NPASS Compound

Structure

CID166712 OpenBabel06191715542D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5132 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1010 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8301 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -0.8660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5132 -1.0570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	329.13
Volume:	324.787
LogP:	3.366
LogD:	3.311
LogS:	-4.051
# Rotatable Bonds:	5
TPSA:	66.25
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	3.374
Fsp3:	0.389
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	3.0514456739183515e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	92.3611831665039%
Volume Distribution (VD):	0.479
Pgp-substrate:	5.780542850494385%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.737
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.707
CYP2C9-substrate:	0.693
CYP2D6-inhibitor:	0.394
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.606
CYP3A4-substrate:	0.75

ADMET: Excretion

Clearance (CL):	8.441
Half-life (T1/2):	0.23

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.908
AMES Toxicity:	0.185
Rat Oral Acute Toxicity:	0.376
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.202
Carcinogencity:	0.569
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC166712

Natural Product ID:	NPC166712
*Common Name:**	Anhydroevoxine
IUPAC Name:	7-[(3,3-dimethyloxiran-2-yl)methoxy]-4,8-dimethoxyfuro[2,3-b]quinoline
Synonyms:
Standard InCHIKey:	ZFZSGUNUXDDUOD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H19NO5/c1-18(2)13(24-18)9-23-12-6-5-10-14(16(12)21-4)19-17-11(7-8-22-17)15(10)20-3/h5-8,13H,9H2,1-4H3
SMILES:	COc1c(OCC2OC2(C)C)ccc2c1nc1occc1c2OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269609
PubChem CID:	161441
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002374] Furanoquinolines

*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
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350171]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12078	Teclea nobilis	Species	Rutaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT852	Organism	Phomopsis obscurans	Phomopsis obscurans	Inhibition	>	80.0	%	PMID[526844]

