NPASS Compound

Structure

NPC472165 OpenBabel07101718322D 29 31 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 -4.3301 -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 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 -2.5000 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 -2.5981 -1.5000 0.0000 C 0 0 2 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 -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 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 -3.4641 -1.0000 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 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 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 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 19 14 1 1 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 1 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 26 2 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	399.24
Volume:	428.33
LogP:	5.078
LogD:	3.519
LogS:	-5.757
# Rotatable Bonds:	9
TPSA:	49.69
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.579
Synthetic Accessibility Score:	3.662
Fsp3:	0.542
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:	-4.688
MDCK Permeability:	1.541093661217019e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.892

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.555
Plasma Protein Binding (PPB):	96.95941925048828%
Volume Distribution (VD):	0.51
Pgp-substrate:	1.0053845643997192%

ADMET: Metabolism

CYP1A2-inhibitor:	0.474
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.134
CYP2D6-substrate:	0.715
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	2.969
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.554
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.383
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC472165

Natural Product ID:	NPC472165
*Common Name:**	HBUDYOSKHDWTOS-VQTJNVASSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HBUDYOSKHDWTOS-VQTJNVASSA-N
Standard InCHI:	InChI=1S/C24H33NO4/c1-17-24(28-3)23(26)21-19(15-16-20(27-2)22(21)25(17)29-4)14-10-6-9-13-18-11-7-5-8-12-18/h5,7-8,11-12,19-20H,6,9-10,13-16H2,1-4H3/t19-,20+/m0/s1
SMILES:	CO[C@@H]1CC[C@@H](c2c1n(OC)c(C)c(c2=O)OC)CCCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342752
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	3
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	260.0	nM	PMID[543169]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	35900.0	nM	PMID[543169]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	40.0	nM	PMID[543169]
NPT2	Others	Unspecified		Ratio IC50	=	6.5	n.a.	PMID[543169]

