NPASS Compound

Structure

CID111492 OpenBabel06191715462D 31 33 0 0 0 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -0.8660 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 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 -0.0000 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 6 1 0 0 0 0 4 16 2 0 0 0 0 5 7 2 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 15 2 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 23 3 0 0 0 0 14 22 2 0 0 0 0 15 22 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 20 26 1 0 0 0 0 21 31 1 0 0 0 0 22 31 1 0 0 0 0 25 27 2 0 0 0 0 25 28 2 0 0 0 0 26 29 2 0 0 0 0 26 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.13
Volume:	417.063
LogP:	5.688
LogD:	4.373
LogS:	-7.482
# Rotatable Bonds:	6
TPSA:	131.33
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	2.486
Fsp3:	0.136
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:	-4.771
MDCK Permeability:	0.00011889643792528659
Pgp-inhibitor:	0.023
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.679
Plasma Protein Binding (PPB):	101.20137786865234%
Volume Distribution (VD):	0.676
Pgp-substrate:	0.6998693346977234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.754
CYP2C19-inhibitor:	0.797
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.831
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.653
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.467

ADMET: Excretion

Clearance (CL):	6.24
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.927
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.871
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.95
Carcinogencity:	0.736
Eye Corrosion:	0.005
Eye Irritation:	0.892
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC111492

Natural Product ID:	NPC111492
*Common Name:**	4-[2,4-Dinitro-5-(2,4,6-Trimethylphenoxy)Anilino]Benzonitrile
IUPAC Name:	4-[2,4-dinitro-5-(2,4,6-trimethylphenoxy)anilino]benzonitrile
Synonyms:
Standard InCHIKey:	IQTVWGJWEJIBHJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H18N4O5/c1-13-8-14(2)22(15(3)9-13)31-21-10-18(19(25(27)28)11-20(21)26(29)30)24-17-6-4-16(12-23)5-7-17/h4-11,24H,1-3H3
SMILES:	Cc1cc(C)c(c(C)c1)Oc1cc(c(cc1N(=O)=O)N(=O)=O)Nc1ccc(cc1)C#N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173109
PubChem CID:	49777919
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
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	Radix	n.a.	n.a.	PMID[29236488]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	CC50	>	59810.0	nM	PMID[552617]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	280.0	nM	PMID[552617]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	214.0	n.a.	PMID[552617]

☑ 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 NPC111492 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	754
0.1-0.2	7785
0.2-0.3	10211
0.3-0.4	10030
0.4-0.5	12041
0.5-0.6	1791
0.6-0.7	84
0.7-0.8	0
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
0.6834	Remote Similarity	NPC473432
0.6651	Remote Similarity	NPC162484
0.6573	Remote Similarity	NPC72211
0.6567	Remote Similarity	NPC73280
0.6562	Remote Similarity	NPC40209
0.6557	Remote Similarity	NPC70259
0.6544	Remote Similarity	NPC470930
0.6526	Remote Similarity	NPC314948
0.6516	Remote Similarity	NPC471532
0.6509	Remote Similarity	NPC205934
0.6509	Remote Similarity	NPC43787
0.6504	Remote Similarity	NPC86078
0.65	Remote Similarity	NPC201697
0.6481	Remote Similarity	NPC470586
0.6456	Remote Similarity	NPC288305
0.6452	Remote Similarity	NPC475085
0.6452	Remote Similarity	NPC475112
