NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	624.22
Volume:	613.023
LogP:	3.853
LogD:	1.444
LogS:	-3.789
# Rotatable Bonds:	10
TPSA:	193.33
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.118
Synthetic Accessibility Score:	5.062
Fsp3:	0.455
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.744
MDCK Permeability:	4.812514816876501e-06
Pgp-inhibitor:	0.64
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.832
20% Bioavailability (F20%):	0.295
30% Bioavailability (F30%):	0.783

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	77.34960174560547%
Volume Distribution (VD):	1.165
Pgp-substrate:	16.392351150512695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.38
CYP2C9-inhibitor:	0.463
CYP2C9-substrate:	0.523
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.303
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	5.877
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.958
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.814
Carcinogencity:	0.08
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC208060

Natural Product ID:	NPC208060
*Common Name:**	2-Benzyl-1H-Quinazolin-4-One
IUPAC Name:	2-benzyl-1H-quinazolin-4-one
Synonyms:
Standard InCHIKey:	ZDUVLDCZFKNYHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12N2O/c18-15-12-8-4-5-9-13(12)16-14(17-15)10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17,18)
SMILES:	c1ccc(cc1)Cc1nc2ccccc2c(n1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1604716
PubChem CID:	63121
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828480]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14552774]
NPO33632	Bacillus cereus 041381	Species	n.a.	n.a.	isolated from the Coastal mud	Baimajin, Danzhou, Hainan province of China	n.a.	PMID[21612927]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	leaf and stem	n.a.	n.a.	PMID[9584399]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28694	Sanguisorba tenuifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23819	Baccharis peruviana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23277	Lobophora papenfussii	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24585	Ocotea macropoda	Species	Lauraceae	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
MIC	1
Potency	5

Activity Type	# Activity
Individual Protein	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	8912.5	nM	PMID[526256]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[526256]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[526256]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[526256]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	10600.0	nM	PMID[526257]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[526256]

☑ 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 NPC208060 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	849
0.1-0.2	9574
0.2-0.3	8436
0.3-0.4	16058
0.4-0.5	4628
0.5-0.6	2480
0.6-0.7	609
0.7-0.8	50
0.8-0.85	2
0.85-0.9	2
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9679	High Similarity	NPC278874
0.9627	High Similarity	NPC477891
0.9627	High Similarity	NPC144114
0.9557	High Similarity	NPC105758
0.9557	High Similarity	NPC476688
0.9557	High Similarity	NPC476686
0.9423	High Similarity	NPC224632
0.913	High Similarity	NPC164664
0.8663	High Similarity	NPC254762
0.8613	High Similarity	NPC230805
0.8295	Intermediate Similarity	NPC472289
0.8113	Intermediate Similarity	NPC60553
0.7562	Intermediate Similarity	NPC130570
0.7544	Intermediate Similarity	NPC26850
0.75	Intermediate Similarity	NPC288445
0.7471	Intermediate Similarity	NPC97367
0.743	Intermediate Similarity	NPC288943
0.7411	Intermediate Similarity	NPC471603
0.7371	Intermediate Similarity	NPC159319
0.7368	Intermediate Similarity	NPC26872