☑ 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 NPC166712 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	625
0.1-0.2	3483
0.2-0.3	12351
0.3-0.4	5451
0.4-0.5	12115
0.5-0.6	7599
0.6-0.7	921
0.7-0.8	126
0.8-0.85	9
0.85-0.9	8
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9718	High Similarity	NPC34770
0.9679	High Similarity	NPC58209
0.9409	High Similarity	NPC160100
0.9409	High Similarity	NPC208364
0.9372	High Similarity	NPC203373
0.9241	High Similarity	NPC173250
0.9128	High Similarity	NPC217176
0.9062	High Similarity	NPC188400
0.9	High Similarity	NPC120513
0.8991	High Similarity	NPC140296
0.8972	High Similarity	NPC131885
0.8844	High Similarity	NPC168922
0.8756	High Similarity	NPC298436
0.8682	High Similarity	NPC205372
0.8667	High Similarity	NPC101312
0.8615	High Similarity	NPC1608
0.8559	High Similarity	NPC97746
0.8402	Intermediate Similarity	NPC16066
0.8387	Intermediate Similarity	NPC269367
0.8387	Intermediate Similarity	NPC219664
0.8311	Intermediate Similarity	NPC203168
0.7818	Intermediate Similarity	NPC66815
0.7751	Intermediate Similarity	NPC230683
0.7619	Intermediate Similarity	NPC208084
0.7602	Intermediate Similarity	NPC473188
0.7564	Intermediate Similarity	NPC314633
0.7544	Intermediate Similarity	NPC146418
0.754	Intermediate Similarity	NPC209981
0.753	Intermediate Similarity	NPC185197
0.7451	Intermediate Similarity	NPC470042
0.7412	Intermediate Similarity	NPC315634
0.7412	Intermediate Similarity	NPC100734
0.7412	Intermediate Similarity	NPC88923
0.7404	Intermediate Similarity	NPC198503
0.7384	Intermediate Similarity	NPC179287
0.7362	Intermediate Similarity	NPC225279
0.7352	Intermediate Similarity	NPC284685
0.7347	Intermediate Similarity	NPC475844
0.7321	Intermediate Similarity	NPC112937
0.7316	Intermediate Similarity	NPC187501
0.7303	Intermediate Similarity	NPC474688
0.7297	Intermediate Similarity	NPC279401
0.7297	Intermediate Similarity	NPC79293
0.7277	Intermediate Similarity	NPC46561
0.7276	Intermediate Similarity	NPC119134
0.7255	Intermediate Similarity	NPC191489
0.7255	Intermediate Similarity	NPC89549
0.7247	Intermediate Similarity	NPC124300
0.7227	Intermediate Similarity	NPC144452
0.722	Intermediate Similarity	NPC274640
0.7218	Intermediate Similarity	NPC291609
0.721	Intermediate Similarity	NPC308137
0.721	Intermediate Similarity	NPC310211
0.7208	Intermediate Similarity	NPC200888
0.7179	Intermediate Similarity	NPC39500
0.7173	Intermediate Similarity	NPC288987
0.7173	Intermediate Similarity	NPC148409
0.7162	Intermediate Similarity	NPC41216
0.7161	Intermediate Similarity	NPC169402
0.716	Intermediate Similarity	NPC310618
0.716	Intermediate Similarity	NPC282346
0.7154	Intermediate Similarity	NPC6786
0.7143	Intermediate Similarity	NPC249583
0.7143	Intermediate Similarity	NPC150239
0.7137	Intermediate Similarity	NPC318068
0.7131	Intermediate Similarity	NPC87560
0.7115	Intermediate Similarity	NPC227824
0.7106	Intermediate Similarity	NPC268223
0.7103	Intermediate Similarity	NPC270515
0.7102	Intermediate Similarity	NPC329631
0.7087	Intermediate Similarity	NPC317572
0.7082	Intermediate Similarity	NPC129897
0.7076	Intermediate Similarity	NPC116238
0.7073	Intermediate Similarity	NPC39370
0.7063	Intermediate Similarity	NPC161801
0.7059	Intermediate Similarity	NPC184408
0.7059	Intermediate Similarity	NPC195120
0.7059	Intermediate Similarity	NPC247803
0.7056	Intermediate Similarity	NPC470930
0.7047	Intermediate Similarity	NPC67401
0.7037	Intermediate Similarity	NPC13249
0.702	Intermediate Similarity	NPC476999
0.7016	Intermediate Similarity	NPC477587
0.7016	Intermediate Similarity	NPC477589
0.7008	Intermediate Similarity	NPC134637
0.7004	Intermediate Similarity	NPC253675
0.7004	Intermediate Similarity	NPC207620
0.7004	Intermediate Similarity	NPC148391
0.7	Intermediate Similarity	NPC469439
0.7	Intermediate Similarity	NPC174760
