NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	2.847
LogD:	3.033
LogS:	-4.321
# Rotatable Bonds:	5
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	2.149
Fsp3:	0.211
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:	-4.605
MDCK Permeability:	6.130792462499812e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	74.93987274169922%
Volume Distribution (VD):	0.883
Pgp-substrate:	17.70585823059082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.603
CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.584
CYP3A4-substrate:	0.627

ADMET: Excretion

Clearance (CL):	10.082
Half-life (T1/2):	0.478

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.301
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.522
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.201
Carcinogencity:	0.125
Eye Corrosion:	0.005
Eye Irritation:	0.06
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC286843

Natural Product ID:	NPC286843
*Common Name:**	4-(4-Methoxyphenyl)-5,7,8-trimethoxy-2H-1-benzopyran-2-one
IUPAC Name:	5,7,8-trimethoxy-4-(4-methoxyphenyl)chromen-2-one
Synonyms:	O-Methylexostemin
Standard InCHIKey:	ATUWQWOHLKRHRS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-21-12-7-5-11(6-8-12)13-9-16(20)25-19-17(13)14(22-2)10-15(23-3)18(19)24-4/h5-10H,1-4H3
SMILES:	COC1=CC=C(C=C1)C2=CC(=O)OC3=C2C(=CC(=C3OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	13989375
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0001389] Neoflavones

*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
NPO2528	Exostema mexicanum	Species	Rubiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[19299148]
NPO2528	Exostema mexicanum	Species	Rubiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.6	ug/ml	PMID[19299148]

