NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.09
Volume:	282.198
LogP:	4.227
LogD:	3.096
LogS:	-3.842
# Rotatable Bonds:	2
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	2.445
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:	-4.813
MDCK Permeability:	1.2769684872182552e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.109
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	99.49883270263672%
Volume Distribution (VD):	0.781
Pgp-substrate:	1.170863389968872%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.893
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	6.973
Half-life (T1/2):	0.566

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.243
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.653
Carcinogencity:	0.403
Eye Corrosion:	0.01
Eye Irritation:	0.95
Respiratory Toxicity:	0.649

Download Data

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

Natural Product: NPC225884

Natural Product ID:	NPC225884
*Common Name:**	2-(2,4-Dihydroxyphenyl)-5-(E)-Propenylbenzofuran
IUPAC Name:	4-[5-[(E)-prop-1-enyl]-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	SDWZWUUOXFFJSA-NSCUHMNNSA-N
Standard InCHI:	InChI=1S/C17H14O3/c1-2-3-11-4-7-16-12(8-11)9-17(20-16)14-6-5-13(18)10-15(14)19/h2-10,18-19H,1H3/b3-2+
SMILES:	C/C=C/c1ccc2c(c1)cc(c1ccc(cc1O)O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147420
PubChem CID:	10355545
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]
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]
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]

☑ 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	6
Others	6

Activity Type	# Activity
Individual Protein	6
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	7100.0	nM	PMID[545065]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	>	50000.0	nM	PMID[545065]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	=	57.2	%	PMID[545065]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	Inhibition	=	57.2	%	PMID[545065]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	3800.0	nM	PMID[545065]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	7400.0	nM	PMID[545065]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	15.0	%	PMID[545065]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	29.0	%	PMID[545065]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	64.0	%	PMID[545065]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.6	umol/cm2	PMID[545065]
NPT2	Others	Unspecified		IC50	=	3400.0	nM	PMID[545065]
NPT1	Others	Radical scavenging activity		IC50	=	22100.0	nM	PMID[545065]

