NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.08
Volume:	191.916
LogP:	4.04
LogD:	3.466
LogS:	-4.996
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	1.545
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.458
MDCK Permeability:	2.9236649425001815e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.713
Plasma Protein Binding (PPB):	96.87873840332031%
Volume Distribution (VD):	1.177
Pgp-substrate:	2.419436454772949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.887
CYP1A2-substrate:	0.56
CYP2C19-inhibitor:	0.782
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.684
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.44

ADMET: Excretion

Clearance (CL):	9.716
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.721
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.124
Skin Sensitization:	0.169
Carcinogencity:	0.768
Eye Corrosion:	0.036
Eye Irritation:	0.988
Respiratory Toxicity:	0.037

Download Data

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

Natural Product: NPC263385

Natural Product ID:	NPC263385
*Common Name:**	Fluorene
IUPAC Name:	9H-fluorene
Synonyms:	9H-Fluorene; Fluorene
Standard InCHIKey:	NIHNNTQXNPWCJQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H10/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)12/h1-8H,9H2
SMILES:	c1ccc2c(c1)Cc1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL16236
PubChem CID:	6853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
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]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
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]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
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]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18046	Mosla chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	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
NPO163	NPC263385	Raw, Dried	n.a.	0.00425	0.00359	0.00491	ug/kg of DW	DOI[10.1016/0045-6535(91)90110-Y]

☑ 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	1
IC50	1
Others	4
Potency	8

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Organism	1
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[463153]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	5.6	nM	PMID[463153]
NPT5554	Individual Protein	Botulinum neurotoxin type E	Clostridium botulinum	Inhibition	=	17.3	%	PMID[463154]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[463155]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT35	Others	n.a.		Log S	=	-5.0	n.a.	PMID[463150]
NPT3573	Organism	Bovine viral diarrhea virus	Bovine viral diarrhea virus 1	EC50	=	71000.0	nM	PMID[463151]
NPT27	Others	Unspecified		CC50	>	100000.0	nM	PMID[463151]
NPT35	Others	n.a.		LogP	=	4.225	n.a.	PMID[463152]
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set

