NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	241.07
Volume:	243.943
LogP:	3.389
LogD:	3.037
LogS:	-4.696
# Rotatable Bonds:	2
TPSA:	62.32
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	2.342
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.994
MDCK Permeability:	6.205633326317184e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	95.15477752685547%
Volume Distribution (VD):	0.755
Pgp-substrate:	4.429694175720215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.864
CYP2C19-inhibitor:	0.378
CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.629
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.468
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	4.579
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.769
AMES Toxicity:	0.814
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.908
Carcinogencity:	0.501
Eye Corrosion:	0.153
Eye Irritation:	0.987
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC247803

Natural Product ID:	NPC247803
*Common Name:**	2-Hydroxy-3-Formyl-7-Methoxycarbazole
IUPAC Name:	2-hydroxy-7-methoxy-9H-carbazole-3-carbaldehyde
Synonyms:
Standard InCHIKey:	JLWFCPLXNANORV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11NO3/c1-18-9-2-3-10-11-4-8(7-16)14(17)6-13(11)15-12(10)5-9/h2-7,15,17H,1H3
SMILES:	COc1ccc2c3cc(C=O)c(cc3[nH]c2c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463264
PubChem CID:	189687
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
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757740]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	flower	n.a.	PMID[10757740]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[10757740]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10757740]
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]
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]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28639	Trixis grisebachii	Species	Asteraceae	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]
NPO28961	Croton hutchinsonianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29095	Yucca elata	Species	Asparagaceae	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]
NPO28943	Daldinia vernicosa	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28544	Podocalyx loranthoides	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25073	Saccharina latissima	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29161	Hyptis urticoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29497	Delphinium speciosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19266	Clausena excavata	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]
NPO28427	Gutenbergia marginata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29070	Bulbine asphodeloides	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29028	Cicer cuneatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27349	Rhododendron edgeworthii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4806	Clausena wallichii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27603	Populus candicans	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23710	Otholobium pubescens	Species	Fabaceae	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]
NPO29073	Ipomoea carnea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29461	Sarcophyton infundibuliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29518	Nardia scalaris	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17480	Murraya siamensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29387	Eudendrium racemosum	Species	Eudendriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29180	Monachosorum maximowiczii	Species	Dennstaedtiaceae	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
ED50	5
IC50	4
MIC	2
Others	2

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	3
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.74	ug ml-1	PMID[482330]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[482330]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	28600.0	nM	PMID[482331]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	181400.0	nM	PMID[482332]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	69100.0	nM	PMID[482332]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	45900.0	nM	PMID[482332]
