NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	614.27
Volume:	618.063
LogP:	3.369
LogD:	2.049
LogS:	-4.451
# Rotatable Bonds:	10
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	5.193
Fsp3:	0.606
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:	-5.169
MDCK Permeability:	4.528017598204315e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.3
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.717
Plasma Protein Binding (PPB):	73.0338134765625%
Volume Distribution (VD):	1.288
Pgp-substrate:	29.683134078979492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.668
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.36

ADMET: Excretion

Clearance (CL):	2.388
Half-life (T1/2):	0.742

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.66
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.129
Carcinogencity:	0.102
Eye Corrosion:	0.006
Eye Irritation:	0.022
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC70949

Natural Product ID:	NPC70949
*Common Name:**	Cleistopholine
IUPAC Name:	4-methylbenzo[g]quinoline-5,10-dione
Synonyms:	Cleistopholine
Standard InCHIKey:	GVRYUHXXENMGEV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H9NO2/c1-8-6-7-15-12-11(8)13(16)9-4-2-3-5-10(9)14(12)17/h2-7H,1H3
SMILES:	Cc1ccnc2c1C(=O)c1ccccc1C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444067
PubChem CID:	457732
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines

*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
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11374955]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	flower buds	Thailand	n.a.	PMID[24601675]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9348	Cananga odorata	Species	Annonaceae	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	3
MIC	18
Others	8

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	2
Organism	17
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.22	ug.mL-1	PMID[477080]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[477081]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[477081]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	12.5	ug.mL-1	PMID[477078]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	1.56	ug.mL-1	PMID[477078]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	100.0	ug.mL-1	PMID[477078]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	12.5	ug.mL-1	PMID[477078]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	=	50.0	ug.mL-1	PMID[477079]
NPT2593	Organism	Rhodotorula mucilaginosa	Rhodotorula mucilaginosa	MIC	=	50.0	ug.mL-1	PMID[477079]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[477079]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	100.0	ug.mL-1	PMID[477079]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	50.0	ug.mL-1	PMID[477079]
NPT770	Organism	Rhizopus microsporus var. chinensis	Rhizopus microsporus var. chinensis	MIC	>	100.0	ug.mL-1	PMID[477079]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	=	50.0	ug.mL-1	PMID[477079]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	25.0	ug.mL-1	PMID[477079]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[477079]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	50.0	ug.mL-1	PMID[477079]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	50.0	ug.mL-1	PMID[477079]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	100.0	ug.mL-1	PMID[477079]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	=	25.0	ug.mL-1	PMID[477079]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.54	ug.mL-1	PMID[477080]
NPT2	Others	Unspecified		Inhibition	=	100.0	%	PMID[477081]
NPT2	Others	Unspecified		Inhibition	=	77.5	%	PMID[477081]
NPT2	Others	Unspecified		Inhibition	=	48.7	%	PMID[477081]
NPT2	Others	Unspecified		Inhibition	=	40.6	%	PMID[477081]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	12.5	ug.mL-1	PMID[477082]
NPT2	Others	Unspecified		IC50	=	196600.0	nM	PMID[477083]

☑ 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 NPC70949 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	558
0.1-0.2	4374
