NPASS Compound

Structure

NPC28160 OpenBabel07101719242D 28 29 0 0 0 0 0 0 0 0999 V2000 -0.8372 -2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1858 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1858 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 -1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1858 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 -1.4500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 -1.4500 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 5.0229 -1.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5115 0.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 -1.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1858 1.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 1.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 0.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 10 2 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 21 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 28 1 0 0 0 0 16 28 1 0 0 0 0 17 23 2 0 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.02
Volume:	382.424
LogP:	4.638
LogD:	3.129
LogS:	-4.336
# Rotatable Bonds:	7
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	2.74
Fsp3:	0.222
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:	-4.858
MDCK Permeability:	2.0897765352856368e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	100.25926208496094%
Volume Distribution (VD):	0.465
Pgp-substrate:	3.08622145652771%

ADMET: Metabolism

CYP1A2-inhibitor:	0.685
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.908
CYP2C19-substrate:	0.27
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.405
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	10.424
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.495
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.765
Respiratory Toxicity:	0.378

Download Data

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

Natural Product: NPC28160

Natural Product ID:	NPC28160
*Common Name:**	Metyl Dichloroasterrate
IUPAC Name:	methyl 3,5-dichloro-2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoate
Synonyms:	Methyl 3,5-Dichloroasterric Acid; Metyl Dichloroasterrate
Standard InCHIKey:	UWTOESDPWKUNBD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16Cl2O8/c1-7-12(19)14(22)11(18(24)27-4)16(13(7)20)28-15-9(17(23)26-3)5-8(21)6-10(15)25-2/h5-6,21-22H,1-4H3
SMILES:	COc1cc(O)cc(c1Oc1c(Cl)c(C)c(c(c1C(=O)OC)O)Cl)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511994
PubChem CID:	637419
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO32471	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809055]
NPO40445	Aspergillus flavipes HN4-13	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933892]

☑ 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	2
Ki	1
Others	8

Activity Type	# Activity
Cell Line	6
Organism	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI	<	34.0	%	PMID[513579]
NPT65	Cell Line	HepG2	Homo sapiens	GI	<	34.0	%	PMID[513579]
NPT15	Cell Line	Jurkat	Homo sapiens	GI	<	34.0	%	PMID[513579]
NPT81	Cell Line	A549	Homo sapiens	GI	<	34.0	%	PMID[513579]
NPT111	Cell Line	K562	Homo sapiens	GI	<	34.0	%	PMID[513579]
NPT492	Cell Line	Caco-2	Homo sapiens	CC50	>	800000.0	nM	PMID[513579]
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	LD90	=	75.0	ppm	PMID[513576]
NPT2	Others	Unspecified		IC50	=	1452.0	nM	PMID[513578]
NPT2	Others	Unspecified		IC50	=	90000.0	nM	PMID[513579]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	8.9	n.a.	PMID[513579]
NPT2	Others	Unspecified		Ki	=	2800.0	nM	PMID[513579]

