NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.729
LogD:	2.081
LogS:	-2.896
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	4.629
Fsp3:	0.667
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:	-4.712
MDCK Permeability:	7.954752072691917e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.494
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.534
Plasma Protein Binding (PPB):	56.93381881713867%
Volume Distribution (VD):	1.161
Pgp-substrate:	48.9848518371582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.352
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.253
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	7.825
Half-life (T1/2):	0.239

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.897
Drug-inuced Liver Injury (DILI):	0.568
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.595
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.132
Carcinogencity:	0.144
Eye Corrosion:	0.147
Eye Irritation:	0.439
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC126248

Natural Product ID:	NPC126248
*Common Name:**	11Beta,13-Dihydro-3-Epizaluzanin C
IUPAC Name:	(3S,3aS,6aR,8R,9aR,9bS)-8-hydroxy-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	DOTNUPYMOWSLMW-WWTHEZKUSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h8,10-14,16H,1,3-6H2,2H3/t8-,10-,11-,12+,13-,14-/m0/s1
SMILES:	C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@H](C3=C)O)OC(=O)[C@H]2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518008
PubChem CID:	44559655
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:0001770] Guaianolides 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
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[14510592]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572418]
NPO22235	Azorella madreporica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677287]
NPO23053	Strychnos nitida	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11723	Pleurotus eryngii	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25693	Populus x canadensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11723	Pleurotus eryngii	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23053	Strychnos nitida	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15979	Erigeron multiradiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30115	Aucklandia lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23053	Strychnos nitida	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22989	Penicillium daleae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11723	Pleurotus eryngii	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21624	Chondrophycus papillosus	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23053	Strychnos nitida	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO698	Podocarpus totara	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18513	Saccobasis polita	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22235	Azorella madreporica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25825	Saussurea lappa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20035	Empleurum unicapsulare	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22628	Centaurea derventana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20175	Aegopodium podagraria	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15979	Erigeron multiradiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25693	Populus x canadensis	Species	Salicaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell Line	OVCAR-3	Homo sapiens	CD50	=	65.0	ug ml-1	PMID[476839]
NPT165	Cell Line	HeLa	Homo sapiens	CD50	=	65.0	ug ml-1	PMID[476839]
NPT65	Cell Line	HepG2	Homo sapiens	CD50	=	75.0	ug ml-1	PMID[476839]

☑ 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 NPC126248 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	211
