NPASS Compound

Structure

NPC245122 OpenBabel07101718302D 29 30 0 0 1 0 0 0 0 0999 V2000 3.5686 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 0.7957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8736 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1667 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 -2.9945 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.8988 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4727 -0.7626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0327 -3.9945 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 25 2 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 21 2 0 0 0 0 18 14 1 6 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 26 2 0 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.17
Volume:	429.958
LogP:	5.015
LogD:	3.135
LogS:	-4.822
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	4.004
Fsp3:	0.478
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:	-4.681
MDCK Permeability:	2.564030364737846e-05
Pgp-inhibitor:	0.423
Pgp-substrate:	0.106
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.496
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	97.62337493896484%
Volume Distribution (VD):	0.913
Pgp-substrate:	0.9146738648414612%

ADMET: Metabolism

CYP1A2-inhibitor:	0.242
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.585
CYP2C19-substrate:	0.717
CYP2C9-inhibitor:	0.608
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.58
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	5.044
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.444
Drug-inuced Liver Injury (DILI):	0.132
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.461
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.842
Carcinogencity:	0.551
Eye Corrosion:	0.03
Eye Irritation:	0.657
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC245122

Natural Product ID:	NPC245122
*Common Name:**	Ascofuranone
IUPAC Name:	5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde
Synonyms:	Ascofuranone
Standard InCHIKey:	VGYPZLGWVQQOST-JUERRSSISA-N
Standard InCHI:	InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
SMILES:	C/C(=CCc1c(c(C=O)c(C)c(c1O)Cl)O)/CC/C=C(C)/[C@@H]1CC(=O)C(C)(C)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL133046
PubChem CID:	6434242
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]
NPO32557	aschochyta viciae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9084049]

☑ 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	3
Ki	2
MIC	4
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	5
Others	2
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4727	Cell Line	C3H 10T1/2	Mus musculus	IC50	=	3200.0	nM	PMID[506793]
NPT543	Individual Protein	Pregnane X receptor	Homo sapiens	MEC	=	3.0	uM	PMID[506793]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC100	=	0.03	uM	PMID[506795]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	250000.0	nM	PMID[506796]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	30.0	nM	PMID[506796]
NPT26630	SINGLE PROTEIN	Alternative oxidase, mitochondrial	Trypanosoma brucei brucei	IC50	=	2.0	nM	PMID[506796]
NPT2	Others	Unspecified		IC50	=	2.0	nM	PMID[506797]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	30000.0	nM	PMID[506797]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	250000.0	nM	PMID[506797]
NPT2	Others	Unspecified		Ki	=	2.38	nM	PMID[506797]
NPT26630	SINGLE PROTEIN	Alternative oxidase, mitochondrial	Trypanosoma brucei brucei	Ki	=	0.13	nM	PMID[506798]

☑ 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 NPC245122 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	409
0.1-0.2	1813
0.2-0.3	4301
0.3-0.4	11662
0.4-0.5	9318
0.5-0.6	8289
0.6-0.7	6328
0.7-0.8	547
0.8-0.85	22
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8976	High Similarity	NPC477568
0.8931	High Similarity	NPC280497
0.879	High Similarity	NPC477566
0.879	High Similarity	NPC477567
0.8782	High Similarity	NPC477569
0.8494	Intermediate Similarity	NPC470081
0.8485	Intermediate Similarity	NPC298401
