NPASS Compound

Structure

CID169402 OpenBabel06191715542D 21 23 0 0 0 0 0 0 0 0999 V2000 -4.0054 -0.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4589 0.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0261 -2.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6791 -1.9383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6787 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 -1.9389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5179 -0.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 -1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8393 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5180 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8395 -0.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5182 -0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3571 -1.9392 0.0000 C 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 3.2556 -2.9028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3569 0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3574 -0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2423 -1.5452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.1
Volume:	287.325
LogP:	3.434
LogD:	3.564
LogS:	-5.509
# Rotatable Bonds:	4
TPSA:	60.55
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	2.032
Fsp3:	0.188
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:	-4.976
MDCK Permeability:	2.380470141361002e-05
Pgp-inhibitor:	0.772
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.138

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.628
Plasma Protein Binding (PPB):	87.1612777709961%
Volume Distribution (VD):	0.74
Pgp-substrate:	11.172837257385254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.825
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.511
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	7.777
Half-life (T1/2):	0.459

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.799
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.498
Carcinogencity:	0.082
Eye Corrosion:	0.005
Eye Irritation:	0.761
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC169402

Natural Product ID:	NPC169402
*Common Name:**	Clauszoline C
IUPAC Name:	methyl 2,7-dimethoxy-9H-carbazole-3-carboxylate
Synonyms:	Clauszoline C; Clauszoline-C
Standard InCHIKey:	BWOCIAHZUOFDLV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H15NO4/c1-19-9-4-5-10-11-7-12(16(18)21-3)15(20-2)8-14(11)17-13(10)6-9/h4-8,17H,1-3H3
SMILES:	COc1ccc2c(c1)[nH]c1c2cc(c(c1)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1927324
PubChem CID:	5315952
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]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11720530]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724858]
NPO29161	Hyptis urticoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19265396]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[21774474]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22050382]
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	whole plants	Yunnan Province, China	2008-JAN	PMID[22093759]
NPO4806	Clausena wallichii	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22482432]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[23164710]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26203536]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28951079]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29461	Sarcophyton infundibuliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29073	Ipomoea carnea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29387	Eudendrium racemosum	Species	Eudendriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29518	Nardia scalaris	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28639	Trixis grisebachii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29180	Monachosorum maximowiczii	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29035	Pseudomonas cichorii	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28500	Griselinia scandens	Species	Griseliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29095	Yucca elata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28961	Croton hutchinsonianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28544	Podocalyx loranthoides	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28943	Daldinia vernicosa	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29070	Bulbine asphodeloides	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29161	Hyptis urticoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25073	Saccharina latissima	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4806	Clausena wallichii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29321	Octopus octopodia	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29497	Delphinium speciosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23710	Otholobium pubescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29028	Cicer cuneatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28427	Gutenbergia marginata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27603	Populus candicans	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27349	Rhododendron edgeworthii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28735	Helicia erratica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25248	Gloydius blomhoffii	Species	Viperidae	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	2
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	160000.0	nM	PMID[521584]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[521585]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[521585]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	5.5	ug.mL-1	PMID[521586]

☑ 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 NPC169402 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	445
0.1-0.2	3008
0.2-0.3	11963
0.3-0.4	4868
0.4-0.5	12685
0.5-0.6	7516
0.6-0.7	1604
0.7-0.8	527
0.8-0.85	52
0.85-0.9	15
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC116238
0.9745	High Similarity	NPC174760
0.9531	High Similarity	NPC4687
0.9487	High Similarity	NPC310211
0.9487	High Similarity	NPC308137
0.9442	High Similarity	NPC3207
0.9337	High Similarity	NPC87413
0.9254	High Similarity	NPC150239
0.925	High Similarity	NPC247803
0.925	High Similarity	NPC46561
0.9231	High Similarity	NPC249583
0.9208	High Similarity	NPC198503
0.9086	High Similarity	NPC39679
0.8985	High Similarity	NPC300156
0.8856	High Similarity	NPC23294
0.8806	High Similarity	NPC303951
0.88	High Similarity	NPC86834
0.88	High Similarity	NPC210828
0.8738	High Similarity	NPC208084
0.87	High Similarity	NPC45190
0.8676	High Similarity	NPC39500
0.8654	High Similarity	NPC280799
0.8651	High Similarity	NPC6786
0.8612	High Similarity	NPC144452
0.8594	High Similarity	NPC160381
0.8531	High Similarity	NPC179287
0.8519	High Similarity	NPC473187
0.851	High Similarity	NPC184408
0.8498	Intermediate Similarity	NPC274640
0.8485	Intermediate Similarity	NPC243834
0.8485	Intermediate Similarity	NPC70956
0.8477	Intermediate Similarity	NPC131017
0.8442	Intermediate Similarity	NPC72211
0.8398	Intermediate Similarity	NPC187501
0.8342	Intermediate Similarity	NPC70259
0.8341	Intermediate Similarity	NPC225279
0.8333	Intermediate Similarity	NPC474688
0.8333	Intermediate Similarity	NPC473041
0.8325	Intermediate Similarity	NPC148183
0.8325	Intermediate Similarity	NPC152768
0.8291	Intermediate Similarity	NPC43787
0.8291	Intermediate Similarity	NPC205934
0.8278	Intermediate Similarity	NPC118228
0.8235	Intermediate Similarity	NPC162484
0.8224	Intermediate Similarity	NPC51388
0.8186	Intermediate Similarity	NPC291535
0.8186	Intermediate Similarity	NPC475085
0.8186	Intermediate Similarity	NPC475112
0.8117	Intermediate Similarity	NPC475844
0.8116	Intermediate Similarity	NPC193777
0.8116	Intermediate Similarity	NPC321428
0.8102	Intermediate Similarity	NPC21638
0.8068	Intermediate Similarity	NPC476106
0.806	Intermediate Similarity	NPC89549
0.8049	Intermediate Similarity	NPC476044
0.8049	Intermediate Similarity	NPC267423
0.8048	Intermediate Similarity	NPC9894
0.802	Intermediate Similarity	NPC84478
0.8	Intermediate Similarity	NPC474701
0.7991	Intermediate Similarity	NPC194740
0.7991	Intermediate Similarity	NPC471762
0.798	Intermediate Similarity	NPC94943
0.7974	Intermediate Similarity	NPC475666
0.797	Intermediate Similarity	NPC212535
0.7963	Intermediate Similarity	NPC60621
0.7953	Intermediate Similarity	NPC298436
0.7952	Intermediate Similarity	NPC201697
0.793	Intermediate Similarity	NPC81939
0.7929	Intermediate Similarity	NPC190007
0.7924	Intermediate Similarity	NPC88923
0.7924	Intermediate Similarity	NPC100734
0.7924	Intermediate Similarity	NPC315634
0.7919	Intermediate Similarity	NPC260434
0.7907	Intermediate Similarity	NPC96321
0.7902	Intermediate Similarity	NPC306376
0.789	Intermediate Similarity	NPC122436
0.7877	Intermediate Similarity	NPC146418
0.7863	Intermediate Similarity	NPC284685
0.786	Intermediate Similarity	NPC305984
0.7848	Intermediate Similarity	NPC473105
