NPASS Compound

Structure

CID126723 OpenBabel06191715482D 36 41 0 0 1 0 0 0 0 0999 V2000 -1.6908 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8873 -1.3762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5512 -2.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8189 -2.5134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3639 -4.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2734 -0.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6999 -3.4058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9266 -1.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4837 -1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3374 -4.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5995 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.4405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8254 -4.8938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4385 -2.1500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8873 -3.2418 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 1 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 32 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 6 0 0 0 19 27 1 1 0 0 0 19 33 1 0 0 0 0 20 30 2 0 0 0 0 20 35 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 22 36 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 28 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.23
Volume:	496.008
LogP:	4.169
LogD:	2.581
LogS:	-4.626
# Rotatable Bonds:	3
TPSA:	104.57
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.658
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.352
MDCK Permeability:	1.385295490763383e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.457
Plasma Protein Binding (PPB):	88.66329193115234%
Volume Distribution (VD):	2.081
Pgp-substrate:	13.539595603942871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.39
CYP2C19-substrate:	0.493
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	6.016
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.845
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.331
Carcinogencity:	0.11
Eye Corrosion:	0.384
Eye Irritation:	0.352
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC126723

Natural Product ID:	NPC126723
*Common Name:**	VGEVFODMPBFOHX-OLMYNIEVSA-N
IUPAC Name:	n.a.
Synonyms:	7Alpha-Obacunyl Acetate
Standard InCHIKey:	VGEVFODMPBFOHX-OLMYNIEVSA-N
Standard InCHI:	InChI=1S/C28H34O8/c1-15(29)33-19-13-18-24(2,3)35-20(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,36-22)27(17,19)6/h8-10,12,14,17-19,21-22H,7,11,13H2,1-6H3/t17-,18+,19-,21+,22-,25-,26+,27+,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)OC(=O)C=C[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)O[C@H]([C@@]3(CC2)C)c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928575
PubChem CID:	57390140
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11473427]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18198838]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[21985060]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29135252]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5799	Streptomyces chryseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1329	Esenbeckia hartmanii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5451	Ageratina saltillensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11119	Salta triflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7966	Grewia villosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3560	Trifolium montanum	Species	Fabaceae	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	2
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[488815]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	=	9.3	ug.mL-1	PMID[488815]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	=	45.0	ug.mL-1	PMID[488815]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	>	125.0	ug.mL-1	PMID[488815]

☑ 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 NPC126723 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	424
0.1-0.2	1542
0.2-0.3	3382
0.3-0.4	6259
0.4-0.5	10850
0.5-0.6	9932
0.6-0.7	8858
0.7-0.8	1075
0.8-0.85	241
0.85-0.9	84
0.9-0.95	41
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC286722
0.9603	High Similarity	NPC475295
0.9603	High Similarity	NPC473473
0.9603	High Similarity	NPC237155
0.96	High Similarity	NPC209364
0.96	High Similarity	NPC107646
0.96	High Similarity	NPC263265
0.9539	High Similarity	NPC475381
0.9539	High Similarity	NPC472653
0.9481	High Similarity	NPC476860
0.9477	High Similarity	NPC470939
0.9419	High Similarity	NPC23387
0.9416	High Similarity	NPC39986
0.9416	High Similarity	NPC469846
0.9416	High Similarity	NPC134254
