NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.13
Volume:	263.212
LogP:	2.214
LogD:	2.797
LogS:	-2.775
# Rotatable Bonds:	6
TPSA:	41.13
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.847
Synthetic Accessibility Score:	1.346
Fsp3:	0.133
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:	-4.642
MDCK Permeability:	2.860355016309768e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.426
Human Intestinal Absorption (HIA):	0.506
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.618
Plasma Protein Binding (PPB):	94.4006118774414%
Volume Distribution (VD):	2.125
Pgp-substrate:	7.191380023956299%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.707
CYP2C9-inhibitor:	0.424
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.164
CYP2D6-substrate:	0.859
CYP3A4-inhibitor:	0.328
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	7.767
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.271
Human Hepatotoxicity (H-HT):	0.055
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.513
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC108339

Natural Product ID:	NPC108339
*Common Name:**	1,3-Dibenzylurea
IUPAC Name:	1,3-dibenzylurea
Synonyms:	1,3-Dibenzyl Urea
Standard InCHIKey:	KATOLVAXCGIBLO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16N2O/c18-15(16-11-13-7-3-1-4-8-13)17-12-14-9-5-2-6-10-14/h1-10H,11-12H2,(H2,16,17,18)
SMILES:	OC(=NCc1ccccc1)NCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504463
PubChem CID:	72889
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted 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
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)83306-8]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932128]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24024688]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798960]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11021	Moringa oleifera	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2501	Trifolium strepens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5937	Garrya laurifolia	Species	Garryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2703	Petteria ramentacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4858	Helipterum gnaphaloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5021	Podospora curvicolla	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO823	Senecio cathcartensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8703	Monopteryx uaucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5536	Papaver persicum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3905	Medinilla magnifica	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4221	Fusarium sacchari	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6187	Sequoia sempervirens	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7963	Excoecaria acerifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO681	Mesua ferrea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4410	Laggera alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8339	Lithothamnion corallioides	Species	Hapalidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3302	Fusarium avenaceum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7266	Goupia glabra	Species	Goupiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1585	Onobrychis bobrovii	Species	Fabaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT468	Individual Protein	Vanilloid receptor	Rattus norvegicus	IC50	=	10.0	nM	PMID[541854]

☑ 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 NPC108339 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	455
0.1-0.2	7288
0.2-0.3	13787
0.3-0.4	15432
0.4-0.5	4723
0.5-0.6	861
0.6-0.7	123
0.7-0.8	23
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9239	High Similarity	NPC471320
0.9239	High Similarity	NPC471319
0.8242	Intermediate Similarity	NPC169016
0.7978	Intermediate Similarity	NPC12857
0.7857	Intermediate Similarity	NPC469330
0.7677	Intermediate Similarity	NPC322040
0.7556	Intermediate Similarity	NPC271642
