NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	251.09
Volume:	267.108
LogP:	3.704
LogD:	3.402
LogS:	-5.423
# Rotatable Bonds:	3
TPSA:	42.09
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	2.456
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	1.877296563179698e-05
Pgp-inhibitor:	0.416
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858
Plasma Protein Binding (PPB):	88.62248992919922%
Volume Distribution (VD):	1.0
Pgp-substrate:	7.564741134643555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.499
CYP2C19-inhibitor:	0.802
CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.841
CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.806
CYP3A4-inhibitor:	0.546
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	2.565
Half-life (T1/2):	0.433

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.376
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.284
Skin Sensitization:	0.949
Carcinogencity:	0.826
Eye Corrosion:	0.375
Eye Irritation:	0.987
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475190

Natural Product ID:	NPC475190
*Common Name:**	1-Vinyl-8-Acetoxy-Beta-Carboline
IUPAC Name:	(8-ethenyl-9H-carbazol-1-yl) acetate
Synonyms:
Standard InCHIKey:	UBPDJQFHBYIKRS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H13NO2/c1-3-11-6-4-7-12-13-8-5-9-14(19-10(2)18)16(13)17-15(11)12/h3-9,17H,1H2,2H3
SMILES:	C=Cc1cccc2c1[nH]c1c2cccc1OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500577
PubChem CID:	44576079
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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]
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
IC50	1
MIC	6
Others	3

Activity Type	# Activity
Cell Line	1
Organism	8
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.65	ug.mL-1	PMID[470960]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[470960]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7.5	ug	PMID[470960]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[470960]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	15.0	ug	PMID[470960]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	0.9	ug	PMID[470960]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	>	60.0	ug	PMID[470960]
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IZ	=	1.0	mm	PMID[470960]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	IZ	=	1.0	mm	PMID[470960]
NPT27	Others	Unspecified		IZ	=	2.0	mm	PMID[470960]

☑ 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 NPC475190 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	463
0.1-0.2	3419
0.2-0.3	13622
0.3-0.4	4130
0.4-0.5	15826
0.5-0.6	3551
0.6-0.7	1413
0.7-0.8	239
0.8-0.85	26
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9302	High Similarity	NPC474798
0.8989	High Similarity	NPC242928
0.8824	High Similarity	NPC470930
0.8656	High Similarity	NPC128823
0.8653	High Similarity	NPC476287
0.8557	High Similarity	NPC39500
0.8542	High Similarity	NPC209769
0.8384	Intermediate Similarity	NPC184408
0.8359	Intermediate Similarity	NPC187501
0.8308	Intermediate Similarity	NPC144452
0.8308	Intermediate Similarity	NPC199667
0.8256	Intermediate Similarity	NPC473181
0.8223	Intermediate Similarity	NPC473180
0.8223	Intermediate Similarity	NPC94157
0.8119	Intermediate Similarity	NPC225279
0.8116	Intermediate Similarity	NPC474688
0.8115	Intermediate Similarity	NPC72211
0.8107	Intermediate Similarity	NPC274640
0.8105	Intermediate Similarity	NPC70259
0.8103	Intermediate Similarity	NPC300156
0.8093	Intermediate Similarity	NPC476138
0.8093	Intermediate Similarity	NPC245816
0.8093	Intermediate Similarity	NPC162484
0.8079	Intermediate Similarity	NPC118511
0.8069	Intermediate Similarity	NPC208084
0.8053	Intermediate Similarity	NPC131017
0.8053	Intermediate Similarity	NPC43787
0.8053	Intermediate Similarity	NPC205934
0.805	Intermediate Similarity	NPC118228
