NPASS Compound

Structure

NPC85613 OpenBabel07101719512D 27 30 0 0 0 0 0 0 0 0999 V2000 9.6113 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2094 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 24 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 20 2 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 16 27 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 1 0 0 0 0 21 25 2 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	363.18
Volume:	388.414
LogP:	5.33
LogD:	3.683
LogS:	-6.499
# Rotatable Bonds:	7
TPSA:	40.46
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	2.274
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	1.4604538591811433e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.115
30% Bioavailability (F30%):	0.52

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	98.41938018798828%
Volume Distribution (VD):	1.341
Pgp-substrate:	0.8530387878417969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.252
CYP2C19-inhibitor:	0.929
CYP2C19-substrate:	0.203
CYP2C9-inhibitor:	0.646
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.962
CYP2D6-substrate:	0.942
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	8.2
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.236
AMES Toxicity:	0.854
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.904
Carcinogencity:	0.833
Eye Corrosion:	0.003
Eye Irritation:	0.599
Respiratory Toxicity:	0.309

Download Data

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

Natural Product: NPC85613

Natural Product ID:	NPC85613
*Common Name:**	2-[6-(1,3-Benzodioxol-5-Yl)Hexyl]-1-Methylquinolin-4-One
IUPAC Name:	2-[6-(1,3-benzodioxol-5-yl)hexyl]-1-methylquinolin-4-one
Synonyms:
Standard InCHIKey:	NTOLOAOKRJSWIN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H25NO3/c1-24-18(15-21(25)19-10-6-7-11-20(19)24)9-5-3-2-4-8-17-12-13-22-23(14-17)27-16-26-22/h6-7,10-15H,2-5,8-9,16H2,1H3
SMILES:	O=c1cc(CCCCCCc2ccc3c(c2)OCO3)n(c2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2270127
PubChem CID:	11824628
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12568545]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28093914]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3854	Ruta graveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT852	Organism	Phomopsis obscurans	Phomopsis obscurans	GI	=	100.0	%	PMID[473242]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	67.7	%	PMID[473242]
NPT2241	Organism	Glomerella acutata	Glomerella acutata	GI	=	57.0	%	PMID[473242]
NPT852	Organism	Phomopsis obscurans	Phomopsis obscurans	GI	=	100.0	%	PMID[473243]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	67.7	%	PMID[473243]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	GI	=	100.0	%	PMID[473243]
NPT851	Organism	Colletotrichum fragariae	Colletotrichum fragariae	GI	=	57.0	%	PMID[473243]
NPT2241	Organism	Glomerella acutata	Glomerella acutata	GI	=	57.0	%	PMID[473243]

