NPASS Compound

Structure

CID170333 OpenBabel06191715542D 24 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 1.7321 -2.0000 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 -2.5981 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 1.7321 0.0000 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 -1.7321 -2.0000 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 0.8660 -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 0.0000 -2.0000 0.0000 C 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 11 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 19 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	336.577
LogP:	4.2
LogD:	2.786
LogS:	-3.579
# Rotatable Bonds:	2
TPSA:	82.69
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	2.94
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.876
MDCK Permeability:	9.895290531858336e-06
Pgp-inhibitor:	0.046
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.234
30% Bioavailability (F30%):	0.459

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	94.93971252441406%
Volume Distribution (VD):	0.613
Pgp-substrate:	3.054258108139038%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.72
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.771
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.268
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	5.018
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.516
AMES Toxicity:	0.837
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.904
Carcinogencity:	0.674
Eye Corrosion:	0.007
Eye Irritation:	0.94
Respiratory Toxicity:	0.277

Download Data

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

Natural Product: NPC170333

Natural Product ID:	NPC170333
*Common Name:**	Glycocitrine-I
IUPAC Name:	1,3,5-trihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
Synonyms:	Glycocitrine-I
Standard InCHIKey:	OPPJKACRWCPJGU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO4/c1-10(2)7-8-11-14(22)9-15(23)16-18(11)20(3)17-12(19(16)24)5-4-6-13(17)21/h4-7,9,21-23H,8H2,1-3H3
SMILES:	CC(=CCc1c(cc(c2c1n(C)c1c(cccc1O)c2=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668598
PubChem CID:	11580650
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
NPO14038	Oriciopsis glaberrima	n.a.	n.a.	n.a.	n.a.	stem	n.a.	PMID[16508179]
NPO10647	Gentiana lactea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14038	Oriciopsis glaberrima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
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]
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]
NPO14038	Oriciopsis glaberrima	n.a.	n.a.	n.a.	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	1
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	IC50	=	25000.0	nM	PMID[539158]
NPT601	Individual Protein	Cathepsin L2	Homo sapiens	Ki	=	10000.0	nM	PMID[539158]

