NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.09
Volume:	247.009
LogP:	2.187
LogD:	1.64
LogS:	-3.497
# Rotatable Bonds:	0
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	3.198
Fsp3:	0.357
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:	-4.795
MDCK Permeability:	1.8712298697209917e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.905
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	89.76070404052734%
Volume Distribution (VD):	1.021
Pgp-substrate:	11.039514541625977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.931
CYP1A2-substrate:	0.826
CYP2C19-inhibitor:	0.313
CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.186
CYP2C9-substrate:	0.807
CYP2D6-inhibitor:	0.335
CYP2D6-substrate:	0.583
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	10.475
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.973
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.286
Carcinogencity:	0.914
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC224543

Natural Product ID:	NPC224543
*Common Name:**	(+)-Lomatin
IUPAC Name:	(9R)-9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
Synonyms:	(+)-Lomatin; Lomatin
Standard InCHIKey:	UJSHBYQGQRPVNO-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C14H14O4/c1-14(2)11(15)7-9-10(18-14)5-3-8-4-6-12(16)17-13(8)9/h3-6,11,15H,7H2,1-2H3/t11-/m1/s1
SMILES:	O=c1ccc2c(o1)c1C[C@@H](O)C(Oc1cc2)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503137
PubChem CID:	759302
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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO32915	prionosciadium watsoni	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088423]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
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]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6800	Libanotis buchtormensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6800	Libanotis buchtormensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	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[TCM_Taiwan]
NPO2921	Angelica acutiloba	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[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14809	Talaromyces avellaneus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5497	Stachys chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6800	Libanotis buchtormensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6444	Humulus scandens	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2741	Ribes sanguineum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16614	Zanthoxylum spinosum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1821	Kopsia albiflora	Species	Apocynaceae	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	2
Potency	7

Activity Type	# Activity
Individual Protein	4
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[564325]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	4466.8	nM	PMID[564325]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[564326]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	344000.0	nM	PMID[564324]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	296000.0	nM	PMID[564324]
NPT2	Others	Unspecified		Potency	=	25929.0	nM	PMID[564325]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[564325]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[564325]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	22387.2	nM	PMID[564326]

☑ 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 NPC224543 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	355
0.1-0.2	1583
0.2-0.3	3907
0.3-0.4	9007
0.4-0.5	9588
0.5-0.6	4093
0.6-0.7	5931
0.7-0.8	4966
0.8-0.85	2521
0.85-0.9	561
0.9-0.95	135
0.95-1	50

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188380
1.0	High Similarity	NPC78746
0.9923	High Similarity	NPC294456
0.9923	High Similarity	NPC153818
0.9923	High Similarity	NPC212124
0.9923	High Similarity	NPC281014
0.9923	High Similarity	NPC184861
0.9923	High Similarity	NPC232246
0.9923	High Similarity	NPC225106
0.9773	High Similarity	NPC312881
0.9699	High Similarity	NPC152771
0.9699	High Similarity	NPC195357
0.9699	High Similarity	NPC287286
0.9697	High Similarity	NPC279573
0.9692	High Similarity	NPC62366
0.9621	High Similarity	NPC155963
0.9618	High Similarity	NPC472525
0.9618	High Similarity	NPC33986
0.9549	High Similarity	NPC211110
0.9549	High Similarity	NPC151946
0.9545	High Similarity	NPC38099
0.9545	High Similarity	NPC26954
0.9542	High Similarity	NPC224475
0.9542	High Similarity	NPC180716
0.9542	High Similarity	NPC253574
0.9542	High Similarity	NPC50896
