NPASS Compound

Structure

CID205850 OpenBabel06191715592D 27 31 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 -1.7321 -2.0000 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 -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 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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -1.7321 0.0000 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 2.5000 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 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 3.4641 4.0000 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 6 2 0 0 0 0 1 8 1 0 0 0 0 2 7 2 0 0 0 0 2 9 1 0 0 0 0 3 6 1 0 0 0 0 3 11 2 0 0 0 0 4 7 1 0 0 0 0 4 12 2 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 14 2 0 0 0 0 8 21 1 0 0 0 0 9 15 2 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 13 24 1 0 0 0 0 14 24 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:	370.03
Volume:	332.486
LogP:	3.574
LogD:	2.718
LogS:	-3.244
# Rotatable Bonds:	0
TPSA:	153.71
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	3.305
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.406
MDCK Permeability:	3.747148366528563e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.677
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	84.83972930908203%
Volume Distribution (VD):	0.671
Pgp-substrate:	23.963464736938477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.314
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	12.347
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.997
AMES Toxicity:	0.672
Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.843
Carcinogencity:	0.386
Eye Corrosion:	0.003
Eye Irritation:	0.672
Respiratory Toxicity:	0.089

Download Data

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

Natural Product: NPC205850

Natural Product ID:	NPC205850
*Common Name:**	Dioxinodehydroeckol
IUPAC Name:	[1,4]benzodioxino[2,3-a]oxanthrene-1,3,6,9,11-pentol
Synonyms:	Dioxinodehydroeckol
Standard InCHIKey:	LBHQACSAGWCMAB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10O9/c19-6-1-8(21)14-11(3-6)26-17-13(24-14)5-10(23)16-18(17)27-15-9(22)2-7(20)4-12(15)25-16/h1-5,19-23H
SMILES:	Oc1cc(O)c2c(c1)oc1c(o2)c2oc3cc(O)cc(c3oc2cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559870
PubChem CID:	10429214
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647823]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22789	Ecklonia cava	Species	Lessoniaceae	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]

☑ 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	3
Ki	1
Others	7

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Others	6

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[527994]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	158300.0	nM	PMID[527994]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	146500.0	nM	PMID[527994]
NPT2	Others	Unspecified		Inhibition	=	25.2	%	PMID[527992]
NPT2	Others	Unspecified		Inhibition	=	23.1	%	PMID[527992]
NPT2	Others	Unspecified		Inhibition	=	19.5	%	PMID[527992]
NPT2	Others	Unspecified		Inhibition	=	16.9	%	PMID[527992]
NPT27	Others	Unspecified		Activity	=	1.0	uM	PMID[527992]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	8000.0	nM	PMID[527993]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	5350.0	nM	PMID[527993]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	1.4	n.a.	PMID[527994]