☑ 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 NPC28160 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	449
0.1-0.2	2475
0.2-0.3	7504
0.3-0.4	12159
0.4-0.5	4167
0.5-0.6	6030
0.6-0.7	7926
0.7-0.8	1937
0.8-0.85	21
0.85-0.9	23
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC188618
0.8927	High Similarity	NPC471804
0.8927	High Similarity	NPC471812
0.8876	High Similarity	NPC39409
0.8827	High Similarity	NPC471806
0.8827	High Similarity	NPC471807
0.8827	High Similarity	NPC471810
0.88	High Similarity	NPC471801
0.8771	High Similarity	NPC471805
0.8771	High Similarity	NPC471813
0.8771	High Similarity	NPC121100
0.8715	High Similarity	NPC471803
0.8659	High Similarity	NPC285527
0.8659	High Similarity	NPC106334
0.8626	High Similarity	NPC214901
0.8606	High Similarity	NPC213382
0.8606	High Similarity	NPC164527
0.8571	High Similarity	NPC470422
0.8571	High Similarity	NPC220369
0.8531	High Similarity	NPC471802
0.85	High Similarity	NPC471811
0.85	High Similarity	NPC471809
0.8475	Intermediate Similarity	NPC108278
0.8475	Intermediate Similarity	NPC45072
0.8444	Intermediate Similarity	NPC195675
0.8444	Intermediate Similarity	NPC471814
0.8444	Intermediate Similarity	NPC471808
0.8441	Intermediate Similarity	NPC154720
0.8432	Intermediate Similarity	NPC198163
0.8274	Intermediate Similarity	NPC225129
0.8256	Intermediate Similarity	NPC287458
0.8208	Intermediate Similarity	NPC98892
0.8167	Intermediate Similarity	NPC175804
0.8138	Intermediate Similarity	NPC193676
0.807	Intermediate Similarity	NPC289968
0.8034	Intermediate Similarity	NPC472032
0.7965	Intermediate Similarity	NPC75069
0.7957	Intermediate Similarity	NPC474499
0.7944	Intermediate Similarity	NPC277865
0.7912	Intermediate Similarity	NPC264922
0.7901	Intermediate Similarity	NPC474857
0.7898	Intermediate Similarity	NPC130955
0.7889	Intermediate Similarity	NPC49487
0.7889	Intermediate Similarity	NPC99613
0.7884	Intermediate Similarity	NPC221185
0.7882	Intermediate Similarity	NPC46941
0.7874	Intermediate Similarity	NPC208197
0.7865	Intermediate Similarity	NPC300984
0.7853	Intermediate Similarity	NPC217950
0.7845	Intermediate Similarity	NPC109827
0.7845	Intermediate Similarity	NPC124470
0.7845	Intermediate Similarity	NPC72696
0.7842	Intermediate Similarity	NPC247104
0.7829	Intermediate Similarity	NPC54928
0.7816	Intermediate Similarity	NPC280937
0.7816	Intermediate Similarity	NPC75279
0.7816	Intermediate Similarity	NPC276409
0.7816	Intermediate Similarity	NPC250822
0.7816	Intermediate Similarity	NPC472915
0.7814	Intermediate Similarity	NPC477568
0.7803	Intermediate Similarity	NPC226973
0.7803	Intermediate Similarity	NPC308451
0.7803	Intermediate Similarity	NPC208043
0.7802	Intermediate Similarity	NPC158226
0.7791	Intermediate Similarity	NPC200221
0.7791	Intermediate Similarity	NPC328119
0.7791	Intermediate Similarity	NPC294502
0.7778	Intermediate Similarity	NPC119660
0.7778	Intermediate Similarity	NPC29160
0.7778	Intermediate Similarity	NPC20216
0.7778	Intermediate Similarity	NPC470100
0.7778	Intermediate Similarity	NPC470099
0.7778	Intermediate Similarity	NPC93034
0.7771	Intermediate Similarity	NPC256612
0.7771	Intermediate Similarity	NPC92659
0.7771	Intermediate Similarity	NPC128863
0.7771	Intermediate Similarity	NPC138360
0.7771	Intermediate Similarity	NPC280339
0.7771	Intermediate Similarity	NPC50715
0.7771	Intermediate Similarity	NPC196439
0.7771	Intermediate Similarity	NPC201136
0.7771	Intermediate Similarity	NPC163780
0.7771	Intermediate Similarity	NPC146165
0.7771	Intermediate Similarity	NPC4455
0.7771	Intermediate Similarity	NPC471800
0.7771	Intermediate Similarity	NPC227325
0.7771	Intermediate Similarity	NPC2476
0.7771	Intermediate Similarity	NPC20830
0.7771	Intermediate Similarity	NPC183597
0.7771	Intermediate Similarity	NPC167815
0.7765	Intermediate Similarity	NPC474350
0.7765	Intermediate Similarity	NPC156082
0.776	Intermediate Similarity	NPC181523
0.7759	Intermediate Similarity	NPC199773
0.7753	Intermediate Similarity	NPC298401
0.7753	Intermediate Similarity	NPC303565
0.7747	Intermediate Similarity	NPC246716
0.7747	Intermediate Similarity	NPC107283
0.7747	Intermediate Similarity	NPC470565
