NPASS Compound

Structure

NPC472163 OpenBabel07101718322D 24 25 0 0 0 0 0 0 0 0999 V2000 0.8660 6.5000 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 -3.0000 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 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 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 3.4641 -1.0000 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 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 0.0000 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 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 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 14 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 15 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.21
Volume:	361.548
LogP:	5.25
LogD:	4.1
LogS:	-4.616
# Rotatable Bonds:	9
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.674
Synthetic Accessibility Score:	2.42
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.845
MDCK Permeability:	1.5455027096322738e-05
Pgp-inhibitor:	0.581
Pgp-substrate:	0.474
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.802
30% Bioavailability (F30%):	0.571

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.27
Plasma Protein Binding (PPB):	98.91615295410156%
Volume Distribution (VD):	1.432
Pgp-substrate:	1.5039469003677368%

ADMET: Metabolism

CYP1A2-inhibitor:	0.932
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	3.063
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.636
AMES Toxicity:	0.293
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.103
Skin Sensitization:	0.947
Carcinogencity:	0.15
Eye Corrosion:	0.076
Eye Irritation:	0.831
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC472163

Natural Product ID:	NPC472163
*Common Name:**	IJGDGRMCHJUXEN-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IJGDGRMCHJUXEN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H29NO3/c1-5-6-7-8-9-10-11-15-12-13-16(23-3)18-17(15)19(22)20(24-4)14(2)21-18/h12-13H,5-11H2,1-4H3,(H,21,22)
SMILES:	CCCCCCCCc1ccc(c2c1c(=O)c(c(C)[nH]2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342750
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO22669	Waltheria indica	Species	Malvaceae	Eukaryota	roots	n.a.	n.a.	PMID[25314007]
NPO22669	Waltheria indica	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26848627]
NPO40548	Melochia umbellata var. deglabrata	Strain	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32946697]
NPO22669	Waltheria indica	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33095014]
NPO22669	Waltheria indica	Species	Malvaceae	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	10
MIC	10
Others	2

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Organism	12
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	25700.0	nM	PMID[550281]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	14.4	ug.mL-1	PMID[550282]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[550283]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[550283]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[550283]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[550283]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	38600.0	nM	PMID[550281]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	31000.0	nM	PMID[550281]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	1100.0	nM	PMID[550281]
NPT2	Others	Unspecified		Ratio IC50	=	22.7	n.a.	PMID[550281]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	16.0	ug.mL-1	PMID[550282]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	8.0	ug.mL-1	PMID[550282]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32.0	ug.mL-1	PMID[550282]
NPT2	Others	Unspecified		Selectivity Index	=	1.8	n.a.	PMID[550282]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[550283]

