NPASS Compound

Structure

CID307651 OpenBabel06191716112D 21 22 0 0 1 0 0 0 0 0999 V2000 0.3810 7.0506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6483 4.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3393 3.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2882 6.3074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9479 2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0208 5.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6389 3.4543 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9990 5.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6681 5.8916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3080 4.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 11 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.14
Volume:	304.817
LogP:	3.074
LogD:	2.372
LogS:	-2.683
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	3.444
Fsp3:	0.412
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:	-4.588
MDCK Permeability:	2.3836844775360078e-05
Pgp-inhibitor:	0.772
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	94.42613983154297%
Volume Distribution (VD):	1.571
Pgp-substrate:	2.9416418075561523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.453
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.939
CYP2C19-substrate:	0.479
CYP2C9-inhibitor:	0.905
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.389
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	7.532
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.578
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.204
Skin Sensitization:	0.646
Carcinogencity:	0.355
Eye Corrosion:	0.014
Eye Irritation:	0.448
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC307651

Natural Product ID:	NPC307651
*Common Name:**	10-Angeloylbutylphthalide
IUPAC Name:	4-(3-oxo-1H-2-benzofuran-1-yl)butan-2-yl (Z)-2-methylbut-2-enoate
Synonyms:	10-Angeloylbutylphthalide
Standard InCHIKey:	JSAGVPHDQLARCV-WCIBSUBMSA-N
Standard InCHI:	InChI=1S/C17H20O4/c1-4-11(2)16(18)20-12(3)9-10-15-13-7-5-6-8-14(13)17(19)21-15/h4-8,12,15H,9-10H2,1-3H3/b11-4-
SMILES:	C/C=C(/C)C(=O)OC(C)CCC1c2ccccc2C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500589
PubChem CID:	11572826
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	21.0	%	PMID[529485]

☑ 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 NPC307651 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	238
0.1-0.2	1123
0.2-0.3	2585
0.3-0.4	7183
0.4-0.5	11634
0.5-0.6	11937
0.6-0.7	6806
0.7-0.8	1076
0.8-0.85	59
0.85-0.9	34
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC265407
0.9524	High Similarity	NPC83628
0.934	High Similarity	NPC17417
0.934	High Similarity	NPC10251
0.9259	High Similarity	NPC270699
0.9259	High Similarity	NPC82899
0.9252	High Similarity	NPC251854
0.9252	High Similarity	NPC93084
0.9252	High Similarity	NPC214067
0.9252	High Similarity	NPC196246
0.9245	High Similarity	NPC56493
0.9167	High Similarity	NPC305912
0.9167	High Similarity	NPC1082
0.9151	High Similarity	NPC119271
0.9099	High Similarity	NPC149691
0.9074	High Similarity	NPC174099
0.9048	High Similarity	NPC89886
0.8981	High Similarity	NPC469636
0.8972	High Similarity	NPC30594
0.8972	High Similarity	NPC37622
0.8962	High Similarity	NPC31786
0.8919	High Similarity	NPC153053
0.8909	High Similarity	NPC321852
0.8868	High Similarity	NPC301943
0.8868	High Similarity	NPC474365
0.8829	High Similarity	NPC128368
0.8818	High Similarity	NPC260818
0.8818	High Similarity	NPC474157
0.8814	High Similarity	NPC246166
0.8774	High Similarity	NPC45613
0.8673	High Similarity	NPC210092
0.8667	High Similarity	NPC35448
0.8667	High Similarity	NPC78701
0.8649	High Similarity	NPC210089
0.8636	High Similarity	NPC85493
