NPASS Compound

Structure

NPC208537 OpenBabel07101719512D 40 40 0 0 1 0 0 0 0 0999 V2000 -13.8564 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 -13.8564 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 1.7321 -4.0000 0.0000 C 0 0 0 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 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 1.7321 -3.0000 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 -1.7321 -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 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 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 -2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 N 0 0 0 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 2.5981 -2.5000 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 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 -0.0000 -3.0000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 6 18 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 16 1 0 0 0 0 16 17 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 33 1 0 0 0 0 22 20 1 6 0 0 0 22 27 1 0 0 0 0 22 39 1 0 0 0 0 23 32 2 3 0 0 0 23 34 1 0 0 0 0 24 31 2 3 0 0 0 24 35 1 0 0 0 0 25 21 1 6 0 0 0 25 29 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 26 32 1 1 0 0 0 27 28 1 0 0 0 0 27 36 1 1 0 0 0 28 37 1 6 0 0 0 29 38 2 0 0 0 0 29 40 1 0 0 0 0 30 39 1 0 0 0 0 30 40 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.4
Volume:	603.286
LogP:	4.667
LogD:	3.793
LogS:	-3.435
# Rotatable Bonds:	24
TPSA:	154.42
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.103
Synthetic Accessibility Score:	4.004
Fsp3:	0.9
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:	-5.136
MDCK Permeability:	3.52E-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	97.26%
Volume Distribution (VD):	0.856
Pgp-substrate:	3.21%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.375
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.084

ADMET: Excretion

Clearance (CL):	3.699
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.334
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.125
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC208537

Natural Product ID:	NPC208537
*Common Name:**	[(2R,3R,4R,5S,6R)-3-(Butanoylamino)-4,5-Dihydroxy-6-(Hydroxymethyl)Oxan-2-Yl] (2S)-3-Methyl-2-(Pentadecanoylamino)Butanoate
IUPAC Name:	[(2R,3R,4R,5S,6R)-3-(butanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S)-3-methyl-2-(pentadecanoylamino)butanoate
Synonyms:
Standard InCHIKey:	KHSLDHWSUXNVCW-SONSSPRBSA-N
Standard InCHI:	InChI=1S/C30H56N2O8/c1-5-7-8-9-10-11-12-13-14-15-16-17-19-24(35)31-25(21(3)4)29(38)40-30-26(32-23(34)18-6-2)28(37)27(36)22(20-33)39-30/h21-22,25-28,30,33,36-37H,5-20H2,1-4H3,(H,31,35)(H,32,34)/t22-,25+,26-,27-,28-,30-/m1/s1
SMILES:	CCCCCCCCCCCCCCC(=N[C@@H](C(C)C)C(=O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)N=C(CCC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464667
PubChem CID:	24862331
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0003305] Aminosaccharides [CHEMONTID:0001148] Amino sugars [CHEMONTID:0000146] Acylaminosugars

*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
NPO33361	Serratia sp.	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18303848]
NPO33361	Serratia sp.	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	PMID[28335605]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4585	Organism	Mycobacterium diernhoferi	Mycobacterium diernhoferi	MIC	=	180000.0	nM	PMID[498588]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	180000.0	nM	PMID[498588]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	180000.0	nM	PMID[498588]