☑ 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 NPC472163 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	477
0.1-0.2	3067
0.2-0.3	12640
0.3-0.4	4129
0.4-0.5	15447
0.5-0.6	5307
0.6-0.7	1361
0.7-0.8	238
0.8-0.85	17
0.85-0.9	9
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.7965	Intermediate Similarity	NPC257763
0.7907	Intermediate Similarity	NPC93653
0.7833	Intermediate Similarity	NPC283810
0.776	Intermediate Similarity	NPC49184
0.7747	Intermediate Similarity	NPC314659
0.7704	Intermediate Similarity	NPC25961
0.7692	Intermediate Similarity	NPC197335
0.7644	Intermediate Similarity	NPC301163
0.7622	Intermediate Similarity	NPC87391
0.7541	Intermediate Similarity	NPC85613
0.7437	Intermediate Similarity	NPC474366
0.7374	Intermediate Similarity	NPC299582
0.7363	Intermediate Similarity	NPC73280
0.7358	Intermediate Similarity	NPC470021
0.7351	Intermediate Similarity	NPC5167
0.7313	Intermediate Similarity	NPC218303
0.7291	Intermediate Similarity	NPC176113
0.7286	Intermediate Similarity	NPC212123
0.7277	Intermediate Similarity	NPC1820
0.7241	Intermediate Similarity	NPC30749
0.7194	Intermediate Similarity	NPC241263
0.7157	Intermediate Similarity	NPC268223
0.7143	Intermediate Similarity	NPC112937
0.7128	Intermediate Similarity	NPC470023
0.7115	Intermediate Similarity	NPC225279
0.7114	Intermediate Similarity	NPC222561
0.7114	Intermediate Similarity	NPC478075
0.7109	Intermediate Similarity	NPC285254
0.7108	Intermediate Similarity	NPC305542
0.7097	Intermediate Similarity	NPC472894
0.7097	Intermediate Similarity	NPC8467
0.7092	Intermediate Similarity	NPC41488
0.7065	Intermediate Similarity	NPC246140
0.7065	Intermediate Similarity	NPC195787
0.7048	Intermediate Similarity	NPC251071
0.7048	Intermediate Similarity	NPC144452
0.7039	Intermediate Similarity	NPC148391
0.7037	Intermediate Similarity	NPC270301
0.7027	Intermediate Similarity	NPC471604
0.7023	Intermediate Similarity	NPC49547
0.7019	Intermediate Similarity	NPC87560
0.7019	Intermediate Similarity	NPC195120
0.7	Intermediate Similarity	NPC76478
0.6984	Remote Similarity	NPC98416
0.6979	Remote Similarity	NPC262725
0.6949	Remote Similarity	NPC144691
0.6938	Remote Similarity	NPC182853
0.6938	Remote Similarity	NPC134702
0.6931	Remote Similarity	NPC133156
0.6927	Remote Similarity	NPC313886
0.6923	Remote Similarity	NPC22476
0.6919	Remote Similarity	NPC118189
0.6916	Remote Similarity	NPC74575
0.6915	Remote Similarity	NPC288759
0.6908	Remote Similarity	NPC114468
0.6884	Remote Similarity	NPC234933
0.6884	Remote Similarity	NPC274640
0.6884	Remote Similarity	NPC71124
0.6878	Remote Similarity	NPC315631
0.6875	Remote Similarity	NPC2905
0.6875	Remote Similarity	NPC298449
0.6872	Remote Similarity	NPC118154
0.6872	Remote Similarity	NPC157983
0.6868	Remote Similarity	NPC57512
0.6865	Remote Similarity	NPC476569
0.6865	Remote Similarity	NPC314861
0.6859	Remote Similarity	NPC116096
0.6853	Remote Similarity	NPC254957
0.6847	Remote Similarity	NPC313112
0.6847	Remote Similarity	NPC301292
0.6842	Remote Similarity	NPC287152
0.684	Remote Similarity	NPC7560
0.6837	Remote Similarity	NPC13249
0.682	Remote Similarity	NPC474688
0.6802	Remote Similarity	NPC114039
0.6802	Remote Similarity	NPC206109
0.6789	Remote Similarity	NPC4669
0.6786	Remote Similarity	NPC208522
0.6784	Remote Similarity	NPC170333
0.6784	Remote Similarity	NPC173295
0.678	Remote Similarity	NPC308943
0.6777	Remote Similarity	NPC77777
0.6771	Remote Similarity	NPC28368
0.6766	Remote Similarity	NPC5374
0.6765	Remote Similarity	NPC87714
0.6765	Remote Similarity	NPC268077
0.6765	Remote Similarity	NPC475147
0.676	Remote Similarity	NPC241392
0.6748	Remote Similarity	NPC329567
0.6748	Remote Similarity	NPC330683
0.6735	Remote Similarity	NPC477998
0.6734	Remote Similarity	NPC198401
