NPASS Compound

Structure

NPC310621 OpenBabel07101718292D 45 50 0 0 1 0 0 0 0 0999 V2000 -4.7415 -0.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1265 -1.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5275 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0943 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0558 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4795 1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 -3.9216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0373 -0.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1484 2.3662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7825 -0.7452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4795 0.1872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4904 -3.9216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 -4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5471 -2.4510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2452 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5471 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8490 0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5471 1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0177 -0.6215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1734 2.4687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3395 -4.4118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 -5.3922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 2 0 0 0 0 2 24 1 0 0 0 0 5 37 1 0 0 0 0 7 10 2 0 0 0 0 7 25 1 0 0 0 0 8 12 2 0 0 0 0 8 25 1 0 0 0 0 9 11 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 31 1 0 0 0 0 12 33 1 0 0 0 0 13 18 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 32 1 0 0 0 0 16 35 1 0 0 0 0 17 38 1 0 0 0 0 18 39 1 0 0 0 0 19 20 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 25 2 0 0 0 0 21 29 1 0 0 0 0 22 36 1 0 0 0 0 22 40 1 0 0 0 0 23 41 1 0 0 0 0 26 24 1 6 0 0 0 26 34 1 0 0 0 0 27 34 1 0 0 0 0 27 37 1 6 0 0 0 28 29 2 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 35 1 1 0 0 0 30 36 1 0 0 0 0 31 35 1 1 0 0 0 31 38 1 0 0 0 0 32 36 1 1 0 0 0 32 45 1 0 0 0 0 33 44 2 0 0 0 0 33 45 1 0 0 0 0 34 39 1 1 0 0 0 35 3 1 1 0 0 0 36 4 1 1 0 0 0 37 38 1 1 0 0 0 38 6 1 1 0 0 0 39 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.41
Volume:	668.684
LogP:	5.992
LogD:	4.723
LogS:	-4.553
# Rotatable Bonds:	7
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.113
Synthetic Accessibility Score:	5.126
Fsp3:	0.718
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.313
MDCK Permeability:	2.1862999346922152e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.258
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	100.00782012939453%
Volume Distribution (VD):	0.738
Pgp-substrate:	2.3261756896972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.712
CYP2D6-inhibitor:	0.501
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	4.611
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.529
Human Hepatotoxicity (H-HT):	0.261
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.962
Carcinogencity:	0.01
Eye Corrosion:	0.005
Eye Irritation:	0.193
Respiratory Toxicity:	0.824

Download Data

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

Natural Product: NPC310621

Natural Product ID:	NPC310621
*Common Name:**	23,28-Dihydroxylupan-20(29)-Ene-3Beta-Caffeate
IUPAC Name:	[(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-3a,8-bis(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	SSEGSBMQGFCSBY-KEMSSATHSA-N
Standard InCHI:	InChI=1S/C39H56O6/c1-24(2)26-13-18-39(23-41)20-19-37(5)27(34(26)39)9-11-31-35(3)16-15-32(36(4,22-40)30(35)14-17-38(31,37)6)45-33(44)12-8-25-7-10-28(42)29(43)21-25/h7-8,10,12,21,26-27,30-32,34,40-43H,1,9,11,13-20,22-23H2,2-6H3/b12-8+/t26-,27+,30+,31+,32-,34+,35-,36-,37+,38+,39+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)OC(=O)/C=C/c3ccc(c(c3)O)O)[C@@H]12)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224891
PubChem CID:	46939047
