NPASS Compound

Structure

NPC100333 OpenBabel07101719522D 49 54 0 0 1 0 0 0 0 0999 V2000 -4.2575 -1.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9477 1.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1383 2.6742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1031 -1.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3619 -0.2235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1371 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7615 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2167 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0158 0.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -1.0933 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6548 0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7570 -0.2929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4300 -0.7412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9817 0.9319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 -5.9136 1.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5329 0.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6888 0.2247 0.0000 C 0 0 2 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 6.0622 -1.5000 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 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -5.2065 2.1566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5669 0.8024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8795 1.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7167 -1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1452 1.1560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 43 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 20 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 44 1 0 0 0 0 9 16 1 0 0 0 0 9 21 1 0 0 0 0 10 32 1 0 0 0 0 11 34 1 0 0 0 0 12 14 2 0 0 0 0 12 44 1 0 0 0 0 13 45 1 0 0 0 0 14 17 1 0 0 0 0 15 28 1 0 0 0 0 15 33 1 0 0 0 0 16 29 1 0 0 0 0 16 32 1 1 0 0 0 17 10 1 1 0 0 0 17 46 1 0 0 0 0 18 11 1 1 0 0 0 18 22 1 0 0 0 0 18 47 1 0 0 0 0 19 13 1 1 0 0 0 19 23 1 0 0 0 0 19 48 1 0 0 0 0 20 32 1 6 0 0 0 20 33 1 0 0 0 0 21 33 1 1 0 0 0 21 49 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 25 1 0 0 0 0 23 36 1 6 0 0 0 24 26 1 0 0 0 0 24 37 1 1 0 0 0 25 27 1 0 0 0 0 25 38 1 1 0 0 0 26 30 1 0 0 0 0 26 39 1 6 0 0 0 27 31 1 0 0 0 0 27 40 1 6 0 0 0 28 41 2 0 0 0 0 28 43 1 0 0 0 0 29 42 2 0 0 0 0 29 49 1 0 0 0 0 30 45 1 1 0 0 0 30 47 1 0 0 0 0 31 46 1 1 0 0 0 31 48 1 0 0 0 0 32 1 1 6 0 0 0 33 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	698.28
Volume:	655.447
LogP:	0.338
LogD:	-0.15
LogS:	-3.093
# Rotatable Bonds:	11
TPSA:	244.27
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	6.49
Fsp3:	0.758
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:	-6.263
MDCK Permeability:	0.00017458110232837498
Pgp-inhibitor:	0.706
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.984
20% Bioavailability (F20%):	0.481
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	61.705135345458984%
Volume Distribution (VD):	0.527
Pgp-substrate:	19.341514587402344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	1.16
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.126
Carcinogencity:	0.759
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC100333

Natural Product ID:	NPC100333
*Common Name:**	Borapetoside D
IUPAC Name:	n.a.
Synonyms:	Borapetoside D
Standard InCHIKey:	RDANOZJKKFLLEO-KBAPQYMASA-N
Standard InCHI:	InChI=1S/C33H46O16/c1-32(16-9-21(49-29(16)42)33(2)15(28(41)43-3)5-4-6-20(32)33)10-17(14-7-8-44-12-14)46-31-27(40)25(38)23(36)19(48-31)13-45-30-26(39)24(37)22(35)18(11-34)47-30/h5,7-8,12,16-27,30-31,34-40H,4,6,9-11,13H2,1-3H3/t16-,17+,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,30+,31+,32+,33-/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](c3cocc3)C[C@]3(C)[C@H]4C[C@@H]([C@@]5([C@H]3CCC=C5C(=O)OC)C)OC4=O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097582