0.7847	Intermediate Similarity	NPC470930
0.784	Intermediate Similarity	NPC48353
0.783	Intermediate Similarity	NPC269367
0.7828	Intermediate Similarity	NPC66777
0.7826	Intermediate Similarity	NPC329747
0.7824	Intermediate Similarity	NPC303658
0.7814	Intermediate Similarity	NPC330009
0.7812	Intermediate Similarity	NPC39370
0.7803	Intermediate Similarity	NPC473186
0.7799	Intermediate Similarity	NPC134848
0.7778	Intermediate Similarity	NPC293151
0.7773	Intermediate Similarity	NPC283117
0.7773	Intermediate Similarity	NPC97746
0.7772	Intermediate Similarity	NPC242928
0.7759	Intermediate Similarity	NPC473188
0.7754	Intermediate Similarity	NPC191489
0.7743	Intermediate Similarity	NPC235685
0.7717	Intermediate Similarity	NPC477532
0.771	Intermediate Similarity	NPC294375
0.7709	Intermediate Similarity	NPC101350
0.7706	Intermediate Similarity	NPC473179
0.7685	Intermediate Similarity	NPC16066
0.7681	Intermediate Similarity	NPC153042
0.7671	Intermediate Similarity	NPC323969
0.7671	Intermediate Similarity	NPC477533
0.7668	Intermediate Similarity	NPC311906
0.7667	Intermediate Similarity	NPC135887
0.7667	Intermediate Similarity	NPC199277
0.7664	Intermediate Similarity	NPC471304
0.765	Intermediate Similarity	NPC170114
0.7626	Intermediate Similarity	NPC84347
0.7623	Intermediate Similarity	NPC478078
0.7621	Intermediate Similarity	NPC475190
0.7617	Intermediate Similarity	NPC209769
0.7617	Intermediate Similarity	NPC325297
0.7608	Intermediate Similarity	NPC128823
0.7604	Intermediate Similarity	NPC470549
0.76	Intermediate Similarity	NPC217176
0.7597	Intermediate Similarity	NPC91868
0.7597	Intermediate Similarity	NPC63971
0.7594	Intermediate Similarity	NPC132539
0.7594	Intermediate Similarity	NPC285558
0.7593	Intermediate Similarity	NPC264176
0.7591	Intermediate Similarity	NPC472099
0.7578	Intermediate Similarity	NPC470018
0.757	Intermediate Similarity	NPC475910
0.7566	Intermediate Similarity	NPC475720
0.7566	Intermediate Similarity	NPC132329
0.7566	Intermediate Similarity	NPC474192
0.7553	Intermediate Similarity	NPC478083
0.7545	Intermediate Similarity	NPC157931
0.7543	Intermediate Similarity	NPC78609
0.7536	Intermediate Similarity	NPC232727
0.7525	Intermediate Similarity	NPC474409
0.7525	Intermediate Similarity	NPC176127
0.7511	Intermediate Similarity	NPC184680
0.7511	Intermediate Similarity	NPC252251
0.75	Intermediate Similarity	NPC470020
0.75	Intermediate Similarity	NPC11464
0.749	Intermediate Similarity	NPC195788
0.749	Intermediate Similarity	NPC237901
0.7488	Intermediate Similarity	NPC11017
0.7478	Intermediate Similarity	NPC470785
0.7478	Intermediate Similarity	NPC470784
0.7477	Intermediate Similarity	NPC89508
0.7475	Intermediate Similarity	NPC474798
0.7467	Intermediate Similarity	NPC473185
0.7465	Intermediate Similarity	NPC220337
0.7464	Intermediate Similarity	NPC13880
0.7457	Intermediate Similarity	NPC473540
0.7455	Intermediate Similarity	NPC312645
0.7446	Intermediate Similarity	NPC475816
0.7446	Intermediate Similarity	NPC168922
0.7445	Intermediate Similarity	NPC477531
0.7442	Intermediate Similarity	NPC183777
0.7437	Intermediate Similarity	NPC303374
0.7436	Intermediate Similarity	NPC469734
0.7431	Intermediate Similarity	NPC12344
0.7421	Intermediate Similarity	NPC264285
0.7419	Intermediate Similarity	NPC199667
0.7419	Intermediate Similarity	NPC167860
0.7419	Intermediate Similarity	NPC123976
0.7418	Intermediate Similarity	NPC295898
0.7416	Intermediate Similarity	NPC276517
0.7415	Intermediate Similarity	NPC165964
0.7414	Intermediate Similarity	NPC477066
0.7409	Intermediate Similarity	NPC469928
0.7409	Intermediate Similarity	NPC74969
0.7409	Intermediate Similarity	NPC471303
0.7407	Intermediate Similarity	NPC470931
0.7406	Intermediate Similarity	NPC472589
0.7404	Intermediate Similarity	NPC55493
0.7404	Intermediate Similarity	NPC17437
0.7404	Intermediate Similarity	NPC1608
0.7401	Intermediate Similarity	NPC209174
0.7395	Intermediate Similarity	NPC472588
0.7391	Intermediate Similarity	NPC83111
0.7389	Intermediate Similarity	NPC74575
0.7387	Intermediate Similarity	NPC74360
0.7384	Intermediate Similarity	NPC67401
0.7383	Intermediate Similarity	NPC165599
0.7383	Intermediate Similarity	NPC223427
0.7383	Intermediate Similarity	NPC317572
0.7382	Intermediate Similarity	NPC478082
0.7382	Intermediate Similarity	NPC477067
0.7382	Intermediate Similarity	NPC478081
0.7376	Intermediate Similarity	NPC88363
0.7376	Intermediate Similarity	NPC72980
0.7373	Intermediate Similarity	NPC473181
0.7373	Intermediate Similarity	NPC270515
