NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	528.27
Volume:	556.917
LogP:	4.792
LogD:	1.441
LogS:	-2.561
# Rotatable Bonds:	13
TPSA:	135.04
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	4.364
Fsp3:	0.567
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.767
MDCK Permeability:	2.037464946624823e-05
Pgp-inhibitor:	0.864
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.292
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.047

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	94.13530731201172%
Volume Distribution (VD):	1.073
Pgp-substrate:	1.7279443740844727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.417
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.75
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.086
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.887
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	16.552
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.037
Carcinogencity:	0.24
Eye Corrosion:	0.019
Eye Irritation:	0.123
Respiratory Toxicity:	0.846

Download Data

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

Natural Product: NPC477048

Natural Product ID:	NPC477048
*Common Name:**	Elaphopilosin E
IUPAC Name:	n.a.
Synonyms:	elaphopilosin E
Standard InCHIKey:	IFBHKANUCDMETJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H40O8/c1-7-9-10-12-21(32)24-23(38-6)16-22(33)18(26(24)34)15-19-27(35)25(20(31)11-8-2)29(37)30(5,28(19)36)14-13-17(3)4/h13,16,33-34,36-37H,7-12,14-15H2,1-6H3
SMILES:	CCCCCC(=O)c1c(OC)cc(O)c(CC2=C(O)C(C)(CC=C(C)C)C(O)=C(C(=O)CCC)C2=O)C1o
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	2005-DEC	PMID[19239238]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	Eukaryota	n.a.	La Banderita, Tucumn, Argentina	n.a.	PMID[20384357]
NPO7440	Elaphoglossum piloselloides	Species	Dryopteridaceae	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
LD50	1
Others	4

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	Activity	=	81	%	PMID[20384357]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	Activity	=	52	%	PMID[20384357]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	Activity	=	14	%	PMID[20384357]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	LD50	=	22.2	nM	PMID[20384357]
NPT6698	Organism	Biomphalaria peregrina	Biomphalaria peregrina	LD90	=	42.2	nM	PMID[20384357]

