NPASS Compound

Structure

NPC206601 OpenBabel07101718222D 34 34 0 0 1 0 0 0 0 0999 V2000 -15.5885 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 0.8660 -1.5000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 2.5981 0.5000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 2 1 0 0 0 0 2 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 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 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 1 0 0 0 0 14 15 1 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 18 33 1 0 0 0 0 19 27 1 1 0 0 0 20 16 1 6 0 0 0 20 22 1 0 0 0 0 20 34 1 0 0 0 0 21 28 2 0 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 6 0 0 0 24 25 1 0 0 0 0 24 31 1 1 0 0 0 25 33 1 6 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.33
Volume:	508.875
LogP:	4.061
LogD:	3.081
LogS:	-3.917
# Rotatable Bonds:	21
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.127
Synthetic Accessibility Score:	3.821
Fsp3:	0.96
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.307
MDCK Permeability:	1.8777087461785413e-05
Pgp-inhibitor:	0.84
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	96.5042495727539%
Volume Distribution (VD):	0.824
Pgp-substrate:	3.2120201587677%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	4.374
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.413
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.411
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.95
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.099

Download Data

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

Natural Product: NPC206601

Natural Product ID:	NPC206601
*Common Name:**	(2S)-1-O-Palmitoyl-3-O-Beta-D-Galactopyranosylglycerol
IUPAC Name:	[(2S)-2-hydroxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] hexadecanoate
Synonyms:
Standard InCHIKey:	DWKQIHQQZYILDB-DISYYVGZSA-N
Standard InCHI:	InChI=1S/C25H48O9/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(28)32-17-19(27)18-33-25-24(31)23(30)22(29)20(16-26)34-25/h19-20,22-27,29-31H,2-18H2,1H3/t19-,20-,22+,23+,24-,25-/m1/s1
SMILES:	CCCCCCCCCCCCCCCC(=O)OC[C@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465806
PubChem CID:	10413348
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0000637] Glycosylglycerols [CHEMONTID:0003819] Glycosylmonoradylglycerols [CHEMONTID:0001773] Glycosylmonoacylglycerols

*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
NPO32972	oscillatoria rosea	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8882435]

☑ 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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	Activity	>	50.0	ug ml-1	PMID[488397]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	60000.0	nM	PMID[488397]

