NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	235.1
Volume:	258.318
LogP:	4.153
LogD:	3.889
LogS:	-5.22
# Rotatable Bonds:	2
TPSA:	22.12
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	1.52
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.714
MDCK Permeability:	1.8321394236409105e-05
Pgp-inhibitor:	0.082
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.753
Plasma Protein Binding (PPB):	97.7254409790039%
Volume Distribution (VD):	1.014
Pgp-substrate:	1.4406638145446777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.618
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.209
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	5.886
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.684
AMES Toxicity:	0.866
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.098
Skin Sensitization:	0.344
Carcinogencity:	0.738
Eye Corrosion:	0.025
Eye Irritation:	0.979
Respiratory Toxicity:	0.216

Download Data

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

Natural Product: NPC26850

Natural Product ID:	NPC26850
*Common Name:**	4-Methoxy-2-Phenylquinoline
IUPAC Name:	4-methoxy-2-phenylquinoline
Synonyms:
Standard InCHIKey:	CVJHRDUVYHASOG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H13NO/c1-18-16-11-15(12-7-3-2-4-8-12)17-14-10-6-5-9-13(14)16/h2-11H,1H3
SMILES:	COc1cc(nc2c1cccc2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL279335
PubChem CID:	826247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

*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
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374942]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499324]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14518	Ateleia herbert-smithii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16708	Pinus abies	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16452	Iochroma coccineum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19489	Tylosema esculentum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19680	Haminoea orteai	Species	Haminoeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16032	Xanthoparmelia quintaria	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17983	Nigrosabulum globosum	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13657	Peperomia pellucida	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18972	Astropecten indicus	Species	Astropectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18402	Tecoma peroba	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17868	Eucryphia glutinosa	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO83	Saccharina angustata	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18897	Cephalosporium gregatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	6
IC50	2
Kd	1
MIC	1
Others	25
Potency	11

Activity Type	# Activity
Cell Line	7
Individual Protein	9
NON-MOLECULAR	1
Organism	26
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[505158]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[505158]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[505158]
NPT168	Cell Line	P388	Mus musculus	EC50	=	4.5	ug.mL-1	PMID[505158]
NPT1868	Cell Line	L1210 (1565)		EC50	>	10.0	ug.mL-1	PMID[505158]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	35481.3	nM	PMID[505160]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	8912.5	nM	PMID[505160]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	28183.8	nM	PMID[505160]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[505160]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[505160]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[505160]
NPT804	Cell Line	HT-22	Mus musculus	EC50	=	750.0	nM	PMID[505162]
NPT848	Cell Line	N9	Homo sapiens	Activity	=	6.0	%	PMID[505162]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[505160]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[505160]
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	=	2130.0	nM	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	92.5	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	90.9	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	89.2	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	92.0	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	56.8	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	0.0	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	65.8	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	87.2	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	9.4	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	9.3	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	18.5	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	53.4	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	38.6	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	86.0	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	62.8	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	90.8	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	Aggregation	=	85.0	%	PMID[505157]
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	=	1700.0	nM	PMID[505157]
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC90	=	50.0	ug.mL-1	PMID[505159]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC90	=	100.0	ug.mL-1	PMID[505159]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	11220.2	nM	PMID[505160]
NPT2	Others	Unspecified		Potency	=	20596.2	nM	PMID[505160]
NPT2	Others	Unspecified		Kd	>	1000000.0	nM	PMID[505161]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.12	equiv	PMID[505162]
NPT2	Others	Unspecified		Potency	n.a.	4466.8	nM	PMID[505160]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	16.0	ug.mL-1	PMID[505163]