PubChem CID:	46886851
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO26700	Tinospora crispa	Species	Menispermaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[468689]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	10000.0	nM	PMID[468689]

☑ 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 NPC100333 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	349
0.1-0.2	1347
0.2-0.3	3095
0.3-0.4	5239
0.4-0.5	9489
0.5-0.6	10140
0.6-0.7	9802
0.7-0.8	2732
0.8-0.85	316
0.85-0.9	142
0.9-0.95	36
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9742	High Similarity	NPC211777
0.9679	High Similarity	NPC198047
0.9563	High Similarity	NPC160818
0.9563	High Similarity	NPC169299
0.95	High Similarity	NPC82602
0.949	High Similarity	NPC207978
0.9487	High Similarity	NPC262872
0.9434	High Similarity	NPC97574
0.9434	High Similarity	NPC93172
0.929	High Similarity	NPC476939
0.929	High Similarity	NPC476940
0.9241	High Similarity	NPC307383
0.913	High Similarity	NPC470182
0.9057	High Similarity	NPC472776
0.9057	High Similarity	NPC472778
0.9057	High Similarity	NPC472777
0.9051	High Similarity	NPC44675
0.9051	High Similarity	NPC214541
0.9045	High Similarity	NPC469503
0.9036	High Similarity	NPC262386
0.9032	High Similarity	NPC476941
0.9032	High Similarity	NPC7388
0.9032	High Similarity	NPC476942
0.9012	High Similarity	NPC146991
0.9006	High Similarity	NPC200782
0.9006	High Similarity	NPC69028
0.8968	High Similarity	NPC476937
0.8968	High Similarity	NPC476938
0.8957	High Similarity	NPC472141
0.8957	High Similarity	NPC470875
0.8951	High Similarity	NPC477405
0.8951	High Similarity	NPC472139
0.8938	High Similarity	NPC36655
0.8938	High Similarity	NPC261597
0.8938	High Similarity	NPC45101
0.8931	High Similarity	NPC35000
0.8931	High Similarity	NPC469336
0.8924	High Similarity	NPC147168
0.8896	High Similarity	NPC276551
0.8896	High Similarity	NPC469849
0.8882	High Similarity	NPC475967
0.8868	High Similarity	NPC57998
0.8868	High Similarity	NPC178932
0.8868	High Similarity	NPC282445
0.8868	High Similarity	NPC30222
0.8848	High Similarity	NPC472652
0.8848	High Similarity	NPC271235
0.8846	High Similarity	NPC250228
0.8841	High Similarity	NPC472670
0.8841	High Similarity	NPC307781
0.8834	High Similarity	NPC292389
0.8834	High Similarity	NPC419
0.8834	High Similarity	NPC469338
0.8827	High Similarity	NPC477402
0.882	High Similarity	NPC299038
0.882	High Similarity	NPC187149
0.8812	High Similarity	NPC264943
0.8812	High Similarity	NPC476262
0.8805	High Similarity	NPC476201
0.8797	High Similarity	NPC476936
0.8788	High Similarity	NPC472282
0.8788	High Similarity	NPC472651
0.878	High Similarity	NPC470940
0.878	High Similarity	NPC271657
0.8773	High Similarity	NPC5079
0.8773	High Similarity	NPC82851
0.8773	High Similarity	NPC149896
0.8765	High Similarity	NPC475226
0.8735	High Similarity	NPC471397
0.8735	High Similarity	NPC472673
0.8734	High Similarity	NPC195325
0.872	High Similarity	NPC302369
0.872	High Similarity	NPC234660
0.872	High Similarity	NPC472773
0.872	High Similarity	NPC51568
0.872	High Similarity	NPC39986
0.872	High Similarity	NPC134254
0.8712	High Similarity	NPC472653
0.8712	High Similarity	NPC335761
0.8704	High Similarity	NPC472283
0.8704	High Similarity	NPC249021
0.8688	High Similarity	NPC44577
0.8679	High Similarity	NPC476122
0.8679	High Similarity	NPC469335
0.8679	High Similarity	NPC159927
0.8675	High Similarity	NPC476850
0.8675	High Similarity	NPC173516
0.8675	High Similarity	NPC476861
0.8667	High Similarity	NPC123088
0.8662	High Similarity	NPC346
0.8659	High Similarity	NPC472771
0.8659	High Similarity	NPC18347
0.8659	High Similarity	NPC329938
0.8659	High Similarity	NPC263432
0.8659	High Similarity	NPC117986
0.8659	High Similarity	NPC470792
0.8655	High Similarity	NPC470938
0.865	High Similarity	NPC477403
0.8625	High Similarity	NPC18135
0.8623	High Similarity	NPC160651
0.8616	High Similarity	NPC472654
0.8608	High Similarity	NPC470941