0.6731	Remote Similarity	NPC295479
0.6731	Remote Similarity	NPC220241
0.6731	Remote Similarity	NPC187501
0.672	Remote Similarity	NPC153631
0.6716	Remote Similarity	NPC138615
0.6716	Remote Similarity	NPC218733
0.6716	Remote Similarity	NPC23080
0.6716	Remote Similarity	NPC132874
0.6716	Remote Similarity	NPC193906
0.6716	Remote Similarity	NPC207971
0.6716	Remote Similarity	NPC17677
0.6716	Remote Similarity	NPC265642
0.6716	Remote Similarity	NPC100863
0.6713	Remote Similarity	NPC470018
0.6705	Remote Similarity	NPC43218
0.6703	Remote Similarity	NPC476580
0.67	Remote Similarity	NPC214368
0.6699	Remote Similarity	NPC198160
0.6697	Remote Similarity	NPC154922
0.6684	Remote Similarity	NPC121400
0.6684	Remote Similarity	NPC127362
0.6684	Remote Similarity	NPC471652
0.6683	Remote Similarity	NPC78284
0.6682	Remote Similarity	NPC257851
0.6667	Remote Similarity	NPC39500
0.6667	Remote Similarity	NPC288987
0.6667	Remote Similarity	NPC470019
0.6667	Remote Similarity	NPC1464
0.6667	Remote Similarity	NPC100573
0.6667	Remote Similarity	NPC207873
0.6667	Remote Similarity	NPC474815
0.6667	Remote Similarity	NPC471316
0.6667	Remote Similarity	NPC314702
0.6667	Remote Similarity	NPC316282
0.6667	Remote Similarity	NPC15987
0.6667	Remote Similarity	NPC122886
0.6667	Remote Similarity	NPC90185
0.6667	Remote Similarity	NPC208084
0.6649	Remote Similarity	NPC231862
0.6646	Remote Similarity	NPC179605
0.6646	Remote Similarity	NPC279385
0.6638	Remote Similarity	NPC67401
0.6635	Remote Similarity	NPC475133
0.6634	Remote Similarity	NPC41216
0.6628	Remote Similarity	NPC266425
0.662	Remote Similarity	NPC51388
0.6619	Remote Similarity	NPC470482
0.6619	Remote Similarity	NPC470481
0.6617	Remote Similarity	NPC108847
0.6616	Remote Similarity	NPC45389
0.6616	Remote Similarity	NPC474059
0.6616	Remote Similarity	NPC5630
0.6611	Remote Similarity	NPC242000
0.6607	Remote Similarity	NPC41501
0.6606	Remote Similarity	NPC103292
0.6601	Remote Similarity	NPC317727
0.6598	Remote Similarity	NPC190461
0.6592	Remote Similarity	NPC472061
0.6589	Remote Similarity	NPC222046
0.6587	Remote Similarity	NPC217277
0.6584	Remote Similarity	NPC314948
0.6579	Remote Similarity	NPC469671
0.6579	Remote Similarity	NPC126676
0.6578	Remote Similarity	NPC148889
0.6578	Remote Similarity	NPC475844
0.6573	Remote Similarity	NPC195636
0.657	Remote Similarity	NPC477161
0.6567	Remote Similarity	NPC243626
0.6567	Remote Similarity	NPC198205
0.6567	Remote Similarity	NPC230313
0.6567	Remote Similarity	NPC21483
0.6561	Remote Similarity	NPC306669
0.6557	Remote Similarity	NPC119669
0.6557	Remote Similarity	NPC476579
0.6557	Remote Similarity	NPC55470
0.6555	Remote Similarity	NPC477160
0.655	Remote Similarity	NPC270515
0.655	Remote Similarity	NPC196231
0.6549	Remote Similarity	NPC113455
0.6546	Remote Similarity	NPC70092
0.6542	Remote Similarity	NPC184408
0.654	Remote Similarity	NPC116178
0.654	Remote Similarity	NPC474428
0.654	Remote Similarity	NPC38237
0.654	Remote Similarity	NPC119722
0.6537	Remote Similarity	NPC471489
0.6534	Remote Similarity	NPC314252
0.6529	Remote Similarity	NPC122235
0.6528	Remote Similarity	NPC280799
0.6528	Remote Similarity	NPC285941
0.6528	Remote Similarity	NPC9475
0.6524	Remote Similarity	NPC57105
0.6522	Remote Similarity	NPC58661
0.6518	Remote Similarity	NPC470022
0.6515	Remote Similarity	NPC21425
0.6514	Remote Similarity	NPC231924
0.6509	Remote Similarity	NPC217903
0.6509	Remote Similarity	NPC321166
0.6509	Remote Similarity	NPC324361
0.6502	Remote Similarity	NPC478049
0.6502	Remote Similarity	NPC198390
0.65	Remote Similarity	NPC203628
0.65	Remote Similarity	NPC472840
0.6495	Remote Similarity	NPC293151
0.6492	Remote Similarity	NPC284842
0.6488	Remote Similarity	NPC226794
0.6486	Remote Similarity	NPC139373
0.6481	Remote Similarity	NPC476069