0.7371	Intermediate Similarity	NPC260909
0.7368	Intermediate Similarity	NPC475253
0.7366	Intermediate Similarity	NPC16352
0.7364	Intermediate Similarity	NPC478080
0.7359	Intermediate Similarity	NPC15801
0.7356	Intermediate Similarity	NPC138370
0.7354	Intermediate Similarity	NPC86078
0.7352	Intermediate Similarity	NPC473180
0.735	Intermediate Similarity	NPC188400
0.7346	Intermediate Similarity	NPC141454

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 NPC169402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	695
0.2-0.3	949
0.3-0.4	1384
0.4-0.5	2819
0.5-0.6	2121
0.6-0.7	762
0.7-0.8	109
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8436	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5632	Approved
0.8036	Intermediate Similarity	NPD6790	Phase 1
0.7924	Intermediate Similarity	NPD7803	Approved
0.7911	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5488	Discontinued
0.7873	Intermediate Similarity	NPD4952	Phase 3
0.7863	Intermediate Similarity	NPD7956	Approved
0.7863	Intermediate Similarity	NPD7955	Approved
0.785	Intermediate Similarity	NPD3257	Approved
0.7792	Intermediate Similarity	NPD5482	Discontinued
0.7783	Intermediate Similarity	NPD3259	Approved
0.7768	Intermediate Similarity	NPD4373	Phase 2
0.7767	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7708	Approved
0.7713	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3258	Approved
0.7679	Intermediate Similarity	NPD6962	Phase 2
0.7671	Intermediate Similarity	NPD6242	Discontinued
0.7596	Intermediate Similarity	NPD5003	Discontinued
0.757	Intermediate Similarity	NPD5658	Approved
0.7559	Intermediate Similarity	NPD3003	Approved
0.7543	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5901	Discontinued
0.75	Intermediate Similarity	NPD4418	Discontinued
0.749	Intermediate Similarity	NPD8466	Approved
0.749	Intermediate Similarity	NPD8429	Approved
0.749	Intermediate Similarity	NPD8465	Approved
0.749	Intermediate Similarity	NPD8427	Approved
0.749	Intermediate Similarity	NPD8428	Approved
0.749	Intermediate Similarity	NPD8467	Approved
0.7489	Intermediate Similarity	NPD7417	Discontinued
0.7476	Intermediate Similarity	NPD2564	Approved
0.7476	Intermediate Similarity	NPD2565	Phase 2
0.7467	Intermediate Similarity	NPD4328	Approved
0.7465	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5512	Phase 3
0.7459	Intermediate Similarity	NPD8364	Approved
0.7459	Intermediate Similarity	NPD8363	Approved
0.7455	Intermediate Similarity	NPD3925	Approved
0.743	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4885	Approved
0.7407	Intermediate Similarity	NPD5450	Discontinued
0.7404	Intermediate Similarity	NPD8358	Approved
0.7398	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7994	Phase 2
0.7385	Intermediate Similarity	NPD5416	Discontinued
0.7373	Intermediate Similarity	NPD4506	Discontinued
0.7371	Intermediate Similarity	NPD8459	Approved
0.7371	Intermediate Similarity	NPD8425	Approved
0.7371	Intermediate Similarity	NPD8426	Approved
0.7371	Intermediate Similarity	NPD8460	Approved
0.7364	Intermediate Similarity	NPD5902	Approved
0.7364	Intermediate Similarity	NPD5903	Approved
0.7358	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7069	Discontinued
0.7342	Intermediate Similarity	NPD7395	Discontinued
0.7325	Intermediate Similarity	NPD5479	Discontinued
0.7313	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5429	Discontinued
0.7277	Intermediate Similarity	NPD1768	Approved
0.7269	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7689	Approved
0.7217	Intermediate Similarity	NPD1867	Approved
0.721	Intermediate Similarity	NPD5805	Approved
0.7207	Intermediate Similarity	NPD5293	Phase 2
0.7195	Intermediate Similarity	NPD5866	Approved
0.7189	Intermediate Similarity	NPD3947	Discontinued
0.7178	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2916	Discontinued
0.7167	Intermediate Similarity	NPD7853	Phase 2
0.7161	Intermediate Similarity	NPD6716	Phase 1
0.7156	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6974	Phase 3
0.7156	Intermediate Similarity	NPD6770	Approved
0.7143	Intermediate Similarity	NPD6176	Phase 1
0.7137	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4948	Discontinued
0.7123	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1038	Approved
0.7111	Intermediate Similarity	NPD3354	Phase 2
0.7111	Intermediate Similarity	NPD4429	Discontinued
0.7111	Intermediate Similarity	NPD6985	Discontinued
0.7111	Intermediate Similarity	NPD1926	Approved
0.7105	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6530	Approved
