NPASS Compound

Structure

NPC471482 OpenBabel07101719132D 35 39 0 0 1 0 0 0 0 0999 V2000 5.2693 3.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0103 6.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2672 6.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9330 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0670 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6244 2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6244 -0.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0670 1.6160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9310 4.7043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6220 3.7532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5699 1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9092 4.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9821 0.4410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2912 3.0101 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9821 2.0590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1651 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4330 0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 -0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4330 0.7500 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.2182 5.8632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0311 1.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0311 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2990 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4330 -0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1651 -1.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1964 6.0712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0670 1.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 15 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 20 1 1 1 0 0 0 20 21 1 0 0 0 0 21 28 1 1 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 30 1 1 0 0 0 23 31 1 0 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 30 1 0 0 0 0 25 34 1 0 0 0 0 25 35 1 0 0 0 0 26 33 1 0 0 0 0 27 31 1 0 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 19 1 6 0 0 0 31 17 1 1 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.37
Volume:	531.838
LogP:	5.531
LogD:	4.452
LogS:	-5.254
# Rotatable Bonds:	5
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.45
Synthetic Accessibility Score:	6.698
Fsp3:	0.871
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.775
MDCK Permeability:	1.679229535511695e-05
Pgp-inhibitor:	0.933
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.816
Plasma Protein Binding (PPB):	96.98775482177734%
Volume Distribution (VD):	1.275
Pgp-substrate:	4.672824859619141%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.817
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.228
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.519
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.629

ADMET: Excretion

Clearance (CL):	6.189
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.663
Carcinogencity:	0.395
Eye Corrosion:	0.005
Eye Irritation:	0.032
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC471482

Natural Product ID:	NPC471482
*Common Name:**	LZKVXEZYUAJCDF-JMBQWPKISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LZKVXEZYUAJCDF-JMBQWPKISA-N
Standard InCHI:	InChI=1S/C31H50O4/c1-20(10-9-15-26(2,3)33)21-13-16-29(7)22-14-17-31-23(11-12-24(32)27(31,4)5)30(22,25(34-8)35-31)19-18-28(21,29)6/h9,14-15,17,20-25,32-33H,10-13,16,18-19H2,1-8H3/b15-9+/t20-,21-,22+,23+,24+,25?,28-,29+,30+,31-/m1/s1
SMILES:	CC(CC=CC(C)(C)O)C1CCC2(C1(CCC34C2C=CC5(C3CCC(C5(C)C)O)OC4OC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252510
PubChem CID:	44445561
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8182	Momordica charantia	Species	Cucurbitaceae	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
Others	7

Activity Type	# Activity
Cell Line	1
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[524221]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[524221]
NPT2	Others	Unspecified		Inhibition	=	27.6	%	PMID[524221]