0.8636	High Similarity	NPC474364
0.8632	High Similarity	NPC50872
0.8585	High Similarity	NPC325497
0.8585	High Similarity	NPC146351
0.8571	High Similarity	NPC276775
0.8571	High Similarity	NPC92754
0.8571	High Similarity	NPC249912
0.8547	High Similarity	NPC473243
0.8532	High Similarity	NPC209632
0.8505	High Similarity	NPC70624
0.8496	Intermediate Similarity	NPC272524
0.8491	Intermediate Similarity	NPC225060
0.844	Intermediate Similarity	NPC114594
0.843	Intermediate Similarity	NPC121272
0.843	Intermediate Similarity	NPC476599
0.8421	Intermediate Similarity	NPC477411
0.8421	Intermediate Similarity	NPC237366
0.8421	Intermediate Similarity	NPC308744
0.8411	Intermediate Similarity	NPC203925
0.8381	Intermediate Similarity	NPC130398
0.8364	Intermediate Similarity	NPC269457
0.8361	Intermediate Similarity	NPC51292
0.8361	Intermediate Similarity	NPC169913
0.8349	Intermediate Similarity	NPC60679
0.8348	Intermediate Similarity	NPC474685
0.8333	Intermediate Similarity	NPC161611
0.8333	Intermediate Similarity	NPC474176
0.8333	Intermediate Similarity	NPC42211
0.8319	Intermediate Similarity	NPC167504
0.8319	Intermediate Similarity	NPC476003
0.8306	Intermediate Similarity	NPC147561
0.8304	Intermediate Similarity	NPC269023
0.8304	Intermediate Similarity	NPC99846
0.8279	Intermediate Similarity	NPC275576
0.8276	Intermediate Similarity	NPC226093
0.8261	Intermediate Similarity	NPC474363
0.8257	Intermediate Similarity	NPC188895
0.8246	Intermediate Similarity	NPC79496
0.8241	Intermediate Similarity	NPC118343
0.824	Intermediate Similarity	NPC470278
0.819	Intermediate Similarity	NPC474095
0.8182	Intermediate Similarity	NPC234305
0.8182	Intermediate Similarity	NPC472703
0.8175	Intermediate Similarity	NPC7012
0.816	Intermediate Similarity	NPC475508
0.816	Intermediate Similarity	NPC42234
0.812	Intermediate Similarity	NPC100353
0.8115	Intermediate Similarity	NPC472704
0.8103	Intermediate Similarity	NPC196075
0.8087	Intermediate Similarity	NPC474314
0.8065	Intermediate Similarity	NPC472706
0.8051	Intermediate Similarity	NPC190298
0.8049	Intermediate Similarity	NPC295664
0.8047	Intermediate Similarity	NPC329913
0.8047	Intermediate Similarity	NPC474608
0.8034	Intermediate Similarity	NPC306740
0.8034	Intermediate Similarity	NPC228936
0.8033	Intermediate Similarity	NPC223351
0.8031	Intermediate Similarity	NPC472394
0.8031	Intermediate Similarity	NPC477360
0.8031	Intermediate Similarity	NPC238370
0.8017	Intermediate Similarity	NPC144547
0.8016	Intermediate Similarity	NPC272946
0.8	Intermediate Similarity	NPC204784
0.8	Intermediate Similarity	NPC472707
0.8	Intermediate Similarity	NPC473325
0.8	Intermediate Similarity	NPC282895
0.7984	Intermediate Similarity	NPC473216
0.7984	Intermediate Similarity	NPC195647
0.7984	Intermediate Similarity	NPC311339
0.7984	Intermediate Similarity	NPC66761
0.7984	Intermediate Similarity	NPC17877
0.7984	Intermediate Similarity	NPC291638
0.7984	Intermediate Similarity	NPC472577
0.7984	Intermediate Similarity	NPC473399
0.7983	Intermediate Similarity	NPC469574
0.7982	Intermediate Similarity	NPC229242
0.7967	Intermediate Similarity	NPC471466
0.7966	Intermediate Similarity	NPC135730
0.7946	Intermediate Similarity	NPC85977
0.7934	Intermediate Similarity	NPC289432
0.7934	Intermediate Similarity	NPC988
0.7934	Intermediate Similarity	NPC77000
0.7934	Intermediate Similarity	NPC238861
0.7934	Intermediate Similarity	NPC232958
0.7931	Intermediate Similarity	NPC158282
0.7931	Intermediate Similarity	NPC212415
0.792	Intermediate Similarity	NPC470753
0.792	Intermediate Similarity	NPC473220
0.7907	Intermediate Similarity	NPC203486
0.7907	Intermediate Similarity	NPC48929
0.7907	Intermediate Similarity	NPC477359
