NPASS Compound

Structure

NPC473208 OpenBabel07101718192D 43 50 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 -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 2.5981 0.5000 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 -5.8684 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.5388 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 -4.7894 0.9135 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 1.2321 -1.5388 0.0000 C 0 0 0 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 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 1.7321 -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 1 0 0 0 0 0 0 0 0 0 0.9230 -0.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3772 1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6443 -2.3479 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 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 0.0000 2.0000 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 2.5411 -0.5878 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 28 1 0 0 0 0 3 4 1 0 0 0 0 3 19 1 0 0 0 0 4 22 1 0 0 0 0 5 7 1 0 0 0 0 5 21 1 0 0 0 0 6 8 1 0 0 0 0 6 20 1 0 0 0 0 7 28 1 0 0 0 0 8 30 1 0 0 0 0 9 18 2 0 0 0 0 9 26 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 31 1 0 0 0 0 12 29 1 0 0 0 0 13 18 1 0 0 0 0 13 39 1 0 0 0 0 14 25 1 0 0 0 0 14 43 1 0 0 0 0 15 34 2 0 0 0 0 16 35 1 0 0 0 0 17 1 1 6 0 0 0 17 40 1 0 0 0 0 18 20 1 0 0 0 0 19 29 1 1 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 30 1 6 0 0 0 23 10 1 1 0 0 0 23 24 1 0 0 0 0 23 41 1 0 0 0 0 24 12 1 6 0 0 0 24 42 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 37 2 0 0 0 0 26 39 1 0 0 0 0 27 32 1 6 0 0 0 27 40 1 0 0 0 0 27 41 1 0 0 0 0 28 30 1 1 0 0 0 29 15 1 1 0 0 0 30 16 1 1 0 0 0 31 32 1 6 0 0 0 31 33 1 0 0 0 0 31 43 1 0 0 0 0 32 38 1 1 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	617.27
Volume:	591.648
LogP:	3.245
LogD:	3.191
LogS:	-4.293
# Rotatable Bonds:	3
TPSA:	147.69
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.294
Synthetic Accessibility Score:	6.643
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
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:	-5.619
MDCK Permeability:	9.846812645264436e-06
Pgp-inhibitor:	0.053
Pgp-substrate:	0.134
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.319
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	84.4406967163086%
Volume Distribution (VD):	1.561
Pgp-substrate:	5.84591007232666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.839
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.23
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.854

ADMET: Excretion

Clearance (CL):	4.6
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.332
Drug-inuced Liver Injury (DILI):	0.762
AMES Toxicity:	0.942
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.932
Carcinogencity:	0.781
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC473208

Natural Product ID:	NPC473208
*Common Name:**	JENFELCBBWGKDL-DMHYMSEJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JENFELCBBWGKDL-DMHYMSEJSA-N
Standard InCHI:	InChI=1S/C32H43NO9S/c1-17-11-31(33-25(36)14-43-31)32(38)27(40-17)41-23-10-19-3-4-22-21(29(19,15-34)12-24(23)42-32)5-7-28(2)20(6-8-30(22,28)16-35)18-9-26(37)39-13-18/h9,15,17,19-24,27,35,38H,3-8,10-14,16H2,1-2H3,(H,33,36)/t17-,19+,20-,21+,22-,23-,24-,27+,28-,29-,30+,31+,32-/m1/s1
SMILES:	CC1CC2(C3(C(O1)OC4CC5CCC6C(C5(CC4O3)C=O)CCC7(C6(CCC7C8=CC(=O)OC8)CO)C)O)NC(=O)CS2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL368047
PubChem CID:	44387904
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
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	root barks	n.a.	n.a.	PMID[15689169]
