NPASS Compound

Structure

NPC472164 OpenBabel07101718322D 27 29 0 0 1 0 0 0 0 0999 V2000 -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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 0.8660 -2.5000 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 5.1962 -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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -2.5981 -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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 19 14 1 1 0 0 0 19 21 1 0 0 0 0 20 21 2 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.23
Volume:	402.243
LogP:	5.635
LogD:	4.01
LogS:	-6.02
# Rotatable Bonds:	8
TPSA:	40.46
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	3.224
Fsp3:	0.522
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:	-4.741
MDCK Permeability:	1.4655973245680798e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.434
Plasma Protein Binding (PPB):	96.7806167602539%
Volume Distribution (VD):	0.741
Pgp-substrate:	0.658470094203949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.864
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.852
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.553
CYP2D6-substrate:	0.767
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	3.197
Half-life (T1/2):	0.315

ADMET: Toxicity

hERG Blockers:	0.259
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.344
AMES Toxicity:	0.291
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.673
Carcinogencity:	0.268
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC472164

Natural Product ID:	NPC472164
*Common Name:**	QTWGFCPXTHDILL-IBGZPJMESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QTWGFCPXTHDILL-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C23H31NO3/c1-17-23(26-2)22(25)21-19(15-10-16-20(21)24(17)27-3)14-9-5-8-13-18-11-6-4-7-12-18/h4,6-7,11-12,19H,5,8-10,13-16H2,1-3H3/t19-/m0/s1
SMILES:	COn1c2CCC[C@@H](c2c(=O)c(c1C)OC)CCCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342751
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0000128] Alkyl aryl ethers

*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]
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	5
MIC	10
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	640.0	nM	PMID[509966]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	9.5	ug.mL-1	PMID[509967]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	30400.0	nM	PMID[509966]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	24100.0	nM	PMID[509966]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	20.0	nM	PMID[509966]
NPT2	Others	Unspecified		Ratio IC50	=	33.8	n.a.	PMID[509966]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	2.0	ug.mL-1	PMID[509967]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	32.0	ug.mL-1	PMID[509967]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[509967]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	16.0	ug.mL-1	PMID[509967]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	32.0	ug.mL-1	PMID[509967]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	32.0	ug.mL-1	PMID[509967]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	32.0	ug.mL-1	PMID[509967]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[509967]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32.0	ug.mL-1	PMID[509967]
NPT2	Others	Unspecified		Selectivity Index	=	0.3	n.a.	PMID[509967]

☑ 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 NPC472164 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	416
0.1-0.2	2548
0.2-0.3	10753
0.3-0.4	5752
0.4-0.5	16799
0.5-0.6	5056
0.6-0.7	1257
0.7-0.8	91
0.8-0.85	9
0.85-0.9	9
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.906	High Similarity	NPC472165
0.7909	Intermediate Similarity	NPC145052
0.7818	Intermediate Similarity	NPC103048
0.7727	Intermediate Similarity	NPC12695
