NPASS Compound

Structure

CID66815 OpenBabel06191715402D 22 23 0 0 0 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 3.4641 -2.0000 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 -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 -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 -1.7321 0.0000 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 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 6 10 2 0 0 0 0 7 12 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 13 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	303.15
Volume:	315.814
LogP:	3.29
LogD:	2.88
LogS:	-3.386
# Rotatable Bonds:	5
TPSA:	60.55
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.862
Synthetic Accessibility Score:	2.581
Fsp3:	0.353
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:	-4.749
MDCK Permeability:	1.3097414921503514e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	79.52050018310547%
Volume Distribution (VD):	0.652
Pgp-substrate:	11.153617858886719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.92
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.883
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.49
CYP2C9-substrate:	0.878
CYP2D6-inhibitor:	0.263
CYP2D6-substrate:	0.667
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	8.151
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.764
Drug-inuced Liver Injury (DILI):	0.862
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.608
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.117
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.047
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC66815

Natural Product ID:	NPC66815
*Common Name:**	Preskimmianine
IUPAC Name:	4,7,8-trimethoxy-3-(3-methylbut-2-enyl)-1H-quinolin-2-one
Synonyms:
Standard InCHIKey:	OAEZQCLAAGSHHA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H21NO4/c1-10(2)6-7-12-15(21-4)11-8-9-13(20-3)16(22-5)14(11)18-17(12)19/h6,8-9H,7H2,1-5H3,(H,18,19)
SMILES:	CC(=CCc1c(c2ccc(c(c2nc1O)OC)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487794
PubChem CID:	12305721
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
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11473427]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568765]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	root bark	n.a.	n.a.	PMID[18198838]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29135252]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7171	Salvia polystachya	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7966	Grewia villosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10830	Dictamnus dasycarpus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3560	Trifolium montanum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5799	Streptomyces chryseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1329	Esenbeckia hartmanii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO340	Orixa japonica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5451	Ageratina saltillensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11119	Salta triflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7171	Salvia polystachya	Species	Lamiaceae	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	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[559398]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[559398]
NPT2	Others	Unspecified		Activity	=	12.3	%	PMID[559398]
NPT2	Others	Unspecified		Activity	=	43.1	%	PMID[559398]
NPT2	Others	Unspecified		Activity	=	70.0	%	PMID[559398]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[559398]

☑ 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 NPC66815 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	527
0.1-0.2	2812
0.2-0.3	13616
0.3-0.4	4089
0.4-0.5	11794
0.5-0.6	8105
0.6-0.7	1441
0.7-0.8	298
0.8-0.85	7
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9215	High Similarity	NPC203168
0.9211	High Similarity	NPC219664
0.8856	High Similarity	NPC200888
0.8846	High Similarity	NPC42591