0.8434	Intermediate Similarity	NPC473696
0.8434	Intermediate Similarity	NPC474096
0.8415	Intermediate Similarity	NPC472404
0.8412	Intermediate Similarity	NPC474857
0.8383	Intermediate Similarity	NPC470563
0.8373	Intermediate Similarity	NPC472405
0.8333	Intermediate Similarity	NPC58653
0.8333	Intermediate Similarity	NPC173352
0.8323	Intermediate Similarity	NPC470561
0.8284	Intermediate Similarity	NPC474061
0.8284	Intermediate Similarity	NPC28669
0.8249	Intermediate Similarity	NPC474499
0.8246	Intermediate Similarity	NPC277865
0.8235	Intermediate Similarity	NPC472032
0.8208	Intermediate Similarity	NPC264922
0.8161	Intermediate Similarity	NPC45072
0.8144	Intermediate Similarity	NPC470559
0.8136	Intermediate Similarity	NPC99937
0.809	Intermediate Similarity	NPC470103
0.8066	Intermediate Similarity	NPC221185
0.8035	Intermediate Similarity	NPC470562
0.8024	Intermediate Similarity	NPC470564
0.8023	Intermediate Similarity	NPC151292
0.8022	Intermediate Similarity	NPC247104
0.7989	Intermediate Similarity	NPC191606
0.7989	Intermediate Similarity	NPC470560
0.7956	Intermediate Similarity	NPC470100
0.7943	Intermediate Similarity	NPC470422
0.7935	Intermediate Similarity	NPC198163
0.7931	Intermediate Similarity	NPC470565
0.7923	Intermediate Similarity	NPC214901
0.7907	Intermediate Similarity	NPC73544
0.7898	Intermediate Similarity	NPC471684
0.7869	Intermediate Similarity	NPC220369
0.7857	Intermediate Similarity	NPC470099
0.7849	Intermediate Similarity	NPC154720
0.7829	Intermediate Similarity	NPC107283
0.7807	Intermediate Similarity	NPC108744
0.7803	Intermediate Similarity	NPC471685
0.7803	Intermediate Similarity	NPC68850
0.7784	Intermediate Similarity	NPC48822
0.7771	Intermediate Similarity	NPC184518
0.7765	Intermediate Similarity	NPC471686
0.7759	Intermediate Similarity	NPC311679
0.7758	Intermediate Similarity	NPC8817
0.7756	Intermediate Similarity	NPC320819
0.7744	Intermediate Similarity	NPC75694
0.7742	Intermediate Similarity	NPC193676
0.773	Intermediate Similarity	NPC159721
0.773	Intermediate Similarity	NPC200207
0.7722	Intermediate Similarity	NPC474519
0.7716	Intermediate Similarity	NPC37530
0.7705	Intermediate Similarity	NPC313386
0.7702	Intermediate Similarity	NPC162939
0.7697	Intermediate Similarity	NPC470570
0.7697	Intermediate Similarity	NPC470357
0.7692	Intermediate Similarity	NPC62219
0.7692	Intermediate Similarity	NPC471695
0.7683	Intermediate Similarity	NPC151607
0.7683	Intermediate Similarity	NPC42540
0.7674	Intermediate Similarity	NPC313368
0.767	Intermediate Similarity	NPC108948
0.7657	Intermediate Similarity	NPC131078
0.7657	Intermediate Similarity	NPC301846
0.7654	Intermediate Similarity	NPC99441
0.7651	Intermediate Similarity	NPC137296
0.764	Intermediate Similarity	NPC191835
0.7636	Intermediate Similarity	NPC34482
0.7625	Intermediate Similarity	NPC472599
0.7622	Intermediate Similarity	NPC471731
0.7609	Intermediate Similarity	NPC316091
0.7609	Intermediate Similarity	NPC136411
0.7607	Intermediate Similarity	NPC472603
0.7607	Intermediate Similarity	NPC244923
0.76	Intermediate Similarity	NPC234053
0.7578	Intermediate Similarity	NPC70380
0.7578	Intermediate Similarity	NPC71256
0.7576	Intermediate Similarity	NPC48762
0.7571	Intermediate Similarity	NPC148480
0.7562	Intermediate Similarity	NPC278375
0.7561	Intermediate Similarity	NPC471733
0.7558	Intermediate Similarity	NPC197326
0.7553	Intermediate Similarity	NPC313541
0.7546	Intermediate Similarity	NPC472600
0.7546	Intermediate Similarity	NPC472601
0.7545	Intermediate Similarity	NPC166583
0.7545	Intermediate Similarity	NPC53362
0.7531	Intermediate Similarity	NPC33144
0.7531	Intermediate Similarity	NPC212693
0.7531	Intermediate Similarity	NPC94248
0.7531	Intermediate Similarity	NPC478200
0.753	Intermediate Similarity	NPC474630
0.7529	Intermediate Similarity	NPC117985
0.7516	Intermediate Similarity	NPC156967
0.7516	Intermediate Similarity	NPC158481
0.7515	Intermediate Similarity	NPC354984
0.75	Intermediate Similarity	NPC470359
0.75	Intermediate Similarity	NPC478217