☑ 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 NPC472165 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	406
0.1-0.2	1759
0.2-0.3	7792
0.3-0.4	9440
0.4-0.5	12476
0.5-0.6	9387
0.6-0.7	1324
0.7-0.8	89
0.8-0.85	9
0.85-0.9	8
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.906	High Similarity	NPC472164
0.7692	Intermediate Similarity	NPC472167
0.7556	Intermediate Similarity	NPC103605
0.7556	Intermediate Similarity	NPC81092
0.7448	Intermediate Similarity	NPC246412
0.7333	Intermediate Similarity	NPC145052
0.725	Intermediate Similarity	NPC103048
0.7246	Intermediate Similarity	NPC179224
0.7154	Intermediate Similarity	NPC474408
0.7107	Intermediate Similarity	NPC472166
0.7107	Intermediate Similarity	NPC472162
0.708	Intermediate Similarity	NPC477248
0.708	Intermediate Similarity	NPC477249
0.7054	Intermediate Similarity	NPC477250
0.7025	Intermediate Similarity	NPC12695
0.7008	Intermediate Similarity	NPC470391
0.6975	Remote Similarity	NPC476484
0.697	Remote Similarity	NPC471616
0.6963	Remote Similarity	NPC474223
0.6963	Remote Similarity	NPC475827
0.6953	Remote Similarity	NPC40178
0.6894	Remote Similarity	NPC228936
0.6891	Remote Similarity	NPC67585
0.6891	Remote Similarity	NPC303967
0.6891	Remote Similarity	NPC110420
0.6875	Remote Similarity	NPC470007
0.6875	Remote Similarity	NPC47536
0.6861	Remote Similarity	NPC160493
0.6857	Remote Similarity	NPC105114
0.6857	Remote Similarity	NPC152850
0.6857	Remote Similarity	NPC89923
0.6857	Remote Similarity	NPC71933
0.6857	Remote Similarity	NPC239990
0.6846	Remote Similarity	NPC477247
0.6846	Remote Similarity	NPC291799
0.6838	Remote Similarity	NPC472136
0.6838	Remote Similarity	NPC473243
0.6829	Remote Similarity	NPC472788
0.6812	Remote Similarity	NPC474254
0.6812	Remote Similarity	NPC474159
0.6797	Remote Similarity	NPC477251
0.6791	Remote Similarity	NPC190298
0.6786	Remote Similarity	NPC136453
0.6767	Remote Similarity	NPC470764
0.6742	Remote Similarity	NPC13784
0.6731	Remote Similarity	NPC63370
0.6731	Remote Similarity	NPC36836
0.6721	Remote Similarity	NPC23453
0.6718	Remote Similarity	NPC137315
0.6715	Remote Similarity	NPC475804
0.6715	Remote Similarity	NPC474222
0.6715	Remote Similarity	NPC190663
0.6715	Remote Similarity	NPC476225
0.6714	Remote Similarity	NPC474479
0.6713	Remote Similarity	NPC157311
0.6692	Remote Similarity	NPC475282
0.6692	Remote Similarity	NPC196075
0.6692	Remote Similarity	NPC326664
0.6667	Remote Similarity	NPC112552
0.6667	Remote Similarity	NPC5472
0.6667	Remote Similarity	NPC119326
0.6667	Remote Similarity	NPC8761
0.6667	Remote Similarity	NPC476599
0.6667	Remote Similarity	NPC44805
0.6643	Remote Similarity	NPC285394
0.6642	Remote Similarity	NPC210092
0.6642	Remote Similarity	NPC204784
0.6639	Remote Similarity	NPC77273
0.6618	Remote Similarity	NPC471553
0.6617	Remote Similarity	NPC161611
0.6615	Remote Similarity	NPC203732
0.6612	Remote Similarity	NPC108026
0.6597	Remote Similarity	NPC49272
0.6593	Remote Similarity	NPC135730
0.6591	Remote Similarity	NPC474157
0.6587	Remote Similarity	NPC476042
0.6585	Remote Similarity	NPC34243
0.6575	Remote Similarity	NPC477680
0.6575	Remote Similarity	NPC132308
0.6573	Remote Similarity	NPC472413
0.6571	Remote Similarity	NPC65627
0.6569	Remote Similarity	NPC64340
0.6567	Remote Similarity	NPC477411
0.6565	Remote Similarity	NPC469636
0.6565	Remote Similarity	NPC192577
0.6544	Remote Similarity	NPC108532
0.6544	Remote Similarity	NPC28951
0.6544	Remote Similarity	NPC325646
0.6541	Remote Similarity	NPC474689
0.6541	Remote Similarity	NPC212415
0.6536	Remote Similarity	NPC473541
0.6529	Remote Similarity	NPC231591
0.6525	Remote Similarity	NPC469742
0.6519	Remote Similarity	NPC474095
