NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	238.27
LogP:	2.046
LogD:	1.81
LogS:	-2.776
# Rotatable Bonds:	3
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	3.327
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.636
MDCK Permeability:	1.1680424904625397e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	63.86164474487305%
Volume Distribution (VD):	1.09
Pgp-substrate:	40.72513198852539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.401
CYP2D6-inhibitor:	0.269
CYP2D6-substrate:	0.632
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	10.75
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.874
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.709
Carcinogencity:	0.89
Eye Corrosion:	0.198
Eye Irritation:	0.957
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC37206

Natural Product ID:	NPC37206
*Common Name:**	(S)-1-(6-Hydroxy-2-(1-Hydroxyprop-2-En-2-Yl)-2,3-Dihydrobenzofuran-5-Yl)Ethanone
IUPAC Name:	1-[(2S)-6-hydroxy-2-(3-hydroxyprop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone
Synonyms:
Standard InCHIKey:	KPJMESMRKLJVPB-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-7(6-14)12-4-9-3-10(8(2)15)11(16)5-13(9)17-12/h3,5,12,14,16H,1,4,6H2,2H3/t12-/m0/s1
SMILES:	OCC(=C)[C@H]1Oc2c(C1)cc(c(c2)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462941
PubChem CID:	10036992
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
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11992775]
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387647]
NPO11187	Fraxinus mandshurica	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20988	Geum urbanum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18184	Macaranga triloba	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20988	Geum urbanum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11187	Fraxinus mandshurica	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18184	Macaranga triloba	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11187	Fraxinus mandshurica	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20988	Geum urbanum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21186	Polyporus tumulosus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21123	Pecten opercularis	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19421	Myristica moschata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21583	Brenania brieyi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19941	Ophryosporus macrodon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20525	Swartzia leiocalycina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18184	Macaranga triloba	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18934	Liatris mucronata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12675	Prunus maximowiczii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19854	Dorstenia foetida	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19727	Angelica edulis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20853	Scaphander lignarius	Species	Scaphandridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17421	Solanum crispum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19116	Lachnum papyraceum	Species	Hyaloscyphaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11239	Dittrichia viscosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20027	Streptomyces versipellis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21259	Crescentia alata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	73.0	%	PMID[530078]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	11.6	day	PMID[530078]

☑ 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 NPC37206 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	341
0.1-0.2	1540
0.2-0.3	4014
0.3-0.4	9683
0.4-0.5	8800
0.5-0.6	3775
0.6-0.7	5948
0.7-0.8	5387
0.8-0.85	1867
0.85-0.9	1008
0.9-0.95	329
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC171870
0.9704	High Similarity	NPC137009
0.9496	High Similarity	NPC297788
0.9416	High Similarity	NPC139554
0.9407	High Similarity	NPC84699
0.9407	High Similarity	NPC60667
0.9403	High Similarity	NPC247743
0.9362	High Similarity	NPC202494
0.9357	High Similarity	NPC470857
0.9338	High Similarity	NPC470397
0.9338	High Similarity	NPC156910
0.9333	High Similarity	NPC164136
0.9333	High Similarity	NPC125920
0.9296	High Similarity	NPC168085