☑ 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 NPC26850 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	4759
0.2-0.3	12608
0.3-0.4	5165
0.4-0.5	14089
0.5-0.6	3528
0.6-0.7	1448
0.7-0.8	353
0.8-0.85	16
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC26872
0.9051	High Similarity	NPC312872
0.9026	High Similarity	NPC177404
0.8846	High Similarity	NPC118511
0.8788	High Similarity	NPC204385
0.8704	High Similarity	NPC283152
0.8659	High Similarity	NPC206201
0.8642	High Similarity	NPC288943
0.8443	Intermediate Similarity	NPC62069
0.8402	Intermediate Similarity	NPC66083
0.8373	Intermediate Similarity	NPC222592
0.8373	Intermediate Similarity	NPC168486
0.8284	Intermediate Similarity	NPC42591
0.8225	Intermediate Similarity	NPC84478
0.817	Intermediate Similarity	NPC60553
0.8137	Intermediate Similarity	NPC285635
0.8095	Intermediate Similarity	NPC472168
0.809	Intermediate Similarity	NPC329747
0.8079	Intermediate Similarity	NPC72211
0.8068	Intermediate Similarity	NPC70259
0.8059	Intermediate Similarity	NPC176127
0.8035	Intermediate Similarity	NPC242928
0.8023	Intermediate Similarity	NPC70956
0.8023	Intermediate Similarity	NPC267928
0.8023	Intermediate Similarity	NPC243834
0.8011	Intermediate Similarity	NPC131017
0.8011	Intermediate Similarity	NPC205934
0.8011	Intermediate Similarity	NPC43787
0.8011	Intermediate Similarity	NPC285558
0.8	Intermediate Similarity	NPC114335
0.8	Intermediate Similarity	NPC474798
0.8	Intermediate Similarity	NPC141915
0.8	Intermediate Similarity	NPC280964
0.7989	Intermediate Similarity	NPC11017
0.7955	Intermediate Similarity	NPC79293
0.7955	Intermediate Similarity	NPC279401
0.7898	Intermediate Similarity	NPC133140
0.7898	Intermediate Similarity	NPC195268
0.7892	Intermediate Similarity	NPC1527
0.7889	Intermediate Similarity	NPC19872
0.7857	Intermediate Similarity	NPC223427
0.7857	Intermediate Similarity	NPC162484
0.7845	Intermediate Similarity	NPC476044
0.7845	Intermediate Similarity	NPC267423
0.7845	Intermediate Similarity	NPC232727
0.7844	Intermediate Similarity	NPC477888
0.7814	Intermediate Similarity	NPC16452
0.7814	Intermediate Similarity	NPC36229
0.7814	Intermediate Similarity	NPC476581
0.7802	Intermediate Similarity	NPC475112
0.7802	Intermediate Similarity	NPC291535
0.7802	Intermediate Similarity	NPC475085
0.7798	Intermediate Similarity	NPC258773
0.7796	Intermediate Similarity	NPC167860
0.7796	Intermediate Similarity	NPC123976
0.7791	Intermediate Similarity	NPC118776
0.779	Intermediate Similarity	NPC329793
0.779	Intermediate Similarity	NPC234197
0.7784	Intermediate Similarity	NPC44161
0.7784	Intermediate Similarity	NPC470931
0.7751	Intermediate Similarity	NPC474409
0.7747	Intermediate Similarity	NPC470586
0.7738	Intermediate Similarity	NPC476518
0.7735	Intermediate Similarity	NPC4071
0.7735	Intermediate Similarity	NPC476582
0.7735	Intermediate Similarity	NPC476578
0.7733	Intermediate Similarity	NPC478032
0.7727	Intermediate Similarity	NPC296527
0.7705	Intermediate Similarity	NPC199277
0.7705	Intermediate Similarity	NPC295898
0.7705	Intermediate Similarity	NPC135887
0.7692	Intermediate Similarity	NPC176538
0.7692	Intermediate Similarity	NPC14651
0.7692	Intermediate Similarity	NPC121658
0.7692	Intermediate Similarity	NPC315957
0.7688	Intermediate Similarity	NPC475910
0.7688	Intermediate Similarity	NPC287208
0.7684	Intermediate Similarity	NPC471593
0.7684	Intermediate Similarity	NPC76748
0.7676	Intermediate Similarity	NPC476106
0.7676	Intermediate Similarity	NPC472111
0.7676	Intermediate Similarity	NPC304183
0.7667	Intermediate Similarity	NPC13880
0.7655	Intermediate Similarity	NPC54102
0.7655	Intermediate Similarity	NPC162689
0.765	Intermediate Similarity	NPC31930
0.7647	Intermediate Similarity	NPC174672
0.7647	Intermediate Similarity	NPC469589
0.7647	Intermediate Similarity	NPC174758
0.7647	Intermediate Similarity	NPC111624
0.764	Intermediate Similarity	NPC92111
0.764	Intermediate Similarity	NPC469390
0.7637	Intermediate Similarity	NPC128823
0.7637	Intermediate Similarity	NPC287437
0.7634	Intermediate Similarity	NPC193777
0.7625	Intermediate Similarity	NPC161292
0.7622	Intermediate Similarity	NPC47059
0.7622	Intermediate Similarity	NPC118832
