NPASS Compound

Structure

NPC472554 OpenBabel07101719252D 35 37 0 0 1 0 0 0 0 0999 V2000 3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3770 -2.3507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1271 -1.9390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9737 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1330 0.4708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4225 1.6319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8302 0.1101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3175 -2.0987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0735 0.7228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8810 -0.4697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3948 1.5809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0060 -2.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0076 2.3376 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4868 0.8432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6468 0.6404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5695 -1.1582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 25 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 14 2 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 32 1 0 0 0 0 14 24 1 0 0 0 0 15 27 2 0 0 0 0 15 33 1 0 0 0 0 16 28 2 0 0 0 0 16 34 1 0 0 0 0 17 29 2 0 0 0 0 17 35 1 0 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 11 1 1 0 0 0 20 25 1 0 0 0 0 20 33 1 0 0 0 0 21 30 2 0 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 6 0 0 0 22 34 1 0 0 0 0 23 26 1 1 0 0 0 23 35 1 0 0 0 0 24 5 1 6 0 0 0 25 26 1 6 0 0 0 26 7 1 6 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	495.876
LogP:	2.676
LogD:	1.884
LogS:	-4.124
# Rotatable Bonds:	9
TPSA:	132.5
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	5.189
Fsp3:	0.654
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:	-5.067
MDCK Permeability:	6.934449629625306e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.326
Human Intestinal Absorption (HIA):	0.804
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	77.26417541503906%
Volume Distribution (VD):	1.051
Pgp-substrate:	24.86561393737793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.638
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	3.322
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.721
Drug-inuced Liver Injury (DILI):	0.579
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.251
Skin Sensitization:	0.159
Carcinogencity:	0.288
Eye Corrosion:	0.039
Eye Irritation:	0.033
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC472554

Natural Product ID:	NPC472554
*Common Name:**	RPLOTRILOONHRJ-GUQPKPMOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RPLOTRILOONHRJ-GUQPKPMOSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-14-9-8-10-19-24(14,5)22(34-16(3)28)23(35-17(4)29)26(7,31)25(19,6)20(33-15(2)27)11-18-12-21(30)32-13-18/h9,12,19-20,22-23,31H,8,10-11,13H2,1-7H3/t19-,20-,22-,23-,24-,25-,26-/m0/s1
SMILES:	CC(=O)O[C@H]([C@]1(C)[C@H]2CCC=C([C@]2(C)[C@H]([C@@H]([C@]1(C)O)OC(=O)C)OC(=O)C)C)CC1=CC(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577090
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	<	50.0	%	PMID[454024]

☑ 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 NPC472554 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	201
0.1-0.2	1367
0.2-0.3	4200
0.3-0.4	6570
0.4-0.5	14340
0.5-0.6	7560
0.6-0.7	6344
0.7-0.8	1945
0.8-0.85	142
0.85-0.9	22
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC472552
0.9479	High Similarity	NPC11956
0.9381	High Similarity	NPC23584
0.9271	High Similarity	NPC38855
0.92	High Similarity	NPC50124
0.9053	High Similarity	NPC276110
0.902	High Similarity	NPC177047
0.9	High Similarity	NPC51719
