NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.05
Volume:	229.138
LogP:	1.007
LogD:	1.223
LogS:	-3.313
# Rotatable Bonds:	1
TPSA:	88.26
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	2.594
Fsp3:	0.083
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:	-5.134
MDCK Permeability:	6.712241429340793e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.084
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	64.8790283203125%
Volume Distribution (VD):	0.658
Pgp-substrate:	23.327974319458008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.619
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.527
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	5.964
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.617
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.391
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.775
Carcinogencity:	0.037
Eye Corrosion:	0.005
Eye Irritation:	0.738
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC288987

Natural Product ID:	NPC288987
*Common Name:**	8-Methoxy-9H-Pyrido[3,4-B]Indole-1,3,4-Trione
IUPAC Name:	8-methoxy-9H-pyrido[3,4-b]indole-1,3,4-trione
Synonyms:
Standard InCHIKey:	VELKHFGMMALQQU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H8N2O4/c1-18-6-4-2-3-5-7-9(13-8(5)6)11(16)14-12(17)10(7)15/h2-4,13H,1H3,(H,14,16,17)
SMILES:	COc1cccc2c1[nH]c1c2c(=O)c(=O)[nH]c1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229715
PubChem CID:	5320565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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
EC50	2
Others	6

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	EC50	=	183000.0	nM	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	EC50	=	257000.0	nM	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	55.9	%	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	50.0	%	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	59.8	%	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	35.1	%	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	47.3	%	PMID[491154]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	39.5	%	PMID[491154]

☑ 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 NPC288987 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	542
0.1-0.2	4189
0.2-0.3	12953
0.3-0.4	5173
0.4-0.5	15162
0.5-0.6	3045
0.6-0.7	1371
0.7-0.8	256
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8371	Intermediate Similarity	NPC148889
0.823	Intermediate Similarity	NPC187501
0.8152	Intermediate Similarity	NPC39500
0.8037	Intermediate Similarity	NPC478078
0.8029	Intermediate Similarity	NPC132539
0.8009	Intermediate Similarity	NPC323969
0.8	Intermediate Similarity	NPC184408
0.7963	Intermediate Similarity	NPC208084
0.7955	Intermediate Similarity	NPC257851
0.7952	Intermediate Similarity	NPC321428
0.794	Intermediate Similarity	NPC53534
0.7929	Intermediate Similarity	NPC474798
0.7926	Intermediate Similarity	NPC225279
0.7919	Intermediate Similarity	NPC194740
0.7857	Intermediate Similarity	NPC329631
0.7854	Intermediate Similarity	NPC144452
0.7848	Intermediate Similarity	NPC260434
0.7848	Intermediate Similarity	NPC474688
0.7834	Intermediate Similarity	NPC131885
0.7818	Intermediate Similarity	NPC122436
0.7802	Intermediate Similarity	NPC165964
0.7793	Intermediate Similarity	NPC157931
0.7783	Intermediate Similarity	NPC270918
0.7758	Intermediate Similarity	NPC274640
0.7741	Intermediate Similarity	NPC152620
0.7736	Intermediate Similarity	NPC45190
0.7736	Intermediate Similarity	NPC300156
0.7718	Intermediate Similarity	NPC475190
0.7703	Intermediate Similarity	NPC179287
0.7696	Intermediate Similarity	NPC118228
0.7696	Intermediate Similarity	NPC242928
0.7655	Intermediate Similarity	NPC473186
