NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	162.04
Volume:	156.203
LogP:	0.536
LogD:	0.906
LogS:	-2.808
# Rotatable Bonds:	0
TPSA:	65.72
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.581
Synthetic Accessibility Score:	1.874
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.239
MDCK Permeability:	2.3990442059584893e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	21.997535705566406%
Volume Distribution (VD):	0.558
Pgp-substrate:	48.68230438232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.522
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	7.728
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.562
Carcinogencity:	0.4
Eye Corrosion:	0.005
Eye Irritation:	0.956
Respiratory Toxicity:	0.148

Download Data

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

Natural Product: NPC224632

Natural Product ID:	NPC224632
*Common Name:**	Benzoylenurea
IUPAC Name:	1H-quinazoline-2,4-dione
Synonyms:	Quinazoline-2,4-Diol
Standard InCHIKey:	SDQJTWBNWQABLE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H6N2O2/c11-7-5-3-1-2-4-6(5)9-8(12)10-7/h1-4H,(H2,9,10,11,12)
SMILES:	Oc1nc2ccccc2c(n1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL421646
PubChem CID:	64048
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
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32004936]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9069	Persicaria tinctoria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4554	Isatis tinctoria	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9069	Persicaria tinctoria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9069	Persicaria tinctoria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4554	Isatis tinctoria	Species	Brassicaceae	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
Ki	4
Others	6
Potency	5

Activity Type	# Activity
Individual Protein	14
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2562	Individual Protein	Poly [ADP-ribose] polymerase-1	Homo sapiens	IC50	=	8100.0	nM	PMID[557368]
NPT5279	Individual Protein	Phosphodiesterase 7A	Homo sapiens	Inhibition	=	8.4	%	PMID[557369]
NPT5104	Individual Protein	Phosphodiesterase 3A	Homo sapiens	Inhibition	=	59.0	%	PMID[557369]
NPT4735	Individual Protein	Phosphodiesterase 4B	Homo sapiens	Inhibition	=	1.7	%	PMID[557369]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[557370]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[557370]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1636.0	nM	PMID[557370]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	4.5	nM	PMID[557370]
NPT2818	Individual Protein	Dihydrofolate reductase	Homo sapiens	log(1/C)	=	3.89	n.a.	PMID[557371]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	500000.0	nM	PMID[557372]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[557370]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8650.0	nM	PMID[557372]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	13700.0	nM	PMID[557372]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	500000.0	nM	PMID[557372]
NPT27633	SINGLE PROTEIN	Dihydrofolate reductase	Rattus norvegicus	Log 1/C	=	3.89	n.a.	PMID[557366]
NPT27633	SINGLE PROTEIN	Dihydrofolate reductase	Rattus norvegicus	Log 1/C	=	3.89	n.a.	PMID[557367]

☑ 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 NPC224632 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	774
0.1-0.2	9523
0.2-0.3	8521
0.3-0.4	15868
0.4-0.5	4902
0.5-0.6	2515
0.6-0.7	542
0.7-0.8	39
0.8-0.85	3
0.85-0.9	1
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9608	High Similarity	NPC278874
0.9545	High Similarity	NPC164664
0.9484	High Similarity	NPC476688
0.9484	High Similarity	NPC476686
0.9484	High Similarity	NPC105758
0.9423	High Similarity	NPC208060
0.9193	High Similarity	NPC477891
0.9193	High Similarity	NPC144114