0.7747	Intermediate Similarity	NPC10576
0.7747	Intermediate Similarity	NPC17219
0.7746	Intermediate Similarity	NPC179183
0.7746	Intermediate Similarity	NPC306821
0.7742	Intermediate Similarity	NPC151292
0.774	Intermediate Similarity	NPC190487
0.774	Intermediate Similarity	NPC154304
0.774	Intermediate Similarity	NPC83763
0.774	Intermediate Similarity	NPC238381
0.774	Intermediate Similarity	NPC168616
0.7735	Intermediate Similarity	NPC234331
0.7732	Intermediate Similarity	NPC108744
0.7727	Intermediate Similarity	NPC472916
0.7727	Intermediate Similarity	NPC178854
0.7727	Intermediate Similarity	NPC474520
0.7725	Intermediate Similarity	NPC316091
0.7722	Intermediate Similarity	NPC267153
0.7722	Intermediate Similarity	NPC68850
0.7722	Intermediate Similarity	NPC173352
0.7722	Intermediate Similarity	NPC112981
0.7722	Intermediate Similarity	NPC58653
0.7714	Intermediate Similarity	NPC298802
0.7714	Intermediate Similarity	NPC22519
0.7714	Intermediate Similarity	NPC176775
0.7714	Intermediate Similarity	NPC47781
0.7714	Intermediate Similarity	NPC183878
0.7714	Intermediate Similarity	NPC86485
0.7714	Intermediate Similarity	NPC471981
0.7714	Intermediate Similarity	NPC255350
0.7714	Intermediate Similarity	NPC246204
0.7714	Intermediate Similarity	NPC145379
0.7714	Intermediate Similarity	NPC160951
0.7714	Intermediate Similarity	NPC274327
0.7714	Intermediate Similarity	NPC231018
0.7714	Intermediate Similarity	NPC475895
0.7714	Intermediate Similarity	NPC69394
0.7713	Intermediate Similarity	NPC191606
0.7709	Intermediate Similarity	NPC473696
0.7709	Intermediate Similarity	NPC93739
0.7708	Intermediate Similarity	NPC48822
0.7701	Intermediate Similarity	NPC117579
0.7701	Intermediate Similarity	NPC149614
0.7701	Intermediate Similarity	NPC474663
0.7697	Intermediate Similarity	NPC188967
0.7692	Intermediate Similarity	NPC280493
0.7692	Intermediate Similarity	NPC163130
0.7692	Intermediate Similarity	NPC26568
0.7692	Intermediate Similarity	NPC476279
0.7692	Intermediate Similarity	NPC165979
0.7692	Intermediate Similarity	NPC214919
0.7692	Intermediate Similarity	NPC124467
0.7688	Intermediate Similarity	NPC92722
0.7688	Intermediate Similarity	NPC102003
0.7684	Intermediate Similarity	NPC7973
0.7684	Intermediate Similarity	NPC235215
0.7684	Intermediate Similarity	NPC262286
0.7684	Intermediate Similarity	NPC476981
0.7684	Intermediate Similarity	NPC93376
0.7684	Intermediate Similarity	NPC75215
0.7684	Intermediate Similarity	NPC78302
0.7684	Intermediate Similarity	NPC181960
0.7684	Intermediate Similarity	NPC189179
0.7684	Intermediate Similarity	NPC472438
0.7684	Intermediate Similarity	NPC29841
0.7684	Intermediate Similarity	NPC227192
0.7684	Intermediate Similarity	NPC224137
0.7684	Intermediate Similarity	NPC36852
0.768	Intermediate Similarity	NPC28669
0.768	Intermediate Similarity	NPC474061
0.7674	Intermediate Similarity	NPC33265
0.7674	Intermediate Similarity	NPC62536
0.767	Intermediate Similarity	NPC37392
0.767	Intermediate Similarity	NPC286052
0.767	Intermediate Similarity	NPC189960
0.767	Intermediate Similarity	NPC32557
0.767	Intermediate Similarity	NPC213622
0.767	Intermediate Similarity	NPC2928
0.767	Intermediate Similarity	NPC472909
0.7668	Intermediate Similarity	NPC313541
0.7667	Intermediate Similarity	NPC470081
0.7667	Intermediate Similarity	NPC284007
0.7667	Intermediate Similarity	NPC477689
0.7657	Intermediate Similarity	NPC293183
0.7657	Intermediate Similarity	NPC142540
0.7657	Intermediate Similarity	NPC60972
0.7657	Intermediate Similarity	NPC187498
0.7657	Intermediate Similarity	NPC134677
0.7657	Intermediate Similarity	NPC275722
0.7657	Intermediate Similarity	NPC256283
0.7657	Intermediate Similarity	NPC212678
0.7657	Intermediate Similarity	NPC25270
0.7657	Intermediate Similarity	NPC156222
0.7657	Intermediate Similarity	NPC57030
0.7657	Intermediate Similarity	NPC162313
0.7657	Intermediate Similarity	NPC101996
0.7657	Intermediate Similarity	NPC120163
0.7657	Intermediate Similarity	NPC131624
0.7657	Intermediate Similarity	NPC71334
0.7657	Intermediate Similarity	NPC39732
0.7657	Intermediate Similarity	NPC222830
0.7657	Intermediate Similarity	NPC301123