0.9	High Similarity	NPC471206
0.898	High Similarity	NPC11974
0.8911	High Similarity	NPC122816
0.8911	High Similarity	NPC471205
0.8878	High Similarity	NPC188968
0.8866	High Similarity	NPC473244
0.8842	High Similarity	NPC7349
0.8824	High Similarity	NPC38948
0.8824	High Similarity	NPC181994
0.88	High Similarity	NPC281378
0.88	High Similarity	NPC474124
0.8788	High Similarity	NPC475617
0.8763	High Similarity	NPC129569
0.8763	High Similarity	NPC284194
0.8763	High Similarity	NPC211810
0.8763	High Similarity	NPC471765
0.8763	High Similarity	NPC221801
0.875	High Similarity	NPC105490
0.8738	High Similarity	NPC475586
0.8738	High Similarity	NPC206618
0.8725	High Similarity	NPC187435
0.8725	High Similarity	NPC473586
0.8725	High Similarity	NPC67321
0.8713	High Similarity	NPC473543
0.87	High Similarity	NPC475344
0.87	High Similarity	NPC476471
0.8687	High Similarity	NPC271295
0.8687	High Similarity	NPC79303
0.8673	High Similarity	NPC199099
0.8646	High Similarity	NPC53555
0.8646	High Similarity	NPC110022
0.8641	High Similarity	NPC475263
0.8614	High Similarity	NPC120009
0.8614	High Similarity	NPC474575
0.8614	High Similarity	NPC473523
0.8602	High Similarity	NPC471219
0.8586	High Similarity	NPC278673
0.8571	High Similarity	NPC165632
0.8571	High Similarity	NPC472995
0.8557	High Similarity	NPC140277
0.8557	High Similarity	NPC105375
0.8557	High Similarity	NPC472360
0.8557	High Similarity	NPC472416
0.8557	High Similarity	NPC182826
0.8526	High Similarity	NPC246028
0.8515	High Similarity	NPC109195
0.8515	High Similarity	NPC476081
0.8515	High Similarity	NPC475038
0.8515	High Similarity	NPC470972
0.85	High Similarity	NPC272223
0.85	High Similarity	NPC473510
0.85	High Similarity	NPC230546
0.8491	Intermediate Similarity	NPC328074
0.8491	Intermediate Similarity	NPC470025
0.8491	Intermediate Similarity	NPC317460
0.8491	Intermediate Similarity	NPC321272
0.8485	Intermediate Similarity	NPC51499
0.8485	Intermediate Similarity	NPC210337
0.8485	Intermediate Similarity	NPC205143
0.8476	Intermediate Similarity	NPC316708
0.8462	Intermediate Similarity	NPC48548
0.8462	Intermediate Similarity	NPC135015
0.8462	Intermediate Similarity	NPC128795
0.8462	Intermediate Similarity	NPC217921
0.8462	Intermediate Similarity	NPC306265
0.8447	Intermediate Similarity	NPC88349
0.8447	Intermediate Similarity	NPC111952
0.8438	Intermediate Similarity	NPC78973
0.8431	Intermediate Similarity	NPC45897
0.8431	Intermediate Similarity	NPC474822
0.8411	Intermediate Similarity	NPC470027
0.8411	Intermediate Similarity	NPC471204
0.84	Intermediate Similarity	NPC325229
0.84	Intermediate Similarity	NPC275086
0.8396	Intermediate Similarity	NPC17791
0.8396	Intermediate Similarity	NPC470026
0.8384	Intermediate Similarity	NPC209297
0.8384	Intermediate Similarity	NPC194132
0.8384	Intermediate Similarity	NPC88009
0.8384	Intermediate Similarity	NPC475380
0.8381	Intermediate Similarity	NPC316974
0.8381	Intermediate Similarity	NPC40728
0.8365	Intermediate Similarity	NPC88013
0.8365	Intermediate Similarity	NPC143609
0.8365	Intermediate Similarity	NPC125423
0.8349	Intermediate Similarity	NPC203862
0.8333	Intermediate Similarity	NPC295791
0.8333	Intermediate Similarity	NPC261320
0.8333	Intermediate Similarity	NPC82876
0.8333	Intermediate Similarity	NPC472815
0.8317	Intermediate Similarity	NPC324841
0.8317	Intermediate Similarity	NPC16601
0.8317	Intermediate Similarity	NPC474190
0.83	Intermediate Similarity	NPC472998
0.83	Intermediate Similarity	NPC311241
0.83	Intermediate Similarity	NPC254121
0.83	Intermediate Similarity	NPC475446
0.83	Intermediate Similarity	NPC120446
0.83	Intermediate Similarity	NPC100912
0.8286	Intermediate Similarity	NPC88701
0.8286	Intermediate Similarity	NPC469916
