NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.14
Volume:	259.979
LogP:	1.735
LogD:	1.82
LogS:	-2.148
# Rotatable Bonds:	3
TPSA:	58.2
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	2.776
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.698
MDCK Permeability:	5.600159784080461e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.806
Plasma Protein Binding (PPB):	67.01347351074219%
Volume Distribution (VD):	0.623
Pgp-substrate:	26.18316650390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.488
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.201
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	4.207
Half-life (T1/2):	0.691

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.299
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.049
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC303045

Natural Product ID:	NPC303045
*Common Name:**	Cyclo(Lphe-L-Val)
IUPAC Name:	(3S,6S)-3-benzyl-6-propan-2-ylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	OQQPOHUVAQPSHJ-RYUDHWBXSA-N
Standard InCHI:	InChI=1S/C14H18N2O2/c1-9(2)12-14(18)15-11(13(17)16-12)8-10-6-4-3-5-7-10/h3-7,9,11-12H,8H2,1-2H3,(H,15,18)(H,16,17)/t11-,12-/m0/s1
SMILES:	CC([C@@H]1N=C(O)[C@@H](N=C1O)Cc1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503815
PubChem CID:	13783105
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:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[12880307]
NPO40546	Paecilomyces marquandii	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190466]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Stems	n.a.	n.a.	PMID[17663584]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[18186611]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	Steamed Roots	n.a.	n.a.	PMID[26200131]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562741]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517238]
NPO40546	Paecilomyces marquandii	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31432669]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31625751]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Herb	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21891	Panax notoginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21891	Panax notoginseng	Species	Araliaceae	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
IC50	1
Others	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	9.0	mm	PMID[469874]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.0	mm	PMID[469874]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	61.07	%	PMID[469875]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	3890.0	nM	PMID[469875]

☑ 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 NPC303045 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	102
0.1-0.2	1127
0.2-0.3	8324
0.3-0.4	18602
0.4-0.5	11140
0.5-0.6	2684
0.6-0.7	545
0.7-0.8	131
0.8-0.85	27
0.85-0.9	8
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC161972
0.9659	High Similarity	NPC226438
0.9348	High Similarity	NPC311242
0.9239	High Similarity	NPC25565
0.914	High Similarity	NPC475439
0.914	High Similarity	NPC473501
0.8587	High Similarity	NPC470877
0.8586	High Similarity	NPC224610
0.8586	High Similarity	NPC113326
0.8586	High Similarity	NPC88267
0.8586	High Similarity	NPC194390
0.8571	High Similarity	NPC471638
0.8495	Intermediate Similarity	NPC78041
0.8495	Intermediate Similarity	NPC471307
0.8495	Intermediate Similarity	NPC141139
0.8495	Intermediate Similarity	NPC172128
0.8495	Intermediate Similarity	NPC159178
0.8495	Intermediate Similarity	NPC74936
0.8495	Intermediate Similarity	NPC316108
0.8495	Intermediate Similarity	NPC209764
0.8495	Intermediate Similarity	NPC121872
0.8416	Intermediate Similarity	NPC327481
0.8333	Intermediate Similarity	NPC58674
0.8302	Intermediate Similarity	NPC118202
0.8229	Intermediate Similarity	NPC471309
0.8211	Intermediate Similarity	NPC245259
