NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	2.85
LogD:	2.706
LogS:	-4.02
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	4.199
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.62
MDCK Permeability:	2.0093375496799126e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.402
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.728
Plasma Protein Binding (PPB):	92.86247253417969%
Volume Distribution (VD):	2.807
Pgp-substrate:	10.178547859191895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.157
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.456

ADMET: Excretion

Clearance (CL):	5.281
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.279
Drug-inuced Liver Injury (DILI):	0.607
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.092
Carcinogencity:	0.929
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC61157

Natural Product ID:	NPC61157
*Common Name:**	Epicacalone
IUPAC Name:	(4S,5S)-4-hydroxy-3,4,5-trimethyl-5,6,7,8-tetrahydrobenzo[f][1]benzofuran-9-one
Synonyms:	Epicacalone
Standard InCHIKey:	VNNQNPHIASWXBS-AYVTZFPOSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8-5-4-6-10-11(8)15(3,17)12-9(2)7-18-14(12)13(10)16/h7-8,17H,4-6H2,1-3H3/t8-,15-/m0/s1
SMILES:	C[C@H]1CCCC2=C1[C@](C)(O)c1c(C2=O)occ1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491540
PubChem CID:	21635815
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO25807	Psacalium decompositum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10479309]
NPO25807	Psacalium decompositum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32672964]
NPO28508	Flourensia cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28034	Artemisia sylvatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28508	Flourensia cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28034	Artemisia sylvatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28508	Flourensia cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25807	Psacalium decompositum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23760	Scytonema hofmannii	Species	Scytonemataceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28317	Marinobacter hydrocarbonoclasticus	Species	Alteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20198	Lobaria isidiosa	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28034	Artemisia sylvatica	Species	Asteraceae	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
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.6	g	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	45.0	g	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-13.4	mg/dl	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-105.1	mg/dl	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-42.4	mg/dl	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	30.9	mg/dl	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	43.3	g	PMID[447932]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.0	g	PMID[447932]

☑ 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 NPC61157 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	300
0.1-0.2	1453
0.2-0.3	3679
0.3-0.4	9677
0.4-0.5	10759
0.5-0.6	6756
0.6-0.7	8379
0.7-0.8	1659
0.8-0.85	29
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC218204
1.0	High Similarity	NPC473681
0.9097	High Similarity	NPC472787
0.8912	High Similarity	NPC472785
0.8671	High Similarity	NPC64568
0.8649	High Similarity	NPC475777
0.8621	High Similarity	NPC97904
0.8592	High Similarity	NPC18904
0.8582	High Similarity	NPC177262
0.8533	High Similarity	NPC75310
0.8411	Intermediate Similarity	NPC472786
0.8377	Intermediate Similarity	NPC472781
0.8377	Intermediate Similarity	NPC472782
0.8323	Intermediate Similarity	NPC472780
0.8323	Intermediate Similarity	NPC472783
0.8322	Intermediate Similarity	NPC471996
0.8322	Intermediate Similarity	NPC472376