0.7907	Intermediate Similarity	NPC134937
0.7907	Intermediate Similarity	NPC126516
0.7907	Intermediate Similarity	NPC477368
0.7907	Intermediate Similarity	NPC324898
0.7907	Intermediate Similarity	NPC298547
0.7905	Intermediate Similarity	NPC173443
0.7891	Intermediate Similarity	NPC233692
0.7891	Intermediate Similarity	NPC233860
0.7891	Intermediate Similarity	NPC239358
0.789	Intermediate Similarity	NPC270654
0.7881	Intermediate Similarity	NPC470764
0.7879	Intermediate Similarity	NPC477904
0.7879	Intermediate Similarity	NPC475400
0.7879	Intermediate Similarity	NPC183270
0.7874	Intermediate Similarity	NPC473247
0.7863	Intermediate Similarity	NPC13784
0.7863	Intermediate Similarity	NPC183122
0.7863	Intermediate Similarity	NPC475373
0.7863	Intermediate Similarity	NPC283375
0.7857	Intermediate Similarity	NPC115797
0.7857	Intermediate Similarity	NPC255676
0.7857	Intermediate Similarity	NPC51448
0.7846	Intermediate Similarity	NPC475262
0.7846	Intermediate Similarity	NPC477896
0.7846	Intermediate Similarity	NPC279637
0.7846	Intermediate Similarity	NPC477367
0.7846	Intermediate Similarity	NPC232888
0.7846	Intermediate Similarity	NPC149401
0.7846	Intermediate Similarity	NPC477893
0.7846	Intermediate Similarity	NPC200154
0.7846	Intermediate Similarity	NPC270364
0.7846	Intermediate Similarity	NPC265459
0.7846	Intermediate Similarity	NPC290833
0.7845	Intermediate Similarity	NPC243355
0.784	Intermediate Similarity	NPC470765
0.784	Intermediate Similarity	NPC476033
0.7833	Intermediate Similarity	NPC228318
0.7829	Intermediate Similarity	NPC472248
0.7829	Intermediate Similarity	NPC472656
0.7829	Intermediate Similarity	NPC477364
0.7823	Intermediate Similarity	NPC228739
0.7823	Intermediate Similarity	NPC51079
0.7812	Intermediate Similarity	NPC72915
0.7812	Intermediate Similarity	NPC475478
0.7812	Intermediate Similarity	NPC282230
0.7812	Intermediate Similarity	NPC183348
0.781	Intermediate Similarity	NPC304760
0.7803	Intermediate Similarity	NPC475652
0.7803	Intermediate Similarity	NPC214550
0.7803	Intermediate Similarity	NPC210591
0.7786	Intermediate Similarity	NPC477358
0.7786	Intermediate Similarity	NPC285221
0.7786	Intermediate Similarity	NPC194769
0.7769	Intermediate Similarity	NPC28836
0.7769	Intermediate Similarity	NPC153617
0.7769	Intermediate Similarity	NPC472250
0.7769	Intermediate Similarity	NPC311492
0.7768	Intermediate Similarity	NPC284477
0.7768	Intermediate Similarity	NPC304873
0.7768	Intermediate Similarity	NPC25458
0.776	Intermediate Similarity	NPC125053
0.7752	Intermediate Similarity	NPC470976
0.7752	Intermediate Similarity	NPC196979
0.7752	Intermediate Similarity	NPC470977
0.7752	Intermediate Similarity	NPC475569
0.7752	Intermediate Similarity	NPC15083
0.7748	Intermediate Similarity	NPC217621
0.7744	Intermediate Similarity	NPC43241
0.7744	Intermediate Similarity	NPC473081
0.7744	Intermediate Similarity	NPC275592
0.7744	Intermediate Similarity	NPC171207
0.7744	Intermediate Similarity	NPC147880
0.7744	Intermediate Similarity	NPC473109

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 NPC307651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	835
0.2-0.3	1252
0.3-0.4	2568
0.4-0.5	2481
0.5-0.6	1310
0.6-0.7	441
0.7-0.8	50
0.8-0.85	4
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9714	High Similarity	NPD2181	Clinical (unspecified phase)
0.934	High Similarity	NPD2182	Approved
0.8962	High Similarity	NPD164	Approved
0.8241	Intermediate Similarity	NPD1238	Approved
0.823	Intermediate Similarity	NPD2067	Discontinued
0.816	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6287	Discontinued
0.7734	Intermediate Similarity	NPD7008	Discontinued
0.7731	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3764	Approved
