NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	2.121
LogD:	1.995
LogS:	-3.32
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.497
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.577
MDCK Permeability:	2.7855014195665717e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.425
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.898
Plasma Protein Binding (PPB):	55.92267608642578%
Volume Distribution (VD):	1.247
Pgp-substrate:	46.11311721801758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.703
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.531
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	12.24
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.526
Carcinogencity:	0.915
Eye Corrosion:	0.884
Eye Irritation:	0.564
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC215294

Natural Product ID:	NPC215294
*Common Name:**	Neoambrosin
IUPAC Name:	(3aS,6S,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,6,8,9b-hexahydroazuleno[8,7-b]furan-2,9-dione
Synonyms:
Standard InCHIKey:	ALDYHLYMNPPSIB-XJFVKYJOSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h6,8,10,13H,2,4-5,7H2,1,3H3/t8-,10-,13+,15-/m0/s1
SMILES:	C[C@H]1CC[C@@H]2[C@H]([C@]3(C1=CCC3=O)C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2286471
PubChem CID:	11128594
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO16340	Heterostemma brownii	Species	Apocynaceae	Eukaryota	Stems	n.a.	n.a.	PMID[9358639]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16152	Phlebia radiata	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO14970	Vitex polygama	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16152	Phlebia radiata	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12242	Lactuca tatarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16668	Lonas annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2736	Penstemon diffusus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16340	Heterostemma brownii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13843	Peronema canescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9557	Rumex bequaertii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16262	Bacillus mojavensis	Species	Bacillaceae	Bacteria	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
EC50	2
Others	15

Activity Type	# Activity
Organism	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT936	Organism	Avena fatua	Avena fatua	EC50	=	960000.0	nM	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	84.8	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	43.8	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	20.5	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	10.7	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	2.7	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	EC50	=	480000.0	nM	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	94.8	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	61.5	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	45.6	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	40.6	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	11.5	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	23.3	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	40.0	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	36.7	%	PMID[490508]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	46.7	%	PMID[490508]

☑ 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 NPC215294 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	207
0.1-0.2	1526
0.2-0.3	6635
0.3-0.4	15668
0.4-0.5	9333
0.5-0.6	6357
0.6-0.7	2407
0.7-0.8	476
0.8-0.85	60
0.85-0.9	21