0.7622	Intermediate Similarity	NPC329708
0.7622	Intermediate Similarity	NPC274291
0.7622	Intermediate Similarity	NPC264166
0.7622	Intermediate Similarity	NPC165349
0.7614	Intermediate Similarity	NPC61350
0.7596	Intermediate Similarity	NPC477019
0.7586	Intermediate Similarity	NPC144114
0.7584	Intermediate Similarity	NPC122718
0.7568	Intermediate Similarity	NPC475774
0.7568	Intermediate Similarity	NPC245816
0.7568	Intermediate Similarity	NPC476138
0.7566	Intermediate Similarity	NPC208284
0.7558	Intermediate Similarity	NPC473432
0.7557	Intermediate Similarity	NPC94943
0.7556	Intermediate Similarity	NPC307963
0.7556	Intermediate Similarity	NPC475190
0.7553	Intermediate Similarity	NPC201697
0.7544	Intermediate Similarity	NPC208060
0.7543	Intermediate Similarity	NPC212535
0.754	Intermediate Similarity	NPC4687
0.754	Intermediate Similarity	NPC249583
0.7531	Intermediate Similarity	NPC288445
0.7528	Intermediate Similarity	NPC110741
0.7527	Intermediate Similarity	NPC164374
0.7527	Intermediate Similarity	NPC137929
0.7527	Intermediate Similarity	NPC470930
0.7526	Intermediate Similarity	NPC202768
0.7526	Intermediate Similarity	NPC296482
0.7526	Intermediate Similarity	NPC264176
0.7526	Intermediate Similarity	NPC202605
0.7526	Intermediate Similarity	NPC53069
0.7526	Intermediate Similarity	NPC112206
0.7517	Intermediate Similarity	NPC148140
0.7514	Intermediate Similarity	NPC194040
0.7514	Intermediate Similarity	NPC314573
0.7514	Intermediate Similarity	NPC66815
0.7513	Intermediate Similarity	NPC269367
0.7513	Intermediate Similarity	NPC471304
0.7513	Intermediate Similarity	NPC470020
0.75	Intermediate Similarity	NPC82548
0.75	Intermediate Similarity	NPC320394
0.75	Intermediate Similarity	NPC190007
0.7487	Intermediate Similarity	NPC471080
0.7487	Intermediate Similarity	NPC469592
0.7474	Intermediate Similarity	NPC213530
0.7474	Intermediate Similarity	NPC193267
0.7473	Intermediate Similarity	NPC251090
0.7471	Intermediate Similarity	NPC72980
0.7471	Intermediate Similarity	NPC88363
0.7468	Intermediate Similarity	NPC280853
0.7466	Intermediate Similarity	NPC81561
0.746	Intermediate Similarity	NPC473181
0.7457	Intermediate Similarity	NPC56618
0.7457	Intermediate Similarity	NPC84347
0.7447	Intermediate Similarity	NPC313189
0.7446	Intermediate Similarity	NPC18487
0.7439	Intermediate Similarity	NPC153769
0.7435	Intermediate Similarity	NPC48353
0.7435	Intermediate Similarity	NPC171409
0.7435	Intermediate Similarity	NPC472098
0.7435	Intermediate Similarity	NPC96405
0.7427	Intermediate Similarity	NPC314940
0.7427	Intermediate Similarity	NPC473764
0.7423	Intermediate Similarity	NPC473041
0.7421	Intermediate Similarity	NPC285016
0.7421	Intermediate Similarity	NPC245657
0.7421	Intermediate Similarity	NPC199667
0.7409	Intermediate Similarity	NPC152768
0.7409	Intermediate Similarity	NPC274982
0.7409	Intermediate Similarity	NPC148183
0.7405	Intermediate Similarity	NPC121772
0.7405	Intermediate Similarity	NPC471596
0.7396	Intermediate Similarity	NPC159319
0.7396	Intermediate Similarity	NPC478074
0.7394	Intermediate Similarity	NPC45190
0.7394	Intermediate Similarity	NPC323345
0.7394	Intermediate Similarity	NPC470164
0.7394	Intermediate Similarity	NPC300156
0.7391	Intermediate Similarity	NPC471598
0.7386	Intermediate Similarity	NPC266551
0.7386	Intermediate Similarity	NPC161887
0.7386	Intermediate Similarity	NPC219963
0.7386	Intermediate Similarity	NPC477891
0.7386	Intermediate Similarity	NPC470474
0.7382	Intermediate Similarity	NPC87413
0.738	Intermediate Similarity	NPC469440
0.7371	Intermediate Similarity	NPC305984
0.7368	Intermediate Similarity	NPC278874
0.7368	Intermediate Similarity	NPC185782
0.7363	Intermediate Similarity	NPC230403
0.7358	Intermediate Similarity	NPC235076
0.7358	Intermediate Similarity	NPC16066
0.7358	Intermediate Similarity	NPC470549
0.7354	Intermediate Similarity	NPC193238
0.7354	Intermediate Similarity	NPC135549
0.7344	Intermediate Similarity	NPC94157
0.7344	Intermediate Similarity	NPC310211
0.7344	Intermediate Similarity	NPC308137
0.7344	Intermediate Similarity	NPC473180
0.7344	Intermediate Similarity	NPC26679
0.7337	Intermediate Similarity	NPC224928
0.7337	Intermediate Similarity	NPC59779

