NPASS Compound

Structure

NPC472025 OpenBabel07101718222D 28 29 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 2 1 6 0 0 0 9 27 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 6 0 0 0 11 8 1 1 0 0 0 11 13 1 0 0 0 0 11 28 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 1 0 0 0 13 14 1 0 0 0 0 13 21 1 6 0 0 0 14 16 1 0 0 0 0 14 22 1 1 0 0 0 15 17 1 0 0 0 0 15 23 1 6 0 0 0 16 18 1 0 0 0 0 16 24 1 6 0 0 0 17 25 1 0 0 0 0 17 26 1 1 0 0 0 18 27 1 1 0 0 0 18 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.22
Volume:	390.674
LogP:	0.068
LogD:	-0.066
LogS:	-1.899
# Rotatable Bonds:	9
TPSA:	158.3
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	4.438
Fsp3:	1.0
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:	-5.471
MDCK Permeability:	5.891158798476681e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.936
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	48.56029510498047%
Volume Distribution (VD):	0.455
Pgp-substrate:	35.799217224121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.176
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.004
Half-life (T1/2):	0.729

ADMET: Toxicity

hERG Blockers:	0.322
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.454
Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.924
Carcinogencity:	0.098
Eye Corrosion:	0.007
Eye Irritation:	0.424
Respiratory Toxicity:	0.137

Download Data

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

Natural Product: NPC472025

Natural Product ID:	NPC472025
*Common Name:**	CMNGMGGJQXLNNS-BJNPHDPWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CMNGMGGJQXLNNS-BJNPHDPWSA-N
Standard InCHI:	InChI=1S/C18H34O10/c1-3-4-5-6-9(2)27-18-16(24)14(22)13(21)11(28-18)8-26-17-15(23)12(20)10(19)7-25-17/h9-24H,3-8H2,1-2H3/t9-,10+,11+,12-,13+,14-,15+,16+,17-,18+/m0/s1
SMILES:	CCCCCC(C)OC1C(C(C(C(O1)COC2C(C(C(CO2)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326717
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	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	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Inhibition	=	8.54	%	PMID[521745]
NPT35	Others	n.a.	""	Activity	=	0.48	uM	PMID[521745]
NPT35	Others	n.a.	""	Activity	=	2.26	uM	PMID[521745]
NPT35	Others	n.a.	""	Activity	=	0.17	uM	PMID[521745]
NPT35	Others	n.a.	""	Activity	=	0.59	uM	PMID[521745]
NPT35	Others	n.a.	""	Activity	=	20.58	%	PMID[521745]