☑ 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 NPC208537 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	146
0.1-0.2	2692
0.2-0.3	18628
0.3-0.4	14351
0.4-0.5	5705
0.5-0.6	876
0.6-0.7	259
0.7-0.8	32
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC270005
0.8763	High Similarity	NPC475918
0.8696	High Similarity	NPC470283
0.8352	Intermediate Similarity	NPC470284
0.8315	Intermediate Similarity	NPC476523
0.8046	Intermediate Similarity	NPC316807
0.798	Intermediate Similarity	NPC42320
0.798	Intermediate Similarity	NPC188453
0.7766	Intermediate Similarity	NPC292345
0.7634	Intermediate Similarity	NPC83839
0.7529	Intermediate Similarity	NPC327753
0.7529	Intermediate Similarity	NPC223174
0.7529	Intermediate Similarity	NPC327486
0.7474	Intermediate Similarity	NPC470282
0.7419	Intermediate Similarity	NPC155670
0.7419	Intermediate Similarity	NPC95478
0.7419	Intermediate Similarity	NPC145748
0.734	Intermediate Similarity	NPC192025
0.734	Intermediate Similarity	NPC125253
0.734	Intermediate Similarity	NPC227051
0.734	Intermediate Similarity	NPC253975
0.7188	Intermediate Similarity	NPC477728
0.7172	Intermediate Similarity	NPC475603
0.7172	Intermediate Similarity	NPC61894
0.7143	Intermediate Similarity	NPC477729
0.7097	Intermediate Similarity	NPC471420
0.7079	Intermediate Similarity	NPC43219
0.7065	Intermediate Similarity	NPC473984
0.7048	Intermediate Similarity	NPC477198
0.7011	Intermediate Similarity	NPC474299
0.7011	Intermediate Similarity	NPC28348
0.7011	Intermediate Similarity	NPC475808
0.7011	Intermediate Similarity	NPC473985
0.7011	Intermediate Similarity	NPC474298
0.7	Intermediate Similarity	NPC328646
0.7	Intermediate Similarity	NPC86064
0.6989	Remote Similarity	NPC318258
0.6961	Remote Similarity	NPC330590
0.6932	Remote Similarity	NPC476291
0.6932	Remote Similarity	NPC478256
0.6932	Remote Similarity	NPC476285
0.6893	Remote Similarity	NPC189629
0.6887	Remote Similarity	NPC227622
0.6882	Remote Similarity	NPC150557
0.6857	Remote Similarity	NPC271207
0.6857	Remote Similarity	NPC255175
0.6857	Remote Similarity	NPC206711
0.6857	Remote Similarity	NPC225978
0.681	Remote Similarity	NPC305261
0.6789	Remote Similarity	NPC59589
0.6778	Remote Similarity	NPC185419
0.6778	Remote Similarity	NPC141325
0.6778	Remote Similarity	NPC184550
0.6774	Remote Similarity	NPC314968
0.6774	Remote Similarity	NPC314772
0.6771	Remote Similarity	NPC477730
0.6759	Remote Similarity	NPC74035
0.6739	Remote Similarity	NPC476130
0.6739	Remote Similarity	NPC476324
0.6733	Remote Similarity	NPC74672
0.6733	Remote Similarity	NPC242503
0.6733	Remote Similarity	NPC139782
0.6733	Remote Similarity	NPC43074
0.6733	Remote Similarity	NPC209047
0.6731	Remote Similarity	NPC313821
0.6705	Remote Similarity	NPC206601
0.6703	Remote Similarity	NPC308096
0.6703	Remote Similarity	NPC291228
0.6703	Remote Similarity	NPC138435
0.6699	Remote Similarity	NPC3568
0.6699	Remote Similarity	NPC256570
0.6699	Remote Similarity	NPC192066
0.6699	Remote Similarity	NPC17290
0.6667	Remote Similarity	NPC186840
0.6667	Remote Similarity	NPC15851
0.6667	Remote Similarity	NPC473604
0.6667	Remote Similarity	NPC473950
0.6667	Remote Similarity	NPC309898
0.6667	Remote Similarity	NPC306838
0.6667	Remote Similarity	NPC473581
0.6667	Remote Similarity	NPC111567
0.6667	Remote Similarity	NPC475125
0.6667	Remote Similarity	NPC263545
0.6667	Remote Similarity	NPC475472
0.6636	Remote Similarity	NPC137453
0.6634	Remote Similarity	NPC39290
0.6634	Remote Similarity	NPC159369
0.6629	Remote Similarity	NPC50228
