NPASS Compound

Structure

CID291962 OpenBabel06191716102D 23 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 -7.5000 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 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 1.7321 2.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 14 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 17 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.22
Volume:	358.627
LogP:	5.079
LogD:	4.049
LogS:	-3.224
# Rotatable Bonds:	9
TPSA:	22.0
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	2.335
Fsp3:	0.476
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:	-4.715
MDCK Permeability:	1.8545071725384332e-05
Pgp-inhibitor:	0.08
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	97.69833374023438%
Volume Distribution (VD):	1.307
Pgp-substrate:	0.829808235168457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.626
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.678
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.413
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	4.642
Half-life (T1/2):	0.59

ADMET: Toxicity

hERG Blockers:	0.314
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.721
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.562
Skin Sensitization:	0.956
Carcinogencity:	0.311
Eye Corrosion:	0.005
Eye Irritation:	0.949
Respiratory Toxicity:	0.662

Download Data

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

Natural Product: NPC291962

Natural Product ID:	NPC291962
*Common Name:**	1-Methyl-2-[(Z)-Undec-5-Enyl]Quinolin-4-One
IUPAC Name:	1-methyl-2-[(Z)-undec-5-enyl]quinolin-4-one
Synonyms:
Standard InCHIKey:	JWKBGGZMJGQAIK-FPLPWBNLSA-N
Standard InCHI:	InChI=1S/C21H29NO/c1-3-4-5-6-7-8-9-10-11-14-18-17-21(23)19-15-12-13-16-20(19)22(18)2/h7-8,12-13,15-17H,3-6,9-11,14H2,1-2H3/b8-7-
SMILES:	CCCCC/C=CCCCCc1cc(=O)c2ccccc2n1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1643834
PubChem CID:	5319809
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
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7463094]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201313]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699182]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4877	Euodia officinalis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8314	Euodia ruticarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16845	Euodia bodinieri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19935	Evodia rutaecarpa	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
MIC	1
Others	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	Activity	=	88.5	%	PMID[485538]
NPT171	Cell Line	MRC5	Homo sapiens	Activity	=	94.9	%	PMID[485538]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	12900.0	nM	PMID[485538]

