NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.09
Volume:	261.239
LogP:	3.6
LogD:	3.667
LogS:	-5.096
# 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:	1.84
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:	-4.905
MDCK Permeability:	2.0486921130213886e-05
Pgp-inhibitor:	0.579
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.42

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.69
Plasma Protein Binding (PPB):	93.424072265625%
Volume Distribution (VD):	0.704
Pgp-substrate:	5.589014053344727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.767
CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.432
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.755
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.765
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	7.57
Half-life (T1/2):	0.604

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.511
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.529
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.608
Carcinogencity:	0.494
Eye Corrosion:	0.005
Eye Irritation:	0.875
Respiratory Toxicity:	0.826

Download Data

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

Natural Product: NPC300156

Natural Product ID:	NPC300156
*Common Name:**	Methyl 6-Methoxycarbazole-3-Carboxylate
IUPAC Name:	methyl 6-methoxy-9H-carbazole-3-carboxylate
Synonyms:
Standard InCHIKey:	ANFDUFMLLFNVTE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO3/c1-18-10-4-6-14-12(8-10)11-7-9(15(17)19-2)3-5-13(11)16-14/h3-8,16H,1-2H3
SMILES:	COc1ccc2c(c1)c1cc(ccc1[nH]2)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036043
PubChem CID:	14804151
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
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19327990]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22372931]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24798144]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26523463]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23546	Clausena lansium	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	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	128000.0	nM	PMID[504055]
NPT2	Others	Unspecified		Selectivity Index	>	4.0	n.a.	PMID[504055]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	=	32000.0	nM	PMID[504055]

☑ 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 NPC300156 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	506
0.1-0.2	3220
0.2-0.3	12662
0.3-0.4	3951
0.4-0.5	16350
0.5-0.6	3582
0.6-0.7	1779
0.7-0.8	569
0.8-0.85	46
0.85-0.9	21
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9676	High Similarity	NPC45190
0.9415	High Similarity	NPC4687
0.9323	High Similarity	NPC39500
0.9286	High Similarity	NPC280799
0.9219	High Similarity	NPC87413
0.9133	High Similarity	NPC46561
0.9133	High Similarity	NPC184408
0.911	High Similarity	NPC249583
0.9077	High Similarity	NPC116238
0.9066	High Similarity	NPC160381
0.9021	High Similarity	NPC187501
0.901	High Similarity	NPC321428
0.8985	High Similarity	NPC169402
0.8964	High Similarity	NPC39679
0.895	High Similarity	NPC144452
0.8883	High Similarity	NPC118228
0.8878	High Similarity	NPC308137
0.8878	High Similarity	NPC310211
0.885	High Similarity	NPC174760
0.88	High Similarity	NPC208084
0.8732	High Similarity	NPC274640
0.8663	High Similarity	NPC225279
0.8657	High Similarity	NPC247803
0.865	High Similarity	NPC3207
0.8647	High Similarity	NPC474688
0.8636	High Similarity	NPC9894
0.8632	High Similarity	NPC131017
0.8585	High Similarity	NPC179287
0.8571	High Similarity	NPC150239
0.8564	High Similarity	NPC96321
0.8543	High Similarity	NPC294375
0.8537	High Similarity	NPC51388
0.8529	High Similarity	NPC198503
0.8443	Intermediate Similarity	NPC6786
0.84	Intermediate Similarity	NPC471304
0.8396	Intermediate Similarity	NPC176127