NPT2	Others	Unspecified		Inhibition	=	72.5	%	PMID[524221]
NPT2	Others	Unspecified		Inhibition	=	94.5	%	PMID[524221]
NPT2	Others	Unspecified		Ratio	=	1.9	n.a.	PMID[524221]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.5	n.a.	PMID[524221]

☑ 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 NPC471482 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	216
0.1-0.2	1605
0.2-0.3	5153
0.3-0.4	11974
0.4-0.5	10712
0.5-0.6	6452
0.6-0.7	4976
0.7-0.8	1487
0.8-0.85	82
0.85-0.9	23
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300399
0.9789	High Similarity	NPC37207
0.9688	High Similarity	NPC471885
0.9688	High Similarity	NPC471887
0.9688	High Similarity	NPC471888
0.9688	High Similarity	NPC471886
0.9485	High Similarity	NPC471450
0.9381	High Similarity	NPC471889
0.9307	High Similarity	NPC65155
0.9208	High Similarity	NPC473318
0.9208	High Similarity	NPC28844
0.9208	High Similarity	NPC473328
0.9149	High Similarity	NPC27531
0.9118	High Similarity	NPC191439
0.9118	High Similarity	NPC170974
0.9118	High Similarity	NPC103627
0.9053	High Similarity	NPC144202
0.9029	High Similarity	NPC208189
0.9029	High Similarity	NPC65034
0.8942	High Similarity	NPC231797
0.8878	High Similarity	NPC216260
0.8878	High Similarity	NPC5358
0.8788	High Similarity	NPC324598
0.8762	High Similarity	NPC216595
0.8762	High Similarity	NPC473567
0.87	High Similarity	NPC176406
0.8654	High Similarity	NPC157530
0.8654	High Similarity	NPC14630
0.8654	High Similarity	NPC250089
0.8641	High Similarity	NPC33053
0.8571	High Similarity	NPC100892
0.8571	High Similarity	NPC477969
0.8571	High Similarity	NPC477970
0.8571	High Similarity	NPC135224
0.8542	High Similarity	NPC470817
0.8542	High Similarity	NPC295668
0.8515	High Similarity	NPC21568
0.8515	High Similarity	NPC285231
0.8515	High Similarity	NPC474022
0.8511	High Similarity	NPC299068
0.8485	Intermediate Similarity	NPC288970
0.8476	Intermediate Similarity	NPC128133
0.8469	Intermediate Similarity	NPC189513
0.8447	Intermediate Similarity	NPC85593
0.8447	Intermediate Similarity	NPC75608
0.8447	Intermediate Similarity	NPC93352
0.8447	Intermediate Similarity	NPC31430
0.8438	Intermediate Similarity	NPC470819
0.8411	Intermediate Similarity	NPC475354
0.8404	Intermediate Similarity	NPC470360
0.84	Intermediate Similarity	NPC177818
0.8384	Intermediate Similarity	NPC8774
0.8381	Intermediate Similarity	NPC38376
0.8381	Intermediate Similarity	NPC472897
0.8381	Intermediate Similarity	NPC472896
0.8381	Intermediate Similarity	NPC80210
0.8381	Intermediate Similarity	NPC235824
0.8365	Intermediate Similarity	NPC472899
0.8365	Intermediate Similarity	NPC472900
0.8365	Intermediate Similarity	NPC472898
0.835	Intermediate Similarity	NPC120009
0.835	Intermediate Similarity	NPC213190
0.8333	Intermediate Similarity	NPC470434
0.8333	Intermediate Similarity	NPC51154
0.8318	Intermediate Similarity	NPC13190
0.8302	Intermediate Similarity	NPC195116
0.8302	Intermediate Similarity	NPC472901
0.8302	Intermediate Similarity	NPC180459
0.8302	Intermediate Similarity	NPC206618
0.8302	Intermediate Similarity	NPC285253
0.8302	Intermediate Similarity	NPC221110
0.83	Intermediate Similarity	NPC98457
0.83	Intermediate Similarity	NPC90583
0.83	Intermediate Similarity	NPC227583
0.83	Intermediate Similarity	NPC12103
0.8286	Intermediate Similarity	NPC226642
0.8286	Intermediate Similarity	NPC475781
0.8286	Intermediate Similarity	NPC231340
0.8283	Intermediate Similarity	NPC65402
0.8283	Intermediate Similarity	NPC127718
0.8269	Intermediate Similarity	NPC475365
0.8265	Intermediate Similarity	NPC41554
0.8265	Intermediate Similarity	NPC97404
0.8252	Intermediate Similarity	NPC471363
0.8252	Intermediate Similarity	NPC238397
0.8241	Intermediate Similarity	NPC112274
0.8235	Intermediate Similarity	NPC477971
0.8235	Intermediate Similarity	NPC228251
0.8235	Intermediate Similarity	NPC20113
0.8235	Intermediate Similarity	NPC477968
0.8235	Intermediate Similarity	NPC469942
0.8235	Intermediate Similarity	NPC477972
0.8235	Intermediate Similarity	NPC161527