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 NPC28160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	1177
0.2-0.3	2287
0.3-0.4	2703
0.4-0.5	1601
0.5-0.6	723
0.6-0.7	219
0.7-0.8	31
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
0.7733	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2801	Approved
0.7527	Intermediate Similarity	NPD2403	Approved
0.7514	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7472	Intermediate Similarity	NPD5402	Approved
0.7472	Intermediate Similarity	NPD3817	Phase 2
0.747	Intermediate Similarity	NPD447	Suspended
0.743	Intermediate Similarity	NPD3882	Suspended
0.743	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7473	Discontinued
0.7365	Intermediate Similarity	NPD1184	Approved
0.736	Intermediate Similarity	NPD1934	Approved
0.734	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5844	Phase 1
0.7258	Intermediate Similarity	NPD3818	Discontinued
0.7222	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1511	Approved
0.7193	Intermediate Similarity	NPD2935	Discontinued
0.7151	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6166	Phase 2
0.7151	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7054	Approved
0.7127	Intermediate Similarity	NPD1465	Phase 2
0.712	Intermediate Similarity	NPD5494	Approved
0.7119	Intermediate Similarity	NPD1512	Approved
0.7104	Intermediate Similarity	NPD7075	Discontinued
0.7102	Intermediate Similarity	NPD6799	Approved
0.709	Intermediate Similarity	NPD7472	Approved
0.709	Intermediate Similarity	NPD7074	Phase 3
0.7079	Intermediate Similarity	NPD5403	Approved
0.7062	Intermediate Similarity	NPD1578	Phase 2
0.7059	Intermediate Similarity	NPD1933	Approved
0.7056	Intermediate Similarity	NPD6599	Discontinued
0.7033	Intermediate Similarity	NPD7819	Suspended
0.7016	Intermediate Similarity	NPD6559	Discontinued
0.7011	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3226	Approved
0.6995	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1203	Approved
0.6979	Remote Similarity	NPD7808	Phase 3
0.6966	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2534	Approved
0.6966	Remote Similarity	NPD5401	Approved
0.6966	Remote Similarity	NPD2532	Approved
0.6966	Remote Similarity	NPD2533	Approved
0.6963	Remote Similarity	NPD6797	Phase 2
0.6963	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD230	Phase 1
0.694	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7251	Discontinued
0.6923	Remote Similarity	NPD7411	Suspended
0.6919	Remote Similarity	NPD1607	Approved
0.6919	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6801	Discontinued
0.6882	Remote Similarity	NPD411	Approved
0.6868	Remote Similarity	NPD4380	Phase 2
0.6868	Remote Similarity	NPD4972	Discontinued
0.6865	Remote Similarity	NPD7768	Phase 2
0.6864	Remote Similarity	NPD6832	Phase 2
0.686	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2346	Discontinued
0.6853	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD1653	Approved
0.6836	Remote Similarity	NPD3750	Approved
0.6831	Remote Similarity	NPD958	Approved
0.6825	Remote Similarity	NPD3926	Phase 2
0.6818	Remote Similarity	NPD1549	Phase 2
0.6809	Remote Similarity	NPD6959	Discontinued
0.6809	Remote Similarity	NPD1247	Approved
0.6807	Remote Similarity	NPD9717	Approved
0.6802	Remote Similarity	NPD1240	Approved
0.68	Remote Similarity	NPD6312	Discontinued
0.6796	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD37	Approved
0.6791	Remote Similarity	NPD919	Approved
0.6791	Remote Similarity	NPD6234	Discontinued
0.6778	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4966	Approved
0.6774	Remote Similarity	NPD4967	Phase 2
0.6774	Remote Similarity	NPD4965	Approved
0.6761	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD957	Approved
0.6743	Remote Similarity	NPD1510	Phase 2
0.6742	Remote Similarity	NPD4628	Phase 3
0.6706	Remote Similarity	NPD454	Approved
0.6705	Remote Similarity	NPD2796	Approved
0.6702	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2313	Discontinued
0.6684	Remote Similarity	NPD8312	Approved
0.6684	Remote Similarity	NPD8313	Approved
0.6649	Remote Similarity	NPD3749	Approved
