NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.08
Volume:	235.583
LogP:	2.93
LogD:	2.82
LogS:	-4.37
# Rotatable Bonds:	1
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	3.053
Fsp3:	0.214
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:	-4.682
MDCK Permeability:	1.6719515770091675e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.731

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	92.38805389404297%
Volume Distribution (VD):	0.842
Pgp-substrate:	5.661044120788574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.709
CYP2C19-substrate:	0.215
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.501
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.406

ADMET: Excretion

Clearance (CL):	11.886
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.852
Drug-inuced Liver Injury (DILI):	0.813
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.901
Skin Sensitization:	0.091
Carcinogencity:	0.928
Eye Corrosion:	0.036
Eye Irritation:	0.813
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC234109

Natural Product ID:	NPC234109
*Common Name:**	2-Prop-1-En-2-Yl-2,3-Dihydrofuro[3,2-G]Chromen-7-One
IUPAC Name:	2-prop-1-en-2-yl-2,3-dihydrofuro[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	VMWUHWZFDITAOL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O3/c1-8(2)11-6-10-5-9-3-4-14(15)17-12(9)7-13(10)16-11/h3-5,7,11H,1,6H2,2H3
SMILES:	CC(=C)C1Cc2c(O1)cc1c(c2)ccc(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1467672
PubChem CID:	611672
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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]
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]
NPO11438	Angelica gigas	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]
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[TCMID]
NPO2921	Angelica acutiloba	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]
NPO11438	Angelica gigas	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[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]
NPO2921	Angelica acutiloba	Species	Apiaceae	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]

☑ 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
Potency	27

Activity Type	# Activity
Individual Protein	21
Organism	2
Others	2
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	7.1	nM	PMID[515871]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[515871]
NPT537	Individual Protein	Ras-related protein Rab-9A	Homo sapiens	Potency	=	2511.9	nM	PMID[515871]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	2818.4	nM	PMID[515871]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	25118.9	nM	PMID[515871]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	22.4	nM	PMID[515871]
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Potency	=	22387.2	nM	PMID[515871]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[515871]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[515871]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[515871]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	13459.1	nM	PMID[515871]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	631.0	nM	PMID[515871]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[515871]
NPT157	Individual Protein	Breast cancer type 1 susceptibility protein	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[515871]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[515871]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[515871]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[515871]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	16481.6	nM	PMID[515871]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[515871]
NPT2	Others	Unspecified		Potency	=	9200.0	nM	PMID[515871]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[515871]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	89125.1	nM	PMID[515871]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[515871]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	39810.7	nM	PMID[515871]