0.1-0.2	1687
0.2-0.3	6829
0.3-0.4	16487
0.4-0.5	8695
0.5-0.6	6605
0.6-0.7	1857
0.7-0.8	243
0.8-0.85	39
0.85-0.9	34
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC128246
0.9367	High Similarity	NPC224386
0.9367	High Similarity	NPC194859
0.9241	High Similarity	NPC111409
0.9146	High Similarity	NPC217983
0.9146	High Similarity	NPC207114
0.9136	High Similarity	NPC187661
0.9103	High Similarity	NPC156658
0.9103	High Similarity	NPC258965
0.8929	High Similarity	NPC19087
0.8902	High Similarity	NPC56593
0.8824	High Similarity	NPC475925
0.8824	High Similarity	NPC184063
0.881	High Similarity	NPC215556
0.881	High Similarity	NPC155935
0.881	High Similarity	NPC38392
0.878	High Similarity	NPC204105
0.878	High Similarity	NPC284534
0.878	High Similarity	NPC300082
0.8721	High Similarity	NPC475788
0.8706	High Similarity	NPC216284
0.8706	High Similarity	NPC54065
0.8706	High Similarity	NPC35809
0.8706	High Similarity	NPC297474
0.869	High Similarity	NPC79549
0.8642	High Similarity	NPC246076
0.8625	High Similarity	NPC51507
0.8605	High Similarity	NPC63193
0.8605	High Similarity	NPC57304
0.8605	High Similarity	NPC293001
0.8605	High Similarity	NPC133888
0.8605	High Similarity	NPC35959
0.8605	High Similarity	NPC29821
0.8605	High Similarity	NPC171360
0.8571	High Similarity	NPC118601
0.8533	High Similarity	NPC5714
0.8506	High Similarity	NPC258216
0.8471	Intermediate Similarity	NPC178875
0.8427	Intermediate Similarity	NPC474297
0.8409	Intermediate Similarity	NPC473331
0.8391	Intermediate Similarity	NPC155215
0.8333	Intermediate Similarity	NPC474313
0.8315	Intermediate Similarity	NPC476053
0.8315	Intermediate Similarity	NPC472873
0.8315	Intermediate Similarity	NPC170120
0.8313	Intermediate Similarity	NPC245665
0.8295	Intermediate Similarity	NPC200237
0.8256	Intermediate Similarity	NPC91248
0.8235	Intermediate Similarity	NPC64153
0.8235	Intermediate Similarity	NPC67493
0.8235	Intermediate Similarity	NPC470242
0.8235	Intermediate Similarity	NPC309757
0.8235	Intermediate Similarity	NPC304558
0.8235	Intermediate Similarity	NPC236692
0.8222	Intermediate Similarity	NPC142529
0.8222	Intermediate Similarity	NPC18019
0.8222	Intermediate Similarity	NPC24956
0.8222	Intermediate Similarity	NPC91771
0.8202	Intermediate Similarity	NPC470013
0.8202	Intermediate Similarity	NPC470010
0.8202	Intermediate Similarity	NPC198853
0.8202	Intermediate Similarity	NPC262133
0.8202	Intermediate Similarity	NPC323008
0.8182	Intermediate Similarity	NPC131209
0.814	Intermediate Similarity	NPC270270
0.814	Intermediate Similarity	NPC24728
0.8132	Intermediate Similarity	NPC304445
0.8132	Intermediate Similarity	NPC311904
0.8132	Intermediate Similarity	NPC236580
0.8132	Intermediate Similarity	NPC471150
0.8111	Intermediate Similarity	NPC213698
0.8111	Intermediate Similarity	NPC163228
0.8111	Intermediate Similarity	NPC52044
0.8101	Intermediate Similarity	NPC143979
0.8101	Intermediate Similarity	NPC320537
0.809	Intermediate Similarity	NPC153590
0.8068	Intermediate Similarity	NPC37607
0.8068	Intermediate Similarity	NPC301969
0.8065	Intermediate Similarity	NPC67296
0.8046	Intermediate Similarity	NPC471149
0.8	Intermediate Similarity	NPC127019
0.7978	Intermediate Similarity	NPC133698
0.7957	Intermediate Similarity	NPC471381
0.7955	Intermediate Similarity	NPC472872
0.7955	Intermediate Similarity	NPC12872
0.7955	Intermediate Similarity	NPC283409
0.7955	Intermediate Similarity	NPC168679
0.7935	Intermediate Similarity	NPC181151
0.7935	Intermediate Similarity	NPC261372
0.7935	Intermediate Similarity	NPC58267
0.7935	Intermediate Similarity	NPC263674
0.7935	Intermediate Similarity	NPC161493
0.7931	Intermediate Similarity	NPC237540
0.7912	Intermediate Similarity	NPC304886
0.7912	Intermediate Similarity	NPC67584
0.7889	Intermediate Similarity	NPC308656
0.7889	Intermediate Similarity	NPC135776