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 NPC26850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	461
0.1-0.2	732
0.2-0.3	795
0.3-0.4	1044
0.4-0.5	2794
0.5-0.6	2350
0.6-0.7	823
0.7-0.8	145
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD5083	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD3920	Phase 2
0.8324	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD6590	Discontinued
0.8214	Intermediate Similarity	NPD4203	Approved
0.8214	Intermediate Similarity	NPD4204	Approved
0.8171	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6550	Discontinued
0.8114	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2410	Phase 2
0.8068	Intermediate Similarity	NPD5512	Phase 3
0.8023	Intermediate Similarity	NPD6988	Phase 1
0.8023	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2882	Phase 1
0.7967	Intermediate Similarity	NPD6150	Discontinued
0.7965	Intermediate Similarity	NPD4889	Approved
0.7933	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3923	Approved
0.7898	Intermediate Similarity	NPD3924	Approved
0.7898	Intermediate Similarity	NPD6569	Phase 2
0.7898	Intermediate Similarity	NPD3922	Approved
0.7898	Intermediate Similarity	NPD3921	Approved
0.7895	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD5658	Approved
0.7875	Intermediate Similarity	NPD6158	Phase 2
0.7875	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6159	Phase 2
0.7809	Intermediate Similarity	NPD4418	Discontinued
0.7809	Intermediate Similarity	NPD6251	Discontinued
0.7802	Intermediate Similarity	NPD6208	Discontinued
0.7791	Intermediate Similarity	NPD3386	Phase 2
0.7778	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD5530	Phase 1
0.7765	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3477	Phase 2
0.776	Intermediate Similarity	NPD6991	Approved
0.7746	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5429	Discontinued
0.773	Intermediate Similarity	NPD7222	Phase 2
0.7719	Intermediate Similarity	NPD3503	Approved
0.7719	Intermediate Similarity	NPD3504	Approved
0.7717	Intermediate Similarity	NPD4795	Phase 2
0.7709	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD112	Approved
0.7697	Intermediate Similarity	NPD4372	Phase 1
0.7697	Intermediate Similarity	NPD9705	Discontinued
0.7692	Intermediate Similarity	NPD1740	Approved
0.7692	Intermediate Similarity	NPD1739	Approved
0.7676	Intermediate Similarity	NPD3003	Approved
0.7665	Intermediate Similarity	NPD2782	Approved
0.7665	Intermediate Similarity	NPD2780	Approved
0.766	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD32	Approved
0.7622	Intermediate Similarity	NPD31	Approved
0.7622	Intermediate Similarity	NPD4122	Approved
0.7622	Intermediate Similarity	NPD4036	Approved
0.7622	Intermediate Similarity	NPD4033	Approved
0.7622	Intermediate Similarity	NPD4039	Approved
0.7622	Intermediate Similarity	NPD4038	Approved
0.7622	Intermediate Similarity	NPD4037	Approved
0.7622	Intermediate Similarity	NPD4034	Approved
0.7622	Intermediate Similarity	NPD4035	Approved
0.7611	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7672	Approved
0.7594	Intermediate Similarity	NPD7671	Approved
0.7581	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2781	Approved
0.7571	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2749	Discontinued
0.7562	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD4354	Approved
0.7556	Intermediate Similarity	NPD1038	Approved
0.7542	Intermediate Similarity	NPD2334	Discontinued
0.7541	Intermediate Similarity	NPD3825	Phase 3
0.754	Intermediate Similarity	NPD7452	Approved
0.754	Intermediate Similarity	NPD7453	Approved
0.7527	Intermediate Similarity	NPD4673	Phase 2
0.7526	Intermediate Similarity	NPD3816	Phase 1
0.7526	Intermediate Similarity	NPD7069	Discontinued
0.7526	Intermediate Similarity	NPD3815	Phase 1
0.7514	Intermediate Similarity	NPD3396	Approved
0.7514	Intermediate Similarity	NPD3395	Approved
0.7485	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4502	Phase 2
0.7474	Intermediate Similarity	NPD5416	Discontinued
0.7474	Intermediate Similarity	NPD6220	Phase 3
0.747	Intermediate Similarity	NPD2582	Approved
0.747	Intermediate Similarity	NPD2581	Approved