☑ 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 NPC225884 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	427
0.1-0.2	1902
0.2-0.3	4626
0.3-0.4	11876
0.4-0.5	5840
0.5-0.6	4332
0.6-0.7	5888
0.7-0.8	4355
0.8-0.85	1965
0.85-0.9	1163
0.9-0.95	300
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC51641
0.9856	High Similarity	NPC300267
0.9856	High Similarity	NPC210826
0.9786	High Similarity	NPC130581
0.9786	High Similarity	NPC12148
0.9716	High Similarity	NPC272194
0.9716	High Similarity	NPC135325
0.9712	High Similarity	NPC302181
0.9648	High Similarity	NPC226644
0.9648	High Similarity	NPC37226
0.9648	High Similarity	NPC39929
0.9648	High Similarity	NPC221868
0.9648	High Similarity	NPC37208
0.9648	High Similarity	NPC296030
0.9643	High Similarity	NPC230943
0.964	High Similarity	NPC53192
0.958	High Similarity	NPC78335
0.958	High Similarity	NPC230713
0.9514	High Similarity	NPC170169
0.951	High Similarity	NPC178202
0.9496	High Similarity	NPC28337
0.9416	High Similarity	NPC163029
0.9384	High Similarity	NPC235333
0.9384	High Similarity	NPC213608
0.9384	High Similarity	NPC1477
0.9384	High Similarity	NPC122365
0.9384	High Similarity	NPC472462
0.9379	High Similarity	NPC116604
0.9371	High Similarity	NPC17816
0.9366	High Similarity	NPC155144
0.932	High Similarity	NPC213936
0.932	High Similarity	NPC297531
0.932	High Similarity	NPC198490
0.932	High Similarity	NPC148938
0.9315	High Similarity	NPC5871
0.9315	High Similarity	NPC263676
0.931	High Similarity	NPC167576
0.9296	High Similarity	NPC17262
0.9281	High Similarity	NPC62735
0.9281	High Similarity	NPC228661
0.9257	High Similarity	NPC247677
0.9257	High Similarity	NPC160015
0.9252	High Similarity	NPC183874
0.9247	High Similarity	NPC115324
0.9247	High Similarity	NPC156244
0.9247	High Similarity	NPC193976
0.9247	High Similarity	NPC23668
0.9231	High Similarity	NPC98926
0.9225	High Similarity	NPC144499
0.922	High Similarity	NPC270883
0.922	High Similarity	NPC305355
0.922	High Similarity	NPC261227
0.922	High Similarity	NPC475680
0.922	High Similarity	NPC69769
0.922	High Similarity	NPC172986
0.9214	High Similarity	NPC201395
0.9195	High Similarity	NPC212967
0.9195	High Similarity	NPC268360
0.9195	High Similarity	NPC96342
0.9195	High Similarity	NPC164110
0.9195	High Similarity	NPC65504
0.9195	High Similarity	NPC296957
0.9195	High Similarity	NPC260902
0.9195	High Similarity	NPC246647
0.9184	High Similarity	NPC207624
0.9184	High Similarity	NPC67654
0.9184	High Similarity	NPC142308
0.9172	High Similarity	NPC168085
0.9161	High Similarity	NPC166138
0.9161	High Similarity	NPC18585
0.9161	High Similarity	NPC106985
0.9155	High Similarity	NPC147688
0.9155	High Similarity	NPC64908
0.9155	High Similarity	NPC156590
0.9155	High Similarity	NPC118840
0.9155	High Similarity	NPC3188
0.9155	High Similarity	NPC205006
0.9155	High Similarity	NPC110969
0.9149	High Similarity	NPC303633
0.9149	High Similarity	NPC137009
0.9149	High Similarity	NPC96565
0.9149	High Similarity	NPC216978
0.9149	High Similarity	NPC220062
0.9149	High Similarity	NPC55018
0.9149	High Similarity	NPC18260
0.9149	High Similarity	NPC78913
0.9149	High Similarity	NPC301217
0.9137	High Similarity	NPC151113
0.9133	High Similarity	NPC476350
0.9133	High Similarity	NPC244750
0.9133	High Similarity	NPC476349
0.9133	High Similarity	NPC40583
0.9128	High Similarity	NPC180924
0.9122	High Similarity	NPC72370
0.9116	High Similarity	NPC58668
0.9116	High Similarity	NPC106372