☑ 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 NPC206601 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	723
0.1-0.2	4784
0.2-0.3	13402
0.3-0.4	11921
0.4-0.5	8363
0.5-0.6	2939
0.6-0.7	359
0.7-0.8	167
0.8-0.85	23
0.85-0.9	6
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC241265
0.9688	High Similarity	NPC285003
0.9531	High Similarity	NPC50228
0.9531	High Similarity	NPC97736
0.9394	High Similarity	NPC185419
0.9394	High Similarity	NPC184550
0.9385	High Similarity	NPC211428
0.9355	High Similarity	NPC325773
0.9254	High Similarity	NPC206823
0.9254	High Similarity	NPC291228
0.9254	High Similarity	NPC163812
0.9254	High Similarity	NPC308096
0.9062	High Similarity	NPC12040
0.9062	High Similarity	NPC76881
0.8971	High Similarity	NPC169085
0.8971	High Similarity	NPC225748
0.8971	High Similarity	NPC39266
0.8971	High Similarity	NPC9763
0.8857	High Similarity	NPC477350
0.8769	High Similarity	NPC471760
0.8769	High Similarity	NPC190418
0.8769	High Similarity	NPC471761
0.8732	High Similarity	NPC216883
0.8732	High Similarity	NPC476782
0.8732	High Similarity	NPC476783
0.8732	High Similarity	NPC476781
0.8657	High Similarity	NPC250619
0.8611	High Similarity	NPC477326
0.8611	High Similarity	NPC477320
0.8611	High Similarity	NPC113745
0.8611	High Similarity	NPC281563
0.8611	High Similarity	NPC477323
0.8611	High Similarity	NPC477325
0.8611	High Similarity	NPC477330
0.8611	High Similarity	NPC109887
0.8611	High Similarity	NPC477329
0.8611	High Similarity	NPC475425
0.8611	High Similarity	NPC146380
0.8611	High Similarity	NPC477328
0.8493	Intermediate Similarity	NPC477346
0.8493	Intermediate Similarity	NPC22742
0.8493	Intermediate Similarity	NPC85759
0.8493	Intermediate Similarity	NPC146992
0.8493	Intermediate Similarity	NPC158302
0.8493	Intermediate Similarity	NPC477344
0.8493	Intermediate Similarity	NPC294748
0.8387	Intermediate Similarity	NPC148424
0.8382	Intermediate Similarity	NPC67099
0.8378	Intermediate Similarity	NPC267592
0.8267	Intermediate Similarity	NPC119583
0.8267	Intermediate Similarity	NPC307400
0.8267	Intermediate Similarity	NPC27289
0.8267	Intermediate Similarity	NPC472201
0.8267	Intermediate Similarity	NPC21693
0.8267	Intermediate Similarity	NPC475270
0.8267	Intermediate Similarity	NPC477319
0.8267	Intermediate Similarity	NPC126685
0.8267	Intermediate Similarity	NPC475327
0.8267	Intermediate Similarity	NPC259294
0.8267	Intermediate Similarity	NPC477317
0.8267	Intermediate Similarity	NPC475667
0.8267	Intermediate Similarity	NPC472204
0.8267	Intermediate Similarity	NPC477347
0.8267	Intermediate Similarity	NPC123204
0.8267	Intermediate Similarity	NPC89843
0.8267	Intermediate Similarity	NPC169345
0.8267	Intermediate Similarity	NPC472202
0.8267	Intermediate Similarity	NPC236649
0.8267	Intermediate Similarity	NPC183888
0.8267	Intermediate Similarity	NPC290012
0.8267	Intermediate Similarity	NPC173328
0.8267	Intermediate Similarity	NPC472200
0.8267	Intermediate Similarity	NPC477318
0.8267	Intermediate Similarity	NPC44782
0.8267	Intermediate Similarity	NPC238056
0.8267	Intermediate Similarity	NPC186992
0.8267	Intermediate Similarity	NPC297768
0.8267	Intermediate Similarity	NPC476087
0.8267	Intermediate Similarity	NPC269318
0.8267	Intermediate Similarity	NPC115013
0.8267	Intermediate Similarity	NPC477331
0.8267	Intermediate Similarity	NPC472203
0.8267	Intermediate Similarity	NPC184915
0.8267	Intermediate Similarity	NPC143421
0.8267	Intermediate Similarity	NPC472205
0.8267	Intermediate Similarity	NPC224953
0.8154	Intermediate Similarity	NPC477757
0.8154	Intermediate Similarity	NPC477755
0.8154	Intermediate Similarity	NPC477762
0.8154	Intermediate Similarity	NPC477763
0.8154	Intermediate Similarity	NPC477750
0.8154	Intermediate Similarity	NPC477753
0.8143	Intermediate Similarity	NPC52268
0.8143	Intermediate Similarity	NPC53760
0.8125	Intermediate Similarity	NPC322855
0.8125	Intermediate Similarity	NPC320032
0.8065	Intermediate Similarity	NPC320588
0.8065	Intermediate Similarity	NPC469937
0.8065	Intermediate Similarity	NPC23155