☑ 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 NPC472025 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	856
0.1-0.2	7443
0.2-0.3	16819
0.3-0.4	10860
0.4-0.5	5091
0.5-0.6	1293
0.6-0.7	212
0.7-0.8	63
0.8-0.85	18
0.85-0.9	24
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC477757
0.9464	High Similarity	NPC477763
0.9464	High Similarity	NPC477755
0.9464	High Similarity	NPC477762
0.9464	High Similarity	NPC477753
0.9464	High Similarity	NPC477750
0.9434	High Similarity	NPC303727
0.9245	High Similarity	NPC246558
0.9245	High Similarity	NPC58629
0.9245	High Similarity	NPC89145
0.9245	High Similarity	NPC107914
0.9245	High Similarity	NPC145112
0.9245	High Similarity	NPC269166
0.9245	High Similarity	NPC67660
0.9245	High Similarity	NPC242073
0.9245	High Similarity	NPC157514
0.9245	High Similarity	NPC165198
0.9107	High Similarity	NPC34877
0.9107	High Similarity	NPC317023
0.9107	High Similarity	NPC290179
0.9091	High Similarity	NPC148424
0.8868	High Similarity	NPC124963
0.8868	High Similarity	NPC326533
0.8868	High Similarity	NPC233726
0.8868	High Similarity	NPC23134
0.8833	High Similarity	NPC471761
0.8833	High Similarity	NPC190418
0.8833	High Similarity	NPC471760
0.8793	High Similarity	NPC472026
0.8689	High Similarity	NPC477756
0.8689	High Similarity	NPC477751
0.8689	High Similarity	NPC477752
0.8689	High Similarity	NPC477764
0.8548	High Similarity	NPC477761
0.8548	High Similarity	NPC477760
0.8548	High Similarity	NPC477759
0.8548	High Similarity	NPC477754
0.8548	High Similarity	NPC477758
0.8545	High Similarity	NPC323361
0.8545	High Similarity	NPC130683
0.8525	High Similarity	NPC12040
0.8525	High Similarity	NPC76881
0.8491	Intermediate Similarity	NPC282143
0.8491	Intermediate Similarity	NPC42503
0.8491	Intermediate Similarity	NPC299781
0.8491	Intermediate Similarity	NPC157193
0.8413	Intermediate Similarity	NPC50228
0.8413	Intermediate Similarity	NPC97736
0.8413	Intermediate Similarity	NPC67099
0.8361	Intermediate Similarity	NPC6848
0.8302	Intermediate Similarity	NPC14144
0.8281	Intermediate Similarity	NPC241265
0.8281	Intermediate Similarity	NPC211428
0.8281	Intermediate Similarity	NPC285003
0.8276	Intermediate Similarity	NPC219040
0.8226	Intermediate Similarity	NPC147292
0.8154	Intermediate Similarity	NPC52268
0.8154	Intermediate Similarity	NPC474078
0.8154	Intermediate Similarity	NPC53760
0.8125	Intermediate Similarity	NPC250619
0.8113	Intermediate Similarity	NPC277475
0.8113	Intermediate Similarity	NPC321087
0.8	Intermediate Similarity	NPC323574
0.7969	Intermediate Similarity	NPC206601
0.7925	Intermediate Similarity	NPC199857
0.7925	Intermediate Similarity	NPC92246
0.7925	Intermediate Similarity	NPC289758
0.7925	Intermediate Similarity	NPC176017
0.7925	Intermediate Similarity	NPC285364
0.7925	Intermediate Similarity	NPC255377
0.7925	Intermediate Similarity	NPC73906
0.7925	Intermediate Similarity	NPC165846
0.7925	Intermediate Similarity	NPC69445
0.7925	Intermediate Similarity	NPC21209
0.791	Intermediate Similarity	NPC169085
0.791	Intermediate Similarity	NPC163812
0.791	Intermediate Similarity	NPC39266
0.791	Intermediate Similarity	NPC206823
0.791	Intermediate Similarity	NPC9763
0.791	Intermediate Similarity	NPC225748
0.7833	Intermediate Similarity	NPC322855
0.7833	Intermediate Similarity	NPC320032
0.7818	Intermediate Similarity	NPC82512
0.7705	Intermediate Similarity	NPC143326
0.7647	Intermediate Similarity	NPC55652
0.7619	Intermediate Similarity	NPC325773
0.7619	Intermediate Similarity	NPC277570
0.7581	Intermediate Similarity	NPC155457
0.7571	Intermediate Similarity	NPC477350
0.7547	Intermediate Similarity	NPC320240
0.7547	Intermediate Similarity	NPC70756
0.75	Intermediate Similarity	NPC184550
0.75	Intermediate Similarity	NPC185419
0.7465	Intermediate Similarity	NPC476781
0.7465	Intermediate Similarity	NPC476782
0.7465	Intermediate Similarity	NPC476783
0.7465	Intermediate Similarity	NPC216883
0.7455	Intermediate Similarity	NPC230789
0.7455	Intermediate Similarity	NPC252918