0.2-0.3	14648
0.3-0.4	16174
0.4-0.5	3268
0.5-0.6	2162
0.6-0.7	1304
0.7-0.8	193
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8742	High Similarity	NPC80681
0.8675	High Similarity	NPC237188
0.8662	High Similarity	NPC70406
0.858	High Similarity	NPC265100
0.8491	Intermediate Similarity	NPC251391
0.8365	Intermediate Similarity	NPC313889
0.8302	Intermediate Similarity	NPC123906
0.8239	Intermediate Similarity	NPC105811
0.8235	Intermediate Similarity	NPC157583
0.8228	Intermediate Similarity	NPC467188
0.8086	Intermediate Similarity	NPC217021
0.8086	Intermediate Similarity	NPC470679
0.8056	Intermediate Similarity	NPC128244
0.8035	Intermediate Similarity	NPC73994
0.7989	Intermediate Similarity	NPC191415
0.7988	Intermediate Similarity	NPC209362
0.7976	Intermediate Similarity	NPC115232
0.7966	Intermediate Similarity	NPC206186
0.7964	Intermediate Similarity	NPC242116
0.7931	Intermediate Similarity	NPC477042
0.7919	Intermediate Similarity	NPC284775
0.7907	Intermediate Similarity	NPC469529
0.7889	Intermediate Similarity	NPC216550
0.7879	Intermediate Similarity	NPC229055
0.7831	Intermediate Similarity	NPC74357
0.7824	Intermediate Similarity	NPC114637
0.7821	Intermediate Similarity	NPC255909
0.7805	Intermediate Similarity	NPC473878
0.7803	Intermediate Similarity	NPC293216
0.7803	Intermediate Similarity	NPC139763
0.7798	Intermediate Similarity	NPC470680
0.7798	Intermediate Similarity	NPC100104
0.7797	Intermediate Similarity	NPC477003
0.7784	Intermediate Similarity	NPC213914
0.7772	Intermediate Similarity	NPC34837
0.7765	Intermediate Similarity	NPC71132
0.7754	Intermediate Similarity	NPC317701
0.7747	Intermediate Similarity	NPC326422
0.7738	Intermediate Similarity	NPC474492
0.7735	Intermediate Similarity	NPC476460
0.7722	Intermediate Similarity	NPC103119
0.7717	Intermediate Similarity	NPC167710
0.7714	Intermediate Similarity	NPC83774
0.765	Intermediate Similarity	NPC304203
0.764	Intermediate Similarity	NPC102755
0.7634	Intermediate Similarity	NPC81535
0.7627	Intermediate Similarity	NPC61011
0.7625	Intermediate Similarity	NPC169433
0.7584	Intermediate Similarity	NPC470677
0.7582	Intermediate Similarity	NPC324091
0.7576	Intermediate Similarity	NPC100726
0.7558	Intermediate Similarity	NPC42372
0.7557	Intermediate Similarity	NPC151635
0.7556	Intermediate Similarity	NPC133003
0.7543	Intermediate Similarity	NPC252572
0.7514	Intermediate Similarity	NPC41717
0.75	Intermediate Similarity	NPC46895
0.75	Intermediate Similarity	NPC313823
0.75	Intermediate Similarity	NPC47190
0.75	Intermediate Similarity	NPC471589
0.744	Intermediate Similarity	NPC472260
0.743	Intermediate Similarity	NPC471997
0.7421	Intermediate Similarity	NPC106757
0.7403	Intermediate Similarity	NPC207851
0.7403	Intermediate Similarity	NPC467063
0.7391	Intermediate Similarity	NPC469489
0.7386	Intermediate Similarity	NPC262338
0.7381	Intermediate Similarity	NPC471655
0.7365	Intermediate Similarity	NPC477974
0.7356	Intermediate Similarity	NPC233380
0.7354	Intermediate Similarity	NPC237414
0.7346	Intermediate Similarity	NPC251722
0.7346	Intermediate Similarity	NPC314102
0.7345	Intermediate Similarity	NPC477976
0.7344	Intermediate Similarity	NPC88115
0.733	Intermediate Similarity	NPC328596
0.733	Intermediate Similarity	NPC328318
0.7326	Intermediate Similarity	NPC135950
0.7322	Intermediate Similarity	NPC118084
0.7314	Intermediate Similarity	NPC56233
0.7302	Intermediate Similarity	NPC477044
0.7302	Intermediate Similarity	NPC477041
0.7299	Intermediate Similarity	NPC274981
0.7288	Intermediate Similarity	NPC249614
0.7288	Intermediate Similarity	NPC273532
0.7287	Intermediate Similarity	NPC79356
0.7287	Intermediate Similarity	NPC102592
0.7268	Intermediate Similarity	NPC282103
0.7263	Intermediate Similarity	NPC477004
0.7263	Intermediate Similarity	NPC103361
0.7258	Intermediate Similarity	NPC114974
0.7254	Intermediate Similarity	NPC327592
0.7253	Intermediate Similarity	NPC159125
0.725	Intermediate Similarity	NPC256893
0.7245	Intermediate Similarity	NPC470020
0.7241	Intermediate Similarity	NPC214106
0.7225	Intermediate Similarity	NPC121327
