NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.1
Volume:	167.921
LogP:	3.625
LogD:	3.839
LogS:	-3.617
# Rotatable Bonds:	0
TPSA:	13.14
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.554
Synthetic Accessibility Score:	3.337
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.574
MDCK Permeability:	2.9343611458898522e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.463
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.599
Plasma Protein Binding (PPB):	95.46707916259766%
Volume Distribution (VD):	2.914
Pgp-substrate:	4.908022403717041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.882
CYP1A2-substrate:	0.851
CYP2C19-inhibitor:	0.62
CYP2C19-substrate:	0.321
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.753
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	11.56
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.383
Drug-inuced Liver Injury (DILI):	0.436
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.307
Skin Sensitization:	0.253
Carcinogencity:	0.653
Eye Corrosion:	0.031
Eye Irritation:	0.441
Respiratory Toxicity:	0.731

Download Data

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

Natural Product: NPC79202

Natural Product ID:	NPC79202
*Common Name:**	(R)-(+)-Menthofuran
IUPAC Name:	(6R)-3,6-dimethyl-4,5,6,7-tetrahydro-1-benzofuran
Synonyms:
Standard InCHIKey:	YGWKXXYGDYYFJU-SSDOTTSWSA-N
Standard InCHI:	InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3/t7-/m1/s1
SMILES:	C[C@@H]1CCc2c(C)coc2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3526658
PubChem CID:	442478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1880	Schizonepeta tenuisfolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8789	Schizonepeta tenuifolia	Species	Lamiaceae	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
Kd	2
Ki	2
Others	2

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	Ki	=	2000.0	nM	PMID[542411]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	Kd	=	4500.0	nM	PMID[542411]
NPT2599	Individual Protein	Cytochrome P450 2A13	Homo sapiens	Kd	=	580.0	nM	PMID[542411]
NPT2599	Individual Protein	Cytochrome P450 2A13	Homo sapiens	Ki	=	54000.0	nM	PMID[542411]
NPT27	Others	Unspecified		Ratio Ki	=	27.0	n.a.	PMID[542411]
NPT27	Others	Unspecified		Ratio	=	0.13	n.a.	PMID[542411]

☑ 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 NPC79202 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	380
0.1-0.2	1708
0.2-0.3	4702
0.3-0.4	12543
0.4-0.5	7354
0.5-0.6	9608
0.6-0.7	5889
0.7-0.8	475
0.8-0.85	25
0.85-0.9	8
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC59035
0.931	High Similarity	NPC178382
0.9217	High Similarity	NPC97566
0.8929	High Similarity	NPC22678
0.8926	High Similarity	NPC59502
0.8689	High Similarity	NPC329707
0.864	High Similarity	NPC293253
0.8595	High Similarity	NPC471074
0.8595	High Similarity	NPC473885
0.8559	High Similarity	NPC137710
0.8547	High Similarity	NPC227660
0.8534	High Similarity	NPC205523
0.8512	High Similarity	NPC118853
0.8504	High Similarity	NPC209858
0.8504	High Similarity	NPC324117
0.8475	Intermediate Similarity	NPC206007
0.839	Intermediate Similarity	NPC217180
0.839	Intermediate Similarity	NPC312525
0.839	Intermediate Similarity	NPC212918
0.8376	Intermediate Similarity	NPC150895
0.8372	Intermediate Similarity	NPC307401
0.8308	Intermediate Similarity	NPC177262
0.8268	Intermediate Similarity	NPC473982
0.8244	Intermediate Similarity	NPC202260
0.8244	Intermediate Similarity	NPC233707
0.823	Intermediate Similarity	NPC42471
0.8226	Intermediate Similarity	NPC83301
0.8217	Intermediate Similarity	NPC265793
0.8189	Intermediate Similarity	NPC477645
0.8182	Intermediate Similarity	NPC246214
0.816	Intermediate Similarity	NPC141059
