NPASS Compound

Structure

NPC476221 OpenBabel07101718302D 49 56 0 0 1 0 0 0 0 0999 V2000 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7894 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -6.7350 -0.5000 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 -6.1472 0.3090 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 -7.4073 -2.5691 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 -1.7321 0.0000 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 -5.8684 -3.0691 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 2 0 0 0 0 0 0 0 0 0 -6.4562 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4073 -3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 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 -8.2163 -4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 -4.7894 0.9135 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 -6.4562 -3.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 0.0000 2.0000 0.0000 O 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 32 1 0 0 0 0 3 4 1 0 0 0 0 3 18 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 20 1 0 0 0 0 6 8 1 0 0 0 0 6 19 1 0 0 0 0 7 32 1 0 0 0 0 8 34 1 0 0 0 0 9 16 1 0 0 0 0 9 25 1 0 0 0 0 10 17 2 0 0 0 0 10 26 1 0 0 0 0 11 18 1 0 0 0 0 12 33 1 0 0 0 0 13 36 1 0 0 0 0 14 17 1 0 0 0 0 14 44 1 0 0 0 0 15 37 2 0 0 0 0 16 1 1 6 0 0 0 16 45 1 0 0 0 0 17 19 1 0 0 0 0 18 33 1 1 0 0 0 19 32 1 1 0 0 0 20 21 1 0 0 0 0 20 33 1 1 0 0 0 21 34 1 6 0 0 0 22 11 1 1 0 0 0 22 23 1 0 0 0 0 22 47 1 0 0 0 0 23 12 1 6 0 0 0 23 49 1 0 0 0 0 24 13 1 6 0 0 0 24 27 1 0 0 0 0 24 46 1 0 0 0 0 25 35 1 1 0 0 0 25 48 1 0 0 0 0 26 38 2 0 0 0 0 26 44 1 0 0 0 0 27 28 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 30 1 0 0 0 0 29 41 1 1 0 0 0 30 46 1 0 0 0 0 30 48 1 1 0 0 0 31 35 1 6 0 0 0 31 45 1 0 0 0 0 31 47 1 0 0 0 0 32 34 1 1 0 0 0 33 15 1 1 0 0 0 34 42 1 1 0 0 0 35 43 1 1 0 0 0 35 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.32
Volume:	660.618
LogP:	1.914
LogD:	1.014
LogS:	-2.92
# Rotatable Bonds:	5
TPSA:	217.97
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	6.094
Fsp3:	0.857
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.311
MDCK Permeability:	6.445046165026724e-05
Pgp-inhibitor:	0.477
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	70.35163116455078%
Volume Distribution (VD):	0.488
Pgp-substrate:	16.78638458251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.373
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	1.009
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.411
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.196
AMES Toxicity:	0.474
Rat Oral Acute Toxicity:	0.727
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.842
Carcinogencity:	0.27
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC476221

Natural Product ID:	NPC476221
*Common Name:**	QHTLPWXBPOENQB-KTGBMRPESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QHTLPWXBPOENQB-KTGBMRPESA-N
Standard InCHI:	InChI=1S/C35H50O14/c1-16-9-25(48-30-29(41)28(40)27(39)24(13-36)46-30)35(43)31(45-16)47-22-11-18-3-4-21-20(33(18,15-37)12-23(22)49-35)5-7-32(2)19(6-8-34(21,32)42)17-10-26(38)44-14-17/h10,15-16,18-25,27-31,36,39-43H,3-9,11-14H2,1-2H3/t16-,18+,19-,20+,21-,22-,23-,24-,25-,27-,28+,29-,30-,31+,32-,33-,34+,35+/m1/s1
SMILES:	CC1CC(C2(C(O1)OC3CC4CCC5C(C4(CC3O2)C=O)CCC6(C5(CCC6C7=CC(=O)OC7)O)C)O)OC8C(C(C(C(O8)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555674
PubChem CID:	45269892
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	roots	Wadi Um Hebal, Egypt	2001-JAN	PMID[16989527]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555122]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30629433]

☑ 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	7

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	200.0	nM	PMID[523952]