NPO27807	Calotropis procera	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27807	Calotropis procera	Species	Apocynaceae	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

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT933	Cell Line	U373 MG	Homo sapiens	IC50	=	15.0	nM	PMID[459750]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	16.0	nM	PMID[459750]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	10.0	nM	PMID[459750]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	74.0	nM	PMID[459750]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.0	nM	PMID[459750]

☑ 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 NPC473208 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	199
0.1-0.2	1378
0.2-0.3	5667
0.3-0.4	15604
0.4-0.5	10991
0.5-0.6	6253
0.6-0.7	2212
0.7-0.8	387
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9329	High Similarity	NPC163365
0.8447	Intermediate Similarity	NPC470094
0.8418	Intermediate Similarity	NPC473040
0.7823	Intermediate Similarity	NPC476221
0.7823	Intermediate Similarity	NPC477709
0.7808	Intermediate Similarity	NPC253456
0.7808	Intermediate Similarity	NPC16569
0.7808	Intermediate Similarity	NPC159338
0.7755	Intermediate Similarity	NPC42670
0.7755	Intermediate Similarity	NPC19124
0.7755	Intermediate Similarity	NPC93416
0.774	Intermediate Similarity	NPC140092
0.774	Intermediate Similarity	NPC276838
0.774	Intermediate Similarity	NPC91
0.774	Intermediate Similarity	NPC232785
0.774	Intermediate Similarity	NPC125077
0.774	Intermediate Similarity	NPC329986
0.774	Intermediate Similarity	NPC188234
0.7703	Intermediate Similarity	NPC225385
0.7703	Intermediate Similarity	NPC298783
0.7703	Intermediate Similarity	NPC142756
0.7703	Intermediate Similarity	NPC104585
0.7703	Intermediate Similarity	NPC157817
0.7603	Intermediate Similarity	NPC329784
0.7603	Intermediate Similarity	NPC240070
0.7584	Intermediate Similarity	NPC469749
0.7584	Intermediate Similarity	NPC146857
0.7584	Intermediate Similarity	NPC247190
0.7584	Intermediate Similarity	NPC116075
0.7584	Intermediate Similarity	NPC32793
0.755	Intermediate Similarity	NPC59288
0.7534	Intermediate Similarity	NPC469750
0.7534	Intermediate Similarity	NPC250556
0.7533	Intermediate Similarity	NPC329636
0.7483	Intermediate Similarity	NPC471356
0.7483	Intermediate Similarity	NPC171619
0.7483	Intermediate Similarity	NPC194716
0.7483	Intermediate Similarity	NPC179412
0.7434	Intermediate Similarity	NPC329675
0.7431	Intermediate Similarity	NPC470312
0.7397	Intermediate Similarity	NPC27363
0.7383	Intermediate Similarity	NPC17896
0.7383	Intermediate Similarity	NPC89514
0.7383	Intermediate Similarity	NPC471360
0.7383	Intermediate Similarity	NPC70542
0.7383	Intermediate Similarity	NPC469754
0.7383	Intermediate Similarity	NPC471358
0.7383	Intermediate Similarity	NPC251866
0.7383	Intermediate Similarity	NPC10823
0.7383	Intermediate Similarity	NPC197707
0.7383	Intermediate Similarity	NPC469755
0.7383	Intermediate Similarity	NPC471359
0.7383	Intermediate Similarity	NPC219085
0.7383	Intermediate Similarity	NPC180079
0.7383	Intermediate Similarity	NPC471361
0.7383	Intermediate Similarity	NPC6108
0.7383	Intermediate Similarity	NPC469752
0.7383	Intermediate Similarity	NPC469753
0.7383	Intermediate Similarity	NPC471352
0.7383	Intermediate Similarity	NPC9499
0.7383	Intermediate Similarity	NPC284406
0.7383	Intermediate Similarity	NPC469751
0.7383	Intermediate Similarity	NPC86159
0.7351	Intermediate Similarity	NPC88668
0.7284	Intermediate Similarity	NPC265699
0.7248	Intermediate Similarity	NPC146456
0.7248	Intermediate Similarity	NPC471357
0.7248	Intermediate Similarity	NPC117702
