approved
0.6941	Remote Similarity	NPD4420	Approved
0.6937	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7654	Discontinued
0.6931	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6104	Discontinued
0.6903	Remote Similarity	NPD3372	Discontinued
0.6895	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2821	Approved
0.6889	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4111	Phase 1
0.6883	Remote Similarity	NPD4665	Approved
0.6881	Remote Similarity	NPD1934	Approved
0.6878	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD683	Approved
0.6864	Remote Similarity	NPD5071	Phase 2
0.6854	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD2494	Approved
0.6847	Remote Similarity	NPD2493	Approved
0.6847	Remote Similarity	NPD3450	Approved
0.6847	Remote Similarity	NPD3452	Approved
0.6844	Remote Similarity	NPD7584	Approved
0.6842	Remote Similarity	NPD4492	Approved
0.6842	Remote Similarity	NPD4494	Approved
0.6838	Remote Similarity	NPD7279	Phase 2
0.6838	Remote Similarity	NPD7278	Phase 2
0.6826	Remote Similarity	NPD8149	Discontinued
0.6822	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7701	Phase 2
0.6805	Remote Similarity	NPD7048	Phase 3
0.6802	Remote Similarity	NPD2339	Phase 3
0.6795	Remote Similarity	NPD6997	Phase 2
0.6787	Remote Similarity	NPD5196	Approved
0.6787	Remote Similarity	NPD5194	Approved
0.6787	Remote Similarity	NPD5197	Approved
0.6787	Remote Similarity	NPD4668	Phase 2
0.6779	Remote Similarity	NPD5183	Approved
0.6779	Remote Similarity	NPD5186	Approved
0.6777	Remote Similarity	NPD3793	Phase 3
0.6765	Remote Similarity	NPD6199	Discontinued
0.6765	Remote Similarity	NPD4981	Phase 2
0.6756	Remote Similarity	NPD4465	Phase 2
0.6756	Remote Similarity	NPD4467	Phase 2
0.6756	Remote Similarity	NPD4582	Approved
0.6756	Remote Similarity	NPD4583	Approved
0.674	Remote Similarity	NPD7585	Approved
0.6733	Remote Similarity	NPD824	Approved
0.6732	Remote Similarity	NPD5978	Approved
0.6732	Remote Similarity	NPD5977	Approved
0.6727	Remote Similarity	NPD4363	Phase 3
0.6727	Remote Similarity	NPD4360	Phase 2
0.6725	Remote Similarity	NPD4493	Discontinued
0.6724	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1220	Phase 1
0.6711	Remote Similarity	NPD4002	Approved
0.6711	Remote Similarity	NPD4004	Approved
0.6709	Remote Similarity	NPD7224	Discontinued
0.6709	Remote Similarity	NPD7223	Discontinued
0.6699	Remote Similarity	NPD3882	Suspended
0.6698	Remote Similarity	NPD1221	Approved
0.6697	Remote Similarity	NPD5928	Phase 1
0.6696	Remote Similarity	NPD7583	Approved
0.6683	Remote Similarity	NPD5494	Approved
0.6681	Remote Similarity	NPD3893	Discontinued
0.6681	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7803	Approved
0.6667	Remote Similarity	NPD2975	Approved
0.6667	Remote Similarity	NPD2973	Approved
0.6667	Remote Similarity	NPD4604	Approved
0.6667	Remote Similarity	NPD2974	Approved
0.6667	Remote Similarity	NPD4605	Approved
0.665	Remote Similarity	NPD5353	Approved
0.664	Remote Similarity	NPD8091	Phase 3
0.6635	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2898	Approved
0.6635	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6166	Phase 2
0.6624	Remote Similarity	NPD6198	Phase 1
0.6623	Remote Similarity	NPD3888	Discontinued
0.6623	Remote Similarity	NPD7225	Discontinued
0.6622	Remote Similarity	NPD4361	Phase 2
0.6622	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6020	Phase 2
0.6619	Remote Similarity	NPD6232	Discontinued
0.6619	Remote Similarity	NPD5711	Approved
0.6619	Remote Similarity	NPD5710	Approved
0.6618	Remote Similarity	NPD4380	Phase 2
0.6609	Remote Similarity	NPD5914	Approved
0.6609	Remote Similarity	NPD7047	Phase 3
0.6607	Remote Similarity	NPD5608	Approved
0.6607	Remote Similarity	NPD5609	Approved
0.6606	Remote Similarity	NPD4515	Suspended
0.6606	Remote Similarity	NPD4539	Phase 1
0.6604	Remote Similarity	NPD3446	Phase 1
0.6604	Remote Similarity	NPD7473	Discontinued
0.6597	Remote Similarity	NPD3925	Approved
0.6595	Remote Similarity	NPD4455	Discontinued
0.6592	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8053	Approved
0.659	Remote Similarity	NPD8054	Approved
0.6578	Remote Similarity	NPD4580	Approved
0.6575	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3818	Discontinued
0.6569	Remote Similarity	NPD7186	Phase 3
0.6567	Remote Similarity	NPD1511	Approved
0.6558	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2248	Approved
0.6557	Remote Similarity	NPD2246	Approved
0.6553	Remote Similarity	NPD6844	Discontinued
0.655	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7043	Discontinued
0.6546	Remote Similarity	NPD5488	Discontinued
0.6543	Remote Similarity	NPD6723	Discontinued
0.6542	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.654	Remote Similarity	NPD7805	Phase 3
0.6537	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6644	Discontinued
0.6534	Remote Similarity	NPD3986	Discontinued
0.653	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6523	Remote Similarity	NPD7708	Approved
0.6522	Remote Similarity	NPD4859	Phase 1
0.6518	Remote Similarity	NPD5195	Discontinued
0.6518	Remote Similarity	NPD6790	Phase 1
0.6516	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD2490	Approved
0.6516	Remote Similarity	NPD2488	Approved
0.6512	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7074	Phase 3
0.6505	Remote Similarity	NPD6385	Approved
0.6505	Remote Similarity	NPD6386	Approved
0.6502	Remote Similarity	NPD1512	Approved
0.65	Remote Similarity	NPD7906	Approved
0.65	Remote Similarity	NPD1898	Discontinued
0.6498	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD3437	Discontinued
0.6496	Remote Similarity	NPD7559	Phase 2
0.6484	Remote Similarity	NPD7955	Approved
0.6484	Remote Similarity	NPD7956	Approved
0.6481	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7886	Phase 2
0.6478	Remote Similarity	NPD7885	Phase 2
0.6475	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5582	Discontinued
0.6473	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7054	Approved
0.6461	Remote Similarity	NPD1505	Phase 2
0.6459	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7125	Discontinued
0.6455	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7302	Phase 3

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