NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	482.34
Volume:	538.405
LogP:	6.113
LogD:	4.208
LogS:	-4.918
# Rotatable Bonds:	10
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	5.01
Fsp3:	0.677
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.424
MDCK Permeability:	1.804126804927364e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.162
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	94.7481460571289%
Volume Distribution (VD):	0.569
Pgp-substrate:	2.039238691329956%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.359
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	1.711
Half-life (T1/2):	0.338

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.829
Carcinogencity:	0.722
Eye Corrosion:	0.018
Eye Irritation:	0.015
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC274982

Natural Product ID:	NPC274982
*Common Name:**	IADUHWGVUSHTRQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IADUHWGVUSHTRQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10N2O3/c1-20-9-2-3-10-11-6-7-16(19)12-4-5-14(18)17(15(11)12)13(10)8-9/h2-8H,1H3
SMILES:	COc1ccc2c3ccn(=O)c4ccc(=O)n(c2c1)c34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462673
PubChem CID:	44593495
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	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	10

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[497479]
NPT168	Cell Line	P388	Mus musculus	ED50	=	11.7	ug ml-1	PMID[497479]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	18.9	ug ml-1	PMID[497480]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	18.5	ug ml-1	PMID[497480]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[497479]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.5	ug ml-1	PMID[497479]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	6.5	ug ml-1	PMID[497479]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.2	ug ml-1	PMID[497479]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	6.0	ug ml-1	PMID[497479]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.1	ug ml-1	PMID[497479]

☑ 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 NPC274982 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	791
0.1-0.2	4206
0.2-0.3	12791
0.3-0.4	7666
0.4-0.5	12594
0.5-0.6	2366
0.6-0.7	1865
0.7-0.8	374
0.8-0.85	28
0.85-0.9	4
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9686	High Similarity	NPC174758
0.9381	High Similarity	NPC174672
0.9235	High Similarity	NPC85273
0.9133	High Similarity	NPC82548
0.8939	High Similarity	NPC287208
0.8929	High Similarity	NPC53144
0.8643	High Similarity	NPC200836
0.8636	High Similarity	NPC232727
0.8593	High Similarity	NPC295898
0.8564	High Similarity	NPC198673
0.8408	Intermediate Similarity	NPC211813
0.8402	Intermediate Similarity	NPC99891
0.8392	Intermediate Similarity	NPC168911
0.8392	Intermediate Similarity	NPC239954
0.839	Intermediate Similarity	NPC167860
0.839	Intermediate Similarity	NPC123976
0.8342	Intermediate Similarity	NPC267928
0.8325	Intermediate Similarity	NPC285558
0.8263	Intermediate Similarity	NPC122436
0.8169	Intermediate Similarity	NPC60621
0.816	Intermediate Similarity	NPC213530
0.816	Intermediate Similarity	NPC193267
0.8128	Intermediate Similarity	NPC176538
0.8128	Intermediate Similarity	NPC141053
0.8119	Intermediate Similarity	NPC212213
0.8075	Intermediate Similarity	NPC17565
0.8048	Intermediate Similarity	NPC264176
0.8037	Intermediate Similarity	NPC260434
0.8018	Intermediate Similarity	NPC235685
0.801	Intermediate Similarity	NPC32534
0.7982	Intermediate Similarity	NPC101350
0.7951	Intermediate Similarity	NPC19872
0.7933	Intermediate Similarity	NPC470164
0.7933	Intermediate Similarity	NPC323345
0.7926	Intermediate Similarity	NPC65277
0.7923	Intermediate Similarity	NPC245816
