NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	232.35
LogP:	2.57
LogD:	1.914
LogS:	-3.044
# Rotatable Bonds:	2
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	3.626
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.665
MDCK Permeability:	1.4963644389354158e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.352

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	90.56481170654297%
Volume Distribution (VD):	0.769
Pgp-substrate:	7.718051433563232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.695
CYP2C19-substrate:	0.498
CYP2C9-inhibitor:	0.33
CYP2C9-substrate:	0.716
CYP2D6-inhibitor:	0.15
CYP2D6-substrate:	0.679
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.378

ADMET: Excretion

Clearance (CL):	8.388
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.626
Drug-inuced Liver Injury (DILI):	0.399
AMES Toxicity:	0.759
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.713
Carcinogencity:	0.912
Eye Corrosion:	0.004
Eye Irritation:	0.161
Respiratory Toxicity:	0.119

Download Data

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

Natural Product: NPC470857

Natural Product ID:	NPC470857
*Common Name:**	10,11-Epoxy-4-Hydroxy Tremetone
IUPAC Name:	1-[(2R)-4-hydroxy-2-(2-methyloxiran-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone
Synonyms:
Standard InCHIKey:	UAVACTVIORNYBH-JTDNENJMSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-7(14)8-3-4-10-9(12(8)15)5-11(17-10)13(2)6-16-13/h3-4,11,15H,5-6H2,1-2H3/t11-,13?/m1/s1
SMILES:	CC(=O)C1=C(C2=C(C=C1)OC(C2)C3(CO3)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2271141
PubChem CID:	76326917
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000119] Acetophenones

*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
NPO32889	baccharis sp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11929285]

☑ 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
GI50	4
IC50	15
Others	3

Activity Type	# Activity
Organism	21
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	30600.0	nM	PMID[530778]
NPT597	Organism	Spinacia oleracea	Spinacia oleracea	IC50	=	13800.0	nM	PMID[530778]
NPT355	Organism	Phaseolus vulgaris	Phaseolus vulgaris	IC50	=	17100.0	nM	PMID[530778]
NPT594	Organism	Trifolium pratense	Trifolium pratense	IC50	=	10100.0	nM	PMID[530778]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	IC50	=	15800.0	nM	PMID[530778]
NPT364	Organism	Lactuca sativa	Lactuca sativa	IC50	=	11000.0	nM	PMID[530778]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	IC50	=	18000.0	nM	PMID[530778]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	Inhibition	=	100.0	%	PMID[530778]
NPT594	Organism	Trifolium pratense	Trifolium pratense	Inhibition	=	100.0	%	PMID[530778]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	Inhibition	=	100.0	%	PMID[530778]
NPT594	Organism	Trifolium pratense	Trifolium pratense	IC50	=	7100.0	nM	PMID[530778]
NPT594	Organism	Trifolium pratense	Trifolium pratense	IC50	=	7200.0	nM	PMID[530778]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	IC50	=	9900.0	nM	PMID[530778]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	IC50	=	7700.0	nM	PMID[530778]
NPT364	Organism	Lactuca sativa	Lactuca sativa	IC50	=	10900.0	nM	PMID[530778]
NPT364	Organism	Lactuca sativa	Lactuca sativa	IC50	=	10500.0	nM	PMID[530778]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	IC50	=	11900.0	nM	PMID[530778]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	IC50	=	11200.0	nM	PMID[530778]
NPT594	Organism	Trifolium pratense	Trifolium pratense	GI50	=	7100.0	nM	PMID[530778]
NPT596	Organism	Lolium multiflorum	Lolium multiflorum	GI50	=	10400.0	nM	PMID[530778]
NPT364	Organism	Lactuca sativa	Lactuca sativa	GI50	=	11500.0	nM	PMID[530778]
NPT595	Organism	Physalis ixocarpa	Physalis ixocarpa	GI50	=	8700.0	nM	PMID[530778]

