NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.08
Volume:	220.063
LogP:	2.874
LogD:	2.57
LogS:	-3.378
# Rotatable Bonds:	1
TPSA:	48.91
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	2.743
Fsp3:	0.0
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:	-4.982
MDCK Permeability:	1.8244410966872238e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.494
Plasma Protein Binding (PPB):	91.67760467529297%
Volume Distribution (VD):	0.751
Pgp-substrate:	6.356071472167969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.749
CYP2C19-inhibitor:	0.351
CYP2C19-substrate:	0.153
CYP2C9-inhibitor:	0.654
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.499
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	6.088
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.815
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.327
Skin Sensitization:	0.898
Carcinogencity:	0.475
Eye Corrosion:	0.199
Eye Irritation:	0.985
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC192315

Natural Product ID:	NPC192315
*Common Name:**	1-Vinyl-8-Hydroxy-Beta-Carboline
IUPAC Name:	1-ethenyl-9H-pyrido[3,4-b]indol-8-ol
Synonyms:
Standard InCHIKey:	RZWQZVWQFRVQCI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10N2O/c1-2-10-12-9(6-7-14-10)8-4-3-5-11(16)13(8)15-12/h2-7,15-16H,1H2
SMILES:	C=Cc1nccc2c1[nH]c1c2cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444237
PubChem CID:	5353368
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
NPO2833	Cribricellina cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791472]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	Alderman Islands off the North Island of New Zealand	n.a.	PMID[18052329]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	New Zealand	n.a.	PMID[19220033]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19220033]
NPO21386	Catenicella cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277321]
NPO25419	Pterocella vesiculosa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21386	Catenicella cribraria	Species	Catenicellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2833	Cribricellina cribraria	Species	Catenicellidae	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
GI50	1
IC50	2
MIC	6
Others	8

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	11
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[513267]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.1	ug.mL-1	PMID[513269]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[513267]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7.5	ug	PMID[513267]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[513267]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	15.0	ug	PMID[513267]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	0.45	ug	PMID[513267]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	=	3.7	ug	PMID[513267]
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IZ	=	1.0	mm	PMID[513267]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	IZ	=	1.0	mm	PMID[513267]
NPT27	Others	Unspecified		IZ	=	2.0	mm	PMID[513267]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	1800.0	nM	PMID[513268]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	5800.0	nM	PMID[513268]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	19000.0	nM	PMID[513268]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MID	=	0.45	ug ml-1	PMID[513269]
NPT20	Organism	Candida albicans	Candida albicans	MID	=	15.0	ug ml-1	PMID[513269]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MID	=	7.5	ug ml-1	PMID[513269]

☑ 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 NPC192315 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	695
0.1-0.2	6388
0.2-0.3	11253
0.3-0.4	15200
0.4-0.5	4927
0.5-0.6	2036
0.6-0.7	1681
0.7-0.8	461
0.8-0.85	35
0.85-0.9	17
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9943	High Similarity	NPC476167
0.9086	High Similarity	NPC476138
0.9086	High Similarity	NPC245816
0.8964	High Similarity	NPC470799
0.8964	High Similarity	NPC8022
0.8901	High Similarity	NPC5145
0.8852	High Similarity	NPC324149
0.8836	High Similarity	NPC475070
