NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	774.46
Volume:	811.005
LogP:	4.634
LogD:	3.616
LogS:	-4.422
# Rotatable Bonds:	28
TPSA:	186.12
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.047
Synthetic Accessibility Score:	5.327
Fsp3:	0.721
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.142
MDCK Permeability:	3.8161040720297024e-05
Pgp-inhibitor:	0.836
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.5
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	96.03052520751953%
Volume Distribution (VD):	1.35
Pgp-substrate:	0.40722769498825073%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.614
CYP2D6-inhibitor:	0.166
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.924
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	3.537
Half-life (T1/2):	0.953

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.272
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.679
Skin Sensitization:	0.331
Carcinogencity:	0.645
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC476612

Natural Product ID:	NPC476612
*Common Name:**	[(2S)-2-[6-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]hexanoyloxy]-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] 8-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoate
IUPAC Name:	[(2S)-2-[6-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]hexanoyloxy]-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] 8-[(1R,5R)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoate
Synonyms:	Arabidopside A
Standard InCHIKey:	FXAOGBMUKJMRHB-YGJAHLLZSA-N
Standard InCHI:	InChI=1S/C43H66O12/c1-3-5-11-19-33-30(23-25-35(33)45)17-13-8-7-9-15-21-38(47)52-28-32(29-53-43-42(51)41(50)40(49)37(27-44)55-43)54-39(48)22-16-10-14-18-31-24-26-36(46)34(31)20-12-6-4-2/h5-6,11-12,23-26,30-34,37,40-44,49-51H,3-4,7-10,13-22,27-29H2,1-2H3/b11-5-,12-6-/t30-,31-,32-,33-,34-,37-,40+,41+,42-,43-/m1/s1
SMILES:	CC/C=C\C[C@@H]1[C@@H](C=CC1=O)CCCCCCCC(=O)OC[C@H](CO[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)OC(=O)CCCCC[C@@H]3C=CC(=O)[C@@H]3C/C=C\CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3130	Organism	Lepidium sativum	Lepidium sativum	Inhibition	=	30	%	PMID[15844959]

☑ 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 NPC476612 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	196
0.1-0.2	1167
0.2-0.3	5163
0.3-0.4	10941
0.4-0.5	11797
0.5-0.6	7895
0.6-0.7	5051
0.7-0.8	464
0.8-0.85	19
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476613
0.9677	High Similarity	NPC476611
0.866	High Similarity	NPC472015
0.8557	High Similarity	NPC278506
0.8333	Intermediate Similarity	NPC21693
0.8333	Intermediate Similarity	NPC236649
0.8229	Intermediate Similarity	NPC472197
0.8163	Intermediate Similarity	NPC108141
0.8152	Intermediate Similarity	NPC38295
0.8152	Intermediate Similarity	NPC470313
0.8152	Intermediate Similarity	NPC473500
0.8152	Intermediate Similarity	NPC156089
0.8144	Intermediate Similarity	NPC238090
0.8144	Intermediate Similarity	NPC472195
0.8144	Intermediate Similarity	NPC472196
0.8144	Intermediate Similarity	NPC320089
0.8125	Intermediate Similarity	NPC478003
0.8125	Intermediate Similarity	NPC478004
0.8125	Intermediate Similarity	NPC158388
0.81	Intermediate Similarity	NPC56071
0.81	Intermediate Similarity	NPC70733
0.8081	Intermediate Similarity	NPC54731
0.8061	Intermediate Similarity	NPC159698
0.8041	Intermediate Similarity	NPC472199
0.802	Intermediate Similarity	NPC473146
0.8	Intermediate Similarity	NPC392
0.8	Intermediate Similarity	NPC177524
0.8	Intermediate Similarity	NPC475309
0.8	Intermediate Similarity	NPC219900
0.8	Intermediate Similarity	NPC472290
0.7959	Intermediate Similarity	NPC478036
