NPASS Compound

Structure

CID86078 OpenBabel06191715422D 24 28 0 0 0 0 0 0 0 0999 V2000 2.4587 -2.9028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4235 -2.4143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9070 -0.1026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4233 -1.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5109 0.7876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5798 -2.9017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3341 -0.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5795 -0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5419 0.8897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2034 -3.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7355 -2.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3651 -0.7886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2032 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7353 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9690 0.1016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0474 -2.4150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6409 -1.4404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0472 -1.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2028 -0.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6407 -2.4153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2836 -4.7206 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8914 -0.9527 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4844 -2.9027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 11 2 0 0 0 0 7 12 2 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 10 13 1 0 0 0 0 10 21 3 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.11
Volume:	324.473
LogP:	4.853
LogD:	3.887
LogS:	-6.994
# Rotatable Bonds:	1
TPSA:	64.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	2.589
Fsp3:	0.05
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:	-5.213
MDCK Permeability:	8.518772119714413e-06
Pgp-inhibitor:	0.177
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.316
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	97.62140655517578%
Volume Distribution (VD):	0.399
Pgp-substrate:	2.159297227859497%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.933
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.703
CYP2D6-substrate:	0.87
CYP3A4-inhibitor:	0.427
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	4.211
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.882
Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.948
Carcinogencity:	0.918
Eye Corrosion:	0.092
Eye Irritation:	0.99
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC86078

Natural Product ID:	NPC86078
*Common Name:**	6-Cyano-5-Methoxyindolo[2,3-A]Carbazole
IUPAC Name:	5-methoxy-11,12-dihydroindolo[2,3-a]carbazole-6-carbonitrile
Synonyms:
Standard InCHIKey:	ADLSFYJDHWUKFP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H13N3O/c1-24-20-13(10-21)16-11-6-2-4-8-14(11)22-18(16)19-17(20)12-7-3-5-9-15(12)23-19/h2-9,22-23H,1H3
SMILES:	COc1c2c([nH]c3c2cccc3)c2c(c1C#N)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL596128
PubChem CID:	131448
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1021/jo00416a020]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608844]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24476550]
NPO8305	Katsuwonus pelamis	Species	Scombridae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12744	Ajuga nipponensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10879	Lasius meridionalis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4198	Ungernia vvedenskyi	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12744	Ajuga nipponensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23436	Cladrastis sikokiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8811	Cytisus prolifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1969	Streptomyces pilosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19804	Lycopodium saururus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28833	Eleutherococcus sieboldianus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO834	Peperomia clusiifolia	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5335	0stoc sp	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8623	Anneissia japonica	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18618	Neurolaena lobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9705	Meyerozyma guilliermondii	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7788	Rana catesbeiana	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4541	Capnella lacertiliensis	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19541	Smilax moranensis	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8305	Katsuwonus pelamis	Species	Scombridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1537	Vaccinium arctostaphylos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8426	Tinospora rumphii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7240	Osteospermum oppositifolium	Species	Asteraceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	=	6300.0	nM	PMID[488084]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	128000.0	nM	PMID[488084]

☑ 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 NPC86078 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	1032
0.1-0.2	6612
0.2-0.3	10942
0.3-0.4	14270
0.4-0.5	5984
0.5-0.6	2647
0.6-0.7	961
0.7-0.8	215
0.8-0.85	30
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC227908
0.8442	Intermediate Similarity	NPC131017
0.8439	Intermediate Similarity	NPC193777
0.8413	Intermediate Similarity	NPC473180
0.838	Intermediate Similarity	NPC252251
0.8357	Intermediate Similarity	NPC201697
0.8325	Intermediate Similarity	NPC294620
0.8303	Intermediate Similarity	NPC477531
0.8293	Intermediate Similarity	NPC162484
0.8278	Intermediate Similarity	NPC208284
0.8257	Intermediate Similarity	NPC209174
0.8238	Intermediate Similarity	NPC48353
0.8195	Intermediate Similarity	NPC267423
0.8182	Intermediate Similarity	NPC473181
0.816	Intermediate Similarity	NPC470549
0.8143	Intermediate Similarity	NPC199667
0.8122	Intermediate Similarity	NPC170114
0.8116	Intermediate Similarity	NPC223427
0.8093	Intermediate Similarity	NPC473179
0.8079	Intermediate Similarity	NPC43787
0.8079	Intermediate Similarity	NPC205934
0.8049	Intermediate Similarity	NPC72211
0.8039	Intermediate Similarity	NPC70259
0.8037	Intermediate Similarity	NPC202503
0.8	Intermediate Similarity	NPC243834
0.8	Intermediate Similarity	NPC153042
0.8	Intermediate Similarity	NPC70956
0.799	Intermediate Similarity	NPC195314
0.7982	Intermediate Similarity	NPC473182
0.7936	Intermediate Similarity	NPC477532
0.7933	Intermediate Similarity	NPC476044
0.7921	Intermediate Similarity	NPC128751
0.7921	Intermediate Similarity	NPC246700
0.7919	Intermediate Similarity	NPC473185
0.7897	Intermediate Similarity	NPC94157
0.789	Intermediate Similarity	NPC477533
0.7885	Intermediate Similarity	NPC176538
0.7882	Intermediate Similarity	NPC106833
0.7882	Intermediate Similarity	NPC469497
0.786	Intermediate Similarity	NPC478074
0.785	Intermediate Similarity	NPC176127
0.7812	Intermediate Similarity	NPC475253
0.781	Intermediate Similarity	NPC475085
0.781	Intermediate Similarity	NPC475112
0.781	Intermediate Similarity	NPC291535
0.7804	Intermediate Similarity	NPC167860
0.7804	Intermediate Similarity	NPC123976
0.7783	Intermediate Similarity	NPC476106
0.7778	Intermediate Similarity	NPC13880
0.7762	Intermediate Similarity	NPC232727
0.7745	Intermediate Similarity	NPC242928
0.7723	Intermediate Similarity	NPC84478
0.7699	Intermediate Similarity	NPC132329
0.7692	Intermediate Similarity	NPC280799
0.7672	Intermediate Similarity	NPC160898
0.7653	Intermediate Similarity	NPC470930
0.7647	Intermediate Similarity	NPC132642
0.7642	Intermediate Similarity	NPC473183
0.7642	Intermediate Similarity	NPC135887
0.7642	Intermediate Similarity	NPC199277
0.7636	Intermediate Similarity	NPC46561
0.7635	Intermediate Similarity	NPC190007
0.7632	Intermediate Similarity	NPC473184
0.763	Intermediate Similarity	NPC11017
0.763	Intermediate Similarity	NPC329793
0.763	Intermediate Similarity	NPC315957
0.763	Intermediate Similarity	NPC329747
0.7619	Intermediate Similarity	NPC477066
0.7612	Intermediate Similarity	NPC88363
0.7602	Intermediate Similarity	NPC193267
0.7602	Intermediate Similarity	NPC213530
0.7598	Intermediate Similarity	NPC94943
0.7598	Intermediate Similarity	NPC473189
0.7586	Intermediate Similarity	NPC212535
0.7586	Intermediate Similarity	NPC478081
0.757	Intermediate Similarity	NPC285558
0.7565	Intermediate Similarity	NPC6786
0.7558	Intermediate Similarity	NPC11464
0.7555	Intermediate Similarity	NPC277351
0.7535	Intermediate Similarity	NPC300156
0.7535	Intermediate Similarity	NPC45190