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10507	Sorbus decora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20738101]
NPO10507	Sorbus decora	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10507	Sorbus decora	Species	Rosaceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2219	Cell Line	C2C12	Mus musculus	EC50	=	1470.0	nM	PMID[559252]

☑ 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 NPC310621 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	319
0.1-0.2	1282
0.2-0.3	2775
0.3-0.4	5422
0.4-0.5	9466
0.5-0.6	13578
0.6-0.7	8505
0.7-0.8	1189
0.8-0.85	60
0.85-0.9	57
0.9-0.95	26
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC35212
0.9853	High Similarity	NPC252133
0.9852	High Similarity	NPC473612
0.9708	High Similarity	NPC235557
0.9638	High Similarity	NPC26045
0.9632	High Similarity	NPC473591
0.9632	High Similarity	NPC271494
0.9632	High Similarity	NPC155192
0.9559	High Similarity	NPC182249
0.95	High Similarity	NPC8102
0.95	High Similarity	NPC66894
0.9416	High Similarity	NPC116742
0.9416	High Similarity	NPC139243
0.9407	High Similarity	NPC11266
0.9348	High Similarity	NPC470617
0.9348	High Similarity	NPC470616
0.9236	High Similarity	NPC470618
0.9236	High Similarity	NPC145527
0.9236	High Similarity	NPC208785
0.9236	High Similarity	NPC470619
0.9167	High Similarity	NPC298647
0.9167	High Similarity	NPC273358
0.9155	High Similarity	NPC19862
0.9155	High Similarity	NPC235195
0.9149	High Similarity	NPC477873
0.9149	High Similarity	NPC469447
0.9097	High Similarity	NPC32017
0.9097	High Similarity	NPC96930
0.9048	High Similarity	NPC205392
0.9048	High Similarity	NPC105942
0.9037	High Similarity	NPC30174
0.9034	High Similarity	NPC292206
0.9021	High Similarity	NPC53520
0.9021	High Similarity	NPC280717
0.9021	High Similarity	NPC271607
0.9021	High Similarity	NPC307205
0.9	High Similarity	NPC234548
0.9	High Similarity	NPC248287
0.8993	High Similarity	NPC476699
0.8897	High Similarity	NPC86257
0.8873	High Similarity	NPC27518
0.8873	High Similarity	NPC304110
0.8851	High Similarity	NPC473773
0.8851	High Similarity	NPC475579
0.8803	High Similarity	NPC471875
0.8794	High Similarity	NPC198621
0.8794	High Similarity	NPC22676
0.8794	High Similarity	NPC475482
0.8794	High Similarity	NPC216940
0.8784	High Similarity	NPC118033
0.8723	High Similarity	NPC249817
0.869	High Similarity	NPC25491
0.8662	High Similarity	NPC471152
0.8658	High Similarity	NPC475311
0.8658	High Similarity	NPC473680
0.8658	High Similarity	NPC475454
0.8658	High Similarity	NPC473579
0.8652	High Similarity	NPC173569
0.8652	High Similarity	NPC477874
0.8601	High Similarity	NPC132723
0.8601	High Similarity	NPC76032
0.8535	High Similarity	NPC200726
0.8529	High Similarity	NPC265413
0.8529	High Similarity	NPC10154
0.8523	High Similarity	NPC279442
0.8521	High Similarity	NPC43353
0.8489	Intermediate Similarity	NPC288290
0.8483	Intermediate Similarity	NPC472801
0.8481	Intermediate Similarity	NPC286809
0.8481	Intermediate Similarity	NPC177362
0.8462	Intermediate Similarity	NPC154485
0.8462	Intermediate Similarity	NPC471872
0.8435	Intermediate Similarity	NPC96447
0.8428	Intermediate Similarity	NPC266545
0.8428	Intermediate Similarity	NPC202428
0.8411	Intermediate Similarity	NPC77310
0.8394	Intermediate Similarity	NPC474532
0.8389	Intermediate Similarity	NPC472937
0.8389	Intermediate Similarity	NPC472938
0.8389	Intermediate Similarity	NPC472936
0.838	Intermediate Similarity	NPC475346
0.838	Intermediate Similarity	NPC18982
0.838	Intermediate Similarity	NPC475457
0.838	Intermediate Similarity	NPC475627
0.8356	Intermediate Similarity	NPC172311
0.8288	Intermediate Similarity	NPC164743
0.828	Intermediate Similarity	NPC266365
0.8278	Intermediate Similarity	NPC477206
0.8235	Intermediate Similarity	NPC470849
0.8235	Intermediate Similarity	NPC470848
0.8227	Intermediate Similarity	NPC475138
0.8224	Intermediate Similarity	NPC472939
0.8217	Intermediate Similarity	NPC269668
0.8212	Intermediate Similarity	NPC477483