0.75	Intermediate Similarity	NPC313123
0.75	Intermediate Similarity	NPC110810
0.75	Intermediate Similarity	NPC314653
0.75	Intermediate Similarity	NPC472623
0.75	Intermediate Similarity	NPC472604
0.75	Intermediate Similarity	NPC316262
0.75	Intermediate Similarity	NPC472605
0.7485	Intermediate Similarity	NPC473023
0.7485	Intermediate Similarity	NPC472211
0.7485	Intermediate Similarity	NPC52358
0.7485	Intermediate Similarity	NPC275356
0.7473	Intermediate Similarity	NPC471801
0.7471	Intermediate Similarity	NPC470810
0.7471	Intermediate Similarity	NPC232645
0.7471	Intermediate Similarity	NPC478148
0.7471	Intermediate Similarity	NPC149526
0.7471	Intermediate Similarity	NPC474417
0.7471	Intermediate Similarity	NPC72958
0.747	Intermediate Similarity	NPC471906
0.747	Intermediate Similarity	NPC193703
0.747	Intermediate Similarity	NPC21599
0.747	Intermediate Similarity	NPC469385
0.7469	Intermediate Similarity	NPC194579
0.7469	Intermediate Similarity	NPC474771
0.7469	Intermediate Similarity	NPC245058
0.7469	Intermediate Similarity	NPC474849
0.7469	Intermediate Similarity	NPC149372
0.7469	Intermediate Similarity	NPC65837
0.7469	Intermediate Similarity	NPC178467
0.7468	Intermediate Similarity	NPC296158
0.7457	Intermediate Similarity	NPC272196
0.7456	Intermediate Similarity	NPC198927
0.7456	Intermediate Similarity	NPC84142
0.7455	Intermediate Similarity	NPC474961
0.7455	Intermediate Similarity	NPC74397
0.7455	Intermediate Similarity	NPC135524
0.7443	Intermediate Similarity	NPC100849
0.744	Intermediate Similarity	NPC469425
0.744	Intermediate Similarity	NPC34802
0.744	Intermediate Similarity	NPC471734
0.7438	Intermediate Similarity	NPC37299
0.7438	Intermediate Similarity	NPC180261
0.7427	Intermediate Similarity	NPC115249
0.7427	Intermediate Similarity	NPC87708
0.7425	Intermediate Similarity	NPC28632
0.7423	Intermediate Similarity	NPC475974
0.7423	Intermediate Similarity	NPC472602
0.7412	Intermediate Similarity	NPC470568
0.7412	Intermediate Similarity	NPC164762
0.7412	Intermediate Similarity	NPC472891
0.741	Intermediate Similarity	NPC472610
0.741	Intermediate Similarity	NPC84266
0.741	Intermediate Similarity	NPC478202
0.741	Intermediate Similarity	NPC472006
0.7407	Intermediate Similarity	NPC191976
0.7394	Intermediate Similarity	NPC478201
0.7394	Intermediate Similarity	NPC472035
0.7394	Intermediate Similarity	NPC187843
0.7394	Intermediate Similarity	NPC67650
0.7394	Intermediate Similarity	NPC305845
0.7394	Intermediate Similarity	NPC1704
0.7394	Intermediate Similarity	NPC204045
0.7394	Intermediate Similarity	NPC53649
0.7391	Intermediate Similarity	NPC474394
0.7384	Intermediate Similarity	NPC169990
0.7384	Intermediate Similarity	NPC210942
0.7384	Intermediate Similarity	NPC137301
0.7384	Intermediate Similarity	NPC470102
0.7381	Intermediate Similarity	NPC471735
0.7381	Intermediate Similarity	NPC136878
0.7378	Intermediate Similarity	NPC88269
0.7378	Intermediate Similarity	NPC105456
0.7378	Intermediate Similarity	NPC139634
0.7377	Intermediate Similarity	NPC306240
0.7372	Intermediate Similarity	NPC477454
0.7368	Intermediate Similarity	NPC470569
0.7368	Intermediate Similarity	NPC91809
0.7356	Intermediate Similarity	NPC472889
0.7356	Intermediate Similarity	NPC246466
0.7356	Intermediate Similarity	NPC478225
0.7353	Intermediate Similarity	NPC65589
0.7353	Intermediate Similarity	NPC97028
0.7353	Intermediate Similarity	NPC158338
0.7353	Intermediate Similarity	NPC288036
0.7353	Intermediate Similarity	NPC97029
0.7353	Intermediate Similarity	NPC100985
0.7353	Intermediate Similarity	NPC329933
0.7349	Intermediate Similarity	NPC308572
0.7349	Intermediate Similarity	NPC182255
0.7349	Intermediate Similarity	NPC94076
0.7346	Intermediate Similarity	NPC474076
0.7346	Intermediate Similarity	NPC475917
0.7346	Intermediate Similarity	NPC290803
0.7341	Intermediate Similarity	NPC149618
0.7341	Intermediate Similarity	NPC471456

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 NPC245122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	1099