0.7318	Intermediate Similarity	NPC474409
0.7314	Intermediate Similarity	NPC315214
0.7314	Intermediate Similarity	NPC47298
0.73	Intermediate Similarity	NPC62995
0.7293	Intermediate Similarity	NPC283152
0.7278	Intermediate Similarity	NPC161292
0.7277	Intermediate Similarity	NPC48317
0.7273	Intermediate Similarity	NPC32028
0.7247	Intermediate Similarity	NPC44161
0.7213	Intermediate Similarity	NPC478032
0.7119	Intermediate Similarity	NPC177404
0.7112	Intermediate Similarity	NPC314573
0.7111	Intermediate Similarity	NPC314940
0.7111	Intermediate Similarity	NPC473764
0.7111	Intermediate Similarity	NPC126481
0.711	Intermediate Similarity	NPC153769
0.7102	Intermediate Similarity	NPC84508
0.7097	Intermediate Similarity	NPC62069
0.7088	Intermediate Similarity	NPC303225
0.7086	Intermediate Similarity	NPC477889
0.7074	Intermediate Similarity	NPC66083
0.7069	Intermediate Similarity	NPC36168
0.7067	Intermediate Similarity	NPC2497
0.7065	Intermediate Similarity	NPC72980
0.7059	Intermediate Similarity	NPC42591
0.7043	Intermediate Similarity	NPC212535
0.7033	Intermediate Similarity	NPC471294
0.7033	Intermediate Similarity	NPC259545
0.7024	Intermediate Similarity	NPC280853
0.7022	Intermediate Similarity	NPC124542
0.7022	Intermediate Similarity	NPC59779
0.7022	Intermediate Similarity	NPC471177
0.7005	Intermediate Similarity	NPC190007
0.6982	Remote Similarity	NPC245657
0.6982	Remote Similarity	NPC285016
0.6973	Remote Similarity	NPC88363
0.6968	Remote Similarity	NPC94943
0.6964	Remote Similarity	NPC471596
0.6944	Remote Similarity	NPC471178
0.6943	Remote Similarity	NPC54102
0.6943	Remote Similarity	NPC162689
0.6936	Remote Similarity	NPC114209
0.6927	Remote Similarity	NPC324149
0.6907	Remote Similarity	NPC472193
0.6907	Remote Similarity	NPC242209
0.6905	Remote Similarity	NPC132631
0.6905	Remote Similarity	NPC103687
0.6902	Remote Similarity	NPC312872
0.6893	Remote Similarity	NPC141353
0.6891	Remote Similarity	NPC329541
0.6889	Remote Similarity	NPC118511
0.6882	Remote Similarity	NPC232340
0.6872	Remote Similarity	NPC120798
0.6872	Remote Similarity	NPC474188
0.686	Remote Similarity	NPC471598
0.6847	Remote Similarity	NPC472067
0.6847	Remote Similarity	NPC472031
0.6847	Remote Similarity	NPC472066
0.6842	Remote Similarity	NPC194040
0.6833	Remote Similarity	NPC79911
0.6816	Remote Similarity	NPC243850
0.6793	Remote Similarity	NPC252590
0.6778	Remote Similarity	NPC25899
0.6778	Remote Similarity	NPC131718
0.6778	Remote Similarity	NPC322644
0.6772	Remote Similarity	NPC133306
0.6766	Remote Similarity	NPC477113
0.6765	Remote Similarity	NPC471594
0.6754	Remote Similarity	NPC204385
0.674	Remote Similarity	NPC48192
0.6738	Remote Similarity	NPC219848
0.6738	Remote Similarity	NPC96890
0.6736	Remote Similarity	NPC144381
0.672	Remote Similarity	NPC206201
0.6719	Remote Similarity	NPC46580
0.6709	Remote Similarity	NPC148140
0.6703	Remote Similarity	NPC473057
0.6702	Remote Similarity	NPC256268
0.67	Remote Similarity	NPC477111
0.6699	Remote Similarity	NPC250178
0.6687	Remote Similarity	NPC122718
0.6684	Remote Similarity	NPC150048
0.6684	Remote Similarity	NPC128751
0.6684	Remote Similarity	NPC220765
0.6684	Remote Similarity	NPC246700
0.6684	Remote Similarity	NPC243058
0.6684	Remote Similarity	NPC203754
0.6682	Remote Similarity	NPC472068
0.6682	Remote Similarity	NPC220851
0.6667	Remote Similarity	NPC184437
0.6667	Remote Similarity	NPC237740
0.6667	Remote Similarity	NPC222592
0.6667	Remote Similarity	NPC99666
0.6667	Remote Similarity	NPC168486
0.6667	Remote Similarity	NPC30540
0.6667	Remote Similarity	NPC81561
0.6667	Remote Similarity	NPC53144
0.6667	Remote Similarity	NPC200836
0.6651	Remote Similarity	NPC116622
0.6649	Remote Similarity	NPC477888
0.6649	Remote Similarity	NPC469497