NPT1081	Cell Line	BXPC-3	Homo sapiens	IC50	=	500.0	nM	PMID[523952]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	400.0	nM	PMID[523952]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	200.0	nM	PMID[523952]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	300.0	nM	PMID[523952]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	400.0	nM	PMID[523952]
NPT2	Others	Unspecified		IC50	=	500.0	nM	PMID[523952]

☑ 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 NPC476221 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	309
0.1-0.2	1803
0.2-0.3	5130
0.3-0.4	9588
0.4-0.5	11077
0.5-0.6	6948
0.6-0.7	4689
0.7-0.8	2071
0.8-0.85	757
0.85-0.9	185
0.9-0.95	95
0.95-1	45

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477709
0.9835	High Similarity	NPC159338
0.9835	High Similarity	NPC253456
0.9835	High Similarity	NPC16569
0.9754	High Similarity	NPC19124
0.9754	High Similarity	NPC93416
0.9754	High Similarity	NPC42670
0.9752	High Similarity	NPC276838
0.9752	High Similarity	NPC232785
0.9752	High Similarity	NPC140092
0.9752	High Similarity	NPC188234
0.9752	High Similarity	NPC329986
0.9752	High Similarity	NPC91
0.9752	High Similarity	NPC125077
0.9675	High Similarity	NPC142756
0.9675	High Similarity	NPC225385
0.9675	High Similarity	NPC298783
0.9675	High Similarity	NPC104585
0.9675	High Similarity	NPC157817
0.9597	High Similarity	NPC329636
0.9587	High Similarity	NPC329784
0.9587	High Similarity	NPC240070
0.952	High Similarity	NPC194716
0.9516	High Similarity	NPC247190
0.9516	High Similarity	NPC146857
0.9516	High Similarity	NPC469749
0.9516	High Similarity	NPC116075
0.9516	High Similarity	NPC32793
0.9504	High Similarity	NPC250556
0.9504	High Similarity	NPC469750
0.9444	High Similarity	NPC329675
0.9444	High Similarity	NPC59288
0.9426	High Similarity	NPC471356
0.9426	High Similarity	NPC179412
0.9339	High Similarity	NPC27363
0.9274	High Similarity	NPC17896
0.9274	High Similarity	NPC251866
0.9274	High Similarity	NPC70542
0.9274	High Similarity	NPC284406
0.9274	High Similarity	NPC469753
0.9274	High Similarity	NPC10823
0.9274	High Similarity	NPC6108
0.9274	High Similarity	NPC471359
0.9274	High Similarity	NPC469755
0.9274	High Similarity	NPC86159
0.9274	High Similarity	NPC471358
0.9274	High Similarity	NPC471361
0.9274	High Similarity	NPC471352
0.9274	High Similarity	NPC471360
0.9274	High Similarity	NPC9499
0.9274	High Similarity	NPC469751
0.9274	High Similarity	NPC469752
0.9274	High Similarity	NPC89514
0.9274	High Similarity	NPC219085
0.9274	High Similarity	NPC197707
0.9274	High Similarity	NPC180079
0.9274	High Similarity	NPC469754
0.9213	High Similarity	NPC171619
0.9113	High Similarity	NPC117702
0.9113	High Similarity	NPC146456
0.9113	High Similarity	NPC469757
0.9113	High Similarity	NPC471357
0.9091	High Similarity	NPC72260
0.9055	High Similarity	NPC88668
0.9016	High Similarity	NPC474908
0.9016	High Similarity	NPC475419
0.9016	High Similarity	NPC120390
0.9016	High Similarity	NPC173555
0.9016	High Similarity	NPC314535
0.9016	High Similarity	NPC475590
0.9008	High Similarity	NPC236973
0.9008	High Similarity	NPC32177
0.9008	High Similarity	NPC470897
0.9008	High Similarity	NPC329905
0.9008	High Similarity	NPC292467
0.9008	High Similarity	NPC469756
0.9008	High Similarity	NPC55532
0.9008	High Similarity	NPC30483
0.8943	High Similarity	NPC474423
0.8943	High Similarity	NPC74259
0.8943	High Similarity	NPC193893
0.8934	High Similarity	NPC475629
0.8934	High Similarity	NPC474466
0.8934	High Similarity	NPC470312
0.8934	High Similarity	NPC475556
0.8934	High Similarity	NPC475136
0.8889	High Similarity	NPC311534
0.8871	High Similarity	NPC208193
0.8871	High Similarity	NPC117445
0.8871	High Similarity	NPC308262
0.8862	High Similarity	NPC40749
0.8862	High Similarity	NPC475219
0.8862	High Similarity	NPC231518
0.8855	High Similarity	NPC290746
0.8855	High Similarity	NPC79250
0.8846	High Similarity	NPC127656
0.8843	High Similarity	NPC152615
0.8843	High Similarity	NPC93883
0.8828	High Similarity	NPC471855
