NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.15
Volume:	251.998
LogP:	3.879
LogD:	3.954
LogS:	-4.051
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	4.349
Fsp3:	0.6
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:	-4.699
MDCK Permeability:	2.3864287868491374e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.336
Plasma Protein Binding (PPB):	96.9725570678711%
Volume Distribution (VD):	1.419
Pgp-substrate:	3.6543781757354736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.346
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.103
CYP2C19-substrate:	0.683
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.657
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	7.879
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.742
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.279
Maximum Recommended Daily Dose:	0.587
Skin Sensitization:	0.312
Carcinogencity:	0.552
Eye Corrosion:	0.008
Eye Irritation:	0.264
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC189206

Natural Product ID:	NPC189206
*Common Name:**	Atractylenolide Ii
IUPAC Name:	(4aS,8aR,9aS)-3,8a-dimethyl-5-methylidene-4a,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:	Atractylenolide II
Standard InCHIKey:	OQYBLUDOOFOBPO-KCQAQPDRSA-N
Standard InCHI:	InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h12-13H,1,4-8H2,2-3H3/t12-,13-,15+/m0/s1
SMILES:	C=C1CCC[C@]2(C)C[C@H]3C(=C(C)C(=O)O3)C[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485805
PubChem CID:	14448070
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO40789	Atractylodes rhizomes	Species	Asteraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[6418860]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	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
IC50	2
Others	7

Activity Type	# Activity
Cell Line	2
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	74.0	%	PMID[488785]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	94.0	%	PMID[488785]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	200000.0	nM	PMID[488786]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	200000.0	nM	PMID[488786]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.0	n.a.	PMID[488787]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.5	n.a.	PMID[488787]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	RLU	=	1.5	n.a.	PMID[488787]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Inhibition	=	50.0	%	PMID[488787]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	RLU	=	0.9	n.a.	PMID[488787]

☑ 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 NPC189206 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	178
0.1-0.2	1253
0.2-0.3	5180
0.3-0.4	14832
0.4-0.5	9111
0.5-0.6	7458
0.6-0.7	3928
0.7-0.8	671
0.8-0.85	69
0.85-0.9	15
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC268827
0.9067	High Similarity	NPC184737
0.8861	High Similarity	NPC96055
0.8831	High Similarity	NPC10636
0.8765	High Similarity	NPC473891
0.875	High Similarity	NPC474013
0.8642	High Similarity	NPC131813
0.8625	High Similarity	NPC32223
0.8608	High Similarity	NPC471218
0.85	High Similarity	NPC311070
0.8452	Intermediate Similarity	NPC221111
0.8452	Intermediate Similarity	NPC310479
0.8452	Intermediate Similarity	NPC280149
0.8452	Intermediate Similarity	NPC182136
0.8442	Intermediate Similarity	NPC54996
0.8434	Intermediate Similarity	NPC93411
0.8395	Intermediate Similarity	NPC30486
0.8375	Intermediate Similarity	NPC200513
0.8354	Intermediate Similarity	NPC469802
0.8333	Intermediate Similarity	NPC50488
0.8333	Intermediate Similarity	NPC474396
0.8272	Intermediate Similarity	NPC474193
0.8272	Intermediate Similarity	NPC12283
