NPASS Compound

Structure

CID126216 OpenBabel06191715482D 36 40 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 6.0622 0.5000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 3.4641 2.0000 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 9 2 0 0 0 0 1 10 1 0 0 0 0 2 9 1 0 0 0 0 2 12 2 0 0 0 0 3 10 2 0 0 0 0 3 12 1 0 0 0 0 4 11 2 0 0 0 0 4 14 1 0 0 0 0 5 11 1 0 0 0 0 5 15 2 0 0 0 0 6 13 2 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 19 2 0 0 0 0 8 17 2 0 0 0 0 8 18 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 34 1 0 0 0 0 13 33 1 0 0 0 0 14 20 2 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 29 1 0 0 0 0 16 21 2 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 31 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 21 1 0 0 0 0 19 35 1 0 0 0 0 20 33 1 0 0 0 0 21 36 1 0 0 0 0 22 24 2 0 0 0 0 22 34 1 0 0 0 0 23 24 1 0 0 0 0 23 35 1 0 0 0 0 24 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.06
Volume:	454.723
LogP:	3.601
LogD:	2.359
LogS:	-6.773
# Rotatable Bonds:	4
TPSA:	198.76
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	3.326
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.369
MDCK Permeability:	1.1228865332668647e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	90.71354675292969%
Volume Distribution (VD):	0.435
Pgp-substrate:	7.471755027770996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.872
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.562
CYP2C9-substrate:	0.694
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	9.671
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.551
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.985
Carcinogencity:	0.103
Eye Corrosion:	0.004
Eye Irritation:	0.951
Respiratory Toxicity:	0.268

Download Data

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

Natural Product: NPC126216

Natural Product ID:	NPC126216
*Common Name:**	7-Phloroethol
IUPAC Name:	4-(3,5-dihydroxyphenoxy)-8-(2,4,6-trihydroxyphenoxy)dibenzo-p-dioxin-1,3,6-triol
Synonyms:	7-Phloroethol
Standard InCHIKey:	JLEVVQRBEATTCM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H16O12/c25-9-1-10(26)3-12(2-9)34-22-17(31)8-18(32)23-24(22)36-21-16(30)6-13(7-19(21)35-23)33-20-14(28)4-11(27)5-15(20)29/h1-8,25-32H
SMILES:	Oc1cc(O)c(c(c1)O)Oc1cc(O)c2c(c1)Oc1c(O2)c(Oc2cc(O)cc(c2)O)c(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456228
PubChem CID:	10480940
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
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]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647823]
NPO22789	Ecklonia cava	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]

☑ 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	8
Ki	2
Others	2

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	200000.0	nM	PMID[486873]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	112000.0	nM	PMID[486873]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	42100.0	nM	PMID[486873]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	Ki	=	19300.0	nM	PMID[486873]
NPT1	Others	Radical scavenging activity		IC50	=	18640.0	nM	PMID[486871]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39600.0	nM	PMID[486871]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21900.0	nM	PMID[486871]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22700.0	nM	PMID[486871]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	7200.0	nM	PMID[486872]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	8590.0	nM	PMID[486872]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	1.8	n.a.	PMID[486873]
NPT2	Others	Unspecified		IC50	=	42100.0	nM	PMID[486874]