0.6629	Remote Similarity	NPC193280
0.6629	Remote Similarity	NPC97736
0.6629	Remote Similarity	NPC314273
0.6613	Remote Similarity	NPC119794
0.6613	Remote Similarity	NPC73829
0.6598	Remote Similarity	NPC165119
0.6596	Remote Similarity	NPC316242
0.6593	Remote Similarity	NPC474403
0.6571	Remote Similarity	NPC197294
0.6571	Remote Similarity	NPC8098
0.6571	Remote Similarity	NPC183449
0.6562	Remote Similarity	NPC314466
0.656	Remote Similarity	NPC477072
0.656	Remote Similarity	NPC76999
0.6556	Remote Similarity	NPC211428
0.6556	Remote Similarity	NPC285003
0.6556	Remote Similarity	NPC241265
0.6545	Remote Similarity	NPC201128
0.6542	Remote Similarity	NPC315036
0.6542	Remote Similarity	NPC56298
0.6542	Remote Similarity	NPC471628
0.6538	Remote Similarity	NPC23454
0.6538	Remote Similarity	NPC70323
0.6538	Remote Similarity	NPC156782
0.6538	Remote Similarity	NPC262312
0.6538	Remote Similarity	NPC35269
0.6538	Remote Similarity	NPC282088
0.6538	Remote Similarity	NPC157353
0.6538	Remote Similarity	NPC54961
0.6538	Remote Similarity	NPC158445
0.6531	Remote Similarity	NPC320936
0.6526	Remote Similarity	NPC315131
0.6526	Remote Similarity	NPC315535
0.6526	Remote Similarity	NPC478017
0.6522	Remote Similarity	NPC476248
0.6517	Remote Similarity	NPC195165
0.6508	Remote Similarity	NPC75318
0.6508	Remote Similarity	NPC280941
0.6508	Remote Similarity	NPC235772
0.6505	Remote Similarity	NPC182632
0.6505	Remote Similarity	NPC282705
0.65	Remote Similarity	NPC313552
0.6495	Remote Similarity	NPC36927
0.6495	Remote Similarity	NPC271772
0.6477	Remote Similarity	NPC190418
0.6477	Remote Similarity	NPC471760
0.6477	Remote Similarity	NPC471761
0.6458	Remote Similarity	NPC22742
0.6458	Remote Similarity	NPC294748
0.6458	Remote Similarity	NPC85759
0.6458	Remote Similarity	NPC158302
0.6458	Remote Similarity	NPC146992
0.6458	Remote Similarity	NPC477344
0.6458	Remote Similarity	NPC477346
0.6457	Remote Similarity	NPC145899
0.6449	Remote Similarity	NPC474952
0.6441	Remote Similarity	NPC477237
0.6436	Remote Similarity	NPC477060
0.6436	Remote Similarity	NPC214376
0.6436	Remote Similarity	NPC314408
0.6436	Remote Similarity	NPC43850
0.6436	Remote Similarity	NPC123746
0.6436	Remote Similarity	NPC314007
0.6429	Remote Similarity	NPC47135
0.6415	Remote Similarity	NPC45313
0.6404	Remote Similarity	NPC291650
0.6404	Remote Similarity	NPC29501
0.6404	Remote Similarity	NPC322801
0.6404	Remote Similarity	NPC129100
0.6357	Remote Similarity	NPC200788
0.6357	Remote Similarity	NPC243680
0.6344	Remote Similarity	NPC169085
0.6344	Remote Similarity	NPC206823
0.6344	Remote Similarity	NPC9763
0.6344	Remote Similarity	NPC225748
0.6344	Remote Similarity	NPC163812
0.6344	Remote Similarity	NPC39266
0.6339	Remote Similarity	NPC317534
0.6333	Remote Similarity	NPC477238
0.6333	Remote Similarity	NPC470110
0.6327	Remote Similarity	NPC169345
0.6327	Remote Similarity	NPC259294
0.6327	Remote Similarity	NPC307400
0.6327	Remote Similarity	NPC477318
0.6327	Remote Similarity	NPC119583
0.6327	Remote Similarity	NPC472201
0.6327	Remote Similarity	NPC126685
0.6327	Remote Similarity	NPC115013
0.6327	Remote Similarity	NPC238056
0.6327	Remote Similarity	NPC477347
0.6327	Remote Similarity	NPC186992
0.6327	Remote Similarity	NPC472203
0.6327	Remote Similarity	NPC183888
0.6327	Remote Similarity	NPC89843
0.6327	Remote Similarity	NPC297768
0.6327	Remote Similarity	NPC475270
0.6327	Remote Similarity	NPC123204
0.6327	Remote Similarity	NPC315969
0.6327	Remote Similarity	NPC477331
0.6327	Remote Similarity	NPC173328
0.6327	Remote Similarity	NPC44782
0.6327	Remote Similarity	NPC290012
