NPASS Compound

Structure

NPC470026 OpenBabel07101718242D 45 47 0 0 1 0 0 0 0 0999 V2000 3.9937 10.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4345 3.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -0.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7450 -0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3765 -1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9937 9.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 3.6808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 8.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1277 7.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 7.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2617 6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 5.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9345 2.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0540 0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 -1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -0.4173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 0.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0322 0.5862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0238 -2.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -0.4173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9345 2.8147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 4.0827 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 -5.4345 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 2 0 0 0 0 3 20 2 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 8 10 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 28 1 0 0 0 0 17 24 1 0 0 0 0 17 25 2 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 19 33 1 0 0 0 0 20 26 1 0 0 0 0 21 29 1 0 0 0 0 21 33 1 1 0 0 0 22 35 2 0 0 0 0 22 41 1 0 0 0 0 23 36 2 0 0 0 0 23 42 1 0 0 0 0 24 43 1 1 0 0 0 25 31 1 0 0 0 0 26 19 1 1 0 0 0 26 45 1 0 0 0 0 27 33 1 6 0 0 0 27 34 1 0 0 0 0 28 37 2 0 0 0 0 28 43 1 0 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 34 1 6 0 0 0 30 39 1 0 0 0 0 31 41 1 1 0 0 0 31 44 1 0 0 0 0 32 34 1 1 0 0 0 32 42 1 0 0 0 0 32 44 1 0 0 0 0 33 7 1 6 0 0 0 34 25 1 6 0 0 0 40 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.32
Volume:	646.551
LogP:	4.152
LogD:	1.964
LogS:	-3.944
# Rotatable Bonds:	17
TPSA:	158.05
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.036
Synthetic Accessibility Score:	6.26
Fsp3:	0.618
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.108
MDCK Permeability:	7.627821469213814e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	0.302
Human Intestinal Absorption (HIA):	0.584
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	92.49394989013672%
Volume Distribution (VD):	1.937
Pgp-substrate:	4.093392848968506%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.425
CYP2C9-substrate:	0.172
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.534
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	1.835
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.876
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.964
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.905
Carcinogencity:	0.509
Eye Corrosion:	0.013
Eye Irritation:	0.013
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC470026

Natural Product ID:	NPC470026
*Common Name:**	Argutin G
IUPAC Name:	[(1S,3R,5R,6aS,7S,8S,9R,10S,10aS)-1,3-diacetyloxy-7-[(2R)-2-hydroperoxy-3-methylidenepent-4-enyl]-9,10-dihydroxy-7,8-dimethyl-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] (2Z,4E)-deca-2,4-dienoate