0.8125	Intermediate Similarity	NPC279596
0.811	Intermediate Similarity	NPC45947
0.808	Intermediate Similarity	NPC470858
0.8065	Intermediate Similarity	NPC65735
0.8065	Intermediate Similarity	NPC188377
0.8065	Intermediate Similarity	NPC141252
0.8065	Intermediate Similarity	NPC11799
0.806	Intermediate Similarity	NPC263337
0.8049	Intermediate Similarity	NPC36255
0.8045	Intermediate Similarity	NPC218204
0.8045	Intermediate Similarity	NPC61157
0.8045	Intermediate Similarity	NPC473681
0.8045	Intermediate Similarity	NPC18904
0.8031	Intermediate Similarity	NPC198904
0.8031	Intermediate Similarity	NPC50583
0.8017	Intermediate Similarity	NPC243704
0.8016	Intermediate Similarity	NPC184391
0.8	Intermediate Similarity	NPC64568
0.8	Intermediate Similarity	NPC205071
0.8	Intermediate Similarity	NPC45536
0.7984	Intermediate Similarity	NPC272899
0.7967	Intermediate Similarity	NPC115859
0.7955	Intermediate Similarity	NPC278832
0.7955	Intermediate Similarity	NPC170604
0.7955	Intermediate Similarity	NPC215109
0.7955	Intermediate Similarity	NPC64157
0.7941	Intermediate Similarity	NPC158871
0.7941	Intermediate Similarity	NPC84479
0.7937	Intermediate Similarity	NPC216810
0.792	Intermediate Similarity	NPC83115
0.792	Intermediate Similarity	NPC130275
0.7917	Intermediate Similarity	NPC28054
0.7907	Intermediate Similarity	NPC61788
0.7907	Intermediate Similarity	NPC475092
0.7895	Intermediate Similarity	NPC130976
0.7883	Intermediate Similarity	NPC56731
0.7881	Intermediate Similarity	NPC54626
0.7874	Intermediate Similarity	NPC290955
0.7874	Intermediate Similarity	NPC246392
0.7869	Intermediate Similarity	NPC171023
0.7869	Intermediate Similarity	NPC87466
0.7863	Intermediate Similarity	NPC106247
0.7857	Intermediate Similarity	NPC230979
0.7857	Intermediate Similarity	NPC303010
0.7851	Intermediate Similarity	NPC316062
0.784	Intermediate Similarity	NPC16922
0.7833	Intermediate Similarity	NPC252004
0.7826	Intermediate Similarity	NPC97904
0.7826	Intermediate Similarity	NPC62799
0.7812	Intermediate Similarity	NPC26532
0.7812	Intermediate Similarity	NPC279877
0.781	Intermediate Similarity	NPC117674
0.7805	Intermediate Similarity	NPC473969
0.7795	Intermediate Similarity	NPC23086
0.7788	Intermediate Similarity	NPC156768
0.7786	Intermediate Similarity	NPC218838
0.7778	Intermediate Similarity	NPC148374
0.7778	Intermediate Similarity	NPC201370
0.7778	Intermediate Similarity	NPC473983
0.777	Intermediate Similarity	NPC71821
0.7761	Intermediate Similarity	NPC472376
0.7754	Intermediate Similarity	NPC245522
0.7754	Intermediate Similarity	NPC27798
0.7754	Intermediate Similarity	NPC114513
0.7754	Intermediate Similarity	NPC290038
0.7754	Intermediate Similarity	NPC93241
0.7752	Intermediate Similarity	NPC208389
0.775	Intermediate Similarity	NPC53953
0.7744	Intermediate Similarity	NPC217914
0.7744	Intermediate Similarity	NPC46896
0.7727	Intermediate Similarity	NPC200718
0.7724	Intermediate Similarity	NPC21831
0.7724	Intermediate Similarity	NPC187547
0.7717	Intermediate Similarity	NPC179354
0.7714	Intermediate Similarity	NPC19747
0.7714	Intermediate Similarity	NPC93666
0.771	Intermediate Similarity	NPC196979
0.771	Intermediate Similarity	NPC470976
0.771	Intermediate Similarity	NPC471995
0.771	Intermediate Similarity	NPC470977
0.7698	Intermediate Similarity	NPC233763
0.7698	Intermediate Similarity	NPC478166
0.7692	Intermediate Similarity	NPC170546
0.7692	Intermediate Similarity	NPC66246
0.7692	Intermediate Similarity	NPC939
0.7687	Intermediate Similarity	NPC473268
0.768	Intermediate Similarity	NPC79557
0.7674	Intermediate Similarity	NPC477040
0.7674	Intermediate Similarity	NPC476917
0.7674	Intermediate Similarity	NPC327527
0.7674	Intermediate Similarity	NPC112706
0.7674	Intermediate Similarity	NPC477123
