NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.14
Volume:	290.158
LogP:	4.008
LogD:	3.722
LogS:	-5.299
# Rotatable Bonds:	5
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	2.345
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.695
MDCK Permeability:	2.0799561752937734e-05
Pgp-inhibitor:	0.195
Pgp-substrate:	0.488
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	93.8719253540039%
Volume Distribution (VD):	0.621
Pgp-substrate:	5.480658054351807%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.797
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.28
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.385

ADMET: Excretion

Clearance (CL):	9.919
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.329
Carcinogencity:	0.421
Eye Corrosion:	0.004
Eye Irritation:	0.196
Respiratory Toxicity:	0.274

Download Data

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

Natural Product: NPC471827

Natural Product ID:	NPC471827
*Common Name:**	5,7-Dimethoxy-6-(3-Methylbutyl)-Coumarin
IUPAC Name:	5,7-dimethoxy-6-(3-methylbutyl)chromen-2-one
Synonyms:
Standard InCHIKey:	CKUPAJFPLMPMSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H20O4/c1-10(2)5-6-11-13(18-3)9-14-12(16(11)19-4)7-8-15(17)20-14/h7-10H,5-6H2,1-4H3
SMILES:	COc1cc2oc(=O)ccc2c(c1CCC(C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3235997
PubChem CID:	90655370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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	=	11490.0	nM	PMID[470602]

