NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.09
Volume:	160.121
LogP:	-3.739
LogD:	-1.638
LogS:	-1.171
# Rotatable Bonds:	6
TPSA:	134.45
# H-Bond Aceptor:	7
# H-Bond Donor:	7
# Rings:	0
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.145
Synthetic Accessibility Score:	3.546
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.434
MDCK Permeability:	0.0036078013945370913
Pgp-inhibitor:	0.0
Pgp-substrate:	0.874
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	13.233007431030273%
Volume Distribution (VD):	0.66
Pgp-substrate:	84.52605438232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	4.102
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.24
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.035
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC60667

Natural Product ID:	NPC60667
*Common Name:**	6-Methoxymethyleugenin
IUPAC Name:	5-hydroxy-7-methoxy-6-(methoxymethyl)-2-methylchromen-4-one
Synonyms:	6-Methoxymethyleugenin
Standard InCHIKey:	QVJKPZADVVATSS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O5/c1-7-4-9(14)12-11(18-7)5-10(17-3)8(6-16-2)13(12)15/h4-5,15H,6H2,1-3H3
SMILES:	Cc1cc(=O)c2c(cc(c(COC)c2O)OC)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463447
PubChem CID:	637447
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO28469	Tolypocladium extinguens	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444701]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18406151]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28469	Tolypocladium extinguens	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27585	Ocellularia praestans	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28190	Virola guggenheimii	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27730	Silene viscidula	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16583	Asarum takaoi	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27378	Scirpus kysoor	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6033	Anthriscus neglecta	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7017	Monas vulgaris	Species	Chromulinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27531	Aethusa cynapium	Species	Apiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ID50	=	6.0	ug ml-1	PMID[506285]

☑ 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 NPC60667 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	355
0.1-0.2	1635
0.2-0.3	4408
0.3-0.4	11330
0.4-0.5	6904
0.5-0.6	4238
0.6-0.7	5720
0.7-0.8	4294
0.8-0.85	1988
0.85-0.9	1212
0.9-0.95	588
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC125920
0.9845	High Similarity	NPC93756
0.9845	High Similarity	NPC108113
0.9771	High Similarity	NPC174999
0.9699	High Similarity	NPC471697
0.9699	High Similarity	NPC23257
0.9699	High Similarity	NPC139554
0.9692	High Similarity	NPC223457
0.969	High Similarity	NPC31872
0.969	High Similarity	NPC475589
0.969	High Similarity	NPC473584
0.9627	High Similarity	NPC471587
0.9624	High Similarity	NPC131130
0.9621	High Similarity	NPC156910
0.9615	High Similarity	NPC25937
0.9612	High Similarity	NPC270369
0.9612	High Similarity	NPC5515
0.9552	High Similarity	NPC473076
0.9552	High Similarity	NPC18260
0.9552	High Similarity	NPC78913
0.9545	High Similarity	NPC151113
0.9481	High Similarity	NPC241100
0.9481	High Similarity	NPC159275
0.9478	High Similarity	NPC470668
0.9478	High Similarity	NPC201395
0.9478	High Similarity	NPC470669
0.947	High Similarity	NPC236974
0.947	High Similarity	NPC144027
0.9466	High Similarity	NPC203817
0.9466	High Similarity	NPC10971
0.9457	High Similarity	NPC230818
0.9416	High Similarity	NPC255133
0.9416	High Similarity	NPC242100
0.9412	High Similarity	NPC324386
0.9412	High Similarity	NPC96408
0.9412	High Similarity	NPC279650
0.9412	High Similarity	NPC3188
0.9412	High Similarity	NPC166689
0.9412	High Similarity	NPC258630
0.9412	High Similarity	NPC312391
0.9412	High Similarity	NPC213322
0.9412	High Similarity	NPC110969
0.9412	High Similarity	NPC17170
0.9412	High Similarity	NPC282300
0.9412	High Similarity	NPC156190
0.9412	High Similarity	NPC4743
0.9407	High Similarity	NPC220062
0.9407	High Similarity	NPC53181
0.9407	High Similarity	NPC55018
0.9407	High Similarity	NPC216978
0.9407	High Similarity	NPC301217