0.7923	Intermediate Similarity	NPC476138
0.7879	Intermediate Similarity	NPC84478
0.7864	Intermediate Similarity	NPC471762
0.7834	Intermediate Similarity	NPC310118
0.782	Intermediate Similarity	NPC185782
0.7778	Intermediate Similarity	NPC315957
0.7766	Intermediate Similarity	NPC12649
0.7757	Intermediate Similarity	NPC476287
0.7749	Intermediate Similarity	NPC26543
0.7743	Intermediate Similarity	NPC30540
0.7736	Intermediate Similarity	NPC469589
0.7732	Intermediate Similarity	NPC476518
0.7731	Intermediate Similarity	NPC305984
0.771	Intermediate Similarity	NPC26679
0.7703	Intermediate Similarity	NPC66777
0.7692	Intermediate Similarity	NPC121772
0.7692	Intermediate Similarity	NPC234197
0.7692	Intermediate Similarity	NPC14651
0.7692	Intermediate Similarity	NPC121658
0.767	Intermediate Similarity	NPC13880
0.7658	Intermediate Similarity	NPC110151
0.7656	Intermediate Similarity	NPC177404
0.7652	Intermediate Similarity	NPC472434
0.7644	Intermediate Similarity	NPC287437
0.7644	Intermediate Similarity	NPC293487
0.763	Intermediate Similarity	NPC476581
0.763	Intermediate Similarity	NPC36229
0.763	Intermediate Similarity	NPC16452
0.7629	Intermediate Similarity	NPC91868
0.7629	Intermediate Similarity	NPC63971
0.7626	Intermediate Similarity	NPC128115
0.7623	Intermediate Similarity	NPC314954
0.7617	Intermediate Similarity	NPC478182
0.7617	Intermediate Similarity	NPC470020
0.7615	Intermediate Similarity	NPC303658
0.7608	Intermediate Similarity	NPC329747
0.7608	Intermediate Similarity	NPC477019
0.7604	Intermediate Similarity	NPC170114
0.7604	Intermediate Similarity	NPC8022
0.7604	Intermediate Similarity	NPC470799
0.7583	Intermediate Similarity	NPC475774
0.7561	Intermediate Similarity	NPC92111
0.756	Intermediate Similarity	NPC4071
0.756	Intermediate Similarity	NPC476578
0.756	Intermediate Similarity	NPC476582
0.7558	Intermediate Similarity	NPC470549
0.755	Intermediate Similarity	NPC24864
0.7549	Intermediate Similarity	NPC296527
0.7546	Intermediate Similarity	NPC202768
0.7546	Intermediate Similarity	NPC296482
0.7546	Intermediate Similarity	NPC53069
0.7533	Intermediate Similarity	NPC253675
0.7524	Intermediate Similarity	NPC195268
0.7524	Intermediate Similarity	NPC133140
0.7512	Intermediate Similarity	NPC162530
0.7512	Intermediate Similarity	NPC76748
0.75	Intermediate Similarity	NPC223427
0.7489	Intermediate Similarity	NPC21638
0.7489	Intermediate Similarity	NPC473513
0.7488	Intermediate Similarity	NPC307963
0.7488	Intermediate Similarity	NPC31930
0.7477	Intermediate Similarity	NPC313189
0.7476	Intermediate Similarity	NPC81535
0.7474	Intermediate Similarity	NPC478185
0.7468	Intermediate Similarity	NPC472435
0.7467	Intermediate Similarity	NPC194740
0.7466	Intermediate Similarity	NPC323969
0.7465	Intermediate Similarity	NPC96405
0.7465	Intermediate Similarity	NPC171409
0.7455	Intermediate Similarity	NPC173080
0.7454	Intermediate Similarity	NPC11464
0.7449	Intermediate Similarity	NPC478183
0.7445	Intermediate Similarity	NPC469554
0.7443	Intermediate Similarity	NPC152768
0.7443	Intermediate Similarity	NPC148183
0.7442	Intermediate Similarity	NPC475910
0.744	Intermediate Similarity	NPC324149
0.7438	Intermediate Similarity	NPC284678
0.7436	Intermediate Similarity	NPC478184
0.7431	Intermediate Similarity	NPC471080
0.7431	Intermediate Similarity	NPC469592
0.743	Intermediate Similarity	NPC238457
0.743	Intermediate Similarity	NPC472111
0.7426	Intermediate Similarity	NPC266551
0.7424	Intermediate Similarity	NPC470017
0.7424	Intermediate Similarity	NPC295228
0.7422	Intermediate Similarity	NPC157931
0.7419	Intermediate Similarity	NPC208284
0.7416	Intermediate Similarity	NPC251090
0.7415	Intermediate Similarity	NPC46580
0.7409	Intermediate Similarity	NPC26850