☑ 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 NPC471827 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	431
0.1-0.2	1857
0.2-0.3	5146
0.3-0.4	11243
0.4-0.5	6552
0.5-0.6	4693
0.6-0.7	6107
0.7-0.8	4692
0.8-0.85	1365
0.85-0.9	431
0.9-0.95	153
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471828
0.9748	High Similarity	NPC27671
0.9748	High Similarity	NPC201667
0.9748	High Similarity	NPC73413
0.9664	High Similarity	NPC109675
0.9664	High Similarity	NPC273772
0.9664	High Similarity	NPC472518
0.9587	High Similarity	NPC471826
0.958	High Similarity	NPC248429
0.958	High Similarity	NPC96286
0.9496	High Similarity	NPC144418
0.9431	High Similarity	NPC185066
0.9431	High Similarity	NPC472519
0.9365	High Similarity	NPC54503
0.9355	High Similarity	NPC168710
0.9339	High Similarity	NPC154176
0.9339	High Similarity	NPC173350
0.9339	High Similarity	NPC290605
0.9286	High Similarity	NPC14248
0.928	High Similarity	NPC80170
0.9274	High Similarity	NPC199204
0.9268	High Similarity	NPC234109
0.9268	High Similarity	NPC188327
0.9262	High Similarity	NPC291899
0.9262	High Similarity	NPC111347
0.9256	High Similarity	NPC150214
0.925	High Similarity	NPC235190
0.925	High Similarity	NPC180006
0.925	High Similarity	NPC163200
0.9244	High Similarity	NPC298796
0.9219	High Similarity	NPC471909
0.9219	High Similarity	NPC281241
0.9219	High Similarity	NPC86892
0.9219	High Similarity	NPC471625
0.9219	High Similarity	NPC472424
0.9213	High Similarity	NPC133956
0.9213	High Similarity	NPC7526
0.9213	High Similarity	NPC222036
0.9213	High Similarity	NPC55147
0.9213	High Similarity	NPC318400
0.9213	High Similarity	NPC471910
0.9213	High Similarity	NPC31849
0.9213	High Similarity	NPC296624
0.9213	High Similarity	NPC207002
0.9213	High Similarity	NPC167111
0.9194	High Similarity	NPC243688
0.9194	High Similarity	NPC289316
0.918	High Similarity	NPC315807
0.918	High Similarity	NPC50720
0.916	High Similarity	NPC152306
0.916	High Similarity	NPC96705
0.916	High Similarity	NPC265547
0.9147	High Similarity	NPC128529
0.9147	High Similarity	NPC177281
0.9147	High Similarity	NPC283019
0.9147	High Similarity	NPC149320
0.9147	High Similarity	NPC471630
0.9147	High Similarity	NPC55615
0.9147	High Similarity	NPC160727
0.9147	High Similarity	NPC476455
0.9141	High Similarity	NPC267412
0.9141	High Similarity	NPC198381
0.9141	High Similarity	NPC18804
0.9141	High Similarity	NPC100986
0.9141	High Similarity	NPC164269
0.9141	High Similarity	NPC260265
0.9141	High Similarity	NPC47163
0.9141	High Similarity	NPC213173
0.9141	High Similarity	NPC84894
0.9141	High Similarity	NPC224475
0.9141	High Similarity	NPC287182
0.9141	High Similarity	NPC74655
0.9141	High Similarity	NPC127888
0.9141	High Similarity	NPC55149
0.9141	High Similarity	NPC195343
0.9141	High Similarity	NPC307412
0.9141	High Similarity	NPC166672
0.9141	High Similarity	NPC180716
0.9141	High Similarity	NPC319859
0.9134	High Similarity	NPC19157
0.9113	High Similarity	NPC163248
0.9098	High Similarity	NPC257188
0.9098	High Similarity	NPC13007
0.9083	High Similarity	NPC281356
0.907	High Similarity	NPC469675
0.907	High Similarity	NPC472525
0.9032	High Similarity	NPC232692
0.9032	High Similarity	NPC244495
0.9032	High Similarity	NPC202594
0.9032	High Similarity	NPC93219
0.9024	High Similarity	NPC143725
0.9	High Similarity	NPC26954
0.9	High Similarity	NPC283331
0.9	High Similarity	NPC38099
0.8992	High Similarity	NPC50896
0.8992	High Similarity	NPC62366
