NPASS Compound

Structure

NPC224660 OpenBabel07101719252D 44 46 0 0 1 0 0 0 0 0999 V2000 3.9087 9.8682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3189 3.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8720 2.7548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7196 -0.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7079 -0.5606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0234 -2.4867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3614 1.9072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9087 8.8894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3401 3.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0611 8.4001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0611 7.4213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2135 6.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2135 5.9533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3659 5.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3659 4.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5183 3.9958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0244 -0.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3293 2.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0244 2.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8508 1.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8508 2.7548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8720 0.0809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0103 0.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9807 -2.2832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 3.0171 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3293 1.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3401 1.9072 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0244 1.5490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1768 0.0809 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3293 4.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3981 0.8941 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9734 0.1023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8720 1.0596 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1768 1.0596 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9676 0.5738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6356 -3.0105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3293 -0.4084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3293 5.4639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8082 2.7548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 1.0976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2831 -1.3524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1768 3.9958 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 -5.3189 1.9072 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 21 2 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 10 1 0 0 0 0 9 21 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 30 1 0 0 0 0 17 22 1 0 0 0 0 17 29 1 0 0 0 0 18 25 1 0 0 0 0 18 26 2 0 0 0 0 19 25 1 0 0 0 0 19 28 1 0 0 0 0 20 33 1 0 0 0 0 21 27 1 0 0 0 0 22 33 1 1 0 0 0 23 35 2 0 0 0 0 23 40 1 0 0 0 0 24 36 2 0 0 0 0 24 41 1 0 0 0 0 25 42 1 1 0 0 0 26 31 1 0 0 0 0 27 20 1 1 0 0 0 27 44 1 0 0 0 0 28 33 1 6 0 0 0 28 34 1 0 0 0 0 29 34 1 6 0 0 0 29 37 1 0 0 0 0 30 38 2 0 0 0 0 30 42 1 0 0 0 0 31 40 1 1 0 0 0 31 43 1 0 0 0 0 32 34 1 1 0 0 0 32 41 1 0 0 0 0 32 43 1 0 0 0 0 33 7 1 6 0 0 0 34 26 1 6 0 0 0 39 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.32
Volume:	637.761
LogP:	4.585
LogD:	2.352
LogS:	-4.212
# Rotatable Bonds:	17
TPSA:	137.82
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.036
Synthetic Accessibility Score:	6.133
Fsp3:	0.618
Lipinski Rule-of-5:	Accepted
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:	-4.996
MDCK Permeability:	4.167631050222553e-05
Pgp-inhibitor:	0.908
Pgp-substrate:	0.193
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	95.74822235107422%
Volume Distribution (VD):	2.401
Pgp-substrate:	3.4814887046813965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.191
CYP2C9-inhibitor:	0.646
CYP2C9-substrate:	0.517
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	2.265
Half-life (T1/2):	0.095

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.949
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.944
Carcinogencity:	0.196
Eye Corrosion:	0.014
Eye Irritation:	0.02
Respiratory Toxicity:	0.924

Download Data

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

Natural Product: NPC224660

Natural Product ID:	NPC224660
*Common Name:**	Argutin F
IUPAC Name:	[(1S,3R,5R,6aS,7R,8R,10R,10aS)-1,3-diacetyloxy-7-[(2R)-2-hydroperoxy-3-methylidenepent-4-enyl]-10-hydroxy-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 F
Standard InCHIKey:	HXZWRWDSAJYAQI-ASVRBJFWSA-N
Standard InCHI:	InChI=1S/C34H48O10/c1-8-10-11-12-13-14-15-16-30(38)42-25-18-26-31(40-23(5)35)43-32(41-24(6)36)34(26)28(19-25)33(7,22(4)17-29(34)37)20-27(44-39)21(3)9-2/h9,13-16,18,22,25,27-29,31-32,37,39H,2-3,8,10-12,17,19-20H2,1,4-7H3/b14-13+,16-15-/t22-,25+,27-,28+,29-,31+,32-,33-,34-/m1/s1
SMILES:	CCCCC/C=C/C=CC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@]32[C@@H](C1)[C@](C)(C[C@H](C(=C)C=C)OO)[C@H](C)C[C@H]3O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651117
PubChem CID:	53322212
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	=	7100.0	nM	PMID[484526]
NPT369	Cell Line	ACHN	Homo sapiens	EC50	=	10400.0	nM	PMID[484526]
NPT369	Cell Line	ACHN	Homo sapiens	Ratio EC50	=	1.5	n.a.	PMID[484526]