0.7248	Intermediate Similarity	NPC469757
0.7239	Intermediate Similarity	NPC475599
0.7239	Intermediate Similarity	NPC187497
0.7239	Intermediate Similarity	NPC113620
0.7239	Intermediate Similarity	NPC100612
0.7239	Intermediate Similarity	NPC174336
0.7237	Intermediate Similarity	NPC119794
0.7237	Intermediate Similarity	NPC73829
0.7208	Intermediate Similarity	NPC145899
0.7188	Intermediate Similarity	NPC244380
0.7188	Intermediate Similarity	NPC61717
0.7179	Intermediate Similarity	NPC302276
0.7179	Intermediate Similarity	NPC180770
0.7178	Intermediate Similarity	NPC475527
0.7171	Intermediate Similarity	NPC477195
0.7171	Intermediate Similarity	NPC139585
0.7171	Intermediate Similarity	NPC475472
0.7143	Intermediate Similarity	NPC280941
0.7143	Intermediate Similarity	NPC235772
0.7143	Intermediate Similarity	NPC75318
0.7134	Intermediate Similarity	NPC82931
0.7134	Intermediate Similarity	NPC172365
0.7134	Intermediate Similarity	NPC210729
0.7123	Intermediate Similarity	NPC470897
0.7123	Intermediate Similarity	NPC292467
0.7123	Intermediate Similarity	NPC469756
0.7123	Intermediate Similarity	NPC55532
0.7123	Intermediate Similarity	NPC32177
0.7123	Intermediate Similarity	NPC236973
0.7123	Intermediate Similarity	NPC329905
0.7123	Intermediate Similarity	NPC30483
0.7115	Intermediate Similarity	NPC243680
0.7115	Intermediate Similarity	NPC200788
0.7114	Intermediate Similarity	NPC318135
0.7107	Intermediate Similarity	NPC141669
0.7099	Intermediate Similarity	NPC36463
0.7099	Intermediate Similarity	NPC298005
0.7089	Intermediate Similarity	NPC162910
0.7086	Intermediate Similarity	NPC311534
0.7078	Intermediate Similarity	NPC476778
0.7078	Intermediate Similarity	NPC76999
0.7078	Intermediate Similarity	NPC477072
0.7078	Intermediate Similarity	NPC476777
0.7075	Intermediate Similarity	NPC476127
0.7075	Intermediate Similarity	NPC72260
0.7075	Intermediate Similarity	NPC476150
0.7075	Intermediate Similarity	NPC475556
0.7075	Intermediate Similarity	NPC475136
0.7075	Intermediate Similarity	NPC475629
0.7075	Intermediate Similarity	NPC474466
0.7063	Intermediate Similarity	NPC214821
0.7063	Intermediate Similarity	NPC298067
0.7059	Intermediate Similarity	NPC471855
0.7039	Intermediate Similarity	NPC477196
0.7039	Intermediate Similarity	NPC476966
0.7034	Intermediate Similarity	NPC196931
0.7034	Intermediate Similarity	NPC244127
0.7032	Intermediate Similarity	NPC279915
0.7032	Intermediate Similarity	NPC110700
0.7027	Intermediate Similarity	NPC475419
0.7027	Intermediate Similarity	NPC40749
0.7027	Intermediate Similarity	NPC475219
0.7027	Intermediate Similarity	NPC120390
0.7027	Intermediate Similarity	NPC173555
0.7027	Intermediate Similarity	NPC231518
0.7027	Intermediate Similarity	NPC314535
0.7027	Intermediate Similarity	NPC474908
0.7027	Intermediate Similarity	NPC475590
0.7013	Intermediate Similarity	NPC476779
0.7007	Intermediate Similarity	NPC122971
0.7007	Intermediate Similarity	NPC477071
0.7006	Intermediate Similarity	NPC79250
0.7006	Intermediate Similarity	NPC290746
0.7	Intermediate Similarity	NPC475892
0.7	Intermediate Similarity	NPC298469
0.6993	Remote Similarity	NPC264566
0.6993	Remote Similarity	NPC478065
0.6993	Remote Similarity	NPC262796
0.6993	Remote Similarity	NPC476074
0.6993	Remote Similarity	NPC45346
0.6993	Remote Similarity	NPC173347
0.6993	Remote Similarity	NPC301639
0.6993	Remote Similarity	NPC25998
0.6993	Remote Similarity	NPC475377
0.6993	Remote Similarity	NPC477197
0.6993	Remote Similarity	NPC173435
0.6993	Remote Similarity	NPC329993
0.6993	Remote Similarity	NPC172374
0.6993	Remote Similarity	NPC478064
0.6993	Remote Similarity	NPC475167
0.6993	Remote Similarity	NPC134914
0.6993	Remote Similarity	NPC478155