0.6648	Remote Similarity	NPD2799	Discontinued
0.6648	Remote Similarity	NPD4308	Phase 3
0.6634	Remote Similarity	NPD4360	Phase 2
0.6634	Remote Similarity	NPD4363	Phase 3
0.6631	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5953	Discontinued
0.6611	Remote Similarity	NPD6190	Approved
0.6611	Remote Similarity	NPD2354	Approved
0.6609	Remote Similarity	NPD943	Approved
0.6598	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD3748	Approved
0.6546	Remote Similarity	NPD7228	Approved
0.6545	Remote Similarity	NPD7199	Phase 2
0.6543	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5353	Approved
0.6538	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD920	Approved
0.652	Remote Similarity	NPD4361	Phase 2
0.652	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3887	Approved
0.6517	Remote Similarity	NPD6100	Approved
0.6517	Remote Similarity	NPD6099	Approved
0.6513	Remote Similarity	NPD7286	Phase 2
0.6512	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5710	Approved
0.651	Remote Similarity	NPD5711	Approved
0.65	Remote Similarity	NPD1243	Approved
0.65	Remote Similarity	NPD2800	Approved
0.65	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD9493	Approved
0.648	Remote Similarity	NPD2353	Approved
0.648	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5242	Approved
0.6477	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD1019	Discontinued
0.6452	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.645	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3027	Phase 3
0.6425	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1613	Approved
0.642	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4307	Phase 2
0.6418	Remote Similarity	NPD8150	Discontinued
0.6418	Remote Similarity	NPD8434	Phase 2
0.6414	Remote Similarity	NPD7685	Pre-registration
0.6414	Remote Similarity	NPD7038	Approved
0.6414	Remote Similarity	NPD7039	Approved
0.6413	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD9269	Phase 2
0.6404	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2797	Approved
0.6394	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6385	Approved
0.6383	Remote Similarity	NPD6386	Approved
0.6381	Remote Similarity	NPD7435	Discontinued
0.6378	Remote Similarity	NPD3751	Discontinued
0.6374	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD9268	Approved
0.6359	Remote Similarity	NPD4357	Discontinued
0.6359	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4534	Discontinued
0.6353	Remote Similarity	NPD422	Phase 1
0.6349	Remote Similarity	NPD6844	Discontinued
0.6343	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3225	Approved
0.6331	Remote Similarity	NPD1778	Approved
0.6322	Remote Similarity	NPD3018	Phase 2
0.6322	Remote Similarity	NPD9494	Approved
0.6316	Remote Similarity	NPD6782	Approved
0.6316	Remote Similarity	NPD6779	Approved
0.6316	Remote Similarity	NPD6781	Approved
0.6316	Remote Similarity	NPD6777	Approved
0.6316	Remote Similarity	NPD6778	Approved
0.6316	Remote Similarity	NPD1608	Approved
0.6316	Remote Similarity	NPD6776	Approved
0.6316	Remote Similarity	NPD6780	Approved
0.6308	Remote Similarity	NPD8151	Discontinued
0.6307	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD3268	Approved
0.6304	Remote Similarity	NPD643	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7549	Discontinued
0.6298	Remote Similarity	NPD2344	Approved
0.6294	Remote Similarity	NPD3496	Discontinued
0.6294	Remote Similarity	NPD915	Approved
0.6289	Remote Similarity	NPD8127	Discontinued
0.6279	Remote Similarity	NPD4749	Approved
0.6278	Remote Similarity	NPD7033	Discontinued
0.6278	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6233	Phase 2
0.627	Remote Similarity	NPD7390	Discontinued
0.6264	Remote Similarity	NPD2798	Approved
0.6264	Remote Similarity	NPD5958	Discontinued
0.6257	Remote Similarity	NPD6651	Approved
0.6256	Remote Similarity	NPD3787	Discontinued
0.6256	Remote Similarity	NPD6823	Phase 2
0.625	Remote Similarity	NPD7240	Approved
0.625	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4625	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