0.8322	Intermediate Similarity	NPC211625
0.8235	Intermediate Similarity	NPC178382
0.8224	Intermediate Similarity	NPC114880
0.8163	Intermediate Similarity	NPC205071
0.8129	Intermediate Similarity	NPC329707
0.8113	Intermediate Similarity	NPC191012
0.8077	Intermediate Similarity	NPC333139
0.8071	Intermediate Similarity	NPC59502
0.8058	Intermediate Similarity	NPC184391
0.8052	Intermediate Similarity	NPC88958
0.805	Intermediate Similarity	NPC472784
0.8045	Intermediate Similarity	NPC59035
0.8045	Intermediate Similarity	NPC79202
0.8042	Intermediate Similarity	NPC106247
0.8028	Intermediate Similarity	NPC471995
0.8013	Intermediate Similarity	NPC252208
0.8013	Intermediate Similarity	NPC19747
0.8013	Intermediate Similarity	NPC477403
0.8	Intermediate Similarity	NPC62799
0.7987	Intermediate Similarity	NPC84479
0.7987	Intermediate Similarity	NPC476931
0.7987	Intermediate Similarity	NPC158871
0.7973	Intermediate Similarity	NPC62103
0.7973	Intermediate Similarity	NPC20578
0.7973	Intermediate Similarity	NPC263337
0.7971	Intermediate Similarity	NPC118853
0.7961	Intermediate Similarity	NPC280025
0.7949	Intermediate Similarity	NPC221992
0.7937	Intermediate Similarity	NPC473766
0.7937	Intermediate Similarity	NPC473753
0.7935	Intermediate Similarity	NPC469966
0.7933	Intermediate Similarity	NPC245522
0.7933	Intermediate Similarity	NPC114513
0.7922	Intermediate Similarity	NPC471613
0.7919	Intermediate Similarity	NPC476946
0.7911	Intermediate Similarity	NPC43490
0.7911	Intermediate Similarity	NPC475107
0.7898	Intermediate Similarity	NPC116639
0.7898	Intermediate Similarity	NPC472823
0.7891	Intermediate Similarity	NPC265181
0.7891	Intermediate Similarity	NPC202260
0.7888	Intermediate Similarity	NPC62444
0.7888	Intermediate Similarity	NPC476255
0.7883	Intermediate Similarity	NPC97566
0.7881	Intermediate Similarity	NPC262198
0.7881	Intermediate Similarity	NPC346
0.7877	Intermediate Similarity	NPC473268
0.7875	Intermediate Similarity	NPC475779
0.7872	Intermediate Similarity	NPC279877
0.7862	Intermediate Similarity	NPC663
0.7862	Intermediate Similarity	NPC158525
0.7862	Intermediate Similarity	NPC224394
0.7848	Intermediate Similarity	NPC477402
0.7848	Intermediate Similarity	NPC287559
0.7847	Intermediate Similarity	NPC293253
0.7843	Intermediate Similarity	NPC192069
0.7838	Intermediate Similarity	NPC148374
0.7838	Intermediate Similarity	NPC90296
0.7834	Intermediate Similarity	NPC81405
0.7832	Intermediate Similarity	NPC61788
0.7821	Intermediate Similarity	NPC42458
0.7821	Intermediate Similarity	NPC158261
0.7815	Intermediate Similarity	NPC469385
0.7812	Intermediate Similarity	NPC470940
0.7812	Intermediate Similarity	NPC94796
0.7808	Intermediate Similarity	NPC217914
0.7808	Intermediate Similarity	NPC46896
0.7801	Intermediate Similarity	NPC246392
0.78	Intermediate Similarity	NPC267632
0.78	Intermediate Similarity	NPC243577
0.7799	Intermediate Similarity	NPC329938
0.7799	Intermediate Similarity	NPC193798
0.7799	Intermediate Similarity	NPC18986
0.7799	Intermediate Similarity	NPC286422
0.7793	Intermediate Similarity	NPC200718
0.7792	Intermediate Similarity	NPC226578
0.7785	Intermediate Similarity	NPC474611
0.7785	Intermediate Similarity	NPC294300
0.7785	Intermediate Similarity	NPC476404
0.7785	Intermediate Similarity	NPC10051
0.7785	Intermediate Similarity	NPC317900
0.7785	Intermediate Similarity	NPC140952
0.7785	Intermediate Similarity	NPC299094
0.7785	Intermediate Similarity	NPC473368
0.7778	Intermediate Similarity	NPC469425
0.7778	Intermediate Similarity	NPC473982
0.7771	Intermediate Similarity	NPC104736
0.7771	Intermediate Similarity	NPC469485
0.7771	Intermediate Similarity	NPC41880
0.777	Intermediate Similarity	NPC474722
0.7764	Intermediate Similarity	NPC132054
0.7764	Intermediate Similarity	NPC121995
0.7763	Intermediate Similarity	NPC233763
0.7763	Intermediate Similarity	NPC478166