☑ 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 NPC126216 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	774
0.1-0.2	4140
0.2-0.3	13808
0.3-0.4	5926
0.4-0.5	5270
0.5-0.6	7200
0.6-0.7	4783
0.7-0.8	767
0.8-0.85	21
0.85-0.9	1
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC105147
1.0	High Similarity	NPC228875
0.9664	High Similarity	NPC110677
0.9655	High Similarity	NPC205850
0.9652	High Similarity	NPC214289
0.9478	High Similarity	NPC76915
0.9478	High Similarity	NPC151617
0.8561	High Similarity	NPC48956
0.8433	Intermediate Similarity	NPC262189
0.8425	Intermediate Similarity	NPC189589
0.8425	Intermediate Similarity	NPC469622
0.8359	Intermediate Similarity	NPC37074
0.8333	Intermediate Similarity	NPC150714
0.8333	Intermediate Similarity	NPC95652
0.8333	Intermediate Similarity	NPC192810
0.8321	Intermediate Similarity	NPC131128
0.8321	Intermediate Similarity	NPC474134
0.8308	Intermediate Similarity	NPC208769
0.8295	Intermediate Similarity	NPC247146
0.8281	Intermediate Similarity	NPC298845
0.8268	Intermediate Similarity	NPC221090
0.8258	Intermediate Similarity	NPC60982
0.8254	Intermediate Similarity	NPC152722
0.8244	Intermediate Similarity	NPC287780
0.8235	Intermediate Similarity	NPC8577
0.8217	Intermediate Similarity	NPC469621
0.8214	Intermediate Similarity	NPC281549
0.8205	Intermediate Similarity	NPC232654
0.8195	Intermediate Similarity	NPC66840
0.8195	Intermediate Similarity	NPC256307
0.8189	Intermediate Similarity	NPC217854
0.8188	Intermediate Similarity	NPC28440
0.8188	Intermediate Similarity	NPC171932
0.8168	Intermediate Similarity	NPC60756
0.8156	Intermediate Similarity	NPC476969
0.8148	Intermediate Similarity	NPC474390
0.8136	Intermediate Similarity	NPC124712
0.8125	Intermediate Similarity	NPC25817
0.8095	Intermediate Similarity	NPC276195
0.8077	Intermediate Similarity	NPC216836
0.803	Intermediate Similarity	NPC214860
0.8029	Intermediate Similarity	NPC20520
0.8029	Intermediate Similarity	NPC61783
0.8029	Intermediate Similarity	NPC22317
0.7966	Intermediate Similarity	NPC307875
0.7956	Intermediate Similarity	NPC55947
0.7955	Intermediate Similarity	NPC45824
0.7943	Intermediate Similarity	NPC96576
0.7926	Intermediate Similarity	NPC310854
0.7926	Intermediate Similarity	NPC170694
0.791	Intermediate Similarity	NPC127624
0.7902	Intermediate Similarity	NPC321657
0.7902	Intermediate Similarity	NPC211561
0.7902	Intermediate Similarity	NPC318373
0.7891	Intermediate Similarity	NPC145780
0.7887	Intermediate Similarity	NPC236202
0.7887	Intermediate Similarity	NPC204770
0.7887	Intermediate Similarity	NPC82917
0.7887	Intermediate Similarity	NPC294558
0.7887	Intermediate Similarity	NPC170103
0.7887	Intermediate Similarity	NPC18185
0.7887	Intermediate Similarity	NPC263940
0.7887	Intermediate Similarity	NPC262911
0.7887	Intermediate Similarity	NPC70409
0.7887	Intermediate Similarity	NPC108811
0.7887	Intermediate Similarity	NPC202742
0.7887	Intermediate Similarity	NPC58190
0.7883	Intermediate Similarity	NPC107551
0.7883	Intermediate Similarity	NPC326797
0.7883	Intermediate Similarity	NPC102904
0.7883	Intermediate Similarity	NPC474282
0.7883	Intermediate Similarity	NPC276490
0.7883	Intermediate Similarity	NPC176051
0.7883	Intermediate Similarity	NPC103976
0.7863	Intermediate Similarity	NPC181361
0.7863	Intermediate Similarity	NPC171533
0.7852	Intermediate Similarity	NPC37196
0.7852	Intermediate Similarity	NPC94236
0.7847	Intermediate Similarity	NPC477612
0.7846	Intermediate Similarity	NPC228972
0.7846	Intermediate Similarity	NPC122792
0.7842	Intermediate Similarity	NPC178054
0.7832	Intermediate Similarity	NPC227516
0.7832	Intermediate Similarity	NPC20757
0.7826	Intermediate Similarity	NPC22517
0.7826	Intermediate Similarity	NPC25966
0.7826	Intermediate Similarity	NPC319647
0.7826	Intermediate Similarity	NPC245207
0.7826	Intermediate Similarity	NPC127218
0.782	Intermediate Similarity	NPC210655
0.7803	Intermediate Similarity	NPC250432
0.7803	Intermediate Similarity	NPC210355
0.7803	Intermediate Similarity	NPC470699
0.7803	Intermediate Similarity	NPC5447
0.7778	Intermediate Similarity	NPC202762
0.7778	Intermediate Similarity	NPC35932
0.7778	Intermediate Similarity	NPC86655