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC33570
0.95	High Similarity	NPC21471
0.9114	High Similarity	NPC69271
0.9114	High Similarity	NPC6823
0.9114	High Similarity	NPC302426
0.9114	High Similarity	NPC276356
0.9114	High Similarity	NPC74673
0.9024	High Similarity	NPC161957
0.8837	High Similarity	NPC74103
0.8837	High Similarity	NPC70595
0.8837	High Similarity	NPC150978
0.8837	High Similarity	NPC123177
0.878	High Similarity	NPC39588
0.8765	High Similarity	NPC10276
0.8765	High Similarity	NPC35089
0.875	High Similarity	NPC182550
0.8734	High Similarity	NPC65603
0.8721	High Similarity	NPC253144
0.8718	High Similarity	NPC226669
0.8718	High Similarity	NPC138408
0.8718	High Similarity	NPC193351
0.8675	High Similarity	NPC115786
0.8642	High Similarity	NPC290508
0.8642	High Similarity	NPC73052
0.8642	High Similarity	NPC223904
0.8642	High Similarity	NPC293418
0.8636	High Similarity	NPC167219
0.8621	High Similarity	NPC284185
0.8539	High Similarity	NPC193645
0.8539	High Similarity	NPC48803
0.8539	High Similarity	NPC90121
0.8539	High Similarity	NPC275960
0.85	High Similarity	NPC476794
0.85	High Similarity	NPC470240
0.85	High Similarity	NPC15975
0.85	High Similarity	NPC195785
0.8481	Intermediate Similarity	NPC155587
0.8471	Intermediate Similarity	NPC107787
0.8471	Intermediate Similarity	NPC238593
0.8395	Intermediate Similarity	NPC299235
0.8375	Intermediate Similarity	NPC235906
0.8372	Intermediate Similarity	NPC201658
0.8354	Intermediate Similarity	NPC143979
0.8354	Intermediate Similarity	NPC320537
0.8353	Intermediate Similarity	NPC78089
0.8352	Intermediate Similarity	NPC169205
0.8333	Intermediate Similarity	NPC318468
0.8333	Intermediate Similarity	NPC54468
0.8313	Intermediate Similarity	NPC25684
0.8313	Intermediate Similarity	NPC281949
0.8313	Intermediate Similarity	NPC301477
0.8293	Intermediate Similarity	NPC264227
0.8293	Intermediate Similarity	NPC470239
0.8293	Intermediate Similarity	NPC472965
0.8293	Intermediate Similarity	NPC63649
0.8293	Intermediate Similarity	NPC470244
0.8276	Intermediate Similarity	NPC91248
0.8272	Intermediate Similarity	NPC122264
0.8272	Intermediate Similarity	NPC208223
0.8261	Intermediate Similarity	NPC141191
0.8261	Intermediate Similarity	NPC54843
0.8256	Intermediate Similarity	NPC70422
0.8256	Intermediate Similarity	NPC104961
0.8256	Intermediate Similarity	NPC70555
0.8242	Intermediate Similarity	NPC185553
0.8214	Intermediate Similarity	NPC178676
0.8182	Intermediate Similarity	NPC168679
0.8182	Intermediate Similarity	NPC268298
0.8182	Intermediate Similarity	NPC12872
0.8182	Intermediate Similarity	NPC4986
0.814	Intermediate Similarity	NPC110405
0.8101	Intermediate Similarity	NPC163003
0.8095	Intermediate Similarity	NPC255580
0.8095	Intermediate Similarity	NPC39411
0.809	Intermediate Similarity	NPC129419
0.8072	Intermediate Similarity	NPC617
0.8049	Intermediate Similarity	NPC187568
0.8049	Intermediate Similarity	NPC41780
0.8023	Intermediate Similarity	NPC156485
0.8	Intermediate Similarity	NPC133698
0.8	Intermediate Similarity	NPC191339
0.8	Intermediate Similarity	NPC286341
0.8	Intermediate Similarity	NPC300312
0.8	Intermediate Similarity	NPC58956
0.8	Intermediate Similarity	NPC131209
0.8	Intermediate Similarity	NPC111114
0.8	Intermediate Similarity	NPC269206
0.8	Intermediate Similarity	NPC295633
0.8	Intermediate Similarity	NPC261607
0.8	Intermediate Similarity	NPC173609
0.7978	Intermediate Similarity	NPC117405
0.7978	Intermediate Similarity	NPC52198
0.7957	Intermediate Similarity	NPC108475
0.7957	Intermediate Similarity	NPC213947
0.7957	Intermediate Similarity	NPC170143
0.7952	Intermediate Similarity	NPC472960
0.7935	Intermediate Similarity	NPC474490