0.7959	Intermediate Similarity	NPC478037
0.7935	Intermediate Similarity	NPC280367
0.79	Intermediate Similarity	NPC306041
0.7889	Intermediate Similarity	NPC110813
0.7885	Intermediate Similarity	NPC474917
0.7879	Intermediate Similarity	NPC472198
0.783	Intermediate Similarity	NPC475960
0.7802	Intermediate Similarity	NPC133377
0.7789	Intermediate Similarity	NPC477746
0.7789	Intermediate Similarity	NPC477747
0.7757	Intermediate Similarity	NPC118225
0.7727	Intermediate Similarity	NPC165439
0.7723	Intermediate Similarity	NPC256230
0.7706	Intermediate Similarity	NPC471967
0.7692	Intermediate Similarity	NPC223834
0.7684	Intermediate Similarity	NPC266718
0.7679	Intermediate Similarity	NPC234522
0.7677	Intermediate Similarity	NPC477749
0.767	Intermediate Similarity	NPC469871
0.767	Intermediate Similarity	NPC469870
0.7664	Intermediate Similarity	NPC473288
0.7647	Intermediate Similarity	NPC261372
0.7647	Intermediate Similarity	NPC263674
0.7647	Intermediate Similarity	NPC266842
0.7647	Intermediate Similarity	NPC40812
0.7647	Intermediate Similarity	NPC58267
0.7642	Intermediate Similarity	NPC162033
0.7642	Intermediate Similarity	NPC239961
0.7642	Intermediate Similarity	NPC478038
0.7636	Intermediate Similarity	NPC477944
0.7619	Intermediate Similarity	NPC473148
0.7604	Intermediate Similarity	NPC475206
0.76	Intermediate Similarity	NPC61201
0.7596	Intermediate Similarity	NPC57586
0.7596	Intermediate Similarity	NPC154132
0.7596	Intermediate Similarity	NPC471637
0.7596	Intermediate Similarity	NPC475655
0.7596	Intermediate Similarity	NPC2313
0.7596	Intermediate Similarity	NPC198992
0.7596	Intermediate Similarity	NPC475157
0.7596	Intermediate Similarity	NPC154127
0.7593	Intermediate Similarity	NPC246205
0.7576	Intermediate Similarity	NPC473311
0.7576	Intermediate Similarity	NPC473448
0.7576	Intermediate Similarity	NPC202886
0.7573	Intermediate Similarity	NPC40182
0.7573	Intermediate Similarity	NPC49833
0.7573	Intermediate Similarity	NPC203627
0.7573	Intermediate Similarity	NPC249171
0.7573	Intermediate Similarity	NPC198422
0.757	Intermediate Similarity	NPC254538
0.757	Intermediate Similarity	NPC474285
0.757	Intermediate Similarity	NPC293512
0.7568	Intermediate Similarity	NPC74727
0.7553	Intermediate Similarity	NPC469469
0.7549	Intermediate Similarity	NPC143446
0.7549	Intermediate Similarity	NPC241911
0.7549	Intermediate Similarity	NPC474297
0.7547	Intermediate Similarity	NPC264584
0.7547	Intermediate Similarity	NPC86095
0.7547	Intermediate Similarity	NPC472748
0.7547	Intermediate Similarity	NPC223741
0.7547	Intermediate Similarity	NPC231271
0.7547	Intermediate Similarity	NPC470519
0.7545	Intermediate Similarity	NPC1111
0.7545	Intermediate Similarity	NPC261750
0.7544	Intermediate Similarity	NPC48692
0.7544	Intermediate Similarity	NPC241192
0.7544	Intermediate Similarity	NPC470312
0.7526	Intermediate Similarity	NPC477015
0.7525	Intermediate Similarity	NPC63897
0.7525	Intermediate Similarity	NPC2003
0.7525	Intermediate Similarity	NPC25701
0.7525	Intermediate Similarity	NPC256368
0.7524	Intermediate Similarity	NPC106668
0.7524	Intermediate Similarity	NPC261117
0.7524	Intermediate Similarity	NPC310804
0.7524	Intermediate Similarity	NPC13171
0.7524	Intermediate Similarity	NPC222062
0.7524	Intermediate Similarity	NPC225353
0.7524	Intermediate Similarity	NPC476235
0.7524	Intermediate Similarity	NPC195510
0.7524	Intermediate Similarity	NPC476126
0.7523	Intermediate Similarity	NPC83005
0.7523	Intermediate Similarity	NPC127153
0.7523	Intermediate Similarity	NPC129340
0.7523	Intermediate Similarity	NPC114961
0.7523	Intermediate Similarity	NPC27551
0.7522	Intermediate Similarity	NPC473617