0.9416	High Similarity	NPC302369
0.9412	High Similarity	NPC25255
0.9412	High Similarity	NPC335761
0.9359	High Similarity	NPC472651
0.9359	High Similarity	NPC476853
0.9355	High Similarity	NPC476856
0.9355	High Similarity	NPC476857
0.9355	High Similarity	NPC476858
0.9351	High Similarity	NPC193798
0.9351	High Similarity	NPC5079
0.9342	High Similarity	NPC60973
0.9333	High Similarity	NPC18135
0.9299	High Similarity	NPC472652
0.929	High Similarity	NPC51568
0.929	High Similarity	NPC234660
0.9286	High Similarity	NPC305016
0.9281	High Similarity	NPC472283
0.9272	High Similarity	NPC476201
0.9236	High Similarity	NPC473753
0.9236	High Similarity	NPC473766
0.9236	High Similarity	NPC476850
0.9236	High Similarity	NPC476861
0.9231	High Similarity	NPC123088
0.9195	High Similarity	NPC470941
0.9195	High Similarity	NPC221809
0.9177	High Similarity	NPC271235
0.9156	High Similarity	NPC45101
0.9156	High Similarity	NPC167142
0.915	High Similarity	NPC469850
0.915	High Similarity	NPC476262
0.9139	High Similarity	NPC476122
0.9122	High Similarity	NPC86935
0.9114	High Similarity	NPC173516
0.9114	High Similarity	NPC472282
0.9103	High Similarity	NPC117986
0.9103	High Similarity	NPC96443
0.9103	High Similarity	NPC82851
0.9103	High Similarity	NPC290400
0.9097	High Similarity	NPC477403
0.9057	High Similarity	NPC160651
0.9057	High Similarity	NPC471397
0.9045	High Similarity	NPC469338
0.9045	High Similarity	NPC476197
0.9045	High Similarity	NPC477405
0.9045	High Similarity	NPC292389
0.9038	High Similarity	NPC191828
0.9032	High Similarity	NPC187149
0.9032	High Similarity	NPC299038
0.9032	High Similarity	NPC249021
0.9026	High Similarity	NPC44675
0.9026	High Similarity	NPC214541
0.9013	High Similarity	NPC196864
0.9013	High Similarity	NPC159927
0.9013	High Similarity	NPC469335
0.9013	High Similarity	NPC477404
0.9	High Similarity	NPC302392
0.9	High Similarity	NPC262198
0.8994	High Similarity	NPC472774
0.8994	High Similarity	NPC472775
0.8987	High Similarity	NPC469849
0.8987	High Similarity	NPC276551
0.8987	High Similarity	NPC271657
0.8987	High Similarity	NPC470940
0.8981	High Similarity	NPC69028
0.8981	High Similarity	NPC472771
0.8981	High Similarity	NPC472668
0.8981	High Similarity	NPC149896
0.8981	High Similarity	NPC18347
0.8981	High Similarity	NPC329938
0.8974	High Similarity	NPC475967
0.8961	High Similarity	NPC282445
0.8931	High Similarity	NPC470875
0.8924	High Similarity	NPC472773
0.8917	High Similarity	NPC477402
0.891	High Similarity	NPC472772
0.891	High Similarity	NPC261597
0.891	High Similarity	NPC36655
0.8896	High Similarity	NPC469503
0.8889	High Similarity	NPC156189
0.8889	High Similarity	NPC46551
0.8861	High Similarity	NPC263432
0.8861	High Similarity	NPC200782
0.8861	High Similarity	NPC197596
0.8854	High Similarity	NPC473368
0.8839	High Similarity	NPC57998
0.8824	High Similarity	NPC470791
0.8824	High Similarity	NPC470790
0.882	High Similarity	NPC327922
0.8805	High Similarity	NPC472669
0.8797	High Similarity	NPC470789
0.8782	High Similarity	NPC469336
0.8782	High Similarity	NPC264943
0.8773	High Similarity	NPC469848
0.8765	High Similarity	NPC470995
0.8765	High Similarity	NPC82602
0.8758	High Similarity	NPC476224
0.875	High Similarity	NPC470182
0.8742	High Similarity	NPC6326
0.8734	High Similarity	NPC307383
0.8726	High Similarity	NPC469485
0.8718	High Similarity	NPC178932
0.8716	High Similarity	NPC476943
0.8712	High Similarity	NPC160818
0.8712	High Similarity	NPC169299
0.8712	High Similarity	NPC159232
0.8696	High Similarity	NPC478178
0.8693	High Similarity	NPC255414
0.8671	High Similarity	NPC173544
0.8667	High Similarity	NPC262386
0.8654	High Similarity	NPC268905
0.8654	High Similarity	NPC75906
0.8654	High Similarity	NPC44577
0.8649	High Similarity	NPC310830
0.8636	High Similarity	NPC19747
0.8625	High Similarity	NPC188649
0.8625	High Similarity	NPC207978
0.8625	High Similarity	NPC471166
0.8625	High Similarity	NPC471167
0.8625	High Similarity	NPC211777
0.8618	High Similarity	NPC476944
0.8616	High Similarity	NPC474932
0.8609	High Similarity	NPC121158
0.8608	High Similarity	NPC204663
0.8606	High Similarity	NPC236004
0.8599	High Similarity	NPC30222
0.8581	High Similarity	NPC195325
0.8581	High Similarity	NPC69647
0.8581	High Similarity	NPC472654
0.8581	High Similarity	NPC125182
0.858	High Similarity	NPC97574
0.858	High Similarity	NPC472141
0.858	High Similarity	NPC93172
0.858	High Similarity	NPC475779
0.8571	High Similarity	NPC472139
0.8571	High Similarity	NPC224394
0.8571	High Similarity	NPC88841
0.8571	High Similarity	NPC198047
0.8571	High Similarity	NPC471168
0.8571	High Similarity	NPC288602
0.8571	High Similarity	NPC663
0.8553	High Similarity	NPC472776
0.8553	High Similarity	NPC472777