0.9407	High Similarity	NPC303633
0.9407	High Similarity	NPC217186
0.9407	High Similarity	NPC37206
0.9407	High Similarity	NPC96565
0.9398	High Similarity	NPC101752
0.9385	High Similarity	NPC84772
0.9348	High Similarity	NPC319752
0.9348	High Similarity	NPC224714
0.9348	High Similarity	NPC297788
0.9343	High Similarity	NPC76372
0.9343	High Similarity	NPC161506
0.9343	High Similarity	NPC32739
0.9343	High Similarity	NPC324436
0.9343	High Similarity	NPC177354
0.9343	High Similarity	NPC66515
0.9343	High Similarity	NPC148757
0.9343	High Similarity	NPC64915
0.9343	High Similarity	NPC167624
0.9343	High Similarity	NPC194432
0.9343	High Similarity	NPC306829
0.9343	High Similarity	NPC226636
0.9343	High Similarity	NPC328164
0.9343	High Similarity	NPC125855
0.9343	High Similarity	NPC324134
0.9343	High Similarity	NPC166934
0.9343	High Similarity	NPC228504
0.9343	High Similarity	NPC325346
0.9343	High Similarity	NPC220998
0.9343	High Similarity	NPC182852
0.9343	High Similarity	NPC37496
0.9343	High Similarity	NPC296917
0.9343	High Similarity	NPC10937
0.9343	High Similarity	NPC40833
0.9343	High Similarity	NPC162476
0.9343	High Similarity	NPC76338
0.9343	High Similarity	NPC107572
0.9343	High Similarity	NPC227579
0.9343	High Similarity	NPC223500
0.9343	High Similarity	NPC11561
0.9343	High Similarity	NPC265040
0.9343	High Similarity	NPC1089
0.9343	High Similarity	NPC78
0.9343	High Similarity	NPC166482
0.9338	High Similarity	NPC307990
0.9338	High Similarity	NPC150522
0.9338	High Similarity	NPC16455
0.9338	High Similarity	NPC270883
0.9338	High Similarity	NPC172986
0.9338	High Similarity	NPC261227
0.9333	High Similarity	NPC470671
0.9333	High Similarity	NPC470672
0.9333	High Similarity	NPC474504
0.9333	High Similarity	NPC124269
0.9333	High Similarity	NPC474487
0.9328	High Similarity	NPC127447
0.9328	High Similarity	NPC234133
0.9328	High Similarity	NPC29353
0.9328	High Similarity	NPC124784
0.9328	High Similarity	NPC47815
0.9328	High Similarity	NPC473887
0.9328	High Similarity	NPC194281
0.9328	High Similarity	NPC470398
0.9328	High Similarity	NPC187826
0.9328	High Similarity	NPC470397
0.9328	High Similarity	NPC231772
0.9323	High Similarity	NPC164136
0.9313	High Similarity	NPC250057
0.9313	High Similarity	NPC324482
0.9308	High Similarity	NPC69235
0.9308	High Similarity	NPC212379
0.9302	High Similarity	NPC128428
0.9302	High Similarity	NPC49852
0.9302	High Similarity	NPC475496
0.9302	High Similarity	NPC305518
0.9281	High Similarity	NPC470458
0.9281	High Similarity	NPC195621
0.9281	High Similarity	NPC476088
0.9281	High Similarity	NPC142405
0.9281	High Similarity	NPC246948
0.9281	High Similarity	NPC267375
0.9281	High Similarity	NPC214774
0.9281	High Similarity	NPC20488
0.9281	High Similarity	NPC176229
0.9281	High Similarity	NPC312973
0.9281	High Similarity	NPC54577
0.9281	High Similarity	NPC111786
0.9281	High Similarity	NPC83357
0.9281	High Similarity	NPC470647
0.9281	High Similarity	NPC67805
0.9281	High Similarity	NPC475052
0.9281	High Similarity	NPC474161
0.9281	High Similarity	NPC88964
0.9281	High Similarity	NPC301276
0.9275	High Similarity	NPC125894
0.9275	High Similarity	NPC316816
0.9275	High Similarity	NPC150408
0.9275	High Similarity	NPC175504
0.9275	High Similarity	NPC107177
0.9275	High Similarity	NPC158874
0.9275	High Similarity	NPC68104
0.9275	High Similarity	NPC91560
0.9275	High Similarity	NPC478086
0.9275	High Similarity	NPC81697
0.9275	High Similarity	NPC221432
0.9275	High Similarity	NPC185276
0.9275	High Similarity	NPC214166
0.9275	High Similarity	NPC85162
0.9275	High Similarity	NPC223812
0.9275	High Similarity	NPC164980
0.9275	High Similarity	NPC169591
0.9275	High Similarity	NPC75049
0.9275	High Similarity	NPC77794
0.9275	High Similarity	NPC39329
0.9275	High Similarity	NPC278249
0.9275	High Similarity	NPC143896
0.9275	High Similarity	NPC149026
0.9275	High Similarity	NPC310130
0.9275	High Similarity	NPC257097
0.927	High Similarity	NPC205006
0.927	High Similarity	NPC147688
0.927	High Similarity	NPC156590
0.927	High Similarity	NPC64908
0.927	High Similarity	NPC103362
0.927	High Similarity	NPC118840
0.927	High Similarity	NPC171870
0.927	High Similarity	NPC248372
0.927	High Similarity	NPC110038
0.9265	High Similarity	NPC329203
0.9265	High Similarity	NPC265871