☑ 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 NPC224660 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	195
0.1-0.2	1157
0.2-0.3	3950
0.3-0.4	7404
0.4-0.5	13767
0.5-0.6	8128
0.6-0.7	6119
0.7-0.8	1814
0.8-0.85	73
0.85-0.9	40
0.9-0.95	39
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9899	High Similarity	NPC109376
0.98	High Similarity	NPC470024
0.9798	High Similarity	NPC172867
0.9706	High Similarity	NPC470026
0.9608	High Similarity	NPC316708
0.9519	High Similarity	NPC470027
0.9515	High Similarity	NPC17791
0.9423	High Similarity	NPC470025
0.9423	High Similarity	NPC321272
0.9423	High Similarity	NPC317460
0.9423	High Similarity	NPC328074
0.9406	High Similarity	NPC218158
0.9307	High Similarity	NPC470321
0.9307	High Similarity	NPC201880
0.9307	High Similarity	NPC473207
0.9307	High Similarity	NPC264867
0.9307	High Similarity	NPC81567
0.9208	High Similarity	NPC127933
0.9208	High Similarity	NPC7644
0.9208	High Similarity	NPC134270
0.9208	High Similarity	NPC7613
0.9208	High Similarity	NPC475889
0.9126	High Similarity	NPC184512
0.9109	High Similarity	NPC471363
0.9109	High Similarity	NPC238397
0.9038	High Similarity	NPC311223
0.9029	High Similarity	NPC252296
0.899	High Similarity	NPC171598
0.8952	High Similarity	NPC316974
0.8952	High Similarity	NPC40728
0.8942	High Similarity	NPC125423
0.8942	High Similarity	NPC88013
0.8911	High Similarity	NPC472187
0.8911	High Similarity	NPC473204
0.8911	High Similarity	NPC473545
0.89	High Similarity	NPC98112
0.8889	High Similarity	NPC471362
0.8889	High Similarity	NPC471372
0.8889	High Similarity	NPC472189
0.8868	High Similarity	NPC119550
0.8857	High Similarity	NPC48548
0.8857	High Similarity	NPC135015
0.8857	High Similarity	NPC217921
0.8857	High Similarity	NPC128795
0.8812	High Similarity	NPC471366
0.8812	High Similarity	NPC476800
0.8812	High Similarity	NPC318917
0.8812	High Similarity	NPC472186
0.8713	High Similarity	NPC472188
0.8654	High Similarity	NPC120009
0.8627	High Similarity	NPC474440
0.8585	High Similarity	NPC475074
0.8544	High Similarity	NPC477968
0.8544	High Similarity	NPC477971
0.8544	High Similarity	NPC477972
0.8544	High Similarity	NPC219285
0.8544	High Similarity	NPC161527
0.8544	High Similarity	NPC228251
0.8544	High Similarity	NPC20113
0.8491	Intermediate Similarity	NPC82251
0.8476	Intermediate Similarity	NPC45897
0.8447	Intermediate Similarity	NPC473154
0.8426	Intermediate Similarity	NPC206618
0.8416	Intermediate Similarity	NPC88507
0.8407	Intermediate Similarity	NPC470914
0.8384	Intermediate Similarity	NPC470819
0.8365	Intermediate Similarity	NPC324841
0.8349	Intermediate Similarity	NPC177047
0.8348	Intermediate Similarity	NPC471082
0.8333	Intermediate Similarity	NPC38948
0.8319	Intermediate Similarity	NPC473828
0.8319	Intermediate Similarity	NPC473617
0.8318	Intermediate Similarity	NPC239961
0.83	Intermediate Similarity	NPC469403
0.83	Intermediate Similarity	NPC470817
0.8288	Intermediate Similarity	NPC264153
0.8288	Intermediate Similarity	NPC473159
0.8288	Intermediate Similarity	NPC157441
0.8286	Intermediate Similarity	NPC280991
0.8286	Intermediate Similarity	NPC198992
0.8252	Intermediate Similarity	NPC94905
0.8252	Intermediate Similarity	NPC8954
0.8252	Intermediate Similarity	NPC165632
0.8252	Intermediate Similarity	NPC311166
0.8241	Intermediate Similarity	NPC472390
0.8235	Intermediate Similarity	NPC470255
0.8224	Intermediate Similarity	NPC470768
0.8208	Intermediate Similarity	NPC11956
0.8198	Intermediate Similarity	NPC194951
0.8198	Intermediate Similarity	NPC12046
0.8198	Intermediate Similarity	NPC473125
0.8174	Intermediate Similarity	NPC257610
0.8155	Intermediate Similarity	NPC100892
0.8155	Intermediate Similarity	NPC477970
0.8155	Intermediate Similarity	NPC477969
0.8155	Intermediate Similarity	NPC13924
0.8155	Intermediate Similarity	NPC135224
0.8155	Intermediate Similarity	NPC276110
0.8148	Intermediate Similarity	NPC470767
0.8148	Intermediate Similarity	NPC470763
0.8142	Intermediate Similarity	NPC207637
0.8137	Intermediate Similarity	NPC472812
