NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.07
Volume:	237.644
LogP:	2.421
LogD:	2.23
LogS:	-3.475
# Rotatable Bonds:	2
TPSA:	75.21
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.641
Synthetic Accessibility Score:	2.425
Fsp3:	0.077
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:	-4.984
MDCK Permeability:	1.1936044757021591e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.266

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.837
Plasma Protein Binding (PPB):	89.54596710205078%
Volume Distribution (VD):	0.692
Pgp-substrate:	10.539433479309082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.435
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.572
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.772
CYP2D6-substrate:	0.661
CYP3A4-inhibitor:	0.559
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	7.684
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.444
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.157
Rat Oral Acute Toxicity:	0.497
Maximum Recommended Daily Dose:	0.713
Skin Sensitization:	0.714
Carcinogencity:	0.134
Eye Corrosion:	0.029
Eye Irritation:	0.966
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC182222

Natural Product ID:	NPC182222
*Common Name:**	4-Hydroxy-1-Methoxycarbonyl-Beta-Carboline
IUPAC Name:	methyl 4-hydroxy-9H-pyrido[3,4-b]indole-1-carboxylate
Synonyms:
Standard InCHIKey:	SRJGEVLILAHFEY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10N2O3/c1-18-13(17)12-11-10(9(16)6-14-12)7-4-2-3-5-8(7)15-11/h2-6,15-16H,1H3
SMILES:	COC(=O)c1c2c(c3ccccc3[nH]2)c(cn1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229721
PubChem CID:	15573072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
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]
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]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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
Others	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	69.2	%	PMID[573184]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	60.0	%	PMID[573184]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	62.3	%	PMID[573184]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	45.7	%	PMID[573184]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	55.6	%	PMID[573184]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	41.7	%	PMID[573184]

☑ 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 NPC182222 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	467
0.1-0.2	3021
0.2-0.3	12817
0.3-0.4	7087
0.4-0.5	14543
0.5-0.6	2108
0.6-0.7	2160
0.7-0.8	464
0.8-0.85	24
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC266249
0.8874	High Similarity	NPC148889
0.8853	High Similarity	NPC260434
0.8804	High Similarity	NPC123839
0.8565	High Similarity	NPC74360
0.8558	High Similarity	NPC27041
0.8493	Intermediate Similarity	NPC122436
0.8462	Intermediate Similarity	NPC258048
0.8372	Intermediate Similarity	NPC118940
0.8341	Intermediate Similarity	NPC8022
0.8341	Intermediate Similarity	NPC470799
0.834	Intermediate Similarity	NPC53534
0.824	Intermediate Similarity	NPC91868
0.824	Intermediate Similarity	NPC63971
0.8235	Intermediate Similarity	NPC60621
0.823	Intermediate Similarity	NPC207686
0.8199	Intermediate Similarity	NPC19872
0.8166	Intermediate Similarity	NPC15801
0.8133	Intermediate Similarity	NPC152620
0.8131	Intermediate Similarity	NPC132539
0.8128	Intermediate Similarity	NPC165964
0.8087	Intermediate Similarity	NPC235685
0.8082	Intermediate Similarity	NPC89508
0.808	Intermediate Similarity	NPC229893
0.807	Intermediate Similarity	NPC279189
0.807	Intermediate Similarity	NPC200553
0.8065	Intermediate Similarity	NPC185782
0.8052	Intermediate Similarity	NPC101350
0.8047	Intermediate Similarity	NPC472259
0.8045	Intermediate Similarity	NPC477979
0.8	Intermediate Similarity	NPC97902
