NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.07
Volume:	220.974
LogP:	2.298
LogD:	2.108
LogS:	-2.408
# Rotatable Bonds:	2
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	2.135
Fsp3:	0.25
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:	-4.679
MDCK Permeability:	2.974395283672493e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.879

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.53
Plasma Protein Binding (PPB):	75.45508575439453%
Volume Distribution (VD):	0.984
Pgp-substrate:	19.728578567504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.708
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	6.645
Half-life (T1/2):	0.563

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.537
AMES Toxicity:	0.537
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.182
Skin Sensitization:	0.371
Carcinogencity:	0.047
Eye Corrosion:	0.197
Eye Irritation:	0.967
Respiratory Toxicity:	0.416

Download Data

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

Natural Product: NPC49852

Natural Product ID:	NPC49852
*Common Name:**	5,7-Dimethoxy-2-Methylchromen-4-One
IUPAC Name:	5,7-dimethoxy-2-methylchromen-4-one
Synonyms:
Standard InCHIKey:	ARFUTALOPVWOBA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12O4/c1-7-4-9(13)12-10(15-3)5-8(14-2)6-11(12)16-7/h4-6H,1-3H3
SMILES:	COc1cc(OC)c2c(c1)oc(cc2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449227
PubChem CID:	14986079
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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	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
ED50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	315.1	ug.mL-1	PMID[455054]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	>	10.0	umol/cm2	PMID[455055]

