NPASS Compound

Structure

NPC198427 OpenBabel07101719242D 21 23 0 0 0 0 0 0 0 0999 V2000 3.3412 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8053 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 11 15 1 0 0 0 0 12 21 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	278.09
Volume:	296.857
LogP:	3.93
LogD:	3.616
LogS:	-5.829
# Rotatable Bonds:	4
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	2.182
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.753
MDCK Permeability:	1.3825680071022362e-05
Pgp-inhibitor:	0.229
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	98.2551040649414%
Volume Distribution (VD):	0.457
Pgp-substrate:	1.3193836212158203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.546
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.674
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	8.723
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.277
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.109
Skin Sensitization:	0.218
Carcinogencity:	0.782
Eye Corrosion:	0.005
Eye Irritation:	0.966
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC198427

Natural Product ID:	NPC198427
*Common Name:**	Ovalitenin A
IUPAC Name:	(E)-1-(4-methoxy-1-benzofuran-5-yl)-3-phenylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	KEJNXXMRDHDOCO-VQHVLOKHSA-N
Standard InCHI:	InChI=1S/C18H14O3/c1-20-18-14(8-10-17-15(18)11-12-21-17)16(19)9-7-13-5-3-2-4-6-13/h2-12H,1H3/b9-7+
SMILES:	COc1c(ccc2c1cco2)C(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401053
PubChem CID:	10923878
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003542] Furanochalcones

*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
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
NPO19856	Millettia pulchra	Species	Fabaceae	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
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	2.01	n.a.	PMID[512925]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	81.0	%	PMID[512925]