☑ 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 NPC205850 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	697
0.1-0.2	3793
0.2-0.3	11076
0.3-0.4	8638
0.4-0.5	4580
0.5-0.6	6329
0.6-0.7	5053
0.7-0.8	2445
0.8-0.85	85
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9823	High Similarity	NPC214289
0.9655	High Similarity	NPC228875
0.9655	High Similarity	NPC126216
0.9655	High Similarity	NPC105147
0.9646	High Similarity	NPC151617
0.9646	High Similarity	NPC76915
0.9496	High Similarity	NPC110677
0.856	High Similarity	NPC189589
0.856	High Similarity	NPC469622
0.8492	Intermediate Similarity	NPC37074
0.8438	Intermediate Similarity	NPC208769
0.8425	Intermediate Similarity	NPC247146
0.8413	Intermediate Similarity	NPC298845
0.8385	Intermediate Similarity	NPC60982
0.8372	Intermediate Similarity	NPC287780
0.8348	Intermediate Similarity	NPC232654
0.8346	Intermediate Similarity	NPC469621
0.832	Intermediate Similarity	NPC217854
0.832	Intermediate Similarity	NPC192810
0.8295	Intermediate Similarity	NPC60756
0.8276	Intermediate Similarity	NPC124712
0.8271	Intermediate Similarity	NPC48956
0.8254	Intermediate Similarity	NPC25817
0.8254	Intermediate Similarity	NPC221090
0.824	Intermediate Similarity	NPC152722
0.8188	Intermediate Similarity	NPC150714
0.8188	Intermediate Similarity	NPC95652
0.8148	Intermediate Similarity	NPC262189
0.8103	Intermediate Similarity	NPC307875
0.8088	Intermediate Similarity	NPC8577
0.808	Intermediate Similarity	NPC276195
0.8071	Intermediate Similarity	NPC281549
0.8062	Intermediate Similarity	NPC216836
0.8043	Intermediate Similarity	NPC28440
0.8043	Intermediate Similarity	NPC171932
0.803	Intermediate Similarity	NPC131128
0.803	Intermediate Similarity	NPC474134
0.8016	Intermediate Similarity	NPC145780
0.8015	Intermediate Similarity	NPC214860
0.7939	Intermediate Similarity	NPC45824
0.7923	Intermediate Similarity	NPC5447
0.7923	Intermediate Similarity	NPC250432
0.791	Intermediate Similarity	NPC310854
0.791	Intermediate Similarity	NPC256307
0.791	Intermediate Similarity	NPC170694
0.791	Intermediate Similarity	NPC66840
0.7895	Intermediate Similarity	NPC127624
0.7895	Intermediate Similarity	NPC202762
0.7895	Intermediate Similarity	NPC161203
0.7895	Intermediate Similarity	NPC86655
0.7887	Intermediate Similarity	NPC476969
0.7868	Intermediate Similarity	NPC276490
0.7868	Intermediate Similarity	NPC102904
0.7868	Intermediate Similarity	NPC176051
0.7868	Intermediate Similarity	NPC211549
0.7868	Intermediate Similarity	NPC474282
0.7868	Intermediate Similarity	NPC326797
0.7868	Intermediate Similarity	NPC474390
0.7868	Intermediate Similarity	NPC103976
0.7868	Intermediate Similarity	NPC107551
0.7863	Intermediate Similarity	NPC46274
0.7863	Intermediate Similarity	NPC226331
0.7846	Intermediate Similarity	NPC181361
0.7846	Intermediate Similarity	NPC171533
0.784	Intermediate Similarity	NPC228907
0.7836	Intermediate Similarity	NPC37196
0.7836	Intermediate Similarity	NPC94236
0.7829	Intermediate Similarity	NPC228972
0.7829	Intermediate Similarity	NPC122792
0.7826	Intermediate Similarity	NPC178054
0.781	Intermediate Similarity	NPC127218
0.781	Intermediate Similarity	NPC319647
0.781	Intermediate Similarity	NPC25966
0.781	Intermediate Similarity	NPC245207
0.781	Intermediate Similarity	NPC22517
0.7801	Intermediate Similarity	NPC96576
0.7786	Intermediate Similarity	NPC470699
0.7786	Intermediate Similarity	NPC210355
0.7786	Intermediate Similarity	NPC50368
0.7778	Intermediate Similarity	NPC106215
0.7762	Intermediate Similarity	NPC318373
0.7762	Intermediate Similarity	NPC321657
0.7762	Intermediate Similarity	NPC211561
0.7761	Intermediate Similarity	NPC16208
0.7761	Intermediate Similarity	NPC160991
0.7761	Intermediate Similarity	NPC7903
0.7761	Intermediate Similarity	NPC184447
0.7761	Intermediate Similarity	NPC35932
0.776	Intermediate Similarity	NPC9248
0.7754	Intermediate Similarity	NPC22317
0.7754	Intermediate Similarity	NPC61783
0.7754	Intermediate Similarity	NPC20520
0.7754	Intermediate Similarity	NPC259519
0.7754	Intermediate Similarity	NPC266197
0.7754	Intermediate Similarity	NPC291101
0.7746	Intermediate Similarity	NPC202742
0.7746	Intermediate Similarity	NPC294558
0.7746	Intermediate Similarity	NPC204770