0.911	High Similarity	NPC317492
0.9103	High Similarity	NPC198427
0.9097	High Similarity	NPC234629
0.9097	High Similarity	NPC311741
0.9091	High Similarity	NPC226636
0.9091	High Similarity	NPC473042
0.9091	High Similarity	NPC11561
0.9085	High Similarity	NPC159275
0.9085	High Similarity	NPC235239
0.9085	High Similarity	NPC241100
0.9078	High Similarity	NPC124269
0.9078	High Similarity	NPC21350
0.9073	High Similarity	NPC115432
0.9073	High Similarity	NPC260296
0.9071	High Similarity	NPC150399
0.9071	High Similarity	NPC98115
0.9071	High Similarity	NPC29638
0.9071	High Similarity	NPC41461
0.9071	High Similarity	NPC25287
0.9071	High Similarity	NPC477242
0.9071	High Similarity	NPC477243
0.9071	High Similarity	NPC1486
0.9071	High Similarity	NPC186838
0.9071	High Similarity	NPC240593
0.9071	High Similarity	NPC249606
0.9071	High Similarity	NPC12165
0.9071	High Similarity	NPC168105
0.9071	High Similarity	NPC274109
0.9071	High Similarity	NPC477244
0.9071	High Similarity	NPC66349
0.906	High Similarity	NPC99199
0.9054	High Similarity	NPC253872
0.9048	High Similarity	NPC472421
0.9034	High Similarity	NPC477955
0.9028	High Similarity	NPC257097
0.9028	High Similarity	NPC75049
0.9028	High Similarity	NPC164980
0.9028	High Similarity	NPC219915
0.9028	High Similarity	NPC91560
0.9028	High Similarity	NPC169591
0.9028	High Similarity	NPC190637
0.9028	High Similarity	NPC212932
0.9028	High Similarity	NPC68104
0.9028	High Similarity	NPC9117
0.9028	High Similarity	NPC175504
0.9028	High Similarity	NPC38219
0.9028	High Similarity	NPC221432
0.9028	High Similarity	NPC150408
0.9028	High Similarity	NPC149026
0.9028	High Similarity	NPC293053
0.9028	High Similarity	NPC310130
0.9028	High Similarity	NPC39329
0.9028	High Similarity	NPC143896
0.9028	High Similarity	NPC24821
0.9028	High Similarity	NPC11700
0.9021	High Similarity	NPC282300
0.9021	High Similarity	NPC312391
0.9021	High Similarity	NPC14871
0.9021	High Similarity	NPC213322
0.9021	High Similarity	NPC103362
0.9021	High Similarity	NPC254010
0.9021	High Similarity	NPC4743
0.9021	High Similarity	NPC324386
0.9014	High Similarity	NPC37206
0.9014	High Similarity	NPC477956
0.9014	High Similarity	NPC53181
0.9014	High Similarity	NPC262635
0.9014	High Similarity	NPC217186
0.9014	High Similarity	NPC295384
0.9007	High Similarity	NPC254841
0.9007	High Similarity	NPC153979
0.9007	High Similarity	NPC317119
0.9007	High Similarity	NPC266597
0.9007	High Similarity	NPC250266
0.9007	High Similarity	NPC188879
0.9007	High Similarity	NPC472419
0.9	High Similarity	NPC131039
0.9	High Similarity	NPC156092
0.9	High Similarity	NPC9985
0.9	High Similarity	NPC13575
0.9	High Similarity	NPC239495
0.8993	High Similarity	NPC108113
0.8993	High Similarity	NPC57601
0.8993	High Similarity	NPC93756
0.8986	High Similarity	NPC308037
0.8986	High Similarity	NPC472580
0.8986	High Similarity	NPC258249
0.8986	High Similarity	NPC64359
0.8986	High Similarity	NPC472423
0.8986	High Similarity	NPC318424
0.8986	High Similarity	NPC313618
0.8986	High Similarity	NPC474772
0.8986	High Similarity	NPC474744
0.8973	High Similarity	NPC201731
0.8973	High Similarity	NPC97716
0.8973	High Similarity	NPC237635
0.8973	High Similarity	NPC104406
0.8973	High Similarity	NPC79469
0.8973	High Similarity	NPC24673
0.8966	High Similarity	NPC216538
0.8966	High Similarity	NPC273538
0.8966	High Similarity	NPC473013
0.8966	High Similarity	NPC271288
0.8966	High Similarity	NPC236766