☑ 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 NPC170333 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	469
0.1-0.2	3083
0.2-0.3	12037
0.3-0.4	5413
0.4-0.5	10659
0.5-0.6	9459
0.6-0.7	1369
0.7-0.8	161
0.8-0.85	21
0.85-0.9	19
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9454	High Similarity	NPC212123
0.9451	High Similarity	NPC133156
0.9202	High Similarity	NPC305542
0.9053	High Similarity	NPC30749
0.9029	High Similarity	NPC298320
0.8995	High Similarity	NPC474366
0.8848	High Similarity	NPC218303
0.8827	High Similarity	NPC7560
0.8808	High Similarity	NPC176113
0.8808	High Similarity	NPC148391
0.8711	High Similarity	NPC2905
0.8673	High Similarity	NPC182853
0.866	High Similarity	NPC114468
0.8636	High Similarity	NPC76478
0.8607	High Similarity	NPC13249
0.8579	High Similarity	NPC134702
0.8557	High Similarity	NPC285254
0.8541	High Similarity	NPC114039
0.8541	High Similarity	NPC206109
0.8526	High Similarity	NPC15987
0.845	Intermediate Similarity	NPC118189
0.8446	Intermediate Similarity	NPC198160
0.84	Intermediate Similarity	NPC204867
0.8367	Intermediate Similarity	NPC220241
0.8367	Intermediate Similarity	NPC295479
0.8325	Intermediate Similarity	NPC116178
0.8283	Intermediate Similarity	NPC321166
0.8283	Intermediate Similarity	NPC268223
0.8283	Intermediate Similarity	NPC217903
0.822	Intermediate Similarity	NPC234933
0.8144	Intermediate Similarity	NPC288759
0.8119	Intermediate Similarity	NPC87560
0.8119	Intermediate Similarity	NPC195120
0.8095	Intermediate Similarity	NPC1820
0.8061	Intermediate Similarity	NPC313112
0.8061	Intermediate Similarity	NPC301292
0.8	Intermediate Similarity	NPC329830
0.7951	Intermediate Similarity	NPC157983
0.7951	Intermediate Similarity	NPC118154
0.7897	Intermediate Similarity	NPC241263
0.766	Intermediate Similarity	NPC474815
0.7627	Intermediate Similarity	NPC144691
0.7487	Intermediate Similarity	NPC327005
0.7371	Intermediate Similarity	NPC132751
0.7366	Intermediate Similarity	NPC299582
0.7333	Intermediate Similarity	NPC288854
0.729	Intermediate Similarity	NPC251071
0.7273	Intermediate Similarity	NPC70340
0.7211	Intermediate Similarity	NPC112336
0.7211	Intermediate Similarity	NPC474814
0.7166	Intermediate Similarity	NPC199737
0.7071	Intermediate Similarity	NPC150308
0.7065	Intermediate Similarity	NPC56170
0.7062	Intermediate Similarity	NPC9475
0.7059	Intermediate Similarity	NPC17677
0.7053	Intermediate Similarity	NPC41216
0.7045	Intermediate Similarity	NPC166480
0.7045	Intermediate Similarity	NPC282780
0.7028	Intermediate Similarity	NPC470481
0.7028	Intermediate Similarity	NPC470482
0.7005	Intermediate Similarity	NPC1464
0.699	Remote Similarity	NPC166169
0.6976	Remote Similarity	NPC218733
0.6976	Remote Similarity	NPC265642
0.6976	Remote Similarity	NPC138615
0.6976	Remote Similarity	NPC132874
0.6976	Remote Similarity	NPC112937
0.6959	Remote Similarity	NPC469439
0.6954	Remote Similarity	NPC474998
0.6944	Remote Similarity	NPC242994
0.6944	Remote Similarity	NPC138099
0.6942	Remote Similarity	NPC317727
0.6936	Remote Similarity	NPC162612
0.6936	Remote Similarity	NPC103356
0.6936	Remote Similarity	NPC169250
0.6936	Remote Similarity	NPC30501
0.6936	Remote Similarity	NPC98254
0.6936	Remote Similarity	NPC105157
0.6936	Remote Similarity	NPC266689
0.6936	Remote Similarity	NPC72158
0.6936	Remote Similarity	NPC100067
0.6936	Remote Similarity	NPC190043
0.6936	Remote Similarity	NPC23126
0.6931	Remote Similarity	NPC93653
0.6927	Remote Similarity	NPC33507
0.6923	Remote Similarity	NPC129578
0.6906	Remote Similarity	NPC181560
0.6906	Remote Similarity	NPC169452
0.6904	Remote Similarity	NPC98416
0.69	Remote Similarity	NPC262725
0.6897	Remote Similarity	NPC473017
0.6897	Remote Similarity	NPC221777
0.6897	Remote Similarity	NPC21305
