NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	2.61
LogD:	2.186
LogS:	-3.325
# Rotatable Bonds:	1
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	3.669
Fsp3:	0.333
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:	-4.65
MDCK Permeability:	3.511465183692053e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.454
30% Bioavailability (F30%):	0.889

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.958
Plasma Protein Binding (PPB):	86.53899383544922%
Volume Distribution (VD):	0.988
Pgp-substrate:	17.529071807861328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.41
CYP1A2-substrate:	0.525
CYP2C19-inhibitor:	0.764
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.482
CYP2C9-substrate:	0.507
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.482
CYP3A4-inhibitor:	0.422
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	2.747
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.45
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.216
Carcinogencity:	0.234
Eye Corrosion:	0.009
Eye Irritation:	0.207
Respiratory Toxicity:	0.202

Download Data

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

Natural Product: NPC149691

Natural Product ID:	NPC149691
*Common Name:**	Catalpalactone
IUPAC Name:	3-(2,2-dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-one
Synonyms:	Catalpalactone
Standard InCHIKey:	GFYSRANGENPXDF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-15(2)8-7-11(14(17)19-15)12-9-5-3-4-6-10(9)13(16)18-12/h3-7,12H,8H2,1-2H3
SMILES:	O=C1OC(C)(C)CC=C1C1OC(=O)c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471809
PubChem CID:	3014018
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
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00579992]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.foodchem.2010.03.088]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO18077	Liquidambar formosana	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29019685]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31738062]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4013523]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18077	Liquidambar formosana	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO18077	Liquidambar formosana	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10226	Fructus vitis viniferae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18077	Liquidambar formosana	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18077	Liquidambar formosana	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3359	Psidium guajava	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18077	Liquidambar formosana	Species	Altingiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1879	Feijoa sellowiana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[564928]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[564928]
NPT2	Others	Unspecified		Activity	=	27.9	%	PMID[564928]
NPT2	Others	Unspecified		Activity	=	52.8	%	PMID[564928]
NPT2	Others	Unspecified		Activity	=	89.5	%	PMID[564928]

☑ 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 NPC149691 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	255
0.1-0.2	1142
0.2-0.3	2650
0.3-0.4	7221
0.4-0.5	11791
0.5-0.6	11022
0.6-0.7	7560
0.7-0.8	959
0.8-0.85	69
0.85-0.9	26
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC83628
0.9167	High Similarity	NPC265407
0.9099	High Similarity	NPC307651
0.9009	High Similarity	NPC474176
0.9	High Similarity	NPC474157
0.8879	High Similarity	NPC89886
0.8807	High Similarity	NPC119271
0.8807	High Similarity	NPC37622
0.8807	High Similarity	NPC30594
0.8761	High Similarity	NPC308744
0.8727	High Similarity	NPC56493
0.8716	High Similarity	NPC209632
0.8673	High Similarity	NPC272524
0.8649	High Similarity	NPC10251
0.8649	High Similarity	NPC17417
0.8624	High Similarity	NPC114594
0.8624	High Similarity	NPC31786
0.8611	High Similarity	NPC45613
