NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.13
Volume:	211.303
LogP:	3.789
LogD:	3.398
LogS:	-3.944
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	3.615
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.611
MDCK Permeability:	3.051479325222317e-05
Pgp-inhibitor:	0.136
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.358
Plasma Protein Binding (PPB):	94.8199234008789%
Volume Distribution (VD):	1.269
Pgp-substrate:	3.3392152786254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.32
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.394
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.176
CYP2C9-substrate:	0.697
CYP2D6-inhibitor:	0.291
CYP2D6-substrate:	0.464
CYP3A4-inhibitor:	0.5
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	8.489
Half-life (T1/2):	0.324

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.168
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.945
Carcinogencity:	0.647
Eye Corrosion:	0.183
Eye Irritation:	0.944
Respiratory Toxicity:	0.819

Download Data

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

Natural Product: NPC41780

Natural Product ID:	NPC41780
*Common Name:**	Sedanolide
IUPAC Name:	3-butyl-3a,4,5,6-tetrahydro-3H-2-benzofuran-1-one
Synonyms:	Sedanolide
Standard InCHIKey:	UPJFTVFLSIQQAV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H18O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h7,9,11H,2-6,8H2,1H3
SMILES:	CCCCC1C2CCCC=C2C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2165230
PubChem CID:	5018391
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[9987830]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8583	Angelica japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	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
NPO26721	NPC41780	Raw	Plant	16.5	7	26	mg/100g	Database [DUKE]

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-0.57	%	PMID[495392]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	4.12	%	PMID[495392]