0.8182	Intermediate Similarity	NPC12730
0.8131	Intermediate Similarity	NPC33742
0.8085	Intermediate Similarity	NPC12429
0.8085	Intermediate Similarity	NPC325441
0.7961	Intermediate Similarity	NPC211551
0.7944	Intermediate Similarity	NPC474584
0.7941	Intermediate Similarity	NPC164859
0.7925	Intermediate Similarity	NPC319579
0.7917	Intermediate Similarity	NPC258627
0.7818	Intermediate Similarity	NPC470544
0.7818	Intermediate Similarity	NPC82963
0.78	Intermediate Similarity	NPC33168
0.7767	Intermediate Similarity	NPC471317
0.7748	Intermediate Similarity	NPC38458
0.7748	Intermediate Similarity	NPC311737
0.7748	Intermediate Similarity	NPC470545
0.7727	Intermediate Similarity	NPC317254
0.7706	Intermediate Similarity	NPC35850
0.7706	Intermediate Similarity	NPC1986
0.7706	Intermediate Similarity	NPC276949
0.7706	Intermediate Similarity	NPC474544
0.7685	Intermediate Similarity	NPC329011
0.7684	Intermediate Similarity	NPC203076
0.7679	Intermediate Similarity	NPC470546
0.7658	Intermediate Similarity	NPC2265
0.7634	Intermediate Similarity	NPC14326
0.7609	Intermediate Similarity	NPC192623
0.7604	Intermediate Similarity	NPC473031
0.7596	Intermediate Similarity	NPC471310
0.7596	Intermediate Similarity	NPC202613
0.7589	Intermediate Similarity	NPC254088
0.7589	Intermediate Similarity	NPC169328
0.7579	Intermediate Similarity	NPC3210
0.7573	Intermediate Similarity	NPC469457
0.7568	Intermediate Similarity	NPC197470
0.7544	Intermediate Similarity	NPC477061
0.7544	Intermediate Similarity	NPC45777
0.7522	Intermediate Similarity	NPC310467
0.7522	Intermediate Similarity	NPC314992
0.7522	Intermediate Similarity	NPC237420
0.75	Intermediate Similarity	NPC14672
0.75	Intermediate Similarity	NPC315276
0.75	Intermediate Similarity	NPC285926
0.7478	Intermediate Similarity	NPC71684
0.7456	Intermediate Similarity	NPC283760
0.7431	Intermediate Similarity	NPC474149
0.7423	Intermediate Similarity	NPC198747
0.7404	Intermediate Similarity	NPC228400
0.7404	Intermediate Similarity	NPC214200
0.74	Intermediate Similarity	NPC265521
0.7391	Intermediate Similarity	NPC478015
0.7391	Intermediate Similarity	NPC478016
0.7391	Intermediate Similarity	NPC476990
0.7391	Intermediate Similarity	NPC478014
0.7383	Intermediate Similarity	NPC231705
0.7358	Intermediate Similarity	NPC275467
0.735	Intermediate Similarity	NPC35996
0.7339	Intermediate Similarity	NPC258056
0.7328	Intermediate Similarity	NPC202521
0.7321	Intermediate Similarity	NPC205652
0.7282	Intermediate Similarity	NPC10781
0.7282	Intermediate Similarity	NPC293628
0.7282	Intermediate Similarity	NPC122493
0.7265	Intermediate Similarity	NPC252878
0.7264	Intermediate Similarity	NPC178902
0.7257	Intermediate Similarity	NPC188010
0.7227	Intermediate Similarity	NPC47667
0.7222	Intermediate Similarity	NPC274089
0.7222	Intermediate Similarity	NPC191215
0.7212	Intermediate Similarity	NPC164514
0.7212	Intermediate Similarity	NPC290515
0.7212	Intermediate Similarity	NPC108606
0.7212	Intermediate Similarity	NPC303611
0.7212	Intermediate Similarity	NPC322598
0.7212	Intermediate Similarity	NPC226096
0.7203	Intermediate Similarity	NPC6975
0.7203	Intermediate Similarity	NPC46427
0.7184	Intermediate Similarity	NPC3371
0.7172	Intermediate Similarity	NPC262393
0.717	Intermediate Similarity	NPC318154
0.7167	Intermediate Similarity	NPC477937
0.7157	Intermediate Similarity	NPC476483
0.7156	Intermediate Similarity	NPC142297
0.7154	Intermediate Similarity	NPC325479
0.7143	Intermediate Similarity	NPC273814
0.713	Intermediate Similarity	NPC67043
0.7115	Intermediate Similarity	NPC324569
0.7094	Intermediate Similarity	NPC190663
0.7094	Intermediate Similarity	NPC200964
0.7094	Intermediate Similarity	NPC80150
0.7091	Intermediate Similarity	NPC24101
0.7091	Intermediate Similarity	NPC153690
0.7091	Intermediate Similarity	NPC96224
0.7083	Intermediate Similarity	NPC474479
