NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	271.08
Volume:	270.029
LogP:	3.289
LogD:	3.13
LogS:	-3.702
# Rotatable Bonds:	3
TPSA:	71.55
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	2.018
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:	-5.003
MDCK Permeability:	5.495502591656987e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.111

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	84.69483184814453%
Volume Distribution (VD):	0.574
Pgp-substrate:	12.707917213439941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.65
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.115
CYP2C9-substrate:	0.475
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	3.816
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.721
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.751
Skin Sensitization:	0.204
Carcinogencity:	0.262
Eye Corrosion:	0.004
Eye Irritation:	0.88
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC174760

Natural Product ID:	NPC174760
*Common Name:**	Clausine K
IUPAC Name:	2,7-dimethoxy-9H-carbazole-3-carboxylic acid
Synonyms:	Clausine K
Standard InCHIKey:	LDKCHJXUOLZQQV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO4/c1-19-8-3-4-9-10-6-11(15(17)18)14(20-2)7-13(10)16-12(9)5-8/h3-7,16H,1-2H3,(H,17,18)
SMILES:	COc1ccc2c3cc(c(cc3[nH]c2c1)OC)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689806
PubChem CID:	504070
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]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21302964]
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]
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]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
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]
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]
NPO21978	Clausena harmandiana	Species	Rutaceae	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]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29161	Hyptis urticoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28943	Daldinia vernicosa	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29070	Bulbine asphodeloides	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29321	Octopus octopodia	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29028	Cicer cuneatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25073	Saccharina latissima	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23710	Otholobium pubescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29497	Delphinium speciosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27603	Populus candicans	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28427	Gutenbergia marginata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28735	Helicia erratica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27349	Rhododendron edgeworthii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29461	Sarcophyton infundibuliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25248	Gloydius blomhoffii	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29387	Eudendrium racemosum	Species	Eudendriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29073	Ipomoea carnea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28639	Trixis grisebachii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29518	Nardia scalaris	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29035	Pseudomonas cichorii	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29180	Monachosorum maximowiczii	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28500	Griselinia scandens	Species	Griseliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	3

Activity Type	# Activity
Cell Line	5
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	138830.0	nM	PMID[558677]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	200000.0	nM	PMID[558677]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	177500.0	nM	PMID[558677]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	24400.0	nM	PMID[558678]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	25000.0	nM	PMID[558679]
NPT2	Others	Unspecified		Selectivity Index	<	0.2	n.a.	PMID[558679]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	>	128000.0	nM	PMID[558679]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC90	=	100.0	ug.mL-1	PMID[558679]