0.7	Intermediate Similarity	NPC148889
0.7	Intermediate Similarity	NPC118154
0.7	Intermediate Similarity	NPC157983
0.6992	Remote Similarity	NPC264176
0.6992	Remote Similarity	NPC473186
0.6989	Remote Similarity	NPC196449
0.6989	Remote Similarity	NPC314222
0.6988	Remote Similarity	NPC470785
0.6978	Remote Similarity	NPC169716
0.6971	Remote Similarity	NPC76478
0.6962	Remote Similarity	NPC114468
0.696	Remote Similarity	NPC477586
0.696	Remote Similarity	NPC477585
0.696	Remote Similarity	NPC477588
0.696	Remote Similarity	NPC477590
0.6953	Remote Similarity	NPC45190
0.6948	Remote Similarity	NPC184680
0.6941	Remote Similarity	NPC165964
0.6939	Remote Similarity	NPC476997
0.6935	Remote Similarity	NPC471978
0.6935	Remote Similarity	NPC90875
0.6933	Remote Similarity	NPC146976
0.6923	Remote Similarity	NPC474595
0.6923	Remote Similarity	NPC4687
0.692	Remote Similarity	NPC471979
0.6917	Remote Similarity	NPC134702
0.6914	Remote Similarity	NPC133609
0.6914	Remote Similarity	NPC94842
0.6911	Remote Similarity	NPC476996
0.6911	Remote Similarity	NPC476998
0.6906	Remote Similarity	NPC42591
0.6901	Remote Similarity	NPC118189
0.6899	Remote Similarity	NPC472435
0.6892	Remote Similarity	NPC41501
0.6891	Remote Similarity	NPC30749
0.6891	Remote Similarity	NPC474594
0.6891	Remote Similarity	NPC236668
0.6891	Remote Similarity	NPC321166
0.6885	Remote Similarity	NPC473449
0.6883	Remote Similarity	NPC474701
0.688	Remote Similarity	NPC472286
0.688	Remote Similarity	NPC472287
0.6875	Remote Similarity	NPC204385
0.687	Remote Similarity	NPC476994
0.6865	Remote Similarity	NPC49672
0.6862	Remote Similarity	NPC2905
0.6861	Remote Similarity	NPC62069
0.686	Remote Similarity	NPC54066
0.6858	Remote Similarity	NPC45389
0.6857	Remote Similarity	NPC470018
0.6853	Remote Similarity	NPC470784
0.6853	Remote Similarity	NPC474183
0.685	Remote Similarity	NPC124313
0.6849	Remote Similarity	NPC38237
0.6849	Remote Similarity	NPC312872
0.6846	Remote Similarity	NPC182853
0.6844	Remote Similarity	NPC132385
0.6844	Remote Similarity	NPC51388
0.6842	Remote Similarity	NPC24019
0.684	Remote Similarity	NPC280714
0.684	Remote Similarity	NPC473187
0.6838	Remote Similarity	NPC207283
0.6838	Remote Similarity	NPC84164
0.6831	Remote Similarity	NPC7560
0.6828	Remote Similarity	NPC471303
0.6827	Remote Similarity	NPC172222
0.6824	Remote Similarity	NPC72715
0.6824	Remote Similarity	NPC107123
0.6822	Remote Similarity	NPC189079
0.682	Remote Similarity	NPC472436
0.6816	Remote Similarity	NPC21638
0.6813	Remote Similarity	NPC476995
0.6809	Remote Similarity	NPC304183
0.6807	Remote Similarity	NPC23294
0.6807	Remote Similarity	NPC87413
0.6805	Remote Similarity	NPC293151
0.6802	Remote Similarity	NPC194740
0.6798	Remote Similarity	NPC99891
0.6794	Remote Similarity	NPC473833
0.6793	Remote Similarity	NPC209769
0.6792	Remote Similarity	NPC118228
0.6787	Remote Similarity	NPC233334
0.6787	Remote Similarity	NPC196718
0.6786	Remote Similarity	NPC166722
0.6783	Remote Similarity	NPC302807
0.6781	Remote Similarity	NPC470586
0.678	Remote Similarity	NPC152620
0.6778	Remote Similarity	NPC305542
0.6778	Remote Similarity	NPC116178
0.6778	Remote Similarity	NPC26679
0.6769	Remote Similarity	NPC230403
0.6769	Remote Similarity	NPC475190
0.6769	Remote Similarity	NPC303374
0.6768	Remote Similarity	NPC215837
0.6765	Remote Similarity	NPC303951
0.6763	Remote Similarity	NPC3207
0.6762	Remote Similarity	NPC280799
0.675	Remote Similarity	NPC217903
0.6746	Remote Similarity	NPC189903
0.6746	Remote Similarity	NPC182907
0.6745	Remote Similarity	NPC316224
0.6743	Remote Similarity	NPC472589
0.6743	Remote Similarity	NPC13603
0.6743	Remote Similarity	NPC53534
0.6737	Remote Similarity	NPC300156
0.6736	Remote Similarity	NPC218303
0.6736	Remote Similarity	NPC294375
0.6734	Remote Similarity	NPC74216
0.6723	Remote Similarity	NPC207971
0.6722	Remote Similarity	NPC176113

