NPASS Compound

Structure

CID237740 OpenBabel06191716042D 23 27 0 0 0 0 0 0 0 0999 V2000 5.6036 -1.3644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6028 -0.4463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8090 -1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8072 0.0120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2102 -2.7572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7869 1.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4144 -3.2158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0123 0.9299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0134 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2149 -1.8293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0125 -0.4478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5984 0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4188 -1.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6107 0.0213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4116 -0.4412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6083 -1.8324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8115 -0.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8074 -1.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6183 -2.7561 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2164 0.0118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3919 1.4234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0065 -1.8300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 9 2 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 13 2 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 17 18 1 0 0 0 0 17 20 2 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.07
Volume:	298.672
LogP:	2.279
LogD:	1.88
LogS:	-6.205
# Rotatable Bonds:	0
TPSA:	75.71
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.446
Synthetic Accessibility Score:	2.791
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.995
MDCK Permeability:	1.1654828995233402e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.592
Plasma Protein Binding (PPB):	95.54657745361328%
Volume Distribution (VD):	0.71
Pgp-substrate:	2.2892892360687256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.312
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.239
CYP2C9-substrate:	0.643
CYP2D6-inhibitor:	0.468
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.647
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	1.697
Half-life (T1/2):	0.201

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.927
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.777
Skin Sensitization:	0.642
Carcinogencity:	0.65
Eye Corrosion:	0.004
Eye Irritation:	0.883
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC237740

Natural Product ID:	NPC237740
*Common Name:**	Meridine
IUPAC Name:	n.a.
Synonyms:	Meridine
Standard InCHIKey:	QSJNAFJALFWFMT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H9N3O2/c22-12-6-8-20-17-14(12)15-13-10(5-7-19-16(13)18(17)23)9-3-1-2-4-11(9)21-15/h1-8H,(H,20,22)
SMILES:	Oc1ccnc2c1c1nc3ccccc3c3c1c(C2=O)ncc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL327101
PubChem CID:	72473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO40484	Corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1479383]
NPO40484	Corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17391049]
NPO17574	Cytospora ceratosperma	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20155	Acer argutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22251	Cynanchum caudatum	Species	Apocynaceae	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	22
MIC	23
Others	3

Activity Type	# Activity
Cell Line	13
Individual Protein	2
NON-MOLECULAR	1
Organism	30
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1535	Cell Line	U-87 MG	Homo sapiens	IC50	=	100.0	nM	PMID[521723]
NPT933	Cell Line	U373 MG	Homo sapiens	IC50	=	100.0	nM	PMID[521723]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	8200.0	nM	PMID[521723]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	200.0	nM	PMID[521723]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	70.0	nM	PMID[521723]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	90.0	nM	PMID[521723]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	70.0	nM	PMID[521723]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	80.0	nM	PMID[521723]
NPT2331	Cell Line	A-427	Homo sapiens	IC50	=	200.0	nM	PMID[521723]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	500.0	nM	PMID[521723]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.2	ug.mL-1	PMID[521724]