0.8137	Intermediate Similarity	NPC205034
0.8137	Intermediate Similarity	NPC152778
0.8137	Intermediate Similarity	NPC162615
0.8131	Intermediate Similarity	NPC471887
0.8131	Intermediate Similarity	NPC132395
0.8131	Intermediate Similarity	NPC471886
0.8131	Intermediate Similarity	NPC471888
0.8131	Intermediate Similarity	NPC471365
0.8131	Intermediate Similarity	NPC471885
0.8131	Intermediate Similarity	NPC23584
0.8131	Intermediate Similarity	NPC471364
0.8131	Intermediate Similarity	NPC471450
0.8131	Intermediate Similarity	NPC281378
0.8125	Intermediate Similarity	NPC290608
0.8125	Intermediate Similarity	NPC40133
0.8125	Intermediate Similarity	NPC49413
0.8125	Intermediate Similarity	NPC44298
0.8125	Intermediate Similarity	NPC473128
0.8113	Intermediate Similarity	NPC477717
0.8113	Intermediate Similarity	NPC472554
0.8103	Intermediate Similarity	NPC476204
0.8103	Intermediate Similarity	NPC170084
0.81	Intermediate Similarity	NPC263079
0.8099	Intermediate Similarity	NPC230331
0.8095	Intermediate Similarity	NPC278673
0.8077	Intermediate Similarity	NPC16967
0.807	Intermediate Similarity	NPC203862
0.807	Intermediate Similarity	NPC23046
0.8058	Intermediate Similarity	NPC104925
0.8058	Intermediate Similarity	NPC189513
0.8058	Intermediate Similarity	NPC105490
0.8058	Intermediate Similarity	NPC469491
0.8058	Intermediate Similarity	NPC298973
0.8053	Intermediate Similarity	NPC475163
0.8039	Intermediate Similarity	NPC472811
0.8037	Intermediate Similarity	NPC201191
0.8037	Intermediate Similarity	NPC475344
0.8037	Intermediate Similarity	NPC471889
0.8037	Intermediate Similarity	NPC31058
0.8037	Intermediate Similarity	NPC37207
0.8037	Intermediate Similarity	NPC469606
0.8037	Intermediate Similarity	NPC121423
0.8037	Intermediate Similarity	NPC475038
0.8037	Intermediate Similarity	NPC472815
0.8037	Intermediate Similarity	NPC109195
0.8037	Intermediate Similarity	NPC476471
0.8037	Intermediate Similarity	NPC472552
0.8037	Intermediate Similarity	NPC470571
0.8037	Intermediate Similarity	NPC273005
0.8037	Intermediate Similarity	NPC150463
0.8036	Intermediate Similarity	NPC231797
0.802	Intermediate Similarity	NPC470734
0.802	Intermediate Similarity	NPC261320
0.8019	Intermediate Similarity	NPC477721
0.8019	Intermediate Similarity	NPC477716
0.8017	Intermediate Similarity	NPC48692
0.8017	Intermediate Similarity	NPC135369
0.8	Intermediate Similarity	NPC239547
0.8	Intermediate Similarity	NPC309503
0.8	Intermediate Similarity	NPC155319
0.8	Intermediate Similarity	NPC470515
0.8	Intermediate Similarity	NPC475263
0.8	Intermediate Similarity	NPC125551
0.8	Intermediate Similarity	NPC91197
0.8	Intermediate Similarity	NPC96597
0.7983	Intermediate Similarity	NPC179261
0.7982	Intermediate Similarity	NPC51719
0.7982	Intermediate Similarity	NPC469607
0.7981	Intermediate Similarity	NPC230347
0.7981	Intermediate Similarity	NPC275310
0.7981	Intermediate Similarity	NPC286612
0.7966	Intermediate Similarity	NPC41129
0.7965	Intermediate Similarity	NPC287075
0.7963	Intermediate Similarity	NPC474575
0.7963	Intermediate Similarity	NPC474124
0.7963	Intermediate Similarity	NPC85742
0.7961	Intermediate Similarity	NPC7349
0.7949	Intermediate Similarity	NPC233500
0.7946	Intermediate Similarity	NPC65034
0.7946	Intermediate Similarity	NPC208189
0.7944	Intermediate Similarity	NPC11974
0.7941	Intermediate Similarity	NPC471371
0.7941	Intermediate Similarity	NPC78973
0.7941	Intermediate Similarity	NPC310479
0.7941	Intermediate Similarity	NPC471370
0.7941	Intermediate Similarity	NPC220216
0.7931	Intermediate Similarity	NPC470911
0.7931	Intermediate Similarity	NPC304260
0.7931	Intermediate Similarity	NPC153085
0.7931	Intermediate Similarity	NPC268326
0.7931	Intermediate Similarity	NPC5883
0.7931	Intermediate Similarity	NPC470517
0.7931	Intermediate Similarity	NPC29639
0.7931	Intermediate Similarity	NPC219656
0.7931	Intermediate Similarity	NPC44899
0.7931	Intermediate Similarity	NPC470915
0.7928	Intermediate Similarity	NPC475586
0.7928	Intermediate Similarity	NPC112457

