NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	3.815
LogD:	3.94
LogS:	-3.996
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	3.869
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761
MDCK Permeability:	1.6174693882931024e-05
Pgp-inhibitor:	0.748
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	80.2791976928711%
Volume Distribution (VD):	1.849
Pgp-substrate:	10.759269714355469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.663
CYP2C19-inhibitor:	0.455
CYP2C19-substrate:	0.632
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.9
CYP2D6-substrate:	0.368
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	3.942
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.155
AMES Toxicity:	0.289
Rat Oral Acute Toxicity:	0.579
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.919
Carcinogencity:	0.276
Eye Corrosion:	0.077
Eye Irritation:	0.942
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC477139

Natural Product ID:	NPC477139
*Common Name:**	(4aR,10aS)-6-hydroxy-1,1-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthrene-4a-carbaldehyde
IUPAC Name:	(4aR,10aS)-6-hydroxy-1,1-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthrene-4a-carbaldehyde
Synonyms:	(+)-Pisiferal
Standard InCHIKey:	NFRKTUHCQSVVEY-ICSRJNTNSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-12(2)13-8-14-15(9-16(13)22)20(11-21)7-5-6-19(3,4)18(20)10-17(14)23/h8-9,11-12,18,22H,5-7,10H2,1-4H3/t18-,20-/m0/s1
SMILES:	CC(C)C1=C(C=C2C(=C1)C(=O)C[C@@H]3[C@@]2(CCCC3(C)C)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53320910
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

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

Biological Activity

Activity Type	# Activity
IC50	5
Others	1

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000	nM	PMID[20961093]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000	nM	PMID[20961093]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000	nM	PMID[20961093]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000	nM	PMID[20961093]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	PMID[20961093]
NPT2	Others	Unspecified		Inhibition	=	65.9	%	PMID[20961093]

☑ 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 NPC477139 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	313
0.1-0.2	1532
0.2-0.3	3056
0.3-0.4	8039
0.4-0.5	10868
0.5-0.6	6926
0.6-0.7	9047
0.7-0.8	2589
0.8-0.85	262
0.85-0.9	42
0.9-0.95	14
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9603	High Similarity	NPC3009
0.9531	High Similarity	NPC471851
0.9524	High Similarity	NPC69424
0.9524	High Similarity	NPC84672
0.9524	High Similarity	NPC176130
0.9524	High Similarity	NPC78364
0.9394	High Similarity	NPC475957
0.9385	High Similarity	NPC78307
0.937	High Similarity	NPC72667
0.9365	High Similarity	NPC137750
0.9313	High Similarity	NPC202225
0.9302	High Similarity	NPC108129
0.9291	High Similarity	NPC254492
0.9225	High Similarity	NPC303910
0.9225	High Similarity	NPC276238
0.9225	High Similarity	NPC171460
0.9134	High Similarity	NPC199273
0.9127	High Similarity	NPC11250
0.9	High Similarity	NPC96024
0.8976	High Similarity	NPC282577
0.8947	High Similarity	NPC111845
0.8906	High Similarity	NPC471187
0.8898	High Similarity	NPC154696
0.8898	High Similarity	NPC253627
0.8837	High Similarity	NPC181334
0.8806	High Similarity	NPC138472
0.8797	High Similarity	NPC291001
0.8797	High Similarity	NPC41847
0.8777	High Similarity	NPC477209
0.8769	High Similarity	NPC123506
0.8768	High Similarity	NPC471853
0.8768	High Similarity	NPC476534
0.8732	High Similarity	NPC5568
0.8714	High Similarity	NPC100242