0.7674	Intermediate Similarity	NPC477966
0.7674	Intermediate Similarity	NPC207294
0.7669	Intermediate Similarity	NPC476947
0.7669	Intermediate Similarity	NPC158525
0.766	Intermediate Similarity	NPC211625
0.7656	Intermediate Similarity	NPC74612
0.7656	Intermediate Similarity	NPC138139
0.7656	Intermediate Similarity	NPC224657
0.7656	Intermediate Similarity	NPC46536
0.7652	Intermediate Similarity	NPC470740
0.7652	Intermediate Similarity	NPC471006
0.7643	Intermediate Similarity	NPC281398
0.7643	Intermediate Similarity	NPC224418
0.7642	Intermediate Similarity	NPC208906
0.7642	Intermediate Similarity	NPC131801
0.7642	Intermediate Similarity	NPC144745
0.7638	Intermediate Similarity	NPC243269
0.7634	Intermediate Similarity	NPC282230
0.7634	Intermediate Similarity	NPC183348
0.7634	Intermediate Similarity	NPC298190
0.7634	Intermediate Similarity	NPC136340
0.763	Intermediate Similarity	NPC471996
0.7626	Intermediate Similarity	NPC469642
0.7619	Intermediate Similarity	NPC477967
0.7619	Intermediate Similarity	NPC317217
0.7619	Intermediate Similarity	NPC314329
0.7615	Intermediate Similarity	NPC120836
0.7615	Intermediate Similarity	NPC223063
0.7612	Intermediate Similarity	NPC214572
0.7609	Intermediate Similarity	NPC27220
0.7606	Intermediate Similarity	NPC212257
0.7606	Intermediate Similarity	NPC228842
0.7597	Intermediate Similarity	NPC474737
0.7597	Intermediate Similarity	NPC83178
0.7583	Intermediate Similarity	NPC57879
0.7583	Intermediate Similarity	NPC23332
0.7581	Intermediate Similarity	NPC293424
0.7578	Intermediate Similarity	NPC290193
0.7576	Intermediate Similarity	NPC324488
0.7576	Intermediate Similarity	NPC477412
0.7576	Intermediate Similarity	NPC15083
0.7574	Intermediate Similarity	NPC265181
0.7561	Intermediate Similarity	NPC476031
0.7561	Intermediate Similarity	NPC476014
0.7557	Intermediate Similarity	NPC476925
0.7556	Intermediate Similarity	NPC310043
0.7556	Intermediate Similarity	NPC286130
0.7556	Intermediate Similarity	NPC4764
0.7552	Intermediate Similarity	NPC472787
0.7541	Intermediate Similarity	NPC292036
0.7538	Intermediate Similarity	NPC477039
0.7535	Intermediate Similarity	NPC95526
0.752	Intermediate Similarity	NPC35744
0.752	Intermediate Similarity	NPC201284
0.7519	Intermediate Similarity	NPC470859
0.7518	Intermediate Similarity	NPC56197
0.75	Intermediate Similarity	NPC477965
0.75	Intermediate Similarity	NPC115869
0.75	Intermediate Similarity	NPC294511
0.75	Intermediate Similarity	NPC183648
0.75	Intermediate Similarity	NPC475777
0.75	Intermediate Similarity	NPC182646
0.75	Intermediate Similarity	NPC477038
0.75	Intermediate Similarity	NPC121615
0.7483	Intermediate Similarity	NPC472298
0.7481	Intermediate Similarity	NPC204592
0.7481	Intermediate Similarity	NPC146872
0.748	Intermediate Similarity	NPC323118
0.7465	Intermediate Similarity	NPC113428
0.7465	Intermediate Similarity	NPC61284
0.7463	Intermediate Similarity	NPC477536
0.7462	Intermediate Similarity	NPC474264
0.7459	Intermediate Similarity	NPC279916
0.7448	Intermediate Similarity	NPC114880
0.7445	Intermediate Similarity	NPC98395
0.7445	Intermediate Similarity	NPC474722
0.7444	Intermediate Similarity	NPC301717

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 NPC79202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1059
0.2-0.3	1772
0.3-0.4	2939
0.4-0.5	1817
0.5-0.6	938
0.6-0.7	242
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.797	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1241	Discontinued
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1471	Phase 3
0.7442	Intermediate Similarity	NPD1876	Approved
0.7347	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD17	Approved
0.7319	Intermediate Similarity	NPD2344	Approved