0.9265	High Similarity	NPC150648
0.9265	High Similarity	NPC274784
0.9265	High Similarity	NPC295384
0.9265	High Similarity	NPC225153
0.9265	High Similarity	NPC222342
0.9265	High Similarity	NPC137009
0.9265	High Similarity	NPC20709
0.9265	High Similarity	NPC140890
0.9265	High Similarity	NPC310135
0.9259	High Similarity	NPC188879
0.9259	High Similarity	NPC12296
0.9259	High Similarity	NPC296490
0.9259	High Similarity	NPC295261
0.9259	High Similarity	NPC13768
0.9259	High Similarity	NPC32441
0.9259	High Similarity	NPC250266
0.9259	High Similarity	NPC243083
0.9259	High Similarity	NPC107586
0.9259	High Similarity	NPC79943
0.9259	High Similarity	NPC287246

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 NPC60667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	967
0.2-0.3	1656
0.3-0.4	2717
0.4-0.5	1785
0.5-0.6	1154
0.6-0.7	382
0.7-0.8	110
0.8-0.85	40
0.85-0.9	18
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9259	High Similarity	NPD1552	Clinical (unspecified phase)
0.9259	High Similarity	NPD1550	Clinical (unspecified phase)
0.9209	High Similarity	NPD4378	Clinical (unspecified phase)
0.9191	High Similarity	NPD1549	Phase 2
0.9111	High Similarity	NPD1510	Phase 2
0.9098	High Similarity	NPD1240	Approved
0.8963	High Similarity	NPD1607	Approved
0.8936	High Similarity	NPD7410	Clinical (unspecified phase)
0.8777	High Similarity	NPD970	Clinical (unspecified phase)
0.8768	High Similarity	NPD2796	Approved
0.8714	High Similarity	NPD2800	Approved
0.8707	High Similarity	NPD2393	Clinical (unspecified phase)
0.8699	High Similarity	NPD7411	Suspended
0.8649	High Similarity	NPD8443	Clinical (unspecified phase)
0.863	High Similarity	NPD4380	Phase 2
0.8601	High Similarity	NPD1511	Approved
0.8582	High Similarity	NPD1243	Approved
0.8551	High Similarity	NPD6651	Approved
0.8533	High Similarity	NPD7075	Discontinued
0.8514	High Similarity	NPD6801	Discontinued
0.8514	High Similarity	NPD1934	Approved
0.8483	Intermediate Similarity	NPD1512	Approved
0.8472	Intermediate Similarity	NPD6799	Approved
0.8456	Intermediate Similarity	NPD7819	Suspended
0.8456	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD920	Approved
0.8403	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1551	Phase 2
0.8333	Intermediate Similarity	NPD2801	Approved
0.8322	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2533	Approved
0.8288	Intermediate Similarity	NPD2534	Approved
0.8288	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2532	Approved
0.8264	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD3750	Approved
0.8261	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6599	Discontinued
0.8247	Intermediate Similarity	NPD6959	Discontinued
0.8224	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD3882	Suspended
0.8205	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD422	Phase 1
0.8074	Intermediate Similarity	NPD9717	Approved
0.8039	Intermediate Similarity	NPD3817	Phase 2
0.8029	Intermediate Similarity	NPD1203	Approved
0.8	Intermediate Similarity	NPD919	Approved
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD1548	Phase 1
0.7963	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5953	Discontinued
0.7937	Intermediate Similarity	NPD7286	Phase 2
0.7935	Intermediate Similarity	NPD3749	Approved
0.7933	Intermediate Similarity	NPD5403	Approved
0.7931	Intermediate Similarity	NPD2344	Approved
0.7919	Intermediate Similarity	NPD5401	Approved
0.7917	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3748	Approved
0.7917	Intermediate Similarity	NPD2799	Discontinued
0.7898	Intermediate Similarity	NPD1247	Approved
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7872	Intermediate Similarity	NPD2313	Discontinued
0.7868	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD9545	Approved
0.7834	Intermediate Similarity	NPD5494	Approved
0.7826	Intermediate Similarity	NPD7054	Approved
0.7823	Intermediate Similarity	NPD2654	Approved
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD7472	Approved
0.7762	Intermediate Similarity	NPD943	Approved
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1296	Phase 2
0.7746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD6100	Approved
0.7737	Intermediate Similarity	NPD1610	Phase 2
0.7736	Intermediate Similarity	NPD6232	Discontinued