☑ 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 NPC41780 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	172
0.1-0.2	1132
0.2-0.3	5621
0.3-0.4	14408
0.4-0.5	10643
0.5-0.6	6300
0.6-0.7	3419
0.7-0.8	836
0.8-0.85	110
0.85-0.9	39
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC187568
0.9054	High Similarity	NPC235906
0.9041	High Similarity	NPC476355
0.9028	High Similarity	NPC163003
0.8933	High Similarity	NPC65603
0.8919	High Similarity	NPC226669
0.8919	High Similarity	NPC155587
0.8919	High Similarity	NPC193351
0.8919	High Similarity	NPC138408
0.8904	High Similarity	NPC58956
0.8904	High Similarity	NPC295633
0.8904	High Similarity	NPC269206
0.8846	High Similarity	NPC178676
0.88	High Similarity	NPC123360
0.8784	High Similarity	NPC140287
0.8734	High Similarity	NPC22611
0.8701	High Similarity	NPC472965
0.8701	High Similarity	NPC264227
0.8701	High Similarity	NPC63649
0.8684	High Similarity	NPC470240
0.8684	High Similarity	NPC476794
0.8608	High Similarity	NPC173609
0.859	High Similarity	NPC302426
0.8571	High Similarity	NPC108816
0.8571	High Similarity	NPC472960
0.8571	High Similarity	NPC128276
0.8571	High Similarity	NPC93763
0.8571	High Similarity	NPC471220
0.8553	High Similarity	NPC473223
0.8519	High Similarity	NPC110405
0.8514	High Similarity	NPC129665
0.85	High Similarity	NPC193198
0.8493	Intermediate Similarity	NPC199557
0.8481	Intermediate Similarity	NPC141810
0.8481	Intermediate Similarity	NPC281949
0.8481	Intermediate Similarity	NPC301477
0.8481	Intermediate Similarity	NPC25684
0.8481	Intermediate Similarity	NPC471325
0.8462	Intermediate Similarity	NPC270126
0.8462	Intermediate Similarity	NPC470244
0.8462	Intermediate Similarity	NPC470239
0.8462	Intermediate Similarity	NPC178277
0.8462	Intermediate Similarity	NPC617
0.8462	Intermediate Similarity	NPC182550
0.8442	Intermediate Similarity	NPC141789
0.8442	Intermediate Similarity	NPC57744
0.8442	Intermediate Similarity	NPC7563
0.8442	Intermediate Similarity	NPC320630
0.8442	Intermediate Similarity	NPC116177
0.8442	Intermediate Similarity	NPC476028
0.8442	Intermediate Similarity	NPC97516
0.8442	Intermediate Similarity	NPC171204
0.8434	Intermediate Similarity	NPC215831
0.8434	Intermediate Similarity	NPC226863
0.8395	Intermediate Similarity	NPC159635
0.8395	Intermediate Similarity	NPC30486
0.8375	Intermediate Similarity	NPC186276
0.8356	Intermediate Similarity	NPC470256
0.8354	Intermediate Similarity	NPC281132
0.8354	Intermediate Similarity	NPC195424
0.8354	Intermediate Similarity	NPC69271
0.8354	Intermediate Similarity	NPC74673
0.8354	Intermediate Similarity	NPC223904
0.8354	Intermediate Similarity	NPC276356
0.8333	Intermediate Similarity	NPC267231
0.8333	Intermediate Similarity	NPC299235
0.8333	Intermediate Similarity	NPC471465
0.8333	Intermediate Similarity	NPC196653
0.8333	Intermediate Similarity	NPC73995
0.8312	Intermediate Similarity	NPC27205
0.8293	Intermediate Similarity	NPC177932
0.8272	Intermediate Similarity	NPC475947
0.8272	Intermediate Similarity	NPC39588
0.8272	Intermediate Similarity	NPC318468
0.8256	Intermediate Similarity	NPC475657
0.825	Intermediate Similarity	NPC10276
0.825	Intermediate Similarity	NPC35089
0.8235	Intermediate Similarity	NPC152467
0.8235	Intermediate Similarity	NPC220454
0.8235	Intermediate Similarity	NPC212679
0.8235	Intermediate Similarity	NPC469595
0.8228	Intermediate Similarity	NPC471299
0.8228	Intermediate Similarity	NPC167881
0.8228	Intermediate Similarity	NPC98557
0.8219	Intermediate Similarity	NPC194871
0.8193	Intermediate Similarity	NPC107787
0.8193	Intermediate Similarity	NPC305475
0.8193	Intermediate Similarity	NPC475461
0.8193	Intermediate Similarity	NPC284902
0.8171	Intermediate Similarity	NPC191476
0.8171	Intermediate Similarity	NPC141193
0.8171	Intermediate Similarity	NPC114979
0.8171	Intermediate Similarity	NPC96259
0.8171	Intermediate Similarity	NPC115786
0.8161	Intermediate Similarity	NPC477130
0.8161	Intermediate Similarity	NPC477129
0.8158	Intermediate Similarity	NPC472956
0.8148	Intermediate Similarity	NPC475690
0.8133	Intermediate Similarity	NPC472955
0.8118	Intermediate Similarity	NPC168131