0.6452	Remote Similarity	NPC291535
0.6449	Remote Similarity	NPC478049
0.6432	Remote Similarity	NPC131017
0.6425	Remote Similarity	NPC471561
0.6413	Remote Similarity	NPC48353
0.6406	Remote Similarity	NPC267423
0.6377	Remote Similarity	NPC118776
0.6364	Remote Similarity	NPC227908
0.6351	Remote Similarity	NPC209769
0.6338	Remote Similarity	NPC79213
0.633	Remote Similarity	NPC476044
0.6327	Remote Similarity	NPC471531
0.6325	Remote Similarity	NPC475253
0.6316	Remote Similarity	NPC473179
0.6313	Remote Similarity	NPC241263
0.6311	Remote Similarity	NPC285941
0.6296	Remote Similarity	NPC243834
0.6296	Remote Similarity	NPC70956
0.629	Remote Similarity	NPC476106
0.629	Remote Similarity	NPC261388
0.6261	Remote Similarity	NPC193777
0.6261	Remote Similarity	NPC477532
0.625	Remote Similarity	NPC306366
0.6244	Remote Similarity	NPC473422
0.6244	Remote Similarity	NPC313112
0.6244	Remote Similarity	NPC301292
0.6239	Remote Similarity	NPC252251
0.6238	Remote Similarity	NPC204179
0.622	Remote Similarity	NPC190461
0.6217	Remote Similarity	NPC477533
0.6213	Remote Similarity	NPC209174
0.6211	Remote Similarity	NPC176113
0.6205	Remote Similarity	NPC475133
0.6204	Remote Similarity	NPC230313
0.6199	Remote Similarity	NPC473460
0.6197	Remote Similarity	NPC473185
0.6197	Remote Similarity	NPC110741
0.6186	Remote Similarity	NPC477531
0.6184	Remote Similarity	NPC170114
0.6168	Remote Similarity	NPC474059
0.6154	Remote Similarity	NPC288759
0.614	Remote Similarity	NPC470549
0.614	Remote Similarity	NPC22476
0.6136	Remote Similarity	NPC11017
0.6136	Remote Similarity	NPC25897
0.6129	Remote Similarity	NPC243626
0.6106	Remote Similarity	NPC474366
0.6103	Remote Similarity	NPC33902
0.6103	Remote Similarity	NPC276674
0.6099	Remote Similarity	NPC475147
0.6095	Remote Similarity	NPC70092
0.6091	Remote Similarity	NPC212163
0.6089	Remote Similarity	NPC470931
0.6083	Remote Similarity	NPC78284
0.6079	Remote Similarity	NPC218303
0.6077	Remote Similarity	NPC127082
0.6065	Remote Similarity	NPC475411
0.6056	Remote Similarity	NPC249405
0.6047	Remote Similarity	NPC320088
0.6047	Remote Similarity	NPC477186
0.6045	Remote Similarity	NPC234933
0.6043	Remote Similarity	NPC115588
0.6043	Remote Similarity	NPC231924
0.6036	Remote Similarity	NPC295676
0.6035	Remote Similarity	NPC199667
0.6035	Remote Similarity	NPC11464
0.6029	Remote Similarity	NPC168153
0.6019	Remote Similarity	NPC1527
0.6019	Remote Similarity	NPC312531
0.601	Remote Similarity	NPC285635
0.6009	Remote Similarity	NPC179704
0.6	Remote Similarity	NPC473182
0.5992	Remote Similarity	NPC473183
0.5991	Remote Similarity	NPC473181
0.5991	Remote Similarity	NPC329747
0.5983	Remote Similarity	NPC94157
0.5983	Remote Similarity	NPC473180
0.5983	Remote Similarity	NPC198503
0.5982	Remote Similarity	NPC223427
0.5972	Remote Similarity	NPC242928
0.5964	Remote Similarity	NPC232600
0.5963	Remote Similarity	NPC473004
0.5959	Remote Similarity	NPC469722
0.5957	Remote Similarity	NPC30749
0.5956	Remote Similarity	NPC156728
0.5956	Remote Similarity	NPC244606
0.5955	Remote Similarity	NPC303214
0.5955	Remote Similarity	NPC470023
0.5949	Remote Similarity	NPC202503
0.5945	Remote Similarity	NPC473008
0.594	Remote Similarity	NPC476069
0.5938	Remote Similarity	NPC15987
0.5929	Remote Similarity	NPC477161
0.5928	Remote Similarity	NPC153042
0.5928	Remote Similarity	NPC470021
0.5922	Remote Similarity	NPC299582
0.5921	Remote Similarity	NPC477160
0.5919	Remote Similarity	NPC315957
0.5913	Remote Similarity	NPC127996
0.5913	Remote Similarity	NPC119722
0.5913	Remote Similarity	NPC305542
