NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.09
Volume:	208.091
LogP:	0.686
LogD:	0.738
LogS:	-1.703
# Rotatable Bonds:	2
TPSA:	58.2
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	2.487
Fsp3:	0.273
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:	-4.945
MDCK Permeability:	5.5059932492440566e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.233
20% Bioavailability (F20%):	0.596
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.975
Plasma Protein Binding (PPB):	32.24169921875%
Volume Distribution (VD):	0.484
Pgp-substrate:	58.85890579223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	5.794
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.304
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC226438

Natural Product ID:	NPC226438
*Common Name:**	Cyclo(Gly-Phe)
IUPAC Name:	(3S)-3-benzylpiperazine-2,5-dione
Synonyms:
Standard InCHIKey:	UZOJHXFWJFSFAI-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C11H12N2O2/c14-10-7-12-11(15)9(13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,15)(H,13,14)/t9-/m0/s1
SMILES:	OC1=NCC(=N[C@H]1Cc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2074841
PubChem CID:	7076549
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
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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
Individual Protein	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1237	Individual Protein	Oligopeptide transporter small intestine isoform	Homo sapiens	Km	=	90900.0	nM	PMID[465808]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	Activity	=	70.37	%	PMID[465809]
NPT474	Organism	Plasmodium berghei	Plasmodium berghei	IC50	=	4260.0	nM	PMID[465809]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[465810]

☑ 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 NPC226438 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	118
0.1-0.2	1837
0.2-0.3	10616
0.3-0.4	17521
0.4-0.5	9603
0.5-0.6	2381
0.6-0.7	458
0.7-0.8	124
0.8-0.85	27
0.85-0.9	8
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC161972
0.9659	High Similarity	NPC303045
0.9444	High Similarity	NPC311242
0.8913	High Similarity	NPC25565
0.8817	High Similarity	NPC475439
0.8817	High Similarity	NPC473501
0.8778	High Similarity	NPC316108
0.8652	High Similarity	NPC471638
0.8571	High Similarity	NPC172128
0.8462	Intermediate Similarity	NPC470877
0.837	Intermediate Similarity	NPC159178
0.837	Intermediate Similarity	NPC74936
0.837	Intermediate Similarity	NPC141139
0.837	Intermediate Similarity	NPC471307
0.837	Intermediate Similarity	NPC78041
0.837	Intermediate Similarity	NPC209764
0.837	Intermediate Similarity	NPC121872
0.8352	Intermediate Similarity	NPC325441
0.8283	Intermediate Similarity	NPC88267
0.8283	Intermediate Similarity	NPC224610
0.8283	Intermediate Similarity	NPC113326
0.8283	Intermediate Similarity	NPC194390
0.8247	Intermediate Similarity	NPC12730
0.8211	Intermediate Similarity	NPC58674
0.8182	Intermediate Similarity	NPC164859
0.8172	Intermediate Similarity	NPC258627
0.8119	Intermediate Similarity	NPC327481
0.8105	Intermediate Similarity	NPC471309
0.8085	Intermediate Similarity	NPC245259
0.802	Intermediate Similarity	NPC211551
0.8019	Intermediate Similarity	NPC118202
0.8019	Intermediate Similarity	NPC33742
0.7981	Intermediate Similarity	NPC319579
0.7957	Intermediate Similarity	NPC12429
0.787	Intermediate Similarity	NPC82963
0.7865	Intermediate Similarity	NPC192623
0.7857	Intermediate Similarity	NPC33168
0.7798	Intermediate Similarity	NPC38458
0.7798	Intermediate Similarity	NPC311737
0.7742	Intermediate Similarity	NPC203076
0.7736	Intermediate Similarity	NPC329011
0.7664	Intermediate Similarity	NPC474584
0.7647	Intermediate Similarity	NPC471317