0.8368	Intermediate Similarity	NPC242928
0.8349	Intermediate Similarity	NPC39370
0.8342	Intermediate Similarity	NPC283117
0.8341	Intermediate Similarity	NPC473186
0.8326	Intermediate Similarity	NPC475844
0.8325	Intermediate Similarity	NPC478078
0.8294	Intermediate Similarity	NPC474701
0.8283	Intermediate Similarity	NPC162484
0.8238	Intermediate Similarity	NPC157931
0.8235	Intermediate Similarity	NPC88363
0.8213	Intermediate Similarity	NPC472099
0.8209	Intermediate Similarity	NPC210828
0.8209	Intermediate Similarity	NPC86834
0.8199	Intermediate Similarity	NPC311906
0.8177	Intermediate Similarity	NPC23294
0.8173	Intermediate Similarity	NPC128823
0.8159	Intermediate Similarity	NPC193777
0.8154	Intermediate Similarity	NPC276517
0.8128	Intermediate Similarity	NPC303951
0.8116	Intermediate Similarity	NPC473041
0.8107	Intermediate Similarity	NPC148183
0.8107	Intermediate Similarity	NPC152768
0.8103	Intermediate Similarity	NPC475190
0.8084	Intermediate Similarity	NPC474192
0.8084	Intermediate Similarity	NPC475720
0.8077	Intermediate Similarity	NPC74360
0.8071	Intermediate Similarity	NPC243834
0.8071	Intermediate Similarity	NPC70956
0.8068	Intermediate Similarity	NPC293151
0.8053	Intermediate Similarity	NPC474798
0.804	Intermediate Similarity	NPC213308
0.8032	Intermediate Similarity	NPC84347
0.803	Intermediate Similarity	NPC72211
0.8019	Intermediate Similarity	NPC469928
0.801	Intermediate Similarity	NPC476098
0.799	Intermediate Similarity	NPC296527
0.799	Intermediate Similarity	NPC280714
0.799	Intermediate Similarity	NPC201697
0.798	Intermediate Similarity	NPC270918
0.797	Intermediate Similarity	NPC132539
0.796	Intermediate Similarity	NPC135887
0.796	Intermediate Similarity	NPC199277
0.795	Intermediate Similarity	NPC329793
0.7949	Intermediate Similarity	NPC76748
0.7945	Intermediate Similarity	NPC475816
0.7936	Intermediate Similarity	NPC15801
0.7929	Intermediate Similarity	NPC70259
0.7929	Intermediate Similarity	NPC251090
0.7921	Intermediate Similarity	NPC223427
0.7919	Intermediate Similarity	NPC307963
0.7915	Intermediate Similarity	NPC60621
0.7913	Intermediate Similarity	NPC208284
0.7908	Intermediate Similarity	NPC92111
0.7897	Intermediate Similarity	NPC246700
0.7892	Intermediate Similarity	NPC193238
0.789	Intermediate Similarity	NPC473187
0.7885	Intermediate Similarity	NPC478083
0.7885	Intermediate Similarity	NPC16066
0.7879	Intermediate Similarity	NPC43787
0.7879	Intermediate Similarity	NPC205934
0.7876	Intermediate Similarity	NPC84478
0.7874	Intermediate Similarity	NPC48353
0.7874	Intermediate Similarity	NPC472098
0.7861	Intermediate Similarity	NPC176538
0.785	Intermediate Similarity	NPC470018
0.7828	Intermediate Similarity	NPC477066
0.7816	Intermediate Similarity	NPC325297
0.7804	Intermediate Similarity	NPC21638
0.7795	Intermediate Similarity	NPC194040
0.7793	Intermediate Similarity	NPC478082
0.7793	Intermediate Similarity	NPC477067
0.7793	Intermediate Similarity	NPC478081
0.7793	Intermediate Similarity	NPC473540
0.7788	Intermediate Similarity	NPC94157
0.7788	Intermediate Similarity	NPC260434
0.7783	Intermediate Similarity	NPC89549
0.7783	Intermediate Similarity	NPC323969
0.7783	Intermediate Similarity	NPC475085
0.7783	Intermediate Similarity	NPC475112
0.7783	Intermediate Similarity	NPC291535
0.7778	Intermediate Similarity	NPC470020
0.7778	Intermediate Similarity	NPC471762
0.7772	Intermediate Similarity	NPC315491
0.7772	Intermediate Similarity	NPC45459
0.7766	Intermediate Similarity	NPC83111
0.7761	Intermediate Similarity	NPC306376
0.7757	Intermediate Similarity	NPC122436
0.7751	Intermediate Similarity	NPC89508
0.7736	Intermediate Similarity	NPC288987
0.7734	Intermediate Similarity	NPC267423
0.7733	Intermediate Similarity	NPC17437
0.7731	Intermediate Similarity	NPC257851
0.7727	Intermediate Similarity	NPC138370