0.7672	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9259	Approved
0.7619	Intermediate Similarity	NPD9257	Approved
0.7615	Intermediate Similarity	NPD1202	Approved
0.7583	Intermediate Similarity	NPD5951	Approved
0.7544	Intermediate Similarity	NPD6647	Phase 2
0.7477	Intermediate Similarity	NPD1989	Approved
0.7391	Intermediate Similarity	NPD1930	Approved
0.7391	Intermediate Similarity	NPD1929	Approved
0.7391	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2567	Approved
0.7388	Intermediate Similarity	NPD2569	Approved
0.7381	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2199	Approved
0.7344	Intermediate Similarity	NPD1876	Approved
0.7344	Intermediate Similarity	NPD2198	Approved
0.7339	Intermediate Similarity	NPD3673	Approved
0.7339	Intermediate Similarity	NPD9258	Approved
0.7339	Intermediate Similarity	NPD9545	Approved
0.7339	Intermediate Similarity	NPD9256	Approved
0.7339	Intermediate Similarity	NPD3672	Approved
0.7338	Intermediate Similarity	NPD7236	Approved
0.7328	Intermediate Similarity	NPD5909	Discontinued
0.7328	Intermediate Similarity	NPD1237	Approved
0.7302	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD2629	Approved
0.7281	Intermediate Similarity	NPD2066	Phase 3
0.7273	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6085	Phase 2
0.7226	Intermediate Similarity	NPD2346	Discontinued
0.7222	Intermediate Similarity	NPD1087	Approved
0.7222	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9495	Approved
0.7188	Intermediate Similarity	NPD6637	Approved
0.7177	Intermediate Similarity	NPD9493	Approved
0.7164	Intermediate Similarity	NPD2979	Phase 3
0.7155	Intermediate Similarity	NPD1932	Approved
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7094	Approved
0.7131	Intermediate Similarity	NPD6858	Approved
0.712	Intermediate Similarity	NPD6065	Approved
0.7101	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1019	Discontinued
0.7097	Intermediate Similarity	NPD4198	Discontinued
0.7083	Intermediate Similarity	NPD7239	Suspended
0.708	Intermediate Similarity	NPD1693	Approved
0.708	Intermediate Similarity	NPD9260	Approved
0.708	Intermediate Similarity	NPD2799	Discontinued
0.7077	Intermediate Similarity	NPD5667	Approved
0.7073	Intermediate Similarity	NPD1241	Discontinued
0.7071	Intermediate Similarity	NPD4628	Phase 3
0.7063	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD6685	Approved
0.7059	Intermediate Similarity	NPD3134	Approved
0.7059	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3972	Approved
0.7049	Intermediate Similarity	NPD969	Suspended
0.7037	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1089	Approved
0.7027	Intermediate Similarity	NPD1086	Approved
0.7027	Intermediate Similarity	NPD1090	Approved
0.7	Intermediate Similarity	NPD1358	Approved
0.6993	Remote Similarity	NPD2533	Approved
0.6993	Remote Similarity	NPD2532	Approved
0.6993	Remote Similarity	NPD2534	Approved
0.6985	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2347	Approved
0.6983	Remote Similarity	NPD7798	Approved
0.6977	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1281	Approved
0.697	Remote Similarity	NPD2798	Approved
0.6964	Remote Similarity	NPD7609	Phase 3
0.6963	Remote Similarity	NPD7713	Phase 3
0.6957	Remote Similarity	NPD3748	Approved
0.6953	Remote Similarity	NPD5126	Approved
0.6953	Remote Similarity	NPD5125	Phase 3
0.6952	Remote Similarity	NPD9490	Approved
0.6949	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2329	Discontinued
0.694	Remote Similarity	NPD6039	Approved
0.6937	Remote Similarity	NPD800	Approved
0.693	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9717	Approved
0.6912	Remote Similarity	NPD3373	Approved
0.6912	Remote Similarity	NPD4307	Phase 2