Synonyms:	Argutin G
Standard InCHIKey:	SHPSAYQITLDCQK-FMYGESEKSA-N
Standard InCHI:	InChI=1S/C34H48O11/c1-8-10-11-12-13-14-15-16-28(37)43-24-17-25-31(41-22(5)35)44-32(42-23(6)36)34(25)27(18-24)33(7,21(4)29(38)30(34)39)19-26(45-40)20(3)9-2/h9,13-17,21,24,26-27,29-32,38-40H,2-3,8,10-12,18-19H2,1,4-7H3/b14-13+,16-15-/t21-,24+,26-,27+,29-,30-,31+,32-,33-,34-/m1/s1
SMILES:	CCCCCC=CC=CC(=O)OC1CC2C(C(C(C(C23C(OC(C3=C1)OC(=O)C)OC(=O)C)O)O)C)(C)CC(C(=C)C=C)OO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651118
PubChem CID:	53319584
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21067210]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21067210]
NPO22840	Casearia arguta	Species	Salicaceae	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
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	2800.0	nM	PMID[502475]
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	4200.0	nM	PMID[502475]
NPT369	Cell Line	ACHN	Homo sapiens	Ratio EC50	=	1.5	n.a.	PMID[502475]

☑ 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 NPC470026 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	202
0.1-0.2	1193
0.2-0.3	3957
0.3-0.4	7098
0.4-0.5	13684
0.5-0.6	8537
0.6-0.7	5805
0.7-0.8	2070
0.8-0.85	63
0.85-0.9	50
0.9-0.95	24
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC316708
0.9808	High Similarity	NPC470027
0.9712	High Similarity	NPC328074
0.9712	High Similarity	NPC317460
0.9712	High Similarity	NPC470025
0.9712	High Similarity	NPC321272
0.9706	High Similarity	NPC224660
0.9615	High Similarity	NPC17791
0.9608	High Similarity	NPC109376
0.9515	High Similarity	NPC470024
0.951	High Similarity	NPC172867
0.9327	High Similarity	NPC311223
0.9238	High Similarity	NPC40728
0.9238	High Similarity	NPC316974
0.9231	High Similarity	NPC125423
0.9231	High Similarity	NPC88013
0.9151	High Similarity	NPC119550
0.9143	High Similarity	NPC217921
0.9143	High Similarity	NPC135015
0.9143	High Similarity	NPC128795
0.9143	High Similarity	NPC48548
0.9135	High Similarity	NPC218158
0.9038	High Similarity	NPC470321
0.9038	High Similarity	NPC201880
0.9038	High Similarity	NPC264867
0.9038	High Similarity	NPC473207
0.9038	High Similarity	NPC81567
0.8942	High Similarity	NPC7613
0.8942	High Similarity	NPC475889
0.8942	High Similarity	NPC134270
0.8942	High Similarity	NPC127933
0.8942	High Similarity	NPC7644
0.8868	High Similarity	NPC184512
0.8846	High Similarity	NPC238397
0.8846	High Similarity	NPC471363
0.8774	High Similarity	NPC252296
0.8725	High Similarity	NPC171598
0.8673	High Similarity	NPC470914
0.8654	High Similarity	NPC473545
0.8654	High Similarity	NPC472187
0.8654	High Similarity	NPC473204
0.8641	High Similarity	NPC98112
0.8627	High Similarity	NPC472189
0.8627	High Similarity	NPC471372
0.8627	High Similarity	NPC471362
0.8624	High Similarity	NPC177047
0.8598	High Similarity	NPC82251
0.8558	High Similarity	NPC471366
0.8558	High Similarity	NPC472186
0.8558	High Similarity	NPC318917
0.8558	High Similarity	NPC476800
0.8532	High Similarity	NPC206618
0.8491	Intermediate Similarity	NPC11956
0.8462	Intermediate Similarity	NPC472188
0.8448	Intermediate Similarity	NPC471082
0.844	Intermediate Similarity	NPC38948
0.8426	Intermediate Similarity	NPC239961
0.8421	Intermediate Similarity	NPC473828
0.8421	Intermediate Similarity	NPC473617
0.8411	Intermediate Similarity	NPC23584
0.8411	Intermediate Similarity	NPC281378
0.8411	Intermediate Similarity	NPC120009