☑ 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 NPC49852 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	484
0.1-0.2	2183
0.2-0.3	6081
0.3-0.4	12470
0.4-0.5	4300
0.5-0.6	5243
0.6-0.7	5790
0.7-0.8	4182
0.8-0.85	1413
0.85-0.9	450
0.9-0.95	90
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475496
0.9917	High Similarity	NPC473907
0.9836	High Similarity	NPC473894
0.96	High Similarity	NPC278556
0.96	High Similarity	NPC31872
0.96	High Similarity	NPC473584
0.96	High Similarity	NPC475589
0.9524	High Similarity	NPC101294
0.9524	High Similarity	NPC473655
0.9524	High Similarity	NPC25937
0.952	High Similarity	NPC270369
0.952	High Similarity	NPC5515
0.9449	High Similarity	NPC223457
0.9444	High Similarity	NPC284424
0.9375	High Similarity	NPC125920
0.937	High Similarity	NPC10971
0.937	High Similarity	NPC229646
0.935	High Similarity	NPC65041
0.9302	High Similarity	NPC60667
0.9302	High Similarity	NPC46869
0.9297	High Similarity	NPC292998
0.9297	High Similarity	NPC108113
0.9297	High Similarity	NPC93756
0.9231	High Similarity	NPC194281
0.9231	High Similarity	NPC268081
0.9231	High Similarity	NPC72452
0.9231	High Similarity	NPC231772
0.9231	High Similarity	NPC254741
0.9231	High Similarity	NPC174999
0.9231	High Similarity	NPC473887
0.9231	High Similarity	NPC127447
0.9231	High Similarity	NPC47815
0.9231	High Similarity	NPC234133
0.9231	High Similarity	NPC61546
0.9231	High Similarity	NPC29353
0.9231	High Similarity	NPC124784
0.9231	High Similarity	NPC472883
0.9231	High Similarity	NPC161196
0.9225	High Similarity	NPC125269
0.9219	High Similarity	NPC203817
0.9206	High Similarity	NPC211120
0.92	High Similarity	NPC305518
0.92	High Similarity	NPC41721
0.92	High Similarity	NPC128428
0.916	High Similarity	NPC266597
0.916	High Similarity	NPC250266
0.916	High Similarity	NPC253616
0.9154	High Similarity	NPC99854
0.9147	High Similarity	NPC274121
0.9147	High Similarity	NPC213216
0.9147	High Similarity	NPC50898
0.9147	High Similarity	NPC78540
0.9091	High Similarity	NPC17848
0.9091	High Similarity	NPC276905
0.9091	High Similarity	NPC36414
0.9091	High Similarity	NPC131130
0.9084	High Similarity	NPC13408
0.9077	High Similarity	NPC144027
0.9077	High Similarity	NPC172262
0.9077	High Similarity	NPC236974
0.907	High Similarity	NPC182428
0.9055	High Similarity	NPC212379
0.9055	High Similarity	NPC69235
0.9023	High Similarity	NPC23257
0.9023	High Similarity	NPC136095
0.9023	High Similarity	NPC78913
0.9023	High Similarity	NPC241838
0.9023	High Similarity	NPC143799
0.9023	High Similarity	NPC139554
0.9023	High Similarity	NPC18260
0.9023	High Similarity	NPC152042
0.9023	High Similarity	NPC471697
0.9015	High Similarity	NPC103001
0.9015	High Similarity	NPC188879
0.9015	High Similarity	NPC259685
0.9008	High Similarity	NPC242712
0.9008	High Similarity	NPC151113
0.9	High Similarity	NPC223354
0.9	High Similarity	NPC57601
0.9	High Similarity	NPC247743
0.8992	High Similarity	NPC113006
0.8984	High Similarity	NPC185497
0.8976	High Similarity	NPC475017
0.8976	High Similarity	NPC186098
0.8976	High Similarity	NPC80694
0.896	High Similarity	NPC255073
0.8955	High Similarity	NPC241100
0.8955	High Similarity	NPC146679
0.8955	High Similarity	NPC184536
0.8955	High Similarity	NPC159275
0.8955	High Similarity	NPC471587
0.8955	High Similarity	NPC103342
0.8955	High Similarity	NPC230285
0.8955	High Similarity	NPC269652
0.8955	High Similarity	NPC103904
0.8955	High Similarity	NPC281207