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.0	ug.mL-1	PMID[521724]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4.5	ug.mL-1	PMID[521724]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	IC50	=	11000.0	nM	PMID[521726]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	IC50	=	11.0	ug.mL-1	PMID[521727]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[521723]
NPT2	Others	Unspecified		IC50	=	50.0	nM	PMID[521723]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.8	ug.mL-1	PMID[521724]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.1	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3.1	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	3.1	ug ml-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	2.5	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.2	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	0.2	ug ml-1	PMID[521725]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	0.8	ug.mL-1	PMID[521725]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MFC	=	6.2	ug ml-1	PMID[521725]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	6.2	ug.mL-1	PMID[521725]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	1.6	ug.mL-1	PMID[521725]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	=	25.0	ug.mL-1	PMID[521725]
NPT3610	Organism	Trichosporon beigelii	Trichosporon beigelii	MIC	>	25.0	ug.mL-1	PMID[521725]
NPT1155	Organism	Sporothrix schenckii	Sporothrix schenckii	MIC	>	25.0	ug.mL-1	PMID[521725]
NPT3683	Organism	Scopulariopsis brevicaulis	Scopulariopsis brevicaulis	MIC	>	25.0	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.62	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.31	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1.2	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	1.0	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	50.0	ug.mL-1	PMID[521725]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	100.0	ug.mL-1	PMID[521725]

☑ 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 NPC237740 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	618
0.1-0.2	3684
0.2-0.3	13140
0.3-0.4	8662
0.4-0.5	12199
0.5-0.6	2158
0.6-0.7	1967
0.7-0.8	255
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8636	High Similarity	NPC328318
0.8636	High Similarity	NPC328596
0.8565	High Similarity	NPC322482
0.8507	High Similarity	NPC317373
0.8458	Intermediate Similarity	NPC327592
0.8221	Intermediate Similarity	NPC317752
0.8173	Intermediate Similarity	NPC318299
0.8125	Intermediate Similarity	NPC157583
0.8084	Intermediate Similarity	NPC216612
0.8019	Intermediate Similarity	NPC469727
0.799	Intermediate Similarity	NPC309845
0.7955	Intermediate Similarity	NPC207686
0.7934	Intermediate Similarity	NPC27041
0.7909	Intermediate Similarity	NPC477112
0.7885	Intermediate Similarity	NPC175602
0.7846	Intermediate Similarity	NPC237188
0.7843	Intermediate Similarity	NPC90229
0.782	Intermediate Similarity	NPC470020
0.7773	Intermediate Similarity	NPC61038
0.7761	Intermediate Similarity	NPC255909
0.775	Intermediate Similarity	NPC118084
0.7749	Intermediate Similarity	NPC97367
0.7731	Intermediate Similarity	NPC264285
0.7729	Intermediate Similarity	NPC178858
0.7707	Intermediate Similarity	NPC128244
0.7696	Intermediate Similarity	NPC329541
0.7664	Intermediate Similarity	NPC110182
0.7662	Intermediate Similarity	NPC91868
0.7662	Intermediate Similarity	NPC63971
0.7661	Intermediate Similarity	NPC276657
0.7642	Intermediate Similarity	NPC477111
0.7639	Intermediate Similarity	NPC477110
0.763	Intermediate Similarity	NPC472065
0.763	Intermediate Similarity	NPC477113
0.7628	Intermediate Similarity	NPC207866
0.7619	Intermediate Similarity	NPC53144
0.7609	Intermediate Similarity	NPC208522
0.7577	Intermediate Similarity	NPC235685
0.7571	Intermediate Similarity	NPC57398
0.7568	Intermediate Similarity	NPC470018
0.7563	Intermediate Similarity	NPC303225
0.7562	Intermediate Similarity	NPC207851
0.7557	Intermediate Similarity	NPC229893
0.7548	Intermediate Similarity	NPC474916
0.7547	Intermediate Similarity	NPC472064
0.7544	Intermediate Similarity	NPC101350
0.7536	Intermediate Similarity	NPC200836
0.7534	Intermediate Similarity	NPC74575
0.7533	Intermediate Similarity	NPC477549
0.7526	Intermediate Similarity	NPC471178
0.7512	Intermediate Similarity	NPC183777
0.7511	Intermediate Similarity	NPC16352
0.75	Intermediate Similarity	NPC472259
0.75	Intermediate Similarity	NPC103119
0.7488	Intermediate Similarity	NPC211813
0.7478	Intermediate Similarity	NPC200553
0.7478	Intermediate Similarity	NPC279189
0.7477	Intermediate Similarity	NPC122436
0.7464	Intermediate Similarity	NPC34837