0.6893	Remote Similarity	NPC83019
0.6891	Remote Similarity	NPC471778
0.6888	Remote Similarity	NPC127082
0.6884	Remote Similarity	NPC302235
0.6881	Remote Similarity	NPC469437
0.6879	Remote Similarity	NPC62952
0.6879	Remote Similarity	NPC8745
0.6879	Remote Similarity	NPC267846
0.6875	Remote Similarity	NPC155792
0.6875	Remote Similarity	NPC471489
0.6872	Remote Similarity	NPC194764
0.6872	Remote Similarity	NPC478075
0.6872	Remote Similarity	NPC264112
0.6872	Remote Similarity	NPC65005
0.6869	Remote Similarity	NPC309692
0.6865	Remote Similarity	NPC241392
0.6854	Remote Similarity	NPC25961
0.6847	Remote Similarity	NPC92803
0.6845	Remote Similarity	NPC204580
0.6839	Remote Similarity	NPC116513
0.6834	Remote Similarity	NPC99723
0.6833	Remote Similarity	NPC53414
0.6833	Remote Similarity	NPC53206
0.6833	Remote Similarity	NPC471905
0.6832	Remote Similarity	NPC18890
0.6831	Remote Similarity	NPC193555
0.6821	Remote Similarity	NPC73280
0.6821	Remote Similarity	NPC10926
0.6816	Remote Similarity	NPC43218
0.6808	Remote Similarity	NPC477825
0.6798	Remote Similarity	NPC213485
0.6798	Remote Similarity	NPC40524
0.6798	Remote Similarity	NPC139074
0.6794	Remote Similarity	NPC232600
0.6791	Remote Similarity	NPC68967
0.6791	Remote Similarity	NPC477826
0.6791	Remote Similarity	NPC477827
0.6784	Remote Similarity	NPC472163
0.678	Remote Similarity	NPC470485
0.678	Remote Similarity	NPC471825
0.678	Remote Similarity	NPC78284
0.678	Remote Similarity	NPC475042
0.6778	Remote Similarity	NPC254847
0.6778	Remote Similarity	NPC191976
0.6776	Remote Similarity	NPC297322
0.6763	Remote Similarity	NPC13238
0.6761	Remote Similarity	NPC109123
0.6761	Remote Similarity	NPC329567
0.6761	Remote Similarity	NPC207873
0.6761	Remote Similarity	NPC92624
0.6761	Remote Similarity	NPC100573
0.6761	Remote Similarity	NPC330683
0.676	Remote Similarity	NPC44437
0.6757	Remote Similarity	NPC477394
0.6756	Remote Similarity	NPC227033
0.6752	Remote Similarity	NPC317567
0.6749	Remote Similarity	NPC329790
0.6744	Remote Similarity	NPC220337
0.6742	Remote Similarity	NPC175738
0.6739	Remote Similarity	NPC135524
0.6734	Remote Similarity	NPC85613
0.673	Remote Similarity	NPC317572
0.6723	Remote Similarity	NPC259942
0.6722	Remote Similarity	NPC283590
0.6722	Remote Similarity	NPC130899
0.6722	Remote Similarity	NPC70859
0.6722	Remote Similarity	NPC61153
0.6717	Remote Similarity	NPC477187
0.6716	Remote Similarity	NPC208890
0.6715	Remote Similarity	NPC303214
0.6714	Remote Similarity	NPC308943
0.6714	Remote Similarity	NPC469732
0.6712	Remote Similarity	NPC94842
0.6704	Remote Similarity	NPC267205
0.6702	Remote Similarity	NPC37135
0.6702	Remote Similarity	NPC186397
0.6698	Remote Similarity	NPC470484
0.6698	Remote Similarity	NPC163829
0.6697	Remote Similarity	NPC253314
0.6686	Remote Similarity	NPC305717
0.6685	Remote Similarity	NPC246638
0.6685	Remote Similarity	NPC118919
0.6685	Remote Similarity	NPC305845
0.6685	Remote Similarity	NPC204045
0.6684	Remote Similarity	NPC85393
0.6684	Remote Similarity	NPC110882
0.6684	Remote Similarity	NPC271944
0.6683	Remote Similarity	NPC316282
0.6683	Remote Similarity	NPC470483
0.6682	Remote Similarity	NPC122886
0.6681	Remote Similarity	NPC289905
0.6681	Remote Similarity	NPC316065
0.6667	Remote Similarity	NPC476119
0.6667	Remote Similarity	NPC477828
0.6667	Remote Similarity	NPC158551
0.6667	Remote Similarity	NPC475088
0.6667	Remote Similarity	NPC23294
0.6667	Remote Similarity	NPC223988
0.6667	Remote Similarity	NPC21599
0.6667	Remote Similarity	NPC143438
0.6667	Remote Similarity	NPC264938
0.6667	Remote Similarity	NPC246140
0.6667	Remote Similarity	NPC193703
0.6667	Remote Similarity	NPC266499
0.6667	Remote Similarity	NPC195787
0.6653	Remote Similarity	NPC132385
0.6652	Remote Similarity	NPC151171