0.879	High Similarity	NPC28532
0.879	High Similarity	NPC264336
0.876	High Similarity	NPC310341
0.876	High Similarity	NPC193382
0.876	High Similarity	NPC199428
0.876	High Similarity	NPC5311
0.876	High Similarity	NPC99620
0.876	High Similarity	NPC196931
0.875	High Similarity	NPC173347
0.875	High Similarity	NPC477493
0.874	High Similarity	NPC114306
0.874	High Similarity	NPC477490
0.8702	High Similarity	NPC62172
0.8702	High Similarity	NPC289700
0.8699	High Similarity	NPC44899
0.8699	High Similarity	NPC304260
0.8699	High Similarity	NPC5883
0.8699	High Similarity	NPC29639
0.8689	High Similarity	NPC471354
0.8689	High Similarity	NPC309034
0.8689	High Similarity	NPC142066
0.8689	High Similarity	NPC196429
0.8689	High Similarity	NPC87250
0.8689	High Similarity	NPC27507
0.8689	High Similarity	NPC84987
0.8689	High Similarity	NPC243196
0.8689	High Similarity	NPC34390
0.8689	High Similarity	NPC77319
0.8689	High Similarity	NPC474418
0.8689	High Similarity	NPC158344
0.8689	High Similarity	NPC99728
0.8689	High Similarity	NPC50305
0.8689	High Similarity	NPC471353
0.8689	High Similarity	NPC471351
0.8689	High Similarity	NPC157376
0.8689	High Similarity	NPC471355
0.8689	High Similarity	NPC244402
0.8689	High Similarity	NPC473852
0.8682	High Similarity	NPC155529
0.8678	High Similarity	NPC69576
0.8678	High Similarity	NPC84949
0.8678	High Similarity	NPC31354
0.8678	High Similarity	NPC471633
0.8672	High Similarity	NPC471407
0.8629	High Similarity	NPC476150
0.8629	High Similarity	NPC107607
0.8629	High Similarity	NPC476127
0.8626	High Similarity	NPC158350
0.8618	High Similarity	NPC83287
0.8618	High Similarity	NPC218093
0.8571	High Similarity	NPC75616
0.855	High Similarity	NPC476777
0.855	High Similarity	NPC476778
0.8548	High Similarity	NPC291820
0.8548	High Similarity	NPC81222
0.8548	High Similarity	NPC477071
0.8538	High Similarity	NPC477195
0.8537	High Similarity	NPC203862
0.8537	High Similarity	NPC290693
0.8527	High Similarity	NPC476966
0.8504	High Similarity	NPC473505
0.8485	Intermediate Similarity	NPC279915
0.8485	Intermediate Similarity	NPC110700
0.848	Intermediate Similarity	NPC135369
0.848	Intermediate Similarity	NPC108072
0.8473	Intermediate Similarity	NPC476779
0.8468	Intermediate Similarity	NPC45475
0.8468	Intermediate Similarity	NPC471548
0.8462	Intermediate Similarity	NPC241008
0.8455	Intermediate Similarity	NPC138372
0.8455	Intermediate Similarity	NPC106228
0.845	Intermediate Similarity	NPC69273
0.845	Intermediate Similarity	NPC45606
0.845	Intermediate Similarity	NPC293623
0.845	Intermediate Similarity	NPC168899
0.845	Intermediate Similarity	NPC220838
0.8438	Intermediate Similarity	NPC174367
0.8438	Intermediate Similarity	NPC47113
0.8425	Intermediate Similarity	NPC41129
0.8425	Intermediate Similarity	NPC256983
0.8421	Intermediate Similarity	NPC477236
0.8409	Intermediate Similarity	NPC248703
0.84	Intermediate Similarity	NPC19028
0.84	Intermediate Similarity	NPC122971
0.84	Intermediate Similarity	NPC9674
0.84	Intermediate Similarity	NPC473401
0.84	Intermediate Similarity	NPC161738
0.8397	Intermediate Similarity	NPC473519
0.8397	Intermediate Similarity	NPC473805
0.8397	Intermediate Similarity	NPC476776
0.8397	Intermediate Similarity	NPC478154
0.8387	Intermediate Similarity	NPC473405
0.8387	Intermediate Similarity	NPC474483
0.8387	Intermediate Similarity	NPC477252
0.8385	Intermediate Similarity	NPC141600
0.8385	Intermediate Similarity	NPC252657
0.8385	Intermediate Similarity	NPC97918
0.8385	Intermediate Similarity	NPC107536
0.8385	Intermediate Similarity	NPC280029
0.8385	Intermediate Similarity	NPC470518
0.8385	Intermediate Similarity	NPC231529

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 NPC476221 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	1992
0.2-0.3	3995
0.3-0.4	1912
0.4-0.5	524
0.5-0.6	259
0.6-0.7	147
0.7-0.8	39
0.8-0.85	1
0.85-0.9	4
0.9-0.95	10
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9504	High Similarity	NPD7507	Approved
