NPASS Compound

Structure

CID34243 OpenBabel06191715362D 22 24 0 0 0 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -1.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.07
Volume:	303.011
LogP:	3.124
LogD:	2.732
LogS:	-4.088
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	2.06
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.686
MDCK Permeability:	1.1940133845200762e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	101.22252655029297%
Volume Distribution (VD):	0.341
Pgp-substrate:	0.5681193470954895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.795
CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.116
CYP2C9-inhibitor:	0.604
CYP2C9-substrate:	0.75
CYP2D6-inhibitor:	0.231
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	0.314
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.278
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.546
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC34243

Natural Product ID:	NPC34243
*Common Name:**	2,5-Dihydroxy-3,6-Diphenyl-1,4-Benzoquinone
IUPAC Name:	2,5-dihydroxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	HZKFHDXTSAYOSN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O4/c19-15-13(11-7-3-1-4-8-11)16(20)18(22)14(17(15)21)12-9-5-2-6-10-12/h1-10,19,22H
SMILES:	c1ccc(cc1)C1=C(C(=O)C(=C(C1=O)O)c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480678
PubChem CID:	11056
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003–2005	DOI[10.1016/j.jfca.2006.05.007]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO12163	Pteraster pulvillus	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608872]
NPO3162	Bituminaria morisiana	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12943781]
NPO33054	stilbella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[15787429]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	alkaloids	n.a.	PMID[19757855]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO12471	Rhodotorula mucilaginosa	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23490182]
NPO342	Dichotomomyces cejpii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24471526]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3162	Bituminaria morisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO3162	Bituminaria morisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12719.1	Iris spuria subsp. carthaliniae	Subspecies	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3097	Pachybolus brachysternus	Species	Pachybolidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2061	Schizymenia dubyi	Species	Schizymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12719.1	Iris spuria subsp. carthaliniae	Subspecies	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12353	Trichia fragilis	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3162	Bituminaria morisiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2620	Thelypteris oligophlebia	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11251	Trianthema pentandra	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13464	Dendrolimus pini	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12471	Rhodotorula mucilaginosa	Species	Sporidiobolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO314	Bulbophyllum kwangtungense	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10237	Polyporus rutilans	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12163	Pteraster pulvillus	Species	Pterasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3235	Sticta colensoi	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14459	Canthium multiflorum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9905	Paraquilegia microphylla	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO342	Dichotomomyces cejpii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2269	Panulirus cygnus	Species	Palinuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2138	Erythroxylum cuneatum	Species	Erythroxylaceae	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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	>	50000.0	nM	PMID[449868]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	17.0	%	PMID[449868]