0.7219	Intermediate Similarity	NPC272458
0.7216	Intermediate Similarity	NPC317373
0.7211	Intermediate Similarity	NPC474916
0.7209	Intermediate Similarity	NPC51054
0.7204	Intermediate Similarity	NPC154339
0.7196	Intermediate Similarity	NPC472116
0.7193	Intermediate Similarity	NPC200743
0.7193	Intermediate Similarity	NPC281094
0.7192	Intermediate Similarity	NPC216612
0.7192	Intermediate Similarity	NPC210434
0.719	Intermediate Similarity	NPC143603
0.719	Intermediate Similarity	NPC91958
0.7188	Intermediate Similarity	NPC282398
0.7181	Intermediate Similarity	NPC267343
0.7179	Intermediate Similarity	NPC46358
0.7175	Intermediate Similarity	NPC470894
0.7173	Intermediate Similarity	NPC477045
0.7168	Intermediate Similarity	NPC76982
0.7158	Intermediate Similarity	NPC106824
0.7157	Intermediate Similarity	NPC322482
0.7152	Intermediate Similarity	NPC471574
0.715	Intermediate Similarity	NPC57398
0.7143	Intermediate Similarity	NPC202812
0.7143	Intermediate Similarity	NPC79777
0.7143	Intermediate Similarity	NPC182940
0.7135	Intermediate Similarity	NPC471943
0.7134	Intermediate Similarity	NPC65408
0.7128	Intermediate Similarity	NPC472065
0.7126	Intermediate Similarity	NPC56765
0.7126	Intermediate Similarity	NPC293487
0.7121	Intermediate Similarity	NPC220337
0.7118	Intermediate Similarity	NPC102664
0.7117	Intermediate Similarity	NPC291517
0.7105	Intermediate Similarity	NPC109922
0.7102	Intermediate Similarity	NPC478182
0.7088	Intermediate Similarity	NPC248462
0.7088	Intermediate Similarity	NPC164340
0.7086	Intermediate Similarity	NPC44773
0.7086	Intermediate Similarity	NPC215584
0.7083	Intermediate Similarity	NPC159630
0.7083	Intermediate Similarity	NPC230085
0.7083	Intermediate Similarity	NPC284338
0.7083	Intermediate Similarity	NPC123395
0.7077	Intermediate Similarity	NPC477043
0.7074	Intermediate Similarity	NPC138370
0.7068	Intermediate Similarity	NPC90229
0.7065	Intermediate Similarity	NPC470205
0.7062	Intermediate Similarity	NPC143977
0.7056	Intermediate Similarity	NPC116555
0.7053	Intermediate Similarity	NPC74575
0.705	Intermediate Similarity	NPC236668
0.7049	Intermediate Similarity	NPC234403
0.7041	Intermediate Similarity	NPC472064
0.703	Intermediate Similarity	NPC472288
0.703	Intermediate Similarity	NPC27041
0.7027	Intermediate Similarity	NPC110158
0.7024	Intermediate Similarity	NPC136002
0.7021	Intermediate Similarity	NPC268966
0.7019	Intermediate Similarity	NPC71236
0.7016	Intermediate Similarity	NPC472293
0.7015	Intermediate Similarity	NPC146976
0.7006	Intermediate Similarity	NPC478184
0.7006	Intermediate Similarity	NPC21174
0.7006	Intermediate Similarity	NPC271797
0.7005	Intermediate Similarity	NPC470018
0.7005	Intermediate Similarity	NPC278434
0.7	Intermediate Similarity	NPC247735
0.7	Intermediate Similarity	NPC472295
0.7	Intermediate Similarity	NPC318299
0.7	Intermediate Similarity	NPC81802
0.7	Intermediate Similarity	NPC472210
0.7	Intermediate Similarity	NPC110182
0.7	Intermediate Similarity	NPC269886
0.6995	Remote Similarity	NPC213468
0.6995	Remote Similarity	NPC55772
0.6994	Remote Similarity	NPC107287
0.6994	Remote Similarity	NPC312860
0.699	Remote Similarity	NPC472259
0.699	Remote Similarity	NPC229893
0.6989	Remote Similarity	NPC295158
0.6986	Remote Similarity	NPC24019
0.6979	Remote Similarity	NPC227582
0.6974	Remote Similarity	NPC472062
0.6974	Remote Similarity	NPC472063
0.6974	Remote Similarity	NPC472069
0.6973	Remote Similarity	NPC117027
0.697	Remote Similarity	NPC266249
0.6968	Remote Similarity	NPC44354
0.6965	Remote Similarity	NPC317752
0.6963	Remote Similarity	NPC195239
0.6963	Remote Similarity	NPC157828
0.6959	Remote Similarity	NPC112741
0.6952	Remote Similarity	NPC135601
0.6952	Remote Similarity	NPC141612
0.6952	Remote Similarity	NPC17273
0.6949	Remote Similarity	NPC478185
0.6947	Remote Similarity	NPC472292
0.6944	Remote Similarity	NPC32534
0.6942	Remote Similarity	NPC477788
0.6941	Remote Similarity	NPC167400
0.694	Remote Similarity	NPC14113
0.694	Remote Similarity	NPC84827
0.694	Remote Similarity	NPC145885

