NPASS Compound

Structure

NPC140092 OpenBabel07101719252D 49 55 0 0 1 0 0 0 0 0999 V2000 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 2.5691 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6723 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 6.9282 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 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 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 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 7.7942 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2111 3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2583 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 -3.5000 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 -3.0201 4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 3.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 34 1 0 0 0 0 3 44 1 0 0 0 0 4 5 1 0 0 0 0 4 20 1 0 0 0 0 5 24 1 0 0 0 0 6 10 1 0 0 0 0 6 21 1 0 0 0 0 7 9 1 0 0 0 0 7 23 1 0 0 0 0 8 11 1 0 0 0 0 8 22 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 36 1 0 0 0 0 12 19 2 0 0 0 0 12 27 1 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 14 28 1 0 0 0 0 15 37 1 0 0 0 0 16 19 1 0 0 0 0 16 45 1 0 0 0 0 17 38 2 0 0 0 0 18 1 1 6 0 0 0 18 32 1 0 0 0 0 18 46 1 0 0 0 0 19 22 1 0 0 0 0 20 35 1 6 0 0 0 21 47 1 6 0 0 0 22 34 1 6 0 0 0 23 24 1 0 0 0 0 23 35 1 6 0 0 0 24 36 1 1 0 0 0 25 32 1 0 0 0 0 25 44 1 1 0 0 0 26 15 1 1 0 0 0 26 29 1 0 0 0 0 26 48 1 0 0 0 0 27 39 2 0 0 0 0 27 45 1 0 0 0 0 28 46 1 0 0 0 0 28 47 1 6 0 0 0 29 30 1 0 0 0 0 29 40 1 6 0 0 0 30 31 1 0 0 0 0 30 41 1 1 0 0 0 31 33 1 0 0 0 0 31 42 1 6 0 0 0 32 49 1 6 0 0 0 33 48 1 0 0 0 0 33 49 1 1 0 0 0 34 36 1 6 0 0 0 35 17 1 6 0 0 0 36 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.36
Volume:	677.68
LogP:	1.832
LogD:	1.818
LogS:	-3.445
# Rotatable Bonds:	8
TPSA:	197.74
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	5.82
Fsp3:	0.861
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:	-5.94
MDCK Permeability:	5.7435707276454195e-05
Pgp-inhibitor:	0.774
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.927
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	64.42784881591797%
Volume Distribution (VD):	0.713
Pgp-substrate:	20.463665008544922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.714
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	1.689
Half-life (T1/2):	0.522

ADMET: Toxicity

hERG Blockers:	0.456
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.59
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.935
Carcinogencity:	0.64
Eye Corrosion:	0.003
Eye Irritation:	0.01
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: NPC140092

Natural Product ID:	NPC140092
*Common Name:**	Boivinide B
IUPAC Name:	(3S,5S,8R,9S,10R,13R,14S,17R)-14-hydroxy-3-[(2R,4S,5S,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:	boivinide B
Standard InCHIKey:	CSVNMGCNZRUZHN-UMPKUIGKSA-N
Standard InCHI:	InChI=1S/C36H54O13/c1-18-32(49-33-31(42)30(41)29(40)26(15-37)48-33)25(44-3)14-28(46-18)47-21-6-10-35(17-38)20(13-21)4-5-24-23(35)7-9-34(2)22(8-11-36(24,34)43)19-12-27(39)45-16-19/h12,17-18,20-26,28-33,37,40-43H,4-11,13-16H2,1-3H3/t18-,20+,21+,22-,23+,24-,25+,26-,28+,29-,30+,31-,32+,33+,34-,35-,36+/m1/s1
SMILES:	CO[C@H]1C[C@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C=O)O[C@@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398881
PubChem CID:	24180056
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
NPO33407	roupellina boivinii	Species	n.a.	n.a.	n.a.	Madagascar rainforest	n.a.	PMID[17988099]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	660.0	nM	PMID[557091]

☑ 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 NPC140092 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	299
0.1-0.2	1762
0.2-0.3	5069
0.3-0.4	9771
0.4-0.5	11017
0.5-0.6	6814