0.7534	Intermediate Similarity	NPC310118
0.7522	Intermediate Similarity	NPC473187
0.7511	Intermediate Similarity	NPC477067
0.7511	Intermediate Similarity	NPC478082
0.751	Intermediate Similarity	NPC89549
0.75	Intermediate Similarity	NPC128823
0.7488	Intermediate Similarity	NPC474188
0.7488	Intermediate Similarity	NPC296527
0.7467	Intermediate Similarity	NPC469554
0.7465	Intermediate Similarity	NPC121772
0.7457	Intermediate Similarity	NPC11408
0.7455	Intermediate Similarity	NPC469592
0.7455	Intermediate Similarity	NPC471080
0.7452	Intermediate Similarity	NPC76748
0.7451	Intermediate Similarity	NPC474798
0.7436	Intermediate Similarity	NPC473540
0.7431	Intermediate Similarity	NPC209769
0.7419	Intermediate Similarity	NPC4687
0.7419	Intermediate Similarity	NPC249583
0.7416	Intermediate Similarity	NPC92111
0.7413	Intermediate Similarity	NPC474409
0.7409	Intermediate Similarity	NPC308137
0.7409	Intermediate Similarity	NPC310211
0.7397	Intermediate Similarity	NPC471304
0.7393	Intermediate Similarity	NPC217554
0.7391	Intermediate Similarity	NPC101543
0.7385	Intermediate Similarity	NPC470931
0.7384	Intermediate Similarity	NPC17437
0.7383	Intermediate Similarity	NPC19872
0.7376	Intermediate Similarity	NPC31700
0.7368	Intermediate Similarity	NPC110151
0.7361	Intermediate Similarity	NPC476138
0.7361	Intermediate Similarity	NPC245816
0.7354	Intermediate Similarity	NPC169402
0.7346	Intermediate Similarity	NPC307963
0.7342	Intermediate Similarity	NPC116238
0.7336	Intermediate Similarity	NPC18487
0.7336	Intermediate Similarity	NPC314954
0.7327	Intermediate Similarity	NPC475070
0.7321	Intermediate Similarity	NPC469594
0.7306	Intermediate Similarity	NPC475910
0.7301	Intermediate Similarity	NPC198503
0.73	Intermediate Similarity	NPC284141
0.7299	Intermediate Similarity	NPC280964
0.7299	Intermediate Similarity	NPC141915
0.7299	Intermediate Similarity	NPC114335
0.7296	Intermediate Similarity	NPC295228
0.7293	Intermediate Similarity	NPC470126
0.7285	Intermediate Similarity	NPC87413
0.7285	Intermediate Similarity	NPC9894
0.7277	Intermediate Similarity	NPC251090
0.7277	Intermediate Similarity	NPC305984
0.7273	Intermediate Similarity	NPC478080
0.7273	Intermediate Similarity	NPC185782
0.7273	Intermediate Similarity	NPC285635
0.7269	Intermediate Similarity	NPC280272
0.7265	Intermediate Similarity	NPC235685
0.7261	Intermediate Similarity	NPC253580
0.7257	Intermediate Similarity	NPC150239
0.7255	Intermediate Similarity	NPC56618
0.7253	Intermediate Similarity	NPC39370
0.7252	Intermediate Similarity	NPC26679
0.7244	Intermediate Similarity	NPC96321
0.7244	Intermediate Similarity	NPC247803
0.7241	Intermediate Similarity	NPC473186
0.724	Intermediate Similarity	NPC5145
0.7237	Intermediate Similarity	NPC211416
0.7234	Intermediate Similarity	NPC101350
0.7232	Intermediate Similarity	NPC152768
0.7232	Intermediate Similarity	NPC148183
0.7225	Intermediate Similarity	NPC60621
0.7212	Intermediate Similarity	NPC208084
0.7212	Intermediate Similarity	NPC46451
0.7205	Intermediate Similarity	NPC98371
0.7205	Intermediate Similarity	NPC313884
0.7202	Intermediate Similarity	NPC477135
0.72	Intermediate Similarity	NPC314552
0.72	Intermediate Similarity	NPC304926
0.72	Intermediate Similarity	NPC476041
0.7197	Intermediate Similarity	NPC475666
0.7195	Intermediate Similarity	NPC174672
0.7193	Intermediate Similarity	NPC144452
0.7188	Intermediate Similarity	NPC235076
0.7181	Intermediate Similarity	NPC174760
0.7181	Intermediate Similarity	NPC225279
0.7172	Intermediate Similarity	NPC26850
0.7168	Intermediate Similarity	NPC303658
0.7155	Intermediate Similarity	NPC81939
0.7149	Intermediate Similarity	NPC82548
0.7103	Intermediate Similarity	NPC475190
0.7102	Intermediate Similarity	NPC478083
0.7101	Intermediate Similarity	NPC72980
0.7098	Intermediate Similarity	NPC316981
0.7095	Intermediate Similarity	NPC476319
0.7093	Intermediate Similarity	NPC23614
0.7093	Intermediate Similarity	NPC473041
0.7093	Intermediate Similarity	NPC100079
0.7087	Intermediate Similarity	NPC122436
0.708	Intermediate Similarity	NPC8022
0.708	Intermediate Similarity	NPC470799
0.708	Intermediate Similarity	NPC183407
0.7072	Intermediate Similarity	NPC39679
0.7067	Intermediate Similarity	NPC39500
0.7067	Intermediate Similarity	NPC266931
0.7066	Intermediate Similarity	NPC91868
0.7066	Intermediate Similarity	NPC63971
0.7064	Intermediate Similarity	NPC249040