0.9275	High Similarity	NPC471697
0.9259	High Similarity	NPC93756
0.9259	High Similarity	NPC108113
0.9259	High Similarity	NPC223457
0.9236	High Similarity	NPC472423
0.9236	High Similarity	NPC474772
0.9236	High Similarity	NPC474744
0.9231	High Similarity	NPC39929
0.9231	High Similarity	NPC317492
0.9231	High Similarity	NPC296030
0.922	High Similarity	NPC224714
0.922	High Similarity	NPC470890
0.9214	High Similarity	NPC130206
0.9214	High Similarity	NPC162476
0.9209	High Similarity	NPC28337
0.9203	High Similarity	NPC131130
0.9197	High Similarity	NPC470398
0.9197	High Similarity	NPC174999
0.9191	High Similarity	NPC144027
0.9191	High Similarity	NPC236974
0.9185	High Similarity	NPC203817
0.9173	High Similarity	NPC230818
0.9172	High Similarity	NPC285623
0.9167	High Similarity	NPC472421
0.9155	High Similarity	NPC472629
0.9149	High Similarity	NPC39329
0.9149	High Similarity	NPC68104
0.9149	High Similarity	NPC257097
0.9149	High Similarity	NPC169591
0.9149	High Similarity	NPC175504
0.9149	High Similarity	NPC164980
0.9149	High Similarity	NPC149026
0.9149	High Similarity	NPC143896
0.9149	High Similarity	NPC310130
0.9149	High Similarity	NPC150408
0.9149	High Similarity	NPC91560
0.9149	High Similarity	NPC221432
0.9149	High Similarity	NPC75049
0.9143	High Similarity	NPC213322
0.9143	High Similarity	NPC258630
0.9143	High Similarity	NPC321980
0.9143	High Similarity	NPC312391
0.9143	High Similarity	NPC470087
0.9143	High Similarity	NPC156190
0.9143	High Similarity	NPC324386
0.9143	High Similarity	NPC279650
0.9143	High Similarity	NPC17170
0.9143	High Similarity	NPC166689
0.9143	High Similarity	NPC4743
0.9143	High Similarity	NPC96408
0.9143	High Similarity	NPC74397
0.9143	High Similarity	NPC3188
0.9137	High Similarity	NPC473076
0.9137	High Similarity	NPC23257
0.9137	High Similarity	NPC470211
0.9124	High Similarity	NPC151113
0.9111	High Similarity	NPC27490
0.9111	High Similarity	NPC475589
0.9111	High Similarity	NPC31872
0.9111	High Similarity	NPC473584
0.9104	High Similarity	NPC84772
0.9103	High Similarity	NPC472580
0.9091	High Similarity	NPC85773
0.9091	High Similarity	NPC473133
0.9091	High Similarity	NPC130581
0.9091	High Similarity	NPC91902
0.9091	High Similarity	NPC12148
0.9091	High Similarity	NPC470670
0.9091	High Similarity	NPC47388
0.9085	High Similarity	NPC236766
0.9085	High Similarity	NPC87486
0.9085	High Similarity	NPC124780
0.9085	High Similarity	NPC316535
0.9085	High Similarity	NPC473015
0.9085	High Similarity	NPC209040
0.9085	High Similarity	NPC473013
0.9085	High Similarity	NPC197252
0.9078	High Similarity	NPC296917
0.9078	High Similarity	NPC64915
0.9078	High Similarity	NPC10937
0.9078	High Similarity	NPC324134
0.9078	High Similarity	NPC76338
0.9078	High Similarity	NPC40833
0.9078	High Similarity	NPC166934
0.9078	High Similarity	NPC161506
0.9078	High Similarity	NPC148757
0.9078	High Similarity	NPC37496
0.9078	High Similarity	NPC167624
0.9078	High Similarity	NPC107572
0.9078	High Similarity	NPC1089
0.9078	High Similarity	NPC166482
0.9078	High Similarity	NPC220998
0.9078	High Similarity	NPC53192
0.9078	High Similarity	NPC32739
0.9078	High Similarity	NPC265040
0.9078	High Similarity	NPC177354
0.9078	High Similarity	NPC78
0.9078	High Similarity	NPC227579
0.9078	High Similarity	NPC324436
0.9078	High Similarity	NPC194432
0.9078	High Similarity	NPC223500
0.9078	High Similarity	NPC125855
0.9078	High Similarity	NPC66515
0.9078	High Similarity	NPC76372
0.9078	High Similarity	NPC328164
0.9078	High Similarity	NPC182852
0.9078	High Similarity	NPC228504
0.9078	High Similarity	NPC306829
0.9071	High Similarity	NPC307990
0.9071	High Similarity	NPC16455
0.9071	High Similarity	NPC470856
0.9071	High Similarity	NPC471587
0.9065	High Similarity	NPC147686
0.9065	High Similarity	NPC474487
0.9065	High Similarity	NPC474504
0.9065	High Similarity	NPC470399
0.9065	High Similarity	NPC470672
0.9065	High Similarity	NPC472460
0.9065	High Similarity	NPC329225
0.9065	High Similarity	NPC124269
0.9065	High Similarity	NPC470671
0.9058	High Similarity	NPC121243
0.9058	High Similarity	NPC222633
0.9058	High Similarity	NPC187826
0.9058	High Similarity	NPC240147
0.9044	High Similarity	NPC25937
0.9041	High Similarity	NPC327269
0.9041	High Similarity	NPC477957
0.9041	High Similarity	NPC31627
0.9041	High Similarity	NPC473996
0.9041	High Similarity	NPC476238
0.9037	High Similarity	NPC324482
0.9037	High Similarity	NPC270369