0.6-0.7	4740
0.7-0.8	2117
0.8-0.85	798
0.85-0.9	166
0.9-0.95	95
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329986
1.0	High Similarity	NPC276838
1.0	High Similarity	NPC125077
1.0	High Similarity	NPC232785
1.0	High Similarity	NPC188234
0.9831	High Similarity	NPC329784
0.9831	High Similarity	NPC240070
0.9752	High Similarity	NPC477709
0.9752	High Similarity	NPC116075
0.9752	High Similarity	NPC247190
0.9752	High Similarity	NPC476221
0.9752	High Similarity	NPC32793
0.9752	High Similarity	NPC146857
0.9752	High Similarity	NPC469749
0.975	High Similarity	NPC16569
0.975	High Similarity	NPC253456
0.975	High Similarity	NPC159338
0.9746	High Similarity	NPC469750
0.9746	High Similarity	NPC250556
0.9672	High Similarity	NPC329636
0.9669	High Similarity	NPC93416
0.9669	High Similarity	NPC42670
0.9669	High Similarity	NPC19124
0.9667	High Similarity	NPC91
0.9664	High Similarity	NPC471356
0.9664	High Similarity	NPC179412
0.9593	High Similarity	NPC194716
0.959	High Similarity	NPC142756
0.959	High Similarity	NPC298783
0.959	High Similarity	NPC157817
0.959	High Similarity	NPC225385
0.959	High Similarity	NPC104585
0.9576	High Similarity	NPC27363
0.9516	High Similarity	NPC329675
0.9516	High Similarity	NPC59288
0.9504	High Similarity	NPC469753
0.9504	High Similarity	NPC180079
0.9504	High Similarity	NPC89514
0.9504	High Similarity	NPC469751
0.9504	High Similarity	NPC86159
0.9504	High Similarity	NPC197707
0.9504	High Similarity	NPC471358
0.9504	High Similarity	NPC284406
0.9504	High Similarity	NPC471361
0.9504	High Similarity	NPC469752
0.9504	High Similarity	NPC219085
0.9504	High Similarity	NPC6108
0.9504	High Similarity	NPC9499
0.9504	High Similarity	NPC10823
0.9504	High Similarity	NPC251866
0.9504	High Similarity	NPC471352
0.9504	High Similarity	NPC70542
0.9504	High Similarity	NPC17896
0.9504	High Similarity	NPC469754
0.9504	High Similarity	NPC471360
0.9504	High Similarity	NPC469755
0.9504	High Similarity	NPC471359
0.9339	High Similarity	NPC469757
0.9339	High Similarity	NPC471357
0.9339	High Similarity	NPC117702
0.9339	High Similarity	NPC146456
0.9237	High Similarity	NPC55532
0.9237	High Similarity	NPC236973
0.9237	High Similarity	NPC30483
0.9237	High Similarity	NPC32177
0.9237	High Similarity	NPC292467
0.9237	High Similarity	NPC469756
0.9237	High Similarity	NPC470897
0.916	High Similarity	NPC475556
0.916	High Similarity	NPC470312
0.916	High Similarity	NPC72260
0.916	High Similarity	NPC475629
0.9127	High Similarity	NPC171619
0.9106	High Similarity	NPC311534
0.9083	High Similarity	NPC314535
0.9083	High Similarity	NPC173555
0.9083	High Similarity	NPC475590
0.9083	High Similarity	NPC231518
0.9083	High Similarity	NPC120390
0.9083	High Similarity	NPC475219
0.9083	High Similarity	NPC474908
0.9083	High Similarity	NPC475419
0.9083	High Similarity	NPC40749
0.9076	High Similarity	NPC329905
0.9068	High Similarity	NPC93883
0.9008	High Similarity	NPC193893
0.9008	High Similarity	NPC474423
0.9008	High Similarity	NPC74259
0.9008	High Similarity	NPC264336
0.9	High Similarity	NPC474466
0.9	High Similarity	NPC475136
0.8983	High Similarity	NPC193382
0.8983	High Similarity	NPC199428
0.8983	High Similarity	NPC5311
0.8983	High Similarity	NPC310341
0.8983	High Similarity	NPC99620
0.8968	High Similarity	NPC88668
0.896	High Similarity	NPC173347
0.8934	High Similarity	NPC117445
0.8934	High Similarity	NPC308262
0.8934	High Similarity	NPC208193
0.8917	High Similarity	NPC5883
0.8917	High Similarity	NPC44899
0.8917	High Similarity	NPC29639
0.8917	High Similarity	NPC304260
0.8908	High Similarity	NPC77319
0.8908	High Similarity	NPC474418
0.8908	High Similarity	NPC142066
0.8908	High Similarity	NPC152615
0.8908	High Similarity	NPC157376
0.8908	High Similarity	NPC158344
0.8908	High Similarity	NPC471351
0.8908	High Similarity	NPC471353
0.8908	High Similarity	NPC87250
0.8908	High Similarity	NPC473852