☑ 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 NPC470857 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	379
0.1-0.2	1606
0.2-0.3	4345
0.3-0.4	10217
0.4-0.5	7933
0.5-0.6	4051
0.6-0.7	6229
0.7-0.8	5417
0.8-0.85	1842
0.85-0.9	642
0.9-0.95	35
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC171870
0.9496	High Similarity	NPC137009
0.9379	High Similarity	NPC472421
0.9357	High Similarity	NPC37206
0.9315	High Similarity	NPC472423
0.9315	High Similarity	NPC474772
0.9315	High Similarity	NPC474744
0.9306	High Similarity	NPC202494
0.9301	High Similarity	NPC297788
0.9296	High Similarity	NPC130206
0.9252	High Similarity	NPC31627
0.9252	High Similarity	NPC473996
0.9252	High Similarity	NPC327269
0.9252	High Similarity	NPC476238
0.9225	High Similarity	NPC74397
0.9184	High Similarity	NPC471675
0.9184	High Similarity	NPC472636
0.9184	High Similarity	NPC472580
0.9172	High Similarity	NPC14875
0.9161	High Similarity	NPC162476
0.9122	High Similarity	NPC285623
0.9122	High Similarity	NPC477957
0.911	High Similarity	NPC168085
0.9085	High Similarity	NPC473076
0.9054	High Similarity	NPC472422
0.9054	High Similarity	NPC471676
0.9054	High Similarity	NPC263384
0.9054	High Similarity	NPC244577
0.9054	High Similarity	NPC472420
0.9048	High Similarity	NPC317492
0.9041	High Similarity	NPC473133
0.9041	High Similarity	NPC47388
0.9041	High Similarity	NPC470670
0.9041	High Similarity	NPC91902
0.9041	High Similarity	NPC85773
0.9034	High Similarity	NPC316535
0.9014	High Similarity	NPC470399
0.8986	High Similarity	NPC180351
0.8973	High Similarity	NPC316769
0.8966	High Similarity	NPC242100
0.8966	High Similarity	NPC255133
0.8951	High Similarity	NPC471697
0.8951	High Similarity	NPC23257
0.8936	High Similarity	NPC84699
0.8936	High Similarity	NPC151113
0.8936	High Similarity	NPC60667
0.8933	High Similarity	NPC7989
0.8933	High Similarity	NPC223701
0.8933	High Similarity	NPC472583
0.8929	High Similarity	NPC247743
0.8926	High Similarity	NPC471677
0.8921	High Similarity	NPC470859
0.8904	High Similarity	NPC209040
0.8903	High Similarity	NPC108433
0.8897	High Similarity	NPC276565
0.8889	High Similarity	NPC470856
0.8889	High Similarity	NPC328102
0.8889	High Similarity	NPC471587
0.8881	High Similarity	NPC131130
0.8874	High Similarity	NPC470681
0.8874	High Similarity	NPC279218
0.8874	High Similarity	NPC108937
0.8874	High Similarity	NPC477958
0.8873	High Similarity	NPC187826
0.8873	High Similarity	NPC156910
0.8867	High Similarity	NPC171651
0.8867	High Similarity	NPC475790
0.8867	High Similarity	NPC35567
0.8867	High Similarity	NPC256141
0.8867	High Similarity	NPC243171
0.8865	High Similarity	NPC125920
0.8865	High Similarity	NPC164136
0.8859	High Similarity	NPC321896
0.8859	High Similarity	NPC61258
0.8859	High Similarity	NPC476185
0.8851	High Similarity	NPC10097
0.8844	High Similarity	NPC474302
0.8844	High Similarity	NPC472629
0.8841	High Similarity	NPC230818
0.8836	High Similarity	NPC18886
0.8836	High Similarity	NPC149026
0.8836	High Similarity	NPC166138
0.8836	High Similarity	NPC68104
0.8836	High Similarity	NPC18585
0.8836	High Similarity	NPC214166
0.8836	High Similarity	NPC150408
0.8836	High Similarity	NPC257097
0.8836	High Similarity	NPC39329
0.8836	High Similarity	NPC478086
0.8836	High Similarity	NPC164980
0.8836	High Similarity	NPC221432
0.8836	High Similarity	NPC143896
0.8836	High Similarity	NPC106985
0.8836	High Similarity	NPC91560
0.8836	High Similarity	NPC316816
