NPASS Compound

Structure

NPC476120 OpenBabel07101718242D 23 24 0 0 0 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 12 18 2 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.14
Volume:	334.136
LogP:	3.136
LogD:	2.06
LogS:	-4.407
# Rotatable Bonds:	4
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.633
Synthetic Accessibility Score:	3.294
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.709
MDCK Permeability:	2.6912352041108534e-05
Pgp-inhibitor:	0.219
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	88.77625274658203%
Volume Distribution (VD):	0.552
Pgp-substrate:	6.7459025382995605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.781
CYP1A2-substrate:	0.632
CYP2C19-inhibitor:	0.629
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.276
CYP2D6-inhibitor:	0.4
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.844
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	5.05
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.577
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.464
Carcinogencity:	0.489
Eye Corrosion:	0.075
Eye Irritation:	0.371
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC476120

Natural Product ID:	NPC476120
*Common Name:**	Desmosdumotin C
IUPAC Name:	3-hydroxy-5-methoxy-4,6,6-trimethyl-2-[(E)-3-phenylprop-2-enoyl]cyclohexa-2,4-dien-1-one
Synonyms:	Desmosdumotin C
Standard InCHIKey:	ATPDRDNAXQXSQJ-ZHACJKMWSA-N
Standard InCHI:	InChI=1S/C19H20O4/c1-12-16(21)15(17(22)19(2,3)18(12)23-4)14(20)11-10-13-8-6-5-7-9-13/h5-11,21H,1-4H3/b11-10+
SMILES:	CC1=C(C(C(=O)C(=C1O)C(=O)C=CC2=CC=CC=C2)(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL53628
PubChem CID:	6478368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives

*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
NPO33071	desmos spp.	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12729671]

☑ 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
EC50	8
ED50	15
IC50	1
Others	1
Potency	29

Activity Type	# Activity
Cell Line	23
Individual Protein	23
NON-MOLECULAR	2
Organism	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	2.29	ug.mL-1	PMID[492216]
NPT80	Cell Line	Raji	Homo sapiens	Viability	=	70.0	%	PMID[492217]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[492218]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	5.1	ug ml-1	PMID[492218]
NPT309	Cell Line	1A9	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[492218]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[492218]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	11.1	ug ml-1	PMID[492218]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[492218]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[492218]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[492218]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	<	4.0	ug ml-1	PMID[492218]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT309	Cell Line	1A9	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT762	Cell Line	A-431	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT737	Cell Line	HUVEC	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	5623.4	nM	PMID[492220]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	19952.6	nM	PMID[492220]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[492220]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	19952.6	nM	PMID[492220]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	3162.3	nM	PMID[492220]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	22387.2	nM	PMID[492220]
