NPASS Compound

Structure

CID227908 OpenBabel06191716022D 25 29 0 0 0 0 0 0 0 0999 V2000 0.6833 -0.7593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4568 2.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4201 2.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9048 0.1025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4199 1.4383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5090 -0.7870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5771 2.8995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3323 0.8900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5767 0.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5408 -0.8890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2033 3.8738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7334 2.4128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3641 0.7880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2031 2.9002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7332 1.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9683 -0.1015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0466 2.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6404 1.4393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0464 1.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2027 0.9523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6402 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2834 4.7170 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8899 0.9519 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 -1.4832 2.9004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 15 2 0 0 0 0 10 16 2 0 0 0 0 11 14 1 0 0 0 0 11 22 3 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 18 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.12
Volume:	341.769
LogP:	5.034
LogD:	4.036
LogS:	-7.293
# Rotatable Bonds:	1
TPSA:	53.74
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	2.598
Fsp3:	0.095
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:	-5.037
MDCK Permeability:	1.7355232557747513e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.242
20% Bioavailability (F20%):	0.226
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	98.01943969726562%
Volume Distribution (VD):	0.35
Pgp-substrate:	1.6980750560760498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.263
CYP2C9-inhibitor:	0.932
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.618
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	6.816
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.843
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.917
Rat Oral Acute Toxicity:	0.466
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.887
Carcinogencity:	0.975
Eye Corrosion:	0.037
Eye Irritation:	0.982
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC227908

Natural Product ID:	NPC227908
*Common Name:**	6-Cyano-5-Methoxy-12-Methylindolo[2,3-A]Carbazole
IUPAC Name:	5-methoxy-12-methyl-11H-indolo[2,3-a]carbazole-6-carbonitrile
Synonyms:
Standard InCHIKey:	RZBCCAZHJQZKLL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H15N3O/c1-24-16-10-6-4-8-13(16)18-20(24)19-17(14(11-22)21(18)25-2)12-7-3-5-9-15(12)23-19/h3-10,23H,1-2H3
SMILES:	N#Cc1c2c3ccccc3[nH]c2c2c(c1OC)c1ccccc1n2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL596317
PubChem CID:	131447
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]
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]
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]
NPO1969	Streptomyces pilosus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8811	Cytisus prolifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28833	Eleutherococcus sieboldianus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19804	Lycopodium saururus	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5335	0stoc sp	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO834	Peperomia clusiifolia	Species	Piperaceae	Eukaryota	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]

☑ 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	4
Others	1

Activity Type	# Activity
Cell Line	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	MIC	=	5.0	ug.mL-1	PMID[566108]
NPT114	Cell Line	LoVo	Homo sapiens	MIC	=	5.0	ug.mL-1	PMID[566108]