0.7629	Intermediate Similarity	NPC265521
0.7593	Intermediate Similarity	NPC276949
0.7593	Intermediate Similarity	NPC35850
0.7545	Intermediate Similarity	NPC14672
0.7545	Intermediate Similarity	NPC315276
0.7545	Intermediate Similarity	NPC470544
0.7545	Intermediate Similarity	NPC285926
0.75	Intermediate Similarity	NPC293628
0.75	Intermediate Similarity	NPC122493
0.75	Intermediate Similarity	NPC10781
0.7477	Intermediate Similarity	NPC470545
0.7476	Intermediate Similarity	NPC202613
0.7476	Intermediate Similarity	NPC471310
0.7474	Intermediate Similarity	NPC473031
0.7474	Intermediate Similarity	NPC198747
0.7455	Intermediate Similarity	NPC197470
0.7455	Intermediate Similarity	NPC317254
0.7451	Intermediate Similarity	NPC469457
0.7447	Intermediate Similarity	NPC3210
0.7431	Intermediate Similarity	NPC1986
0.7431	Intermediate Similarity	NPC474544
0.7411	Intermediate Similarity	NPC470546
0.74	Intermediate Similarity	NPC3371
0.7396	Intermediate Similarity	NPC262393
0.7387	Intermediate Similarity	NPC2265
0.7364	Intermediate Similarity	NPC205652
0.7327	Intermediate Similarity	NPC324569
0.7321	Intermediate Similarity	NPC254088
0.7321	Intermediate Similarity	NPC169328
0.7312	Intermediate Similarity	NPC14326
0.7308	Intermediate Similarity	NPC178902
0.729	Intermediate Similarity	NPC153690
0.7282	Intermediate Similarity	NPC228400
0.7282	Intermediate Similarity	NPC214200
0.7281	Intermediate Similarity	NPC477061
0.7281	Intermediate Similarity	NPC45777
0.7273	Intermediate Similarity	NPC244738
0.7273	Intermediate Similarity	NPC323164
0.7264	Intermediate Similarity	NPC231705
0.7257	Intermediate Similarity	NPC310467
0.7257	Intermediate Similarity	NPC314992
0.7257	Intermediate Similarity	NPC237420
0.7255	Intermediate Similarity	NPC108606
0.7255	Intermediate Similarity	NPC164514
0.7255	Intermediate Similarity	NPC303611
0.7255	Intermediate Similarity	NPC290515
0.7255	Intermediate Similarity	NPC226096
0.7222	Intermediate Similarity	NPC258056
0.7217	Intermediate Similarity	NPC71684
0.7212	Intermediate Similarity	NPC318154
0.72	Intermediate Similarity	NPC476483
0.7193	Intermediate Similarity	NPC283760
0.717	Intermediate Similarity	NPC67043
0.7159	Intermediate Similarity	NPC208302
0.7156	Intermediate Similarity	NPC474149
0.7143	Intermediate Similarity	NPC178681
0.713	Intermediate Similarity	NPC478015
0.713	Intermediate Similarity	NPC476990
0.713	Intermediate Similarity	NPC24101
0.713	Intermediate Similarity	NPC478016
0.713	Intermediate Similarity	NPC478014
0.713	Intermediate Similarity	NPC96224
0.7129	Intermediate Similarity	NPC20142
0.7129	Intermediate Similarity	NPC215351
0.7103	Intermediate Similarity	NPC191215
0.7103	Intermediate Similarity	NPC274089
0.7097	Intermediate Similarity	NPC309279
0.7094	Intermediate Similarity	NPC474082
0.7094	Intermediate Similarity	NPC35996
0.7094	Intermediate Similarity	NPC175726
0.7091	Intermediate Similarity	NPC275410
0.7087	Intermediate Similarity	NPC322598
0.7075	Intermediate Similarity	NPC275467
0.7075	Intermediate Similarity	NPC304761
0.7075	Intermediate Similarity	NPC150254
0.7075	Intermediate Similarity	NPC226778
0.7075	Intermediate Similarity	NPC147000
0.7069	Intermediate Similarity	NPC202521
0.7037	Intermediate Similarity	NPC142297
0.7009	Intermediate Similarity	NPC252878
0.7	Intermediate Similarity	NPC122327
0.7	Intermediate Similarity	NPC113000
0.7	Intermediate Similarity	NPC112609
0.7	Intermediate Similarity	NPC108218
0.6991	Remote Similarity	NPC188010
0.699	Remote Similarity	NPC472258
0.6975	Remote Similarity	NPC47667
0.6975	Remote Similarity	NPC4974
0.6949	Remote Similarity	NPC46427
0.6949	Remote Similarity	NPC6975
0.6923	Remote Similarity	NPC189371
0.6917	Remote Similarity	NPC477937
0.6911	Remote Similarity	NPC325479