0.8639	High Similarity	NPC230805
0.8471	Intermediate Similarity	NPC254762
0.8314	Intermediate Similarity	NPC472289
0.8247	Intermediate Similarity	NPC60553
0.7429	Intermediate Similarity	NPC288943
0.7386	Intermediate Similarity	NPC283152
0.7378	Intermediate Similarity	NPC161292
0.7365	Intermediate Similarity	NPC26872
0.7341	Intermediate Similarity	NPC44161
0.7289	Intermediate Similarity	NPC288445
0.7273	Intermediate Similarity	NPC303225
0.7267	Intermediate Similarity	NPC97367
0.7235	Intermediate Similarity	NPC26850
0.7222	Intermediate Similarity	NPC280853
0.7214	Intermediate Similarity	NPC130570
0.7209	Intermediate Similarity	NPC315214
0.7209	Intermediate Similarity	NPC47298
0.7209	Intermediate Similarity	NPC177404
0.7202	Intermediate Similarity	NPC153769
0.72	Intermediate Similarity	NPC314940
0.72	Intermediate Similarity	NPC473764
0.7182	Intermediate Similarity	NPC62069
0.7178	Intermediate Similarity	NPC245657
0.7178	Intermediate Similarity	NPC285016
0.7168	Intermediate Similarity	NPC159319
0.7168	Intermediate Similarity	NPC32028
0.716	Intermediate Similarity	NPC471596
0.7143	Intermediate Similarity	NPC42591
0.7119	Intermediate Similarity	NPC474409
0.7102	Intermediate Similarity	NPC126481
0.7093	Intermediate Similarity	NPC84508
0.7065	Intermediate Similarity	NPC66083
0.7056	Intermediate Similarity	NPC72980
0.7048	Intermediate Similarity	NPC471598
0.7035	Intermediate Similarity	NPC62995
0.7017	Intermediate Similarity	NPC478032
0.6977	Remote Similarity	NPC477889
0.697	Remote Similarity	NPC471603
0.6966	Remote Similarity	NPC252590
0.6954	Remote Similarity	NPC322644
0.6933	Remote Similarity	NPC248627
0.6932	Remote Similarity	NPC471178
0.6931	Remote Similarity	NPC48317
0.6927	Remote Similarity	NPC471294
0.6927	Remote Similarity	NPC259545
0.6919	Remote Similarity	NPC194040
0.6919	Remote Similarity	NPC314573
0.6914	Remote Similarity	NPC59779
0.6914	Remote Similarity	NPC124542
0.6914	Remote Similarity	NPC471177
0.6898	Remote Similarity	NPC144381
0.6895	Remote Similarity	NPC242209
0.6879	Remote Similarity	NPC141353
0.6875	Remote Similarity	NPC118511
0.686	Remote Similarity	NPC36168
0.6857	Remote Similarity	NPC25899
0.6848	Remote Similarity	NPC212535
0.6848	Remote Similarity	NPC471594
0.6818	Remote Similarity	NPC48192
0.6813	Remote Similarity	NPC96890
0.6811	Remote Similarity	NPC190007
0.6791	Remote Similarity	NPC46580
0.678	Remote Similarity	NPC473057
0.6776	Remote Similarity	NPC232340
0.6776	Remote Similarity	NPC88363
0.6774	Remote Similarity	NPC94943
0.6761	Remote Similarity	NPC131718
0.6739	Remote Similarity	NPC168486
0.6739	Remote Similarity	NPC222592
0.6731	Remote Similarity	NPC2497
0.6723	Remote Similarity	NPC79911
0.6721	Remote Similarity	NPC184964
0.6719	Remote Similarity	NPC472193
0.6703	Remote Similarity	NPC312872
0.6702	Remote Similarity	NPC329541
0.6688	Remote Similarity	NPC148140
0.6686	Remote Similarity	NPC470403
0.6686	Remote Similarity	NPC314440
0.6686	Remote Similarity	NPC118135
0.6686	Remote Similarity	NPC470404
0.6686	Remote Similarity	NPC470394
0.6685	Remote Similarity	NPC158129
0.6684	Remote Similarity	NPC314002
0.6684	Remote Similarity	NPC474188
0.6667	Remote Similarity	NPC133306
0.6667	Remote Similarity	NPC220765
0.6667	Remote Similarity	NPC120798
0.6651	Remote Similarity	NPC103687
0.6651	Remote Similarity	NPC132631
0.6649	Remote Similarity	NPC249662
0.6649	Remote Similarity	NPC324149
0.6645	Remote Similarity	NPC81561
0.6631	Remote Similarity	NPC320394
0.6631	Remote Similarity	NPC204717
0.663	Remote Similarity	NPC219848
0.6626	Remote Similarity	NPC476685
0.6626	Remote Similarity	NPC476689
0.6626	Remote Similarity	NPC476687
0.6615	Remote Similarity	NPC279401
0.6615	Remote Similarity	NPC230403
0.6615	Remote Similarity	NPC79293
0.6613	Remote Similarity	NPC314394
