NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	223.1
Volume:	243.659
LogP:	4.134
LogD:	3.778
LogS:	-5.429
# Rotatable Bonds:	2
TPSA:	25.02
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.698
Synthetic Accessibility Score:	2.321
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.964
MDCK Permeability:	1.517639248049818e-05
Pgp-inhibitor:	0.466
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.761
Plasma Protein Binding (PPB):	94.56729125976562%
Volume Distribution (VD):	0.786
Pgp-substrate:	2.784388303756714%

ADMET: Metabolism

CYP1A2-inhibitor:	0.993
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.859
CYP2C19-substrate:	0.557
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.897
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.633

ADMET: Excretion

Clearance (CL):	6.13
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.728
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.418
Skin Sensitization:	0.906
Carcinogencity:	0.897
Eye Corrosion:	0.409
Eye Irritation:	0.988
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: NPC474798

Natural Product ID:	NPC474798
*Common Name:**	1-Ethenyl-8-Methoxy-9H-Carbazole
IUPAC Name:	1-ethenyl-8-methoxy-9H-carbazole
Synonyms:
Standard InCHIKey:	ZOHQLPLULJPUBU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO/c1-3-10-6-4-7-11-12-8-5-9-13(17-2)15(12)16-14(10)11/h3-9,16H,1H2,2H3
SMILES:	COC1=CC=CC2=C1NC3=C(C=CC=C23)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483022
PubChem CID:	44576072
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	6

Activity Type	# Activity
Cell Line	1
Organism	10
Others	2

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[542478]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	60.0	ug	PMID[542478]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	7.5	ug	PMID[542478]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	60.0	ug	PMID[542478]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	7.5	ug	PMID[542478]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	0.45	ug	PMID[542478]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	MIC	=	15.0	ug	PMID[542478]
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IZ	=	1.0	mm	PMID[542478]
NPT1106	Organism	Human poliovirus 1	Human poliovirus 1	IZ	=	1.0	mm	PMID[542478]
NPT27	Others	Unspecified		IZ	=	2.0	mm	PMID[542478]
NPT27	Others	Unspecified		IZ	=	1.0	mm	PMID[542478]