0.6903	Remote Similarity	NPC470550
0.6903	Remote Similarity	NPC471318
0.69	Remote Similarity	NPC78154
0.6897	Remote Similarity	NPC319950
0.6887	Remote Similarity	NPC327226
0.6887	Remote Similarity	NPC329375
0.6875	Remote Similarity	NPC146703
0.6875	Remote Similarity	NPC273814
0.6864	Remote Similarity	NPC27581
0.6854	Remote Similarity	NPC229235
0.6838	Remote Similarity	NPC190663
0.6838	Remote Similarity	NPC200964
0.6838	Remote Similarity	NPC80150
0.6833	Remote Similarity	NPC474479
0.6833	Remote Similarity	NPC101719
0.6813	Remote Similarity	NPC299134
0.6803	Remote Similarity	NPC111428
0.6803	Remote Similarity	NPC473322
0.6783	Remote Similarity	NPC239357
0.6783	Remote Similarity	NPC147957
0.6774	Remote Similarity	NPC325662
0.6774	Remote Similarity	NPC98269
0.6774	Remote Similarity	NPC290638
0.6771	Remote Similarity	NPC73637
0.6771	Remote Similarity	NPC121478
0.6762	Remote Similarity	NPC107619
0.6757	Remote Similarity	NPC292758
0.6757	Remote Similarity	NPC65855
0.6754	Remote Similarity	NPC142599
0.6752	Remote Similarity	NPC268572
0.675	Remote Similarity	NPC222466
0.675	Remote Similarity	NPC22746
0.6748	Remote Similarity	NPC325651
0.6737	Remote Similarity	NPC164449
0.6737	Remote Similarity	NPC184030
0.6737	Remote Similarity	NPC127343
0.6723	Remote Similarity	NPC160493
0.6723	Remote Similarity	NPC474862
0.6721	Remote Similarity	NPC199738
0.6721	Remote Similarity	NPC210950
0.6721	Remote Similarity	NPC319766
0.6702	Remote Similarity	NPC224544
0.6701	Remote Similarity	NPC119677
0.6701	Remote Similarity	NPC477770
0.6697	Remote Similarity	NPC476198
0.6696	Remote Similarity	NPC101139
0.6694	Remote Similarity	NPC474926
0.6694	Remote Similarity	NPC255447
0.6667	Remote Similarity	NPC469666
0.6667	Remote Similarity	NPC139658
0.6667	Remote Similarity	NPC472415
0.6667	Remote Similarity	NPC220698
0.6641	Remote Similarity	NPC242159
0.6641	Remote Similarity	NPC313694
0.664	Remote Similarity	NPC246913
0.664	Remote Similarity	NPC326966
0.6639	Remote Similarity	NPC273830
0.6636	Remote Similarity	NPC474804
0.6636	Remote Similarity	NPC473498
0.6636	Remote Similarity	NPC289381
0.6636	Remote Similarity	NPC130898
0.6636	Remote Similarity	NPC474973
0.6636	Remote Similarity	NPC45033
0.6636	Remote Similarity	NPC155847

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 NPC226438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	551
0.2-0.3	1092
0.3-0.4	2634
0.4-0.5	2932
0.5-0.6	1417
0.6-0.7	352
0.7-0.8	63
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8791	High Similarity	NPD1812	Approved
0.8791	High Similarity	NPD1814	Approved
0.8587	High Similarity	NPD6690	Approved
0.8542	High Similarity	NPD4760	Clinical (unspecified phase)
0.8384	Intermediate Similarity	NPD999	Phase 2
0.8191	Intermediate Similarity	NPD752	Approved
0.8105	Intermediate Similarity	NPD1080	Approved
0.8043	Intermediate Similarity	NPD9538	Approved
0.7917	Intermediate Similarity	NPD720	Approved
0.7917	Intermediate Similarity	NPD719	Approved
0.7843	Intermediate Similarity	NPD1040	Phase 2
0.7835	Intermediate Similarity	NPD4814	Discontinued
0.7822	Intermediate Similarity	NPD1542	Approved
0.781	Intermediate Similarity	NPD3642	Approved
0.781	Intermediate Similarity	NPD3643	Approved
0.781	Intermediate Similarity	NPD3644	Approved
0.7745	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD1540	Approved
0.7708	Intermediate Similarity	NPD530	Approved
0.7692	Intermediate Similarity	NPD6038	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1875	Phase 1
0.7677	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD1018	Approved
0.766	Intermediate Similarity	NPD187	Approved
0.7653	Intermediate Similarity	NPD1081	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9566	Approved