0.8286	Intermediate Similarity	NPC472439
0.8286	Intermediate Similarity	NPC311223
0.8283	Intermediate Similarity	NPC469583
0.8273	Intermediate Similarity	NPC218093
0.8269	Intermediate Similarity	NPC220217
0.8269	Intermediate Similarity	NPC470980
0.8269	Intermediate Similarity	NPC119855
0.8269	Intermediate Similarity	NPC239961
0.8269	Intermediate Similarity	NPC186668
0.8257	Intermediate Similarity	NPC471816
0.8252	Intermediate Similarity	NPC97487
0.8252	Intermediate Similarity	NPC196471
0.8252	Intermediate Similarity	NPC472821
0.8252	Intermediate Similarity	NPC159533
0.8252	Intermediate Similarity	NPC189588
0.8252	Intermediate Similarity	NPC187302
0.8252	Intermediate Similarity	NPC120321
0.8252	Intermediate Similarity	NPC10232
0.8247	Intermediate Similarity	NPC220216
0.8241	Intermediate Similarity	NPC477126
0.8235	Intermediate Similarity	NPC198992
0.8235	Intermediate Similarity	NPC235920
0.8235	Intermediate Similarity	NPC96784
0.8229	Intermediate Similarity	NPC93411
0.8224	Intermediate Similarity	NPC470076
0.8218	Intermediate Similarity	NPC477875
0.8218	Intermediate Similarity	NPC222303
0.8218	Intermediate Similarity	NPC107806
0.8218	Intermediate Similarity	NPC477876
0.8218	Intermediate Similarity	NPC72647
0.8218	Intermediate Similarity	NPC475068
0.8211	Intermediate Similarity	NPC131813
0.8211	Intermediate Similarity	NPC102996
0.8208	Intermediate Similarity	NPC284828
0.8208	Intermediate Similarity	NPC299590
0.8208	Intermediate Similarity	NPC5475
0.8208	Intermediate Similarity	NPC173905
0.8208	Intermediate Similarity	NPC472216
0.82	Intermediate Similarity	NPC475304
0.82	Intermediate Similarity	NPC472996
0.82	Intermediate Similarity	NPC472997
0.8198	Intermediate Similarity	NPC291820
0.8198	Intermediate Similarity	NPC81222
0.819	Intermediate Similarity	NPC319438
0.819	Intermediate Similarity	NPC472390
0.819	Intermediate Similarity	NPC475074
0.819	Intermediate Similarity	NPC216636
0.819	Intermediate Similarity	NPC475781
0.819	Intermediate Similarity	NPC109376
0.8182	Intermediate Similarity	NPC469491
0.8182	Intermediate Similarity	NPC87250
0.8182	Intermediate Similarity	NPC142066
0.8182	Intermediate Similarity	NPC471351
0.8182	Intermediate Similarity	NPC471353
0.8182	Intermediate Similarity	NPC158344
0.8182	Intermediate Similarity	NPC473852
0.8182	Intermediate Similarity	NPC161998
0.8182	Intermediate Similarity	NPC309034
0.8182	Intermediate Similarity	NPC243196
0.8182	Intermediate Similarity	NPC474418
0.8182	Intermediate Similarity	NPC196429
0.8182	Intermediate Similarity	NPC473590
0.8182	Intermediate Similarity	NPC471355
0.8182	Intermediate Similarity	NPC244402
0.8182	Intermediate Similarity	NPC157376
0.8182	Intermediate Similarity	NPC99728
0.8182	Intermediate Similarity	NPC471354
0.8182	Intermediate Similarity	NPC50305
0.8182	Intermediate Similarity	NPC34390
0.8182	Intermediate Similarity	NPC473968
0.8182	Intermediate Similarity	NPC77319
0.8182	Intermediate Similarity	NPC84987
0.8182	Intermediate Similarity	NPC27507
0.8182	Intermediate Similarity	NPC152615
0.8173	Intermediate Similarity	NPC473577
0.8173	Intermediate Similarity	NPC146731
0.8173	Intermediate Similarity	NPC475585
0.8173	Intermediate Similarity	NPC474550
0.8172	Intermediate Similarity	NPC471218
0.8163	Intermediate Similarity	NPC124374
0.8155	Intermediate Similarity	NPC162973
0.8155	Intermediate Similarity	NPC258547
0.8155	Intermediate Similarity	NPC121423
0.8155	Intermediate Similarity	NPC273668
0.8155	Intermediate Similarity	NPC165578
0.8155	Intermediate Similarity	NPC283343
0.8148	Intermediate Similarity	NPC269530
0.8148	Intermediate Similarity	NPC470063
0.8144	Intermediate Similarity	NPC20946
0.8144	Intermediate Similarity	NPC314727
0.8137	Intermediate Similarity	NPC274643