0.8955	High Similarity	NPC150522
0.8955	High Similarity	NPC59951
0.8947	High Similarity	NPC99333
0.8947	High Similarity	NPC201395
0.8947	High Similarity	NPC124269
0.8947	High Similarity	NPC470669
0.8947	High Similarity	NPC280284
0.8947	High Similarity	NPC470668
0.8947	High Similarity	NPC57380
0.8947	High Similarity	NPC188947
0.8939	High Similarity	NPC281917
0.8939	High Similarity	NPC156910
0.8939	High Similarity	NPC472516
0.8939	High Similarity	NPC256042
0.8939	High Similarity	NPC216361
0.8939	High Similarity	NPC470398
0.8939	High Similarity	NPC187826
0.8939	High Similarity	NPC121243
0.8939	High Similarity	NPC240147
0.8939	High Similarity	NPC187432
0.8939	High Similarity	NPC240593
0.8939	High Similarity	NPC470397
0.8939	High Similarity	NPC116775
0.8931	High Similarity	NPC66705
0.8923	High Similarity	NPC87231
0.8923	High Similarity	NPC205468
0.8923	High Similarity	NPC257756
0.8923	High Similarity	NPC212631
0.8923	High Similarity	NPC129132
0.8906	High Similarity	NPC187907
0.8906	High Similarity	NPC230818
0.8906	High Similarity	NPC60558
0.8889	High Similarity	NPC282300
0.8889	High Similarity	NPC262094
0.8889	High Similarity	NPC103362
0.8889	High Similarity	NPC29536
0.8889	High Similarity	NPC110969
0.8889	High Similarity	NPC136840
0.8889	High Similarity	NPC471640
0.8889	High Similarity	NPC90582
0.8889	High Similarity	NPC2771
0.8889	High Similarity	NPC471644
0.8881	High Similarity	NPC20709
0.8881	High Similarity	NPC274784
0.8881	High Similarity	NPC11566
0.8881	High Similarity	NPC329203
0.8881	High Similarity	NPC217186
0.8881	High Similarity	NPC301217
0.8881	High Similarity	NPC55018
0.8881	High Similarity	NPC222342
0.8881	High Similarity	NPC140890
0.8881	High Similarity	NPC310135
0.8881	High Similarity	NPC150648
0.8881	High Similarity	NPC96565
0.8881	High Similarity	NPC225153
0.8881	High Similarity	NPC220062
0.8881	High Similarity	NPC472515
0.8881	High Similarity	NPC265871
0.8881	High Similarity	NPC473076
0.8881	High Similarity	NPC303633
0.8881	High Similarity	NPC53181
0.8881	High Similarity	NPC216978
0.8872	High Similarity	NPC160972
0.8872	High Similarity	NPC275055
0.8872	High Similarity	NPC107586
0.8872	High Similarity	NPC157855
0.8872	High Similarity	NPC287246
0.8872	High Similarity	NPC79943
0.8872	High Similarity	NPC296490
0.8872	High Similarity	NPC228661
0.8872	High Similarity	NPC12296
0.8872	High Similarity	NPC299379
0.8872	High Similarity	NPC243083
0.8872	High Similarity	NPC32441
0.8872	High Similarity	NPC295261
0.8872	High Similarity	NPC290291
0.8872	High Similarity	NPC13768
0.8864	High Similarity	NPC9985
0.8864	High Similarity	NPC239495
0.8864	High Similarity	NPC101752
0.8855	High Similarity	NPC204960
0.8855	High Similarity	NPC159623
0.8855	High Similarity	NPC242294
0.8855	High Similarity	NPC263670
0.8855	High Similarity	NPC20560
0.8855	High Similarity	NPC18877
0.8855	High Similarity	NPC472365
0.8855	High Similarity	NPC294593
0.8855	High Similarity	NPC312318
0.8855	High Similarity	NPC337373
0.8855	High Similarity	NPC144051
0.8855	High Similarity	NPC192304
0.8855	High Similarity	NPC28753
0.8855	High Similarity	NPC139813
0.8855	High Similarity	NPC188646
0.8855	High Similarity	NPC56031
0.8855	High Similarity	NPC82225
0.8855	High Similarity	NPC175098
0.8846	High Similarity	NPC313618
0.8846	High Similarity	NPC262359
0.8846	High Similarity	NPC64359
0.8846	High Similarity	NPC65060
0.8846	High Similarity	NPC308037
0.8837	High Similarity	NPC84772

