NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.09
Volume:	261.239
LogP:	3.559
LogD:	3.609
LogS:	-4.974
# Rotatable Bonds:	3
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	1.943
Fsp3:	0.133
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:	-4.954
MDCK Permeability:	2.262964153487701e-05
Pgp-inhibitor:	0.501
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.757
Plasma Protein Binding (PPB):	91.31767272949219%
Volume Distribution (VD):	0.615
Pgp-substrate:	6.350086688995361%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.9
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.76
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.792
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	7.454
Half-life (T1/2):	0.776

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.628
Skin Sensitization:	0.533
Carcinogencity:	0.138
Eye Corrosion:	0.007
Eye Irritation:	0.836
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC39500

Natural Product ID:	NPC39500
*Common Name:**	Mukonine
IUPAC Name:	methyl 1-methoxy-9H-carbazole-3-carboxylate
Synonyms:
Standard InCHIKey:	GIKICDROPGNERQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO3/c1-18-13-8-9(15(17)19-2)7-11-10-5-3-4-6-12(10)16-14(11)13/h3-8,16H,1-2H3
SMILES:	COC(=O)c1cc(OC)c2c(c1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL236143
PubChem CID:	5319913
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
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	Species	Rutaceae	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	5
Others	9

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	30000.0	nM	PMID[453885]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	43000.0	nM	PMID[453885]
NPT2338	Cell Line	SW48	Homo sapiens	IC50	=	62000.0	nM	PMID[453885]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	72000.0	nM	PMID[453885]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	70.8	%	PMID[453885]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	17.4	%	PMID[453885]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	11.7	%	PMID[453885]
NPT2338	Cell Line	SW48	Homo sapiens	Activity	=	76.7	%	PMID[453885]
NPT2338	Cell Line	SW48	Homo sapiens	Activity	=	14.1	%	PMID[453885]
NPT2338	Cell Line	SW48	Homo sapiens	Activity	=	9.0	%	PMID[453885]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	55.8	%	PMID[453885]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	33.8	%	PMID[453885]
NPT660	Cell Line	SW480	Homo sapiens	Activity	=	10.3	%	PMID[453885]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	80000.0	nM	PMID[453885]

☑ 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 NPC39500 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	523
0.1-0.2	3340
0.2-0.3	12864
0.3-0.4	4217
0.4-0.5	16399
0.5-0.6	3259
0.6-0.7	1565
0.7-0.8	475
0.8-0.85	20
0.85-0.9	23
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC184408
0.9594	High Similarity	NPC144452
0.9583	High Similarity	NPC187501
0.9436	High Similarity	NPC118228
0.9356	High Similarity	NPC274640
0.9343	High Similarity	NPC208084
0.9323	High Similarity	NPC300156
0.9265	High Similarity	NPC474688
0.92	High Similarity	NPC225279
0.9077	High Similarity	NPC4687
0.9064	High Similarity	NPC51388
0.9026	High Similarity	NPC45190
0.902	High Similarity	NPC179287
0.8915	High Similarity	NPC475844
0.8894	High Similarity	NPC87413
0.8836	High Similarity	NPC242928
0.8804	High Similarity	NPC474701
0.8788	High Similarity	NPC283117
0.8788	High Similarity	NPC249583
0.8768	High Similarity	NPC39370
0.8762	High Similarity	NPC116238
0.873	High Similarity	NPC160381
0.8718	High Similarity	NPC128823
0.8706	High Similarity	NPC294375
0.8693	High Similarity	NPC321428
0.8689	High Similarity	NPC280799
0.8676	High Similarity	NPC169402
0.8673	High Similarity	NPC473186
0.865	High Similarity	NPC39679
0.8571	High Similarity	NPC310211
0.8571	High Similarity	NPC308137
