NPASS Compound

Structure

CID222561 OpenBabel06191716012D 23 26 0 0 0 0 0 0 0 0999 V2000 0.3597 5.1763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5002 4.3484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1804 0.4810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1847 1.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3477 0.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3561 1.9234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6820 -0.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0065 2.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5191 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5234 1.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0015 1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8430 0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8400 3.3809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8355 1.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6844 1.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8349 1.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6740 2.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6713 1.9244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6669 -0.0054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 4.3430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5054 3.3854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.08
Volume:	308.088
LogP:	3.511
LogD:	2.881
LogS:	-6.856
# Rotatable Bonds:	2
TPSA:	64.63
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	2.508
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.915
MDCK Permeability:	2.860172935470473e-05
Pgp-inhibitor:	0.183
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.471

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	93.3580551147461%
Volume Distribution (VD):	0.49
Pgp-substrate:	7.139577865600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.415
CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.627
CYP2C9-substrate:	0.838
CYP2D6-inhibitor:	0.401
CYP2D6-substrate:	0.414
CYP3A4-inhibitor:	0.497
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	1.989
Half-life (T1/2):	0.329

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.833
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.625
Skin Sensitization:	0.868
Carcinogencity:	0.522
Eye Corrosion:	0.012
Eye Irritation:	0.789
Respiratory Toxicity:	0.585

Download Data

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

Natural Product: NPC222561

Natural Product ID:	NPC222561
*Common Name:**	Norcepharadione
IUPAC Name:	n.a.
Synonyms:	Norcepharadione
Standard InCHIKey:	BAGGDUOPTSQTHD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13NO4/c1-22-13-8-11-14-12(19-18(21)16(11)20)7-9-5-3-4-6-10(9)15(14)17(13)23-2/h3-8H,1-2H3,(H,19,21)
SMILES:	COc1cc2c3c(c1OC)c1ccccc1cc3[nH]c(=O)c2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227414
PubChem CID:	189168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines [CHEMONTID:0003326] 4,5-dioxoaporphines

*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
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	stem	n.a.	n.a.	PMID[17081761]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO14376	Stephania cephalantha	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21214233]
NPO14376	Stephania cephalantha	Species	Menispermaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21214233]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129063]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO989	Piper boehmeriifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14376	Stephania cephalantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18509	Fissistigma oldhamii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1076	Cell Line	B-cells	IC50	=	6720.0	nM	PMID[559346]
NPT27	Others	Unspecified	CC50	=	3910.0	nM	PMID[559346]
NPT2	Others	Unspecified	IC50	=	795.0	nM	PMID[559346]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	5.0	n.a.	PMID[559346]
NPT2	Others	Unspecified	Ratio CC50/IC50	=	0.5	n.a.	PMID[559346]