0.6987	Remote Similarity	NPC289700
0.6987	Remote Similarity	NPC127656
0.6987	Remote Similarity	NPC62172
0.6986	Remote Similarity	NPC474483
0.6986	Remote Similarity	NPC93883
0.6986	Remote Similarity	NPC152615
0.6986	Remote Similarity	NPC477252
0.6986	Remote Similarity	NPC473405
0.698	Remote Similarity	NPC264336
0.698	Remote Similarity	NPC28532
0.698	Remote Similarity	NPC474423
0.698	Remote Similarity	NPC74259
0.698	Remote Similarity	NPC193893
0.6974	Remote Similarity	NPC477192
0.6974	Remote Similarity	NPC477191
0.6974	Remote Similarity	NPC477194
0.6974	Remote Similarity	NPC245094
0.6974	Remote Similarity	NPC114306
0.6974	Remote Similarity	NPC477078
0.6974	Remote Similarity	NPC477193
0.6974	Remote Similarity	NPC477075
0.6974	Remote Similarity	NPC475281
0.6974	Remote Similarity	NPC329923
0.6974	Remote Similarity	NPC477490
0.6968	Remote Similarity	NPC477234
0.6948	Remote Similarity	NPC478152
0.6948	Remote Similarity	NPC476776
0.6948	Remote Similarity	NPC478153
0.6948	Remote Similarity	NPC155529
0.6948	Remote Similarity	NPC478150
0.6948	Remote Similarity	NPC478154
0.6939	Remote Similarity	NPC471548
0.6939	Remote Similarity	NPC45475
0.6939	Remote Similarity	NPC291564
0.6937	Remote Similarity	NPC803
0.6937	Remote Similarity	NPC475152
0.6937	Remote Similarity	NPC475584
0.6937	Remote Similarity	NPC475394
0.6933	Remote Similarity	NPC308262
0.6933	Remote Similarity	NPC208193

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 NPC473208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1067
0.2-0.3	4010
0.3-0.4	2944
0.4-0.5	705
0.5-0.6	238
0.6-0.7	35
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD7625	Phase 1
0.7534	Intermediate Similarity	NPD7507	Approved
0.7383	Intermediate Similarity	NPD7319	Approved
0.7075	Intermediate Similarity	NPD8377	Approved
0.7075	Intermediate Similarity	NPD8294	Approved
0.7027	Intermediate Similarity	NPD8380	Approved
0.7027	Intermediate Similarity	NPD8335	Approved
0.7027	Intermediate Similarity	NPD8378	Approved
0.7027	Intermediate Similarity	NPD8379	Approved
0.7027	Intermediate Similarity	NPD8033	Approved
0.7027	Intermediate Similarity	NPD8296	Approved
0.6892	Remote Similarity	NPD7516	Approved
0.6824	Remote Similarity	NPD7327	Approved
0.6824	Remote Similarity	NPD7328	Approved
0.6783	Remote Similarity	NPD6686	Approved
0.6781	Remote Similarity	NPD8133	Approved
0.6711	Remote Similarity	NPD8328	Phase 3
0.6494	Remote Similarity	NPD6067	Discontinued
0.6481	Remote Similarity	NPD6333	Approved
0.6481	Remote Similarity	NPD6334	Approved
0.6433	Remote Similarity	NPD7736	Approved
0.6424	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8451	Approved
0.6395	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6412	Phase 2
0.6369	Remote Similarity	NPD8074	Phase 3
0.6369	Remote Similarity	NPD8448	Approved
0.6364	Remote Similarity	NPD7503	Approved
0.6352	Remote Similarity	NPD6914	Discontinued
0.6352	Remote Similarity	NPD8390	Approved
0.6352	Remote Similarity	NPD8392	Approved
0.6352	Remote Similarity	NPD8391	Approved
0.6266	Remote Similarity	NPD8293	Discontinued
0.6258	Remote Similarity	NPD8516	Approved
0.6258	Remote Similarity	NPD8513	Phase 3
0.6258	Remote Similarity	NPD8515	Approved
0.6258	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD8517	Approved
0.6242	Remote Similarity	NPD8340	Approved
0.6242	Remote Similarity	NPD8341	Approved
0.6242	Remote Similarity	NPD8299	Approved
0.6242	Remote Similarity	NPD8342	Approved
0.6226	Remote Similarity	NPD8337	Approved
0.6226	Remote Similarity	NPD8336	Approved
0.6224	Remote Similarity	NPD7638	Approved
0.6181	Remote Similarity	NPD7639	Approved
0.6181	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6370	Approved