0.7455	Intermediate Similarity	NPC269270
0.7454	Intermediate Similarity	NPC82370
0.7451	Intermediate Similarity	NPC206186
0.7443	Intermediate Similarity	NPC476041
0.7443	Intermediate Similarity	NPC304926
0.744	Intermediate Similarity	NPC473821
0.7437	Intermediate Similarity	NPC63109
0.7432	Intermediate Similarity	NPC210434
0.7431	Intermediate Similarity	NPC146976
0.743	Intermediate Similarity	NPC270918
0.743	Intermediate Similarity	NPC193238
0.7424	Intermediate Similarity	NPC15801
0.7421	Intermediate Similarity	NPC14686
0.7419	Intermediate Similarity	NPC219087
0.7416	Intermediate Similarity	NPC74153
0.7416	Intermediate Similarity	NPC473814
0.7416	Intermediate Similarity	NPC106824
0.7416	Intermediate Similarity	NPC78767
0.7415	Intermediate Similarity	NPC183805
0.7411	Intermediate Similarity	NPC132631
0.7411	Intermediate Similarity	NPC103687
0.7407	Intermediate Similarity	NPC85273
0.7404	Intermediate Similarity	NPC146724
0.7404	Intermediate Similarity	NPC93390
0.7401	Intermediate Similarity	NPC49547
0.7393	Intermediate Similarity	NPC161801
0.7393	Intermediate Similarity	NPC213308
0.7391	Intermediate Similarity	NPC216550
0.7391	Intermediate Similarity	NPC41679
0.7387	Intermediate Similarity	NPC139763
0.7385	Intermediate Similarity	NPC250448
0.7385	Intermediate Similarity	NPC236668
0.738	Intermediate Similarity	NPC162002
0.7379	Intermediate Similarity	NPC144381
0.7376	Intermediate Similarity	NPC213530
0.7376	Intermediate Similarity	NPC193267
0.7371	Intermediate Similarity	NPC72905
0.7363	Intermediate Similarity	NPC67659
0.7353	Intermediate Similarity	NPC295158
0.7346	Intermediate Similarity	NPC284338
0.7339	Intermediate Similarity	NPC142385
0.7339	Intermediate Similarity	NPC15406
0.7336	Intermediate Similarity	NPC174489
0.7336	Intermediate Similarity	NPC97902
0.7336	Intermediate Similarity	NPC475070
0.7333	Intermediate Similarity	NPC471177
0.7333	Intermediate Similarity	NPC124542
0.7333	Intermediate Similarity	NPC59779
0.7328	Intermediate Similarity	NPC210296
0.7324	Intermediate Similarity	NPC472069
0.7324	Intermediate Similarity	NPC472062
0.7324	Intermediate Similarity	NPC472063
0.7318	Intermediate Similarity	NPC322064
0.7317	Intermediate Similarity	NPC194040
0.7315	Intermediate Similarity	NPC171787
0.7313	Intermediate Similarity	NPC24019
0.7311	Intermediate Similarity	NPC45459
0.7311	Intermediate Similarity	NPC315491
0.7308	Intermediate Similarity	NPC56170
0.7308	Intermediate Similarity	NPC324149
0.7304	Intermediate Similarity	NPC470017
0.7296	Intermediate Similarity	NPC473312
0.7284	Intermediate Similarity	NPC41501
0.7284	Intermediate Similarity	NPC132385
0.7282	Intermediate Similarity	NPC46580
0.7273	Intermediate Similarity	NPC26641
0.7273	Intermediate Similarity	NPC45850
0.7273	Intermediate Similarity	NPC472061
0.7273	Intermediate Similarity	NPC470022
0.7273	Intermediate Similarity	NPC184225
0.7264	Intermediate Similarity	NPC203754
0.7264	Intermediate Similarity	NPC150048
0.7261	Intermediate Similarity	NPC182222
0.7257	Intermediate Similarity	NPC214980
0.7251	Intermediate Similarity	NPC227582
0.725	Intermediate Similarity	NPC53534
0.7248	Intermediate Similarity	NPC5145
0.7246	Intermediate Similarity	NPC218388
0.724	Intermediate Similarity	NPC330009
0.7237	Intermediate Similarity	NPC278525
0.7227	Intermediate Similarity	NPC137353
0.7225	Intermediate Similarity	NPC99666
0.7222	Intermediate Similarity	NPC41717
0.7217	Intermediate Similarity	NPC131887
0.7217	Intermediate Similarity	NPC22481
0.7212	Intermediate Similarity	NPC476818
0.721	Intermediate Similarity	NPC37152
0.721	Intermediate Similarity	NPC477861
0.7205	Intermediate Similarity	NPC260434
0.7203	Intermediate Similarity	NPC469734
0.72	Intermediate Similarity	NPC220851
0.7192	Intermediate Similarity	NPC164340
0.7183	Intermediate Similarity	NPC280714
0.7176	Intermediate Similarity	NPC470500
0.717	Intermediate Similarity	NPC77555
0.717	Intermediate Similarity	NPC156704
0.7169	Intermediate Similarity	NPC167860
0.7169	Intermediate Similarity	NPC123976
0.7162	Intermediate Similarity	NPC469928
0.7157	Intermediate Similarity	NPC271792
0.7156	Intermediate Similarity	NPC210828
0.7156	Intermediate Similarity	NPC86834
0.7156	Intermediate Similarity	NPC60621
0.7156	Intermediate Similarity	NPC39679
0.7155	Intermediate Similarity	NPC183537
0.715	Intermediate Similarity	NPC314940
0.715	Intermediate Similarity	NPC473764
0.715	Intermediate Similarity	NPC252338
0.7149	Intermediate Similarity	NPC258048
0.7143	Intermediate Similarity	NPC74360
0.7143	Intermediate Similarity	NPC270515
0.7136	Intermediate Similarity	NPC23294
