NPASS Compound

Structure

CID195120 OpenBabel06191715582D 23 26 0 0 0 0 0 0 0 0999 V2000 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 11 2 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.1
Volume:	304.855
LogP:	2.292
LogD:	2.616
LogS:	-4.22
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	2.565
Fsp3:	0.235
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:	-4.681
MDCK Permeability:	5.199333099881187e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	88.46219635009766%
Volume Distribution (VD):	0.811
Pgp-substrate:	4.812892913818359%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.776
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	4.412
Half-life (T1/2):	0.255

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.375
AMES Toxicity:	0.885
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.428
Skin Sensitization:	0.116
Carcinogencity:	0.956
Eye Corrosion:	0.008
Eye Irritation:	0.832
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC195120

Natural Product ID:	NPC195120
*Common Name:**	Tecleanthine
IUPAC Name:	6,11-dimethoxy-5-methyl-[1,3]dioxolo[4,5-b]acridin-10-one
Synonyms:	tecleanthine
Standard InCHIKey:	QYWWGVQKWKTLMU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H15NO5/c1-18-10-7-12-16(23-8-22-12)17(21-3)13(10)15(19)9-5-4-6-11(20-2)14(9)18/h4-7H,8H2,1-3H3
SMILES:	COc1c2OCOc2cc2c1c(=O)c1c(n2C)c(OC)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455629
PubChem CID:	628642
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO6049	Teclea trichocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141852]
NPO1947	Nemopilema nomurai	Species	Rhizostomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6049	Teclea trichocarpa	Species	Rutaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23200.0	nM	PMID[492286]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	53000.0	nM	PMID[492286]

☑ 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 NPC195120 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	634
0.1-0.2	3515
0.2-0.3	12131
0.3-0.4	5283
0.4-0.5	9859
0.5-0.6	9556
0.6-0.7	1377
0.7-0.8	279
0.8-0.85	40
0.85-0.9	12
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC87560
0.9796	High Similarity	NPC118154
0.9796	High Similarity	NPC157983
0.9391	High Similarity	NPC268223
0.9204	High Similarity	NPC182853
0.9069	High Similarity	NPC118189
0.9015	High Similarity	NPC134702
0.9	High Similarity	NPC220241
0.9	High Similarity	NPC295479
0.8976	High Similarity	NPC76478
0.896	High Similarity	NPC148391
0.8818	High Similarity	NPC114468
0.8775	High Similarity	NPC2905
0.8614	High Similarity	NPC212123
0.8612	High Similarity	NPC7560
0.8498	Intermediate Similarity	NPC13249
0.8454	Intermediate Similarity	NPC30749
0.8364	Intermediate Similarity	NPC285254
0.8333	Intermediate Similarity	NPC114039
0.8333	Intermediate Similarity	NPC206109
0.8317	Intermediate Similarity	NPC305542
0.8317	Intermediate Similarity	NPC116178
0.8283	Intermediate Similarity	NPC1820
0.8278	Intermediate Similarity	NPC321166
0.8278	Intermediate Similarity	NPC217903
0.8252	Intermediate Similarity	NPC198160
0.8221	Intermediate Similarity	NPC474366
0.8218	Intermediate Similarity	NPC234933
0.8119	Intermediate Similarity	NPC170333
0.8103	Intermediate Similarity	NPC5167
0.8095	Intermediate Similarity	NPC218303
0.801	Intermediate Similarity	NPC85613
0.8009	Intermediate Similarity	NPC329830
0.7981	Intermediate Similarity	NPC176113
0.7971	Intermediate Similarity	NPC15987
0.7931	Intermediate Similarity	NPC254957
0.7913	Intermediate Similarity	NPC241263
0.7895	Intermediate Similarity	NPC268077
0.7895	Intermediate Similarity	NPC133156