0.7059	Intermediate Similarity	NPC304183
0.7056	Intermediate Similarity	NPC179287
0.7054	Intermediate Similarity	NPC187501
0.7051	Intermediate Similarity	NPC474688
0.704	Intermediate Similarity	NPC476116
0.704	Intermediate Similarity	NPC174758
0.704	Intermediate Similarity	NPC469589
0.7039	Intermediate Similarity	NPC274640
0.7026	Intermediate Similarity	NPC200888
0.7024	Intermediate Similarity	NPC258773
0.7018	Intermediate Similarity	NPC477609
0.7009	Intermediate Similarity	NPC188420

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 NPC86078 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	527
0.1-0.2	692
0.2-0.3	929
0.3-0.4	2041
0.4-0.5	2869
0.5-0.6	1626
0.6-0.7	429
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7877	Intermediate Similarity	NPD5658	Approved
0.7867	Intermediate Similarity	NPD5530	Phase 1
0.7751	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD4795	Phase 2
0.7682	Intermediate Similarity	NPD7194	Discontinued
0.7647	Intermediate Similarity	NPD5930	Phase 3
0.7644	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1739	Approved
0.763	Intermediate Similarity	NPD1740	Approved
0.7557	Intermediate Similarity	NPD6985	Discontinued
0.7489	Intermediate Similarity	NPD5488	Discontinued
0.7454	Intermediate Similarity	NPD3003	Approved
0.7429	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5902	Approved
0.7421	Intermediate Similarity	NPD5903	Approved
0.7384	Intermediate Similarity	NPD8358	Approved
0.7346	Intermediate Similarity	NPD1038	Approved
0.7336	Intermediate Similarity	NPD5559	Phase 2
0.7269	Intermediate Similarity	NPD7219	Approved
0.7269	Intermediate Similarity	NPD7221	Approved
0.7241	Intermediate Similarity	NPD3746	Discontinued
0.7212	Intermediate Similarity	NPD3763	Approved
0.7205	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5164	Discontinued
0.7176	Intermediate Similarity	NPD1768	Approved
0.7176	Intermediate Similarity	NPD2151	Approved
0.7143	Intermediate Similarity	NPD6978	Phase 2
0.7143	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5066	Phase 2
0.713	Intermediate Similarity	NPD5067	Phase 2
0.7118	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5913	Phase 3
0.7085	Intermediate Similarity	NPD6531	Approved
0.7085	Intermediate Similarity	NPD6530	Approved
0.7061	Intermediate Similarity	NPD6455	Phase 3
0.7059	Intermediate Similarity	NPD6150	Discontinued
0.7059	Intermediate Similarity	NPD8403	Phase 1
0.7048	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4511	Phase 1
0.7031	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7452	Approved
0.7027	Intermediate Similarity	NPD7453	Approved
0.7027	Intermediate Similarity	NPD7222	Phase 2
0.7019	Intermediate Similarity	NPD3920	Phase 2
0.7018	Intermediate Similarity	NPD3825	Phase 3
0.7012	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD2187	Approved
0.6996	Remote Similarity	NPD2189	Approved
0.6992	Remote Similarity	NPD7558	Phase 2
0.6991	Remote Similarity	NPD4418	Discontinued
0.6987	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5802	Phase 2
0.6967	Remote Similarity	NPD5482	Discontinued
0.6962	Remote Similarity	NPD6760	Discontinued
0.6957	Remote Similarity	NPD6242	Discontinued
0.6951	Remote Similarity	NPD1392	Approved
0.6944	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5632	Approved
0.6941	Remote Similarity	NPD8396	Approved
0.6941	Remote Similarity	NPD8395	Approved
0.6939	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD8512	Phase 3
0.6934	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5612	Discontinued
0.6929	Remote Similarity	NPD6473	Phase 1
0.6923	Remote Similarity	NPD6975	Discontinued
0.6923	Remote Similarity	NPD6208	Discontinued
0.692	Remote Similarity	NPD6494	Phase 2
0.6913	Remote Similarity	NPD3875	Discontinued
0.6912	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6245	Phase 2
0.6893	Remote Similarity	NPD1325	Approved
0.6893	Remote Similarity	NPD1326	Approved
0.6892	Remote Similarity	NPD2920	Discontinued
0.6891	Remote Similarity	NPD8524	Approved
0.689	Remote Similarity	NPD5810	Discontinued
0.6878	Remote Similarity	NPD4885	Approved
0.6872	Remote Similarity	NPD6202	Discontinued
0.6849	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6742	Phase 2
0.6842	Remote Similarity	NPD6743	Phase 2
0.6831	Remote Similarity	NPD6573	Phase 3
0.6831	Remote Similarity	NPD6572	Phase 2
0.6829	Remote Similarity	NPD6244	Phase 3