0.8571	High Similarity	NPC251854
0.8571	High Similarity	NPC196246
0.8571	High Similarity	NPC174099
0.8571	High Similarity	NPC93084
0.8571	High Similarity	NPC214067
0.8532	High Similarity	NPC60679
0.8522	High Similarity	NPC210092
0.8522	High Similarity	NPC474685
0.8496	Intermediate Similarity	NPC210089
0.8496	Intermediate Similarity	NPC260818
0.8496	Intermediate Similarity	NPC305912
0.8496	Intermediate Similarity	NPC1082
0.8482	Intermediate Similarity	NPC99846
0.8482	Intermediate Similarity	NPC269023
0.8421	Intermediate Similarity	NPC82899
0.8421	Intermediate Similarity	NPC321852
0.8421	Intermediate Similarity	NPC270699
0.8411	Intermediate Similarity	NPC92754
0.8411	Intermediate Similarity	NPC249912
0.8411	Intermediate Similarity	NPC276775
0.8364	Intermediate Similarity	NPC474365
0.8364	Intermediate Similarity	NPC234305
0.8364	Intermediate Similarity	NPC301943
0.8361	Intermediate Similarity	NPC246166
0.8349	Intermediate Similarity	NPC70624
0.8349	Intermediate Similarity	NPC42211
0.8348	Intermediate Similarity	NPC128368
0.8333	Intermediate Similarity	NPC35448
0.8333	Intermediate Similarity	NPC225060
0.8333	Intermediate Similarity	NPC50872
0.8333	Intermediate Similarity	NPC78701
0.8319	Intermediate Similarity	NPC469636
0.8319	Intermediate Similarity	NPC474364
0.8319	Intermediate Similarity	NPC85493
0.8276	Intermediate Similarity	NPC477411
0.8276	Intermediate Similarity	NPC474363
0.8276	Intermediate Similarity	NPC153053
0.8257	Intermediate Similarity	NPC203925
0.8257	Intermediate Similarity	NPC146351
0.8257	Intermediate Similarity	NPC325497
0.8257	Intermediate Similarity	NPC118343
0.8224	Intermediate Similarity	NPC130398
0.822	Intermediate Similarity	NPC190298
0.8197	Intermediate Similarity	NPC474283
0.8197	Intermediate Similarity	NPC475692
0.8197	Intermediate Similarity	NPC223351
0.8197	Intermediate Similarity	NPC472703
0.819	Intermediate Similarity	NPC161611
0.8174	Intermediate Similarity	NPC167504
0.8145	Intermediate Similarity	NPC476599
0.8136	Intermediate Similarity	NPC226093
0.8136	Intermediate Similarity	NPC100353
0.813	Intermediate Similarity	NPC475691
0.813	Intermediate Similarity	NPC472704
0.812	Intermediate Similarity	NPC237366
0.812	Intermediate Similarity	NPC196075
0.8108	Intermediate Similarity	NPC188895
0.8103	Intermediate Similarity	NPC79496
0.8103	Intermediate Similarity	NPC212415
0.8099	Intermediate Similarity	NPC473243
0.808	Intermediate Similarity	NPC51292
0.808	Intermediate Similarity	NPC472706
0.8053	Intermediate Similarity	NPC269457
0.8031	Intermediate Similarity	NPC147561
0.8017	Intermediate Similarity	NPC243355
0.8016	Intermediate Similarity	NPC472707
0.8	Intermediate Similarity	NPC121272
0.7965	Intermediate Similarity	NPC85977
0.7949	Intermediate Similarity	NPC158282
0.7949	Intermediate Similarity	NPC474314
0.7913	Intermediate Similarity	NPC277788
0.7907	Intermediate Similarity	NPC7012
0.7899	Intermediate Similarity	NPC306740
0.7899	Intermediate Similarity	NPC474095
0.7895	Intermediate Similarity	NPC477904
0.7895	Intermediate Similarity	NPC183270
0.7881	Intermediate Similarity	NPC13784
0.7863	Intermediate Similarity	NPC476003
0.7845	Intermediate Similarity	NPC40178
0.7838	Intermediate Similarity	NPC229242
0.7833	Intermediate Similarity	NPC135730
0.7829	Intermediate Similarity	NPC470278
0.7815	Intermediate Similarity	NPC87069
0.7795	Intermediate Similarity	NPC169913
0.7786	Intermediate Similarity	NPC153617
0.7786	Intermediate Similarity	NPC474608
0.7778	Intermediate Similarity	NPC265910
0.7778	Intermediate Similarity	NPC91475
0.7769	Intermediate Similarity	NPC238370
0.7768	Intermediate Similarity	NPC472318
0.7768	Intermediate Similarity	NPC98911
0.776	Intermediate Similarity	NPC46634
0.7759	Intermediate Similarity	NPC20485
0.7759	Intermediate Similarity	NPC470391
0.7759	Intermediate Similarity	NPC47536
0.7759	Intermediate Similarity	NPC211439
0.7757	Intermediate Similarity	NPC173443