0.6649	Remote Similarity	NPC204717
0.6649	Remote Similarity	NPC106833
0.6649	Remote Similarity	NPC184964
0.6634	Remote Similarity	NPC475070
0.6634	Remote Similarity	NPC470500
0.6632	Remote Similarity	NPC314394
0.6631	Remote Similarity	NPC317054
0.6618	Remote Similarity	NPC18348
0.6616	Remote Similarity	NPC153042
0.6616	Remote Similarity	NPC77555
0.6616	Remote Similarity	NPC243834
0.6616	Remote Similarity	NPC70956
0.6615	Remote Similarity	NPC314002
0.6613	Remote Similarity	NPC158129
0.6612	Remote Similarity	NPC102423
0.6609	Remote Similarity	NPC470403
0.6609	Remote Similarity	NPC470404
0.6609	Remote Similarity	NPC470394
0.6602	Remote Similarity	NPC242923
0.66	Remote Similarity	NPC249040
0.6598	Remote Similarity	NPC183805
0.6597	Remote Similarity	NPC48938
0.6594	Remote Similarity	NPC63109
0.6584	Remote Similarity	NPC223427
0.6583	Remote Similarity	NPC192315
0.6582	Remote Similarity	NPC141915
0.6582	Remote Similarity	NPC280964
0.6582	Remote Similarity	NPC114335
0.658	Remote Similarity	NPC171171
0.658	Remote Similarity	NPC90415
0.6577	Remote Similarity	NPC171393
0.6577	Remote Similarity	NPC295452
0.6577	Remote Similarity	NPC39092
0.6562	Remote Similarity	NPC320394
0.6562	Remote Similarity	NPC203635
0.6556	Remote Similarity	NPC120070
0.6555	Remote Similarity	NPC477110
0.655	Remote Similarity	NPC476167
0.6548	Remote Similarity	NPC79293
0.6548	Remote Similarity	NPC230403
0.6548	Remote Similarity	NPC279401
0.6548	Remote Similarity	NPC476689
0.6548	Remote Similarity	NPC476685
0.6548	Remote Similarity	NPC476687
0.6546	Remote Similarity	NPC206186
0.6543	Remote Similarity	NPC95898
0.6543	Remote Similarity	NPC215519
0.6537	Remote Similarity	NPC470931
0.6535	Remote Similarity	NPC291535
0.6535	Remote Similarity	NPC211813
0.6535	Remote Similarity	NPC475085
0.6535	Remote Similarity	NPC475112
0.6534	Remote Similarity	NPC470395
0.6533	Remote Similarity	NPC208751
0.6527	Remote Similarity	NPC226662
0.6519	Remote Similarity	NPC248627
0.6515	Remote Similarity	NPC280638
0.6515	Remote Similarity	NPC276517
0.6514	Remote Similarity	NPC477890
0.6504	Remote Similarity	NPC9729
0.65	Remote Similarity	NPC306376
0.6495	Remote Similarity	NPC61350
0.6494	Remote Similarity	NPC284635
0.6492	Remote Similarity	NPC249662
0.6481	Remote Similarity	NPC187145
0.6477	Remote Similarity	NPC84478
0.6476	Remote Similarity	NPC183407
0.6476	Remote Similarity	NPC51854
0.6473	Remote Similarity	NPC309845
0.6473	Remote Similarity	NPC85273
0.6473	Remote Similarity	NPC5145
0.6468	Remote Similarity	NPC280714
0.6467	Remote Similarity	NPC278451
0.6465	Remote Similarity	NPC45850
0.6461	Remote Similarity	NPC257142
0.6459	Remote Similarity	NPC282247
0.6453	Remote Similarity	NPC135887
0.6453	Remote Similarity	NPC199277
0.645	Remote Similarity	NPC90229

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 NPC208060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	484
0.1-0.2	817
0.2-0.3	540
0.3-0.4	2018
0.4-0.5	2520
0.5-0.6	2076
0.6-0.7	647
0.7-0.8	42
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
0.865	High Similarity	NPD444	Approved
0.8613	High Similarity	NPD9714	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2410	Phase 2
0.8122	Intermediate Similarity	NPD6594	Discontinued
0.8033	Intermediate Similarity	NPD7419	Discontinued
0.8023	Intermediate Similarity	NPD3224	Phase 2
0.7978	Intermediate Similarity	NPD3261	Phase 1
0.788	Intermediate Similarity	NPD4673	Phase 2
0.7814	Intermediate Similarity	NPD5428	Discontinued
0.7789	Intermediate Similarity	NPD4403	Phase 3
0.7789	Intermediate Similarity	NPD4401	Phase 2
0.7619	Intermediate Similarity	NPD2882	Phase 1
0.7572	Intermediate Similarity	NPD5925	Phase 1
0.7542	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6158	Phase 2
0.7513	Intermediate Similarity	NPD3814	Phase 1