0.8702	High Similarity	NPC71610
0.8696	High Similarity	NPC162939
0.8682	High Similarity	NPC176208
0.8676	High Similarity	NPC153088
0.8672	High Similarity	NPC259703
0.8672	High Similarity	NPC32322
0.8662	High Similarity	NPC143685
0.8657	High Similarity	NPC93015
0.8657	High Similarity	NPC476847
0.8657	High Similarity	NPC164295
0.8651	High Similarity	NPC174087
0.8643	High Similarity	NPC248068
0.8643	High Similarity	NPC308572
0.8623	High Similarity	NPC477593
0.8615	High Similarity	NPC198014
0.8613	High Similarity	NPC86524
0.8613	High Similarity	NPC471670
0.8613	High Similarity	NPC472308
0.8605	High Similarity	NPC249340
0.8605	High Similarity	NPC162935
0.8571	High Similarity	NPC229894
0.8551	High Similarity	NPC36868
0.854	High Similarity	NPC80035
0.8531	High Similarity	NPC477208
0.8529	High Similarity	NPC49742
0.8529	High Similarity	NPC52407
0.8529	High Similarity	NPC115458
0.8527	High Similarity	NPC216216
0.8519	High Similarity	NPC18798
0.8519	High Similarity	NPC239134
0.8519	High Similarity	NPC85342
0.8511	High Similarity	NPC193555
0.8511	High Similarity	NPC73061
0.8507	High Similarity	NPC117899
0.8489	Intermediate Similarity	NPC230811
0.8489	Intermediate Similarity	NPC13715
0.8489	Intermediate Similarity	NPC4214
0.8485	Intermediate Similarity	NPC87985
0.8478	Intermediate Similarity	NPC474311
0.8473	Intermediate Similarity	NPC275145
0.8473	Intermediate Similarity	NPC273683
0.8472	Intermediate Similarity	NPC52692
0.8467	Intermediate Similarity	NPC474519
0.8462	Intermediate Similarity	NPC478160
0.8462	Intermediate Similarity	NPC120545
0.8462	Intermediate Similarity	NPC295034
0.8456	Intermediate Similarity	NPC165612
0.8433	Intermediate Similarity	NPC193203
0.8433	Intermediate Similarity	NPC48248
0.8417	Intermediate Similarity	NPC277559
0.8417	Intermediate Similarity	NPC53001
0.8417	Intermediate Similarity	NPC477592
0.8417	Intermediate Similarity	NPC49911
0.8406	Intermediate Similarity	NPC477596
0.8397	Intermediate Similarity	NPC121168
0.8397	Intermediate Similarity	NPC91478
0.8394	Intermediate Similarity	NPC59459
0.8394	Intermediate Similarity	NPC53896
0.8392	Intermediate Similarity	NPC309169
0.8392	Intermediate Similarity	NPC196941
0.8385	Intermediate Similarity	NPC241001
0.8382	Intermediate Similarity	NPC17083
0.838	Intermediate Similarity	NPC135524
0.837	Intermediate Similarity	NPC25736
0.8369	Intermediate Similarity	NPC181560
0.8369	Intermediate Similarity	NPC315578
0.8369	Intermediate Similarity	NPC169452
0.8357	Intermediate Similarity	NPC469681
0.8357	Intermediate Similarity	NPC87723
0.8357	Intermediate Similarity	NPC471974
0.8357	Intermediate Similarity	NPC469680
0.8346	Intermediate Similarity	NPC131799
0.8346	Intermediate Similarity	NPC35797
0.8346	Intermediate Similarity	NPC192948
0.8345	Intermediate Similarity	NPC272268
0.8345	Intermediate Similarity	NPC191976
0.8333	Intermediate Similarity	NPC50924
0.8333	Intermediate Similarity	NPC12402
0.8333	Intermediate Similarity	NPC477594
0.8333	Intermediate Similarity	NPC12070
0.8322	Intermediate Similarity	NPC478164
0.8322	Intermediate Similarity	NPC199936
0.8322	Intermediate Similarity	NPC66593
0.831	Intermediate Similarity	NPC204045
0.831	Intermediate Similarity	NPC305845
0.8309	Intermediate Similarity	NPC136588
0.8309	Intermediate Similarity	NPC62219
0.8309	Intermediate Similarity	NPC199253
0.8309	Intermediate Similarity	NPC253488
0.8308	Intermediate Similarity	NPC478121
0.8308	Intermediate Similarity	NPC190501
0.8308	Intermediate Similarity	NPC318552
0.8298	Intermediate Similarity	NPC138099
0.8298	Intermediate Similarity	NPC242994