☑ 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 NPC34243 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	209
0.1-0.2	1170
0.2-0.3	3484
0.3-0.4	11834
0.4-0.5	12990
0.5-0.6	10755
0.6-0.7	1962
0.7-0.8	267
0.8-0.85	20
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC103048
0.8925	High Similarity	NPC12695
0.8778	High Similarity	NPC477693
0.8778	High Similarity	NPC477704
0.8586	High Similarity	NPC134120
0.8529	High Similarity	NPC21162
0.8444	Intermediate Similarity	NPC95965
0.8438	Intermediate Similarity	NPC156021
0.8298	Intermediate Similarity	NPC110704
0.8298	Intermediate Similarity	NPC476484
0.8283	Intermediate Similarity	NPC244427
0.8283	Intermediate Similarity	NPC222390
0.8269	Intermediate Similarity	NPC186128
0.8247	Intermediate Similarity	NPC289201
0.8242	Intermediate Similarity	NPC123476
0.82	Intermediate Similarity	NPC274443
0.8163	Intermediate Similarity	NPC145052
0.8119	Intermediate Similarity	NPC249067
0.8105	Intermediate Similarity	NPC141607
0.8105	Intermediate Similarity	NPC187725
0.8081	Intermediate Similarity	NPC54647
0.8061	Intermediate Similarity	NPC240042
0.8039	Intermediate Similarity	NPC172483
0.8022	Intermediate Similarity	NPC285773
0.802	Intermediate Similarity	NPC329556
0.7978	Intermediate Similarity	NPC139901
0.7978	Intermediate Similarity	NPC151405
0.7961	Intermediate Similarity	NPC70843
0.7961	Intermediate Similarity	NPC100767
0.7925	Intermediate Similarity	NPC292834
0.7909	Intermediate Similarity	NPC318173
0.79	Intermediate Similarity	NPC476042
0.7889	Intermediate Similarity	NPC127343
0.7889	Intermediate Similarity	NPC95868
0.7889	Intermediate Similarity	NPC71664
0.7885	Intermediate Similarity	NPC156648
0.7885	Intermediate Similarity	NPC203732
0.7872	Intermediate Similarity	NPC194326
0.7857	Intermediate Similarity	NPC206764
0.785	Intermediate Similarity	NPC143768
0.7826	Intermediate Similarity	NPC44830
0.7826	Intermediate Similarity	NPC273758
0.7822	Intermediate Similarity	NPC112552
0.7812	Intermediate Similarity	NPC303967
0.7812	Intermediate Similarity	NPC110420
0.7812	Intermediate Similarity	NPC67585
0.7802	Intermediate Similarity	NPC273033
0.7802	Intermediate Similarity	NPC12936
0.7788	Intermediate Similarity	NPC69332
0.7788	Intermediate Similarity	NPC29989
0.7788	Intermediate Similarity	NPC95178
0.7778	Intermediate Similarity	NPC272260
0.7767	Intermediate Similarity	NPC329282
0.7757	Intermediate Similarity	NPC218855
0.7753	Intermediate Similarity	NPC9796
0.7745	Intermediate Similarity	NPC320891
0.7736	Intermediate Similarity	NPC88141
0.7732	Intermediate Similarity	NPC317645
0.7727	Intermediate Similarity	NPC469843
0.7714	Intermediate Similarity	NPC141523
0.7708	Intermediate Similarity	NPC9822
0.7708	Intermediate Similarity	NPC231591
0.7706	Intermediate Similarity	NPC474408
0.7699	Intermediate Similarity	NPC294361
0.7699	Intermediate Similarity	NPC236520
0.7685	Intermediate Similarity	NPC471481
0.7684	Intermediate Similarity	NPC322387
0.7684	Intermediate Similarity	NPC69057
0.7677	Intermediate Similarity	NPC172925
0.767	Intermediate Similarity	NPC247976
0.7658	Intermediate Similarity	NPC222968
0.7658	Intermediate Similarity	NPC80605
0.7658	Intermediate Similarity	NPC323440
0.7642	Intermediate Similarity	NPC281604
0.7624	Intermediate Similarity	NPC317280
0.7624	Intermediate Similarity	NPC329387
0.7619	Intermediate Similarity	NPC188677
0.7615	Intermediate Similarity	NPC234637
0.7615	Intermediate Similarity	NPC130591
0.7615	Intermediate Similarity	NPC67377
0.7604	Intermediate Similarity	NPC329064
0.7596	Intermediate Similarity	NPC8931
0.7596	Intermediate Similarity	NPC120693
0.7596	Intermediate Similarity	NPC269644
0.7596	Intermediate Similarity	NPC261573
0.7582	Intermediate Similarity	NPC300205
0.7576	Intermediate Similarity	NPC261181
0.7556	Intermediate Similarity	NPC245966
0.7556	Intermediate Similarity	NPC179726
0.7549	Intermediate Similarity	NPC474308
0.7547	Intermediate Similarity	NPC470007
0.7526	Intermediate Similarity	NPC418308
0.7525	Intermediate Similarity	NPC270654
0.7524	Intermediate Similarity	NPC13495
0.75	Intermediate Similarity	NPC255676
0.75	Intermediate Similarity	NPC135784
0.75	Intermediate Similarity	NPC164086
0.75	Intermediate Similarity	NPC318067