0.7758	Intermediate Similarity	NPC475080
0.7756	Intermediate Similarity	NPC282793
0.7756	Intermediate Similarity	NPC178932
0.7756	Intermediate Similarity	NPC275878
0.7755	Intermediate Similarity	NPC470742
0.7755	Intermediate Similarity	NPC307401
0.775	Intermediate Similarity	NPC88841
0.775	Intermediate Similarity	NPC292389
0.775	Intermediate Similarity	NPC469338
0.775	Intermediate Similarity	NPC288602
0.7748	Intermediate Similarity	NPC117674
0.7748	Intermediate Similarity	NPC476944
0.7746	Intermediate Similarity	NPC26532
0.7736	Intermediate Similarity	NPC25255
0.773	Intermediate Similarity	NPC223413
0.773	Intermediate Similarity	NPC193222
0.7722	Intermediate Similarity	NPC304692
0.7722	Intermediate Similarity	NPC261597
0.7722	Intermediate Similarity	NPC249021
0.7722	Intermediate Similarity	NPC173544
0.7718	Intermediate Similarity	NPC477408
0.7716	Intermediate Similarity	NPC136641
0.7712	Intermediate Similarity	NPC224418
0.7712	Intermediate Similarity	NPC82534
0.7707	Intermediate Similarity	NPC214541
0.7707	Intermediate Similarity	NPC44675
0.7707	Intermediate Similarity	NPC469336
0.7707	Intermediate Similarity	NPC264943
0.7707	Intermediate Similarity	NPC290927
0.7707	Intermediate Similarity	NPC179170
0.7703	Intermediate Similarity	NPC220094
0.7702	Intermediate Similarity	NPC261184
0.7702	Intermediate Similarity	NPC193998
0.7702	Intermediate Similarity	NPC476856
0.7702	Intermediate Similarity	NPC56358
0.7702	Intermediate Similarity	NPC476857
0.7702	Intermediate Similarity	NPC476858
0.7702	Intermediate Similarity	NPC469849
0.7702	Intermediate Similarity	NPC476860
0.7702	Intermediate Similarity	NPC276551
0.7698	Intermediate Similarity	NPC323118
0.7697	Intermediate Similarity	NPC169018
0.7697	Intermediate Similarity	NPC476159
0.7697	Intermediate Similarity	NPC41182
0.7692	Intermediate Similarity	NPC44577
0.7692	Intermediate Similarity	NPC115869
0.7692	Intermediate Similarity	NPC145830
0.7692	Intermediate Similarity	NPC75906
0.7688	Intermediate Similarity	NPC313368
0.7688	Intermediate Similarity	NPC188649
0.7688	Intermediate Similarity	NPC69028
0.7688	Intermediate Similarity	NPC5079
0.7683	Intermediate Similarity	NPC63514
0.7677	Intermediate Similarity	NPC212257
0.7676	Intermediate Similarity	NPC290955
0.7673	Intermediate Similarity	NPC476930
0.7673	Intermediate Similarity	NPC217602
0.7673	Intermediate Similarity	NPC473282
0.7673	Intermediate Similarity	NPC104380
0.7671	Intermediate Similarity	NPC471998
0.7669	Intermediate Similarity	NPC298071
0.7669	Intermediate Similarity	NPC296558
0.7669	Intermediate Similarity	NPC476056
0.7667	Intermediate Similarity	NPC248795
0.7667	Intermediate Similarity	NPC205765
0.766	Intermediate Similarity	NPC473885
0.766	Intermediate Similarity	NPC471074
0.7658	Intermediate Similarity	NPC60973
0.7654	Intermediate Similarity	NPC23387
0.7654	Intermediate Similarity	NPC470875
0.7654	Intermediate Similarity	NPC131578
0.7651	Intermediate Similarity	NPC233707
0.7643	Intermediate Similarity	NPC471347
0.7643	Intermediate Similarity	NPC471349
0.7643	Intermediate Similarity	NPC30222
0.7643	Intermediate Similarity	NPC253872
0.7643	Intermediate Similarity	NPC263676
0.764	Intermediate Similarity	NPC477405
0.764	Intermediate Similarity	NPC476929
0.764	Intermediate Similarity	NPC234660
0.764	Intermediate Similarity	NPC51568
0.7639	Intermediate Similarity	NPC45947
0.7635	Intermediate Similarity	NPC4764
0.7628	Intermediate Similarity	NPC472406
0.7622	Intermediate Similarity	NPC302392
0.7619	Intermediate Similarity	NPC159786
0.7619	Intermediate Similarity	NPC265793
0.7619	Intermediate Similarity	NPC209858
0.7619	Intermediate Similarity	NPC324117

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 NPC61157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	994
0.2-0.3	1772
0.3-0.4	2755
0.4-0.5	2102
0.5-0.6	968
0.6-0.7	259
0.7-0.8	20