0.7553	Intermediate Similarity	NPC119677
0.75	Intermediate Similarity	NPC258046
0.75	Intermediate Similarity	NPC7067
0.7444	Intermediate Similarity	NPC98976
0.7426	Intermediate Similarity	NPC329430
0.7386	Intermediate Similarity	NPC219246
0.7363	Intermediate Similarity	NPC139658
0.732	Intermediate Similarity	NPC203076
0.7264	Intermediate Similarity	NPC474430
0.7245	Intermediate Similarity	NPC473031
0.7179	Intermediate Similarity	NPC273830
0.7143	Intermediate Similarity	NPC299134
0.71	Intermediate Similarity	NPC470877
0.7097	Intermediate Similarity	NPC325662
0.7097	Intermediate Similarity	NPC98269
0.703	Intermediate Similarity	NPC74936
0.703	Intermediate Similarity	NPC471307
0.703	Intermediate Similarity	NPC209764
0.703	Intermediate Similarity	NPC159178
0.703	Intermediate Similarity	NPC141139
0.703	Intermediate Similarity	NPC121872
0.703	Intermediate Similarity	NPC78041
0.7019	Intermediate Similarity	NPC317400
0.701	Intermediate Similarity	NPC104070
0.7	Intermediate Similarity	NPC229235
0.6961	Remote Similarity	NPC470926
0.6939	Remote Similarity	NPC133162
0.69	Remote Similarity	NPC471638
0.6885	Remote Similarity	NPC477937
0.6863	Remote Similarity	NPC172128
0.6855	Remote Similarity	NPC471321
0.6855	Remote Similarity	NPC471306
0.6848	Remote Similarity	NPC244738
0.6827	Remote Similarity	NPC471309
0.6792	Remote Similarity	NPC311242
0.6786	Remote Similarity	NPC164802
0.6774	Remote Similarity	NPC113000
0.6774	Remote Similarity	NPC112609
0.6774	Remote Similarity	NPC122327
0.6727	Remote Similarity	NPC469974
0.6702	Remote Similarity	NPC276699
0.6667	Remote Similarity	NPC12429
0.6667	Remote Similarity	NPC326232
0.6635	Remote Similarity	NPC245259
0.6635	Remote Similarity	NPC226438
0.6604	Remote Similarity	NPC161972
0.6604	Remote Similarity	NPC303045
0.6569	Remote Similarity	NPC17497
0.6569	Remote Similarity	NPC305602
0.6566	Remote Similarity	NPC14326
0.6562	Remote Similarity	NPC290638
0.6545	Remote Similarity	NPC291610
0.6538	Remote Similarity	NPC78154
0.6525	Remote Similarity	NPC101139
0.6525	Remote Similarity	NPC288232
0.6522	Remote Similarity	NPC319579
0.6504	Remote Similarity	NPC328683
0.6504	Remote Similarity	NPC283130
0.65	Remote Similarity	NPC474088
0.6481	Remote Similarity	NPC33168
0.646	Remote Similarity	NPC45033
0.6434	Remote Similarity	NPC471322
0.6429	Remote Similarity	NPC275467
0.6396	Remote Similarity	NPC239854
0.6396	Remote Similarity	NPC329375
0.6396	Remote Similarity	NPC327226
0.6389	Remote Similarity	NPC25565
0.6381	Remote Similarity	NPC191444
0.6381	Remote Similarity	NPC316108
0.6373	Remote Similarity	NPC3210
0.6364	Remote Similarity	NPC132636
0.6357	Remote Similarity	NPC194857
0.6357	Remote Similarity	NPC32858
0.6356	Remote Similarity	NPC314141
0.6346	Remote Similarity	NPC262393
0.6341	Remote Similarity	NPC71684
0.6339	Remote Similarity	NPC471310
0.6339	Remote Similarity	NPC202613
0.6339	Remote Similarity	NPC164859
0.6339	Remote Similarity	NPC471317
0.633	Remote Similarity	NPC473501
0.633	Remote Similarity	NPC475439
0.633	Remote Similarity	NPC472258
0.6325	Remote Similarity	NPC275410
0.6316	Remote Similarity	NPC327481
0.6316	Remote Similarity	NPC473498
0.63	Remote Similarity	NPC231986
0.6296	Remote Similarity	NPC58674
0.6286	Remote Similarity	NPC176858
0.6283	Remote Similarity	NPC226778
0.6283	Remote Similarity	NPC150254
0.6283	Remote Similarity	NPC304761
0.6283	Remote Similarity	NPC147000
0.6262	Remote Similarity	NPC473661
0.626	Remote Similarity	NPC267237
0.625	Remote Similarity	NPC60408
0.625	Remote Similarity	NPC114327
0.625	Remote Similarity	NPC36357
0.6231	Remote Similarity	NPC476685
0.6231	Remote Similarity	NPC476689
0.6231	Remote Similarity	NPC476687
0.6228	Remote Similarity	NPC474695
0.6228	Remote Similarity	NPC67043
0.6228	Remote Similarity	NPC143516
0.6228	Remote Similarity	NPC211551
0.6222	Remote Similarity	NPC22786
0.622	Remote Similarity	NPC318965
0.6207	Remote Similarity	NPC77294
0.6207	Remote Similarity	NPC302790
0.6202	Remote Similarity	NPC226662
0.62	Remote Similarity	NPC192623
0.6174	Remote Similarity	NPC130898