0.7746	Intermediate Similarity	NPC70409
0.7746	Intermediate Similarity	NPC262911
0.7746	Intermediate Similarity	NPC18185
0.7746	Intermediate Similarity	NPC82917
0.7746	Intermediate Similarity	NPC170103
0.7746	Intermediate Similarity	NPC263940
0.7746	Intermediate Similarity	NPC236202
0.7746	Intermediate Similarity	NPC58190
0.7746	Intermediate Similarity	NPC108811
0.7744	Intermediate Similarity	NPC229231
0.7744	Intermediate Similarity	NPC91291
0.7737	Intermediate Similarity	NPC59324
0.7737	Intermediate Similarity	NPC65530
0.7734	Intermediate Similarity	NPC190454
0.7734	Intermediate Similarity	NPC57751
0.7734	Intermediate Similarity	NPC97432
0.7727	Intermediate Similarity	NPC266691
0.7724	Intermediate Similarity	NPC264875
0.7724	Intermediate Similarity	NPC163598
0.7724	Intermediate Similarity	NPC120774
0.7721	Intermediate Similarity	NPC47398
0.7721	Intermediate Similarity	NPC112939
0.7721	Intermediate Similarity	NPC112246
0.7721	Intermediate Similarity	NPC121812
0.7721	Intermediate Similarity	NPC283009
0.7721	Intermediate Similarity	NPC94750
0.7721	Intermediate Similarity	NPC261873
0.7721	Intermediate Similarity	NPC201357
0.7721	Intermediate Similarity	NPC281521
0.7721	Intermediate Similarity	NPC472337
0.7721	Intermediate Similarity	NPC260898
0.7721	Intermediate Similarity	NPC474206
0.7721	Intermediate Similarity	NPC255147
0.7721	Intermediate Similarity	NPC234333
0.7721	Intermediate Similarity	NPC470356
0.7721	Intermediate Similarity	NPC134968
0.7721	Intermediate Similarity	NPC195022
0.7714	Intermediate Similarity	NPC252169
0.771	Intermediate Similarity	NPC45728
0.7704	Intermediate Similarity	NPC168059
0.7704	Intermediate Similarity	NPC229442
0.7698	Intermediate Similarity	NPC471389
0.7698	Intermediate Similarity	NPC247291
0.7687	Intermediate Similarity	NPC309787
0.7687	Intermediate Similarity	NPC268266
0.7687	Intermediate Similarity	NPC472597
0.7687	Intermediate Similarity	NPC220825
0.7687	Intermediate Similarity	NPC42760
0.7687	Intermediate Similarity	NPC268342
0.7681	Intermediate Similarity	NPC212770
0.7681	Intermediate Similarity	NPC55947
0.7681	Intermediate Similarity	NPC98777
0.7674	Intermediate Similarity	NPC473411
0.7674	Intermediate Similarity	NPC262253
0.7674	Intermediate Similarity	NPC71579
0.7672	Intermediate Similarity	NPC314803
0.7669	Intermediate Similarity	NPC10225
0.7669	Intermediate Similarity	NPC58164
0.7664	Intermediate Similarity	NPC474639
0.7664	Intermediate Similarity	NPC230734
0.7664	Intermediate Similarity	NPC265433
0.7664	Intermediate Similarity	NPC227503
0.7664	Intermediate Similarity	NPC472336
0.7664	Intermediate Similarity	NPC173660
0.7664	Intermediate Similarity	NPC302701
0.7664	Intermediate Similarity	NPC203230
0.7664	Intermediate Similarity	NPC269091
0.7664	Intermediate Similarity	NPC306441
0.7664	Intermediate Similarity	NPC270456
0.7664	Intermediate Similarity	NPC242028
0.7664	Intermediate Similarity	NPC16435
0.7664	Intermediate Similarity	NPC162659
0.7664	Intermediate Similarity	NPC472334
0.7664	Intermediate Similarity	NPC248727
0.7647	Intermediate Similarity	NPC103967
0.7647	Intermediate Similarity	NPC317380
0.7643	Intermediate Similarity	NPC107161
0.763	Intermediate Similarity	NPC201587
0.763	Intermediate Similarity	NPC61477
0.763	Intermediate Similarity	NPC78770
0.763	Intermediate Similarity	NPC261619
0.763	Intermediate Similarity	NPC15658
0.763	Intermediate Similarity	NPC470752
0.763	Intermediate Similarity	NPC219876
0.763	Intermediate Similarity	NPC253105
0.763	Intermediate Similarity	NPC185604
0.763	Intermediate Similarity	NPC126029
0.7623	Intermediate Similarity	NPC247871
0.7622	Intermediate Similarity	NPC97937
0.7622	Intermediate Similarity	NPC275125
0.7622	Intermediate Similarity	NPC170239
0.7622	Intermediate Similarity	NPC101376
0.7619	Intermediate Similarity	NPC8712
0.7615	Intermediate Similarity	NPC95168
0.7612	Intermediate Similarity	NPC311680
0.7612	Intermediate Similarity	NPC472338
0.7612	Intermediate Similarity	NPC469614
0.7612	Intermediate Similarity	NPC299221
0.7612	Intermediate Similarity	NPC469612
0.7612	Intermediate Similarity	NPC220935
0.7612	Intermediate Similarity	NPC51840
0.7612	Intermediate Similarity	NPC234488

