NPASS Compound

Structure

CID214289 OpenBabel06191716002D 27 30 0 0 0 0 0 0 0 0999 V2000 -4.3301 -2.5000 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 -3.4641 -1.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 2.5981 1.5000 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 -0.8660 -2.5000 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 1.7321 -0.0000 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 0.8660 -1.5000 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 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 1 8 1 0 0 0 0 2 7 1 0 0 0 0 2 10 2 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 9 1 0 0 0 0 5 14 2 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.05
Volume:	341.042
LogP:	3.013
LogD:	2.056
LogS:	-5.797
# Rotatable Bonds:	2
TPSA:	149.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	3.156
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.782
MDCK Permeability:	1.2506616258178838e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	0.75

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	91.75772094726562%
Volume Distribution (VD):	0.578
Pgp-substrate:	5.745380878448486%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.61
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.309
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	9.991
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.243
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.975
Carcinogencity:	0.164
Eye Corrosion:	0.009
Eye Irritation:	0.944
Respiratory Toxicity:	0.571

Download Data

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

Natural Product: NPC214289

Natural Product ID:	NPC214289
*Common Name:**	Eckol
IUPAC Name:	4-(3,5-dihydroxyphenoxy)dibenzo-p-dioxin-1,3,6,8-tetrol
Synonyms:	Eckol
Standard InCHIKey:	PCZZRBGISTUIOA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O9/c19-7-1-8(20)3-10(2-7)25-16-12(23)6-13(24)17-18(16)27-15-11(22)4-9(21)5-14(15)26-17/h1-6,19-24H
SMILES:	Oc1cc(O)cc(c1)Oc1c(O)cc(c2c1Oc1c(O)cc(cc1O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471187
PubChem CID:	145937
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins

*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
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12913249]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575430]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738398]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18693022]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19201199]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462757]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647823]
NPO19494	Alstonia boonei	Species	Apocynaceae	Eukaryota	n.a.	bark	n.a.	PMID[25026352]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31270	Laminaria japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19494	Alstonia boonei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19494	Alstonia boonei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31270	Laminaria japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14149	Saccharina japonica	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19494	Alstonia boonei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22789	Ecklonia cava	Species	Lessoniaceae	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	7
Ki	2
Others	9

Activity Type	# Activity
Cell Line	4
Individual Protein	5
NON-MOLECULAR	3
Organism	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	56.5	%	PMID[509946]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	52.0	%	PMID[509946]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	59.6	%	PMID[509946]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	200000.0	nM	PMID[509947]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	Inhibition	=	30.0	%	PMID[509947]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	8800.0	nM	PMID[509947]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	Ki	=	8200.0	nM	PMID[509947]
NPT35	Others	n.a.		Inhibition	=	96.2	%	PMID[509943]
NPT2	Others	Unspecified		Inhibition	=	87.5	%	PMID[509943]
NPT1	Others	Radical scavenging activity		IC50	=	22890.0	nM	PMID[509944]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	51800.0	nM	PMID[509944]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26500.0	nM	PMID[509944]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28400.0	nM	PMID[509944]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	13900.0	nM	PMID[509945]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	12200.0	nM	PMID[509945]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	61.7	%	PMID[509946]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.0	n.a.	PMID[509947]
NPT2	Others	Unspecified		IC50	=	8800.0	nM	PMID[509948]