0.9542	High Similarity	NPC213173
0.9542	High Similarity	NPC204353
0.9542	High Similarity	NPC98179
0.9542	High Similarity	NPC326600
0.9466	High Similarity	NPC471910
0.9466	High Similarity	NPC133956
0.9466	High Similarity	NPC207002
0.9466	High Similarity	NPC296624
0.9466	High Similarity	NPC318400
0.9466	High Similarity	NPC167111
0.9416	High Similarity	NPC85624
0.9416	High Similarity	NPC469701
0.9394	High Similarity	NPC47163
0.9394	High Similarity	NPC198381
0.9394	High Similarity	NPC195343
0.9394	High Similarity	NPC74655
0.9394	High Similarity	NPC319859
0.9394	High Similarity	NPC267412
0.9394	High Similarity	NPC84894
0.9394	High Similarity	NPC127888
0.9394	High Similarity	NPC164269
0.9394	High Similarity	NPC166672
0.9394	High Similarity	NPC18804
0.9394	High Similarity	NPC287182
0.9394	High Similarity	NPC100986
0.9394	High Similarity	NPC260265
0.9389	High Similarity	NPC194277
0.9323	High Similarity	NPC471625
0.9323	High Similarity	NPC281241
0.9323	High Similarity	NPC472424
0.9323	High Similarity	NPC86892
0.9323	High Similarity	NPC471909
0.9318	High Similarity	NPC31849
0.9313	High Similarity	NPC29734
0.9281	High Similarity	NPC471764
0.9281	High Similarity	NPC87950
0.9281	High Similarity	NPC296377
0.9254	High Similarity	NPC160727
0.9254	High Similarity	NPC177281
0.9254	High Similarity	NPC476455
0.9254	High Similarity	NPC55615
0.9254	High Similarity	NPC283019
0.9254	High Similarity	NPC471630
0.9254	High Similarity	NPC128529
0.9254	High Similarity	NPC149320
0.9237	High Similarity	NPC113098
0.9231	High Similarity	NPC185066
0.9214	High Similarity	NPC169510
0.9203	High Similarity	NPC471824
0.9173	High Similarity	NPC163557
0.9167	High Similarity	NPC272650
0.9167	High Similarity	NPC267336
0.916	High Similarity	NPC168710
0.9104	High Similarity	NPC55149
0.9104	High Similarity	NPC307412
0.9098	High Similarity	NPC14248
0.9091	High Similarity	NPC80170
0.9084	High Similarity	NPC199204
0.9077	High Similarity	NPC471826
0.907	High Similarity	NPC111347
0.9065	High Similarity	NPC471763
0.9037	High Similarity	NPC469675
0.903	High Similarity	NPC7526
0.903	High Similarity	NPC469449
0.903	High Similarity	NPC222036
0.8971	High Similarity	NPC103409
0.8951	High Similarity	NPC103116
0.8931	High Similarity	NPC188327
0.8931	High Similarity	NPC234109
0.8905	High Similarity	NPC471069
0.8905	High Similarity	NPC471068
0.8889	High Similarity	NPC469965
0.8889	High Similarity	NPC141822
0.8889	High Similarity	NPC1220
0.8889	High Similarity	NPC291551
0.8889	High Similarity	NPC241165
0.8889	High Similarity	NPC142563
0.8889	High Similarity	NPC205797
0.8864	High Similarity	NPC258567
0.8864	High Similarity	NPC121740
0.8864	High Similarity	NPC224774
0.8864	High Similarity	NPC473993
0.8857	High Similarity	NPC183646
0.8857	High Similarity	NPC119640
0.8855	High Similarity	NPC244495
0.8855	High Similarity	NPC93219
0.8849	High Similarity	NPC476442
0.8849	High Similarity	NPC215512
0.8849	High Similarity	NPC279851
0.8849	High Similarity	NPC472520
0.8849	High Similarity	NPC300611
0.8846	High Similarity	NPC173350
0.8846	High Similarity	NPC290605
0.8846	High Similarity	NPC472518
0.8846	High Similarity	NPC154176
0.8841	High Similarity	NPC35501
0.8841	High Similarity	NPC270256
0.8841	High Similarity	NPC471070
0.8841	High Similarity	NPC278600
0.8841	High Similarity	NPC47040
0.8841	High Similarity	NPC471072
0.8841	High Similarity	NPC144512
0.8841	High Similarity	NPC137262
0.8841	High Similarity	NPC471071
0.8841	High Similarity	NPC37428
0.8832	High Similarity	NPC283331
0.8828	High Similarity	NPC470264
0.8824	High Similarity	NPC131950
0.8803	High Similarity	NPC205361
0.8797	High Similarity	NPC469453
0.8794	High Similarity	NPC476457
0.8779	High Similarity	NPC201667
0.8779	High Similarity	NPC73413
0.8769	High Similarity	NPC248429
0.8769	High Similarity	NPC13007
0.8769	High Similarity	NPC257188
0.8769	High Similarity	NPC96286
0.8768	High Similarity	NPC131198
0.8741	High Similarity	NPC476347
0.8741	High Similarity	NPC15577
0.8741	High Similarity	NPC103799
0.8732	High Similarity	NPC226722
0.8723	High Similarity	NPC236419
0.8722	High Similarity	NPC243688
0.8714	High Similarity	NPC138149
0.8712	High Similarity	NPC471827
0.8712	High Similarity	NPC471828
0.8702	High Similarity	NPC109675
0.8702	High Similarity	NPC273772
0.8696	High Similarity	NPC167517
0.8692	High Similarity	NPC144418
0.8686	High Similarity	NPC309953
0.8681	High Similarity	NPC187398
0.8681	High Similarity	NPC476348
0.8676	High Similarity	NPC123954
0.8676	High Similarity	NPC19157
0.8667	High Similarity	NPC32463
0.8657	High Similarity	NPC60704
0.8657	High Similarity	NPC472519
