NPASS Compound

Structure

CID314835 OpenBabel06191716132D 43 43 0 0 1 0 0 0 0 0999 V2000 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 1.7321 -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 7.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 6.5000 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 -6.9282 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -7.7942 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -6.9282 6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 -7.7942 9.5000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 10.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 9.0000 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 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 9.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 38 2 0 0 0 0 18 10 1 6 0 0 0 18 34 1 0 0 0 0 19 11 1 6 0 0 0 19 22 1 0 0 0 0 19 35 1 0 0 0 0 20 14 1 1 0 0 0 20 24 1 0 0 0 0 20 36 1 0 0 0 0 21 16 1 1 0 0 0 21 23 1 0 0 0 0 21 37 1 0 0 0 0 22 37 2 3 0 0 0 22 39 1 0 0 0 0 23 34 2 3 0 0 0 23 40 1 0 0 0 0 24 41 2 0 0 0 0 24 42 1 0 0 0 0 25 28 2 0 0 0 0 25 29 1 0 0 0 0 25 32 1 0 0 0 0 26 30 2 0 0 0 0 26 31 1 0 0 0 0 26 33 1 0 0 0 0 27 35 2 3 0 0 0 27 36 1 0 0 0 0 27 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.34
Volume:	603.336
LogP:	-2.031
LogD:	-0.696
LogS:	-2.713
# Rotatable Bonds:	25
TPSA:	277.5
# H-Bond Aceptor:	16
# H-Bond Donor:	13
# Rings:	1
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.038
Synthetic Accessibility Score:	3.972
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.944
MDCK Permeability:	4.4478776544565335e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.814
Human Intestinal Absorption (HIA):	0.739
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	14.793123245239258%
Volume Distribution (VD):	0.496
Pgp-substrate:	71.51470184326172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	2.087
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.254
Maximum Recommended Daily Dose:	0.471
Skin Sensitization:	0.231
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.796

Download Data

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

Natural Product: NPC314835

Natural Product ID:	NPC314835
*Common Name:**	Antipain
IUPAC Name:	(2S)-2-[[(2S)-5-(diaminomethylideneamino)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]carbamoylamino]-3-phenylpropanoic acid
Synonyms:	Antipain
Standard InCHIKey:	SDNYTAYICBFYFH-TUFLPTIASA-N
Standard InCHI:	InChI=1S/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
SMILES:	CC(C)[C@@H](C(=N[C@@H](CCCNC(=N)N)C=O)O)N=C([C@H](CCCNC(=N)N)N=C(N[C@@H](Cc1ccccc1)C(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1230912
PubChem CID:	37817
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004830] Dipeptides

*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
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32998509]
NPO14826	Streptomyces mobaraensis	Species	Streptomycetaceae	Bacteria	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
IC50	2
Ki	1
Others	2

Activity Type	# Activity
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT201	Individual Protein	Papain	Carica papaya	Ki	=	0.16	mg/ml	PMID[533968]
NPT201	Individual Protein	Papain	Carica papaya	IC50	=	3.4	nM	PMID[533969]
NPT201	Individual Protein	Papain	Carica papaya	Delta Tm	=	0.9	degrees C	PMID[533969]
NPT2	Others	Unspecified		IC50	>	30000.0	nM	PMID[533969]
NPT2	Others	Unspecified		Delta Tm	=	1.7	degrees C	PMID[533969]