☑ 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 NPC474798 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	740
0.1-0.2	4430
0.2-0.3	12928
0.3-0.4	7051
0.4-0.5	12739
0.5-0.6	3063
0.6-0.7	1412
0.7-0.8	282
0.8-0.85	37
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9641	High Similarity	NPC242928
0.9302	High Similarity	NPC475190
0.9148	High Similarity	NPC128823
0.8895	High Similarity	NPC470930
0.8703	High Similarity	NPC473181
0.8675	High Similarity	NPC118511
0.8656	High Similarity	NPC199667
0.8634	High Similarity	NPC476138
0.8634	High Similarity	NPC245816
0.861	High Similarity	NPC187501
0.8564	High Similarity	NPC473180
0.8564	High Similarity	NPC94157
0.8563	High Similarity	NPC176127
0.8519	High Similarity	NPC39500
0.8503	High Similarity	NPC209769
0.85	High Similarity	NPC131017
0.8404	Intermediate Similarity	NPC185782
0.8342	Intermediate Similarity	NPC184408
0.8305	Intermediate Similarity	NPC84478
0.8299	Intermediate Similarity	NPC473179
0.8299	Intermediate Similarity	NPC208084
0.8272	Intermediate Similarity	NPC26679
0.8256	Intermediate Similarity	NPC225279
0.8256	Intermediate Similarity	NPC132642
0.8207	Intermediate Similarity	NPC243834
0.8207	Intermediate Similarity	NPC70956
0.8182	Intermediate Similarity	NPC88363
0.8173	Intermediate Similarity	NPC144452
0.8162	Intermediate Similarity	NPC72211
0.8156	Intermediate Similarity	NPC42591
0.8152	Intermediate Similarity	NPC70259
0.8144	Intermediate Similarity	NPC8022
0.8144	Intermediate Similarity	NPC470799
0.8138	Intermediate Similarity	NPC162484
0.8135	Intermediate Similarity	NPC476287
0.8122	Intermediate Similarity	NPC296527
0.8098	Intermediate Similarity	NPC43787
0.8098	Intermediate Similarity	NPC205934
0.8077	Intermediate Similarity	NPC76748
0.8075	Intermediate Similarity	NPC19872
0.8053	Intermediate Similarity	NPC45190
0.8053	Intermediate Similarity	NPC300156
0.8042	Intermediate Similarity	NPC475774
0.8033	Intermediate Similarity	NPC92111
0.801	Intermediate Similarity	NPC193777
0.801	Intermediate Similarity	NPC473185
0.8	Intermediate Similarity	NPC179287
0.8	Intermediate Similarity	NPC118228
0.8	Intermediate Similarity	NPC26850
0.7989	Intermediate Similarity	NPC135887
0.7989	Intermediate Similarity	NPC199277
0.7979	Intermediate Similarity	NPC329793
0.7979	Intermediate Similarity	NPC176538
0.797	Intermediate Similarity	NPC274640
0.796	Intermediate Similarity	NPC202503
0.7957	Intermediate Similarity	NPC251090
0.7947	Intermediate Similarity	NPC223427
0.7946	Intermediate Similarity	NPC307963
0.7937	Intermediate Similarity	NPC267423
0.7929	Intermediate Similarity	NPC288987
0.7929	Intermediate Similarity	NPC26872
0.7929	Intermediate Similarity	NPC292958
0.7919	Intermediate Similarity	NPC314552
0.7895	Intermediate Similarity	NPC291535
0.7895	Intermediate Similarity	NPC475085
0.7895	Intermediate Similarity	NPC475112
0.7892	Intermediate Similarity	NPC475253
0.7892	Intermediate Similarity	NPC474688
0.7884	Intermediate Similarity	NPC329747
0.7854	Intermediate Similarity	NPC473186
0.7846	Intermediate Similarity	NPC208284
0.7845	Intermediate Similarity	NPC212535
0.7842	Intermediate Similarity	NPC476044
0.7835	Intermediate Similarity	NPC201697
0.7833	Intermediate Similarity	NPC478032
0.7831	Intermediate Similarity	NPC476167
0.7826	Intermediate Similarity	NPC246700
0.7826	Intermediate Similarity	NPC128751
0.7824	Intermediate Similarity	NPC4687
0.7824	Intermediate Similarity	NPC249583
0.7824	Intermediate Similarity	NPC283117
0.7816	Intermediate Similarity	NPC473182
0.7809	Intermediate Similarity	NPC312872
0.7784	Intermediate Similarity	NPC106833
0.7784	Intermediate Similarity	NPC469497
0.7778	Intermediate Similarity	NPC192315
0.7778	Intermediate Similarity	NPC39370
0.7772	Intermediate Similarity	NPC304183
0.7772	Intermediate Similarity	NPC476106
0.776	Intermediate Similarity	NPC94943
0.7753	Intermediate Similarity	NPC474409
0.7749	Intermediate Similarity	NPC232727
0.772	Intermediate Similarity	NPC285558
0.7716	Intermediate Similarity	NPC48353
0.7705	Intermediate Similarity	NPC190007
0.7704	Intermediate Similarity	NPC471304
0.7704	Intermediate Similarity	NPC11464
0.7703	Intermediate Similarity	NPC473183