0.8256	Intermediate Similarity	NPC139692
0.8256	Intermediate Similarity	NPC152778
0.8256	Intermediate Similarity	NPC205034
0.8256	Intermediate Similarity	NPC162615
0.825	Intermediate Similarity	NPC170303
0.8235	Intermediate Similarity	NPC8062
0.8235	Intermediate Similarity	NPC78973
0.8205	Intermediate Similarity	NPC316500
0.8193	Intermediate Similarity	NPC329692
0.814	Intermediate Similarity	NPC472811
0.814	Intermediate Similarity	NPC329842
0.814	Intermediate Similarity	NPC72845
0.8072	Intermediate Similarity	NPC189311
0.8072	Intermediate Similarity	NPC65661
0.8072	Intermediate Similarity	NPC30984
0.8072	Intermediate Similarity	NPC86316
0.8072	Intermediate Similarity	NPC106416
0.8049	Intermediate Similarity	NPC193198
0.8049	Intermediate Similarity	NPC30502
0.8049	Intermediate Similarity	NPC321385
0.8046	Intermediate Similarity	NPC7349
0.8046	Intermediate Similarity	NPC53555
0.8046	Intermediate Similarity	NPC472812
0.8025	Intermediate Similarity	NPC282293
0.8023	Intermediate Similarity	NPC472642
0.8	Intermediate Similarity	NPC106332
0.8	Intermediate Similarity	NPC226863
0.8	Intermediate Similarity	NPC472810
0.8	Intermediate Similarity	NPC472809
0.7978	Intermediate Similarity	NPC134072
0.7978	Intermediate Similarity	NPC234993
0.7978	Intermediate Similarity	NPC16967
0.7978	Intermediate Similarity	NPC242848
0.7978	Intermediate Similarity	NPC473153
0.7978	Intermediate Similarity	NPC209297
0.7978	Intermediate Similarity	NPC475380
0.7976	Intermediate Similarity	NPC471219
0.7973	Intermediate Similarity	NPC472266
0.7955	Intermediate Similarity	NPC105490
0.7955	Intermediate Similarity	NPC191521
0.7955	Intermediate Similarity	NPC57117
0.7955	Intermediate Similarity	NPC84893
0.7955	Intermediate Similarity	NPC470255
0.7955	Intermediate Similarity	NPC140277
0.7952	Intermediate Similarity	NPC306951
0.7952	Intermediate Similarity	NPC318515
0.7931	Intermediate Similarity	NPC177037
0.7931	Intermediate Similarity	NPC472814
0.7931	Intermediate Similarity	NPC78594
0.7927	Intermediate Similarity	NPC256112
0.7927	Intermediate Similarity	NPC178676
0.7927	Intermediate Similarity	NPC226988
0.7907	Intermediate Similarity	NPC177141
0.7907	Intermediate Similarity	NPC73995
0.7901	Intermediate Similarity	NPC281880
0.7889	Intermediate Similarity	NPC311241
0.7889	Intermediate Similarity	NPC100912
0.7889	Intermediate Similarity	NPC475446
0.7882	Intermediate Similarity	NPC166857
0.7882	Intermediate Similarity	NPC476600
0.7875	Intermediate Similarity	NPC471220
0.7865	Intermediate Similarity	NPC472441
0.7865	Intermediate Similarity	NPC276110
0.7857	Intermediate Similarity	NPC177932
0.7857	Intermediate Similarity	NPC472442
0.7857	Intermediate Similarity	NPC253604
0.7857	Intermediate Similarity	NPC471795
0.7848	Intermediate Similarity	NPC4509
0.7841	Intermediate Similarity	NPC472640
0.7841	Intermediate Similarity	NPC472641
0.7841	Intermediate Similarity	NPC472303
0.7841	Intermediate Similarity	NPC110022
0.7838	Intermediate Similarity	NPC116013
0.7831	Intermediate Similarity	NPC476927
0.7831	Intermediate Similarity	NPC222358
0.7831	Intermediate Similarity	NPC477124
0.7831	Intermediate Similarity	NPC42476
0.7831	Intermediate Similarity	NPC472440
0.7831	Intermediate Similarity	NPC472377
0.7831	Intermediate Similarity	NPC22611
0.7816	Intermediate Similarity	NPC152467
0.7816	Intermediate Similarity	NPC273199
0.7816	Intermediate Similarity	NPC51486
0.7816	Intermediate Similarity	NPC302280
0.7816	Intermediate Similarity	NPC161638
0.7805	Intermediate Similarity	NPC475665
0.7805	Intermediate Similarity	NPC159148
0.7805	Intermediate Similarity	NPC25554
0.7802	Intermediate Similarity	NPC474440