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 NPC166712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	723
0.2-0.3	1287
0.3-0.4	2217
0.4-0.5	2772
0.5-0.6	1404
0.6-0.7	362
0.7-0.8	13
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
0.7565	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6974	Phase 3
0.7448	Intermediate Similarity	NPD1505	Phase 2
0.7412	Intermediate Similarity	NPD7803	Approved
0.7352	Intermediate Similarity	NPD7955	Approved
0.7352	Intermediate Similarity	NPD7956	Approved
0.7333	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6716	Phase 1
0.7289	Intermediate Similarity	NPD2778	Approved
0.7255	Intermediate Similarity	NPD7708	Approved
0.7193	Intermediate Similarity	NPD2779	Approved
0.7143	Intermediate Similarity	NPD7180	Phase 3
0.7131	Intermediate Similarity	NPD5632	Approved
0.7119	Intermediate Similarity	NPD5924	Discontinued
0.7106	Intermediate Similarity	NPD3945	Discontinued
0.7102	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1867	Approved
0.7083	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5482	Discontinued
0.7065	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5022	Discontinued
0.7049	Intermediate Similarity	NPD4952	Phase 3
0.7045	Intermediate Similarity	NPD3006	Discontinued
0.7029	Intermediate Similarity	NPD2899	Discontinued
0.7028	Intermediate Similarity	NPD7885	Phase 2
0.7028	Intermediate Similarity	NPD7886	Phase 2
0.7028	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3925	Approved
0.702	Intermediate Similarity	NPD7859	Phase 2
0.7004	Intermediate Similarity	NPD6964	Approved
0.7004	Intermediate Similarity	NPD6963	Approved
0.7004	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7417	Discontinued
0.6996	Remote Similarity	NPD3263	Phase 3
0.6992	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7853	Phase 2
0.6967	Remote Similarity	NPD4328	Approved
0.6964	Remote Similarity	NPD4373	Phase 2
0.696	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3507	Phase 2
0.6951	Remote Similarity	NPD6962	Phase 2
0.6949	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5922	Phase 3
0.6935	Remote Similarity	NPD2951	Discontinued
0.6933	Remote Similarity	NPD3257	Approved
0.6932	Remote Similarity	NPD6790	Phase 1
0.693	Remote Similarity	NPD5512	Phase 3
0.693	Remote Similarity	NPD6550	Discontinued
0.6926	Remote Similarity	NPD5640	Discontinued
0.6917	Remote Similarity	NPD4429	Discontinued
0.6917	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD3258	Approved
0.6883	Remote Similarity	NPD1467	Approved
0.6883	Remote Similarity	NPD1466	Phase 3
0.688	Remote Similarity	NPD5805	Approved
0.6872	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5532	Phase 2
0.6858	Remote Similarity	NPD6228	Discontinued
0.6846	Remote Similarity	NPD7395	Discontinued
0.6842	Remote Similarity	NPD5479	Discontinued
0.6827	Remote Similarity	NPD6494	Phase 2
0.6818	Remote Similarity	NPD5450	Discontinued
0.6811	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3328	Phase 2
0.6792	Remote Similarity	NPD5293	Phase 2
0.6787	Remote Similarity	NPD4885	Approved
0.6787	Remote Similarity	NPD7031	Phase 1
0.6786	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5429	Discontinued
0.6778	Remote Similarity	NPD5866	Approved
0.6758	Remote Similarity	NPD8359	Phase 2
0.6757	Remote Similarity	NPD5857	Phase 3
0.6757	Remote Similarity	NPD3920	Phase 2
0.6751	Remote Similarity	NPD5658	Approved
0.675	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4846	Phase 2
0.6746	Remote Similarity	NPD4368	Phase 2
0.6736	Remote Similarity	NPD5416	Discontinued
0.6736	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5256	Discontinued
0.6722	Remote Similarity	NPD5902	Approved
0.6722	Remote Similarity	NPD1638	Discovery
0.6722	Remote Similarity	NPD5903	Approved
0.6718	Remote Similarity	NPD8091	Phase 3
0.6706	Remote Similarity	NPD1483	Discontinued
0.6706	Remote Similarity	NPD7022	Phase 2
0.6705	Remote Similarity	NPD8102	Discontinued
0.6695	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD3259	Approved
0.6693	Remote Similarity	NPD6625	Approved