0.7692	Intermediate Similarity	NPC206201
0.7692	Intermediate Similarity	NPC473184
0.7685	Intermediate Similarity	NPC51388
0.7681	Intermediate Similarity	NPC101543
0.7681	Intermediate Similarity	NPC469554
0.7672	Intermediate Similarity	NPC13880
0.7665	Intermediate Similarity	NPC87413
0.7665	Intermediate Similarity	NPC294375
0.7644	Intermediate Similarity	NPC18487
0.7641	Intermediate Similarity	NPC321428
0.7632	Intermediate Similarity	NPC267928
0.7626	Intermediate Similarity	NPC308137
0.7626	Intermediate Similarity	NPC310211
0.7622	Intermediate Similarity	NPC204385
0.7617	Intermediate Similarity	NPC66815
0.7612	Intermediate Similarity	NPC46561
0.7594	Intermediate Similarity	NPC475844
0.7582	Intermediate Similarity	NPC72980
0.7562	Intermediate Similarity	NPC293151
0.755	Intermediate Similarity	NPC470549
0.755	Intermediate Similarity	NPC116238
0.7539	Intermediate Similarity	NPC153042
0.7529	Intermediate Similarity	NPC141353
0.7525	Intermediate Similarity	NPC123976
0.7525	Intermediate Similarity	NPC167860
0.7513	Intermediate Similarity	NPC475910
0.7512	Intermediate Similarity	NPC170114
0.75	Intermediate Similarity	NPC266931
0.75	Intermediate Similarity	NPC280799
0.75	Intermediate Similarity	NPC478074
0.7475	Intermediate Similarity	NPC169402
0.7474	Intermediate Similarity	NPC98685
0.7473	Intermediate Similarity	NPC473189
0.7464	Intermediate Similarity	NPC474701
0.7458	Intermediate Similarity	NPC177404
0.7451	Intermediate Similarity	NPC86078
0.7438	Intermediate Similarity	NPC96321
0.7438	Intermediate Similarity	NPC247803
0.7437	Intermediate Similarity	NPC219664
0.7433	Intermediate Similarity	NPC160381
0.7424	Intermediate Similarity	NPC39679
0.7424	Intermediate Similarity	NPC476465
0.7423	Intermediate Similarity	NPC11017
0.7419	Intermediate Similarity	NPC284678
0.7419	Intermediate Similarity	NPC204717
0.7413	Intermediate Similarity	NPC469592
0.7413	Intermediate Similarity	NPC471080
0.7394	Intermediate Similarity	NPC66083
0.7393	Intermediate Similarity	NPC180504
0.7391	Intermediate Similarity	NPC472168
0.7389	Intermediate Similarity	NPC1527
0.738	Intermediate Similarity	NPC314002
0.7377	Intermediate Similarity	NPC224764
0.7368	Intermediate Similarity	NPC314954
0.7366	Intermediate Similarity	NPC174760
0.7366	Intermediate Similarity	NPC220765
0.7366	Intermediate Similarity	NPC150239
0.7366	Intermediate Similarity	NPC477533
0.7363	Intermediate Similarity	NPC203168
0.7353	Intermediate Similarity	NPC131885
0.7349	Intermediate Similarity	NPC148889
0.734	Intermediate Similarity	NPC171171
0.7337	Intermediate Similarity	NPC283152
0.7333	Intermediate Similarity	NPC121772
0.7333	Intermediate Similarity	NPC234197
0.733	Intermediate Similarity	NPC477532
0.733	Intermediate Similarity	NPC198503
0.733	Intermediate Similarity	NPC99666
0.7321	Intermediate Similarity	NPC257851
0.7318	Intermediate Similarity	NPC473188
0.7317	Intermediate Similarity	NPC148409
0.7311	Intermediate Similarity	NPC329631
0.7297	Intermediate Similarity	NPC42979
0.7295	Intermediate Similarity	NPC280272
0.7292	Intermediate Similarity	NPC230403
0.7286	Intermediate Similarity	NPC252251
0.7283	Intermediate Similarity	NPC288943
0.7277	Intermediate Similarity	NPC474428
0.7277	Intermediate Similarity	NPC316981
0.7273	Intermediate Similarity	NPC227908
0.7268	Intermediate Similarity	NPC469594
0.7268	Intermediate Similarity	NPC303658
0.7268	Intermediate Similarity	NPC473041
0.7264	Intermediate Similarity	NPC188420
0.7254	Intermediate Similarity	NPC276517
0.7253	Intermediate Similarity	NPC314940
0.7253	Intermediate Similarity	NPC473764
0.725	Intermediate Similarity	NPC287208
0.725	Intermediate Similarity	NPC470931
0.7243	Intermediate Similarity	NPC184964
0.7241	Intermediate Similarity	NPC162530
0.724	Intermediate Similarity	NPC141915
0.724	Intermediate Similarity	NPC280964
0.724	Intermediate Similarity	NPC114335
0.7234	Intermediate Similarity	NPC62069
0.7233	Intermediate Similarity	NPC213530
0.7233	Intermediate Similarity	NPC193267
0.7219	Intermediate Similarity	NPC314394
0.7219	Intermediate Similarity	NPC118776
0.7217	Intermediate Similarity	NPC477531
0.7213	Intermediate Similarity	NPC252590
0.7208	Intermediate Similarity	NPC470586