0.6608	Remote Similarity	NPC470395
0.6606	Remote Similarity	NPC472067
0.6606	Remote Similarity	NPC472066
0.6606	Remote Similarity	NPC472031
0.6603	Remote Similarity	NPC54102
0.6603	Remote Similarity	NPC162689
0.6602	Remote Similarity	NPC250178
0.66	Remote Similarity	NPC18348
0.6598	Remote Similarity	NPC90229
0.6595	Remote Similarity	NPC42979
0.6595	Remote Similarity	NPC256268
0.6592	Remote Similarity	NPC102423
0.6591	Remote Similarity	NPC472068
0.6582	Remote Similarity	NPC249040
0.658	Remote Similarity	NPC276517
0.6579	Remote Similarity	NPC183805
0.6576	Remote Similarity	NPC203754
0.6576	Remote Similarity	NPC224764
0.6576	Remote Similarity	NPC150048
0.6566	Remote Similarity	NPC53144
0.6566	Remote Similarity	NPC200836
0.6564	Remote Similarity	NPC306376
0.6562	Remote Similarity	NPC99666
0.6561	Remote Similarity	NPC204385
0.6561	Remote Similarity	NPC171171
0.656	Remote Similarity	NPC295452
0.656	Remote Similarity	NPC171393
0.655	Remote Similarity	NPC243850
0.6545	Remote Similarity	NPC184437
0.6538	Remote Similarity	NPC477888
0.6535	Remote Similarity	NPC309845
0.6532	Remote Similarity	NPC257142
0.6532	Remote Similarity	NPC114209
0.6531	Remote Similarity	NPC280714
0.6524	Remote Similarity	NPC206201
0.6519	Remote Similarity	NPC215519
0.6517	Remote Similarity	NPC477111
0.6513	Remote Similarity	NPC70956
0.6513	Remote Similarity	NPC208751
0.6513	Remote Similarity	NPC243834
0.6513	Remote Similarity	NPC77555
0.6513	Remote Similarity	NPC153042
0.6503	Remote Similarity	NPC226662
0.65	Remote Similarity	NPC477113
0.65	Remote Similarity	NPC476118
0.6498	Remote Similarity	NPC30540
0.6495	Remote Similarity	NPC326634
0.6492	Remote Similarity	NPC246700
0.6492	Remote Similarity	NPC128751
0.6489	Remote Similarity	NPC243058
0.6489	Remote Similarity	NPC48938
0.6488	Remote Similarity	NPC237740
0.6486	Remote Similarity	NPC134586
0.6484	Remote Similarity	NPC39092
0.648	Remote Similarity	NPC192315
0.6474	Remote Similarity	NPC61350
0.6467	Remote Similarity	NPC247980
0.6458	Remote Similarity	NPC106833
0.6458	Remote Similarity	NPC469497
0.6455	Remote Similarity	NPC84478
0.6455	Remote Similarity	NPC203635
0.6453	Remote Similarity	NPC242556
0.6452	Remote Similarity	NPC211997
0.645	Remote Similarity	NPC470500
0.6447	Remote Similarity	NPC476167
0.6443	Remote Similarity	NPC45850
0.6442	Remote Similarity	NPC278451
0.6441	Remote Similarity	NPC120070
0.644	Remote Similarity	NPC206186
0.6439	Remote Similarity	NPC282247
0.6432	Remote Similarity	NPC95898
0.6432	Remote Similarity	NPC211813
0.6429	Remote Similarity	NPC108469
0.6429	Remote Similarity	NPC220851
0.6422	Remote Similarity	NPC242923
0.6421	Remote Similarity	NPC476341
0.642	Remote Similarity	NPC151489
0.642	Remote Similarity	NPC284348
0.641	Remote Similarity	NPC280638
0.6402	Remote Similarity	NPC116622
0.64	Remote Similarity	NPC37548
0.64	Remote Similarity	NPC476098
0.64	Remote Similarity	NPC223427
0.6398	Remote Similarity	NPC46358
0.6395	Remote Similarity	NPC42483
0.6392	Remote Similarity	NPC114335
0.6392	Remote Similarity	NPC141915
0.6392	Remote Similarity	NPC280964
0.639	Remote Similarity	NPC128084
0.6387	Remote Similarity	NPC90415

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 NPC224632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	906
0.2-0.3	514
0.3-0.4	2048
0.4-0.5	2590
0.5-0.6	2133
0.6-0.7	506
0.7-0.8	30
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD444	Approved
0.8639	High Similarity	NPD9714	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD2410	Phase 2
0.7719	Intermediate Similarity	NPD3224	Phase 2
0.7637	Intermediate Similarity	NPD6594	Discontinued
0.7624	Intermediate Similarity	NPD5428	Discontinued
0.7596	Intermediate Similarity	NPD4673	Phase 2
0.7554	Intermediate Similarity	NPD7419	Discontinued
0.75	Intermediate Similarity	NPD3261	Phase 1