0.9274	High Similarity	NPD7319	Approved
0.9091	High Similarity	NPD8377	Approved
0.9091	High Similarity	NPD8294	Approved
0.9016	High Similarity	NPD8296	Approved
0.9016	High Similarity	NPD8335	Approved
0.9016	High Similarity	NPD8380	Approved
0.9016	High Similarity	NPD8378	Approved
0.9016	High Similarity	NPD8379	Approved
0.8862	High Similarity	NPD8033	Approved
0.8699	High Similarity	NPD7516	Approved
0.8618	High Similarity	NPD7327	Approved
0.8618	High Similarity	NPD7328	Approved
0.8443	Intermediate Similarity	NPD8133	Approved
0.8033	Intermediate Similarity	NPD6686	Approved
0.803	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD8328	Phase 3
0.7984	Intermediate Similarity	NPD7503	Approved
0.782	Intermediate Similarity	NPD8293	Discontinued
0.7805	Intermediate Similarity	NPD6412	Phase 2
0.771	Intermediate Similarity	NPD8517	Approved
0.771	Intermediate Similarity	NPD8516	Approved
0.771	Intermediate Similarity	NPD8515	Approved
0.771	Intermediate Similarity	NPD8513	Phase 3
0.768	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD6370	Approved
0.7642	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD7492	Approved
0.7521	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7481	Intermediate Similarity	NPD6616	Approved
0.7459	Intermediate Similarity	NPD7639	Approved
0.7459	Intermediate Similarity	NPD7640	Approved
0.7426	Intermediate Similarity	NPD7078	Approved
0.7405	Intermediate Similarity	NPD6009	Approved
0.7402	Intermediate Similarity	NPD6373	Approved
0.7402	Intermediate Similarity	NPD6372	Approved
0.7368	Intermediate Similarity	NPD6319	Approved
0.7347	Intermediate Similarity	NPD7625	Phase 1
0.7323	Intermediate Similarity	NPD7320	Approved
0.7313	Intermediate Similarity	NPD6016	Approved
0.7313	Intermediate Similarity	NPD6015	Approved
0.7308	Intermediate Similarity	NPD4632	Approved
0.7302	Intermediate Similarity	NPD7128	Approved
0.7302	Intermediate Similarity	NPD6675	Approved
0.7302	Intermediate Similarity	NPD5739	Approved
0.7302	Intermediate Similarity	NPD6402	Approved
0.7287	Intermediate Similarity	NPD6649	Approved
0.7287	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7266	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5988	Approved
0.7209	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6881	Approved
0.7188	Intermediate Similarity	NPD6899	Approved
0.7165	Intermediate Similarity	NPD6008	Approved
0.7154	Intermediate Similarity	NPD8130	Phase 1
0.7154	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5697	Approved
0.7109	Intermediate Similarity	NPD5701	Approved
0.7099	Intermediate Similarity	NPD6053	Discontinued
0.7077	Intermediate Similarity	NPD7102	Approved
0.7077	Intermediate Similarity	NPD7290	Approved
0.7077	Intermediate Similarity	NPD6883	Approved
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6847	Approved
0.7023	Intermediate Similarity	NPD6869	Approved
0.7023	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6033	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6977	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8171	Discontinued
0.6957	Remote Similarity	NPD7604	Phase 2
0.6957	Remote Similarity	NPD6067	Discontinued
0.6934	Remote Similarity	NPD5983	Phase 2
0.6929	Remote Similarity	NPD7632	Discontinued
0.6923	Remote Similarity	NPD6011	Approved
0.6894	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7902	Approved
0.688	Remote Similarity	NPD4755	Approved
0.6857	Remote Similarity	NPD6336	Discontinued
0.6818	Remote Similarity	NPD4634	Approved
0.6809	Remote Similarity	NPD8074	Phase 3
0.6797	Remote Similarity	NPD5211	Phase 2
0.6774	Remote Similarity	NPD7748	Approved
0.6772	Remote Similarity	NPD5286	Approved
0.6772	Remote Similarity	NPD4696	Approved
0.6772	Remote Similarity	NPD5285	Approved
0.6772	Remote Similarity	NPD4700	Approved
0.6748	Remote Similarity	NPD8035	Phase 2
0.6748	Remote Similarity	NPD8034	Phase 2