NPT2	Others	Unspecified		Potency	n.a.	2511.9	nM	PMID[515871]

☑ 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 NPC234109 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	414
0.1-0.2	1813
0.2-0.3	4623
0.3-0.4	10685
0.4-0.5	7497
0.5-0.6	4527
0.6-0.7	6023
0.7-0.8	5200
0.8-0.85	1316
0.85-0.9	420
0.9-0.95	156
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188327
0.952	High Similarity	NPC14248
0.9512	High Similarity	NPC199204
0.95	High Similarity	NPC96286
0.95	High Similarity	NPC248429
0.9444	High Similarity	NPC222036
0.9444	High Similarity	NPC7526
0.9444	High Similarity	NPC163557
0.9435	High Similarity	NPC168710
0.9421	High Similarity	NPC472518
0.937	High Similarity	NPC55149
0.937	High Similarity	NPC307412
0.937	High Similarity	NPC98179
0.937	High Similarity	NPC253574
0.936	High Similarity	NPC80170
0.9344	High Similarity	NPC111347
0.9344	High Similarity	NPC201667
0.9344	High Similarity	NPC73413
0.9328	High Similarity	NPC281356
0.9297	High Similarity	NPC33986
0.9268	High Similarity	NPC471827
0.9268	High Similarity	NPC471828
0.9262	High Similarity	NPC273772
0.9262	High Similarity	NPC109675
0.9256	High Similarity	NPC144418
0.9244	High Similarity	NPC265547
0.9244	High Similarity	NPC96705
0.9225	High Similarity	NPC283331
0.9213	High Similarity	NPC194277
0.92	High Similarity	NPC185066
0.92	High Similarity	NPC472519
0.9194	High Similarity	NPC471826
0.9187	High Similarity	NPC27671
0.918	High Similarity	NPC257188
0.918	High Similarity	NPC13007
0.9174	High Similarity	NPC235190
0.9174	High Similarity	NPC163200
0.9174	High Similarity	NPC180006
0.9167	High Similarity	NPC298796
0.9141	High Similarity	NPC207002
0.9141	High Similarity	NPC133956
0.9141	High Similarity	NPC167111
0.9141	High Similarity	NPC318400
0.9141	High Similarity	NPC471910
0.9141	High Similarity	NPC296624
0.9141	High Similarity	NPC31849
0.9113	High Similarity	NPC244495
0.9113	High Similarity	NPC93219
0.9106	High Similarity	NPC290605
0.9106	High Similarity	NPC173350
0.9106	High Similarity	NPC154176
0.9083	High Similarity	NPC152306
0.9076	High Similarity	NPC128633
0.907	High Similarity	NPC195343
0.907	High Similarity	NPC164269
0.907	High Similarity	NPC74655
0.907	High Similarity	NPC198381
0.907	High Similarity	NPC260265
0.907	High Similarity	NPC100986
0.907	High Similarity	NPC287182
0.907	High Similarity	NPC166672
0.907	High Similarity	NPC50896
0.907	High Similarity	NPC319859
0.907	High Similarity	NPC18804
0.907	High Similarity	NPC84894
0.907	High Similarity	NPC62366
0.907	High Similarity	NPC204353
0.907	High Similarity	NPC326600
0.907	High Similarity	NPC127888
0.907	High Similarity	NPC47163
0.907	High Similarity	NPC267412
0.9032	High Similarity	NPC291899
0.9008	High Similarity	NPC14697
0.9	High Similarity	NPC281241
0.9	High Similarity	NPC471625
0.9	High Similarity	NPC86892
0.9	High Similarity	NPC471909
0.9	High Similarity	NPC472424
0.9	High Similarity	NPC469675
0.8968	High Similarity	NPC243688
0.8952	High Similarity	NPC315807
0.8931	High Similarity	NPC224543
0.8931	High Similarity	NPC160727
0.8931	High Similarity	NPC55615
0.8931	High Similarity	NPC128529
0.8931	High Similarity	NPC177281
0.8931	High Similarity	NPC188380
0.8931	High Similarity	NPC149320
0.8931	High Similarity	NPC78746
0.8931	High Similarity	NPC38099
0.8931	High Similarity	NPC283019
0.8931	High Similarity	NPC476455
0.8931	High Similarity	NPC471630
0.8931	High Similarity	NPC26954
0.8923	High Similarity	NPC224475
0.8923	High Similarity	NPC213173
0.8923	High Similarity	NPC180716
0.8915	High Similarity	NPC19157
0.8915	High Similarity	NPC175159
0.8864	High Similarity	NPC153818
0.8864	High Similarity	NPC232246
0.8864	High Similarity	NPC184861
0.8864	High Similarity	NPC294456
