NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.1
Volume:	273.408
LogP:	4.442
LogD:	3.456
LogS:	-4.482
# Rotatable Bonds:	2
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	2.179
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.735
MDCK Permeability:	1.229507597599877e-05
Pgp-inhibitor:	0.105
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	99.37715911865234%
Volume Distribution (VD):	0.751
Pgp-substrate:	1.4824693202972412%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.297
CYP2C19-inhibitor:	0.802
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.459
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.801
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	6.383
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.188
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.44
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.793
Skin Sensitization:	0.499
Carcinogencity:	0.5
Eye Corrosion:	0.017
Eye Irritation:	0.962
Respiratory Toxicity:	0.176

Download Data

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

Natural Product: NPC163029

Natural Product ID:	NPC163029
*Common Name:**	2-(4-Hydroxyphenyl)-5-(E)-Propenylbenzofuran
IUPAC Name:	4-[5-[(E)-prop-1-enyl]-1-benzofuran-2-yl]phenol
Synonyms:
Standard InCHIKey:	OAMUEWCGJSSPRS-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C17H14O2/c1-2-3-12-4-9-16-14(10-12)11-17(19-16)13-5-7-15(18)8-6-13/h2-11,18H,1H3/b3-2+
SMILES:	C/C=C/c1ccc2c(c1)cc(c1ccc(cc1)O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147422
PubChem CID:	53483951
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO13392	Caiophora coronata	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695811]
NPO15400	Krameria lappacea	Species	Krameriaceae	Eukaryota	n.a.	root	n.a.	PMID[21800856]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5464	Baliospermum axillare	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9820	Nepeta erecta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15864	Skimmia wallichii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15400	Krameria lappacea	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO315	Krameria interior	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3420	Alsomitra graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13392	Caiophora coronata	Species	Loasaceae	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
IC50	5
Others	6

Activity Type	# Activity
Individual Protein	6
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	18300.0	nM	PMID[515261]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	2000.0	nM	PMID[515261]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	50000.0	nM	PMID[515261]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	57.2	%	PMID[515261]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	57.2	%	PMID[515261]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	5300.0	nM	PMID[515261]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	14.0	%	PMID[515261]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	35.0	%	PMID[515261]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	74.0	%	PMID[515261]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.44	umol/cm2	PMID[515261]
NPT2	Others	Unspecified		IC50	=	1400.0	nM	PMID[515261]