0.8	Intermediate Similarity	NPC176127
0.798	Intermediate Similarity	NPC185782
0.798	Intermediate Similarity	NPC473179
0.795	Intermediate Similarity	NPC26679
0.7949	Intermediate Similarity	NPC291535
0.7949	Intermediate Similarity	NPC475112
0.7949	Intermediate Similarity	NPC475085
0.7941	Intermediate Similarity	NPC132642
0.7902	Intermediate Similarity	NPC280799
0.7897	Intermediate Similarity	NPC267423
0.7889	Intermediate Similarity	NPC201697
0.7879	Intermediate Similarity	NPC4687
0.7876	Intermediate Similarity	NPC70956
0.7876	Intermediate Similarity	NPC243834
0.7857	Intermediate Similarity	NPC475253
0.7828	Intermediate Similarity	NPC45190
0.7826	Intermediate Similarity	NPC51388
0.7814	Intermediate Similarity	NPC475844
0.7806	Intermediate Similarity	NPC470586
0.7806	Intermediate Similarity	NPC476044
0.7788	Intermediate Similarity	NPC179287
0.7772	Intermediate Similarity	NPC48353
0.7766	Intermediate Similarity	NPC84478
0.7745	Intermediate Similarity	NPC470799
0.7745	Intermediate Similarity	NPC8022
0.7742	Intermediate Similarity	NPC88363
0.7739	Intermediate Similarity	NPC476106
0.7736	Intermediate Similarity	NPC473186
0.7727	Intermediate Similarity	NPC475774
0.7725	Intermediate Similarity	NPC42591
0.7723	Intermediate Similarity	NPC87413
0.7718	Intermediate Similarity	NPC288987
0.7714	Intermediate Similarity	NPC473185
0.7707	Intermediate Similarity	NPC314552
0.77	Intermediate Similarity	NPC193777
0.77	Intermediate Similarity	NPC321428
0.7689	Intermediate Similarity	NPC474701
0.7667	Intermediate Similarity	NPC202503
0.7664	Intermediate Similarity	NPC39370
0.7638	Intermediate Similarity	NPC223427
0.7621	Intermediate Similarity	NPC169402
0.7612	Intermediate Similarity	NPC283117
0.7612	Intermediate Similarity	NPC249583
0.761	Intermediate Similarity	NPC116238
0.7604	Intermediate Similarity	NPC296527
0.7588	Intermediate Similarity	NPC135887
0.7588	Intermediate Similarity	NPC199277
0.7586	Intermediate Similarity	NPC471304
0.7585	Intermediate Similarity	NPC96321
0.7576	Intermediate Similarity	NPC19872
0.7576	Intermediate Similarity	NPC329793
0.7565	Intermediate Similarity	NPC76748
0.7556	Intermediate Similarity	NPC26850
0.7551	Intermediate Similarity	NPC251090
0.7538	Intermediate Similarity	NPC307963
0.7535	Intermediate Similarity	NPC473182
0.7526	Intermediate Similarity	NPC92111
0.7513	Intermediate Similarity	NPC246700
0.7513	Intermediate Similarity	NPC128751
0.75	Intermediate Similarity	NPC160381
0.7489	Intermediate Similarity	NPC148889
0.7488	Intermediate Similarity	NPC39679
0.7487	Intermediate Similarity	NPC312872
0.7487	Intermediate Similarity	NPC176538
0.7487	Intermediate Similarity	NPC329747
0.7476	Intermediate Similarity	NPC198503
0.7475	Intermediate Similarity	NPC304183
0.7474	Intermediate Similarity	NPC106833
0.7474	Intermediate Similarity	NPC206201
0.7474	Intermediate Similarity	NPC469497
0.7464	Intermediate Similarity	NPC292958
0.7463	Intermediate Similarity	NPC294375
0.7463	Intermediate Similarity	NPC208284
0.7454	Intermediate Similarity	NPC329631
0.7452	Intermediate Similarity	NPC293151
0.7448	Intermediate Similarity	NPC94943
0.7437	Intermediate Similarity	NPC476167
0.7435	Intermediate Similarity	NPC212535
0.7431	Intermediate Similarity	NPC473183
0.7429	Intermediate Similarity	NPC174760
0.7427	Intermediate Similarity	NPC310211
0.7427	Intermediate Similarity	NPC308137
0.7421	Intermediate Similarity	NPC478032
0.7419	Intermediate Similarity	NPC473184
0.7416	Intermediate Similarity	NPC46561
0.7416	Intermediate Similarity	NPC131885
0.7416	Intermediate Similarity	NPC473041
0.7415	Intermediate Similarity	NPC11464
0.7415	Intermediate Similarity	NPC219664
0.7411	Intermediate Similarity	NPC276517
0.7409	Intermediate Similarity	NPC204385
0.7407	Intermediate Similarity	NPC101543
0.7407	Intermediate Similarity	NPC469554