0.7981	Intermediate Similarity	NPC476167
0.7973	Intermediate Similarity	NPC312645
0.7972	Intermediate Similarity	NPC193238
0.7965	Intermediate Similarity	NPC162002
0.7963	Intermediate Similarity	NPC470500
0.7955	Intermediate Similarity	NPC26679
0.7953	Intermediate Similarity	NPC57398
0.7934	Intermediate Similarity	NPC192315
0.7922	Intermediate Similarity	NPC174489
0.7919	Intermediate Similarity	NPC476287
0.7917	Intermediate Similarity	NPC165599
0.7913	Intermediate Similarity	NPC196718
0.7913	Intermediate Similarity	NPC102593
0.7905	Intermediate Similarity	NPC138370
0.7887	Intermediate Similarity	NPC141454
0.7854	Intermediate Similarity	NPC171787
0.7854	Intermediate Similarity	NPC26641
0.7848	Intermediate Similarity	NPC322064
0.7848	Intermediate Similarity	NPC178858
0.7834	Intermediate Similarity	NPC476138
0.7834	Intermediate Similarity	NPC245816
0.783	Intermediate Similarity	NPC230403
0.7819	Intermediate Similarity	NPC74619
0.7811	Intermediate Similarity	NPC477549
0.7808	Intermediate Similarity	NPC244741
0.7804	Intermediate Similarity	NPC267928
0.7793	Intermediate Similarity	NPC219087
0.7788	Intermediate Similarity	NPC284678
0.7788	Intermediate Similarity	NPC276657
0.7787	Intermediate Similarity	NPC37152
0.7778	Intermediate Similarity	NPC315491
0.7778	Intermediate Similarity	NPC45459
0.7773	Intermediate Similarity	NPC287208
0.7767	Intermediate Similarity	NPC474916
0.7762	Intermediate Similarity	NPC278434
0.7752	Intermediate Similarity	NPC476098
0.7741	Intermediate Similarity	NPC161801
0.7727	Intermediate Similarity	NPC183777
0.7723	Intermediate Similarity	NPC118228
0.7718	Intermediate Similarity	NPC473800
0.7709	Intermediate Similarity	NPC323969
0.7703	Intermediate Similarity	NPC5145
0.7696	Intermediate Similarity	NPC24370
0.7696	Intermediate Similarity	NPC319232
0.7692	Intermediate Similarity	NPC191415
0.7689	Intermediate Similarity	NPC36405
0.7676	Intermediate Similarity	NPC26543
0.7673	Intermediate Similarity	NPC216369
0.7665	Intermediate Similarity	NPC213530
0.7665	Intermediate Similarity	NPC193267
0.7661	Intermediate Similarity	NPC232727
0.7656	Intermediate Similarity	NPC48938
0.7647	Intermediate Similarity	NPC321428
0.7647	Intermediate Similarity	NPC270918
0.7639	Intermediate Similarity	NPC90229
0.7627	Intermediate Similarity	NPC240384
0.7623	Intermediate Similarity	NPC309845
0.7617	Intermediate Similarity	NPC324149
0.7615	Intermediate Similarity	NPC213308
0.7615	Intermediate Similarity	NPC176538
0.7615	Intermediate Similarity	NPC316224
0.7613	Intermediate Similarity	NPC39679
0.7607	Intermediate Similarity	NPC101543
0.7607	Intermediate Similarity	NPC469554
0.7598	Intermediate Similarity	NPC310118
0.7589	Intermediate Similarity	NPC82370
0.7588	Intermediate Similarity	NPC288987
0.7574	Intermediate Similarity	NPC323752
0.7571	Intermediate Similarity	NPC102755
0.7569	Intermediate Similarity	NPC81535
0.7565	Intermediate Similarity	NPC216612
0.7565	Intermediate Similarity	NPC478141
0.7556	Intermediate Similarity	NPC110182
0.7549	Intermediate Similarity	NPC314222
0.7549	Intermediate Similarity	NPC196449
0.7546	Intermediate Similarity	NPC276517
0.7544	Intermediate Similarity	NPC184408
0.7523	Intermediate Similarity	NPC239954
0.7522	Intermediate Similarity	NPC221100
0.7522	Intermediate Similarity	NPC234078
0.7512	Intermediate Similarity	NPC102592
0.7512	Intermediate Similarity	NPC79356
0.7511	Intermediate Similarity	NPC57453
0.75	Intermediate Similarity	NPC471944
0.75	Intermediate Similarity	NPC282103
0.75	Intermediate Similarity	NPC295452
0.75	Intermediate Similarity	NPC198673
0.75	Intermediate Similarity	NPC171393
0.7489	Intermediate Similarity	NPC280714
0.7489	Intermediate Similarity	NPC477112
0.7489	Intermediate Similarity	NPC474701
0.748	Intermediate Similarity	NPC472435
0.7477	Intermediate Similarity	NPC156704
0.7477	Intermediate Similarity	NPC475070