0.7102	Intermediate Similarity	NPD6531	Approved
0.7091	Intermediate Similarity	NPD2509	Approved
0.7091	Intermediate Similarity	NPD2510	Approved
0.7085	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3290	Approved
0.7083	Intermediate Similarity	NPD4601	Approved
0.7083	Intermediate Similarity	NPD4501	Approved
0.7083	Intermediate Similarity	NPD4500	Approved
0.7083	Intermediate Similarity	NPD3289	Phase 3
0.7083	Intermediate Similarity	NPD4600	Approved
0.7079	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7688	Phase 1
0.7064	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD2920	Discontinued
0.7061	Intermediate Similarity	NPD8489	Phase 1
0.7056	Intermediate Similarity	NPD6550	Discontinued
0.7054	Intermediate Similarity	NPD3986	Discontinued
0.7045	Intermediate Similarity	NPD1392	Approved
0.7042	Intermediate Similarity	NPD4539	Phase 1
0.704	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5532	Phase 2
0.7037	Intermediate Similarity	NPD2778	Approved
0.7037	Intermediate Similarity	NPD6252	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6228	Discontinued
0.703	Intermediate Similarity	NPD2844	Phase 3
0.7027	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3006	Discontinued
0.702	Intermediate Similarity	NPD8091	Phase 3
0.7012	Intermediate Similarity	NPD8102	Discontinued
0.7009	Intermediate Similarity	NPD7558	Phase 2
0.7005	Intermediate Similarity	NPD484	Approved
0.7004	Intermediate Similarity	NPD7194	Discontinued
0.7	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8403	Phase 1
0.6996	Remote Similarity	NPD6709	Phase 3
0.6995	Remote Similarity	NPD5937	Approved
0.6992	Remote Similarity	NPD4368	Phase 2
0.6987	Remote Similarity	NPD6995	Phase 1
0.6981	Remote Similarity	NPD4499	Approved
0.6965	Remote Similarity	NPD955	Approved
0.6963	Remote Similarity	NPD802	Phase 2
0.6957	Remote Similarity	NPD3920	Phase 2
0.6953	Remote Similarity	NPD4981	Phase 2
0.6947	Remote Similarity	NPD5612	Discontinued
0.6944	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4558	Phase 2
0.6941	Remote Similarity	NPD2779	Approved
0.6936	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3945	Discontinued
0.693	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4312	Approved
0.6927	Remote Similarity	NPD2246	Approved
0.6927	Remote Similarity	NPD2248	Approved
0.6926	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1505	Phase 2
0.692	Remote Similarity	NPD7470	Discontinued
0.692	Remote Similarity	NPD5066	Phase 2
0.692	Remote Similarity	NPD5067	Phase 2
0.6916	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5399	Discovery
0.6903	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7180	Phase 3
0.6898	Remote Similarity	NPD8463	Approved
0.6897	Remote Similarity	NPD3263	Phase 3
0.6886	Remote Similarity	NPD7878	Phase 2
0.6881	Remote Similarity	NPD3825	Phase 3
0.6878	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6517	Phase 3
0.6872	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3389	Approved
0.6872	Remote Similarity	NPD3394	Approved
0.6872	Remote Similarity	NPD4889	Approved
0.6872	Remote Similarity	NPD3393	Approved
0.686	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD3243	Approved
0.6858	Remote Similarity	NPD4356	Discontinued
0.6854	Remote Similarity	NPD1534	Approved
0.6842	Remote Similarity	NPD5164	Discontinued
0.6835	Remote Similarity	NPD4668	Phase 2
0.6833	Remote Similarity	NPD5513	Phase 2
0.6829	Remote Similarity	NPD1325	Approved
0.6829	Remote Similarity	NPD1326	Approved
0.6822	Remote Similarity	NPD3746	Discontinued
0.6814	Remote Similarity	NPD3816	Phase 1
0.6814	Remote Similarity	NPD3815	Phase 1
0.6812	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5022	Discontinued
0.6805	Remote Similarity	NPD1483	Discontinued
0.6802	Remote Similarity	NPD4795	Phase 2
0.6798	Remote Similarity	NPD8160	Phase 2
0.6792	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5913	Phase 3
0.6789	Remote Similarity	NPD6988	Phase 1
0.6789	Remote Similarity	NPD7948	Phase 1
0.6786	Remote Similarity	NPD6376	Discontinued
0.6784	Remote Similarity	NPD3795	Approved
0.6784	Remote Similarity	NPD3794	Approved
0.678	Remote Similarity	NPD1467	Approved
0.678	Remote Similarity	NPD1466	Phase 3
0.6776	Remote Similarity	NPD2792	Approved
0.6771	Remote Similarity	NPD6245	Phase 2
0.6762	Remote Similarity	NPD5445	Approved
0.6761	Remote Similarity	NPD5256	Discontinued
0.6758	Remote Similarity	NPD7946	Pre-registration
0.6754	Remote Similarity	NPD6745	Discontinued

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