0.8235	Intermediate Similarity	NPC219285
0.8229	Intermediate Similarity	NPC149224
0.8218	Intermediate Similarity	NPC240372
0.8218	Intermediate Similarity	NPC476893
0.8208	Intermediate Similarity	NPC38948
0.819	Intermediate Similarity	NPC26798
0.819	Intermediate Similarity	NPC474015
0.8182	Intermediate Similarity	NPC67398
0.8182	Intermediate Similarity	NPC91654
0.8182	Intermediate Similarity	NPC474792
0.8173	Intermediate Similarity	NPC134270
0.8173	Intermediate Similarity	NPC473523
0.8173	Intermediate Similarity	NPC475889
0.8173	Intermediate Similarity	NPC473198
0.8173	Intermediate Similarity	NPC475701
0.8173	Intermediate Similarity	NPC127933
0.8173	Intermediate Similarity	NPC7644
0.8173	Intermediate Similarity	NPC7613
0.8163	Intermediate Similarity	NPC261990
0.8163	Intermediate Similarity	NPC474249
0.8163	Intermediate Similarity	NPC204188
0.8163	Intermediate Similarity	NPC291484
0.8163	Intermediate Similarity	NPC3345
0.8163	Intermediate Similarity	NPC80561
0.8163	Intermediate Similarity	NPC11216
0.8163	Intermediate Similarity	NPC329596
0.8158	Intermediate Similarity	NPC41129
0.8155	Intermediate Similarity	NPC309425
0.8155	Intermediate Similarity	NPC47566
0.8155	Intermediate Similarity	NPC4831
0.8155	Intermediate Similarity	NPC88000
0.8155	Intermediate Similarity	NPC160734
0.8155	Intermediate Similarity	NPC129372
0.8155	Intermediate Similarity	NPC472023
0.8148	Intermediate Similarity	NPC110494
0.8148	Intermediate Similarity	NPC157474
0.8148	Intermediate Similarity	NPC472987
0.8148	Intermediate Similarity	NPC473021
0.8137	Intermediate Similarity	NPC158088
0.8137	Intermediate Similarity	NPC234287
0.8137	Intermediate Similarity	NPC476895
0.8137	Intermediate Similarity	NPC280825
0.8131	Intermediate Similarity	NPC475030
0.8125	Intermediate Similarity	NPC6391
0.8125	Intermediate Similarity	NPC261266
0.8125	Intermediate Similarity	NPC323209
0.8119	Intermediate Similarity	NPC207617
0.8119	Intermediate Similarity	NPC72204
0.8113	Intermediate Similarity	NPC476594
0.8113	Intermediate Similarity	NPC475074
0.8108	Intermediate Similarity	NPC471354
0.8108	Intermediate Similarity	NPC20979
0.8108	Intermediate Similarity	NPC471353
0.8108	Intermediate Similarity	NPC476690
0.8108	Intermediate Similarity	NPC474418
0.8108	Intermediate Similarity	NPC309034
0.8108	Intermediate Similarity	NPC157376
0.8108	Intermediate Similarity	NPC100048
0.8108	Intermediate Similarity	NPC158344
0.8108	Intermediate Similarity	NPC471355
0.8108	Intermediate Similarity	NPC473852
0.8108	Intermediate Similarity	NPC142066
0.8108	Intermediate Similarity	NPC471351
0.8108	Intermediate Similarity	NPC243196
0.8108	Intermediate Similarity	NPC203862
0.8108	Intermediate Similarity	NPC196429
0.8108	Intermediate Similarity	NPC77319
0.8108	Intermediate Similarity	NPC84987
0.8108	Intermediate Similarity	NPC27507
0.8108	Intermediate Similarity	NPC244402
0.8108	Intermediate Similarity	NPC99728
0.8108	Intermediate Similarity	NPC50305
0.8108	Intermediate Similarity	NPC34390
0.8108	Intermediate Similarity	NPC87250
0.8105	Intermediate Similarity	NPC470077
0.81	Intermediate Similarity	NPC305160
0.8095	Intermediate Similarity	NPC264867
0.8095	Intermediate Similarity	NPC470321
0.8095	Intermediate Similarity	NPC221562
0.8095	Intermediate Similarity	NPC187400
0.8095	Intermediate Similarity	NPC470885
0.8095	Intermediate Similarity	NPC474464
0.8095	Intermediate Similarity	NPC81567
0.8095	Intermediate Similarity	NPC201880
0.8095	Intermediate Similarity	NPC473543
0.8095	Intermediate Similarity	NPC473207
0.8091	Intermediate Similarity	NPC84949
0.8091	Intermediate Similarity	NPC69576
0.8091	Intermediate Similarity	NPC11548
0.8091	Intermediate Similarity	NPC31354
0.8091	Intermediate Similarity	NPC471633
0.8081	Intermediate Similarity	NPC302584
0.8077	Intermediate Similarity	NPC136816
0.8077	Intermediate Similarity	NPC228049
0.8077	Intermediate Similarity	NPC68630
0.8077	Intermediate Similarity	NPC52585
0.8073	Intermediate Similarity	NPC473125
0.8073	Intermediate Similarity	NPC477050
0.8073	Intermediate Similarity	NPC476305
