NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.08
Volume:	179.994
LogP:	1.535
LogD:	1.006
LogS:	-2.303
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	1.468
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.359
MDCK Permeability:	3.282825127826072e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.465
Plasma Protein Binding (PPB):	62.71111297607422%
Volume Distribution (VD):	0.666
Pgp-substrate:	20.169679641723633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.684
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.407
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.595

ADMET: Excretion

Clearance (CL):	11.74
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.336
Carcinogencity:	0.465
Eye Corrosion:	0.285
Eye Irritation:	0.919
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC38209

Natural Product ID:	NPC38209
*Common Name:**	1-(4-Methoxyphenyl)Acetone
IUPAC Name:	1-(4-methoxyphenyl)propan-2-one
Synonyms:	1-(4-Methoxyphenyl)Acetone
Standard InCHIKey:	WFWKNGZODAOLEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H12O2/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3
SMILES:	CC(=O)Cc1ccc(cc1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473366
PubChem CID:	31231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18379	Satureja atropatana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14465	Ramalina terebrata	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16137	Mappia foetida	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7027	Metapenaeus macleayi	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6519	Calocera viscosa	Species	Dacrymycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16626	Leucetta microrhaphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13368	Monomorium delagoense	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10773	Dalbergia rubiginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13970	Caryopteris mongholica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10551	Acanthopanax ricinifolius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	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
NPO4626	NPC38209	Other	Seed	73.1	73.1	73.1	mg/100g	Database [DUKE]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	43000.0	nM	PMID[479212]

☑ 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 NPC38209 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	277
0.1-0.2	1978
0.2-0.3	5019
0.3-0.4	12548
0.4-0.5	5028
0.5-0.6	7554
0.6-0.7	8567
0.7-0.8	1602
0.8-0.85	98
0.85-0.9	18
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC298224
0.9596	High Similarity	NPC1065
0.932	High Similarity	NPC23332
0.9314	High Similarity	NPC234639
0.9223	High Similarity	NPC183648
0.9126	High Similarity	NPC259554
0.8962	High Similarity	NPC109241
0.8958	High Similarity	NPC321956
0.8889	High Similarity	NPC175298
0.8854	High Similarity	NPC71853
0.8807	High Similarity	NPC469954
0.8774	High Similarity	NPC57879
0.875	High Similarity	NPC259134
0.875	High Similarity	NPC177844
0.875	High Similarity	NPC8002
0.875	High Similarity	NPC99886
0.8716	High Similarity	NPC19290
0.8624	High Similarity	NPC220540
0.8614	High Similarity	NPC280869
0.8614	High Similarity	NPC100870
0.8559	High Similarity	NPC293424
0.8558	High Similarity	NPC473855
0.8558	High Similarity	NPC238115
0.8545	High Similarity	NPC470860
0.8532	High Similarity	NPC252004
0.8529	High Similarity	NPC13755
0.8515	High Similarity	NPC260000
0.8496	Intermediate Similarity	NPC225245
0.8482	Intermediate Similarity	NPC299406