0.8657	High Similarity	NPC293642
0.8657	High Similarity	NPC139595
0.8652	High Similarity	NPC20631
0.8652	High Similarity	NPC93640
0.8639	High Similarity	NPC256141
0.8636	High Similarity	NPC27671
0.8636	High Similarity	NPC291899
0.8615	High Similarity	NPC163200
0.8613	High Similarity	NPC92805
0.8613	High Similarity	NPC2363
0.8613	High Similarity	NPC469955
0.8613	High Similarity	NPC469952
0.8605	High Similarity	NPC281356
0.8605	High Similarity	NPC298796
0.8603	High Similarity	NPC250727
0.8601	High Similarity	NPC295696
0.8601	High Similarity	NPC475719
0.8601	High Similarity	NPC106126
0.8601	High Similarity	NPC108994
0.8601	High Similarity	NPC101255
0.8601	High Similarity	NPC43716
0.8592	High Similarity	NPC138212
0.8592	High Similarity	NPC229916
0.8571	High Similarity	NPC207179
0.8571	High Similarity	NPC232692
0.8571	High Similarity	NPC167571
0.8571	High Similarity	NPC13067
0.8571	High Similarity	NPC168259
0.8571	High Similarity	NPC43500
0.8571	High Similarity	NPC278552
0.8571	High Similarity	NPC202594
0.8571	High Similarity	NPC164148
0.8562	High Similarity	NPC205727
0.8562	High Similarity	NPC120426
0.8562	High Similarity	NPC294522

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 NPC224543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	901
0.2-0.3	1801
0.3-0.4	2620
0.4-0.5	1890
0.5-0.6	1060
0.6-0.7	358
0.7-0.8	122
0.8-0.85	42
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD5124	Phase 1
0.8889	High Similarity	NPD5123	Clinical (unspecified phase)
0.8849	High Similarity	NPD1652	Phase 2
0.855	High Similarity	NPD422	Phase 1
0.8367	Intermediate Similarity	NPD1653	Approved
0.8273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1613	Approved
0.8212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7075	Discontinued
0.8026	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD2424	Discontinued
0.8	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD1548	Phase 1
0.7914	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1091	Approved
0.7857	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5844	Phase 1
0.7821	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD5401	Approved
0.777	Intermediate Similarity	NPD3750	Approved
0.777	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1549	Phase 2
0.7746	Intermediate Similarity	NPD1296	Phase 2
0.7742	Intermediate Similarity	NPD7819	Suspended
0.7742	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6799	Approved
0.7727	Intermediate Similarity	NPD7411	Suspended
0.7698	Intermediate Similarity	NPD8651	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7697	Intermediate Similarity	NPD5403	Approved
0.7687	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1934	Approved
0.7676	Intermediate Similarity	NPD3027	Phase 3
0.7674	Intermediate Similarity	NPD290	Approved
0.7671	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7639	Intermediate Similarity	NPD4060	Phase 1
0.7622	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6798	Discontinued
0.7619	Intermediate Similarity	NPD2796	Approved
0.7613	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7097	Phase 1
0.7603	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4538	Approved
0.7603	Intermediate Similarity	NPD4536	Approved
0.7584	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1243	Approved
0.7584	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2415	Discontinued
0.758	Intermediate Similarity	NPD5402	Approved
0.758	Intermediate Similarity	NPD3817	Phase 2
0.7576	Intermediate Similarity	NPD6559	Discontinued
0.7571	Intermediate Similarity	NPD3225	Approved
0.7566	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4625	Phase 3
0.7551	Intermediate Similarity	NPD1510	Phase 2
0.7551	Intermediate Similarity	NPD7033	Discontinued
0.755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5058	Phase 3
0.7548	Intermediate Similarity	NPD6599	Discontinued
0.7538	Intermediate Similarity	NPD1358	Approved
0.7532	Intermediate Similarity	NPD7768	Phase 2
0.7519	Intermediate Similarity	NPD9697	Approved
0.7518	Intermediate Similarity	NPD2797	Approved
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7481	Intermediate Similarity	NPD2684	Approved
0.7466	Intermediate Similarity	NPD6355	Discontinued
0.7466	Intermediate Similarity	NPD4340	Discontinued
0.7451	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5763	Approved
0.745	Intermediate Similarity	NPD5762	Approved
0.7448	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD919	Approved
0.7432	Intermediate Similarity	NPD5588	Approved
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7432	Intermediate Similarity	NPD5960	Phase 3