0.75	Intermediate Similarity	NPD5717	Approved
0.7477	Intermediate Similarity	NPD6360	Discontinued
0.7455	Intermediate Similarity	NPD1348	Approved
0.74	Intermediate Similarity	NPD2895	Discontinued
0.7396	Intermediate Similarity	NPD1101	Approved
0.7379	Intermediate Similarity	NPD4119	Approved
0.7353	Intermediate Similarity	NPD1067	Discontinued
0.7345	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1762	Approved
0.7339	Intermediate Similarity	NPD1764	Approved
0.7327	Intermediate Similarity	NPD528	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7522	Discontinued
0.7273	Intermediate Similarity	NPD9728	Phase 1
0.7273	Intermediate Similarity	NPD3149	Approved
0.7273	Intermediate Similarity	NPD3150	Approved
0.7273	Intermediate Similarity	NPD3147	Approved
0.7273	Intermediate Similarity	NPD3148	Approved
0.7273	Intermediate Similarity	NPD2658	Approved
0.7273	Intermediate Similarity	NPD2659	Approved
0.7257	Intermediate Similarity	NPD2217	Approved
0.7257	Intermediate Similarity	NPD2218	Phase 2
0.7255	Intermediate Similarity	NPD9609	Approved
0.7255	Intermediate Similarity	NPD9611	Approved
0.7255	Intermediate Similarity	NPD9612	Approved
0.7248	Intermediate Similarity	NPD3651	Discontinued
0.7217	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD855	Approved
0.7212	Intermediate Similarity	NPD854	Approved
0.7212	Intermediate Similarity	NPD5716	Approved
0.7204	Intermediate Similarity	NPD472	Approved
0.72	Intermediate Similarity	NPD1066	Discontinued
0.72	Intermediate Similarity	NPD1394	Approved
0.7184	Intermediate Similarity	NPD9712	Approved
0.7172	Intermediate Similarity	NPD517	Discontinued
0.717	Intermediate Similarity	NPD563	Approved
0.717	Intermediate Similarity	NPD564	Approved
0.7156	Intermediate Similarity	NPD2583	Phase 2
0.7143	Intermediate Similarity	NPD7508	Discontinued
0.713	Intermediate Similarity	NPD2678	Approved
0.713	Intermediate Similarity	NPD2679	Approved
0.713	Intermediate Similarity	NPD7342	Discontinued
0.7115	Intermediate Similarity	NPD1275	Phase 2
0.71	Intermediate Similarity	NPD159	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1724	Approved
0.7087	Intermediate Similarity	NPD9711	Approved
0.7087	Intermediate Similarity	NPD9710	Approved
0.7087	Intermediate Similarity	NPD4117	Approved
0.7075	Intermediate Similarity	NPD311	Approved
0.7075	Intermediate Similarity	NPD310	Approved
0.7075	Intermediate Similarity	NPD315	Approved
0.7075	Intermediate Similarity	NPD314	Approved
0.7075	Intermediate Similarity	NPD309	Approved
0.7075	Intermediate Similarity	NPD10	Approved
0.7048	Intermediate Similarity	NPD4719	Phase 2
0.7043	Intermediate Similarity	NPD5981	Approved
0.703	Intermediate Similarity	NPD3719	Approved
0.703	Intermediate Similarity	NPD1409	Phase 3
0.703	Intermediate Similarity	NPD3718	Approved
0.7027	Intermediate Similarity	NPD3066	Phase 2
0.7027	Intermediate Similarity	NPD4165	Phase 2
0.7	Intermediate Similarity	NPD9593	Approved
0.7	Intermediate Similarity	NPD9591	Approved
0.7	Intermediate Similarity	NPD9589	Approved
0.7	Intermediate Similarity	NPD9588	Approved
0.7	Intermediate Similarity	NPD9590	Approved
0.7	Intermediate Similarity	NPD80	Approved
0.7	Intermediate Similarity	NPD9592	Approved
0.7	Intermediate Similarity	NPD9594	Approved
0.6957	Remote Similarity	NPD998	Approved
0.6949	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD9701	Discontinued
0.693	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.693	Remote Similarity	NPD3123	Discovery
0.6923	Remote Similarity	NPD253	Approved
0.6917	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1107	Approved
0.6909	Remote Similarity	NPD1108	Approved
0.6897	Remote Similarity	NPD1922	Discontinued
0.6891	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1735	Approved