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 NPC472554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1635
0.2-0.3	3722
0.3-0.4	2284
0.4-0.5	885
0.5-0.6	281
0.6-0.7	146
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
0.8235	Intermediate Similarity	NPD5344	Discontinued
0.8208	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7516	Approved
0.8131	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7328	Approved
0.8108	Intermediate Similarity	NPD7327	Approved
0.7961	Intermediate Similarity	NPD6648	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8033	Approved
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7864	Intermediate Similarity	NPD4225	Approved
0.7864	Intermediate Similarity	NPD7638	Approved
0.785	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD8294	Approved
0.7807	Intermediate Similarity	NPD8377	Approved
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD6686	Approved
0.7586	Intermediate Similarity	NPD7503	Approved
0.7479	Intermediate Similarity	NPD7507	Approved
0.7438	Intermediate Similarity	NPD7319	Approved
0.7391	Intermediate Similarity	NPD7115	Discovery
0.7353	Intermediate Similarity	NPD6698	Approved
0.7353	Intermediate Similarity	NPD7838	Discovery
0.7353	Intermediate Similarity	NPD46	Approved
0.7228	Intermediate Similarity	NPD7524	Approved
0.7156	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6319	Approved
0.7043	Intermediate Similarity	NPD8297	Approved
0.6983	Remote Similarity	NPD4632	Approved
0.6981	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD5739	Approved
0.6964	Remote Similarity	NPD7128	Approved
0.6964	Remote Similarity	NPD6675	Approved
0.6964	Remote Similarity	NPD6402	Approved
0.6944	Remote Similarity	NPD7902	Approved
0.6931	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6372	Approved
0.693	Remote Similarity	NPD6373	Approved
0.693	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6051	Approved
0.6903	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6412	Phase 2
0.69	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6053	Discontinued
0.6887	Remote Similarity	NPD6399	Phase 3
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6371	Approved
0.6842	Remote Similarity	NPD6899	Approved
0.6842	Remote Similarity	NPD6881	Approved
0.6842	Remote Similarity	NPD7320	Approved
0.6838	Remote Similarity	NPD8133	Approved
0.6832	Remote Similarity	NPD6695	Phase 3
0.6814	Remote Similarity	NPD6008	Approved
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6649	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6792	Remote Similarity	NPD7515	Phase 2
0.6757	Remote Similarity	NPD4159	Approved
0.6754	Remote Similarity	NPD5701	Approved
0.6754	Remote Similarity	NPD5697	Approved
0.6752	Remote Similarity	NPD6882	Approved
0.6748	Remote Similarity	NPD8328	Phase 3
0.6724	Remote Similarity	NPD7102	Approved
0.6724	Remote Similarity	NPD7290	Approved
0.6724	Remote Similarity	NPD6883	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.67	Remote Similarity	NPD7525	Registered
0.6699	Remote Similarity	NPD1694	Approved
0.6698	Remote Similarity	NPD3168	Discontinued
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6617	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD6013	Approved
0.6638	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6083	Phase 2
0.6636	Remote Similarity	NPD6084	Phase 2
0.6613	Remote Similarity	NPD7604	Phase 2
0.6606	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD7645	Phase 2
0.6587	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD8293	Discontinued
0.6585	Remote Similarity	NPD5983	Phase 2
0.6585	Remote Similarity	NPD6921	Approved
0.6574	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD7750	Discontinued