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 NPC474798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	711
0.2-0.3	844
0.3-0.4	1355
0.4-0.5	3093
0.5-0.6	2038
0.6-0.7	589
0.7-0.8	89
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
0.8118	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD1038	Approved
0.7919	Intermediate Similarity	NPD5164	Discontinued
0.7901	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5658	Approved
0.7772	Intermediate Similarity	NPD3003	Approved
0.7737	Intermediate Similarity	NPD3825	Phase 3
0.7717	Intermediate Similarity	NPD5256	Discontinued
0.7665	Intermediate Similarity	NPD4502	Phase 2
0.7619	Intermediate Similarity	NPD4418	Discontinued
0.7594	Intermediate Similarity	NPD2564	Approved
0.7594	Intermediate Similarity	NPD2565	Phase 2
0.7582	Intermediate Similarity	NPD3920	Phase 2
0.7553	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5913	Phase 3
0.7552	Intermediate Similarity	NPD1768	Approved
0.7551	Intermediate Similarity	NPD7453	Approved
0.7551	Intermediate Similarity	NPD7222	Phase 2
0.7551	Intermediate Similarity	NPD7452	Approved
0.755	Intermediate Similarity	NPD5902	Approved
0.755	Intermediate Similarity	NPD5903	Approved
0.7512	Intermediate Similarity	NPD5612	Discontinued
0.75	Intermediate Similarity	NPD9705	Discontinued
0.75	Intermediate Similarity	NPD112	Approved
0.7488	Intermediate Similarity	NPD4454	Phase 2
0.7435	Intermediate Similarity	NPD6590	Discontinued
0.7424	Intermediate Similarity	NPD2189	Approved
0.7424	Intermediate Similarity	NPD2187	Approved
0.74	Intermediate Similarity	NPD5066	Phase 2
0.74	Intermediate Similarity	NPD5067	Phase 2
0.7396	Intermediate Similarity	NPD5512	Phase 3
0.7374	Intermediate Similarity	NPD5429	Discontinued
0.7358	Intermediate Similarity	NPD5003	Discontinued
0.7353	Intermediate Similarity	NPD4429	Discontinued
0.7348	Intermediate Similarity	NPD1326	Approved
0.7348	Intermediate Similarity	NPD1325	Approved
0.7324	Intermediate Similarity	NPD3006	Discontinued
0.7323	Intermediate Similarity	NPD8403	Phase 1
0.7317	Intermediate Similarity	NPD3875	Discontinued
0.7313	Intermediate Similarity	NPD5936	Approved
0.7313	Intermediate Similarity	NPD5939	Approved
0.7311	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6550	Discontinued
0.7302	Intermediate Similarity	NPD2749	Discontinued
0.7292	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1392	Approved
0.7282	Intermediate Similarity	NPD2176	Approved
0.7282	Intermediate Similarity	NPD6242	Discontinued
0.7282	Intermediate Similarity	NPD2175	Phase 3
0.7282	Intermediate Similarity	NPD2177	Approved
0.7268	Intermediate Similarity	NPD5632	Approved
0.7268	Intermediate Similarity	NPD6985	Discontinued
0.7255	Intermediate Similarity	NPD6643	Discontinued
0.7254	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6251	Discontinued
0.7228	Intermediate Similarity	NPD6220	Phase 3
0.722	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4204	Approved
0.7219	Intermediate Similarity	NPD4203	Approved
0.7208	Intermediate Similarity	NPD4511	Phase 1
0.7206	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5559	Phase 2
0.72	Intermediate Similarity	NPD3835	Phase 3
0.72	Intermediate Similarity	NPD3833	Phase 3
0.7198	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4548	Discontinued
0.7192	Intermediate Similarity	NPD6202	Discontinued
0.7186	Intermediate Similarity	NPD4795	Phase 2
0.7179	Intermediate Similarity	NPD6988	Phase 1
0.7172	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1739	Approved
0.7157	Intermediate Similarity	NPD1740	Approved
0.7151	Intermediate Similarity	NPD6159	Phase 2
0.715	Intermediate Similarity	NPD3924	Approved
0.715	Intermediate Similarity	NPD3923	Approved
0.715	Intermediate Similarity	NPD3922	Approved
0.715	Intermediate Similarity	NPD3402	Phase 1
0.715	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7194	Discontinued
0.715	Intermediate Similarity	NPD3921	Approved
0.7136	Intermediate Similarity	NPD2920	Discontinued
0.7128	Intermediate Similarity	NPD3477	Phase 2
0.7128	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6290	Phase 2
0.7097	Intermediate Similarity	NPD4354	Approved