☑ 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 NPC291962 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	423
0.1-0.2	4249
0.2-0.3	13372
0.3-0.4	16481
0.4-0.5	4082
0.5-0.6	2343
0.6-0.7	1436
0.7-0.8	281
0.8-0.85	14
0.85-0.9	2
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177684
0.9911	High Similarity	NPC112373
0.9911	High Similarity	NPC161956
0.9911	High Similarity	NPC258531
0.9649	High Similarity	NPC257490
0.9391	High Similarity	NPC279385
0.9391	High Similarity	NPC179605
0.931	High Similarity	NPC103292
0.9231	High Similarity	NPC39818
0.8655	High Similarity	NPC226143
0.8443	Intermediate Similarity	NPC268534
0.8421	Intermediate Similarity	NPC172170
0.8372	Intermediate Similarity	NPC300299
0.8195	Intermediate Similarity	NPC471574
0.8189	Intermediate Similarity	NPC209389
0.8151	Intermediate Similarity	NPC57051
0.8125	Intermediate Similarity	NPC194562
0.8095	Intermediate Similarity	NPC472244
0.8095	Intermediate Similarity	NPC470343
0.808	Intermediate Similarity	NPC254698
0.806	Intermediate Similarity	NPC471164
0.8015	Intermediate Similarity	NPC136002
0.791	Intermediate Similarity	NPC83214
0.7907	Intermediate Similarity	NPC150863
0.7879	Intermediate Similarity	NPC316104
0.7879	Intermediate Similarity	NPC162417
0.7874	Intermediate Similarity	NPC192533
0.7857	Intermediate Similarity	NPC144691
0.7852	Intermediate Similarity	NPC207554
0.7846	Intermediate Similarity	NPC314431
0.7846	Intermediate Similarity	NPC280807
0.7846	Intermediate Similarity	NPC472245
0.7786	Intermediate Similarity	NPC316746
0.7727	Intermediate Similarity	NPC207428
0.7664	Intermediate Similarity	NPC2823
0.75	Intermediate Similarity	NPC117032
0.7481	Intermediate Similarity	NPC253476
0.7464	Intermediate Similarity	NPC315051
0.7432	Intermediate Similarity	NPC27904
0.7432	Intermediate Similarity	NPC93653
0.7426	Intermediate Similarity	NPC173295
0.7376	Intermediate Similarity	NPC470822
0.7376	Intermediate Similarity	NPC130797
0.7338	Intermediate Similarity	NPC472243
0.7333	Intermediate Similarity	NPC167336
0.7333	Intermediate Similarity	NPC53044
0.7329	Intermediate Similarity	NPC295021
0.7305	Intermediate Similarity	NPC308197
0.7285	Intermediate Similarity	NPC299582
0.7208	Intermediate Similarity	NPC318183
0.7185	Intermediate Similarity	NPC187231
0.7183	Intermediate Similarity	NPC478040
0.7172	Intermediate Similarity	NPC242000
0.7172	Intermediate Similarity	NPC300596
0.7172	Intermediate Similarity	NPC237649
0.7164	Intermediate Similarity	NPC72473
0.7164	Intermediate Similarity	NPC58827
0.7164	Intermediate Similarity	NPC307437
0.7163	Intermediate Similarity	NPC43477
0.7153	Intermediate Similarity	NPC324445
0.7143	Intermediate Similarity	NPC469560
0.7133	Intermediate Similarity	NPC314186
0.7132	Intermediate Similarity	NPC314098
0.7113	Intermediate Similarity	NPC472241
0.7111	Intermediate Similarity	NPC122235
0.7092	Intermediate Similarity	NPC130251
0.709	Intermediate Similarity	NPC250476
0.7083	Intermediate Similarity	NPC291610
0.708	Intermediate Similarity	NPC40364
0.7071	Intermediate Similarity	NPC122553
0.7059	Intermediate Similarity	NPC477432
0.7059	Intermediate Similarity	NPC75496
0.7042	Intermediate Similarity	NPC301760
0.7042	Intermediate Similarity	NPC316202
0.7034	Intermediate Similarity	NPC478039
0.7032	Intermediate Similarity	NPC472118
0.702	Intermediate Similarity	NPC154478
0.7007	Intermediate Similarity	NPC231382
0.7	Intermediate Similarity	NPC471123
0.7	Intermediate Similarity	NPC84317
0.6993	Remote Similarity	NPC138293
0.6993	Remote Similarity	NPC113056
0.6993	Remote Similarity	NPC204867
0.6967	Remote Similarity	NPC38262
0.6966	Remote Similarity	NPC472242
0.6944	Remote Similarity	NPC314287
0.694	Remote Similarity	NPC226794
0.6937	Remote Similarity	NPC85613
0.6928	Remote Similarity	NPC293458
0.6923	Remote Similarity	NPC192209