0.7778	Intermediate Similarity	NPC9248
0.7778	Intermediate Similarity	NPC16208
0.7778	Intermediate Similarity	NPC160991
0.7778	Intermediate Similarity	NPC7903
0.7778	Intermediate Similarity	NPC184447
0.7778	Intermediate Similarity	NPC161203
0.777	Intermediate Similarity	NPC259519
0.777	Intermediate Similarity	NPC266197
0.777	Intermediate Similarity	NPC291101
0.7754	Intermediate Similarity	NPC59324
0.7754	Intermediate Similarity	NPC65530
0.7754	Intermediate Similarity	NPC211549
0.7744	Intermediate Similarity	NPC226331
0.7744	Intermediate Similarity	NPC266691
0.7744	Intermediate Similarity	NPC46274
0.774	Intermediate Similarity	NPC264875
0.774	Intermediate Similarity	NPC120774
0.774	Intermediate Similarity	NPC163598
0.7737	Intermediate Similarity	NPC260898
0.7737	Intermediate Similarity	NPC474206
0.7737	Intermediate Similarity	NPC255147
0.7737	Intermediate Similarity	NPC234333
0.7737	Intermediate Similarity	NPC470356
0.7737	Intermediate Similarity	NPC121812
0.7737	Intermediate Similarity	NPC134968
0.7737	Intermediate Similarity	NPC195022
0.7737	Intermediate Similarity	NPC47398
0.7737	Intermediate Similarity	NPC112939
0.7737	Intermediate Similarity	NPC112246
0.7737	Intermediate Similarity	NPC283009
0.7737	Intermediate Similarity	NPC261873
0.7737	Intermediate Similarity	NPC201357
0.7737	Intermediate Similarity	NPC94750
0.7737	Intermediate Similarity	NPC281521
0.7737	Intermediate Similarity	NPC472337
0.773	Intermediate Similarity	NPC252169
0.7721	Intermediate Similarity	NPC168059
0.7721	Intermediate Similarity	NPC229442
0.7717	Intermediate Similarity	NPC228907
0.7714	Intermediate Similarity	NPC247291
0.7714	Intermediate Similarity	NPC100482
0.7714	Intermediate Similarity	NPC471389
0.7714	Intermediate Similarity	NPC277331
0.7704	Intermediate Similarity	NPC472597
0.7704	Intermediate Similarity	NPC309787
0.7698	Intermediate Similarity	NPC98777
0.7698	Intermediate Similarity	NPC212770
0.7692	Intermediate Similarity	NPC71579
0.7692	Intermediate Similarity	NPC262253
0.7692	Intermediate Similarity	NPC473411
0.7687	Intermediate Similarity	NPC10225
0.7687	Intermediate Similarity	NPC58164
0.7681	Intermediate Similarity	NPC474639
0.7681	Intermediate Similarity	NPC265433
0.7681	Intermediate Similarity	NPC306441
0.7681	Intermediate Similarity	NPC230734
0.7681	Intermediate Similarity	NPC472336
0.7681	Intermediate Similarity	NPC472334
0.7681	Intermediate Similarity	NPC302701
0.7681	Intermediate Similarity	NPC227503
0.7681	Intermediate Similarity	NPC173660
0.7681	Intermediate Similarity	NPC162659
0.7681	Intermediate Similarity	NPC242028
0.7681	Intermediate Similarity	NPC203230
0.7681	Intermediate Similarity	NPC16435
0.7681	Intermediate Similarity	NPC248727
0.7681	Intermediate Similarity	NPC269091
0.7681	Intermediate Similarity	NPC270456
0.7676	Intermediate Similarity	NPC304894
0.7676	Intermediate Similarity	NPC15659
0.7669	Intermediate Similarity	NPC50368
0.7664	Intermediate Similarity	NPC103967
0.7664	Intermediate Similarity	NPC106215
0.7664	Intermediate Similarity	NPC317380
0.766	Intermediate Similarity	NPC107161
0.7655	Intermediate Similarity	NPC475250
0.7655	Intermediate Similarity	NPC470098
0.7655	Intermediate Similarity	NPC473266
0.7655	Intermediate Similarity	NPC470826
0.7647	Intermediate Similarity	NPC201587
0.7647	Intermediate Similarity	NPC253105
0.7647	Intermediate Similarity	NPC470752
0.7643	Intermediate Similarity	NPC472092
0.7643	Intermediate Similarity	NPC472090
0.7643	Intermediate Similarity	NPC472091
0.7639	Intermediate Similarity	NPC275125
0.7639	Intermediate Similarity	NPC97937
0.7639	Intermediate Similarity	NPC170239
0.7634	Intermediate Similarity	NPC95168
0.763	Intermediate Similarity	NPC234488
0.763	Intermediate Similarity	NPC220935
0.763	Intermediate Similarity	NPC299221
0.763	Intermediate Similarity	NPC311680
0.763	Intermediate Similarity	NPC472338
0.763	Intermediate Similarity	NPC469614
0.763	Intermediate Similarity	NPC91291
0.763	Intermediate Similarity	NPC51840
0.763	Intermediate Similarity	NPC229231
0.763	Intermediate Similarity	NPC469612
0.7626	Intermediate Similarity	NPC25111
0.7626	Intermediate Similarity	NPC6262
0.7626	Intermediate Similarity	NPC272157
0.7626	Intermediate Similarity	NPC73535