0.7129	Intermediate Similarity	NPC83111
0.7124	Intermediate Similarity	NPC182907
0.7124	Intermediate Similarity	NPC189903
0.7123	Intermediate Similarity	NPC472070
0.7119	Intermediate Similarity	NPC74619
0.7112	Intermediate Similarity	NPC90875
0.711	Intermediate Similarity	NPC53344
0.7109	Intermediate Similarity	NPC230403
0.7108	Intermediate Similarity	NPC232340
0.7107	Intermediate Similarity	NPC25899
0.7107	Intermediate Similarity	NPC322644
0.7104	Intermediate Similarity	NPC202605
0.7104	Intermediate Similarity	NPC112206
0.7103	Intermediate Similarity	NPC287437
0.7103	Intermediate Similarity	NPC81535
0.7101	Intermediate Similarity	NPC314002
0.71	Intermediate Similarity	NPC233334
0.7097	Intermediate Similarity	NPC329708
0.7097	Intermediate Similarity	NPC118832
0.7097	Intermediate Similarity	NPC47059
0.7097	Intermediate Similarity	NPC165349
0.7097	Intermediate Similarity	NPC285558
0.7097	Intermediate Similarity	NPC274291
0.7097	Intermediate Similarity	NPC264166
0.7091	Intermediate Similarity	NPC303951
0.7089	Intermediate Similarity	NPC78609
0.7087	Intermediate Similarity	NPC220765
0.7087	Intermediate Similarity	NPC326363
0.7083	Intermediate Similarity	NPC77878

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 NPC237740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	644
0.2-0.3	877
0.3-0.4	1702
0.4-0.5	2770
0.5-0.6	1843
0.6-0.7	873
0.7-0.8	68
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7838	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD7666	Phase 3
0.7559	Intermediate Similarity	NPD7665	Phase 2
0.7479	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4845	Discontinued
0.7429	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6999	Discontinued
0.7426	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD5901	Discontinued
0.7411	Intermediate Similarity	NPD7426	Phase 1
0.7389	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD8091	Phase 3
0.7333	Intermediate Similarity	NPD8289	Discontinued
0.7328	Intermediate Similarity	NPD6790	Phase 1
0.7311	Intermediate Similarity	NPD484	Approved
0.7306	Intermediate Similarity	NPD3243	Approved
0.7302	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD925	Approved
0.7259	Intermediate Similarity	NPD926	Approved
0.7257	Intermediate Similarity	NPD7603	Discontinued
0.7252	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4429	Discontinued
0.7251	Intermediate Similarity	NPD7948	Phase 1
0.724	Intermediate Similarity	NPD3394	Approved
0.724	Intermediate Similarity	NPD7112	Discontinued
0.724	Intermediate Similarity	NPD3389	Approved
0.724	Intermediate Similarity	NPD3393	Approved
0.7238	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2916	Discontinued
0.7207	Intermediate Similarity	NPD4989	Phase 2
0.719	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6242	Discontinued
0.7185	Intermediate Similarity	NPD3809	Discontinued
0.7183	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3330	Phase 1
0.7182	Intermediate Similarity	NPD4852	Phase 2
0.7176	Intermediate Similarity	NPD6987	Phase 1
0.7176	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD3794	Approved
0.7149	Intermediate Similarity	NPD3795	Approved
0.7143	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7001	Phase 3
0.7143	Intermediate Similarity	NPD6159	Phase 2
0.7143	Intermediate Similarity	NPD6569	Phase 2
0.7136	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4886	Phase 2
0.7117	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4948	Discontinued
0.7113	Intermediate Similarity	NPD5482	Discontinued
0.711	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6458	Discontinued
0.7104	Intermediate Similarity	NPD7069	Discontinued
0.71	Intermediate Similarity	NPD2781	Approved
0.7098	Intermediate Similarity	NPD7395	Discontinued
0.7097	Intermediate Similarity	NPD4035	Approved
0.7097	Intermediate Similarity	NPD4037	Approved
0.7097	Intermediate Similarity	NPD4034	Approved
0.7097	Intermediate Similarity	NPD4038	Approved
0.7097	Intermediate Similarity	NPD32	Approved
0.7097	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5426	Phase 3
0.7097	Intermediate Similarity	NPD4036	Approved
0.7097	Intermediate Similarity	NPD31	Approved
0.7097	Intermediate Similarity	NPD4039	Approved
0.7097	Intermediate Similarity	NPD4033	Approved
0.7097	Intermediate Similarity	NPD4122	Approved
0.7095	Intermediate Similarity	NPD2336	Approved
0.7093	Intermediate Similarity	NPD3222	Phase 2
0.7087	Intermediate Similarity	NPD5022	Discontinued
0.7085	Intermediate Similarity	NPD2782	Approved
0.7085	Intermediate Similarity	NPD2780	Approved