0.6693	Remote Similarity	NPD5488	Discontinued
0.668	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5164	Discontinued
0.6667	Remote Similarity	NPD8463	Approved
0.6667	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD6456	Discontinued
0.6654	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7426	Phase 1
0.6641	Remote Similarity	NPD6517	Phase 3
0.6628	Remote Similarity	NPD5817	Discontinued
0.6627	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3392	Approved
0.6618	Remote Similarity	NPD8460	Approved
0.6618	Remote Similarity	NPD8459	Approved
0.6612	Remote Similarity	NPD3875	Discontinued
0.6608	Remote Similarity	NPD6745	Discontinued
0.6595	Remote Similarity	NPD4418	Discontinued
0.659	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5930	Phase 3
0.6584	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7222	Phase 2
0.6565	Remote Similarity	NPD2564	Approved
0.6565	Remote Similarity	NPD2565	Phase 2
0.6561	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5914	Approved
0.6556	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD8255	Phase 2
0.6548	Remote Similarity	NPD3441	Approved
0.6548	Remote Similarity	NPD3442	Approved
0.6542	Remote Similarity	NPD7467	Discontinued
0.654	Remote Similarity	NPD5006	Approved
0.654	Remote Similarity	NPD5005	Approved
0.6533	Remote Similarity	NPD8466	Approved
0.6533	Remote Similarity	NPD8467	Approved
0.6533	Remote Similarity	NPD8465	Approved
0.6531	Remote Similarity	NPD5459	Phase 2
0.6529	Remote Similarity	NPD4502	Phase 2
0.6527	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3003	Approved
0.6517	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4369	Phase 2
0.6511	Remote Similarity	NPD4420	Approved
0.651	Remote Similarity	NPD3250	Phase 1
0.6509	Remote Similarity	NPD3924	Approved
0.6509	Remote Similarity	NPD3921	Approved
0.6509	Remote Similarity	NPD3923	Approved
0.6509	Remote Similarity	NPD3922	Approved
0.6508	Remote Similarity	NPD1659	Phase 1
0.6502	Remote Similarity	NPD7069	Discontinued
0.6498	Remote Similarity	NPD6321	Discontinued
0.6496	Remote Similarity	NPD7558	Phase 2
0.6494	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3986	Discontinued
0.6488	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2884	Phase 1
0.6473	Remote Similarity	NPD3217	Phase 2
0.6468	Remote Similarity	NPD5003	Discontinued
0.6468	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD1955	Discontinued
0.6459	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6590	Discontinued
0.645	Remote Similarity	NPD7012	Phase 3
0.645	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7013	Phase 3
0.6439	Remote Similarity	NPD8425	Approved
0.6439	Remote Similarity	NPD8426	Approved
0.6434	Remote Similarity	NPD3816	Phase 1
0.6434	Remote Similarity	NPD8364	Approved
0.6434	Remote Similarity	NPD3815	Phase 1
0.6434	Remote Similarity	NPD8363	Approved
0.6432	Remote Similarity	NPD7452	Approved
0.6432	Remote Similarity	NPD7453	Approved
0.6429	Remote Similarity	NPD6961	Discontinued
0.6426	Remote Similarity	NPD6243	Phase 3
0.6426	Remote Similarity	NPD6244	Phase 3
0.642	Remote Similarity	NPD7048	Phase 3
0.642	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD1768	Approved
0.6413	Remote Similarity	NPD8429	Approved
0.6413	Remote Similarity	NPD8428	Approved
0.6413	Remote Similarity	NPD8427	Approved
0.6405	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6104	Discontinued
0.6398	Remote Similarity	NPD6988	Phase 1
0.6397	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7797	Approved
0.6392	Remote Similarity	NPD7796	Approved
0.6387	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5850	Phase 3
0.6386	Remote Similarity	NPD6242	Discontinued
0.6386	Remote Similarity	NPD8479	Phase 2
0.6385	Remote Similarity	NPD4876	Phase 3
0.6385	Remote Similarity	NPD4875	Phase 3
0.6382	Remote Similarity	NPD4897	Phase 2
0.6379	Remote Similarity	NPD4506	Discontinued
0.6378	Remote Similarity	NPD4981	Phase 2
0.6374	Remote Similarity	NPD8100	Phase 3
0.6367	Remote Similarity	NPD4927	Discontinued
0.6364	Remote Similarity	NPD7994	Phase 2

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