☑ 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 NPC163029 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	426
0.1-0.2	1807
0.2-0.3	4412
0.3-0.4	11885
0.4-0.5	5857
0.5-0.6	4419
0.6-0.7	7334
0.7-0.8	5295
0.8-0.85	1072
0.85-0.9	172
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC62735
0.9416	High Similarity	NPC225884
0.9281	High Similarity	NPC51641
0.9281	High Similarity	NPC300267
0.9281	High Similarity	NPC210826
0.9214	High Similarity	NPC12148
0.9214	High Similarity	NPC130581
0.9149	High Similarity	NPC272194
0.9149	High Similarity	NPC135325
0.9137	High Similarity	NPC302181
0.9085	High Similarity	NPC296030
0.9085	High Similarity	NPC37226
0.9085	High Similarity	NPC226644
0.9085	High Similarity	NPC37208
0.9085	High Similarity	NPC39929
0.9085	High Similarity	NPC221868
0.9071	High Similarity	NPC230943
0.9065	High Similarity	NPC53192
0.9021	High Similarity	NPC230713
0.9021	High Similarity	NPC78335
0.8958	High Similarity	NPC170169
0.8951	High Similarity	NPC178202
0.8921	High Similarity	NPC28337
0.8836	High Similarity	NPC122365
0.8836	High Similarity	NPC235333
0.8836	High Similarity	NPC472462
0.8836	High Similarity	NPC1477
0.8836	High Similarity	NPC213608
0.8828	High Similarity	NPC116604
0.8811	High Similarity	NPC17816
0.8806	High Similarity	NPC109778
0.8803	High Similarity	NPC155144
0.8776	High Similarity	NPC148938
0.8776	High Similarity	NPC198490
0.8776	High Similarity	NPC297531
0.8776	High Similarity	NPC213936
0.8776	High Similarity	NPC268008
0.8767	High Similarity	NPC5871
0.8767	High Similarity	NPC263676
0.8759	High Similarity	NPC13282
0.8759	High Similarity	NPC167576
0.8732	High Similarity	NPC17262
0.8731	High Similarity	NPC939
0.8716	High Similarity	NPC247677
0.8716	High Similarity	NPC160015
0.8707	High Similarity	NPC183874
0.8705	High Similarity	NPC228661
0.8699	High Similarity	NPC193976
0.8699	High Similarity	NPC23668
0.8699	High Similarity	NPC156244
0.8699	High Similarity	NPC115324
0.8686	High Similarity	NPC27643
0.8681	High Similarity	NPC14875
0.8671	High Similarity	NPC98926
0.8667	High Similarity	NPC327457
0.8667	High Similarity	NPC245395
0.8667	High Similarity	NPC86774
0.8662	High Similarity	NPC144499
0.8658	High Similarity	NPC260902
0.8658	High Similarity	NPC212967
0.8658	High Similarity	NPC96342
0.8658	High Similarity	NPC164110
0.8658	High Similarity	NPC65504
0.8658	High Similarity	NPC246647
0.8658	High Similarity	NPC296957
0.8658	High Similarity	NPC268360
0.8657	High Similarity	NPC2401
0.8652	High Similarity	NPC270883
0.8652	High Similarity	NPC475680
0.8652	High Similarity	NPC69769
0.8652	High Similarity	NPC172986
0.8652	High Similarity	NPC305355
0.8652	High Similarity	NPC261227
0.8643	High Similarity	NPC201395
0.8643	High Similarity	NPC112757
0.8639	High Similarity	NPC67654
0.8639	High Similarity	NPC207624
0.8639	High Similarity	NPC142308
0.8639	High Similarity	NPC60211
0.8633	High Similarity	NPC24394
0.8621	High Similarity	NPC168085
0.8601	High Similarity	NPC106985
0.8601	High Similarity	NPC166138
0.8601	High Similarity	NPC18585
0.86	High Similarity	NPC476349
0.86	High Similarity	NPC476350
0.86	High Similarity	NPC40583
0.86	High Similarity	NPC244750
0.8592	High Similarity	NPC156590
0.8592	High Similarity	NPC64908
0.8592	High Similarity	NPC118840
0.8592	High Similarity	NPC147688
0.8592	High Similarity	NPC110969
0.8592	High Similarity	NPC205006
0.8592	High Similarity	NPC3188
0.8591	High Similarity	NPC180924
0.8582	High Similarity	NPC303633
0.8582	High Similarity	NPC22783
0.8582	High Similarity	NPC220062
0.8582	High Similarity	NPC301217
0.8582	High Similarity	NPC216978