0.8065	Intermediate Similarity	NPC53463
0.8052	Intermediate Similarity	NPC472352
0.8052	Intermediate Similarity	NPC473500
0.8052	Intermediate Similarity	NPC38295
0.8052	Intermediate Similarity	NPC477332
0.8052	Intermediate Similarity	NPC470313
0.8052	Intermediate Similarity	NPC60849
0.8052	Intermediate Similarity	NPC156089
0.7971	Intermediate Similarity	NPC32148
0.7969	Intermediate Similarity	NPC472025
0.7949	Intermediate Similarity	NPC288471
0.791	Intermediate Similarity	NPC268243
0.7848	Intermediate Similarity	NPC83839
0.7733	Intermediate Similarity	NPC110813
0.7639	Intermediate Similarity	NPC321873
0.7632	Intermediate Similarity	NPC133377
0.7612	Intermediate Similarity	NPC472026
0.7581	Intermediate Similarity	NPC233726
0.7581	Intermediate Similarity	NPC23134
0.7581	Intermediate Similarity	NPC326533
0.7581	Intermediate Similarity	NPC124963
0.7571	Intermediate Similarity	NPC477751
0.7571	Intermediate Similarity	NPC477764
0.7571	Intermediate Similarity	NPC477752
0.7571	Intermediate Similarity	NPC477756
0.7561	Intermediate Similarity	NPC470009
0.7531	Intermediate Similarity	NPC470657
0.75	Intermediate Similarity	NPC303727
0.75	Intermediate Similarity	NPC192025
0.75	Intermediate Similarity	NPC125253
0.75	Intermediate Similarity	NPC253975
0.7465	Intermediate Similarity	NPC477758
0.7465	Intermediate Similarity	NPC477760
0.7465	Intermediate Similarity	NPC477759
0.7465	Intermediate Similarity	NPC477754
0.7465	Intermediate Similarity	NPC477761
0.7463	Intermediate Similarity	NPC470363
0.7439	Intermediate Similarity	NPC31349
0.7344	Intermediate Similarity	NPC145112
0.7344	Intermediate Similarity	NPC58629
0.7344	Intermediate Similarity	NPC130683
0.7344	Intermediate Similarity	NPC107914
0.7344	Intermediate Similarity	NPC165198
0.7344	Intermediate Similarity	NPC157514
0.7344	Intermediate Similarity	NPC246558
0.7344	Intermediate Similarity	NPC89145
0.7344	Intermediate Similarity	NPC67660
0.7344	Intermediate Similarity	NPC242073
0.7344	Intermediate Similarity	NPC269166
0.7344	Intermediate Similarity	NPC323361
0.7313	Intermediate Similarity	NPC290179
0.7313	Intermediate Similarity	NPC34877
0.7313	Intermediate Similarity	NPC317023
0.7294	Intermediate Similarity	NPC477349
0.7273	Intermediate Similarity	NPC474003
0.7258	Intermediate Similarity	NPC42503
0.7258	Intermediate Similarity	NPC26253
0.7258	Intermediate Similarity	NPC299781
0.7258	Intermediate Similarity	NPC282143
0.7258	Intermediate Similarity	NPC157193
0.7229	Intermediate Similarity	NPC314364
0.7229	Intermediate Similarity	NPC51662
0.7209	Intermediate Similarity	NPC320089
0.7164	Intermediate Similarity	NPC219040
0.716	Intermediate Similarity	NPC474266
0.7143	Intermediate Similarity	NPC258690
0.7143	Intermediate Similarity	NPC317651
0.7143	Intermediate Similarity	NPC55678
0.7126	Intermediate Similarity	NPC477345
0.7126	Intermediate Similarity	NPC477348
0.7126	Intermediate Similarity	NPC44682
0.7126	Intermediate Similarity	NPC163409
0.7126	Intermediate Similarity	NPC238264
0.7097	Intermediate Similarity	NPC106872
0.7097	Intermediate Similarity	NPC14144
0.7093	Intermediate Similarity	NPC472197
0.7073	Intermediate Similarity	NPC473791
0.7051	Intermediate Similarity	NPC70996
0.7045	Intermediate Similarity	NPC215570
0.7037	Intermediate Similarity	NPC248415
0.7037	Intermediate Similarity	NPC475849
0.6986	Remote Similarity	NPC469925
0.6986	Remote Similarity	NPC286842
0.697	Remote Similarity	NPC289979
0.6966	Remote Similarity	NPC475375
0.6966	Remote Similarity	NPC475241
0.6966	Remote Similarity	NPC143446
0.6966	Remote Similarity	NPC475164
0.6966	Remote Similarity	NPC473605
0.6966	Remote Similarity	NPC476066
0.6966	Remote Similarity	NPC473765
0.6966	Remote Similarity	NPC475593
0.6966	Remote Similarity	NPC475540
0.6966	Remote Similarity	NPC475525
0.6935	Remote Similarity	NPC321087
0.6935	Remote Similarity	NPC324004
0.6935	Remote Similarity	NPC328497
0.6935	Remote Similarity	NPC277475
0.6914	Remote Similarity	NPC216941
0.6914	Remote Similarity	NPC469469
0.6901	Remote Similarity	NPC235788