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 NPC472163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	673
0.2-0.3	1041
0.3-0.4	1415
0.4-0.5	2972
0.5-0.6	2110
0.6-0.7	571
0.7-0.8	43
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.75	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2247	Approved
0.7486	Intermediate Similarity	NPD2249	Approved
0.7459	Intermediate Similarity	NPD3253	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4859	Phase 1
0.731	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5186	Approved
0.7253	Intermediate Similarity	NPD5183	Approved
0.7181	Intermediate Similarity	NPD1891	Discontinued
0.7166	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1945	Phase 1
0.7104	Intermediate Similarity	NPD2680	Approved
0.7104	Intermediate Similarity	NPD2681	Approved
0.7097	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4082	Approved
0.7079	Intermediate Similarity	NPD3472	Approved
0.7079	Intermediate Similarity	NPD4022	Approved
0.7069	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4493	Discontinued
0.7045	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2672	Discontinued
0.7035	Intermediate Similarity	NPD6238	Discontinued
0.7031	Intermediate Similarity	NPD4515	Suspended
0.703	Intermediate Similarity	NPD4596	Phase 1
0.7015	Intermediate Similarity	NPD4456	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3372	Discontinued
0.701	Intermediate Similarity	NPD3893	Discontinued
0.7	Intermediate Similarity	NPD1769	Discontinued
0.6986	Remote Similarity	NPD2899	Discontinued
0.697	Remote Similarity	NPD5071	Phase 2
0.6959	Remote Similarity	NPD1626	Approved
0.6942	Remote Similarity	NPD4494	Approved
0.6942	Remote Similarity	NPD4492	Approved
0.6938	Remote Similarity	NPD4429	Discontinued
0.6927	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5860	Discontinued
0.6908	Remote Similarity	NPD4455	Discontinued
0.6865	Remote Similarity	NPD1559	Discontinued
0.686	Remote Similarity	NPD3888	Discontinued
0.6859	Remote Similarity	NPD6104	Discontinued
0.6835	Remote Similarity	NPD6625	Approved
0.6834	Remote Similarity	NPD5515	Phase 2
0.6829	Remote Similarity	NPD2514	Approved
0.6828	Remote Similarity	NPD2821	Approved
0.6806	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1625	Approved
0.68	Remote Similarity	NPD5197	Approved
0.68	Remote Similarity	NPD5194	Approved
0.68	Remote Similarity	NPD5196	Approved
0.6784	Remote Similarity	NPD3964	Approved
0.678	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8149	Discontinued
0.6757	Remote Similarity	NPD1307	Phase 2
0.6757	Remote Similarity	NPD1309	Phase 2
0.6755	Remote Similarity	NPD5242	Approved
0.6748	Remote Similarity	NPD2906	Approved
0.6748	Remote Similarity	NPD2907	Approved
0.6748	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3558	Approved
0.6739	Remote Similarity	NPD5977	Approved
0.6739	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3560	Approved
0.6739	Remote Similarity	NPD3556	Approved
0.6739	Remote Similarity	NPD3557	Approved
0.6739	Remote Similarity	NPD5978	Approved
0.6738	Remote Similarity	NPD6457	Approved
0.673	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3301	Approved
0.672	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD3684	Discontinued
0.6701	Remote Similarity	NPD7546	Discontinued
0.6699	Remote Similarity	NPD7225	Discontinued
0.6698	Remote Similarity	NPD7278	Phase 2
0.6698	Remote Similarity	NPD7279	Phase 2
0.6684	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4467	Phase 2
0.6683	Remote Similarity	NPD3297	Approved
0.6683	Remote Similarity	NPD6644	Discontinued
0.6683	Remote Similarity	NPD4465	Phase 2
0.6667	Remote Similarity	NPD5950	Discontinued
0.6667	Remote Similarity	NPD4083	Discontinued
0.6667	Remote Similarity	NPD4586	Phase 3
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7256	Discontinued
0.6649	Remote Similarity	NPD1012	Discontinued
0.6648	Remote Similarity	NPD2649	Approved
0.6648	Remote Similarity	NPD2651	Approved