0.7802	Intermediate Similarity	NPC72647
0.7802	Intermediate Similarity	NPC107806
0.7791	Intermediate Similarity	NPC472302
0.7791	Intermediate Similarity	NPC215831
0.7791	Intermediate Similarity	NPC473879
0.7778	Intermediate Similarity	NPC165632
0.7778	Intermediate Similarity	NPC194132
0.7778	Intermediate Similarity	NPC150646
0.7778	Intermediate Similarity	NPC242767
0.7778	Intermediate Similarity	NPC260796
0.7753	Intermediate Similarity	NPC161998
0.7738	Intermediate Similarity	NPC475100
0.7738	Intermediate Similarity	NPC474693
0.7738	Intermediate Similarity	NPC149869
0.7727	Intermediate Similarity	NPC473944
0.7727	Intermediate Similarity	NPC49420
0.7727	Intermediate Similarity	NPC472953
0.7727	Intermediate Similarity	NPC289479
0.7717	Intermediate Similarity	NPC117685
0.7717	Intermediate Similarity	NPC201406
0.7717	Intermediate Similarity	NPC16601
0.7717	Intermediate Similarity	NPC471413
0.7701	Intermediate Similarity	NPC5509
0.7701	Intermediate Similarity	NPC251528
0.7701	Intermediate Similarity	NPC174342
0.7701	Intermediate Similarity	NPC82876
0.7701	Intermediate Similarity	NPC470734
0.7692	Intermediate Similarity	NPC222244
0.7692	Intermediate Similarity	NPC205143
0.7692	Intermediate Similarity	NPC73911
0.7692	Intermediate Similarity	NPC16349
0.7692	Intermediate Similarity	NPC84335
0.7692	Intermediate Similarity	NPC476768
0.7692	Intermediate Similarity	NPC38530
0.7692	Intermediate Similarity	NPC231751
0.7692	Intermediate Similarity	NPC474343
0.7692	Intermediate Similarity	NPC51499
0.7692	Intermediate Similarity	NPC110937
0.7683	Intermediate Similarity	NPC233332
0.7683	Intermediate Similarity	NPC195424
0.7674	Intermediate Similarity	NPC471796
0.7674	Intermediate Similarity	NPC312561
0.7674	Intermediate Similarity	NPC102640
0.7667	Intermediate Similarity	NPC183012
0.7667	Intermediate Similarity	NPC474909
0.7667	Intermediate Similarity	NPC111273
0.7667	Intermediate Similarity	NPC471915
0.7662	Intermediate Similarity	NPC469660
0.7654	Intermediate Similarity	NPC35574
0.7647	Intermediate Similarity	NPC473659
0.7647	Intermediate Similarity	NPC110405
0.7647	Intermediate Similarity	NPC473251
0.7647	Intermediate Similarity	NPC476678
0.7647	Intermediate Similarity	NPC475860
0.7647	Intermediate Similarity	NPC42586
0.7647	Intermediate Similarity	NPC474694
0.764	Intermediate Similarity	NPC475657
0.764	Intermediate Similarity	NPC38232
0.764	Intermediate Similarity	NPC115021
0.7634	Intermediate Similarity	NPC303559
0.7634	Intermediate Similarity	NPC471412
0.7632	Intermediate Similarity	NPC276290
0.7625	Intermediate Similarity	NPC92489
0.7619	Intermediate Similarity	NPC79945
0.7614	Intermediate Similarity	NPC220454
0.7614	Intermediate Similarity	NPC212679
0.7614	Intermediate Similarity	NPC477782
0.7614	Intermediate Similarity	NPC469595
0.7609	Intermediate Similarity	NPC159763
0.7609	Intermediate Similarity	NPC124512
0.7609	Intermediate Similarity	NPC275086
0.7609	Intermediate Similarity	NPC278386
0.7609	Intermediate Similarity	NPC473154
0.7609	Intermediate Similarity	NPC325229
0.7609	Intermediate Similarity	NPC278673
0.76	Intermediate Similarity	NPC185587
0.759	Intermediate Similarity	NPC229584
0.759	Intermediate Similarity	NPC40228
0.759	Intermediate Similarity	NPC14203
0.7586	Intermediate Similarity	NPC242448
0.7586	Intermediate Similarity	NPC69713
0.7586	Intermediate Similarity	NPC277771
0.7586	Intermediate Similarity	NPC477128
0.7582	Intermediate Similarity	NPC154526
0.7582	Intermediate Similarity	NPC472362
0.7582	Intermediate Similarity	NPC472363
0.7582	Intermediate Similarity	NPC29952
0.7564	Intermediate Similarity	NPC257618