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 NPC49852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	1033
0.2-0.3	1744
0.3-0.4	2800
0.4-0.5	1699
0.5-0.6	1000
0.6-0.7	299
0.7-0.8	107
0.8-0.85	24
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9084	High Similarity	NPD2796	Approved
0.8872	High Similarity	NPD1550	Clinical (unspecified phase)
0.8872	High Similarity	NPD1552	Clinical (unspecified phase)
0.8846	High Similarity	NPD1240	Approved
0.8806	High Similarity	NPD1549	Phase 2
0.8741	High Similarity	NPD1243	Approved
0.8722	High Similarity	NPD1510	Phase 2
0.8712	High Similarity	NPD1607	Approved
0.8696	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD970	Clinical (unspecified phase)
0.8623	High Similarity	NPD6799	Approved
0.8489	Intermediate Similarity	NPD1511	Approved
0.844	Intermediate Similarity	NPD920	Approved
0.8429	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD2654	Approved
0.8309	Intermediate Similarity	NPD3748	Approved
0.8298	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD6599	Discontinued
0.8219	Intermediate Similarity	NPD2801	Approved
0.8207	Intermediate Similarity	NPD7411	Suspended
0.8201	Intermediate Similarity	NPD2800	Approved
0.8163	Intermediate Similarity	NPD3817	Phase 2
0.8151	Intermediate Similarity	NPD6801	Discontinued
0.8151	Intermediate Similarity	NPD1934	Approved
0.8145	Intermediate Similarity	NPD1241	Discontinued
0.814	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD1296	Phase 2
0.812	Intermediate Similarity	NPD6832	Phase 2
0.8116	Intermediate Similarity	NPD1551	Phase 2
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD9717	Approved
0.8042	Intermediate Similarity	NPD5401	Approved
0.8041	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD6651	Approved
0.8014	Intermediate Similarity	NPD4380	Phase 2
0.8014	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD422	Phase 1
0.7987	Intermediate Similarity	NPD3882	Suspended
0.797	Intermediate Similarity	NPD1019	Discontinued
0.7933	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7075	Discontinued
0.7931	Intermediate Similarity	NPD5403	Approved
0.7895	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD1203	Approved
0.7852	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5494	Approved
0.7817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD3266	Approved
0.7761	Intermediate Similarity	NPD3267	Approved
0.7698	Intermediate Similarity	NPD1933	Approved
0.7698	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD1548	Phase 1
0.7677	Intermediate Similarity	NPD3926	Phase 2
0.7676	Intermediate Similarity	NPD2344	Approved
0.7671	Intermediate Similarity	NPD2533	Approved
0.7671	Intermediate Similarity	NPD2534	Approved
0.7671	Intermediate Similarity	NPD2532	Approved
0.7669	Intermediate Similarity	NPD3972	Approved
0.7662	Intermediate Similarity	NPD6959	Discontinued
0.766	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD7768	Phase 2
0.7628	Intermediate Similarity	NPD6166	Phase 2
0.7628	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2313	Discontinued
0.7595	Intermediate Similarity	NPD7054	Approved
0.7595	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD17	Approved
0.7574	Intermediate Similarity	NPD2798	Approved
0.7566	Intermediate Similarity	NPD5402	Approved
0.7557	Intermediate Similarity	NPD9545	Approved
0.7547	Intermediate Similarity	NPD7472	Approved
0.7538	Intermediate Similarity	NPD9493	Approved
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD3142	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD3140	Approved
0.75	Intermediate Similarity	NPD4307	Phase 2
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD6099	Approved
0.7482	Intermediate Similarity	NPD411	Approved
0.7482	Intermediate Similarity	NPD3268	Approved
0.7466	Intermediate Similarity	NPD2309	Approved
0.7453	Intermediate Similarity	NPD7251	Discontinued
0.745	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD230	Phase 1
0.7447	Intermediate Similarity	NPD447	Suspended
0.7438	Intermediate Similarity	NPD7074	Phase 3
0.7431	Intermediate Similarity	NPD1471	Phase 3
0.7426	Intermediate Similarity	NPD3225	Approved
0.7413	Intermediate Similarity	NPD7033	Discontinued
0.7413	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7808	Phase 3
0.7407	Intermediate Similarity	NPD1608	Approved
0.7403	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4628	Phase 3
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7375	Intermediate Similarity	NPD7286	Phase 2
0.7372	Intermediate Similarity	NPD2797	Approved
0.7333	Intermediate Similarity	NPD1610	Phase 2
0.7301	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1876	Approved
0.7296	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4308	Phase 3
0.7279	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.725	Intermediate Similarity	NPD7473	Discontinued
0.7239	Intermediate Similarity	NPD6104	Discontinued
0.7237	Intermediate Similarity	NPD3226	Approved
0.7226	Intermediate Similarity	NPD4288	Approved
0.7222	Intermediate Similarity	NPD9697	Approved
0.7214	Intermediate Similarity	NPD4908	Phase 1
0.7211	Intermediate Similarity	NPD1652	Phase 2
0.7203	Intermediate Similarity	NPD5124	Phase 1
0.7203	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9261	Approved
0.7192	Intermediate Similarity	NPD2353	Approved
0.7192	Intermediate Similarity	NPD2346	Discontinued
0.7192	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD5889	Approved
0.7143	Intermediate Similarity	NPD5890	Approved
0.7134	Intermediate Similarity	NPD6559	Discontinued
0.7117	Intermediate Similarity	NPD1729	Discontinued
0.7114	Intermediate Similarity	NPD3887	Approved
0.7113	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6280	Approved
0.7097	Intermediate Similarity	NPD6279	Approved
0.7078	Intermediate Similarity	NPD6585	Discontinued
0.7063	Intermediate Similarity	NPD5710	Approved
0.7063	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD1778	Approved
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.7037	Intermediate Similarity	NPD1894	Discontinued
0.7029	Intermediate Similarity	NPD1481	Phase 2
0.7023	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7390	Discontinued
0.7006	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD2354	Approved
0.6994	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6798	Discontinued
0.6985	Remote Similarity	NPD1651	Approved
0.6978	Remote Similarity	NPD4749	Approved
0.6977	Remote Similarity	NPD9263	Approved
0.6977	Remote Similarity	NPD4363	Phase 3
0.6977	Remote Similarity	NPD4360	Phase 2
0.6977	Remote Similarity	NPD1358	Approved
0.6977	Remote Similarity	NPD9264	Approved
0.6977	Remote Similarity	NPD9267	Approved
0.6974	Remote Similarity	NPD4662	Approved
0.6974	Remote Similarity	NPD4661	Approved
0.6972	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5535	Approved
0.697	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6808	Phase 2
0.6957	Remote Similarity	NPD1535	Discovery
0.6936	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4361	Phase 2
0.6928	Remote Similarity	NPD2186	Approved
0.6923	Remote Similarity	NPD9266	Approved
0.6923	Remote Similarity	NPD74	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD9494	Approved
0.6899	Remote Similarity	NPD3134	Approved
0.6899	Remote Similarity	NPD2296	Approved
0.6897	Remote Similarity	NPD1613	Approved
0.6897	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6844	Discontinued
0.6863	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD9268	Approved
0.6849	Remote Similarity	NPD6355	Discontinued
0.6846	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD290	Approved
0.6846	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5536	Phase 2
0.6835	Remote Similarity	NPD1281	Approved
0.6835	Remote Similarity	NPD1201	Approved
0.6828	Remote Similarity	NPD6233	Phase 2
0.6813	Remote Similarity	NPD6971	Discontinued
0.681	Remote Similarity	NPD5242	Approved
0.68	Remote Similarity	NPD2424	Discontinued
0.6797	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD2684	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