0.6327	Remote Similarity	NPC475667
0.6327	Remote Similarity	NPC472205
0.6327	Remote Similarity	NPC477317
0.6327	Remote Similarity	NPC472200
0.6327	Remote Similarity	NPC476087
0.6327	Remote Similarity	NPC472202
0.6327	Remote Similarity	NPC475327
0.6327	Remote Similarity	NPC477319
0.6327	Remote Similarity	NPC27289
0.6327	Remote Similarity	NPC472204

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 NPC208537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	1892
0.2-0.3	4634
0.3-0.4	1907
0.4-0.5	404
0.5-0.6	137
0.6-0.7	67
0.7-0.8	17
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD6428	Approved
0.8261	Intermediate Similarity	NPD3716	Discontinued
0.8242	Intermediate Similarity	NPD4759	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6941	Approved
0.7766	Intermediate Similarity	NPD618	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8045	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD1446	Phase 3
0.7629	Intermediate Similarity	NPD1447	Phase 3
0.7549	Intermediate Similarity	NPD7141	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD7139	Approved
0.7549	Intermediate Similarity	NPD7140	Approved
0.7529	Intermediate Similarity	NPD9445	Approved
0.7429	Intermediate Similarity	NPD8307	Discontinued
0.7426	Intermediate Similarity	NPD2255	Approved
0.7374	Intermediate Similarity	NPD8394	Approved
0.729	Intermediate Similarity	NPD8306	Approved
0.729	Intermediate Similarity	NPD8305	Approved
0.7264	Intermediate Similarity	NPD8140	Approved
0.7222	Intermediate Similarity	NPD8087	Discontinued
0.7037	Intermediate Similarity	NPD8174	Phase 2
0.6981	Remote Similarity	NPD8275	Approved
0.6981	Remote Similarity	NPD8276	Approved
0.6961	Remote Similarity	NPD5377	Approved
0.6961	Remote Similarity	NPD7844	Discontinued
0.6961	Remote Similarity	NPD5378	Approved
0.6961	Remote Similarity	NPD5381	Approved
0.6957	Remote Similarity	NPD3160	Suspended
0.6947	Remote Similarity	NPD882	Phase 2
0.6947	Remote Similarity	NPD883	Phase 2
0.6887	Remote Similarity	NPD8138	Approved
0.6887	Remote Similarity	NPD8085	Approved
0.6887	Remote Similarity	NPD8086	Approved
0.6887	Remote Similarity	NPD8084	Approved
0.6887	Remote Similarity	NPD8083	Approved
0.6887	Remote Similarity	NPD8139	Approved
0.6887	Remote Similarity	NPD8082	Approved
0.6852	Remote Similarity	NPD8393	Approved
0.6852	Remote Similarity	NPD5376	Approved
0.681	Remote Similarity	NPD8345	Approved
0.681	Remote Similarity	NPD8346	Approved
0.681	Remote Similarity	NPD8347	Approved
0.6774	Remote Similarity	NPD9435	Approved
0.6774	Remote Similarity	NPD9434	Approved
0.6759	Remote Similarity	NPD8081	Approved
0.6733	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3189	Approved
0.6731	Remote Similarity	NPD3190	Approved
0.6731	Remote Similarity	NPD3191	Approved
0.6607	Remote Similarity	NPD6421	Discontinued
0.6593	Remote Similarity	NPD6704	Discontinued
0.6566	Remote Similarity	NPD619	Phase 3
0.6542	Remote Similarity	NPD4838	Approved
0.6542	Remote Similarity	NPD4837	Approved
0.6542	Remote Similarity	NPD4835	Approved
0.6542	Remote Similarity	NPD4836	Approved
0.6526	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7916	Approved
0.6522	Remote Similarity	NPD7915	Approved
0.6514	Remote Similarity	NPD1407	Approved
0.65	Remote Similarity	NPD3200	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD2700	Approved
0.6444	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3207	Approved
0.6436	Remote Similarity	NPD3201	Approved
0.6436	Remote Similarity	NPD3208	Approved
0.6436	Remote Similarity	NPD2698	Approved
0.6436	Remote Similarity	NPD3202	Approved