0.8908	High Similarity	NPC84987
0.8908	High Similarity	NPC243196
0.8908	High Similarity	NPC196429
0.8908	High Similarity	NPC471355
0.8908	High Similarity	NPC471354
0.8908	High Similarity	NPC244402
0.8908	High Similarity	NPC309034
0.8908	High Similarity	NPC99728
0.8908	High Similarity	NPC50305
0.8908	High Similarity	NPC27507
0.8908	High Similarity	NPC34390
0.8906	High Similarity	NPC127656
0.8906	High Similarity	NPC62172
0.8906	High Similarity	NPC289700
0.8898	High Similarity	NPC84949
0.8898	High Similarity	NPC69576
0.8898	High Similarity	NPC471633
0.8898	High Similarity	NPC31354
0.8889	High Similarity	NPC155529
0.8843	High Similarity	NPC107607
0.8833	High Similarity	NPC83287
0.8833	High Similarity	NPC218093
0.8828	High Similarity	NPC158350
0.8769	High Similarity	NPC75616
0.876	High Similarity	NPC291820
0.876	High Similarity	NPC81222
0.875	High Similarity	NPC290693
0.875	High Similarity	NPC203862
0.874	High Similarity	NPC471855
0.8699	High Similarity	NPC28532
0.8689	High Similarity	NPC476150
0.8689	High Similarity	NPC476127
0.8667	High Similarity	NPC196931
0.8651	High Similarity	NPC477490
0.8651	High Similarity	NPC114306
0.8626	High Similarity	NPC290746
0.8626	High Similarity	NPC79250
0.8607	High Similarity	NPC477071
0.8595	High Similarity	NPC474483
0.8583	High Similarity	NPC477580
0.8583	High Similarity	NPC471407
0.856	High Similarity	NPC318135
0.8548	High Similarity	NPC115349
0.8537	High Similarity	NPC135369
0.8525	High Similarity	NPC45475
0.8516	High Similarity	NPC477493
0.8512	High Similarity	NPC138372
0.8512	High Similarity	NPC72772
0.8512	High Similarity	NPC469794
0.8512	High Similarity	NPC106228
0.8504	High Similarity	NPC168899
0.8504	High Similarity	NPC293623
0.8504	High Similarity	NPC245094
0.8504	High Similarity	NPC69273
0.85	High Similarity	NPC260665
0.8492	Intermediate Similarity	NPC47113
0.8492	Intermediate Similarity	NPC174367
0.848	Intermediate Similarity	NPC41129
0.8468	Intermediate Similarity	NPC476204
0.8468	Intermediate Similarity	NPC202051
0.8468	Intermediate Similarity	NPC170084
0.8462	Intermediate Similarity	NPC248703
0.8455	Intermediate Similarity	NPC19028
0.8455	Intermediate Similarity	NPC122971
0.8455	Intermediate Similarity	NPC9674
0.845	Intermediate Similarity	NPC477195
0.8443	Intermediate Similarity	NPC473405
0.8438	Intermediate Similarity	NPC476966
0.843	Intermediate Similarity	NPC178289
0.843	Intermediate Similarity	NPC473882
0.843	Intermediate Similarity	NPC472274
0.8425	Intermediate Similarity	NPC298841
0.8425	Intermediate Similarity	NPC42399
0.8413	Intermediate Similarity	NPC473505
0.839	Intermediate Similarity	NPC38217
0.839	Intermediate Similarity	NPC472988
0.8387	Intermediate Similarity	NPC281840
0.8387	Intermediate Similarity	NPC108072
0.8385	Intermediate Similarity	NPC316915
0.8385	Intermediate Similarity	NPC476779
0.8374	Intermediate Similarity	NPC473828
0.8374	Intermediate Similarity	NPC471548
0.8374	Intermediate Similarity	NPC473617
0.8374	Intermediate Similarity	NPC239293
0.8372	Intermediate Similarity	NPC241008

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 NPC140092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	1969
0.2-0.3	3989
0.3-0.4	1944
0.4-0.5	514
0.5-0.6	265
0.6-0.7	153
0.7-0.8	44
0.8-0.85	1
0.85-0.9	4
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9746	High Similarity	NPD7507	Approved
0.9504	High Similarity	NPD7319	Approved
0.916	High Similarity	NPD8377	Approved
0.916	High Similarity	NPD8294	Approved
0.9083	High Similarity	NPD8380	Approved
0.9083	High Similarity	NPD8335	Approved
0.9083	High Similarity	NPD8379	Approved
0.9083	High Similarity	NPD8296	Approved
0.9083	High Similarity	NPD8378	Approved
0.9083	High Similarity	NPD8033	Approved
0.8833	High Similarity	NPD7327	Approved
0.8833	High Similarity	NPD7328	Approved
0.876	High Similarity	NPD7516	Approved