0.6634	Remote Similarity	NPD4668	Phase 2
0.663	Remote Similarity	NPD3641	Approved
0.663	Remote Similarity	NPD3639	Approved
0.663	Remote Similarity	NPD3640	Phase 3
0.6622	Remote Similarity	NPD3006	Discontinued
0.6621	Remote Similarity	NPD5022	Discontinued
0.6618	Remote Similarity	NPD6321	Discontinued
0.6616	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4888	Discontinued
0.6602	Remote Similarity	NPD3298	Approved
0.6601	Remote Similarity	NPD5608	Approved
0.6601	Remote Similarity	NPD5609	Approved
0.6599	Remote Similarity	NPD4587	Phase 3
0.6599	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7324	Discontinued
0.6595	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4505	Phase 1
0.6585	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5195	Discontinued
0.658	Remote Similarity	NPD7479	Phase 2
0.6576	Remote Similarity	NPD2836	Approved
0.6573	Remote Similarity	NPD6719	Approved
0.6569	Remote Similarity	NPD3290	Approved
0.6569	Remote Similarity	NPD3289	Phase 3
0.6566	Remote Similarity	NPD1898	Discontinued
0.655	Remote Similarity	NPD5937	Approved
0.6548	Remote Similarity	NPD3153	Approved
0.6548	Remote Similarity	NPD3154	Approved
0.6546	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6199	Discontinued
0.6538	Remote Similarity	NPD2434	Approved
0.6537	Remote Similarity	NPD7476	Discontinued
0.6532	Remote Similarity	NPD7922	Phase 1
0.653	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5810	Discontinued
0.6528	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6874	Approved
0.6508	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD5416	Discontinued
0.6488	Remote Similarity	NPD6519	Phase 2
0.6486	Remote Similarity	NPD6386	Approved
0.6486	Remote Similarity	NPD6385	Approved
0.6461	Remote Similarity	NPD4597	Approved
0.6461	Remote Similarity	NPD4598	Approved
0.6458	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3416	Discontinued
0.6453	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4259	Approved
0.645	Remote Similarity	NPD4258	Approved
0.6443	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.644	Remote Similarity	NPD5847	Phase 1
0.6439	Remote Similarity	NPD1880	Phase 3
0.6437	Remote Similarity	NPD3142	Approved
0.6437	Remote Similarity	NPD3140	Approved
0.6436	Remote Similarity	NPD5610	Approved
0.6432	Remote Similarity	NPD3538	Suspended
0.6429	Remote Similarity	NPD7302	Phase 3
0.6429	Remote Similarity	NPD7300	Phase 3
0.6425	Remote Similarity	NPD7316	Discontinued
0.6425	Remote Similarity	NPD5938	Phase 3
0.6425	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7626	Approved
0.6425	Remote Similarity	NPD7627	Approved
0.6425	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6037	Discontinued
0.6417	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4502	Phase 2
0.6415	Remote Similarity	NPD7272	Discontinued
0.6414	Remote Similarity	NPD6618	Phase 2
0.641	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD2339	Phase 3
0.6406	Remote Similarity	NPD3437	Discontinued
0.6406	Remote Similarity	NPD6242	Discontinued
0.6398	Remote Similarity	NPD4205	Phase 3
0.6398	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4981	Phase 2
0.6394	Remote Similarity	NPD3802	Phase 3
0.639	Remote Similarity	NPD4420	Approved
0.6386	Remote Similarity	NPD3479	Discontinued
0.6384	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5429	Discontinued
0.6381	Remote Similarity	NPD7263	Phase 2
0.6378	Remote Similarity	NPD5086	Approved
0.6374	Remote Similarity	NPD1801	Approved
0.6374	Remote Similarity	NPD1802	Approved
0.6373	Remote Similarity	NPD2248	Approved
0.6373	Remote Similarity	NPD2246	Approved
0.6373	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5025	Approved
0.6369	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1189	Approved
0.6368	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8067	Phase 3
0.6364	Remote Similarity	NPD3925	Approved
0.6364	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6030	Approved

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