☑ 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 NPC286843 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	495
0.1-0.2	2043
0.2-0.3	5102
0.3-0.4	11316
0.4-0.5	6190
0.5-0.6	4155
0.6-0.7	5780
0.7-0.8	5031
0.8-0.85	1884
0.85-0.9	600
0.9-0.95	98
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC234865
0.9692	High Similarity	NPC474600
0.9538	High Similarity	NPC319969
0.9466	High Similarity	NPC233018
0.9466	High Similarity	NPC36437
0.9466	High Similarity	NPC241341
0.9412	High Similarity	NPC7439
0.9412	High Similarity	NPC34245
0.9412	High Similarity	NPC91492
0.9412	High Similarity	NPC110067
0.9412	High Similarity	NPC256555
0.9403	High Similarity	NPC270256
0.9389	High Similarity	NPC137669
0.9385	High Similarity	NPC240722
0.9385	High Similarity	NPC244799
0.9323	High Similarity	NPC224941
0.9323	High Similarity	NPC311430
0.9318	High Similarity	NPC472522
0.9308	High Similarity	NPC27239
0.9308	High Similarity	NPC123127
0.9254	High Similarity	NPC167517
0.9248	High Similarity	NPC309953
0.9237	High Similarity	NPC19242
0.9237	High Similarity	NPC476399
0.9231	High Similarity	NPC474623
0.9231	High Similarity	NPC474651
0.9185	High Similarity	NPC474530
0.9185	High Similarity	NPC474521
0.9185	High Similarity	NPC474540
0.9154	High Similarity	NPC194841
0.9154	High Similarity	NPC474670
0.9143	High Similarity	NPC15577
0.9118	High Similarity	NPC43500
0.9118	High Similarity	NPC164148
0.9104	High Similarity	NPC147030
0.9084	High Similarity	NPC210674
0.9084	High Similarity	NPC474616
0.9044	High Similarity	NPC38874
0.9044	High Similarity	NPC474886
0.9037	High Similarity	NPC73071
0.9014	High Similarity	NPC176903
0.9014	High Similarity	NPC30688
0.9008	High Similarity	NPC474821
0.8992	High Similarity	NPC315807
0.8986	High Similarity	NPC300611
0.8955	High Similarity	NPC123954
0.8951	High Similarity	NPC205727
0.8951	High Similarity	NPC294522
0.8951	High Similarity	NPC21184
0.8951	High Similarity	NPC120426
0.8947	High Similarity	NPC307042
0.8947	High Similarity	NPC474617
0.8947	High Similarity	NPC79184
0.8944	High Similarity	NPC139839
0.8939	High Similarity	NPC31707
0.8939	High Similarity	NPC474636
0.8936	High Similarity	NPC205361
0.8931	High Similarity	NPC474632
0.8905	High Similarity	NPC52086
0.8905	High Similarity	NPC20511
0.8905	High Similarity	NPC20796
0.8905	High Similarity	NPC95162
0.8905	High Similarity	NPC76336
0.8905	High Similarity	NPC148835
0.8905	High Similarity	NPC139548
0.8897	High Similarity	NPC472521
0.8897	High Similarity	NPC240915
0.8873	High Similarity	NPC476347
0.8873	High Similarity	NPC231149
0.8865	High Similarity	NPC125617
0.8857	High Similarity	NPC138212
0.8841	High Similarity	NPC13067
0.8836	High Similarity	NPC186507
0.8832	High Similarity	NPC126682
0.8832	High Similarity	NPC82271
0.8828	High Similarity	NPC264875
0.8828	High Similarity	NPC163598
0.8828	High Similarity	NPC120774
0.8824	High Similarity	NPC474478
0.8824	High Similarity	NPC7163
0.8815	High Similarity	NPC245120
0.8815	High Similarity	NPC5423
0.8811	High Similarity	NPC476348
0.8811	High Similarity	NPC187398
0.8803	High Similarity	NPC287275
0.8788	High Similarity	NPC244364
0.8788	High Similarity	NPC127604
0.8769	High Similarity	NPC194626
0.8768	High Similarity	NPC476171
0.876	High Similarity	NPC472596
0.8759	High Similarity	NPC195022
0.875	High Similarity	NPC277021
0.875	High Similarity	NPC296624
0.875	High Similarity	NPC318400
0.875	High Similarity	NPC207002
0.875	High Similarity	NPC133956