0.8557	High Similarity	NPC475190
0.8551	High Similarity	NPC174760
0.8544	High Similarity	NPC46561
0.8519	High Similarity	NPC474798
0.8495	Intermediate Similarity	NPC293151
0.8365	Intermediate Similarity	NPC247803
0.8357	Intermediate Similarity	NPC3207
0.8286	Intermediate Similarity	NPC150239
0.8246	Intermediate Similarity	NPC198503
0.8152	Intermediate Similarity	NPC288987
0.8125	Intermediate Similarity	NPC94157
0.8116	Intermediate Similarity	NPC199667
0.8093	Intermediate Similarity	NPC470018
0.8077	Intermediate Similarity	NPC9894
0.8068	Intermediate Similarity	NPC473181
0.805	Intermediate Similarity	NPC131017
0.8049	Intermediate Similarity	NPC470930
0.8049	Intermediate Similarity	NPC132539
0.8038	Intermediate Similarity	NPC473180
0.8019	Intermediate Similarity	NPC96321
0.8	Intermediate Similarity	NPC230403
0.7944	Intermediate Similarity	NPC132642
0.7933	Intermediate Similarity	NPC86834
0.7933	Intermediate Similarity	NPC210828
0.7928	Intermediate Similarity	NPC6786
0.7909	Intermediate Similarity	NPC49547
0.7905	Intermediate Similarity	NPC23294
0.7897	Intermediate Similarity	NPC473179
0.789	Intermediate Similarity	NPC74575
0.789	Intermediate Similarity	NPC257851
0.7864	Intermediate Similarity	NPC260434
0.7857	Intermediate Similarity	NPC303951
0.7857	Intermediate Similarity	NPC471304
0.785	Intermediate Similarity	NPC473041
0.785	Intermediate Similarity	NPC131885
0.783	Intermediate Similarity	NPC476287
0.7817	Intermediate Similarity	NPC176127
0.7808	Intermediate Similarity	NPC478078
0.7794	Intermediate Similarity	NPC243834
0.7794	Intermediate Similarity	NPC70956
0.7768	Intermediate Similarity	NPC15801
0.7757	Intermediate Similarity	NPC148183
0.7757	Intermediate Similarity	NPC152768
0.7756	Intermediate Similarity	NPC72211
0.7746	Intermediate Similarity	NPC89508
0.7743	Intermediate Similarity	NPC148889
0.774	Intermediate Similarity	NPC245816
0.774	Intermediate Similarity	NPC162484
0.774	Intermediate Similarity	NPC476138
0.7736	Intermediate Similarity	NPC146418
0.7727	Intermediate Similarity	NPC157931
0.7725	Intermediate Similarity	NPC209769
0.7707	Intermediate Similarity	NPC141454
0.7706	Intermediate Similarity	NPC473188
0.77	Intermediate Similarity	NPC118940
0.7696	Intermediate Similarity	NPC472099
0.7696	Intermediate Similarity	NPC276517
0.7696	Intermediate Similarity	NPC118511
0.7692	Intermediate Similarity	NPC311906
0.7665	Intermediate Similarity	NPC88363
0.7662	Intermediate Similarity	NPC165964
0.7659	Intermediate Similarity	NPC70259
0.7656	Intermediate Similarity	NPC476098
0.7656	Intermediate Similarity	NPC165599
0.7653	Intermediate Similarity	NPC84347
0.7647	Intermediate Similarity	NPC473185
0.7644	Intermediate Similarity	NPC473187
0.7644	Intermediate Similarity	NPC470017
0.7642	Intermediate Similarity	NPC208522
0.7639	Intermediate Similarity	NPC312645
0.7634	Intermediate Similarity	NPC329631
0.7633	Intermediate Similarity	NPC280714
0.763	Intermediate Similarity	NPC193777
0.7613	Intermediate Similarity	NPC194740
0.7612	Intermediate Similarity	NPC194040
0.761	Intermediate Similarity	NPC43787
0.761	Intermediate Similarity	NPC205934
0.7606	Intermediate Similarity	NPC470020
0.7604	Intermediate Similarity	NPC174576
0.76	Intermediate Similarity	NPC84478
0.7593	Intermediate Similarity	NPC36405
0.7591	Intermediate Similarity	NPC205372
0.7589	Intermediate Similarity	NPC475720
0.7589	Intermediate Similarity	NPC474192
0.7586	Intermediate Similarity	NPC144381
0.7585	Intermediate Similarity	NPC306376
0.758	Intermediate Similarity	NPC60621
0.7574	Intermediate Similarity	NPC53534
0.7569	Intermediate Similarity	NPC74360
0.7568	Intermediate Similarity	NPC140296
0.7559	Intermediate Similarity	NPC325297
0.7557	Intermediate Similarity	NPC21638
0.7546	Intermediate Similarity	NPC16066
0.7545	Intermediate Similarity	NPC475253
0.7534	Intermediate Similarity	NPC323969
0.7534	Intermediate Similarity	NPC471762