☑ 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 NPC222561 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	458
0.1-0.2	2844
0.2-0.3	10561
0.3-0.4	6293
0.4-0.5	7864
0.5-0.6	12696
0.6-0.7	1826
0.7-0.8	143
0.8-0.85	5
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9632	High Similarity	NPC298449
0.9572	High Similarity	NPC308943
0.9227	High Similarity	NPC55470
0.8724	High Similarity	NPC90185
0.8629	High Similarity	NPC207873
0.8629	High Similarity	NPC100573
0.8316	Intermediate Similarity	NPC5374
0.8247	Intermediate Similarity	NPC254957
0.8173	Intermediate Similarity	NPC71124
0.815	Intermediate Similarity	NPC207971
0.8138	Intermediate Similarity	NPC285941
0.8081	Intermediate Similarity	NPC193906
0.8081	Intermediate Similarity	NPC23080
0.8081	Intermediate Similarity	NPC17677
0.802	Intermediate Similarity	NPC268077
0.801	Intermediate Similarity	NPC190461
0.7887	Intermediate Similarity	NPC249405
0.7871	Intermediate Similarity	NPC471489
0.7846	Intermediate Similarity	NPC33902
0.7846	Intermediate Similarity	NPC276674
0.7843	Intermediate Similarity	NPC38961
0.7766	Intermediate Similarity	NPC320088
0.7757	Intermediate Similarity	NPC210434
0.7727	Intermediate Similarity	NPC312531
0.7706	Intermediate Similarity	NPC24019
0.7692	Intermediate Similarity	NPC85661
0.7685	Intermediate Similarity	NPC212163
0.7656	Intermediate Similarity	NPC25961
0.7653	Intermediate Similarity	NPC179704
0.7644	Intermediate Similarity	NPC46679
0.7619	Intermediate Similarity	NPC61731
0.7619	Intermediate Similarity	NPC186569
0.761	Intermediate Similarity	NPC295676
0.7608	Intermediate Similarity	NPC171882
0.7608	Intermediate Similarity	NPC121510
0.7602	Intermediate Similarity	NPC22481
0.759	Intermediate Similarity	NPC287588
0.7588	Intermediate Similarity	NPC270515
0.755	Intermediate Similarity	NPC474904
0.7547	Intermediate Similarity	NPC227361
0.7547	Intermediate Similarity	NPC124658
0.7534	Intermediate Similarity	NPC154922
0.75	Intermediate Similarity	NPC244606
0.75	Intermediate Similarity	NPC156728
0.75	Intermediate Similarity	NPC182907
0.75	Intermediate Similarity	NPC91234
0.75	Intermediate Similarity	NPC222524
0.75	Intermediate Similarity	NPC283810
0.75	Intermediate Similarity	NPC189903
0.7489	Intermediate Similarity	NPC90875
0.7477	Intermediate Similarity	NPC233334
0.7466	Intermediate Similarity	NPC278525
0.7455	Intermediate Similarity	NPC108342
0.7454	Intermediate Similarity	NPC256422
0.7438	Intermediate Similarity	NPC78284
0.743	Intermediate Similarity	NPC290227
0.7409	Intermediate Similarity	NPC470018
0.7407	Intermediate Similarity	NPC170503
0.7407	Intermediate Similarity	NPC203784
0.7407	Intermediate Similarity	NPC126519
0.7395	Intermediate Similarity	NPC240684
0.7368	Intermediate Similarity	NPC113455
0.7353	Intermediate Similarity	NPC132385
0.7353	Intermediate Similarity	NPC302001
0.7349	Intermediate Similarity	NPC146976
0.7344	Intermediate Similarity	NPC153631
0.7336	Intermediate Similarity	NPC15406
0.7336	Intermediate Similarity	NPC10732
0.7323	Intermediate Similarity	NPC5167
0.7313	Intermediate Similarity	NPC166722
0.7304	Intermediate Similarity	NPC124313
0.7302	Intermediate Similarity	NPC236668
0.7293	Intermediate Similarity	NPC84164
0.7293	Intermediate Similarity	NPC207283
0.729	Intermediate Similarity	NPC220241
0.729	Intermediate Similarity	NPC295479
0.7287	Intermediate Similarity	NPC119669
0.7286	Intermediate Similarity	NPC121400
0.7282	Intermediate Similarity	NPC471604
0.7282	Intermediate Similarity	NPC162653
0.7277	Intermediate Similarity	NPC46990
0.7273	Intermediate Similarity	NPC120239
0.7264	Intermediate Similarity	NPC49184
0.7261	Intermediate Similarity	NPC142385
0.726	Intermediate Similarity	NPC241263
0.7257	Intermediate Similarity	NPC160113
0.7257	Intermediate Similarity	NPC476220
0.7252	Intermediate Similarity	NPC285254
0.7249	Intermediate Similarity	NPC210296
0.7243	Intermediate Similarity	NPC470020
0.7241	Intermediate Similarity	NPC477259
0.7241	Intermediate Similarity	NPC169387
0.7236	Intermediate Similarity	NPC85613
0.7228	Intermediate Similarity	NPC116007
0.722	Intermediate Similarity	NPC74575
0.7206	Intermediate Similarity	NPC208890