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	Activity	=	95.0	%	PMID[566108]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	128000.0	nM	PMID[566108]
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	>	200000.0	nM	PMID[566108]

☑ 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 NPC227908 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	1028
0.1-0.2	7263
0.2-0.3	10314
0.3-0.4	15141
0.4-0.5	4862
0.5-0.6	2759
0.6-0.7	1060
0.7-0.8	250
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC86078
0.8341	Intermediate Similarity	NPC208284
0.8238	Intermediate Similarity	NPC193777
0.8235	Intermediate Similarity	NPC131017
0.8224	Intermediate Similarity	NPC470549
0.8216	Intermediate Similarity	NPC294620
0.8216	Intermediate Similarity	NPC473180
0.819	Intermediate Similarity	NPC252251
0.8186	Intermediate Similarity	NPC170114
0.816	Intermediate Similarity	NPC201697
0.8145	Intermediate Similarity	NPC473185
0.8131	Intermediate Similarity	NPC94157
0.8119	Intermediate Similarity	NPC477533
0.8117	Intermediate Similarity	NPC477531
0.8095	Intermediate Similarity	NPC162484
0.8072	Intermediate Similarity	NPC209174
0.8047	Intermediate Similarity	NPC48353
0.8036	Intermediate Similarity	NPC475253
0.8	Intermediate Similarity	NPC267423
0.7991	Intermediate Similarity	NPC473181
0.7953	Intermediate Similarity	NPC199667
0.7952	Intermediate Similarity	NPC176538
0.7926	Intermediate Similarity	NPC478074
0.7925	Intermediate Similarity	NPC223427
0.7909	Intermediate Similarity	NPC473179
0.7885	Intermediate Similarity	NPC205934
0.7885	Intermediate Similarity	NPC195314
0.7885	Intermediate Similarity	NPC43787
0.7873	Intermediate Similarity	NPC132642
0.787	Intermediate Similarity	NPC123976
0.787	Intermediate Similarity	NPC167860
0.786	Intermediate Similarity	NPC473183
0.7857	Intermediate Similarity	NPC202503
0.7857	Intermediate Similarity	NPC72211
0.7851	Intermediate Similarity	NPC473184
0.7847	Intermediate Similarity	NPC13880
0.7847	Intermediate Similarity	NPC70259
0.783	Intermediate Similarity	NPC232727
0.781	Intermediate Similarity	NPC70956
0.781	Intermediate Similarity	NPC153042
0.781	Intermediate Similarity	NPC243834
0.7807	Intermediate Similarity	NPC473182
0.7758	Intermediate Similarity	NPC477532
0.7746	Intermediate Similarity	NPC476044
0.7745	Intermediate Similarity	NPC176127
0.7729	Intermediate Similarity	NPC246700
0.7729	Intermediate Similarity	NPC128751
0.77	Intermediate Similarity	NPC329793
0.77	Intermediate Similarity	NPC329747
0.77	Intermediate Similarity	NPC315957
0.7692	Intermediate Similarity	NPC106833
0.7692	Intermediate Similarity	NPC469497
0.7682	Intermediate Similarity	NPC477066
0.7668	Intermediate Similarity	NPC213530
0.7668	Intermediate Similarity	NPC193267
0.765	Intermediate Similarity	NPC478081
0.7639	Intermediate Similarity	NPC285558
0.7628	Intermediate Similarity	NPC291535
0.7628	Intermediate Similarity	NPC475085
0.7628	Intermediate Similarity	NPC475112
0.7626	Intermediate Similarity	NPC11464
0.7621	Intermediate Similarity	NPC84478
0.7617	Intermediate Similarity	NPC11017
0.7604	Intermediate Similarity	NPC476106
0.76	Intermediate Similarity	NPC310118
0.7574	Intermediate Similarity	NPC478082
0.7574	Intermediate Similarity	NPC477067
0.7571	Intermediate Similarity	NPC92111
0.756	Intermediate Similarity	NPC242928
0.756	Intermediate Similarity	NPC296527
0.7555	Intermediate Similarity	NPC314954
0.7535	Intermediate Similarity	NPC121772
0.7532	Intermediate Similarity	NPC469554
0.7532	Intermediate Similarity	NPC132329
0.7524	Intermediate Similarity	NPC76748
0.7523	Intermediate Similarity	NPC469592
0.7523	Intermediate Similarity	NPC471080
0.7522	Intermediate Similarity	NPC280799
0.7521	Intermediate Similarity	NPC11408
0.7511	Intermediate Similarity	NPC160898
0.75	Intermediate Similarity	NPC473540
0.7478	Intermediate Similarity	NPC253580
0.7477	Intermediate Similarity	NPC475070
0.7477	Intermediate Similarity	NPC470930
0.7468	Intermediate Similarity	NPC39370
0.7467	Intermediate Similarity	NPC46561
0.7466	Intermediate Similarity	NPC471304
0.7465	Intermediate Similarity	NPC135887
0.7465	Intermediate Similarity	NPC199277
0.7458	Intermediate Similarity	NPC217554
0.7457	Intermediate Similarity	NPC101543
0.7457	Intermediate Similarity	NPC473186
0.7454	Intermediate Similarity	NPC19872
