NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.08
Volume:	188.785
LogP:	1.983
LogD:	1.798
LogS:	-2.39
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	1.736
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.485
MDCK Permeability:	1.9641849576146342e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.555
Plasma Protein Binding (PPB):	77.32608795166016%
Volume Distribution (VD):	0.733
Pgp-substrate:	15.504433631896973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.317
CYP2C19-substrate:	0.305
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.72
CYP2D6-inhibitor:	0.253
CYP2D6-substrate:	0.677
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	10.964
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.207
Rat Oral Acute Toxicity:	0.312
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.18
Carcinogencity:	0.39
Eye Corrosion:	0.141
Eye Irritation:	0.952
Respiratory Toxicity:	0.28

Download Data

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

Natural Product: NPC16651

Natural Product ID:	NPC16651
*Common Name:**	1-(4-Hydroxy-3-Methoxyphenyl)Propan-1-One
IUPAC Name:	1-(4-hydroxy-3-methoxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	FBGXENQFSMMBNY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O3/c1-3-8(11)7-4-5-9(12)10(6-7)13-2/h4-6,12H,3H2,1-2H3
SMILES:	CCC(=O)c1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452723
PubChem CID:	15782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8463799]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792629]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214738]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11678	Aeonium cuneatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13891	Scolytus multistriatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11855	Streptomyces xanthocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14480	Tornabea scutellifera	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12707	Lithospermum canescens	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	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	1
Potency	3

Activity Type	# Activity
Cell Line	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	18.8	ug.mL-1	PMID[450008]
NPT2	Others	Unspecified		Potency	=	6513.1	nM	PMID[450009]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3.3	nM	PMID[450009]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[450010]