0.8553	High Similarity	NPC472778
0.8553	High Similarity	NPC223415
0.8553	High Similarity	NPC195131
0.8544	High Similarity	NPC35000
0.8544	High Similarity	NPC281258
0.8537	High Similarity	NPC472659
0.8535	High Similarity	NPC84063
0.8535	High Similarity	NPC182427
0.8535	High Similarity	NPC29695
0.8528	High Similarity	NPC478179
0.8506	High Similarity	NPC346
0.8503	High Similarity	NPC478177
0.85	High Similarity	NPC475226
0.8497	Intermediate Similarity	NPC251865
0.8497	Intermediate Similarity	NPC142113
0.8494	Intermediate Similarity	NPC94763
0.8467	Intermediate Similarity	NPC220094
0.8466	Intermediate Similarity	NPC149945
0.8462	Intermediate Similarity	NPC471001
0.8457	Intermediate Similarity	NPC476035
0.8457	Intermediate Similarity	NPC165218
0.8457	Intermediate Similarity	NPC14499
0.8457	Intermediate Similarity	NPC419
0.8457	Intermediate Similarity	NPC475039
0.8452	Intermediate Similarity	NPC250228
0.8452	Intermediate Similarity	NPC71821
0.8442	Intermediate Similarity	NPC41182
0.8438	Intermediate Similarity	NPC88007
0.8438	Intermediate Similarity	NPC195954
0.8431	Intermediate Similarity	NPC243577
0.8431	Intermediate Similarity	NPC470741
0.8431	Intermediate Similarity	NPC80635
0.8421	Intermediate Similarity	NPC20500
0.8418	Intermediate Similarity	NPC322546
0.8418	Intermediate Similarity	NPC147168
0.8418	Intermediate Similarity	NPC308205
0.8415	Intermediate Similarity	NPC472764
0.8415	Intermediate Similarity	NPC100333
0.8405	Intermediate Similarity	NPC276735
0.8405	Intermediate Similarity	NPC261184
0.8405	Intermediate Similarity	NPC146991
0.8402	Intermediate Similarity	NPC470938
0.84	Intermediate Similarity	NPC310043

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 NPC126723 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	1040
0.2-0.3	2219
0.3-0.4	2681
0.4-0.5	1812
0.5-0.6	774
0.6-0.7	256
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8313	Intermediate Similarity	NPD5760	Phase 2
0.8313	Intermediate Similarity	NPD5761	Phase 2
0.8221	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD8434	Phase 2
0.76	Intermediate Similarity	NPD6764	Approved
0.76	Intermediate Similarity	NPD6765	Approved
0.7545	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.747	Intermediate Similarity	NPD6599	Discontinued
0.743	Intermediate Similarity	NPD6784	Approved
0.743	Intermediate Similarity	NPD6785	Approved
0.7368	Intermediate Similarity	NPD919	Approved
0.7337	Intermediate Similarity	NPD7819	Suspended
0.7326	Intermediate Similarity	NPD5494	Approved
0.7289	Intermediate Similarity	NPD920	Approved
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7212	Intermediate Similarity	NPD6799	Approved
0.7207	Intermediate Similarity	NPD6559	Discontinued
0.7193	Intermediate Similarity	NPD3817	Phase 2
0.7184	Intermediate Similarity	NPD1247	Approved
0.7169	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5402	Approved
0.7048	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8404	Phase 2
0.7011	Intermediate Similarity	NPD3749	Approved
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.6994	Remote Similarity	NPD2796	Approved
0.6982	Remote Similarity	NPD5403	Approved
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5401	Approved
0.6962	Remote Similarity	NPD6832	Phase 2
0.6954	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3882	Suspended
0.6951	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7473	Discontinued
0.6919	Remote Similarity	NPD7411	Suspended
0.6901	Remote Similarity	NPD3226	Approved
0.6897	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8127	Discontinued
0.6889	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3751	Discontinued
0.6889	Remote Similarity	NPD7799	Discontinued
0.6867	Remote Similarity	NPD1243	Approved
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.686	Remote Similarity	NPD4380	Phase 2
0.6854	Remote Similarity	NPD3787	Discontinued
0.6854	Remote Similarity	NPD6232	Discontinued
0.6852	Remote Similarity	NPD6355	Discontinued
0.6848	Remote Similarity	NPD8313	Approved
0.6848	Remote Similarity	NPD8312	Approved
0.6848	Remote Similarity	NPD2346	Discontinued
0.6845	Remote Similarity	NPD7236	Approved
0.6839	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2799	Discontinued
0.6828	Remote Similarity	NPD8150	Discontinued
0.6824	Remote Similarity	NPD6273	Approved
0.6823	Remote Similarity	NPD8285	Discontinued
0.6818	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3818	Discontinued
0.6793	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4107	Approved
0.6786	Remote Similarity	NPD3887	Approved
0.6784	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1934	Approved
