NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	264.305
LogP:	3.265
LogD:	3.008
LogS:	-4.622
# Rotatable Bonds:	1
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.61
Fsp3:	0.4
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:	-4.646
MDCK Permeability:	2.2395417545340024e-05
Pgp-inhibitor:	0.203
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.158

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	91.62264251708984%
Volume Distribution (VD):	0.787
Pgp-substrate:	9.60415267944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.662
CYP2C19-substrate:	0.585
CYP2C9-inhibitor:	0.405
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.638
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	10.571
Half-life (T1/2):	0.405

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.197
Maximum Recommended Daily Dose:	0.109
Skin Sensitization:	0.156
Carcinogencity:	0.883
Eye Corrosion:	0.004
Eye Irritation:	0.041
Respiratory Toxicity:	0.534

Download Data

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

Natural Product: NPC471826

Natural Product ID:	NPC471826
*Common Name:**	5-Methoxydihydroseselin
IUPAC Name:	5-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	FFEMDYNYWWCISJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-15(2)7-6-10-12(19-15)8-11(17-3)9-4-5-13(16)18-14(9)10/h4-5,8H,6-7H2,1-3H3
SMILES:	CC1(CCC2=C3C(=C(C=C2O1)OC)C=CC(=O)O3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235993
PubChem CID:	12112042
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7213	Toddalia asiatica	Species	Rutaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1464	Individual Protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	2200.0	nM	PMID[496703]