0.7652	Intermediate Similarity	NPC475844
0.765	Intermediate Similarity	NPC232225
0.7642	Intermediate Similarity	NPC476138
0.7642	Intermediate Similarity	NPC245816
0.7634	Intermediate Similarity	NPC140296
0.7633	Intermediate Similarity	NPC230403
0.7626	Intermediate Similarity	NPC305984
0.761	Intermediate Similarity	NPC221873
0.76	Intermediate Similarity	NPC66777
0.76	Intermediate Similarity	NPC471762
0.7588	Intermediate Similarity	NPC182222
0.7588	Intermediate Similarity	NPC39370
0.7578	Intermediate Similarity	NPC205372
0.7578	Intermediate Similarity	NPC94842
0.7578	Intermediate Similarity	NPC314633
0.7577	Intermediate Similarity	NPC102593
0.7577	Intermediate Similarity	NPC196718
0.7546	Intermediate Similarity	NPC185782
0.7535	Intermediate Similarity	NPC4687
0.7535	Intermediate Similarity	NPC283117
0.7535	Intermediate Similarity	NPC249583
0.7534	Intermediate Similarity	NPC477979
0.7531	Intermediate Similarity	NPC258048
0.7522	Intermediate Similarity	NPC235685
0.7522	Intermediate Similarity	NPC311906
0.7511	Intermediate Similarity	NPC303658
0.7489	Intermediate Similarity	NPC89508
0.7489	Intermediate Similarity	NPC476287
0.7489	Intermediate Similarity	NPC101350
0.7477	Intermediate Similarity	NPC146418
0.7456	Intermediate Similarity	NPC474701
0.7453	Intermediate Similarity	NPC128823
0.7443	Intermediate Similarity	NPC26679
0.7431	Intermediate Similarity	NPC471304
0.7426	Intermediate Similarity	NPC26543
0.7424	Intermediate Similarity	NPC49547
0.7422	Intermediate Similarity	NPC51388
0.7421	Intermediate Similarity	NPC322064
0.7419	Intermediate Similarity	NPC266249
0.7411	Intermediate Similarity	NPC118511
0.7406	Intermediate Similarity	NPC244543
0.7401	Intermediate Similarity	NPC74575
0.7397	Intermediate Similarity	NPC87413
0.7397	Intermediate Similarity	NPC220337
0.7397	Intermediate Similarity	NPC294375
0.7395	Intermediate Similarity	NPC476098
0.7387	Intermediate Similarity	NPC312645
0.7371	Intermediate Similarity	NPC184680
0.7364	Intermediate Similarity	NPC308137
0.7364	Intermediate Similarity	NPC310211
0.7364	Intermediate Similarity	NPC474428
0.7364	Intermediate Similarity	NPC118940
0.7362	Intermediate Similarity	NPC142385
0.7359	Intermediate Similarity	NPC34770
0.7358	Intermediate Similarity	NPC141454
0.7357	Intermediate Similarity	NPC470018
0.7354	Intermediate Similarity	NPC46561
0.7352	Intermediate Similarity	NPC123839
0.7342	Intermediate Similarity	NPC470799
0.7342	Intermediate Similarity	NPC152768
0.7342	Intermediate Similarity	NPC8022
0.7342	Intermediate Similarity	NPC148183
0.7339	Intermediate Similarity	NPC470785
0.7325	Intermediate Similarity	NPC185197
0.7322	Intermediate Similarity	NPC67401
0.7322	Intermediate Similarity	NPC473188
0.7315	Intermediate Similarity	NPC165599
0.7315	Intermediate Similarity	NPC134848
0.7313	Intermediate Similarity	NPC21638
0.7309	Intermediate Similarity	NPC293151
0.7309	Intermediate Similarity	NPC169402
0.7308	Intermediate Similarity	NPC475816
0.7303	Intermediate Similarity	NPC303374
0.7297	Intermediate Similarity	NPC116238
0.7297	Intermediate Similarity	NPC16066
0.7289	Intermediate Similarity	NPC472099
0.7282	Intermediate Similarity	NPC176127
0.7281	Intermediate Similarity	NPC470930
0.7277	Intermediate Similarity	NPC96321
0.7273	Intermediate Similarity	NPC269367
0.7269	Intermediate Similarity	NPC295898
0.7265	Intermediate Similarity	NPC470784
0.7257	Intermediate Similarity	NPC280799
0.7238	Intermediate Similarity	NPC91868
0.7238	Intermediate Similarity	NPC63971
0.7225	Intermediate Similarity	NPC216612
0.7222	Intermediate Similarity	NPC472061
0.7222	Intermediate Similarity	NPC240384
0.7222	Intermediate Similarity	NPC15801
0.7215	Intermediate Similarity	NPC244741
0.7212	Intermediate Similarity	NPC174760