0.7471	Intermediate Similarity	NPD5925	Phase 1
0.744	Intermediate Similarity	NPD639	Discontinued
0.735	Intermediate Similarity	NPD4403	Phase 3
0.735	Intermediate Similarity	NPD4401	Phase 2
0.7345	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1954	Phase 1
0.7325	Intermediate Similarity	NPD9187	Approved
0.7305	Intermediate Similarity	NPD2882	Phase 1
0.7302	Intermediate Similarity	NPD6132	Phase 1
0.7287	Intermediate Similarity	NPD1838	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1684	Approved
0.7209	Intermediate Similarity	NPD1685	Approved
0.7202	Intermediate Similarity	NPD6158	Phase 2
0.7202	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6159	Phase 2
0.7174	Intermediate Similarity	NPD1043	Phase 3
0.716	Intermediate Similarity	NPD852	Discontinued
0.7143	Intermediate Similarity	NPD3814	Phase 1
0.7143	Intermediate Similarity	NPD2762	Phase 2
0.7097	Intermediate Similarity	NPD4615	Phase 2
0.709	Intermediate Similarity	NPD5885	Approved
0.7079	Intermediate Similarity	NPD9690	Approved
0.7071	Intermediate Similarity	NPD4358	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1197	Approved
0.7044	Intermediate Similarity	NPD983	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD926	Approved
0.7029	Intermediate Similarity	NPD925	Approved
0.7026	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5529	Phase 1
0.7021	Intermediate Similarity	NPD1912	Approved
0.701	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD1234	Discontinued
0.6995	Remote Similarity	NPD3234	Phase 3
0.6995	Remote Similarity	NPD3233	Phase 2
0.6989	Remote Similarity	NPD1215	Discontinued
0.6989	Remote Similarity	NPD3439	Approved
0.6978	Remote Similarity	NPD4204	Approved
0.6978	Remote Similarity	NPD4203	Approved
0.6976	Remote Similarity	NPD1273	Discontinued
0.6973	Remote Similarity	NPD2383	Phase 1
0.697	Remote Similarity	NPD2794	Discontinued
0.6968	Remote Similarity	NPD9695	Approved
0.6954	Remote Similarity	NPD9705	Discontinued
0.6954	Remote Similarity	NPD112	Approved
0.6952	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6490	Phase 2
0.6947	Remote Similarity	NPD3830	Phase 1
0.694	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD509	Phase 3
0.6931	Remote Similarity	NPD4312	Approved
0.6931	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1468	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4950	Approved
0.6915	Remote Similarity	NPD6887	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7935	Phase 2
0.6893	Remote Similarity	NPD425	Approved
0.6893	Remote Similarity	NPD424	Approved
0.6878	Remote Similarity	NPD5176	Approved
0.6878	Remote Similarity	NPD38	Approved
0.6866	Remote Similarity	NPD7112	Discontinued
0.6866	Remote Similarity	NPD6957	Approved
0.6866	Remote Similarity	NPD6958	Approved
0.686	Remote Similarity	NPD6326	Phase 2
0.686	Remote Similarity	NPD6327	Phase 1
0.6856	Remote Similarity	NPD3765	Approved
0.6842	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7423	Phase 2
0.6829	Remote Similarity	NPD4945	Discontinued
0.6828	Remote Similarity	NPD7757	Approved
0.6828	Remote Similarity	NPD7758	Approved
0.6828	Remote Similarity	NPD706	Phase 1
0.6828	Remote Similarity	NPD2591	Phase 2
0.6826	Remote Similarity	NPD1592	Phase 3
0.6825	Remote Similarity	NPD2757	Phase 2
0.6811	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2524	Discontinued
0.6798	Remote Similarity	NPD6794	Approved
0.6798	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6492	Phase 2
0.6784	Remote Similarity	NPD3013	Phase 3
0.6784	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6711	Approved
0.678	Remote Similarity	NPD404	Discontinued
0.6778	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5905	Phase 1
0.6776	Remote Similarity	NPD443	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4998	Phase 3
0.6754	Remote Similarity	NPD4999	Phase 3