0.875	High Similarity	NPC167111
0.875	High Similarity	NPC471910
0.8741	High Similarity	NPC178129
0.8741	High Similarity	NPC170239
0.8741	High Similarity	NPC97937
0.8741	High Similarity	NPC275125
0.8732	High Similarity	NPC23955
0.8731	High Similarity	NPC474227
0.8723	High Similarity	NPC236419
0.8714	High Similarity	NPC279851
0.8714	High Similarity	NPC472520
0.8702	High Similarity	NPC279379
0.8696	High Similarity	NPC173660
0.8686	High Similarity	NPC195343
0.8686	High Similarity	NPC319859
0.8686	High Similarity	NPC267412
0.8686	High Similarity	NPC74655
0.8686	High Similarity	NPC18804
0.8686	High Similarity	NPC47163
0.8686	High Similarity	NPC84894
0.8686	High Similarity	NPC309744
0.8686	High Similarity	NPC260265
0.8686	High Similarity	NPC100986
0.8686	High Similarity	NPC106215
0.8686	High Similarity	NPC198381
0.8686	High Similarity	NPC166672
0.8686	High Similarity	NPC164269
0.8686	High Similarity	NPC127888
0.8686	High Similarity	NPC111635
0.8686	High Similarity	NPC92830
0.8686	High Similarity	NPC287182
0.8681	High Similarity	NPC93924
0.8681	High Similarity	NPC48366
0.8681	High Similarity	NPC96294
0.8676	High Similarity	NPC19157
0.8671	High Similarity	NPC475872
0.8662	High Similarity	NPC185127
0.8649	High Similarity	NPC122623
0.8649	High Similarity	NPC241774
0.8649	High Similarity	NPC34725
0.8649	High Similarity	NPC276059
0.8647	High Similarity	NPC101894
0.8639	High Similarity	NPC150442
0.8636	High Similarity	NPC201667
0.8636	High Similarity	NPC73413
0.8633	High Similarity	NPC102904
0.8633	High Similarity	NPC326797
0.8633	High Similarity	NPC276490
0.8633	High Similarity	NPC474282
0.8633	High Similarity	NPC107551
0.8633	High Similarity	NPC103976
0.8633	High Similarity	NPC176051
0.8626	High Similarity	NPC261661
0.8626	High Similarity	NPC288238
0.8623	High Similarity	NPC472424
0.8623	High Similarity	NPC281241
0.8623	High Similarity	NPC471625
0.8623	High Similarity	NPC86892
0.8623	High Similarity	NPC471909
0.8621	High Similarity	NPC113790
0.8613	High Similarity	NPC229442
0.8613	High Similarity	NPC263064
0.8613	High Similarity	NPC26673
0.8613	High Similarity	NPC168059
0.8613	High Similarity	NPC474810
0.8611	High Similarity	NPC14958
0.8611	High Similarity	NPC137352
0.8611	High Similarity	NPC215932
0.8611	High Similarity	NPC106461
0.8611	High Similarity	NPC183083
0.8611	High Similarity	NPC40818
0.8611	High Similarity	NPC110639
0.8605	High Similarity	NPC254625
0.8605	High Similarity	NPC308217
0.8605	High Similarity	NPC475961
0.8603	High Similarity	NPC474238
0.8592	High Similarity	NPC124467
0.8592	High Similarity	NPC230157
0.8592	High Similarity	NPC6568
0.8592	High Similarity	NPC214919
0.8591	High Similarity	NPC257277
0.8582	High Similarity	NPC189248
0.8582	High Similarity	NPC202904
0.8581	High Similarity	NPC8712
0.8571	High Similarity	NPC169404
0.8571	High Similarity	NPC471827
0.8571	High Similarity	NPC127218
0.8571	High Similarity	NPC25966
0.8571	High Similarity	NPC215060
0.8571	High Similarity	NPC474170
0.8571	High Similarity	NPC53587
0.8571	High Similarity	NPC198615
0.8571	High Similarity	NPC474663
0.8571	High Similarity	NPC472535
0.8571	High Similarity	NPC474388
0.8571	High Similarity	NPC176186
0.8571	High Similarity	NPC476352
0.8571	High Similarity	NPC245207
0.8571	High Similarity	NPC319647
0.8571	High Similarity	NPC471828
0.8571	High Similarity	NPC471388
0.8562	High Similarity	NPC114740
0.8561	High Similarity	NPC472518
0.8561	High Similarity	NPC149320

