NPASS Compound

Structure

CID232872 OpenBabel06191716032D 33 35 0 0 0 0 0 0 0 0999 V2000 9.5263 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 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 0.0000 -2.0000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 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 1.7321 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 32 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 33 1 0 0 0 0 21 29 2 0 0 0 0 21 33 1 0 0 0 0 22 28 2 3 0 0 0 22 30 1 0 0 0 0 23 27 2 3 0 0 0 23 31 1 0 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.02
Volume:	460.635
LogP:	5.384
LogD:	3.07
LogS:	-6.163
# Rotatable Bonds:	11
TPSA:	93.73
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	2.137
Fsp3:	0.087
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151
MDCK Permeability:	1.6767295164754614e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	100.22708129882812%
Volume Distribution (VD):	0.37
Pgp-substrate:	0.8876679539680481%

ADMET: Metabolism

CYP1A2-inhibitor:	0.925
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.957
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.83
CYP3A4-inhibitor:	0.791
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	4.213
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.504
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.387
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.463
Skin Sensitization:	0.847
Carcinogencity:	0.183
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC232872

Natural Product ID:	NPC232872
*Common Name:**	4-Chloro-2-(3,4-Dichlorophenylcarbamoyl)Phenyl 2-(Benzyloxycarbonylamino)Acetate
IUPAC Name:	[4-chloro-2-[(3,4-dichlorophenyl)carbamoyl]phenyl] 2-(phenylmethoxycarbonylamino)acetate
Synonyms:
Standard InCHIKey:	GGXAZDHTOYOERN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H17Cl3N2O5/c24-15-6-9-20(17(10-15)22(30)28-16-7-8-18(25)19(26)11-16)33-21(29)12-27-23(31)32-13-14-4-2-1-3-5-14/h1-11H,12-13H2,(H,27,31)(H,28,30)
SMILES:	OC(=NCC(=O)Oc1ccc(cc1C(=Nc1ccc(c(c1)Cl)Cl)O)Cl)OCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468087
PubChem CID:	44593573
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000285] Anilides [CHEMONTID:0004712] Aromatic anilides [CHEMONTID:0004713] Benzanilides

*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
NPO15730.2	Citrus medica var. sarcodactylis	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730.2	Citrus medica var. sarcodactylis	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2784	Radix rubiae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730.2	Citrus medica var. sarcodactylis	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	11
Others	19

Activity Type	# Activity
Organism	28
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC80	>	62.5	ug ml-1	PMID[569948]
NPT186	Organism	Candida tropicalis	Candida tropicalis	IC80	>	62.5	ug ml-1	PMID[569948]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	IC80	>	62.5	ug ml-1	PMID[569948]
NPT554	Organism	Candida glabrata	Candida glabrata	IC80	>	62.5	ug ml-1	PMID[569948]
NPT3610	Organism	Trichosporon beigelii	Trichosporon beigelii	IC80	>	62.5	ug ml-1	PMID[569948]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	IC80	>	62.5	ug ml-1	PMID[569948]
NPT3611	Organism	Absidia corymbifera	Lichtheimia corymbifera	IC80	=	62.5	ug ml-1	PMID[569948]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IC80	=	31.25	ug ml-1	PMID[569948]
NPT3611	Organism	Absidia corymbifera	Lichtheimia corymbifera	IC80	>	62.5	ug ml-1	PMID[569948]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	6.25	ug.mL-1	PMID[569948]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	0.0	%	PMID[569948]
NPT35	Others	n.a.		log K	=	0.8639	n.a.	PMID[569948]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	1000.0	nM	PMID[569949]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	2000.0	nM	PMID[569949]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	MIC	=	16000.0	nM	PMID[569949]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	MIC	=	32000.0	nM	PMID[569949]
NPT1828	Organism	Mycobacterium kansasii	Mycobacterium kansasii	MIC	=	8000.0	nM	PMID[569949]
NPT1828	Organism	Mycobacterium kansasii	Mycobacterium kansasii	MIC	=	16000.0	nM	PMID[569949]
NPT35	Others	n.a.		log K	=	0.8639	n.a.	PMID[569949]