0.7752	Intermediate Similarity	NPC42234
0.7752	Intermediate Similarity	NPC475508
0.775	Intermediate Similarity	NPC228936
0.775	Intermediate Similarity	NPC470764
0.775	Intermediate Similarity	NPC474408
0.7748	Intermediate Similarity	NPC270654
0.7742	Intermediate Similarity	NPC144547
0.7727	Intermediate Similarity	NPC291638
0.7727	Intermediate Similarity	NPC195647
0.7727	Intermediate Similarity	NPC17877
0.7727	Intermediate Similarity	NPC66761
0.7727	Intermediate Similarity	NPC472577
0.7719	Intermediate Similarity	NPC255676
0.7717	Intermediate Similarity	NPC275576
0.7717	Intermediate Similarity	NPC476033
0.7705	Intermediate Similarity	NPC469574
0.7705	Intermediate Similarity	NPC217423
0.7704	Intermediate Similarity	NPC187566
0.7699	Intermediate Similarity	NPC473325
0.7699	Intermediate Similarity	NPC282895
0.7698	Intermediate Similarity	NPC471466
0.7698	Intermediate Similarity	NPC228739
0.7692	Intermediate Similarity	NPC60825
0.7692	Intermediate Similarity	NPC473271
0.7692	Intermediate Similarity	NPC291419
0.7686	Intermediate Similarity	NPC216387
0.7681	Intermediate Similarity	NPC184702
0.7672	Intermediate Similarity	NPC475203
0.7672	Intermediate Similarity	NPC474376
0.7672	Intermediate Similarity	NPC472316
0.7672	Intermediate Similarity	NPC472315
0.7669	Intermediate Similarity	NPC217673
0.7669	Intermediate Similarity	NPC52523
0.7664	Intermediate Similarity	NPC304760
0.7664	Intermediate Similarity	NPC297985
0.7661	Intermediate Similarity	NPC988
0.7661	Intermediate Similarity	NPC232958
0.7661	Intermediate Similarity	NPC289432
0.7656	Intermediate Similarity	NPC470753
0.7656	Intermediate Similarity	NPC473220
0.7652	Intermediate Similarity	NPC43627
0.7652	Intermediate Similarity	NPC324898
0.7652	Intermediate Similarity	NPC298547
0.7652	Intermediate Similarity	NPC134937
0.7642	Intermediate Similarity	NPC94637
0.7638	Intermediate Similarity	NPC125053
0.7638	Intermediate Similarity	NPC295664
0.7636	Intermediate Similarity	NPC261181
0.7634	Intermediate Similarity	NPC470831
0.7634	Intermediate Similarity	NPC214702
0.7634	Intermediate Similarity	NPC477360
0.7632	Intermediate Similarity	NPC284477
0.763	Intermediate Similarity	NPC61590
0.7619	Intermediate Similarity	NPC65627
0.7619	Intermediate Similarity	NPC217756
0.7615	Intermediate Similarity	NPC272946
0.7615	Intermediate Similarity	NPC82712
0.7612	Intermediate Similarity	NPC183122
0.7612	Intermediate Similarity	NPC475373
0.7612	Intermediate Similarity	NPC86772
0.7612	Intermediate Similarity	NPC283375
0.7609	Intermediate Similarity	NPC21873
0.7609	Intermediate Similarity	NPC471100
0.7609	Intermediate Similarity	NPC471107
0.7597	Intermediate Similarity	NPC181715
0.7594	Intermediate Similarity	NPC79699
0.7594	Intermediate Similarity	NPC279637
0.7594	Intermediate Similarity	NPC474097
0.7594	Intermediate Similarity	NPC473399
0.7594	Intermediate Similarity	NPC149401
0.7594	Intermediate Similarity	NPC473216
0.7581	Intermediate Similarity	NPC328459
0.7581	Intermediate Similarity	NPC204784
0.7581	Intermediate Similarity	NPC90522
0.7578	Intermediate Similarity	NPC79608
0.7578	Intermediate Similarity	NPC470765
0.7578	Intermediate Similarity	NPC236405
0.7574	Intermediate Similarity	NPC77493
0.7574	Intermediate Similarity	NPC295339
0.757	Intermediate Similarity	NPC89377
0.7563	Intermediate Similarity	NPC291799
0.7561	Intermediate Similarity	NPC228318
0.7561	Intermediate Similarity	NPC45104
0.7557	Intermediate Similarity	NPC469519
0.7556	Intermediate Similarity	NPC325805

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 NPC149691 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	832
0.2-0.3	1296
0.3-0.4	2638
0.4-0.5	2476
0.5-0.6	1215
0.6-0.7	426
0.7-0.8	44
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD2181	Clinical (unspecified phase)
0.8649	High Similarity	NPD2182	Approved
0.8624	High Similarity	NPD164	Approved
0.8257	Intermediate Similarity	NPD1238	Approved