0.74	Intermediate Similarity	NPC11017
0.7396	Intermediate Similarity	NPC190007
0.7389	Intermediate Similarity	NPC26872
0.7387	Intermediate Similarity	NPC192315
0.736	Intermediate Similarity	NPC230403
0.735	Intermediate Similarity	NPC18487
0.7346	Intermediate Similarity	NPC477533
0.7343	Intermediate Similarity	NPC203168
0.734	Intermediate Similarity	NPC285558
0.734	Intermediate Similarity	NPC474409
0.7337	Intermediate Similarity	NPC153042
0.7327	Intermediate Similarity	NPC66815
0.7317	Intermediate Similarity	NPC470931
0.7316	Intermediate Similarity	NPC283152
0.7311	Intermediate Similarity	NPC477532
0.7294	Intermediate Similarity	NPC180504
0.7291	Intermediate Similarity	NPC476098
0.7282	Intermediate Similarity	NPC66083
0.7277	Intermediate Similarity	NPC232727
0.7269	Intermediate Similarity	NPC252251
0.7268	Intermediate Similarity	NPC473189
0.7264	Intermediate Similarity	NPC150239
0.7263	Intermediate Similarity	NPC288943
0.7251	Intermediate Similarity	NPC247803
0.725	Intermediate Similarity	NPC267928
0.7243	Intermediate Similarity	NPC314633
0.7238	Intermediate Similarity	NPC152768
0.7238	Intermediate Similarity	NPC3207
0.7238	Intermediate Similarity	NPC148183
0.7238	Intermediate Similarity	NPC170114
0.7235	Intermediate Similarity	NPC209174
0.7233	Intermediate Similarity	NPC475910
0.7225	Intermediate Similarity	NPC266931
0.7225	Intermediate Similarity	NPC478074
0.7225	Intermediate Similarity	NPC473188
0.7222	Intermediate Similarity	NPC257851
0.7214	Intermediate Similarity	NPC306376
0.7202	Intermediate Similarity	NPC476999
0.7202	Intermediate Similarity	NPC477531
0.7202	Intermediate Similarity	NPC260434
0.7202	Intermediate Similarity	NPC118776
0.72	Intermediate Similarity	NPC13880
0.7195	Intermediate Similarity	NPC6786
0.719	Intermediate Similarity	NPC470549
0.7189	Intermediate Similarity	NPC311906
0.7188	Intermediate Similarity	NPC72980
0.7183	Intermediate Similarity	NPC472099
0.7177	Intermediate Similarity	NPC38237
0.7177	Intermediate Similarity	NPC472098
0.717	Intermediate Similarity	NPC303658
0.7169	Intermediate Similarity	NPC475720
0.7169	Intermediate Similarity	NPC474192
0.7163	Intermediate Similarity	NPC205372
0.7163	Intermediate Similarity	NPC167860
0.7163	Intermediate Similarity	NPC123976
0.7156	Intermediate Similarity	NPC288349
0.715	Intermediate Similarity	NPC60621
0.7143	Intermediate Similarity	NPC471080
0.7143	Intermediate Similarity	NPC140296
0.7143	Intermediate Similarity	NPC469592
0.7136	Intermediate Similarity	NPC99666
0.712	Intermediate Similarity	NPC141353
0.711	Intermediate Similarity	NPC314954
0.7108	Intermediate Similarity	NPC98685
0.7105	Intermediate Similarity	NPC26543
0.7105	Intermediate Similarity	NPC165964
0.7104	Intermediate Similarity	NPC277351
0.7103	Intermediate Similarity	NPC86078
0.7098	Intermediate Similarity	NPC472168
0.7097	Intermediate Similarity	NPC470018
0.7095	Intermediate Similarity	NPC474428
0.7092	Intermediate Similarity	NPC314002
0.7091	Intermediate Similarity	NPC49547
0.7087	Intermediate Similarity	NPC132539
0.7083	Intermediate Similarity	NPC224764
0.7081	Intermediate Similarity	NPC188420
0.7079	Intermediate Similarity	NPC156704
0.7075	Intermediate Similarity	NPC469928

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 NPC475190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	748
0.2-0.3	898
0.3-0.4	1232
0.4-0.5	3081
0.5-0.6	2175
0.6-0.7	648
0.7-0.8	82
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8245	Intermediate Similarity	NPD4418	Discontinued
0.7877	Intermediate Similarity	NPD4454	Phase 2
0.7865	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD2565	Phase 2
0.7842	Intermediate Similarity	NPD2564	Approved
0.7824	Intermediate Similarity	NPD5512	Phase 3
0.7789	Intermediate Similarity	NPD5429	Discontinued
0.7739	Intermediate Similarity	NPD3003	Approved
0.7732	Intermediate Similarity	NPD6550	Discontinued