0.8455	Intermediate Similarity	NPC322358
0.8447	Intermediate Similarity	NPC300166
0.8447	Intermediate Similarity	NPC307425
0.844	Intermediate Similarity	NPC279916
0.844	Intermediate Similarity	NPC53953
0.8426	Intermediate Similarity	NPC54626
0.84	Intermediate Similarity	NPC471581
0.8393	Intermediate Similarity	NPC205502
0.8393	Intermediate Similarity	NPC171023
0.8365	Intermediate Similarity	NPC179686
0.835	Intermediate Similarity	NPC107101
0.8319	Intermediate Similarity	NPC61779
0.8288	Intermediate Similarity	NPC51345
0.8288	Intermediate Similarity	NPC188907
0.8286	Intermediate Similarity	NPC109637
0.8286	Intermediate Similarity	NPC2518
0.8286	Intermediate Similarity	NPC283546
0.8286	Intermediate Similarity	NPC292792
0.8286	Intermediate Similarity	NPC108875
0.8286	Intermediate Similarity	NPC38079
0.8276	Intermediate Similarity	NPC473942
0.8276	Intermediate Similarity	NPC141252
0.8276	Intermediate Similarity	NPC11799
0.8276	Intermediate Similarity	NPC474691
0.8269	Intermediate Similarity	NPC84325
0.8261	Intermediate Similarity	NPC201777
0.8257	Intermediate Similarity	NPC233238
0.823	Intermediate Similarity	NPC166591
0.823	Intermediate Similarity	NPC152159
0.8208	Intermediate Similarity	NPC470393
0.8208	Intermediate Similarity	NPC128730
0.8198	Intermediate Similarity	NPC114144
0.819	Intermediate Similarity	NPC114298
0.819	Intermediate Similarity	NPC305205
0.8173	Intermediate Similarity	NPC52472
0.8165	Intermediate Similarity	NPC473809
0.8165	Intermediate Similarity	NPC231251
0.8165	Intermediate Similarity	NPC88868
0.8165	Intermediate Similarity	NPC25067
0.8158	Intermediate Similarity	NPC201284
0.8155	Intermediate Similarity	NPC470161
0.8148	Intermediate Similarity	NPC291837
0.8142	Intermediate Similarity	NPC45104
0.8142	Intermediate Similarity	NPC217423
0.8142	Intermediate Similarity	NPC240664
0.8136	Intermediate Similarity	NPC470858
0.8136	Intermediate Similarity	NPC65041
0.8136	Intermediate Similarity	NPC2771
0.8131	Intermediate Similarity	NPC113457
0.8131	Intermediate Similarity	NPC326447
0.8131	Intermediate Similarity	NPC176971
0.812	Intermediate Similarity	NPC163083
0.812	Intermediate Similarity	NPC257976
0.812	Intermediate Similarity	NPC164778
0.812	Intermediate Similarity	NPC4181
0.812	Intermediate Similarity	NPC244876
0.812	Intermediate Similarity	NPC242372
0.8113	Intermediate Similarity	NPC241224
0.8103	Intermediate Similarity	NPC194416
0.8103	Intermediate Similarity	NPC177291
0.8095	Intermediate Similarity	NPC12714
0.8095	Intermediate Similarity	NPC310905
0.8095	Intermediate Similarity	NPC51633
0.8087	Intermediate Similarity	NPC470092
0.8077	Intermediate Similarity	NPC471576
0.8077	Intermediate Similarity	NPC245561
0.807	Intermediate Similarity	NPC32298
0.8067	Intermediate Similarity	NPC177925
0.8067	Intermediate Similarity	NPC474264
0.8056	Intermediate Similarity	NPC251306
0.8056	Intermediate Similarity	NPC157473
0.8056	Intermediate Similarity	NPC151530
0.8056	Intermediate Similarity	NPC226699
0.8051	Intermediate Similarity	NPC273686
0.8051	Intermediate Similarity	NPC111088
0.8051	Intermediate Similarity	NPC75432
0.8051	Intermediate Similarity	NPC312404
0.8051	Intermediate Similarity	NPC30216
0.8037	Intermediate Similarity	NPC227255
0.8037	Intermediate Similarity	NPC13495
0.8037	Intermediate Similarity	NPC473393
0.8034	Intermediate Similarity	NPC69403
0.8034	Intermediate Similarity	NPC291189
0.8019	Intermediate Similarity	NPC192596
0.8018	Intermediate Similarity	NPC199462
0.8018	Intermediate Similarity	NPC17693
0.8017	Intermediate Similarity	NPC295317