☑ 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 NPC263385 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	1652
0.1-0.2	3708
0.2-0.3	14906
0.3-0.4	16316
0.4-0.5	5012
0.5-0.6	824
0.6-0.7	187
0.7-0.8	50
0.8-0.85	22
0.85-0.9	14
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC1901
0.9231	High Similarity	NPC291066
0.9118	High Similarity	NPC251490
0.9077	High Similarity	NPC21211
0.9077	High Similarity	NPC113670
0.9028	High Similarity	NPC255345
0.8971	High Similarity	NPC246822
0.8971	High Similarity	NPC213570
0.8971	High Similarity	NPC139416
0.8923	High Similarity	NPC71009
0.8841	High Similarity	NPC72670
0.8769	High Similarity	NPC246588
0.8714	High Similarity	NPC226999
0.8714	High Similarity	NPC158028
0.8714	High Similarity	NPC39799
0.8714	High Similarity	NPC1008
0.8714	High Similarity	NPC193578
0.8714	High Similarity	NPC135433
0.8714	High Similarity	NPC87099
0.8714	High Similarity	NPC280135
0.8696	High Similarity	NPC473206
0.8676	High Similarity	NPC267443
0.8657	High Similarity	NPC264470
0.8636	High Similarity	NPC66517
0.8551	High Similarity	NPC22760
0.8485	Intermediate Similarity	NPC310758
0.8485	Intermediate Similarity	NPC238023
0.8472	Intermediate Similarity	NPC258492
0.8472	Intermediate Similarity	NPC96835
0.8462	Intermediate Similarity	NPC114327
0.8462	Intermediate Similarity	NPC36357
0.8429	Intermediate Similarity	NPC297358
0.8382	Intermediate Similarity	NPC155172
0.8358	Intermediate Similarity	NPC22786
0.8356	Intermediate Similarity	NPC307195
0.8209	Intermediate Similarity	NPC135924
0.8154	Intermediate Similarity	NPC198841
0.8143	Intermediate Similarity	NPC6107
0.8088	Intermediate Similarity	NPC29680
0.8088	Intermediate Similarity	NPC200745
0.8082	Intermediate Similarity	NPC54269
0.803	Intermediate Similarity	NPC300345
0.803	Intermediate Similarity	NPC120441
0.803	Intermediate Similarity	NPC212114
0.803	Intermediate Similarity	NPC65873
0.8026	Intermediate Similarity	NPC66270
0.8026	Intermediate Similarity	NPC245896
0.8	Intermediate Similarity	NPC149436
0.8	Intermediate Similarity	NPC113837
0.8	Intermediate Similarity	NPC289915
0.7971	Intermediate Similarity	NPC88566
0.7941	Intermediate Similarity	NPC54368
0.7941	Intermediate Similarity	NPC210849
0.7941	Intermediate Similarity	NPC150196
0.7941	Intermediate Similarity	NPC248705
0.7922	Intermediate Similarity	NPC159661
0.7879	Intermediate Similarity	NPC269586
0.7857	Intermediate Similarity	NPC32312
0.7857	Intermediate Similarity	NPC198023
0.7831	Intermediate Similarity	NPC113307
0.7821	Intermediate Similarity	NPC315216
0.7821	Intermediate Similarity	NPC50063
0.7794	Intermediate Similarity	NPC147062
0.7746	Intermediate Similarity	NPC36440
0.7746	Intermediate Similarity	NPC178527
0.7727	Intermediate Similarity	NPC277704
0.7714	Intermediate Similarity	NPC45756
0.7662	Intermediate Similarity	NPC249018
0.7662	Intermediate Similarity	NPC3190
0.7647	Intermediate Similarity	NPC64270
0.7647	Intermediate Similarity	NPC8235
0.7536	Intermediate Similarity	NPC169110
0.7432	Intermediate Similarity	NPC5324
0.7432	Intermediate Similarity	NPC200936
0.7308	Intermediate Similarity	NPC110264
0.7303	Intermediate Similarity	NPC21959
0.7229	Intermediate Similarity	NPC133162
0.7222	Intermediate Similarity	NPC50266
0.7215	Intermediate Similarity	NPC9796
0.7183	Intermediate Similarity	NPC45255
0.7143	Intermediate Similarity	NPC212463
0.7059	Intermediate Similarity	NPC148231
0.7042	Intermediate Similarity	NPC147578
0.7037	Intermediate Similarity	NPC272260
0.7011	Intermediate Similarity	NPC325709
0.7011	Intermediate Similarity	NPC199567
0.7011	Intermediate Similarity	NPC418308
0.6989	Remote Similarity	NPC472879
0.6951	Remote Similarity	NPC184030
0.6951	Remote Similarity	NPC164449
0.6951	Remote Similarity	NPC95868
0.6944	Remote Similarity	NPC200624