0.8212	Intermediate Similarity	NPC325032
0.82	Intermediate Similarity	NPC320734
0.8194	Intermediate Similarity	NPC472807
0.8194	Intermediate Similarity	NPC471913
0.8188	Intermediate Similarity	NPC477207
0.8188	Intermediate Similarity	NPC471876
0.8182	Intermediate Similarity	NPC471874
0.8163	Intermediate Similarity	NPC106055
0.8163	Intermediate Similarity	NPC110699
0.8148	Intermediate Similarity	NPC309434
0.8148	Intermediate Similarity	NPC203124
0.8138	Intermediate Similarity	NPC472804
0.8125	Intermediate Similarity	NPC476282
0.8121	Intermediate Similarity	NPC204644
0.8116	Intermediate Similarity	NPC321402
0.8116	Intermediate Similarity	NPC478058
0.8108	Intermediate Similarity	NPC470035
0.8105	Intermediate Similarity	NPC327962
0.8088	Intermediate Similarity	NPC263386
0.8088	Intermediate Similarity	NPC109371
0.8088	Intermediate Similarity	NPC141791
0.8088	Intermediate Similarity	NPC470215
0.8088	Intermediate Similarity	NPC470214
0.8082	Intermediate Similarity	NPC470733
0.8082	Intermediate Similarity	NPC120852
0.8071	Intermediate Similarity	NPC137416
0.8065	Intermediate Similarity	NPC115203
0.8037	Intermediate Similarity	NPC472803
0.8015	Intermediate Similarity	NPC86198
0.8014	Intermediate Similarity	NPC103082
0.8	Intermediate Similarity	NPC281277
0.7988	Intermediate Similarity	NPC469772
0.7988	Intermediate Similarity	NPC469777
0.7988	Intermediate Similarity	NPC469774
0.7988	Intermediate Similarity	NPC100925
0.7988	Intermediate Similarity	NPC469773
0.7988	Intermediate Similarity	NPC135334
0.7988	Intermediate Similarity	NPC469778
0.7988	Intermediate Similarity	NPC32723
0.7988	Intermediate Similarity	NPC469776
0.7988	Intermediate Similarity	NPC469775
0.7988	Intermediate Similarity	NPC295941
0.7987	Intermediate Similarity	NPC142654
0.7986	Intermediate Similarity	NPC243305
0.7973	Intermediate Similarity	NPC475757
0.7973	Intermediate Similarity	NPC474640
0.7972	Intermediate Similarity	NPC470747
0.7956	Intermediate Similarity	NPC70084
0.7941	Intermediate Similarity	NPC145023
0.7941	Intermediate Similarity	NPC175799
0.7941	Intermediate Similarity	NPC610
0.7941	Intermediate Similarity	NPC200988
0.7933	Intermediate Similarity	NPC67467
0.7931	Intermediate Similarity	NPC321502
0.7926	Intermediate Similarity	NPC233669
0.7926	Intermediate Similarity	NPC474967
0.7914	Intermediate Similarity	NPC147654
0.7908	Intermediate Similarity	NPC477208
0.7895	Intermediate Similarity	NPC163898
0.7895	Intermediate Similarity	NPC473909
0.7895	Intermediate Similarity	NPC143120
0.7895	Intermediate Similarity	NPC274960
0.7887	Intermediate Similarity	NPC190849
0.7887	Intermediate Similarity	NPC171007
0.7885	Intermediate Similarity	NPC478268
0.7883	Intermediate Similarity	NPC275519
0.7881	Intermediate Similarity	NPC264632
0.7881	Intermediate Similarity	NPC476380
0.7881	Intermediate Similarity	NPC476378
0.7881	Intermediate Similarity	NPC476384
0.7881	Intermediate Similarity	NPC477209
0.7881	Intermediate Similarity	NPC205864
0.7881	Intermediate Similarity	NPC298257
0.7881	Intermediate Similarity	NPC96795
0.7881	Intermediate Similarity	NPC112
0.7881	Intermediate Similarity	NPC247032
0.7881	Intermediate Similarity	NPC476375
0.7881	Intermediate Similarity	NPC476397
0.7881	Intermediate Similarity	NPC476381
0.7881	Intermediate Similarity	NPC184935
0.7881	Intermediate Similarity	NPC76406
0.7881	Intermediate Similarity	NPC269141
0.7881	Intermediate Similarity	NPC175214
0.7881	Intermediate Similarity	NPC119537
0.7868	Intermediate Similarity	NPC137496
0.7868	Intermediate Similarity	NPC154511
0.7868	Intermediate Similarity	NPC257540
0.7868	Intermediate Similarity	NPC247858
0.7868	Intermediate Similarity	NPC474358
0.7868	Intermediate Similarity	NPC474387
0.7867	Intermediate Similarity	NPC476377
0.7867	Intermediate Similarity	NPC47471
0.7866	Intermediate Similarity	NPC471870
0.7862	Intermediate Similarity	NPC125495
0.7862	Intermediate Similarity	NPC312341
0.7857	Intermediate Similarity	NPC471794
0.7857	Intermediate Similarity	NPC95990