☑ 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 NPC214289 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	740
0.1-0.2	3988
0.2-0.3	13790
0.3-0.4	5955
0.4-0.5	4985
0.5-0.6	7116
0.6-0.7	5199
0.7-0.8	886
0.8-0.85	28
0.85-0.9	3
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9823	High Similarity	NPC205850
0.982	High Similarity	NPC151617
0.982	High Similarity	NPC76915
0.9652	High Similarity	NPC228875
0.9652	High Similarity	NPC126216
0.9652	High Similarity	NPC105147
0.9328	High Similarity	NPC110677
0.8548	High Similarity	NPC189589
0.8548	High Similarity	NPC469622
0.8496	Intermediate Similarity	NPC232654
0.848	Intermediate Similarity	NPC37074
0.8455	Intermediate Similarity	NPC192810
0.8425	Intermediate Similarity	NPC208769
0.8421	Intermediate Similarity	NPC124712
0.8413	Intermediate Similarity	NPC247146
0.84	Intermediate Similarity	NPC298845
0.8397	Intermediate Similarity	NPC48956
0.8387	Intermediate Similarity	NPC221090
0.8374	Intermediate Similarity	NPC152722
0.8359	Intermediate Similarity	NPC287780
0.8333	Intermediate Similarity	NPC469621
0.8306	Intermediate Similarity	NPC217854
0.8281	Intermediate Similarity	NPC60756
0.8246	Intermediate Similarity	NPC307875
0.824	Intermediate Similarity	NPC25817
0.8231	Intermediate Similarity	NPC60982
0.8211	Intermediate Similarity	NPC276195
0.8189	Intermediate Similarity	NPC216836
0.8154	Intermediate Similarity	NPC474134
0.8154	Intermediate Similarity	NPC131128
0.8145	Intermediate Similarity	NPC145780
0.814	Intermediate Similarity	NPC214860
0.8134	Intermediate Similarity	NPC262189
0.8074	Intermediate Similarity	NPC8577
0.8062	Intermediate Similarity	NPC45824
0.8047	Intermediate Similarity	NPC5447
0.8047	Intermediate Similarity	NPC250432
0.8043	Intermediate Similarity	NPC95652
0.8043	Intermediate Similarity	NPC150714
0.803	Intermediate Similarity	NPC66840
0.803	Intermediate Similarity	NPC310854
0.803	Intermediate Similarity	NPC256307
0.803	Intermediate Similarity	NPC170694
0.8015	Intermediate Similarity	NPC127624
0.8015	Intermediate Similarity	NPC161203
0.8015	Intermediate Similarity	NPC202762
0.8015	Intermediate Similarity	NPC86655
0.7985	Intermediate Similarity	NPC102904
0.7985	Intermediate Similarity	NPC107551
0.7985	Intermediate Similarity	NPC276490
0.7985	Intermediate Similarity	NPC176051
0.7985	Intermediate Similarity	NPC474282
0.7985	Intermediate Similarity	NPC326797
0.7985	Intermediate Similarity	NPC474390
0.7985	Intermediate Similarity	NPC103976
0.7984	Intermediate Similarity	NPC46274
0.7984	Intermediate Similarity	NPC226331
0.7969	Intermediate Similarity	NPC181361
0.7969	Intermediate Similarity	NPC171533
0.7955	Intermediate Similarity	NPC94236
0.7955	Intermediate Similarity	NPC37196
0.7953	Intermediate Similarity	NPC228972
0.7953	Intermediate Similarity	NPC122792
0.7941	Intermediate Similarity	NPC178054
0.7929	Intermediate Similarity	NPC281549
0.7926	Intermediate Similarity	NPC127218
0.7926	Intermediate Similarity	NPC319647
0.7926	Intermediate Similarity	NPC25966
0.7926	Intermediate Similarity	NPC22517
0.7926	Intermediate Similarity	NPC245207
0.7907	Intermediate Similarity	NPC50368
0.7907	Intermediate Similarity	NPC210355
0.7907	Intermediate Similarity	NPC470699
0.7899	Intermediate Similarity	NPC28440
0.7899	Intermediate Similarity	NPC171932
0.7895	Intermediate Similarity	NPC106215
0.7886	Intermediate Similarity	NPC9248
0.7879	Intermediate Similarity	NPC160991
0.7879	Intermediate Similarity	NPC16208
0.7879	Intermediate Similarity	NPC184447
0.7879	Intermediate Similarity	NPC7903
0.7879	Intermediate Similarity	NPC35932
0.7872	Intermediate Similarity	NPC476969
0.7868	Intermediate Similarity	NPC22317
0.7868	Intermediate Similarity	NPC20520
0.7868	Intermediate Similarity	NPC61783
0.7868	Intermediate Similarity	NPC291101
0.7868	Intermediate Similarity	NPC266197
0.7868	Intermediate Similarity	NPC259519
0.7863	Intermediate Similarity	NPC91291
0.7863	Intermediate Similarity	NPC229231
0.7857	Intermediate Similarity	NPC97432
0.7857	Intermediate Similarity	NPC190454
0.7852	Intermediate Similarity	NPC65530
0.7852	Intermediate Similarity	NPC211549
0.7852	Intermediate Similarity	NPC59324
0.7846	Intermediate Similarity	NPC266691