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 NPC126216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	571
0.1-0.2	1221
0.2-0.3	3161
0.3-0.4	2252
0.4-0.5	1226
0.5-0.6	612
0.6-0.7	99
0.7-0.8	8
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
0.7803	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1613	Approved
0.7518	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3027	Phase 3
0.7353	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD291	Approved
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9296	Approved
0.7101	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1653	Approved
0.7045	Intermediate Similarity	NPD1548	Phase 1
0.7014	Intermediate Similarity	NPD3454	Phase 3
0.6985	Remote Similarity	NPD2982	Phase 2
0.6985	Remote Similarity	NPD2983	Phase 2
0.6983	Remote Similarity	NPD9094	Approved
0.6981	Remote Similarity	NPD6166	Phase 2
0.6981	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1610	Phase 2
0.6948	Remote Similarity	NPD2801	Approved
0.6917	Remote Similarity	NPD7533	Approved
0.6917	Remote Similarity	NPD7534	Approved
0.6912	Remote Similarity	NPD2981	Phase 2
0.6905	Remote Similarity	NPD968	Approved
0.6871	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4749	Approved
0.6838	Remote Similarity	NPD1091	Approved
0.6809	Remote Similarity	NPD4625	Phase 3
0.6807	Remote Similarity	NPD9365	Approved
0.6786	Remote Similarity	NPD3018	Phase 2
0.678	Remote Similarity	NPD9295	Approved
0.6774	Remote Similarity	NPD1934	Approved
0.6744	Remote Similarity	NPD556	Approved
0.6689	Remote Similarity	NPD1511	Approved
0.6689	Remote Similarity	NPD7213	Phase 3
0.6689	Remote Similarity	NPD7212	Phase 2
0.6667	Remote Similarity	NPD2861	Phase 2
0.6646	Remote Similarity	NPD7054	Approved
0.6645	Remote Similarity	NPD7447	Phase 1
0.6643	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD915	Approved
0.6624	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1465	Phase 2
0.6619	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8053	Approved
0.6607	Remote Similarity	NPD8054	Approved
0.6606	Remote Similarity	NPD7472	Approved
0.6606	Remote Similarity	NPD7074	Phase 3
0.6601	Remote Similarity	NPD1512	Approved
0.6597	Remote Similarity	NPD6233	Phase 2
0.6587	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7228	Approved
0.6567	Remote Similarity	NPD6671	Approved
0.6562	Remote Similarity	NPD6234	Discontinued
0.6552	Remote Similarity	NPD1558	Phase 1
0.6545	Remote Similarity	NPD5844	Phase 1
0.6528	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9093	Approved
0.6515	Remote Similarity	NPD228	Approved
0.6488	Remote Similarity	NPD7549	Discontinued
0.6475	Remote Similarity	NPD422	Phase 1
0.6467	Remote Similarity	NPD6797	Phase 2
0.6466	Remote Similarity	NPD9089	Approved
0.6454	Remote Similarity	NPD3225	Approved
0.6449	Remote Similarity	NPD6516	Phase 2
0.6449	Remote Similarity	NPD5846	Approved
0.6438	Remote Similarity	NPD3882	Suspended
0.6433	Remote Similarity	NPD4380	Phase 2
0.6433	Remote Similarity	NPD4678	Approved
0.6433	Remote Similarity	NPD4675	Approved
0.6429	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7251	Discontinued
0.6415	Remote Similarity	NPD8455	Phase 2
0.6414	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7266	Discontinued
0.6398	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7808	Phase 3
0.6386	Remote Similarity	NPD3818	Discontinued
0.638	Remote Similarity	NPD7199	Phase 2
0.638	Remote Similarity	NPD6959	Discontinued
0.6375	Remote Similarity	NPD5402	Approved
0.6375	Remote Similarity	NPD3817	Phase 2
0.637	Remote Similarity	NPD9299	Approved
0.6352	Remote Similarity	NPD37	Approved
0.6346	Remote Similarity	NPD5403	Approved
0.6343	Remote Similarity	NPD7843	Approved
0.6341	Remote Similarity	NPD3787	Discontinued
0.634	Remote Similarity	NPD6190	Approved
0.6336	Remote Similarity	NPD9552	Approved
0.6336	Remote Similarity	NPD290	Approved
0.6335	Remote Similarity	NPD4967	Phase 2
0.6335	Remote Similarity	NPD4966	Approved
0.6335	Remote Similarity	NPD4965	Approved