0.7685	Intermediate Similarity	NPC476484
0.7593	Intermediate Similarity	NPC110420
0.7593	Intermediate Similarity	NPC67585
0.7593	Intermediate Similarity	NPC303967
0.75	Intermediate Similarity	NPC472788
0.7383	Intermediate Similarity	NPC472136
0.7328	Intermediate Similarity	NPC179224
0.7304	Intermediate Similarity	NPC112552
0.7295	Intermediate Similarity	NPC326664
0.7252	Intermediate Similarity	NPC81092
0.7252	Intermediate Similarity	NPC103605
0.7227	Intermediate Similarity	NPC470007
0.7227	Intermediate Similarity	NPC203732
0.7217	Intermediate Similarity	NPC476042
0.719	Intermediate Similarity	NPC137315
0.7167	Intermediate Similarity	NPC192577
0.7163	Intermediate Similarity	NPC246412
0.7099	Intermediate Similarity	NPC119326
0.708	Intermediate Similarity	NPC34243
0.7016	Intermediate Similarity	NPC67377
0.6964	Remote Similarity	NPC108026
0.696	Remote Similarity	NPC474408
0.6942	Remote Similarity	NPC470391
0.6937	Remote Similarity	NPC477704
0.6937	Remote Similarity	NPC477693
0.6917	Remote Similarity	NPC167336
0.6911	Remote Similarity	NPC291799
0.6909	Remote Similarity	NPC472161
0.6875	Remote Similarity	NPC231591
0.6825	Remote Similarity	NPC228936
0.68	Remote Similarity	NPC469547
0.6797	Remote Similarity	NPC471553
0.6794	Remote Similarity	NPC39818
0.6786	Remote Similarity	NPC116231
0.6752	Remote Similarity	NPC472167
0.6752	Remote Similarity	NPC472166
0.675	Remote Similarity	NPC274443
0.6748	Remote Similarity	NPC475282
0.6746	Remote Similarity	NPC241851
0.6724	Remote Similarity	NPC5472
0.6721	Remote Similarity	NPC100767
0.672	Remote Similarity	NPC292834
0.6719	Remote Similarity	NPC28951
0.6719	Remote Similarity	NPC325646
0.6694	Remote Similarity	NPC158854
0.6693	Remote Similarity	NPC470764
0.6692	Remote Similarity	NPC285394
0.6667	Remote Similarity	NPC477476
0.6667	Remote Similarity	NPC143768
0.6667	Remote Similarity	NPC477475
0.6667	Remote Similarity	NPC222390
0.6667	Remote Similarity	NPC13784
0.6667	Remote Similarity	NPC244427
0.6642	Remote Similarity	NPC477249
0.6642	Remote Similarity	NPC477248
0.6641	Remote Similarity	NPC235421
0.6641	Remote Similarity	NPC471616
0.6639	Remote Similarity	NPC7435
0.6639	Remote Similarity	NPC134120
0.6639	Remote Similarity	NPC474308
0.6639	Remote Similarity	NPC172483
0.6639	Remote Similarity	NPC474307
0.6639	Remote Similarity	NPC54647
0.6619	Remote Similarity	NPC477680
0.6615	Remote Similarity	NPC318173
0.6614	Remote Similarity	NPC196075
0.6613	Remote Similarity	NPC40178
0.6612	Remote Similarity	NPC247976
0.661	Remote Similarity	NPC156021
0.6587	Remote Similarity	NPC477250
0.6587	Remote Similarity	NPC212415
0.6585	Remote Similarity	NPC473498
0.6581	Remote Similarity	NPC260233
0.6581	Remote Similarity	NPC256452
0.6557	Remote Similarity	NPC329282
0.6555	Remote Similarity	NPC317280
0.6555	Remote Similarity	NPC322598
0.6555	Remote Similarity	NPC329387
0.6555	Remote Similarity	NPC179411
0.6552	Remote Similarity	NPC1682
0.6552	Remote Similarity	NPC153885
0.6552	Remote Similarity	NPC188844
0.6544	Remote Similarity	NPC152850
0.6544	Remote Similarity	NPC89923
0.6544	Remote Similarity	NPC105114
0.6544	Remote Similarity	NPC71933
0.6544	Remote Similarity	NPC239990
0.6541	Remote Similarity	NPC291027
0.6541	Remote Similarity	NPC213126
0.6541	Remote Similarity	NPC317474
0.6541	Remote Similarity	NPC169485
0.6541	Remote Similarity	NPC84281
0.6538	Remote Similarity	NPC323440
0.6538	Remote Similarity	NPC222968
0.6538	Remote Similarity	NPC80605
0.6538	Remote Similarity	NPC61651
0.6532	Remote Similarity	NPC47536
0.6531	Remote Similarity	NPC2672
0.6522	Remote Similarity	NPC84288
0.6519	Remote Similarity	NPC474479
0.6519	Remote Similarity	NPC474766
0.6515	Remote Similarity	NPC475827
0.6515	Remote Similarity	NPC476225
0.6515	Remote Similarity	NPC474223
0.6514	Remote Similarity	NPC285716
0.6514	Remote Similarity	NPC17408
0.6512	Remote Similarity	NPC260886
0.6512	Remote Similarity	NPC135730