0.7092	Intermediate Similarity	NPD7948	Phase 1
0.7085	Intermediate Similarity	NPD1897	Discontinued
0.7077	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3945	Discontinued
0.7067	Intermediate Similarity	NPD3514	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6150	Discontinued
0.7043	Intermediate Similarity	NPD9690	Approved
0.7039	Intermediate Similarity	NPD3257	Approved
0.7024	Intermediate Similarity	NPD4927	Discontinued
0.7023	Intermediate Similarity	NPD4885	Approved
0.702	Intermediate Similarity	NPD8396	Approved
0.702	Intermediate Similarity	NPD2778	Approved
0.702	Intermediate Similarity	NPD8395	Approved
0.7014	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5022	Discontinued
0.7009	Intermediate Similarity	NPD5479	Discontinued
0.7005	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3763	Approved
0.698	Remote Similarity	NPD5530	Phase 1
0.6979	Remote Similarity	NPD4920	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4921	Phase 3
0.6979	Remote Similarity	NPD4919	Phase 3
0.6974	Remote Similarity	NPD3963	Phase 1
0.6974	Remote Similarity	NPD6569	Phase 2
0.6967	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6736	Discontinued
0.6965	Remote Similarity	NPD6324	Phase 1
0.6961	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3746	Discontinued
0.6943	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1034	Phase 3
0.6939	Remote Similarity	NPD802	Phase 2
0.6938	Remote Similarity	NPD7395	Discontinued
0.6935	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5999	Phase 2
0.6933	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4122	Approved
0.6931	Remote Similarity	NPD3397	Phase 2
0.6931	Remote Similarity	NPD4037	Approved
0.6931	Remote Similarity	NPD31	Approved
0.6931	Remote Similarity	NPD4038	Approved
0.6931	Remote Similarity	NPD4034	Approved
0.6931	Remote Similarity	NPD32	Approved
0.6931	Remote Similarity	NPD4036	Approved
0.6931	Remote Similarity	NPD4039	Approved
0.6931	Remote Similarity	NPD4035	Approved
0.6931	Remote Similarity	NPD4033	Approved
0.6923	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6208	Discontinued
0.6915	Remote Similarity	NPD2779	Approved
0.6912	Remote Similarity	NPD7558	Phase 2
0.6911	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3258	Approved
0.6904	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.69	Remote Similarity	NPD484	Approved
0.6897	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1592	Phase 3
0.6893	Remote Similarity	NPD5416	Discontinued
0.689	Remote Similarity	NPD3440	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1856	Discontinued
0.6884	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD565	Phase 2
0.6872	Remote Similarity	NPD3342	Phase 2
0.6872	Remote Similarity	NPD5930	Phase 3
0.6869	Remote Similarity	NPD7603	Discontinued
0.686	Remote Similarity	NPD3815	Phase 1
0.686	Remote Similarity	NPD3816	Phase 1
0.6857	Remote Similarity	NPD3354	Phase 2
0.6857	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD2383	Phase 1
0.6856	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4889	Approved
0.6839	Remote Similarity	NPD2762	Phase 2
0.6834	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7671	Approved
0.6829	Remote Similarity	NPD7672	Approved
0.6822	Remote Similarity	NPD4890	Phase 2
0.682	Remote Similarity	NPD1867	Approved
0.6812	Remote Similarity	NPD6961	Discontinued
0.6806	Remote Similarity	NPD7555	Discontinued
0.6804	Remote Similarity	NPD2951	Discontinued
0.6804	Remote Similarity	NPD2444	Phase 2
0.6798	Remote Similarity	NPD6991	Approved
0.6793	Remote Similarity	NPD1684	Approved
0.6793	Remote Similarity	NPD1685	Approved
0.6793	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3503	Approved
0.6789	Remote Similarity	NPD3504	Approved
0.6786	Remote Similarity	NPD2410	Phase 2
0.6772	Remote Similarity	NPD5065	Approved
0.6771	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3814	Phase 1
0.6765	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3392	Approved
0.6758	Remote Similarity	NPD6494	Phase 2
0.6754	Remote Similarity	NPD8386	Phase 2
0.674	Remote Similarity	NPD5482	Discontinued
0.6739	Remote Similarity	NPD1418	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