0.7707	Intermediate Similarity	NPD5164	Discontinued
0.7704	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5256	Discontinued
0.7677	Intermediate Similarity	NPD1897	Discontinued
0.767	Intermediate Similarity	NPD5632	Approved
0.7614	Intermediate Similarity	NPD3825	Phase 3
0.7602	Intermediate Similarity	NPD5003	Discontinued
0.7602	Intermediate Similarity	NPD6988	Phase 1
0.7546	Intermediate Similarity	NPD3006	Discontinued
0.7538	Intermediate Similarity	NPD1038	Approved
0.7538	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7452	Approved
0.7525	Intermediate Similarity	NPD2778	Approved
0.7525	Intermediate Similarity	NPD7453	Approved
0.7525	Intermediate Similarity	NPD7222	Phase 2
0.7524	Intermediate Similarity	NPD5903	Approved
0.7524	Intermediate Similarity	NPD5902	Approved
0.7488	Intermediate Similarity	NPD5658	Approved
0.7488	Intermediate Similarity	NPD5612	Discontinued
0.7454	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4889	Approved
0.7437	Intermediate Similarity	NPD1768	Approved
0.7413	Intermediate Similarity	NPD2779	Approved
0.7411	Intermediate Similarity	NPD6590	Discontinued
0.7387	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5067	Phase 2
0.7379	Intermediate Similarity	NPD5066	Phase 2
0.7379	Intermediate Similarity	NPD4502	Phase 2
0.7376	Intermediate Similarity	NPD2920	Discontinued
0.7356	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5559	Phase 2
0.7333	Intermediate Similarity	NPD7395	Discontinued
0.7304	Intermediate Similarity	NPD8403	Phase 1
0.7299	Intermediate Similarity	NPD3875	Discontinued
0.7295	Intermediate Similarity	NPD5416	Discontinued
0.7285	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1867	Approved
0.7277	Intermediate Similarity	NPD3920	Phase 2
0.7259	Intermediate Similarity	NPD5913	Phase 3
0.7259	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6985	Discontinued
0.7251	Intermediate Similarity	NPD4429	Discontinued
0.7238	Intermediate Similarity	NPD6643	Discontinued
0.7236	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3945	Discontinued
0.7212	Intermediate Similarity	NPD6220	Phase 3
0.7202	Intermediate Similarity	NPD4204	Approved
0.7202	Intermediate Similarity	NPD4203	Approved
0.719	Intermediate Similarity	NPD3257	Approved
0.7184	Intermediate Similarity	NPD1392	Approved
0.7183	Intermediate Similarity	NPD6242	Discontinued
0.7171	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5022	Discontinued
0.7156	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6251	Discontinued
0.7136	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7194	Discontinued
0.7129	Intermediate Similarity	NPD7468	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5482	Discontinued
0.7103	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD112	Approved
0.7097	Intermediate Similarity	NPD9705	Discontinued
0.7095	Intermediate Similarity	NPD6202	Discontinued
0.7095	Intermediate Similarity	NPD7069	Discontinued
0.7078	Intermediate Similarity	NPD5479	Discontinued
0.7067	Intermediate Similarity	NPD2189	Approved
0.7067	Intermediate Similarity	NPD2187	Approved
0.7065	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7994	Phase 2
0.7059	Intermediate Similarity	NPD484	Approved
0.7056	Intermediate Similarity	NPD3258	Approved
0.7056	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3402	Phase 1
0.7053	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5939	Approved
0.7048	Intermediate Similarity	NPD5936	Approved
0.7048	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3477	Phase 2
0.703	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2951	Discontinued
0.702	Intermediate Similarity	NPD2749	Discontinued
0.7015	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4927	Discontinued
0.7014	Intermediate Similarity	NPD4885	Approved
0.701	Intermediate Similarity	NPD2177	Approved