0.6504	Remote Similarity	NPC471186
0.6503	Remote Similarity	NPC315051
0.65	Remote Similarity	NPC474473
0.65	Remote Similarity	NPC221825
0.6496	Remote Similarity	NPC478162
0.6496	Remote Similarity	NPC238219
0.6496	Remote Similarity	NPC478165
0.6496	Remote Similarity	NPC23453
0.6493	Remote Similarity	NPC65627
0.6486	Remote Similarity	NPC288903
0.6486	Remote Similarity	NPC242000
0.6475	Remote Similarity	NPC471317
0.6471	Remote Similarity	NPC278228
0.6471	Remote Similarity	NPC289201
0.6471	Remote Similarity	NPC226041
0.6471	Remote Similarity	NPC136453
0.6471	Remote Similarity	NPC239185
0.6466	Remote Similarity	NPC133461
0.6466	Remote Similarity	NPC141607
0.6466	Remote Similarity	NPC187725
0.6466	Remote Similarity	NPC284475
0.6462	Remote Similarity	NPC108532
0.6462	Remote Similarity	NPC469843
0.6462	Remote Similarity	NPC190298
0.6457	Remote Similarity	NPC218855
0.6457	Remote Similarity	NPC186128
0.6457	Remote Similarity	NPC474689
0.6457	Remote Similarity	NPC280789
0.6457	Remote Similarity	NPC471189
0.6444	Remote Similarity	NPC318067
0.6444	Remote Similarity	NPC325740
0.6444	Remote Similarity	NPC328107
0.6441	Remote Similarity	NPC473347
0.6439	Remote Similarity	NPC291962
0.6439	Remote Similarity	NPC204784
0.6439	Remote Similarity	NPC177684
0.6438	Remote Similarity	NPC190945
0.6435	Remote Similarity	NPC9822
0.6434	Remote Similarity	NPC474095
0.6434	Remote Similarity	NPC210092
0.6434	Remote Similarity	NPC33742
0.6434	Remote Similarity	NPC93181
0.6434	Remote Similarity	NPC153007
0.6422	Remote Similarity	NPC272260
0.6422	Remote Similarity	NPC151405
0.6422	Remote Similarity	NPC139901
0.6417	Remote Similarity	NPC49994
0.6417	Remote Similarity	NPC134882
0.6417	Remote Similarity	NPC476120
0.6417	Remote Similarity	NPC75724
0.6412	Remote Similarity	NPC268930
0.641	Remote Similarity	NPC155232
0.641	Remote Similarity	NPC77273
0.6406	Remote Similarity	NPC471481
0.6406	Remote Similarity	NPC470253
0.6404	Remote Similarity	NPC96625
0.6404	Remote Similarity	NPC69057
0.6403	Remote Similarity	NPC316746
0.6403	Remote Similarity	NPC157311
0.6391	Remote Similarity	NPC232958
0.6391	Remote Similarity	NPC279385
0.6391	Remote Similarity	NPC112373
0.6391	Remote Similarity	NPC238861
0.6391	Remote Similarity	NPC258531
0.6391	Remote Similarity	NPC179605
0.6391	Remote Similarity	NPC988
0.6391	Remote Similarity	NPC473243
0.6391	Remote Similarity	NPC161956
0.6391	Remote Similarity	NPC289432
0.6391	Remote Similarity	NPC105709
0.6391	Remote Similarity	NPC77000
0.6389	Remote Similarity	NPC9796
0.6385	Remote Similarity	NPC188010
0.6383	Remote Similarity	NPC132308
0.6378	Remote Similarity	NPC265513
0.6378	Remote Similarity	NPC474157
0.6378	Remote Similarity	NPC477247
0.6377	Remote Similarity	NPC472413
0.6377	Remote Similarity	NPC116057
0.6372	Remote Similarity	NPC95965
0.6372	Remote Similarity	NPC123476
0.6372	Remote Similarity	NPC294134
0.6371	Remote Similarity	NPC209632
0.637	Remote Similarity	NPC164947
0.637	Remote Similarity	NPC308197
0.637	Remote Similarity	NPC474254
0.637	Remote Similarity	NPC474159
0.6364	Remote Similarity	NPC152159

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 NPC472164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	664
0.2-0.3	819
0.3-0.4	1157
0.4-0.5	3094
0.5-0.6	2534
0.6-0.7	568
0.7-0.8	29
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7	Intermediate Similarity	NPD6637	Approved
0.696	Remote Similarity	NPD2319	Discontinued
0.696	Remote Similarity	NPD1711	Phase 2
0.693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4574	Approved
0.685	Remote Similarity	NPD4576	Approved
0.6833	Remote Similarity	NPD5909	Discontinued
0.6807	Remote Similarity	NPD2193	Phase 2
0.6807	Remote Similarity	NPD2648	Phase 3
0.68	Remote Similarity	NPD2607	Approved
0.6746	Remote Similarity	NPD1370	Approved
0.6746	Remote Similarity	NPD1373	Approved
0.6746	Remote Similarity	NPD1374	Approved