0.7512	Intermediate Similarity	NPD1954	Phase 1
0.7487	Intermediate Similarity	NPD6132	Phase 1
0.7432	Intermediate Similarity	NPD2762	Phase 2
0.7426	Intermediate Similarity	NPD3233	Phase 2
0.7426	Intermediate Similarity	NPD3234	Phase 3
0.7389	Intermediate Similarity	NPD6159	Phase 2
0.7333	Intermediate Similarity	NPD1197	Approved
0.7323	Intermediate Similarity	NPD2794	Discontinued
0.7314	Intermediate Similarity	NPD1684	Approved
0.7314	Intermediate Similarity	NPD1685	Approved
0.7296	Intermediate Similarity	NPD5529	Phase 1
0.7296	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1838	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6490	Phase 2
0.7277	Intermediate Similarity	NPD5885	Approved
0.7273	Intermediate Similarity	NPD1043	Phase 3
0.7263	Intermediate Similarity	NPD7935	Phase 2
0.7228	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4615	Phase 2
0.7192	Intermediate Similarity	NPD4312	Approved
0.7169	Intermediate Similarity	NPD852	Discontinued
0.7165	Intermediate Similarity	NPD6145	Phase 1
0.7143	Intermediate Similarity	NPD639	Discontinued
0.7136	Intermediate Similarity	NPD983	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7112	Discontinued
0.7117	Intermediate Similarity	NPD9187	Approved
0.7115	Intermediate Similarity	NPD6327	Phase 1
0.7115	Intermediate Similarity	NPD6326	Phase 2
0.711	Intermediate Similarity	NPD3262	Approved
0.7107	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1215	Discontinued
0.7095	Intermediate Similarity	NPD6794	Approved
0.7094	Intermediate Similarity	NPD7423	Phase 2
0.7085	Intermediate Similarity	NPD7409	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4358	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2757	Phase 2
0.7067	Intermediate Similarity	NPD1273	Discontinued
0.705	Intermediate Similarity	NPD3013	Phase 3
0.705	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3830	Phase 1
0.7044	Intermediate Similarity	NPD6957	Approved
0.7044	Intermediate Similarity	NPD6958	Approved
0.7041	Intermediate Similarity	NPD3765	Approved
0.7033	Intermediate Similarity	NPD5996	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1912	Approved
0.7031	Intermediate Similarity	NPD4998	Phase 3
0.7031	Intermediate Similarity	NPD4999	Phase 3
0.7031	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4950	Approved
0.7016	Intermediate Similarity	NPD1234	Discontinued
0.7014	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2524	Discontinued
0.7005	Intermediate Similarity	NPD4945	Discontinued
0.7005	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3439	Approved
0.6995	Remote Similarity	NPD6492	Phase 2
0.6995	Remote Similarity	NPD9690	Approved
0.6995	Remote Similarity	NPD5065	Approved
0.6995	Remote Similarity	NPD3799	Suspended
0.699	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4511	Phase 1
0.6983	Remote Similarity	NPD404	Discontinued
0.6963	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6711	Approved
0.6957	Remote Similarity	NPD5943	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3931	Approved
0.6954	Remote Similarity	NPD3928	Approved
0.6948	Remote Similarity	NPD4306	Phase 1
0.6946	Remote Similarity	NPD4457	Phase 2
0.6944	Remote Similarity	NPD925	Approved
0.6944	Remote Similarity	NPD926	Approved
0.6944	Remote Similarity	NPD3889	Approved
0.6944	Remote Similarity	NPD5905	Phase 1
0.6944	Remote Similarity	NPD509	Phase 3
0.6943	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6285	Phase 2
0.6931	Remote Similarity	NPD1468	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2591	Phase 2
0.6927	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7188	Phase 3
0.6912	Remote Similarity	NPD5413	Phase 2
0.6902	Remote Similarity	NPD7006	Approved
0.6901	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6605	Phase 3