0.7452	Intermediate Similarity	NPC190007
0.7448	Intermediate Similarity	NPC17437
0.7436	Intermediate Similarity	NPC295228
0.7435	Intermediate Similarity	NPC110151
0.7435	Intermediate Similarity	NPC470126
0.7434	Intermediate Similarity	NPC46451
0.7431	Intermediate Similarity	NPC476138
0.7431	Intermediate Similarity	NPC245816
0.7427	Intermediate Similarity	NPC88363
0.7424	Intermediate Similarity	NPC313884
0.7424	Intermediate Similarity	NPC98371
0.7421	Intermediate Similarity	NPC174672
0.7418	Intermediate Similarity	NPC307963
0.7416	Intermediate Similarity	NPC473189
0.7416	Intermediate Similarity	NPC94943
0.7404	Intermediate Similarity	NPC212535
0.7404	Intermediate Similarity	NPC6786
0.7393	Intermediate Similarity	NPC277351
0.7389	Intermediate Similarity	NPC469594
0.7376	Intermediate Similarity	NPC475910
0.7376	Intermediate Similarity	NPC470931
0.7376	Intermediate Similarity	NPC82548
0.7364	Intermediate Similarity	NPC284141
0.7364	Intermediate Similarity	NPC45190
0.7364	Intermediate Similarity	NPC300156
0.7362	Intermediate Similarity	NPC473187
0.7358	Intermediate Similarity	NPC89549
0.7349	Intermediate Similarity	NPC251090
0.7345	Intermediate Similarity	NPC476041
0.7345	Intermediate Similarity	NPC304926
0.7345	Intermediate Similarity	NPC305984
0.7342	Intermediate Similarity	NPC185782
0.7336	Intermediate Similarity	NPC478080
0.7336	Intermediate Similarity	NPC280272
0.7331	Intermediate Similarity	NPC235685
0.7327	Intermediate Similarity	NPC128823
0.7321	Intermediate Similarity	NPC26679
0.7315	Intermediate Similarity	NPC474188
0.7313	Intermediate Similarity	NPC96321
0.7313	Intermediate Similarity	NPC23614
0.7313	Intermediate Similarity	NPC100079
0.7309	Intermediate Similarity	NPC5145
0.7301	Intermediate Similarity	NPC152768
0.7301	Intermediate Similarity	NPC148183
0.73	Intermediate Similarity	NPC101350
0.7293	Intermediate Similarity	NPC60621
0.7273	Intermediate Similarity	NPC474798
0.7265	Intermediate Similarity	NPC174758
0.7265	Intermediate Similarity	NPC469589
0.7265	Intermediate Similarity	NPC209769
0.7261	Intermediate Similarity	NPC475666
0.7257	Intermediate Similarity	NPC235076
0.7252	Intermediate Similarity	NPC249583
0.7252	Intermediate Similarity	NPC4687
0.7244	Intermediate Similarity	NPC308137
0.7244	Intermediate Similarity	NPC310211
0.7237	Intermediate Similarity	NPC303658
0.7233	Intermediate Similarity	NPC474409
0.722	Intermediate Similarity	NPC81939
0.7212	Intermediate Similarity	NPC31700
0.7207	Intermediate Similarity	NPC472111
0.7198	Intermediate Similarity	NPC45048
0.7195	Intermediate Similarity	NPC475774
0.7193	Intermediate Similarity	NPC169402
0.7181	Intermediate Similarity	NPC116238
0.7169	Intermediate Similarity	NPC18487
0.7168	Intermediate Similarity	NPC316981
0.7168	Intermediate Similarity	NPC472098
0.7166	Intermediate Similarity	NPC478083
0.7162	Intermediate Similarity	NPC473041
0.716	Intermediate Similarity	NPC279589
0.7155	Intermediate Similarity	NPC30540
0.7155	Intermediate Similarity	NPC122436
0.7149	Intermediate Similarity	NPC8022
0.7149	Intermediate Similarity	NPC183407
0.7149	Intermediate Similarity	NPC470799
0.7143	Intermediate Similarity	NPC198503
0.7137	Intermediate Similarity	NPC271215
0.7137	Intermediate Similarity	NPC266931
0.7137	Intermediate Similarity	NPC149471
0.7136	Intermediate Similarity	NPC249040
0.7131	Intermediate Similarity	NPC63971
0.7131	Intermediate Similarity	NPC91868
0.713	Intermediate Similarity	NPC141915
0.713	Intermediate Similarity	NPC114335
0.713	Intermediate Similarity	NPC280964
0.7125	Intermediate Similarity	NPC477861
0.7124	Intermediate Similarity	NPC87413
0.7124	Intermediate Similarity	NPC9894
0.7112	Intermediate Similarity	NPC162748
0.7111	Intermediate Similarity	NPC476116
0.7102	Intermediate Similarity	NPC26543
0.71	Intermediate Similarity	NPC150239
0.71	Intermediate Similarity	NPC472099
0.7094	Intermediate Similarity	NPC285635
0.7087	Intermediate Similarity	NPC247803
0.7087	Intermediate Similarity	NPC477609
0.7082	Intermediate Similarity	NPC211416
0.7081	Intermediate Similarity	NPC56618
0.708	Intermediate Similarity	NPC188420
0.7074	Intermediate Similarity	NPC274982
0.7072	Intermediate Similarity	NPC295898
0.7067	Intermediate Similarity	NPC476465
0.7064	Intermediate Similarity	NPC6215
0.7064	Intermediate Similarity	NPC157931