☑ 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 NPC16651 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	329
0.1-0.2	1718
0.2-0.3	4942
0.3-0.4	11529
0.4-0.5	5775
0.5-0.6	4164
0.6-0.7	8209
0.7-0.8	5481
0.8-0.85	370
0.85-0.9	133
0.9-0.95	42
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32163
0.96	High Similarity	NPC50763
0.9512	High Similarity	NPC203719
0.9512	High Similarity	NPC117237
0.944	High Similarity	NPC66905
0.9421	High Similarity	NPC114298
0.9417	High Similarity	NPC225245
0.9375	High Similarity	NPC139519
0.9344	High Similarity	NPC242372
0.9344	High Similarity	NPC164778
0.9344	High Similarity	NPC4181
0.9344	High Similarity	NPC257976
0.9291	High Similarity	NPC111888
0.9286	High Similarity	NPC298268
0.9268	High Similarity	NPC312404
0.9268	High Similarity	NPC273686
0.925	High Similarity	NPC299406
0.9225	High Similarity	NPC208760
0.9219	High Similarity	NPC159418
0.9219	High Similarity	NPC283823
0.9187	High Similarity	NPC474691
0.916	High Similarity	NPC325625
0.912	High Similarity	NPC179777
0.9083	High Similarity	NPC150919
0.9048	High Similarity	NPC123228
0.9048	High Similarity	NPC5018
0.9048	High Similarity	NPC151167
0.9048	High Similarity	NPC276466
0.9048	High Similarity	NPC123722
0.9024	High Similarity	NPC201777
0.9023	High Similarity	NPC908
0.9023	High Similarity	NPC138438
0.9	High Similarity	NPC144662
0.8984	High Similarity	NPC285776
0.8968	High Similarity	NPC84076
0.8968	High Similarity	NPC303680
0.8968	High Similarity	NPC90128
0.896	High Similarity	NPC30216
0.8955	High Similarity	NPC84273
0.8947	High Similarity	NPC4796
0.8943	High Similarity	NPC158949
0.8943	High Similarity	NPC295317
0.8931	High Similarity	NPC204592
0.8906	High Similarity	NPC304622
0.8906	High Similarity	NPC261759
0.8898	High Similarity	NPC281020
0.8898	High Similarity	NPC286683
0.8889	High Similarity	NPC169214
0.8889	High Similarity	NPC229218
0.8889	High Similarity	NPC176030
0.8889	High Similarity	NPC312256
0.8889	High Similarity	NPC141817
0.8889	High Similarity	NPC192597
0.8881	High Similarity	NPC50823
0.888	High Similarity	NPC163083
0.8871	High Similarity	NPC194416
0.8871	High Similarity	NPC177291
0.8855	High Similarity	NPC237330
0.8837	High Similarity	NPC172673
0.8824	High Similarity	NPC46161
0.8824	High Similarity	NPC239608
0.8824	High Similarity	NPC46880
0.8815	High Similarity	NPC110419
0.8797	High Similarity	NPC112068
0.8797	High Similarity	NPC110899
0.8797	High Similarity	NPC25305
0.8797	High Similarity	NPC125417
0.8797	High Similarity	NPC95679
0.8788	High Similarity	NPC274613
0.8779	High Similarity	NPC327410
0.8759	High Similarity	NPC207732
0.8759	High Similarity	NPC142165
0.875	High Similarity	NPC158654
0.8741	High Similarity	NPC326065
0.874	High Similarity	NPC53305
0.874	High Similarity	NPC257589
0.8731	High Similarity	NPC284409
0.8722	High Similarity	NPC324929
0.8702	High Similarity	NPC239302
0.8696	High Similarity	NPC160777
0.8696	High Similarity	NPC73416
0.8686	High Similarity	NPC469615
0.8686	High Similarity	NPC254659
0.8686	High Similarity	NPC50954
0.8672	High Similarity	NPC92207
0.8672	High Similarity	NPC154275
0.8672	High Similarity	NPC127937
0.8672	High Similarity	NPC276014
0.8651	High Similarity	NPC286573
0.8633	High Similarity	NPC165389
0.8623	High Similarity	NPC469683
0.8618	High Similarity	NPC39793
0.8615	High Similarity	NPC226855
0.8613	High Similarity	NPC299154
0.8605	High Similarity	NPC293641
0.8605	High Similarity	NPC20404
0.8605	High Similarity	NPC12022
0.8605	High Similarity	NPC20287
0.8603	High Similarity	NPC28398
0.8594	High Similarity	NPC473626
0.8594	High Similarity	NPC280767
0.8583	High Similarity	NPC156840
0.8583	High Similarity	NPC160900
0.8583	High Similarity	NPC8547