0.7391	Intermediate Similarity	NPC291228
0.7391	Intermediate Similarity	NPC308096
0.7361	Intermediate Similarity	NPC477326
0.7361	Intermediate Similarity	NPC477328
0.7361	Intermediate Similarity	NPC109887
0.7361	Intermediate Similarity	NPC477325
0.7361	Intermediate Similarity	NPC146380
0.7361	Intermediate Similarity	NPC113745
0.7361	Intermediate Similarity	NPC477323
0.7361	Intermediate Similarity	NPC477320
0.7361	Intermediate Similarity	NPC477329
0.7361	Intermediate Similarity	NPC475425
0.7361	Intermediate Similarity	NPC281563
0.7361	Intermediate Similarity	NPC477330
0.7358	Intermediate Similarity	NPC134252
0.7358	Intermediate Similarity	NPC317182
0.7358	Intermediate Similarity	NPC291502
0.7358	Intermediate Similarity	NPC86191
0.7358	Intermediate Similarity	NPC213159
0.7358	Intermediate Similarity	NPC298699
0.7353	Intermediate Similarity	NPC471879
0.7344	Intermediate Similarity	NPC268243
0.7324	Intermediate Similarity	NPC279575
0.7288	Intermediate Similarity	NPC317501
0.7288	Intermediate Similarity	NPC314821
0.7288	Intermediate Similarity	NPC317626
0.7286	Intermediate Similarity	NPC308489
0.7286	Intermediate Similarity	NPC166250
0.7286	Intermediate Similarity	NPC138273
0.726	Intermediate Similarity	NPC85759
0.726	Intermediate Similarity	NPC146992
0.726	Intermediate Similarity	NPC22742
0.726	Intermediate Similarity	NPC294748
0.726	Intermediate Similarity	NPC158302
0.726	Intermediate Similarity	NPC477346
0.726	Intermediate Similarity	NPC477344
0.7231	Intermediate Similarity	NPC13143
0.7231	Intermediate Similarity	NPC294813
0.7231	Intermediate Similarity	NPC31496
0.7162	Intermediate Similarity	NPC267592
0.7162	Intermediate Similarity	NPC471420
0.7123	Intermediate Similarity	NPC272841
0.7067	Intermediate Similarity	NPC477319
0.7067	Intermediate Similarity	NPC123204
0.7067	Intermediate Similarity	NPC477331
0.7067	Intermediate Similarity	NPC269318
0.7067	Intermediate Similarity	NPC477318
0.7067	Intermediate Similarity	NPC290012
0.7067	Intermediate Similarity	NPC472205
0.7067	Intermediate Similarity	NPC119583
0.7067	Intermediate Similarity	NPC472201
0.7067	Intermediate Similarity	NPC27289
0.7067	Intermediate Similarity	NPC472204
0.7067	Intermediate Similarity	NPC477347
0.7067	Intermediate Similarity	NPC238056
0.7067	Intermediate Similarity	NPC169345
0.7067	Intermediate Similarity	NPC307400
0.7067	Intermediate Similarity	NPC184915
0.7067	Intermediate Similarity	NPC224953
0.7067	Intermediate Similarity	NPC475327
0.7067	Intermediate Similarity	NPC297768
0.7067	Intermediate Similarity	NPC143421
0.7067	Intermediate Similarity	NPC472203
0.7067	Intermediate Similarity	NPC115013
0.7067	Intermediate Similarity	NPC477317
0.7067	Intermediate Similarity	NPC259294
0.7067	Intermediate Similarity	NPC186992
0.7067	Intermediate Similarity	NPC476087
0.7067	Intermediate Similarity	NPC126685
0.7067	Intermediate Similarity	NPC472202
0.7067	Intermediate Similarity	NPC472200
0.7067	Intermediate Similarity	NPC475270
0.7067	Intermediate Similarity	NPC173328
0.7067	Intermediate Similarity	NPC183888
0.7067	Intermediate Similarity	NPC89843
0.7067	Intermediate Similarity	NPC44782
0.7067	Intermediate Similarity	NPC475667
0.7027	Intermediate Similarity	NPC170595
0.6981	Remote Similarity	NPC266553
0.6974	Remote Similarity	NPC20072
0.6933	Remote Similarity	NPC163362
0.6933	Remote Similarity	NPC127295
0.6912	Remote Similarity	NPC179823
0.6912	Remote Similarity	NPC32148
0.6909	Remote Similarity	NPC29721
0.6901	Remote Similarity	NPC470659
0.6901	Remote Similarity	NPC470660
0.6892	Remote Similarity	NPC150557
0.6892	Remote Similarity	NPC316807
0.6892	Remote Similarity	NPC177343
0.6883	Remote Similarity	NPC472352
0.6883	Remote Similarity	NPC156089
0.6883	Remote Similarity	NPC60849
0.6883	Remote Similarity	NPC473500
0.6883	Remote Similarity	NPC38295
0.6883	Remote Similarity	NPC477332
0.6883	Remote Similarity	NPC470313
0.68	Remote Similarity	NPC318258
0.6757	Remote Similarity	NPC110813
0.6757	Remote Similarity	NPC188793
0.6727	Remote Similarity	NPC320189