0.721	Intermediate Similarity	NPC208898
0.7209	Intermediate Similarity	NPC280714
0.7207	Intermediate Similarity	NPC38237
0.7206	Intermediate Similarity	NPC151635
0.72	Intermediate Similarity	NPC247803
0.72	Intermediate Similarity	NPC174576
0.7198	Intermediate Similarity	NPC207686
0.7197	Intermediate Similarity	NPC161801
0.7195	Intermediate Similarity	NPC199667
0.7185	Intermediate Similarity	NPC208522
0.7182	Intermediate Similarity	NPC39679
0.7181	Intermediate Similarity	NPC60621
0.7178	Intermediate Similarity	NPC473800
0.7177	Intermediate Similarity	NPC160381
0.7176	Intermediate Similarity	NPC19872
0.7173	Intermediate Similarity	NPC166712
0.7173	Intermediate Similarity	NPC72905
0.7168	Intermediate Similarity	NPC74360
0.7163	Intermediate Similarity	NPC112937
0.7156	Intermediate Similarity	NPC144381
0.7156	Intermediate Similarity	NPC27041
0.715	Intermediate Similarity	NPC102592
0.715	Intermediate Similarity	NPC79356
0.7149	Intermediate Similarity	NPC473181
0.7143	Intermediate Similarity	NPC160100
0.7143	Intermediate Similarity	NPC208364
0.7137	Intermediate Similarity	NPC203373
0.7137	Intermediate Similarity	NPC150239
0.7137	Intermediate Similarity	NPC276657
0.7131	Intermediate Similarity	NPC478083
0.713	Intermediate Similarity	NPC264176
0.713	Intermediate Similarity	NPC472098
0.713	Intermediate Similarity	NPC94157
0.713	Intermediate Similarity	NPC473180
0.713	Intermediate Similarity	NPC219087
0.7129	Intermediate Similarity	NPC470894
0.7129	Intermediate Similarity	NPC42591
0.7124	Intermediate Similarity	NPC473041
0.7124	Intermediate Similarity	NPC474192
0.7124	Intermediate Similarity	NPC475720
0.7109	Intermediate Similarity	NPC196449
0.7109	Intermediate Similarity	NPC314222
0.7107	Intermediate Similarity	NPC137353
0.7106	Intermediate Similarity	NPC477549
0.7105	Intermediate Similarity	NPC198503
0.7104	Intermediate Similarity	NPC287208
0.7098	Intermediate Similarity	NPC324361
0.7097	Intermediate Similarity	NPC176538
0.7095	Intermediate Similarity	NPC270515
0.7093	Intermediate Similarity	NPC292958
0.7093	Intermediate Similarity	NPC269270
0.7083	Intermediate Similarity	NPC58209
0.7081	Intermediate Similarity	NPC84478
0.7078	Intermediate Similarity	NPC223427
0.7076	Intermediate Similarity	NPC470022
0.7061	Intermediate Similarity	NPC14686
0.7059	Intermediate Similarity	NPC193238
0.7056	Intermediate Similarity	NPC247735
0.7056	Intermediate Similarity	NPC472210
0.7056	Intermediate Similarity	NPC81802
0.7056	Intermediate Similarity	NPC230683
0.7056	Intermediate Similarity	NPC269886
0.7056	Intermediate Similarity	NPC472295
0.7037	Intermediate Similarity	NPC133609
0.7035	Intermediate Similarity	NPC36405
0.7034	Intermediate Similarity	NPC470017
0.703	Intermediate Similarity	NPC115232
0.7027	Intermediate Similarity	NPC171787
0.7027	Intermediate Similarity	NPC82548
0.7025	Intermediate Similarity	NPC173250
0.7023	Intermediate Similarity	NPC276517
0.7022	Intermediate Similarity	NPC236668
0.7019	Intermediate Similarity	NPC469896
0.7018	Intermediate Similarity	NPC298436
0.7015	Intermediate Similarity	NPC257763
0.7	Intermediate Similarity	NPC220851
0.6996	Remote Similarity	NPC325297

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 NPC288987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	723
0.2-0.3	937
0.3-0.4	1456
0.4-0.5	3196
0.5-0.6	1967
0.6-0.7	506
0.7-0.8	46
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7946	Intermediate Similarity	NPD3006	Discontinued
0.7936	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD4429	Discontinued
0.7742	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2951	Discontinued
0.7536	Intermediate Similarity	NPD2778	Approved
0.7532	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4368	Phase 2