0.7061	Intermediate Similarity	NPC476287
0.7059	Intermediate Similarity	NPC180504

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 NPC227908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	481
0.1-0.2	711
0.2-0.3	863
0.3-0.4	2047
0.4-0.5	2742
0.5-0.6	1752
0.6-0.7	499
0.7-0.8	55
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
0.7944	Intermediate Similarity	NPD5658	Approved
0.7934	Intermediate Similarity	NPD5530	Phase 1
0.7887	Intermediate Similarity	NPD4795	Phase 2
0.782	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7194	Discontinued
0.77	Intermediate Similarity	NPD1740	Approved
0.77	Intermediate Similarity	NPD1739	Approved
0.7634	Intermediate Similarity	NPD5930	Phase 3
0.763	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD6985	Discontinued
0.7553	Intermediate Similarity	NPD5488	Discontinued
0.75	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5559	Phase 2
0.7448	Intermediate Similarity	NPD8358	Approved
0.7443	Intermediate Similarity	NPD3003	Approved
0.7434	Intermediate Similarity	NPD3763	Approved
0.7424	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD1038	Approved
0.7411	Intermediate Similarity	NPD5902	Approved
0.7411	Intermediate Similarity	NPD5903	Approved
0.7359	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7359	Intermediate Similarity	NPD6978	Phase 2
0.7336	Intermediate Similarity	NPD7219	Approved
0.7336	Intermediate Similarity	NPD7221	Approved
0.7281	Intermediate Similarity	NPD6455	Phase 3
0.7252	Intermediate Similarity	NPD7222	Phase 2
0.7252	Intermediate Similarity	NPD7452	Approved
0.7252	Intermediate Similarity	NPD7453	Approved
0.7249	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2151	Approved
0.7222	Intermediate Similarity	NPD4418	Discontinued
0.7218	Intermediate Similarity	NPD6531	Approved
0.7218	Intermediate Similarity	NPD6530	Approved
0.72	Intermediate Similarity	NPD5066	Phase 2
0.72	Intermediate Similarity	NPD5067	Phase 2
0.7178	Intermediate Similarity	NPD5802	Phase 2
0.717	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1768	Approved
0.7163	Intermediate Similarity	NPD5913	Phase 3
0.7163	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6975	Discontinued
0.713	Intermediate Similarity	NPD8403	Phase 1
0.7118	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4511	Phase 1
0.71	Intermediate Similarity	NPD6242	Discontinued
0.7097	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3825	Phase 3
0.7089	Intermediate Similarity	NPD3746	Discontinued
0.7078	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2189	Approved
0.7067	Intermediate Similarity	NPD2187	Approved
0.7059	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7558	Phase 2
0.7054	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6743	Phase 2
0.7045	Intermediate Similarity	NPD6742	Phase 2
0.7043	Intermediate Similarity	NPD5164	Discontinued
0.7037	Intermediate Similarity	NPD6573	Phase 3
0.7037	Intermediate Similarity	NPD6572	Phase 2
0.7034	Intermediate Similarity	NPD7555	Discontinued
0.7033	Intermediate Similarity	NPD5482	Discontinued
0.7029	Intermediate Similarity	NPD6760	Discontinued
0.7022	Intermediate Similarity	NPD1392	Approved
0.7015	Intermediate Similarity	NPD8524	Approved
0.7009	Intermediate Similarity	NPD5425	Phase 1
0.7004	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD8512	Phase 3
0.7	Intermediate Similarity	NPD5612	Discontinued
0.6996	Remote Similarity	NPD6473	Phase 1
0.6987	Remote Similarity	NPD6494	Phase 2
0.6983	Remote Similarity	NPD8016	Phase 3
0.6983	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7068	Approved
0.6967	Remote Similarity	NPD7067	Approved
0.6966	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6995	Phase 1
0.6964	Remote Similarity	NPD6244	Phase 3
0.6964	Remote Similarity	NPD6243	Phase 3
0.6957	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4885	Approved
0.6943	Remote Similarity	NPD3816	Phase 1
0.6943	Remote Similarity	NPD3815	Phase 1
0.6943	Remote Similarity	NPD6202	Discontinued
0.6943	Remote Similarity	NPD3330	Phase 1
0.6941	Remote Similarity	NPD802	Phase 2
0.694	Remote Similarity	NPD5632	Approved
0.6935	Remote Similarity	NPD7181	Phase 3
0.6933	Remote Similarity	NPD6969	Phase 2
0.6933	Remote Similarity	NPD6968	Phase 2
0.6929	Remote Similarity	NPD6456	Discontinued