0.8061	Intermediate Similarity	NPC477917
0.8061	Intermediate Similarity	NPC473058
0.8061	Intermediate Similarity	NPC470361
0.8058	Intermediate Similarity	NPC7341
0.8058	Intermediate Similarity	NPC473200
0.8058	Intermediate Similarity	NPC324841
0.8056	Intermediate Similarity	NPC472717
0.8056	Intermediate Similarity	NPC101450

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 NPC471482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1771
0.2-0.3	4165
0.3-0.4	2074
0.4-0.5	516
0.5-0.6	233
0.6-0.7	169
0.7-0.8	36
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8036	Intermediate Similarity	NPD7328	Approved
0.8036	Intermediate Similarity	NPD7327	Approved
0.7965	Intermediate Similarity	NPD7516	Approved
0.7826	Intermediate Similarity	NPD8378	Approved
0.7826	Intermediate Similarity	NPD8296	Approved
0.7826	Intermediate Similarity	NPD8335	Approved
0.7826	Intermediate Similarity	NPD8380	Approved
0.7826	Intermediate Similarity	NPD8379	Approved
0.7739	Intermediate Similarity	NPD8294	Approved
0.7739	Intermediate Similarity	NPD8377	Approved
0.7672	Intermediate Similarity	NPD8033	Approved
0.7672	Intermediate Similarity	NPD7503	Approved
0.7551	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7640	Approved
0.7547	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7458	Intermediate Similarity	NPD6370	Approved
0.7453	Intermediate Similarity	NPD7638	Approved
0.7449	Intermediate Similarity	NPD6695	Phase 3
0.7417	Intermediate Similarity	NPD7507	Approved
0.7377	Intermediate Similarity	NPD7319	Approved
0.7288	Intermediate Similarity	NPD6054	Approved
0.7157	Intermediate Similarity	NPD7750	Discontinued
0.7157	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7524	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD6931	Approved
0.7143	Intermediate Similarity	NPD6930	Phase 2
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD7514	Phase 3
0.7083	Intermediate Similarity	NPD6015	Approved
0.7083	Intermediate Similarity	NPD6016	Approved
0.708	Intermediate Similarity	NPD6686	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7049	Intermediate Similarity	NPD7492	Approved
0.7041	Intermediate Similarity	NPD6929	Approved
0.7025	Intermediate Similarity	NPD5988	Approved
0.6992	Remote Similarity	NPD6616	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.6979	Remote Similarity	NPD6942	Approved
0.6979	Remote Similarity	NPD7339	Approved
0.697	Remote Similarity	NPD7332	Phase 2
0.697	Remote Similarity	NPD6928	Phase 2
0.6939	Remote Similarity	NPD7145	Approved
0.6937	Remote Similarity	NPD7632	Discontinued
0.6935	Remote Similarity	NPD7078	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.69	Remote Similarity	NPD6902	Approved
0.6891	Remote Similarity	NPD7115	Discovery
0.6887	Remote Similarity	NPD7087	Discontinued
0.6887	Remote Similarity	NPD7637	Suspended
0.6869	Remote Similarity	NPD7645	Phase 2
0.6857	Remote Similarity	NPD6051	Approved
0.6837	Remote Similarity	NPD6932	Approved
0.6837	Remote Similarity	NPD6925	Approved
0.6837	Remote Similarity	NPD5776	Phase 2
0.6829	Remote Similarity	NPD6067	Discontinued
0.6822	Remote Similarity	NPD8171	Discontinued
0.6796	Remote Similarity	NPD6893	Approved
0.6786	Remote Similarity	NPD5211	Phase 2
0.6783	Remote Similarity	NPD6881	Approved
0.6783	Remote Similarity	NPD7320	Approved
0.6783	Remote Similarity	NPD6899	Approved
0.6754	Remote Similarity	NPD6675	Approved
0.6754	Remote Similarity	NPD7128	Approved
0.6754	Remote Similarity	NPD6402	Approved
0.6754	Remote Similarity	NPD5739	Approved
0.675	Remote Similarity	NPD6009	Approved
0.6735	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6614	Remote Similarity	NPD6033	Approved
0.661	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6617	Approved
0.661	Remote Similarity	NPD8130	Phase 1
0.661	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD6008	Approved
0.6607	Remote Similarity	NPD5285	Approved
0.6607	Remote Similarity	NPD4696	Approved
0.6607	Remote Similarity	NPD5286	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6013	Approved