0.7864	Intermediate Similarity	NPC71124
0.7828	Intermediate Similarity	NPC298320
0.7799	Intermediate Similarity	NPC328700
0.7799	Intermediate Similarity	NPC202771
0.7799	Intermediate Similarity	NPC119818
0.7799	Intermediate Similarity	NPC2173
0.7762	Intermediate Similarity	NPC207971
0.774	Intermediate Similarity	NPC5374
0.7719	Intermediate Similarity	NPC304837
0.7719	Intermediate Similarity	NPC476258
0.7714	Intermediate Similarity	NPC288759
0.765	Intermediate Similarity	NPC55470
0.765	Intermediate Similarity	NPC283810
0.7608	Intermediate Similarity	NPC14622
0.7608	Intermediate Similarity	NPC46744
0.7608	Intermediate Similarity	NPC124302
0.7608	Intermediate Similarity	NPC193906
0.7608	Intermediate Similarity	NPC23080
0.7608	Intermediate Similarity	NPC215098
0.7608	Intermediate Similarity	NPC70290
0.7608	Intermediate Similarity	NPC73020
0.76	Intermediate Similarity	NPC287152
0.7595	Intermediate Similarity	NPC120513
0.759	Intermediate Similarity	NPC299582
0.7559	Intermediate Similarity	NPC313112
0.7559	Intermediate Similarity	NPC301292
0.7554	Intermediate Similarity	NPC120239
0.7544	Intermediate Similarity	NPC476220
0.7544	Intermediate Similarity	NPC160113
0.7536	Intermediate Similarity	NPC72788
0.7536	Intermediate Similarity	NPC63152
0.7536	Intermediate Similarity	NPC226652
0.7536	Intermediate Similarity	NPC314100
0.7536	Intermediate Similarity	NPC120671
0.7533	Intermediate Similarity	NPC476429
0.7521	Intermediate Similarity	NPC1608
0.75	Intermediate Similarity	NPC113455
0.7489	Intermediate Similarity	NPC148124
0.7489	Intermediate Similarity	NPC173250
0.7463	Intermediate Similarity	NPC116007
0.7458	Intermediate Similarity	NPC203373
0.7444	Intermediate Similarity	NPC99724
0.7436	Intermediate Similarity	NPC93653
0.743	Intermediate Similarity	NPC41216
0.7402	Intermediate Similarity	NPC27887
0.7389	Intermediate Similarity	NPC476436
0.7379	Intermediate Similarity	NPC83511
0.7359	Intermediate Similarity	NPC154922
0.7358	Intermediate Similarity	NPC112937
0.7357	Intermediate Similarity	NPC248903
0.7356	Intermediate Similarity	NPC208890
0.7343	Intermediate Similarity	NPC18306
0.7342	Intermediate Similarity	NPC195636
0.7339	Intermediate Similarity	NPC46990
0.7327	Intermediate Similarity	NPC303581
0.7327	Intermediate Similarity	NPC308943
0.7327	Intermediate Similarity	NPC67978
0.7323	Intermediate Similarity	NPC24954
0.7319	Intermediate Similarity	NPC208364
0.7313	Intermediate Similarity	NPC26928
0.7308	Intermediate Similarity	NPC477259
0.7308	Intermediate Similarity	NPC169387
0.7288	Intermediate Similarity	NPC124313
0.7286	Intermediate Similarity	NPC226708
0.7277	Intermediate Similarity	NPC207283
0.7277	Intermediate Similarity	NPC84164
0.7273	Intermediate Similarity	NPC204867
0.7265	Intermediate Similarity	NPC168922
0.726	Intermediate Similarity	NPC477825
0.7255	Intermediate Similarity	NPC308267
0.7244	Intermediate Similarity	NPC476069
0.724	Intermediate Similarity	NPC10732
0.7227	Intermediate Similarity	NPC477396
0.7215	Intermediate Similarity	NPC477393
0.7193	Intermediate Similarity	NPC231924
0.719	Intermediate Similarity	NPC312531
0.7189	Intermediate Similarity	NPC101312
0.7167	Intermediate Similarity	NPC34770
0.7163	Intermediate Similarity	NPC207239
0.7162	Intermediate Similarity	NPC470482
0.7162	Intermediate Similarity	NPC477827
0.7162	Intermediate Similarity	NPC470481
0.7162	Intermediate Similarity	NPC477826
0.7161	Intermediate Similarity	NPC119134
0.715	Intermediate Similarity	NPC224687
0.7149	Intermediate Similarity	NPC166722
0.7137	Intermediate Similarity	NPC183537
0.7136	Intermediate Similarity	NPC98416
0.7136	Intermediate Similarity	NPC469815