0.8606	High Similarity	NPC469846
0.8598	High Similarity	NPC470789
0.8589	High Similarity	NPC197137
0.8589	High Similarity	NPC286722
0.8589	High Similarity	NPC173544
0.8589	High Similarity	NPC472772
0.858	High Similarity	NPC141538
0.858	High Similarity	NPC296807
0.858	High Similarity	NPC281258
0.858	High Similarity	NPC155939
0.858	High Similarity	NPC469850
0.8563	High Similarity	NPC472774
0.8563	High Similarity	NPC472775
0.8562	High Similarity	NPC196864
0.8562	High Similarity	NPC477404
0.8554	High Similarity	NPC476857
0.8554	High Similarity	NPC476858
0.8554	High Similarity	NPC476856
0.8545	High Similarity	NPC96443
0.8545	High Similarity	NPC290400
0.8537	High Similarity	NPC472779
0.8537	High Similarity	NPC475295
0.8537	High Similarity	NPC473473
0.8537	High Similarity	NPC472671
0.8535	High Similarity	NPC476944
0.8529	High Similarity	NPC94763
0.8528	High Similarity	NPC469485
0.8528	High Similarity	NPC209364
0.8521	High Similarity	NPC159232
0.8519	High Similarity	NPC253201
0.8519	High Similarity	NPC302054
0.8506	High Similarity	NPC242068
0.8506	High Similarity	NPC247563
0.8503	High Similarity	NPC475779
0.8503	High Similarity	NPC214600
0.85	High Similarity	NPC125182
0.85	High Similarity	NPC69647
0.8494	Intermediate Similarity	NPC165218
0.8491	Intermediate Similarity	NPC10088
0.8491	Intermediate Similarity	NPC221809
0.8488	Intermediate Similarity	NPC11062
0.8485	Intermediate Similarity	NPC305016
0.8485	Intermediate Similarity	NPC25255
0.8481	Intermediate Similarity	NPC41182
0.8476	Intermediate Similarity	NPC214495
0.8476	Intermediate Similarity	NPC475066
0.8476	Intermediate Similarity	NPC470118
0.8476	Intermediate Similarity	NPC167142
0.8476	Intermediate Similarity	NPC470119
0.8471	Intermediate Similarity	NPC223415
0.8466	Intermediate Similarity	NPC92979
0.8457	Intermediate Similarity	NPC472672
0.8457	Intermediate Similarity	NPC33938
0.8457	Intermediate Similarity	NPC268905
0.8457	Intermediate Similarity	NPC75906
0.8452	Intermediate Similarity	NPC476853
0.8447	Intermediate Similarity	NPC470997
0.8443	Intermediate Similarity	NPC472664
0.8434	Intermediate Similarity	NPC188649
0.8434	Intermediate Similarity	NPC193798
0.8424	Intermediate Similarity	NPC474611
0.8421	Intermediate Similarity	NPC236004
0.8421	Intermediate Similarity	NPC477824
0.8418	Intermediate Similarity	NPC137295
0.8418	Intermediate Similarity	NPC251865
0.8415	Intermediate Similarity	NPC107646
0.8415	Intermediate Similarity	NPC126723
0.8412	Intermediate Similarity	NPC475641
0.8412	Intermediate Similarity	NPC475237
0.8405	Intermediate Similarity	NPC237259
0.8405	Intermediate Similarity	NPC98206
0.8405	Intermediate Similarity	NPC34421
0.8402	Intermediate Similarity	NPC472766
0.8402	Intermediate Similarity	NPC472765
0.84	Intermediate Similarity	NPC105395
0.8395	Intermediate Similarity	NPC471000
0.8393	Intermediate Similarity	NPC478178
0.8393	Intermediate Similarity	NPC23387
0.8385	Intermediate Similarity	NPC234494
0.8383	Intermediate Similarity	NPC288602
0.8383	Intermediate Similarity	NPC476197
0.8383	Intermediate Similarity	NPC88841
0.8375	Intermediate Similarity	NPC471174
0.8375	Intermediate Similarity	NPC255414
0.8373	Intermediate Similarity	NPC191828
0.8373	Intermediate Similarity	NPC475381
0.8354	Intermediate Similarity	NPC470741
0.8353	Intermediate Similarity	NPC472659
0.8343	Intermediate Similarity	NPC472764
0.8333	Intermediate Similarity	NPC476860
0.8333	Intermediate Similarity	NPC90953
0.8333	Intermediate Similarity	NPC196846
0.8324	Intermediate Similarity	NPC478177
0.8324	Intermediate Similarity	NPC472665
0.8323	Intermediate Similarity	NPC470939
0.8323	Intermediate Similarity	NPC310830
0.8323	Intermediate Similarity	NPC472767
0.8314	Intermediate Similarity	NPC471632

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 NPC100333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	937
0.2-0.3	2167
0.3-0.4	2659
0.4-0.5	1937
0.5-0.6	843
0.6-0.7	270
0.7-0.8	38