☑ 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 NPC314835 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	117
0.1-0.2	985
0.2-0.3	5999
0.3-0.4	22234
0.4-0.5	11053
0.5-0.6	1660
0.6-0.7	487
0.7-0.8	155
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8978	High Similarity	NPC314114
0.8915	High Similarity	NPC477937
0.8273	Intermediate Similarity	NPC132636
0.8254	Intermediate Similarity	NPC474584
0.8027	Intermediate Similarity	NPC300443
0.7947	Intermediate Similarity	NPC62104
0.7947	Intermediate Similarity	NPC1390
0.7826	Intermediate Similarity	NPC311753
0.7778	Intermediate Similarity	NPC327481
0.7771	Intermediate Similarity	NPC274198
0.7771	Intermediate Similarity	NPC198254
0.7763	Intermediate Similarity	NPC324850
0.7755	Intermediate Similarity	NPC311658
0.7742	Intermediate Similarity	NPC22883
0.7742	Intermediate Similarity	NPC210377
0.7742	Intermediate Similarity	NPC217804
0.7742	Intermediate Similarity	NPC5719
0.7712	Intermediate Similarity	NPC24617
0.7708	Intermediate Similarity	NPC48202
0.7698	Intermediate Similarity	NPC67043
0.7692	Intermediate Similarity	NPC15068
0.7674	Intermediate Similarity	NPC319579
0.7669	Intermediate Similarity	NPC169328
0.7662	Intermediate Similarity	NPC114806
0.7658	Intermediate Similarity	NPC276506
0.7652	Intermediate Similarity	NPC197470
0.7643	Intermediate Similarity	NPC63040
0.7615	Intermediate Similarity	NPC329011
0.7612	Intermediate Similarity	NPC314992
0.7612	Intermediate Similarity	NPC310467
0.7591	Intermediate Similarity	NPC35996
0.7578	Intermediate Similarity	NPC196243
0.754	Intermediate Similarity	NPC164859
0.75	Intermediate Similarity	NPC315266
0.7463	Intermediate Similarity	NPC2265
0.7445	Intermediate Similarity	NPC71684
0.7417	Intermediate Similarity	NPC2501
0.7403	Intermediate Similarity	NPC473580
0.7372	Intermediate Similarity	NPC478014
0.7372	Intermediate Similarity	NPC478016
0.7372	Intermediate Similarity	NPC478015
0.7357	Intermediate Similarity	NPC101719
0.7353	Intermediate Similarity	NPC237420
0.7338	Intermediate Similarity	NPC6975
0.7333	Intermediate Similarity	NPC153554
0.7325	Intermediate Similarity	NPC469243
0.7315	Intermediate Similarity	NPC52748
0.7302	Intermediate Similarity	NPC12730
0.7286	Intermediate Similarity	NPC222466
0.7273	Intermediate Similarity	NPC122590
0.7267	Intermediate Similarity	NPC66490
0.7246	Intermediate Similarity	NPC200964
0.7234	Intermediate Similarity	NPC47667
0.723	Intermediate Similarity	NPC163392
0.723	Intermediate Similarity	NPC239762
0.7222	Intermediate Similarity	NPC130309
0.7215	Intermediate Similarity	NPC475544
0.7203	Intermediate Similarity	NPC111428
0.72	Intermediate Similarity	NPC476978
0.7194	Intermediate Similarity	NPC202521
0.7188	Intermediate Similarity	NPC223207
0.7186	Intermediate Similarity	NPC473404
0.7185	Intermediate Similarity	NPC33742
0.7181	Intermediate Similarity	NPC269398
0.7181	Intermediate Similarity	NPC263493
0.7179	Intermediate Similarity	NPC469903
0.7162	Intermediate Similarity	NPC470884
0.7162	Intermediate Similarity	NPC476133
0.7162	Intermediate Similarity	NPC178662
0.7162	Intermediate Similarity	NPC98424
0.7162	Intermediate Similarity	NPC92784
0.7161	Intermediate Similarity	NPC473341
0.716	Intermediate Similarity	NPC129486
0.7153	Intermediate Similarity	NPC470545
0.7152	Intermediate Similarity	NPC209509
0.7152	Intermediate Similarity	NPC5620
0.7143	Intermediate Similarity	NPC304074
0.7143	Intermediate Similarity	NPC10781
0.7143	Intermediate Similarity	NPC293628
0.7143	Intermediate Similarity	NPC471771
0.7143	Intermediate Similarity	NPC122493
0.7143	Intermediate Similarity	NPC290755
0.7133	Intermediate Similarity	NPC161069
0.7133	Intermediate Similarity	NPC77905
0.7124	Intermediate Similarity	NPC471821
0.7124	Intermediate Similarity	NPC471820
0.7122	Intermediate Similarity	NPC190663
0.7122	Intermediate Similarity	NPC476990
0.7114	Intermediate Similarity	NPC214988
0.7111	Intermediate Similarity	NPC35850
0.7111	Intermediate Similarity	NPC276949