☑ 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 NPC477048 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	423
0.1-0.2	1644
0.2-0.3	4022
0.3-0.4	9585
0.4-0.5	8922
0.5-0.6	3596
0.6-0.7	5809
0.7-0.8	6631
0.8-0.85	1706
0.85-0.9	353
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477047
0.9103	High Similarity	NPC32694
0.9085	High Similarity	NPC89474
0.9038	High Similarity	NPC45146
0.9038	High Similarity	NPC235018
0.9032	High Similarity	NPC236796
0.9032	High Similarity	NPC300727
0.9032	High Similarity	NPC241904
0.9013	High Similarity	NPC103509
0.8987	High Similarity	NPC220313
0.8981	High Similarity	NPC40491
0.8981	High Similarity	NPC278052
0.8974	High Similarity	NPC476242
0.8974	High Similarity	NPC329091
0.8968	High Similarity	NPC274730
0.8968	High Similarity	NPC142339
0.8968	High Similarity	NPC470762
0.8968	High Similarity	NPC474167
0.8961	High Similarity	NPC250557
0.8954	High Similarity	NPC202157
0.8947	High Similarity	NPC102003
0.8947	High Similarity	NPC92722
0.8938	High Similarity	NPC478060
0.8938	High Similarity	NPC470377
0.8938	High Similarity	NPC470374
0.8938	High Similarity	NPC478059
0.8938	High Similarity	NPC471975
0.8931	High Similarity	NPC473286
0.8924	High Similarity	NPC470694
0.8917	High Similarity	NPC80375
0.8917	High Similarity	NPC56085
0.8917	High Similarity	NPC228785
0.8917	High Similarity	NPC119224
0.8917	High Similarity	NPC14353
0.8917	High Similarity	NPC320359
0.8903	High Similarity	NPC472048
0.8889	High Similarity	NPC85131
0.8889	High Similarity	NPC10467
0.8882	High Similarity	NPC15329
0.8882	High Similarity	NPC131451
0.8882	High Similarity	NPC287395
0.8882	High Similarity	NPC183655
0.8868	High Similarity	NPC7483
0.8868	High Similarity	NPC236132
0.8861	High Similarity	NPC61010
0.8861	High Similarity	NPC472275
0.8861	High Similarity	NPC87431
0.8861	High Similarity	NPC278427
0.8854	High Similarity	NPC172770
0.8854	High Similarity	NPC185258
0.8854	High Similarity	NPC100123
0.8846	High Similarity	NPC317383
0.8839	High Similarity	NPC276409
0.8839	High Similarity	NPC124714
0.8839	High Similarity	NPC75279
0.8839	High Similarity	NPC250822
0.8834	High Similarity	NPC471969
0.8831	High Similarity	NPC19980
0.8831	High Similarity	NPC45291
0.8816	High Similarity	NPC61871
0.8816	High Similarity	NPC93034
0.8816	High Similarity	NPC30647
0.8816	High Similarity	NPC55557
0.8816	High Similarity	NPC119660
0.8812	High Similarity	NPC39306
0.88	High Similarity	NPC287722
0.88	High Similarity	NPC471417
0.8797	High Similarity	NPC155302
0.8797	High Similarity	NPC475886
0.8797	High Similarity	NPC161947
0.8797	High Similarity	NPC84571
0.8797	High Similarity	NPC200746
0.8797	High Similarity	NPC474287
0.879	High Similarity	NPC469584
0.879	High Similarity	NPC165977
0.879	High Similarity	NPC217677
0.879	High Similarity	NPC179732
0.879	High Similarity	NPC79053
0.879	High Similarity	NPC78103
0.8784	High Similarity	NPC477055
0.8784	High Similarity	NPC477056
0.8782	High Similarity	NPC79998
0.8782	High Similarity	NPC234485
0.8782	High Similarity	NPC227325
0.8782	High Similarity	NPC134287
0.8782	High Similarity	NPC50715
0.8782	High Similarity	NPC2476
0.8782	High Similarity	NPC68727
0.8782	High Similarity	NPC196439
0.8782	High Similarity	NPC280339
0.8782	High Similarity	NPC167815
0.8782	High Similarity	NPC16082
0.8782	High Similarity	NPC4455
0.8782	High Similarity	NPC183597
0.8782	High Similarity	NPC138360
0.8782	High Similarity	NPC201136