0.8298	Intermediate Similarity	NPC26924
0.8286	Intermediate Similarity	NPC471905
0.8284	Intermediate Similarity	NPC15837
0.8284	Intermediate Similarity	NPC295202
0.8284	Intermediate Similarity	NPC227741
0.8284	Intermediate Similarity	NPC49647
0.8284	Intermediate Similarity	NPC136342
0.8284	Intermediate Similarity	NPC474737
0.8281	Intermediate Similarity	NPC38893
0.8281	Intermediate Similarity	NPC308311
0.8281	Intermediate Similarity	NPC477137
0.8276	Intermediate Similarity	NPC314437
0.8273	Intermediate Similarity	NPC249272
0.8273	Intermediate Similarity	NPC475917
0.8273	Intermediate Similarity	NPC283088
0.8271	Intermediate Similarity	NPC142956
0.8271	Intermediate Similarity	NPC173978
0.8271	Intermediate Similarity	NPC152525
0.8271	Intermediate Similarity	NPC68756
0.8264	Intermediate Similarity	NPC79627
0.8261	Intermediate Similarity	NPC225051
0.8261	Intermediate Similarity	NPC267205
0.8261	Intermediate Similarity	NPC114183
0.8261	Intermediate Similarity	NPC314048
0.8252	Intermediate Similarity	NPC30846
0.8252	Intermediate Similarity	NPC469855
0.8252	Intermediate Similarity	NPC184935
0.8252	Intermediate Similarity	NPC471972
0.8252	Intermediate Similarity	NPC471971
0.8252	Intermediate Similarity	NPC474961
0.8248	Intermediate Similarity	NPC72669
0.8248	Intermediate Similarity	NPC474517
0.8244	Intermediate Similarity	NPC472981
0.8244	Intermediate Similarity	NPC190971
0.8235	Intermediate Similarity	NPC99731
0.8231	Intermediate Similarity	NPC474310
0.8231	Intermediate Similarity	NPC42657
0.8231	Intermediate Similarity	NPC473767
0.8227	Intermediate Similarity	NPC289358
0.8227	Intermediate Similarity	NPC28592
0.8227	Intermediate Similarity	NPC42384
0.8227	Intermediate Similarity	NPC245760
0.8227	Intermediate Similarity	NPC23667
0.8227	Intermediate Similarity	NPC473479
0.8227	Intermediate Similarity	NPC149773
0.8227	Intermediate Similarity	NPC477849
0.8227	Intermediate Similarity	NPC469857
0.8227	Intermediate Similarity	NPC91887
0.8227	Intermediate Similarity	NPC473779
0.8227	Intermediate Similarity	NPC51531
0.8227	Intermediate Similarity	NPC114333
0.8227	Intermediate Similarity	NPC50615
0.8227	Intermediate Similarity	NPC5014
0.8227	Intermediate Similarity	NPC157284
0.8227	Intermediate Similarity	NPC165191
0.8227	Intermediate Similarity	NPC46242
0.8227	Intermediate Similarity	NPC297797
0.8222	Intermediate Similarity	NPC19432
0.8222	Intermediate Similarity	NPC30491
0.8222	Intermediate Similarity	NPC262936
0.8217	Intermediate Similarity	NPC304510
0.8217	Intermediate Similarity	NPC172219
0.8214	Intermediate Similarity	NPC254847
0.8214	Intermediate Similarity	NPC193358
0.8207	Intermediate Similarity	NPC34482
0.8203	Intermediate Similarity	NPC322197
0.8201	Intermediate Similarity	NPC474224
0.8201	Intermediate Similarity	NPC270899
0.8201	Intermediate Similarity	NPC474117
0.8201	Intermediate Similarity	NPC194970
0.8195	Intermediate Similarity	NPC85511
0.8194	Intermediate Similarity	NPC163948

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 NPC477139 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	971
0.2-0.3	1323
0.3-0.4	2656
0.4-0.5	2243
0.5-0.6	1166
0.6-0.7	425
0.7-0.8	54
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD3019	Approved
0.8231	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD2932	Approved
0.8045	Intermediate Similarity	NPD1201	Approved
0.7959	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1470	Approved
0.7931	Intermediate Similarity	NPD7003	Approved
0.7891	Intermediate Similarity	NPD7390	Discontinued
0.7778	Intermediate Similarity	NPD5408	Approved