☑ 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 NPC198427 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	463
0.1-0.2	1878
0.2-0.3	4816
0.3-0.4	11733
0.4-0.5	6270
0.5-0.6	4656
0.6-0.7	5804
0.7-0.8	4676
0.8-0.85	1780
0.85-0.9	541
0.9-0.95	71
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC472406
0.979	High Similarity	NPC148423
0.979	High Similarity	NPC135303
0.9789	High Similarity	NPC306788
0.9655	High Similarity	NPC263676
0.9655	High Similarity	NPC130015
0.9655	High Similarity	NPC38361
0.9648	High Similarity	NPC190572
0.9589	High Similarity	NPC41719
0.9586	High Similarity	NPC116604
0.9586	High Similarity	NPC472407
0.9524	High Similarity	NPC233776
0.9315	High Similarity	NPC88445
0.9286	High Similarity	NPC29638
0.9257	High Similarity	NPC253872
0.9252	High Similarity	NPC191104
0.9236	High Similarity	NPC17262
0.92	High Similarity	NPC247677
0.92	High Similarity	NPC160015
0.9184	High Similarity	NPC37226
0.9184	High Similarity	NPC226644
0.9178	High Similarity	NPC74539
0.9178	High Similarity	NPC304443
0.9172	High Similarity	NPC246903
0.915	High Similarity	NPC193998
0.9139	High Similarity	NPC296957
0.9139	High Similarity	NPC260902
0.9128	High Similarity	NPC67654
0.9116	High Similarity	NPC266743
0.911	High Similarity	NPC51641
0.911	High Similarity	NPC300267
0.9103	High Similarity	NPC225884
0.9091	High Similarity	NPC65846
0.9085	High Similarity	NPC304387
0.9079	High Similarity	NPC476349
0.9079	High Similarity	NPC476350
0.9067	High Similarity	NPC1477
0.9067	High Similarity	NPC122365
0.9067	High Similarity	NPC213608
0.906	High Similarity	NPC170169
0.906	High Similarity	NPC156244
0.9054	High Similarity	NPC39929
0.9054	High Similarity	NPC296030
0.9048	High Similarity	NPC12148
0.9048	High Similarity	NPC130581
0.9034	High Similarity	NPC166858
0.9034	High Similarity	NPC51146
0.9034	High Similarity	NPC313036
0.9007	High Similarity	NPC198490
0.9	High Similarity	NPC5871
0.8993	High Similarity	NPC230713
0.8993	High Similarity	NPC78335
0.8986	High Similarity	NPC135325
0.898	High Similarity	NPC210826
0.8973	High Similarity	NPC302181
0.8966	High Similarity	NPC22467
0.894	High Similarity	NPC183874
0.8926	High Similarity	NPC178202
0.8919	High Similarity	NPC17816
0.8912	High Similarity	NPC208584
0.8912	High Similarity	NPC230943
0.891	High Similarity	NPC38914
0.8904	High Similarity	NPC53192
0.8903	High Similarity	NPC219861
0.8897	High Similarity	NPC28337
0.8889	High Similarity	NPC65504
0.8889	High Similarity	NPC269495
0.8882	High Similarity	NPC278010
0.8882	High Similarity	NPC250769
0.8882	High Similarity	NPC295608
0.8882	High Similarity	NPC148938
0.8861	High Similarity	NPC41853
0.8859	High Similarity	NPC272194
0.8846	High Similarity	NPC109180
0.8846	High Similarity	NPC472581
0.8839	High Similarity	NPC264293
0.8836	High Similarity	NPC254010
0.8831	High Similarity	NPC40583
0.8831	High Similarity	NPC250076
0.8828	High Similarity	NPC262635
0.8816	High Similarity	NPC131725
0.8816	High Similarity	NPC472462
0.8816	High Similarity	NPC235333
0.8808	High Similarity	NPC115324
0.8805	High Similarity	NPC190351
0.8803	High Similarity	NPC292998
0.8803	High Similarity	NPC247743
0.88	High Similarity	NPC221868
0.88	High Similarity	NPC317492
0.88	High Similarity	NPC37208
0.8797	High Similarity	NPC241820
0.8797	High Similarity	NPC167479
0.8784	High Similarity	NPC155144
0.8784	High Similarity	NPC98926
0.8774	High Similarity	NPC169
0.8774	High Similarity	NPC49009