0.75	Intermediate Similarity	NPC285679
0.75	Intermediate Similarity	NPC116842
0.7477	Intermediate Similarity	NPC192577
0.7477	Intermediate Similarity	NPC17525
0.7473	Intermediate Similarity	NPC36342
0.7473	Intermediate Similarity	NPC285470
0.7473	Intermediate Similarity	NPC2785
0.7455	Intermediate Similarity	NPC326664
0.7455	Intermediate Similarity	NPC294458
0.7451	Intermediate Similarity	NPC175852
0.7451	Intermediate Similarity	NPC210529
0.7451	Intermediate Similarity	NPC476120
0.7451	Intermediate Similarity	NPC160548
0.7451	Intermediate Similarity	NPC179411
0.7449	Intermediate Similarity	NPC19256
0.7449	Intermediate Similarity	NPC274455
0.7449	Intermediate Similarity	NPC86670
0.7449	Intermediate Similarity	NPC70940
0.7447	Intermediate Similarity	NPC288903
0.7447	Intermediate Similarity	NPC215008
0.7436	Intermediate Similarity	NPC295664
0.7431	Intermediate Similarity	NPC474689
0.7423	Intermediate Similarity	NPC267262
0.7411	Intermediate Similarity	NPC28951
0.7411	Intermediate Similarity	NPC325646
0.7404	Intermediate Similarity	NPC25458
0.7387	Intermediate Similarity	NPC285350
0.7387	Intermediate Similarity	NPC93181
0.7386	Intermediate Similarity	NPC74458
0.7383	Intermediate Similarity	NPC211439
0.7383	Intermediate Similarity	NPC470391
0.7379	Intermediate Similarity	NPC280869
0.7368	Intermediate Similarity	NPC204784
0.7364	Intermediate Similarity	NPC470253
0.7358	Intermediate Similarity	NPC474307
0.7358	Intermediate Similarity	NPC105899
0.7358	Intermediate Similarity	NPC471186
0.7353	Intermediate Similarity	NPC278228
0.7353	Intermediate Similarity	NPC472788
0.7353	Intermediate Similarity	NPC477767
0.735	Intermediate Similarity	NPC328107
0.7345	Intermediate Similarity	NPC471553
0.734	Intermediate Similarity	NPC121478
0.734	Intermediate Similarity	NPC73637
0.7339	Intermediate Similarity	NPC291799
0.7339	Intermediate Similarity	NPC265513
0.7339	Intermediate Similarity	NPC137315
0.7333	Intermediate Similarity	NPC68269
0.7327	Intermediate Similarity	NPC473347
0.7327	Intermediate Similarity	NPC472880
0.7321	Intermediate Similarity	NPC322197
0.7321	Intermediate Similarity	NPC471616
0.7321	Intermediate Similarity	NPC23402
0.732	Intermediate Similarity	NPC43945
0.7315	Intermediate Similarity	NPC475282
0.7312	Intermediate Similarity	NPC190567
0.7312	Intermediate Similarity	NPC184030
0.7312	Intermediate Similarity	NPC164449
0.7312	Intermediate Similarity	NPC477703
0.7308	Intermediate Similarity	NPC158623
0.7297	Intermediate Similarity	NPC471721
0.7297	Intermediate Similarity	NPC196673
0.7292	Intermediate Similarity	NPC294134
0.7288	Intermediate Similarity	NPC164014
0.7282	Intermediate Similarity	NPC229242
0.7282	Intermediate Similarity	NPC49994
0.7282	Intermediate Similarity	NPC260000
0.7273	Intermediate Similarity	NPC62765
0.7273	Intermediate Similarity	NPC268388
0.7273	Intermediate Similarity	NPC177576
0.7273	Intermediate Similarity	NPC108026
0.7273	Intermediate Similarity	NPC471189
0.7273	Intermediate Similarity	NPC212718
0.7257	Intermediate Similarity	NPC299252
0.7257	Intermediate Similarity	NPC128249
0.7257	Intermediate Similarity	NPC61062
0.7257	Intermediate Similarity	NPC277394
0.7257	Intermediate Similarity	NPC108532
0.7257	Intermediate Similarity	NPC158157
0.7255	Intermediate Similarity	NPC61944
0.725	Intermediate Similarity	NPC156539
0.7245	Intermediate Similarity	NPC157778
0.7238	Intermediate Similarity	NPC284477
0.7234	Intermediate Similarity	NPC145053
0.7234	Intermediate Similarity	NPC73978
0.7228	Intermediate Similarity	NPC289883
0.7222	Intermediate Similarity	NPC34715
0.7222	Intermediate Similarity	NPC20485
0.7222	Intermediate Similarity	NPC226699
0.7217	Intermediate Similarity	NPC476645
0.7212	Intermediate Similarity	NPC217621
0.7212	Intermediate Similarity	NPC130193
0.7207	Intermediate Similarity	NPC477475
0.7207	Intermediate Similarity	NPC93287
0.7207	Intermediate Similarity	NPC477476
0.72	Intermediate Similarity	NPC284475
0.7184	Intermediate Similarity	NPC239185
0.7184	Intermediate Similarity	NPC253423
0.7182	Intermediate Similarity	NPC321252
0.7182	Intermediate Similarity	NPC474057
0.7182	Intermediate Similarity	NPC252544
0.7182	Intermediate Similarity	NPC222905