0.6513	Remote Similarity	NPC282578
0.6513	Remote Similarity	NPC190945
0.6508	Remote Similarity	NPC329387
0.6508	Remote Similarity	NPC317280
0.6507	Remote Similarity	NPC475569
0.65	Remote Similarity	NPC26285
0.6496	Remote Similarity	NPC61651
0.6496	Remote Similarity	NPC152812
0.6494	Remote Similarity	NPC2672
0.6493	Remote Similarity	NPC469547
0.6493	Remote Similarity	NPC477245
0.6493	Remote Similarity	NPC477246
0.6489	Remote Similarity	NPC20485
0.6486	Remote Similarity	NPC196708
0.6483	Remote Similarity	NPC471832
0.6479	Remote Similarity	NPC477369
0.6479	Remote Similarity	NPC295664
0.6475	Remote Similarity	NPC289432
0.6475	Remote Similarity	NPC80150
0.6475	Remote Similarity	NPC77000
0.6475	Remote Similarity	NPC988
0.6475	Remote Similarity	NPC238861
0.6471	Remote Similarity	NPC226093
0.6458	Remote Similarity	NPC213969
0.6458	Remote Similarity	NPC116057
0.6458	Remote Similarity	NPC165726
0.6457	Remote Similarity	NPC80115
0.6454	Remote Similarity	NPC472415
0.6452	Remote Similarity	NPC242000
0.6449	Remote Similarity	NPC310467
0.6449	Remote Similarity	NPC152159
0.6444	Remote Similarity	NPC241851
0.6444	Remote Similarity	NPC67377
0.6443	Remote Similarity	NPC77992
0.6443	Remote Similarity	NPC281104
0.6443	Remote Similarity	NPC106606
0.6438	Remote Similarity	NPC60825
0.6438	Remote Similarity	NPC291419
0.6434	Remote Similarity	NPC236405
0.6434	Remote Similarity	NPC301943
0.6434	Remote Similarity	NPC474365
0.6429	Remote Similarity	NPC289201
0.6429	Remote Similarity	NPC50872
0.6429	Remote Similarity	NPC144547
0.6418	Remote Similarity	NPC82899
0.6418	Remote Similarity	NPC270699
0.6414	Remote Similarity	NPC469930
0.6412	Remote Similarity	NPC51174
0.6408	Remote Similarity	NPC8990
0.6408	Remote Similarity	NPC325740
0.6408	Remote Similarity	NPC51079
0.6406	Remote Similarity	NPC316797
0.6383	Remote Similarity	NPC39818
0.6382	Remote Similarity	NPC475128
0.6378	Remote Similarity	NPC154517
0.6378	Remote Similarity	NPC179411
0.6378	Remote Similarity	NPC135951
0.6377	Remote Similarity	NPC169328
0.6376	Remote Similarity	NPC208725
0.637	Remote Similarity	NPC314473
0.637	Remote Similarity	NPC272524
0.637	Remote Similarity	NPC477476
0.637	Remote Similarity	NPC183722
0.637	Remote Similarity	NPC196026
0.637	Remote Similarity	NPC477475
0.637	Remote Similarity	NPC128368
0.637	Remote Similarity	NPC200555
0.6364	Remote Similarity	NPC135121
0.6364	Remote Similarity	NPC474803
0.6364	Remote Similarity	NPC96625
0.6364	Remote Similarity	NPC474766
0.6357	Remote Similarity	NPC232958
0.6351	Remote Similarity	NPC280476
0.6351	Remote Similarity	NPC119985
0.6351	Remote Similarity	NPC474473
0.635	Remote Similarity	NPC235421
0.6345	Remote Similarity	NPC71271
0.6345	Remote Similarity	NPC195224
0.6343	Remote Similarity	NPC305912
0.6343	Remote Similarity	NPC1082
0.6343	Remote Similarity	NPC323007
0.6341	Remote Similarity	NPC476569
0.634	Remote Similarity	NPC308197
0.6336	Remote Similarity	NPC209632
0.6336	Remote Similarity	NPC474307
0.6336	Remote Similarity	NPC167336
0.6335	Remote Similarity	NPC57512
0.6331	Remote Similarity	NPC318173
0.6328	Remote Similarity	NPC474308
0.6324	Remote Similarity	NPC308744
0.6324	Remote Similarity	NPC307651
0.6324	Remote Similarity	NPC1986
0.6324	Remote Similarity	NPC474544
0.6319	Remote Similarity	NPC477363
0.6319	Remote Similarity	NPC65310
0.6319	Remote Similarity	NPC470818
0.6316	Remote Similarity	NPC281604
0.6316	Remote Similarity	NPC474364
0.6311	Remote Similarity	NPC477693
0.6311	Remote Similarity	NPC477704
0.6309	Remote Similarity	NPC9687
0.6309	Remote Similarity	NPC293377
0.6309	Remote Similarity	NPC475318
0.6309	Remote Similarity	NPC76785
0.6309	Remote Similarity	NPC49577
0.6309	Remote Similarity	NPC90194