0.6923	Remote Similarity	NPC313449
0.6899	Remote Similarity	NPC469529
0.6899	Remote Similarity	NPC288232
0.6892	Remote Similarity	NPC13526
0.6879	Remote Similarity	NPC292265
0.6875	Remote Similarity	NPC296163
0.6875	Remote Similarity	NPC187036
0.687	Remote Similarity	NPC228515
0.6864	Remote Similarity	NPC256452
0.6855	Remote Similarity	NPC471743
0.6855	Remote Similarity	NPC475607
0.6839	Remote Similarity	NPC471130
0.6838	Remote Similarity	NPC322433
0.6832	Remote Similarity	NPC5167
0.6818	Remote Similarity	NPC88970
0.6815	Remote Similarity	NPC471943
0.6813	Remote Similarity	NPC474081
0.6803	Remote Similarity	NPC470579
0.68	Remote Similarity	NPC55529
0.6792	Remote Similarity	NPC475594
0.678	Remote Similarity	NPC246757
0.678	Remote Similarity	NPC291070
0.6772	Remote Similarity	NPC355
0.6767	Remote Similarity	NPC130931
0.6732	Remote Similarity	NPC123241
0.6721	Remote Similarity	NPC326792
0.6712	Remote Similarity	NPC469537
0.671	Remote Similarity	NPC469741
0.6691	Remote Similarity	NPC179224
0.6688	Remote Similarity	NPC279527
0.6688	Remote Similarity	NPC214960
0.6667	Remote Similarity	NPC475094
0.6667	Remote Similarity	NPC473329
0.6667	Remote Similarity	NPC475761
0.6667	Remote Similarity	NPC20322
0.6667	Remote Similarity	NPC265100
0.6667	Remote Similarity	NPC78154
0.6667	Remote Similarity	NPC474041
0.6646	Remote Similarity	NPC470317
0.6645	Remote Similarity	NPC315368
0.6642	Remote Similarity	NPC316582
0.6626	Remote Similarity	NPC475685
0.6626	Remote Similarity	NPC73994
0.6624	Remote Similarity	NPC115232
0.6623	Remote Similarity	NPC113946
0.6623	Remote Similarity	NPC243756
0.6623	Remote Similarity	NPC314223
0.6623	Remote Similarity	NPC154602
0.6605	Remote Similarity	NPC83774
0.6603	Remote Similarity	NPC242116
0.6603	Remote Similarity	NPC472117
0.6603	Remote Similarity	NPC35510
0.6603	Remote Similarity	NPC253667
0.6584	Remote Similarity	NPC470548
0.6582	Remote Similarity	NPC114637
0.6579	Remote Similarity	NPC122106
0.6579	Remote Similarity	NPC285381
0.6575	Remote Similarity	NPC470301
0.6568	Remote Similarity	NPC1820
0.6566	Remote Similarity	NPC476341
0.6561	Remote Similarity	NPC189116
0.6547	Remote Similarity	NPC476950
0.6541	Remote Similarity	NPC223595
0.6541	Remote Similarity	NPC475248
0.6541	Remote Similarity	NPC63047
0.6541	Remote Similarity	NPC224970
0.6541	Remote Similarity	NPC167724
0.6541	Remote Similarity	NPC70949
0.6535	Remote Similarity	NPC79618
0.6531	Remote Similarity	NPC238499
0.6524	Remote Similarity	NPC61011
0.6524	Remote Similarity	NPC283810
0.6524	Remote Similarity	NPC298320
0.6522	Remote Similarity	NPC79698
0.6516	Remote Similarity	NPC61013
0.6507	Remote Similarity	NPC242933
0.6503	Remote Similarity	NPC284775
0.6497	Remote Similarity	NPC214106
0.6497	Remote Similarity	NPC476231
0.6494	Remote Similarity	NPC114808
0.6486	Remote Similarity	NPC285470
0.6486	Remote Similarity	NPC36342
0.6486	Remote Similarity	NPC2785
0.6484	Remote Similarity	NPC164802
0.6474	Remote Similarity	NPC36495
0.6474	Remote Similarity	NPC193410
0.6471	Remote Similarity	NPC70406
0.6467	Remote Similarity	NPC467188
0.6463	Remote Similarity	NPC22082
0.6463	Remote Similarity	NPC186284
0.6456	Remote Similarity	NPC313757
0.6452	Remote Similarity	NPC29285
0.6439	Remote Similarity	NPC472164
0.6439	Remote Similarity	NPC113099
0.6438	Remote Similarity	NPC319645
0.6433	Remote Similarity	NPC248117
0.6433	Remote Similarity	NPC474058
0.6433	Remote Similarity	NPC309531
0.6433	Remote Similarity	NPC472102
0.6429	Remote Similarity	NPC478076
0.6429	Remote Similarity	NPC251391
0.6429	Remote Similarity	NPC300205
0.6429	Remote Similarity	NPC281094
0.6412	Remote Similarity	NPC313293
0.641	Remote Similarity	NPC104345
0.641	Remote Similarity	NPC69057
0.6407	Remote Similarity	NPC21429
0.6407	Remote Similarity	NPC46895
0.6405	Remote Similarity	NPC66936
0.6405	Remote Similarity	NPC313889