0.6436	Remote Similarity	NPD3209	Approved
0.6436	Remote Similarity	NPD3203	Approved
0.6429	Remote Similarity	NPD7345	Approved
0.6413	Remote Similarity	NPD3187	Discontinued
0.6404	Remote Similarity	NPD9030	Approved
0.6404	Remote Similarity	NPD9033	Approved
0.6404	Remote Similarity	NPD9031	Approved
0.6404	Remote Similarity	NPD9032	Approved
0.6373	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4282	Approved
0.6355	Remote Similarity	NPD881	Approved
0.6316	Remote Similarity	NPD2689	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5795	Approved
0.6311	Remote Similarity	NPD5797	Approved
0.6311	Remote Similarity	NPD5796	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5798	Approved
0.6311	Remote Similarity	NPD5794	Approved
0.6273	Remote Similarity	NPD8301	Approved
0.6273	Remote Similarity	NPD8300	Approved
0.6261	Remote Similarity	NPD2690	Discontinued
0.6222	Remote Similarity	NPD2263	Discontinued
0.6211	Remote Similarity	NPD1453	Phase 1
0.6211	Remote Similarity	NPD2257	Approved
0.617	Remote Similarity	NPD67	Phase 2
0.617	Remote Similarity	NPD9034	Approved
0.6162	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD361	Discontinued
0.6134	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3185	Approved
0.6126	Remote Similarity	NPD3182	Approved
0.6126	Remote Similarity	NPD3183	Approved
0.6126	Remote Similarity	NPD3184	Approved
0.6102	Remote Similarity	NPD3204	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7641	Discontinued
0.6071	Remote Similarity	NPD1449	Approved
0.6071	Remote Similarity	NPD1450	Approved
0.6064	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4833	Approved
0.6034	Remote Similarity	NPD35	Approved
0.6016	Remote Similarity	NPD4827	Approved
0.6016	Remote Similarity	NPD4826	Approved
0.6016	Remote Similarity	NPD6436	Phase 3
0.6016	Remote Similarity	NPD4828	Approved
0.5957	Remote Similarity	NPD9446	Approved
0.5938	Remote Similarity	NPD8390	Approved
0.5938	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD8392	Approved
0.5935	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8340	Approved
0.592	Remote Similarity	NPD8342	Approved
0.592	Remote Similarity	NPD8341	Approved
0.592	Remote Similarity	NPD8299	Approved
0.5897	Remote Similarity	NPD3188	Approved
0.5887	Remote Similarity	NPD8080	Discontinued
0.5873	Remote Similarity	NPD8451	Approved
0.587	Remote Similarity	NPD5380	Approved
0.584	Remote Similarity	NPD7642	Approved
0.5827	Remote Similarity	NPD8448	Approved
0.5826	Remote Similarity	NPD1385	Discontinued
0.5816	Remote Similarity	NPD372	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD8444	Approved
0.5789	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6940	Discontinued
0.5714	Remote Similarity	NPD7830	Approved
0.5714	Remote Similarity	NPD11	Approved
0.5714	Remote Similarity	NPD376	Approved
0.5714	Remote Similarity	NPD7829	Approved
0.569	Remote Similarity	NPD1428	Phase 2
0.5688	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD2691	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD574	Approved
0.5664	Remote Similarity	NPD8418	Phase 2
0.5652	Remote Similarity	NPD3161	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD1457	Discontinued
0.5647	Remote Similarity	NPD2269	Approved
0.5638	Remote Similarity	NPD896	Approved
0.5638	Remote Similarity	NPD898	Approved
0.5638	Remote Similarity	NPD897	Approved
0.563	Remote Similarity	NPD1805	Phase 2
0.563	Remote Similarity	NPD1804	Phase 2
0.562	Remote Similarity	NPD3731	Phase 3
0.5619	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD575	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