0.8992	High Similarity	NPC204353
0.8992	High Similarity	NPC128633
0.8992	High Similarity	NPC326600
0.8984	High Similarity	NPC194277
0.8976	High Similarity	NPC32463
0.8968	High Similarity	NPC157212
0.8968	High Similarity	NPC60704
0.8968	High Similarity	NPC139595
0.8968	High Similarity	NPC293642
0.896	High Similarity	NPC101894
0.8931	High Similarity	NPC155963
0.8931	High Similarity	NPC14697
0.8931	High Similarity	NPC306365
0.8923	High Similarity	NPC229128
0.8923	High Similarity	NPC61499
0.8915	High Similarity	NPC469955
0.8915	High Similarity	NPC469952
0.8915	High Similarity	NPC163557
0.8906	High Similarity	NPC472517
0.8889	High Similarity	NPC258567
0.8889	High Similarity	NPC121740
0.8889	High Similarity	NPC224774
0.8872	High Similarity	NPC472523
0.8872	High Similarity	NPC287286
0.8872	High Similarity	NPC472515
0.8864	High Similarity	NPC307883
0.8864	High Similarity	NPC279573
0.8864	High Similarity	NPC151946
0.8864	High Similarity	NPC211110
0.8846	High Similarity	NPC131950
0.8846	High Similarity	NPC253574
0.8846	High Similarity	NPC98179
0.8837	High Similarity	NPC469956
0.8837	High Similarity	NPC175159
0.8828	High Similarity	NPC19242
0.8828	High Similarity	NPC113098
0.8819	High Similarity	NPC469453
0.8797	High Similarity	NPC312881
0.8797	High Similarity	NPC36414
0.8788	High Similarity	NPC232246
0.8788	High Similarity	NPC153818
0.8788	High Similarity	NPC472516
0.8788	High Similarity	NPC131198
0.8779	High Similarity	NPC33986
0.8769	High Similarity	NPC472522
0.8769	High Similarity	NPC472524
0.876	High Similarity	NPC37009
0.876	High Similarity	NPC66430
0.876	High Similarity	NPC272650
0.876	High Similarity	NPC267336
0.876	High Similarity	NPC29734
0.875	High Similarity	NPC474289
0.8731	High Similarity	NPC195357
0.8731	High Similarity	NPC138149
0.8731	High Similarity	NPC155552
0.8731	High Similarity	NPC152771
0.8722	High Similarity	NPC253616
0.8722	High Similarity	NPC270256
0.8712	High Similarity	NPC78746
0.8712	High Similarity	NPC188380
0.8712	High Similarity	NPC224543
0.871	High Similarity	NPC52247
0.871	High Similarity	NPC187868
0.8692	High Similarity	NPC123954
0.8667	High Similarity	NPC20631
0.8667	High Similarity	NPC93640
0.8647	High Similarity	NPC294456
0.8647	High Similarity	NPC212124
0.8647	High Similarity	NPC225106
0.8647	High Similarity	NPC184861
0.8647	High Similarity	NPC281014
0.8647	High Similarity	NPC268081
0.8629	High Similarity	NPC319378
0.8629	High Similarity	NPC302107
0.8626	High Similarity	NPC469965
0.8626	High Similarity	NPC241341
0.8626	High Similarity	NPC1220
0.8626	High Similarity	NPC83535
0.8626	High Similarity	NPC233018
0.8626	High Similarity	NPC205797
0.8626	High Similarity	NPC469449
0.8626	High Similarity	NPC36437
0.8626	High Similarity	NPC141822
0.8626	High Similarity	NPC241165
0.8626	High Similarity	NPC2363
0.8626	High Similarity	NPC142563
0.8626	High Similarity	NPC291551
0.8613	High Similarity	NPC475719
0.8613	High Similarity	NPC469701
0.8613	High Similarity	NPC101255
0.8613	High Similarity	NPC43716
0.8607	High Similarity	NPC471503
0.8607	High Similarity	NPC471498
0.8605	High Similarity	NPC123127
0.8605	High Similarity	NPC27239
0.8603	High Similarity	NPC119640
0.8603	High Similarity	NPC229916
0.8603	High Similarity	NPC183646
0.8593	High Similarity	NPC310370
0.8593	High Similarity	NPC183642
0.8583	High Similarity	NPC168259
0.8582	High Similarity	NPC278600
0.8582	High Similarity	NPC35501
0.8582	High Similarity	NPC47040