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 NPC34243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	923
0.2-0.3	1171
0.3-0.4	3020
0.4-0.5	2489
0.5-0.6	1077
0.6-0.7	230
0.7-0.8	45
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD1237	Approved
0.8081	Intermediate Similarity	NPD2066	Phase 3
0.8022	Intermediate Similarity	NPD9491	Approved
0.802	Intermediate Similarity	NPD1930	Approved
0.802	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD1929	Approved
0.7921	Intermediate Similarity	NPD1932	Approved
0.7917	Intermediate Similarity	NPD1239	Approved
0.7889	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD942	Approved
0.7802	Intermediate Similarity	NPD226	Approved
0.7677	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5909	Discontinued
0.7582	Intermediate Similarity	NPD9490	Approved
0.7576	Intermediate Similarity	NPD1202	Approved
0.7544	Intermediate Similarity	NPD4879	Approved
0.7526	Intermediate Similarity	NPD800	Approved
0.7525	Intermediate Similarity	NPD1566	Phase 3
0.7525	Intermediate Similarity	NPD1565	Approved
0.7525	Intermediate Similarity	NPD1564	Approved
0.75	Intermediate Similarity	NPD1693	Approved
0.75	Intermediate Similarity	NPD4793	Discontinued
0.7477	Intermediate Similarity	NPD2329	Discontinued
0.7473	Intermediate Similarity	NPD225	Approved
0.7473	Intermediate Similarity	NPD227	Approved
0.7451	Intermediate Similarity	NPD9495	Approved
0.7449	Intermediate Similarity	NPD1086	Approved
0.7449	Intermediate Similarity	NPD1090	Approved
0.7449	Intermediate Similarity	NPD1089	Approved
0.7426	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5346	Phase 2
0.7347	Intermediate Similarity	NPD5347	Phase 2
0.7339	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD650	Approved
0.7315	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD1088	Approved
0.7273	Intermediate Similarity	NPD9256	Approved
0.7273	Intermediate Similarity	NPD9258	Approved
0.7255	Intermediate Similarity	NPD1989	Approved
0.7228	Intermediate Similarity	NPD1563	Approved
0.7212	Intermediate Similarity	NPD7798	Approved
0.72	Intermediate Similarity	NPD7609	Phase 3
0.7184	Intermediate Similarity	NPD3495	Discontinued
0.7143	Intermediate Similarity	NPD1087	Approved
0.7129	Intermediate Similarity	NPD1508	Approved
0.7129	Intermediate Similarity	NPD7631	Approved
0.7119	Intermediate Similarity	NPD4878	Approved
0.708	Intermediate Similarity	NPD5951	Approved
0.708	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1238	Approved
0.7041	Intermediate Similarity	NPD9259	Approved
0.7041	Intermediate Similarity	NPD9257	Approved
0.7009	Intermediate Similarity	NPD6647	Phase 2
0.6983	Remote Similarity	NPD7009	Phase 2
0.6981	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD2067	Discontinued
0.6937	Remote Similarity	NPD1317	Discontinued
0.693	Remote Similarity	NPD2629	Approved
0.6923	Remote Similarity	NPD1843	Approved
0.6897	Remote Similarity	NPD7610	Discontinued
0.6891	Remote Similarity	NPD1201	Approved
0.6881	Remote Similarity	NPD5048	Discontinued
0.6864	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2345	Approved
0.6827	Remote Similarity	NPD2934	Approved
0.6827	Remote Similarity	NPD2933	Approved
0.681	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1470	Approved
0.68	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1246	Approved
0.678	Remote Similarity	NPD4105	Approved
0.678	Remote Similarity	NPD4102	Approved
0.6777	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5159	Phase 2
0.6777	Remote Similarity	NPD5157	Phase 1
0.6765	Remote Similarity	NPD3673	Approved
0.6765	Remote Similarity	NPD3672	Approved
0.6762	Remote Similarity	NPD2859	Approved
0.6762	Remote Similarity	NPD2860	Approved
0.6754	Remote Similarity	NPD7094	Approved
0.6754	Remote Similarity	NPD6858	Approved
0.6735	Remote Similarity	NPD3971	Phase 1
0.6729	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2932	Approved
0.6698	Remote Similarity	NPD9566	Approved
0.6698	Remote Similarity	NPD1875	Phase 1
0.6697	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6636	Remote Similarity	NPD253	Approved
0.6636	Remote Similarity	NPD164	Approved
0.6613	Remote Similarity	NPD4980	Approved
0.6613	Remote Similarity	NPD2798	Approved