0.7136	Intermediate Similarity	NPC207873
0.7136	Intermediate Similarity	NPC469816
0.7136	Intermediate Similarity	NPC100573
0.7125	Intermediate Similarity	NPC270515
0.7123	Intermediate Similarity	NPC80472
0.7122	Intermediate Similarity	NPC329992
0.7118	Intermediate Similarity	NPC19175
0.7116	Intermediate Similarity	NPC83019
0.7115	Intermediate Similarity	NPC179704
0.7112	Intermediate Similarity	NPC217176
0.7106	Intermediate Similarity	NPC182907
0.7106	Intermediate Similarity	NPC189903
0.7105	Intermediate Similarity	NPC251071
0.7103	Intermediate Similarity	NPC477258
0.7101	Intermediate Similarity	NPC121400
0.7098	Intermediate Similarity	NPC290227
0.7091	Intermediate Similarity	NPC478075
0.7091	Intermediate Similarity	NPC222561
0.7081	Intermediate Similarity	NPC249405
0.7078	Intermediate Similarity	NPC38961
0.7078	Intermediate Similarity	NPC475147
0.7071	Intermediate Similarity	NPC148497
0.7071	Intermediate Similarity	NPC153008
0.707	Intermediate Similarity	NPC272706
0.707	Intermediate Similarity	NPC204580
0.707	Intermediate Similarity	NPC24228
0.7068	Intermediate Similarity	NPC470042
0.7067	Intermediate Similarity	NPC240684
0.7066	Intermediate Similarity	NPC77878
0.7064	Intermediate Similarity	NPC108342
0.7062	Intermediate Similarity	NPC296575
0.7059	Intermediate Similarity	NPC73280
0.7059	Intermediate Similarity	NPC166712
0.7059	Intermediate Similarity	NPC86469
0.7049	Intermediate Similarity	NPC303374
0.7039	Intermediate Similarity	NPC9475
0.7037	Intermediate Similarity	NPC17677
0.7035	Intermediate Similarity	NPC313327
0.7035	Intermediate Similarity	NPC478213
0.7035	Intermediate Similarity	NPC477828
0.7035	Intermediate Similarity	NPC244371
0.7028	Intermediate Similarity	NPC315634
0.7028	Intermediate Similarity	NPC100734
0.7028	Intermediate Similarity	NPC88923
0.7028	Intermediate Similarity	NPC45389
0.7027	Intermediate Similarity	NPC168250
0.7025	Intermediate Similarity	NPC134637
0.7023	Intermediate Similarity	NPC125924
0.7019	Intermediate Similarity	NPC472163
0.7009	Intermediate Similarity	NPC302001
0.6996	Remote Similarity	NPC25961
0.6992	Remote Similarity	NPC291173
0.6987	Remote Similarity	NPC477395
0.6987	Remote Similarity	NPC128476
0.6986	Remote Similarity	NPC286135
0.6985	Remote Similarity	NPC68882
0.6983	Remote Similarity	NPC473458
0.6983	Remote Similarity	NPC471513
0.6982	Remote Similarity	NPC90185
0.6981	Remote Similarity	NPC474009
0.698	Remote Similarity	NPC153631
0.6979	Remote Similarity	NPC22481
0.6971	Remote Similarity	NPC58209
0.6971	Remote Similarity	NPC222524
0.6971	Remote Similarity	NPC107123
0.6971	Remote Similarity	NPC287588
0.6964	Remote Similarity	NPC82541
0.6962	Remote Similarity	NPC314702
0.6961	Remote Similarity	NPC474858
0.6958	Remote Similarity	NPC188400
0.6958	Remote Similarity	NPC160100
0.6952	Remote Similarity	NPC473562

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 NPC195120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	699
0.2-0.3	1120
0.3-0.4	1935
0.4-0.5	2683
0.5-0.6	1794
0.6-0.7	501
0.7-0.8	53
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8971	High Similarity	NPD2899	Discontinued
0.8303	Intermediate Similarity	NPD6625	Approved
0.8058	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5005	Approved
0.7799	Intermediate Similarity	NPD5006	Approved
0.7788	Intermediate Similarity	NPD4846	Phase 2
0.7674	Intermediate Similarity	NPD683	Approved
0.7608	Intermediate Similarity	NPD4420	Approved
0.7393	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD7223	Discontinued
0.7313	Intermediate Similarity	NPD7224	Discontinued
0.7269	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5242	Approved