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 NPC286843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	1004
0.2-0.3	1877
0.3-0.4	2682
0.4-0.5	1759
0.5-0.6	896
0.6-0.7	358
0.7-0.8	96
0.8-0.85	41
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD1653	Approved
0.8356	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD3817	Phase 2
0.8248	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2801	Approved
0.8175	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD1613	Approved
0.8143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD422	Phase 1
0.8058	Intermediate Similarity	NPD3027	Phase 3
0.805	Intermediate Similarity	NPD5844	Phase 1
0.8043	Intermediate Similarity	NPD3018	Phase 2
0.7963	Intermediate Similarity	NPD7549	Discontinued
0.7949	Intermediate Similarity	NPD5494	Approved
0.7945	Intermediate Similarity	NPD1652	Phase 2
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7933	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD5535	Approved
0.7917	Intermediate Similarity	NPD3748	Approved
0.7908	Intermediate Similarity	NPD1934	Approved
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7872	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5283	Phase 1
0.7857	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD5124	Phase 1
0.7832	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD3496	Discontinued
0.7771	Intermediate Similarity	NPD919	Approved
0.7761	Intermediate Similarity	NPD5536	Phase 2
0.7746	Intermediate Similarity	NPD1296	Phase 2
0.7742	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD2796	Approved
0.7737	Intermediate Similarity	NPD1611	Approved
0.7733	Intermediate Similarity	NPD1511	Approved
0.773	Intermediate Similarity	NPD4908	Phase 1
0.7704	Intermediate Similarity	NPD1548	Phase 1
0.7692	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7651	Intermediate Similarity	NPD3750	Approved
0.7643	Intermediate Similarity	NPD3266	Approved
0.7643	Intermediate Similarity	NPD3267	Approved
0.7643	Intermediate Similarity	NPD2797	Approved
0.7636	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1512	Approved
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7625	Intermediate Similarity	NPD6232	Discontinued
0.7622	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6799	Approved
0.7616	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD5677	Discontinued
0.7609	Intermediate Similarity	NPD1610	Phase 2
0.7586	Intermediate Similarity	NPD1933	Approved
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3225	Approved
0.7566	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD37	Approved
0.7562	Intermediate Similarity	NPD1247	Approved
0.7546	Intermediate Similarity	NPD3818	Discontinued
0.7535	Intermediate Similarity	NPD2861	Phase 2
0.7532	Intermediate Similarity	NPD4965	Approved
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7532	Intermediate Similarity	NPD4967	Phase 2
0.7532	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6166	Phase 2
0.7518	Intermediate Similarity	NPD5691	Approved
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3705	Approved
0.7466	Intermediate Similarity	NPD4340	Discontinued
0.7466	Intermediate Similarity	NPD447	Suspended
0.7455	Intermediate Similarity	NPD7472	Approved
0.7455	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD6801	Discontinued
0.745	Intermediate Similarity	NPD3540	Phase 1
0.7448	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD6234	Discontinued
0.7436	Intermediate Similarity	NPD6599	Discontinued
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.7431	Intermediate Similarity	NPD7095	Approved
0.7417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1358	Approved
0.7397	Intermediate Similarity	NPD4307	Phase 2
0.7385	Intermediate Similarity	NPD9697	Approved
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7376	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4749	Approved
0.7375	Intermediate Similarity	NPD7075	Discontinued
0.7372	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3926	Phase 2
0.7362	Intermediate Similarity	NPD5242	Approved
0.7361	Intermediate Similarity	NPD6832	Phase 2
0.7355	Intermediate Similarity	NPD920	Approved
0.7355	Intermediate Similarity	NPD5403	Approved
0.7351	Intermediate Similarity	NPD1243	Approved
0.7347	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5401	Approved
0.7338	Intermediate Similarity	NPD17	Approved
0.7338	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD7266	Discontinued
0.7321	Intermediate Similarity	NPD7808	Phase 3
0.7314	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6797	Phase 2
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7411	Suspended
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5585	Approved
0.7262	Intermediate Similarity	NPD7251	Discontinued
0.7261	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7237	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6671	Approved
0.7219	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4380	Phase 2
0.7208	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7124	Phase 2
0.7205	Intermediate Similarity	NPD7768	Phase 2
0.72	Intermediate Similarity	NPD1510	Phase 2
0.72	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7033	Discontinued
0.72	Intermediate Similarity	NPD4308	Phase 3
0.72	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3134	Approved
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4110	Phase 3
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7183	Intermediate Similarity	NPD1608	Approved
0.7181	Intermediate Similarity	NPD2653	Approved
0.7172	Intermediate Similarity	NPD2237	Approved
0.7171	Intermediate Similarity	NPD1549	Phase 2
0.717	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6386	Approved
0.717	Intermediate Similarity	NPD6385	Approved
0.7161	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7152	Intermediate Similarity	NPD6032	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7228	Approved
0.7124	Intermediate Similarity	NPD6674	Discontinued
0.7124	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD230	Phase 1
0.7107	Intermediate Similarity	NPD4675	Approved
0.7107	Intermediate Similarity	NPD4678	Approved
0.7105	Intermediate Similarity	NPD5762	Approved
0.7105	Intermediate Similarity	NPD5763	Approved
0.7092	Intermediate Similarity	NPD1778	Approved
0.7091	Intermediate Similarity	NPD7229	Phase 3
0.709	Intermediate Similarity	NPD2684	Approved
0.7089	Intermediate Similarity	NPD3687	Approved
0.7089	Intermediate Similarity	NPD3686	Approved
0.7083	Intermediate Similarity	NPD8651	Approved
0.707	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5090	Approved
0.7063	Intermediate Similarity	NPD5089	Approved
0.7059	Intermediate Similarity	NPD6559	Discontinued
0.7059	Intermediate Similarity	NPD228	Approved
0.7055	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6971	Discontinued
0.7051	Intermediate Similarity	NPD5297	Approved
0.7047	Intermediate Similarity	NPD1240	Approved
0.7047	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD4005	Discontinued
0.7039	Intermediate Similarity	NPD6099	Approved
0.7039	Intermediate Similarity	NPD6100	Approved
0.7037	Intermediate Similarity	NPD4288	Approved
0.7037	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2313	Discontinued
0.702	Intermediate Similarity	NPD6111	Discontinued
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7014	Intermediate Similarity	NPD4359	Approved
0.7007	Intermediate Similarity	NPD7843	Approved
0.7006	Intermediate Similarity	NPD4481	Phase 3
0.7006	Intermediate Similarity	NPD3146	Approved
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7447	Phase 1
0.7	Intermediate Similarity	NPD7644	Approved
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD1375	Discontinued
0.6993	Remote Similarity	NPD1091	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