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7417	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3496	Discontinued
0.7405	Intermediate Similarity	NPD1465	Phase 2
0.7403	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5691	Approved
0.7388	Intermediate Similarity	NPD5535	Approved
0.7388	Intermediate Similarity	NPD7843	Approved
0.7386	Intermediate Similarity	NPD1511	Approved
0.7379	Intermediate Similarity	NPD3268	Approved
0.7379	Intermediate Similarity	NPD2313	Discontinued
0.7358	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7157	Approved
0.7342	Intermediate Similarity	NPD4433	Discontinued
0.7338	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD6005	Phase 3
0.7333	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7333	Intermediate Similarity	NPD6002	Phase 3
0.7333	Intermediate Similarity	NPD6004	Phase 3
0.7333	Intermediate Similarity	NPD7266	Discontinued
0.7317	Intermediate Similarity	NPD6166	Phase 2
0.7317	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD9717	Approved
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2801	Approved
0.7292	Intermediate Similarity	NPD2861	Phase 2
0.729	Intermediate Similarity	NPD1512	Approved
0.7289	Intermediate Similarity	NPD7054	Approved
0.7284	Intermediate Similarity	NPD5494	Approved
0.7279	Intermediate Similarity	NPD4140	Approved
0.7279	Intermediate Similarity	NPD4307	Phase 2
0.7279	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD3266	Approved
0.7273	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7261	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7472	Approved
0.7246	Intermediate Similarity	NPD7074	Phase 3
0.7239	Intermediate Similarity	NPD7199	Phase 2
0.7237	Intermediate Similarity	NPD6674	Discontinued
0.7234	Intermediate Similarity	NPD1611	Approved
0.7233	Intermediate Similarity	NPD37	Approved
0.723	Intermediate Similarity	NPD447	Suspended
0.723	Intermediate Similarity	NPD230	Phase 1
0.7219	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1778	Approved
0.7208	Intermediate Similarity	NPD6667	Approved
0.7208	Intermediate Similarity	NPD6666	Approved
0.7205	Intermediate Similarity	NPD4967	Phase 2
0.7205	Intermediate Similarity	NPD4966	Approved
0.7205	Intermediate Similarity	NPD4965	Approved
0.7202	Intermediate Similarity	NPD6797	Phase 2
0.72	Intermediate Similarity	NPD2799	Discontinued
0.7197	Intermediate Similarity	NPD3134	Approved
0.7181	Intermediate Similarity	NPD1607	Approved
0.7161	Intermediate Similarity	NPD7212	Phase 2
0.7161	Intermediate Similarity	NPD7213	Phase 3
0.716	Intermediate Similarity	NPD7251	Discontinued
0.7153	Intermediate Similarity	NPD987	Approved
0.7153	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7985	Registered
0.7134	Intermediate Similarity	NPD8127	Discontinued
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7123	Intermediate Similarity	NPD6832	Phase 2
0.7118	Intermediate Similarity	NPD7808	Phase 3
0.7117	Intermediate Similarity	NPD6234	Discontinued
0.7115	Intermediate Similarity	NPD7447	Phase 1
0.7115	Intermediate Similarity	NPD2532	Approved
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2533	Approved
0.7115	Intermediate Similarity	NPD2534	Approved
0.7105	Intermediate Similarity	NPD2346	Discontinued
0.7103	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1019	Discontinued
0.7101	Intermediate Similarity	NPD6671	Approved
0.7099	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD4062	Phase 3
0.7091	Intermediate Similarity	NPD7229	Phase 3
0.7091	Intermediate Similarity	NPD6232	Discontinued
0.708	Intermediate Similarity	NPD1241	Discontinued
0.7078	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4535	Phase 3
0.707	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6653	Approved
0.7063	Intermediate Similarity	NPD1608	Approved
0.7049	Intermediate Similarity	NPD7583	Approved
0.7048	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3226	Approved
0.7039	Intermediate Similarity	NPD6032	Approved
0.7039	Intermediate Similarity	NPD6099	Approved
0.7039	Intermediate Similarity	NPD6100	Approved
0.7037	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD6190	Approved
0.703	Intermediate Similarity	NPD6959	Discontinued
0.703	Intermediate Similarity	NPD1247	Approved
0.7027	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1048	Approved
0.7024	Intermediate Similarity	NPD7228	Approved
0.7013	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD7585	Approved
0.7	Intermediate Similarity	NPD1933	Approved
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3787	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