0.6552	Remote Similarity	NPD6011	Approved
0.6535	Remote Similarity	NPD6930	Phase 2
0.6535	Remote Similarity	NPD6931	Approved
0.6535	Remote Similarity	NPD7736	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6529	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7260	Phase 2
0.6508	Remote Similarity	NPD6336	Discontinued
0.6486	Remote Similarity	NPD4755	Approved
0.6481	Remote Similarity	NPD7983	Approved
0.6476	Remote Similarity	NPD6409	Approved
0.6476	Remote Similarity	NPD7521	Approved
0.6476	Remote Similarity	NPD7146	Approved
0.6476	Remote Similarity	NPD3618	Phase 1
0.6476	Remote Similarity	NPD5330	Approved
0.6476	Remote Similarity	NPD6684	Approved
0.6476	Remote Similarity	NPD7334	Approved
0.6457	Remote Similarity	NPD8074	Phase 3
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD6016	Approved
0.6449	Remote Similarity	NPD5328	Approved
0.6449	Remote Similarity	NPD7625	Phase 1
0.6441	Remote Similarity	NPD4634	Approved
0.6436	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6422	Remote Similarity	NPD4202	Approved
0.6415	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5211	Phase 2
0.6404	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5988	Approved
0.6373	Remote Similarity	NPD7514	Phase 3
0.6373	Remote Similarity	NPD7332	Phase 2
0.6372	Remote Similarity	NPD5285	Approved
0.6372	Remote Similarity	NPD5286	Approved
0.6372	Remote Similarity	NPD4700	Approved
0.6372	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD7339	Approved
0.6364	Remote Similarity	NPD6942	Approved
0.6355	Remote Similarity	NPD5737	Approved
0.6355	Remote Similarity	NPD6903	Approved
0.6355	Remote Similarity	NPD6672	Approved
0.6355	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8035	Phase 2
0.633	Remote Similarity	NPD5693	Phase 1
0.633	Remote Similarity	NPD7087	Discontinued
0.633	Remote Similarity	NPD6079	Approved
0.633	Remote Similarity	NPD8034	Phase 2
0.633	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD6274	Approved
0.6306	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6933	Approved
0.6293	Remote Similarity	NPD5141	Approved
0.629	Remote Similarity	NPD7101	Approved
0.629	Remote Similarity	NPD7100	Approved
0.6286	Remote Similarity	NPD4786	Approved
0.6286	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3573	Approved
0.6261	Remote Similarity	NPD5226	Approved
0.6261	Remote Similarity	NPD5225	Approved
0.6261	Remote Similarity	NPD5224	Approved
0.6261	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD6640	Phase 3
0.6239	Remote Similarity	NPD5357	Phase 1
0.6239	Remote Similarity	NPD4767	Approved
0.6238	Remote Similarity	NPD6932	Approved
0.6238	Remote Similarity	NPD6925	Approved
0.6238	Remote Similarity	NPD5776	Phase 2
0.6226	Remote Similarity	NPD6893	Approved
0.622	Remote Similarity	NPD6067	Discontinued
0.6216	Remote Similarity	NPD5282	Discontinued
0.6212	Remote Similarity	NPD6845	Suspended
0.621	Remote Similarity	NPD6335	Approved
0.6207	Remote Similarity	NPD5175	Approved
0.6207	Remote Similarity	NPD5174	Approved
0.62	Remote Similarity	NPD8264	Approved
0.619	Remote Similarity	NPD6909	Approved
0.619	Remote Similarity	NPD6908	Approved
0.6182	Remote Similarity	NPD5284	Approved
0.6182	Remote Similarity	NPD5281	Approved
0.6176	Remote Similarity	NPD7145	Approved
0.6174	Remote Similarity	NPD5223	Approved
0.6161	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD6902	Approved
0.6154	Remote Similarity	NPD6898	Phase 1
0.6147	Remote Similarity	NPD6080	Approved
0.6147	Remote Similarity	NPD6904	Approved
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD6673	Approved
0.6147	Remote Similarity	NPD4753	Phase 2
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)

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