0.6613	Remote Similarity	NPD2788	Approved
0.6607	Remote Similarity	NPD9263	Approved
0.6607	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD9264	Approved
0.6607	Remote Similarity	NPD9267	Approved
0.6596	Remote Similarity	NPD9716	Approved
0.6583	Remote Similarity	NPD5305	Approved
0.6583	Remote Similarity	NPD3019	Approved
0.6583	Remote Similarity	NPD5306	Approved
0.6583	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1018	Approved
0.6574	Remote Similarity	NPD3020	Approved
0.6555	Remote Similarity	NPD1894	Discontinued
0.6549	Remote Similarity	NPD9266	Approved
0.6549	Remote Similarity	NPD2182	Approved
0.6549	Remote Similarity	NPD74	Approved
0.6545	Remote Similarity	NPD5765	Approved
0.6542	Remote Similarity	NPD4657	Approved
0.6542	Remote Similarity	NPD4655	Approved
0.6535	Remote Similarity	NPD3268	Approved
0.6535	Remote Similarity	NPD3764	Approved
0.6532	Remote Similarity	NPD2797	Approved
0.6529	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3772	Phase 3
0.6509	Remote Similarity	NPD9260	Approved
0.65	Remote Similarity	NPD6993	Approved
0.65	Remote Similarity	NPD1245	Approved
0.65	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6994	Approved
0.6491	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7961	Discontinued
0.648	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD4807	Approved
0.6475	Remote Similarity	NPD4806	Approved
0.6475	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6287	Discontinued
0.6471	Remote Similarity	NPD2347	Approved
0.6466	Remote Similarity	NPD5277	Phase 2
0.6458	Remote Similarity	NPD9294	Approved
0.6457	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6027	Approved
0.6455	Remote Similarity	NPD6024	Approved
0.6452	Remote Similarity	NPD1574	Approved
0.6441	Remote Similarity	NPD4198	Discontinued
0.6435	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3643	Approved
0.6435	Remote Similarity	NPD3642	Approved
0.6435	Remote Similarity	NPD3644	Approved
0.6429	Remote Similarity	NPD4695	Discontinued
0.6423	Remote Similarity	NPD1481	Phase 2
0.6423	Remote Similarity	NPD3972	Approved
0.6417	Remote Similarity	NPD3798	Phase 3
0.6415	Remote Similarity	NPD1066	Discontinued
0.641	Remote Similarity	NPD2650	Approved
0.641	Remote Similarity	NPD2652	Approved
0.6406	Remote Similarity	NPD6798	Discontinued
0.64	Remote Similarity	NPD1164	Approved
0.64	Remote Similarity	NPD1593	Approved
0.64	Remote Similarity	NPD1203	Approved
0.64	Remote Similarity	NPD3266	Approved
0.64	Remote Similarity	NPD3267	Approved
0.6396	Remote Similarity	NPD9261	Approved
0.6393	Remote Similarity	NPD3023	Approved
0.6393	Remote Similarity	NPD3026	Approved
0.6387	Remote Similarity	NPD3797	Approved
0.6387	Remote Similarity	NPD4576	Approved
0.6387	Remote Similarity	NPD4574	Approved
0.6387	Remote Similarity	NPD9493	Approved
0.6379	Remote Similarity	NPD9508	Approved
0.6378	Remote Similarity	NPD5201	Approved
0.6378	Remote Similarity	NPD5203	Approved
0.6378	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4617	Approved
0.6378	Remote Similarity	NPD4620	Approved
0.6372	Remote Similarity	NPD6685	Approved
0.6372	Remote Similarity	NPD467	Phase 1
0.6364	Remote Similarity	NPD3028	Approved
0.6364	Remote Similarity	NPD3024	Approved
0.6364	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3025	Approved
0.6357	Remote Similarity	NPD6233	Phase 2
0.6356	Remote Similarity	NPD9281	Approved
0.6348	Remote Similarity	NPD664	Approved
0.6348	Remote Similarity	NPD5278	Discontinued
0.6341	Remote Similarity	NPD1535	Discovery
0.633	Remote Similarity	NPD5926	Approved
0.6328	Remote Similarity	NPD7008	Discontinued
0.632	Remote Similarity	NPD3225	Approved
0.632	Remote Similarity	NPD1876	Approved
0.632	Remote Similarity	NPD1888	Phase 1
0.6311	Remote Similarity	NPD1282	Approved
0.6311	Remote Similarity	NPD9538	Approved
0.6308	Remote Similarity	NPD4453	Approved
0.6308	Remote Similarity	NPD4452	Approved
0.6308	Remote Similarity	NPD943	Approved
0.6308	Remote Similarity	NPD4445	Approved
0.6306	Remote Similarity	NPD2193	Phase 2
0.6306	Remote Similarity	NPD2171	Approved
0.6306	Remote Similarity	NPD2648	Phase 3
0.6299	Remote Similarity	NPD5204	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