0.85	High Similarity	NPD8133	Approved
0.8235	Intermediate Similarity	NPD6686	Approved
0.8217	Intermediate Similarity	NPD7736	Approved
0.8175	Intermediate Similarity	NPD7503	Approved
0.8047	Intermediate Similarity	NPD8328	Phase 3
0.8	Intermediate Similarity	NPD6412	Phase 2
0.8	Intermediate Similarity	NPD8293	Discontinued
0.7829	Intermediate Similarity	NPD6370	Approved
0.7717	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7638	Approved
0.771	Intermediate Similarity	NPD7492	Approved
0.7686	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8297	Approved
0.768	Intermediate Similarity	NPD6882	Approved
0.7674	Intermediate Similarity	NPD6054	Approved
0.7674	Intermediate Similarity	NPD6059	Approved
0.7652	Intermediate Similarity	NPD6616	Approved
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7615	Intermediate Similarity	NPD8516	Approved
0.7615	Intermediate Similarity	NPD8513	Phase 3
0.7615	Intermediate Similarity	NPD8517	Approved
0.7615	Intermediate Similarity	NPD8515	Approved
0.7594	Intermediate Similarity	NPD7078	Approved
0.7581	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6009	Approved
0.7538	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.7481	Intermediate Similarity	NPD6016	Approved
0.7481	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD4632	Approved
0.748	Intermediate Similarity	NPD6402	Approved
0.748	Intermediate Similarity	NPD5739	Approved
0.748	Intermediate Similarity	NPD7128	Approved
0.748	Intermediate Similarity	NPD6675	Approved
0.744	Intermediate Similarity	NPD6372	Approved
0.744	Intermediate Similarity	NPD6373	Approved
0.7424	Intermediate Similarity	NPD5988	Approved
0.7379	Intermediate Similarity	NPD7625	Phase 1
0.736	Intermediate Similarity	NPD6899	Approved
0.736	Intermediate Similarity	NPD6881	Approved
0.7323	Intermediate Similarity	NPD8130	Phase 1
0.7323	Intermediate Similarity	NPD6650	Approved
0.7323	Intermediate Similarity	NPD6649	Approved
0.7308	Intermediate Similarity	NPD7115	Discovery
0.7302	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD5697	Approved
0.728	Intermediate Similarity	NPD5701	Approved
0.7266	Intermediate Similarity	NPD6053	Discontinued
0.7244	Intermediate Similarity	NPD7102	Approved
0.7244	Intermediate Similarity	NPD7290	Approved
0.7244	Intermediate Similarity	NPD6883	Approved
0.72	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD6617	Approved
0.7188	Intermediate Similarity	NPD6847	Approved
0.7188	Intermediate Similarity	NPD6869	Approved
0.7165	Intermediate Similarity	NPD6013	Approved
0.7165	Intermediate Similarity	NPD6012	Approved
0.7165	Intermediate Similarity	NPD6014	Approved
0.7153	Intermediate Similarity	NPD6033	Approved
0.7111	Intermediate Similarity	NPD6067	Discontinued
0.7111	Intermediate Similarity	NPD7604	Phase 2
0.7109	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7632	Discontinued
0.709	Intermediate Similarity	NPD5983	Phase 2
0.7087	Intermediate Similarity	NPD6011	Approved
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4755	Approved
0.7007	Intermediate Similarity	NPD6336	Discontinued
0.7	Intermediate Similarity	NPD8171	Discontinued
0.6977	Remote Similarity	NPD4634	Approved
0.696	Remote Similarity	NPD5211	Phase 2
0.6953	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7748	Approved
0.6935	Remote Similarity	NPD5286	Approved
0.6935	Remote Similarity	NPD4700	Approved
0.6935	Remote Similarity	NPD4696	Approved
0.6935	Remote Similarity	NPD5285	Approved
0.6911	Remote Similarity	NPD7902	Approved
0.6911	Remote Similarity	NPD6083	Phase 2
0.6911	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5141	Approved
0.6842	Remote Similarity	NPD6274	Approved
0.6835	Remote Similarity	NPD8074	Phase 3
0.6825	Remote Similarity	NPD5225	Approved
0.6825	Remote Similarity	NPD5224	Approved
0.6825	Remote Similarity	NPD4633	Approved
0.6825	Remote Similarity	NPD5226	Approved