0.7107	Intermediate Similarity	NPC469901
0.7107	Intermediate Similarity	NPC469902
0.7103	Intermediate Similarity	NPC255447
0.7101	Intermediate Similarity	NPC470546
0.7095	Intermediate Similarity	NPC471265
0.7095	Intermediate Similarity	NPC471264
0.7093	Intermediate Similarity	NPC61332
0.7093	Intermediate Similarity	NPC240130
0.7089	Intermediate Similarity	NPC197743
0.7089	Intermediate Similarity	NPC297145
0.7087	Intermediate Similarity	NPC322598
0.7083	Intermediate Similarity	NPC473322
0.708	Intermediate Similarity	NPC470544
0.7075	Intermediate Similarity	NPC267237
0.7075	Intermediate Similarity	NPC141050
0.7063	Intermediate Similarity	NPC25565
0.7055	Intermediate Similarity	NPC280022
0.7039	Intermediate Similarity	NPC316008
0.7039	Intermediate Similarity	NPC313867
0.7032	Intermediate Similarity	NPC475168
0.7032	Intermediate Similarity	NPC7817
0.703	Intermediate Similarity	NPC475532
0.7021	Intermediate Similarity	NPC252878
0.7021	Intermediate Similarity	NPC160493
0.702	Intermediate Similarity	NPC139326
0.702	Intermediate Similarity	NPC197682
0.7014	Intermediate Similarity	NPC319766
0.7008	Intermediate Similarity	NPC475439
0.7008	Intermediate Similarity	NPC473501
0.7008	Intermediate Similarity	NPC324569
0.7	Intermediate Similarity	NPC477061
0.7	Intermediate Similarity	NPC471527
0.7	Intermediate Similarity	NPC476259
0.7	Intermediate Similarity	NPC45777
0.7	Intermediate Similarity	NPC80150
0.6993	Remote Similarity	NPC262077
0.6993	Remote Similarity	NPC314358
0.6988	Remote Similarity	NPC165285
0.698	Remote Similarity	NPC68865
0.6974	Remote Similarity	NPC315283
0.6974	Remote Similarity	NPC314388
0.6972	Remote Similarity	NPC46427
0.6971	Remote Similarity	NPC302715
0.6968	Remote Similarity	NPC129666
0.6959	Remote Similarity	NPC248283
0.6954	Remote Similarity	NPC168113
0.6948	Remote Similarity	NPC138775
0.6947	Remote Similarity	NPC194390
0.6947	Remote Similarity	NPC88267
0.6947	Remote Similarity	NPC224610
0.6947	Remote Similarity	NPC113326
0.6939	Remote Similarity	NPC326966
0.6936	Remote Similarity	NPC102959
0.6923	Remote Similarity	NPC22746
0.6912	Remote Similarity	NPC273814
0.6908	Remote Similarity	NPC176226
0.6908	Remote Similarity	NPC168861
0.6899	Remote Similarity	NPC470902
0.6897	Remote Similarity	NPC60516
0.6892	Remote Similarity	NPC287401
0.6886	Remote Similarity	NPC17698
0.6879	Remote Similarity	NPC94862
0.6875	Remote Similarity	NPC4974
0.6867	Remote Similarity	NPC127741
0.6848	Remote Similarity	NPC473000
0.6848	Remote Similarity	NPC469904
0.6845	Remote Similarity	NPC469900
0.6839	Remote Similarity	NPC329761
0.6839	Remote Similarity	NPC225648
0.6835	Remote Similarity	NPC239357
0.6832	Remote Similarity	NPC469898
0.6824	Remote Similarity	NPC472999
0.6824	Remote Similarity	NPC246913
0.6821	Remote Similarity	NPC287358
0.6803	Remote Similarity	NPC300315
0.6803	Remote Similarity	NPC325651
0.6803	Remote Similarity	NPC200589
0.6795	Remote Similarity	NPC240848
0.6792	Remote Similarity	NPC473002
0.679	Remote Similarity	NPC473003
0.6776	Remote Similarity	NPC307357
0.6776	Remote Similarity	NPC46098
0.6776	Remote Similarity	NPC268841
0.6765	Remote Similarity	NPC97526
0.6765	Remote Similarity	NPC119652
0.6748	Remote Similarity	NPC73655
0.6742	Remote Similarity	NPC471317
0.6732	Remote Similarity	NPC469427
0.6732	Remote Similarity	NPC469426
0.6731	Remote Similarity	NPC145113
0.6731	Remote Similarity	NPC135121
0.6722	Remote Similarity	NPC477552
0.6722	Remote Similarity	NPC477550
0.6714	Remote Similarity	NPC285926
0.6714	Remote Similarity	NPC14672
0.6714	Remote Similarity	NPC315276
0.671	Remote Similarity	NPC477217
0.671	Remote Similarity	NPC201244
0.671	Remote Similarity	NPC322878
0.6707	Remote Similarity	NPC46009
0.6688	Remote Similarity	NPC105717
0.6667	Remote Similarity	NPC63931
0.6667	Remote Similarity	NPC162104
0.6667	Remote Similarity	NPC27581
0.6648	Remote Similarity	NPC477551
0.6645	Remote Similarity	NPC326241
0.6642	Remote Similarity	NPC476198
0.6627	Remote Similarity	NPC306804
0.6622	Remote Similarity	NPC296712