0.6746	Remote Similarity	NPD1371	Approved
0.6694	Remote Similarity	NPD1756	Approved
0.6694	Remote Similarity	NPD1752	Approved
0.6694	Remote Similarity	NPD2067	Discontinued
0.6692	Remote Similarity	NPD5157	Phase 1
0.6692	Remote Similarity	NPD5159	Phase 2
0.6692	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3399	Approved
0.6667	Remote Similarity	NPD6024	Approved
0.6667	Remote Similarity	NPD6027	Approved
0.6667	Remote Similarity	NPD2171	Approved
0.6667	Remote Similarity	NPD2196	Discontinued
0.6642	Remote Similarity	NPD5667	Approved
0.6639	Remote Similarity	NPD2066	Phase 3
0.6612	Remote Similarity	NPD3357	Discontinued
0.661	Remote Similarity	NPD1099	Approved
0.661	Remote Similarity	NPD4657	Approved
0.661	Remote Similarity	NPD1100	Approved
0.661	Remote Similarity	NPD4655	Approved
0.6587	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4094	Approved
0.6557	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7631	Approved
0.6541	Remote Similarity	NPD3132	Approved
0.6541	Remote Similarity	NPD4217	Approved
0.6541	Remote Similarity	NPD2610	Approved
0.6541	Remote Similarity	NPD4216	Approved
0.6541	Remote Similarity	NPD2608	Approved
0.6541	Remote Similarity	NPD4218	Approved
0.6541	Remote Similarity	NPD2611	Approved
0.6541	Remote Similarity	NPD2609	Approved
0.6541	Remote Similarity	NPD2612	Approved
0.6541	Remote Similarity	NPD4215	Approved
0.6541	Remote Similarity	NPD3131	Approved
0.6538	Remote Similarity	NPD2115	Approved
0.6538	Remote Similarity	NPD2117	Pre-registration
0.6538	Remote Similarity	NPD2116	Approved
0.6535	Remote Similarity	NPD7094	Approved
0.6535	Remote Similarity	NPD6858	Approved
0.6528	Remote Similarity	NPD2923	Approved
0.6522	Remote Similarity	NPD3673	Approved
0.6522	Remote Similarity	NPD6039	Approved
0.6522	Remote Similarity	NPD3672	Approved
0.6507	Remote Similarity	NPD6185	Discontinued
0.6504	Remote Similarity	NPD2192	Approved
0.6504	Remote Similarity	NPD2197	Approved
0.6489	Remote Similarity	NPD2994	Approved
0.6471	Remote Similarity	NPD3495	Discontinued
0.6466	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7609	Phase 3
0.6463	Remote Similarity	NPD4607	Approved
0.6452	Remote Similarity	NPD5706	Approved
0.6452	Remote Similarity	NPD5705	Approved
0.6452	Remote Similarity	NPD5704	Approved
0.6449	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3031	Approved
0.6439	Remote Similarity	NPD3030	Approved
0.6439	Remote Similarity	NPD3032	Approved
0.6438	Remote Similarity	NPD2435	Approved
0.6434	Remote Similarity	NPD4766	Approved
0.6429	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6758	Approved
0.6419	Remote Similarity	NPD3352	Approved
0.6419	Remote Similarity	NPD7478	Approved
0.6404	Remote Similarity	NPD1087	Approved
0.64	Remote Similarity	NPD7606	Phase 3
0.64	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5305	Approved
0.6391	Remote Similarity	NPD5306	Approved
0.6387	Remote Similarity	NPD1989	Approved
0.6378	Remote Similarity	NPD3643	Approved
0.6378	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD3644	Approved
0.6378	Remote Similarity	NPD3642	Approved
0.6378	Remote Similarity	NPD2201	Approved
0.6377	Remote Similarity	NPD7084	Phase 3
0.6371	Remote Similarity	NPD1677	Discontinued
0.6371	Remote Similarity	NPD1018	Approved
0.637	Remote Similarity	NPD7082	Approved
0.6357	Remote Similarity	NPD3598	Phase 3
0.6351	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4041	Approved
0.635	Remote Similarity	NPD2625	Approved
0.635	Remote Similarity	NPD2627	Approved
0.635	Remote Similarity	NPD2626	Approved
0.635	Remote Similarity	NPD2159	Approved
0.635	Remote Similarity	NPD2628	Approved
0.635	Remote Similarity	NPD2160	Approved
0.6343	Remote Similarity	NPD2946	Phase 2
0.6341	Remote Similarity	NPD1929	Approved
0.6341	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD1930	Approved
0.6333	Remote Similarity	NPD4513	Discontinued
0.6331	Remote Similarity	NPD4617	Approved