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 NPC170333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	694
0.2-0.3	978
0.3-0.4	1716
0.4-0.5	3028
0.5-0.6	1961
0.6-0.7	446
0.7-0.8	37
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
0.8535	High Similarity	NPD2899	Discontinued
0.7868	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5937	Approved
0.7421	Intermediate Similarity	NPD6020	Phase 2
0.7228	Intermediate Similarity	NPD5194	Approved
0.7228	Intermediate Similarity	NPD5197	Approved
0.7228	Intermediate Similarity	NPD5196	Approved
0.7184	Intermediate Similarity	NPD3298	Approved
0.715	Intermediate Similarity	NPD5496	Approved
0.7122	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5860	Discontinued
0.7092	Intermediate Similarity	NPD3253	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5637	Discontinued
0.7024	Intermediate Similarity	NPD6874	Approved
0.7024	Intermediate Similarity	NPD3297	Approved
0.701	Intermediate Similarity	NPD5195	Discontinued
0.7009	Intermediate Similarity	NPD8461	Discontinued
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD1220	Phase 1
0.6977	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1221	Approved
0.6971	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5610	Approved
0.6942	Remote Similarity	NPD5608	Approved
0.6942	Remote Similarity	NPD5609	Approved
0.692	Remote Similarity	NPD6625	Approved
0.6908	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1945	Phase 1
0.6869	Remote Similarity	NPD6104	Discontinued
0.6869	Remote Similarity	NPD7301	Phase 3
0.6857	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3229	Phase 2
0.6842	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4082	Approved
0.6812	Remote Similarity	NPD4668	Phase 2
0.681	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5183	Approved
0.6804	Remote Similarity	NPD5186	Approved
0.6792	Remote Similarity	NPD4596	Phase 1
0.6778	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4467	Phase 2
0.6777	Remote Similarity	NPD4465	Phase 2
0.6761	Remote Similarity	NPD7302	Phase 3
0.6761	Remote Similarity	NPD4022	Approved
0.6761	Remote Similarity	NPD7300	Phase 3
0.6761	Remote Similarity	NPD2906	Approved
0.6761	Remote Similarity	NPD2907	Approved
0.6761	Remote Similarity	NPD3472	Approved
0.6756	Remote Similarity	NPD8067	Phase 3
0.6752	Remote Similarity	NPD8367	Approved
0.6752	Remote Similarity	NPD3986	Discontinued
0.6741	Remote Similarity	NPD7654	Discontinued
0.6728	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5928	Phase 1
0.6714	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD8492	Approved
0.6698	Remote Similarity	NPD3372	Discontinued
0.6698	Remote Similarity	NPD1294	Discontinued
0.6684	Remote Similarity	NPD1913	Phase 1
0.6667	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD4360	Phase 2
0.665	Remote Similarity	NPD5968	Phase 3
0.6648	Remote Similarity	NPD943	Approved
0.6638	Remote Similarity	NPD1483	Discontinued
0.6637	Remote Similarity	NPD6199	Discontinued
0.6637	Remote Similarity	NPD4981	Phase 2
0.6636	Remote Similarity	NPD7293	Approved
0.6636	Remote Similarity	NPD6198	Phase 1
0.6636	Remote Similarity	NPD4494	Approved
0.6636	Remote Similarity	NPD4492	Approved
0.6635	Remote Similarity	NPD4361	Phase 2
0.6635	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3793	Phase 3
0.6623	Remote Similarity	NPD7922	Phase 1
0.6617	Remote Similarity	NPD5027	Approved
0.6617	Remote Similarity	NPD5031	Approved
0.6617	Remote Similarity	NPD5029	Approved
0.6616	Remote Similarity	NPD3446	Phase 1
0.6615	Remote Similarity	NPD5823	Approved
0.6613	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7292	Approved
0.6558	Remote Similarity	NPD7584	Approved
0.6537	Remote Similarity	NPD4515	Suspended
0.6537	Remote Similarity	NPD5037	Approved
0.6537	Remote Similarity	NPD5038	Approved
0.6526	Remote Similarity	NPD5005	Approved
0.6526	Remote Similarity	NPD5006	Approved
0.6524	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5242	Approved