☑ 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 NPC174760 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	442
0.1-0.2	2778
0.2-0.3	11087
0.3-0.4	5563
0.4-0.5	11376
0.5-0.6	9081
0.6-0.7	1735
0.7-0.8	554
0.8-0.85	51
0.85-0.9	15
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC169402
0.9744	High Similarity	NPC116238
0.9694	High Similarity	NPC3207
0.959	High Similarity	NPC87413
0.9497	High Similarity	NPC247803
0.9403	High Similarity	NPC150239
0.9385	High Similarity	NPC4687
0.9343	High Similarity	NPC308137
0.9343	High Similarity	NPC310211
0.9337	High Similarity	NPC39679
0.9113	High Similarity	NPC46561
0.9091	High Similarity	NPC249583
0.9045	High Similarity	NPC86834
0.9045	High Similarity	NPC210828
0.9005	High Similarity	NPC23294
0.8981	High Similarity	NPC198503
0.8955	High Similarity	NPC303951
0.885	High Similarity	NPC300156
0.8791	High Similarity	NPC6786
0.8762	High Similarity	NPC179287
0.8744	High Similarity	NPC184408
0.8657	High Similarity	NPC473187
0.8636	High Similarity	NPC70956
0.8636	High Similarity	NPC243834
0.8612	High Similarity	NPC208084
0.8571	High Similarity	NPC45190
0.8551	High Similarity	NPC39500
0.8551	High Similarity	NPC274640
0.851	High Similarity	NPC118228
0.8462	Intermediate Similarity	NPC160381
0.8443	Intermediate Similarity	NPC280799
0.8404	Intermediate Similarity	NPC144452
0.8364	Intermediate Similarity	NPC51388
0.835	Intermediate Similarity	NPC131017
0.835	Intermediate Similarity	NPC321428
0.8333	Intermediate Similarity	NPC475112
0.8333	Intermediate Similarity	NPC475085
0.8333	Intermediate Similarity	NPC291535
0.8278	Intermediate Similarity	NPC187501
0.8261	Intermediate Similarity	NPC193777
0.8227	Intermediate Similarity	NPC72211
0.8214	Intermediate Similarity	NPC212535
0.8213	Intermediate Similarity	NPC476106
0.819	Intermediate Similarity	NPC9894
0.819	Intermediate Similarity	NPC89549
0.817	Intermediate Similarity	NPC475844
0.814	Intermediate Similarity	NPC225279
0.8137	Intermediate Similarity	NPC306376
0.8136	Intermediate Similarity	NPC474688
0.8136	Intermediate Similarity	NPC474701
0.8131	Intermediate Similarity	NPC94943
0.8131	Intermediate Similarity	NPC473041
0.8128	Intermediate Similarity	NPC70259
0.8122	Intermediate Similarity	NPC148183
0.8122	Intermediate Similarity	NPC152768
0.8102	Intermediate Similarity	NPC60621
0.8081	Intermediate Similarity	NPC190007
0.8079	Intermediate Similarity	NPC43787
0.8079	Intermediate Similarity	NPC205934
0.8045	Intermediate Similarity	NPC194740
0.8029	Intermediate Similarity	NPC162484
0.8029	Intermediate Similarity	NPC134848
0.8	Intermediate Similarity	NPC283117
0.7991	Intermediate Similarity	NPC97746
0.7981	Intermediate Similarity	NPC48353
0.7953	Intermediate Similarity	NPC330009
0.7934	Intermediate Similarity	NPC294375
0.7917	Intermediate Similarity	NPC293151
0.7909	Intermediate Similarity	NPC21638
0.7902	Intermediate Similarity	NPC473105
0.79	Intermediate Similarity	NPC84478
0.7895	Intermediate Similarity	NPC199277
0.7895	Intermediate Similarity	NPC135887
0.7888	Intermediate Similarity	NPC473188
0.788	Intermediate Similarity	NPC303658
0.7854	Intermediate Similarity	NPC477532
0.7847	Intermediate Similarity	NPC476044
0.7847	Intermediate Similarity	NPC267423
0.7844	Intermediate Similarity	NPC298436
0.7844	Intermediate Similarity	NPC473179
0.784	Intermediate Similarity	NPC325297
0.7837	Intermediate Similarity	NPC128823
0.7826	Intermediate Similarity	NPC153042
0.7812	Intermediate Similarity	NPC260434
0.7803	Intermediate Similarity	NPC471762
0.7792	Intermediate Similarity	NPC475666
0.7783	Intermediate Similarity	NPC122436
0.7767	Intermediate Similarity	NPC146418
0.7766	Intermediate Similarity	NPC474409
0.7757	Intermediate Similarity	NPC201697
0.7757	Intermediate Similarity	NPC209769
0.775	Intermediate Similarity	NPC100734
0.775	Intermediate Similarity	NPC88923
0.775	Intermediate Similarity	NPC315634
0.7749	Intermediate Similarity	NPC81939
0.7725	Intermediate Similarity	NPC63971
0.7725	Intermediate Similarity	NPC91868
0.7721	Intermediate Similarity	NPC269367
0.7717	Intermediate Similarity	NPC96321
0.7699	Intermediate Similarity	NPC132329
0.7696	Intermediate Similarity	NPC89508