0.8396	Intermediate Similarity	NPC472554
0.8396	Intermediate Similarity	NPC280991
0.8396	Intermediate Similarity	NPC198992
0.8393	Intermediate Similarity	NPC264153
0.8393	Intermediate Similarity	NPC473159
0.8381	Intermediate Similarity	NPC474440
0.8349	Intermediate Similarity	NPC475074
0.8349	Intermediate Similarity	NPC472390
0.8333	Intermediate Similarity	NPC470768
0.8318	Intermediate Similarity	NPC472552
0.8304	Intermediate Similarity	NPC473125
0.8302	Intermediate Similarity	NPC161527
0.8302	Intermediate Similarity	NPC219285
0.8302	Intermediate Similarity	NPC477968
0.8302	Intermediate Similarity	NPC477972
0.8302	Intermediate Similarity	NPC20113
0.8302	Intermediate Similarity	NPC477971
0.8302	Intermediate Similarity	NPC228251
0.8273	Intermediate Similarity	NPC475263
0.8261	Intermediate Similarity	NPC470515
0.8257	Intermediate Similarity	NPC470767
0.8257	Intermediate Similarity	NPC470763
0.8246	Intermediate Similarity	NPC207637
0.8241	Intermediate Similarity	NPC474124
0.8241	Intermediate Similarity	NPC474575
0.8241	Intermediate Similarity	NPC45897
0.823	Intermediate Similarity	NPC40133
0.823	Intermediate Similarity	NPC49413
0.823	Intermediate Similarity	NPC290608
0.823	Intermediate Similarity	NPC473128
0.823	Intermediate Similarity	NPC44298
0.8208	Intermediate Similarity	NPC473154
0.8205	Intermediate Similarity	NPC233500
0.8205	Intermediate Similarity	NPC170084
0.8205	Intermediate Similarity	NPC476204
0.819	Intermediate Similarity	NPC470517
0.819	Intermediate Similarity	NPC470915
0.819	Intermediate Similarity	NPC219656
0.819	Intermediate Similarity	NPC470911
0.8182	Intermediate Similarity	NPC473586
0.8174	Intermediate Similarity	NPC203862
0.8174	Intermediate Similarity	NPC473968
0.8174	Intermediate Similarity	NPC23046
0.8173	Intermediate Similarity	NPC469491
0.8173	Intermediate Similarity	NPC88507
0.8158	Intermediate Similarity	NPC475163
0.8148	Intermediate Similarity	NPC201191
0.8148	Intermediate Similarity	NPC476471
0.8148	Intermediate Similarity	NPC472815
0.8148	Intermediate Similarity	NPC150463
0.8148	Intermediate Similarity	NPC121423
0.8148	Intermediate Similarity	NPC470571
0.8148	Intermediate Similarity	NPC475344
0.8142	Intermediate Similarity	NPC231797
0.8137	Intermediate Similarity	NPC470819
0.8136	Intermediate Similarity	NPC196130
0.8131	Intermediate Similarity	NPC324841
0.812	Intermediate Similarity	NPC48692
0.812	Intermediate Similarity	NPC135369
0.8113	Intermediate Similarity	NPC91197
0.8113	Intermediate Similarity	NPC309503
0.8113	Intermediate Similarity	NPC155319
0.8113	Intermediate Similarity	NPC96597
0.8113	Intermediate Similarity	NPC125551
0.8113	Intermediate Similarity	NPC239547
0.8108	Intermediate Similarity	NPC50124
0.8095	Intermediate Similarity	NPC275310
0.8095	Intermediate Similarity	NPC286612
0.8095	Intermediate Similarity	NPC230347
0.8091	Intermediate Similarity	NPC88349
0.8091	Intermediate Similarity	NPC51719
0.8087	Intermediate Similarity	NPC471816
0.8083	Intermediate Similarity	NPC179261
0.8073	Intermediate Similarity	NPC473070
0.807	Intermediate Similarity	NPC157441
0.807	Intermediate Similarity	NPC287075
0.8067	Intermediate Similarity	NPC219804
0.8067	Intermediate Similarity	NPC41129
0.8058	Intermediate Similarity	NPC469403
0.8058	Intermediate Similarity	NPC470817
0.8056	Intermediate Similarity	NPC11974
0.8056	Intermediate Similarity	NPC475617
0.8053	Intermediate Similarity	NPC208189
0.8053	Intermediate Similarity	NPC65034