0.6778	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6166	Phase 2
0.6776	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7435	Discontinued
0.6766	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7239	Suspended
0.6739	Remote Similarity	NPD7685	Pre-registration
0.6739	Remote Similarity	NPD7251	Discontinued
0.6727	Remote Similarity	NPD3748	Approved
0.6725	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8407	Phase 2
0.6707	Remote Similarity	NPD1549	Phase 2
0.6705	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7458	Discontinued
0.6704	Remote Similarity	NPD6959	Discontinued
0.6703	Remote Similarity	NPD7808	Phase 3
0.6687	Remote Similarity	NPD6099	Approved
0.6687	Remote Similarity	NPD6100	Approved
0.6687	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD37	Approved
0.6685	Remote Similarity	NPD6797	Phase 2
0.6685	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD4482	Phase 3
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8368	Discontinued
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1933	Approved
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7074	Phase 3
0.6627	Remote Similarity	NPD7033	Discontinued
0.6626	Remote Similarity	NPD8032	Phase 2
0.6607	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7095	Approved
0.6603	Remote Similarity	NPD17	Approved
0.6593	Remote Similarity	NPD2403	Approved
0.6593	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6234	Discontinued
0.6587	Remote Similarity	NPD2438	Suspended
0.6587	Remote Similarity	NPD2935	Discontinued
0.6585	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4307	Phase 2
0.6576	Remote Similarity	NPD7054	Approved
0.6575	Remote Similarity	NPD7229	Phase 3
0.6575	Remote Similarity	NPD6808	Phase 2
0.657	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7907	Approved
0.6568	Remote Similarity	NPD2800	Approved
0.6567	Remote Similarity	NPD7874	Approved
0.6567	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7097	Phase 1
0.6564	Remote Similarity	NPD2313	Discontinued
0.6564	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6798	Discontinued
0.6554	Remote Similarity	NPD2801	Approved
0.6554	Remote Similarity	NPD1465	Phase 2
0.6548	Remote Similarity	NPD2353	Approved
0.6548	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2344	Approved
0.6541	Remote Similarity	NPD7472	Approved
0.6531	Remote Similarity	NPD6781	Approved
0.6531	Remote Similarity	NPD6779	Approved
0.6531	Remote Similarity	NPD6780	Approved
0.6531	Remote Similarity	NPD6776	Approved
0.6531	Remote Similarity	NPD6782	Approved
0.6531	Remote Similarity	NPD6777	Approved
0.6531	Remote Similarity	NPD6778	Approved
0.6529	Remote Similarity	NPD3750	Approved
0.6524	Remote Similarity	NPD6233	Phase 2
0.6522	Remote Similarity	NPD7228	Approved
0.6519	Remote Similarity	NPD7199	Phase 2
0.6519	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5353	Approved
0.6515	Remote Similarity	NPD7697	Approved
0.6515	Remote Similarity	NPD7696	Phase 3
0.6515	Remote Similarity	NPD7698	Approved
0.6509	Remote Similarity	NPD2897	Discontinued
0.6507	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6190	Approved
0.6484	Remote Similarity	NPD5710	Approved
0.6484	Remote Similarity	NPD5711	Approved
0.6482	Remote Similarity	NPD7871	Phase 2
0.6482	Remote Similarity	NPD8320	Phase 1
0.6482	Remote Similarity	NPD7870	Phase 2
0.6482	Remote Similarity	NPD8319	Approved
0.6478	Remote Similarity	NPD1608	Approved
0.6478	Remote Similarity	NPD3972	Approved
0.6473	Remote Similarity	NPD4111	Phase 1
0.6463	Remote Similarity	NPD3764	Approved
0.6461	Remote Similarity	NPD8455	Phase 2
0.646	Remote Similarity	NPD3267	Approved
0.646	Remote Similarity	NPD3266	Approved
0.6446	Remote Similarity	NPD447	Suspended
0.6441	Remote Similarity	NPD6385	Approved
0.6441	Remote Similarity	NPD6386	Approved
0.6441	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1512	Approved
0.6433	Remote Similarity	NPD4110	Phase 3
0.6433	Remote Similarity	NPD7003	Approved
0.6433	Remote Similarity	NPD5585	Approved
0.6433	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7497	Discontinued
0.6429	Remote Similarity	NPD1510	Phase 2
0.6429	Remote Similarity	NPD4308	Phase 3
0.6425	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1019	Discontinued
0.6416	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8435	Approved
0.6395	Remote Similarity	NPD2354	Approved
0.6395	Remote Similarity	NPD2309	Approved
0.6394	Remote Similarity	NPD4665	Approved
0.6389	Remote Similarity	NPD7057	Phase 3
0.6389	Remote Similarity	NPD7058	Phase 2
0.6387	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7701	Phase 2
0.6386	Remote Similarity	NPD2979	Phase 3

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