0.2-0.3	2161
0.3-0.4	3052
0.4-0.5	1810
0.5-0.6	543
0.6-0.7	128
0.7-0.8	4
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
0.7744	Intermediate Similarity	NPD2533	Approved
0.7744	Intermediate Similarity	NPD2532	Approved
0.7744	Intermediate Similarity	NPD2534	Approved
0.76	Intermediate Similarity	NPD2403	Approved
0.7195	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5711	Approved
0.7095	Intermediate Similarity	NPD5710	Approved
0.7059	Intermediate Similarity	NPD7390	Discontinued
0.7039	Intermediate Similarity	NPD6959	Discontinued
0.7024	Intermediate Similarity	NPD2800	Approved
0.7018	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD970	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3882	Suspended
0.6893	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7819	Suspended
0.6872	Remote Similarity	NPD7075	Discontinued
0.6854	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4361	Phase 2
0.6798	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6651	Approved
0.6766	Remote Similarity	NPD1607	Approved
0.676	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4363	Phase 3
0.6753	Remote Similarity	NPD4360	Phase 2
0.6724	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4380	Phase 2
0.6723	Remote Similarity	NPD6599	Discontinued
0.6721	Remote Similarity	NPD6232	Discontinued
0.6706	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7473	Discontinued
0.6702	Remote Similarity	NPD6559	Discontinued
0.6686	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD1549	Phase 2
0.6648	Remote Similarity	NPD6801	Discontinued
0.6648	Remote Similarity	NPD1934	Approved
0.6648	Remote Similarity	NPD919	Approved
0.6647	Remote Similarity	NPD5404	Approved
0.6647	Remote Similarity	NPD5405	Approved
0.6647	Remote Similarity	NPD1240	Approved
0.6647	Remote Similarity	NPD5406	Approved
0.6647	Remote Similarity	NPD5408	Approved
0.6629	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD1247	Approved
0.6571	Remote Similarity	NPD6799	Approved
0.6564	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6166	Phase 2
0.655	Remote Similarity	NPD2796	Approved
0.6548	Remote Similarity	NPD943	Approved
0.6543	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1578	Phase 2
0.6522	Remote Similarity	NPD5494	Approved
0.6503	Remote Similarity	NPD3749	Approved
0.65	Remote Similarity	NPD7411	Suspended
0.65	Remote Similarity	NPD4914	Approved
0.65	Remote Similarity	NPD958	Approved
0.6497	Remote Similarity	NPD1512	Approved
0.6484	Remote Similarity	NPD3817	Phase 2
0.6481	Remote Similarity	NPD1201	Approved
0.6461	Remote Similarity	NPD920	Approved
0.6455	Remote Similarity	NPD5844	Phase 1
0.6453	Remote Similarity	NPD2935	Discontinued
0.6453	Remote Similarity	NPD6100	Approved
0.6453	Remote Similarity	NPD1551	Phase 2
0.6453	Remote Similarity	NPD6099	Approved
0.6443	Remote Similarity	NPD8150	Discontinued
0.6429	Remote Similarity	NPD2801	Approved
0.6429	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD957	Approved
0.6424	Remote Similarity	NPD1470	Approved
0.642	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6534	Approved
0.6414	Remote Similarity	NPD6535	Approved
0.6412	Remote Similarity	NPD230	Phase 1
0.6402	Remote Similarity	NPD3818	Discontinued
0.6392	Remote Similarity	NPD6784	Approved
0.6392	Remote Similarity	NPD6785	Approved
0.6387	Remote Similarity	NPD6797	Phase 2
0.6384	Remote Similarity	NPD1511	Approved
0.6383	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3887	Approved
0.6359	Remote Similarity	NPD7768	Phase 2
0.6355	Remote Similarity	NPD4386	Approved
0.6355	Remote Similarity	NPD4387	Approved
0.6354	Remote Similarity	NPD7251	Discontinued
0.635	Remote Similarity	NPD4915	Approved
0.6348	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1243	Approved
0.6324	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2346	Discontinued
0.6321	Remote Similarity	NPD7808	Phase 3
0.6321	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7700	Phase 2
0.6318	Remote Similarity	NPD7699	Phase 2
0.6307	Remote Similarity	NPD3750	Approved