0.6742	Remote Similarity	NPD3889	Approved
0.6742	Remote Similarity	NPD1313	Approved
0.674	Remote Similarity	NPD1599	Approved
0.674	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD2127	Suspended
0.6736	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7409	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7188	Phase 3
0.6732	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6605	Phase 3
0.6721	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6145	Phase 1
0.6718	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3976	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4925	Approved
0.6705	Remote Similarity	NPD3262	Approved
0.6705	Remote Similarity	NPD2128	Phase 1
0.6703	Remote Similarity	NPD1570	Approved
0.6703	Remote Similarity	NPD5065	Approved
0.6699	Remote Similarity	NPD2714	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3525	Discontinued
0.6684	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3928	Approved
0.6684	Remote Similarity	NPD3931	Approved
0.6683	Remote Similarity	NPD537	Phase 2
0.6683	Remote Similarity	NPD534	Phase 2
0.6682	Remote Similarity	NPD5804	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4996	Approved
0.6682	Remote Similarity	NPD4995	Approved
0.6667	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD408	Approved
0.6667	Remote Similarity	NPD5943	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD1572	Phase 2
0.665	Remote Similarity	NPD5413	Phase 2
0.6649	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2599	Approved
0.6649	Remote Similarity	NPD2601	Approved
0.6649	Remote Similarity	NPD3084	Phase 3
0.6649	Remote Similarity	NPD3315	Phase 3
0.6649	Remote Similarity	NPD2600	Approved
0.6637	Remote Similarity	NPD4438	Approved
0.6636	Remote Similarity	NPD5873	Phase 3
0.6636	Remote Similarity	NPD5874	Phase 3
0.6636	Remote Similarity	NPD5833	Phase 1
0.6634	Remote Similarity	NPD3330	Phase 1
0.6633	Remote Similarity	NPD796	Phase 2
0.6633	Remote Similarity	NPD4511	Phase 1
0.6633	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6285	Phase 2
0.662	Remote Similarity	NPD4306	Phase 1
0.6618	Remote Similarity	NPD7726	Phase 1
0.6618	Remote Similarity	NPD6643	Discontinued
0.6617	Remote Similarity	NPD8321	Discontinued
0.6616	Remote Similarity	NPD1915	Phase 1
0.6616	Remote Similarity	NPD3500	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD5425	Phase 1
0.6615	Remote Similarity	NPD2176	Approved
0.6615	Remote Similarity	NPD2175	Phase 3
0.6615	Remote Similarity	NPD2177	Approved
0.6615	Remote Similarity	NPD2805	Phase 2
0.6614	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3799	Suspended
0.6612	Remote Similarity	NPD7006	Approved
0.6609	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD758	Approved
0.6607	Remote Similarity	NPD6458	Discontinued
0.6606	Remote Similarity	NPD7068	Approved
0.6606	Remote Similarity	NPD7067	Approved
0.6588	Remote Similarity	NPD1571	Phase 2
0.6584	Remote Similarity	NPD949	Phase 1
0.6584	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD2381	Approved
0.6576	Remote Similarity	NPD5100	Phase 3
0.6576	Remote Similarity	NPD2380	Approved
0.6576	Remote Similarity	NPD2382	Approved
0.6575	Remote Similarity	NPD3962	Phase 2
0.6575	Remote Similarity	NPD3959	Phase 2
0.6574	Remote Similarity	NPD6750	Phase 2
0.6571	Remote Similarity	NPD7051	Phase 3
0.6571	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6856	Discontinued
0.6564	Remote Similarity	NPD2727	Phase 2
0.6564	Remote Similarity	NPD947	Approved
0.6562	Remote Similarity	NPD9689	Approved
0.6561	Remote Similarity	NPD2917	Approved
0.6561	Remote Similarity	NPD6047	Phase 1
0.6555	Remote Similarity	NPD5045	Phase 2
0.655	Remote Similarity	NPD3813	Approved
0.6546	Remote Similarity	NPD774	Phase 3
0.6541	Remote Similarity	NPD3503	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