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
0.8077	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1471	Phase 3
0.7533	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD5761	Phase 2
0.7484	Intermediate Similarity	NPD5760	Phase 2
0.732	Intermediate Similarity	NPD2800	Approved
0.7317	Intermediate Similarity	NPD1247	Approved
0.7308	Intermediate Similarity	NPD2532	Approved
0.7308	Intermediate Similarity	NPD2534	Approved
0.7308	Intermediate Similarity	NPD2533	Approved
0.7303	Intermediate Similarity	NPD2344	Approved
0.7235	Intermediate Similarity	NPD6764	Approved
0.7235	Intermediate Similarity	NPD6765	Approved
0.7197	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2309	Approved
0.7107	Intermediate Similarity	NPD920	Approved
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2346	Discontinued
0.7073	Intermediate Similarity	NPD3882	Suspended
0.7069	Intermediate Similarity	NPD6784	Approved
0.7069	Intermediate Similarity	NPD6785	Approved
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7019	Intermediate Similarity	NPD3226	Approved
0.7012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3268	Approved
0.6988	Remote Similarity	NPD919	Approved
0.6962	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2935	Discontinued
0.6887	Remote Similarity	NPD2313	Discontinued
0.6887	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2403	Approved
0.6879	Remote Similarity	NPD1243	Approved
0.6879	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6599	Discontinued
0.6859	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7819	Suspended
0.6848	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6559	Discontinued
0.6829	Remote Similarity	NPD7411	Suspended
0.6826	Remote Similarity	NPD7075	Discontinued
0.6826	Remote Similarity	NPD3749	Approved
0.6818	Remote Similarity	NPD6651	Approved
0.6818	Remote Similarity	NPD1607	Approved
0.6815	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD6799	Approved
0.6809	Remote Similarity	NPD1241	Discontinued
0.6805	Remote Similarity	NPD6959	Discontinued
0.6803	Remote Similarity	NPD9717	Approved
0.6797	Remote Similarity	NPD1240	Approved
0.6795	Remote Similarity	NPD1551	Phase 2
0.6795	Remote Similarity	NPD6099	Approved
0.6795	Remote Similarity	NPD6100	Approved
0.6795	Remote Similarity	NPD2796	Approved
0.6779	Remote Similarity	NPD2797	Approved
0.677	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5711	Approved
0.6765	Remote Similarity	NPD5710	Approved
0.6753	Remote Similarity	NPD447	Suspended
0.6753	Remote Similarity	NPD6355	Discontinued
0.675	Remote Similarity	NPD7236	Approved
0.6746	Remote Similarity	NPD5494	Approved
0.6736	Remote Similarity	NPD9092	Discovery
0.6735	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2798	Approved
0.6731	Remote Similarity	NPD1510	Phase 2
0.673	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6273	Approved
0.6728	Remote Similarity	NPD1512	Approved
0.6712	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3817	Phase 2
0.6687	Remote Similarity	NPD1934	Approved
0.6687	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD411	Approved
0.6667	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2801	Approved
0.6645	Remote Similarity	NPD6832	Phase 2
0.6628	Remote Similarity	NPD3926	Phase 2
0.6625	Remote Similarity	NPD4628	Phase 3
0.6625	Remote Similarity	NPD3750	Approved
0.6624	Remote Similarity	NPD4308	Phase 3
0.6607	Remote Similarity	NPD2296	Approved
0.6607	Remote Similarity	NPD5402	Approved
0.6605	Remote Similarity	NPD1511	Approved
0.6604	Remote Similarity	NPD2424	Discontinued
0.66	Remote Similarity	NPD1283	Approved
0.66	Remote Similarity	NPD1876	Approved
0.659	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6166	Phase 2
0.659	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.659	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6279	Approved