0.7778	Intermediate Similarity	NPD5404	Approved
0.7778	Intermediate Similarity	NPD5406	Approved
0.7778	Intermediate Similarity	NPD5405	Approved
0.7748	Intermediate Similarity	NPD7458	Discontinued
0.773	Intermediate Similarity	NPD6663	Approved
0.771	Intermediate Similarity	NPD5951	Approved
0.7704	Intermediate Similarity	NPD3026	Approved
0.7704	Intermediate Similarity	NPD3023	Approved
0.7698	Intermediate Similarity	NPD5736	Approved
0.7687	Intermediate Similarity	NPD3024	Approved
0.7687	Intermediate Similarity	NPD3025	Approved
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3091	Approved
0.7594	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3972	Approved
0.7586	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8166	Discontinued
0.7434	Intermediate Similarity	NPD6273	Approved
0.7403	Intermediate Similarity	NPD3226	Approved
0.7391	Intermediate Similarity	NPD3092	Approved
0.7372	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1283	Approved
0.7308	Intermediate Similarity	NPD2342	Discontinued
0.7305	Intermediate Similarity	NPD1164	Approved
0.7299	Intermediate Similarity	NPD1651	Approved
0.7297	Intermediate Similarity	NPD6100	Approved
0.7297	Intermediate Similarity	NPD6099	Approved
0.7297	Intermediate Similarity	NPD2935	Discontinued
0.7293	Intermediate Similarity	NPD7635	Approved
0.729	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7248	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD4059	Approved
0.7246	Intermediate Similarity	NPD3095	Discontinued
0.7246	Intermediate Similarity	NPD4626	Approved
0.7237	Intermediate Similarity	NPD3300	Phase 2
0.7222	Intermediate Similarity	NPD7008	Discontinued
0.7222	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.7215	Intermediate Similarity	NPD7819	Suspended
0.7211	Intermediate Similarity	NPD1607	Approved
0.7195	Intermediate Similarity	NPD7473	Discontinued
0.7192	Intermediate Similarity	NPD943	Approved
0.7183	Intermediate Similarity	NPD3094	Phase 2
0.7172	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD2798	Approved
0.7117	Intermediate Similarity	NPD6232	Discontinued
0.7114	Intermediate Similarity	NPD1510	Phase 2
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7113	Intermediate Similarity	NPD1876	Approved
0.7101	Intermediate Similarity	NPD9545	Approved
0.7089	Intermediate Similarity	NPD7411	Suspended
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9494	Approved
0.7075	Intermediate Similarity	NPD1240	Approved
0.7063	Intermediate Similarity	NPD1809	Phase 2
0.705	Intermediate Similarity	NPD5691	Approved
0.7045	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1755	Approved
0.7032	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3020	Approved
0.7029	Intermediate Similarity	NPD7610	Discontinued
0.702	Intermediate Similarity	NPD2344	Approved
0.702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD288	Approved
0.7007	Intermediate Similarity	NPD8032	Phase 2
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4097	Suspended
0.6972	Remote Similarity	NPD4878	Approved
0.6966	Remote Similarity	NPD4208	Discontinued
0.6959	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.694	Remote Similarity	NPD4750	Phase 3
0.6939	Remote Similarity	NPD3268	Approved
0.6929	Remote Similarity	NPD844	Approved
0.6928	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4380	Phase 2
0.6903	Remote Similarity	NPD7236	Approved
0.6883	Remote Similarity	NPD3750	Approved
0.6879	Remote Similarity	NPD2286	Discontinued
0.6875	Remote Similarity	NPD3495	Discontinued
0.687	Remote Similarity	NPD1930	Approved
0.687	Remote Similarity	NPD1929	Approved