0.6932	Remote Similarity	NPC277277
0.6897	Remote Similarity	NPC267262
0.6883	Remote Similarity	NPC229235
0.6867	Remote Similarity	NPC12936
0.6867	Remote Similarity	NPC273033
0.6867	Remote Similarity	NPC242628
0.6854	Remote Similarity	NPC475023
0.6854	Remote Similarity	NPC103346
0.6854	Remote Similarity	NPC475059
0.6842	Remote Similarity	NPC78954
0.6842	Remote Similarity	NPC311343
0.6842	Remote Similarity	NPC239931
0.6842	Remote Similarity	NPC82770
0.6829	Remote Similarity	NPC139901
0.6829	Remote Similarity	NPC151405
0.6824	Remote Similarity	NPC95429
0.6795	Remote Similarity	NPC74458
0.6795	Remote Similarity	NPC208302
0.679	Remote Similarity	NPC298023
0.679	Remote Similarity	NPC179726
0.6786	Remote Similarity	NPC73637
0.6786	Remote Similarity	NPC121478
0.6782	Remote Similarity	NPC60408
0.6778	Remote Similarity	NPC128645
0.6778	Remote Similarity	NPC475057
0.6771	Remote Similarity	NPC327811
0.6771	Remote Similarity	NPC254965
0.6753	Remote Similarity	NPC98880
0.6753	Remote Similarity	NPC169222
0.6753	Remote Similarity	NPC235059
0.6753	Remote Similarity	NPC16190
0.675	Remote Similarity	NPC276699
0.675	Remote Similarity	NPC189371
0.6747	Remote Similarity	NPC477703
0.6747	Remote Similarity	NPC71664
0.6742	Remote Similarity	NPC19256
0.6711	Remote Similarity	NPC52330
0.6709	Remote Similarity	NPC285679
0.6709	Remote Similarity	NPC244738
0.6709	Remote Similarity	NPC271437
0.6707	Remote Similarity	NPC103488
0.6707	Remote Similarity	NPC224544
0.6706	Remote Similarity	NPC104070
0.6706	Remote Similarity	NPC119677
0.6706	Remote Similarity	NPC273758
0.6667	Remote Similarity	NPC243166
0.6667	Remote Similarity	NPC95289
0.6667	Remote Similarity	NPC470926
0.663	Remote Similarity	NPC472880
0.663	Remote Similarity	NPC172925
0.6629	Remote Similarity	NPC176858
0.6629	Remote Similarity	NPC298115
0.6628	Remote Similarity	NPC267704
0.6625	Remote Similarity	NPC208075
0.6625	Remote Similarity	NPC108218
0.6625	Remote Similarity	NPC113000
0.6625	Remote Similarity	NPC122327
0.6625	Remote Similarity	NPC112609
0.6615	Remote Similarity	NPC11150
0.6593	Remote Similarity	NPC108800
0.6593	Remote Similarity	NPC314690
0.6588	Remote Similarity	NPC283012
0.6588	Remote Similarity	NPC475199
0.6585	Remote Similarity	NPC290638
0.6582	Remote Similarity	NPC155429
0.6582	Remote Similarity	NPC326200
0.6556	Remote Similarity	NPC26224
0.6556	Remote Similarity	NPC191444
0.6552	Remote Similarity	NPC475710
0.6552	Remote Similarity	NPC99482
0.6548	Remote Similarity	NPC328178
0.6548	Remote Similarity	NPC17408
0.6548	Remote Similarity	NPC285716
0.6548	Remote Similarity	NPC157055
0.6522	Remote Similarity	NPC289883
0.6517	Remote Similarity	NPC157778
0.6512	Remote Similarity	NPC39600
0.6512	Remote Similarity	NPC172984
0.6512	Remote Similarity	NPC215008
0.6489	Remote Similarity	NPC133135
0.6489	Remote Similarity	NPC251579
0.6484	Remote Similarity	NPC220596
0.6484	Remote Similarity	NPC125226
0.6477	Remote Similarity	NPC258046
0.6477	Remote Similarity	NPC160339
0.6477	Remote Similarity	NPC307
0.6471	Remote Similarity	NPC231986
0.6471	Remote Similarity	NPC133050
0.6471	Remote Similarity	NPC165212
0.6463	Remote Similarity	NPC139658
0.6458	Remote Similarity	NPC474582
0.6456	Remote Similarity	NPC219246
0.6452	Remote Similarity	NPC329430
0.6437	Remote Similarity	NPC169016
0.6429	Remote Similarity	NPC56168
0.6421	Remote Similarity	NPC49994
0.6413	Remote Similarity	NPC59677
0.641	Remote Similarity	NPC181786
0.6404	Remote Similarity	NPC43945
0.6404	Remote Similarity	NPC69057
0.6395	Remote Similarity	NPC230068
0.6386	Remote Similarity	NPC245966
0.6386	Remote Similarity	NPC98269
0.6386	Remote Similarity	NPC325662
0.6374	Remote Similarity	NPC173413
0.6364	Remote Similarity	NPC123476
0.6353	Remote Similarity	NPC190567
0.6344	Remote Similarity	NPC271440