☑ 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 NPC85613 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	447
0.1-0.2	2402
0.2-0.3	11756
0.3-0.4	5048
0.4-0.5	10579
0.5-0.6	10022
0.6-0.7	2020
0.7-0.8	385
0.8-0.85	26
0.85-0.9	9
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9632	High Similarity	NPC5167
0.9512	High Similarity	NPC283810
0.872	High Similarity	NPC93653
0.8508	High Similarity	NPC71124
0.8492	Intermediate Similarity	NPC254957
0.8361	Intermediate Similarity	NPC5374
0.8343	Intermediate Similarity	NPC299582
0.8333	Intermediate Similarity	NPC268077
0.828	Intermediate Similarity	NPC207971
0.8129	Intermediate Similarity	NPC24954
0.801	Intermediate Similarity	NPC195120
0.801	Intermediate Similarity	NPC87560
0.7943	Intermediate Similarity	NPC471604
0.7914	Intermediate Similarity	NPC193906
0.7914	Intermediate Similarity	NPC23080
0.7904	Intermediate Similarity	NPC144691
0.788	Intermediate Similarity	NPC1820
0.7857	Intermediate Similarity	NPC55470
0.7857	Intermediate Similarity	NPC116007
0.7839	Intermediate Similarity	NPC118154
0.7839	Intermediate Similarity	NPC157983
0.7831	Intermediate Similarity	NPC469978
0.7809	Intermediate Similarity	NPC67978
0.7809	Intermediate Similarity	NPC303581
0.7797	Intermediate Similarity	NPC86469
0.7727	Intermediate Similarity	NPC306669
0.7722	Intermediate Similarity	NPC308267
0.768	Intermediate Similarity	NPC287588
0.7663	Intermediate Similarity	NPC83511
0.7647	Intermediate Similarity	NPC470088
0.7614	Intermediate Similarity	NPC295479
0.7614	Intermediate Similarity	NPC220241
0.7609	Intermediate Similarity	NPC249405
0.7596	Intermediate Similarity	NPC27887
0.759	Intermediate Similarity	NPC16249
0.7577	Intermediate Similarity	NPC475147
0.7569	Intermediate Similarity	NPC4669
0.7566	Intermediate Similarity	NPC198401
0.7554	Intermediate Similarity	NPC179704
0.7551	Intermediate Similarity	NPC100573
0.7551	Intermediate Similarity	NPC207873
0.7541	Intermediate Similarity	NPC472163
0.7541	Intermediate Similarity	NPC121400
0.7538	Intermediate Similarity	NPC268223
0.7529	Intermediate Similarity	NPC93593
0.7527	Intermediate Similarity	NPC287152
0.75	Intermediate Similarity	NPC308943
0.7471	Intermediate Similarity	NPC470708
0.7448	Intermediate Similarity	NPC234933
0.7447	Intermediate Similarity	NPC312531
0.7432	Intermediate Similarity	NPC207721
0.7429	Intermediate Similarity	NPC169742
0.7424	Intermediate Similarity	NPC475133
0.7423	Intermediate Similarity	NPC118419
0.7416	Intermediate Similarity	NPC153631
0.7401	Intermediate Similarity	NPC257763
0.7394	Intermediate Similarity	NPC477259
0.7394	Intermediate Similarity	NPC169387
0.7389	Intermediate Similarity	NPC182853
0.7389	Intermediate Similarity	NPC134702
0.7386	Intermediate Similarity	NPC57512
0.7386	Intermediate Similarity	NPC301163
0.7384	Intermediate Similarity	NPC475959
0.738	Intermediate Similarity	NPC204385
0.7374	Intermediate Similarity	NPC476569
0.7368	Intermediate Similarity	NPC206109
0.7368	Intermediate Similarity	NPC114039
0.7354	Intermediate Similarity	NPC474904
0.7351	Intermediate Similarity	NPC206201
0.735	Intermediate Similarity	NPC82541
0.7341	Intermediate Similarity	NPC469539
0.7341	Intermediate Similarity	NPC469540
0.7327	Intermediate Similarity	NPC148391
0.7323	Intermediate Similarity	NPC198160
0.7316	Intermediate Similarity	NPC22476
0.7314	Intermediate Similarity	NPC58661
0.7313	Intermediate Similarity	NPC116178
0.7313	Intermediate Similarity	NPC119722
0.7305	Intermediate Similarity	NPC252107
0.7305	Intermediate Similarity	NPC225745
0.7303	Intermediate Similarity	NPC106786
0.7299	Intermediate Similarity	NPC223125
0.7289	Intermediate Similarity	NPC11147
0.7286	Intermediate Similarity	NPC90185
0.7283	Intermediate Similarity	NPC285941
0.7282	Intermediate Similarity	NPC118189
0.7278	Intermediate Similarity	NPC59567
0.7277	Intermediate Similarity	NPC226708
0.7277	Intermediate Similarity	NPC114468
0.7277	Intermediate Similarity	NPC321166
0.7277	Intermediate Similarity	NPC217903
0.7273	Intermediate Similarity	NPC266425
0.7268	Intermediate Similarity	NPC17677
0.7263	Intermediate Similarity	NPC45389
0.7259	Intermediate Similarity	NPC41216
0.7251	Intermediate Similarity	NPC125134
0.7251	Intermediate Similarity	NPC86455