NPT309	Cell Line	1A9	Homo sapiens	ED50	=	11.2	uM	PMID[492221]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	11.8	uM	PMID[492221]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	11.2	uM	PMID[492221]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	35.6	uM	PMID[492221]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	12.8	uM	PMID[492221]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[492220]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[492220]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29081.0	nM	PMID[492220]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[492220]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	16833.6	nM	PMID[492220]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[492220]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[492220]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	2909.3	nM	PMID[492220]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	4610.9	nM	PMID[492220]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[492220]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[492220]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	5623.4	nM	PMID[492220]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	580.5	nM	PMID[492220]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[492220]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[492220]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[492220]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	3.0	ug.mL-1	PMID[492219]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	9.6	uM	PMID[492221]
NPT2	Others	Unspecified		Potency	n.a.	16360.1	nM	PMID[492220]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[492220]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[492220]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[492220]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[492220]
NPT2	Others	Unspecified		Potency	n.a.	22387.2	nM	PMID[492220]

☑ 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 NPC476120 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	181
0.1-0.2	1021
0.2-0.3	3276
0.3-0.4	10053
0.4-0.5	13583
0.5-0.6	12048
0.6-0.7	2387
0.7-0.8	134
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC278228
0.8571	High Similarity	NPC179411
0.8485	Intermediate Similarity	NPC474308
0.8485	Intermediate Similarity	NPC54647
0.8211	Intermediate Similarity	NPC477704
0.8211	Intermediate Similarity	NPC477693
0.8105	Intermediate Similarity	NPC194326
0.8081	Intermediate Similarity	NPC473347
0.8019	Intermediate Similarity	NPC469511
0.8	Intermediate Similarity	NPC471616
0.7921	Intermediate Similarity	NPC240042
0.787	Intermediate Similarity	NPC222905
0.785	Intermediate Similarity	NPC475282
0.7807	Intermediate Similarity	NPC474223
0.7807	Intermediate Similarity	NPC475827
0.7798	Intermediate Similarity	NPC218855
0.7768	Intermediate Similarity	NPC108532
0.7757	Intermediate Similarity	NPC20485
0.7745	Intermediate Similarity	NPC289201
0.7727	Intermediate Similarity	NPC471481
0.7727	Intermediate Similarity	NPC477475
0.7727	Intermediate Similarity	NPC477476
0.7723	Intermediate Similarity	NPC206764
0.7708	Intermediate Similarity	NPC123476
0.767	Intermediate Similarity	NPC329387
0.767	Intermediate Similarity	NPC145052
0.767	Intermediate Similarity	NPC317280
0.7664	Intermediate Similarity	NPC51174
0.7658	Intermediate Similarity	NPC234637
0.7658	Intermediate Similarity	NPC130591
0.7652	Intermediate Similarity	NPC475804
0.7652	Intermediate Similarity	NPC474222
0.7619	Intermediate Similarity	NPC472585
0.7607	Intermediate Similarity	NPC474254
0.7607	Intermediate Similarity	NPC474159
0.76	Intermediate Similarity	NPC476484
0.7593	Intermediate Similarity	NPC470007
0.7593	Intermediate Similarity	NPC47536
0.7589	Intermediate Similarity	NPC469509