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 NPC205850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	515
0.1-0.2	1381
0.2-0.3	2957
0.3-0.4	2490
0.4-0.5	1287
0.5-0.6	379
0.6-0.7	104
0.7-0.8	37
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
0.7923	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1613	Approved
0.763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7395	Intermediate Similarity	NPD291	Approved
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7328	Intermediate Similarity	NPD9296	Approved
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1548	Phase 1
0.7105	Intermediate Similarity	NPD9094	Approved
0.708	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6166	Phase 2
0.707	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1610	Phase 2
0.7059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1653	Approved
0.7016	Intermediate Similarity	NPD968	Approved
0.6993	Remote Similarity	NPD3454	Phase 3
0.6963	Remote Similarity	NPD2983	Phase 2
0.6963	Remote Similarity	NPD2982	Phase 2
0.6928	Remote Similarity	NPD2801	Approved
0.6923	Remote Similarity	NPD9365	Approved
0.6897	Remote Similarity	NPD9295	Approved
0.6894	Remote Similarity	NPD7534	Approved
0.6894	Remote Similarity	NPD7533	Approved
0.6889	Remote Similarity	NPD2981	Phase 2
0.6863	Remote Similarity	NPD1934	Approved
0.685	Remote Similarity	NPD556	Approved
0.6838	Remote Similarity	NPD4749	Approved
0.6818	Remote Similarity	NPD1465	Phase 2
0.6815	Remote Similarity	NPD1091	Approved
0.6786	Remote Similarity	NPD4625	Phase 3
0.6779	Remote Similarity	NPD1511	Approved
0.6763	Remote Similarity	NPD3018	Phase 2
0.6748	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD915	Approved
0.6728	Remote Similarity	NPD7054	Approved
0.6689	Remote Similarity	NPD1512	Approved
0.6687	Remote Similarity	NPD7074	Phase 3
0.6687	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD7212	Phase 2
0.6667	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD7213	Phase 3
0.6643	Remote Similarity	NPD2861	Phase 2
0.6643	Remote Similarity	NPD1558	Phase 1
0.6637	Remote Similarity	NPD9093	Approved
0.6623	Remote Similarity	NPD7447	Phase 1
0.6619	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD228	Approved
0.6603	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD9089	Approved
0.6573	Remote Similarity	NPD6233	Phase 2
0.6569	Remote Similarity	NPD422	Phase 1
0.6566	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3225	Approved
0.6545	Remote Similarity	NPD6797	Phase 2
0.6541	Remote Similarity	NPD6234	Discontinued
0.6541	Remote Similarity	NPD6671	Approved
0.6524	Remote Similarity	NPD5844	Phase 1
0.6506	Remote Similarity	NPD7251	Discontinued
0.6503	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD8054	Approved
0.6488	Remote Similarity	NPD8053	Approved
0.6486	Remote Similarity	NPD7266	Discontinued
0.6467	Remote Similarity	NPD7808	Phase 3
0.6467	Remote Similarity	NPD7549	Discontinued
0.6466	Remote Similarity	NPD9299	Approved
0.6434	Remote Similarity	NPD290	Approved
0.6434	Remote Similarity	NPD9552	Approved
0.6423	Remote Similarity	NPD6516	Phase 2
0.6423	Remote Similarity	NPD5846	Approved
0.6415	Remote Similarity	NPD3882	Suspended
0.641	Remote Similarity	NPD4678	Approved
0.641	Remote Similarity	NPD4675	Approved
0.641	Remote Similarity	NPD4380	Phase 2
0.6405	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3818	Discontinued
0.6358	Remote Similarity	NPD3750	Approved
0.6358	Remote Similarity	NPD7199	Phase 2
0.6352	Remote Similarity	NPD5402	Approved
0.6352	Remote Similarity	NPD3817	Phase 2
0.6349	Remote Similarity	NPD1242	Phase 1
0.6338	Remote Similarity	NPD1469	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1549	Phase 2
0.6331	Remote Similarity	NPD1535	Discovery
0.6329	Remote Similarity	NPD37	Approved
0.6328	Remote Similarity	NPD9501	Approved
0.6323	Remote Similarity	NPD5403	Approved
0.6316	Remote Similarity	NPD6190	Approved
0.6316	Remote Similarity	NPD7843	Approved
0.6312	Remote Similarity	NPD4966	Approved
0.6312	Remote Similarity	NPD4965	Approved