0.8782	High Similarity	NPC146165
0.8782	High Similarity	NPC128863
0.8782	High Similarity	NPC67396
0.8782	High Similarity	NPC92659
0.8782	High Similarity	NPC208197
0.8782	High Similarity	NPC163780
0.8782	High Similarity	NPC82592
0.8782	High Similarity	NPC113906
0.8782	High Similarity	NPC130589
0.8774	High Similarity	NPC181209
0.8774	High Similarity	NPC100263
0.8774	High Similarity	NPC100971
0.8774	High Similarity	NPC216769
0.8774	High Similarity	NPC291802
0.8774	High Similarity	NPC121522
0.8774	High Similarity	NPC209487
0.8774	High Similarity	NPC269451
0.8774	High Similarity	NPC474993
0.8774	High Similarity	NPC245382
0.8774	High Similarity	NPC35763
0.8774	High Similarity	NPC131266
0.8774	High Similarity	NPC249570
0.8766	High Similarity	NPC62042
0.8766	High Similarity	NPC239363
0.8766	High Similarity	NPC184136
0.8758	High Similarity	NPC218490
0.8758	High Similarity	NPC39091
0.875	High Similarity	NPC475985
0.875	High Similarity	NPC226987
0.875	High Similarity	NPC138978
0.875	High Similarity	NPC133065
0.875	High Similarity	NPC270837
0.875	High Similarity	NPC473313
0.875	High Similarity	NPC143903
0.875	High Similarity	NPC476822
0.875	High Similarity	NPC165389
0.875	High Similarity	NPC248638
0.875	High Similarity	NPC329669
0.875	High Similarity	NPC152659
0.875	High Similarity	NPC236521
0.875	High Similarity	NPC472278
0.8742	High Similarity	NPC474187
0.8742	High Similarity	NPC201560
0.8742	High Similarity	NPC474186
0.8742	High Similarity	NPC311740
0.8742	High Similarity	NPC474351
0.8742	High Similarity	NPC475883
0.8734	High Similarity	NPC210459
0.8734	High Similarity	NPC235448
0.8734	High Similarity	NPC477410
0.8734	High Similarity	NPC197856
0.8733	High Similarity	NPC284556
0.8733	High Similarity	NPC49108
0.8733	High Similarity	NPC301178
0.8726	High Similarity	NPC24640
0.8726	High Similarity	NPC475799
0.8726	High Similarity	NPC474520
0.8726	High Similarity	NPC54928
0.8726	High Similarity	NPC13779
0.8726	High Similarity	NPC150227
0.8718	High Similarity	NPC476631
0.8718	High Similarity	NPC183878
0.8718	High Similarity	NPC22519
0.8718	High Similarity	NPC160951
0.8718	High Similarity	NPC255350
0.8718	High Similarity	NPC281477
0.8718	High Similarity	NPC274327
0.8718	High Similarity	NPC231018
0.8718	High Similarity	NPC69394
0.8718	High Similarity	NPC127172
0.8718	High Similarity	NPC273248
0.8718	High Similarity	NPC155686
0.8718	High Similarity	NPC107109
0.8718	High Similarity	NPC145379
0.8718	High Similarity	NPC47781
0.8718	High Similarity	NPC176775
0.8718	High Similarity	NPC93552
0.871	High Similarity	NPC262623
0.871	High Similarity	NPC272566
0.8701	High Similarity	NPC134293
0.8696	High Similarity	NPC472450
0.8696	High Similarity	NPC275780
0.8696	High Similarity	NPC8070
0.8696	High Similarity	NPC267153
0.8696	High Similarity	NPC239752
0.8696	High Similarity	NPC326520
0.8688	High Similarity	NPC48860
0.8688	High Similarity	NPC294965
0.8688	High Similarity	NPC329760
0.8688	High Similarity	NPC25152
0.8679	High Similarity	NPC321399
0.8679	High Similarity	NPC139036
0.8679	High Similarity	NPC297212
0.8671	High Similarity	NPC222814
0.8671	High Similarity	NPC474208
0.8671	High Similarity	NPC472963
0.8671	High Similarity	NPC162869
0.8671	High Similarity	NPC111969
0.8671	High Similarity	NPC37543
0.8671	High Similarity	NPC78302
0.8671	High Similarity	NPC472914
0.8671	High Similarity	NPC472438
0.8671	High Similarity	NPC75215
0.8671	High Similarity	NPC29841