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 NPC189206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1475
0.2-0.3	4124
0.3-0.4	2332
0.4-0.5	673
0.5-0.6	253
0.6-0.7	121
0.7-0.8	12
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
0.8375	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1694	Approved
0.7609	Intermediate Similarity	NPD7638	Approved
0.7609	Intermediate Similarity	NPD4225	Approved
0.7527	Intermediate Similarity	NPD7640	Approved
0.7527	Intermediate Similarity	NPD7639	Approved
0.7356	Intermediate Similarity	NPD6684	Approved
0.7356	Intermediate Similarity	NPD6409	Approved
0.7356	Intermediate Similarity	NPD7146	Approved
0.7356	Intermediate Similarity	NPD5330	Approved
0.7356	Intermediate Similarity	NPD7334	Approved
0.7356	Intermediate Similarity	NPD7521	Approved
0.7303	Intermediate Similarity	NPD6051	Approved
0.7237	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6903	Approved
0.7191	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.6989	Remote Similarity	NPD7748	Approved
0.6989	Remote Similarity	NPD7900	Approved
0.6989	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5693	Phase 1
0.6932	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5209	Approved
0.6889	Remote Similarity	NPD3573	Approved
0.6867	Remote Similarity	NPD8039	Approved
0.6832	Remote Similarity	NPD6686	Approved
0.6778	Remote Similarity	NPD3618	Phase 1
0.6774	Remote Similarity	NPD7515	Phase 2
0.6771	Remote Similarity	NPD7902	Approved
0.6765	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6399	Phase 3
0.6699	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5208	Approved
0.6596	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5328	Approved
0.6559	Remote Similarity	NPD6904	Approved
0.6559	Remote Similarity	NPD6673	Approved
0.6559	Remote Similarity	NPD6080	Approved
0.6556	Remote Similarity	NPD3666	Approved
0.6556	Remote Similarity	NPD3133	Approved
0.6556	Remote Similarity	NPD3665	Phase 1
0.6517	Remote Similarity	NPD3667	Approved
0.6484	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7115	Discovery
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6465	Remote Similarity	NPD6648	Approved
0.6458	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD6083	Phase 2
0.6429	Remote Similarity	NPD6084	Phase 2
0.6422	Remote Similarity	NPD7327	Approved
0.6422	Remote Similarity	NPD7328	Approved
0.6421	Remote Similarity	NPD8035	Phase 2
0.6421	Remote Similarity	NPD6079	Approved
0.6421	Remote Similarity	NPD8034	Phase 2
0.6413	Remote Similarity	NPD6098	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.6408	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD5344	Discontinued
0.6395	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5695	Phase 3
0.6392	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3668	Phase 3
0.6374	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD5696	Approved
0.6354	Remote Similarity	NPD4202	Approved
0.6353	Remote Similarity	NPD6926	Approved
0.6353	Remote Similarity	NPD6924	Approved
0.6346	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6316	Remote Similarity	NPD5785	Approved
0.6316	Remote Similarity	NPD5207	Approved
0.6316	Remote Similarity	NPD5692	Phase 3
0.6306	Remote Similarity	NPD8294	Approved
0.6306	Remote Similarity	NPD8377	Approved
0.6304	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7525	Registered
0.6286	Remote Similarity	NPD6014	Approved
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6013	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6286	Remote Similarity	NPD6012	Approved
0.6279	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD7339	Approved
0.6264	Remote Similarity	NPD6695	Phase 3