0.7524	Intermediate Similarity	NPC475085
0.7524	Intermediate Similarity	NPC475112
0.7524	Intermediate Similarity	NPC291535
0.7523	Intermediate Similarity	NPC303658
0.7523	Intermediate Similarity	NPC269367
0.7512	Intermediate Similarity	NPC469928
0.7512	Intermediate Similarity	NPC213308
0.7511	Intermediate Similarity	NPC122436
0.75	Intermediate Similarity	NPC478083
0.75	Intermediate Similarity	NPC476106
0.75	Intermediate Similarity	NPC83111
0.7479	Intermediate Similarity	NPC191489
0.7478	Intermediate Similarity	NPC473182
0.7477	Intermediate Similarity	NPC201697
0.7477	Intermediate Similarity	NPC185782
0.7476	Intermediate Similarity	NPC267423
0.7475	Intermediate Similarity	NPC42591
0.7467	Intermediate Similarity	NPC475816
0.7465	Intermediate Similarity	NPC244741
0.7465	Intermediate Similarity	NPC477979
0.7465	Intermediate Similarity	NPC270918
0.7458	Intermediate Similarity	NPC152620
0.7456	Intermediate Similarity	NPC470022
0.7454	Intermediate Similarity	NPC472098
0.7454	Intermediate Similarity	NPC474428
0.7451	Intermediate Similarity	NPC296527
0.745	Intermediate Similarity	NPC478032
0.7441	Intermediate Similarity	NPC199277
0.7441	Intermediate Similarity	NPC135887
0.7432	Intermediate Similarity	NPC314633
0.7429	Intermediate Similarity	NPC329793
0.7415	Intermediate Similarity	NPC76748
0.7407	Intermediate Similarity	NPC208284
0.7406	Intermediate Similarity	NPC134848
0.7406	Intermediate Similarity	NPC223427
0.7406	Intermediate Similarity	NPC475774
0.7406	Intermediate Similarity	NPC89549
0.7404	Intermediate Similarity	NPC251090
0.7404	Intermediate Similarity	NPC473800
0.7397	Intermediate Similarity	NPC305984
0.7396	Intermediate Similarity	NPC76982
0.7393	Intermediate Similarity	NPC476044
0.7391	Intermediate Similarity	NPC307963
0.7383	Intermediate Similarity	NPC193238
0.738	Intermediate Similarity	NPC473183
0.7379	Intermediate Similarity	NPC138370
0.7379	Intermediate Similarity	NPC92111
0.7378	Intermediate Similarity	NPC66777
0.7376	Intermediate Similarity	NPC212535
0.7373	Intermediate Similarity	NPC48353
0.7373	Intermediate Similarity	NPC26679
0.7371	Intermediate Similarity	NPC142385
0.7368	Intermediate Similarity	NPC182222
0.7368	Intermediate Similarity	NPC34770
0.7368	Intermediate Similarity	NPC253675
0.7368	Intermediate Similarity	NPC473184
0.7366	Intermediate Similarity	NPC221873
0.7366	Intermediate Similarity	NPC202503
0.7366	Intermediate Similarity	NPC246700
0.7359	Intermediate Similarity	NPC477066
0.7355	Intermediate Similarity	NPC315634
0.7355	Intermediate Similarity	NPC88923
0.7355	Intermediate Similarity	NPC100734
0.7352	Intermediate Similarity	NPC330009
0.7349	Intermediate Similarity	NPC266249
0.7346	Intermediate Similarity	NPC315491
0.7346	Intermediate Similarity	NPC176538
0.7346	Intermediate Similarity	NPC45459
0.7346	Intermediate Similarity	NPC19872
0.7346	Intermediate Similarity	NPC329747
0.7337	Intermediate Similarity	NPC303225
0.7331	Intermediate Similarity	NPC67401
0.733	Intermediate Similarity	NPC298436

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 NPC39500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	686
0.2-0.3	987
0.3-0.4	1297
0.4-0.5	2975
0.5-0.6	2032
0.6-0.7	710
0.7-0.8	129
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.93	High Similarity	NPD6160	Clinical (unspecified phase)
0.8104	Intermediate Similarity	NPD5632	Approved
0.8036	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD3257	Approved
0.7934	Intermediate Similarity	NPD4429	Discontinued
0.786	Intermediate Similarity	NPD6242	Discontinued
0.7814	Intermediate Similarity	NPD3258	Approved
0.7793	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD1467	Approved
0.7783	Intermediate Similarity	NPD1466	Phase 3
0.7778	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD5482	Discontinued
0.7723	Intermediate Similarity	NPD3006	Discontinued
0.7718	Intermediate Similarity	NPD2778	Approved