0.7477	Intermediate Similarity	NPC44354
0.7467	Intermediate Similarity	NPC264285
0.7465	Intermediate Similarity	NPC62749
0.7457	Intermediate Similarity	NPC51388
0.7444	Intermediate Similarity	NPC82053
0.7443	Intermediate Similarity	NPC306376
0.7443	Intermediate Similarity	NPC212213
0.7442	Intermediate Similarity	NPC144381
0.7436	Intermediate Similarity	NPC110151
0.7435	Intermediate Similarity	NPC313804
0.7435	Intermediate Similarity	NPC315804
0.7434	Intermediate Similarity	NPC87413
0.7414	Intermediate Similarity	NPC470501
0.7411	Intermediate Similarity	NPC88008
0.7404	Intermediate Similarity	NPC194740
0.7404	Intermediate Similarity	NPC314954
0.739	Intermediate Similarity	NPC472436
0.7389	Intermediate Similarity	NPC167860
0.7389	Intermediate Similarity	NPC123976
0.738	Intermediate Similarity	NPC3207
0.7371	Intermediate Similarity	NPC470502
0.7368	Intermediate Similarity	NPC39500
0.7366	Intermediate Similarity	NPC175602
0.7364	Intermediate Similarity	NPC168911
0.7362	Intermediate Similarity	NPC192712
0.7362	Intermediate Similarity	NPC257851
0.7359	Intermediate Similarity	NPC269270
0.7355	Intermediate Similarity	NPC473312
0.7354	Intermediate Similarity	NPC200836
0.7354	Intermediate Similarity	NPC53144
0.7353	Intermediate Similarity	NPC141053
0.735	Intermediate Similarity	NPC21638
0.735	Intermediate Similarity	NPC179287
0.7349	Intermediate Similarity	NPC63109
0.7349	Intermediate Similarity	NPC46580
0.7348	Intermediate Similarity	NPC472285
0.7345	Intermediate Similarity	NPC61038
0.7339	Intermediate Similarity	NPC220851
0.7336	Intermediate Similarity	NPC314002
0.7333	Intermediate Similarity	NPC283117
0.733	Intermediate Similarity	NPC18487
0.7328	Intermediate Similarity	NPC14686
0.7311	Intermediate Similarity	NPC474192
0.7311	Intermediate Similarity	NPC475720
0.7309	Intermediate Similarity	NPC211813
0.7308	Intermediate Similarity	NPC470503
0.7304	Intermediate Similarity	NPC330009
0.7304	Intermediate Similarity	NPC288349
0.7304	Intermediate Similarity	NPC469928
0.73	Intermediate Similarity	NPC326363
0.7295	Intermediate Similarity	NPC78609
0.7295	Intermediate Similarity	NPC208522
0.729	Intermediate Similarity	NPC207851
0.729	Intermediate Similarity	NPC204717
0.7288	Intermediate Similarity	NPC186351
0.7288	Intermediate Similarity	NPC478078
0.7284	Intermediate Similarity	NPC292958
0.7281	Intermediate Similarity	NPC469489
0.7281	Intermediate Similarity	NPC294375
0.728	Intermediate Similarity	NPC473105
0.7277	Intermediate Similarity	NPC125597
0.7273	Intermediate Similarity	NPC469727
0.7269	Intermediate Similarity	NPC174672
0.7269	Intermediate Similarity	NPC267853
0.7269	Intermediate Similarity	NPC174758
0.7269	Intermediate Similarity	NPC315062
0.7265	Intermediate Similarity	NPC16352
0.7264	Intermediate Similarity	NPC248041
0.7264	Intermediate Similarity	NPC126709
0.7261	Intermediate Similarity	NPC184225
0.7261	Intermediate Similarity	NPC237740
0.726	Intermediate Similarity	NPC307963
0.726	Intermediate Similarity	NPC326422
0.7257	Intermediate Similarity	NPC471762
0.7257	Intermediate Similarity	NPC4687

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 NPC182222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	630
0.2-0.3	893
0.3-0.4	1455
0.4-0.5	2901
0.5-0.6	1910
0.6-0.7	1022
0.7-0.8	74
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8414	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8362	Intermediate Similarity	NPD5482	Discontinued
0.819	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD3006	Discontinued
0.8	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD5450	Discontinued
0.7854	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD7603	Discontinued
0.7778	Intermediate Similarity	NPD484	Approved
0.7773	Intermediate Similarity	NPD2509	Approved
0.7773	Intermediate Similarity	NPD2510	Approved
0.7699	Intermediate Similarity	NPD4429	Discontinued