0.8689	High Similarity	NPC62069
0.865	High Similarity	NPC148409
0.8418	Intermediate Similarity	NPC304183
0.8191	Intermediate Similarity	NPC474595
0.8128	Intermediate Similarity	NPC474594
0.8118	Intermediate Similarity	NPC283152
0.8108	Intermediate Similarity	NPC312872
0.8063	Intermediate Similarity	NPC66083
0.8041	Intermediate Similarity	NPC79293
0.8041	Intermediate Similarity	NPC279401
0.8028	Intermediate Similarity	NPC160100
0.8022	Intermediate Similarity	NPC118511
0.7955	Intermediate Similarity	NPC58209
0.7917	Intermediate Similarity	NPC204385
0.791	Intermediate Similarity	NPC164374
0.791	Intermediate Similarity	NPC137929
0.79	Intermediate Similarity	NPC199277
0.79	Intermediate Similarity	NPC135887
0.7887	Intermediate Similarity	NPC476997
0.7872	Intermediate Similarity	NPC194724
0.7872	Intermediate Similarity	NPC288943
0.787	Intermediate Similarity	NPC34770
0.785	Intermediate Similarity	NPC476998
0.785	Intermediate Similarity	NPC476996
0.7843	Intermediate Similarity	NPC209769
0.7818	Intermediate Similarity	NPC166712
0.7804	Intermediate Similarity	NPC476994
0.7799	Intermediate Similarity	NPC173080
0.7755	Intermediate Similarity	NPC469390
0.7742	Intermediate Similarity	NPC473182
0.7734	Intermediate Similarity	NPC470930
0.7732	Intermediate Similarity	NPC61350
0.772	Intermediate Similarity	NPC320394
0.7716	Intermediate Similarity	NPC141915
0.7716	Intermediate Similarity	NPC114335
0.7716	Intermediate Similarity	NPC280964
0.7714	Intermediate Similarity	NPC473822
0.7708	Intermediate Similarity	NPC206201
0.7678	Intermediate Similarity	NPC473179
0.7662	Intermediate Similarity	NPC128823
0.7656	Intermediate Similarity	NPC478032
0.7644	Intermediate Similarity	NPC202605
0.7644	Intermediate Similarity	NPC112206
0.7642	Intermediate Similarity	NPC174049
0.7637	Intermediate Similarity	NPC26872
0.7636	Intermediate Similarity	NPC473183
0.7626	Intermediate Similarity	NPC473184
0.7623	Intermediate Similarity	NPC208364
0.7619	Intermediate Similarity	NPC8022
0.7619	Intermediate Similarity	NPC470799
0.7617	Intermediate Similarity	NPC474798
0.7611	Intermediate Similarity	NPC203373
0.7608	Intermediate Similarity	NPC162530
0.7586	Intermediate Similarity	NPC31930
0.757	Intermediate Similarity	NPC122463
0.7562	Intermediate Similarity	NPC243834
0.7562	Intermediate Similarity	NPC224928
0.7562	Intermediate Similarity	NPC70956
0.7557	Intermediate Similarity	NPC476995
0.7551	Intermediate Similarity	NPC314573
0.7546	Intermediate Similarity	NPC202503
0.7538	Intermediate Similarity	NPC133140
0.7538	Intermediate Similarity	NPC195268
0.7514	Intermediate Similarity	NPC26850
0.7513	Intermediate Similarity	NPC472168
0.7512	Intermediate Similarity	NPC469440
0.75	Intermediate Similarity	NPC469589
0.75	Intermediate Similarity	NPC470586
0.75	Intermediate Similarity	NPC473513
0.7489	Intermediate Similarity	NPC173250
0.7476	Intermediate Similarity	NPC36229
0.7476	Intermediate Similarity	NPC26679
0.7476	Intermediate Similarity	NPC16452
0.7476	Intermediate Similarity	NPC476581
0.7476	Intermediate Similarity	NPC316981
0.7475	Intermediate Similarity	NPC110741
0.7468	Intermediate Similarity	NPC101312
0.7466	Intermediate Similarity	NPC277351
0.7465	Intermediate Similarity	NPC469594
0.7445	Intermediate Similarity	NPC472068
0.7435	Intermediate Similarity	NPC252590
0.7431	Intermediate Similarity	NPC473185
0.7427	Intermediate Similarity	NPC475774
0.7424	Intermediate Similarity	NPC473188
0.7418	Intermediate Similarity	NPC314552
0.7416	Intermediate Similarity	NPC185782
0.7409	Intermediate Similarity	NPC476999
0.7409	Intermediate Similarity	NPC201508
0.7407	Intermediate Similarity	NPC118121
0.7404	Intermediate Similarity	NPC193777
0.7402	Intermediate Similarity	NPC476582
0.7402	Intermediate Similarity	NPC4071
0.7402	Intermediate Similarity	NPC476578
0.7389	Intermediate Similarity	NPC188400
0.7387	Intermediate Similarity	NPC242928
0.7383	Intermediate Similarity	NPC204446
0.738	Intermediate Similarity	NPC472067
0.738	Intermediate Similarity	NPC472031
0.738	Intermediate Similarity	NPC472066