0.8766	High Similarity	NPC164110
0.8766	High Similarity	NPC246647
0.8766	High Similarity	NPC212967
0.8766	High Similarity	NPC270044
0.8766	High Similarity	NPC96342
0.8758	High Similarity	NPC297531
0.8758	High Similarity	NPC213936
0.875	High Similarity	NPC254741
0.875	High Similarity	NPC207624
0.875	High Similarity	NPC157522
0.8742	High Similarity	NPC167576
0.8742	High Similarity	NPC155882
0.8733	High Similarity	NPC168085
0.8718	High Similarity	NPC14822
0.871	High Similarity	NPC472877
0.8701	High Similarity	NPC180924
0.8699	High Similarity	NPC11566
0.8699	High Similarity	NPC137009
0.8696	High Similarity	NPC62640
0.869	High Similarity	NPC259685
0.8684	High Similarity	NPC106372
0.8684	High Similarity	NPC58668
0.8684	High Similarity	NPC193976
0.8684	High Similarity	NPC23668
0.8667	High Similarity	NPC471285
0.8662	High Similarity	NPC284424
0.8658	High Similarity	NPC179970
0.8658	High Similarity	NPC271590
0.8658	High Similarity	NPC110776
0.8654	High Similarity	NPC239270
0.8654	High Similarity	NPC260296
0.8654	High Similarity	NPC303210
0.8654	High Similarity	NPC115432
0.8654	High Similarity	NPC304839
0.8654	High Similarity	NPC95472
0.8654	High Similarity	NPC220582
0.8645	High Similarity	NPC268360
0.8643	High Similarity	NPC50583
0.8642	High Similarity	NPC66804
0.8639	High Similarity	NPC470856
0.8639	High Similarity	NPC472409
0.8636	High Similarity	NPC473193
0.8627	High Similarity	NPC142308
0.8621	High Similarity	NPC161196
0.8618	High Similarity	NPC472421
0.8611	High Similarity	NPC125269
0.8609	High Similarity	NPC39195
0.8601	High Similarity	NPC182428
0.8601	High Similarity	NPC229646
0.86	High Similarity	NPC215885
0.86	High Similarity	NPC476153
0.86	High Similarity	NPC2416
0.8599	High Similarity	NPC74854
0.8599	High Similarity	NPC30655
0.8599	High Similarity	NPC45124
0.8591	High Similarity	NPC172182
0.8591	High Similarity	NPC251182
0.8591	High Similarity	NPC262935
0.859	High Similarity	NPC244750
0.8581	High Similarity	NPC3188
0.8581	High Similarity	NPC474386
0.8571	High Similarity	NPC136095
0.8571	High Similarity	NPC473194
0.8571	High Similarity	NPC131866
0.8571	High Similarity	NPC72370
0.8562	High Similarity	NPC472423
0.8562	High Similarity	NPC157855
0.8562	High Similarity	NPC474744
0.8562	High Similarity	NPC318424
0.8562	High Similarity	NPC474772
0.8553	High Similarity	NPC214493
0.8553	High Similarity	NPC136641
0.8552	High Similarity	NPC163029
0.8552	High Similarity	NPC99854
0.8543	High Similarity	NPC308200
0.8542	High Similarity	NPC223354
0.8535	High Similarity	NPC243509
0.8533	High Similarity	NPC87486
0.8533	High Similarity	NPC234629
0.8533	High Similarity	NPC184649
0.8533	High Similarity	NPC303185
0.8533	High Similarity	NPC124780
0.8533	High Similarity	NPC311741
0.8531	High Similarity	NPC278556
0.8523	High Similarity	NPC147145
0.8516	High Similarity	NPC99199
0.8514	High Similarity	NPC101366
0.8506	High Similarity	NPC327269
0.8506	High Similarity	NPC31627
0.8506	High Similarity	NPC473996
0.8506	High Similarity	NPC476238
0.8503	High Similarity	NPC471620
0.8503	High Similarity	NPC17848
0.8503	High Similarity	NPC124269
0.85	High Similarity	NPC210460
0.85	High Similarity	NPC155264
0.85	High Similarity	NPC67450
0.85	High Similarity	NPC277480
0.85	High Similarity	NPC193881
0.85	High Similarity	NPC53640
0.8497	Intermediate Similarity	NPC13282
0.8497	Intermediate Similarity	NPC476185
0.8497	Intermediate Similarity	NPC321896
0.8493	Intermediate Similarity	NPC222633