0.7461	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5902	Approved
0.7448	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5903	Approved
0.7448	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD1768	Approved
0.7436	Intermediate Similarity	NPD5930	Phase 3
0.7432	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6060	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4375	Approved
0.7416	Intermediate Similarity	NPD2917	Approved
0.7416	Intermediate Similarity	NPD5256	Discontinued
0.7399	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8403	Phase 1
0.7385	Intermediate Similarity	NPD7194	Discontinued
0.7384	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD5066	Phase 2
0.7382	Intermediate Similarity	NPD5067	Phase 2
0.7371	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4548	Discontinued
0.7344	Intermediate Similarity	NPD4927	Discontinued
0.734	Intermediate Similarity	NPD3397	Phase 2
0.7337	Intermediate Similarity	NPD1684	Approved
0.7337	Intermediate Similarity	NPD1685	Approved
0.7329	Intermediate Similarity	NPD3525	Discontinued
0.7318	Intermediate Similarity	NPD4921	Phase 3
0.7318	Intermediate Similarity	NPD4919	Phase 3
0.7318	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD5529	Phase 1
0.7316	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5670	Approved
0.7314	Intermediate Similarity	NPD4072	Approved
0.7314	Intermediate Similarity	NPD4071	Approved
0.7312	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6492	Phase 2
0.7278	Intermediate Similarity	NPD1034	Phase 3
0.7278	Intermediate Similarity	NPD2383	Phase 1
0.7278	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6985	Discontinued
0.7245	Intermediate Similarity	NPD4429	Discontinued
0.7245	Intermediate Similarity	NPD7395	Discontinued
0.7241	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2601	Approved
0.7232	Intermediate Similarity	NPD2599	Approved
0.7232	Intermediate Similarity	NPD2600	Approved
0.7216	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4457	Phase 2
0.7208	Intermediate Similarity	NPD3763	Approved
0.7204	Intermediate Similarity	NPD2727	Phase 2
0.7202	Intermediate Similarity	NPD7468	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9690	Approved
0.7198	Intermediate Similarity	NPD6281	Approved
0.7186	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3257	Approved
0.7173	Intermediate Similarity	NPD1392	Approved
0.7169	Intermediate Similarity	NPD3833	Phase 3
0.7169	Intermediate Similarity	NPD3835	Phase 3
0.7164	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7674	Phase 3
0.7164	Intermediate Similarity	NPD7675	Phase 3
0.7164	Intermediate Similarity	NPD7426	Phase 1
0.7158	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1924	Approved
0.7158	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5913	Phase 3
0.7157	Intermediate Similarity	NPD5632	Approved
0.7152	Intermediate Similarity	NPD3385	Approved
0.7151	Intermediate Similarity	NPD2952	Discontinued
0.715	Intermediate Similarity	NPD7548	Discontinued
0.7143	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2187	Approved
0.7135	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2189	Approved
0.7135	Intermediate Similarity	NPD3853	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6219	Discontinued
0.7121	Intermediate Similarity	NPD3875	Discontinued
0.7115	Intermediate Similarity	NPD947	Approved
0.7114	Intermediate Similarity	NPD6246	Approved
0.7113	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6324	Phase 1
0.7105	Intermediate Similarity	NPD5513	Phase 2
0.7102	Intermediate Similarity	NPD5065	Approved
0.71	Intermediate Similarity	NPD1954	Phase 1
0.71	Intermediate Similarity	NPD7221	Approved
0.71	Intermediate Similarity	NPD7219	Approved
0.7095	Intermediate Similarity	NPD3037	Phase 1
0.7092	Intermediate Similarity	NPD5293	Phase 2
0.7086	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6242	Discontinued
0.7085	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6357	Discontinued
0.7081	Intermediate Similarity	NPD6361	Phase 2
0.7081	Intermediate Similarity	NPD4551	Phase 2
0.7081	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6202	Discontinued

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