0.8836	High Similarity	NPC175504
0.8836	High Similarity	NPC75049
0.8836	High Similarity	NPC310130
0.8836	High Similarity	NPC169591
0.8831	High Similarity	NPC92589
0.8828	High Similarity	NPC312391
0.8828	High Similarity	NPC3188
0.8828	High Similarity	NPC470087
0.8828	High Similarity	NPC4743
0.8828	High Similarity	NPC321980
0.8828	High Similarity	NPC150023
0.8828	High Similarity	NPC470089
0.8828	High Similarity	NPC324386
0.8828	High Similarity	NPC213322
0.8819	High Similarity	NPC139554
0.8816	High Similarity	NPC474609
0.8816	High Similarity	NPC474738
0.8816	High Similarity	NPC78554
0.8816	High Similarity	NPC475797
0.8816	High Similarity	NPC469936
0.8816	High Similarity	NPC109967
0.8816	High Similarity	NPC129053
0.8816	High Similarity	NPC321372
0.8808	High Similarity	NPC311579
0.8808	High Similarity	NPC236756
0.8808	High Similarity	NPC293286
0.8808	High Similarity	NPC469405
0.88	High Similarity	NPC262038
0.88	High Similarity	NPC319910
0.88	High Similarity	NPC474023
0.88	High Similarity	NPC254412
0.88	High Similarity	NPC278476
0.88	High Similarity	NPC318424
0.88	High Similarity	NPC262039
0.88	High Similarity	NPC474021
0.8794	High Similarity	NPC108113
0.8794	High Similarity	NPC93756
0.8792	High Similarity	NPC39929
0.8792	High Similarity	NPC296030
0.8792	High Similarity	NPC89442
0.8792	High Similarity	NPC307052
0.8792	High Similarity	NPC472628
0.8792	High Similarity	NPC226644
0.8792	High Similarity	NPC139966
0.8792	High Similarity	NPC5173
0.8792	High Similarity	NPC37226
0.8786	High Similarity	NPC27490
0.8784	High Similarity	NPC201731
0.8784	High Similarity	NPC130581
0.8784	High Similarity	NPC473077
0.8784	High Similarity	NPC104406
0.8784	High Similarity	NPC12148
0.8784	High Similarity	NPC79469
0.8784	High Similarity	NPC97716
0.8784	High Similarity	NPC23728
0.8784	High Similarity	NPC222298
0.8784	High Similarity	NPC296998
0.8784	High Similarity	NPC472627
0.8784	High Similarity	NPC110303
0.8784	High Similarity	NPC24673
0.8784	High Similarity	NPC51070
0.8784	High Similarity	NPC237635
0.8777	High Similarity	NPC84772
0.8776	High Similarity	NPC131568
0.8776	High Similarity	NPC311741
0.8776	High Similarity	NPC473015
0.8776	High Similarity	NPC236766
0.8776	High Similarity	NPC234629
0.8776	High Similarity	NPC470890
0.8776	High Similarity	NPC87486
0.8776	High Similarity	NPC473013
0.8776	High Similarity	NPC224714
0.8776	High Similarity	NPC197252
0.8776	High Similarity	NPC124780
0.8776	High Similarity	NPC131579
0.8767	High Similarity	NPC177354
0.8767	High Similarity	NPC10937
0.8767	High Similarity	NPC37496
0.8767	High Similarity	NPC167624
0.8767	High Similarity	NPC107572
0.8767	High Similarity	NPC194432
0.8767	High Similarity	NPC40833
0.8767	High Similarity	NPC161506
0.8767	High Similarity	NPC220998
0.8767	High Similarity	NPC11561
0.8767	High Similarity	NPC144499
0.8767	High Similarity	NPC265040
0.8767	High Similarity	NPC147145
0.8767	High Similarity	NPC1089
0.8767	High Similarity	NPC53192
0.8767	High Similarity	NPC76338
0.8767	High Similarity	NPC227579
0.8767	High Similarity	NPC148757
0.8767	High Similarity	NPC32739
0.8767	High Similarity	NPC66515
0.8767	High Similarity	NPC228504
0.8767	High Similarity	NPC328164
0.8767	High Similarity	NPC306829
0.8767	High Similarity	NPC76372
0.8767	High Similarity	NPC324436
0.8767	High Similarity	NPC226636
0.8767	High Similarity	NPC64915
0.8767	High Similarity	NPC125855
0.8767	High Similarity	NPC296917
0.8767	High Similarity	NPC324134