☑ 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 NPC232872 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	316
0.1-0.2	3062
0.2-0.3	13520
0.3-0.4	4248
0.4-0.5	16302
0.5-0.6	5093
0.6-0.7	153
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7083	Intermediate Similarity	NPC469831
0.7047	Intermediate Similarity	NPC469829
0.6939	Remote Similarity	NPC469830
0.6825	Remote Similarity	NPC208280
0.6816	Remote Similarity	NPC473874
0.6772	Remote Similarity	NPC238430
0.6734	Remote Similarity	NPC295287
0.6702	Remote Similarity	NPC269383
0.6702	Remote Similarity	NPC151030
0.6684	Remote Similarity	NPC314861
0.6649	Remote Similarity	NPC306366
0.6632	Remote Similarity	NPC204179
0.6632	Remote Similarity	NPC49315
0.6597	Remote Similarity	NPC127362
0.6587	Remote Similarity	NPC311357
0.6578	Remote Similarity	NPC56635
0.6571	Remote Similarity	NPC471953
0.6561	Remote Similarity	NPC231862
0.6557	Remote Similarity	NPC245974
0.6548	Remote Similarity	NPC263507
0.6548	Remote Similarity	NPC45112
0.6548	Remote Similarity	NPC134413
0.6548	Remote Similarity	NPC271958
0.6538	Remote Similarity	NPC247298
0.6534	Remote Similarity	NPC66643
0.6526	Remote Similarity	NPC57105
0.6482	Remote Similarity	NPC86678
0.6447	Remote Similarity	NPC9475
0.6441	Remote Similarity	NPC105541
0.6433	Remote Similarity	NPC151237
0.6429	Remote Similarity	NPC106183
0.6413	Remote Similarity	NPC313414
0.641	Remote Similarity	NPC83241
0.6409	Remote Similarity	NPC212850
0.6409	Remote Similarity	NPC189724
0.6409	Remote Similarity	NPC314113
0.6409	Remote Similarity	NPC83289
0.6384	Remote Similarity	NPC470392
0.635	Remote Similarity	NPC314025
0.6346	Remote Similarity	NPC314948
0.6346	Remote Similarity	NPC478049
0.6345	Remote Similarity	NPC227778
0.6345	Remote Similarity	NPC95412
0.6341	Remote Similarity	NPC475411
0.6337	Remote Similarity	NPC313886
0.6319	Remote Similarity	NPC477837
0.6319	Remote Similarity	NPC477838
0.6318	Remote Similarity	NPC314656
0.6318	Remote Similarity	NPC314213
0.6294	Remote Similarity	NPC43275
0.629	Remote Similarity	NPC132771
0.6287	Remote Similarity	NPC315913
0.6281	Remote Similarity	NPC315631
0.6262	Remote Similarity	NPC28510
0.6257	Remote Similarity	NPC263835
0.6256	Remote Similarity	NPC474498
0.6244	Remote Similarity	NPC197141
0.6231	Remote Similarity	NPC8467
0.623	Remote Similarity	NPC315257
0.623	Remote Similarity	NPC10875
0.623	Remote Similarity	NPC10730
0.6229	Remote Similarity	NPC29477
0.6216	Remote Similarity	NPC178466
0.6216	Remote Similarity	NPC63628
0.62	Remote Similarity	NPC474902
0.6199	Remote Similarity	NPC256369
0.619	Remote Similarity	NPC182119
0.6188	Remote Similarity	NPC274268
0.6186	Remote Similarity	NPC191863
0.6186	Remote Similarity	NPC133470
0.6186	Remote Similarity	NPC289776
0.6183	Remote Similarity	NPC97004
0.6183	Remote Similarity	NPC136951
0.6183	Remote Similarity	NPC161155
0.6171	Remote Similarity	NPC4974
0.6168	Remote Similarity	NPC159101
0.6167	Remote Similarity	NPC273984
0.6167	Remote Similarity	NPC297584
0.615	Remote Similarity	NPC97282
0.615	Remote Similarity	NPC168153
0.6149	Remote Similarity	NPC471314
0.6149	Remote Similarity	NPC471315
0.6146	Remote Similarity	NPC305700
0.6146	Remote Similarity	NPC18249
0.6146	Remote Similarity	NPC187028
0.6146	Remote Similarity	NPC140915
0.6146	Remote Similarity	NPC197741
0.6146	Remote Similarity	NPC207675
0.6146	Remote Similarity	NPC10221
0.6146	Remote Similarity	NPC212699
0.6134	Remote Similarity	NPC235628
0.6127	Remote Similarity	NPC477392
0.6127	Remote Similarity	NPC315934
0.6114	Remote Similarity	NPC211218
0.6114	Remote Similarity	NPC255253
0.6111	Remote Similarity	NPC193334