0.8864	High Similarity	NPC155963
0.8864	High Similarity	NPC225106
0.8864	High Similarity	NPC212124
0.8864	High Similarity	NPC281014
0.8855	High Similarity	NPC472525
0.8846	High Similarity	NPC472524
0.8846	High Similarity	NPC55147
0.8837	High Similarity	NPC472517
0.8819	High Similarity	NPC224774
0.8819	High Similarity	NPC258567
0.8819	High Similarity	NPC121740
0.88	High Similarity	NPC50720
0.8797	High Similarity	NPC279573
0.8797	High Similarity	NPC211110
0.8797	High Similarity	NPC151946
0.879	High Similarity	NPC52247
0.8769	High Similarity	NPC469956
0.876	High Similarity	NPC113098
0.875	High Similarity	NPC157212
0.875	High Similarity	NPC139595
0.875	High Similarity	NPC60704
0.875	High Similarity	NPC469453
0.875	High Similarity	NPC293642
0.874	High Similarity	NPC101894
0.8731	High Similarity	NPC312881
0.8722	High Similarity	NPC306365
0.872	High Similarity	NPC150214
0.8702	High Similarity	NPC469955
0.8702	High Similarity	NPC469952
0.8702	High Similarity	NPC54503
0.8692	High Similarity	NPC267336
0.8692	High Similarity	NPC272650
0.8692	High Similarity	NPC29734
0.8686	High Similarity	NPC76657
0.8672	High Similarity	NPC289316
0.8667	High Similarity	NPC195357
0.8667	High Similarity	NPC287286
0.8667	High Similarity	NPC152771
0.864	High Similarity	NPC187868
0.8629	High Similarity	NPC247553
0.8626	High Similarity	NPC123954
0.8615	High Similarity	NPC32463
0.8615	High Similarity	NPC19242
0.8603	High Similarity	NPC470856
0.8594	High Similarity	NPC163248
0.8582	High Similarity	NPC131198
0.8582	High Similarity	NPC472516
0.8571	High Similarity	NPC229128
0.8561	High Similarity	NPC2363
0.8561	High Similarity	NPC296377
0.8561	High Similarity	NPC469449
0.856	High Similarity	NPC319378
0.856	High Similarity	NPC302107
0.854	High Similarity	NPC119640
0.854	High Similarity	NPC229916
0.854	High Similarity	NPC183646
0.8529	High Similarity	NPC472523
0.8529	High Similarity	NPC138149
0.8519	High Similarity	NPC307883
0.8519	High Similarity	NPC270256
0.8516	High Similarity	NPC232692
0.8516	High Similarity	NPC168259
0.8516	High Similarity	NPC202594
0.8507	High Similarity	NPC104796
0.8507	High Similarity	NPC167517
0.8504	High Similarity	NPC143725
0.85	High Similarity	NPC169510
0.8496	Intermediate Similarity	NPC309953
0.8496	Intermediate Similarity	NPC131950
0.8489	Intermediate Similarity	NPC208584
0.8487	Intermediate Similarity	NPC149545
0.8485	Intermediate Similarity	NPC137669
0.848	Intermediate Similarity	NPC473290
0.848	Intermediate Similarity	NPC471504
0.8478	Intermediate Similarity	NPC471824
0.8478	Intermediate Similarity	NPC476457
0.8473	Intermediate Similarity	NPC244799
0.8473	Intermediate Similarity	NPC240722
0.8467	Intermediate Similarity	NPC20631
0.8467	Intermediate Similarity	NPC93640
0.8456	Intermediate Similarity	NPC36414
0.8444	Intermediate Similarity	NPC471069
0.8444	Intermediate Similarity	NPC20796
0.8444	Intermediate Similarity	NPC471068
0.8433	Intermediate Similarity	NPC61499
0.8421	Intermediate Similarity	NPC241341
0.8421	Intermediate Similarity	NPC36437
0.8421	Intermediate Similarity	NPC142563
0.8421	Intermediate Similarity	NPC1220
0.8421	Intermediate Similarity	NPC241165
0.8421	Intermediate Similarity	NPC205797
0.8421	Intermediate Similarity	NPC141822
0.8421	Intermediate Similarity	NPC291551
0.8421	Intermediate Similarity	NPC472522
0.8421	Intermediate Similarity	NPC469965
0.8421	Intermediate Similarity	NPC233018
0.8417	Intermediate Similarity	NPC43716

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 NPC234109 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	990
0.2-0.3	1671
0.3-0.4	2709
0.4-0.5	1835
0.5-0.6	1086
0.6-0.7	354
0.7-0.8	99
0.8-0.85	31
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.879	High Similarity	NPD422	Phase 1
0.8421	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD5124	Phase 1
0.8394	Intermediate Similarity	NPD1243	Approved