0.7395	Intermediate Similarity	NPC135549
0.7391	Intermediate Similarity	NPC470022
0.7389	Intermediate Similarity	NPC176127
0.7387	Intermediate Similarity	NPC472099
0.7387	Intermediate Similarity	NPC111624
0.7385	Intermediate Similarity	NPC202605
0.7385	Intermediate Similarity	NPC112206
0.7385	Intermediate Similarity	NPC472098
0.7385	Intermediate Similarity	NPC316981
0.7383	Intermediate Similarity	NPC470500
0.7383	Intermediate Similarity	NPC475070
0.7375	Intermediate Similarity	NPC472436
0.7374	Intermediate Similarity	NPC91895
0.7368	Intermediate Similarity	NPC101543
0.7366	Intermediate Similarity	NPC322482
0.7346	Intermediate Similarity	NPC72211
0.7344	Intermediate Similarity	NPC26872
0.7342	Intermediate Similarity	NPC292958
0.734	Intermediate Similarity	NPC470474
0.7339	Intermediate Similarity	NPC146418
0.7317	Intermediate Similarity	NPC20249
0.7316	Intermediate Similarity	NPC472061
0.7315	Intermediate Similarity	NPC4687
0.7315	Intermediate Similarity	NPC249583
0.7311	Intermediate Similarity	NPC476167
0.7301	Intermediate Similarity	NPC470018
0.7297	Intermediate Similarity	NPC473041
0.7297	Intermediate Similarity	NPC469594
0.7297	Intermediate Similarity	NPC100079
0.7297	Intermediate Similarity	NPC23614
0.7294	Intermediate Similarity	NPC290689
0.7294	Intermediate Similarity	NPC5145
0.729	Intermediate Similarity	NPC57398
0.7286	Intermediate Similarity	NPC131017
0.7284	Intermediate Similarity	NPC474183
0.7277	Intermediate Similarity	NPC11017
0.7273	Intermediate Similarity	NPC149471
0.7273	Intermediate Similarity	NPC477549
0.7273	Intermediate Similarity	NPC271215
0.7273	Intermediate Similarity	NPC236668
0.7269	Intermediate Similarity	NPC74575
0.7269	Intermediate Similarity	NPC476121
0.7269	Intermediate Similarity	NPC476124
0.7268	Intermediate Similarity	NPC62069
0.7265	Intermediate Similarity	NPC298436
0.7265	Intermediate Similarity	NPC46451
0.7264	Intermediate Similarity	NPC192315
0.726	Intermediate Similarity	NPC134079
0.7255	Intermediate Similarity	NPC161887
0.7255	Intermediate Similarity	NPC219963
0.7251	Intermediate Similarity	NPC70259
0.7251	Intermediate Similarity	NPC194967
0.7246	Intermediate Similarity	NPC206251
0.7246	Intermediate Similarity	NPC74382
0.7243	Intermediate Similarity	NPC470586
0.7241	Intermediate Similarity	NPC72980
0.724	Intermediate Similarity	NPC146976
0.724	Intermediate Similarity	NPC235076
0.7235	Intermediate Similarity	NPC193238
0.7232	Intermediate Similarity	NPC477533
0.7227	Intermediate Similarity	NPC118940
0.7222	Intermediate Similarity	NPC148889
0.722	Intermediate Similarity	NPC264285
0.7217	Intermediate Similarity	NPC243834
0.7217	Intermediate Similarity	NPC70956
0.7217	Intermediate Similarity	NPC224928
0.7215	Intermediate Similarity	NPC188420
0.7206	Intermediate Similarity	NPC222592
0.7206	Intermediate Similarity	NPC168486
0.7204	Intermediate Similarity	NPC43787
0.7204	Intermediate Similarity	NPC205934
0.7202	Intermediate Similarity	NPC470931
0.7198	Intermediate Similarity	NPC204385

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 NPC274982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	439
0.1-0.2	596
0.2-0.3	918
0.3-0.4	1624
0.4-0.5	2552
0.5-0.6	1971
0.6-0.7	935
0.7-0.8	114
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7885	Intermediate Similarity	NPD4795	Phase 2
0.7832	Intermediate Similarity	NPD6790	Phase 1
0.7778	Intermediate Similarity	NPD1739	Approved
0.7778	Intermediate Similarity	NPD1740	Approved
0.7696	Intermediate Similarity	NPD4372	Phase 1
0.7689	Intermediate Similarity	NPD5658	Approved
0.7659	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5601	Phase 2
0.7548	Intermediate Similarity	NPD1622	Discontinued
0.7546	Intermediate Similarity	NPD3816	Phase 1
0.7546	Intermediate Similarity	NPD3815	Phase 1