0.6746	Remote Similarity	NPD6083	Phase 2
0.6746	Remote Similarity	NPD6084	Phase 2
0.6718	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4225	Approved
0.6692	Remote Similarity	NPD5141	Approved
0.6691	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6647	Remote Similarity	NPD7799	Discontinued
0.6641	Remote Similarity	NPD4768	Approved
0.6641	Remote Similarity	NPD4767	Approved
0.664	Remote Similarity	NPD7900	Approved
0.664	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5174	Approved
0.6615	Remote Similarity	NPD5175	Approved
0.6613	Remote Similarity	NPD7515	Phase 2
0.6594	Remote Similarity	NPD6335	Approved
0.6589	Remote Similarity	NPD5223	Approved
0.6587	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5328	Approved
0.6571	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6909	Approved
0.6571	Remote Similarity	NPD6908	Approved
0.6571	Remote Similarity	NPD6921	Approved
0.6567	Remote Similarity	NPD6371	Approved
0.6562	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5696	Approved
0.656	Remote Similarity	NPD6399	Phase 3
0.656	Remote Similarity	NPD4202	Approved
0.6552	Remote Similarity	NPD8392	Approved
0.6552	Remote Similarity	NPD8391	Approved
0.6552	Remote Similarity	NPD8390	Approved
0.6541	Remote Similarity	NPD4730	Approved
0.6541	Remote Similarity	NPD4729	Approved
0.6532	Remote Similarity	NPD6698	Approved
0.6532	Remote Similarity	NPD46	Approved
0.6522	Remote Similarity	NPD6317	Approved
0.6504	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD8451	Approved
0.6489	Remote Similarity	NPD4754	Approved
0.648	Remote Similarity	NPD6079	Approved
0.6475	Remote Similarity	NPD6313	Approved
0.6475	Remote Similarity	NPD6314	Approved
0.6463	Remote Similarity	NPD8449	Approved
0.6458	Remote Similarity	NPD8448	Approved
0.6457	Remote Similarity	NPD5695	Phase 3
0.6444	Remote Similarity	NPD5251	Approved
0.6444	Remote Similarity	NPD5249	Phase 3
0.6444	Remote Similarity	NPD5250	Approved
0.6444	Remote Similarity	NPD5247	Approved
0.6444	Remote Similarity	NPD5248	Approved
0.6419	Remote Similarity	NPD8450	Suspended
0.6418	Remote Similarity	NPD5128	Approved
0.6414	Remote Similarity	NPD8336	Approved
0.6414	Remote Similarity	NPD8337	Approved
0.6395	Remote Similarity	NPD7260	Phase 2
0.6393	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6903	Approved
0.6351	Remote Similarity	NPD8338	Approved
0.6349	Remote Similarity	NPD5693	Phase 1
0.6341	Remote Similarity	NPD3618	Phase 1
0.6341	Remote Similarity	NPD7521	Approved
0.6341	Remote Similarity	NPD7334	Approved
0.6341	Remote Similarity	NPD7146	Approved
0.6341	Remote Similarity	NPD6684	Approved
0.6341	Remote Similarity	NPD6409	Approved
0.6341	Remote Similarity	NPD5330	Approved
0.6336	Remote Similarity	NPD5344	Discontinued
0.6327	Remote Similarity	NPD5956	Approved
0.632	Remote Similarity	NPD4753	Phase 2
0.6319	Remote Similarity	NPD8342	Approved
0.6319	Remote Similarity	NPD8340	Approved
0.6319	Remote Similarity	NPD8341	Approved
0.6319	Remote Similarity	NPD8299	Approved
0.6279	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5221	Approved
0.6279	Remote Similarity	NPD5222	Approved
0.6277	Remote Similarity	NPD5215	Approved
0.6277	Remote Similarity	NPD5217	Approved
0.6277	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD6001	Approved
0.625	Remote Similarity	NPD7830	Approved
0.6242	Remote Similarity	NPD6845	Suspended
0.6231	Remote Similarity	NPD5173	Approved
0.622	Remote Similarity	NPD5281	Approved
0.622	Remote Similarity	NPD5284	Approved
0.6214	Remote Similarity	NPD6868	Approved
0.6204	Remote Similarity	NPD5135	Approved
0.6204	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5169	Approved
0.6202	Remote Similarity	NPD5210	Approved
0.6202	Remote Similarity	NPD4629	Approved
0.619	Remote Similarity	NPD6051	Approved
0.619	Remote Similarity	NPD6080	Approved
0.619	Remote Similarity	NPD6673	Approved
0.619	Remote Similarity	NPD6904	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