NPT140	Organism	Artemia	Artemia	LC50	=	35.0	ppm	PMID[482330]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.7	ug ml-1	PMID[482330]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.48	ug ml-1	PMID[482330]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[482330]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[482332]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[482332]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	24300.0	nM	PMID[482333]

☑ 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 NPC247803 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	461
0.1-0.2	3113
0.2-0.3	12748
0.3-0.4	3787
0.4-0.5	12687
0.5-0.6	7679
0.6-0.7	1660
0.7-0.8	473
0.8-0.85	53
0.85-0.9	14
0.9-0.95	17
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC150239
0.9741	High Similarity	NPC310211
0.9741	High Similarity	NPC308137
0.9534	High Similarity	NPC210828
0.9534	High Similarity	NPC86834
0.9497	High Similarity	NPC174760
0.9495	High Similarity	NPC46561
0.9487	High Similarity	NPC23294
0.9482	High Similarity	NPC249583
0.9436	High Similarity	NPC303951
0.9394	High Similarity	NPC3207
0.9388	High Similarity	NPC87413
0.9353	High Similarity	NPC198503
0.9343	High Similarity	NPC116238
0.925	High Similarity	NPC169402
0.9235	High Similarity	NPC39679
0.9234	High Similarity	NPC6786
0.9216	High Similarity	NPC179287
0.9184	High Similarity	NPC4687
0.9005	High Similarity	NPC473187
0.8971	High Similarity	NPC208084
0.8939	High Similarity	NPC45190
0.8821	High Similarity	NPC70956
0.8821	High Similarity	NPC243834
0.8657	High Similarity	NPC300156
0.8627	High Similarity	NPC187501
0.8627	High Similarity	NPC9894
0.8558	High Similarity	NPC184408
0.8507	High Similarity	NPC291535
0.8507	High Similarity	NPC475085
0.8507	High Similarity	NPC475112
0.8502	High Similarity	NPC89549
0.8476	Intermediate Similarity	NPC225279
0.8434	Intermediate Similarity	NPC131017
0.8431	Intermediate Similarity	NPC193777
0.8431	Intermediate Similarity	NPC283117
0.8413	Intermediate Similarity	NPC118228
0.8394	Intermediate Similarity	NPC212535
0.8382	Intermediate Similarity	NPC476106
0.8365	Intermediate Similarity	NPC39500
0.8357	Intermediate Similarity	NPC294375
0.8333	Intermediate Similarity	NPC293151
0.8308	Intermediate Similarity	NPC94943
0.8308	Intermediate Similarity	NPC72211
0.8287	Intermediate Similarity	NPC274640
0.8271	Intermediate Similarity	NPC51388
0.8265	Intermediate Similarity	NPC160381
0.8263	Intermediate Similarity	NPC280799
0.8256	Intermediate Similarity	NPC190007
0.8233	Intermediate Similarity	NPC97746
0.8224	Intermediate Similarity	NPC144452
0.8209	Intermediate Similarity	NPC70259
0.8195	Intermediate Similarity	NPC134848
0.8194	Intermediate Similarity	NPC473188
0.8164	Intermediate Similarity	NPC321428
0.8159	Intermediate Similarity	NPC205934
0.8159	Intermediate Similarity	NPC43787
0.8143	Intermediate Similarity	NPC48353
0.8128	Intermediate Similarity	NPC474701
0.8107	Intermediate Similarity	NPC162484
0.8077	Intermediate Similarity	NPC183777
0.8058	Intermediate Similarity	NPC135887
0.8058	Intermediate Similarity	NPC199277
0.8045	Intermediate Similarity	NPC474688
0.8039	Intermediate Similarity	NPC306376
0.8037	Intermediate Similarity	NPC194740
0.8	Intermediate Similarity	NPC128823
0.8	Intermediate Similarity	NPC475844
0.8	Intermediate Similarity	NPC473179
0.8	Intermediate Similarity	NPC298436
0.799	Intermediate Similarity	NPC153042
0.798	Intermediate Similarity	NPC84478
0.7953	Intermediate Similarity	NPC303658
0.7953	Intermediate Similarity	NPC473041
0.7944	Intermediate Similarity	NPC152768
0.7944	Intermediate Similarity	NPC148183
0.7938	Intermediate Similarity	NPC474409
0.7937	Intermediate Similarity	NPC39370
0.7928	Intermediate Similarity	NPC473186
0.7926	Intermediate Similarity	NPC477532
0.7926	Intermediate Similarity	NPC60621
0.7925	Intermediate Similarity	NPC146418
0.7923	Intermediate Similarity	NPC476044
0.7923	Intermediate Similarity	NPC267423
0.7915	Intermediate Similarity	NPC209769
0.7887	Intermediate Similarity	NPC12344
0.7877	Intermediate Similarity	NPC269367
0.7873	Intermediate Similarity	NPC471762
0.787	Intermediate Similarity	NPC91868
0.787	Intermediate Similarity	NPC63971
0.786	Intermediate Similarity	NPC330009
0.7854	Intermediate Similarity	NPC122436