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 NPC470857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	985
0.2-0.3	1942
0.3-0.4	2634
0.4-0.5	1739
0.5-0.6	1021
0.6-0.7	360
0.7-0.8	113
0.8-0.85	23
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD1549	Phase 2
0.8681	High Similarity	NPD1552	Clinical (unspecified phase)
0.8681	High Similarity	NPD1550	Clinical (unspecified phase)
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8609	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD2800	Approved
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8542	High Similarity	NPD1510	Phase 2
0.8521	High Similarity	NPD1240	Approved
0.8516	High Similarity	NPD7075	Discontinued
0.8497	Intermediate Similarity	NPD1934	Approved
0.8442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD920	Approved
0.8403	Intermediate Similarity	NPD1607	Approved
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6801	Discontinued
0.8356	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD3882	Suspended
0.828	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1511	Approved
0.8212	Intermediate Similarity	NPD6799	Approved
0.8194	Intermediate Similarity	NPD7411	Suspended
0.8188	Intermediate Similarity	NPD1243	Approved
0.8176	Intermediate Similarity	NPD5494	Approved
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2534	Approved
0.8146	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1512	Approved
0.8098	Intermediate Similarity	NPD3818	Discontinued
0.8089	Intermediate Similarity	NPD2801	Approved
0.8089	Intermediate Similarity	NPD7819	Suspended
0.8049	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3749	Approved
0.7905	Intermediate Similarity	NPD6651	Approved
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7866	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2344	Approved
0.7812	Intermediate Similarity	NPD3817	Phase 2
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7725	Intermediate Similarity	NPD7054	Approved
0.7707	Intermediate Similarity	NPD5403	Approved
0.7692	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD9717	Approved
0.7679	Intermediate Similarity	NPD1729	Discontinued
0.7679	Intermediate Similarity	NPD7472	Approved
0.7662	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6232	Discontinued
0.7635	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5953	Discontinued
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD5844	Phase 1
0.7613	Intermediate Similarity	NPD2309	Approved
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD447	Suspended
0.76	Intermediate Similarity	NPD230	Phase 1
0.7593	Intermediate Similarity	NPD5402	Approved
0.7588	Intermediate Similarity	NPD7251	Discontinued
0.7566	Intermediate Similarity	NPD2799	Discontinued
0.7544	Intermediate Similarity	NPD7808	Phase 3
0.7534	Intermediate Similarity	NPD1203	Approved
0.7533	Intermediate Similarity	NPD943	Approved
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD2654	Approved
0.7465	Intermediate Similarity	NPD9545	Approved
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3748	Approved
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2403	Approved
0.7425	Intermediate Similarity	NPD5711	Approved
0.7425	Intermediate Similarity	NPD5710	Approved
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7419	Intermediate Similarity	NPD2424	Discontinued
0.7391	Intermediate Similarity	NPD3226	Approved
0.7379	Intermediate Similarity	NPD422	Phase 1
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9493	Approved
0.7303	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1613	Approved
0.729	Intermediate Similarity	NPD6100	Approved
0.729	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD411	Approved
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6832	Phase 2
0.726	Intermediate Similarity	NPD1610	Phase 2
0.7255	Intermediate Similarity	NPD5124	Phase 1
0.7255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2346	Discontinued
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7222	Intermediate Similarity	NPD1548	Phase 1
0.7222	Intermediate Similarity	NPD4363	Phase 3
0.7222	Intermediate Similarity	NPD4360	Phase 2
0.7207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9494	Approved
0.7195	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4361	Phase 2
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7171	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD4308	Phase 3
0.7108	Intermediate Similarity	NPD5760	Phase 2
0.7108	Intermediate Similarity	NPD5761	Phase 2
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7086	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7390	Discontinued
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.7066	Intermediate Similarity	NPD2296	Approved
0.7059	Intermediate Similarity	NPD1296	Phase 2
0.7059	Intermediate Similarity	NPD3764	Approved
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1652	Phase 2
0.7032	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD1933	Approved
0.7027	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2798	Approved
0.7018	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD8313	Approved
0.7	Intermediate Similarity	NPD4287	Approved
0.6993	Remote Similarity	NPD3027	Phase 3
0.698	Remote Similarity	NPD1608	Approved
0.6975	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7199	Phase 2
0.6957	Remote Similarity	NPD3887	Approved
0.6957	Remote Similarity	NPD2354	Approved
0.6954	Remote Similarity	NPD1164	Approved
0.6948	Remote Similarity	NPD3268	Approved
0.6948	Remote Similarity	NPD6798	Discontinued
0.6946	Remote Similarity	NPD37	Approved
0.6941	Remote Similarity	NPD6234	Discontinued
0.6935	Remote Similarity	NPD6777	Approved
0.6935	Remote Similarity	NPD6776	Approved
0.6935	Remote Similarity	NPD6782	Approved
0.6935	Remote Similarity	NPD6780	Approved
0.6935	Remote Similarity	NPD6778	Approved
0.6935	Remote Similarity	NPD6781	Approved
0.6935	Remote Similarity	NPD6779	Approved
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4662	Approved
0.6933	Remote Similarity	NPD4661	Approved
0.6932	Remote Similarity	NPD3823	Discontinued
0.6927	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD1653	Approved
0.6906	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5049	Phase 3
0.6883	Remote Similarity	NPD4625	Phase 3
0.6879	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD9269	Phase 2
0.6867	Remote Similarity	NPD3972	Approved
0.6867	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4288	Approved
0.6859	Remote Similarity	NPD4307	Phase 2
0.6845	Remote Similarity	NPD6280	Approved
0.6845	Remote Similarity	NPD6279	Approved
0.6842	Remote Similarity	NPD1470	Approved
0.6842	Remote Similarity	NPD2797	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