0.8108	Intermediate Similarity	NPC218477
0.8101	Intermediate Similarity	NPC35574
0.8095	Intermediate Similarity	NPC475703
0.8095	Intermediate Similarity	NPC312561
0.8077	Intermediate Similarity	NPC472967
0.8077	Intermediate Similarity	NPC266159
0.8077	Intermediate Similarity	NPC472959
0.8072	Intermediate Similarity	NPC33570
0.8072	Intermediate Similarity	NPC21471
0.8072	Intermediate Similarity	NPC165162
0.8072	Intermediate Similarity	NPC189311
0.8072	Intermediate Similarity	NPC255307
0.8072	Intermediate Similarity	NPC215364
0.8072	Intermediate Similarity	NPC78089
0.8072	Intermediate Similarity	NPC161957
0.8068	Intermediate Similarity	NPC183012
0.8052	Intermediate Similarity	NPC117746
0.8052	Intermediate Similarity	NPC294434
0.8052	Intermediate Similarity	NPC15499
0.8052	Intermediate Similarity	NPC259599
0.8049	Intermediate Similarity	NPC272814
0.8049	Intermediate Similarity	NPC59097
0.8049	Intermediate Similarity	NPC40746
0.8049	Intermediate Similarity	NPC250315
0.8049	Intermediate Similarity	NPC215294
0.8049	Intermediate Similarity	NPC170286
0.8049	Intermediate Similarity	NPC53867
0.8049	Intermediate Similarity	NPC169575
0.8026	Intermediate Similarity	NPC257618
0.8025	Intermediate Similarity	NPC24417
0.8025	Intermediate Similarity	NPC475665
0.8025	Intermediate Similarity	NPC42470
0.8025	Intermediate Similarity	NPC325031
0.8025	Intermediate Similarity	NPC38642
0.8023	Intermediate Similarity	NPC158488
0.8023	Intermediate Similarity	NPC469372
0.8	Intermediate Similarity	NPC89128
0.8	Intermediate Similarity	NPC477302
0.8	Intermediate Similarity	NPC136879
0.8	Intermediate Similarity	NPC144511
0.8	Intermediate Similarity	NPC296522
0.8	Intermediate Similarity	NPC473981
0.8	Intermediate Similarity	NPC477128
0.8	Intermediate Similarity	NPC277771
0.8	Intermediate Similarity	NPC473980
0.7976	Intermediate Similarity	NPC150755
0.7976	Intermediate Similarity	NPC50637
0.7976	Intermediate Similarity	NPC220478
0.7976	Intermediate Similarity	NPC38576
0.7976	Intermediate Similarity	NPC279859
0.7975	Intermediate Similarity	NPC15975
0.7975	Intermediate Similarity	NPC474760
0.7975	Intermediate Similarity	NPC103987
0.7975	Intermediate Similarity	NPC195785
0.7975	Intermediate Similarity	NPC53581
0.7973	Intermediate Similarity	NPC472266
0.7955	Intermediate Similarity	NPC476596
0.7952	Intermediate Similarity	NPC474359
0.7952	Intermediate Similarity	NPC475100
0.7952	Intermediate Similarity	NPC476804
0.7952	Intermediate Similarity	NPC295799
0.7952	Intermediate Similarity	NPC149869
0.7949	Intermediate Similarity	NPC244166
0.7931	Intermediate Similarity	NPC65513
0.7931	Intermediate Similarity	NPC186363
0.7931	Intermediate Similarity	NPC233345
0.7927	Intermediate Similarity	NPC200513
0.7927	Intermediate Similarity	NPC229825
0.7927	Intermediate Similarity	NPC89555
0.7927	Intermediate Similarity	NPC35556
0.7922	Intermediate Similarity	NPC135703
0.7917	Intermediate Similarity	NPC474658
0.7907	Intermediate Similarity	NPC218927
0.7907	Intermediate Similarity	NPC206001
0.7907	Intermediate Similarity	NPC295312
0.7907	Intermediate Similarity	NPC268298
0.7907	Intermediate Similarity	NPC288699
0.7907	Intermediate Similarity	NPC166919
0.7895	Intermediate Similarity	NPC469660
0.7882	Intermediate Similarity	NPC160138
0.7882	Intermediate Similarity	NPC231889
0.7875	Intermediate Similarity	NPC184737
0.7875	Intermediate Similarity	NPC474341
0.7875	Intermediate Similarity	NPC475699
0.7857	Intermediate Similarity	NPC50362
0.7857	Intermediate Similarity	NPC470755
0.7857	Intermediate Similarity	NPC319795
0.7857	Intermediate Similarity	NPC38468
0.7848	Intermediate Similarity	NPC40353
0.7841	Intermediate Similarity	NPC476597
0.7841	Intermediate Similarity	NPC166346
0.7841	Intermediate Similarity	NPC476598
0.7831	Intermediate Similarity	NPC473390
0.7831	Intermediate Similarity	NPC474703
0.7831	Intermediate Similarity	NPC131669
0.7821	Intermediate Similarity	NPC474758
0.7821	Intermediate Similarity	NPC320537
0.7821	Intermediate Similarity	NPC143979
0.7816	Intermediate Similarity	NPC232426
0.7816	Intermediate Similarity	NPC129419