0.6111	Remote Similarity	NPC477888
0.6111	Remote Similarity	NPC274732
0.6108	Remote Similarity	NPC227553
0.6103	Remote Similarity	NPC475983
0.6102	Remote Similarity	NPC210950
0.6102	Remote Similarity	NPC199738
0.6098	Remote Similarity	NPC477391
0.6098	Remote Similarity	NPC315542
0.6089	Remote Similarity	NPC473987
0.608	Remote Similarity	NPC310894
0.608	Remote Similarity	NPC62101
0.608	Remote Similarity	NPC95733
0.6073	Remote Similarity	NPC219383
0.6069	Remote Similarity	NPC31314
0.6069	Remote Similarity	NPC193193
0.6069	Remote Similarity	NPC41801
0.6066	Remote Similarity	NPC108847
0.6058	Remote Similarity	NPC112676
0.6058	Remote Similarity	NPC296742
0.6057	Remote Similarity	NPC27198
0.605	Remote Similarity	NPC225381
0.6047	Remote Similarity	NPC5932
0.6041	Remote Similarity	NPC254700
0.604	Remote Similarity	NPC228040
0.604	Remote Similarity	NPC283152
0.6039	Remote Similarity	NPC69213
0.6031	Remote Similarity	NPC70549
0.6029	Remote Similarity	NPC260118
0.6023	Remote Similarity	NPC315632
0.6022	Remote Similarity	NPC244866
0.6022	Remote Similarity	NPC208022
0.602	Remote Similarity	NPC199737
0.6019	Remote Similarity	NPC29472
0.6019	Remote Similarity	NPC322424
0.6017	Remote Similarity	NPC300114
0.601	Remote Similarity	NPC474661
0.601	Remote Similarity	NPC475919
0.601	Remote Similarity	NPC224293
0.6	Remote Similarity	NPC471785
0.6	Remote Similarity	NPC214368
0.6	Remote Similarity	NPC215747
0.6	Remote Similarity	NPC238309
0.6	Remote Similarity	NPC192939
0.6	Remote Similarity	NPC272375
0.5991	Remote Similarity	NPC473422
0.5991	Remote Similarity	NPC475702
0.599	Remote Similarity	NPC184161
0.5988	Remote Similarity	NPC323948
0.598	Remote Similarity	NPC472157
0.598	Remote Similarity	NPC265383
0.5979	Remote Similarity	NPC9373
0.5979	Remote Similarity	NPC112766
0.5979	Remote Similarity	NPC473769
0.5978	Remote Similarity	NPC477839
0.5978	Remote Similarity	NPC126637
0.5977	Remote Similarity	NPC289330
0.5977	Remote Similarity	NPC160120
0.5977	Remote Similarity	NPC17388
0.5977	Remote Similarity	NPC53596
0.5977	Remote Similarity	NPC471308
0.5971	Remote Similarity	NPC320394
0.5969	Remote Similarity	NPC471032
0.5969	Remote Similarity	NPC470935
0.5967	Remote Similarity	NPC313466
0.5967	Remote Similarity	NPC45191
0.5965	Remote Similarity	NPC303370
0.5964	Remote Similarity	NPC66191
0.5964	Remote Similarity	NPC314817
0.5964	Remote Similarity	NPC316297
0.5962	Remote Similarity	NPC180253
0.5962	Remote Similarity	NPC219170
0.5956	Remote Similarity	NPC2363
0.5945	Remote Similarity	NPC473460
0.5943	Remote Similarity	NPC83279
0.5942	Remote Similarity	NPC28425
0.5942	Remote Similarity	NPC276060
0.5941	Remote Similarity	NPC474953
0.5938	Remote Similarity	NPC139699
0.5938	Remote Similarity	NPC114659
0.5931	Remote Similarity	NPC316161
0.593	Remote Similarity	NPC258992
0.593	Remote Similarity	NPC19555
0.593	Remote Similarity	NPC33717
0.5926	Remote Similarity	NPC472330
0.5926	Remote Similarity	NPC472329
0.5926	Remote Similarity	NPC319774
0.5924	Remote Similarity	NPC138365
0.5924	Remote Similarity	NPC294244
0.5922	Remote Similarity	NPC311936
0.5916	Remote Similarity	NPC277857
0.5916	Remote Similarity	NPC115144
0.5914	Remote Similarity	NPC36434
0.5909	Remote Similarity	NPC314743
0.5905	Remote Similarity	NPC474059
0.5901	Remote Similarity	NPC326333
0.5899	Remote Similarity	NPC229113
0.5896	Remote Similarity	NPC471825
0.5894	Remote Similarity	NPC119579
0.5891	Remote Similarity	NPC474881
0.5888	Remote Similarity	NPC19023
0.5886	Remote Similarity	NPC317564
0.5882	Remote Similarity	NPC298821
0.5882	Remote Similarity	NPC127082
0.5879	Remote Similarity	NPC50380