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 NPC291962 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	707
0.2-0.3	897
0.3-0.4	1715
0.4-0.5	2593
0.5-0.6	2069
0.6-0.7	798
0.7-0.8	104
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.864	High Similarity	NPD486	Clinical (unspecified phase)
0.8504	High Similarity	NPD441	Approved
0.8417	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD6017	Discontinued
0.8217	Intermediate Similarity	NPD1527	Phase 2
0.8217	Intermediate Similarity	NPD2950	Approved
0.8217	Intermediate Similarity	NPD2949	Approved
0.814	Intermediate Similarity	NPD1919	Approved
0.814	Intermediate Similarity	NPD1920	Approved
0.8017	Intermediate Similarity	NPD1064	Approved
0.8017	Intermediate Similarity	NPD1065	Approved
0.7939	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1541	Approved
0.7891	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD1175	Approved
0.7836	Intermediate Similarity	NPD6342	Discontinued
0.7737	Intermediate Similarity	NPD6513	Approved
0.7737	Intermediate Similarity	NPD6512	Approved
0.7734	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5933	Phase 3
0.7571	Intermediate Similarity	NPD5932	Phase 3
0.7571	Intermediate Similarity	NPD5931	Phase 3
0.7535	Intermediate Similarity	NPD4942	Approved
0.7521	Intermediate Similarity	NPD708	Approved
0.7517	Intermediate Similarity	NPD4042	Phase 2
0.7517	Intermediate Similarity	NPD4045	Phase 2
0.75	Intermediate Similarity	NPD3248	Phase 1
0.75	Intermediate Similarity	NPD5918	Discontinued
0.75	Intermediate Similarity	NPD1124	Approved
0.75	Intermediate Similarity	NPD1123	Approved
0.7482	Intermediate Similarity	NPD6768	Approved
0.7482	Intermediate Similarity	NPD3482	Approved
0.748	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD1099	Approved
0.7478	Intermediate Similarity	NPD1100	Approved
0.7444	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5179	Approved
0.7419	Intermediate Similarity	NPD5180	Approved
0.7419	Intermediate Similarity	NPD5181	Approved
0.7391	Intermediate Similarity	NPD1626	Approved
0.7376	Intermediate Similarity	NPD3481	Approved
0.7376	Intermediate Similarity	NPD4043	Approved
0.7376	Intermediate Similarity	NPD4046	Approved
0.7373	Intermediate Similarity	NPD2193	Phase 2
0.7373	Intermediate Similarity	NPD2648	Phase 3
0.7357	Intermediate Similarity	NPD6566	Discontinued
0.7329	Intermediate Similarity	NPD2790	Discontinued
0.7315	Intermediate Similarity	NPD2506	Approved
0.7299	Intermediate Similarity	NPD1410	Phase 1
0.7299	Intermediate Similarity	NPD2331	Discontinued
0.7292	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3546	Approved
0.7273	Intermediate Similarity	NPD3545	Approved
0.7241	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4549	Discontinued
0.7227	Intermediate Similarity	NPD2196	Discontinued
0.7227	Intermediate Similarity	NPD2171	Approved
0.7227	Intermediate Similarity	NPD813	Approved
0.7213	Intermediate Similarity	NPD4115	Approved
0.7213	Intermediate Similarity	NPD4114	Approved
0.719	Intermediate Similarity	NPD2192	Approved
0.719	Intermediate Similarity	NPD2197	Approved
0.7185	Intermediate Similarity	NPD5131	Approved
0.7183	Intermediate Similarity	NPD2820	Phase 3
0.7183	Intermediate Similarity	NPD1625	Approved
0.7174	Intermediate Similarity	NPD2791	Discontinued
0.7172	Intermediate Similarity	NPD4888	Discontinued
0.7163	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1342	Approved
0.7133	Intermediate Similarity	NPD2427	Approved
0.7124	Intermediate Similarity	NPD4645	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2365	Approved
0.7111	Intermediate Similarity	NPD1781	Discontinued
0.7099	Intermediate Similarity	NPD1079	Discontinued
0.7097	Intermediate Similarity	NPD4116	Approved
0.7083	Intermediate Similarity	NPD4735	Approved
0.7083	Intermediate Similarity	NPD4734	Approved
0.7078	Intermediate Similarity	NPD2037	Approved
0.7071	Intermediate Similarity	NPD2670	Approved
0.7042	Intermediate Similarity	NPD4461	Discontinued
0.7032	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1854	Approved
0.7021	Intermediate Similarity	NPD7254	Discontinued
0.7021	Intermediate Similarity	NPD6655	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4393	Approved
0.702	Intermediate Similarity	NPD33	Approved
0.7015	Intermediate Similarity	NPD1574	Approved
0.7007	Intermediate Similarity	NPD1619	Phase 3