0.9037	High Similarity	NPC5515
0.9034	High Similarity	NPC321896
0.9034	High Similarity	NPC476185
0.9034	High Similarity	NPC61258
0.903	High Similarity	NPC69235
0.903	High Similarity	NPC939
0.903	High Similarity	NPC212379
0.9028	High Similarity	NPC6511
0.9028	High Similarity	NPC10097
0.9028	High Similarity	NPC135325
0.9023	High Similarity	NPC128428
0.9023	High Similarity	NPC305518
0.9021	High Similarity	NPC187282
0.9021	High Similarity	NPC290133
0.9021	High Similarity	NPC300267
0.9021	High Similarity	NPC210826
0.9021	High Similarity	NPC24136
0.9021	High Similarity	NPC51641
0.9014	High Similarity	NPC475705
0.9014	High Similarity	NPC106985
0.9014	High Similarity	NPC185276
0.9014	High Similarity	NPC81697
0.9014	High Similarity	NPC214166
0.9014	High Similarity	NPC245482
0.9014	High Similarity	NPC85162
0.9014	High Similarity	NPC51887
0.9014	High Similarity	NPC225884
0.9014	High Similarity	NPC316816
0.9014	High Similarity	NPC125894
0.9014	High Similarity	NPC302181
0.9014	High Similarity	NPC476178
0.9014	High Similarity	NPC301751
0.9014	High Similarity	NPC278249
0.9014	High Similarity	NPC117836
0.9014	High Similarity	NPC223812
0.9014	High Similarity	NPC77794
0.9014	High Similarity	NPC107177
0.9014	High Similarity	NPC255133
0.9014	High Similarity	NPC166138
0.9014	High Similarity	NPC18585
0.9014	High Similarity	NPC478086
0.9014	High Similarity	NPC242100
0.9007	High Similarity	NPC110969
0.9007	High Similarity	NPC248372
0.9007	High Similarity	NPC470089
0.9007	High Similarity	NPC110038
0.9	High Similarity	NPC78913
0.9	High Similarity	NPC295384
0.9	High Similarity	NPC329203
0.9	High Similarity	NPC140890
0.9	High Similarity	NPC310135
0.9	High Similarity	NPC225153
0.9	High Similarity	NPC274784

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 NPC37206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	969
0.2-0.3	1776
0.3-0.4	2591
0.4-0.5	1816
0.5-0.6	1119
0.6-0.7	409
0.7-0.8	130
0.8-0.85	29
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9065	High Similarity	NPD1549	Phase 2
0.8993	High Similarity	NPD1552	Clinical (unspecified phase)
0.8993	High Similarity	NPD1550	Clinical (unspecified phase)
0.8849	High Similarity	NPD1510	Phase 2
0.8832	High Similarity	NPD1240	Approved
0.8819	High Similarity	NPD4378	Clinical (unspecified phase)
0.8732	High Similarity	NPD2800	Approved
0.8705	High Similarity	NPD1607	Approved
0.8652	High Similarity	NPD2796	Approved
0.8649	High Similarity	NPD4380	Phase 2
0.8601	High Similarity	NPD1243	Approved
0.86	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8553	High Similarity	NPD7075	Discontinued
0.8543	High Similarity	NPD8443	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD7411	Suspended
0.8446	Intermediate Similarity	NPD920	Approved
0.8435	Intermediate Similarity	NPD2532	Approved
0.8435	Intermediate Similarity	NPD2533	Approved
0.8435	Intermediate Similarity	NPD2534	Approved
0.8425	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1934	Approved
0.8411	Intermediate Similarity	NPD6801	Discontinued
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD3882	Suspended
0.8355	Intermediate Similarity	NPD7819	Suspended
0.8312	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD1511	Approved
0.8243	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD6651	Approved
0.8163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8133	Intermediate Similarity	NPD1512	Approved
0.8129	Intermediate Similarity	NPD7768	Phase 2
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5494	Approved
0.8082	Intermediate Similarity	NPD2344	Approved
0.8077	Intermediate Similarity	NPD3749	Approved
0.8075	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3750	Approved
0.8039	Intermediate Similarity	NPD6599	Discontinued
0.8037	Intermediate Similarity	NPD6559	Discontinued
0.8025	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2801	Approved
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD9717	Approved
0.7925	Intermediate Similarity	NPD1247	Approved
0.7902	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD2309	Approved
0.7866	Intermediate Similarity	NPD5953	Discontinued
0.7852	Intermediate Similarity	NPD2654	Approved
0.7843	Intermediate Similarity	NPD5403	Approved
0.7829	Intermediate Similarity	NPD5401	Approved
0.7823	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.7805	Intermediate Similarity	NPD1729	Discontinued