0.7489	Intermediate Similarity	NPD5479	Discontinued
0.7489	Intermediate Similarity	NPD5022	Discontinued
0.7489	Intermediate Similarity	NPD3945	Discontinued
0.7477	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD2779	Approved
0.7424	Intermediate Similarity	NPD4885	Approved
0.7412	Intermediate Similarity	NPD4952	Phase 3
0.7376	Intermediate Similarity	NPD3257	Approved
0.7353	Intermediate Similarity	NPD5482	Discontinued
0.7328	Intermediate Similarity	NPD7853	Phase 2
0.7316	Intermediate Similarity	NPD4373	Phase 2
0.7304	Intermediate Similarity	NPD1867	Approved
0.7301	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6242	Discontinued
0.7273	Intermediate Similarity	NPD3746	Discontinued
0.726	Intermediate Similarity	NPD6376	Discontinued
0.7244	Intermediate Similarity	NPD3258	Approved
0.7238	Intermediate Similarity	NPD4558	Phase 2
0.7232	Intermediate Similarity	NPD5443	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5293	Phase 2
0.722	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3263	Phase 3
0.7203	Intermediate Similarity	NPD6790	Phase 1
0.7193	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8463	Approved
0.7186	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5924	Discontinued
0.7186	Intermediate Similarity	NPD1659	Phase 1
0.7173	Intermediate Similarity	NPD6716	Phase 1
0.7169	Intermediate Similarity	NPD3507	Phase 2
0.7162	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5416	Discontinued
0.7155	Intermediate Similarity	NPD1505	Phase 2
0.7155	Intermediate Similarity	NPD1466	Phase 3
0.7155	Intermediate Similarity	NPD1467	Approved
0.7143	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5850	Phase 3
0.713	Intermediate Similarity	NPD7603	Discontinued
0.7124	Intermediate Similarity	NPD5632	Approved
0.7117	Intermediate Similarity	NPD3392	Approved
0.71	Intermediate Similarity	NPD3259	Approved
0.71	Intermediate Similarity	NPD7994	Phase 2
0.7093	Intermediate Similarity	NPD6974	Phase 3
0.708	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2565	Phase 2
0.7075	Intermediate Similarity	NPD2564	Approved
0.7072	Intermediate Similarity	NPD4506	Discontinued
0.704	Intermediate Similarity	NPD2081	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4328	Approved
0.7005	Intermediate Similarity	NPD772	Phase 3
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5450	Discontinued
0.6991	Remote Similarity	NPD5512	Phase 3
0.6987	Remote Similarity	NPD7180	Phase 3
0.6979	Remote Similarity	NPD7031	Phase 1
0.6972	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5658	Approved
0.6943	Remote Similarity	NPD6770	Approved
0.6926	Remote Similarity	NPD6209	Approved
0.6913	Remote Similarity	NPD1996	Discontinued
0.6908	Remote Similarity	NPD7708	Approved
0.6907	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7395	Discontinued
0.6898	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD1038	Approved
0.6891	Remote Similarity	NPD3250	Phase 1
0.6881	Remote Similarity	NPD5003	Discontinued
0.688	Remote Similarity	NPD4845	Discontinued
0.6875	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6962	Phase 2
0.6856	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5256	Discontinued
0.6851	Remote Similarity	NPD5559	Phase 2
0.6849	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5429	Discontinued
0.6828	Remote Similarity	NPD5866	Approved
0.6816	Remote Similarity	NPD3947	Discontinued
0.6812	Remote Similarity	NPD3389	Approved
0.6812	Remote Similarity	NPD3394	Approved
0.6812	Remote Similarity	NPD3393	Approved
0.68	Remote Similarity	NPD2510	Approved
0.68	Remote Similarity	NPD2509	Approved
0.6798	Remote Similarity	NPD7803	Approved
0.6795	Remote Similarity	NPD3925	Approved