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 NPC198427 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	1005
0.2-0.3	1593
0.3-0.4	2808
0.4-0.5	1863
0.5-0.6	992
0.6-0.7	325
0.7-0.8	104
0.8-0.85	34
0.85-0.9	5
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD920	Approved
0.9172	High Similarity	NPD642	Clinical (unspecified phase)
0.9034	High Similarity	NPD643	Clinical (unspecified phase)
0.8839	High Similarity	NPD1247	Approved
0.8828	High Similarity	NPD1243	Approved
0.875	High Similarity	NPD2796	Approved
0.8471	Intermediate Similarity	NPD919	Approved
0.8442	Intermediate Similarity	NPD7411	Suspended
0.8411	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD2344	Approved
0.8302	Intermediate Similarity	NPD5494	Approved
0.828	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1240	Approved
0.8255	Intermediate Similarity	NPD1549	Phase 2
0.8188	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3749	Approved
0.8176	Intermediate Similarity	NPD1510	Phase 2
0.817	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1607	Approved
0.8148	Intermediate Similarity	NPD3926	Phase 2
0.8133	Intermediate Similarity	NPD6559	Discontinued
0.8105	Intermediate Similarity	NPD6799	Approved
0.8101	Intermediate Similarity	NPD7819	Suspended
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2309	Approved
0.8079	Intermediate Similarity	NPD2800	Approved
0.8079	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3882	Suspended
0.795	Intermediate Similarity	NPD7075	Discontinued
0.7947	Intermediate Similarity	NPD1471	Phase 3
0.7925	Intermediate Similarity	NPD1934	Approved
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7911	Intermediate Similarity	NPD6599	Discontinued
0.7888	Intermediate Similarity	NPD7768	Phase 2
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7815	Intermediate Similarity	NPD3748	Approved
0.7812	Intermediate Similarity	NPD6279	Approved
0.7812	Intermediate Similarity	NPD6280	Approved
0.7805	Intermediate Similarity	NPD6959	Discontinued
0.7764	Intermediate Similarity	NPD2801	Approved
0.7762	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6808	Phase 2
0.7756	Intermediate Similarity	NPD1511	Approved
0.773	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3817	Phase 2
0.7707	Intermediate Similarity	NPD2533	Approved
0.7707	Intermediate Similarity	NPD2534	Approved
0.7707	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD2799	Discontinued
0.7679	Intermediate Similarity	NPD3818	Discontinued
0.7658	Intermediate Similarity	NPD1512	Approved
0.7651	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7635	Intermediate Similarity	NPD6832	Phase 2
0.7625	Intermediate Similarity	NPD3226	Approved
0.7564	Intermediate Similarity	NPD3750	Approved
0.756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6166	Phase 2
0.756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6232	Discontinued
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD2296	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5401	Approved
0.7457	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2403	Approved
0.7455	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD5402	Approved
0.7391	Intermediate Similarity	NPD5403	Approved
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7347	Intermediate Similarity	NPD3972	Approved
0.7338	Intermediate Similarity	NPD6651	Approved
0.7337	Intermediate Similarity	NPD7229	Phase 3
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7283	Intermediate Similarity	NPD1729	Discontinued
0.7283	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7262	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1876	Approved
0.7244	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7225	Intermediate Similarity	NPD7054	Approved
0.7212	Intermediate Similarity	NPD5890	Approved
0.7212	Intermediate Similarity	NPD5889	Approved
0.7208	Intermediate Similarity	NPD943	Approved
0.7207	Intermediate Similarity	NPD4287	Approved
0.72	Intermediate Similarity	NPD1203	Approved
0.719	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7472	Approved
0.7161	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7114	Intermediate Similarity	NPD9717	Approved
0.7102	Intermediate Similarity	NPD7251	Discontinued
0.7099	Intermediate Similarity	NPD7390	Discontinued
0.7097	Intermediate Similarity	NPD4307	Phase 2
0.7078	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7062	Intermediate Similarity	NPD7808	Phase 3
0.7062	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4908	Phase 1
0.7048	Intermediate Similarity	NPD6585	Discontinued
0.7047	Intermediate Similarity	NPD1610	Phase 2
0.7045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD1465	Phase 2
0.7011	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4361	Phase 2
0.7007	Intermediate Similarity	NPD1548	Phase 1
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1608	Approved
0.6987	Remote Similarity	NPD3140	Approved
0.6987	Remote Similarity	NPD3142	Approved
0.6981	Remote Similarity	NPD6099	Approved
0.6981	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD3764	Approved
0.6959	Remote Similarity	NPD1651	Approved
0.6957	Remote Similarity	NPD4360	Phase 2
0.6957	Remote Similarity	NPD4363	Phase 3
0.6954	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD447	Suspended
0.6943	Remote Similarity	NPD230	Phase 1
0.6941	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD422	Phase 1
0.6918	Remote Similarity	NPD4308	Phase 3
0.6914	Remote Similarity	NPD7003	Approved
0.6897	Remote Similarity	NPD5242	Approved
0.6894	Remote Similarity	NPD2424	Discontinued
0.6892	Remote Similarity	NPD9545	Approved
0.6886	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4288	Approved
0.6879	Remote Similarity	NPD7199	Phase 2
0.6875	Remote Similarity	NPD3751	Discontinued
0.6871	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3887	Approved
0.6867	Remote Similarity	NPD3869	Phase 3
0.6867	Remote Similarity	NPD3873	Phase 3
0.6863	Remote Similarity	NPD2797	Approved
0.6863	Remote Similarity	NPD1164	Approved
0.6857	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4661	Approved
0.6848	Remote Similarity	NPD4662	Approved
0.6839	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2353	Approved
0.6821	Remote Similarity	NPD1281	Approved
0.6816	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6104	Discontinued
0.681	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3225	Approved
0.6795	Remote Similarity	NPD4625	Phase 3
0.6788	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD2163	Approved
0.6774	Remote Similarity	NPD9494	Approved
0.6772	Remote Similarity	NPD2979	Phase 3
0.677	Remote Similarity	NPD4476	Approved
0.677	Remote Similarity	NPD4477	Approved
0.6765	Remote Similarity	NPD6844	Discontinued
0.6757	Remote Similarity	NPD9493	Approved
0.6757	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD411	Approved
0.6752	Remote Similarity	NPD6798	Discontinued
0.6744	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3787	Discontinued
0.674	Remote Similarity	NPD8313	Approved
0.674	Remote Similarity	NPD8312	Approved
0.6739	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.673	Remote Similarity	NPD6355	Discontinued
0.673	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5124	Phase 1

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