0.7083	Intermediate Similarity	NPC4974
0.7083	Intermediate Similarity	NPC101719
0.7059	Intermediate Similarity	NPC323164
0.7059	Intermediate Similarity	NPC175726
0.7059	Intermediate Similarity	NPC474082
0.7049	Intermediate Similarity	NPC473322
0.7043	Intermediate Similarity	NPC239357
0.7037	Intermediate Similarity	NPC147000
0.7037	Intermediate Similarity	NPC150254
0.7037	Intermediate Similarity	NPC226778
0.7037	Intermediate Similarity	NPC304761
0.7033	Intermediate Similarity	NPC244738
0.7018	Intermediate Similarity	NPC471318
0.701	Intermediate Similarity	NPC477770
0.7	Intermediate Similarity	NPC22746
0.7	Intermediate Similarity	NPC222466
0.6975	Remote Similarity	NPC474862
0.6975	Remote Similarity	NPC160493
0.6967	Remote Similarity	NPC319766
0.6957	Remote Similarity	NPC122327
0.6957	Remote Similarity	NPC113000
0.6957	Remote Similarity	NPC112609
0.6952	Remote Similarity	NPC472258
0.6944	Remote Similarity	NPC178681
0.6935	Remote Similarity	NPC255447
0.6923	Remote Similarity	NPC208302
0.6923	Remote Similarity	NPC20142
0.6923	Remote Similarity	NPC215351
0.6917	Remote Similarity	NPC472415
0.6911	Remote Similarity	NPC111428
0.6909	Remote Similarity	NPC474804
0.6909	Remote Similarity	NPC474973
0.6909	Remote Similarity	NPC130898
0.6903	Remote Similarity	NPC275410
0.6882	Remote Similarity	NPC189371
0.688	Remote Similarity	NPC326966
0.688	Remote Similarity	NPC246913
0.6875	Remote Similarity	NPC292758
0.6875	Remote Similarity	NPC309279
0.6875	Remote Similarity	NPC65855
0.687	Remote Similarity	NPC470550
0.6864	Remote Similarity	NPC319950
0.6863	Remote Similarity	NPC78154
0.6855	Remote Similarity	NPC300315
0.6852	Remote Similarity	NPC327226
0.6842	Remote Similarity	NPC224544
0.6833	Remote Similarity	NPC109151
0.6818	Remote Similarity	NPC143516
0.681	Remote Similarity	NPC235421
0.6807	Remote Similarity	NPC476183
0.6803	Remote Similarity	NPC474926
0.6803	Remote Similarity	NPC472414
0.68	Remote Similarity	NPC130309
0.678	Remote Similarity	NPC220698
0.6774	Remote Similarity	NPC469666
0.6774	Remote Similarity	NPC108218
0.6757	Remote Similarity	NPC45033
0.6757	Remote Similarity	NPC473498
0.675	Remote Similarity	NPC476184
0.675	Remote Similarity	NPC476281
0.6748	Remote Similarity	NPC278097
0.6737	Remote Similarity	NPC325662
0.6737	Remote Similarity	NPC290638
0.6737	Remote Similarity	NPC98269
0.6735	Remote Similarity	NPC121478
0.6735	Remote Similarity	NPC73637
0.6724	Remote Similarity	NPC142599
0.6723	Remote Similarity	NPC43275
0.6723	Remote Similarity	NPC268572
0.672	Remote Similarity	NPC325651
0.672	Remote Similarity	NPC200589
0.672	Remote Similarity	NPC478147
0.6701	Remote Similarity	NPC184030
0.6701	Remote Similarity	NPC164449
0.6698	Remote Similarity	NPC471319
0.6698	Remote Similarity	NPC471320
0.6697	Remote Similarity	NPC329375
0.6694	Remote Similarity	NPC199738
0.6694	Remote Similarity	NPC27581
0.6694	Remote Similarity	NPC210950

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 NPC303045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	90
0.1-0.2	512
0.2-0.3	931
0.3-0.4	2618
0.4-0.5	3010
0.5-0.6	1500
0.6-0.7	413
0.7-0.8	69
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD1814	Approved
0.8913	High Similarity	NPD1812	Approved
0.8854	High Similarity	NPD4760	Clinical (unspecified phase)
0.871	High Similarity	NPD6690	Approved
0.8229	Intermediate Similarity	NPD1080	Approved
0.8144	Intermediate Similarity	NPD4814	Discontinued
0.8137	Intermediate Similarity	NPD999	Phase 2
0.8125	Intermediate Similarity	NPD752	Approved
0.8095	Intermediate Similarity	NPD3642	Approved
0.8095	Intermediate Similarity	NPD3644	Approved
0.8095	Intermediate Similarity	NPD3643	Approved
0.7981	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD719	Approved
0.7857	Intermediate Similarity	NPD720	Approved
0.7835	Intermediate Similarity	NPD530	Approved
0.78	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD9538	Approved