0.7545	Intermediate Similarity	NPD6242	Discontinued
0.7536	Intermediate Similarity	NPD4418	Discontinued
0.7534	Intermediate Similarity	NPD7426	Phase 1
0.7533	Intermediate Similarity	NPD2757	Phase 2
0.7524	Intermediate Similarity	NPD3923	Approved
0.7524	Intermediate Similarity	NPD3921	Approved
0.7524	Intermediate Similarity	NPD3922	Approved
0.7524	Intermediate Similarity	NPD3924	Approved
0.7488	Intermediate Similarity	NPD4889	Approved
0.7488	Intermediate Similarity	NPD1038	Approved
0.7476	Intermediate Similarity	NPD2334	Discontinued
0.7464	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5482	Discontinued
0.744	Intermediate Similarity	NPD6569	Phase 2
0.7404	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD7222	Phase 2
0.7389	Intermediate Similarity	NPD5559	Phase 2
0.7383	Intermediate Similarity	NPD3397	Phase 2
0.7364	Intermediate Similarity	NPD6961	Discontinued
0.7353	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3386	Phase 2
0.734	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD5513	Phase 2
0.7331	Intermediate Similarity	NPD4558	Phase 2
0.7323	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6968	Phase 2
0.7281	Intermediate Similarity	NPD6969	Phase 2
0.7269	Intermediate Similarity	NPD5530	Phase 1
0.7265	Intermediate Similarity	NPD3763	Approved
0.7261	Intermediate Similarity	NPD7558	Phase 2
0.7261	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4369	Phase 2
0.7255	Intermediate Similarity	NPD4203	Approved
0.7255	Intermediate Similarity	NPD4204	Approved
0.7253	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1392	Approved
0.7235	Intermediate Similarity	NPD7453	Approved
0.7235	Intermediate Similarity	NPD7452	Approved
0.7229	Intermediate Similarity	NPD6963	Approved
0.7229	Intermediate Similarity	NPD6964	Approved
0.721	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3395	Approved
0.7204	Intermediate Similarity	NPD3396	Approved
0.7193	Intermediate Similarity	NPD3259	Approved
0.7167	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7068	Approved
0.7161	Intermediate Similarity	NPD7067	Approved
0.7156	Intermediate Similarity	NPD802	Phase 2
0.715	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7674	Phase 3
0.7149	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7675	Phase 3
0.7149	Intermediate Similarity	NPD7069	Discontinued
0.7143	Intermediate Similarity	NPD4034	Approved
0.7143	Intermediate Similarity	NPD4038	Approved
0.7143	Intermediate Similarity	NPD4035	Approved
0.7143	Intermediate Similarity	NPD4037	Approved
0.7143	Intermediate Similarity	NPD4039	Approved
0.7143	Intermediate Similarity	NPD4033	Approved
0.7143	Intermediate Similarity	NPD31	Approved
0.7143	Intermediate Similarity	NPD32	Approved
0.7143	Intermediate Similarity	NPD4036	Approved
0.7143	Intermediate Similarity	NPD4122	Approved
0.7137	Intermediate Similarity	NPD6306	Phase 2
0.7123	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8091	Phase 3
0.7116	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD3570	Phase 2
0.7095	Intermediate Similarity	NPD3321	Discontinued
0.7093	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1856	Discontinued
0.7089	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3477	Phase 2
0.7085	Intermediate Similarity	NPD5450	Discontinued
0.7085	Intermediate Similarity	NPD4897	Phase 2
0.7081	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1034	Phase 3
0.7081	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8049	Phase 2
0.7075	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3920	Phase 2
0.707	Intermediate Similarity	NPD4548	Discontinued
0.707	Intermediate Similarity	NPD3825	Phase 3
0.7069	Intermediate Similarity	NPD4885	Approved
0.7067	Intermediate Similarity	NPD5948	Phase 2