0.6829	Remote Similarity	NPD6243	Phase 3
0.6828	Remote Similarity	NPD4502	Phase 2
0.6826	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7555	Discontinued
0.681	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6145	Phase 1
0.6798	Remote Similarity	NPD3330	Phase 1
0.6793	Remote Similarity	NPD6969	Phase 2
0.6793	Remote Similarity	NPD6968	Phase 2
0.6793	Remote Similarity	NPD5479	Discontinued
0.6789	Remote Similarity	NPD802	Phase 2
0.6786	Remote Similarity	NPD5425	Phase 1
0.6777	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8016	Phase 3
0.6771	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2916	Discontinued
0.6762	Remote Similarity	NPD7067	Approved
0.6762	Remote Similarity	NPD7068	Approved
0.6758	Remote Similarity	NPD8363	Approved
0.6758	Remote Similarity	NPD8364	Approved
0.6752	Remote Similarity	NPD6995	Phase 1
0.6743	Remote Similarity	NPD7181	Phase 3
0.674	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6230	Discontinued
0.6732	Remote Similarity	NPD6456	Discontinued
0.6727	Remote Similarity	NPD774	Phase 3
0.6726	Remote Similarity	NPD5429	Discontinued
0.6725	Remote Similarity	NPD2794	Discontinued
0.6725	Remote Similarity	NPD3815	Phase 1
0.6725	Remote Similarity	NPD3816	Phase 1
0.672	Remote Similarity	NPD8442	Discontinued
0.6717	Remote Similarity	NPD8525	Approved
0.6706	Remote Similarity	NPD7956	Approved
0.6706	Remote Similarity	NPD7955	Approved
0.6705	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7671	Approved
0.6696	Remote Similarity	NPD4457	Phase 2
0.6696	Remote Similarity	NPD7672	Approved
0.6694	Remote Similarity	NPD7592	Phase 2
0.6694	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6251	Discontinued
0.6681	Remote Similarity	NPD6220	Phase 3
0.6681	Remote Similarity	NPD5939	Approved
0.6681	Remote Similarity	NPD5936	Approved
0.6681	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3921	Approved
0.6667	Remote Similarity	NPD3835	Phase 3
0.6667	Remote Similarity	NPD3922	Approved
0.6667	Remote Similarity	NPD3923	Approved
0.6667	Remote Similarity	NPD3924	Approved
0.6667	Remote Similarity	NPD3833	Phase 3
0.6653	Remote Similarity	NPD7392	Phase 2
0.6653	Remote Similarity	NPD7567	Approved
0.6651	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5450	Discontinued
0.6639	Remote Similarity	NPD2471	Approved
0.6639	Remote Similarity	NPD2472	Approved
0.6639	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4203	Approved
0.6636	Remote Similarity	NPD4204	Approved
0.6624	Remote Similarity	NPD3402	Phase 1
0.6622	Remote Similarity	NPD7948	Phase 1
0.6605	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8427	Approved
0.6603	Remote Similarity	NPD8465	Approved
0.6603	Remote Similarity	NPD8428	Approved
0.6603	Remote Similarity	NPD8467	Approved
0.6603	Remote Similarity	NPD8429	Approved
0.6603	Remote Similarity	NPD8466	Approved
0.6595	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4437	Phase 3
0.659	Remote Similarity	NPD5256	Discontinued
0.6589	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6306	Phase 2
0.658	Remote Similarity	NPD4927	Discontinued
0.6576	Remote Similarity	NPD3343	Phase 3
0.6576	Remote Similarity	NPD7803	Approved
0.6576	Remote Similarity	NPD8284	Discontinued
0.6568	Remote Similarity	NPD7726	Phase 1
0.6567	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8244	Phase 2
0.6556	Remote Similarity	NPD7688	Phase 1
0.655	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD5003	Discontinued
0.6544	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6963	Approved
0.6543	Remote Similarity	NPD6964	Approved
0.6542	Remote Similarity	NPD7479	Phase 2
0.654	Remote Similarity	NPD1954	Phase 1
0.654	Remote Similarity	NPD6736	Discontinued
0.654	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7051	Phase 3
0.6527	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7675	Phase 3
0.6527	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7674	Phase 3
0.6524	Remote Similarity	NPD3257	Approved
0.652	Remote Similarity	NPD4886	Phase 2
0.652	Remote Similarity	NPD6991	Approved
0.652	Remote Similarity	NPD4558	Phase 2
0.6518	Remote Similarity	NPD7770	Phase 3
0.6504	Remote Similarity	NPD8460	Approved
0.6504	Remote Similarity	NPD8425	Approved
0.6504	Remote Similarity	NPD8459	Approved
0.6504	Remote Similarity	NPD8426	Approved
0.6502	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6741	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