0.8037	Intermediate Similarity	NPC477928
0.8036	Intermediate Similarity	NPC257853
0.8036	Intermediate Similarity	NPC475586
0.8034	Intermediate Similarity	NPC44899
0.8034	Intermediate Similarity	NPC304260
0.8034	Intermediate Similarity	NPC476529
0.8034	Intermediate Similarity	NPC475775
0.8034	Intermediate Similarity	NPC153085
0.8034	Intermediate Similarity	NPC268326
0.8034	Intermediate Similarity	NPC122971
0.8034	Intermediate Similarity	NPC29639
0.8034	Intermediate Similarity	NPC5883
0.8033	Intermediate Similarity	NPC471407
0.8033	Intermediate Similarity	NPC476966
0.8019	Intermediate Similarity	NPC8954
0.8019	Intermediate Similarity	NPC165632
0.8019	Intermediate Similarity	NPC473153
0.8019	Intermediate Similarity	NPC94905
0.8019	Intermediate Similarity	NPC311166
0.8018	Intermediate Similarity	NPC33053
0.8018	Intermediate Similarity	NPC471205
0.8018	Intermediate Similarity	NPC293512
0.8018	Intermediate Similarity	NPC122816
0.8017	Intermediate Similarity	NPC93883
0.8017	Intermediate Similarity	NPC152615
0.8017	Intermediate Similarity	NPC474483
0.8	Intermediate Similarity	NPC473068
0.8	Intermediate Similarity	NPC31430
0.8	Intermediate Similarity	NPC470255
0.8	Intermediate Similarity	NPC86346
0.8	Intermediate Similarity	NPC256368
0.8	Intermediate Similarity	NPC194941
0.8	Intermediate Similarity	NPC473543
0.8	Intermediate Similarity	NPC75856
0.8	Intermediate Similarity	NPC93352
0.8	Intermediate Similarity	NPC469379
0.8	Intermediate Similarity	NPC85593
0.7982	Intermediate Similarity	NPC273668
0.7982	Intermediate Similarity	NPC214277
0.7982	Intermediate Similarity	NPC194951
0.7982	Intermediate Similarity	NPC12046
0.7966	Intermediate Similarity	NPC476150
0.7966	Intermediate Similarity	NPC107607
0.7966	Intermediate Similarity	NPC109607
0.7966	Intermediate Similarity	NPC107338
0.7966	Intermediate Similarity	NPC470312
0.7966	Intermediate Similarity	NPC257610
0.7966	Intermediate Similarity	NPC476127
0.7965	Intermediate Similarity	NPC103627
0.7965	Intermediate Similarity	NPC170974
0.7965	Intermediate Similarity	NPC83005
0.7965	Intermediate Similarity	NPC235014
0.7965	Intermediate Similarity	NPC191439
0.7963	Intermediate Similarity	NPC64348

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 NPC470026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1356
0.2-0.3	3702
0.3-0.4	2563
0.4-0.5	871
0.5-0.6	303
0.6-0.7	160
0.7-0.8	22
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
0.8205	Intermediate Similarity	NPD7503	Approved
0.7946	Intermediate Similarity	NPD6686	Approved
0.7899	Intermediate Similarity	NPD8033	Approved
0.7881	Intermediate Similarity	NPD7516	Approved
0.7815	Intermediate Similarity	NPD8294	Approved
0.7815	Intermediate Similarity	NPD8377	Approved
0.7797	Intermediate Similarity	NPD7327	Approved
0.7797	Intermediate Similarity	NPD7328	Approved
0.775	Intermediate Similarity	NPD8296	Approved
0.775	Intermediate Similarity	NPD8378	Approved
0.775	Intermediate Similarity	NPD8335	Approved
0.775	Intermediate Similarity	NPD8379	Approved
0.775	Intermediate Similarity	NPD8380	Approved
0.7568	Intermediate Similarity	NPD5344	Discontinued
0.7547	Intermediate Similarity	NPD7838	Discovery
0.7545	Intermediate Similarity	NPD4225	Approved
0.7477	Intermediate Similarity	NPD6648	Approved
0.7459	Intermediate Similarity	NPD8513	Phase 3
0.7459	Intermediate Similarity	NPD8516	Approved
0.7459	Intermediate Similarity	NPD8517	Approved
0.7459	Intermediate Similarity	NPD8515	Approved