0.6331	Remote Similarity	NPD4620	Approved
0.6331	Remote Similarity	NPD5201	Approved
0.6331	Remote Similarity	NPD5203	Approved
0.6327	Remote Similarity	NPD7487	Discontinued
0.6312	Remote Similarity	NPD7713	Phase 3
0.6311	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1693	Approved
0.6299	Remote Similarity	NPD5236	Approved
0.6299	Remote Similarity	NPD4233	Approved
0.6299	Remote Similarity	NPD5239	Approved
0.6299	Remote Similarity	NPD4234	Approved
0.6299	Remote Similarity	NPD5237	Approved
0.6299	Remote Similarity	NPD5235	Approved
0.6299	Remote Similarity	NPD5240	Approved
0.6296	Remote Similarity	NPD4807	Approved
0.6296	Remote Similarity	NPD6287	Discontinued
0.6296	Remote Similarity	NPD7437	Approved
0.6296	Remote Similarity	NPD4806	Approved
0.6296	Remote Similarity	NPD7436	Approved
0.6293	Remote Similarity	NPD800	Approved
0.6293	Remote Similarity	NPD5347	Phase 2
0.6293	Remote Similarity	NPD5346	Phase 2
0.6291	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.629	Remote Similarity	NPD1237	Approved
0.6288	Remote Similarity	NPD6065	Approved
0.6286	Remote Similarity	NPD2754	Discontinued
0.6281	Remote Similarity	NPD5926	Approved
0.6277	Remote Similarity	NPD2198	Approved
0.6277	Remote Similarity	NPD2199	Approved
0.6268	Remote Similarity	NPD5120	Approved
0.6268	Remote Similarity	NPD5121	Approved
0.6268	Remote Similarity	NPD5119	Approved
0.6268	Remote Similarity	NPD3142	Approved
0.6268	Remote Similarity	NPD3140	Approved
0.6261	Remote Similarity	NPD650	Approved
0.6259	Remote Similarity	NPD7179	Phase 2
0.625	Remote Similarity	NPD2948	Discontinued
0.6242	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD4619	Approved
0.6241	Remote Similarity	NPD4621	Approved
0.6239	Remote Similarity	NPD1086	Approved
0.6239	Remote Similarity	NPD1090	Approved
0.6239	Remote Similarity	NPD1089	Approved
0.6234	Remote Similarity	NPD6570	Approved
0.6234	Remote Similarity	NPD6571	Approved
0.6231	Remote Similarity	NPD2652	Approved
0.6231	Remote Similarity	NPD2650	Approved
0.6224	Remote Similarity	NPD4067	Approved
0.6224	Remote Similarity	NPD4066	Approved
0.6224	Remote Similarity	NPD4069	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD2863	Approved
0.6224	Remote Similarity	NPD4065	Approved
0.6224	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4068	Approved
0.6222	Remote Similarity	NPD4879	Approved
0.6222	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4106	Approved
0.6222	Remote Similarity	NPD4136	Approved
0.6222	Remote Similarity	NPD4135	Approved
0.6218	Remote Similarity	NPD1066	Discontinued
0.6216	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD2613	Approved
0.6212	Remote Similarity	NPD5162	Approved
0.62	Remote Similarity	NPD3950	Discontinued
0.6194	Remote Similarity	NPD5981	Approved
0.6194	Remote Similarity	NPD4102	Approved
0.6194	Remote Similarity	NPD4105	Approved
0.619	Remote Similarity	NPD3526	Approved
0.619	Remote Similarity	NPD3524	Approved
0.6187	Remote Similarity	NPD4980	Approved
0.6183	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD227	Approved
0.6182	Remote Similarity	NPD225	Approved
0.6174	Remote Similarity	NPD7295	Approved
0.6161	Remote Similarity	NPD942	Approved
0.6159	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8265	Approved
0.6154	Remote Similarity	NPD5185	Approved
0.6154	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5182	Approved
0.6154	Remote Similarity	NPD5184	Approved
0.6154	Remote Similarity	NPD6311	Approved
0.6154	Remote Similarity	NPD6310	Approved
0.6154	Remote Similarity	NPD6309	Approved
0.6148	Remote Similarity	NPD466	Approved
0.6148	Remote Similarity	NPD5836	Discontinued
0.6148	Remote Similarity	NPD253	Approved
0.6143	Remote Similarity	NPD5204	Approved
0.6143	Remote Similarity	NPD3661	Approved
0.6143	Remote Similarity	NPD3664	Approved
0.6143	Remote Similarity	NPD3662	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