☑ 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 NPC471826 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	446
0.1-0.2	1970
0.2-0.3	5340
0.3-0.4	11683
0.4-0.5	5876
0.5-0.6	4973
0.6-0.7	5804
0.7-0.8	4728
0.8-0.85	1306
0.85-0.9	406
0.9-0.95	132
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC111347
0.9587	High Similarity	NPC471827
0.9587	High Similarity	NPC471828
0.9583	High Similarity	NPC173350
0.9583	High Similarity	NPC290605
0.9583	High Similarity	NPC472518
0.9583	High Similarity	NPC154176
0.9512	High Similarity	NPC185066
0.9504	High Similarity	NPC73413
0.9504	High Similarity	NPC201667
0.95	High Similarity	NPC96286
0.95	High Similarity	NPC248429
0.9444	High Similarity	NPC318400
0.9444	High Similarity	NPC471910
0.9444	High Similarity	NPC296624
0.9444	High Similarity	NPC207002
0.9444	High Similarity	NPC133956
0.9444	High Similarity	NPC167111
0.9421	High Similarity	NPC273772
0.9421	High Similarity	NPC109675
0.9417	High Similarity	NPC144418
0.937	High Similarity	NPC166672
0.937	High Similarity	NPC195343
0.937	High Similarity	NPC127888
0.937	High Similarity	NPC74655
0.937	High Similarity	NPC164269
0.937	High Similarity	NPC198381
0.937	High Similarity	NPC100986
0.937	High Similarity	NPC260265
0.937	High Similarity	NPC287182
0.937	High Similarity	NPC319859
0.937	High Similarity	NPC84894
0.937	High Similarity	NPC18804
0.937	High Similarity	NPC267412
0.937	High Similarity	NPC47163
0.936	High Similarity	NPC80170
0.9344	High Similarity	NPC291899
0.9344	High Similarity	NPC27671
0.9339	High Similarity	NPC257188
0.9339	High Similarity	NPC13007
0.9339	High Similarity	NPC150214
0.9297	High Similarity	NPC281241
0.9297	High Similarity	NPC86892
0.9297	High Similarity	NPC471909
0.9297	High Similarity	NPC471625
0.9297	High Similarity	NPC472424
0.928	High Similarity	NPC168710
0.9274	High Similarity	NPC289316
0.9262	High Similarity	NPC50720
0.9225	High Similarity	NPC471630
0.9225	High Similarity	NPC283019
0.9225	High Similarity	NPC128529
0.9225	High Similarity	NPC177281
0.9225	High Similarity	NPC476455
0.9225	High Similarity	NPC160727
0.9225	High Similarity	NPC149320
0.9225	High Similarity	NPC55615
0.9213	High Similarity	NPC14248
0.92	High Similarity	NPC199204
0.92	High Similarity	NPC472519
0.9194	High Similarity	NPC188327
0.9194	High Similarity	NPC163248
0.9194	High Similarity	NPC234109
0.9174	High Similarity	NPC163200
0.9167	High Similarity	NPC298796
0.9154	High Similarity	NPC153818
0.9154	High Similarity	NPC232246
0.9141	High Similarity	NPC222036
0.9141	High Similarity	NPC7526
0.9113	High Similarity	NPC232692
0.9113	High Similarity	NPC202594
0.9106	High Similarity	NPC315807
0.9106	High Similarity	NPC143725
0.9084	High Similarity	NPC279573
0.9084	High Similarity	NPC270256
0.9084	High Similarity	NPC211110
0.9083	High Similarity	NPC265547
0.9083	High Similarity	NPC96705
0.9083	High Similarity	NPC152306
0.9077	High Similarity	NPC188380
0.9077	High Similarity	NPC78746
0.9077	High Similarity	NPC224543
0.907	High Similarity	NPC180716
0.907	High Similarity	NPC131950
0.907	High Similarity	NPC62366
0.907	High Similarity	NPC224475
0.907	High Similarity	NPC55149
0.907	High Similarity	NPC213173
0.907	High Similarity	NPC307412
0.9062	High Similarity	NPC19157
0.9048	High Similarity	NPC139595
0.9048	High Similarity	NPC157212
0.9048	High Similarity	NPC60704
0.9048	High Similarity	NPC293642
0.9016	High Similarity	NPC235190
0.9016	High Similarity	NPC180006