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 NPC70949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	671
0.2-0.3	965
0.3-0.4	2104
0.4-0.5	2548
0.5-0.6	1849
0.6-0.7	615
0.7-0.8	79
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD2481	Approved
0.8462	Intermediate Similarity	NPD2479	Phase 3
0.8393	Intermediate Similarity	NPD3238	Discontinued
0.8343	Intermediate Similarity	NPD2753	Discontinued
0.8239	Intermediate Similarity	NPD1270	Approved
0.8105	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD4988	Discontinued
0.7929	Intermediate Similarity	NPD6446	Discontinued
0.7901	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD2336	Approved
0.7751	Intermediate Similarity	NPD5400	Approved
0.774	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1630	Approved
0.7674	Intermediate Similarity	NPD1343	Approved
0.7674	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD2307	Discontinued
0.7644	Intermediate Similarity	NPD4524	Discontinued
0.7627	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3583	Phase 2
0.7602	Intermediate Similarity	NPD1631	Approved
0.7568	Intermediate Similarity	NPD4848	Phase 1
0.7547	Intermediate Similarity	NPD272	Approved
0.7526	Intermediate Similarity	NPD6987	Phase 1
0.7514	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7564	Discontinued
0.75	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6787	Phase 2
0.7448	Intermediate Similarity	NPD3839	Phase 2
0.7448	Intermediate Similarity	NPD3840	Phase 2
0.744	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4051	Discontinued
0.7419	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3944	Approved
0.7375	Intermediate Similarity	NPD3942	Approved
0.736	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3905	Phase 3
0.7356	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6664	Approved
0.733	Intermediate Similarity	NPD1575	Approved
0.733	Intermediate Similarity	NPD1573	Approved
0.7325	Intermediate Similarity	NPD2119	Approved
0.7325	Intermediate Similarity	NPD2118	Approved
0.7322	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2896	Discontinued
0.7296	Intermediate Similarity	NPD6152	Phase 1
0.7287	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2770	Discontinued
0.7283	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4028	Approved
0.7267	Intermediate Similarity	NPD4030	Approved
0.7267	Intermediate Similarity	NPD4029	Approved
0.7258	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD175	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7233	Approved
0.7243	Intermediate Similarity	NPD7234	Approved
0.724	Intermediate Similarity	NPD7187	Phase 2
0.724	Intermediate Similarity	NPD2879	Approved
0.724	Intermediate Similarity	NPD2881	Approved
0.724	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5809	Phase 3
0.7222	Intermediate Similarity	NPD5888	Phase 2
0.7207	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4883	Approved
0.7207	Intermediate Similarity	NPD1586	Approved
0.7202	Intermediate Similarity	NPD4304	Discovery
0.7188	Intermediate Similarity	NPD3475	Approved
0.7188	Intermediate Similarity	NPD3476	Approved
0.7186	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD460	Discontinued
0.7151	Intermediate Similarity	NPD7175	Phase 1
0.7143	Intermediate Similarity	NPD5473	Discontinued
0.7134	Intermediate Similarity	NPD200	Phase 2
0.7134	Intermediate Similarity	NPD201	Phase 2
0.7128	Intermediate Similarity	NPD7098	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7010	Phase 3
0.7128	Intermediate Similarity	NPD4922	Phase 2
0.7113	Intermediate Similarity	NPD4912	Phase 3
0.7108	Intermediate Similarity	NPD107	Approved
0.7107	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD991	Phase 2
0.7088	Intermediate Similarity	NPD1587	Approved
0.7085	Intermediate Similarity	NPD7454	Approved
0.7085	Intermediate Similarity	NPD7455	Approved
0.7083	Intermediate Similarity	NPD2405	Phase 3
0.7079	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3947	Discontinued
0.7072	Intermediate Similarity	NPD4075	Phase 2
0.7065	Intermediate Similarity	NPD3318	Approved