0.6333	Remote Similarity	NPD6099	Approved
0.6333	Remote Similarity	NPD6100	Approved
0.6316	Remote Similarity	NPD6674	Discontinued
0.6316	Remote Similarity	NPD1652	Phase 2
0.6309	Remote Similarity	NPD7097	Phase 1
0.6309	Remote Similarity	NPD4538	Approved
0.6309	Remote Similarity	NPD4536	Approved
0.6309	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5283	Phase 1
0.6291	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD3540	Phase 1
0.6291	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7411	Suspended
0.6288	Remote Similarity	NPD2684	Approved
0.6275	Remote Similarity	NPD3750	Approved
0.6273	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD6583	Phase 3
0.6268	Remote Similarity	NPD6582	Phase 2
0.6267	Remote Similarity	NPD5588	Approved
0.6267	Remote Similarity	NPD5960	Phase 3
0.6265	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD4357	Discontinued
0.625	Remote Similarity	NPD3384	Approved
0.625	Remote Similarity	NPD1242	Phase 1
0.625	Remote Similarity	NPD1549	Phase 2
0.625	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3382	Approved
0.625	Remote Similarity	NPD3383	Approved
0.6242	Remote Similarity	NPD6232	Discontinued
0.6241	Remote Similarity	NPD1535	Discovery
0.6235	Remote Similarity	NPD7768	Phase 2
0.6231	Remote Similarity	NPD9501	Approved
0.6225	Remote Similarity	NPD3539	Phase 1
0.6222	Remote Similarity	NPD5535	Approved
0.622	Remote Similarity	NPD5494	Approved
0.6218	Remote Similarity	NPD5401	Approved
0.6218	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3620	Phase 2
0.6216	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7157	Approved
0.6197	Remote Similarity	NPD1481	Phase 2
0.6196	Remote Similarity	NPD7075	Discontinued
0.6194	Remote Similarity	NPD2673	Approved
0.6194	Remote Similarity	NPD2671	Approved
0.619	Remote Similarity	NPD6798	Discontinued
0.619	Remote Similarity	NPD8099	Discontinued
0.619	Remote Similarity	NPD8251	Approved
0.619	Remote Similarity	NPD8252	Approved
0.6178	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5124	Phase 1
0.6174	Remote Similarity	NPD4340	Discontinued
0.6174	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8156	Discontinued
0.6154	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD6382	Discontinued
0.6143	Remote Similarity	NPD1797	Approved
0.6143	Remote Similarity	NPD1798	Approved
0.614	Remote Similarity	NPD7240	Approved
0.6139	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6584	Phase 3
0.6133	Remote Similarity	NPD2224	Approved
0.6133	Remote Similarity	NPD2223	Approved
0.6131	Remote Similarity	NPD7473	Discontinued
0.6129	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2219	Phase 1
0.6127	Remote Similarity	NPD3705	Approved
0.6122	Remote Similarity	NPD7095	Approved
0.6121	Remote Similarity	NPD9088	Approved
0.6121	Remote Similarity	NPD5677	Discontinued
0.6119	Remote Similarity	NPD3022	Approved
0.6119	Remote Similarity	NPD3021	Approved
0.6118	Remote Similarity	NPD1551	Phase 2
0.6115	Remote Similarity	NPD4123	Phase 3
0.6115	Remote Similarity	NPD1102	Approved
0.6115	Remote Similarity	NPD5536	Phase 2
0.6115	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD1103	Approved
0.6111	Remote Similarity	NPD6696	Suspended
0.6104	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3749	Approved
0.6095	Remote Similarity	NPD3751	Discontinued
0.609	Remote Similarity	NPD5058	Phase 3
0.608	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD2797	Approved
0.6067	Remote Similarity	NPD1933	Approved
0.6067	Remote Similarity	NPD230	Phase 1
0.6065	Remote Similarity	NPD7466	Approved
0.6062	Remote Similarity	NPD4005	Discontinued
0.6056	Remote Similarity	NPD3447	Discontinued
0.6051	Remote Similarity	NPD6799	Approved
0.6038	Remote Similarity	NPD2122	Discontinued
0.6027	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7906	Approved
0.6013	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5177	Phase 3
0.6	Remote Similarity	NPD4060	Phase 1

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