0.783	Intermediate Similarity	NPC201697
0.7793	Intermediate Similarity	NPC11464
0.7783	Intermediate Similarity	NPC475910
0.7778	Intermediate Similarity	NPC88363
0.7778	Intermediate Similarity	NPC72980
0.7768	Intermediate Similarity	NPC132329
0.7757	Intermediate Similarity	NPC220337
0.7748	Intermediate Similarity	NPC473185
0.7742	Intermediate Similarity	NPC305984
0.7739	Intermediate Similarity	NPC78609
0.7738	Intermediate Similarity	NPC21638
0.7734	Intermediate Similarity	NPC242928
0.7733	Intermediate Similarity	NPC473105
0.7731	Intermediate Similarity	NPC16066
0.7725	Intermediate Similarity	NPC470930
0.7721	Intermediate Similarity	NPC264176
0.7713	Intermediate Similarity	NPC252251
0.7713	Intermediate Similarity	NPC66777
0.7706	Intermediate Similarity	NPC264285
0.7703	Intermediate Similarity	NPC329747
0.77	Intermediate Similarity	NPC470931
0.7678	Intermediate Similarity	NPC223427
0.7675	Intermediate Similarity	NPC470784
0.7664	Intermediate Similarity	NPC325297
0.7647	Intermediate Similarity	NPC246700
0.7644	Intermediate Similarity	NPC260434
0.7644	Intermediate Similarity	NPC477531
0.7632	Intermediate Similarity	NPC235685
0.7632	Intermediate Similarity	NPC184680
0.7613	Intermediate Similarity	NPC205372
0.76	Intermediate Similarity	NPC209174
0.7598	Intermediate Similarity	NPC470785
0.7598	Intermediate Similarity	NPC101350
0.7577	Intermediate Similarity	NPC473182
0.757	Intermediate Similarity	NPC270918
0.7566	Intermediate Similarity	NPC217176
0.7557	Intermediate Similarity	NPC323969
0.7554	Intermediate Similarity	NPC475666
0.7549	Intermediate Similarity	NPC194040
0.7548	Intermediate Similarity	NPC276517
0.7546	Intermediate Similarity	NPC471304
0.7545	Intermediate Similarity	NPC96321
0.7537	Intermediate Similarity	NPC62069
0.7535	Intermediate Similarity	NPC171787
0.7534	Intermediate Similarity	NPC170114
0.7523	Intermediate Similarity	NPC469592
0.7523	Intermediate Similarity	NPC471080
0.7523	Intermediate Similarity	NPC89508
0.7513	Intermediate Similarity	NPC76982
0.7512	Intermediate Similarity	NPC165599
0.7511	Intermediate Similarity	NPC213530
0.7511	Intermediate Similarity	NPC193267
0.7511	Intermediate Similarity	NPC478078
0.7511	Intermediate Similarity	NPC81939
0.7511	Intermediate Similarity	NPC74360
0.75	Intermediate Similarity	NPC67401
0.75	Intermediate Similarity	NPC232727
0.7489	Intermediate Similarity	NPC220851
0.7489	Intermediate Similarity	NPC470549
0.7489	Intermediate Similarity	NPC16352
0.7488	Intermediate Similarity	NPC176127
0.7479	Intermediate Similarity	NPC469734
0.7478	Intermediate Similarity	NPC473183
0.7477	Intermediate Similarity	NPC285558
0.7477	Intermediate Similarity	NPC477533
0.7476	Intermediate Similarity	NPC128751
0.7468	Intermediate Similarity	NPC188400
0.7467	Intermediate Similarity	NPC202503
0.7467	Intermediate Similarity	NPC473184
0.7467	Intermediate Similarity	NPC470018
0.7456	Intermediate Similarity	NPC474192
0.7456	Intermediate Similarity	NPC475720
0.7455	Intermediate Similarity	NPC74969
0.7455	Intermediate Similarity	NPC469928
0.7449	Intermediate Similarity	NPC88923
0.7449	Intermediate Similarity	NPC315634
0.7449	Intermediate Similarity	NPC100734
0.7448	Intermediate Similarity	NPC472589
0.744	Intermediate Similarity	NPC83111
0.744	Intermediate Similarity	NPC106833
0.744	Intermediate Similarity	NPC469497
0.7438	Intermediate Similarity	NPC474798
0.7437	Intermediate Similarity	NPC472588
0.7436	Intermediate Similarity	NPC160898
0.7434	Intermediate Similarity	NPC157931
0.7429	Intermediate Similarity	NPC13880
0.7429	Intermediate Similarity	NPC251090
0.7427	Intermediate Similarity	NPC46580
0.7421	Intermediate Similarity	NPC312645
0.7397	Intermediate Similarity	NPC316981
0.7397	Intermediate Similarity	NPC219087
0.7395	Intermediate Similarity	NPC189079
0.7393	Intermediate Similarity	NPC141454
0.7393	Intermediate Similarity	NPC160100
0.7387	Intermediate Similarity	NPC131885
0.7387	Intermediate Similarity	NPC469594
0.7386	Intermediate Similarity	NPC284685
0.7385	Intermediate Similarity	NPC470020
0.7384	Intermediate Similarity	NPC165964
0.7376	Intermediate Similarity	NPC322064
0.7371	Intermediate Similarity	NPC131486
0.7371	Intermediate Similarity	NPC213308
0.7371	Intermediate Similarity	NPC11017
0.7364	Intermediate Similarity	NPC244543
0.7362	Intermediate Similarity	NPC208522