0.5909	Remote Similarity	NPC473184
0.5909	Remote Similarity	NPC277351
0.5907	Remote Similarity	NPC94943
0.5903	Remote Similarity	NPC198160
0.5903	Remote Similarity	NPC222561
0.5902	Remote Similarity	NPC7393
0.5896	Remote Similarity	NPC472168
0.589	Remote Similarity	NPC141915
0.589	Remote Similarity	NPC114335
0.589	Remote Similarity	NPC280964
0.5887	Remote Similarity	NPC268223
0.5885	Remote Similarity	NPC470017
0.5885	Remote Similarity	NPC258773
0.5885	Remote Similarity	NPC87714
0.5882	Remote Similarity	NPC13880
0.5882	Remote Similarity	NPC203784
0.5882	Remote Similarity	NPC170503
0.5882	Remote Similarity	NPC200888
0.5882	Remote Similarity	NPC126519
0.588	Remote Similarity	NPC195636
0.588	Remote Similarity	NPC314573
0.5874	Remote Similarity	NPC18487
0.5874	Remote Similarity	NPC128823
0.5872	Remote Similarity	NPC474904
0.5871	Remote Similarity	NPC219383
0.5869	Remote Similarity	NPC287588
0.5864	Remote Similarity	NPC471825
0.5864	Remote Similarity	NPC302001
0.5864	Remote Similarity	NPC475190
0.5861	Remote Similarity	NPC470022
0.586	Remote Similarity	NPC190007
0.586	Remote Similarity	NPC84478
0.5858	Remote Similarity	NPC187145
0.5856	Remote Similarity	NPC161804
0.5855	Remote Similarity	NPC77777
0.5855	Remote Similarity	NPC46561
0.5854	Remote Similarity	NPC79328
0.5853	Remote Similarity	NPC469830
0.5853	Remote Similarity	NPC21425
0.5849	Remote Similarity	NPC477187
0.5846	Remote Similarity	NPC314113
0.5844	Remote Similarity	NPC116178
0.5841	Remote Similarity	NPC116096
0.5833	Remote Similarity	NPC212123
0.583	Remote Similarity	NPC17565
0.583	Remote Similarity	NPC100863
0.583	Remote Similarity	NPC208084
0.5829	Remote Similarity	NPC95898
0.5826	Remote Similarity	NPC269449
0.5819	Remote Similarity	NPC217903
0.5819	Remote Similarity	NPC321166
0.5817	Remote Similarity	NPC475393
0.5814	Remote Similarity	NPC212535
0.5812	Remote Similarity	NPC169402
0.5808	Remote Similarity	NPC475910
0.5808	Remote Similarity	NPC90185
0.5805	Remote Similarity	NPC132642
0.5796	Remote Similarity	NPC6786
0.5796	Remote Similarity	NPC131977
0.5796	Remote Similarity	NPC135887
0.5796	Remote Similarity	NPC199277
0.5792	Remote Similarity	NPC13249
0.5789	Remote Similarity	NPC209377
0.5787	Remote Similarity	NPC87560
0.5787	Remote Similarity	NPC195120
0.5781	Remote Similarity	NPC280799
0.5778	Remote Similarity	NPC67904
0.5778	Remote Similarity	NPC127178
0.5778	Remote Similarity	NPC121772
0.5776	Remote Similarity	NPC308137
0.5776	Remote Similarity	NPC310211
0.5773	Remote Similarity	NPC203628
0.5773	Remote Similarity	NPC1820
0.5772	Remote Similarity	NPC151171
0.5769	Remote Similarity	NPC470001
0.5769	Remote Similarity	NPC24954
0.5769	Remote Similarity	NPC470002
0.5767	Remote Similarity	NPC474798
0.5764	Remote Similarity	NPC4687
0.5764	Remote Similarity	NPC249583
0.5763	Remote Similarity	NPC219397
0.5762	Remote Similarity	NPC193853

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 NPC111492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	973
0.2-0.3	943
0.3-0.4	2558
0.4-0.5	3025
0.5-0.6	1190
0.6-0.7	84
0.7-0.8	1
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
0.7143	Intermediate Similarity	NPD4740	Approved
0.7041	Intermediate Similarity	NPD2525	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3511	Discontinued
0.6834	Remote Similarity	NPD4354	Approved
0.6829	Remote Similarity	NPD3398	Discontinued
0.6811	Remote Similarity	NPD965	Approved
0.68	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD1909	Discontinued
0.6702	Remote Similarity	NPD1084	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2804	Phase 1