0.7707	Intermediate Similarity	NPD5003	Discontinued
0.7703	Intermediate Similarity	NPD1867	Approved
0.7659	Intermediate Similarity	NPD5512	Phase 3
0.7658	Intermediate Similarity	NPD5479	Discontinued
0.7653	Intermediate Similarity	NPD5416	Discontinued
0.7634	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD5429	Discontinued
0.7608	Intermediate Similarity	NPD2779	Approved
0.7604	Intermediate Similarity	NPD7395	Discontinued
0.7586	Intermediate Similarity	NPD2564	Approved
0.7586	Intermediate Similarity	NPD2565	Phase 2
0.7581	Intermediate Similarity	NPD3945	Discontinued
0.7578	Intermediate Similarity	NPD5022	Discontinued
0.7568	Intermediate Similarity	NPD4328	Approved
0.7548	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD5901	Discontinued
0.7512	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD3746	Discontinued
0.75	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD7853	Phase 2
0.7479	Intermediate Similarity	NPD7708	Approved
0.744	Intermediate Similarity	NPD4418	Discontinued
0.7432	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD4952	Phase 3
0.7411	Intermediate Similarity	NPD3259	Approved
0.7411	Intermediate Similarity	NPD7994	Phase 2
0.7391	Intermediate Similarity	NPD1038	Approved
0.7391	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD4885	Approved
0.7356	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5450	Discontinued
0.7355	Intermediate Similarity	NPD7803	Approved
0.7346	Intermediate Similarity	NPD484	Approved
0.7336	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6716	Phase 1
0.7327	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4373	Phase 2
0.7321	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1505	Phase 2
0.7309	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2951	Discontinued
0.7292	Intermediate Similarity	NPD7956	Approved
0.7292	Intermediate Similarity	NPD7955	Approved
0.7277	Intermediate Similarity	NPD8358	Approved
0.7269	Intermediate Similarity	NPD5658	Approved
0.7265	Intermediate Similarity	NPD8363	Approved
0.7265	Intermediate Similarity	NPD8364	Approved
0.7257	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3003	Approved
0.7255	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6770	Approved
0.7243	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4506	Discontinued
0.7229	Intermediate Similarity	NPD4368	Phase 2
0.7227	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5850	Phase 3
0.722	Intermediate Similarity	NPD7180	Phase 3
0.7215	Intermediate Similarity	NPD5866	Approved
0.7207	Intermediate Similarity	NPD3354	Phase 2
0.7206	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2920	Discontinued
0.7162	Intermediate Similarity	NPD5164	Discontinued
0.7162	Intermediate Similarity	NPD7688	Phase 1
0.7162	Intermediate Similarity	NPD6962	Phase 2
0.7161	Intermediate Similarity	NPD5488	Discontinued
0.7156	Intermediate Similarity	NPD6550	Discontinued
0.7155	Intermediate Similarity	NPD5805	Approved
0.7143	Intermediate Similarity	NPD3986	Discontinued
0.7137	Intermediate Similarity	NPD6790	Phase 1
0.7131	Intermediate Similarity	NPD5399	Discovery
0.713	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3947	Discontinued
0.713	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD8463	Approved
0.7112	Intermediate Similarity	NPD4454	Phase 2
0.7112	Intermediate Similarity	NPD3250	Phase 1
0.7103	Intermediate Similarity	NPD3290	Approved
0.7103	Intermediate Similarity	NPD3289	Phase 3
0.7101	Intermediate Similarity	NPD5256	Discontinued
0.7101	Intermediate Similarity	NPD4558	Phase 2
0.7098	Intermediate Similarity	NPD6974	Phase 3
0.7092	Intermediate Similarity	NPD8429	Approved
0.7092	Intermediate Similarity	NPD8466	Approved
0.7092	Intermediate Similarity	NPD8467	Approved
0.7092	Intermediate Similarity	NPD8427	Approved
0.7092	Intermediate Similarity	NPD8428	Approved
0.7092	Intermediate Similarity	NPD8465	Approved