0.8582	High Similarity	NPC55018
0.8582	High Similarity	NPC78913
0.8582	High Similarity	NPC18260
0.8582	High Similarity	NPC137009
0.8582	High Similarity	NPC96565
0.8581	High Similarity	NPC72370
0.8571	High Similarity	NPC106372
0.8571	High Similarity	NPC58668
0.8571	High Similarity	NPC23870
0.8562	High Similarity	NPC317492
0.8561	High Similarity	NPC141252
0.8561	High Similarity	NPC151113
0.8561	High Similarity	NPC11799
0.8552	High Similarity	NPC198427
0.8543	High Similarity	NPC115432
0.8543	High Similarity	NPC260296
0.8542	High Similarity	NPC311741
0.8542	High Similarity	NPC234629
0.854	High Similarity	NPC164236
0.854	High Similarity	NPC112192
0.854	High Similarity	NPC128348
0.854	High Similarity	NPC189106
0.854	High Similarity	NPC309717
0.854	High Similarity	NPC66384
0.8538	High Similarity	NPC246214
0.8531	High Similarity	NPC226636
0.8531	High Similarity	NPC11561
0.8531	High Similarity	NPC473042
0.8529	High Similarity	NPC247779
0.8523	High Similarity	NPC99199
0.8521	High Similarity	NPC235239
0.8521	High Similarity	NPC241100
0.8521	High Similarity	NPC159275
0.8519	High Similarity	NPC125887
0.8519	High Similarity	NPC50583
0.8514	High Similarity	NPC253872
0.8511	High Similarity	NPC473988
0.8511	High Similarity	NPC124269
0.8511	High Similarity	NPC21350
0.8503	High Similarity	NPC472421
0.85	High Similarity	NPC186838
0.85	High Similarity	NPC41461
0.85	High Similarity	NPC477242
0.85	High Similarity	NPC249606
0.85	High Similarity	NPC25287
0.85	High Similarity	NPC29638
0.85	High Similarity	NPC12165
0.85	High Similarity	NPC274109
0.85	High Similarity	NPC477243
0.85	High Similarity	NPC168105
0.85	High Similarity	NPC240593
0.85	High Similarity	NPC66349
0.85	High Similarity	NPC150399
0.85	High Similarity	NPC1486
0.85	High Similarity	NPC477244
0.85	High Similarity	NPC98115
0.8483	Intermediate Similarity	NPC477955
0.8472	Intermediate Similarity	NPC164980
0.8472	Intermediate Similarity	NPC190637
0.8472	Intermediate Similarity	NPC24821
0.8472	Intermediate Similarity	NPC75049
0.8472	Intermediate Similarity	NPC212932
0.8472	Intermediate Similarity	NPC143896
0.8472	Intermediate Similarity	NPC221432
0.8472	Intermediate Similarity	NPC169591
0.8472	Intermediate Similarity	NPC219915
0.8472	Intermediate Similarity	NPC150408
0.8472	Intermediate Similarity	NPC293053
0.8472	Intermediate Similarity	NPC9117
0.8472	Intermediate Similarity	NPC149026
0.8472	Intermediate Similarity	NPC310130
0.8472	Intermediate Similarity	NPC68104
0.8472	Intermediate Similarity	NPC38219
0.8472	Intermediate Similarity	NPC39329
0.8472	Intermediate Similarity	NPC91560
0.8472	Intermediate Similarity	NPC257097
0.8472	Intermediate Similarity	NPC11700
0.8472	Intermediate Similarity	NPC175504
0.8462	Intermediate Similarity	NPC4743
0.8462	Intermediate Similarity	NPC14871
0.8462	Intermediate Similarity	NPC213322
0.8462	Intermediate Similarity	NPC103362
0.8462	Intermediate Similarity	NPC254010
0.8462	Intermediate Similarity	NPC282300
0.8462	Intermediate Similarity	NPC312391
0.8462	Intermediate Similarity	NPC324386
0.8451	Intermediate Similarity	NPC37206
0.8451	Intermediate Similarity	NPC295384
0.8451	Intermediate Similarity	NPC262635
0.8451	Intermediate Similarity	NPC477956
0.8451	Intermediate Similarity	NPC217186
0.8451	Intermediate Similarity	NPC53181
0.8446	Intermediate Similarity	NPC258249
0.8446	Intermediate Similarity	NPC472423
0.8446	Intermediate Similarity	NPC472580
0.8446	Intermediate Similarity	NPC474772
0.8446	Intermediate Similarity	NPC474744
0.8446	Intermediate Similarity	NPC318424
0.844	Intermediate Similarity	NPC188879