0.6307	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3226	Approved
0.6296	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5544	Approved
0.6271	Remote Similarity	NPD2354	Approved
0.6256	Remote Similarity	NPD6779	Approved
0.6256	Remote Similarity	NPD6777	Approved
0.6256	Remote Similarity	NPD6778	Approved
0.6256	Remote Similarity	NPD6781	Approved
0.6256	Remote Similarity	NPD6776	Approved
0.6256	Remote Similarity	NPD6782	Approved
0.6256	Remote Similarity	NPD6780	Approved
0.625	Remote Similarity	NPD2654	Approved
0.625	Remote Similarity	NPD7074	Phase 3
0.6244	Remote Similarity	NPD7435	Discontinued
0.6243	Remote Similarity	NPD3926	Phase 2
0.6238	Remote Similarity	NPD4974	Approved
0.6238	Remote Similarity	NPD4975	Approved
0.6237	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD3300	Phase 2
0.6235	Remote Similarity	NPD3764	Approved
0.6229	Remote Similarity	NPD1471	Phase 3
0.6229	Remote Similarity	NPD2344	Approved
0.6219	Remote Similarity	NPD4931	Phase 2
0.6216	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5402	Approved
0.6215	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8319	Approved
0.6214	Remote Similarity	NPD8320	Phase 1
0.6198	Remote Similarity	NPD7054	Approved
0.6193	Remote Similarity	NPD8434	Phase 2
0.6188	Remote Similarity	NPD5403	Approved
0.6188	Remote Similarity	NPD4388	Approved
0.6183	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD7472	Approved
0.6165	Remote Similarity	NPD7696	Phase 3
0.6165	Remote Similarity	NPD7697	Approved
0.6165	Remote Similarity	NPD7698	Approved
0.6158	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD454	Approved
0.6149	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2353	Approved
0.6135	Remote Similarity	NPD7871	Phase 2
0.6135	Remote Similarity	NPD7870	Phase 2
0.6135	Remote Similarity	NPD9545	Approved
0.6134	Remote Similarity	NPD5953	Discontinued
0.6124	Remote Similarity	NPD4628	Phase 3
0.612	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6234	Discontinued
0.6117	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6020	Phase 2
0.6114	Remote Similarity	NPD2799	Discontinued
0.6111	Remote Similarity	NPD9493	Approved
0.6111	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7041	Phase 2
0.6108	Remote Similarity	NPD37	Approved
0.6106	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD4967	Phase 2
0.6096	Remote Similarity	NPD4965	Approved
0.6096	Remote Similarity	NPD4966	Approved
0.6089	Remote Similarity	NPD2309	Approved
0.6089	Remote Similarity	NPD6190	Approved
0.6087	Remote Similarity	NPD4972	Discontinued
0.6083	Remote Similarity	NPD8366	Approved
0.6082	Remote Similarity	NPD4625	Phase 3
0.6077	Remote Similarity	NPD5401	Approved
0.6075	Remote Similarity	NPD5761	Phase 2
0.6075	Remote Similarity	NPD5760	Phase 2
0.6073	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7874	Approved
0.6066	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD3751	Discontinued
0.6061	Remote Similarity	NPD4626	Approved
0.6061	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD7236	Approved
0.6051	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.605	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7701	Phase 2
0.6047	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD1164	Approved
0.6034	Remote Similarity	NPD5124	Phase 1
0.6034	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7286	Phase 2
0.6029	Remote Similarity	NPD5543	Approved
0.6023	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3748	Approved
0.6021	Remote Similarity	NPD3787	Discontinued
0.6021	Remote Similarity	NPD7229	Phase 3
0.602	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3303	Discontinued
0.6019	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD8151	Discontinued
0.6011	Remote Similarity	NPD4534	Discontinued
0.6011	Remote Similarity	NPD5958	Discontinued
0.6009	Remote Similarity	NPD1852	Discontinued
0.6	Remote Similarity	NPD1729	Discontinued
0.6	Remote Similarity	NPD3365	Discontinued
0.6	Remote Similarity	NPD5691	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