0.7689	Intermediate Similarity	NPC284685
0.7685	Intermediate Similarity	NPC220337
0.7672	Intermediate Similarity	NPC78609
0.7671	Intermediate Similarity	NPC305984
0.7664	Intermediate Similarity	NPC183777
0.7659	Intermediate Similarity	NPC242928
0.7653	Intermediate Similarity	NPC470930
0.765	Intermediate Similarity	NPC12344
0.7644	Intermediate Similarity	NPC276517
0.7644	Intermediate Similarity	NPC252251
0.7644	Intermediate Similarity	NPC66777
0.7639	Intermediate Similarity	NPC11464
0.7632	Intermediate Similarity	NPC39370
0.763	Intermediate Similarity	NPC329747
0.7628	Intermediate Similarity	NPC475910
0.7621	Intermediate Similarity	NPC473186
0.7621	Intermediate Similarity	NPC83111
0.7621	Intermediate Similarity	NPC474192
0.7621	Intermediate Similarity	NPC475720
0.7612	Intermediate Similarity	NPC88363
0.7612	Intermediate Similarity	NPC72980
0.7609	Intermediate Similarity	NPC470784
0.7606	Intermediate Similarity	NPC165599
0.7602	Intermediate Similarity	NPC74360
0.76	Intermediate Similarity	NPC473185
0.7591	Intermediate Similarity	NPC312645
0.7583	Intermediate Similarity	NPC191489
0.758	Intermediate Similarity	NPC16066
0.7577	Intermediate Similarity	NPC477531
0.7571	Intermediate Similarity	NPC141454
0.7565	Intermediate Similarity	NPC184680
0.7565	Intermediate Similarity	NPC235685
0.7564	Intermediate Similarity	NPC469734
0.7561	Intermediate Similarity	NPC194040
0.7557	Intermediate Similarity	NPC264285
0.7549	Intermediate Similarity	NPC62069
0.7546	Intermediate Similarity	NPC470931
0.7545	Intermediate Similarity	NPC469928
0.7545	Intermediate Similarity	NPC74969
0.7542	Intermediate Similarity	NPC165964
0.754	Intermediate Similarity	NPC195788
0.754	Intermediate Similarity	NPC237901
0.7533	Intermediate Similarity	NPC209174
0.7532	Intermediate Similarity	NPC470785
0.7532	Intermediate Similarity	NPC101350
0.7531	Intermediate Similarity	NPC472589
0.7523	Intermediate Similarity	NPC223427
0.7523	Intermediate Similarity	NPC317572
0.7521	Intermediate Similarity	NPC472588
0.7511	Intermediate Similarity	NPC67401
0.75	Intermediate Similarity	NPC16352
0.75	Intermediate Similarity	NPC280714
0.75	Intermediate Similarity	NPC244741
0.75	Intermediate Similarity	NPC217176
0.75	Intermediate Similarity	NPC475816
0.7489	Intermediate Similarity	NPC311906
0.7489	Intermediate Similarity	NPC15801
0.7489	Intermediate Similarity	NPC477533
0.7489	Intermediate Similarity	NPC323969
0.7488	Intermediate Similarity	NPC246700
0.7488	Intermediate Similarity	NPC132539
0.7477	Intermediate Similarity	NPC471304
0.7466	Intermediate Similarity	NPC170114
0.7465	Intermediate Similarity	NPC213308
0.7445	Intermediate Similarity	NPC478078
0.7442	Intermediate Similarity	NPC476098
0.7435	Intermediate Similarity	NPC473182
0.743	Intermediate Similarity	NPC232727
0.7429	Intermediate Similarity	NPC475190
0.7426	Intermediate Similarity	NPC84347
0.7421	Intermediate Similarity	NPC260909
0.7421	Intermediate Similarity	NPC470549
0.7419	Intermediate Similarity	NPC270918
0.7417	Intermediate Similarity	NPC478080
0.7415	Intermediate Similarity	NPC176127
0.7411	Intermediate Similarity	NPC472099
0.7411	Intermediate Similarity	NPC128115
0.7411	Intermediate Similarity	NPC469439
0.7409	Intermediate Similarity	NPC264176
0.7407	Intermediate Similarity	NPC285558
0.7404	Intermediate Similarity	NPC188400
0.7401	Intermediate Similarity	NPC202503
0.7401	Intermediate Similarity	NPC470018
0.7389	Intermediate Similarity	NPC205372
0.7389	Intermediate Similarity	NPC314633
0.7386	Intermediate Similarity	NPC478083
0.7376	Intermediate Similarity	NPC471080
0.7376	Intermediate Similarity	NPC469592
0.7375	Intermediate Similarity	NPC244543
0.7373	Intermediate Similarity	NPC160898
0.7368	Intermediate Similarity	NPC157931
0.7366	Intermediate Similarity	NPC474798
0.7366	Intermediate Similarity	NPC193267
0.7366	Intermediate Similarity	NPC213530
0.7358	Intermediate Similarity	NPC13880
0.735	Intermediate Similarity	NPC168922
0.7345	Intermediate Similarity	NPC220851
0.7339	Intermediate Similarity	NPC473183
0.7339	Intermediate Similarity	NPC193238

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 NPC174760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	670
0.2-0.3	944
0.3-0.4	1389
0.4-0.5	2767