0.773	Intermediate Similarity	NPD6832	Phase 2
0.773	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD1241	Discontinued
0.7718	Intermediate Similarity	NPD2309	Approved
0.7708	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5124	Phase 1
0.7708	Intermediate Similarity	NPD230	Phase 1
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD9493	Approved
0.7683	Intermediate Similarity	NPD6559	Discontinued
0.7683	Intermediate Similarity	NPD7251	Discontinued
0.7671	Intermediate Similarity	NPD7033	Discontinued
0.7669	Intermediate Similarity	NPD1729	Discontinued
0.7651	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7636	Intermediate Similarity	NPD7808	Phase 3
0.7625	Intermediate Similarity	NPD5710	Approved
0.7625	Intermediate Similarity	NPD5711	Approved
0.7622	Intermediate Similarity	NPD3268	Approved
0.7606	Intermediate Similarity	NPD4908	Phase 1
0.7597	Intermediate Similarity	NPD3226	Approved
0.7589	Intermediate Similarity	NPD1019	Discontinued
0.758	Intermediate Similarity	NPD5402	Approved
0.753	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD4360	Phase 2
0.7466	Intermediate Similarity	NPD447	Suspended
0.7465	Intermediate Similarity	NPD2798	Approved
0.7457	Intermediate Similarity	NPD4361	Phase 2
0.7457	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2346	Discontinued
0.7447	Intermediate Similarity	NPD3225	Approved
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7429	Intermediate Similarity	NPD1608	Approved
0.7414	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1465	Phase 2
0.7394	Intermediate Similarity	NPD3266	Approved
0.7394	Intermediate Similarity	NPD3267	Approved
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6104	Discontinued
0.7362	Intermediate Similarity	NPD3926	Phase 2
0.7361	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3972	Approved
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1613	Approved
0.7273	Intermediate Similarity	NPD1164	Approved
0.7266	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4749	Approved
0.725	Intermediate Similarity	NPD4288	Approved
0.7241	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1652	Phase 2
0.7234	Intermediate Similarity	NPD1201	Approved
0.723	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD17	Approved
0.7212	Intermediate Similarity	NPD2403	Approved
0.7192	Intermediate Similarity	NPD4625	Phase 3
0.7183	Intermediate Similarity	NPD1481	Phase 2
0.7172	Intermediate Similarity	NPD9494	Approved
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.717	Intermediate Similarity	NPD5889	Approved
0.717	Intermediate Similarity	NPD5890	Approved
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.7162	Intermediate Similarity	NPD3142	Approved
0.7162	Intermediate Similarity	NPD3140	Approved
0.7153	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD2296	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7105	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6005	Phase 3
0.7105	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6004	Phase 3
0.7105	Intermediate Similarity	NPD6002	Phase 3
0.7095	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1778	Approved
0.7091	Intermediate Similarity	NPD7229	Phase 3
0.709	Intermediate Similarity	NPD74	Approved
0.709	Intermediate Similarity	NPD9266	Approved
0.7071	Intermediate Similarity	NPD1894	Discontinued
0.7049	Intermediate Similarity	NPD7584	Approved
0.7044	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4477	Approved
0.7039	Intermediate Similarity	NPD4476	Approved
0.7032	Intermediate Similarity	NPD2354	Approved
0.7027	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3764	Approved
0.7024	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD846	Approved
0.7023	Intermediate Similarity	NPD940	Approved
0.7015	Intermediate Similarity	NPD9264	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4661	Approved
0.7006	Intermediate Similarity	NPD4662	Approved
0.7006	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD6585	Discontinued
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4287	Approved
0.6968	Remote Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD1876	Approved
0.6966	Remote Similarity	NPD1283	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