0.7573	Intermediate Similarity	NPC103048
0.7547	Intermediate Similarity	NPC68269
0.7523	Intermediate Similarity	NPC40178
0.7522	Intermediate Similarity	NPC23402
0.75	Intermediate Similarity	NPC294458
0.7476	Intermediate Similarity	NPC12695
0.7451	Intermediate Similarity	NPC34243
0.7434	Intermediate Similarity	NPC114144
0.7426	Intermediate Similarity	NPC187725
0.7426	Intermediate Similarity	NPC141607
0.7419	Intermediate Similarity	NPC179726
0.7414	Intermediate Similarity	NPC43435
0.7414	Intermediate Similarity	NPC204784
0.74	Intermediate Similarity	NPC231591
0.7391	Intermediate Similarity	NPC471553
0.7391	Intermediate Similarity	NPC61651
0.7379	Intermediate Similarity	NPC5472
0.7368	Intermediate Similarity	NPC260886
0.7358	Intermediate Similarity	NPC158623
0.735	Intermediate Similarity	NPC476225
0.7347	Intermediate Similarity	NPC53299
0.7339	Intermediate Similarity	NPC477251
0.7327	Intermediate Similarity	NPC110420
0.7327	Intermediate Similarity	NPC303967
0.7327	Intermediate Similarity	NPC67585
0.7321	Intermediate Similarity	NPC470355
0.7321	Intermediate Similarity	NPC477250
0.7304	Intermediate Similarity	NPC28951
0.7304	Intermediate Similarity	NPC325646
0.7297	Intermediate Similarity	NPC88141
0.7281	Intermediate Similarity	NPC285350
0.7273	Intermediate Similarity	NPC328997
0.7273	Intermediate Similarity	NPC294050
0.7264	Intermediate Similarity	NPC130193
0.7264	Intermediate Similarity	NPC476042
0.7245	Intermediate Similarity	NPC44546
0.7241	Intermediate Similarity	NPC268930
0.7213	Intermediate Similarity	NPC146239
0.7207	Intermediate Similarity	NPC281604
0.72	Intermediate Similarity	NPC96625
0.7196	Intermediate Similarity	NPC112552
0.7193	Intermediate Similarity	NPC87069
0.7182	Intermediate Similarity	NPC69332
0.7182	Intermediate Similarity	NPC70843
0.7182	Intermediate Similarity	NPC29989
0.7182	Intermediate Similarity	NPC95178
0.7177	Intermediate Similarity	NPC471832
0.717	Intermediate Similarity	NPC135951
0.717	Intermediate Similarity	NPC201967
0.717	Intermediate Similarity	NPC271475
0.717	Intermediate Similarity	NPC154517
0.7168	Intermediate Similarity	NPC474689
0.7167	Intermediate Similarity	NPC139171
0.7167	Intermediate Similarity	NPC65627
0.7157	Intermediate Similarity	NPC108026
0.7156	Intermediate Similarity	NPC329282
0.7155	Intermediate Similarity	NPC19290
0.7154	Intermediate Similarity	NPC316553
0.7143	Intermediate Similarity	NPC30361
0.713	Intermediate Similarity	NPC215419
0.713	Intermediate Similarity	NPC93181
0.713	Intermediate Similarity	NPC222390
0.713	Intermediate Similarity	NPC244427
0.7117	Intermediate Similarity	NPC470391
0.7117	Intermediate Similarity	NPC156648
0.7115	Intermediate Similarity	NPC181709
0.7107	Intermediate Similarity	NPC325740
0.7103	Intermediate Similarity	NPC80115
0.7091	Intermediate Similarity	NPC321670
0.7083	Intermediate Similarity	NPC151405
0.7083	Intermediate Similarity	NPC139901
0.708	Intermediate Similarity	NPC477247
0.708	Intermediate Similarity	NPC265513
0.708	Intermediate Similarity	NPC116842
0.7075	Intermediate Similarity	NPC133135
0.7075	Intermediate Similarity	NPC156021
0.7075	Intermediate Similarity	NPC477767
0.7075	Intermediate Similarity	NPC251579
0.7064	Intermediate Similarity	NPC247976
0.7064	Intermediate Similarity	NPC274443
0.7064	Intermediate Similarity	NPC474365
0.7064	Intermediate Similarity	NPC301943
0.7054	Intermediate Similarity	NPC317305
0.7054	Intermediate Similarity	NPC224584
0.7049	Intermediate Similarity	NPC478108
0.7049	Intermediate Similarity	NPC295664
0.7043	Intermediate Similarity	NPC196075
0.7043	Intermediate Similarity	NPC474363
0.7043	Intermediate Similarity	NPC326664
0.7041	Intermediate Similarity	NPC475199