0.7889	Intermediate Similarity	NPC473273
0.7889	Intermediate Similarity	NPC60386
0.7889	Intermediate Similarity	NPC473263
0.7889	Intermediate Similarity	NPC473234
0.7875	Intermediate Similarity	NPC472966
0.7872	Intermediate Similarity	NPC171759
0.7872	Intermediate Similarity	NPC150923
0.7857	Intermediate Similarity	NPC470241
0.7849	Intermediate Similarity	NPC249171
0.7849	Intermediate Similarity	NPC45125
0.7849	Intermediate Similarity	NPC49833
0.7849	Intermediate Similarity	NPC221615
0.7841	Intermediate Similarity	NPC224652
0.7826	Intermediate Similarity	NPC213078
0.7805	Intermediate Similarity	NPC208223
0.7802	Intermediate Similarity	NPC477131
0.7791	Intermediate Similarity	NPC165287
0.7791	Intermediate Similarity	NPC156485
0.7789	Intermediate Similarity	NPC80144
0.7778	Intermediate Similarity	NPC191339
0.7778	Intermediate Similarity	NPC286341
0.7778	Intermediate Similarity	NPC471491
0.7766	Intermediate Similarity	NPC186861
0.7765	Intermediate Similarity	NPC89555
0.7753	Intermediate Similarity	NPC4986
0.7753	Intermediate Similarity	NPC32922
0.7738	Intermediate Similarity	NPC290508
0.7738	Intermediate Similarity	NPC293418
0.7738	Intermediate Similarity	NPC6823
0.7738	Intermediate Similarity	NPC73052
0.7727	Intermediate Similarity	NPC186148
0.7727	Intermediate Similarity	NPC190753
0.7727	Intermediate Similarity	NPC475773
0.7727	Intermediate Similarity	NPC201658
0.7708	Intermediate Similarity	NPC473148
0.7701	Intermediate Similarity	NPC235792
0.7674	Intermediate Similarity	NPC54468
0.7667	Intermediate Similarity	NPC153853
0.7654	Intermediate Similarity	NPC215030
0.7647	Intermediate Similarity	NPC191711
0.7647	Intermediate Similarity	NPC47635
0.764	Intermediate Similarity	NPC177629
0.764	Intermediate Similarity	NPC58219
0.7619	Intermediate Similarity	NPC182550
0.7619	Intermediate Similarity	NPC470239
0.7619	Intermediate Similarity	NPC470244
0.7619	Intermediate Similarity	NPC89128
0.7614	Intermediate Similarity	NPC162071
0.7604	Intermediate Similarity	NPC86077
0.7586	Intermediate Similarity	NPC472958
0.7586	Intermediate Similarity	NPC472957
0.7586	Intermediate Similarity	NPC97505
0.7586	Intermediate Similarity	NPC151176
0.7586	Intermediate Similarity	NPC475963
0.7586	Intermediate Similarity	NPC3464
0.7579	Intermediate Similarity	NPC70865
0.7561	Intermediate Similarity	NPC217725
0.7556	Intermediate Similarity	NPC194642
0.7556	Intermediate Similarity	NPC92974
0.7556	Intermediate Similarity	NPC268298
0.7556	Intermediate Similarity	NPC295312
0.7553	Intermediate Similarity	NPC170143
0.7553	Intermediate Similarity	NPC213947
0.7553	Intermediate Similarity	NPC108475
0.7551	Intermediate Similarity	NPC236644
0.7551	Intermediate Similarity	NPC44004
0.7551	Intermediate Similarity	NPC54737
0.7529	Intermediate Similarity	NPC69271
0.7529	Intermediate Similarity	NPC276356
0.7529	Intermediate Similarity	NPC74673
0.7528	Intermediate Similarity	NPC316629
0.7527	Intermediate Similarity	NPC167893
0.75	Intermediate Similarity	NPC165162
0.75	Intermediate Similarity	NPC147272
0.75	Intermediate Similarity	NPC472874
0.75	Intermediate Similarity	NPC18543
0.7473	Intermediate Similarity	NPC129419
0.7473	Intermediate Similarity	NPC206614
0.7473	Intermediate Similarity	NPC474323
0.7473	Intermediate Similarity	NPC246173
0.7471	Intermediate Similarity	NPC250315
0.7447	Intermediate Similarity	NPC476009
0.7447	Intermediate Similarity	NPC126156
0.7444	Intermediate Similarity	NPC53158
0.7444	Intermediate Similarity	NPC202672
0.7442	Intermediate Similarity	NPC52861
0.7442	Intermediate Similarity	NPC209318
0.7442	Intermediate Similarity	NPC223330
0.7439	Intermediate Similarity	NPC469641
0.7439	Intermediate Similarity	NPC469643
0.7416	Intermediate Similarity	NPC475019
0.7416	Intermediate Similarity	NPC474949
0.7416	Intermediate Similarity	NPC238593
0.74	Intermediate Similarity	NPC68248