0.5-0.6	2195
0.6-0.7	774
0.7-0.8	114
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8233	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD5632	Approved
0.8026	Intermediate Similarity	NPD5488	Discontinued
0.7907	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD6790	Phase 1
0.7768	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3258	Approved
0.7758	Intermediate Similarity	NPD3259	Approved
0.775	Intermediate Similarity	NPD7803	Approved
0.7743	Intermediate Similarity	NPD4373	Phase 2
0.7733	Intermediate Similarity	NPD6962	Phase 2
0.7729	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD7955	Approved
0.7689	Intermediate Similarity	NPD7956	Approved
0.7689	Intermediate Similarity	NPD4952	Phase 3
0.7661	Intermediate Similarity	NPD3257	Approved
0.7656	Intermediate Similarity	NPD5003	Discontinued
0.7653	Intermediate Similarity	NPD5901	Discontinued
0.7639	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7417	Discontinued
0.7617	Intermediate Similarity	NPD5482	Discontinued
0.7589	Intermediate Similarity	NPD3925	Approved
0.7583	Intermediate Similarity	NPD7708	Approved
0.757	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD8466	Approved
0.754	Intermediate Similarity	NPD8429	Approved
0.754	Intermediate Similarity	NPD8465	Approved
0.754	Intermediate Similarity	NPD8427	Approved
0.754	Intermediate Similarity	NPD8428	Approved
0.754	Intermediate Similarity	NPD8467	Approved
0.7536	Intermediate Similarity	NPD2564	Approved
0.7536	Intermediate Similarity	NPD2565	Phase 2
0.7535	Intermediate Similarity	NPD3003	Approved
0.7524	Intermediate Similarity	NPD5512	Phase 3
0.7523	Intermediate Similarity	NPD5416	Discontinued
0.751	Intermediate Similarity	NPD8364	Approved
0.751	Intermediate Similarity	NPD8363	Approved
0.7489	Intermediate Similarity	NPD6242	Discontinued
0.7477	Intermediate Similarity	NPD7395	Discontinued
0.7449	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4328	Approved
0.7421	Intermediate Similarity	NPD8460	Approved
0.7421	Intermediate Similarity	NPD8426	Approved
0.7421	Intermediate Similarity	NPD8425	Approved
0.7421	Intermediate Similarity	NPD8459	Approved
0.7409	Intermediate Similarity	NPD7069	Discontinued
0.7385	Intermediate Similarity	NPD5658	Approved
0.7379	Intermediate Similarity	NPD7689	Approved
0.7373	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5902	Approved
0.7342	Intermediate Similarity	NPD5903	Approved
0.7339	Intermediate Similarity	NPD5429	Discontinued
0.7339	Intermediate Similarity	NPD5805	Approved
0.7336	Intermediate Similarity	NPD1768	Approved
0.7311	Intermediate Similarity	NPD4418	Discontinued
0.7306	Intermediate Similarity	NPD2916	Discontinued
0.7288	Intermediate Similarity	NPD6716	Phase 1
0.7285	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4948	Discontinued
0.7273	Intermediate Similarity	NPD1867	Approved
0.7252	Intermediate Similarity	NPD5866	Approved
0.7247	Intermediate Similarity	NPD5450	Discontinued
0.7244	Intermediate Similarity	NPD1926	Approved
0.7241	Intermediate Similarity	NPD4885	Approved
0.7238	Intermediate Similarity	NPD8358	Approved
0.7224	Intermediate Similarity	NPD6531	Approved
0.7224	Intermediate Similarity	NPD6530	Approved
0.7222	Intermediate Similarity	NPD7853	Phase 2
0.7222	Intermediate Similarity	NPD484	Approved
0.7217	Intermediate Similarity	NPD7994	Phase 2
0.7212	Intermediate Similarity	NPD6974	Phase 3
0.7207	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD955	Approved
0.7195	Intermediate Similarity	NPD4506	Discontinued
0.7193	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1038	Approved
0.7183	Intermediate Similarity	NPD4539	Phase 1
0.7178	Intermediate Similarity	NPD3986	Discontinued
0.7178	Intermediate Similarity	NPD2844	Phase 3
0.7176	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3354	Phase 2
0.7162	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5479	Discontinued
0.7143	Intermediate Similarity	NPD8091	Phase 3
0.7143	Intermediate Similarity	NPD4601	Approved
0.7143	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4600	Approved
0.7137	Intermediate Similarity	NPD7558	Phase 2
0.7136	Intermediate Similarity	NPD5937	Approved
0.7136	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1505	Phase 2