0.7007	Intermediate Similarity	NPD2754	Discontinued
0.7007	Intermediate Similarity	NPD1190	Approved
0.6993	Remote Similarity	NPD1189	Approved
0.6993	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1360	Approved
0.6984	Remote Similarity	NPD2999	Approved
0.6984	Remote Similarity	NPD3001	Approved
0.6981	Remote Similarity	NPD3782	Discontinued
0.697	Remote Similarity	NPD678	Discontinued
0.6967	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1593	Approved
0.696	Remote Similarity	NPD3548	Approved
0.6947	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4430	Phase 2
0.6944	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9539	Approved
0.694	Remote Similarity	NPD9541	Approved
0.6937	Remote Similarity	NPD4329	Approved
0.6937	Remote Similarity	NPD4330	Approved
0.6935	Remote Similarity	NPD5253	Approved
0.6933	Remote Similarity	NPD7072	Phase 2
0.6929	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7481	Approved
0.6923	Remote Similarity	NPD2010	Phase 3
0.6923	Remote Similarity	NPD2369	Discontinued
0.6923	Remote Similarity	NPD1222	Discontinued
0.6923	Remote Similarity	NPD7480	Approved
0.6918	Remote Similarity	NPD3792	Approved
0.6911	Remote Similarity	NPD1677	Discontinued
0.6901	Remote Similarity	NPD7142	Discontinued
0.6887	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2431	Approved
0.6879	Remote Similarity	NPD2432	Approved
0.6875	Remote Similarity	NPD2914	Approved
0.6875	Remote Similarity	NPD2913	Approved
0.6875	Remote Similarity	NPD3387	Approved
0.6871	Remote Similarity	NPD7088	Discontinued
0.6859	Remote Similarity	NPD2455	Approved
0.6859	Remote Similarity	NPD2454	Approved
0.6855	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5660	Approved
0.6842	Remote Similarity	NPD5659	Approved
0.6842	Remote Similarity	NPD6018	Approved
0.6842	Remote Similarity	NPD6019	Approved
0.6838	Remote Similarity	NPD9540	Approved
0.6838	Remote Similarity	NPD2840	Approved
0.6831	Remote Similarity	NPD6358	Phase 2
0.6831	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7082	Approved
0.6825	Remote Similarity	NPD7633	Discontinued
0.681	Remote Similarity	NPD8241	Phase 2
0.6803	Remote Similarity	NPD1524	Phase 1
0.68	Remote Similarity	NPD6299	Approved
0.68	Remote Similarity	NPD6300	Approved
0.6788	Remote Similarity	NPD5993	Phase 1
0.6781	Remote Similarity	NPD7259	Approved
0.6781	Remote Similarity	NPD7487	Discontinued
0.6779	Remote Similarity	NPD5748	Phase 2
0.6776	Remote Similarity	NPD951	Approved
0.6776	Remote Similarity	NPD2351	Discontinued
0.6769	Remote Similarity	NPD1323	Discontinued
0.6755	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5992	Approved
0.6752	Remote Similarity	NPD2404	Discontinued
0.675	Remote Similarity	NPD4657	Approved
0.675	Remote Similarity	NPD4655	Approved
0.6748	Remote Similarity	NPD3357	Discontinued
0.6746	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5657	Phase 3
0.6735	Remote Similarity	NPD7295	Approved
0.6733	Remote Similarity	NPD1230	Approved
0.673	Remote Similarity	NPD3377	Discontinued
0.6723	Remote Similarity	NPD4094	Approved
0.6721	Remote Similarity	NPD479	Approved
0.672	Remote Similarity	NPD990	Approved
0.672	Remote Similarity	NPD993	Approved
0.6719	Remote Similarity	NPD3865	Approved
0.6718	Remote Similarity	NPD6070	Approved
0.6718	Remote Similarity	NPD6069	Approved
0.6711	Remote Similarity	NPD979	Approved
0.6692	Remote Similarity	NPD5631	Phase 3
0.6689	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6629	Discontinued
0.6687	Remote Similarity	NPD3423	Phase 2
0.6687	Remote Similarity	NPD3471	Approved
0.6687	Remote Similarity	NPD3422	Phase 3
0.6687	Remote Similarity	NPD4988	Discontinued
0.6687	Remote Similarity	NPD3470	Approved
0.6667	Remote Similarity	NPD2836	Approved
0.6667	Remote Similarity	NPD1054	Approved
0.6667	Remote Similarity	NPD6024	Approved
0.6667	Remote Similarity	NPD3170	Approved
0.6667	Remote Similarity	NPD6027	Approved
0.6667	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7478	Approved
0.6644	Remote Similarity	NPD1802	Approved
0.6644	Remote Similarity	NPD1801	Approved
0.6643	Remote Similarity	NPD1070	Approved
0.6643	Remote Similarity	NPD1069	Approved
0.6642	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1531	Approved
0.6618	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD922	Approved
0.6613	Remote Similarity	NPD2244	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