0.7718	Intermediate Similarity	NPC88008
0.7716	Intermediate Similarity	NPC128751
0.7711	Intermediate Similarity	NPC153042
0.7711	Intermediate Similarity	NPC141454
0.7703	Intermediate Similarity	NPC219087
0.77	Intermediate Similarity	NPC276657
0.7696	Intermediate Similarity	NPC194740
0.7692	Intermediate Similarity	NPC269367
0.7692	Intermediate Similarity	NPC199667
0.7681	Intermediate Similarity	NPC171787
0.7677	Intermediate Similarity	NPC106833
0.7677	Intermediate Similarity	NPC469497
0.7676	Intermediate Similarity	NPC76982
0.767	Intermediate Similarity	NPC476106
0.7659	Intermediate Similarity	NPC165599
0.7659	Intermediate Similarity	NPC134848
0.765	Intermediate Similarity	NPC74575
0.7647	Intermediate Similarity	NPC476044
0.7644	Intermediate Similarity	NPC473181
0.7642	Intermediate Similarity	NPC312645
0.7642	Intermediate Similarity	NPC305984
0.7641	Intermediate Similarity	NPC212535
0.7629	Intermediate Similarity	NPC191489
0.7621	Intermediate Similarity	NPC470930
0.7619	Intermediate Similarity	NPC473180
0.7619	Intermediate Similarity	NPC118940
0.7615	Intermediate Similarity	NPC66777
0.7611	Intermediate Similarity	NPC475666
0.7608	Intermediate Similarity	NPC309845
0.7606	Intermediate Similarity	NPC303658
0.7602	Intermediate Similarity	NPC253675
0.7598	Intermediate Similarity	NPC329747
0.7594	Intermediate Similarity	NPC330009
0.7591	Intermediate Similarity	NPC49547
0.7583	Intermediate Similarity	NPC478074
0.7566	Intermediate Similarity	NPC81939
0.7565	Intermediate Similarity	NPC329982
0.7563	Intermediate Similarity	NPC94943
0.7562	Intermediate Similarity	NPC230403
0.7557	Intermediate Similarity	NPC473105
0.7555	Intermediate Similarity	NPC473800
0.7548	Intermediate Similarity	NPC244741
0.7538	Intermediate Similarity	NPC63199
0.7538	Intermediate Similarity	NPC196251
0.7538	Intermediate Similarity	NPC102338
0.7538	Intermediate Similarity	NPC111602
0.7537	Intermediate Similarity	NPC156704
0.7535	Intermediate Similarity	NPC132642
0.7535	Intermediate Similarity	NPC86078
0.7534	Intermediate Similarity	NPC235685
0.7532	Intermediate Similarity	NPC303374
0.7513	Intermediate Similarity	NPC303225
0.7513	Intermediate Similarity	NPC190007
0.7512	Intermediate Similarity	NPC82548
0.7512	Intermediate Similarity	NPC36405
0.75	Intermediate Similarity	NPC88923
0.75	Intermediate Similarity	NPC315634
0.75	Intermediate Similarity	NPC101350
0.75	Intermediate Similarity	NPC266931
0.75	Intermediate Similarity	NPC67288
0.75	Intermediate Similarity	NPC100734
0.7488	Intermediate Similarity	NPC473179
0.7488	Intermediate Similarity	NPC220337
0.7488	Intermediate Similarity	NPC146418
0.7488	Intermediate Similarity	NPC298436
0.7464	Intermediate Similarity	NPC53344
0.7461	Intermediate Similarity	NPC474409
0.7457	Intermediate Similarity	NPC478080
0.7455	Intermediate Similarity	NPC252251
0.7436	Intermediate Similarity	NPC284685
0.7435	Intermediate Similarity	NPC165964

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 NPC300156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	678
0.2-0.3	962
0.3-0.4	1198
0.4-0.5	2865
0.5-0.6	2122
0.6-0.7	834
0.7-0.8	145
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
0.8856	High Similarity	NPD6160	Clinical (unspecified phase)
0.8507	High Similarity	NPD3257	Approved
0.839	Intermediate Similarity	NPD6242	Discontinued
0.8341	Intermediate Similarity	NPD3258	Approved
0.8204	Intermediate Similarity	NPD5632	Approved
0.8081	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD4328	Approved
0.8045	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD4418	Discontinued
0.7919	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1038	Approved
0.7879	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5416	Discontinued
0.7824	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD5901	Discontinued