0.6587	Remote Similarity	NPD6280	Approved
0.6581	Remote Similarity	NPD4060	Phase 1
0.6579	Remote Similarity	NPD9494	Approved
0.6577	Remote Similarity	NPD3972	Approved
0.6577	Remote Similarity	NPD1608	Approved
0.6571	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6808	Phase 2
0.6566	Remote Similarity	NPD4380	Phase 2
0.6552	Remote Similarity	NPD3446	Phase 1
0.6552	Remote Similarity	NPD7473	Discontinued
0.6549	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7239	Suspended
0.6541	Remote Similarity	NPD6004	Phase 3
0.6541	Remote Similarity	NPD6002	Phase 3
0.6541	Remote Similarity	NPD6005	Phase 3
0.6541	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1651	Approved
0.6522	Remote Similarity	NPD7003	Approved
0.6519	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3751	Discontinued
0.6514	Remote Similarity	NPD3818	Discontinued
0.6513	Remote Similarity	NPD1019	Discontinued
0.6503	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5403	Approved
0.6474	Remote Similarity	NPD6232	Discontinued
0.6471	Remote Similarity	NPD7768	Phase 2
0.6463	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1398	Phase 1
0.6452	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6798	Discontinued
0.6447	Remote Similarity	NPD8404	Phase 2
0.6442	Remote Similarity	NPD3300	Phase 2
0.6438	Remote Similarity	NPD7340	Approved
0.6438	Remote Similarity	NPD9493	Approved
0.6438	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD4749	Approved
0.6424	Remote Similarity	NPD5049	Phase 3
0.642	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7033	Discontinued
0.6415	Remote Similarity	NPD3748	Approved
0.641	Remote Similarity	NPD6233	Phase 2
0.641	Remote Similarity	NPD8032	Phase 2
0.6409	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7458	Discontinued
0.6405	Remote Similarity	NPD5647	Approved
0.6404	Remote Similarity	NPD6797	Phase 2
0.64	Remote Similarity	NPD1201	Approved
0.64	Remote Similarity	NPD1281	Approved
0.64	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD37	Approved
0.6384	Remote Similarity	NPD5844	Phase 1
0.638	Remote Similarity	NPD3887	Approved
0.638	Remote Similarity	NPD2354	Approved
0.6379	Remote Similarity	NPD3787	Discontinued
0.6376	Remote Similarity	NPD1778	Approved
0.6376	Remote Similarity	NPD17	Approved
0.6376	Remote Similarity	NPD4626	Approved
0.6375	Remote Similarity	NPD4476	Approved
0.6375	Remote Similarity	NPD4477	Approved
0.6374	Remote Similarity	NPD8150	Discontinued
0.6374	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4967	Phase 2
0.6374	Remote Similarity	NPD4966	Approved
0.6374	Remote Similarity	NPD4965	Approved
0.6369	Remote Similarity	NPD2979	Phase 3
0.6369	Remote Similarity	NPD7028	Phase 2
0.6369	Remote Similarity	NPD7251	Discontinued
0.6369	Remote Similarity	NPD4307	Phase 2
0.6368	Remote Similarity	NPD3057	Approved
0.6368	Remote Similarity	NPD3533	Approved
0.6368	Remote Similarity	NPD2972	Approved
0.6364	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5401	Approved
0.6346	Remote Similarity	NPD3764	Approved
0.6346	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7985	Registered
0.634	Remote Similarity	NPD1470	Approved
0.6335	Remote Similarity	NPD5762	Approved
0.6335	Remote Similarity	NPD5763	Approved
0.6333	Remote Similarity	NPD7808	Phase 3
0.6333	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5890	Approved
0.6331	Remote Similarity	NPD5889	Approved
0.6319	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7907	Approved
0.6309	Remote Similarity	NPD5691	Approved
0.6301	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6234	Discontinued
0.63	Remote Similarity	NPD4665	Approved
0.63	Remote Similarity	NPD4111	Phase 1
0.6299	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8312	Approved
0.6298	Remote Similarity	NPD8313	Approved
0.6296	Remote Similarity	NPD5958	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data