0.7251	Intermediate Similarity	NPC137920
0.7246	Intermediate Similarity	NPC148124
0.7246	Intermediate Similarity	NPC99078
0.7241	Intermediate Similarity	NPC2905
0.724	Intermediate Similarity	NPC302001
0.7236	Intermediate Similarity	NPC478075
0.7236	Intermediate Similarity	NPC222561
0.7235	Intermediate Similarity	NPC28398
0.7225	Intermediate Similarity	NPC476436
0.7222	Intermediate Similarity	NPC38961
0.7219	Intermediate Similarity	NPC314659
0.7216	Intermediate Similarity	NPC223124
0.7216	Intermediate Similarity	NPC476580
0.7208	Intermediate Similarity	NPC15987
0.7202	Intermediate Similarity	NPC248505
0.7202	Intermediate Similarity	NPC193528
0.7202	Intermediate Similarity	NPC220923
0.7202	Intermediate Similarity	NPC194359
0.7202	Intermediate Similarity	NPC470707
0.7202	Intermediate Similarity	NPC95366
0.7202	Intermediate Similarity	NPC28641
0.7198	Intermediate Similarity	NPC76478
0.7198	Intermediate Similarity	NPC7560
0.7198	Intermediate Similarity	NPC99724
0.7186	Intermediate Similarity	NPC251454
0.7186	Intermediate Similarity	NPC136330
0.7186	Intermediate Similarity	NPC255817
0.7186	Intermediate Similarity	NPC230698
0.7186	Intermediate Similarity	NPC196609
0.7186	Intermediate Similarity	NPC180647
0.7186	Intermediate Similarity	NPC205178
0.7186	Intermediate Similarity	NPC73883
0.7186	Intermediate Similarity	NPC277042
0.7178	Intermediate Similarity	NPC286683
0.7171	Intermediate Similarity	NPC313327
0.7171	Intermediate Similarity	NPC126556
0.7167	Intermediate Similarity	NPC204867
0.7166	Intermediate Similarity	NPC197335
0.7165	Intermediate Similarity	NPC477258
0.715	Intermediate Similarity	NPC212123
0.7143	Intermediate Similarity	NPC207239
0.7143	Intermediate Similarity	NPC470482
0.7143	Intermediate Similarity	NPC241263
0.7143	Intermediate Similarity	NPC470481
0.7143	Intermediate Similarity	NPC137172
0.7143	Intermediate Similarity	NPC145446
0.7135	Intermediate Similarity	NPC908
0.7135	Intermediate Similarity	NPC76079
0.7135	Intermediate Similarity	NPC216459
0.7135	Intermediate Similarity	NPC41178
0.7135	Intermediate Similarity	NPC138487
0.7135	Intermediate Similarity	NPC138438
0.7128	Intermediate Similarity	NPC24228
0.7126	Intermediate Similarity	NPC242000
0.7126	Intermediate Similarity	NPC167096
0.7119	Intermediate Similarity	NPC233029
0.7119	Intermediate Similarity	NPC210148
0.7113	Intermediate Similarity	NPC469816
0.7113	Intermediate Similarity	NPC469815
0.711	Intermediate Similarity	NPC46880
0.7109	Intermediate Similarity	NPC248903
0.7109	Intermediate Similarity	NPC13249
0.7095	Intermediate Similarity	NPC146288
0.7094	Intermediate Similarity	NPC61731
0.7094	Intermediate Similarity	NPC186569
0.7092	Intermediate Similarity	NPC124302
0.7092	Intermediate Similarity	NPC100863
0.7092	Intermediate Similarity	NPC14622
0.7092	Intermediate Similarity	NPC46744
0.7092	Intermediate Similarity	NPC70290
0.7092	Intermediate Similarity	NPC73020
0.7092	Intermediate Similarity	NPC215098
0.7092	Intermediate Similarity	NPC112937
0.7083	Intermediate Similarity	NPC96406
0.7081	Intermediate Similarity	NPC312872
0.7079	Intermediate Similarity	NPC85661
0.7077	Intermediate Similarity	NPC162653
0.7074	Intermediate Similarity	NPC190461
0.7073	Intermediate Similarity	NPC172403
0.7072	Intermediate Similarity	NPC160298
0.7072	Intermediate Similarity	NPC477559
0.7072	Intermediate Similarity	NPC306902
0.7072	Intermediate Similarity	NPC232924
0.7072	Intermediate Similarity	NPC266753
0.7071	Intermediate Similarity	NPC471489
0.707	Intermediate Similarity	NPC253675
0.7068	Intermediate Similarity	NPC21425
0.7063	Intermediate Similarity	NPC257490
0.7062	Intermediate Similarity	NPC26928
0.7062	Intermediate Similarity	NPC119669
0.7059	Intermediate Similarity	NPC10732
0.7056	Intermediate Similarity	NPC476429
0.7049	Intermediate Similarity	NPC231198
0.7044	Intermediate Similarity	NPC269449
0.7044	Intermediate Similarity	NPC25961
0.7042	Intermediate Similarity	NPC278525
0.7041	Intermediate Similarity	NPC7018
0.7037	Intermediate Similarity	NPC149285
0.7035	Intermediate Similarity	NPC308197
0.7033	Intermediate Similarity	NPC46259
0.7033	Intermediate Similarity	NPC329830
0.7031	Intermediate Similarity	NPC477186
0.703	Intermediate Similarity	NPC46679