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 NPC471827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	990
0.2-0.3	1770
0.3-0.4	2719
0.4-0.5	1799
0.5-0.6	1008
0.6-0.7	320
0.7-0.8	102
0.8-0.85	30
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD422	Phase 1
0.8626	High Similarity	NPD5124	Phase 1
0.8626	High Similarity	NPD5123	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1296	Phase 2
0.8162	Intermediate Similarity	NPD3748	Approved
0.812	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD9697	Approved
0.8058	Intermediate Similarity	NPD1243	Approved
0.8049	Intermediate Similarity	NPD5535	Approved
0.8042	Intermediate Similarity	NPD920	Approved
0.8031	Intermediate Similarity	NPD5691	Approved
0.8	Intermediate Similarity	NPD3134	Approved
0.7971	Intermediate Similarity	NPD2796	Approved
0.797	Intermediate Similarity	NPD4908	Phase 1
0.7929	Intermediate Similarity	NPD1652	Phase 2
0.7887	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD3267	Approved
0.7879	Intermediate Similarity	NPD3266	Approved
0.7879	Intermediate Similarity	NPD2797	Approved
0.7872	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3750	Approved
0.7846	Intermediate Similarity	NPD1610	Phase 2
0.7829	Intermediate Similarity	NPD4626	Approved
0.7812	Intermediate Similarity	NPD1548	Phase 1
0.7787	Intermediate Similarity	NPD1358	Approved
0.7778	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6801	Discontinued
0.7721	Intermediate Similarity	NPD3268	Approved
0.7718	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7819	Suspended
0.7708	Intermediate Similarity	NPD6799	Approved
0.7704	Intermediate Similarity	NPD6832	Phase 2
0.7703	Intermediate Similarity	NPD7411	Suspended
0.7676	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3225	Approved
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.7634	Intermediate Similarity	NPD3496	Discontinued
0.7616	Intermediate Similarity	NPD7768	Phase 2
0.7609	Intermediate Similarity	NPD4060	Phase 1
0.7609	Intermediate Similarity	NPD4307	Phase 2
0.7606	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD4749	Approved
0.7576	Intermediate Similarity	NPD1611	Approved
0.7566	Intermediate Similarity	NPD7075	Discontinued
0.7534	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4625	Phase 3
0.7517	Intermediate Similarity	NPD6599	Discontinued
0.7516	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.7483	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1551	Phase 2
0.7465	Intermediate Similarity	NPD2935	Discontinued
0.7464	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD17	Approved
0.7422	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD8651	Approved
0.7397	Intermediate Similarity	NPD6667	Approved
0.7397	Intermediate Similarity	NPD6666	Approved
0.7394	Intermediate Similarity	NPD4308	Phase 3
0.7394	Intermediate Similarity	NPD1510	Phase 2
0.7388	Intermediate Similarity	NPD9717	Approved
0.7379	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1549	Phase 2
0.7357	Intermediate Similarity	NPD1240	Approved
0.7347	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7328	Intermediate Similarity	NPD7644	Approved
0.732	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3817	Phase 2
0.7319	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5403	Approved
0.7305	Intermediate Similarity	NPD4340	Discontinued
0.7305	Intermediate Similarity	NPD6355	Discontinued
0.7305	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2684	Approved
0.7299	Intermediate Similarity	NPD1019	Discontinued
0.7299	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5401	Approved
0.7293	Intermediate Similarity	NPD1778	Approved
0.7292	Intermediate Similarity	NPD6002	Phase 3
0.7292	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6005	Phase 3
0.7292	Intermediate Similarity	NPD6004	Phase 3
0.7292	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4380	Phase 2
0.7278	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7033	Discontinued
0.726	Intermediate Similarity	NPD4628	Phase 3
0.7259	Intermediate Similarity	NPD1608	Approved
0.7255	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1607	Approved
0.725	Intermediate Similarity	NPD5844	Phase 1
0.7248	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3018	Phase 2
0.7244	Intermediate Similarity	NPD5494	Approved
0.7241	Intermediate Similarity	NPD2424	Discontinued
0.7234	Intermediate Similarity	NPD4140	Approved
0.7234	Intermediate Similarity	NPD1613	Approved
0.7234	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1203	Approved
0.7218	Intermediate Similarity	NPD5585	Approved
0.7214	Intermediate Similarity	NPD6798	Discontinued
0.7209	Intermediate Similarity	NPD7843	Approved
0.7208	Intermediate Similarity	NPD4288	Approved
0.72	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2800	Approved
0.7185	Intermediate Similarity	NPD1281	Approved
0.7181	Intermediate Similarity	NPD2533	Approved
0.7181	Intermediate Similarity	NPD2534	Approved
0.7181	Intermediate Similarity	NPD2532	Approved
0.7176	Intermediate Similarity	NPD7157	Approved
0.7172	Intermediate Similarity	NPD5763	Approved
0.7172	Intermediate Similarity	NPD5762	Approved
0.7163	Intermediate Similarity	NPD8032	Phase 2
0.7161	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5283	Phase 1
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD7466	Approved
0.7133	Intermediate Similarity	NPD6651	Approved
0.7132	Intermediate Similarity	NPD2981	Phase 2
0.7132	Intermediate Similarity	NPD1137	Approved
0.7132	Intermediate Similarity	NPD1139	Approved
0.7122	Intermediate Similarity	NPD2861	Phase 2
0.7122	Intermediate Similarity	NPD2237	Approved
0.7115	Intermediate Similarity	NPD3749	Approved
0.7115	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2979	Phase 3
0.7111	Intermediate Similarity	NPD3847	Discontinued
0.7103	Intermediate Similarity	NPD4477	Approved
0.7103	Intermediate Similarity	NPD6100	Approved
0.7103	Intermediate Similarity	NPD4476	Approved
0.7103	Intermediate Similarity	NPD6099	Approved
0.7097	Intermediate Similarity	NPD846	Approved
0.7097	Intermediate Similarity	NPD940	Approved
0.7097	Intermediate Similarity	NPD5402	Approved
0.7083	Intermediate Similarity	NPD2200	Suspended
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.708	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2982	Phase 2
0.708	Intermediate Similarity	NPD2983	Phase 2
0.7077	Intermediate Similarity	NPD1138	Approved
0.7073	Intermediate Similarity	NPD7549	Discontinued
0.7071	Intermediate Similarity	NPD2614	Approved
0.7068	Intermediate Similarity	NPD5536	Phase 2
0.7067	Intermediate Similarity	NPD7447	Phase 1
0.7063	Intermediate Similarity	NPD1933	Approved
0.7059	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5953	Discontinued
0.705	Intermediate Similarity	NPD2798	Approved
0.705	Intermediate Similarity	NPD3690	Phase 2
0.705	Intermediate Similarity	NPD3691	Phase 2
0.7045	Intermediate Similarity	NPD6387	Discontinued
0.7045	Intermediate Similarity	NPD6671	Approved
0.7037	Intermediate Similarity	NPD7286	Phase 2
0.7032	Intermediate Similarity	NPD2801	Approved
0.7029	Intermediate Similarity	NPD1283	Approved
0.7027	Intermediate Similarity	NPD7003	Approved
0.7021	Intermediate Similarity	NPD7095	Approved
0.7015	Intermediate Similarity	NPD1894	Discontinued
0.7006	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD7212	Phase 2
0.6993	Remote Similarity	NPD3226	Approved
0.6993	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2438	Suspended
0.6981	Remote Similarity	NPD1247	Approved
0.6981	Remote Similarity	NPD7199	Phase 2
0.6977	Remote Similarity	NPD5451	Approved
0.6972	Remote Similarity	NPD411	Approved
0.6972	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1934	Approved
0.6963	Remote Similarity	NPD1651	Approved
0.6959	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4359	Approved
0.6957	Remote Similarity	NPD5327	Phase 3
0.6954	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD290	Approved
0.6944	Remote Similarity	NPD447	Suspended
0.6943	Remote Similarity	NPD3882	Suspended
0.6939	Remote Similarity	NPD2346	Discontinued
0.6937	Remote Similarity	NPD6232	Discontinued
0.6934	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD1465	Phase 2
0.6917	Remote Similarity	NPD2557	Approved
0.6914	Remote Similarity	NPD7473	Discontinued
0.6913	Remote Similarity	NPD3892	Phase 2

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