0.7361	Intermediate Similarity	NPC472287
0.7361	Intermediate Similarity	NPC472286
0.7353	Intermediate Similarity	NPC133609

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 NPC247803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	700
0.2-0.3	964
0.3-0.4	1408
0.4-0.5	2783
0.5-0.6	2119
0.6-0.7	761
0.7-0.8	100
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
0.8056	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5632	Approved
0.7841	Intermediate Similarity	NPD6790	Phase 1
0.7814	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD3003	Approved
0.7642	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5488	Discontinued
0.7577	Intermediate Similarity	NPD4373	Phase 2
0.7566	Intermediate Similarity	NPD6962	Phase 2
0.7557	Intermediate Similarity	NPD6242	Discontinued
0.7522	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4952	Phase 3
0.7511	Intermediate Similarity	NPD3258	Approved
0.7511	Intermediate Similarity	NPD3259	Approved
0.7488	Intermediate Similarity	NPD1768	Approved
0.7477	Intermediate Similarity	NPD5901	Discontinued
0.7476	Intermediate Similarity	NPD5003	Discontinued
0.7458	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5482	Discontinued
0.7454	Intermediate Similarity	NPD5658	Approved
0.7454	Intermediate Similarity	NPD2916	Discontinued
0.7449	Intermediate Similarity	NPD7803	Approved
0.7445	Intermediate Similarity	NPD5479	Discontinued
0.7431	Intermediate Similarity	NPD5416	Discontinued
0.7429	Intermediate Similarity	NPD5512	Phase 3
0.7409	Intermediate Similarity	NPD5903	Approved
0.7409	Intermediate Similarity	NPD3257	Approved
0.7409	Intermediate Similarity	NPD5902	Approved
0.7386	Intermediate Similarity	NPD7956	Approved
0.7386	Intermediate Similarity	NPD7955	Approved
0.7357	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2564	Approved
0.7356	Intermediate Similarity	NPD2565	Phase 2
0.7352	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3925	Approved
0.732	Intermediate Similarity	NPD8427	Approved
0.732	Intermediate Similarity	NPD8466	Approved
0.732	Intermediate Similarity	NPD8467	Approved
0.732	Intermediate Similarity	NPD8429	Approved
0.732	Intermediate Similarity	NPD8465	Approved
0.732	Intermediate Similarity	NPD8428	Approved
0.7315	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD3986	Discontinued
0.7309	Intermediate Similarity	NPD7395	Discontinued
0.7308	Intermediate Similarity	NPD7417	Discontinued
0.7306	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8364	Approved
0.7287	Intermediate Similarity	NPD8363	Approved
0.7286	Intermediate Similarity	NPD5937	Approved
0.7284	Intermediate Similarity	NPD6530	Approved
0.7284	Intermediate Similarity	NPD7708	Approved
0.7284	Intermediate Similarity	NPD6531	Approved
0.7281	Intermediate Similarity	NPD4328	Approved
0.7273	Intermediate Similarity	NPD8460	Approved
0.7273	Intermediate Similarity	NPD8459	Approved
0.7261	Intermediate Similarity	NPD1505	Phase 2
0.7257	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1038	Approved
0.7248	Intermediate Similarity	NPD5429	Discontinued
0.7248	Intermediate Similarity	NPD1392	Approved
0.7243	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5612	Discontinued
0.7215	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD8426	Approved
0.7205	Intermediate Similarity	NPD8425	Approved
0.7198	Intermediate Similarity	NPD7558	Phase 2
0.7181	Intermediate Similarity	NPD6995	Phase 1
0.7175	Intermediate Similarity	NPD5293	Phase 2
0.7162	Intermediate Similarity	NPD7069	Discontinued
0.7156	Intermediate Similarity	NPD6985	Discontinued
0.7155	Intermediate Similarity	NPD4885	Approved
0.7143	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8091	Phase 3
0.7131	Intermediate Similarity	NPD6716	Phase 1
0.713	Intermediate Similarity	NPD484	Approved
0.7129	Intermediate Similarity	NPD1326	Approved
0.7129	Intermediate Similarity	NPD1325	Approved
0.7124	Intermediate Similarity	NPD7194	Discontinued
0.7112	Intermediate Similarity	NPD1867	Approved
0.7111	Intermediate Similarity	NPD5164	Discontinued
0.7106	Intermediate Similarity	NPD5805	Approved
0.7097	Intermediate Similarity	NPD5450	Discontinued
0.7095	Intermediate Similarity	NPD4948	Discontinued
0.7091	Intermediate Similarity	NPD7222	Phase 2
0.7091	Intermediate Similarity	NPD7453	Approved