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 NPC85613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	680
0.2-0.3	916
0.3-0.4	1170
0.4-0.5	2577
0.5-0.6	2548
0.6-0.7	850
0.7-0.8	120
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8128	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD2821	Approved
0.801	Intermediate Similarity	NPD4859	Phase 1
0.7784	Intermediate Similarity	NPD5183	Approved
0.7784	Intermediate Similarity	NPD5186	Approved
0.7746	Intermediate Similarity	NPD5977	Approved
0.7746	Intermediate Similarity	NPD5978	Approved
0.7704	Intermediate Similarity	NPD683	Approved
0.7665	Intermediate Similarity	NPD7225	Discontinued
0.7632	Intermediate Similarity	NPD5071	Phase 2
0.7579	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5950	Discontinued
0.7528	Intermediate Similarity	NPD6457	Approved
0.7475	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4515	Suspended
0.7322	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD6386	Approved
0.7273	Intermediate Similarity	NPD6873	Phase 2
0.7254	Intermediate Similarity	NPD5582	Discontinued
0.7253	Intermediate Similarity	NPD5242	Approved
0.7241	Intermediate Similarity	NPD3640	Phase 3
0.7241	Intermediate Similarity	NPD3639	Approved
0.7241	Intermediate Similarity	NPD3641	Approved
0.7216	Intermediate Similarity	NPD5515	Phase 2
0.7214	Intermediate Similarity	NPD5860	Discontinued
0.7206	Intermediate Similarity	NPD5025	Approved
0.7206	Intermediate Similarity	NPD8149	Discontinued
0.7204	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2492	Phase 1
0.7184	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2899	Discontinued
0.7151	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6874	Approved
0.7129	Intermediate Similarity	NPD5914	Approved
0.712	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5457	Discontinued
0.7092	Intermediate Similarity	NPD4420	Approved
0.709	Intermediate Similarity	NPD7281	Phase 3
0.709	Intermediate Similarity	NPD7280	Phase 3
0.709	Intermediate Similarity	NPD7546	Discontinued
0.7081	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3297	Approved
0.7052	Intermediate Similarity	NPD3301	Approved
0.7049	Intermediate Similarity	NPD3983	Phase 3
0.7049	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3252	Approved
0.7031	Intermediate Similarity	NPD7291	Discontinued
0.7031	Intermediate Similarity	NPD3349	Phase 2
0.7027	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6493	Phase 3
0.7022	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6211	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5519	Discontinued
0.7005	Intermediate Similarity	NPD4846	Phase 2
0.7	Intermediate Similarity	NPD3802	Phase 3
0.7	Intermediate Similarity	NPD2842	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7559	Phase 2
0.6989	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2672	Discontinued
0.6977	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4083	Discontinued
0.697	Remote Similarity	NPD1880	Phase 3
0.6967	Remote Similarity	NPD7279	Phase 2
0.6967	Remote Similarity	NPD7278	Phase 2
0.6966	Remote Similarity	NPD824	Approved
0.6965	Remote Similarity	NPD3298	Approved
0.6954	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5006	Approved
0.695	Remote Similarity	NPD5005	Approved
0.6946	Remote Similarity	NPD4082	Approved
0.6944	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6625	Approved
0.6943	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5496	Approved
0.6931	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4493	Discontinued
0.6915	Remote Similarity	NPD3965	Phase 1
0.6915	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5866	Approved
0.6879	Remote Similarity	NPD4597	Approved
0.6879	Remote Similarity	NPD4598	Approved
0.6875	Remote Similarity	NPD6618	Phase 2
0.6865	Remote Similarity	NPD2681	Approved