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 NPC206601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	891
0.1-0.2	4292
0.2-0.3	2584
0.3-0.4	818
0.4-0.5	368
0.5-0.6	128
0.6-0.7	45
0.7-0.8	24
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
0.8065	Intermediate Similarity	NPD3730	Approved
0.8065	Intermediate Similarity	NPD3728	Approved
0.7971	Intermediate Similarity	NPD898	Approved
0.7971	Intermediate Similarity	NPD897	Approved
0.7971	Intermediate Similarity	NPD896	Approved
0.7742	Intermediate Similarity	NPD2269	Approved
0.7581	Intermediate Similarity	NPD905	Approved
0.7581	Intermediate Similarity	NPD904	Phase 3
0.7532	Intermediate Similarity	NPD7329	Approved
0.7432	Intermediate Similarity	NPD3181	Approved
0.7344	Intermediate Similarity	NPD895	Approved
0.7344	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD893	Approved
0.7344	Intermediate Similarity	NPD894	Approved
0.7344	Intermediate Similarity	NPD889	Approved
0.7344	Intermediate Similarity	NPD892	Phase 3
0.7344	Intermediate Similarity	NPD887	Approved
0.7344	Intermediate Similarity	NPD888	Phase 3
0.7344	Intermediate Similarity	NPD891	Phase 3
0.7273	Intermediate Similarity	NPD2267	Suspended
0.7143	Intermediate Similarity	NPD8961	Approved
0.7101	Intermediate Similarity	NPD6123	Approved
0.7097	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9000	Phase 3
0.6774	Remote Similarity	NPD8998	Phase 2
0.6774	Remote Similarity	NPD8993	Phase 1
0.6774	Remote Similarity	NPD8997	Approved
0.6774	Remote Similarity	NPD8999	Phase 3
0.6716	Remote Similarity	NPD7346	Approved
0.6667	Remote Similarity	NPD8959	Approved
0.6613	Remote Similarity	NPD2699	Approved
0.6596	Remote Similarity	NPD8139	Approved
0.6596	Remote Similarity	NPD8084	Approved
0.6596	Remote Similarity	NPD8085	Approved
0.6596	Remote Similarity	NPD8086	Approved
0.6596	Remote Similarity	NPD8138	Approved
0.6596	Remote Similarity	NPD8082	Approved
0.6596	Remote Similarity	NPD8083	Approved
0.6575	Remote Similarity	NPD7909	Approved
0.6562	Remote Similarity	NPD8966	Approved
0.6562	Remote Similarity	NPD8965	Approved
0.6526	Remote Similarity	NPD8276	Approved
0.6526	Remote Similarity	NPD8275	Approved
0.6522	Remote Similarity	NPD73	Approved
0.6471	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8081	Approved
0.6438	Remote Similarity	NPD847	Phase 1
0.6404	Remote Similarity	NPD46	Approved
0.6404	Remote Similarity	NPD6698	Approved
0.6392	Remote Similarity	NPD8393	Approved
0.6364	Remote Similarity	NPD618	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3669	Approved
0.6327	Remote Similarity	NPD8307	Discontinued
0.6327	Remote Similarity	NPD8140	Approved
0.6324	Remote Similarity	NPD9036	Phase 3
0.6324	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8788	Approved
0.6269	Remote Similarity	NPD1399	Approved
0.6269	Remote Similarity	NPD1400	Approved
0.6263	Remote Similarity	NPD6686	Approved
0.62	Remote Similarity	NPD6941	Approved
0.62	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.62	Remote Similarity	NPD8306	Approved
0.62	Remote Similarity	NPD8305	Approved
0.6197	Remote Similarity	NPD369	Approved
0.6145	Remote Similarity	NPD4238	Approved
0.6145	Remote Similarity	NPD4802	Phase 2
0.6139	Remote Similarity	NPD8087	Discontinued
0.6129	Remote Similarity	NPD2270	Approved
0.6122	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1780	Approved
0.6118	Remote Similarity	NPD1779	Approved
0.6111	Remote Similarity	NPD3716	Discontinued
0.6087	Remote Similarity	NPD1447	Phase 3
0.6087	Remote Similarity	NPD1446	Phase 3
0.6064	Remote Similarity	NPD6428	Approved
0.5978	Remote Similarity	NPD7983	Approved
0.5976	Remote Similarity	NPD11	Approved
0.5976	Remote Similarity	NPD376	Approved
0.5968	Remote Similarity	NPD7536	Approved
0.5962	Remote Similarity	NPD8133	Approved
0.596	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD8277	Approved
0.5942	Remote Similarity	NPD66	Approved
0.5942	Remote Similarity	NPD9008	Approved
0.5942	Remote Similarity	NPD9011	Approved
0.5942	Remote Similarity	NPD9007	Approved
0.5942	Remote Similarity	NPD9009	Approved
0.5942	Remote Similarity	NPD72	Approved
0.5942	Remote Similarity	NPD65	Approved
0.5942	Remote Similarity	NPD8960	Approved
0.5942	Remote Similarity	NPD9010	Approved
0.5942	Remote Similarity	NPD64	Approved
0.5938	Remote Similarity	NPD2255	Approved
0.5938	Remote Similarity	NPD9006	Approved
0.5921	Remote Similarity	NPD3197	Phase 1
0.5921	Remote Similarity	NPD1457	Discontinued
0.5918	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7140	Approved
0.5918	Remote Similarity	NPD7139	Approved
0.5862	Remote Similarity	NPD883	Phase 2
0.5862	Remote Similarity	NPD882	Phase 2
0.5846	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6412	Phase 2
0.5823	Remote Similarity	NPD8278	Approved
0.5811	Remote Similarity	NPD3198	Approved
0.5806	Remote Similarity	NPD9448	Phase 2
0.5806	Remote Similarity	NPD633	Phase 3
0.5806	Remote Similarity	NPD9655	Approved
0.5794	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD2257	Approved
0.5769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8300	Approved
0.5758	Remote Similarity	NPD8301	Approved
0.5741	Remote Similarity	NPD7641	Discontinued
0.5701	Remote Similarity	NPD6940	Discontinued
0.5699	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD885	Approved
0.5694	Remote Similarity	NPD884	Clinical (unspecified phase)
0.567	Remote Similarity	NPD881	Approved
0.5663	Remote Similarity	NPD1811	Approved
0.5663	Remote Similarity	NPD1810	Approved
0.5645	Remote Similarity	NPD3206	Approved
0.5636	Remote Similarity	NPD8347	Approved
0.5636	Remote Similarity	NPD8346	Approved
0.5636	Remote Similarity	NPD8345	Approved
0.5612	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6704	Discontinued
0.5606	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD9219	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