0.7778	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6360	Discontinued
0.7708	Intermediate Similarity	NPD1101	Approved
0.77	Intermediate Similarity	NPD2895	Discontinued
0.77	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1018	Approved
0.7619	Intermediate Similarity	NPD1040	Phase 2
0.7619	Intermediate Similarity	NPD5717	Approved
0.7596	Intermediate Similarity	NPD1542	Approved
0.7589	Intermediate Similarity	NPD7522	Discontinued
0.7568	Intermediate Similarity	NPD1348	Approved
0.7523	Intermediate Similarity	NPD3651	Discontinued
0.7522	Intermediate Similarity	NPD2218	Phase 2
0.7522	Intermediate Similarity	NPD2217	Approved
0.75	Intermediate Similarity	NPD4119	Approved
0.75	Intermediate Similarity	NPD1540	Approved
0.7476	Intermediate Similarity	NPD1067	Discontinued
0.7455	Intermediate Similarity	NPD1764	Approved
0.7455	Intermediate Similarity	NPD1762	Approved
0.7451	Intermediate Similarity	NPD1875	Phase 1
0.7431	Intermediate Similarity	NPD2583	Phase 2
0.7423	Intermediate Similarity	NPD187	Approved
0.7391	Intermediate Similarity	NPD7342	Discontinued
0.7387	Intermediate Similarity	NPD3149	Approved
0.7387	Intermediate Similarity	NPD3148	Approved
0.7387	Intermediate Similarity	NPD3150	Approved
0.7387	Intermediate Similarity	NPD3147	Approved
0.7387	Intermediate Similarity	NPD2659	Approved
0.7387	Intermediate Similarity	NPD2658	Approved
0.735	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5716	Approved
0.7333	Intermediate Similarity	NPD855	Approved
0.7333	Intermediate Similarity	NPD854	Approved
0.7327	Intermediate Similarity	NPD1066	Discontinued
0.7327	Intermediate Similarity	NPD1409	Phase 3
0.7304	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5981	Approved
0.7297	Intermediate Similarity	NPD3066	Phase 2
0.7297	Intermediate Similarity	NPD4165	Phase 2
0.729	Intermediate Similarity	NPD564	Approved
0.729	Intermediate Similarity	NPD563	Approved
0.7282	Intermediate Similarity	NPD9566	Approved
0.7257	Intermediate Similarity	NPD7508	Discontinued
0.7248	Intermediate Similarity	NPD2679	Approved
0.7248	Intermediate Similarity	NPD2678	Approved
0.7212	Intermediate Similarity	NPD4117	Approved
0.7212	Intermediate Similarity	NPD9609	Approved
0.7212	Intermediate Similarity	NPD9612	Approved
0.7212	Intermediate Similarity	NPD9611	Approved
0.7203	Intermediate Similarity	NPD5702	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4719	Phase 2
0.7158	Intermediate Similarity	NPD472	Approved
0.7157	Intermediate Similarity	NPD1394	Approved
0.7157	Intermediate Similarity	NPD3718	Approved
0.7157	Intermediate Similarity	NPD3719	Approved
0.7156	Intermediate Similarity	NPD6406	Approved
0.7143	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD517	Discontinued
0.7115	Intermediate Similarity	NPD528	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5367	Discontinued
0.7069	Intermediate Similarity	NPD6093	Discontinued
0.7048	Intermediate Similarity	NPD1724	Approved
0.7043	Intermediate Similarity	NPD3123	Discovery
0.7037	Intermediate Similarity	NPD10	Approved
0.7037	Intermediate Similarity	NPD315	Approved
0.7037	Intermediate Similarity	NPD314	Approved
0.7037	Intermediate Similarity	NPD311	Approved
0.7037	Intermediate Similarity	NPD309	Approved
0.7037	Intermediate Similarity	NPD310	Approved
0.7033	Intermediate Similarity	NPD9728	Phase 1
0.7027	Intermediate Similarity	NPD1107	Approved
0.7027	Intermediate Similarity	NPD1108	Approved
0.7009	Intermediate Similarity	NPD1419	Approved
0.7009	Intermediate Similarity	NPD4817	Approved
0.7009	Intermediate Similarity	NPD1737	Approved
0.7009	Intermediate Similarity	NPD4818	Approved
0.7009	Intermediate Similarity	NPD1735	Approved
0.7009	Intermediate Similarity	NPD1417	Approved
0.7009	Intermediate Similarity	NPD1736	Approved
0.6992	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD9712	Approved
0.6979	Remote Similarity	NPD3035	Approved