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 NPC163029 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	992
0.2-0.3	1307
0.3-0.4	2690
0.4-0.5	1926
0.5-0.6	1217
0.6-0.7	434
0.7-0.8	139
0.8-0.85	25
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD2344	Approved
0.8857	High Similarity	NPD2309	Approved
0.8714	High Similarity	NPD7421	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1243	Approved
0.844	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD1240	Approved
0.8289	Intermediate Similarity	NPD3749	Approved
0.8286	Intermediate Similarity	NPD1607	Approved
0.8252	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1510	Phase 2
0.8169	Intermediate Similarity	NPD2799	Discontinued
0.8158	Intermediate Similarity	NPD2296	Approved
0.8151	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD3750	Approved
0.8112	Intermediate Similarity	NPD2796	Approved
0.8079	Intermediate Similarity	NPD7411	Suspended
0.8069	Intermediate Similarity	NPD2800	Approved
0.8054	Intermediate Similarity	NPD920	Approved
0.8041	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD2313	Discontinued
0.8	Intermediate Similarity	NPD3764	Approved
0.7974	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1608	Approved
0.7935	Intermediate Similarity	NPD7075	Discontinued
0.7895	Intermediate Similarity	NPD4380	Phase 2
0.7871	Intermediate Similarity	NPD3882	Suspended
0.7871	Intermediate Similarity	NPD7768	Phase 2
0.7862	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7852	Intermediate Similarity	NPD1511	Approved
0.7836	Intermediate Similarity	NPD9545	Approved
0.7829	Intermediate Similarity	NPD3226	Approved
0.781	Intermediate Similarity	NPD3972	Approved
0.7808	Intermediate Similarity	NPD1471	Phase 3
0.7793	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD1934	Approved
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.777	Intermediate Similarity	NPD1203	Approved
0.777	Intermediate Similarity	NPD7003	Approved
0.7748	Intermediate Similarity	NPD1512	Approved
0.7746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6799	Approved
0.7727	Intermediate Similarity	NPD1241	Discontinued
0.7721	Intermediate Similarity	NPD17	Approved
0.7714	Intermediate Similarity	NPD2798	Approved
0.7698	Intermediate Similarity	NPD1876	Approved
0.7687	Intermediate Similarity	NPD2346	Discontinued
0.7677	Intermediate Similarity	NPD6280	Approved
0.7677	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD6279	Approved
0.7673	Intermediate Similarity	NPD6959	Discontinued
0.7671	Intermediate Similarity	NPD4308	Phase 3
0.7658	Intermediate Similarity	NPD919	Approved
0.7654	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2797	Approved
0.764	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2801	Approved
0.7622	Intermediate Similarity	NPD3268	Approved
0.7619	Intermediate Similarity	NPD1551	Phase 2
0.7616	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3926	Phase 2
0.7562	Intermediate Similarity	NPD1247	Approved
0.7554	Intermediate Similarity	NPD9717	Approved
0.7548	Intermediate Similarity	NPD6599	Discontinued
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD2354	Approved
0.7482	Intermediate Similarity	NPD422	Phase 1
0.7451	Intermediate Similarity	NPD2533	Approved
0.7451	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2534	Approved
0.7451	Intermediate Similarity	NPD2532	Approved
0.7447	Intermediate Similarity	NPD1283	Approved
0.7447	Intermediate Similarity	NPD3225	Approved
0.7439	Intermediate Similarity	NPD3818	Discontinued
0.7432	Intermediate Similarity	NPD7033	Discontinued
0.7429	Intermediate Similarity	NPD1481	Phase 2
0.7425	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6166	Phase 2
0.7421	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6651	Approved
0.741	Intermediate Similarity	NPD5953	Discontinued
0.7407	Intermediate Similarity	NPD6232	Discontinued
0.7403	Intermediate Similarity	NPD5049	Phase 3
0.7397	Intermediate Similarity	NPD4307	Phase 2
0.7394	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3266	Approved
0.7394	Intermediate Similarity	NPD1164	Approved
0.7394	Intermediate Similarity	NPD3267	Approved
0.7391	Intermediate Similarity	NPD1651	Approved
0.7383	Intermediate Similarity	NPD4476	Approved
0.7383	Intermediate Similarity	NPD4477	Approved
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7378	Intermediate Similarity	NPD7473	Discontinued
0.7372	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6832	Phase 2
0.7361	Intermediate Similarity	NPD4908	Phase 1
0.7357	Intermediate Similarity	NPD1610	Phase 2
0.7357	Intermediate Similarity	NPD1535	Discovery
0.7357	Intermediate Similarity	NPD1201	Approved
0.7355	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD2353	Approved
0.7333	Intermediate Similarity	NPD7177	Discontinued
0.7333	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1548	Phase 1
0.7319	Intermediate Similarity	NPD1894	Discontinued
0.7315	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4625	Phase 3
0.7305	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6808	Phase 2
0.7296	Intermediate Similarity	NPD1465	Phase 2
0.7292	Intermediate Similarity	NPD9494	Approved
0.7292	Intermediate Similarity	NPD2861	Phase 2
0.729	Intermediate Similarity	NPD6273	Approved
0.7289	Intermediate Similarity	NPD7286	Phase 2
0.7279	Intermediate Similarity	NPD3140	Approved
0.7279	Intermediate Similarity	NPD943	Approved
0.7279	Intermediate Similarity	NPD3142	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4287	Approved
0.725	Intermediate Similarity	NPD3817	Phase 2
0.725	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1729	Discontinued
0.7244	Intermediate Similarity	NPD3869	Phase 3
0.7244	Intermediate Similarity	NPD3873	Phase 3
0.7234	Intermediate Similarity	NPD1281	Approved
0.7233	Intermediate Similarity	NPD7577	Discontinued
0.7219	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6002	Phase 3
0.7219	Intermediate Similarity	NPD6004	Phase 3
0.7219	Intermediate Similarity	NPD6005	Phase 3
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7174	Intermediate Similarity	NPD9493	Approved
0.7162	Intermediate Similarity	NPD4060	Phase 1
0.7161	Intermediate Similarity	NPD7390	Discontinued
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD411	Approved
0.7134	Intermediate Similarity	NPD5403	Approved
0.7133	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5401	Approved
0.7114	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD447	Suspended
0.7101	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6671	Approved
0.7097	Intermediate Similarity	NPD7440	Discontinued
0.7092	Intermediate Similarity	NPD4626	Approved
0.7092	Intermediate Similarity	NPD1778	Approved
0.7086	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6696	Suspended
0.7083	Intermediate Similarity	NPD7054	Approved
0.7081	Intermediate Similarity	NPD5760	Phase 2
0.7081	Intermediate Similarity	NPD5761	Phase 2
0.7081	Intermediate Similarity	NPD8455	Phase 2
0.7059	Intermediate Similarity	NPD2424	Discontinued
0.7052	Intermediate Similarity	NPD8434	Phase 2
0.7045	Intermediate Similarity	NPD4466	Phase 1
0.7041	Intermediate Similarity	NPD7472	Approved
0.7027	Intermediate Similarity	NPD1296	Phase 2
0.7024	Intermediate Similarity	NPD2163	Approved
0.7014	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2654	Approved
0.7007	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5535	Approved
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD4662	Approved
0.7	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD230	Phase 1
0.7	Intermediate Similarity	NPD6797	Phase 2
0.7	Intermediate Similarity	NPD3823	Discontinued
0.6987	Remote Similarity	NPD6667	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