0.701	Intermediate Similarity	NPD2176	Approved
0.701	Intermediate Similarity	NPD2175	Phase 3
0.7009	Intermediate Similarity	NPD3354	Phase 2
0.7005	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7853	Phase 2
0.6995	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6974	Phase 3
0.6972	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6150	Discontinued
0.6971	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1466	Phase 3
0.6968	Remote Similarity	NPD1467	Approved
0.6965	Remote Similarity	NPD6569	Phase 2
0.6963	Remote Similarity	NPD1325	Approved
0.6963	Remote Similarity	NPD1326	Approved
0.6959	Remote Similarity	NPD6159	Phase 2
0.6957	Remote Similarity	NPD6324	Phase 1
0.6953	Remote Similarity	NPD6961	Discontinued
0.6948	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7180	Phase 3
0.6942	Remote Similarity	NPD4511	Phase 1
0.6941	Remote Similarity	NPD3263	Phase 3
0.6938	Remote Similarity	NPD6290	Phase 2
0.6937	Remote Similarity	NPD3746	Discontinued
0.6927	Remote Similarity	NPD4548	Discontinued
0.6926	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4952	Phase 3
0.6923	Remote Similarity	NPD3397	Phase 2
0.6923	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.692	Remote Similarity	NPD3250	Phase 1
0.6912	Remote Similarity	NPD7948	Phase 1
0.6909	Remote Similarity	NPD4328	Approved
0.6906	Remote Similarity	NPD7558	Phase 2
0.69	Remote Similarity	NPD8100	Phase 3
0.6884	Remote Similarity	NPD4921	Phase 3
0.6884	Remote Similarity	NPD4919	Phase 3
0.6884	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3924	Approved
0.6881	Remote Similarity	NPD3921	Approved
0.6881	Remote Similarity	NPD3922	Approved
0.6881	Remote Similarity	NPD3923	Approved
0.6878	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8358	Approved
0.6869	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5850	Phase 3
0.6866	Remote Similarity	NPD5930	Phase 3
0.6864	Remote Similarity	NPD7603	Discontinued
0.6862	Remote Similarity	NPD4442	Phase 2
0.6854	Remote Similarity	NPD5866	Approved
0.685	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8396	Approved
0.6845	Remote Similarity	NPD8395	Approved
0.6842	Remote Similarity	NPD4795	Phase 2
0.6842	Remote Similarity	NPD6716	Phase 1
0.6833	Remote Similarity	NPD3259	Approved
0.683	Remote Similarity	NPD4373	Phase 2
0.6829	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6208	Discontinued
0.6827	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4354	Approved
0.682	Remote Similarity	NPD3763	Approved
0.6816	Remote Similarity	NPD1505	Phase 2
0.6816	Remote Similarity	NPD6962	Phase 2
0.6811	Remote Similarity	NPD3833	Phase 3
0.6811	Remote Similarity	NPD3835	Phase 3
0.681	Remote Similarity	NPD8101	Phase 3
0.6804	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6736	Discontinued
0.68	Remote Similarity	NPD2444	Phase 2
0.6798	Remote Similarity	NPD4372	Phase 1
0.6797	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5924	Discontinued
0.6766	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1034	Phase 3
0.6761	Remote Similarity	NPD5420	Discontinued
0.6761	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6494	Phase 2
0.675	Remote Similarity	NPD5450	Discontinued
0.6749	Remote Similarity	NPD1924	Approved
0.6744	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5811	Approved
0.6736	Remote Similarity	NPD2844	Phase 3
0.6736	Remote Similarity	NPD6457	Approved
0.6731	Remote Similarity	NPD1739	Approved
0.6731	Remote Similarity	NPD1740	Approved
0.673	Remote Similarity	NPD5530	Phase 1
0.6729	Remote Similarity	NPD7470	Discontinued
0.6725	Remote Similarity	NPD7417	Discontinued
0.6718	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6452	Discontinued
0.6716	Remote Similarity	NPD3963	Phase 1
0.6714	Remote Similarity	NPD2125	Clinical (unspecified phase)

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