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 NPC232872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	786
0.2-0.3	1135
0.3-0.4	1636
0.4-0.5	3354
0.5-0.6	1842
0.6-0.7	192
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7529	Intermediate Similarity	NPD1159	Approved
0.7526	Intermediate Similarity	NPD5650	Approved
0.7526	Intermediate Similarity	NPD5651	Approved
0.7526	Intermediate Similarity	NPD5652	Approved
0.7513	Intermediate Similarity	NPD4523	Approved
0.7461	Intermediate Similarity	NPD5984	Phase 2
0.7435	Intermediate Similarity	NPD5800	Discontinued
0.7354	Intermediate Similarity	NPD4012	Approved
0.725	Intermediate Similarity	NPD2498	Approved
0.7207	Intermediate Similarity	NPD1162	Approved
0.7202	Intermediate Similarity	NPD3065	Discontinued
0.7196	Intermediate Similarity	NPD2827	Approved
0.7196	Intermediate Similarity	NPD2826	Approved
0.7196	Intermediate Similarity	NPD2825	Approved
0.7166	Intermediate Similarity	NPD5858	Discontinued
0.715	Intermediate Similarity	NPD5565	Discontinued
0.7143	Intermediate Similarity	NPD6905	Phase 2
0.7135	Intermediate Similarity	NPD1413	Approved
0.7135	Intermediate Similarity	NPD1414	Approved
0.712	Intermediate Similarity	NPD1533	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5649	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1381	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4113	Discontinued
0.7071	Intermediate Similarity	NPD6312	Discontinued
0.7068	Intermediate Similarity	NPD2168	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2167	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5587	Approved
0.7047	Intermediate Similarity	NPD2374	Approved
0.7017	Intermediate Similarity	NPD5811	Approved
0.7006	Intermediate Similarity	NPD1835	Phase 1
0.6991	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3952	Approved
0.6984	Remote Similarity	NPD3951	Phase 3
0.6984	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD4590	Approved
0.6927	Remote Similarity	NPD1716	Phase 3
0.6907	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6502	Phase 2
0.6862	Remote Similarity	NPD1850	Phase 3
0.6853	Remote Similarity	NPD3119	Phase 1
0.6853	Remote Similarity	NPD3120	Approved
0.6837	Remote Similarity	NPD6045	Phase 3
0.6825	Remote Similarity	NPD5623	Approved
0.6816	Remote Similarity	NPD4771	Phase 2
0.6804	Remote Similarity	NPD6184	Discontinued
0.6782	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7548	Discontinued
0.6772	Remote Similarity	NPD7129	Suspended
0.6763	Remote Similarity	NPD7477	Discontinued
0.6757	Remote Similarity	NPD2366	Approved
0.6755	Remote Similarity	NPD4064	Discontinued
0.6735	Remote Similarity	NPD1361	Discontinued
0.6735	Remote Similarity	NPD2166	Phase 3
0.6705	Remote Similarity	NPD1048	Approved
0.6701	Remote Similarity	NPD3965	Phase 1
0.6685	Remote Similarity	NPD4003	Phase 3
0.6684	Remote Similarity	NPD4485	Approved
0.6667	Remote Similarity	NPD2941	Discontinued
0.6667	Remote Similarity	NPD6034	Phase 2
0.665	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1339	Discontinued
0.665	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3601	Discontinued
0.6631	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3296	Phase 1
0.6606	Remote Similarity	NPD6981	Phase 2
0.6596	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3453	Discontinued
0.6578	Remote Similarity	NPD3778	Approved
0.6567	Remote Similarity	NPD1898	Discontinued
0.6556	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3819	Phase 2
0.6548	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1393	Approved
0.6531	Remote Similarity	NPD5670	Approved
0.6526	Remote Similarity	NPD5420	Discontinued
0.6515	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5845	Phase 2
0.6509	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8027	Approved
0.6502	Remote Similarity	NPD5871	Discontinued
0.65	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD5545	Phase 2
0.6489	Remote Similarity	NPD2326	Approved
0.6479	Remote Similarity	NPD4917	Discontinued
0.6476	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD6604	Discontinued