0.7396	Intermediate Similarity	NPC473146
0.7391	Intermediate Similarity	NPC208886
0.7391	Intermediate Similarity	NPC471747
0.7391	Intermediate Similarity	NPC12172
0.7386	Intermediate Similarity	NPC191476
0.7386	Intermediate Similarity	NPC114979
0.7386	Intermediate Similarity	NPC474780
0.7381	Intermediate Similarity	NPC195785
0.7381	Intermediate Similarity	NPC15975

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 NPC126248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	2526
0.2-0.3	3933
0.3-0.4	1691
0.4-0.5	478
0.5-0.6	229
0.6-0.7	28
0.7-0.8	10
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
0.7753	Intermediate Similarity	NPD1695	Approved
0.7614	Intermediate Similarity	NPD4249	Approved
0.7528	Intermediate Similarity	NPD4250	Approved
0.7528	Intermediate Similarity	NPD4251	Approved
0.7471	Intermediate Similarity	NPD5362	Discontinued
0.7159	Intermediate Similarity	NPD4270	Approved
0.7159	Intermediate Similarity	NPD4269	Approved
0.7158	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7154	Phase 3
0.7045	Intermediate Similarity	NPD5369	Approved
0.7033	Intermediate Similarity	NPD5786	Approved
0.6966	Remote Similarity	NPD6435	Approved
0.6932	Remote Similarity	NPD4822	Approved
0.6932	Remote Similarity	NPD4821	Approved
0.6932	Remote Similarity	NPD4820	Approved
0.6932	Remote Similarity	NPD4252	Approved
0.6932	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4268	Approved
0.6897	Remote Similarity	NPD4271	Approved
0.6889	Remote Similarity	NPD5332	Approved
0.6889	Remote Similarity	NPD5331	Approved
0.6854	Remote Similarity	NPD4790	Discontinued
0.6762	Remote Similarity	NPD6371	Approved
0.6742	Remote Similarity	NPD5368	Approved
0.6737	Remote Similarity	NPD5785	Approved
0.6705	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD3198	Approved
0.6636	Remote Similarity	NPD6053	Discontinued
0.6598	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6598	Remote Similarity	NPD6399	Phase 3
0.6562	Remote Similarity	NPD46	Approved
0.6562	Remote Similarity	NPD6698	Approved
0.6559	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD7639	Approved
0.6531	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD8034	Phase 2
0.6495	Remote Similarity	NPD8035	Phase 2
0.6436	Remote Similarity	NPD7638	Approved
0.6383	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6008	Approved
0.6333	Remote Similarity	NPD4802	Phase 2
0.6333	Remote Similarity	NPD4238	Approved
0.6327	Remote Similarity	NPD7637	Suspended
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3667	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.6146	Remote Similarity	NPD5330	Approved
0.6146	Remote Similarity	NPD7146	Approved
0.6146	Remote Similarity	NPD7521	Approved
0.6146	Remote Similarity	NPD6409	Approved
0.6146	Remote Similarity	NPD6684	Approved
0.6146	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6101	Approved
0.6105	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD3666	Approved
0.6105	Remote Similarity	NPD4786	Approved
0.6105	Remote Similarity	NPD3665	Phase 1
0.6105	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7632	Discontinued
0.6078	Remote Similarity	NPD7839	Suspended
0.6061	Remote Similarity	NPD7838	Discovery
0.6042	Remote Similarity	NPD1694	Approved
0.602	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6083	Phase 2
0.6019	Remote Similarity	NPD6412	Phase 2
0.6019	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD6411	Approved
0.5982	Remote Similarity	NPD8133	Approved
0.598	Remote Similarity	NPD5695	Phase 3
0.5979	Remote Similarity	NPD3618	Phase 1
0.5963	Remote Similarity	NPD6686	Approved
0.5963	Remote Similarity	NPD7320	Approved
0.5962	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4225	Approved
0.5962	Remote Similarity	NPD5696	Approved
0.596	Remote Similarity	NPD5370	Suspended
0.5926	Remote Similarity	NPD5739	Approved
0.5926	Remote Similarity	NPD6675	Approved