0.7287	Intermediate Similarity	NPD3972	Approved
0.7197	Intermediate Similarity	NPD2798	Approved
0.7183	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1608	Approved
0.7121	Intermediate Similarity	NPD3267	Approved
0.7121	Intermediate Similarity	NPD3266	Approved
0.7113	Intermediate Similarity	NPD2309	Approved
0.7109	Intermediate Similarity	NPD1651	Approved
0.7103	Intermediate Similarity	NPD920	Approved
0.7092	Intermediate Similarity	NPD1243	Approved
0.709	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1281	Approved
0.7073	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2346	Discontinued
0.7068	Intermediate Similarity	NPD1019	Discontinued
0.7054	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2799	Discontinued
0.7023	Intermediate Similarity	NPD9717	Approved
0.7016	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD2796	Approved
0.6992	Remote Similarity	NPD2797	Approved
0.6985	Remote Similarity	NPD2313	Discontinued
0.6977	Remote Similarity	NPD5585	Approved
0.6977	Remote Similarity	NPD5691	Approved
0.6974	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8032	Phase 2
0.6923	Remote Similarity	NPD1778	Approved
0.6918	Remote Similarity	NPD6273	Approved
0.6917	Remote Similarity	NPD1283	Approved
0.6889	Remote Similarity	NPD9494	Approved
0.6884	Remote Similarity	NPD3142	Approved
0.6884	Remote Similarity	NPD3140	Approved
0.6879	Remote Similarity	NPD1551	Phase 2
0.6871	Remote Similarity	NPD3869	Phase 3
0.6871	Remote Similarity	NPD3873	Phase 3
0.6867	Remote Similarity	NPD6280	Approved
0.6867	Remote Similarity	NPD6279	Approved
0.6863	Remote Similarity	NPD919	Approved
0.6861	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD411	Approved
0.6861	Remote Similarity	NPD3268	Approved
0.6835	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD4308	Phase 3
0.6809	Remote Similarity	NPD3748	Approved
0.6806	Remote Similarity	NPD4628	Phase 3
0.6774	Remote Similarity	NPD1247	Approved
0.6769	Remote Similarity	NPD1894	Discontinued
0.6763	Remote Similarity	NPD2979	Phase 3
0.6748	Remote Similarity	NPD3134	Approved
0.6742	Remote Similarity	NPD3496	Discontinued
0.6741	Remote Similarity	NPD1203	Approved
0.6741	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2800	Approved
0.6735	Remote Similarity	NPD2532	Approved
0.6735	Remote Similarity	NPD2534	Approved
0.6735	Remote Similarity	NPD2533	Approved
0.6716	Remote Similarity	NPD4359	Approved
0.6714	Remote Similarity	NPD4618	Approved
0.6714	Remote Similarity	NPD447	Suspended
0.6714	Remote Similarity	NPD4622	Approved
0.6713	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6002	Phase 3
0.6713	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6005	Phase 3
0.6713	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6004	Phase 3
0.6713	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5760	Phase 2
0.6711	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD9697	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1240	Approved
0.6643	Remote Similarity	NPD6100	Approved
0.6643	Remote Similarity	NPD6099	Approved
0.6642	Remote Similarity	NPD2237	Approved
0.6641	Remote Similarity	NPD9545	Approved
0.664	Remote Similarity	NPD2182	Approved
0.664	Remote Similarity	NPD2684	Approved
0.6623	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5688	Approved
0.662	Remote Similarity	NPD5689	Approved
0.6615	Remote Similarity	NPD9493	Approved
0.6605	Remote Similarity	NPD6764	Approved
0.6605	Remote Similarity	NPD6765	Approved
0.6603	Remote Similarity	NPD5494	Approved
0.6596	Remote Similarity	NPD1933	Approved
0.6593	Remote Similarity	NPD5327	Phase 3
0.6589	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD164	Approved
0.6575	Remote Similarity	NPD7003	Approved