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 NPC224660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1312
0.2-0.3	3694
0.3-0.4	2599
0.4-0.5	893
0.5-0.6	283
0.6-0.7	185
0.7-0.8	19
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
0.8103	Intermediate Similarity	NPD7503	Approved
0.7838	Intermediate Similarity	NPD6686	Approved
0.7797	Intermediate Similarity	NPD8033	Approved
0.7712	Intermediate Similarity	NPD8294	Approved
0.7712	Intermediate Similarity	NPD8377	Approved
0.7692	Intermediate Similarity	NPD7327	Approved
0.7692	Intermediate Similarity	NPD7328	Approved
0.7647	Intermediate Similarity	NPD8296	Approved
0.7647	Intermediate Similarity	NPD8380	Approved
0.7647	Intermediate Similarity	NPD8335	Approved
0.7647	Intermediate Similarity	NPD8378	Approved
0.7647	Intermediate Similarity	NPD8379	Approved
0.7627	Intermediate Similarity	NPD7516	Approved
0.7593	Intermediate Similarity	NPD7638	Approved
0.7523	Intermediate Similarity	NPD7640	Approved
0.7523	Intermediate Similarity	NPD7639	Approved
0.7431	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4225	Approved
0.7429	Intermediate Similarity	NPD7838	Discovery
0.7364	Intermediate Similarity	NPD6648	Approved
0.7355	Intermediate Similarity	NPD8513	Phase 3
0.7355	Intermediate Similarity	NPD8516	Approved
0.7355	Intermediate Similarity	NPD8515	Approved
0.7355	Intermediate Similarity	NPD8517	Approved
0.7353	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5344	Discontinued
0.7258	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7736	Approved
0.7119	Intermediate Similarity	NPD6882	Approved
0.7087	Intermediate Similarity	NPD7319	Approved
0.7016	Intermediate Similarity	NPD6370	Approved
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6412	Phase 2
0.696	Remote Similarity	NPD8328	Phase 3
0.693	Remote Similarity	NPD7632	Discontinued
0.6929	Remote Similarity	NPD8293	Discontinued
0.6917	Remote Similarity	NPD8133	Approved
0.6905	Remote Similarity	NPD7492	Approved
0.6885	Remote Similarity	NPD7115	Discovery
0.6881	Remote Similarity	NPD7637	Suspended
0.6864	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6054	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6833	Remote Similarity	NPD8297	Approved
0.6818	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD5779	Approved
0.6807	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7078	Approved
0.6797	Remote Similarity	NPD8074	Phase 3
0.6792	Remote Similarity	NPD1694	Approved
0.678	Remote Similarity	NPD6899	Approved
0.678	Remote Similarity	NPD6881	Approved
0.6757	Remote Similarity	NPD7748	Approved
0.675	Remote Similarity	NPD6650	Approved
0.675	Remote Similarity	NPD6649	Approved
0.675	Remote Similarity	NPD8130	Phase 1
0.6748	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6009	Approved
0.6726	Remote Similarity	NPD7902	Approved
0.6698	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD6698	Approved
0.6636	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD8264	Approved
0.6614	Remote Similarity	NPD5988	Approved
0.6612	Remote Similarity	NPD6847	Approved
0.6612	Remote Similarity	NPD6617	Approved
0.6612	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6869	Approved
0.661	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD5739	Approved
0.661	Remote Similarity	NPD6402	Approved
0.661	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6695	Phase 3
0.6587	Remote Similarity	NPD6319	Approved
0.6587	Remote Similarity	NPD6059	Approved
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6013	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6583	Remote Similarity	NPD6012	Approved
0.6583	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD6411	Approved
0.6577	Remote Similarity	NPD7515	Phase 2
0.6562	Remote Similarity	NPD6067	Discontinued
0.6557	Remote Similarity	NPD6053	Discontinued
0.6555	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6399	Phase 3
0.6514	Remote Similarity	NPD7750	Discontinued
0.6509	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD6011	Approved