0.6898	Remote Similarity	NPD4204	Approved
0.6898	Remote Similarity	NPD4203	Approved
0.6895	Remote Similarity	NPD2383	Phase 1
0.689	Remote Similarity	NPD947	Approved
0.6887	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4925	Approved
0.6885	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5425	Phase 1
0.6881	Remote Similarity	NPD8321	Discontinued
0.6878	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD112	Approved
0.6872	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD9705	Discontinued
0.686	Remote Similarity	NPD3813	Approved
0.6854	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4996	Approved
0.6854	Remote Similarity	NPD4995	Approved
0.6854	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5804	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD1313	Approved
0.6848	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6458	Discontinued
0.6842	Remote Similarity	NPD6721	Phase 1
0.6842	Remote Similarity	NPD706	Phase 1
0.6842	Remote Similarity	NPD7758	Approved
0.6842	Remote Similarity	NPD1592	Phase 3
0.6842	Remote Similarity	NPD7757	Approved
0.6839	Remote Similarity	NPD2127	Suspended
0.6839	Remote Similarity	NPD7722	Suspended
0.6837	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6469	Phase 3
0.6832	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6202	Discontinued
0.6813	Remote Similarity	NPD425	Approved
0.6813	Remote Similarity	NPD424	Approved
0.6813	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5153	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5873	Phase 3
0.6804	Remote Similarity	NPD5874	Phase 3
0.6804	Remote Similarity	NPD9695	Approved
0.6802	Remote Similarity	NPD5828	Phase 2
0.6794	Remote Similarity	NPD6589	Phase 1
0.6794	Remote Similarity	NPD7726	Phase 1
0.6777	Remote Similarity	NPD4932	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7067	Approved
0.6773	Remote Similarity	NPD7068	Approved
0.6772	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5493	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6251	Discontinued
0.6766	Remote Similarity	NPD6150	Discontinued
0.6758	Remote Similarity	NPD3872	Phase 3
0.6757	Remote Similarity	NPD1599	Approved
0.6754	Remote Similarity	NPD3315	Phase 3
0.6754	Remote Similarity	NPD2917	Approved
0.6753	Remote Similarity	NPD3404	Approved
0.6751	Remote Similarity	NPD2727	Phase 2
0.6746	Remote Similarity	NPD5827	Discontinued
0.6745	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7051	Phase 3
0.6744	Remote Similarity	NPD1572	Phase 2
0.6743	Remote Similarity	NPD6750	Phase 2
0.6742	Remote Similarity	NPD3962	Phase 2
0.6742	Remote Similarity	NPD3959	Phase 2
0.6738	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3976	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3330	Phase 1
0.673	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5833	Phase 1
0.6726	Remote Similarity	NPD4438	Approved
0.672	Remote Similarity	NPD1570	Approved
0.6719	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD38	Approved
0.6718	Remote Similarity	NPD5176	Approved
0.6718	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7103	Approved
0.6715	Remote Similarity	NPD6643	Discontinued
0.6714	Remote Similarity	NPD2714	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1251	Discontinued
0.6705	Remote Similarity	NPD3525	Discontinued
0.6704	Remote Similarity	NPD2927	Phase 3
0.6703	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1842	Approved
0.67	Remote Similarity	NPD4612	Discontinued
0.6698	Remote Similarity	NPD8004	Discontinued
0.6685	Remote Similarity	NPD2781	Approved
0.6684	Remote Similarity	NPD2751	Phase 1
0.6684	Remote Similarity	NPD2380	Approved
0.6684	Remote Similarity	NPD6590	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