0.8	Intermediate Similarity	NPC54243
0.8	Intermediate Similarity	NPC264976
0.8	Intermediate Similarity	NPC32163
0.8	Intermediate Similarity	NPC428300
0.8	Intermediate Similarity	NPC286683
0.8	Intermediate Similarity	NPC293387
0.8	Intermediate Similarity	NPC35744
0.8	Intermediate Similarity	NPC16651
0.7983	Intermediate Similarity	NPC53305
0.7983	Intermediate Similarity	NPC257589
0.7982	Intermediate Similarity	NPC317305
0.7982	Intermediate Similarity	NPC75440
0.7982	Intermediate Similarity	NPC31274
0.7981	Intermediate Similarity	NPC95755
0.7966	Intermediate Similarity	NPC182646
0.7963	Intermediate Similarity	NPC6984
0.7949	Intermediate Similarity	NPC314329
0.7946	Intermediate Similarity	NPC11824
0.7946	Intermediate Similarity	NPC303522
0.7944	Intermediate Similarity	NPC474603
0.7944	Intermediate Similarity	NPC8931
0.7944	Intermediate Similarity	NPC261573
0.7944	Intermediate Similarity	NPC120693
0.7944	Intermediate Similarity	NPC12987
0.7934	Intermediate Similarity	NPC125887
0.7934	Intermediate Similarity	NPC80694
0.7934	Intermediate Similarity	NPC186098
0.7934	Intermediate Similarity	NPC475017
0.7931	Intermediate Similarity	NPC230951
0.7917	Intermediate Similarity	NPC474737
0.7917	Intermediate Similarity	NPC303680
0.7917	Intermediate Similarity	NPC179777
0.7917	Intermediate Similarity	NPC127937
0.7917	Intermediate Similarity	NPC92207
0.7917	Intermediate Similarity	NPC474476
0.7917	Intermediate Similarity	NPC90128
0.7917	Intermediate Similarity	NPC84076
0.7917	Intermediate Similarity	NPC237868
0.7913	Intermediate Similarity	NPC206007
0.7909	Intermediate Similarity	NPC474272
0.7909	Intermediate Similarity	NPC95172
0.7899	Intermediate Similarity	NPC221798
0.7899	Intermediate Similarity	NPC56332
0.7899	Intermediate Similarity	NPC255073
0.7895	Intermediate Similarity	NPC268317
0.7895	Intermediate Similarity	NPC131192
0.7895	Intermediate Similarity	NPC316062
0.789	Intermediate Similarity	NPC228737
0.7881	Intermediate Similarity	NPC116562
0.7876	Intermediate Similarity	NPC235250
0.787	Intermediate Similarity	NPC42383
0.787	Intermediate Similarity	NPC8302
0.787	Intermediate Similarity	NPC288760
0.7869	Intermediate Similarity	NPC211120
0.7869	Intermediate Similarity	NPC170546
0.7869	Intermediate Similarity	NPC66246
0.7869	Intermediate Similarity	NPC939
0.7863	Intermediate Similarity	NPC158949
0.7851	Intermediate Similarity	NPC123722
0.7851	Intermediate Similarity	NPC123228
0.7851	Intermediate Similarity	NPC276466
0.7851	Intermediate Similarity	NPC281020
0.7851	Intermediate Similarity	NPC128428
0.7851	Intermediate Similarity	NPC151167
0.7851	Intermediate Similarity	NPC20404
0.7851	Intermediate Similarity	NPC20287
0.7851	Intermediate Similarity	NPC475496
0.7851	Intermediate Similarity	NPC293641
0.7851	Intermediate Similarity	NPC305518
0.7851	Intermediate Similarity	NPC12022
0.7851	Intermediate Similarity	NPC5018
0.7851	Intermediate Similarity	NPC49852
0.785	Intermediate Similarity	NPC12870
0.785	Intermediate Similarity	NPC24327
0.7838	Intermediate Similarity	NPC475852
0.7838	Intermediate Similarity	NPC137685
0.7838	Intermediate Similarity	NPC179309
0.7833	Intermediate Similarity	NPC224657
0.7833	Intermediate Similarity	NPC165556
0.7833	Intermediate Similarity	NPC280767
0.7826	Intermediate Similarity	NPC185738
0.7818	Intermediate Similarity	NPC97811
0.7818	Intermediate Similarity	NPC201959
0.7815	Intermediate Similarity	NPC472888

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 NPC38209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	1075