0.8103	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1202	Approved
0.7603	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3764	Approved
0.752	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9493	Approved
0.7479	Intermediate Similarity	NPD2067	Discontinued
0.7477	Intermediate Similarity	NPD9257	Approved
0.7477	Intermediate Similarity	NPD9259	Approved
0.7407	Intermediate Similarity	NPD2569	Approved
0.7407	Intermediate Similarity	NPD2567	Approved
0.7405	Intermediate Similarity	NPD6832	Phase 2
0.7402	Intermediate Similarity	NPD6287	Discontinued
0.7348	Intermediate Similarity	NPD7008	Discontinued
0.7266	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1019	Discontinued
0.725	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1282	Approved
0.7222	Intermediate Similarity	NPD9545	Approved
0.7209	Intermediate Similarity	NPD9717	Approved
0.7207	Intermediate Similarity	NPD9258	Approved
0.7207	Intermediate Similarity	NPD9256	Approved
0.7203	Intermediate Similarity	NPD1237	Approved
0.7177	Intermediate Similarity	NPD5951	Approved
0.7164	Intermediate Similarity	NPD2313	Discontinued
0.7132	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2346	Discontinued
0.7119	Intermediate Similarity	NPD1929	Approved
0.7119	Intermediate Similarity	NPD1930	Approved
0.7119	Intermediate Similarity	NPD9261	Approved
0.7119	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6647	Phase 2
0.7113	Intermediate Similarity	NPD7236	Approved
0.7099	Intermediate Similarity	NPD2199	Approved
0.7099	Intermediate Similarity	NPD2198	Approved
0.7099	Intermediate Similarity	NPD1876	Approved
0.7097	Intermediate Similarity	NPD1241	Discontinued
0.7077	Intermediate Similarity	NPD6637	Approved
0.7071	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9495	Approved
0.7059	Intermediate Similarity	NPD5909	Discontinued
0.7059	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4307	Phase 2
0.7054	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1203	Approved
0.7043	Intermediate Similarity	NPD1989	Approved
0.7	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6085	Phase 2
0.6992	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2798	Approved
0.6992	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3748	Approved
0.6978	Remote Similarity	NPD2799	Discontinued
0.6972	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9260	Approved
0.6939	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD969	Suspended
0.6929	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD920	Approved
0.6905	Remote Similarity	NPD2629	Approved
0.6891	Remote Similarity	NPD1932	Approved
0.6885	Remote Similarity	NPD9263	Approved
0.6885	Remote Similarity	NPD9264	Approved
0.6885	Remote Similarity	NPD9267	Approved
0.6884	Remote Similarity	NPD447	Suspended
0.6884	Remote Similarity	NPD1933	Approved
0.6875	Remote Similarity	NPD2347	Approved
0.6871	Remote Similarity	NPD7239	Suspended
0.687	Remote Similarity	NPD1281	Approved
0.6864	Remote Similarity	NPD2066	Phase 3
0.6864	Remote Similarity	NPD7798	Approved
0.6857	Remote Similarity	NPD4308	Phase 3
0.685	Remote Similarity	NPD4198	Discontinued
0.6846	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5667	Approved
0.6829	Remote Similarity	NPD74	Approved
0.6829	Remote Similarity	NPD9266	Approved
0.6825	Remote Similarity	NPD2650	Approved
0.6825	Remote Similarity	NPD2652	Approved
0.6822	Remote Similarity	NPD9490	Approved
0.681	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2796	Approved
0.6809	Remote Similarity	NPD2935	Discontinued
0.6809	Remote Similarity	NPD1551	Phase 2
0.6791	Remote Similarity	NPD3267	Approved
0.6791	Remote Similarity	NPD3266	Approved
0.6788	Remote Similarity	NPD411	Approved
0.6786	Remote Similarity	NPD650	Approved
0.6786	Remote Similarity	NPD1087	Approved
0.6783	Remote Similarity	NPD1243	Approved
0.6781	Remote Similarity	NPD2532	Approved