0.7857	Intermediate Similarity	NPC102934
0.7857	Intermediate Similarity	NPC252402
0.7852	Intermediate Similarity	NPC81515
0.7852	Intermediate Similarity	NPC261453
0.7852	Intermediate Similarity	NPC328593
0.7852	Intermediate Similarity	NPC68092
0.7852	Intermediate Similarity	NPC33749
0.7852	Intermediate Similarity	NPC64141
0.7852	Intermediate Similarity	NPC197316

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 NPC310621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	817
0.2-0.3	1547
0.3-0.4	2818
0.4-0.5	2151
0.5-0.6	1258
0.6-0.7	271
0.7-0.8	25
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD8166	Discontinued
0.8085	Intermediate Similarity	NPD5736	Approved
0.805	Intermediate Similarity	NPD8127	Discontinued
0.7931	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3620	Phase 2
0.7862	Intermediate Similarity	NPD6663	Approved
0.7852	Intermediate Similarity	NPD7266	Discontinued
0.7817	Intermediate Similarity	NPD3094	Phase 2
0.7808	Intermediate Similarity	NPD4140	Approved
0.7786	Intermediate Similarity	NPD3092	Approved
0.7754	Intermediate Similarity	NPD3091	Approved
0.7677	Intermediate Similarity	NPD6273	Approved
0.7518	Intermediate Similarity	NPD3095	Discontinued
0.7517	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD5762	Approved
0.75	Intermediate Similarity	NPD5763	Approved
0.7394	Intermediate Similarity	NPD3019	Approved
0.7355	Intermediate Similarity	NPD7003	Approved
0.7353	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD3022	Approved
0.7341	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.731	Intermediate Similarity	NPD5327	Phase 3
0.7308	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2932	Approved
0.7273	Intermediate Similarity	NPD4059	Approved
0.7267	Intermediate Similarity	NPD8032	Phase 2
0.7261	Intermediate Similarity	NPD7236	Approved
0.7254	Intermediate Similarity	NPD7741	Discontinued
0.7244	Intermediate Similarity	NPD4110	Phase 3
0.7244	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6353	Approved
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7162	Intermediate Similarity	NPD4624	Approved
0.716	Intermediate Similarity	NPD7028	Phase 2
0.7153	Intermediate Similarity	NPD4626	Approved
0.7133	Intermediate Similarity	NPD7095	Approved
0.7119	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7685	Pre-registration
0.7108	Intermediate Similarity	NPD7833	Phase 2
0.7108	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7831	Phase 2
0.7083	Intermediate Similarity	NPD5691	Approved
0.7078	Intermediate Similarity	NPD7097	Phase 1
0.7075	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD37	Approved
0.707	Intermediate Similarity	NPD6674	Discontinued
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7059	Intermediate Similarity	NPD3657	Discovery
0.7048	Intermediate Similarity	NPD4967	Phase 2
0.7048	Intermediate Similarity	NPD4965	Approved
0.7048	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD7239	Suspended
0.7032	Intermediate Similarity	NPD7742	Approved
0.7032	Intermediate Similarity	NPD7743	Approved
0.7025	Intermediate Similarity	NPD4628	Phase 3
0.702	Intermediate Similarity	NPD3027	Phase 3
0.7013	Intermediate Similarity	NPD6653	Approved
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3026	Approved
0.6986	Remote Similarity	NPD3023	Approved
0.6982	Remote Similarity	NPD7199	Phase 2
0.6981	Remote Similarity	NPD8131	Suspended
0.6981	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3024	Approved
0.6966	Remote Similarity	NPD3025	Approved
0.6957	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3645	Discontinued
0.6957	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5844	Phase 1
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD4198	Discontinued
0.6918	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2861	Phase 2
0.6883	Remote Similarity	NPD1613	Approved
0.6883	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD5404	Approved
0.6879	Remote Similarity	NPD5408	Approved