0.662	Remote Similarity	NPD6644	Discontinued
0.6606	Remote Similarity	NPD5845	Phase 2
0.6603	Remote Similarity	NPD5641	Discontinued
0.6578	Remote Similarity	NPD4597	Approved
0.6578	Remote Similarity	NPD4598	Approved
0.652	Remote Similarity	NPD3370	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7479	Phase 2
0.6517	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD204	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6379	Discontinued
0.6497	Remote Similarity	NPD3241	Phase 2
0.6495	Remote Similarity	NPD6357	Discontinued
0.6484	Remote Similarity	NPD1314	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5847	Phase 1
0.6462	Remote Similarity	NPD7262	Phase 1
0.6453	Remote Similarity	NPD5938	Phase 3
0.645	Remote Similarity	NPD2341	Discontinued
0.6449	Remote Similarity	NPD4605	Approved
0.6449	Remote Similarity	NPD4604	Approved
0.6447	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.641	Remote Similarity	NPD789	Phase 2
0.6409	Remote Similarity	NPD6296	Discontinued
0.6392	Remote Similarity	NPD3627	Approved
0.6388	Remote Similarity	NPD7194	Discontinued
0.6376	Remote Similarity	NPD3765	Approved
0.6372	Remote Similarity	NPD1622	Discontinued
0.6372	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2334	Discontinued
0.6359	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4324	Phase 2
0.6338	Remote Similarity	NPD4325	Phase 2
0.6332	Remote Similarity	NPD1012	Discontinued
0.6324	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5810	Discontinued
0.6293	Remote Similarity	NPD7032	Approved
0.6281	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6985	Discontinued
0.6269	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3369	Phase 2
0.6256	Remote Similarity	NPD1405	Approved
0.6244	Remote Similarity	NPD5858	Discontinued
0.6244	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7877	Suspended
0.6233	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD3793	Phase 3
0.6231	Remote Similarity	NPD1769	Discontinued
0.6226	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5637	Discontinued
0.6217	Remote Similarity	NPD5930	Phase 3
0.6215	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD3296	Phase 1
0.6212	Remote Similarity	NPD1557	Discontinued
0.6207	Remote Similarity	NPD6037	Discontinued
0.6199	Remote Similarity	NPD3804	Discontinued
0.6198	Remote Similarity	NPD7413	Phase 3
0.6186	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7476	Discontinued
0.6172	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD2843	Phase 2
0.6168	Remote Similarity	NPD2845	Phase 2
0.6164	Remote Similarity	NPD6757	Phase 3
0.6157	Remote Similarity	NPD4590	Approved
0.6157	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3515	Approved
0.6154	Remote Similarity	NPD3516	Approved
0.6146	Remote Similarity	NPD5719	Approved
0.6146	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5903	Approved
0.614	Remote Similarity	NPD5902	Approved
0.6132	Remote Similarity	NPD7068	Approved
0.6132	Remote Similarity	NPD7067	Approved
0.6122	Remote Similarity	NPD2335	Discontinued
0.6119	Remote Similarity	NPD6283	Phase 2
0.6114	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD9715	Phase 2
0.6109	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD3557	Approved
0.6089	Remote Similarity	NPD3558	Approved
0.6089	Remote Similarity	NPD5658	Approved
0.6089	Remote Similarity	NPD3560	Approved
0.6089	Remote Similarity	NPD3556	Approved
0.6089	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD1603	Discontinued
0.6083	Remote Similarity	NPD4539	Phase 1
0.6083	Remote Similarity	NPD5150	Phase 2