0.7805	Intermediate Similarity	NPD7074	Phase 3
0.7801	Intermediate Similarity	NPD1203	Approved
0.78	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7054	Approved
0.7744	Intermediate Similarity	NPD7286	Phase 2
0.774	Intermediate Similarity	NPD230	Phase 1
0.7737	Intermediate Similarity	NPD9545	Approved
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7703	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD7472	Approved
0.7671	Intermediate Similarity	NPD943	Approved
0.7655	Intermediate Similarity	NPD2313	Discontinued
0.7654	Intermediate Similarity	NPD5710	Approved
0.7654	Intermediate Similarity	NPD5711	Approved
0.7651	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD422	Phase 1
0.7636	Intermediate Similarity	NPD5844	Phase 1
0.761	Intermediate Similarity	NPD5402	Approved
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.7591	Intermediate Similarity	NPD9493	Approved
0.7584	Intermediate Similarity	NPD7033	Discontinued
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7808	Phase 3
0.7546	Intermediate Similarity	NPD6232	Discontinued
0.7534	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD411	Approved
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD3226	Approved
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7482	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4360	Phase 2
0.7429	Intermediate Similarity	NPD4363	Phase 3
0.7397	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD2346	Discontinued
0.7368	Intermediate Similarity	NPD1471	Phase 3
0.7368	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1465	Phase 2
0.732	Intermediate Similarity	NPD2424	Discontinued
0.7315	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1296	Phase 2
0.7284	Intermediate Similarity	NPD2296	Approved
0.7278	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2798	Approved
0.7246	Intermediate Similarity	NPD2403	Approved
0.7237	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD5760	Phase 2
0.7222	Intermediate Similarity	NPD5761	Phase 2
0.7222	Intermediate Similarity	NPD1608	Approved
0.7211	Intermediate Similarity	NPD9494	Approved
0.7205	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7193	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1164	Approved
0.7188	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3764	Approved
0.7181	Intermediate Similarity	NPD3268	Approved
0.7181	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3972	Approved
0.7102	Intermediate Similarity	NPD4287	Approved
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD7584	Approved
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7075	Intermediate Similarity	NPD2797	Approved
0.7075	Intermediate Similarity	NPD1470	Approved
0.7073	Intermediate Similarity	NPD4288	Approved
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7059	Intermediate Similarity	NPD3751	Discontinued
0.7055	Intermediate Similarity	NPD6280	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7055	Intermediate Similarity	NPD6279	Approved
0.7055	Intermediate Similarity	NPD37	Approved
0.7051	Intermediate Similarity	NPD1652	Phase 2
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4661	Approved
0.7044	Intermediate Similarity	NPD4662	Approved
0.7039	Intermediate Similarity	NPD1933	Approved
0.7039	Intermediate Similarity	NPD6355	Discontinued
0.7034	Intermediate Similarity	NPD1201	Approved
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4966	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.703	Intermediate Similarity	NPD4965	Approved
0.7024	Intermediate Similarity	NPD6808	Phase 2
0.7014	Intermediate Similarity	NPD17	Approved
0.7014	Intermediate Similarity	NPD1778	Approved
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7007	Intermediate Similarity	NPD3225	Approved
0.7007	Intermediate Similarity	NPD74	Approved
0.7007	Intermediate Similarity	NPD1876	Approved
0.7007	Intermediate Similarity	NPD9266	Approved
0.7	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6986	Remote Similarity	NPD9269	Phase 2
0.6981	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3142	Approved
0.6974	Remote Similarity	NPD3140	Approved
0.6974	Remote Similarity	NPD4307	Phase 2
0.6959	Remote Similarity	NPD3267	Approved
0.6959	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD6798	Discontinued
0.6951	Remote Similarity	NPD6844	Discontinued

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