0.72	Intermediate Similarity	NPC260118
0.7196	Intermediate Similarity	NPC81733
0.7196	Intermediate Similarity	NPC326316
0.7183	Intermediate Similarity	NPC478075
0.7181	Intermediate Similarity	NPC253675
0.7168	Intermediate Similarity	NPC49547
0.7165	Intermediate Similarity	NPC24954
0.7164	Intermediate Similarity	NPC215747
0.7164	Intermediate Similarity	NPC192939
0.7163	Intermediate Similarity	NPC474366
0.7157	Intermediate Similarity	NPC477998
0.7157	Intermediate Similarity	NPC241055
0.7157	Intermediate Similarity	NPC73280
0.715	Intermediate Similarity	NPC265383
0.7149	Intermediate Similarity	NPC183537
0.7149	Intermediate Similarity	NPC280799
0.7149	Intermediate Similarity	NPC137353
0.7143	Intermediate Similarity	NPC35627
0.7143	Intermediate Similarity	NPC83511
0.7143	Intermediate Similarity	NPC476573
0.7143	Intermediate Similarity	NPC86144
0.7143	Intermediate Similarity	NPC81247
0.7143	Intermediate Similarity	NPC304659
0.7143	Intermediate Similarity	NPC268223
0.7136	Intermediate Similarity	NPC79213
0.713	Intermediate Similarity	NPC220337
0.713	Intermediate Similarity	NPC476258
0.713	Intermediate Similarity	NPC304837
0.7129	Intermediate Similarity	NPC100863
0.7128	Intermediate Similarity	NPC189470
0.7124	Intermediate Similarity	NPC474688
0.7117	Intermediate Similarity	NPC251071
0.7114	Intermediate Similarity	NPC472163
0.7107	Intermediate Similarity	NPC204947
0.71	Intermediate Similarity	NPC475844
0.7098	Intermediate Similarity	NPC476572
0.7098	Intermediate Similarity	NPC93653
0.7097	Intermediate Similarity	NPC159815
0.7094	Intermediate Similarity	NPC28425
0.7091	Intermediate Similarity	NPC195120
0.7091	Intermediate Similarity	NPC182853
0.7089	Intermediate Similarity	NPC313112
0.7089	Intermediate Similarity	NPC301292
0.7089	Intermediate Similarity	NPC475147
0.7085	Intermediate Similarity	NPC303581
0.7085	Intermediate Similarity	NPC67978
0.7085	Intermediate Similarity	NPC94842
0.7083	Intermediate Similarity	NPC325871
0.7083	Intermediate Similarity	NPC99659
0.7079	Intermediate Similarity	NPC27887
0.7079	Intermediate Similarity	NPC311936
0.7077	Intermediate Similarity	NPC299582
0.7076	Intermediate Similarity	NPC77878
0.7075	Intermediate Similarity	NPC288759
0.7074	Intermediate Similarity	NPC470017
0.7072	Intermediate Similarity	NPC7560
0.7069	Intermediate Similarity	NPC72905
0.7067	Intermediate Similarity	NPC469816
0.7067	Intermediate Similarity	NPC469815
0.7056	Intermediate Similarity	NPC41501
0.7056	Intermediate Similarity	NPC261388
0.705	Intermediate Similarity	NPC192135
0.705	Intermediate Similarity	NPC477020
0.705	Intermediate Similarity	NPC66341
0.7044	Intermediate Similarity	NPC119579
0.7044	Intermediate Similarity	NPC298339
0.7041	Intermediate Similarity	NPC476569
0.704	Intermediate Similarity	NPC144452
0.7035	Intermediate Similarity	NPC477562
0.7035	Intermediate Similarity	NPC6152
0.7035	Intermediate Similarity	NPC69712
0.7035	Intermediate Similarity	NPC26240
0.7033	Intermediate Similarity	NPC477258
0.7033	Intermediate Similarity	NPC470023
0.7032	Intermediate Similarity	NPC176113
0.7027	Intermediate Similarity	NPC225279
0.7026	Intermediate Similarity	NPC135006
0.7024	Intermediate Similarity	NPC219170
0.7024	Intermediate Similarity	NPC180253
0.7021	Intermediate Similarity	NPC308006
0.7021	Intermediate Similarity	NPC472836
0.7018	Intermediate Similarity	NPC470481
0.7018	Intermediate Similarity	NPC470482
0.7015	Intermediate Similarity	NPC308267
0.7014	Intermediate Similarity	NPC134702
0.7014	Intermediate Similarity	NPC207239
0.7014	Intermediate Similarity	NPC87560
0.7012	Intermediate Similarity	NPC89549
0.701	Intermediate Similarity	NPC276060
0.7009	Intermediate Similarity	NPC208522
0.7005	Intermediate Similarity	NPC168409
0.7	Intermediate Similarity	NPC38964
0.7	Intermediate Similarity	NPC227683
0.7	Intermediate Similarity	NPC24228
0.6995	Remote Similarity	NPC220961
0.6991	Remote Similarity	NPC13249
0.6978	Remote Similarity	NPC231924
0.6977	Remote Similarity	NPC45190
0.6977	Remote Similarity	NPC300156
0.6972	Remote Similarity	NPC218303
0.6968	Remote Similarity	NPC126556
0.6967	Remote Similarity	NPC234933
0.6963	Remote Similarity	NPC41216
0.6963	Remote Similarity	NPC472839