0.7091	Intermediate Similarity	NPD7452	Approved
0.7089	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4539	Phase 1
0.7064	Intermediate Similarity	NPD7853	Phase 2
0.7059	Intermediate Similarity	NPD6376	Discontinued
0.7056	Intermediate Similarity	NPD4418	Discontinued
0.7056	Intermediate Similarity	NPD7994	Phase 2
0.7045	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5067	Phase 2
0.704	Intermediate Similarity	NPD5066	Phase 2
0.704	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4506	Discontinued
0.7024	Intermediate Similarity	NPD7689	Approved
0.7018	Intermediate Similarity	NPD4511	Phase 1
0.7012	Intermediate Similarity	NPD8358	Approved
0.7009	Intermediate Similarity	NPD3746	Discontinued
0.7009	Intermediate Similarity	NPD5866	Approved
0.7009	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD1926	Approved
0.7004	Intermediate Similarity	NPD4429	Discontinued
0.7004	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4981	Phase 2
0.6995	Remote Similarity	NPD2844	Phase 3
0.6991	Remote Similarity	NPD7948	Phase 1
0.6981	Remote Similarity	NPD2792	Approved
0.6979	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4600	Approved
0.6972	Remote Similarity	NPD4601	Approved
0.6968	Remote Similarity	NPD8403	Phase 1
0.696	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD2920	Discontinued
0.6952	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2951	Discontinued
0.6947	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5532	Phase 2
0.6931	Remote Similarity	NPD955	Approved
0.693	Remote Similarity	NPD3354	Phase 2
0.693	Remote Similarity	NPD802	Phase 2
0.6923	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5022	Discontinued
0.6919	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6517	Phase 3
0.6912	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8489	Phase 1
0.6903	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3945	Discontinued
0.69	Remote Similarity	NPD6974	Phase 3
0.69	Remote Similarity	NPD4312	Approved
0.6898	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5530	Phase 1
0.6889	Remote Similarity	NPD6220	Phase 3
0.6889	Remote Similarity	NPD4502	Phase 2
0.688	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6176	Phase 1
0.687	Remote Similarity	NPD8463	Approved
0.6867	Remote Similarity	NPD7426	Phase 1
0.6867	Remote Similarity	NPD3263	Phase 3
0.6864	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7181	Phase 3
0.6857	Remote Similarity	NPD4203	Approved
0.6857	Remote Similarity	NPD4204	Approved
0.6852	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3825	Phase 3
0.6847	Remote Similarity	NPD3947	Discontinued
0.6847	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD8102	Discontinued
0.6844	Remote Similarity	NPD4558	Phase 2
0.6842	Remote Similarity	NPD3920	Phase 2
0.6838	Remote Similarity	NPD4845	Discontinued
0.6833	Remote Similarity	NPD4561	Discontinued
0.6833	Remote Similarity	NPD2779	Approved
0.683	Remote Similarity	NPD2509	Approved
0.683	Remote Similarity	NPD2510	Approved
0.6828	Remote Similarity	NPD3243	Approved
0.6826	Remote Similarity	NPD6770	Approved
0.6822	Remote Similarity	NPD1466	Phase 3
0.6822	Remote Similarity	NPD1467	Approved
0.6822	Remote Similarity	NPD1534	Approved
0.682	Remote Similarity	NPD6590	Discontinued
0.682	Remote Similarity	NPD4368	Phase 2
0.6818	Remote Similarity	NPD4500	Approved
0.6818	Remote Similarity	NPD4501	Approved
0.6814	Remote Similarity	NPD7470	Discontinued
0.6812	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5513	Phase 2
0.6783	Remote Similarity	NPD7878	Phase 2
0.6778	Remote Similarity	NPD3006	Discontinued
0.677	Remote Similarity	NPD6709	Phase 3
0.6765	Remote Similarity	NPD6494	Phase 2
0.6763	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5913	Phase 3
0.6759	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7688	Phase 1
0.6746	Remote Similarity	NPD5399	Discovery
0.6742	Remote Similarity	NPD3289	Phase 3
0.6742	Remote Similarity	NPD3290	Approved
0.6741	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD6245	Phase 2
0.6739	Remote Similarity	NPD1976	Approved
0.6738	Remote Similarity	NPD7219	Approved
0.6738	Remote Similarity	NPD7221	Approved
0.6733	Remote Similarity	NPD6228	Discontinued
0.673	Remote Similarity	NPD5445	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data