0.8345	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD920	Approved
0.8227	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD1296	Phase 2
0.8151	Intermediate Similarity	NPD9697	Approved
0.8043	Intermediate Similarity	NPD2796	Approved
0.8031	Intermediate Similarity	NPD1548	Phase 1
0.8	Intermediate Similarity	NPD1652	Phase 2
0.7971	Intermediate Similarity	NPD3748	Approved
0.7969	Intermediate Similarity	NPD5691	Approved
0.7926	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD1610	Phase 2
0.7815	Intermediate Similarity	NPD919	Approved
0.7794	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD3134	Approved
0.7724	Intermediate Similarity	NPD1358	Approved
0.7698	Intermediate Similarity	NPD5535	Approved
0.7692	Intermediate Similarity	NPD3750	Approved
0.7667	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4908	Phase 1
0.7638	Intermediate Similarity	NPD1241	Discontinued
0.7634	Intermediate Similarity	NPD4626	Approved
0.76	Intermediate Similarity	NPD6801	Discontinued
0.7568	Intermediate Similarity	NPD1653	Approved
0.7556	Intermediate Similarity	NPD3266	Approved
0.7556	Intermediate Similarity	NPD3267	Approved
0.7556	Intermediate Similarity	NPD2797	Approved
0.7552	Intermediate Similarity	NPD1549	Phase 2
0.755	Intermediate Similarity	NPD7819	Suspended
0.7535	Intermediate Similarity	NPD1551	Phase 2
0.7534	Intermediate Similarity	NPD6799	Approved
0.7533	Intermediate Similarity	NPD7411	Suspended
0.7519	Intermediate Similarity	NPD1611	Approved
0.7518	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3225	Approved
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.7451	Intermediate Similarity	NPD7768	Phase 2
0.7448	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3496	Discontinued
0.7431	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1240	Approved
0.7429	Intermediate Similarity	NPD1613	Approved
0.7429	Intermediate Similarity	NPD4307	Phase 2
0.7429	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1019	Discontinued
0.7368	Intermediate Similarity	NPD1778	Approved
0.7368	Intermediate Similarity	NPD17	Approved
0.7365	Intermediate Similarity	NPD5401	Approved
0.7361	Intermediate Similarity	NPD6004	Phase 3
0.7361	Intermediate Similarity	NPD6002	Phase 3
0.7361	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6005	Phase 3
0.7361	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6599	Discontinued
0.7343	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD9717	Approved
0.7329	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1607	Approved
0.7315	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2424	Discontinued
0.7308	Intermediate Similarity	NPD5494	Approved
0.7305	Intermediate Similarity	NPD4140	Approved
0.7305	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD290	Approved
0.7286	Intermediate Similarity	NPD3268	Approved
0.7286	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4749	Approved
0.7267	Intermediate Similarity	NPD5403	Approved
0.7266	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1247	Approved
0.7259	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6355	Discontinued
0.7254	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2532	Approved
0.7248	Intermediate Similarity	NPD2533	Approved
0.7248	Intermediate Similarity	NPD2534	Approved
0.7248	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2684	Approved
0.7241	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4380	Phase 2
0.723	Intermediate Similarity	NPD6666	Approved
0.723	Intermediate Similarity	NPD6667	Approved
0.7226	Intermediate Similarity	NPD8651	Approved
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD7466	Approved
0.7211	Intermediate Similarity	NPD4628	Phase 3
0.7208	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD5844	Phase 1
0.7194	Intermediate Similarity	NPD2861	Phase 2
0.7194	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3749	Approved