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD8335	Approved
0.625	Remote Similarity	NPD8296	Approved
0.625	Remote Similarity	NPD8380	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD8378	Approved
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD8379	Approved
0.625	Remote Similarity	NPD6050	Approved
0.6237	Remote Similarity	NPD4623	Approved
0.6237	Remote Similarity	NPD4519	Discontinued
0.6237	Remote Similarity	NPD5279	Phase 3
0.6226	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD7102	Approved
0.6211	Remote Similarity	NPD1695	Approved
0.6207	Remote Similarity	NPD6933	Approved
0.6196	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD5778	Approved
0.618	Remote Similarity	NPD6929	Approved
0.618	Remote Similarity	NPD4195	Approved
0.6174	Remote Similarity	NPD7507	Approved
0.6168	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD6869	Approved
0.6168	Remote Similarity	NPD6847	Approved
0.6168	Remote Similarity	NPD6650	Approved
0.6168	Remote Similarity	NPD8130	Phase 1
0.6162	Remote Similarity	NPD5221	Approved
0.6162	Remote Similarity	NPD4697	Phase 3
0.6162	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5222	Approved
0.6154	Remote Similarity	NPD4223	Phase 3
0.6154	Remote Similarity	NPD4221	Approved
0.6146	Remote Similarity	NPD7838	Discovery
0.6146	Remote Similarity	NPD6698	Approved
0.6146	Remote Similarity	NPD46	Approved
0.6129	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD7151	Approved
0.6118	Remote Similarity	NPD7152	Approved
0.6118	Remote Similarity	NPD7150	Approved
0.6111	Remote Similarity	NPD6931	Approved
0.6111	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD6930	Phase 2
0.6111	Remote Similarity	NPD7509	Discontinued
0.6111	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD4695	Discontinued
0.61	Remote Similarity	NPD4755	Approved
0.61	Remote Similarity	NPD5173	Approved
0.6092	Remote Similarity	NPD8264	Approved
0.6076	Remote Similarity	NPD1145	Discontinued
0.6071	Remote Similarity	NPD4137	Phase 3
0.6071	Remote Similarity	NPD6923	Approved
0.6071	Remote Similarity	NPD6922	Approved
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3617	Approved
0.6067	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4753	Phase 2
0.6042	Remote Similarity	NPD6101	Approved
0.6022	Remote Similarity	NPD4197	Approved
0.6019	Remote Similarity	NPD5211	Phase 2
0.6017	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD7143	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD4191	Approved
0.6	Remote Similarity	NPD7144	Approved
0.598	Remote Similarity	NPD4700	Approved
0.598	Remote Similarity	NPD5286	Approved
0.598	Remote Similarity	NPD5285	Approved
0.598	Remote Similarity	NPD4696	Approved
0.5965	Remote Similarity	NPD7503	Approved
0.5957	Remote Similarity	NPD1696	Phase 3
0.5957	Remote Similarity	NPD5329	Approved
0.5955	Remote Similarity	NPD6925	Approved
0.5955	Remote Similarity	NPD5776	Phase 2
0.5946	Remote Similarity	NPD6274	Approved
0.5946	Remote Similarity	NPD6868	Approved
0.5934	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7514	Phase 3
0.5934	Remote Similarity	NPD7332	Phase 2
0.593	Remote Similarity	NPD5777	Approved
0.5922	Remote Similarity	NPD5223	Approved
0.5918	Remote Similarity	NPD5284	Approved
0.5918	Remote Similarity	NPD5281	Approved
0.5914	Remote Similarity	NPD5362	Discontinued
0.5914	Remote Similarity	NPD7154	Phase 3
0.5909	Remote Similarity	NPD4632	Approved
0.5905	Remote Similarity	NPD5141	Approved
0.59	Remote Similarity	NPD5654	Approved
0.5895	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4689	Approved
0.5895	Remote Similarity	NPD5205	Approved
0.5895	Remote Similarity	NPD4138	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