0.7387	Intermediate Similarity	NPD7638	Approved
0.7387	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7507	Approved
0.7321	Intermediate Similarity	NPD7640	Approved
0.7321	Intermediate Similarity	NPD7639	Approved
0.7265	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7736	Approved
0.7094	Intermediate Similarity	NPD6412	Phase 2
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.7025	Intermediate Similarity	NPD8133	Approved
0.6992	Remote Similarity	NPD7115	Discovery
0.6984	Remote Similarity	NPD6370	Approved
0.6942	Remote Similarity	NPD6882	Approved
0.6917	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD8074	Phase 3
0.6899	Remote Similarity	NPD8293	Discontinued
0.6875	Remote Similarity	NPD7492	Approved
0.6855	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6054	Approved
0.6822	Remote Similarity	NPD6616	Approved
0.6803	Remote Similarity	NPD8297	Approved
0.6769	Remote Similarity	NPD7078	Approved
0.6757	Remote Similarity	NPD46	Approved
0.6757	Remote Similarity	NPD6698	Approved
0.6752	Remote Similarity	NPD7632	Discontinued
0.6721	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6009	Approved
0.6696	Remote Similarity	NPD7637	Suspended
0.6693	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6015	Approved
0.6641	Remote Similarity	NPD6016	Approved
0.6637	Remote Similarity	NPD5778	Approved
0.6637	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6613	Remote Similarity	NPD4632	Approved
0.6612	Remote Similarity	NPD6899	Approved
0.6612	Remote Similarity	NPD6881	Approved
0.6606	Remote Similarity	NPD1694	Approved
0.6589	Remote Similarity	NPD5988	Approved
0.6585	Remote Similarity	NPD6649	Approved
0.6585	Remote Similarity	NPD6650	Approved
0.6585	Remote Similarity	NPD8130	Phase 1
0.6579	Remote Similarity	NPD7748	Approved
0.6562	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD7902	Approved
0.6549	Remote Similarity	NPD7983	Approved
0.6538	Remote Similarity	NPD7829	Approved
0.6538	Remote Similarity	NPD7830	Approved
0.6538	Remote Similarity	NPD6067	Discontinued
0.6529	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5697	Approved
0.6514	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6883	Approved
0.6504	Remote Similarity	NPD7290	Approved
0.6504	Remote Similarity	NPD7102	Approved
0.6475	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6847	Approved
0.6452	Remote Similarity	NPD6869	Approved
0.6452	Remote Similarity	NPD6617	Approved
0.6446	Remote Similarity	NPD6675	Approved
0.6446	Remote Similarity	NPD6402	Approved
0.6446	Remote Similarity	NPD7128	Approved
0.6446	Remote Similarity	NPD5739	Approved
0.6444	Remote Similarity	NPD7260	Phase 2
0.6442	Remote Similarity	NPD8264	Approved
0.6423	Remote Similarity	NPD6012	Approved
0.6423	Remote Similarity	NPD6372	Approved
0.6423	Remote Similarity	NPD6013	Approved
0.6423	Remote Similarity	NPD6373	Approved
0.6423	Remote Similarity	NPD6014	Approved
0.6422	Remote Similarity	NPD6695	Phase 3
0.6404	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD6411	Approved
0.64	Remote Similarity	NPD6053	Discontinued
0.6389	Remote Similarity	NPD7625	Phase 1
0.6371	Remote Similarity	NPD6371	Approved
0.6348	Remote Similarity	NPD6399	Phase 3
0.6341	Remote Similarity	NPD6011	Approved
0.6341	Remote Similarity	NPD7320	Approved
0.6339	Remote Similarity	NPD7750	Discontinued
0.6331	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6008	Approved
0.6293	Remote Similarity	NPD7900	Approved
0.6293	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7604	Phase 2