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 NPC222561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	834
0.2-0.3	921
0.3-0.4	1769
0.4-0.5	2814
0.5-0.6	2003
0.6-0.7	460
0.7-0.8	31
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
0.8265	Intermediate Similarity	NPD5071	Phase 2
0.8086	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8149	Discontinued
0.7816	Intermediate Similarity	NPD4859	Phase 1
0.7794	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5186	Approved
0.7684	Intermediate Similarity	NPD5183	Approved
0.7602	Intermediate Similarity	NPD7922	Phase 1
0.7571	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7279	Phase 2
0.7477	Intermediate Similarity	NPD7278	Phase 2
0.7476	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7225	Discontinued
0.7393	Intermediate Similarity	NPD5950	Discontinued
0.7391	Intermediate Similarity	NPD3289	Phase 3
0.7391	Intermediate Similarity	NPD3290	Approved
0.735	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6321	Discontinued
0.7246	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6618	Phase 2
0.7121	Intermediate Similarity	NPD5919	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8311	Discontinued
0.7098	Intermediate Similarity	NPD5978	Approved
0.7098	Intermediate Similarity	NPD5977	Approved
0.7073	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD8091	Phase 3
0.705	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5928	Phase 1
0.7027	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6250	Discontinued
0.7	Intermediate Similarity	NPD3752	Phase 2
0.6995	Remote Similarity	NPD7626	Approved
0.6995	Remote Similarity	NPD7627	Approved
0.6986	Remote Similarity	NPD4356	Discontinued
0.6985	Remote Similarity	NPD5997	Discontinued
0.698	Remote Similarity	NPD6297	Approved
0.6977	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4846	Phase 2
0.6965	Remote Similarity	NPD5810	Discontinued
0.6961	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4885	Approved
0.6941	Remote Similarity	NPD7301	Phase 3
0.6938	Remote Similarity	NPD7262	Phase 1
0.6931	Remote Similarity	NPD7479	Phase 2
0.693	Remote Similarity	NPD4981	Phase 2
0.6919	Remote Similarity	NPD6457	Approved
0.6916	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7291	Discontinued
0.6901	Remote Similarity	NPD4107	Approved
0.6897	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2968	Approved
0.6878	Remote Similarity	NPD2971	Approved
0.6878	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7708	Approved
0.6866	Remote Similarity	NPD7324	Discontinued
0.6859	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3297	Approved
0.6853	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5025	Approved
0.6845	Remote Similarity	NPD6853	Approved
0.6845	Remote Similarity	NPD6851	Approved
0.6839	Remote Similarity	NPD5086	Approved
0.6837	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5488	Discontinued
0.683	Remote Similarity	NPD2899	Discontinued
0.6829	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1891	Discontinued
0.6823	Remote Similarity	NPD6031	Approved
0.6823	Remote Similarity	NPD6030	Approved
0.6822	Remote Similarity	NPD6612	Phase 2
0.6816	Remote Similarity	NPD6719	Approved
0.6814	Remote Similarity	NPD5445	Approved
0.6812	Remote Similarity	NPD7654	Discontinued
0.6808	Remote Similarity	NPD5197	Approved
0.6808	Remote Similarity	NPD5196	Approved
0.6808	Remote Similarity	NPD4668	Phase 2
0.6808	Remote Similarity	NPD5194	Approved
0.6804	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3437	Discontinued
0.6791	Remote Similarity	NPD4482	Phase 3
0.6782	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5466	Approved
0.6779	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5610	Approved
0.6777	Remote Similarity	NPD6181	Discontinued
0.6767	Remote Similarity	NPD6625	Approved
0.6767	Remote Similarity	NPD6723	Discontinued
0.6765	Remote Similarity	NPD3920	Phase 2
0.6761	Remote Similarity	NPD7803	Approved
0.6761	Remote Similarity	NPD5564	Approved
0.6759	Remote Similarity	NPD3057	Approved