0.6575	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3750	Approved
0.6575	Remote Similarity	NPD4110	Phase 3
0.6573	Remote Similarity	NPD1510	Phase 2
0.6569	Remote Similarity	NPD5647	Approved
0.6567	Remote Similarity	NPD1611	Approved
0.6565	Remote Similarity	NPD7644	Approved
0.6565	Remote Similarity	NPD9092	Discovery
0.656	Remote Similarity	NPD1358	Approved
0.656	Remote Similarity	NPD290	Approved
0.6558	Remote Similarity	NPD2296	Approved
0.6556	Remote Similarity	NPD2651	Approved
0.6556	Remote Similarity	NPD3226	Approved
0.6556	Remote Similarity	NPD2649	Approved
0.6538	Remote Similarity	NPD7157	Approved
0.6531	Remote Similarity	NPD3887	Approved
0.6528	Remote Similarity	NPD2935	Discontinued
0.6528	Remote Similarity	NPD2438	Suspended
0.6528	Remote Similarity	NPD4476	Approved
0.6528	Remote Similarity	NPD4477	Approved
0.6528	Remote Similarity	NPD2531	Phase 2
0.6522	Remote Similarity	NPD1712	Approved
0.6519	Remote Similarity	NPD6808	Phase 2
0.6513	Remote Similarity	NPD6599	Discontinued
0.651	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4661	Approved
0.651	Remote Similarity	NPD4662	Approved
0.651	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8434	Phase 2
0.6503	Remote Similarity	NPD6559	Discontinued
0.65	Remote Similarity	NPD6798	Discontinued
0.6497	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7819	Suspended
0.6483	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2353	Approved
0.6478	Remote Similarity	NPD3926	Phase 2
0.6466	Remote Similarity	NPD3443	Approved
0.6466	Remote Similarity	NPD3445	Approved
0.6466	Remote Similarity	NPD3444	Approved
0.646	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD4870	Approved
0.6452	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7458	Discontinued
0.6446	Remote Similarity	NPD6785	Approved
0.6446	Remote Similarity	NPD6784	Approved
0.6444	Remote Similarity	NPD1201	Approved
0.6443	Remote Similarity	NPD6799	Approved
0.6439	Remote Similarity	NPD5536	Phase 2
0.6438	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2897	Discontinued
0.6434	Remote Similarity	NPD6653	Approved
0.6434	Remote Similarity	NPD7843	Approved
0.6434	Remote Similarity	NPD5535	Approved
0.6429	Remote Similarity	NPD1934	Approved
0.6419	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6671	Approved
0.6412	Remote Similarity	NPD2557	Approved
0.641	Remote Similarity	NPD3882	Suspended
0.6408	Remote Similarity	NPD4140	Approved
0.6403	Remote Similarity	NPD454	Approved
0.6397	Remote Similarity	NPD1481	Phase 2
0.6395	Remote Similarity	NPD2654	Approved
0.6387	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5283	Phase 1
0.6385	Remote Similarity	NPD592	Approved
0.6385	Remote Similarity	NPD594	Approved
0.6385	Remote Similarity	NPD1398	Phase 1
0.6383	Remote Similarity	NPD3764	Approved
0.6383	Remote Similarity	NPD7985	Registered
0.6383	Remote Similarity	NPD1296	Phase 2
0.6383	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6362	Approved
0.637	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3749	Approved
0.6364	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7340	Approved
0.6357	Remote Similarity	NPD1139	Approved
0.6357	Remote Similarity	NPD1137	Approved
0.6357	Remote Similarity	NPD2614	Approved
0.6351	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.635	Remote Similarity	NPD4749	Approved
0.6349	Remote Similarity	NPD968	Approved
0.6343	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1511	Approved
0.6328	Remote Similarity	NPD2067	Discontinued
0.6327	Remote Similarity	NPD2424	Discontinued
0.6327	Remote Similarity	NPD5958	Discontinued
0.6324	Remote Similarity	NPD6287	Discontinued
0.6324	Remote Similarity	NPD1535	Discovery
0.6324	Remote Similarity	NPD1610	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data