0.7041	Intermediate Similarity	NPC283012
0.7041	Intermediate Similarity	NPC99240
0.704	Intermediate Similarity	NPC25736
0.7034	Intermediate Similarity	NPC249435
0.7033	Intermediate Similarity	NPC98880
0.7027	Intermediate Similarity	NPC193640
0.7027	Intermediate Similarity	NPC6984
0.7027	Intermediate Similarity	NPC100767
0.7027	Intermediate Similarity	NPC475905
0.7027	Intermediate Similarity	NPC25385
0.7027	Intermediate Similarity	NPC188677
0.7021	Intermediate Similarity	NPC206800
0.7021	Intermediate Similarity	NPC32203
0.7019	Intermediate Similarity	NPC77273
0.7018	Intermediate Similarity	NPC177576
0.7018	Intermediate Similarity	NPC292834
0.7018	Intermediate Similarity	NPC114682
0.7016	Intermediate Similarity	NPC268607
0.701	Intermediate Similarity	NPC164086
0.7	Intermediate Similarity	NPC99482
0.7	Intermediate Similarity	NPC472981
0.7	Intermediate Similarity	NPC249067
0.6992	Remote Similarity	NPC236405
0.6992	Remote Similarity	NPC478107
0.6992	Remote Similarity	NPC470649
0.6991	Remote Similarity	NPC95172
0.6981	Remote Similarity	NPC469893
0.6979	Remote Similarity	NPC50192
0.6972	Remote Similarity	NPC25458
0.697	Remote Similarity	NPC44830
0.6967	Remote Similarity	NPC85511
0.6967	Remote Similarity	NPC140118
0.6967	Remote Similarity	NPC472704
0.6967	Remote Similarity	NPC12881
0.6964	Remote Similarity	NPC226699
0.696	Remote Similarity	NPC469930
0.6957	Remote Similarity	NPC51698
0.6957	Remote Similarity	NPC477245
0.6957	Remote Similarity	NPC143768
0.6957	Remote Similarity	NPC470253
0.6957	Remote Similarity	NPC477246
0.6957	Remote Similarity	NPC95289
0.6952	Remote Similarity	NPC23453
0.6949	Remote Similarity	NPC222968
0.6949	Remote Similarity	NPC80605
0.6949	Remote Similarity	NPC323440
0.6939	Remote Similarity	NPC71795
0.6937	Remote Similarity	NPC172483
0.6937	Remote Similarity	NPC127676
0.6935	Remote Similarity	NPC81135
0.6935	Remote Similarity	NPC51037
0.693	Remote Similarity	NPC252544
0.693	Remote Similarity	NPC21162
0.693	Remote Similarity	NPC321252
0.693	Remote Similarity	NPC474057
0.693	Remote Similarity	NPC476003
0.693	Remote Similarity	NPC137315
0.6923	Remote Similarity	NPC235421
0.6923	Remote Similarity	NPC311343
0.6923	Remote Similarity	NPC226093
0.6923	Remote Similarity	NPC216387
0.6916	Remote Similarity	NPC469892
0.6916	Remote Similarity	NPC253423
0.6916	Remote Similarity	NPC469890
0.6916	Remote Similarity	NPC469891
0.6916	Remote Similarity	NPC472788
0.6911	Remote Similarity	NPC474766
0.6909	Remote Similarity	NPC91820
0.6909	Remote Similarity	NPC135784
0.6909	Remote Similarity	NPC82426
0.6909	Remote Similarity	NPC202613

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 NPC476120 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	818
0.2-0.3	1367
0.3-0.4	3127
0.4-0.5	2529
0.5-0.6	1004
0.6-0.7	140
0.7-0.8	4
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
0.7714	Intermediate Similarity	NPD6647	Phase 2
0.7624	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5048	Discontinued
0.7364	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5909	Discontinued
0.7193	Intermediate Similarity	NPD6010	Discontinued
0.7103	Intermediate Similarity	NPD2066	Phase 3
0.7021	Intermediate Similarity	NPD9716	Approved
0.7	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1237	Approved
0.697	Remote Similarity	NPD3971	Phase 1
0.693	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1282	Approved
0.6829	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9258	Approved
0.6827	Remote Similarity	NPD9256	Approved
0.6768	Remote Similarity	NPD226	Approved
0.6762	Remote Similarity	NPD7609	Phase 3
0.6759	Remote Similarity	NPD3495	Discontinued