0.6458	Remote Similarity	NPD3363	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7805	Phase 3
0.6452	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7546	Discontinued
0.645	Remote Similarity	NPD7877	Suspended
0.6448	Remote Similarity	NPD2743	Approved
0.6447	Remote Similarity	NPD4873	Discontinued
0.6442	Remote Similarity	NPD6874	Approved
0.6437	Remote Similarity	NPD4993	Discontinued
0.6425	Remote Similarity	NPD6746	Phase 2
0.6425	Remote Similarity	NPD3251	Approved
0.6421	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5542	Phase 2
0.6402	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3804	Discontinued
0.6396	Remote Similarity	NPD7542	Phase 3
0.6364	Remote Similarity	NPD3933	Discontinued
0.6364	Remote Similarity	NPD5096	Phase 3
0.6364	Remote Similarity	NPD5095	Phase 3
0.6359	Remote Similarity	NPD5847	Phase 1
0.6359	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6511	Phase 1
0.6351	Remote Similarity	NPD6510	Phase 1
0.6349	Remote Similarity	NPD4675	Approved
0.6349	Remote Similarity	NPD4678	Approved
0.6346	Remote Similarity	NPD5872	Discontinued
0.6344	Remote Similarity	NPD4123	Phase 3
0.634	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2425	Phase 1
0.6318	Remote Similarity	NPD2802	Phase 3
0.6316	Remote Similarity	NPD3274	Phase 2
0.6313	Remote Similarity	NPD1859	Approved
0.6308	Remote Similarity	NPD2034	Discontinued
0.6308	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7131	Phase 3
0.6276	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5938	Phase 3
0.6257	Remote Similarity	NPD756	Suspended
0.625	Remote Similarity	NPD4487	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD2216	Approved
0.6244	Remote Similarity	NPD4083	Discontinued
0.6244	Remote Similarity	NPD2215	Approved
0.6244	Remote Similarity	NPD779	Phase 2
0.6238	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD955	Approved
0.6237	Remote Similarity	NPD6815	Approved
0.6232	Remote Similarity	NPD4740	Approved
0.6231	Remote Similarity	NPD5132	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3236	Phase 3
0.6224	Remote Similarity	NPD2821	Approved
0.622	Remote Similarity	NPD5512	Phase 3
0.622	Remote Similarity	NPD6550	Discontinued
0.6218	Remote Similarity	NPD3557	Approved
0.6218	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3556	Approved
0.6218	Remote Similarity	NPD1012	Discontinued
0.6218	Remote Similarity	NPD6063	Approved
0.6218	Remote Similarity	NPD3560	Approved
0.6218	Remote Similarity	NPD7318	Phase 3
0.6218	Remote Similarity	NPD3558	Approved
0.6212	Remote Similarity	NPD2246	Approved
0.6212	Remote Similarity	NPD2248	Approved
0.6209	Remote Similarity	NPD3260	Discontinued
0.6207	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7391	Discontinued
0.6196	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7608	Discontinued
0.619	Remote Similarity	NPD4605	Approved
0.619	Remote Similarity	NPD3627	Approved
0.619	Remote Similarity	NPD4454	Phase 2
0.619	Remote Similarity	NPD4604	Approved
0.619	Remote Similarity	NPD6988	Phase 1
0.6186	Remote Similarity	NPD7773	Phase 2
0.6183	Remote Similarity	NPD3692	Discontinued
0.6178	Remote Similarity	NPD1714	Approved
0.6178	Remote Similarity	NPD1715	Phase 1
0.6176	Remote Similarity	NPD4889	Approved
0.6169	Remote Similarity	NPD3885	Approved
0.6165	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3975	Discontinued
0.6154	Remote Similarity	NPD4372	Phase 1
0.6154	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.615	Remote Similarity	NPD3909	Discontinued
0.6146	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1858	Approved
0.6143	Remote Similarity	NPD4931	Phase 2
0.6141	Remote Similarity	NPD2377	Approved
0.6141	Remote Similarity	NPD3656	Approved
0.6141	Remote Similarity	NPD2378	Approved
0.6141	Remote Similarity	NPD2376	Approved
0.614	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2772	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2314	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD2845	Phase 2
0.6135	Remote Similarity	NPD1213	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