0.7067	Intermediate Similarity	NPD6568	Discontinued
0.7067	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4952	Phase 3
0.7056	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5612	Discontinued
0.705	Intermediate Similarity	NPD2782	Approved
0.705	Intermediate Similarity	NPD2780	Approved
0.7039	Intermediate Similarity	NPD2601	Approved
0.7039	Intermediate Similarity	NPD2599	Approved
0.7039	Intermediate Similarity	NPD2600	Approved
0.7039	Intermediate Similarity	NPD6494	Phase 2
0.7039	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8246	Approved
0.7037	Intermediate Similarity	NPD8247	Approved
0.7034	Intermediate Similarity	NPD8016	Phase 3
0.7034	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3003	Approved
0.7027	Intermediate Similarity	NPD3939	Suspended
0.7009	Intermediate Similarity	NPD5293	Phase 2
0.7009	Intermediate Similarity	NPD3257	Approved
0.7009	Intermediate Similarity	NPD6550	Discontinued
0.7004	Intermediate Similarity	NPD5930	Phase 3
0.7004	Intermediate Similarity	NPD8479	Phase 2
0.7004	Intermediate Similarity	NPD6856	Discontinued
0.7	Intermediate Similarity	NPD1603	Discontinued
0.6996	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7797	Approved
0.6996	Remote Similarity	NPD7796	Approved
0.6995	Remote Similarity	NPD4551	Phase 2
0.6992	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD3354	Phase 2
0.6991	Remote Similarity	NPD4429	Discontinued
0.6987	Remote Similarity	NPD6230	Discontinued
0.6982	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2781	Approved
0.6977	Remote Similarity	NPD7948	Phase 1
0.6974	Remote Similarity	NPD4923	Phase 1
0.6974	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2189	Approved
0.6968	Remote Similarity	NPD2187	Approved
0.6968	Remote Similarity	NPD7467	Discontinued
0.6966	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4373	Phase 2
0.6963	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4858	Phase 2
0.696	Remote Similarity	NPD7194	Discontinued
0.6957	Remote Similarity	NPD3938	Phase 1
0.6955	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4375	Approved
0.6951	Remote Similarity	NPD5067	Phase 2
0.6951	Remote Similarity	NPD5066	Phase 2
0.6948	Remote Similarity	NPD8284	Discontinued
0.6946	Remote Similarity	NPD6573	Phase 3
0.6946	Remote Similarity	NPD6572	Phase 2
0.6944	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1032	Phase 2
0.694	Remote Similarity	NPD7555	Discontinued
0.6934	Remote Similarity	NPD6281	Approved
0.6927	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7603	Discontinued
0.6923	Remote Similarity	NPD6228	Discontinued
0.6916	Remote Similarity	NPD5632	Approved
0.6912	Remote Similarity	NPD1768	Approved
0.6912	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6999	Discontinued
0.691	Remote Similarity	NPD8512	Phase 3
0.6908	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4876	Phase 3
0.6904	Remote Similarity	NPD4875	Phase 3
0.6904	Remote Similarity	NPD6716	Phase 1
0.6903	Remote Similarity	NPD7112	Discontinued
0.6903	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9705	Discontinued
0.69	Remote Similarity	NPD5507	Approved
0.69	Remote Similarity	NPD112	Approved
0.69	Remote Similarity	NPD5506	Approved
0.69	Remote Similarity	NPD6298	Discontinued
0.6898	Remote Similarity	NPD2952	Discontinued
0.6895	Remote Similarity	NPD6477	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2916	Discontinued
0.6888	Remote Similarity	NPD8100	Phase 3
0.6888	Remote Similarity	NPD5488	Discontinued
0.6886	Remote Similarity	NPD3258	Approved
0.6886	Remote Similarity	NPD6500	Approved
0.6886	Remote Similarity	NPD6501	Approved
0.6885	Remote Similarity	NPD7859	Phase 2
0.6883	Remote Similarity	NPD6246	Approved
0.6881	Remote Similarity	NPD2915	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