0.6792	Remote Similarity	NPD3488	Phase 1
0.6789	Remote Similarity	NPD3986	Discontinued
0.6787	Remote Similarity	NPD6961	Discontinued
0.6784	Remote Similarity	NPD4502	Phase 2
0.6771	Remote Similarity	NPD2920	Discontinued
0.6769	Remote Similarity	NPD1638	Discovery
0.6761	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6456	Discontinued
0.6757	Remote Similarity	NPD6321	Discontinued
0.6751	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8102	Discontinued
0.6741	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD484	Approved
0.6712	Remote Similarity	NPD4500	Approved
0.6712	Remote Similarity	NPD4501	Approved
0.6707	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8091	Phase 3
0.6682	Remote Similarity	NPD6550	Discontinued
0.6681	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6568	Discontinued
0.6681	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6517	Phase 3
0.668	Remote Similarity	NPD4454	Phase 2
0.668	Remote Similarity	NPD1936	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7688	Phase 1
0.6653	Remote Similarity	NPD946	Discontinued
0.6652	Remote Similarity	NPD7467	Discontinued
0.6652	Remote Similarity	NPD3243	Approved
0.6651	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6530	Approved
0.664	Remote Similarity	NPD6228	Discontinued
0.664	Remote Similarity	NPD8358	Approved
0.664	Remote Similarity	NPD6531	Approved
0.6639	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5164	Discontinued
0.6637	Remote Similarity	NPD3003	Approved
0.6636	Remote Similarity	NPD4418	Discontinued
0.6623	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6176	Phase 1
0.6608	Remote Similarity	NPD7222	Phase 2
0.6603	Remote Similarity	NPD7872	Phase 2
0.6601	Remote Similarity	NPD7956	Approved
0.6601	Remote Similarity	NPD7955	Approved
0.6598	Remote Similarity	NPD8016	Phase 3
0.6598	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4923	Phase 1
0.6593	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD1768	Approved
0.6589	Remote Similarity	NPD4204	Approved
0.6589	Remote Similarity	NPD4203	Approved
0.6582	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD4442	Phase 2
0.6573	Remote Similarity	NPD3328	Phase 2
0.6565	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6590	Discontinued
0.6557	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5902	Approved
0.6552	Remote Similarity	NPD5903	Approved
0.6552	Remote Similarity	NPD4897	Phase 2
0.6545	Remote Similarity	NPD7022	Phase 2
0.6545	Remote Similarity	NPD4322	Discontinued
0.6538	Remote Similarity	NPD1926	Approved
0.6532	Remote Similarity	NPD5488	Discontinued
0.6524	Remote Similarity	NPD5612	Discontinued
0.6524	Remote Similarity	NPD5183	Approved
0.6524	Remote Similarity	NPD5186	Approved
0.6522	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.652	Remote Similarity	NPD4795	Phase 2
0.652	Remote Similarity	NPD6745	Discontinued
0.652	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD2177	Approved
0.6518	Remote Similarity	NPD2176	Approved
0.6518	Remote Similarity	NPD3825	Phase 3
0.6518	Remote Similarity	NPD2175	Phase 3
0.6515	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4515	Suspended
0.6509	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD4353	Phase 2
0.6507	Remote Similarity	NPD2916	Discontinued
0.6496	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD3920	Phase 2
0.6494	Remote Similarity	NPD7470	Discontinued
0.6493	Remote Similarity	NPD1955	Discontinued
0.6492	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1739	Approved
0.6489	Remote Similarity	NPD1740	Approved
0.6488	Remote Similarity	NPD7797	Approved
0.6488	Remote Similarity	NPD7796	Approved
0.6486	Remote Similarity	NPD7924	Phase 2

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