0.6174	Remote Similarity	NPC474804
0.6174	Remote Similarity	NPC474973
0.6161	Remote Similarity	NPC29601
0.6161	Remote Similarity	NPC469457
0.6148	Remote Similarity	NPC313449
0.6147	Remote Similarity	NPC20142
0.6147	Remote Similarity	NPC215351
0.6142	Remote Similarity	NPC52764
0.6111	Remote Similarity	NPC246588
0.6111	Remote Similarity	NPC108800
0.6103	Remote Similarity	NPC2823
0.6098	Remote Similarity	NPC320656
0.609	Remote Similarity	NPC314835
0.6087	Remote Similarity	NPC314114
0.6087	Remote Similarity	NPC473418
0.6083	Remote Similarity	NPC187036
0.608	Remote Similarity	NPC475915
0.6074	Remote Similarity	NPC214988
0.6068	Remote Similarity	NPC96224
0.6068	Remote Similarity	NPC473676
0.6068	Remote Similarity	NPC24101
0.6066	Remote Similarity	NPC470544
0.6066	Remote Similarity	NPC125416
0.6058	Remote Similarity	NPC229477
0.605	Remote Similarity	NPC329011
0.6044	Remote Similarity	NPC200745
0.6042	Remote Similarity	NPC125144
0.6042	Remote Similarity	NPC121708
0.604	Remote Similarity	NPC475289
0.604	Remote Similarity	NPC309279
0.604	Remote Similarity	NPC475573
0.6038	Remote Similarity	NPC325441
0.6036	Remote Similarity	NPC293628
0.6036	Remote Similarity	NPC10781
0.6036	Remote Similarity	NPC122493
0.6034	Remote Similarity	NPC471447
0.6019	Remote Similarity	NPC134825
0.6018	Remote Similarity	NPC228400
0.6018	Remote Similarity	NPC214200
0.6016	Remote Similarity	NPC470545
0.6014	Remote Similarity	NPC469975
0.6	Remote Similarity	NPC474584
0.6	Remote Similarity	NPC256452
0.6	Remote Similarity	NPC194390
0.6	Remote Similarity	NPC88267
0.6	Remote Similarity	NPC113326
0.6	Remote Similarity	NPC311753
0.6	Remote Similarity	NPC224610
0.5985	Remote Similarity	NPC168861
0.5983	Remote Similarity	NPC79618
0.5983	Remote Similarity	NPC434
0.5982	Remote Similarity	NPC303611
0.5982	Remote Similarity	NPC108606
0.5982	Remote Similarity	NPC226096
0.5982	Remote Similarity	NPC290515
0.5982	Remote Similarity	NPC164514
0.598	Remote Similarity	NPC307456
0.5978	Remote Similarity	NPC113670
0.5969	Remote Similarity	NPC252794
0.5968	Remote Similarity	NPC470546
0.5968	Remote Similarity	NPC220698
0.595	Remote Similarity	NPC296163
0.5948	Remote Similarity	NPC476198
0.5943	Remote Similarity	NPC262295
0.5943	Remote Similarity	NPC198747
0.594	Remote Similarity	NPC101165
0.5935	Remote Similarity	NPC313673
0.5932	Remote Similarity	NPC153690
0.5929	Remote Similarity	NPC12730
0.5929	Remote Similarity	NPC125732
0.5926	Remote Similarity	NPC258627
0.5923	Remote Similarity	NPC145754
0.5923	Remote Similarity	NPC476950
0.5917	Remote Similarity	NPC475013
0.5914	Remote Similarity	NPC291066
0.5909	Remote Similarity	NPC291070
0.5909	Remote Similarity	NPC149436
0.5909	Remote Similarity	NPC474974
0.5909	Remote Similarity	NPC246757
0.5902	Remote Similarity	NPC205652
0.5902	Remote Similarity	NPC33742

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 NPC108339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	705
0.2-0.3	1253
0.3-0.4	2533
0.4-0.5	3099
0.5-0.6	1064
0.6-0.7	252
0.7-0.8	33
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8587	High Similarity	NPD9	Approved
0.8587	High Similarity	NPD297	Approved
0.8191	Intermediate Similarity	NPD9349	Approved
0.8191	Intermediate Similarity	NPD9350	Approved
0.8191	Intermediate Similarity	NPD9351	Phase 3
0.8191	Intermediate Similarity	NPD9348	Approved
0.7879	Intermediate Similarity	NPD2507	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1813	Discontinued
0.7684	Intermediate Similarity	NPD304	Approved
0.7684	Intermediate Similarity	NPD305	Approved
0.7677	Intermediate Similarity	NPD243	Approved
0.7677	Intermediate Similarity	NPD8	Approved
0.7544	Intermediate Similarity	NPD6892	Discontinued
0.75	Intermediate Similarity	NPD199	Approved
0.75	Intermediate Similarity	NPD197	Approved
0.7474	Intermediate Similarity	NPD2539	Approved
0.7474	Intermediate Similarity	NPD2538	Approved
0.7473	Intermediate Similarity	NPD603	Approved
0.7453	Intermediate Similarity	NPD414	Discontinued
0.7429	Intermediate Similarity	NPD5655	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5103	Approved