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 NPC225884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	1002
0.2-0.3	1471
0.3-0.4	2750
0.4-0.5	1859
0.5-0.6	1130
0.6-0.7	359
0.7-0.8	106
0.8-0.85	48
0.85-0.9	19
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9014	High Similarity	NPD1243	Approved
0.9007	High Similarity	NPD2344	Approved
0.8986	High Similarity	NPD1240	Approved
0.8966	High Similarity	NPD4378	Clinical (unspecified phase)
0.8966	High Similarity	NPD7410	Clinical (unspecified phase)
0.8857	High Similarity	NPD1607	Approved
0.8816	High Similarity	NPD3749	Approved
0.8811	High Similarity	NPD1549	Phase 2
0.8759	High Similarity	NPD2309	Approved
0.8741	High Similarity	NPD1550	Clinical (unspecified phase)
0.8741	High Similarity	NPD1552	Clinical (unspecified phase)
0.8732	High Similarity	NPD1510	Phase 2
0.8699	High Similarity	NPD643	Clinical (unspecified phase)
0.8671	High Similarity	NPD2796	Approved
0.8621	High Similarity	NPD2800	Approved
0.8609	High Similarity	NPD7411	Suspended
0.8591	High Similarity	NPD920	Approved
0.8581	High Similarity	NPD642	Clinical (unspecified phase)
0.8562	High Similarity	NPD8443	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7075	Discontinued
0.8421	Intermediate Similarity	NPD4380	Phase 2
0.8389	Intermediate Similarity	NPD1511	Approved
0.8387	Intermediate Similarity	NPD3882	Suspended
0.8387	Intermediate Similarity	NPD7768	Phase 2
0.8377	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD7819	Suspended
0.8365	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD1934	Approved
0.8311	Intermediate Similarity	NPD3750	Approved
0.8282	Intermediate Similarity	NPD6559	Discontinued
0.8278	Intermediate Similarity	NPD1512	Approved
0.8267	Intermediate Similarity	NPD6799	Approved
0.8243	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD6959	Discontinued
0.8165	Intermediate Similarity	NPD919	Approved
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.8141	Intermediate Similarity	NPD2801	Approved
0.8101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2799	Discontinued
0.8089	Intermediate Similarity	NPD2296	Approved
0.8075	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD6599	Discontinued
0.8063	Intermediate Similarity	NPD1247	Approved
0.8054	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD2534	Approved
0.7974	Intermediate Similarity	NPD2533	Approved
0.7973	Intermediate Similarity	NPD3748	Approved
0.7959	Intermediate Similarity	NPD6651	Approved
0.7958	Intermediate Similarity	NPD1203	Approved
0.7931	Intermediate Similarity	NPD2313	Discontinued
0.7931	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7914	Intermediate Similarity	NPD6166	Phase 2
0.7914	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD5953	Discontinued
0.7879	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7473	Discontinued
0.7852	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD943	Approved
0.7771	Intermediate Similarity	NPD7286	Phase 2
0.7771	Intermediate Similarity	NPD3226	Approved
0.775	Intermediate Similarity	NPD3817	Phase 2
0.7748	Intermediate Similarity	NPD1471	Phase 3
0.7746	Intermediate Similarity	NPD9717	Approved
0.7733	Intermediate Similarity	NPD4287	Approved
0.7725	Intermediate Similarity	NPD1729	Discontinued
0.7702	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6100	Approved
0.7682	Intermediate Similarity	NPD6099	Approved
0.7677	Intermediate Similarity	NPD7390	Discontinued
0.7676	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD422	Phase 1
0.7665	Intermediate Similarity	NPD5844	Phase 1
0.7655	Intermediate Similarity	NPD2798	Approved
0.7643	Intermediate Similarity	NPD5403	Approved
0.7632	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD5401	Approved
0.7625	Intermediate Similarity	NPD6279	Approved
0.7625	Intermediate Similarity	NPD6280	Approved
0.7619	Intermediate Similarity	NPD7074	Phase 3
0.7605	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD1164	Approved
0.7568	Intermediate Similarity	NPD3764	Approved
0.756	Intermediate Similarity	NPD7054	Approved
0.7552	Intermediate Similarity	NPD1610	Phase 2
0.7551	Intermediate Similarity	NPD4908	Phase 1
0.7551	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2654	Approved
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.7515	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7469	Intermediate Similarity	NPD1465	Phase 2
0.7466	Intermediate Similarity	NPD2797	Approved
0.745	Intermediate Similarity	NPD3268	Approved
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7423	Intermediate Similarity	NPD5402	Approved
0.7416	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4361	Phase 2
0.7394	Intermediate Similarity	NPD9545	Approved
0.7386	Intermediate Similarity	NPD7033	Discontinued
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7379	Intermediate Similarity	NPD3972	Approved
0.7376	Intermediate Similarity	NPD9493	Approved
0.7372	Intermediate Similarity	NPD7003	Approved
0.7365	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD5710	Approved
0.7365	Intermediate Similarity	NPD7229	Phase 3
0.7365	Intermediate Similarity	NPD6808	Phase 2
0.7338	Intermediate Similarity	NPD5405	Approved
0.7338	Intermediate Similarity	NPD5406	Approved
0.7338	Intermediate Similarity	NPD5408	Approved
0.7338	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD411	Approved
0.7317	Intermediate Similarity	NPD4288	Approved
0.731	Intermediate Similarity	NPD1201	Approved
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD447	Suspended
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD17	Approved
0.7286	Intermediate Similarity	NPD1241	Discontinued
0.7283	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3225	Approved
0.7279	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4360	Phase 2
0.7263	Intermediate Similarity	NPD4363	Phase 3
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.7233	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3267	Approved
0.723	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1933	Approved
0.719	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD5761	Phase 2
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7107	Intermediate Similarity	NPD2354	Approved
0.7103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7199	Phase 2
0.7095	Intermediate Similarity	NPD4749	Approved
0.7078	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5124	Phase 1
0.7076	Intermediate Similarity	NPD2403	Approved
0.7067	Intermediate Similarity	NPD1019	Discontinued
0.7066	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1283	Approved
0.7037	Intermediate Similarity	NPD5049	Phase 3
0.7029	Intermediate Similarity	NPD6104	Discontinued
0.7027	Intermediate Similarity	NPD1481	Phase 2
0.7024	Intermediate Similarity	NPD6971	Discontinued
0.7018	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1613	Approved
0.7006	Intermediate Similarity	NPD4477	Approved
0.7006	Intermediate Similarity	NPD4476	Approved
0.6994	Remote Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD3751	Discontinued
0.6993	Remote Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD1651	Approved
0.6975	Remote Similarity	NPD4662	Approved
0.6975	Remote Similarity	NPD4661	Approved
0.6971	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6585	Discontinued
0.6968	Remote Similarity	NPD6355	Discontinued
0.6962	Remote Similarity	NPD6002	Phase 3
0.6962	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2353	Approved
0.6962	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6004	Phase 3
0.6962	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6005	Phase 3

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