0.8743	High Similarity	NPC314940
0.8743	High Similarity	NPC473764
0.8737	High Similarity	NPC470500
0.8722	High Similarity	NPC48938
0.8667	High Similarity	NPC476287
0.8653	High Similarity	NPC185782
0.8619	High Similarity	NPC220765
0.8578	High Similarity	NPC476451
0.8571	High Similarity	NPC204717
0.8526	High Similarity	NPC19872
0.8526	High Similarity	NPC176538
0.8525	High Similarity	NPC314002
0.852	High Similarity	NPC26679
0.8478	Intermediate Similarity	NPC171171
0.8449	Intermediate Similarity	NPC99666
0.8398	Intermediate Similarity	NPC184964
0.838	Intermediate Similarity	NPC252590
0.8358	Intermediate Similarity	NPC292958
0.835	Intermediate Similarity	NPC476041
0.835	Intermediate Similarity	NPC304926
0.8342	Intermediate Similarity	NPC211813
0.8333	Intermediate Similarity	NPC46580
0.8308	Intermediate Similarity	NPC477113
0.829	Intermediate Similarity	NPC232727
0.8272	Intermediate Similarity	NPC77555
0.827	Intermediate Similarity	NPC284678
0.8223	Intermediate Similarity	NPC477111
0.8216	Intermediate Similarity	NPC473312
0.8164	Intermediate Similarity	NPC6215
0.8122	Intermediate Similarity	NPC476121
0.8122	Intermediate Similarity	NPC476124
0.8112	Intermediate Similarity	NPC53144
0.8098	Intermediate Similarity	NPC96890
0.8088	Intermediate Similarity	NPC213530
0.8088	Intermediate Similarity	NPC193267
0.8083	Intermediate Similarity	NPC156704
0.8083	Intermediate Similarity	NPC267928
0.8065	Intermediate Similarity	NPC471891
0.8065	Intermediate Similarity	NPC314394
0.8058	Intermediate Similarity	NPC470501
0.8054	Intermediate Similarity	NPC42979
0.8051	Intermediate Similarity	NPC315491
0.8051	Intermediate Similarity	NPC45459
0.8043	Intermediate Similarity	NPC224764
0.8031	Intermediate Similarity	NPC242209
0.803	Intermediate Similarity	NPC477110
0.802	Intermediate Similarity	NPC475774
0.802	Intermediate Similarity	NPC200836
0.801	Intermediate Similarity	NPC470502
0.8009	Intermediate Similarity	NPC469554
0.8009	Intermediate Similarity	NPC101543
0.7989	Intermediate Similarity	NPC131718
0.7981	Intermediate Similarity	NPC245348
0.798	Intermediate Similarity	NPC470505
0.796	Intermediate Similarity	NPC123976
0.796	Intermediate Similarity	NPC167860
0.7959	Intermediate Similarity	NPC213308
0.7957	Intermediate Similarity	NPC72980
0.7957	Intermediate Similarity	NPC88363
0.7953	Intermediate Similarity	NPC477861
0.7943	Intermediate Similarity	NPC60006
0.7938	Intermediate Similarity	NPC251090
0.7934	Intermediate Similarity	NPC182222
0.7933	Intermediate Similarity	NPC470503
0.7929	Intermediate Similarity	NPC223427
0.7929	Intermediate Similarity	NPC476098
0.7927	Intermediate Similarity	NPC307963
0.7921	Intermediate Similarity	NPC141353
0.7914	Intermediate Similarity	NPC478032
0.7906	Intermediate Similarity	NPC296527
0.7902	Intermediate Similarity	NPC27041
0.7887	Intermediate Similarity	NPC326634
0.7871	Intermediate Similarity	NPC85273
0.7868	Intermediate Similarity	NPC249040
0.7865	Intermediate Similarity	NPC76748
0.7861	Intermediate Similarity	NPC18348
0.7843	Intermediate Similarity	NPC477610
0.784	Intermediate Similarity	NPC207686
0.7838	Intermediate Similarity	NPC474409
0.7837	Intermediate Similarity	NPC310118
0.7837	Intermediate Similarity	NPC60621
0.7835	Intermediate Similarity	NPC329541
0.7824	Intermediate Similarity	NPC92111
0.7824	Intermediate Similarity	NPC41679
0.7817	Intermediate Similarity	NPC128823
0.7812	Intermediate Similarity	NPC242928
0.7812	Intermediate Similarity	NPC32771
0.7802	Intermediate Similarity	NPC102423
0.7794	Intermediate Similarity	NPC471603
0.7789	Intermediate Similarity	NPC470678
0.7778	Intermediate Similarity	NPC474798
0.7767	Intermediate Similarity	NPC142901
0.7766	Intermediate Similarity	NPC212213
0.7762	Intermediate Similarity	NPC167908
0.7755	Intermediate Similarity	NPC222018
0.7752	Intermediate Similarity	NPC81175
0.7734	Intermediate Similarity	NPC476116
0.7731	Intermediate Similarity	NPC295228
0.7727	Intermediate Similarity	NPC63545
0.7723	Intermediate Similarity	NPC88008
0.7723	Intermediate Similarity	NPC283117
0.7717	Intermediate Similarity	NPC171393