0.7064	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3404	Approved
0.7059	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7564	Discontinued
0.704	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD9695	Approved
0.7026	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5100	Phase 3
0.7005	Intermediate Similarity	NPD3931	Approved
0.7005	Intermediate Similarity	NPD3928	Approved
0.7	Intermediate Similarity	NPD6165	Phase 2
0.7	Intermediate Similarity	NPD8430	Approved
0.7	Intermediate Similarity	NPD6376	Discontinued
0.7	Intermediate Similarity	NPD6164	Phase 2
0.6996	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7404	Approved
0.6991	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3315	Phase 3
0.6982	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8356	Approved
0.6974	Remote Similarity	NPD6158	Phase 2
0.6974	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3986	Discontinued
0.6966	Remote Similarity	NPD2757	Phase 2
0.6965	Remote Similarity	NPD424	Approved
0.6965	Remote Similarity	NPD425	Approved
0.6963	Remote Similarity	NPD2307	Discontinued
0.6961	Remote Similarity	NPD9690	Approved
0.6961	Remote Similarity	NPD5065	Approved
0.696	Remote Similarity	NPD5850	Phase 3
0.6955	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6530	Approved
0.6951	Remote Similarity	NPD6531	Approved
0.6948	Remote Similarity	NPD5428	Discontinued
0.6946	Remote Similarity	NPD3962	Phase 2
0.6946	Remote Similarity	NPD3959	Phase 2
0.6935	Remote Similarity	NPD9705	Discontinued
0.6935	Remote Similarity	NPD112	Approved
0.6927	Remote Similarity	NPD6975	Discontinued
0.6927	Remote Similarity	NPD3813	Approved
0.6926	Remote Similarity	NPD3259	Approved
0.692	Remote Similarity	NPD7925	Phase 2
0.692	Remote Similarity	NPD7924	Phase 2
0.6917	Remote Similarity	NPD5488	Discontinued
0.6912	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7568	Phase 1
0.6908	Remote Similarity	NPD9510	Approved
0.6906	Remote Similarity	NPD5416	Discontinued
0.6901	Remote Similarity	NPD8101	Phase 3
0.6901	Remote Similarity	NPD5505	Discontinued
0.6898	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4044	Discontinued
0.689	Remote Similarity	NPD6178	Phase 3
0.6888	Remote Similarity	NPD2882	Phase 1
0.6884	Remote Similarity	NPD5255	Approved
0.6883	Remote Similarity	NPD7923	Phase 2
0.6881	Remote Similarity	NPD6446	Discontinued
0.688	Remote Similarity	NPD7673	Phase 3
0.6867	Remote Similarity	NPD6969	Phase 2
0.6867	Remote Similarity	NPD6968	Phase 2
0.686	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6132	Phase 1
0.6847	Remote Similarity	NPD5862	Discovery
0.6845	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8106	Phase 2
0.6832	Remote Similarity	NPD2720	Phase 1
0.6832	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.683	Remote Similarity	NPD5475	Discontinued
0.6828	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.682	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5513	Phase 2
0.6812	Remote Similarity	NPD3280	Approved
0.6812	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7675	Phase 3
0.681	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7674	Phase 3
0.6809	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD8063	Discontinued
0.6806	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5512	Phase 3
0.6802	Remote Similarity	NPD7222	Phase 2
0.68	Remote Similarity	NPD8093	Discontinued
0.6798	Remote Similarity	NPD3354	Phase 2
0.6798	Remote Similarity	NPD6568	Discontinued
0.679	Remote Similarity	NPD4558	Phase 2
0.6789	Remote Similarity	NPD8396	Approved
0.6789	Remote Similarity	NPD8395	Approved
0.6787	Remote Similarity	NPD8114	Approved
0.6787	Remote Similarity	NPD8115	Approved
0.6786	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5147	Discontinued
0.6783	Remote Similarity	NPD4923	Phase 1
0.6781	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4373	Phase 2
0.678	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4561	Discontinued
0.6777	Remote Similarity	NPD8100	Phase 3
0.6777	Remote Similarity	NPD4889	Approved
0.6773	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD5450	Discontinued
0.677	Remote Similarity	NPD8094	Discontinued
0.6769	Remote Similarity	NPD7168	Phase 3
0.6761	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7944	Discontinued
0.6757	Remote Similarity	NPD7010	Phase 3
0.6757	Remote Similarity	NPD5530	Phase 1
0.6753	Remote Similarity	NPD6209	Approved
0.6753	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4945	Discontinued
0.675	Remote Similarity	NPD7417	Discontinued
0.6748	Remote Similarity	NPD750	Phase 2

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