0.7174	Intermediate Similarity	NPD1203	Approved
0.7172	Intermediate Similarity	NPD2935	Discontinued
0.7163	Intermediate Similarity	NPD6798	Discontinued
0.7163	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2313	Discontinued
0.7161	Intermediate Similarity	NPD3817	Phase 2
0.7161	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2800	Approved
0.7133	Intermediate Similarity	NPD4340	Discontinued
0.7132	Intermediate Similarity	NPD1281	Approved
0.7132	Intermediate Similarity	NPD1091	Approved
0.7125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5762	Approved
0.7123	Intermediate Similarity	NPD5763	Approved
0.7122	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7229	Phase 3
0.7092	Intermediate Similarity	NPD3027	Phase 3
0.709	Intermediate Similarity	NPD1894	Discontinued
0.709	Intermediate Similarity	NPD9545	Approved
0.7086	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6559	Discontinued
0.707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4476	Approved
0.7055	Intermediate Similarity	NPD4477	Approved
0.7051	Intermediate Similarity	NPD5402	Approved
0.7051	Intermediate Similarity	NPD4288	Approved
0.704	Intermediate Similarity	NPD940	Approved
0.704	Intermediate Similarity	NPD846	Approved
0.7037	Intermediate Similarity	NPD5585	Approved
0.7032	Intermediate Similarity	NPD1934	Approved
0.7029	Intermediate Similarity	NPD5327	Phase 3
0.7023	Intermediate Similarity	NPD7843	Approved
0.7006	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD3691	Phase 2
0.7	Intermediate Similarity	NPD3690	Phase 2
0.6993	Remote Similarity	NPD8032	Phase 2
0.6992	Remote Similarity	NPD7157	Approved
0.6978	Remote Similarity	NPD1283	Approved
0.6974	Remote Similarity	NPD6273	Approved
0.6954	Remote Similarity	NPD7213	Phase 3
0.6954	Remote Similarity	NPD1511	Approved
0.6954	Remote Similarity	NPD7212	Phase 2
0.695	Remote Similarity	NPD3018	Phase 2
0.695	Remote Similarity	NPD2237	Approved
0.6937	Remote Similarity	NPD7199	Phase 2
0.6933	Remote Similarity	NPD3818	Discontinued
0.6923	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD411	Approved
0.6918	Remote Similarity	NPD7097	Phase 1
0.6918	Remote Similarity	NPD2200	Suspended
0.6913	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1651	Approved
0.6909	Remote Similarity	NPD5953	Discontinued
0.6908	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7447	Phase 1
0.6899	Remote Similarity	NPD4967	Phase 2
0.6899	Remote Similarity	NPD4965	Approved
0.6899	Remote Similarity	NPD4966	Approved
0.6897	Remote Similarity	NPD230	Phase 1
0.6897	Remote Similarity	NPD1933	Approved
0.6897	Remote Similarity	NPD447	Suspended
0.6894	Remote Similarity	NPD821	Approved
0.689	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7644	Approved
0.6887	Remote Similarity	NPD5058	Phase 3
0.6884	Remote Similarity	NPD3705	Approved
0.6875	Remote Similarity	NPD6233	Phase 2
0.6871	Remote Similarity	NPD5588	Approved
0.6866	Remote Similarity	NPD2557	Approved
0.6866	Remote Similarity	NPD6671	Approved
0.6863	Remote Similarity	NPD1512	Approved
0.6857	Remote Similarity	NPD1876	Approved
0.6857	Remote Similarity	NPD6696	Suspended
0.6855	Remote Similarity	NPD6971	Discontinued
0.6852	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD594	Approved
0.6842	Remote Similarity	NPD592	Approved
0.6839	Remote Similarity	NPD3226	Approved
0.6839	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1182	Approved
0.6835	Remote Similarity	NPD2981	Phase 2
0.6829	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2979	Phase 3
0.6826	Remote Similarity	NPD7549	Discontinued
0.6824	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6099	Approved
0.6824	Remote Similarity	NPD2438	Suspended
0.6822	Remote Similarity	NPD968	Approved
0.6818	Remote Similarity	NPD1139	Approved
0.6818	Remote Similarity	NPD1137	Approved
0.6815	Remote Similarity	NPD9493	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data