0.7717	Intermediate Similarity	NPC295452
0.7711	Intermediate Similarity	NPC472259
0.7711	Intermediate Similarity	NPC285558
0.7708	Intermediate Similarity	NPC314573
0.7708	Intermediate Similarity	NPC62749
0.7704	Intermediate Similarity	NPC276517
0.77	Intermediate Similarity	NPC314954
0.77	Intermediate Similarity	NPC473761
0.7692	Intermediate Similarity	NPC25899
0.7692	Intermediate Similarity	NPC279918
0.7689	Intermediate Similarity	NPC132631
0.7689	Intermediate Similarity	NPC103687
0.7685	Intermediate Similarity	NPC82548
0.7685	Intermediate Similarity	NPC97902
0.7685	Intermediate Similarity	NPC287208
0.7684	Intermediate Similarity	NPC201380
0.7684	Intermediate Similarity	NPC179787
0.7684	Intermediate Similarity	NPC469811
0.7677	Intermediate Similarity	NPC265576
0.767	Intermediate Similarity	NPC266931
0.7659	Intermediate Similarity	NPC208284
0.7656	Intermediate Similarity	NPC15102
0.7653	Intermediate Similarity	NPC110151
0.7653	Intermediate Similarity	NPC106937
0.765	Intermediate Similarity	NPC282231
0.765	Intermediate Similarity	NPC48192
0.7644	Intermediate Similarity	NPC212535
0.764	Intermediate Similarity	NPC321911
0.7637	Intermediate Similarity	NPC230869
0.7635	Intermediate Similarity	NPC270918
0.7629	Intermediate Similarity	NPC246700
0.7629	Intermediate Similarity	NPC128751
0.7619	Intermediate Similarity	NPC132642
0.7612	Intermediate Similarity	NPC57398
0.7608	Intermediate Similarity	NPC477609
0.7594	Intermediate Similarity	NPC130570
0.759	Intermediate Similarity	NPC469497
0.759	Intermediate Similarity	NPC106833
0.7588	Intermediate Similarity	NPC239954
0.7581	Intermediate Similarity	NPC63751
0.7573	Intermediate Similarity	NPC294375
0.7571	Intermediate Similarity	NPC159856
0.7565	Intermediate Similarity	NPC94943
0.7563	Intermediate Similarity	NPC198673
0.7557	Intermediate Similarity	NPC39092
0.7553	Intermediate Similarity	NPC313791
0.7552	Intermediate Similarity	NPC176127
0.7549	Intermediate Similarity	NPC166492
0.7549	Intermediate Similarity	NPC473362
0.7546	Intermediate Similarity	NPC260434
0.7536	Intermediate Similarity	NPC276657
0.7536	Intermediate Similarity	NPC94157
0.7536	Intermediate Similarity	NPC316981
0.7536	Intermediate Similarity	NPC219087
0.7534	Intermediate Similarity	NPC184225
0.7527	Intermediate Similarity	NPC54988
0.7527	Intermediate Similarity	NPC49954
0.7527	Intermediate Similarity	NPC474561
0.7524	Intermediate Similarity	NPC264285
0.7523	Intermediate Similarity	NPC24370
0.7523	Intermediate Similarity	NPC319232
0.7514	Intermediate Similarity	NPC469763
0.7514	Intermediate Similarity	NPC469786
0.7514	Intermediate Similarity	NPC259644
0.7514	Intermediate Similarity	NPC469765
0.7514	Intermediate Similarity	NPC469760
0.7514	Intermediate Similarity	NPC25008
0.7514	Intermediate Similarity	NPC325903
0.7514	Intermediate Similarity	NPC73952
0.7514	Intermediate Similarity	NPC97367
0.7513	Intermediate Similarity	NPC190007
0.7512	Intermediate Similarity	NPC122436
0.7512	Intermediate Similarity	NPC121772
0.7512	Intermediate Similarity	NPC229893
0.7512	Intermediate Similarity	NPC315957
0.7512	Intermediate Similarity	NPC171787
0.7511	Intermediate Similarity	NPC148889
0.7511	Intermediate Similarity	NPC26543
0.75	Intermediate Similarity	NPC120798
0.75	Intermediate Similarity	NPC161887
0.75	Intermediate Similarity	NPC60553
0.7489	Intermediate Similarity	NPC477549
0.7488	Intermediate Similarity	NPC473185
0.7487	Intermediate Similarity	NPC44161
0.7487	Intermediate Similarity	NPC13880
0.7486	Intermediate Similarity	NPC236711
0.7476	Intermediate Similarity	NPC174758
0.7474	Intermediate Similarity	NPC42591
0.7473	Intermediate Similarity	NPC211572
0.7473	Intermediate Similarity	NPC75540

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 NPC192315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	721
0.2-0.3	734
0.3-0.4	1740
0.4-0.5	2556
0.5-0.6	2030
0.6-0.7	885
0.7-0.8	121
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8492	Intermediate Similarity	NPD9690	Approved
0.8404	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD9705	Discontinued
0.84	Intermediate Similarity	NPD112	Approved