0.9015	High Similarity	NPC312881
0.9008	High Similarity	NPC281014
0.9008	High Similarity	NPC281356
0.9008	High Similarity	NPC294456
0.9008	High Similarity	NPC212124
0.9008	High Similarity	NPC184861
0.9008	High Similarity	NPC225106
0.9	High Similarity	NPC469675
0.9	High Similarity	NPC472525
0.8992	High Similarity	NPC55147
0.8992	High Similarity	NPC469955
0.8992	High Similarity	NPC469952
0.8992	High Similarity	NPC54503
0.8992	High Similarity	NPC31849
0.8968	High Similarity	NPC243688
0.896	High Similarity	NPC93219
0.896	High Similarity	NPC244495
0.8947	High Similarity	NPC152771
0.8947	High Similarity	NPC195357
0.8947	High Similarity	NPC287286
0.8931	High Similarity	NPC104796
0.8931	High Similarity	NPC283331
0.8923	High Similarity	NPC50896
0.8923	High Similarity	NPC253574
0.8923	High Similarity	NPC98179
0.8923	High Similarity	NPC204353
0.8923	High Similarity	NPC326600
0.8917	High Similarity	NPC128633
0.8915	High Similarity	NPC123954
0.8915	High Similarity	NPC194277
0.8915	High Similarity	NPC469956
0.8906	High Similarity	NPC32463
0.8864	High Similarity	NPC155963
0.8855	High Similarity	NPC33986
0.8846	High Similarity	NPC472524
0.8846	High Similarity	NPC163557
0.8837	High Similarity	NPC66430
0.8837	High Similarity	NPC37009
0.8837	High Similarity	NPC472517
0.8815	High Similarity	NPC119640
0.8815	High Similarity	NPC183646
0.8797	High Similarity	NPC151946
0.8788	High Similarity	NPC26954
0.8788	High Similarity	NPC38099
0.8788	High Similarity	NPC167517
0.8769	High Similarity	NPC175159
0.876	High Similarity	NPC113098
0.875	High Similarity	NPC476457
0.874	High Similarity	NPC101894
0.8722	High Similarity	NPC306365
0.8722	High Similarity	NPC14697
0.8712	High Similarity	NPC61499
0.8712	High Similarity	NPC229128
0.8702	High Similarity	NPC205797
0.8702	High Similarity	NPC142563
0.8702	High Similarity	NPC141822
0.8702	High Similarity	NPC1220
0.8702	High Similarity	NPC291551
0.8702	High Similarity	NPC241165
0.8702	High Similarity	NPC83535
0.8702	High Similarity	NPC469965
0.8692	High Similarity	NPC267336
0.8692	High Similarity	NPC272650
0.8692	High Similarity	NPC29734
0.8686	High Similarity	NPC295696
0.8686	High Similarity	NPC85624
0.8686	High Similarity	NPC469701
0.8672	High Similarity	NPC224774
0.8672	High Similarity	NPC121740
0.8672	High Similarity	NPC258567
0.8667	High Similarity	NPC472523
0.8661	High Similarity	NPC168259
0.8657	High Similarity	NPC35501
0.8657	High Similarity	NPC144512
0.8657	High Similarity	NPC137262
0.8657	High Similarity	NPC307883
0.8657	High Similarity	NPC47040
0.8657	High Similarity	NPC37428
0.8657	High Similarity	NPC278600
0.864	High Similarity	NPC52247
0.864	High Similarity	NPC187868
0.8636	High Similarity	NPC147030
0.8615	High Similarity	NPC19242
0.8613	High Similarity	NPC471824
0.8605	High Similarity	NPC469453
0.8593	High Similarity	NPC36414
0.8593	High Similarity	NPC71903
0.8582	High Similarity	NPC131198
0.8582	High Similarity	NPC472516
0.8561	High Similarity	NPC87950
0.8561	High Similarity	NPC296377
0.8561	High Similarity	NPC469449
0.8561	High Similarity	NPC472522
0.8561	High Similarity	NPC471764
0.856	High Similarity	NPC319378
0.856	High Similarity	NPC302107
0.8551	High Similarity	NPC43716
0.8551	High Similarity	NPC475719
0.8551	High Similarity	NPC101255
0.8538	High Similarity	NPC123127
0.8538	High Similarity	NPC27239
0.8529	High Similarity	NPC155552
0.8529	High Similarity	NPC183642
0.8529	High Similarity	NPC310370