0.8583	High Similarity	NPC106659
0.8583	High Similarity	NPC18984
0.8583	High Similarity	NPC23332
0.8583	High Similarity	NPC229084
0.8583	High Similarity	NPC173746
0.8583	High Similarity	NPC257124
0.8571	High Similarity	NPC469539
0.8571	High Similarity	NPC469540
0.8571	High Similarity	NPC155098
0.8571	High Similarity	NPC471110
0.8561	High Similarity	NPC9370
0.8561	High Similarity	NPC287495
0.8561	High Similarity	NPC153453
0.8561	High Similarity	NPC157133
0.8551	High Similarity	NPC287722
0.8548	High Similarity	NPC137537
0.8548	High Similarity	NPC205502
0.8548	High Similarity	NPC70744
0.8548	High Similarity	NPC164706
0.8548	High Similarity	NPC272471
0.8548	High Similarity	NPC107588
0.8538	High Similarity	NPC278308
0.8538	High Similarity	NPC226661
0.8529	High Similarity	NPC474784
0.8511	High Similarity	NPC287395
0.8511	High Similarity	NPC183655
0.8511	High Similarity	NPC474903
0.85	High Similarity	NPC143903
0.85	High Similarity	NPC226987
0.85	High Similarity	NPC183648
0.8496	Intermediate Similarity	NPC475468
0.8496	Intermediate Similarity	NPC307006
0.8496	Intermediate Similarity	NPC129889
0.8492	Intermediate Similarity	NPC109083
0.8492	Intermediate Similarity	NPC60962
0.8492	Intermediate Similarity	NPC189844
0.8492	Intermediate Similarity	NPC269843
0.8492	Intermediate Similarity	NPC224814
0.8492	Intermediate Similarity	NPC14007
0.8489	Intermediate Similarity	NPC196941
0.8489	Intermediate Similarity	NPC309169
0.8489	Intermediate Similarity	NPC105213
0.8489	Intermediate Similarity	NPC275278
0.8489	Intermediate Similarity	NPC113397
0.8478	Intermediate Similarity	NPC301178
0.8478	Intermediate Similarity	NPC284556
0.8478	Intermediate Similarity	NPC11314
0.8468	Intermediate Similarity	NPC240664
0.8455	Intermediate Similarity	NPC278102
0.8451	Intermediate Similarity	NPC205054
0.8451	Intermediate Similarity	NPC195763
0.8451	Intermediate Similarity	NPC264289
0.8451	Intermediate Similarity	NPC102003
0.8451	Intermediate Similarity	NPC200060
0.8451	Intermediate Similarity	NPC142876
0.8451	Intermediate Similarity	NPC333691
0.8451	Intermediate Similarity	NPC92722
0.8451	Intermediate Similarity	NPC139293
0.8451	Intermediate Similarity	NPC264550
0.8451	Intermediate Similarity	NPC237441
0.8451	Intermediate Similarity	NPC40290
0.8451	Intermediate Similarity	NPC69430
0.845	Intermediate Similarity	NPC3221
0.8444	Intermediate Similarity	NPC90431
0.844	Intermediate Similarity	NPC188074
0.844	Intermediate Similarity	NPC472969
0.844	Intermediate Similarity	NPC125449
0.8433	Intermediate Similarity	NPC45404
0.8429	Intermediate Similarity	NPC225351
0.8417	Intermediate Similarity	NPC119663
0.8417	Intermediate Similarity	NPC7097
0.8417	Intermediate Similarity	NPC246358
0.8417	Intermediate Similarity	NPC473090
0.8417	Intermediate Similarity	NPC36108
0.8417	Intermediate Similarity	NPC233731
0.8417	Intermediate Similarity	NPC471417
0.8413	Intermediate Similarity	NPC202474
0.8409	Intermediate Similarity	NPC65935
0.8409	Intermediate Similarity	NPC137427
0.8409	Intermediate Similarity	NPC195292
0.8409	Intermediate Similarity	NPC215941
0.8409	Intermediate Similarity	NPC319282
0.8409	Intermediate Similarity	NPC244246
0.8409	Intermediate Similarity	NPC275724
0.8409	Intermediate Similarity	NPC311419
0.8409	Intermediate Similarity	NPC123196
0.8409	Intermediate Similarity	NPC142985
0.84	Intermediate Similarity	NPC212743
0.8394	Intermediate Similarity	NPC322021
0.8392	Intermediate Similarity	NPC29231
0.8392	Intermediate Similarity	NPC472279
0.838	Intermediate Similarity	NPC15329
0.838	Intermediate Similarity	NPC254702
0.838	Intermediate Similarity	NPC80710
0.838	Intermediate Similarity	NPC203747
0.838	Intermediate Similarity	NPC194653