0.687	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6651	Approved
0.6863	Remote Similarity	NPD1549	Phase 2
0.6852	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3620	Phase 2
0.6846	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4060	Phase 1
0.6846	Remote Similarity	NPD4140	Approved
0.6846	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7177	Discontinued
0.6842	Remote Similarity	NPD2796	Approved
0.6839	Remote Similarity	NPD2309	Approved
0.6838	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9493	Approved
0.6818	Remote Similarity	NPD1237	Approved
0.6815	Remote Similarity	NPD3022	Approved
0.6815	Remote Similarity	NPD3021	Approved
0.6813	Remote Similarity	NPD6599	Discontinued
0.6809	Remote Similarity	NPD4093	Discontinued
0.6797	Remote Similarity	NPD2860	Approved
0.6797	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2859	Approved
0.6797	Remote Similarity	NPD1471	Phase 3
0.6792	Remote Similarity	NPD7239	Suspended
0.6782	Remote Similarity	NPD8150	Discontinued
0.6781	Remote Similarity	NPD4624	Approved
0.6772	Remote Similarity	NPD845	Approved
0.6769	Remote Similarity	NPD2066	Phase 3
0.6768	Remote Similarity	NPD7075	Discontinued
0.6761	Remote Similarity	NPD1751	Approved
0.6741	Remote Similarity	NPD74	Approved
0.6741	Remote Similarity	NPD9266	Approved
0.6739	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2531	Phase 2
0.6732	Remote Similarity	NPD2438	Suspended
0.6732	Remote Similarity	NPD4476	Approved
0.6732	Remote Similarity	NPD4477	Approved
0.6728	Remote Similarity	NPD1934	Approved
0.6719	Remote Similarity	NPD2933	Approved
0.6719	Remote Similarity	NPD2934	Approved
0.6715	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2797	Approved
0.6711	Remote Similarity	NPD2313	Discontinued
0.671	Remote Similarity	NPD2800	Approved
0.6707	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7768	Phase 2
0.6706	Remote Similarity	NPD6020	Phase 2
0.6705	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2629	Approved
0.669	Remote Similarity	NPD5327	Phase 3
0.6689	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD4207	Discontinued
0.6689	Remote Similarity	NPD2605	Approved
0.6689	Remote Similarity	NPD2606	Approved
0.6687	Remote Similarity	NPD5761	Phase 2
0.6687	Remote Similarity	NPD5760	Phase 2
0.6687	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6559	Discontinued
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD7743	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD7742	Approved
0.6667	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4308	Phase 3
0.6644	Remote Similarity	NPD5155	Approved
0.6644	Remote Similarity	NPD5156	Approved
0.6643	Remote Similarity	NPD1778	Approved
0.6643	Remote Similarity	NPD3317	Approved
0.6629	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7577	Discontinued
0.6623	Remote Similarity	NPD1551	Phase 2
0.6622	Remote Similarity	NPD3635	Approved
0.6622	Remote Similarity	NPD3637	Approved
0.6622	Remote Similarity	NPD3636	Approved
0.6621	Remote Similarity	NPD1608	Approved
0.6621	Remote Similarity	NPD9269	Phase 2
0.662	Remote Similarity	NPD7009	Phase 2
0.6619	Remote Similarity	NPD1241	Discontinued
0.6609	Remote Similarity	NPD8313	Approved
0.6609	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8312	Approved
0.6607	Remote Similarity	NPD5711	Approved
0.6607	Remote Similarity	NPD5710	Approved
0.6606	Remote Similarity	NPD3882	Suspended
0.6605	Remote Similarity	NPD7028	Phase 2
0.66	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3267	Approved
0.6599	Remote Similarity	NPD3266	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