0.8293	Intermediate Similarity	NPD7603	Discontinued
0.8212	Intermediate Similarity	NPD425	Approved
0.8212	Intermediate Similarity	NPD424	Approved
0.8177	Intermediate Similarity	NPD7948	Phase 1
0.8051	Intermediate Similarity	NPD484	Approved
0.8021	Intermediate Similarity	NPD9695	Approved
0.7989	Intermediate Similarity	NPD5065	Approved
0.7927	Intermediate Similarity	NPD1038	Approved
0.7908	Intermediate Similarity	NPD2177	Approved
0.7908	Intermediate Similarity	NPD2175	Phase 3
0.7908	Intermediate Similarity	NPD2176	Approved
0.7876	Intermediate Similarity	NPD9689	Approved
0.7835	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD706	Phase 1
0.7767	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5612	Discontinued
0.7753	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD6159	Phase 2
0.7692	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2615	Phase 3
0.767	Intermediate Similarity	NPD2616	Phase 3
0.7663	Intermediate Similarity	NPD925	Approved
0.7663	Intermediate Similarity	NPD926	Approved
0.7659	Intermediate Similarity	NPD5939	Approved
0.7659	Intermediate Similarity	NPD5936	Approved
0.7656	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD802	Phase 2
0.7638	Intermediate Similarity	NPD9688	Approved
0.7638	Intermediate Similarity	NPD9687	Approved
0.7637	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6290	Phase 2
0.7621	Intermediate Similarity	NPD3330	Phase 1
0.7596	Intermediate Similarity	NPD7112	Discontinued
0.755	Intermediate Similarity	NPD3825	Phase 3
0.7547	Intermediate Similarity	NPD1856	Discontinued
0.7537	Intermediate Similarity	NPD4795	Phase 2
0.7512	Intermediate Similarity	NPD1739	Approved
0.7512	Intermediate Similarity	NPD1740	Approved
0.7488	Intermediate Similarity	NPD4886	Phase 2
0.7488	Intermediate Similarity	NPD4502	Phase 2
0.7476	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4511	Phase 1
0.7447	Intermediate Similarity	NPD1325	Approved
0.7447	Intermediate Similarity	NPD1326	Approved
0.7413	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1213	Phase 3
0.7405	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD2383	Phase 1
0.7395	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2762	Phase 2
0.7385	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6595	Phase 3
0.7358	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5255	Approved
0.735	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5066	Phase 2
0.7321	Intermediate Similarity	NPD5067	Phase 2
0.7318	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7309	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2781	Approved
0.7302	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7222	Phase 2
0.7295	Intermediate Similarity	NPD1197	Approved
0.7295	Intermediate Similarity	NPD1392	Approved
0.7294	Intermediate Similarity	NPD5559	Phase 2
0.7291	Intermediate Similarity	NPD4548	Discontinued
0.7291	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD8395	Approved
0.7291	Intermediate Similarity	NPD8396	Approved
0.7287	Intermediate Similarity	NPD2780	Approved
0.7287	Intermediate Similarity	NPD2782	Approved
0.7282	Intermediate Similarity	NPD4033	Approved
0.7282	Intermediate Similarity	NPD31	Approved
0.7282	Intermediate Similarity	NPD4036	Approved
0.7282	Intermediate Similarity	NPD4037	Approved
0.7282	Intermediate Similarity	NPD4122	Approved
0.7282	Intermediate Similarity	NPD4034	Approved
0.7282	Intermediate Similarity	NPD4039	Approved
0.7282	Intermediate Similarity	NPD4038	Approved
0.7282	Intermediate Similarity	NPD4035	Approved
0.7282	Intermediate Similarity	NPD32	Approved
0.7277	Intermediate Similarity	NPD1229	Phase 2
0.7273	Intermediate Similarity	NPD3746	Discontinued
0.726	Intermediate Similarity	NPD2189	Approved
0.726	Intermediate Similarity	NPD5658	Approved
0.726	Intermediate Similarity	NPD2187	Approved
0.7252	Intermediate Similarity	NPD4454	Phase 2
0.725	Intermediate Similarity	NPD3404	Approved
0.7246	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD534	Phase 2
0.7243	Intermediate Similarity	NPD537	Phase 2
0.724	Intermediate Similarity	NPD7558	Phase 2
0.724	Intermediate Similarity	NPD482	Approved