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 NPC472025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	894
0.1-0.2	5263
0.2-0.3	2089
0.3-0.4	550
0.4-0.5	211
0.5-0.6	96
0.6-0.7	20
0.7-0.8	14
0.8-0.85	5
0.85-0.9	3
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9245	High Similarity	NPD892	Phase 3
0.9245	High Similarity	NPD891	Phase 3
0.9245	High Similarity	NPD890	Clinical (unspecified phase)
0.9245	High Similarity	NPD888	Phase 3
0.9245	High Similarity	NPD893	Approved
0.9057	High Similarity	NPD2269	Approved
0.8868	High Similarity	NPD904	Phase 3
0.8868	High Similarity	NPD905	Approved
0.8793	High Similarity	NPD6123	Approved
0.8545	High Similarity	NPD889	Approved
0.8545	High Similarity	NPD894	Approved
0.8545	High Similarity	NPD895	Approved
0.8545	High Similarity	NPD887	Approved
0.8393	Intermediate Similarity	NPD7346	Approved
0.8103	Intermediate Similarity	NPD2267	Suspended
0.7925	Intermediate Similarity	NPD9000	Phase 3
0.7925	Intermediate Similarity	NPD8997	Approved
0.7925	Intermediate Similarity	NPD8993	Phase 1
0.7925	Intermediate Similarity	NPD8998	Phase 2
0.7925	Intermediate Similarity	NPD8999	Phase 3
0.7667	Intermediate Similarity	NPD369	Approved
0.7636	Intermediate Similarity	NPD8965	Approved
0.7636	Intermediate Similarity	NPD8966	Approved
0.7391	Intermediate Similarity	NPD3181	Approved
0.7358	Intermediate Similarity	NPD8788	Approved
0.7344	Intermediate Similarity	NPD847	Phase 1
0.7288	Intermediate Similarity	NPD9036	Phase 3
0.7288	Intermediate Similarity	NPD9035	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7329	Approved
0.6912	Remote Similarity	NPD897	Approved
0.6912	Remote Similarity	NPD898	Approved
0.6912	Remote Similarity	NPD896	Approved
0.6909	Remote Similarity	NPD9006	Approved
0.6857	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1457	Discontinued
0.6508	Remote Similarity	NPD885	Approved
0.6508	Remote Similarity	NPD884	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD9219	Approved
0.6379	Remote Similarity	NPD8994	Approved
0.6364	Remote Similarity	NPD7536	Approved
0.6351	Remote Similarity	NPD1810	Approved
0.6351	Remote Similarity	NPD1811	Approved
0.629	Remote Similarity	NPD9049	Discontinued
0.629	Remote Similarity	NPD9050	Approved
0.622	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD8171	Discontinued
0.6145	Remote Similarity	NPD3209	Approved
0.6145	Remote Similarity	NPD3207	Approved
0.6145	Remote Similarity	NPD3208	Approved
0.6145	Remote Similarity	NPD3201	Approved
0.6145	Remote Similarity	NPD3203	Approved
0.6145	Remote Similarity	NPD3202	Approved
0.614	Remote Similarity	NPD8958	Phase 2
0.614	Remote Similarity	NPD8957	Approved
0.6129	Remote Similarity	NPD1400	Approved
0.6129	Remote Similarity	NPD1399	Approved
0.6094	Remote Similarity	NPD3728	Approved
0.6094	Remote Similarity	NPD3730	Approved
0.6087	Remote Similarity	NPD8961	Approved
0.6038	Remote Similarity	NPD9051	Approved
0.6038	Remote Similarity	NPD9053	Approved
0.6038	Remote Similarity	NPD9052	Approved
0.6027	Remote Similarity	NPD9445	Approved
0.6	Remote Similarity	NPD5794	Approved
0.6	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5795	Approved
0.6	Remote Similarity	NPD5798	Approved
0.6	Remote Similarity	NPD5797	Approved
0.5952	Remote Similarity	NPD2698	Approved
0.5946	Remote Similarity	NPD2687	Approved
0.5946	Remote Similarity	NPD2686	Approved
0.5946	Remote Similarity	NPD2254	Approved
0.593	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3669	Approved
0.5833	Remote Similarity	NPD9030	Approved
0.5833	Remote Similarity	NPD9031	Approved
0.5833	Remote Similarity	NPD9033	Approved
0.5833	Remote Similarity	NPD9032	Approved
0.5789	Remote Similarity	NPD389	Phase 3
0.5789	Remote Similarity	NPD8995	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD8996	Phase 3
0.5778	Remote Similarity	NPD6428	Approved
0.5775	Remote Similarity	NPD371	Approved
0.569	Remote Similarity	NPD8967	Approved
0.5667	Remote Similarity	NPD5381	Approved
0.5667	Remote Similarity	NPD5377	Approved
0.5667	Remote Similarity	NPD5378	Approved
0.5645	Remote Similarity	NPD9139	Approved
0.5638	Remote Similarity	NPD8083	Approved
0.5638	Remote Similarity	NPD8084	Approved
0.5638	Remote Similarity	NPD8138	Approved
0.5638	Remote Similarity	NPD8082	Approved
0.5638	Remote Similarity	NPD8086	Approved
0.5638	Remote Similarity	NPD8085	Approved
0.5638	Remote Similarity	NPD8139	Approved
0.5618	Remote Similarity	NPD1446	Phase 3
0.5618	Remote Similarity	NPD1447	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data