0.7836	Intermediate Similarity	NPC47398
0.7836	Intermediate Similarity	NPC470356
0.7836	Intermediate Similarity	NPC261873
0.7836	Intermediate Similarity	NPC474206
0.7836	Intermediate Similarity	NPC281521
0.7836	Intermediate Similarity	NPC112939
0.7836	Intermediate Similarity	NPC201357
0.7836	Intermediate Similarity	NPC121812
0.7836	Intermediate Similarity	NPC260898
0.7836	Intermediate Similarity	NPC134968
0.7836	Intermediate Similarity	NPC283009
0.7836	Intermediate Similarity	NPC234333
0.7836	Intermediate Similarity	NPC94750
0.7836	Intermediate Similarity	NPC255147
0.7836	Intermediate Similarity	NPC112246
0.7836	Intermediate Similarity	NPC195022
0.7836	Intermediate Similarity	NPC472337
0.7829	Intermediate Similarity	NPC45728
0.7826	Intermediate Similarity	NPC252169
0.7823	Intermediate Similarity	NPC228907
0.782	Intermediate Similarity	NPC229442
0.782	Intermediate Similarity	NPC168059
0.781	Intermediate Similarity	NPC471389
0.781	Intermediate Similarity	NPC247291
0.7807	Intermediate Similarity	NPC314803
0.7803	Intermediate Similarity	NPC42760
0.7803	Intermediate Similarity	NPC309787
0.7803	Intermediate Similarity	NPC268266
0.7803	Intermediate Similarity	NPC472597
0.7803	Intermediate Similarity	NPC268342
0.7803	Intermediate Similarity	NPC220825
0.7795	Intermediate Similarity	NPC473411
0.7795	Intermediate Similarity	NPC262253
0.7795	Intermediate Similarity	NPC71579
0.7794	Intermediate Similarity	NPC98777
0.7794	Intermediate Similarity	NPC212770
0.7794	Intermediate Similarity	NPC55947
0.7786	Intermediate Similarity	NPC58164
0.7786	Intermediate Similarity	NPC10225
0.7778	Intermediate Similarity	NPC269091
0.7778	Intermediate Similarity	NPC302701
0.7778	Intermediate Similarity	NPC472334
0.7778	Intermediate Similarity	NPC248727
0.7778	Intermediate Similarity	NPC242028
0.7778	Intermediate Similarity	NPC265433
0.7778	Intermediate Similarity	NPC472336
0.7778	Intermediate Similarity	NPC474639
0.7778	Intermediate Similarity	NPC16435
0.7778	Intermediate Similarity	NPC203230
0.7778	Intermediate Similarity	NPC270456
0.7778	Intermediate Similarity	NPC227503
0.7778	Intermediate Similarity	NPC173660
0.7778	Intermediate Similarity	NPC230734
0.7778	Intermediate Similarity	NPC306441
0.7778	Intermediate Similarity	NPC162659
0.7761	Intermediate Similarity	NPC317380
0.7761	Intermediate Similarity	NPC103967
0.7754	Intermediate Similarity	NPC107161
0.775	Intermediate Similarity	NPC247871
0.7744	Intermediate Similarity	NPC15658
0.7744	Intermediate Similarity	NPC219876
0.7744	Intermediate Similarity	NPC61477
0.7744	Intermediate Similarity	NPC185604
0.7744	Intermediate Similarity	NPC201587
0.7744	Intermediate Similarity	NPC470752
0.7744	Intermediate Similarity	NPC126029
0.7744	Intermediate Similarity	NPC253105
0.7744	Intermediate Similarity	NPC78770
0.7744	Intermediate Similarity	NPC261619
0.7734	Intermediate Similarity	NPC95168
0.773	Intermediate Similarity	NPC170239
0.773	Intermediate Similarity	NPC97937
0.773	Intermediate Similarity	NPC275125
0.7727	Intermediate Similarity	NPC299221
0.7727	Intermediate Similarity	NPC469614
0.7727	Intermediate Similarity	NPC469612
0.7727	Intermediate Similarity	NPC51840
0.7727	Intermediate Similarity	NPC311680
0.7727	Intermediate Similarity	NPC220935
0.7727	Intermediate Similarity	NPC234488
0.7727	Intermediate Similarity	NPC472338
0.7721	Intermediate Similarity	NPC25111
0.7721	Intermediate Similarity	NPC73535
0.7721	Intermediate Similarity	NPC6262
0.7721	Intermediate Similarity	NPC272157
0.7721	Intermediate Similarity	NPC201145
0.7721	Intermediate Similarity	NPC90615
0.7717	Intermediate Similarity	NPC57751
0.771	Intermediate Similarity	NPC72529
0.771	Intermediate Similarity	NPC63179
0.7708	Intermediate Similarity	NPC264875
0.7708	Intermediate Similarity	NPC163598
0.7708	Intermediate Similarity	NPC120774
0.7704	Intermediate Similarity	NPC164787
0.7704	Intermediate Similarity	NPC61946
0.7704	Intermediate Similarity	NPC151224
0.7698	Intermediate Similarity	NPC47633
0.7698	Intermediate Similarity	NPC10932
0.7698	Intermediate Similarity	NPC85264
0.7698	Intermediate Similarity	NPC232084
0.7698	Intermediate Similarity	NPC61516
0.7698	Intermediate Similarity	NPC102044
0.7698	Intermediate Similarity	NPC247364