0.7091	Intermediate Similarity	NPD4502	Phase 2
0.7091	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6176	Phase 1
0.7082	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5559	Phase 2
0.7072	Intermediate Similarity	NPD5902	Approved
0.7072	Intermediate Similarity	NPD5903	Approved
0.7067	Intermediate Similarity	NPD4948	Discontinued
0.7064	Intermediate Similarity	NPD7417	Discontinued
0.7061	Intermediate Similarity	NPD7603	Discontinued
0.7056	Intermediate Similarity	NPD1768	Approved
0.7056	Intermediate Similarity	NPD3825	Phase 3
0.705	Intermediate Similarity	NPD2681	Approved
0.705	Intermediate Similarity	NPD2680	Approved
0.705	Intermediate Similarity	NPD2844	Phase 3
0.7049	Intermediate Similarity	NPD6531	Approved
0.7049	Intermediate Similarity	NPD6530	Approved
0.7048	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5913	Phase 3
0.704	Intermediate Similarity	NPD5612	Discontinued
0.7032	Intermediate Similarity	NPD2510	Approved
0.7032	Intermediate Similarity	NPD2509	Approved
0.7029	Intermediate Similarity	NPD8102	Discontinued
0.7027	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD4501	Approved
0.7023	Intermediate Similarity	NPD4500	Approved
0.7014	Intermediate Similarity	NPD7470	Discontinued
0.7009	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7452	Approved
0.6986	Remote Similarity	NPD7222	Phase 2
0.6986	Remote Similarity	NPD7453	Approved
0.6983	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8459	Approved
0.698	Remote Similarity	NPD8426	Approved
0.698	Remote Similarity	NPD8425	Approved
0.698	Remote Similarity	NPD8460	Approved
0.6976	Remote Similarity	NPD4442	Phase 2
0.6976	Remote Similarity	NPD3920	Phase 2
0.697	Remote Similarity	NPD5924	Discontinued
0.6968	Remote Similarity	NPD3392	Approved
0.6964	Remote Similarity	NPD6456	Discontinued
0.6963	Remote Similarity	NPD6988	Phase 1
0.6955	Remote Similarity	NPD7467	Discontinued
0.6955	Remote Similarity	NPD6376	Discontinued
0.6952	Remote Similarity	NPD1534	Approved
0.6951	Remote Similarity	NPD3243	Approved
0.6931	Remote Similarity	NPD1325	Approved
0.6931	Remote Similarity	NPD1326	Approved
0.693	Remote Similarity	NPD6995	Phase 1
0.692	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.692	Remote Similarity	NPD5293	Phase 2
0.6919	Remote Similarity	NPD4499	Approved
0.6914	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3263	Phase 3
0.6906	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7069	Discontinued
0.69	Remote Similarity	NPD7542	Phase 3
0.6897	Remote Similarity	NPD6199	Discontinued
0.6895	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6517	Phase 3
0.688	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2187	Approved
0.6878	Remote Similarity	NPD2189	Approved
0.6875	Remote Similarity	NPD4356	Discontinued
0.6872	Remote Similarity	NPD3875	Discontinued
0.687	Remote Similarity	NPD3925	Approved
0.6868	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5475	Discontinued
0.6861	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5066	Phase 2
0.6861	Remote Similarity	NPD5067	Phase 2
0.6858	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1392	Approved
0.6828	Remote Similarity	NPD6985	Discontinued
0.682	Remote Similarity	NPD7022	Phase 2
0.6816	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3393	Approved
0.6814	Remote Similarity	NPD3389	Approved
0.6814	Remote Similarity	NPD3394	Approved
0.6809	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD8100	Phase 3
0.6796	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2792	Approved
0.6791	Remote Similarity	NPD6590	Discontinued
0.679	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4600	Approved
0.6789	Remote Similarity	NPD6961	Discontinued
0.6789	Remote Similarity	NPD4601	Approved
0.6787	Remote Similarity	NPD8403	Phase 1
0.6787	Remote Similarity	NPD6245	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