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD5761	Phase 2
0.8242	Intermediate Similarity	NPD5760	Phase 2
0.8136	Intermediate Similarity	NPD8434	Phase 2
0.7765	Intermediate Similarity	NPD8312	Approved
0.7765	Intermediate Similarity	NPD8313	Approved
0.7753	Intermediate Similarity	NPD6559	Discontinued
0.7733	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7228	Approved
0.7399	Intermediate Similarity	NPD8455	Phase 2
0.7363	Intermediate Similarity	NPD7240	Approved
0.7363	Intermediate Similarity	NPD6764	Approved
0.7363	Intermediate Similarity	NPD6765	Approved
0.7348	Intermediate Similarity	NPD7472	Approved
0.7348	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD7799	Discontinued
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7322	Intermediate Similarity	NPD7808	Phase 3
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7299	Intermediate Similarity	NPD7819	Suspended
0.7297	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7054	Approved
0.7268	Intermediate Similarity	NPD7251	Discontinued
0.7264	Intermediate Similarity	NPD8404	Phase 2
0.7216	Intermediate Similarity	NPD4966	Approved
0.7216	Intermediate Similarity	NPD4967	Phase 2
0.7216	Intermediate Similarity	NPD4965	Approved
0.7213	Intermediate Similarity	NPD6797	Phase 2
0.7204	Intermediate Similarity	NPD6784	Approved
0.7204	Intermediate Similarity	NPD6785	Approved
0.72	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7075	Discontinued
0.7174	Intermediate Similarity	NPD7685	Pre-registration
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7095	Intermediate Similarity	NPD5494	Approved
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7056	Intermediate Similarity	NPD7199	Phase 2
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7053	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD37	Approved
0.7035	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4380	Phase 2
0.7029	Intermediate Similarity	NPD6599	Discontinued
0.7022	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7783	Phase 2
0.7011	Intermediate Similarity	NPD5844	Phase 1
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD8151	Discontinued
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8407	Phase 2
0.6966	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD920	Approved
0.6949	Remote Similarity	NPD6801	Discontinued
0.6935	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7696	Phase 3
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD7697	Approved
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8368	Discontinued
0.6897	Remote Similarity	NPD6273	Approved
0.6895	Remote Similarity	NPD8150	Discontinued
0.6893	Remote Similarity	NPD7411	Suspended
0.6889	Remote Similarity	NPD3749	Approved
0.6885	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8320	Phase 1
0.6884	Remote Similarity	NPD8319	Approved
0.6881	Remote Similarity	NPD7874	Approved
0.6881	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5402	Approved
0.6866	Remote Similarity	NPD7701	Phase 2
0.6865	Remote Similarity	NPD3751	Discontinued
0.6853	Remote Similarity	NPD6780	Approved
0.6853	Remote Similarity	NPD6782	Approved
0.6853	Remote Similarity	NPD6777	Approved
0.6853	Remote Similarity	NPD6778	Approved
0.6853	Remote Similarity	NPD6779	Approved
0.6853	Remote Similarity	NPD6776	Approved
0.6853	Remote Similarity	NPD6781	Approved
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6839	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD2532	Approved
0.6839	Remote Similarity	NPD2533	Approved
0.6834	Remote Similarity	NPD7680	Approved
0.6828	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7473	Discontinued
0.68	Remote Similarity	NPD7870	Phase 2
0.68	Remote Similarity	NPD7871	Phase 2
0.6782	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6799	Approved
0.678	Remote Similarity	NPD3226	Approved
0.678	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3817	Phase 2