0.6514	Remote Similarity	NPD4493	Discontinued
0.6489	Remote Similarity	NPD7390	Discontinued
0.6488	Remote Similarity	NPD5036	Approved
0.6486	Remote Similarity	NPD9277	Approved
0.6486	Remote Similarity	NPD75	Approved
0.6485	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6836	Approved
0.6468	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD3893	Discontinued
0.6465	Remote Similarity	NPD1839	Phase 1
0.6465	Remote Similarity	NPD5711	Approved
0.6465	Remote Similarity	NPD5710	Approved
0.646	Remote Similarity	NPD3925	Approved
0.6459	Remote Similarity	NPD4539	Phase 1
0.6455	Remote Similarity	NPD4888	Discontinued
0.6452	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5033	Approved
0.6438	Remote Similarity	NPD683	Approved
0.6436	Remote Similarity	NPD4956	Approved
0.6436	Remote Similarity	NPD7479	Phase 2
0.6436	Remote Similarity	NPD5190	Phase 2
0.6435	Remote Similarity	NPD6807	Phase 3
0.6432	Remote Similarity	NPD9275	Approved
0.6432	Remote Similarity	NPD9278	Suspended
0.6432	Remote Similarity	NPD9274	Approved
0.6432	Remote Similarity	NPD9276	Approved
0.6425	Remote Similarity	NPD2672	Discontinued
0.6425	Remote Similarity	NPD1898	Discontinued
0.6418	Remote Similarity	NPD2361	Approved
0.6418	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1196	Approved
0.6415	Remote Similarity	NPD5071	Phase 2
0.6414	Remote Similarity	NPD5488	Discontinued
0.6414	Remote Similarity	NPD2821	Approved
0.6409	Remote Similarity	NPD1527	Phase 2
0.6409	Remote Similarity	NPD3888	Discontinued
0.6407	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5445	Approved
0.6402	Remote Similarity	NPD1543	Discontinued
0.6395	Remote Similarity	NPD4846	Phase 2
0.6393	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4603	Phase 2
0.6383	Remote Similarity	NPD6790	Phase 1
0.638	Remote Similarity	NPD4455	Discontinued
0.6376	Remote Similarity	NPD7585	Approved
0.6373	Remote Similarity	NPD3684	Discontinued
0.6373	Remote Similarity	NPD5039	Approved
0.6368	Remote Similarity	NPD3423	Phase 2
0.6368	Remote Similarity	NPD2359	Approved
0.6368	Remote Similarity	NPD6162	Approved
0.6368	Remote Similarity	NPD3422	Phase 3
0.6368	Remote Similarity	NPD6161	Approved
0.6368	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1195	Approved
0.6364	Remote Similarity	NPD1625	Approved
0.6359	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD3437	Discontinued
0.6355	Remote Similarity	NPD2339	Phase 3
0.6345	Remote Similarity	NPD955	Approved
0.6344	Remote Similarity	NPD7279	Phase 2
0.6344	Remote Similarity	NPD7278	Phase 2
0.6341	Remote Similarity	NPD4955	Approved
0.6341	Remote Similarity	NPD36	Approved
0.6341	Remote Similarity	NPD5034	Approved
0.6341	Remote Similarity	NPD5026	Approved
0.6341	Remote Similarity	NPD5028	Approved
0.6341	Remote Similarity	NPD4954	Approved
0.634	Remote Similarity	NPD4561	Discontinued
0.6339	Remote Similarity	NPD1926	Approved
0.6338	Remote Similarity	NPD4420	Approved
0.6337	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7583	Approved
0.633	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7263	Phase 2
0.633	Remote Similarity	NPD7043	Discontinued
0.6326	Remote Similarity	NPD6321	Discontinued
0.6325	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD1510	Phase 2
0.6323	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD2248	Approved
0.6318	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD3377	Discontinued
0.6318	Remote Similarity	NPD2246	Approved
0.6316	Remote Similarity	NPD2421	Approved
0.6316	Remote Similarity	NPD2420	Approved
0.6314	Remote Similarity	NPD7417	Discontinued
0.6313	Remote Similarity	NPD1168	Approved
0.6308	Remote Similarity	NPD6844	Discontinued
0.6305	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7701	Phase 2
0.6296	Remote Similarity	NPD6017	Discontinued
0.6293	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5030	Phase 2
0.6289	Remote Similarity	NPD4380	Phase 2
0.6289	Remote Similarity	NPD6585	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