0.7202	Intermediate Similarity	NPD8461	Discontinued
0.7163	Intermediate Similarity	NPD3297	Approved
0.713	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5071	Phase 2
0.7103	Intermediate Similarity	NPD5582	Discontinued
0.7095	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7279	Phase 2
0.7074	Intermediate Similarity	NPD7278	Phase 2
0.7072	Intermediate Similarity	NPD5860	Discontinued
0.7035	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7803	Approved
0.7022	Intermediate Similarity	NPD7559	Phase 2
0.7005	Intermediate Similarity	NPD6874	Approved
0.7	Intermediate Similarity	NPD3298	Approved
0.6986	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4859	Phase 1
0.6974	Remote Similarity	NPD5519	Discontinued
0.6972	Remote Similarity	NPD5457	Discontinued
0.6961	Remote Similarity	NPD5183	Approved
0.6961	Remote Similarity	NPD5186	Approved
0.691	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5496	Approved
0.6895	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8067	Phase 3
0.6893	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7708	Approved
0.6864	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1483	Discontinued
0.6844	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5977	Approved
0.6832	Remote Similarity	NPD5978	Approved
0.683	Remote Similarity	NPD4082	Approved
0.6829	Remote Similarity	NPD2821	Approved
0.6827	Remote Similarity	NPD7955	Approved
0.6827	Remote Similarity	NPD7956	Approved
0.6814	Remote Similarity	NPD1945	Phase 1
0.6802	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6104	Discontinued
0.677	Remote Similarity	NPD5914	Approved
0.6763	Remote Similarity	NPD7886	Phase 2
0.6763	Remote Similarity	NPD7885	Phase 2
0.6749	Remote Similarity	NPD5353	Approved
0.6748	Remote Similarity	NPD8367	Approved
0.6746	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3437	Discontinued
0.6712	Remote Similarity	NPD6321	Discontinued
0.6711	Remote Similarity	NPD7584	Approved
0.6711	Remote Similarity	NPD7263	Phase 2
0.6711	Remote Similarity	NPD7225	Discontinued
0.6709	Remote Similarity	NPD4981	Phase 2
0.6709	Remote Similarity	NPD6199	Discontinued
0.6707	Remote Similarity	NPD8492	Approved
0.6704	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7125	Discontinued
0.6696	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6723	Discontinued
0.6683	Remote Similarity	NPD6385	Approved
0.6683	Remote Similarity	NPD6386	Approved
0.6682	Remote Similarity	NPD7626	Approved
0.6682	Remote Similarity	NPD7627	Approved
0.6681	Remote Similarity	NPD4505	Phase 1
0.6681	Remote Similarity	NPD5950	Discontinued
0.6667	Remote Similarity	NPD1898	Discontinued
0.6667	Remote Similarity	NPD4493	Discontinued
0.6667	Remote Similarity	NPD4049	Phase 2
0.6653	Remote Similarity	NPD7186	Phase 3
0.6651	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2248	Approved
0.6651	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2246	Approved
0.6638	Remote Similarity	NPD3912	Discontinued
0.6638	Remote Similarity	NPD4492	Approved
0.6638	Remote Similarity	NPD4494	Approved
0.6637	Remote Similarity	NPD4596	Phase 1
0.6636	Remote Similarity	NPD2845	Phase 2
0.6636	Remote Similarity	NPD2843	Phase 2
0.6625	Remote Similarity	NPD7922	Phase 1
0.6623	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4465	Phase 2
0.6622	Remote Similarity	NPD1880	Phase 3
0.6622	Remote Similarity	NPD4467	Phase 2
0.662	Remote Similarity	NPD4515	Suspended
0.6608	Remote Similarity	NPD3472	Approved
0.6608	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD4022	Approved
0.6608	Remote Similarity	NPD2906	Approved
0.6608	Remote Similarity	NPD2907	Approved