0.6887	Remote Similarity	NPD1737	Approved
0.6887	Remote Similarity	NPD1419	Approved
0.6887	Remote Similarity	NPD1417	Approved
0.6887	Remote Similarity	NPD9722	Approved
0.6887	Remote Similarity	NPD9721	Approved
0.6887	Remote Similarity	NPD1736	Approved
0.6882	Remote Similarity	NPD293	Approved
0.6882	Remote Similarity	NPD296	Approved
0.6882	Remote Similarity	NPD295	Approved
0.6881	Remote Similarity	NPD6406	Approved
0.687	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7451	Discontinued
0.6842	Remote Similarity	NPD4031	Approved
0.6842	Remote Similarity	NPD4032	Approved
0.6833	Remote Similarity	NPD5578	Approved
0.6833	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5367	Discontinued
0.6822	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5103	Approved
0.681	Remote Similarity	NPD6093	Discontinued
0.6809	Remote Similarity	NPD1052	Approved
0.6809	Remote Similarity	NPD1053	Approved
0.6809	Remote Similarity	NPD1051	Approved
0.6803	Remote Similarity	NPD7828	Discontinued
0.6803	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3772	Phase 3
0.6796	Remote Similarity	NPD665	Phase 2
0.6759	Remote Similarity	NPD9608	Approved
0.6759	Remote Similarity	NPD3407	Phase 3
0.6759	Remote Similarity	NPD9610	Approved
0.6752	Remote Similarity	NPD2212	Approved
0.6752	Remote Similarity	NPD2210	Approved
0.6748	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4817	Approved
0.6729	Remote Similarity	NPD4818	Approved
0.6727	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD181	Approved
0.6702	Remote Similarity	NPD9563	Approved
0.6702	Remote Similarity	NPD79	Approved
0.6702	Remote Similarity	NPD9564	Approved
0.67	Remote Similarity	NPD531	Approved
0.6696	Remote Similarity	NPD2622	Approved
0.6696	Remote Similarity	NPD4254	Approved
0.6696	Remote Similarity	NPD4253	Approved
0.6694	Remote Similarity	NPD1001	Discontinued
0.6694	Remote Similarity	NPD1036	Approved
0.6694	Remote Similarity	NPD6325	Discontinued
0.6667	Remote Similarity	NPD1656	Phase 2
0.6667	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4231	Approved
0.6667	Remote Similarity	NPD4658	Approved
0.6667	Remote Similarity	NPD4229	Approved
0.6667	Remote Similarity	NPD3682	Approved
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD3680	Approved
0.6667	Remote Similarity	NPD3683	Approved
0.6667	Remote Similarity	NPD2584	Suspended
0.6667	Remote Similarity	NPD3035	Approved
0.6667	Remote Similarity	NPD4656	Approved
0.6667	Remote Similarity	NPD3681	Approved
0.664	Remote Similarity	NPD8011	Discontinued
0.6639	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD812	Approved
0.6636	Remote Similarity	NPD810	Approved
0.6636	Remote Similarity	NPD811	Approved
0.6633	Remote Similarity	NPD785	Approved
0.6633	Remote Similarity	NPD2539	Approved
0.6633	Remote Similarity	NPD2538	Approved
0.6613	Remote Similarity	NPD4125	Approved
0.661	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD9713	Approved
0.6598	Remote Similarity	NPD4169	Approved
0.6598	Remote Similarity	NPD4170	Approved
0.6598	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4144	Approved
0.6596	Remote Similarity	NPD4147	Approved
0.6593	Remote Similarity	NPD292	Approved
0.6593	Remote Similarity	NPD294	Approved
0.6587	Remote Similarity	NPD8118	Discontinued
0.6585	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1359	Approved
0.6577	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1401	Approved
0.656	Remote Similarity	NPD3136	Phase 2
0.656	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4738	Phase 2
0.6545	Remote Similarity	NPD414	Discontinued
0.6538	Remote Similarity	NPD199	Approved
0.6538	Remote Similarity	NPD197	Approved
0.6535	Remote Similarity	NPD8265	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