0.2-0.3	1272
0.3-0.4	2665
0.4-0.5	1919
0.5-0.6	1216
0.6-0.7	610
0.7-0.8	104
0.8-0.85	9
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9143	High Similarity	NPD1241	Discontinued
0.8482	Intermediate Similarity	NPD1651	Approved
0.8348	Intermediate Similarity	NPD3972	Approved
0.8261	Intermediate Similarity	NPD1281	Approved
0.8205	Intermediate Similarity	NPD1876	Approved
0.8131	Intermediate Similarity	NPD3134	Approved
0.807	Intermediate Similarity	NPD1894	Discontinued
0.8056	Intermediate Similarity	NPD1358	Approved
0.8051	Intermediate Similarity	NPD1283	Approved
0.7982	Intermediate Similarity	NPD2684	Approved
0.7949	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD17	Approved
0.7909	Intermediate Similarity	NPD5451	Approved
0.7881	Intermediate Similarity	NPD1481	Phase 2
0.7863	Intermediate Similarity	NPD3847	Discontinued
0.7857	Intermediate Similarity	NPD5535	Approved
0.7826	Intermediate Similarity	NPD5536	Phase 2
0.7797	Intermediate Similarity	NPD1535	Discovery
0.7768	Intermediate Similarity	NPD228	Approved
0.7759	Intermediate Similarity	NPD9545	Approved
0.775	Intermediate Similarity	NPD196	Phase 1
0.7731	Intermediate Similarity	NPD1608	Approved
0.7705	Intermediate Similarity	NPD454	Approved
0.7699	Intermediate Similarity	NPD7843	Approved
0.7699	Intermediate Similarity	NPD821	Approved
0.768	Intermediate Similarity	NPD3142	Approved
0.768	Intermediate Similarity	NPD3140	Approved
0.768	Intermediate Similarity	NPD1240	Approved
0.7632	Intermediate Similarity	NPD5283	Phase 1
0.7623	Intermediate Similarity	NPD2798	Approved
0.7586	Intermediate Similarity	NPD9493	Approved
0.7583	Intermediate Similarity	NPD9717	Approved
0.7568	Intermediate Similarity	NPD290	Approved
0.7561	Intermediate Similarity	NPD9494	Approved
0.7559	Intermediate Similarity	NPD1607	Approved
0.7545	Intermediate Similarity	NPD9697	Approved
0.7542	Intermediate Similarity	NPD5691	Approved
0.7542	Intermediate Similarity	NPD5585	Approved
0.7541	Intermediate Similarity	NPD3267	Approved
0.7541	Intermediate Similarity	NPD3266	Approved
0.754	Intermediate Similarity	NPD2979	Phase 3
0.752	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.748	Intermediate Similarity	NPD1019	Discontinued
0.7479	Intermediate Similarity	NPD4626	Approved
0.7479	Intermediate Similarity	NPD1778	Approved
0.7477	Intermediate Similarity	NPD968	Approved
0.746	Intermediate Similarity	NPD6233	Phase 2
0.746	Intermediate Similarity	NPD4062	Phase 3
0.746	Intermediate Similarity	NPD8032	Phase 2
0.7398	Intermediate Similarity	NPD2797	Approved
0.7385	Intermediate Similarity	NPD2796	Approved
0.7377	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2614	Approved
0.7358	Intermediate Similarity	NPD2933	Approved
0.7358	Intermediate Similarity	NPD2934	Approved
0.7344	Intermediate Similarity	NPD6355	Discontinued
0.7327	Intermediate Similarity	NPD111	Approved
0.7308	Intermediate Similarity	NPD2799	Discontinued
0.7308	Intermediate Similarity	NPD1510	Phase 2
0.7304	Intermediate Similarity	NPD1139	Approved
0.7304	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1137	Approved
0.7297	Intermediate Similarity	NPD164	Approved
0.729	Intermediate Similarity	NPD2860	Approved
0.729	Intermediate Similarity	NPD2859	Approved
0.7288	Intermediate Similarity	NPD3596	Phase 2
0.7258	Intermediate Similarity	NPD1203	Approved
0.7257	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4476	Approved
0.7252	Intermediate Similarity	NPD4477	Approved
0.7252	Intermediate Similarity	NPD2531	Phase 2
0.7252	Intermediate Similarity	NPD2438	Suspended