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 NPC16651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	996
0.2-0.3	1596
0.3-0.4	2661
0.4-0.5	1806
0.5-0.6	1124
0.6-0.7	523
0.7-0.8	110
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9512	High Similarity	NPD9494	Approved
0.8583	High Similarity	NPD228	Approved
0.8583	High Similarity	NPD4379	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD230	Phase 1
0.8108	Intermediate Similarity	NPD3882	Suspended
0.8095	Intermediate Similarity	NPD2801	Approved
0.8088	Intermediate Similarity	NPD447	Suspended
0.8069	Intermediate Similarity	NPD824	Approved
0.8031	Intermediate Similarity	NPD5536	Phase 2
0.8027	Intermediate Similarity	NPD1934	Approved
0.7972	Intermediate Similarity	NPD1511	Approved
0.7969	Intermediate Similarity	NPD9545	Approved
0.7883	Intermediate Similarity	NPD943	Approved
0.7883	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD1512	Approved
0.7857	Intermediate Similarity	NPD1241	Discontinued
0.7803	Intermediate Similarity	NPD9269	Phase 2
0.7803	Intermediate Similarity	NPD3972	Approved
0.777	Intermediate Similarity	NPD1607	Approved
0.7733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2344	Approved
0.766	Intermediate Similarity	NPD1510	Phase 2
0.766	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4628	Phase 3
0.7632	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1876	Approved
0.7538	Intermediate Similarity	NPD9493	Approved
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.752	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6166	Phase 2
0.7516	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2309	Approved
0.7451	Intermediate Similarity	NPD3817	Phase 2
0.7442	Intermediate Similarity	NPD5283	Phase 1
0.7426	Intermediate Similarity	NPD1283	Approved
0.741	Intermediate Similarity	NPD3027	Phase 3
0.7407	Intermediate Similarity	NPD9717	Approved
0.7407	Intermediate Similarity	NPD1608	Approved
0.7405	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6232	Discontinued
0.7379	Intermediate Similarity	NPD1549	Phase 2
0.7375	Intermediate Similarity	NPD7054	Approved
0.7368	Intermediate Similarity	NPD1651	Approved
0.7368	Intermediate Similarity	NPD6385	Approved
0.7368	Intermediate Similarity	NPD1357	Approved
0.7368	Intermediate Similarity	NPD6386	Approved
0.7358	Intermediate Similarity	NPD7473	Discontinued
0.7351	Intermediate Similarity	NPD3455	Phase 2
0.7347	Intermediate Similarity	NPD2354	Approved
0.7347	Intermediate Similarity	NPD6190	Approved
0.7338	Intermediate Similarity	NPD5977	Approved
0.7338	Intermediate Similarity	NPD5978	Approved
0.7333	Intermediate Similarity	NPD9296	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7472	Approved
0.7329	Intermediate Similarity	NPD7074	Phase 3
0.7319	Intermediate Similarity	NPD2798	Approved
0.731	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2674	Phase 3
0.7303	Intermediate Similarity	NPD4380	Phase 2
0.7292	Intermediate Similarity	NPD2799	Discontinued
0.7279	Intermediate Similarity	NPD8166	Discontinued
0.7273	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3142	Approved
0.7254	Intermediate Similarity	NPD3140	Approved
0.7248	Intermediate Similarity	NPD6799	Approved
0.7246	Intermediate Similarity	NPD1203	Approved
0.7244	Intermediate Similarity	NPD1358	Approved
0.7239	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7685	Pre-registration
0.7237	Intermediate Similarity	NPD7458	Discontinued
0.7234	Intermediate Similarity	NPD411	Approved
0.7206	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1281	Approved
0.7203	Intermediate Similarity	NPD1933	Approved
0.72	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2684	Approved
0.7185	Intermediate Similarity	NPD4626	Approved
0.7185	Intermediate Similarity	NPD17	Approved
0.7178	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6797	Phase 2
0.7162	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4110	Phase 3
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7152	Intermediate Similarity	NPD5494	Approved
0.7134	Intermediate Similarity	NPD7075	Discontinued
0.7134	Intermediate Similarity	NPD7251	Discontinued
0.7133	Intermediate Similarity	NPD3620	Phase 2
0.7133	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1558	Phase 1
0.7132	Intermediate Similarity	NPD3021	Approved
0.7132	Intermediate Similarity	NPD3022	Approved
0.7123	Intermediate Similarity	NPD2796	Approved
0.7113	Intermediate Similarity	NPD3144	Approved
0.7113	Intermediate Similarity	NPD3764	Approved
0.7113	Intermediate Similarity	NPD2313	Discontinued
0.7113	Intermediate Similarity	NPD3145	Approved
0.7107	Intermediate Similarity	NPD1247	Approved
0.7092	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7808	Phase 3
0.7089	Intermediate Similarity	NPD919	Approved
0.708	Intermediate Similarity	NPD1535	Discovery
0.7078	Intermediate Similarity	NPD7028	Phase 2
0.7078	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2353	Approved
0.7075	Intermediate Similarity	NPD2346	Discontinued
0.7075	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD257	Approved
0.7071	Intermediate Similarity	NPD258	Approved
0.7066	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD259	Phase 1
0.7059	Intermediate Similarity	NPD1778	Approved
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.7051	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3750	Approved
0.7047	Intermediate Similarity	NPD7003	Approved
0.7041	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1894	Discontinued
0.7032	Intermediate Similarity	NPD6873	Phase 2
0.7031	Intermediate Similarity	NPD3134	Approved
0.7025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4357	Discontinued
0.7019	Intermediate Similarity	NPD3926	Phase 2
0.7014	Intermediate Similarity	NPD825	Approved
0.7014	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD826	Approved
0.7014	Intermediate Similarity	NPD1613	Approved
0.7013	Intermediate Similarity	NPD2649	Approved
0.7013	Intermediate Similarity	NPD2651	Approved
0.7006	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD2821	Approved
0.7	Intermediate Similarity	NPD3887	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6992	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD290	Approved
0.6974	Remote Similarity	NPD2532	Approved
0.6974	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2534	Approved
0.6974	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2533	Approved
0.6974	Remote Similarity	NPD3146	Approved
0.697	Remote Similarity	NPD7843	Approved
0.6968	Remote Similarity	NPD6599	Discontinued
0.6966	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD555	Phase 2
0.6959	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1471	Phase 3
0.6957	Remote Similarity	NPD1201	Approved
0.695	Remote Similarity	NPD5647	Approved
0.6946	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4062	Phase 3
0.6944	Remote Similarity	NPD6233	Phase 2
0.6943	Remote Similarity	NPD7819	Suspended
0.694	Remote Similarity	NPD7157	Approved
0.6939	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD9266	Approved
0.6923	Remote Similarity	NPD74	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD958	Approved
0.6914	Remote Similarity	NPD5242	Approved
0.6903	Remote Similarity	NPD3226	Approved
0.6901	Remote Similarity	NPD9569	Approved
0.6899	Remote Similarity	NPD2296	Approved
0.6897	Remote Similarity	NPD4060	Phase 1
0.6892	Remote Similarity	NPD1551	Phase 2
0.689	Remote Similarity	NPD2163	Approved
0.6884	Remote Similarity	NPD3847	Discontinued
0.6884	Remote Similarity	NPD3496	Discontinued
0.6883	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD6801	Discontinued
0.6875	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6234	Discontinued
0.6875	Remote Similarity	NPD3268	Approved
0.6867	Remote Similarity	NPD2800	Approved
0.6861	Remote Similarity	NPD5691	Approved
0.6853	Remote Similarity	NPD6832	Phase 2
0.6849	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9267	Approved
0.6846	Remote Similarity	NPD9264	Approved
0.6846	Remote Similarity	NPD7266	Discontinued
0.6846	Remote Similarity	NPD9263	Approved
0.6842	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9377	Approved
0.6842	Remote Similarity	NPD9379	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