0.6757	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1929	Approved
0.6757	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1930	Approved
0.6748	Remote Similarity	NPD3972	Approved
0.6731	Remote Similarity	NPD5346	Phase 2
0.6731	Remote Similarity	NPD5347	Phase 2
0.6724	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9493	Approved
0.6699	Remote Similarity	NPD4793	Discontinued
0.6699	Remote Similarity	NPD650	Approved
0.6698	Remote Similarity	NPD1088	Approved
0.6698	Remote Similarity	NPD7631	Approved
0.6696	Remote Similarity	NPD2067	Discontinued
0.6695	Remote Similarity	NPD2629	Approved
0.6695	Remote Similarity	NPD5951	Approved
0.6695	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD1932	Approved
0.6639	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1202	Approved
0.6634	Remote Similarity	NPD9491	Approved
0.661	Remote Similarity	NPD1241	Discontinued
0.66	Remote Similarity	NPD942	Approved
0.6583	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD1693	Approved
0.6574	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6049	Phase 2
0.6574	Remote Similarity	NPD2933	Approved
0.6574	Remote Similarity	NPD2934	Approved
0.6571	Remote Similarity	NPD800	Approved
0.6545	Remote Similarity	NPD9495	Approved
0.6545	Remote Similarity	NPD5926	Approved
0.6531	Remote Similarity	NPD9294	Approved
0.6525	Remote Similarity	NPD7094	Approved
0.6525	Remote Similarity	NPD6858	Approved
0.6522	Remote Similarity	NPD9263	Approved
0.6522	Remote Similarity	NPD9264	Approved
0.6522	Remote Similarity	NPD9267	Approved
0.6514	Remote Similarity	NPD2860	Approved
0.6514	Remote Similarity	NPD2859	Approved
0.6509	Remote Similarity	NPD1089	Approved
0.6509	Remote Similarity	NPD1090	Approved
0.6509	Remote Similarity	NPD1086	Approved
0.6509	Remote Similarity	NPD3672	Approved
0.6509	Remote Similarity	NPD3673	Approved
0.6504	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD2932	Approved
0.65	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1238	Approved
0.648	Remote Similarity	NPD4878	Approved
0.648	Remote Similarity	NPD9717	Approved
0.6475	Remote Similarity	NPD9545	Approved
0.6475	Remote Similarity	NPD7009	Phase 2
0.6466	Remote Similarity	NPD2182	Approved
0.6466	Remote Similarity	NPD2329	Discontinued
0.6466	Remote Similarity	NPD74	Approved
0.6466	Remote Similarity	NPD9266	Approved
0.6465	Remote Similarity	NPD227	Approved
0.6465	Remote Similarity	NPD225	Approved
0.6442	Remote Similarity	NPD9257	Approved
0.6442	Remote Similarity	NPD9259	Approved
0.6435	Remote Similarity	NPD3134	Approved
0.6435	Remote Similarity	NPD6685	Approved
0.6422	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD689	Discontinued
0.641	Remote Similarity	NPD1317	Discontinued
0.6406	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD2798	Approved
0.6404	Remote Similarity	NPD164	Approved
0.64	Remote Similarity	NPD6287	Discontinued
0.6393	Remote Similarity	NPD7610	Discontinued
0.6387	Remote Similarity	NPD5277	Phase 2
0.6385	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD1358	Approved
0.6371	Remote Similarity	NPD1778	Approved
0.6371	Remote Similarity	NPD3019	Approved
0.6364	Remote Similarity	NPD1240	Approved
0.6364	Remote Similarity	NPD1989	Approved
0.6364	Remote Similarity	NPD4198	Discontinued
0.6364	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD111	Approved
0.6339	Remote Similarity	NPD3020	Approved
0.6339	Remote Similarity	NPD7798	Approved
0.6336	Remote Similarity	NPD3268	Approved
0.633	Remote Similarity	NPD1066	Discontinued
0.6328	Remote Similarity	NPD1203	Approved
0.632	Remote Similarity	NPD3847	Discontinued
0.632	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5765	Approved