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 NPC263385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1048
0.1-0.2	673
0.2-0.3	2733
0.3-0.4	3078
0.4-0.5	1166
0.5-0.6	332
0.6-0.7	99
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9077	High Similarity	NPD675	Discontinued
0.8429	Intermediate Similarity	NPD1673	Approved
0.7671	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD3979	Approved
0.7595	Intermediate Similarity	NPD3981	Approved
0.7595	Intermediate Similarity	NPD3904	Approved
0.7595	Intermediate Similarity	NPD3903	Approved
0.7361	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1508	Approved
0.7326	Intermediate Similarity	NPD3344	Approved
0.7326	Intermediate Similarity	NPD3346	Approved
0.7317	Intermediate Similarity	NPD4635	Approved
0.725	Intermediate Similarity	NPD1475	Approved
0.7229	Intermediate Similarity	NPD3427	Approved
0.7229	Intermediate Similarity	NPD3429	Approved
0.7229	Intermediate Similarity	NPD4544	Approved
0.716	Intermediate Similarity	NPD914	Suspended
0.716	Intermediate Similarity	NPD1617	Discontinued
0.7111	Intermediate Similarity	NPD1843	Approved
0.7108	Intermediate Similarity	NPD423	Phase 3
0.7073	Intermediate Similarity	NPD3035	Approved
0.7059	Intermediate Similarity	NPD4409	Approved
0.7059	Intermediate Similarity	NPD4406	Approved
0.7013	Intermediate Similarity	NPD294	Approved
0.7013	Intermediate Similarity	NPD292	Approved
0.7	Intermediate Similarity	NPD4147	Approved
0.7	Intermediate Similarity	NPD4144	Approved
0.6988	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4170	Approved
0.6988	Remote Similarity	NPD4169	Approved
0.6977	Remote Similarity	NPD3426	Approved
0.6977	Remote Similarity	NPD3428	Approved
0.6951	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1185	Approved
0.6905	Remote Similarity	NPD2001	Discontinued
0.6905	Remote Similarity	NPD3971	Phase 1
0.6897	Remote Similarity	NPD3345	Approved
0.6867	Remote Similarity	NPD4026	Approved
0.6867	Remote Similarity	NPD942	Approved
0.6867	Remote Similarity	NPD4027	Approved
0.686	Remote Similarity	NPD1697	Approved
0.6824	Remote Similarity	NPD5178	Approved
0.6778	Remote Similarity	NPD4405	Approved
0.6778	Remote Similarity	NPD4407	Approved
0.6778	Remote Similarity	NPD4408	Approved
0.6747	Remote Similarity	NPD260	Discontinued
0.6709	Remote Similarity	NPD9728	Phase 1
0.6707	Remote Similarity	NPD9564	Approved
0.6707	Remote Similarity	NPD9563	Approved
0.6707	Remote Similarity	NPD79	Approved
0.6706	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4542	Approved
0.6703	Remote Similarity	NPD4545	Approved
0.6667	Remote Similarity	NPD3099	Discontinued
0.6667	Remote Similarity	NPD4636	Approved
0.6667	Remote Similarity	NPD713	Clinical (unspecified phase)
0.663	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD9592	Approved
0.6625	Remote Similarity	NPD9591	Approved
0.6625	Remote Similarity	NPD9594	Approved
0.6625	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD9593	Approved
0.6625	Remote Similarity	NPD80	Approved
0.6625	Remote Similarity	NPD9589	Approved
0.6625	Remote Similarity	NPD9588	Approved
0.6625	Remote Similarity	NPD9590	Approved
0.6591	Remote Similarity	NPD4146	Approved
0.6591	Remote Similarity	NPD2002	Discontinued
0.6591	Remote Similarity	NPD4145	Approved
0.6559	Remote Similarity	NPD3093	Approved
0.6552	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5916	Discontinued
0.6522	Remote Similarity	NPD3982	Approved
0.6522	Remote Similarity	NPD3980	Approved
0.6522	Remote Similarity	NPD2878	Approved
0.6517	Remote Similarity	NPD5675	Discontinued
0.6512	Remote Similarity	NPD4000	Phase 3
0.65	Remote Similarity	NPD8009	Approved
0.65	Remote Similarity	NPD8010	Approved
0.6489	Remote Similarity	NPD5597	Approved
0.6489	Remote Similarity	NPD5598	Approved
0.6489	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4543	Discontinued
0.6484	Remote Similarity	NPD1239	Approved
0.6444	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2538	Approved
0.6437	Remote Similarity	NPD2539	Approved
0.6429	Remote Similarity	NPD589	Approved
0.6429	Remote Similarity	NPD590	Approved
0.6421	Remote Similarity	NPD5832	Phase 3
0.6404	Remote Similarity	NPD650	Approved
0.6383	Remote Similarity	NPD2005	Discontinued
0.6383	Remote Similarity	NPD3458	Approved
0.6383	Remote Similarity	NPD3457	Approved
0.6383	Remote Similarity	NPD2895	Discontinued