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 NPC214289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	552
0.1-0.2	1171
0.2-0.3	3122
0.3-0.4	2291
0.4-0.5	1207
0.5-0.6	667
0.6-0.7	128
0.7-0.8	12
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
0.8047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1613	Approved
0.7521	Intermediate Similarity	NPD291	Approved
0.7519	Intermediate Similarity	NPD3027	Phase 3
0.7456	Intermediate Similarity	NPD9296	Approved
0.7444	Intermediate Similarity	NPD4908	Phase 1
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1548	Phase 1
0.7232	Intermediate Similarity	NPD9094	Approved
0.7188	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1653	Approved
0.7131	Intermediate Similarity	NPD968	Approved
0.7092	Intermediate Similarity	NPD3454	Phase 3
0.7068	Intermediate Similarity	NPD2983	Phase 2
0.7068	Intermediate Similarity	NPD2982	Phase 2
0.7043	Intermediate Similarity	NPD9365	Approved
0.702	Intermediate Similarity	NPD2801	Approved
0.7018	Intermediate Similarity	NPD9295	Approved
0.7	Intermediate Similarity	NPD7534	Approved
0.7	Intermediate Similarity	NPD7533	Approved
0.6992	Remote Similarity	NPD2981	Phase 2
0.696	Remote Similarity	NPD556	Approved
0.6954	Remote Similarity	NPD1934	Approved
0.6943	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6166	Phase 2
0.6943	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4749	Approved
0.6917	Remote Similarity	NPD1091	Approved
0.6884	Remote Similarity	NPD4625	Phase 3
0.6871	Remote Similarity	NPD1511	Approved
0.6861	Remote Similarity	NPD3018	Phase 2
0.6842	Remote Similarity	NPD915	Approved
0.6797	Remote Similarity	NPD1465	Phase 2
0.6779	Remote Similarity	NPD1512	Approved
0.6757	Remote Similarity	NPD9093	Approved
0.6739	Remote Similarity	NPD2861	Phase 2
0.6738	Remote Similarity	NPD1558	Phase 1
0.6719	Remote Similarity	NPD228	Approved
0.6715	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD9089	Approved
0.6691	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD422	Phase 1
0.6646	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7213	Phase 3
0.6644	Remote Similarity	NPD7212	Phase 2
0.6642	Remote Similarity	NPD3225	Approved
0.6641	Remote Similarity	NPD6671	Approved
0.6626	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6234	Discontinued
0.6605	Remote Similarity	NPD5844	Phase 1
0.6605	Remote Similarity	NPD7054	Approved
0.66	Remote Similarity	NPD7447	Phase 1
0.6596	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD9299	Approved
0.6564	Remote Similarity	NPD7472	Approved
0.6564	Remote Similarity	NPD7074	Phase 3
0.6543	Remote Similarity	NPD7228	Approved
0.6535	Remote Similarity	NPD9552	Approved
0.6535	Remote Similarity	NPD290	Approved
0.6519	Remote Similarity	NPD5846	Approved
0.6519	Remote Similarity	NPD6516	Phase 2
0.6497	Remote Similarity	NPD3882	Suspended
0.6494	Remote Similarity	NPD4675	Approved
0.6494	Remote Similarity	NPD4678	Approved
0.6494	Remote Similarity	NPD4380	Phase 2
0.649	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7266	Discontinued
0.6463	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1242	Phase 1
0.6446	Remote Similarity	NPD7549	Discontinued
0.6443	Remote Similarity	NPD3750	Approved
0.6442	Remote Similarity	NPD3818	Discontinued
0.6438	Remote Similarity	NPD7199	Phase 2
0.6433	Remote Similarity	NPD5402	Approved
0.6433	Remote Similarity	NPD3817	Phase 2
0.6429	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9501	Approved
0.6424	Remote Similarity	NPD6797	Phase 2
0.6423	Remote Similarity	NPD1535	Discovery
0.6419	Remote Similarity	NPD1549	Phase 2
0.6412	Remote Similarity	NPD7843	Approved
0.641	Remote Similarity	NPD37	Approved
0.6405	Remote Similarity	NPD5403	Approved
0.64	Remote Similarity	NPD6190	Approved
0.6395	Remote Similarity	NPD6100	Approved
0.6395	Remote Similarity	NPD6099	Approved
0.6392	Remote Similarity	NPD4967	Phase 2
0.6392	Remote Similarity	NPD4966	Approved
0.6392	Remote Similarity	NPD4965	Approved
0.6386	Remote Similarity	NPD7251	Discontinued