0.7931	Intermediate Similarity	NPC235792
0.7931	Intermediate Similarity	NPC165162
0.7927	Intermediate Similarity	NPC123360
0.7912	Intermediate Similarity	NPC60386
0.7912	Intermediate Similarity	NPC153590
0.7912	Intermediate Similarity	NPC473234
0.7912	Intermediate Similarity	NPC200237
0.7912	Intermediate Similarity	NPC308656
0.7912	Intermediate Similarity	NPC473273
0.7912	Intermediate Similarity	NPC135776
0.7912	Intermediate Similarity	NPC473263
0.7907	Intermediate Similarity	NPC475947
0.7901	Intermediate Similarity	NPC469643
0.7901	Intermediate Similarity	NPC476355
0.7901	Intermediate Similarity	NPC469641
0.7901	Intermediate Similarity	NPC140287
0.7882	Intermediate Similarity	NPC47635
0.7882	Intermediate Similarity	NPC141810
0.7865	Intermediate Similarity	NPC215831
0.7857	Intermediate Similarity	NPC469690
0.7848	Intermediate Similarity	NPC5714
0.7848	Intermediate Similarity	NPC144511
0.7848	Intermediate Similarity	NPC296522
0.7841	Intermediate Similarity	NPC304558
0.7841	Intermediate Similarity	NPC67493
0.7841	Intermediate Similarity	NPC38576
0.7841	Intermediate Similarity	NPC64153
0.7841	Intermediate Similarity	NPC56593
0.7841	Intermediate Similarity	NPC279859
0.7835	Intermediate Similarity	NPC203659
0.7826	Intermediate Similarity	NPC198853
0.7826	Intermediate Similarity	NPC473331
0.7826	Intermediate Similarity	NPC470010
0.7826	Intermediate Similarity	NPC470013
0.7826	Intermediate Similarity	NPC262133
0.7826	Intermediate Similarity	NPC323008
0.7826	Intermediate Similarity	NPC477131
0.7816	Intermediate Similarity	NPC165287
0.7816	Intermediate Similarity	NPC475100
0.7812	Intermediate Similarity	NPC225353
0.7791	Intermediate Similarity	NPC246076
0.7778	Intermediate Similarity	NPC73995
0.7778	Intermediate Similarity	NPC472956
0.7753	Intermediate Similarity	NPC24728
0.7753	Intermediate Similarity	NPC237540
0.7753	Intermediate Similarity	NPC72513
0.7753	Intermediate Similarity	NPC478144
0.775	Intermediate Similarity	NPC472955
0.7738	Intermediate Similarity	NPC128276
0.7732	Intermediate Similarity	NPC110989
0.7727	Intermediate Similarity	NPC177932
0.7711	Intermediate Similarity	NPC266159
0.7711	Intermediate Similarity	NPC472967
0.7708	Intermediate Similarity	NPC171759
0.7701	Intermediate Similarity	NPC193198
0.7701	Intermediate Similarity	NPC245665
0.7701	Intermediate Similarity	NPC272814
0.7701	Intermediate Similarity	NPC22611
0.7692	Intermediate Similarity	NPC71533
0.7692	Intermediate Similarity	NPC301969
0.7692	Intermediate Similarity	NPC152467
0.7692	Intermediate Similarity	NPC106510
0.7692	Intermediate Similarity	NPC37607
0.7692	Intermediate Similarity	NPC62815
0.7674	Intermediate Similarity	NPC38642
0.7674	Intermediate Similarity	NPC471325
0.7667	Intermediate Similarity	NPC471149
0.7667	Intermediate Similarity	NPC471047
0.7667	Intermediate Similarity	NPC469631
0.7667	Intermediate Similarity	NPC224652
0.7667	Intermediate Similarity	NPC469628
0.7667	Intermediate Similarity	NPC475906
0.7667	Intermediate Similarity	NPC226863
0.7667	Intermediate Similarity	NPC469653
0.766	Intermediate Similarity	NPC142529
0.766	Intermediate Similarity	NPC91771
0.7654	Intermediate Similarity	NPC129665
0.7647	Intermediate Similarity	NPC150646
0.7647	Intermediate Similarity	NPC469620
0.7647	Intermediate Similarity	NPC178277
0.7647	Intermediate Similarity	NPC270126
0.764	Intermediate Similarity	NPC284902
0.764	Intermediate Similarity	NPC236692
0.764	Intermediate Similarity	NPC261721
0.764	Intermediate Similarity	NPC309757
0.7634	Intermediate Similarity	NPC289004
0.7619	Intermediate Similarity	NPC320630
0.7619	Intermediate Similarity	NPC103987
0.7619	Intermediate Similarity	NPC474760