0.7373	Intermediate Similarity	NPC205372
0.7368	Intermediate Similarity	NPC470931
0.7358	Intermediate Similarity	NPC266931
0.7358	Intermediate Similarity	NPC471080
0.7358	Intermediate Similarity	NPC469592
0.7343	Intermediate Similarity	NPC223427
0.734	Intermediate Similarity	NPC473053
0.733	Intermediate Similarity	NPC217176
0.7327	Intermediate Similarity	NPC230403
0.7327	Intermediate Similarity	NPC475190
0.7302	Intermediate Similarity	NPC177404
0.7297	Intermediate Similarity	NPC153769
0.7296	Intermediate Similarity	NPC120513
0.7295	Intermediate Similarity	NPC291535
0.7295	Intermediate Similarity	NPC475085
0.7295	Intermediate Similarity	NPC475112
0.7282	Intermediate Similarity	NPC234197
0.7277	Intermediate Similarity	NPC294244
0.7273	Intermediate Similarity	NPC140296
0.7273	Intermediate Similarity	NPC471736
0.7273	Intermediate Similarity	NPC472111
0.7273	Intermediate Similarity	NPC84478
0.7265	Intermediate Similarity	NPC255800
0.7265	Intermediate Similarity	NPC96584
0.726	Intermediate Similarity	NPC97746
0.726	Intermediate Similarity	NPC179287
0.7259	Intermediate Similarity	NPC118776
0.7257	Intermediate Similarity	NPC41501
0.7248	Intermediate Similarity	NPC280272
0.7243	Intermediate Similarity	NPC148391
0.7243	Intermediate Similarity	NPC235076
0.7241	Intermediate Similarity	NPC78284
0.724	Intermediate Similarity	NPC44161
0.7235	Intermediate Similarity	NPC54066
0.7233	Intermediate Similarity	NPC280714
0.723	Intermediate Similarity	NPC296482
0.723	Intermediate Similarity	NPC202768
0.723	Intermediate Similarity	NPC53069
0.7225	Intermediate Similarity	NPC165349
0.7225	Intermediate Similarity	NPC118832
0.7225	Intermediate Similarity	NPC329708
0.7225	Intermediate Similarity	NPC264166
0.7225	Intermediate Similarity	NPC274291
0.7225	Intermediate Similarity	NPC47059
0.7222	Intermediate Similarity	NPC131885
0.7222	Intermediate Similarity	NPC280853
0.7222	Intermediate Similarity	NPC23614
0.7222	Intermediate Similarity	NPC100079
0.7217	Intermediate Similarity	NPC188420
0.7206	Intermediate Similarity	NPC131017
0.7204	Intermediate Similarity	NPC308392
0.7204	Intermediate Similarity	NPC475910
0.7202	Intermediate Similarity	NPC473764
0.7202	Intermediate Similarity	NPC314940
0.7196	Intermediate Similarity	NPC271215
0.7196	Intermediate Similarity	NPC149471
0.719	Intermediate Similarity	NPC476106
0.7182	Intermediate Similarity	NPC285016
0.7182	Intermediate Similarity	NPC473449
0.7182	Intermediate Similarity	NPC245657
0.7177	Intermediate Similarity	NPC317572
0.7167	Intermediate Similarity	NPC471596
0.7158	Intermediate Similarity	NPC235628
0.7158	Intermediate Similarity	NPC471598
0.7157	Intermediate Similarity	NPC226202
0.7156	Intermediate Similarity	NPC132642
0.7156	Intermediate Similarity	NPC313189
0.715	Intermediate Similarity	NPC1527
0.715	Intermediate Similarity	NPC48353
0.715	Intermediate Similarity	NPC18487
0.7143	Intermediate Similarity	NPC134702
0.7143	Intermediate Similarity	NPC174576
0.7143	Intermediate Similarity	NPC60553
0.7136	Intermediate Similarity	NPC474188
0.7136	Intermediate Similarity	NPC11464
0.7136	Intermediate Similarity	NPC199667
0.713	Intermediate Similarity	NPC469792
0.713	Intermediate Similarity	NPC288349
0.7129	Intermediate Similarity	NPC230805
0.7123	Intermediate Similarity	NPC76478
0.7123	Intermediate Similarity	NPC18348
0.7116	Intermediate Similarity	NPC114468
0.7115	Intermediate Similarity	NPC329747
0.7115	Intermediate Similarity	NPC477019
0.711	Intermediate Similarity	NPC208084
0.711	Intermediate Similarity	NPC46451
0.7105	Intermediate Similarity	NPC168922
0.7103	Intermediate Similarity	NPC146418
0.7101	Intermediate Similarity	NPC72211
0.7095	Intermediate Similarity	NPC245816
0.7095	Intermediate Similarity	NPC162484
0.7095	Intermediate Similarity	NPC476138
0.7094	Intermediate Similarity	NPC144381
0.7089	Intermediate Similarity	NPC473181
0.7087	Intermediate Similarity	NPC291609
0.7085	Intermediate Similarity	NPC274640
0.7083	Intermediate Similarity	NPC2905