0.6312	Remote Similarity	NPD4967	Phase 2
0.6309	Remote Similarity	NPD6100	Approved
0.6309	Remote Similarity	NPD6099	Approved
0.6299	Remote Similarity	NPD5401	Approved
0.6296	Remote Similarity	NPD5494	Approved
0.6291	Remote Similarity	NPD6674	Discontinued
0.6291	Remote Similarity	NPD1652	Phase 2
0.6289	Remote Similarity	NPD8455	Phase 2
0.6286	Remote Similarity	NPD1481	Phase 2
0.6284	Remote Similarity	NPD4536	Approved
0.6284	Remote Similarity	NPD4538	Approved
0.6284	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5283	Phase 1
0.6267	Remote Similarity	NPD3540	Phase 1
0.6266	Remote Similarity	NPD7411	Suspended
0.626	Remote Similarity	NPD2684	Approved
0.6258	Remote Similarity	NPD6959	Discontinued
0.6258	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD5588	Approved
0.6242	Remote Similarity	NPD5960	Phase 3
0.6241	Remote Similarity	NPD6582	Phase 2
0.6241	Remote Similarity	NPD6583	Phase 3
0.6234	Remote Similarity	NPD4357	Discontinued
0.6228	Remote Similarity	NPD9088	Approved
0.6228	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD3383	Approved
0.6226	Remote Similarity	NPD3382	Approved
0.6226	Remote Similarity	NPD3384	Approved
0.622	Remote Similarity	NPD3787	Discontinued
0.622	Remote Similarity	NPD6232	Discontinued
0.6213	Remote Similarity	NPD7240	Approved
0.62	Remote Similarity	NPD1551	Phase 2
0.62	Remote Similarity	NPD3539	Phase 1
0.6194	Remote Similarity	NPD5535	Approved
0.6194	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3620	Phase 2
0.6181	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7157	Approved
0.6174	Remote Similarity	NPD7097	Phase 1
0.6173	Remote Similarity	NPD7075	Discontinued
0.6168	Remote Similarity	NPD3751	Discontinued
0.6165	Remote Similarity	NPD2673	Approved
0.6165	Remote Similarity	NPD2671	Approved
0.6164	Remote Similarity	NPD6798	Discontinued
0.6149	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD5124	Phase 1
0.6149	Remote Similarity	NPD230	Phase 1
0.6149	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1933	Approved
0.6149	Remote Similarity	NPD4340	Discontinued
0.6144	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD2122	Discontinued
0.6115	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD1797	Approved
0.6115	Remote Similarity	NPD6382	Discontinued
0.6115	Remote Similarity	NPD1798	Approved
0.6111	Remote Similarity	NPD6584	Phase 3
0.6108	Remote Similarity	NPD7473	Discontinued
0.6107	Remote Similarity	NPD2224	Approved
0.6107	Remote Similarity	NPD2223	Approved
0.6104	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD2219	Phase 1
0.6099	Remote Similarity	NPD3705	Approved
0.6098	Remote Similarity	NPD5677	Discontinued
0.6096	Remote Similarity	NPD7095	Approved
0.609	Remote Similarity	NPD3022	Approved
0.609	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.609	Remote Similarity	NPD3021	Approved
0.609	Remote Similarity	NPD4123	Phase 3
0.6087	Remote Similarity	NPD5536	Phase 2
0.6087	Remote Similarity	NPD1103	Approved
0.6087	Remote Similarity	NPD1102	Approved
0.6084	Remote Similarity	NPD6696	Suspended
0.6078	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD3749	Approved
0.6071	Remote Similarity	NPD8099	Discontinued
0.6071	Remote Similarity	NPD8252	Approved
0.6071	Remote Similarity	NPD8251	Approved
0.6065	Remote Similarity	NPD5058	Phase 3
0.6058	Remote Similarity	NPD191	Approved
0.6048	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD2797	Approved
0.6042	Remote Similarity	NPD1203	Approved
0.604	Remote Similarity	NPD447	Suspended
0.6039	Remote Similarity	NPD7466	Approved
0.6038	Remote Similarity	NPD4005	Discontinued
0.6036	Remote Similarity	NPD8156	Discontinued
0.6028	Remote Similarity	NPD3447	Discontinued
0.6026	Remote Similarity	NPD6799	Approved
0.6026	Remote Similarity	NPD1510	Phase 2
0.6026	Remote Similarity	NPD3748	Approved
0.6012	Remote Similarity	NPD7768	Phase 2
0.6	Remote Similarity	NPD7906	Approved
0.6	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD7096	Clinical (unspecified phase)

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