0.7522	Intermediate Similarity	NPC13710
0.7522	Intermediate Similarity	NPC473828
0.7522	Intermediate Similarity	NPC239293
0.75	Intermediate Similarity	NPC272576
0.75	Intermediate Similarity	NPC255677
0.75	Intermediate Similarity	NPC288471
0.75	Intermediate Similarity	NPC295389
0.75	Intermediate Similarity	NPC31797
0.75	Intermediate Similarity	NPC306344
0.75	Intermediate Similarity	NPC22149
0.7478	Intermediate Similarity	NPC202051
0.7477	Intermediate Similarity	NPC210178
0.7477	Intermediate Similarity	NPC73455
0.7477	Intermediate Similarity	NPC63023
0.7477	Intermediate Similarity	NPC260665
0.7477	Intermediate Similarity	NPC95243
0.7477	Intermediate Similarity	NPC200944
0.7477	Intermediate Similarity	NPC472751
0.7477	Intermediate Similarity	NPC476738
0.7477	Intermediate Similarity	NPC472749
0.7477	Intermediate Similarity	NPC476740
0.7476	Intermediate Similarity	NPC304445
0.7476	Intermediate Similarity	NPC236580
0.7475	Intermediate Similarity	NPC477016
0.7475	Intermediate Similarity	NPC477017
0.7475	Intermediate Similarity	NPC477748
0.7456	Intermediate Similarity	NPC161065
0.7455	Intermediate Similarity	NPC250481
0.7455	Intermediate Similarity	NPC285410
0.7455	Intermediate Similarity	NPC263827
0.7453	Intermediate Similarity	NPC197736
0.7453	Intermediate Similarity	NPC284929
0.7453	Intermediate Similarity	NPC267869
0.7453	Intermediate Similarity	NPC110989
0.7453	Intermediate Similarity	NPC309398
0.7453	Intermediate Similarity	NPC472747
0.7453	Intermediate Similarity	NPC197541
0.7453	Intermediate Similarity	NPC118761
0.7453	Intermediate Similarity	NPC27687
0.7453	Intermediate Similarity	NPC472750
0.7453	Intermediate Similarity	NPC234304
0.7434	Intermediate Similarity	NPC474483
0.7431	Intermediate Similarity	NPC57362
0.7431	Intermediate Similarity	NPC306746
0.7431	Intermediate Similarity	NPC204407
0.7431	Intermediate Similarity	NPC137917
0.7431	Intermediate Similarity	NPC237503
0.7431	Intermediate Similarity	NPC167383
0.7431	Intermediate Similarity	NPC313668
0.7431	Intermediate Similarity	NPC315836
0.7431	Intermediate Similarity	NPC265655
0.7429	Intermediate Similarity	NPC476213
0.7429	Intermediate Similarity	NPC476246
0.7429	Intermediate Similarity	NPC476134
0.7429	Intermediate Similarity	NPC3488
0.7429	Intermediate Similarity	NPC101067
0.7429	Intermediate Similarity	NPC28304
0.7429	Intermediate Similarity	NPC477871
0.7429	Intermediate Similarity	NPC477870
0.7429	Intermediate Similarity	NPC298255
0.7429	Intermediate Similarity	NPC287539
0.7426	Intermediate Similarity	NPC473723
0.7426	Intermediate Similarity	NPC473561
0.7426	Intermediate Similarity	NPC475173
0.7426	Intermediate Similarity	NPC473663
0.7426	Intermediate Similarity	NPC473520
0.7423	Intermediate Similarity	NPC477014
0.7423	Intermediate Similarity	NPC477013
0.7423	Intermediate Similarity	NPC329615
0.7423	Intermediate Similarity	NPC329838
0.7423	Intermediate Similarity	NPC322529
0.7423	Intermediate Similarity	NPC471567
0.7423	Intermediate Similarity	NPC120398
0.7419	Intermediate Similarity	NPC192006
0.7411	Intermediate Similarity	NPC477580
0.7411	Intermediate Similarity	NPC473882
0.7411	Intermediate Similarity	NPC471398
0.7404	Intermediate Similarity	NPC261377
0.7404	Intermediate Similarity	NPC83895
0.7404	Intermediate Similarity	NPC37866

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 NPC476612 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1736
0.2-0.3	3939
0.3-0.4	2185
0.4-0.5	680
0.5-0.6	321
0.6-0.7	116
0.7-0.8	6
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
0.8	Intermediate Similarity	NPD6686	Approved
0.7755	Intermediate Similarity	NPD46	Approved
0.7755	Intermediate Similarity	NPD6698	Approved