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 NPC477048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	1011
0.2-0.3	1908
0.3-0.4	2719
0.4-0.5	1731
0.5-0.6	927
0.6-0.7	354
0.7-0.8	103
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD2801	Approved
0.8481	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD1934	Approved
0.8415	Intermediate Similarity	NPD7473	Discontinued
0.8377	Intermediate Similarity	NPD1511	Approved
0.8344	Intermediate Similarity	NPD6232	Discontinued
0.8322	Intermediate Similarity	NPD6651	Approved
0.8289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD1512	Approved
0.8261	Intermediate Similarity	NPD3882	Suspended
0.8235	Intermediate Similarity	NPD2800	Approved
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD2534	Approved
0.8067	Intermediate Similarity	NPD1240	Approved
0.8067	Intermediate Similarity	NPD943	Approved
0.8047	Intermediate Similarity	NPD7074	Phase 3
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD7054	Approved
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3817	Phase 2
0.7974	Intermediate Similarity	NPD1510	Phase 2
0.7961	Intermediate Similarity	NPD1607	Approved
0.795	Intermediate Similarity	NPD4380	Phase 2
0.7941	Intermediate Similarity	NPD7472	Approved
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7907	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD230	Phase 1
0.7892	Intermediate Similarity	NPD5494	Approved
0.7849	Intermediate Similarity	NPD7251	Discontinued
0.7844	Intermediate Similarity	NPD6959	Discontinued
0.7806	Intermediate Similarity	NPD2935	Discontinued
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6599	Discontinued
0.7707	Intermediate Similarity	NPD1549	Phase 2
0.7701	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7674	Intermediate Similarity	NPD5844	Phase 1
0.7665	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3926	Phase 2
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2796	Approved
0.7578	Intermediate Similarity	NPD6799	Approved
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7545	Intermediate Similarity	NPD5402	Approved
0.7529	Intermediate Similarity	NPD1247	Approved
0.7515	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD5711	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7411	Suspended
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6801	Discontinued
0.7425	Intermediate Similarity	NPD37	Approved
0.7423	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3027	Phase 3
0.74	Intermediate Similarity	NPD9269	Phase 2
0.7386	Intermediate Similarity	NPD9494	Approved
0.7349	Intermediate Similarity	NPD3226	Approved
0.7325	Intermediate Similarity	NPD447	Suspended
0.7314	Intermediate Similarity	NPD7228	Approved
0.7312	Intermediate Similarity	NPD2344	Approved
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3748	Approved
0.7294	Intermediate Similarity	NPD7768	Phase 2
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4966	Approved
0.7294	Intermediate Similarity	NPD4965	Approved
0.7284	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6559	Discontinued
0.7244	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7237	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7209	Intermediate Similarity	NPD919	Approved
0.7208	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3972	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD6190	Approved
0.7133	Intermediate Similarity	NPD9268	Approved
0.7126	Intermediate Similarity	NPD920	Approved
0.7126	Intermediate Similarity	NPD5403	Approved
0.7117	Intermediate Similarity	NPD1243	Approved
0.7102	Intermediate Similarity	NPD2403	Approved
0.7099	Intermediate Similarity	NPD2346	Discontinued
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.709	Intermediate Similarity	NPD6779	Approved
0.709	Intermediate Similarity	NPD6782	Approved
0.709	Intermediate Similarity	NPD6781	Approved
0.709	Intermediate Similarity	NPD6777	Approved
0.709	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD6780	Approved
0.709	Intermediate Similarity	NPD6776	Approved
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7083	Intermediate Similarity	NPD1653	Approved
0.7081	Intermediate Similarity	NPD2799	Discontinued
0.7079	Intermediate Similarity	NPD7286	Phase 2
0.7073	Intermediate Similarity	NPD8166	Discontinued
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7048	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5353	Approved
0.7032	Intermediate Similarity	NPD1470	Approved
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5401	Approved
0.7006	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1201	Approved
0.6988	Remote Similarity	NPD3300	Phase 2
0.6987	Remote Similarity	NPD2798	Approved
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.6979	Remote Similarity	NPD7698	Approved
0.6978	Remote Similarity	NPD8313	Approved
0.6978	Remote Similarity	NPD8312	Approved
0.6961	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7685	Pre-registration
0.6949	Remote Similarity	NPD5242	Approved
0.6943	Remote Similarity	NPD7870	Phase 2
0.6943	Remote Similarity	NPD7871	Phase 2
0.6941	Remote Similarity	NPD7458	Discontinued
0.6931	Remote Similarity	NPD7907	Approved
0.6927	Remote Similarity	NPD6823	Phase 2
0.6923	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7701	Phase 2
0.6903	Remote Similarity	NPD4749	Approved
0.6899	Remote Similarity	NPD6832	Phase 2
0.6893	Remote Similarity	NPD7229	Phase 3
0.6886	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7240	Approved
0.6867	Remote Similarity	NPD7003	Approved
0.6859	Remote Similarity	NPD1876	Approved
0.6859	Remote Similarity	NPD6696	Suspended
0.6853	Remote Similarity	NPD7874	Approved
0.6853	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD9717	Approved
0.6835	Remote Similarity	NPD3018	Phase 2
0.6829	Remote Similarity	NPD5406	Approved
0.6829	Remote Similarity	NPD5408	Approved
0.6829	Remote Similarity	NPD5405	Approved
0.6829	Remote Similarity	NPD5404	Approved
0.6825	Remote Similarity	NPD6534	Approved
0.6825	Remote Similarity	NPD6535	Approved
0.6821	Remote Similarity	NPD9493	Approved
0.6818	Remote Similarity	NPD7801	Approved
0.6818	Remote Similarity	NPD7783	Phase 2
0.6818	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1203	Approved
0.6813	Remote Similarity	NPD2313	Discontinued
0.6813	Remote Similarity	NPD3764	Approved
0.6806	Remote Similarity	NPD7699	Phase 2
0.6806	Remote Similarity	NPD7700	Phase 2
0.6805	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4908	Phase 1
0.6788	Remote Similarity	NPD1471	Phase 3
0.6782	Remote Similarity	NPD5760	Phase 2
0.6782	Remote Similarity	NPD5761	Phase 2
0.6776	Remote Similarity	NPD5536	Phase 2
0.6776	Remote Similarity	NPD6104	Discontinued
0.6774	Remote Similarity	NPD422	Phase 1
0.6763	Remote Similarity	NPD5089	Approved
0.6763	Remote Similarity	NPD6386	Approved
0.6763	Remote Similarity	NPD6385	Approved
0.6763	Remote Similarity	NPD5090	Approved
0.6757	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4626	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