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 NPC41780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1598
0.2-0.3	3934
0.3-0.4	2317
0.4-0.5	736
0.5-0.6	309
0.6-0.7	82
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
0.8293	Intermediate Similarity	NPD1694	Approved
0.7927	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8039	Approved
0.75	Intermediate Similarity	NPD1695	Approved
0.7467	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD46	Approved
0.7222	Intermediate Similarity	NPD5785	Approved
0.7222	Intermediate Similarity	NPD6698	Approved
0.7159	Intermediate Similarity	NPD6684	Approved
0.7159	Intermediate Similarity	NPD7334	Approved
0.7159	Intermediate Similarity	NPD7521	Approved
0.7159	Intermediate Similarity	NPD7146	Approved
0.7159	Intermediate Similarity	NPD6409	Approved
0.7159	Intermediate Similarity	NPD5330	Approved
0.7093	Intermediate Similarity	NPD5209	Approved
0.7053	Intermediate Similarity	NPD4225	Approved
0.7045	Intermediate Similarity	NPD5363	Approved
0.7011	Intermediate Similarity	NPD7154	Phase 3
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6903	Approved
0.6818	Remote Similarity	NPD5362	Discontinued
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6774	Remote Similarity	NPD5693	Phase 1
0.6742	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4756	Discovery
0.6705	Remote Similarity	NPD4269	Approved
0.6705	Remote Similarity	NPD4270	Approved
0.6702	Remote Similarity	NPD6399	Phase 3
0.6702	Remote Similarity	NPD5779	Approved
0.6702	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5207	Approved
0.6635	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7900	Approved
0.6593	Remote Similarity	NPD5786	Approved
0.6591	Remote Similarity	NPD5369	Approved
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6101	Approved
0.6531	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6505	Remote Similarity	NPD6686	Approved
0.65	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7331	Phase 2
0.6489	Remote Similarity	NPD7838	Discovery
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.6465	Remote Similarity	NPD7639	Approved
0.6465	Remote Similarity	NPD7640	Approved
0.6458	Remote Similarity	NPD7748	Approved
0.6458	Remote Similarity	NPD6001	Approved
0.6452	Remote Similarity	NPD5208	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7902	Approved
0.6421	Remote Similarity	NPD6411	Approved
0.6415	Remote Similarity	NPD6053	Discontinued
0.6413	Remote Similarity	NPD3618	Phase 1
0.6392	Remote Similarity	NPD5695	Phase 3
0.6383	Remote Similarity	NPD6904	Approved
0.6383	Remote Similarity	NPD6673	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6383	Remote Similarity	NPD6080	Approved
0.6381	Remote Similarity	NPD6371	Approved
0.6374	Remote Similarity	NPD3133	Approved
0.6374	Remote Similarity	NPD3665	Phase 1
0.6374	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6333	Remote Similarity	NPD6435	Approved
0.6333	Remote Similarity	NPD3667	Approved
0.6316	Remote Similarity	NPD5692	Phase 3
0.6292	Remote Similarity	NPD4695	Discontinued
0.6292	Remote Similarity	NPD4819	Approved
0.6292	Remote Similarity	NPD4822	Approved
0.6292	Remote Similarity	NPD4821	Approved
0.6292	Remote Similarity	NPD4820	Approved
0.6289	Remote Similarity	NPD5282	Discontinued
0.6264	Remote Similarity	NPD5331	Approved
0.6264	Remote Similarity	NPD5332	Approved
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD4271	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6098	Approved
0.6237	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD6422	Discontinued
0.6237	Remote Similarity	NPD5279	Phase 3
0.6226	Remote Similarity	NPD2067	Discontinued
0.6222	Remote Similarity	NPD4790	Discontinued
0.6196	Remote Similarity	NPD4786	Approved
0.6196	Remote Similarity	NPD3668	Phase 3
0.619	Remote Similarity	NPD4691	Approved
0.6173	Remote Similarity	NPD7341	Phase 2
0.617	Remote Similarity	NPD4250	Approved
0.617	Remote Similarity	NPD4251	Approved
0.6168	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD6927	Phase 3
0.6162	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7839	Suspended
0.6139	Remote Similarity	NPD6648	Approved
0.6129	Remote Similarity	NPD1696	Phase 3
0.6125	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5368	Approved
0.6095	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD7637	Suspended
0.6082	Remote Similarity	NPD5284	Approved
0.6082	Remote Similarity	NPD5281	Approved
0.6082	Remote Similarity	NPD6079	Approved
0.6082	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5344	Discontinued
0.6075	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4137	Phase 3
0.6064	Remote Similarity	NPD4623	Approved
0.6064	Remote Similarity	NPD4519	Discontinued
0.6042	Remote Similarity	NPD5328	Approved
0.6042	Remote Similarity	NPD5370	Suspended
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD6011	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6019	Remote Similarity	NPD6650	Approved
0.6019	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD4191	Approved
0.5981	Remote Similarity	NPD6014	Approved
0.5981	Remote Similarity	NPD6372	Approved
0.5981	Remote Similarity	NPD6012	Approved
0.5981	Remote Similarity	NPD2182	Approved
0.5981	Remote Similarity	NPD6013	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6373	Approved
0.5978	Remote Similarity	NPD4223	Phase 3
0.5978	Remote Similarity	NPD4221	Approved
0.5977	Remote Similarity	NPD4058	Approved
0.5962	Remote Similarity	NPD6052	Approved
0.5946	Remote Similarity	NPD28	Approved
0.5946	Remote Similarity	NPD29	Approved
0.5943	Remote Similarity	NPD5701	Approved
0.5934	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5276	Approved
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5904	Remote Similarity	NPD3704	Approved
0.59	Remote Similarity	NPD5654	Approved
0.59	Remote Similarity	NPD5210	Approved
0.59	Remote Similarity	NPD4629	Approved
0.5895	Remote Similarity	NPD5690	Phase 2
0.5895	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7320	Approved
0.5876	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4753	Phase 2
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD6617	Approved
0.5872	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7632	Discontinued
0.5859	Remote Similarity	NPD4202	Approved
0.5854	Remote Similarity	NPD3197	Phase 1
0.5851	Remote Similarity	NPD4197	Approved
0.5842	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD4697	Phase 3
0.5842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5221	Approved
0.5842	Remote Similarity	NPD7732	Phase 3
0.5826	Remote Similarity	NPD8516	Approved
0.5826	Remote Similarity	NPD8515	Approved
0.5826	Remote Similarity	NPD8517	Approved
0.5826	Remote Similarity	NPD8513	Phase 3
0.5825	Remote Similarity	NPD6404	Discontinued
0.5823	Remote Similarity	NPD287	Approved
0.5818	Remote Similarity	NPD8297	Approved
0.5818	Remote Similarity	NPD6882	Approved
0.581	Remote Similarity	NPD6647	Phase 2
0.5802	Remote Similarity	NPD368	Approved
0.5795	Remote Similarity	NPD4687	Approved
0.5795	Remote Similarity	NPD5733	Approved
0.5794	Remote Similarity	NPD6614	Approved
0.5789	Remote Similarity	NPD5329	Approved
0.5789	Remote Similarity	NPD3172	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