0.7619	Intermediate Similarity	NPC97516
0.7619	Intermediate Similarity	NPC53581
0.7619	Intermediate Similarity	NPC116177
0.7619	Intermediate Similarity	NPC171204
0.7619	Intermediate Similarity	NPC7563
0.7619	Intermediate Similarity	NPC57744
0.7619	Intermediate Similarity	NPC141789
0.7619	Intermediate Similarity	NPC476028
0.7614	Intermediate Similarity	NPC114979
0.7614	Intermediate Similarity	NPC191476
0.7614	Intermediate Similarity	NPC96259
0.7614	Intermediate Similarity	NPC238197
0.7614	Intermediate Similarity	NPC141193
0.7609	Intermediate Similarity	NPC472953

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 NPC215294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2108
0.2-0.3	4063
0.3-0.4	1934
0.4-0.5	556
0.5-0.6	246
0.6-0.7	38
0.7-0.8	5
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8539	High Similarity	NPD1698	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1695	Approved
0.7727	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD5785	Approved
0.7386	Intermediate Similarity	NPD5209	Approved
0.7333	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6371	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6915	Remote Similarity	NPD6903	Approved
0.6907	Remote Similarity	NPD5282	Discontinued
0.6889	Remote Similarity	NPD5369	Approved
0.6882	Remote Similarity	NPD7146	Approved
0.6882	Remote Similarity	NPD6684	Approved
0.6882	Remote Similarity	NPD6409	Approved
0.6882	Remote Similarity	NPD7334	Approved
0.6882	Remote Similarity	NPD5330	Approved
0.6882	Remote Similarity	NPD7521	Approved
0.6813	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD4270	Approved
0.68	Remote Similarity	NPD4225	Approved
0.6782	Remote Similarity	NPD8039	Approved
0.6739	Remote Similarity	NPD7154	Phase 3
0.6739	Remote Similarity	NPD5362	Discontinued
0.6737	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5786	Approved
0.6633	Remote Similarity	NPD6399	Phase 3
0.6598	Remote Similarity	NPD5207	Approved
0.6593	Remote Similarity	NPD4252	Approved
0.6562	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD5737	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5693	Phase 1
0.6506	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7115	Discovery
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6008	Approved
0.64	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD6411	Approved
0.6277	Remote Similarity	NPD3667	Approved
0.6277	Remote Similarity	NPD6435	Approved
0.6263	Remote Similarity	NPD46	Approved
0.6263	Remote Similarity	NPD6698	Approved
0.6238	Remote Similarity	NPD7900	Approved
0.6238	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5208	Approved
0.6186	Remote Similarity	NPD3618	Phase 1
0.6186	Remote Similarity	NPD6098	Approved
0.6176	Remote Similarity	NPD5695	Phase 3
0.6162	Remote Similarity	NPD6080	Approved
0.6162	Remote Similarity	NPD6673	Approved
0.6162	Remote Similarity	NPD6101	Approved
0.6162	Remote Similarity	NPD6904	Approved
0.6162	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6146	Remote Similarity	NPD3666	Approved
0.6146	Remote Similarity	NPD3133	Approved
0.6146	Remote Similarity	NPD4786	Approved
0.6146	Remote Similarity	NPD3665	Phase 1
0.6146	Remote Similarity	NPD3668	Phase 3
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6122	Remote Similarity	NPD3573	Approved
0.61	Remote Similarity	NPD5692	Phase 3
0.6095	Remote Similarity	NPD7640	Approved
0.6095	Remote Similarity	NPD7639	Approved
0.6078	Remote Similarity	NPD7748	Approved
0.6064	Remote Similarity	NPD5368	Approved
0.6064	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6083	Phase 2
0.6058	Remote Similarity	NPD6084	Phase 2
0.6058	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD5332	Approved