0.7429	Intermediate Similarity	NPD1396	Approved
0.7426	Intermediate Similarity	NPD5554	Approved
0.7396	Intermediate Similarity	NPD9505	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6561	Approved
0.7387	Intermediate Similarity	NPD6562	Approved
0.7358	Intermediate Similarity	NPD1026	Approved
0.7358	Intermediate Similarity	NPD1028	Approved
0.7353	Intermediate Similarity	NPD2005	Discontinued
0.7345	Intermediate Similarity	NPD2463	Approved
0.7345	Intermediate Similarity	NPD6660	Discontinued
0.7345	Intermediate Similarity	NPD2464	Approved
0.7345	Intermediate Similarity	NPD2467	Approved
0.7311	Intermediate Similarity	NPD6900	Discontinued
0.73	Intermediate Similarity	NPD7160	Approved
0.729	Intermediate Similarity	NPD1268	Approved
0.729	Intermediate Similarity	NPD1269	Approved
0.7234	Intermediate Similarity	NPD5371	Approved
0.7234	Intermediate Similarity	NPD5372	Approved
0.7204	Intermediate Similarity	NPD296	Approved
0.7204	Intermediate Similarity	NPD293	Approved
0.7204	Intermediate Similarity	NPD295	Approved
0.7182	Intermediate Similarity	NPD1539	Approved
0.7129	Intermediate Similarity	NPD3000	Approved
0.7129	Intermediate Similarity	NPD2998	Approved
0.7129	Intermediate Similarity	NPD2997	Approved
0.7128	Intermediate Similarity	NPD590	Approved
0.7128	Intermediate Similarity	NPD507	Approved
0.7128	Intermediate Similarity	NPD508	Approved
0.7128	Intermediate Similarity	NPD589	Approved
0.7113	Intermediate Similarity	NPD785	Approved
0.71	Intermediate Similarity	NPD5656	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4147	Approved
0.7097	Intermediate Similarity	NPD4144	Approved
0.7094	Intermediate Similarity	NPD5961	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1656	Phase 2
0.7071	Intermediate Similarity	NPD4145	Approved
0.7071	Intermediate Similarity	NPD3428	Approved
0.7071	Intermediate Similarity	NPD2002	Discontinued
0.7071	Intermediate Similarity	NPD4146	Approved
0.7071	Intermediate Similarity	NPD187	Approved
0.7071	Intermediate Similarity	NPD3426	Approved
0.7059	Intermediate Similarity	NPD1814	Approved
0.7059	Intermediate Similarity	NPD1812	Approved
0.7037	Intermediate Similarity	NPD3407	Phase 3
0.703	Intermediate Similarity	NPD5915	Approved
0.7027	Intermediate Similarity	NPD1107	Approved
0.7027	Intermediate Similarity	NPD1108	Approved
0.7025	Intermediate Similarity	NPD3606	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD838	Approved
0.7018	Intermediate Similarity	NPD7062	Discontinued
0.701	Intermediate Similarity	NPD830	Approved
0.701	Intermediate Similarity	NPD831	Approved
0.7009	Intermediate Similarity	NPD1540	Approved
0.699	Remote Similarity	NPD6549	Approved
0.699	Remote Similarity	NPD6548	Approved
0.699	Remote Similarity	NPD1080	Approved
0.6981	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD787	Suspended
0.6975	Remote Similarity	NPD4323	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4543	Discontinued
0.6952	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1542	Approved
0.6939	Remote Similarity	NPD3427	Approved
0.6939	Remote Similarity	NPD3429	Approved
0.6935	Remote Similarity	NPD4857	Phase 1
0.6923	Remote Similarity	NPD1216	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD1916	Discontinued
0.6893	Remote Similarity	NPD4407	Approved
0.6893	Remote Similarity	NPD4405	Approved
0.6893	Remote Similarity	NPD6690	Approved
0.6893	Remote Similarity	NPD4408	Approved
0.6881	Remote Similarity	NPD4936	Approved
0.6881	Remote Similarity	NPD4937	Approved
0.6852	Remote Similarity	NPD4119	Approved
0.6848	Remote Similarity	NPD9728	Phase 1
0.6847	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD480	Approved
0.6842	Remote Similarity	NPD7121	Approved
0.6833	Remote Similarity	NPD2131	Approved
0.6827	Remote Similarity	NPD837	Approved
0.6827	Remote Similarity	NPD736	Approved
0.6827	Remote Similarity	NPD2878	Approved
0.6827	Remote Similarity	NPD735	Approved
0.6827	Remote Similarity	NPD4545	Approved
0.6827	Remote Similarity	NPD4542	Approved
0.6818	Remote Similarity	NPD564	Approved