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 NPC471826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1011
0.2-0.3	1769
0.3-0.4	2725
0.4-0.5	1842
0.5-0.6	974
0.6-0.7	294
0.7-0.8	96
0.8-0.85	27
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8702	High Similarity	NPD5123	Clinical (unspecified phase)
0.8702	High Similarity	NPD5124	Phase 1
0.864	High Similarity	NPD422	Phase 1
0.8321	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD1296	Phase 2
0.8129	Intermediate Similarity	NPD1652	Phase 2
0.8102	Intermediate Similarity	NPD3748	Approved
0.806	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD9697	Approved
0.7986	Intermediate Similarity	NPD920	Approved
0.7984	Intermediate Similarity	NPD5535	Approved
0.7943	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD1610	Phase 2
0.7914	Intermediate Similarity	NPD2796	Approved
0.791	Intermediate Similarity	NPD4908	Phase 1
0.7891	Intermediate Similarity	NPD1548	Phase 1
0.7832	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5691	Approved
0.7817	Intermediate Similarity	NPD3750	Approved
0.7785	Intermediate Similarity	NPD7819	Suspended
0.7785	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7411	Suspended
0.7724	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1358	Approved
0.7724	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD4625	Phase 3
0.7718	Intermediate Similarity	NPD6801	Discontinued
0.7687	Intermediate Similarity	NPD1653	Approved
0.7687	Intermediate Similarity	NPD3267	Approved
0.7687	Intermediate Similarity	NPD2797	Approved
0.7687	Intermediate Similarity	NPD3266	Approved
0.7681	Intermediate Similarity	NPD4307	Phase 2
0.7669	Intermediate Similarity	NPD4749	Approved
0.7642	Intermediate Similarity	NPD3134	Approved
0.7634	Intermediate Similarity	NPD4626	Approved
0.7632	Intermediate Similarity	NPD7075	Discontinued
0.7622	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3225	Approved
0.7603	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7768	Phase 2
0.7552	Intermediate Similarity	NPD1549	Phase 2
0.7536	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD3268	Approved
0.7534	Intermediate Similarity	NPD6799	Approved
0.7519	Intermediate Similarity	NPD1611	Approved
0.7518	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD919	Approved
0.7465	Intermediate Similarity	NPD4308	Phase 3
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.7445	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3496	Discontinued
0.7431	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1613	Approved
0.7429	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1551	Phase 2
0.7364	Intermediate Similarity	NPD1241	Discontinued
0.7353	Intermediate Similarity	NPD8651	Approved
0.7351	Intermediate Similarity	NPD6599	Discontinued
0.7351	Intermediate Similarity	NPD4380	Phase 2
0.7343	Intermediate Similarity	NPD7033	Discontinued
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7342	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9717	Approved
0.732	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5844	Phase 1
0.731	Intermediate Similarity	NPD2424	Discontinued
0.7305	Intermediate Similarity	NPD1240	Approved
0.7305	Intermediate Similarity	NPD4060	Phase 1
0.7297	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2935	Discontinued
0.729	Intermediate Similarity	NPD3749	Approved
0.7286	Intermediate Similarity	NPD2313	Discontinued
0.7273	Intermediate Similarity	NPD7644	Approved
0.7273	Intermediate Similarity	NPD3817	Phase 2
0.7273	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5403	Approved
0.7254	Intermediate Similarity	NPD4340	Discontinued
0.7248	Intermediate Similarity	NPD5401	Approved
0.7246	Intermediate Similarity	NPD1019	Discontinued
0.7239	Intermediate Similarity	NPD1778	Approved
0.7239	Intermediate Similarity	NPD17	Approved
0.7226	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7466	Approved
0.7211	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1607	Approved
0.7197	Intermediate Similarity	NPD5494	Approved
0.7179	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1203	Approved
0.7172	Intermediate Similarity	NPD6100	Approved
0.7172	Intermediate Similarity	NPD6099	Approved
0.7163	Intermediate Similarity	NPD6798	Discontinued
0.7161	Intermediate Similarity	NPD4288	Approved
0.7153	Intermediate Similarity	NPD7097	Phase 1
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7549	Discontinued
0.7133	Intermediate Similarity	NPD7447	Phase 1
0.7133	Intermediate Similarity	NPD1933	Approved
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1091	Approved
0.7132	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6671	Approved
0.7114	Intermediate Similarity	NPD6667	Approved
0.7114	Intermediate Similarity	NPD6666	Approved
0.7109	Intermediate Similarity	NPD2684	Approved
0.7097	Intermediate Similarity	NPD1465	Phase 2
0.7095	Intermediate Similarity	NPD4628	Phase 3
0.7092	Intermediate Similarity	NPD7095	Approved
0.7086	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1608	Approved
0.7071	Intermediate Similarity	NPD3018	Phase 2
0.7071	Intermediate Similarity	NPD2861	Phase 2
0.7067	Intermediate Similarity	NPD7213	Phase 3
0.7067	Intermediate Similarity	NPD7212	Phase 2
0.7067	Intermediate Similarity	NPD1511	Approved
0.7063	Intermediate Similarity	NPD4140	Approved
0.7051	Intermediate Similarity	NPD5402	Approved
0.704	Intermediate Similarity	NPD940	Approved
0.704	Intermediate Similarity	NPD846	Approved
0.7034	Intermediate Similarity	NPD2200	Suspended
0.7032	Intermediate Similarity	NPD1934	Approved
0.7027	Intermediate Similarity	NPD2800	Approved
0.7027	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7843	Approved
0.702	Intermediate Similarity	NPD2532	Approved
0.702	Intermediate Similarity	NPD2534	Approved
0.702	Intermediate Similarity	NPD2533	Approved
0.7014	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD6002	Phase 3
0.7007	Intermediate Similarity	NPD2346	Discontinued
0.7007	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1281	Approved
0.7007	Intermediate Similarity	NPD6005	Phase 3
0.7007	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD8032	Phase 2
0.6992	Remote Similarity	NPD7157	Approved
0.6987	Remote Similarity	NPD2801	Approved
0.6974	Remote Similarity	NPD1512	Approved
0.6972	Remote Similarity	NPD3027	Phase 3
0.697	Remote Similarity	NPD6559	Discontinued
0.6962	Remote Similarity	NPD6971	Discontinued
0.6957	Remote Similarity	NPD2981	Phase 2
0.6948	Remote Similarity	NPD3226	Approved
0.6948	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1137	Approved
0.6947	Remote Similarity	NPD1139	Approved
0.6943	Remote Similarity	NPD2415	Discontinued
0.6939	Remote Similarity	NPD4477	Approved
0.6939	Remote Similarity	NPD4476	Approved
0.6937	Remote Similarity	NPD6959	Discontinued
0.6937	Remote Similarity	NPD1247	Approved
0.6934	Remote Similarity	NPD3847	Discontinued
0.6923	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5451	Approved
0.6923	Remote Similarity	NPD411	Approved
0.6918	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4536	Approved
0.6918	Remote Similarity	NPD4538	Approved
0.6912	Remote Similarity	NPD5585	Approved
0.6912	Remote Similarity	NPD1651	Approved
0.6909	Remote Similarity	NPD5953	Discontinued
0.6908	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2982	Phase 2
0.6906	Remote Similarity	NPD2983	Phase 2
0.6903	Remote Similarity	NPD6585	Discontinued
0.6899	Remote Similarity	NPD290	Approved
0.6897	Remote Similarity	NPD447	Suspended
0.6894	Remote Similarity	NPD6232	Discontinued
0.6894	Remote Similarity	NPD1138	Approved
0.6892	Remote Similarity	NPD5763	Approved
0.6892	Remote Similarity	NPD5762	Approved
0.689	Remote Similarity	NPD7286	Phase 2
0.6889	Remote Similarity	NPD5536	Phase 2
0.6887	Remote Similarity	NPD5058	Phase 3
0.6879	Remote Similarity	NPD3690	Phase 2
0.6879	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD8455	Phase 2
0.6879	Remote Similarity	NPD3691	Phase 2
0.6875	Remote Similarity	NPD6233	Phase 2
0.6867	Remote Similarity	NPD7003	Approved
0.6859	Remote Similarity	NPD5890	Approved
0.6859	Remote Similarity	NPD5889	Approved
0.6857	Remote Similarity	NPD6696	Suspended
0.6857	Remote Similarity	NPD1283	Approved
0.6849	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6651	Approved
0.6842	Remote Similarity	NPD5283	Phase 1
0.6838	Remote Similarity	NPD1894	Discontinued
0.6838	Remote Similarity	NPD9545	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