0.6815	Remote Similarity	NPD7101	Approved
0.6815	Remote Similarity	NPD7100	Approved
0.6797	Remote Similarity	NPD4768	Approved
0.6797	Remote Similarity	NPD4767	Approved
0.6777	Remote Similarity	NPD8035	Phase 2
0.6777	Remote Similarity	NPD8034	Phase 2
0.6777	Remote Similarity	NPD7515	Phase 2
0.6772	Remote Similarity	NPD5174	Approved
0.6772	Remote Similarity	NPD5175	Approved
0.6768	Remote Similarity	NPD7799	Discontinued
0.675	Remote Similarity	NPD5328	Approved
0.6746	Remote Similarity	NPD5223	Approved
0.6744	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6335	Approved
0.6721	Remote Similarity	NPD4202	Approved
0.672	Remote Similarity	NPD4225	Approved
0.6715	Remote Similarity	NPD6909	Approved
0.6715	Remote Similarity	NPD6908	Approved
0.6694	Remote Similarity	NPD46	Approved
0.6694	Remote Similarity	NPD4697	Phase 3
0.6694	Remote Similarity	NPD6698	Approved
0.6692	Remote Similarity	NPD4730	Approved
0.6692	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6641	Remote Similarity	NPD4754	Approved
0.6639	Remote Similarity	NPD6079	Approved
0.6618	Remote Similarity	NPD6314	Approved
0.6618	Remote Similarity	NPD6313	Approved
0.6613	Remote Similarity	NPD5695	Phase 3
0.6613	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5251	Approved
0.6591	Remote Similarity	NPD6371	Approved
0.6591	Remote Similarity	NPD5248	Approved
0.6591	Remote Similarity	NPD5247	Approved
0.6591	Remote Similarity	NPD5249	Phase 3
0.6591	Remote Similarity	NPD5250	Approved
0.6587	Remote Similarity	NPD5696	Approved
0.6587	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6399	Phase 3
0.6565	Remote Similarity	NPD5128	Approved
0.6555	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8336	Approved
0.6549	Remote Similarity	NPD8337	Approved
0.6529	Remote Similarity	NPD6903	Approved
0.6525	Remote Similarity	NPD8451	Approved
0.6504	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD7334	Approved
0.65	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD6684	Approved
0.65	Remote Similarity	NPD5330	Approved
0.65	Remote Similarity	NPD7146	Approved
0.6483	Remote Similarity	NPD8449	Approved
0.6479	Remote Similarity	NPD8448	Approved
0.6475	Remote Similarity	NPD6921	Approved
0.6475	Remote Similarity	NPD4753	Phase 2
0.6458	Remote Similarity	NPD8390	Approved
0.6458	Remote Similarity	NPD8391	Approved
0.6458	Remote Similarity	NPD5956	Approved
0.6458	Remote Similarity	NPD8392	Approved
0.6438	Remote Similarity	NPD8450	Suspended
0.6429	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5221	Approved
0.6429	Remote Similarity	NPD5222	Approved
0.6418	Remote Similarity	NPD5216	Approved
0.6418	Remote Similarity	NPD5215	Approved
0.6418	Remote Similarity	NPD5217	Approved
0.6414	Remote Similarity	NPD7260	Phase 2
0.6383	Remote Similarity	NPD7829	Approved
0.6383	Remote Similarity	NPD7830	Approved
0.6378	Remote Similarity	NPD5173	Approved
0.637	Remote Similarity	NPD8338	Approved
0.6364	Remote Similarity	NPD3618	Phase 1
0.6357	Remote Similarity	NPD5344	Discontinued
0.635	Remote Similarity	NPD6868	Approved
0.6343	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5169	Approved
0.6343	Remote Similarity	NPD5135	Approved
0.6341	Remote Similarity	NPD6080	Approved
0.6341	Remote Similarity	NPD6904	Approved
0.6341	Remote Similarity	NPD6051	Approved
0.6341	Remote Similarity	NPD6673	Approved
0.6338	Remote Similarity	NPD8341	Approved
0.6338	Remote Similarity	NPD8340	Approved
0.6338	Remote Similarity	NPD8299	Approved
0.6338	Remote Similarity	NPD8342	Approved
0.6333	Remote Similarity	NPD3666	Approved
0.6333	Remote Similarity	NPD3665	Phase 1
0.6333	Remote Similarity	NPD3133	Approved
0.6311	Remote Similarity	NPD3573	Approved
0.6303	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5127	Approved
0.6282	Remote Similarity	NPD7236	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