0.7783	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD484	Approved
0.7767	Intermediate Similarity	NPD5658	Approved
0.7733	Intermediate Similarity	NPD8358	Approved
0.7714	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD5003	Discontinued
0.7689	Intermediate Similarity	NPD3354	Phase 2
0.7671	Intermediate Similarity	NPD4885	Approved
0.7661	Intermediate Similarity	NPD4952	Phase 3
0.7629	Intermediate Similarity	NPD7708	Approved
0.7611	Intermediate Similarity	NPD5488	Discontinued
0.7606	Intermediate Similarity	NPD4429	Discontinued
0.7588	Intermediate Similarity	NPD2564	Approved
0.7588	Intermediate Similarity	NPD5482	Discontinued
0.7588	Intermediate Similarity	NPD2565	Phase 2
0.7574	Intermediate Similarity	NPD5512	Phase 3
0.7557	Intermediate Similarity	NPD4373	Phase 2
0.7548	Intermediate Similarity	NPD5429	Discontinued
0.7544	Intermediate Similarity	NPD4558	Phase 2
0.7523	Intermediate Similarity	NPD7395	Discontinued
0.75	Intermediate Similarity	NPD7803	Approved
0.7489	Intermediate Similarity	NPD3259	Approved
0.7476	Intermediate Similarity	NPD4506	Discontinued
0.7467	Intermediate Similarity	NPD8102	Discontinued
0.7436	Intermediate Similarity	NPD7955	Approved
0.7436	Intermediate Similarity	NPD7956	Approved
0.7421	Intermediate Similarity	NPD5479	Discontinued
0.7416	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3003	Approved
0.7411	Intermediate Similarity	NPD3006	Discontinued
0.7409	Intermediate Similarity	NPD7994	Phase 2
0.7406	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6530	Approved
0.7404	Intermediate Similarity	NPD6531	Approved
0.7396	Intermediate Similarity	NPD2844	Phase 3
0.7387	Intermediate Similarity	NPD6962	Phase 2
0.7383	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2778	Approved
0.7379	Intermediate Similarity	NPD3825	Phase 3
0.7378	Intermediate Similarity	NPD5805	Approved
0.7368	Intermediate Similarity	NPD3947	Discontinued
0.7368	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6790	Phase 1
0.7349	Intermediate Similarity	NPD5612	Discontinued
0.7346	Intermediate Similarity	NPD2187	Approved
0.7346	Intermediate Similarity	NPD2509	Approved
0.7346	Intermediate Similarity	NPD2189	Approved
0.7346	Intermediate Similarity	NPD2510	Approved
0.7343	Intermediate Similarity	NPD3289	Phase 3
0.7343	Intermediate Similarity	NPD3290	Approved
0.7339	Intermediate Similarity	NPD8463	Approved
0.7336	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6176	Phase 1
0.7313	Intermediate Similarity	NPD4948	Discontinued
0.731	Intermediate Similarity	NPD3920	Phase 2
0.7309	Intermediate Similarity	NPD1867	Approved
0.7297	Intermediate Similarity	NPD5559	Phase 2
0.729	Intermediate Similarity	NPD5866	Approved
0.7273	Intermediate Similarity	NPD2779	Approved
0.7269	Intermediate Similarity	NPD5399	Discovery
0.7265	Intermediate Similarity	NPD5022	Discontinued
0.7265	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4500	Approved
0.726	Intermediate Similarity	NPD4501	Approved
0.7248	Intermediate Similarity	NPD6770	Approved
0.7244	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1466	Phase 3
0.7232	Intermediate Similarity	NPD1467	Approved
0.7227	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5293	Phase 2
0.722	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7452	Approved
0.7217	Intermediate Similarity	NPD7453	Approved
0.7217	Intermediate Similarity	NPD7222	Phase 2
0.7212	Intermediate Similarity	NPD1768	Approved
0.7208	Intermediate Similarity	NPD5450	Discontinued
0.72	Intermediate Similarity	NPD3746	Discontinued
0.7192	Intermediate Similarity	NPD1534	Approved
0.719	Intermediate Similarity	NPD8363	Approved
0.719	Intermediate Similarity	NPD8364	Approved
0.7183	Intermediate Similarity	NPD6376	Discontinued
0.7179	Intermediate Similarity	NPD1325	Approved
0.7179	Intermediate Similarity	NPD1326	Approved