0.6093	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD7642	Approved
0.6076	Remote Similarity	NPD7830	Approved
0.6076	Remote Similarity	NPD7829	Approved
0.6076	Remote Similarity	NPD7122	Discontinued
0.6074	Remote Similarity	NPD8338	Approved
0.6065	Remote Similarity	NPD7641	Discontinued
0.6062	Remote Similarity	NPD7078	Approved
0.6061	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD7505	Discontinued
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD6616	Approved
0.5987	Remote Similarity	NPD6059	Approved
0.5987	Remote Similarity	NPD6054	Approved
0.5975	Remote Similarity	NPD7604	Phase 2
0.5973	Remote Similarity	NPD4211	Phase 1
0.596	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD6921	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5948	Remote Similarity	NPD6882	Approved
0.5924	Remote Similarity	NPD7519	Approved
0.5924	Remote Similarity	NPD7518	Approved
0.5924	Remote Similarity	NPD7517	Approved
0.5921	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD7260	Phase 2
0.5912	Remote Similarity	NPD8080	Discontinued
0.5909	Remote Similarity	NPD4632	Approved
0.5904	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD6319	Approved
0.5882	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD8449	Approved
0.5879	Remote Similarity	NPD6845	Suspended
0.5855	Remote Similarity	NPD6372	Approved
0.5855	Remote Similarity	NPD6373	Approved
0.5849	Remote Similarity	NPD6909	Approved
0.5849	Remote Similarity	NPD6016	Approved
0.5849	Remote Similarity	NPD6908	Approved
0.5849	Remote Similarity	NPD6015	Approved
0.5843	Remote Similarity	NPD8450	Suspended
0.5822	Remote Similarity	NPD7902	Approved
0.5817	Remote Similarity	NPD8462	Phase 1
0.5813	Remote Similarity	NPD5988	Approved
0.5789	Remote Similarity	NPD7320	Approved
0.5789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD7147	Phase 3
0.5786	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD6650	Approved
0.5779	Remote Similarity	NPD6649	Approved
0.5772	Remote Similarity	NPD7632	Discontinued
0.5762	Remote Similarity	NPD5739	Approved
0.5762	Remote Similarity	NPD6008	Approved
0.5762	Remote Similarity	NPD7128	Approved
0.5762	Remote Similarity	NPD6402	Approved
0.5762	Remote Similarity	NPD6675	Approved
0.575	Remote Similarity	NPD8444	Approved
0.575	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD6053	Discontinued
0.5733	Remote Similarity	NPD4754	Approved
0.5733	Remote Similarity	NPD6052	Approved
0.5732	Remote Similarity	NPD6940	Discontinued
0.5732	Remote Similarity	NPD6033	Approved
0.5724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD7748	Approved
0.5722	Remote Similarity	NPD8407	Phase 2
0.5714	Remote Similarity	NPD5135	Approved
0.5714	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD8034	Phase 2
0.5694	Remote Similarity	NPD8035	Phase 2
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.5677	Remote Similarity	NPD8130	Phase 1
0.5663	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD6399	Phase 3
0.5652	Remote Similarity	NPD5983	Phase 2
0.5648	Remote Similarity	NPD8368	Discontinued
0.5646	Remote Similarity	NPD4697	Phase 3
0.5638	Remote Similarity	NPD6404	Discontinued
0.5621	Remote Similarity	NPD5697	Approved
0.5621	Remote Similarity	NPD5701	Approved
0.5616	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD7900	Approved
0.5613	Remote Similarity	NPD7102	Approved
0.5613	Remote Similarity	NPD7290	Approved
0.5613	Remote Similarity	NPD6883	Approved
0.561	Remote Similarity	NPD6336	Discontinued
0.5606	Remote Similarity	NPD8360	Approved
0.5606	Remote Similarity	NPD8361	Approved
0.5606	Remote Similarity	NPD8435	Approved
0.5602	Remote Similarity	NPD7799	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data