0.6383	Remote Similarity	NPD3456	Approved
0.6383	Remote Similarity	NPD1738	Approved
0.6374	Remote Similarity	NPD5915	Approved
0.6374	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD736	Approved
0.6344	Remote Similarity	NPD735	Approved
0.6344	Remote Similarity	NPD1563	Approved
0.6341	Remote Similarity	NPD9716	Approved
0.631	Remote Similarity	NPD296	Approved
0.631	Remote Similarity	NPD225	Approved
0.631	Remote Similarity	NPD9397	Approved
0.631	Remote Similarity	NPD295	Approved
0.631	Remote Similarity	NPD293	Approved
0.631	Remote Similarity	NPD9393	Approved
0.631	Remote Similarity	NPD227	Approved
0.6304	Remote Similarity	NPD517	Discontinued
0.6304	Remote Similarity	NPD7609	Phase 3
0.6292	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6049	Phase 2
0.6264	Remote Similarity	NPD1628	Approved
0.6264	Remote Similarity	NPD1629	Approved
0.6237	Remote Similarity	NPD7631	Approved
0.6235	Remote Similarity	NPD1053	Approved
0.6235	Remote Similarity	NPD1052	Approved
0.6235	Remote Similarity	NPD1051	Approved
0.6224	Remote Similarity	NPD4321	Approved
0.6211	Remote Similarity	NPD1989	Approved
0.6211	Remote Similarity	NPD5963	Phase 2
0.6211	Remote Similarity	NPD5964	Phase 2
0.6211	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6472	Discontinued
0.62	Remote Similarity	NPD1268	Approved
0.62	Remote Similarity	NPD1269	Approved
0.6196	Remote Similarity	NPD4728	Approved
0.619	Remote Similarity	NPD603	Approved
0.618	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.618	Remote Similarity	NPD2205	Approved
0.618	Remote Similarity	NPD2208	Approved
0.6163	Remote Similarity	NPD5372	Approved
0.6163	Remote Similarity	NPD5371	Approved
0.6162	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3495	Discontinued
0.6146	Remote Similarity	NPD1565	Approved
0.6146	Remote Similarity	NPD1564	Approved
0.6146	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD1566	Phase 3
0.6136	Remote Similarity	NPD262	Approved
0.6136	Remote Similarity	NPD263	Approved
0.6129	Remote Similarity	NPD3000	Approved
0.6129	Remote Similarity	NPD2998	Approved
0.6129	Remote Similarity	NPD2997	Approved
0.6122	Remote Similarity	NPD6354	Discontinued
0.6122	Remote Similarity	NPD5630	Phase 1
0.6122	Remote Similarity	NPD1916	Discontinued
0.6105	Remote Similarity	NPD4094	Approved
0.6105	Remote Similarity	NPD5554	Approved
0.6105	Remote Similarity	NPD3772	Phase 3
0.61	Remote Similarity	NPD4936	Approved
0.61	Remote Similarity	NPD4937	Approved
0.6092	Remote Similarity	NPD472	Approved
0.6092	Remote Similarity	NPD226	Approved
0.6087	Remote Similarity	NPD771	Phase 3
0.6078	Remote Similarity	NPD5253	Approved
0.6075	Remote Similarity	NPD4032	Approved
0.6075	Remote Similarity	NPD4031	Approved
0.6064	Remote Similarity	NPD9361	Approved
0.6061	Remote Similarity	NPD2841	Approved
0.6061	Remote Similarity	NPD538	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD508	Approved
0.6047	Remote Similarity	NPD507	Approved
0.6047	Remote Similarity	NPD9490	Approved
0.6044	Remote Similarity	NPD1087	Approved
0.6042	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4737	Phase 2
0.6019	Remote Similarity	NPD1841	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6549	Approved
0.6	Remote Similarity	NPD9294	Approved
0.6	Remote Similarity	NPD8	Approved
0.6	Remote Similarity	NPD243	Approved
0.6	Remote Similarity	NPD6548	Approved
0.598	Remote Similarity	NPD7170	Discontinued
0.5979	Remote Similarity	NPD4655	Approved
0.5979	Remote Similarity	NPD1875	Phase 1
0.5979	Remote Similarity	NPD4657	Approved
0.5978	Remote Similarity	NPD531	Approved
0.5978	Remote Similarity	NPD1101	Approved
0.5963	Remote Similarity	NPD1837	Clinical (unspecified phase)
0.596	Remote Similarity	NPD1616	Discontinued
0.5955	Remote Similarity	NPD831	Approved
0.5955	Remote Similarity	NPD830	Approved
0.5955	Remote Similarity	NPD9491	Approved
0.5955	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3048	Approved
0.5941	Remote Similarity	NPD3047	Approved
0.5941	Remote Similarity	NPD3046	Approved
0.5941	Remote Similarity	NPD1028	Approved
0.5941	Remote Similarity	NPD1026	Approved
0.5938	Remote Similarity	NPD1693	Approved
0.5922	Remote Similarity	NPD2342	Discontinued
0.5918	Remote Similarity	NPD4117	Approved
0.5909	Remote Similarity	NPD4479	Discontinued
0.59	Remote Similarity	NPD1540	Approved
0.59	Remote Similarity	NPD1932	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