0.7176	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3945	Discontinued
0.7175	Intermediate Similarity	NPD4845	Discontinued
0.7174	Intermediate Similarity	NPD6716	Phase 1
0.717	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4499	Approved
0.7156	Intermediate Similarity	NPD7688	Phase 1
0.7156	Intermediate Similarity	NPD2920	Discontinued
0.7149	Intermediate Similarity	NPD6995	Phase 1
0.7143	Intermediate Similarity	NPD5902	Approved
0.7143	Intermediate Similarity	NPD5903	Approved
0.7131	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7417	Discontinued
0.713	Intermediate Similarity	NPD7069	Discontinued
0.7129	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4795	Phase 2
0.7123	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5913	Phase 3
0.7122	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6228	Discontinued
0.711	Intermediate Similarity	NPD3393	Approved
0.711	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3394	Approved
0.711	Intermediate Similarity	NPD3389	Approved
0.7105	Intermediate Similarity	NPD7853	Phase 2
0.7101	Intermediate Similarity	NPD8091	Phase 3
0.7097	Intermediate Similarity	NPD4356	Discontinued
0.7095	Intermediate Similarity	NPD1739	Approved
0.7095	Intermediate Similarity	NPD1740	Approved
0.7085	Intermediate Similarity	NPD8429	Approved
0.7085	Intermediate Similarity	NPD8466	Approved
0.7085	Intermediate Similarity	NPD8467	Approved
0.7085	Intermediate Similarity	NPD8428	Approved
0.7085	Intermediate Similarity	NPD3925	Approved
0.7085	Intermediate Similarity	NPD8427	Approved
0.7085	Intermediate Similarity	NPD8465	Approved
0.7083	Intermediate Similarity	NPD7470	Discontinued
0.7079	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6550	Discontinued
0.705	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6987	Phase 1
0.704	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2916	Discontinued
0.7018	Intermediate Similarity	NPD3243	Approved
0.7014	Intermediate Similarity	NPD4600	Approved
0.7014	Intermediate Similarity	NPD4601	Approved
0.7009	Intermediate Similarity	NPD6245	Phase 2
0.7009	Intermediate Similarity	NPD8403	Phase 1
0.7	Intermediate Similarity	NPD5164	Discontinued
0.6995	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4511	Phase 1
0.6977	Remote Similarity	NPD1392	Approved
0.6972	Remote Similarity	NPD8459	Approved
0.6972	Remote Similarity	NPD8425	Approved
0.6972	Remote Similarity	NPD8426	Approved
0.6972	Remote Similarity	NPD8460	Approved
0.6955	Remote Similarity	NPD8160	Phase 2
0.6953	Remote Similarity	NPD6517	Phase 3
0.6953	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.695	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3853	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8100	Phase 3
0.693	Remote Similarity	NPD5530	Phase 1
0.693	Remote Similarity	NPD7010	Phase 3
0.6927	Remote Similarity	NPD5067	Phase 2
0.6927	Remote Similarity	NPD5066	Phase 2
0.6923	Remote Similarity	NPD3923	Approved
0.6923	Remote Similarity	NPD3921	Approved
0.6923	Remote Similarity	NPD3924	Approved
0.6923	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3922	Approved
0.692	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7946	Pre-registration
0.6916	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2951	Discontinued
0.6909	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4897	Phase 2
0.6906	Remote Similarity	NPD5930	Phase 3
0.69	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.69	Remote Similarity	NPD482	Approved
0.6897	Remote Similarity	NPD4204	Approved
0.6897	Remote Similarity	NPD4203	Approved
0.6892	Remote Similarity	NPD6985	Discontinued
0.6884	Remote Similarity	NPD8283	Approved
0.6884	Remote Similarity	NPD8282	Approved
0.6884	Remote Similarity	NPD56	Approved
0.6881	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4889	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data