0.7689	Intermediate Similarity	NPD3394	Approved
0.7689	Intermediate Similarity	NPD3389	Approved
0.7689	Intermediate Similarity	NPD3393	Approved
0.7555	Intermediate Similarity	NPD1996	Discontinued
0.7521	Intermediate Similarity	NPD5022	Discontinued
0.7511	Intermediate Similarity	NPD5416	Discontinued
0.7468	Intermediate Similarity	NPD3263	Phase 3
0.7434	Intermediate Similarity	NPD5475	Discontinued
0.7426	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6242	Discontinued
0.7395	Intermediate Similarity	NPD2951	Discontinued
0.7391	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7853	Phase 2
0.7339	Intermediate Similarity	NPD8356	Approved
0.7316	Intermediate Similarity	NPD5632	Approved
0.7298	Intermediate Similarity	NPD8370	Discontinued
0.7288	Intermediate Similarity	NPD8430	Approved
0.7288	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4845	Discontinued
0.7281	Intermediate Similarity	NPD7470	Discontinued
0.7277	Intermediate Similarity	NPD3178	Discontinued
0.7276	Intermediate Similarity	NPD4558	Phase 2
0.7273	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1038	Approved
0.7247	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5901	Discontinued
0.7229	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD3794	Approved
0.7217	Intermediate Similarity	NPD3795	Approved
0.7207	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3330	Phase 1
0.717	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2094	Phase 2
0.7163	Intermediate Similarity	NPD2092	Phase 2
0.7163	Intermediate Similarity	NPD2095	Phase 2
0.7162	Intermediate Similarity	NPD5003	Discontinued
0.7161	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6530	Approved
0.7154	Intermediate Similarity	NPD6531	Approved
0.7143	Intermediate Similarity	NPD7994	Phase 2
0.7143	Intermediate Similarity	NPD3259	Approved
0.7137	Intermediate Similarity	NPD7404	Approved
0.7137	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD4373	Phase 2
0.7137	Intermediate Similarity	NPD6770	Approved
0.713	Intermediate Similarity	NPD2096	Phase 2
0.713	Intermediate Similarity	NPD2091	Phase 2
0.7123	Intermediate Similarity	NPD482	Approved
0.7119	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1856	Discontinued
0.7105	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5640	Discontinued
0.7101	Intermediate Similarity	NPD8289	Discontinued
0.71	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7948	Phase 1
0.7083	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4952	Phase 3
0.7082	Intermediate Similarity	NPD5612	Discontinued
0.7074	Intermediate Similarity	NPD6376	Discontinued
0.7066	Intermediate Similarity	NPD7558	Phase 2
0.7066	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3779	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4368	Phase 2
0.704	Intermediate Similarity	NPD5512	Phase 3
0.7039	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4948	Discontinued
0.7008	Intermediate Similarity	NPD8091	Phase 3
0.7	Intermediate Similarity	NPD4086	Phase 1
0.6996	Remote Similarity	NPD3243	Approved
0.6991	Remote Similarity	NPD4501	Approved
0.6991	Remote Similarity	NPD4500	Approved
0.6987	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5066	Phase 2
0.6983	Remote Similarity	NPD5067	Phase 2
0.6979	Remote Similarity	NPD4989	Phase 2
0.6975	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6176	Phase 1
0.6972	Remote Similarity	NPD1096	Discontinued
0.697	Remote Similarity	NPD4506	Discontinued
0.6969	Remote Similarity	NPD8049	Phase 2
0.6968	Remote Similarity	NPD2564	Approved
0.6968	Remote Similarity	NPD2565	Phase 2
0.6968	Remote Similarity	NPD1213	Phase 3
0.6967	Remote Similarity	NPD424	Approved
0.6967	Remote Similarity	NPD425	Approved
0.6966	Remote Similarity	NPD5293	Phase 2
0.6964	Remote Similarity	NPD6790	Phase 1
0.6962	Remote Similarity	NPD3280	Approved