0.6923	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3875	Discontinued
0.6906	Remote Similarity	NPD8525	Approved
0.6903	Remote Similarity	NPD6150	Discontinued
0.6891	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.689	Remote Similarity	NPD1325	Approved
0.689	Remote Similarity	NPD1326	Approved
0.6886	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6230	Discontinued
0.6862	Remote Similarity	NPD5479	Discontinued
0.6862	Remote Similarity	NPD7567	Approved
0.6854	Remote Similarity	NPD3920	Phase 2
0.6849	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2916	Discontinued
0.6829	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4502	Phase 2
0.6822	Remote Similarity	NPD8363	Approved
0.6822	Remote Similarity	NPD8364	Approved
0.6789	Remote Similarity	NPD7392	Phase 2
0.6786	Remote Similarity	NPD8442	Discontinued
0.6786	Remote Similarity	NPD8395	Approved
0.6786	Remote Similarity	NPD8396	Approved
0.678	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7956	Approved
0.6772	Remote Similarity	NPD7955	Approved
0.677	Remote Similarity	NPD6208	Discontinued
0.6769	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7672	Approved
0.6769	Remote Similarity	NPD7671	Approved
0.6767	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3402	Phase 1
0.6763	Remote Similarity	NPD7688	Phase 1
0.6761	Remote Similarity	NPD7592	Phase 2
0.6757	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6245	Phase 2
0.6744	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3923	Approved
0.6742	Remote Similarity	NPD3922	Approved
0.6742	Remote Similarity	NPD3921	Approved
0.6742	Remote Similarity	NPD3924	Approved
0.674	Remote Similarity	NPD2920	Discontinued
0.6729	Remote Similarity	NPD5810	Discontinued
0.6723	Remote Similarity	NPD6306	Phase 2
0.6721	Remote Similarity	NPD7770	Phase 3
0.6713	Remote Similarity	NPD4203	Approved
0.6713	Remote Similarity	NPD4204	Approved
0.6708	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2471	Approved
0.6708	Remote Similarity	NPD2472	Approved
0.6705	Remote Similarity	NPD5450	Discontinued
0.6705	Remote Similarity	NPD8284	Discontinued
0.6697	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7948	Phase 1
0.6695	Remote Similarity	NPD4457	Phase 2
0.6682	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6220	Phase 3
0.6681	Remote Similarity	NPD5939	Approved
0.6681	Remote Similarity	NPD5936	Approved
0.6667	Remote Similarity	NPD8429	Approved
0.6667	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7674	Phase 3
0.6667	Remote Similarity	NPD8467	Approved
0.6667	Remote Similarity	NPD7051	Phase 3
0.6667	Remote Similarity	NPD8466	Approved
0.6667	Remote Similarity	NPD8427	Approved
0.6667	Remote Similarity	NPD7675	Phase 3
0.6667	Remote Similarity	NPD4437	Phase 3
0.6667	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8465	Approved
0.6667	Remote Similarity	NPD8428	Approved
0.6667	Remote Similarity	NPD7921	Approved
0.6653	Remote Similarity	NPD4952	Phase 3
0.6653	Remote Similarity	NPD4558	Phase 2
0.6652	Remote Similarity	NPD6281	Approved
0.6652	Remote Similarity	NPD6145	Phase 1
0.6641	Remote Similarity	NPD7803	Approved
0.6641	Remote Similarity	NPD3343	Phase 3
0.664	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7726	Phase 1
0.6627	Remote Similarity	NPD8244	Phase 2
0.662	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7479	Phase 2
0.6613	Remote Similarity	NPD6790	Phase 1
0.6612	Remote Similarity	NPD6963	Approved
0.6612	Remote Similarity	NPD6964	Approved
0.6611	Remote Similarity	NPD1954	Phase 1
0.6602	Remote Similarity	NPD8091	Phase 3
0.6599	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6991	Approved
0.6594	Remote Similarity	NPD4886	Phase 2
0.6591	Remote Similarity	NPD5256	Discontinued
0.6584	Remote Similarity	NPD5254	Discontinued
0.6581	Remote Similarity	NPD2794	Discontinued
0.658	Remote Similarity	NPD5429	Discontinued
0.6578	Remote Similarity	NPD774	Phase 3
0.6578	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4373	Phase 2
0.6568	Remote Similarity	NPD6643	Discontinued
0.6567	Remote Similarity	NPD8426	Approved
0.6567	Remote Similarity	NPD8460	Approved
0.6567	Remote Similarity	NPD8459	Approved
0.6567	Remote Similarity	NPD8425	Approved
0.6562	Remote Similarity	NPD7262	Phase 1

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