0.6079	Remote Similarity	NPD7272	Discontinued
0.6077	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD5651	Approved
0.6073	Remote Similarity	NPD5652	Approved
0.6073	Remote Similarity	NPD5650	Approved
0.6071	Remote Similarity	NPD3003	Approved
0.6071	Remote Similarity	NPD7598	Phase 2
0.6071	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.607	Remote Similarity	NPD4433	Discontinued
0.6063	Remote Similarity	NPD3290	Approved
0.6063	Remote Similarity	NPD3289	Phase 3
0.6062	Remote Similarity	NPD4437	Phase 3
0.6056	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7256	Discontinued
0.6055	Remote Similarity	NPD4523	Approved
0.6052	Remote Similarity	NPD6560	Approved
0.6049	Remote Similarity	NPD3251	Approved
0.6048	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD6877	Discontinued
0.6039	Remote Similarity	NPD2215	Approved
0.6039	Remote Similarity	NPD4083	Discontinued
0.6039	Remote Similarity	NPD2216	Approved
0.6037	Remote Similarity	NPD4372	Phase 1
0.6028	Remote Similarity	NPD6340	Approved
0.6028	Remote Similarity	NPD6339	Approved
0.6027	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6250	Discontinued
0.6027	Remote Similarity	NPD3964	Approved
0.602	Remote Similarity	NPD2468	Approved
0.602	Remote Similarity	NPD2469	Approved
0.602	Remote Similarity	NPD3778	Approved
0.6019	Remote Similarity	NPD6457	Approved
0.601	Remote Similarity	NPD2246	Approved
0.601	Remote Similarity	NPD7752	Approved
0.601	Remote Similarity	NPD7753	Approved
0.601	Remote Similarity	NPD2248	Approved
0.6009	Remote Similarity	NPD7125	Discontinued
0.6009	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD2374	Approved
0.6	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6723	Discontinued
0.6	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5186	Approved
0.599	Remote Similarity	NPD5183	Approved
0.5983	Remote Similarity	NPD6298	Discontinued
0.5983	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4586	Phase 3
0.5981	Remote Similarity	NPD6045	Phase 3
0.598	Remote Similarity	NPD6030	Approved
0.598	Remote Similarity	NPD6031	Approved
0.598	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.597	Remote Similarity	NPD5617	Suspended
0.597	Remote Similarity	NPD3538	Suspended
0.5969	Remote Similarity	NPD3301	Approved
0.5966	Remote Similarity	NPD5559	Phase 2
0.5964	Remote Similarity	NPD6321	Discontinued
0.5963	Remote Similarity	NPD7288	Phase 3
0.5962	Remote Similarity	NPD4012	Approved
0.5962	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7891	Discontinued
0.5956	Remote Similarity	NPD4795	Phase 2
0.5953	Remote Similarity	NPD6638	Approved
0.5953	Remote Similarity	NPD3316	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD6526	Approved
0.5934	Remote Similarity	NPD6494	Phase 2
0.5933	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5530	Phase 1
0.5928	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD5872	Discontinued
0.5926	Remote Similarity	NPD4587	Phase 3
0.592	Remote Similarity	NPD5811	Approved
0.5919	Remote Similarity	NPD2339	Phase 3
0.5919	Remote Similarity	NPD1740	Approved
0.5919	Remote Similarity	NPD1739	Approved
0.5911	Remote Similarity	NPD4350	Approved
0.5911	Remote Similarity	NPD4349	Approved
0.5909	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5561	Approved
0.5905	Remote Similarity	NPD5562	Approved
0.5905	Remote Similarity	NPD8149	Discontinued
0.5905	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD1191	Discontinued
0.59	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD7326	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