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 NPC472165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	642
0.2-0.3	819
0.3-0.4	1448
0.4-0.5	3057
0.5-0.6	2397
0.6-0.7	489
0.7-0.8	23
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
0.7313	Intermediate Similarity	NPD6637	Approved
0.7194	Intermediate Similarity	NPD6039	Approved
0.7031	Intermediate Similarity	NPD2067	Discontinued
0.6917	Remote Similarity	NPD4576	Approved
0.6917	Remote Similarity	NPD4574	Approved
0.6863	Remote Similarity	NPD3399	Approved
0.6835	Remote Similarity	NPD2198	Approved
0.6835	Remote Similarity	NPD2199	Approved
0.6835	Remote Similarity	NPD5667	Approved
0.6772	Remote Similarity	NPD5909	Discontinued
0.6759	Remote Similarity	NPD4069	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4066	Approved
0.6759	Remote Similarity	NPD4067	Approved
0.6759	Remote Similarity	NPD4068	Approved
0.6759	Remote Similarity	NPD4065	Approved
0.6755	Remote Similarity	NPD4607	Approved
0.6731	Remote Similarity	NPD6571	Approved
0.6731	Remote Similarity	NPD6570	Approved
0.6711	Remote Similarity	NPD3352	Approved
0.6711	Remote Similarity	NPD2923	Approved
0.6711	Remote Similarity	NPD3950	Discontinued
0.6689	Remote Similarity	NPD6185	Discontinued
0.6687	Remote Similarity	NPD7036	Phase 3
0.6687	Remote Similarity	NPD7035	Approved
0.6645	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD5159	Phase 2
0.6643	Remote Similarity	NPD4620	Approved
0.6643	Remote Similarity	NPD5203	Approved
0.6643	Remote Similarity	NPD5201	Approved
0.6643	Remote Similarity	NPD4617	Approved
0.6643	Remote Similarity	NPD5157	Phase 1
0.6642	Remote Similarity	NPD1711	Phase 2
0.6625	Remote Similarity	NPD8007	Approved
0.6625	Remote Similarity	NPD8008	Approved
0.6623	Remote Similarity	NPD4513	Discontinued
0.6621	Remote Similarity	NPD7713	Phase 3
0.6619	Remote Similarity	NPD4807	Approved
0.6619	Remote Similarity	NPD4806	Approved
0.6601	Remote Similarity	NPD6758	Approved
0.6575	Remote Similarity	NPD5121	Approved
0.6575	Remote Similarity	NPD5119	Approved
0.6575	Remote Similarity	NPD5120	Approved
0.6541	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD810	Approved
0.6538	Remote Similarity	NPD811	Approved
0.6538	Remote Similarity	NPD812	Approved
0.6536	Remote Similarity	NPD4041	Approved
0.6536	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD2435	Approved
0.6496	Remote Similarity	NPD6065	Approved
0.649	Remote Similarity	NPD5170	Discontinued
0.6486	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4188	Approved
0.6484	Remote Similarity	NPD4189	Approved
0.6475	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3373	Approved
0.6458	Remote Similarity	NPD3662	Phase 3
0.6458	Remote Similarity	NPD5204	Approved
0.6458	Remote Similarity	NPD3664	Approved
0.6458	Remote Similarity	NPD3661	Approved
0.6458	Remote Similarity	NPD3663	Approved
0.6452	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7179	Phase 2
0.6443	Remote Similarity	NPD2569	Approved
0.6443	Remote Similarity	NPD2567	Approved
0.6438	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD4621	Approved
0.6438	Remote Similarity	NPD4619	Approved
0.6433	Remote Similarity	NPD2948	Discontinued
0.6429	Remote Similarity	NPD4136	Approved
0.6429	Remote Similarity	NPD7775	Approved
0.6429	Remote Similarity	NPD4135	Approved
0.6429	Remote Similarity	NPD4106	Approved
0.6424	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD2863	Approved
0.6412	Remote Similarity	NPD3526	Approved
0.6412	Remote Similarity	NPD3524	Approved
0.6406	Remote Similarity	NPD2558	Approved
0.6406	Remote Similarity	NPD2553	Approved
0.6406	Remote Similarity	NPD2552	Approved
0.6406	Remote Similarity	NPD2555	Approved
0.6406	Remote Similarity	NPD2550	Approved
0.6406	Remote Similarity	NPD2549	Approved
0.6398	Remote Similarity	NPD7244	Discontinued
0.6397	Remote Similarity	NPD2319	Discontinued
0.6391	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD3047	Approved
0.6385	Remote Similarity	NPD3048	Approved
0.6385	Remote Similarity	NPD3046	Approved
0.6383	Remote Similarity	NPD6287	Discontinued
0.6383	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2897	Discontinued
0.6378	Remote Similarity	NPD5926	Approved
0.6376	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2607	Approved