0.6818	Remote Similarity	NPD563	Approved
0.6804	Remote Similarity	NPD4026	Approved
0.6804	Remote Similarity	NPD3035	Approved
0.6804	Remote Similarity	NPD4027	Approved
0.68	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD477	Phase 1
0.6783	Remote Similarity	NPD2665	Clinical (unspecified phase)
0.678	Remote Similarity	NPD483	Approved
0.6774	Remote Similarity	NPD80	Approved
0.6774	Remote Similarity	NPD9591	Approved
0.6774	Remote Similarity	NPD9593	Approved
0.6774	Remote Similarity	NPD9588	Approved
0.6774	Remote Similarity	NPD9594	Approved
0.6774	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9589	Approved
0.6774	Remote Similarity	NPD9592	Approved
0.6774	Remote Similarity	NPD9590	Approved
0.6768	Remote Similarity	NPD9395	Approved
0.6768	Remote Similarity	NPD5178	Approved
0.6754	Remote Similarity	NPD753	Approved
0.6752	Remote Similarity	NPD5162	Approved
0.6748	Remote Similarity	NPD1836	Discontinued
0.6735	Remote Similarity	NPD4169	Approved
0.6735	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4170	Approved
0.6733	Remote Similarity	NPD782	Approved
0.6733	Remote Similarity	NPD780	Approved
0.6733	Remote Similarity	NPD783	Approved
0.6733	Remote Similarity	NPD781	Approved
0.6729	Remote Similarity	NPD6499	Approved
0.6729	Remote Similarity	NPD6498	Approved
0.6729	Remote Similarity	NPD1724	Approved
0.6729	Remote Similarity	NPD4117	Approved
0.6727	Remote Similarity	NPD488	Approved
0.6727	Remote Similarity	NPD489	Approved
0.6726	Remote Similarity	NPD7120	Approved
0.6723	Remote Similarity	NPD1479	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1922	Discontinued
0.6701	Remote Similarity	NPD1617	Discontinued
0.67	Remote Similarity	NPD5916	Discontinued
0.6698	Remote Similarity	NPD2895	Discontinued
0.6698	Remote Similarity	NPD157	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD2483	Discontinued
0.6697	Remote Similarity	NPD1419	Approved
0.6697	Remote Similarity	NPD1417	Approved
0.6696	Remote Similarity	NPD2207	Approved
0.6696	Remote Similarity	NPD2206	Approved
0.6667	Remote Similarity	NPD587	Approved
0.6667	Remote Similarity	NPD5675	Discontinued
0.6667	Remote Similarity	NPD588	Approved
0.6667	Remote Similarity	NPD3980	Approved
0.6667	Remote Similarity	NPD7342	Discontinued
0.6667	Remote Similarity	NPD7508	Discontinued
0.6667	Remote Similarity	NPD1406	Approved
0.6667	Remote Similarity	NPD2001	Discontinued
0.6667	Remote Similarity	NPD9397	Approved
0.6667	Remote Similarity	NPD3982	Approved
0.6667	Remote Similarity	NPD9393	Approved
0.6667	Remote Similarity	NPD5717	Approved
0.6667	Remote Similarity	NPD4635	Approved
0.6667	Remote Similarity	NPD3345	Approved
0.664	Remote Similarity	NPD7582	Discontinued
0.6639	Remote Similarity	NPD5511	Discontinued
0.6639	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5598	Approved
0.6636	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5597	Approved
0.6636	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4651	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3001	Approved
0.6609	Remote Similarity	NPD2999	Approved
0.6598	Remote Similarity	NPD1052	Approved
0.6598	Remote Similarity	NPD1053	Approved
0.6598	Remote Similarity	NPD1051	Approved
0.6589	Remote Similarity	NPD3908	Approved
0.6587	Remote Similarity	NPD3424	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5516	Phase 2
0.6583	Remote Similarity	NPD5517	Phase 2
0.6581	Remote Similarity	NPD5631	Phase 3
0.6581	Remote Similarity	NPD4674	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD9538	Approved
0.6557	Remote Similarity	NPD1948	Approved
0.6552	Remote Similarity	NPD2810	Discontinued
0.6545	Remote Similarity	NPD5716	Approved
0.6545	Remote Similarity	NPD707	Approved
0.6531	Remote Similarity	NPD3903	Approved
0.6531	Remote Similarity	NPD3979	Approved
0.6531	Remote Similarity	NPD3904	Approved
0.6531	Remote Similarity	NPD3981	Approved
0.6531	Remote Similarity	NPD260	Discontinued
0.6529	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3156	Discontinued

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