0.757	Intermediate Similarity	NPD6412	Phase 2
0.7404	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7641	Discontinued
0.7327	Intermediate Similarity	NPD7983	Approved
0.7248	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6435	Approved
0.7059	Intermediate Similarity	NPD8328	Phase 3
0.7059	Intermediate Similarity	NPD7829	Approved
0.7059	Intermediate Similarity	NPD7830	Approved
0.7034	Intermediate Similarity	NPD8515	Approved
0.7034	Intermediate Similarity	NPD8517	Approved
0.7034	Intermediate Similarity	NPD8516	Approved
0.7034	Intermediate Similarity	NPD8513	Phase 3
0.7019	Intermediate Similarity	NPD5282	Discontinued
0.6967	Remote Similarity	NPD7736	Approved
0.6942	Remote Similarity	NPD7507	Approved
0.6917	Remote Similarity	NPD7642	Approved
0.6907	Remote Similarity	NPD5368	Approved
0.6903	Remote Similarity	NPD6371	Approved
0.6891	Remote Similarity	NPD8444	Approved
0.6887	Remote Similarity	NPD7839	Suspended
0.6833	Remote Similarity	NPD6370	Approved
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7319	Approved
0.6765	Remote Similarity	NPD4250	Approved
0.6765	Remote Similarity	NPD4251	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6733	Remote Similarity	NPD5363	Approved
0.6724	Remote Similarity	NPD8133	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.67	Remote Similarity	NPD5362	Discontinued
0.67	Remote Similarity	NPD7154	Phase 3
0.6694	Remote Similarity	NPD8336	Approved
0.6694	Remote Similarity	NPD8337	Approved
0.6694	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD7328	Approved
0.6638	Remote Similarity	NPD6882	Approved
0.6638	Remote Similarity	NPD8297	Approved
0.6614	Remote Similarity	NPD8338	Approved
0.6613	Remote Similarity	NPD7078	Approved
0.6612	Remote Similarity	NPD7503	Approved
0.6612	Remote Similarity	NPD8033	Approved
0.6612	Remote Similarity	NPD8378	Approved
0.6612	Remote Similarity	NPD8380	Approved
0.6612	Remote Similarity	NPD8296	Approved
0.6612	Remote Similarity	NPD8335	Approved
0.6612	Remote Similarity	NPD8379	Approved
0.6585	Remote Similarity	NPD8342	Approved
0.6585	Remote Similarity	NPD8340	Approved
0.6585	Remote Similarity	NPD8341	Approved
0.6585	Remote Similarity	NPD8299	Approved
0.6583	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6009	Approved
0.6532	Remote Similarity	NPD8451	Approved
0.6531	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6319	Approved
0.6486	Remote Similarity	NPD5344	Discontinued
0.648	Remote Similarity	NPD8448	Approved
0.648	Remote Similarity	NPD8074	Phase 3
0.6476	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6101	Approved
0.6475	Remote Similarity	NPD6016	Approved
0.6475	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6015	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6449	Remote Similarity	NPD5779	Approved
0.6441	Remote Similarity	NPD4632	Approved
0.6436	Remote Similarity	NPD4270	Approved
0.6436	Remote Similarity	NPD4269	Approved
0.6423	Remote Similarity	NPD5988	Approved
0.6412	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4819	Approved
0.64	Remote Similarity	NPD4822	Approved
0.64	Remote Similarity	NPD4820	Approved
0.64	Remote Similarity	NPD4821	Approved
0.6393	Remote Similarity	NPD6059	Approved
0.6371	Remote Similarity	NPD6067	Discontinued
0.6364	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6355	Remote Similarity	NPD6411	Approved
0.6346	Remote Similarity	NPD5786	Approved
0.6328	Remote Similarity	NPD8392	Approved
0.6328	Remote Similarity	NPD8390	Approved
0.6328	Remote Similarity	NPD8391	Approved
0.6321	Remote Similarity	NPD1695	Approved
0.6293	Remote Similarity	NPD6881	Approved
0.6293	Remote Similarity	NPD6899	Approved
0.6271	Remote Similarity	NPD6650	Approved