0.637	Remote Similarity	NPD7094	Approved
0.637	Remote Similarity	NPD6858	Approved
0.6369	Remote Similarity	NPD7670	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5166	Discontinued
0.6364	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD8265	Approved
0.6351	Remote Similarity	NPD3140	Approved
0.6351	Remote Similarity	NPD3142	Approved
0.6347	Remote Similarity	NPD7940	Phase 3
0.6343	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2201	Approved
0.6338	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5688	Approved
0.6333	Remote Similarity	NPD5689	Approved
0.6319	Remote Similarity	NPD2625	Approved
0.6319	Remote Similarity	NPD2628	Approved
0.6319	Remote Similarity	NPD2160	Approved
0.6319	Remote Similarity	NPD2626	Approved
0.6319	Remote Similarity	NPD2627	Approved
0.6319	Remote Similarity	NPD2159	Approved
0.6312	Remote Similarity	NPD5889	Approved
0.6312	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5890	Approved
0.6309	Remote Similarity	NPD4618	Approved
0.6309	Remote Similarity	NPD4622	Approved
0.6308	Remote Similarity	NPD6647	Phase 2
0.6301	Remote Similarity	NPD2613	Approved
0.6296	Remote Similarity	NPD4573	Approved
0.6296	Remote Similarity	NPD4571	Approved
0.6296	Remote Similarity	NPD4572	Approved
0.6294	Remote Similarity	NPD6025	Phase 1
0.6289	Remote Similarity	NPD3769	Discontinued
0.6286	Remote Similarity	NPD4102	Approved
0.6286	Remote Similarity	NPD4105	Approved
0.6284	Remote Similarity	NPD3614	Approved
0.6284	Remote Similarity	NPD2570	Approved
0.6284	Remote Similarity	NPD3090	Approved
0.6284	Remote Similarity	NPD3616	Approved
0.6284	Remote Similarity	NPD3088	Approved
0.6284	Remote Similarity	NPD2571	Approved
0.6284	Remote Similarity	NPD2574	Discontinued
0.6284	Remote Similarity	NPD3089	Approved
0.6284	Remote Similarity	NPD4746	Phase 3
0.6284	Remote Similarity	NPD4745	Approved
0.6284	Remote Similarity	NPD3615	Approved
0.6284	Remote Similarity	NPD3087	Approved
0.6284	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2566	Approved
0.6284	Remote Similarity	NPD2573	Approved
0.6277	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5237	Approved
0.6269	Remote Similarity	NPD4234	Approved
0.6269	Remote Similarity	NPD5240	Approved
0.6269	Remote Similarity	NPD5239	Approved
0.6269	Remote Similarity	NPD550	Approved
0.6269	Remote Similarity	NPD1756	Approved
0.6269	Remote Similarity	NPD4233	Approved
0.6269	Remote Similarity	NPD551	Approved
0.6269	Remote Similarity	NPD5236	Approved
0.6269	Remote Similarity	NPD5235	Approved
0.6269	Remote Similarity	NPD1752	Approved
0.6268	Remote Similarity	NPD2612	Approved
0.6268	Remote Similarity	NPD4216	Approved
0.6268	Remote Similarity	NPD2609	Approved
0.6268	Remote Similarity	NPD3131	Approved
0.6268	Remote Similarity	NPD4217	Approved
0.6268	Remote Similarity	NPD3132	Approved
0.6268	Remote Similarity	NPD2610	Approved
0.6268	Remote Similarity	NPD2611	Approved
0.6268	Remote Similarity	NPD4218	Approved
0.6268	Remote Similarity	NPD2608	Approved
0.6268	Remote Similarity	NPD4215	Approved
0.6266	Remote Similarity	NPD7606	Phase 3
0.626	Remote Similarity	NPD1237	Approved
0.6259	Remote Similarity	NPD2484	Approved
0.6259	Remote Similarity	NPD2485	Approved
0.6259	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4173	Approved
0.625	Remote Similarity	NPD4172	Approved
0.6242	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5306	Approved
0.6241	Remote Similarity	NPD5305	Approved
0.6241	Remote Similarity	NPD5723	Approved
0.6235	Remote Similarity	NPD7881	Approved
0.6233	Remote Similarity	NPD7084	Phase 3
0.6231	Remote Similarity	NPD2193	Phase 2
0.6231	Remote Similarity	NPD2648	Phase 3
0.623	Remote Similarity	NPD1282	Approved
0.6225	Remote Similarity	NPD4448	Approved
0.6225	Remote Similarity	NPD4449	Approved
0.6222	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7042	Phase 3
0.6204	Remote Similarity	NPD1371	Approved
0.6204	Remote Similarity	NPD1373	Approved
0.6204	Remote Similarity	NPD1370	Approved
0.6204	Remote Similarity	NPD1374	Approved
0.6204	Remote Similarity	NPD2650	Approved
0.6204	Remote Similarity	NPD1241	Discontinued
0.6204	Remote Similarity	NPD2652	Approved
0.6203	Remote Similarity	NPD2737	Clinical (unspecified phase)

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