0.6261	Remote Similarity	NPD6079	Approved
0.626	Remote Similarity	NPD5701	Approved
0.626	Remote Similarity	NPD5983	Phase 2
0.624	Remote Similarity	NPD4634	Approved
0.6239	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6051	Approved
0.6228	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6101	Approved
0.6204	Remote Similarity	NPD6929	Approved
0.6204	Remote Similarity	NPD7645	Phase 2
0.6198	Remote Similarity	NPD5211	Phase 2
0.6194	Remote Similarity	NPD8451	Approved
0.6194	Remote Similarity	NPD6336	Discontinued
0.6188	Remote Similarity	NPD7799	Discontinued
0.6186	Remote Similarity	NPD7839	Suspended
0.6167	Remote Similarity	NPD5286	Approved
0.6167	Remote Similarity	NPD4696	Approved
0.6167	Remote Similarity	NPD5285	Approved
0.6159	Remote Similarity	NPD6845	Suspended
0.6154	Remote Similarity	NPD7641	Discontinued
0.6149	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8448	Approved
0.6147	Remote Similarity	NPD7525	Registered
0.6147	Remote Similarity	NPD7332	Phase 2
0.6147	Remote Similarity	NPD6930	Phase 2
0.6147	Remote Similarity	NPD6931	Approved
0.6147	Remote Similarity	NPD7514	Phase 3
0.6136	Remote Similarity	NPD8444	Approved
0.6134	Remote Similarity	NPD6083	Phase 2
0.6134	Remote Similarity	NPD6084	Phase 2
0.6111	Remote Similarity	NPD7145	Approved
0.6107	Remote Similarity	NPD7100	Approved
0.6107	Remote Similarity	NPD7101	Approved
0.6106	Remote Similarity	NPD3618	Phase 1
0.6103	Remote Similarity	NPD6033	Approved
0.6098	Remote Similarity	NPD5141	Approved
0.6091	Remote Similarity	NPD6902	Approved
0.609	Remote Similarity	NPD5126	Approved
0.609	Remote Similarity	NPD5125	Phase 3
0.6087	Remote Similarity	NPD5328	Approved
0.6075	Remote Similarity	NPD6933	Approved
0.6069	Remote Similarity	NPD7266	Discontinued
0.6068	Remote Similarity	NPD8171	Discontinued
0.6066	Remote Similarity	NPD4633	Approved
0.6066	Remote Similarity	NPD5224	Approved
0.6066	Remote Similarity	NPD5225	Approved
0.6066	Remote Similarity	NPD5226	Approved
0.6063	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4251	Approved
0.6053	Remote Similarity	NPD4250	Approved
0.605	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5222	Approved
0.605	Remote Similarity	NPD5221	Approved
0.6043	Remote Similarity	NPD8449	Approved
0.6034	Remote Similarity	NPD5785	Approved
0.6034	Remote Similarity	NPD3168	Discontinued
0.6031	Remote Similarity	NPD6335	Approved
0.6019	Remote Similarity	NPD6932	Approved
0.6019	Remote Similarity	NPD5776	Phase 2
0.6019	Remote Similarity	NPD6925	Approved
0.6016	Remote Similarity	NPD5174	Approved
0.6016	Remote Similarity	NPD5175	Approved
0.6015	Remote Similarity	NPD6921	Approved
0.6014	Remote Similarity	NPD8392	Approved
0.6014	Remote Similarity	NPD8390	Approved
0.6014	Remote Similarity	NPD8391	Approved
0.6014	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD8450	Suspended
0.6	Remote Similarity	NPD6868	Approved
0.5984	Remote Similarity	NPD4159	Approved
0.5984	Remote Similarity	NPD5223	Approved
0.5983	Remote Similarity	NPD5284	Approved
0.5983	Remote Similarity	NPD7087	Discontinued
0.5983	Remote Similarity	NPD8035	Phase 2
0.5983	Remote Similarity	NPD5281	Approved
0.5983	Remote Similarity	NPD8034	Phase 2
0.5981	Remote Similarity	NPD6942	Approved
0.5981	Remote Similarity	NPD7339	Approved
0.5981	Remote Similarity	NPD8039	Approved
0.5966	Remote Similarity	NPD5695	Phase 3
0.5965	Remote Similarity	NPD6684	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