0.7065	Intermediate Similarity	NPD3320	Approved
0.7065	Intermediate Similarity	NPD3319	Phase 1
0.7056	Intermediate Similarity	NPD7191	Phase 2
0.7049	Intermediate Similarity	NPD3927	Phase 2
0.7045	Intermediate Similarity	NPD5315	Discontinued
0.7041	Intermediate Similarity	NPD7289	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1527	Phase 2
0.7035	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5755	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2213	Approved
0.7029	Intermediate Similarity	NPD2214	Approved
0.702	Intermediate Similarity	NPD1600	Suspended
0.7016	Intermediate Similarity	NPD6226	Phase 3
0.7006	Intermediate Similarity	NPD5088	Discontinued
0.7006	Intermediate Similarity	NPD3323	Discontinued
0.7005	Intermediate Similarity	NPD4913	Phase 3
0.7	Intermediate Similarity	NPD2411	Approved
0.7	Intermediate Similarity	NPD7469	Discontinued
0.6995	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2511	Approved
0.6984	Remote Similarity	NPD1658	Discontinued
0.6983	Remote Similarity	NPD4639	Approved
0.6983	Remote Similarity	NPD4638	Approved
0.6983	Remote Similarity	NPD4640	Approved
0.6982	Remote Similarity	NPD751	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5020	Approved
0.6961	Remote Similarity	NPD750	Phase 2
0.6959	Remote Similarity	NPD4547	Phase 3
0.6959	Remote Similarity	NPD6479	Discontinued
0.6959	Remote Similarity	NPD9271	Approved
0.6954	Remote Similarity	NPD2061	Approved
0.6954	Remote Similarity	NPD2809	Approved
0.6949	Remote Similarity	NPD6771	Discontinued
0.6949	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD9075	Approved
0.6941	Remote Similarity	NPD9074	Approved
0.6937	Remote Similarity	NPD9583	Approved
0.6935	Remote Similarity	NPD721	Approved
0.6927	Remote Similarity	NPD5636	Discontinued
0.6915	Remote Similarity	NPD6954	Phase 2
0.6907	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6999	Discontinued
0.6905	Remote Similarity	NPD9599	Approved
0.6904	Remote Similarity	NPD5901	Discontinued
0.6904	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3389	Approved
0.6897	Remote Similarity	NPD3394	Approved
0.6897	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3393	Approved
0.6885	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2510	Approved
0.6884	Remote Similarity	NPD2509	Approved
0.6875	Remote Similarity	NPD5855	Phase 3
0.6875	Remote Similarity	NPD7618	Phase 3
0.6875	Remote Similarity	NPD820	Phase 3
0.6875	Remote Similarity	NPD7619	Phase 3
0.6875	Remote Similarity	NPD5853	Phase 3
0.6872	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD2720	Phase 1
0.6871	Remote Similarity	NPD715	Phase 3
0.6869	Remote Similarity	NPD2008	Discontinued
0.6866	Remote Similarity	NPD5475	Discontinued
0.6866	Remote Similarity	NPD4417	Approved
0.6862	Remote Similarity	NPD3315	Phase 3
0.686	Remote Similarity	NPD4703	Approved
0.686	Remote Similarity	NPD4702	Approved
0.6853	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4181	Approved
0.6847	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6178	Phase 3
0.6845	Remote Similarity	NPD2069	Approved
0.6845	Remote Similarity	NPD2073	Approved
0.6845	Remote Similarity	NPD2074	Approved
0.6845	Remote Similarity	NPD2071	Approved
0.6845	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2070	Approved
0.6845	Remote Similarity	NPD2075	Approved
0.6845	Remote Similarity	NPD2068	Approved
0.6845	Remote Similarity	NPD2072	Approved
0.6839	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5017	Discontinued
0.6833	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD482	Approved
0.6829	Remote Similarity	NPD4429	Discontinued
0.6829	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3178	Discontinued
0.6827	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3961	Discontinued
0.6825	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5854	Approved
0.6818	Remote Similarity	NPD4299	Phase 1
0.6818	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6635	Approved
0.6816	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3609	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