0.6776	Remote Similarity	NPD6959	Discontinued
0.6766	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5403	Approved
0.676	Remote Similarity	NPD1934	Approved
0.6758	Remote Similarity	NPD919	Approved
0.6757	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7700	Phase 2
0.6751	Remote Similarity	NPD7699	Phase 2
0.6748	Remote Similarity	NPD7930	Approved
0.6743	Remote Similarity	NPD5401	Approved
0.674	Remote Similarity	NPD7768	Phase 2
0.6739	Remote Similarity	NPD6232	Discontinued
0.6739	Remote Similarity	NPD3787	Discontinued
0.6725	Remote Similarity	NPD2346	Discontinued
0.6724	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD1465	Phase 2
0.6717	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6823	Phase 2
0.6683	Remote Similarity	NPD7999	Approved
0.6648	Remote Similarity	NPD3882	Suspended
0.6647	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7097	Phase 1
0.6647	Remote Similarity	NPD2800	Approved
0.6646	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7236	Approved
0.6628	Remote Similarity	NPD7266	Discontinued
0.6609	Remote Similarity	NPD3750	Approved
0.6609	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2799	Discontinued
0.6599	Remote Similarity	NPD6534	Approved
0.6599	Remote Similarity	NPD6535	Approved
0.6596	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD1247	Approved
0.659	Remote Similarity	NPD1549	Phase 2
0.659	Remote Similarity	NPD970	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2796	Approved
0.657	Remote Similarity	NPD1551	Phase 2
0.6564	Remote Similarity	NPD8360	Approved
0.6564	Remote Similarity	NPD8435	Approved
0.6564	Remote Similarity	NPD8361	Approved
0.6557	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7907	Approved
0.6556	Remote Similarity	NPD7028	Phase 2
0.6554	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1243	Approved
0.6552	Remote Similarity	NPD6674	Discontinued
0.6545	Remote Similarity	NPD7319	Approved
0.6538	Remote Similarity	NPD2801	Approved
0.6536	Remote Similarity	NPD7239	Suspended
0.6536	Remote Similarity	NPD1653	Approved
0.6532	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1471	Phase 3
0.6532	Remote Similarity	NPD6002	Phase 3
0.6532	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6005	Phase 3
0.6532	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6004	Phase 3
0.6529	Remote Similarity	NPD6355	Discontinued
0.6529	Remote Similarity	NPD1933	Approved
0.6527	Remote Similarity	NPD6832	Phase 2
0.6522	Remote Similarity	NPD8513	Phase 3
0.6522	Remote Similarity	NPD8517	Approved
0.6522	Remote Similarity	NPD8515	Approved
0.6522	Remote Similarity	NPD8516	Approved
0.6512	Remote Similarity	NPD3748	Approved
0.6512	Remote Similarity	NPD7033	Discontinued
0.6502	Remote Similarity	NPD7497	Discontinued
0.6488	Remote Similarity	NPD7583	Approved
0.6488	Remote Similarity	NPD7584	Approved
0.6488	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6099	Approved
0.6474	Remote Similarity	NPD2935	Discontinued
0.6474	Remote Similarity	NPD6100	Approved
0.6471	Remote Similarity	NPD5711	Approved
0.6471	Remote Similarity	NPD7229	Phase 3
0.6471	Remote Similarity	NPD5710	Approved
0.6465	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6212	Phase 3
0.6465	Remote Similarity	NPD6213	Phase 3
0.6463	Remote Similarity	NPD7507	Approved
0.6462	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4665	Approved
0.6462	Remote Similarity	NPD4111	Phase 1
0.6461	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7585	Approved
0.6453	Remote Similarity	NPD3057	Approved
0.645	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2313	Discontinued
0.6442	Remote Similarity	NPD8328	Phase 3
0.6437	Remote Similarity	NPD5763	Approved
0.6437	Remote Similarity	NPD5762	Approved
0.6437	Remote Similarity	NPD2344	Approved
0.6436	Remote Similarity	NPD3926	Phase 2
0.6436	Remote Similarity	NPD4107	Approved
0.6433	Remote Similarity	NPD447	Suspended

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