0.7212	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1722	Approved
0.7206	Intermediate Similarity	NPD3814	Phase 1
0.7204	Intermediate Similarity	NPD9382	Approved
0.7204	Intermediate Similarity	NPD9383	Approved
0.7202	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3931	Approved
0.7184	Intermediate Similarity	NPD6975	Discontinued
0.7184	Intermediate Similarity	NPD3928	Approved
0.7174	Intermediate Similarity	NPD2882	Phase 1
0.717	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD6569	Phase 2
0.7164	Intermediate Similarity	NPD996	Phase 2
0.7164	Intermediate Similarity	NPD994	Phase 2
0.715	Intermediate Similarity	NPD5164	Discontinued
0.7143	Intermediate Similarity	NPD4203	Approved
0.7143	Intermediate Similarity	NPD4204	Approved
0.7136	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD2951	Discontinued
0.7129	Intermediate Similarity	NPD7452	Approved
0.7129	Intermediate Similarity	NPD7453	Approved
0.7129	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1273	Discontinued
0.7119	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD4429	Discontinued
0.7115	Intermediate Similarity	NPD5901	Discontinued
0.7114	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5100	Phase 3
0.7103	Intermediate Similarity	NPD6643	Discontinued
0.71	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD408	Approved
0.7097	Intermediate Similarity	NPD7726	Phase 1
0.7097	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1685	Approved
0.709	Intermediate Similarity	NPD1684	Approved
0.7083	Intermediate Similarity	NPD3402	Phase 1
0.7081	Intermediate Similarity	NPD3003	Approved
0.7081	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6158	Phase 2
0.7081	Intermediate Similarity	NPD5530	Phase 1
0.7075	Intermediate Similarity	NPD4131	Phase 3
0.7075	Intermediate Similarity	NPD949	Phase 1
0.7071	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6492	Phase 2
0.7062	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7068	Approved
0.7061	Intermediate Similarity	NPD7067	Approved
0.7061	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3477	Phase 2
0.7059	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5482	Discontinued
0.7053	Intermediate Similarity	NPD5140	Approved
0.7053	Intermediate Similarity	NPD5138	Approved
0.7051	Intermediate Similarity	NPD6242	Discontinued
0.705	Intermediate Similarity	NPD8431	Approved
0.7043	Intermediate Similarity	NPD2837	Discontinued
0.7039	Intermediate Similarity	NPD5999	Phase 2
0.7033	Intermediate Similarity	NPD3813	Approved
0.7031	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD2381	Approved
0.7026	Intermediate Similarity	NPD2382	Approved
0.7026	Intermediate Similarity	NPD2380	Approved
0.7022	Intermediate Similarity	NPD3006	Discontinued
0.7021	Intermediate Similarity	NPD2581	Approved
0.7021	Intermediate Similarity	NPD2582	Approved
0.702	Intermediate Similarity	NPD2092	Phase 2
0.702	Intermediate Similarity	NPD2095	Phase 2
0.702	Intermediate Similarity	NPD2094	Phase 2
0.702	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD1592	Phase 3
0.7015	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4845	Discontinued
0.7011	Intermediate Similarity	NPD4703	Approved
0.7011	Intermediate Similarity	NPD1661	Suspended
0.7011	Intermediate Similarity	NPD4702	Approved
0.7	Intermediate Similarity	NPD786	Approved
0.6995	Remote Similarity	NPD3922	Approved
0.6995	Remote Similarity	NPD3921	Approved
0.6995	Remote Similarity	NPD3924	Approved
0.6995	Remote Similarity	NPD3923	Approved
0.6987	Remote Similarity	NPD3343	Phase 3
0.6985	Remote Similarity	NPD2091	Phase 2
0.6985	Remote Similarity	NPD2096	Phase 2
0.698	Remote Similarity	NPD3321	Discontinued
0.6979	Remote Similarity	NPD6961	Discontinued
0.6967	Remote Similarity	NPD796	Phase 2
0.6965	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD1034	Phase 3
0.6963	Remote Similarity	NPD863	Approved
0.6963	Remote Similarity	NPD862	Approved
0.6963	Remote Similarity	NPD861	Approved
0.6959	Remote Similarity	NPD2123	Phase 3
0.6958	Remote Similarity	NPD4442	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