0.6299	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5157	Phase 1
0.6299	Remote Similarity	NPD5159	Phase 2
0.6296	Remote Similarity	NPD1007	Discontinued
0.6296	Remote Similarity	NPD1239	Approved
0.6281	Remote Similarity	NPD9281	Approved
0.6269	Remote Similarity	NPD6651	Approved
0.6269	Remote Similarity	NPD1607	Approved
0.626	Remote Similarity	NPD7008	Discontinued
0.625	Remote Similarity	NPD3225	Approved
0.625	Remote Similarity	NPD2935	Discontinued
0.6241	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1508	Approved
0.6238	Remote Similarity	NPD9490	Approved
0.623	Remote Similarity	NPD3317	Approved
0.6226	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1087	Approved
0.6216	Remote Similarity	NPD1809	Phase 2
0.6212	Remote Similarity	NPD2313	Discontinued
0.6207	Remote Similarity	NPD1018	Approved
0.6204	Remote Similarity	NPD2344	Approved
0.6202	Remote Similarity	NPD1470	Approved
0.6202	Remote Similarity	NPD2797	Approved
0.6198	Remote Similarity	NPD2652	Approved
0.6198	Remote Similarity	NPD2650	Approved
0.619	Remote Similarity	NPD3496	Discontinued
0.619	Remote Similarity	NPD4879	Approved
0.6187	Remote Similarity	NPD4628	Phase 3
0.6187	Remote Similarity	NPD8166	Discontinued
0.6183	Remote Similarity	NPD6832	Phase 2
0.6182	Remote Similarity	NPD845	Approved
0.6179	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD2799	Discontinued
0.6176	Remote Similarity	NPD1510	Phase 2
0.6174	Remote Similarity	NPD9261	Approved
0.6172	Remote Similarity	NPD1755	Approved
0.6161	Remote Similarity	NPD1566	Phase 3
0.6161	Remote Similarity	NPD1564	Approved
0.6161	Remote Similarity	NPD1565	Approved
0.616	Remote Similarity	NPD5585	Approved
0.6154	Remote Similarity	NPD5647	Approved
0.6154	Remote Similarity	NPD6085	Phase 2
0.6154	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD1201	Approved
0.6142	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.614	Remote Similarity	NPD289	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4094	Approved
0.6126	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD1876	Approved
0.6115	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5306	Approved
0.6111	Remote Similarity	NPD5305	Approved
0.6107	Remote Similarity	NPD4208	Discontinued
0.6107	Remote Similarity	NPD9494	Approved
0.6107	Remote Similarity	NPD5736	Approved
0.6094	Remote Similarity	NPD6637	Approved
0.608	Remote Similarity	NPD1894	Discontinued
0.6071	Remote Similarity	NPD1843	Approved
0.6071	Remote Similarity	NPD844	Approved
0.6071	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD4136	Approved
0.6063	Remote Similarity	NPD4106	Approved
0.6063	Remote Similarity	NPD3023	Approved
0.6063	Remote Similarity	NPD3026	Approved
0.6063	Remote Similarity	NPD4135	Approved
0.6058	Remote Similarity	NPD7033	Discontinued
0.6053	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7961	Discontinued
0.6045	Remote Similarity	NPD520	Approved
0.6043	Remote Similarity	NPD1549	Phase 2
0.6036	Remote Similarity	NPD719	Approved
0.6036	Remote Similarity	NPD720	Approved
0.6034	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD9508	Approved
0.6033	Remote Similarity	NPD969	Suspended
0.6033	Remote Similarity	NPD6912	Phase 3
0.6032	Remote Similarity	NPD4105	Approved
0.6032	Remote Similarity	NPD3024	Approved
0.6032	Remote Similarity	NPD3025	Approved
0.6032	Remote Similarity	NPD4102	Approved
0.6028	Remote Similarity	NPD2309	Approved
0.6018	Remote Similarity	NPD4655	Approved
0.6018	Remote Similarity	NPD4657	Approved
0.6017	Remote Similarity	NPD968	Approved
0.6017	Remote Similarity	NPD467	Phase 1
0.6016	Remote Similarity	NPD4806	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data