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 NPC314835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	89
0.1-0.2	322
0.2-0.3	730
0.3-0.4	2390
0.4-0.5	3978
0.5-0.6	1355
0.6-0.7	229
0.7-0.8	52
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8467	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD7495	Discontinued
0.8406	Intermediate Similarity	NPD6901	Phase 3
0.8357	Intermediate Similarity	NPD8076	Discontinued
0.8309	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7523	Phase 3
0.7652	Intermediate Similarity	NPD1348	Approved
0.763	Intermediate Similarity	NPD7342	Discontinued
0.7612	Intermediate Similarity	NPD2217	Approved
0.7612	Intermediate Similarity	NPD2218	Phase 2
0.7597	Intermediate Similarity	NPD8019	Approved
0.7584	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3606	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6852	Discontinued
0.75	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5367	Discontinued
0.7464	Intermediate Similarity	NPD3071	Approved
0.7464	Intermediate Similarity	NPD3072	Approved
0.7464	Intermediate Similarity	NPD3073	Approved
0.7451	Intermediate Similarity	NPD6670	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4177	Approved
0.7447	Intermediate Similarity	NPD4175	Approved
0.7434	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4762	Approved
0.7391	Intermediate Similarity	NPD4761	Approved
0.7379	Intermediate Similarity	NPD4757	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD8303	Discontinued
0.7338	Intermediate Similarity	NPD2584	Suspended
0.7329	Intermediate Similarity	NPD5725	Approved
0.7329	Intermediate Similarity	NPD6073	Approved
0.7313	Intermediate Similarity	NPD747	Discontinued
0.731	Intermediate Similarity	NPD5323	Approved
0.7273	Intermediate Similarity	NPD3642	Approved
0.7273	Intermediate Similarity	NPD3644	Approved
0.7273	Intermediate Similarity	NPD3643	Approved
0.7273	Intermediate Similarity	NPD4676	Approved
0.7273	Intermediate Similarity	NPD5263	Approved
0.7273	Intermediate Similarity	NPD6359	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7828	Discontinued
0.7203	Intermediate Similarity	NPD3040	Approved
0.7192	Intermediate Similarity	NPD4153	Approved
0.7192	Intermediate Similarity	NPD5296	Approved
0.719	Intermediate Similarity	NPD6088	Approved
0.7183	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5299	Approved
0.7163	Intermediate Similarity	NPD4677	Discontinued
0.7162	Intermediate Similarity	NPD4214	Discontinued
0.7162	Intermediate Similarity	NPD8154	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4125	Approved
0.7143	Intermediate Similarity	NPD3908	Approved
0.7143	Intermediate Similarity	NPD9566	Approved
0.7143	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4151	Approved
0.7125	Intermediate Similarity	NPD4564	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4565	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2887	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1040	Phase 2
0.7021	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5747	Discontinued
0.7	Intermediate Similarity	NPD4158	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3136	Phase 2
0.698	Remote Similarity	NPD8173	Phase 2
0.698	Remote Similarity	NPD8172	Phase 2
0.6968	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8416	Discontinued
0.6959	Remote Similarity	NPD6623	Phase 3
0.695	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5981	Approved
0.6918	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6865	Phase 2
0.6887	Remote Similarity	NPD6864	Phase 2
0.6884	Remote Similarity	NPD7508	Discontinued
0.6871	Remote Similarity	NPD4794	Discontinued
0.6863	Remote Similarity	NPD6681	Discovery
0.6857	Remote Similarity	NPD6093	Discontinued
0.6845	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1812	Approved
0.6825	Remote Similarity	NPD1814	Approved
0.6824	Remote Similarity	NPD5581	Approved
0.6821	Remote Similarity	NPD6294	Approved
0.6821	Remote Similarity	NPD6295	Approved
0.6821	Remote Similarity	NPD4126	Approved