0.675	Remote Similarity	NPD2821	Approved
0.6749	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6790	Phase 1
0.6736	Remote Similarity	NPD3640	Phase 3
0.6736	Remote Similarity	NPD3639	Approved
0.6736	Remote Similarity	NPD3641	Approved
0.6734	Remote Similarity	NPD5430	Discontinued
0.673	Remote Similarity	NPD7570	Approved
0.673	Remote Similarity	NPD7569	Approved
0.6719	Remote Similarity	NPD4584	Approved
0.6714	Remote Similarity	NPD3964	Approved
0.6712	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3912	Discontinued
0.6709	Remote Similarity	NPD6716	Phase 1
0.67	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5637	Discontinued
0.6697	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3298	Approved
0.6684	Remote Similarity	NPD7110	Phase 1
0.6684	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD1309	Phase 2
0.6683	Remote Similarity	NPD4083	Discontinued
0.6683	Remote Similarity	NPD1307	Phase 2
0.6682	Remote Similarity	NPD3533	Approved
0.6682	Remote Similarity	NPD2974	Approved
0.6682	Remote Similarity	NPD2972	Approved
0.6682	Remote Similarity	NPD2490	Approved
0.6682	Remote Similarity	NPD2491	Approved
0.6682	Remote Similarity	NPD2488	Approved
0.6682	Remote Similarity	NPD2975	Approved
0.6682	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3448	Approved
0.6682	Remote Similarity	NPD2973	Approved
0.6681	Remote Similarity	NPD7048	Phase 3
0.6667	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7693	Approved
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1945	Phase 1
0.6667	Remote Similarity	NPD5457	Discontinued
0.6651	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4420	Approved
0.665	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4952	Phase 3
0.6637	Remote Similarity	NPD7395	Discontinued
0.6636	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6238	Discontinued
0.6636	Remote Similarity	NPD7584	Approved
0.6623	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5860	Discontinued
0.6621	Remote Similarity	NPD4465	Phase 2
0.6621	Remote Similarity	NPD4467	Phase 2
0.662	Remote Similarity	NPD6526	Approved
0.662	Remote Similarity	NPD4539	Phase 1
0.6618	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4505	Phase 1
0.6608	Remote Similarity	NPD3763	Approved
0.6607	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7316	Discontinued
0.6605	Remote Similarity	NPD6162	Approved
0.6605	Remote Similarity	NPD6161	Approved
0.6601	Remote Similarity	NPD3776	Discontinued
0.6594	Remote Similarity	NPD6997	Phase 2
0.6594	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD683	Approved
0.659	Remote Similarity	NPD4580	Approved
0.6588	Remote Similarity	NPD3349	Phase 2
0.6587	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7177	Discontinued
0.6583	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3229	Phase 2
0.6582	Remote Similarity	NPD824	Approved
0.6578	Remote Similarity	NPD3257	Approved
0.6573	Remote Similarity	NPD5937	Approved
0.6566	Remote Similarity	NPD7298	Approved
0.6564	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3301	Approved
0.6561	Remote Similarity	NPD5429	Discontinued
0.656	Remote Similarity	NPD3450	Approved
0.656	Remote Similarity	NPD3452	Approved
0.656	Remote Similarity	NPD2493	Approved
0.656	Remote Similarity	NPD2494	Approved
0.6559	Remote Similarity	NPD7956	Approved
0.6559	Remote Similarity	NPD7955	Approved
0.6555	Remote Similarity	NPD7546	Discontinued
0.6553	Remote Similarity	NPD5313	Approved
0.6553	Remote Similarity	NPD4373	Phase 2
0.6553	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD5312	Approved
0.6552	Remote Similarity	NPD4166	Phase 2
0.6545	Remote Similarity	NPD4040	Phase 1
0.6545	Remote Similarity	NPD6644	Discontinued
0.6544	Remote Similarity	NPD6874	Approved
0.6537	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7545	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5496	Approved
0.6535	Remote Similarity	NPD1559	Discontinued
0.6535	Remote Similarity	NPD6037	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