0.6865	Remote Similarity	NPD2680	Approved
0.6864	Remote Similarity	NPD3140	Approved
0.6864	Remote Similarity	NPD3142	Approved
0.686	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4796	Discontinued
0.6837	Remote Similarity	NPD5937	Approved
0.6831	Remote Similarity	NPD1742	Approved
0.6831	Remote Similarity	NPD1743	Approved
0.6831	Remote Similarity	NPD19	Approved
0.6829	Remote Similarity	NPD4917	Discontinued
0.6825	Remote Similarity	NPD5600	Discontinued
0.6825	Remote Similarity	NPD6242	Discontinued
0.6825	Remote Similarity	NPD3793	Phase 3
0.682	Remote Similarity	NPD4885	Approved
0.6816	Remote Similarity	NPD6321	Discontinued
0.6814	Remote Similarity	NPD7263	Phase 2
0.6809	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2836	Approved
0.6786	Remote Similarity	NPD5871	Discontinued
0.6786	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5564	Approved
0.678	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6357	Discontinued
0.6774	Remote Similarity	NPD2249	Approved
0.6774	Remote Similarity	NPD2247	Approved
0.676	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6030	Approved
0.676	Remote Similarity	NPD6031	Approved
0.6749	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5718	Phase 2
0.6744	Remote Similarity	NPD7186	Phase 3
0.6744	Remote Similarity	NPD2670	Approved
0.6744	Remote Similarity	NPD743	Approved
0.6742	Remote Similarity	NPD4584	Approved
0.6735	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3964	Approved
0.6733	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4596	Phase 1
0.6731	Remote Similarity	NPD4492	Approved
0.6731	Remote Similarity	NPD4494	Approved
0.673	Remote Similarity	NPD4429	Discontinued
0.6728	Remote Similarity	NPD6199	Discontinued
0.6726	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD2883	Discontinued
0.6717	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3893	Discontinued
0.6713	Remote Similarity	NPD3259	Approved
0.6706	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1626	Approved
0.6703	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7110	Phase 1
0.6702	Remote Similarity	NPD7479	Phase 2
0.6702	Remote Similarity	NPD3920	Phase 2
0.6699	Remote Similarity	NPD4022	Approved
0.6699	Remote Similarity	NPD3472	Approved
0.6699	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2906	Approved
0.6699	Remote Similarity	NPD2907	Approved
0.6697	Remote Similarity	NPD6962	Phase 2
0.6685	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD4049	Phase 2
0.6667	Remote Similarity	NPD1769	Discontinued
0.6667	Remote Similarity	NPD1670	Discontinued
0.6667	Remote Similarity	NPD7223	Discontinued
0.6667	Remote Similarity	NPD6017	Discontinued
0.6667	Remote Similarity	NPD7224	Discontinued
0.6667	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3888	Discontinued
0.6651	Remote Similarity	NPD3816	Phase 1
0.6651	Remote Similarity	NPD3815	Phase 1
0.665	Remote Similarity	NPD3416	Discontinued
0.665	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5928	Phase 1
0.665	Remote Similarity	NPD6238	Discontinued
0.6649	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6876	Approved
0.6648	Remote Similarity	NPD4888	Discontinued
0.6648	Remote Similarity	NPD6875	Approved
0.6636	Remote Similarity	NPD6723	Discontinued
0.6636	Remote Similarity	NPD7994	Phase 2
0.6635	Remote Similarity	NPD3372	Discontinued
0.6634	Remote Similarity	NPD7891	Discontinued
0.6634	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7038	Approved
0.6632	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7039	Approved
0.6632	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.663	Remote Similarity	NPD814	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6738	Phase 2
0.663	Remote Similarity	NPD6737	Phase 2
0.663	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2791	Discontinued

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