0.6967	Remote Similarity	NPD7451	Discontinued
0.6964	Remote Similarity	NPD4254	Approved
0.6964	Remote Similarity	NPD4253	Approved
0.6957	Remote Similarity	NPD4032	Approved
0.6957	Remote Similarity	NPD80	Approved
0.6957	Remote Similarity	NPD9591	Approved
0.6957	Remote Similarity	NPD9593	Approved
0.6957	Remote Similarity	NPD4031	Approved
0.6957	Remote Similarity	NPD9594	Approved
0.6957	Remote Similarity	NPD9589	Approved
0.6957	Remote Similarity	NPD9592	Approved
0.6957	Remote Similarity	NPD9590	Approved
0.6957	Remote Similarity	NPD9588	Approved
0.6947	Remote Similarity	NPD1053	Approved
0.6947	Remote Similarity	NPD1052	Approved
0.6947	Remote Similarity	NPD1051	Approved
0.6944	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5578	Approved
0.6942	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6325	Discontinued
0.6923	Remote Similarity	NPD998	Approved
0.6916	Remote Similarity	NPD1275	Phase 2
0.6911	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7828	Discontinued
0.6907	Remote Similarity	NPD4170	Approved
0.6907	Remote Similarity	NPD4169	Approved
0.6907	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9711	Approved
0.6887	Remote Similarity	NPD253	Approved
0.6887	Remote Similarity	NPD9710	Approved
0.6885	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3407	Phase 3
0.6864	Remote Similarity	NPD2210	Approved
0.6864	Remote Similarity	NPD2212	Approved
0.6864	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4125	Approved
0.6847	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD295	Approved
0.6842	Remote Similarity	NPD293	Approved
0.6842	Remote Similarity	NPD296	Approved
0.6838	Remote Similarity	NPD1359	Approved
0.6833	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8118	Discontinued
0.681	Remote Similarity	NPD2622	Approved
0.6803	Remote Similarity	NPD1036	Approved
0.68	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3136	Phase 2
0.68	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4738	Phase 2
0.6789	Remote Similarity	NPD3682	Approved
0.6789	Remote Similarity	NPD3681	Approved
0.6789	Remote Similarity	NPD3683	Approved
0.6789	Remote Similarity	NPD1415	Approved
0.6789	Remote Similarity	NPD5103	Approved
0.6789	Remote Similarity	NPD4231	Approved
0.6789	Remote Similarity	NPD4229	Approved
0.6789	Remote Similarity	NPD3680	Approved
0.6783	Remote Similarity	NPD1681	Approved
0.6783	Remote Similarity	NPD1656	Phase 2
0.6783	Remote Similarity	NPD1680	Approved
0.6783	Remote Similarity	NPD1682	Approved
0.678	Remote Similarity	NPD4479	Discontinued
0.6777	Remote Similarity	NPD6624	Discontinued
0.6777	Remote Similarity	NPD2584	Suspended
0.6774	Remote Similarity	NPD9701	Discontinued
0.6772	Remote Similarity	NPD8265	Approved
0.6768	Remote Similarity	NPD2539	Approved
0.6768	Remote Similarity	NPD785	Approved
0.6768	Remote Similarity	NPD2538	Approved
0.6762	Remote Similarity	NPD665	Phase 2
0.6757	Remote Similarity	NPD812	Approved
0.6757	Remote Similarity	NPD810	Approved
0.6757	Remote Similarity	NPD811	Approved
0.6752	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7908	Discontinued
0.6737	Remote Similarity	NPD4144	Approved
0.6737	Remote Similarity	NPD4147	Approved
0.6727	Remote Similarity	NPD9608	Approved
0.6727	Remote Similarity	NPD9610	Approved
0.6723	Remote Similarity	NPD1922	Discontinued
0.67	Remote Similarity	NPD2208	Approved
0.67	Remote Similarity	NPD2205	Approved
0.6697	Remote Similarity	NPD9721	Approved
0.6697	Remote Similarity	NPD9722	Approved
0.6696	Remote Similarity	NPD181	Approved
0.6696	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1401	Approved
0.6695	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD531	Approved
0.6667	Remote Similarity	NPD9563	Approved
0.6667	Remote Similarity	NPD9564	Approved
0.6667	Remote Similarity	NPD1001	Discontinued
0.6667	Remote Similarity	NPD79	Approved

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