0.6606	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7417	Discontinued
0.6592	Remote Similarity	NPD2339	Phase 3
0.659	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3818	Discontinued
0.6587	Remote Similarity	NPD2249	Approved
0.6587	Remote Similarity	NPD8091	Phase 3
0.6587	Remote Similarity	NPD2247	Approved
0.6575	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4952	Phase 3
0.6567	Remote Similarity	NPD6198	Phase 1
0.6564	Remote Similarity	NPD7583	Approved
0.6553	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD6788	Approved
0.6552	Remote Similarity	NPD8149	Discontinued
0.655	Remote Similarity	NPD3372	Discontinued
0.6548	Remote Similarity	NPD2654	Approved
0.6542	Remote Similarity	NPD3441	Approved
0.6542	Remote Similarity	NPD3442	Approved
0.6538	Remote Similarity	NPD5494	Approved
0.6535	Remote Similarity	NPD7585	Approved
0.6533	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2974	Approved
0.6532	Remote Similarity	NPD2975	Approved
0.6532	Remote Similarity	NPD2973	Approved
0.6531	Remote Similarity	NPD6790	Phase 1
0.6524	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6877	Discontinued
0.6495	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD3815	Phase 1
0.6494	Remote Similarity	NPD3816	Phase 1
0.6488	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD4373	Phase 2
0.6486	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD3640	Phase 3
0.6485	Remote Similarity	NPD3259	Approved
0.6485	Remote Similarity	NPD3641	Approved
0.6485	Remote Similarity	NPD3639	Approved
0.6484	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7907	Approved
0.6483	Remote Similarity	NPD7805	Phase 3
0.6482	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5025	Approved
0.6479	Remote Similarity	NPD3793	Phase 3
0.6478	Remote Similarity	NPD3893	Discontinued
0.6476	Remote Similarity	NPD6644	Discontinued
0.6475	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7048	Phase 3
0.6473	Remote Similarity	NPD6962	Phase 2
0.6471	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5658	Approved
0.6463	Remote Similarity	NPD7701	Phase 2
0.646	Remote Similarity	NPD3516	Approved
0.646	Remote Similarity	NPD3515	Approved
0.6459	Remote Similarity	NPD5677	Discontinued
0.6458	Remote Similarity	NPD7654	Discontinued
0.6456	Remote Similarity	NPD6997	Phase 2
0.6452	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4206	Approved
0.6444	Remote Similarity	NPD4580	Approved
0.6439	Remote Similarity	NPD2366	Approved
0.6438	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3006	Discontinued
0.6432	Remote Similarity	NPD8099	Discontinued
0.6432	Remote Similarity	NPD8251	Approved
0.6432	Remote Similarity	NPD8252	Approved
0.6429	Remote Similarity	NPD4668	Phase 2
0.6429	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2680	Approved
0.6429	Remote Similarity	NPD2681	Approved
0.6426	Remote Similarity	NPD5632	Approved
0.6426	Remote Similarity	NPD5488	Discontinued
0.6426	Remote Similarity	NPD4429	Discontinued
0.6425	Remote Similarity	NPD5937	Approved
0.6423	Remote Similarity	NPD4613	Phase 2
0.6423	Remote Similarity	NPD7560	Approved
0.6422	Remote Similarity	NPD3888	Discontinued
0.6419	Remote Similarity	NPD6296	Discontinued
0.6419	Remote Similarity	NPD7043	Discontinued
0.6416	Remote Similarity	NPD2493	Approved
0.6416	Remote Similarity	NPD3450	Approved
0.6416	Remote Similarity	NPD2494	Approved
0.6416	Remote Similarity	NPD3452	Approved
0.6413	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4361	Phase 2
0.6408	Remote Similarity	NPD1934	Approved
0.6406	Remote Similarity	NPD7280	Phase 3

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