0.6042	Remote Similarity	NPD5331	Approved
0.604	Remote Similarity	NPD7637	Suspended
0.604	Remote Similarity	NPD7983	Approved
0.604	Remote Similarity	NPD5694	Approved
0.604	Remote Similarity	NPD6050	Approved
0.602	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.596	Remote Similarity	NPD4250	Approved
0.596	Remote Similarity	NPD4251	Approved
0.5941	Remote Similarity	NPD7838	Discovery
0.5929	Remote Similarity	NPD6053	Discontinued
0.5926	Remote Similarity	NPD6052	Approved
0.5909	Remote Similarity	NPD229	Approved
0.5909	Remote Similarity	NPD5697	Approved
0.5895	Remote Similarity	NPD4695	Discontinued
0.5895	Remote Similarity	NPD4822	Approved
0.5895	Remote Similarity	NPD4821	Approved
0.5895	Remote Similarity	NPD4820	Approved
0.5895	Remote Similarity	NPD4819	Approved
0.5882	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD6079	Approved
0.5882	Remote Similarity	NPD5284	Approved
0.5882	Remote Similarity	NPD7515	Phase 2
0.5856	Remote Similarity	NPD6881	Approved
0.5856	Remote Similarity	NPD6899	Approved
0.5856	Remote Similarity	NPD7320	Approved
0.5856	Remote Similarity	NPD6011	Approved
0.5851	Remote Similarity	NPD4271	Approved
0.5851	Remote Similarity	NPD4268	Approved
0.5842	Remote Similarity	NPD5328	Approved
0.5841	Remote Similarity	NPD6649	Approved
0.5841	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD857	Phase 3
0.5818	Remote Similarity	NPD6675	Approved
0.5818	Remote Similarity	NPD7128	Approved
0.5818	Remote Similarity	NPD5739	Approved
0.5818	Remote Similarity	NPD6402	Approved
0.5816	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7839	Suspended
0.5804	Remote Similarity	NPD6013	Approved
0.5804	Remote Similarity	NPD6012	Approved
0.5804	Remote Similarity	NPD6373	Approved
0.5804	Remote Similarity	NPD6372	Approved
0.5804	Remote Similarity	NPD6014	Approved
0.5778	Remote Similarity	NPD4691	Approved
0.5773	Remote Similarity	NPD4221	Approved
0.5773	Remote Similarity	NPD4223	Phase 3
0.5766	Remote Similarity	NPD5701	Approved
0.5752	Remote Similarity	NPD7102	Approved
0.5752	Remote Similarity	NPD7290	Approved
0.5752	Remote Similarity	NPD6883	Approved
0.5745	Remote Similarity	NPD4756	Discovery
0.5728	Remote Similarity	NPD8035	Phase 2
0.5728	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD5654	Approved
0.5702	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5701	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5690	Phase 2
0.57	Remote Similarity	NPD6422	Discontinued
0.57	Remote Similarity	NPD4623	Approved
0.57	Remote Similarity	NPD4519	Discontinued
0.5686	Remote Similarity	NPD4753	Phase 2
0.5682	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7331	Phase 2
0.5673	Remote Similarity	NPD4202	Approved
0.5667	Remote Similarity	NPD4137	Phase 3
0.5667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5221	Approved
0.566	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4697	Phase 3
0.566	Remote Similarity	NPD5222	Approved
0.566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4197	Approved
0.5656	Remote Similarity	NPD7492	Approved
0.5652	Remote Similarity	NPD6882	Approved
0.5652	Remote Similarity	NPD8297	Approved
0.5625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6614	Approved
0.5612	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.561	Remote Similarity	NPD6616	Approved
0.5607	Remote Similarity	NPD5173	Approved
0.5607	Remote Similarity	NPD5959	Approved
0.5604	Remote Similarity	NPD4747	Approved
0.56	Remote Similarity	NPD1696	Phase 3
0.56	Remote Similarity	NPD5329	Approved
0.56	Remote Similarity	NPD7520	Clinical (unspecified phase)

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