0.65	Remote Similarity	NPD7320	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.6466	Remote Similarity	NPD7260	Phase 2
0.646	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7900	Approved
0.6434	Remote Similarity	NPD7829	Approved
0.6434	Remote Similarity	NPD7830	Approved
0.6429	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD6079	Approved
0.6417	Remote Similarity	NPD5701	Approved
0.6417	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6101	Approved
0.6396	Remote Similarity	NPD6051	Approved
0.6396	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7645	Phase 2
0.6381	Remote Similarity	NPD6929	Approved
0.6364	Remote Similarity	NPD7524	Approved
0.6356	Remote Similarity	NPD5211	Phase 2
0.6348	Remote Similarity	NPD7839	Suspended
0.6325	Remote Similarity	NPD4696	Approved
0.6325	Remote Similarity	NPD5286	Approved
0.6325	Remote Similarity	NPD5285	Approved
0.6321	Remote Similarity	NPD7525	Registered
0.6321	Remote Similarity	NPD6930	Phase 2
0.6321	Remote Similarity	NPD7514	Phase 3
0.6321	Remote Similarity	NPD7332	Phase 2
0.6321	Remote Similarity	NPD6931	Approved
0.6308	Remote Similarity	NPD7604	Phase 2
0.6293	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6084	Phase 2
0.6286	Remote Similarity	NPD7145	Approved
0.6279	Remote Similarity	NPD5983	Phase 2
0.6273	Remote Similarity	NPD3618	Phase 1
0.6262	Remote Similarity	NPD6902	Approved
0.626	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD5328	Approved
0.6232	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5225	Approved
0.6218	Remote Similarity	NPD5226	Approved
0.6218	Remote Similarity	NPD5224	Approved
0.6218	Remote Similarity	NPD4633	Approved
0.6216	Remote Similarity	NPD4251	Approved
0.6216	Remote Similarity	NPD4250	Approved
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5221	Approved
0.6207	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5222	Approved
0.6203	Remote Similarity	NPD7799	Discontinued
0.6195	Remote Similarity	NPD5785	Approved
0.619	Remote Similarity	NPD6925	Approved
0.619	Remote Similarity	NPD6932	Approved
0.619	Remote Similarity	NPD5776	Phase 2
0.6181	Remote Similarity	NPD7625	Phase 1
0.6176	Remote Similarity	NPD6845	Suspended
0.6172	Remote Similarity	NPD6335	Approved
0.6168	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5175	Approved
0.6167	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD8039	Approved
0.6154	Remote Similarity	NPD6942	Approved
0.6154	Remote Similarity	NPD7339	Approved
0.6142	Remote Similarity	NPD6868	Approved
0.6142	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD5284	Approved
0.614	Remote Similarity	NPD5281	Approved
0.614	Remote Similarity	NPD8034	Phase 2
0.614	Remote Similarity	NPD7087	Discontinued
0.614	Remote Similarity	NPD8035	Phase 2
0.6134	Remote Similarity	NPD5223	Approved
0.6129	Remote Similarity	NPD4634	Approved
0.6126	Remote Similarity	NPD6684	Approved
0.6126	Remote Similarity	NPD7521	Approved
0.6126	Remote Similarity	NPD5330	Approved
0.6126	Remote Similarity	NPD7146	Approved
0.6126	Remote Similarity	NPD7334	Approved
0.6126	Remote Similarity	NPD6409	Approved
0.6126	Remote Similarity	NPD4249	Approved
0.6121	Remote Similarity	NPD5695	Phase 3
0.6119	Remote Similarity	NPD6033	Approved
0.6098	Remote Similarity	NPD4729	Approved
0.6098	Remote Similarity	NPD4730	Approved
0.6095	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6317	Approved
0.6091	Remote Similarity	NPD4786	Approved
0.609	Remote Similarity	NPD8451	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.6071	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3573	Approved
0.6058	Remote Similarity	NPD6926	Approved
0.6058	Remote Similarity	NPD6924	Approved
0.6055	Remote Similarity	NPD3667	Approved
0.6055	Remote Similarity	NPD5209	Approved
0.605	Remote Similarity	NPD4700	Approved
0.6047	Remote Similarity	NPD7641	Discontinued
0.6047	Remote Similarity	NPD6314	Approved
0.6047	Remote Similarity	NPD6313	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