0.6879	Remote Similarity	NPD5405	Approved
0.6863	Remote Similarity	NPD3764	Approved
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD230	Phase 1
0.6829	Remote Similarity	NPD1653	Approved
0.6818	Remote Similarity	NPD7240	Approved
0.6816	Remote Similarity	NPD8150	Discontinued
0.6806	Remote Similarity	NPD7157	Approved
0.6802	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4097	Suspended
0.679	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3455	Phase 2
0.6783	Remote Similarity	NPD5283	Phase 1
0.6772	Remote Similarity	NPD2935	Discontinued
0.6768	Remote Similarity	NPD5699	Approved
0.6761	Remote Similarity	NPD228	Approved
0.6757	Remote Similarity	NPD3496	Discontinued
0.6753	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6798	Discontinued
0.6746	Remote Similarity	NPD7768	Phase 2
0.6736	Remote Similarity	NPD2629	Approved
0.6735	Remote Similarity	NPD1357	Approved
0.6733	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4908	Phase 1
0.6731	Remote Similarity	NPD5124	Phase 1
0.6731	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8455	Phase 2
0.6724	Remote Similarity	NPD7473	Discontinued
0.6711	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7961	Discontinued
0.6691	Remote Similarity	NPD3020	Approved
0.6689	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD8651	Approved
0.6688	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD27	Approved
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2489	Approved
0.6667	Remote Similarity	NPD2898	Approved
0.6647	Remote Similarity	NPD7057	Phase 3
0.6647	Remote Similarity	NPD7058	Phase 2
0.6647	Remote Similarity	NPD6232	Discontinued
0.6646	Remote Similarity	NPD3638	Discontinued
0.6646	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2797	Approved
0.6643	Remote Similarity	NPD3134	Approved
0.663	Remote Similarity	NPD8434	Phase 2
0.6627	Remote Similarity	NPD7819	Suspended
0.6623	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7074	Phase 3
0.6607	Remote Similarity	NPD6677	Suspended
0.6606	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6233	Phase 2
0.66	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5536	Phase 2
0.6597	Remote Similarity	NPD7094	Approved
0.6597	Remote Similarity	NPD7843	Approved
0.6597	Remote Similarity	NPD7635	Approved
0.6597	Remote Similarity	NPD5535	Approved
0.6597	Remote Similarity	NPD6858	Approved
0.6596	Remote Similarity	NPD1358	Approved
0.6591	Remote Similarity	NPD7799	Discontinued
0.6585	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7041	Phase 2
0.6584	Remote Similarity	NPD7037	Approved
0.6582	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7680	Approved
0.6568	Remote Similarity	NPD1934	Approved
0.6561	Remote Similarity	NPD2979	Phase 3
0.6558	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7311	Approved
0.6556	Remote Similarity	NPD7313	Approved
0.6556	Remote Similarity	NPD7310	Approved
0.6556	Remote Similarity	NPD7312	Approved
0.6554	Remote Similarity	NPD7054	Approved
0.6552	Remote Similarity	NPD3051	Approved
0.6543	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3268	Approved
0.6536	Remote Similarity	NPD6362	Approved
0.6529	Remote Similarity	NPD5761	Phase 2
0.6529	Remote Similarity	NPD5760	Phase 2
0.6522	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6005	Phase 3
0.6522	Remote Similarity	NPD6004	Phase 3
0.6522	Remote Similarity	NPD6002	Phase 3
0.6522	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7309	Approved
0.6519	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7472	Approved
0.6514	Remote Similarity	NPD2969	Approved
0.6514	Remote Similarity	NPD2970	Approved
0.6512	Remote Similarity	NPD7075	Discontinued
0.651	Remote Similarity	NPD5585	Approved
0.6503	Remote Similarity	NPD7906	Approved
0.6503	Remote Similarity	NPD6331	Phase 2
0.6503	Remote Similarity	NPD3750	Approved
0.65	Remote Similarity	NPD2799	Discontinued
0.65	Remote Similarity	NPD7033	Discontinued
0.65	Remote Similarity	NPD3299	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