0.6581	Remote Similarity	NPD6014	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6581	Remote Similarity	NPD6012	Approved
0.6581	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD6079	Approved
0.6569	Remote Similarity	NPD6898	Phase 1
0.6555	Remote Similarity	NPD6053	Discontinued
0.6555	Remote Similarity	NPD8297	Approved
0.6552	Remote Similarity	NPD5701	Approved
0.6549	Remote Similarity	NPD4159	Approved
0.6542	Remote Similarity	NPD5328	Approved
0.6538	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4786	Approved
0.6535	Remote Similarity	NPD6683	Phase 2
0.6531	Remote Similarity	NPD4784	Approved
0.6531	Remote Similarity	NPD4785	Approved
0.6531	Remote Similarity	NPD6924	Approved
0.6531	Remote Similarity	NPD6926	Approved
0.6525	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD4632	Approved
0.6496	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6011	Approved
0.6495	Remote Similarity	NPD4243	Approved
0.6491	Remote Similarity	NPD5226	Approved
0.6491	Remote Similarity	NPD4633	Approved
0.6491	Remote Similarity	NPD5224	Approved
0.6491	Remote Similarity	NPD5225	Approved
0.646	Remote Similarity	NPD6648	Approved
0.646	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD7741	Discontinued
0.6452	Remote Similarity	NPD6319	Approved
0.6436	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5174	Approved
0.6435	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD3618	Phase 1
0.6412	Remote Similarity	NPD8449	Approved
0.6404	Remote Similarity	NPD5223	Approved
0.64	Remote Similarity	NPD6933	Approved
0.6387	Remote Similarity	NPD4634	Approved
0.6364	Remote Similarity	NPD8450	Suspended
0.6355	Remote Similarity	NPD4251	Approved
0.6355	Remote Similarity	NPD4250	Approved
0.6346	Remote Similarity	NPD3667	Approved
0.6339	Remote Similarity	NPD5221	Approved
0.6339	Remote Similarity	NPD5222	Approved
0.6339	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7151	Approved
0.6327	Remote Similarity	NPD7152	Approved
0.6327	Remote Similarity	NPD7150	Approved
0.6311	Remote Similarity	NPD7509	Discontinued
0.6311	Remote Similarity	NPD4748	Discontinued
0.63	Remote Similarity	NPD8264	Approved
0.6299	Remote Similarity	NPD7604	Phase 2
0.6299	Remote Similarity	NPD8328	Phase 3
0.6289	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7625	Phase 1
0.6283	Remote Similarity	NPD5173	Approved
0.6273	Remote Similarity	NPD8034	Phase 2
0.6273	Remote Similarity	NPD8035	Phase 2
0.6271	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5983	Phase 2
0.6262	Remote Similarity	NPD4249	Approved
0.626	Remote Similarity	NPD5956	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7100	Approved
0.624	Remote Similarity	NPD7101	Approved
0.6239	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4753	Phase 2
0.6224	Remote Similarity	NPD7143	Approved
0.6224	Remote Similarity	NPD7144	Approved
0.6218	Remote Similarity	NPD4730	Approved
0.6218	Remote Similarity	NPD4729	Approved
0.6214	Remote Similarity	NPD4195	Approved
0.621	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD6336	Discontinued
0.6198	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4697	Phase 3
0.6186	Remote Similarity	NPD4767	Approved
0.6186	Remote Similarity	NPD4768	Approved
0.6186	Remote Similarity	NPD6640	Phase 3
0.6182	Remote Similarity	NPD7136	Phase 2
0.6182	Remote Similarity	NPD3168	Discontinued
0.6168	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7748	Approved
0.616	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD4754	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6142	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7902	Approved
0.6139	Remote Similarity	NPD5275	Approved
0.6139	Remote Similarity	NPD4190	Phase 3
0.6129	Remote Similarity	NPD6274	Approved
0.6126	Remote Similarity	NPD7515	Phase 2
0.6122	Remote Similarity	NPD6923	Approved
0.6122	Remote Similarity	NPD6922	Approved
0.6116	Remote Similarity	NPD5249	Phase 3
0.6116	Remote Similarity	NPD5248	Approved
0.6116	Remote Similarity	NPD5250	Approved
0.6116	Remote Similarity	NPD5247	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