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 NPC66815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	698
0.2-0.3	957
0.3-0.4	1754
0.4-0.5	2903
0.5-0.6	1900
0.6-0.7	569
0.7-0.8	49
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
0.7906	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7884	Intermediate Similarity	NPD3920	Phase 2
0.7854	Intermediate Similarity	NPD4502	Phase 2
0.7742	Intermediate Similarity	NPD6494	Phase 2
0.7621	Intermediate Similarity	NPD5658	Approved
0.761	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD2176	Approved
0.7574	Intermediate Similarity	NPD2177	Approved
0.7574	Intermediate Similarity	NPD2175	Phase 3
0.7538	Intermediate Similarity	NPD3922	Approved
0.7538	Intermediate Similarity	NPD3923	Approved
0.7538	Intermediate Similarity	NPD3924	Approved
0.7538	Intermediate Similarity	NPD3921	Approved
0.7488	Intermediate Similarity	NPD7222	Phase 2
0.7463	Intermediate Similarity	NPD6590	Discontinued
0.7463	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6550	Discontinued
0.7418	Intermediate Similarity	NPD5164	Discontinued
0.7374	Intermediate Similarity	NPD5256	Discontinued
0.7347	Intermediate Similarity	NPD4204	Approved
0.7347	Intermediate Similarity	NPD4203	Approved
0.7324	Intermediate Similarity	NPD5903	Approved
0.7324	Intermediate Similarity	NPD5902	Approved
0.7321	Intermediate Similarity	NPD7453	Approved
0.7321	Intermediate Similarity	NPD6290	Phase 2
0.7321	Intermediate Similarity	NPD7452	Approved
0.7315	Intermediate Similarity	NPD5930	Phase 3
0.7292	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6159	Phase 2
0.7273	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD3875	Discontinued
0.7255	Intermediate Similarity	NPD5512	Phase 3
0.7248	Intermediate Similarity	NPD1954	Phase 1
0.723	Intermediate Similarity	NPD3816	Phase 1
0.723	Intermediate Similarity	NPD3815	Phase 1
0.7225	Intermediate Similarity	NPD4037	Approved
0.7225	Intermediate Similarity	NPD4035	Approved
0.7225	Intermediate Similarity	NPD32	Approved
0.7225	Intermediate Similarity	NPD4036	Approved
0.7225	Intermediate Similarity	NPD4038	Approved
0.7225	Intermediate Similarity	NPD4039	Approved
0.7225	Intermediate Similarity	NPD4033	Approved
0.7225	Intermediate Similarity	NPD4034	Approved
0.7225	Intermediate Similarity	NPD4122	Approved
0.7225	Intermediate Similarity	NPD31	Approved
0.7198	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5936	Approved
0.7183	Intermediate Similarity	NPD4131	Phase 3
0.7183	Intermediate Similarity	NPD5939	Approved
0.7169	Intermediate Similarity	NPD1856	Discontinued
0.7167	Intermediate Similarity	NPD7859	Phase 2
0.7156	Intermediate Similarity	NPD5429	Discontinued
0.7156	Intermediate Similarity	NPD6963	Approved
0.7156	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6964	Approved
0.7143	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6988	Phase 1
0.713	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4875	Phase 3
0.7118	Intermediate Similarity	NPD4876	Phase 3
0.711	Intermediate Similarity	NPD3763	Approved
0.711	Intermediate Similarity	NPD2899	Discontinued
0.7109	Intermediate Similarity	NPD3003	Approved
0.7083	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4083	Discontinued
0.7067	Intermediate Similarity	NPD1768	Approved
0.7051	Intermediate Similarity	NPD5612	Discontinued
0.7039	Intermediate Similarity	NPD4418	Discontinued
0.7039	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7558	Phase 2
0.7028	Intermediate Similarity	NPD5530	Phase 1
0.7024	Intermediate Similarity	NPD6569	Phase 2
0.7022	Intermediate Similarity	NPD1505	Phase 2
0.7009	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD9690	Approved
0.7004	Intermediate Similarity	NPD8244	Phase 2
0.7	Intermediate Similarity	NPD3386	Phase 2
0.6985	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4795	Phase 2
0.698	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD112	Approved
0.6979	Remote Similarity	NPD9705	Discontinued
0.6974	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD1740	Approved
0.6952	Remote Similarity	NPD1739	Approved