0.5926	Remote Similarity	NPD7128	Approved
0.5926	Remote Similarity	NPD6402	Approved
0.5914	Remote Similarity	NPD6929	Approved
0.5909	Remote Similarity	NPD6372	Approved
0.5909	Remote Similarity	NPD6373	Approved
0.59	Remote Similarity	NPD5207	Approved
0.5872	Remote Similarity	NPD5701	Approved
0.5872	Remote Similarity	NPD6685	Approved
0.5872	Remote Similarity	NPD5697	Approved
0.5856	Remote Similarity	NPD6420	Discontinued
0.5851	Remote Similarity	NPD6930	Phase 2
0.5851	Remote Similarity	NPD6931	Approved
0.5842	Remote Similarity	NPD5284	Approved
0.5842	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5281	Approved
0.5841	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3702	Approved
0.5818	Remote Similarity	NPD6011	Approved
0.5818	Remote Similarity	NPD6881	Approved
0.5818	Remote Similarity	NPD6899	Approved
0.5816	Remote Similarity	NPD5279	Phase 3
0.5806	Remote Similarity	NPD6114	Approved
0.5806	Remote Similarity	NPD6697	Approved
0.5806	Remote Similarity	NPD6115	Approved
0.5806	Remote Similarity	NPD6118	Approved
0.5804	Remote Similarity	NPD6649	Approved
0.5804	Remote Similarity	NPD6650	Approved
0.5784	Remote Similarity	NPD4202	Approved
0.5766	Remote Similarity	NPD6012	Approved
0.5766	Remote Similarity	NPD6014	Approved
0.5766	Remote Similarity	NPD6013	Approved
0.5765	Remote Similarity	NPD7909	Approved
0.5763	Remote Similarity	NPD8513	Phase 3
0.5763	Remote Similarity	NPD8516	Approved
0.5763	Remote Similarity	NPD8517	Approved
0.5763	Remote Similarity	NPD8515	Approved
0.5758	Remote Similarity	NPD7524	Approved
0.5758	Remote Similarity	NPD7750	Discontinued
0.575	Remote Similarity	NPD7492	Approved
0.5729	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6001	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD6616	Approved
0.5702	Remote Similarity	NPD7507	Approved
0.5701	Remote Similarity	NPD5344	Discontinued
0.5701	Remote Similarity	NPD1700	Approved
0.57	Remote Similarity	NPD5737	Approved
0.57	Remote Similarity	NPD6672	Approved
0.5699	Remote Similarity	NPD6925	Approved
0.5699	Remote Similarity	NPD6116	Phase 1
0.5699	Remote Similarity	NPD5776	Phase 2
0.5698	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.569	Remote Similarity	NPD7115	Discovery
0.569	Remote Similarity	NPD6009	Approved
0.5688	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD229	Approved
0.5678	Remote Similarity	NPD6054	Approved
0.5678	Remote Similarity	NPD6059	Approved
0.5678	Remote Similarity	NPD6319	Approved
0.5676	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5777	Approved
0.5664	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6617	Approved
0.5664	Remote Similarity	NPD6869	Approved
0.5664	Remote Similarity	NPD6847	Approved
0.5664	Remote Similarity	NPD8130	Phase 1
0.5657	Remote Similarity	NPD6098	Approved
0.5656	Remote Similarity	NPD7078	Approved
0.5656	Remote Similarity	NPD8293	Discontinued
0.5648	Remote Similarity	NPD5211	Phase 2
0.5645	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4753	Phase 2
0.5644	Remote Similarity	NPD5328	Approved
0.5638	Remote Similarity	NPD7145	Approved
0.563	Remote Similarity	NPD8267	Approved
0.563	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.563	Remote Similarity	NPD5983	Phase 2
0.563	Remote Similarity	NPD6015	Approved
0.563	Remote Similarity	NPD8269	Approved
0.563	Remote Similarity	NPD8266	Approved
0.563	Remote Similarity	NPD8268	Approved
0.563	Remote Similarity	NPD6016	Approved
0.5625	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD3698	Phase 2
0.5614	Remote Similarity	NPD8297	Approved
0.5614	Remote Similarity	NPD6882	Approved
0.5612	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD3668	Phase 3
0.561	Remote Similarity	NPD7736	Approved
0.56	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.56	Remote Similarity	NPD634	Phase 3

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