0.6781	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2534	Approved
0.6781	Remote Similarity	NPD2533	Approved
0.6763	Remote Similarity	NPD230	Phase 1
0.6761	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD3673	Approved
0.6754	Remote Similarity	NPD3672	Approved
0.6748	Remote Similarity	NPD1358	Approved
0.6746	Remote Similarity	NPD6858	Approved
0.6746	Remote Similarity	NPD7094	Approved
0.6736	Remote Similarity	NPD4628	Phase 3
0.6736	Remote Similarity	NPD3750	Approved
0.6735	Remote Similarity	NPD6273	Approved
0.6729	Remote Similarity	NPD225	Approved
0.6729	Remote Similarity	NPD227	Approved
0.6727	Remote Similarity	NPD9491	Approved
0.6724	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5048	Discontinued
0.6718	Remote Similarity	NPD17	Approved
0.6716	Remote Similarity	NPD1283	Approved
0.6714	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2329	Discontinued
0.6693	Remote Similarity	NPD6010	Discontinued
0.6692	Remote Similarity	NPD3972	Approved
0.6691	Remote Similarity	NPD2979	Phase 3
0.669	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD553	Approved
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD9567	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD1164	Approved
0.6667	Remote Similarity	NPD552	Approved
0.6645	Remote Similarity	NPD7819	Suspended
0.6643	Remote Similarity	NPD2344	Approved
0.6642	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD9281	Approved
0.6641	Remote Similarity	NPD5691	Approved
0.664	Remote Similarity	NPD5240	Approved
0.664	Remote Similarity	NPD5235	Approved
0.664	Remote Similarity	NPD5236	Approved
0.664	Remote Similarity	NPD5239	Approved
0.664	Remote Similarity	NPD5237	Approved
0.6623	Remote Similarity	NPD3749	Approved
0.662	Remote Similarity	NPD7033	Discontinued
0.662	Remote Similarity	NPD1510	Phase 2
0.6619	Remote Similarity	NPD7713	Phase 3
0.6619	Remote Similarity	NPD520	Approved
0.6618	Remote Similarity	NPD5647	Approved
0.6617	Remote Similarity	NPD2609	Approved
0.6617	Remote Similarity	NPD3131	Approved
0.6617	Remote Similarity	NPD4215	Approved
0.6617	Remote Similarity	NPD4216	Approved
0.6617	Remote Similarity	NPD3132	Approved
0.6617	Remote Similarity	NPD2608	Approved
0.6617	Remote Similarity	NPD2610	Approved
0.6617	Remote Similarity	NPD4218	Approved
0.6617	Remote Similarity	NPD2611	Approved
0.6617	Remote Similarity	NPD4217	Approved
0.6617	Remote Similarity	NPD2612	Approved
0.6615	Remote Similarity	NPD6065	Approved
0.6609	Remote Similarity	NPD1089	Approved
0.6609	Remote Similarity	NPD1090	Approved
0.6609	Remote Similarity	NPD1086	Approved
0.66	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3226	Approved
0.6599	Remote Similarity	NPD6799	Approved
0.6594	Remote Similarity	NPD6039	Approved
0.6591	Remote Similarity	NPD5125	Phase 3
0.6591	Remote Similarity	NPD5126	Approved
0.6591	Remote Similarity	NPD5306	Approved
0.6591	Remote Similarity	NPD5305	Approved
0.6587	Remote Similarity	NPD2201	Approved
0.6585	Remote Similarity	NPD9697	Approved
0.6581	Remote Similarity	NPD1563	Approved
0.6577	Remote Similarity	NPD5403	Approved
0.6575	Remote Similarity	NPD3887	Approved
0.6571	Remote Similarity	NPD3373	Approved
0.6569	Remote Similarity	NPD5204	Approved
0.6567	Remote Similarity	NPD1608	Approved
0.6565	Remote Similarity	NPD1894	Discontinued
0.6561	Remote Similarity	NPD6808	Phase 2
0.6558	Remote Similarity	NPD7058	Phase 2
0.6558	Remote Similarity	NPD7057	Phase 3
0.6557	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1239	Approved
0.6552	Remote Similarity	NPD7609	Phase 3
0.6547	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3268	Approved
0.6545	Remote Similarity	NPD226	Approved
0.6541	Remote Similarity	NPD4106	Approved
0.6541	Remote Similarity	NPD4135	Approved
0.6541	Remote Similarity	NPD4136	Approved
0.6535	Remote Similarity	NPD9508	Approved
0.6532	Remote Similarity	NPD6685	Approved
0.6525	Remote Similarity	NPD6355	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