0.6951	Remote Similarity	NPD3925	Approved
0.6948	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7263	Phase 2
0.6912	Remote Similarity	NPD2383	Phase 1
0.6912	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7395	Discontinued
0.6908	Remote Similarity	NPD6361	Phase 2
0.6908	Remote Similarity	NPD4551	Phase 2
0.69	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5833	Phase 1
0.689	Remote Similarity	NPD1229	Phase 2
0.6883	Remote Similarity	NPD5905	Phase 1
0.6875	Remote Similarity	NPD7955	Approved
0.6875	Remote Similarity	NPD7956	Approved
0.687	Remote Similarity	NPD5805	Approved
0.6863	Remote Similarity	NPD4375	Approved
0.6859	Remote Similarity	NPD4675	Approved
0.6859	Remote Similarity	NPD4678	Approved
0.6854	Remote Similarity	NPD6991	Approved
0.6853	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2843	Phase 2
0.6845	Remote Similarity	NPD2845	Phase 2
0.6844	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3477	Phase 2
0.6837	Remote Similarity	NPD1392	Approved
0.6835	Remote Similarity	NPD7069	Discontinued
0.6833	Remote Similarity	NPD7169	Suspended
0.6833	Remote Similarity	NPD6985	Discontinued
0.6832	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7125	Discontinued
0.6827	Remote Similarity	NPD1038	Approved
0.6825	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4605	Approved
0.681	Remote Similarity	NPD4604	Approved
0.6802	Remote Similarity	NPD7194	Discontinued
0.68	Remote Similarity	NPD4354	Approved
0.6798	Remote Similarity	NPD4995	Approved
0.6798	Remote Similarity	NPD4996	Approved
0.6788	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6736	Discontinued
0.6781	Remote Similarity	NPD7417	Discontinued
0.6774	Remote Similarity	NPD4437	Phase 3
0.6772	Remote Similarity	NPD4123	Phase 3
0.677	Remote Similarity	NPD3263	Phase 3
0.6767	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4927	Discontinued
0.6757	Remote Similarity	NPD4429	Discontinued
0.6754	Remote Similarity	NPD5022	Discontinued
0.6754	Remote Similarity	NPD4925	Approved
0.6753	Remote Similarity	NPD4454	Phase 2
0.6751	Remote Similarity	NPD3886	Phase 1
0.675	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD3037	Phase 1
0.6745	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4080	Discontinued
0.6738	Remote Similarity	NPD3525	Discontinued
0.6737	Remote Similarity	NPD8359	Phase 2
0.6735	Remote Similarity	NPD7803	Approved
0.6728	Remote Similarity	NPD7672	Approved
0.6728	Remote Similarity	NPD7671	Approved
0.6726	Remote Similarity	NPD6974	Phase 3
0.6726	Remote Similarity	NPD6246	Approved
0.6726	Remote Similarity	NPD7719	Discontinued
0.6726	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6244	Phase 3
0.6723	Remote Similarity	NPD6243	Phase 3
0.6716	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD408	Approved
0.6714	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4206	Approved
0.6712	Remote Similarity	NPD5416	Discontinued
0.6712	Remote Similarity	NPD6220	Phase 3
0.6711	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3963	Phase 1
0.6698	Remote Similarity	NPD2727	Phase 2
0.6698	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4885	Approved
0.6696	Remote Similarity	NPD5640	Discontinued
0.6695	Remote Similarity	NPD4350	Approved
0.6695	Remote Similarity	NPD6230	Discontinued
0.6695	Remote Similarity	NPD4349	Approved
0.6694	Remote Similarity	NPD8091	Phase 3
0.6683	Remote Similarity	NPD6642	Approved
0.6683	Remote Similarity	NPD2564	Approved
0.6683	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6641	Approved
0.6683	Remote Similarity	NPD2565	Phase 2
0.6681	Remote Similarity	NPD6517	Phase 3
0.6681	Remote Similarity	NPD3006	Discontinued
0.6681	Remote Similarity	NPD6716	Phase 1
0.6681	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2749	Discontinued
0.6667	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6326	Phase 2
0.6667	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6298	Discontinued
0.6667	Remote Similarity	NPD5999	Phase 2
0.6667	Remote Similarity	NPD9695	Approved

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