0.6271	Remote Similarity	NPD6649	Approved
0.6271	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD4252	Approved
0.6218	Remote Similarity	NPD6053	Discontinued
0.6216	Remote Similarity	NPD6083	Phase 2
0.6216	Remote Similarity	NPD6084	Phase 2
0.6216	Remote Similarity	NPD7902	Approved
0.6214	Remote Similarity	NPD6110	Phase 1
0.6207	Remote Similarity	NPD5697	Approved
0.6196	Remote Similarity	NPD3197	Phase 1
0.6186	Remote Similarity	NPD7290	Approved
0.6186	Remote Similarity	NPD6883	Approved
0.6186	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7638	Approved
0.6161	Remote Similarity	NPD4225	Approved
0.6154	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7320	Approved
0.6154	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD7115	Discovery
0.6147	Remote Similarity	NPD6399	Phase 3
0.614	Remote Similarity	NPD8138	Approved
0.614	Remote Similarity	NPD8083	Approved
0.614	Remote Similarity	NPD8086	Approved
0.614	Remote Similarity	NPD8082	Approved
0.614	Remote Similarity	NPD8139	Approved
0.614	Remote Similarity	NPD8085	Approved
0.614	Remote Similarity	NPD8084	Approved
0.6134	Remote Similarity	NPD6617	Approved
0.6134	Remote Similarity	NPD6847	Approved
0.6134	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD5739	Approved
0.6121	Remote Similarity	NPD7128	Approved
0.6121	Remote Similarity	NPD6402	Approved
0.6121	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD7604	Phase 2
0.6111	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6648	Approved
0.6106	Remote Similarity	NPD7639	Approved
0.6106	Remote Similarity	NPD7640	Approved
0.6102	Remote Similarity	NPD6372	Approved
0.6102	Remote Similarity	NPD6012	Approved
0.6102	Remote Similarity	NPD6013	Approved
0.6102	Remote Similarity	NPD6014	Approved
0.6102	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8275	Approved
0.6087	Remote Similarity	NPD8276	Approved
0.608	Remote Similarity	NPD5983	Phase 2
0.6077	Remote Similarity	NPD5956	Approved
0.6075	Remote Similarity	NPD6903	Approved
0.6058	Remote Similarity	NPD5332	Approved
0.6058	Remote Similarity	NPD5331	Approved
0.6055	Remote Similarity	NPD7515	Phase 2
0.6055	Remote Similarity	NPD7637	Suspended
0.605	Remote Similarity	NPD6421	Discontinued
0.6038	Remote Similarity	NPD7521	Approved
0.6038	Remote Similarity	NPD5330	Approved
0.6038	Remote Similarity	NPD6409	Approved
0.6038	Remote Similarity	NPD7334	Approved
0.6038	Remote Similarity	NPD6684	Approved
0.6038	Remote Similarity	NPD7146	Approved
0.6036	Remote Similarity	NPD5695	Phase 3
0.6034	Remote Similarity	NPD8081	Approved
0.6019	Remote Similarity	NPD4790	Discontinued
0.6017	Remote Similarity	NPD6011	Approved
0.6016	Remote Similarity	NPD7500	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8393	Approved
0.5962	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5209	Approved
0.5948	Remote Similarity	NPD6647	Phase 2
0.5946	Remote Similarity	NPD7900	Approved
0.5946	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD1694	Approved
0.5932	Remote Similarity	NPD5701	Approved
0.5926	Remote Similarity	NPD6672	Approved
0.5926	Remote Similarity	NPD5737	Approved
0.5926	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6033	Approved
0.5917	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD4634	Approved
0.5909	Remote Similarity	NPD6079	Approved
0.5909	Remote Similarity	NPD7260	Phase 2
0.5895	Remote Similarity	NPD7331	Phase 2
0.5891	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD4802	Phase 2
0.5882	Remote Similarity	NPD4238	Approved
0.5877	Remote Similarity	NPD5696	Approved
0.5851	Remote Similarity	NPD7909	Approved
0.5849	Remote Similarity	NPD3665	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