0.6957	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1392	Approved
0.6953	Remote Similarity	NPD5866	Approved
0.6953	Remote Similarity	NPD7069	Discontinued
0.695	Remote Similarity	NPD4442	Phase 2
0.6949	Remote Similarity	NPD7395	Discontinued
0.6949	Remote Similarity	NPD3354	Phase 2
0.6948	Remote Similarity	NPD3962	Phase 2
0.6948	Remote Similarity	NPD3959	Phase 2
0.6943	Remote Similarity	NPD4795	Phase 2
0.6943	Remote Similarity	NPD4038	Approved
0.6943	Remote Similarity	NPD4035	Approved
0.6943	Remote Similarity	NPD3947	Discontinued
0.6943	Remote Similarity	NPD4033	Approved
0.6943	Remote Similarity	NPD4037	Approved
0.6943	Remote Similarity	NPD4039	Approved
0.6943	Remote Similarity	NPD32	Approved
0.6943	Remote Similarity	NPD31	Approved
0.6943	Remote Similarity	NPD4034	Approved
0.6943	Remote Similarity	NPD4036	Approved
0.6943	Remote Similarity	NPD4122	Approved
0.6942	Remote Similarity	NPD5479	Discontinued
0.6942	Remote Similarity	NPD1659	Phase 1
0.6939	Remote Similarity	NPD4454	Phase 2
0.6936	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.693	Remote Similarity	NPD2779	Approved
0.6923	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD750	Phase 2
0.6916	Remote Similarity	NPD1739	Approved
0.6916	Remote Similarity	NPD1740	Approved
0.6909	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5559	Phase 2
0.6897	Remote Similarity	NPD6529	Discontinued
0.6895	Remote Similarity	NPD7417	Discontinued
0.6894	Remote Similarity	NPD4897	Phase 2
0.6892	Remote Similarity	NPD6276	Discontinued
0.6891	Remote Similarity	NPD5850	Phase 3
0.6885	Remote Similarity	NPD3746	Discontinued
0.6885	Remote Similarity	NPD1572	Phase 2
0.6884	Remote Similarity	NPD5065	Approved
0.6884	Remote Similarity	NPD9690	Approved
0.6881	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8093	Discontinued
0.6879	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD802	Phase 2
0.6873	Remote Similarity	NPD6456	Discontinued
0.6872	Remote Similarity	NPD2176	Approved
0.6872	Remote Similarity	NPD2177	Approved
0.6872	Remote Similarity	NPD3825	Phase 3
0.6872	Remote Similarity	NPD2175	Phase 3
0.6867	Remote Similarity	NPD6716	Phase 1
0.6867	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1955	Discontinued
0.6851	Remote Similarity	NPD3945	Discontinued
0.6849	Remote Similarity	NPD6974	Phase 3
0.6846	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7803	Approved
0.684	Remote Similarity	NPD7001	Phase 3
0.6838	Remote Similarity	NPD3986	Discontinued
0.6838	Remote Similarity	NPD949	Phase 1
0.6838	Remote Similarity	NPD4502	Phase 2
0.6835	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1571	Phase 2
0.6829	Remote Similarity	NPD3074	Discontinued
0.6824	Remote Similarity	NPD8463	Approved
0.6824	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7708	Approved
0.6822	Remote Similarity	NPD5116	Phase 1
0.682	Remote Similarity	NPD6159	Phase 2
0.6818	Remote Similarity	NPD5018	Phase 3
0.6818	Remote Similarity	NPD1273	Discontinued
0.6816	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7878	Phase 2
0.6805	Remote Similarity	NPD6173	Approved
0.6802	Remote Similarity	NPD5891	Approved
0.68	Remote Similarity	NPD1483	Discontinued
0.6798	Remote Similarity	NPD2778	Approved
0.6798	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4850	Phase 1
0.6787	Remote Similarity	NPD1927	Discontinued
0.6786	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1229	Phase 2
0.6781	Remote Similarity	NPD5658	Approved
0.678	Remote Similarity	NPD7689	Approved
0.6777	Remote Similarity	NPD9705	Discontinued
0.6777	Remote Similarity	NPD112	Approved
0.6776	Remote Similarity	NPD1505	Phase 2
0.6772	Remote Similarity	NPD3809	Discontinued
0.6772	Remote Similarity	NPD8101	Phase 3
0.6769	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7010	Phase 3
0.6767	Remote Similarity	NPD3003	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