0.7123	Intermediate Similarity	NPD2920	Discontinued
0.7115	Intermediate Similarity	NPD6709	Phase 3
0.711	Intermediate Similarity	NPD8489	Phase 1
0.7104	Intermediate Similarity	NPD1392	Approved
0.7093	Intermediate Similarity	NPD6985	Discontinued
0.7091	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5612	Discontinued
0.7061	Intermediate Similarity	NPD4312	Approved
0.7059	Intermediate Similarity	NPD1326	Approved
0.7059	Intermediate Similarity	NPD1325	Approved
0.7043	Intermediate Similarity	NPD6995	Phase 1
0.7035	Intermediate Similarity	NPD5293	Phase 2
0.7035	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3263	Phase 3
0.7023	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8463	Approved
0.702	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5532	Phase 2
0.702	Intermediate Similarity	NPD6252	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7878	Phase 2
0.7014	Intermediate Similarity	NPD3947	Discontinued
0.7014	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2779	Approved
0.7	Intermediate Similarity	NPD1483	Discontinued
0.6996	Remote Similarity	NPD8102	Discontinued
0.6995	Remote Similarity	NPD1534	Approved
0.6991	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3243	Approved
0.6987	Remote Similarity	NPD7194	Discontinued
0.6987	Remote Similarity	NPD6770	Approved
0.6982	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1466	Phase 3
0.6979	Remote Similarity	NPD1467	Approved
0.6978	Remote Similarity	NPD7470	Discontinued
0.6975	Remote Similarity	NPD4368	Phase 2
0.6974	Remote Similarity	NPD5164	Discontinued
0.6972	Remote Similarity	NPD4668	Phase 2
0.6968	Remote Similarity	NPD6176	Phase 1
0.696	Remote Similarity	NPD5399	Discovery
0.6949	Remote Similarity	NPD3746	Discontinued
0.6944	Remote Similarity	NPD802	Phase 2
0.6943	Remote Similarity	NPD4429	Discontinued
0.6943	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4981	Phase 2
0.6933	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6517	Phase 3
0.6927	Remote Similarity	NPD7948	Phase 1
0.692	Remote Similarity	NPD6376	Discontinued
0.692	Remote Similarity	NPD2509	Approved
0.692	Remote Similarity	NPD2510	Approved
0.6917	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD2792	Approved
0.691	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4501	Approved
0.6909	Remote Similarity	NPD4500	Approved
0.6909	Remote Similarity	NPD3290	Approved
0.6909	Remote Similarity	NPD3289	Phase 3
0.6907	Remote Similarity	NPD7688	Phase 1
0.6905	Remote Similarity	NPD5445	Approved
0.6903	Remote Similarity	NPD5067	Phase 2
0.6903	Remote Similarity	NPD5066	Phase 2
0.69	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7946	Pre-registration
0.6893	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7180	Phase 3
0.6881	Remote Similarity	NPD6550	Discontinued
0.688	Remote Similarity	NPD6228	Discontinued
0.6878	Remote Similarity	NPD4511	Phase 1
0.6875	Remote Similarity	NPD7452	Approved
0.6875	Remote Similarity	NPD7453	Approved
0.6875	Remote Similarity	NPD7222	Phase 2
0.6864	Remote Similarity	NPD6874	Approved
0.6864	Remote Similarity	NPD2778	Approved
0.6864	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3006	Discontinued
0.6857	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8160	Phase 2
0.6849	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3794	Approved
0.6842	Remote Similarity	NPD3795	Approved
0.6835	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.683	Remote Similarity	NPD8403	Phase 1
0.683	Remote Similarity	NPD5530	Phase 1
0.6826	Remote Similarity	NPD1976	Approved
0.6822	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.682	Remote Similarity	NPD2951	Discontinued
0.6808	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7181	Phase 3
0.6806	Remote Similarity	NPD4499	Approved
0.6803	Remote Similarity	NPD4350	Approved
0.6803	Remote Similarity	NPD4349	Approved
0.6795	Remote Similarity	NPD7548	Discontinued
0.6793	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5022	Discontinued
0.6789	Remote Similarity	NPD7658	Phase 2
0.6789	Remote Similarity	NPD4558	Phase 2
0.6786	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6987	Phase 1
0.6784	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6778	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