0.6818	Remote Similarity	NPD5265	Approved
0.6818	Remote Similarity	NPD5264	Approved
0.6779	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4738	Phase 2
0.6753	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1374	Approved
0.6739	Remote Similarity	NPD1370	Approved
0.6739	Remote Similarity	NPD1373	Approved
0.6739	Remote Similarity	NPD1371	Approved
0.6714	Remote Similarity	NPD5162	Approved
0.6711	Remote Similarity	NPD1330	Phase 2
0.6711	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD253	Approved
0.6689	Remote Similarity	NPD8643	Discontinued
0.6688	Remote Similarity	NPD7978	Discontinued
0.6667	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD8323	Discontinued
0.6622	Remote Similarity	NPD5759	Approved
0.6605	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7720	Phase 2
0.6581	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7105	Phase 1
0.6564	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7613	Discontinued
0.6541	Remote Similarity	NPD5613	Approved
0.6541	Remote Similarity	NPD5614	Approved
0.6541	Remote Similarity	NPD3988	Approved
0.6541	Remote Similarity	NPD3987	Approved
0.6531	Remote Similarity	NPD3125	Approved
0.6516	Remote Similarity	NPD7512	Approved
0.6516	Remote Similarity	NPD7511	Approved
0.6513	Remote Similarity	NPD8265	Approved
0.6503	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3519	Discontinued
0.6474	Remote Similarity	NPD4152	Approved
0.6474	Remote Similarity	NPD2087	Approved
0.6474	Remote Similarity	NPD2088	Approved
0.6458	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1968	Approved
0.6456	Remote Similarity	NPD1967	Approved
0.6454	Remote Similarity	NPD2635	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6646	Discontinued
0.6443	Remote Similarity	NPD3588	Discontinued
0.6443	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6690	Approved
0.6429	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5982	Phase 2
0.6415	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.641	Remote Similarity	NPD4172	Approved
0.641	Remote Similarity	NPD4173	Approved
0.641	Remote Similarity	NPD7450	Phase 2
0.64	Remote Similarity	NPD3626	Phase 3
0.64	Remote Similarity	NPD4087	Phase 2
0.6398	Remote Similarity	NPD1664	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD999	Phase 2
0.6389	Remote Similarity	NPD4479	Discontinued
0.6386	Remote Similarity	NPD4567	Approved
0.6386	Remote Similarity	NPD4566	Approved
0.6385	Remote Similarity	NPD1066	Discontinued
0.638	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5774	Approved
0.6379	Remote Similarity	NPD5775	Approved
0.637	Remote Similarity	NPD3881	Discontinued
0.6364	Remote Similarity	NPD6679	Phase 3
0.6364	Remote Similarity	NPD6680	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3123	Discovery
0.6364	Remote Similarity	NPD6678	Phase 3
0.6343	Remote Similarity	NPD3518	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD4814	Discontinued
0.6324	Remote Similarity	NPD309	Approved
0.6324	Remote Similarity	NPD10	Approved
0.6324	Remote Similarity	NPD311	Approved
0.6324	Remote Similarity	NPD314	Approved
0.6324	Remote Similarity	NPD315	Approved
0.6324	Remote Similarity	NPD310	Approved
0.6323	Remote Similarity	NPD7510	Approved
0.6322	Remote Similarity	NPD3991	Approved
0.6322	Remote Similarity	NPD3996	Approved
0.6322	Remote Similarity	NPD3994	Approved
0.6322	Remote Similarity	NPD3992	Approved
0.6322	Remote Similarity	NPD3995	Approved
0.6322	Remote Similarity	NPD3993	Approved
0.6319	Remote Similarity	NPD2116	Approved
0.6319	Remote Similarity	NPD2115	Approved
0.6319	Remote Similarity	NPD2117	Pre-registration
0.6319	Remote Similarity	NPD7522	Discontinued
0.6312	Remote Similarity	NPD2607	Approved
0.6312	Remote Similarity	NPD480	Approved
0.6312	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD2198	Approved
0.6309	Remote Similarity	NPD2199	Approved
0.6309	Remote Similarity	NPD6325	Discontinued
0.6301	Remote Similarity	NPD5200	Clinical (unspecified phase)

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