0.6382	Remote Similarity	NPD5401	Approved
0.6377	Remote Similarity	NPD1481	Phase 2
0.6376	Remote Similarity	NPD1652	Phase 2
0.6376	Remote Similarity	NPD6674	Discontinued
0.637	Remote Similarity	NPD4538	Approved
0.637	Remote Similarity	NPD4536	Approved
0.637	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD8054	Approved
0.6369	Remote Similarity	NPD8053	Approved
0.6364	Remote Similarity	NPD5283	Phase 1
0.6358	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD2684	Approved
0.6351	Remote Similarity	NPD3540	Phase 1
0.6347	Remote Similarity	NPD7808	Phase 3
0.6346	Remote Similarity	NPD7411	Suspended
0.634	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD9088	Approved
0.6331	Remote Similarity	NPD6582	Phase 2
0.6331	Remote Similarity	NPD6583	Phase 3
0.6329	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5960	Phase 3
0.6327	Remote Similarity	NPD5588	Approved
0.6316	Remote Similarity	NPD4357	Discontinued
0.6306	Remote Similarity	NPD3382	Approved
0.6306	Remote Similarity	NPD3383	Approved
0.6306	Remote Similarity	NPD3384	Approved
0.6296	Remote Similarity	NPD6232	Discontinued
0.6288	Remote Similarity	NPD5535	Approved
0.6284	Remote Similarity	NPD1551	Phase 2
0.6284	Remote Similarity	NPD3539	Phase 1
0.6276	Remote Similarity	NPD3620	Phase 2
0.6276	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5494	Approved
0.6269	Remote Similarity	NPD7157	Approved
0.6268	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.626	Remote Similarity	NPD2671	Approved
0.626	Remote Similarity	NPD2673	Approved
0.625	Remote Similarity	NPD7075	Discontinued
0.625	Remote Similarity	NPD6798	Discontinued
0.6233	Remote Similarity	NPD5124	Phase 1
0.6233	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD230	Phase 1
0.6233	Remote Similarity	NPD4340	Discontinued
0.6233	Remote Similarity	NPD1933	Approved
0.6226	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD1798	Approved
0.6204	Remote Similarity	NPD1797	Approved
0.6204	Remote Similarity	NPD6382	Discontinued
0.6197	Remote Similarity	NPD6584	Phase 3
0.6196	Remote Similarity	NPD3787	Discontinued
0.6194	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2224	Approved
0.619	Remote Similarity	NPD2223	Approved
0.6187	Remote Similarity	NPD3705	Approved
0.6184	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2219	Phase 1
0.6183	Remote Similarity	NPD3022	Approved
0.6183	Remote Similarity	NPD3021	Approved
0.6182	Remote Similarity	NPD7473	Discontinued
0.6181	Remote Similarity	NPD7095	Approved
0.6176	Remote Similarity	NPD1103	Approved
0.6176	Remote Similarity	NPD1102	Approved
0.6176	Remote Similarity	NPD5536	Phase 2
0.6173	Remote Similarity	NPD5677	Discontinued
0.617	Remote Similarity	NPD6696	Suspended
0.6169	Remote Similarity	NPD4123	Phase 3
0.6169	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD8455	Phase 2
0.6159	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD7097	Phase 1
0.6149	Remote Similarity	NPD3749	Approved
0.6148	Remote Similarity	NPD191	Approved
0.6145	Remote Similarity	NPD3751	Discontinued
0.6144	Remote Similarity	NPD5058	Phase 3
0.6135	Remote Similarity	NPD6959	Discontinued
0.6127	Remote Similarity	NPD1203	Approved
0.6127	Remote Similarity	NPD2797	Approved
0.6122	Remote Similarity	NPD447	Suspended
0.6118	Remote Similarity	NPD7466	Approved
0.6115	Remote Similarity	NPD3447	Discontinued
0.6115	Remote Similarity	NPD4005	Discontinued
0.6108	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD1510	Phase 2
0.6107	Remote Similarity	NPD3748	Approved
0.6104	Remote Similarity	NPD6799	Approved
0.6095	Remote Similarity	NPD7240	Approved
0.609	Remote Similarity	NPD2122	Discontinued
0.6087	Remote Similarity	NPD7768	Phase 2
0.6084	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD7906	Approved
0.6062	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5451	Approved
0.6056	Remote Similarity	NPD8651	Approved
0.6054	Remote Similarity	NPD4060	Phase 1
0.6054	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD1240	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