0.6909	Remote Similarity	NPD1282	Approved
0.6906	Remote Similarity	NPD2438	Suspended
0.6906	Remote Similarity	NPD2935	Discontinued
0.6903	Remote Similarity	NPD7631	Approved
0.6903	Remote Similarity	NPD1088	Approved
0.6897	Remote Similarity	NPD5926	Approved
0.6891	Remote Similarity	NPD3048	Approved
0.6891	Remote Similarity	NPD3047	Approved
0.6891	Remote Similarity	NPD3046	Approved
0.6885	Remote Similarity	NPD1317	Discontinued
0.6885	Remote Similarity	NPD5239	Approved
0.6885	Remote Similarity	NPD5240	Approved
0.6885	Remote Similarity	NPD4234	Approved
0.6885	Remote Similarity	NPD5236	Approved
0.6885	Remote Similarity	NPD4233	Approved
0.6885	Remote Similarity	NPD5235	Approved
0.6885	Remote Similarity	NPD5237	Approved
0.688	Remote Similarity	NPD4766	Approved
0.6875	Remote Similarity	NPD5585	Approved
0.687	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6355	Discontinued
0.6861	Remote Similarity	NPD230	Phase 1
0.6857	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6005	Phase 3
0.6857	Remote Similarity	NPD227	Approved
0.6857	Remote Similarity	NPD6002	Phase 3
0.6857	Remote Similarity	NPD6004	Phase 3
0.6857	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD225	Approved
0.6857	Remote Similarity	NPD1471	Phase 3
0.6855	Remote Similarity	NPD5277	Phase 2
0.6852	Remote Similarity	NPD9491	Approved
0.6838	Remote Similarity	NPD7961	Discontinued
0.6831	Remote Similarity	NPD7003	Approved
0.6829	Remote Similarity	NPD2201	Approved
0.6822	Remote Similarity	NPD5305	Approved
0.6822	Remote Similarity	NPD4626	Approved
0.6822	Remote Similarity	NPD5306	Approved
0.6822	Remote Similarity	NPD17	Approved
0.6818	Remote Similarity	NPD1283	Approved
0.6812	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5765	Approved
0.6807	Remote Similarity	NPD9261	Approved
0.6803	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2652	Approved
0.68	Remote Similarity	NPD2650	Approved
0.6794	Remote Similarity	NPD1877	Discontinued
0.6791	Remote Similarity	NPD5204	Approved
0.6791	Remote Similarity	NPD3661	Approved
0.6791	Remote Similarity	NPD3664	Approved
0.6791	Remote Similarity	NPD3663	Approved
0.6791	Remote Similarity	NPD3662	Phase 3
0.6786	Remote Similarity	NPD2531	Phase 2
0.6783	Remote Similarity	NPD3887	Approved
0.6769	Remote Similarity	NPD4136	Approved
0.6769	Remote Similarity	NPD4135	Approved
0.6769	Remote Similarity	NPD3496	Discontinued
0.6769	Remote Similarity	NPD4106	Approved
0.6767	Remote Similarity	NPD3267	Approved
0.6767	Remote Similarity	NPD553	Approved
0.6767	Remote Similarity	NPD552	Approved
0.6767	Remote Similarity	NPD2797	Approved
0.6767	Remote Similarity	NPD3266	Approved
0.6767	Remote Similarity	NPD9567	Approved
0.6761	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD650	Approved
0.6755	Remote Similarity	NPD7058	Phase 2
0.6755	Remote Similarity	NPD7057	Phase 3
0.6744	Remote Similarity	NPD1651	Approved
0.6739	Remote Similarity	NPD447	Suspended
0.6739	Remote Similarity	NPD4622	Approved
0.6739	Remote Similarity	NPD4618	Approved
0.6718	Remote Similarity	NPD4807	Approved
0.6718	Remote Similarity	NPD4806	Approved
0.6716	Remote Similarity	NPD5647	Approved
0.6715	Remote Similarity	NPD8032	Phase 2
0.6715	Remote Similarity	NPD6663	Approved
0.6714	Remote Similarity	NPD7305	Phase 1
0.6714	Remote Similarity	NPD4308	Phase 3
0.6713	Remote Similarity	NPD3750	Approved
0.6696	Remote Similarity	NPD1563	Approved
0.6694	Remote Similarity	NPD5048	Discontinued
0.669	Remote Similarity	NPD2897	Discontinued
0.6689	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD1239	Approved
0.6667	Remote Similarity	NPD4477	Approved
0.6667	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD3495	Discontinued

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