0.7252	Intermediate Similarity	NPD2935	Discontinued
0.7248	Intermediate Similarity	NPD1238	Approved
0.7244	Intermediate Similarity	NPD1296	Phase 2
0.7244	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD1138	Approved
0.7236	Intermediate Similarity	NPD4359	Approved
0.7218	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD422	Phase 1
0.7212	Intermediate Similarity	NPD9295	Approved
0.7209	Intermediate Similarity	NPD4618	Approved
0.7209	Intermediate Similarity	NPD4622	Approved
0.7207	Intermediate Similarity	NPD9261	Approved
0.7203	Intermediate Similarity	NPD255	Approved
0.7203	Intermediate Similarity	NPD256	Approved
0.72	Intermediate Similarity	NPD5647	Approved
0.7197	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2344	Approved
0.7197	Intermediate Similarity	NPD2353	Approved
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2668	Approved
0.719	Intermediate Similarity	NPD2667	Approved
0.7176	Intermediate Similarity	NPD3748	Approved
0.7167	Intermediate Similarity	NPD1548	Phase 1
0.7167	Intermediate Similarity	NPD6580	Approved
0.7167	Intermediate Similarity	NPD6581	Approved
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7132	Intermediate Similarity	NPD4307	Phase 2
0.7131	Intermediate Similarity	NPD3496	Discontinued
0.7121	Intermediate Similarity	NPD2239	Approved
0.7121	Intermediate Similarity	NPD2240	Approved
0.712	Intermediate Similarity	NPD987	Approved
0.7119	Intermediate Similarity	NPD595	Approved
0.7119	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD593	Approved
0.7111	Intermediate Similarity	NPD3887	Approved
0.7109	Intermediate Similarity	NPD2313	Discontinued
0.7107	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3025	Approved
0.7107	Intermediate Similarity	NPD3024	Approved
0.7099	Intermediate Similarity	NPD743	Approved
0.7099	Intermediate Similarity	NPD5689	Approved
0.7099	Intermediate Similarity	NPD5688	Approved
0.7091	Intermediate Similarity	NPD3020	Approved
0.709	Intermediate Similarity	NPD2654	Approved
0.7077	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD1933	Approved
0.7075	Intermediate Similarity	NPD9365	Approved
0.7071	Intermediate Similarity	NPD9490	Approved
0.7069	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2557	Approved
0.7059	Intermediate Similarity	NPD709	Approved
0.7059	Intermediate Similarity	NPD6671	Approved
0.7049	Intermediate Similarity	NPD2932	Approved
0.7049	Intermediate Similarity	NPD5846	Approved
0.7049	Intermediate Similarity	NPD6516	Phase 2
0.7049	Intermediate Similarity	NPD3019	Approved
0.7043	Intermediate Similarity	NPD2182	Approved
0.7037	Intermediate Similarity	NPD7003	Approved
0.7037	Intermediate Similarity	NPD4628	Phase 3
0.7031	Intermediate Similarity	NPD7095	Approved
0.7031	Intermediate Similarity	NPD5163	Phase 2
0.7027	Intermediate Similarity	NPD3028	Approved
0.7025	Intermediate Similarity	NPD1182	Approved
0.7015	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4534	Discontinued
0.7007	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD9568	Approved
0.7	Intermediate Similarity	NPD9495	Approved
0.6992	Remote Similarity	NPD3023	Approved
0.6992	Remote Similarity	NPD3026	Approved
0.6985	Remote Similarity	NPD2309	Approved
0.6985	Remote Similarity	NPD2354	Approved
0.6984	Remote Similarity	NPD6362	Approved
0.6977	Remote Similarity	NPD411	Approved
0.697	Remote Similarity	NPD1536	Approved
0.6967	Remote Similarity	NPD1357	Approved
0.6967	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD940	Approved
0.6964	Remote Similarity	NPD846	Approved
0.6963	Remote Similarity	NPD1243	Approved
0.6963	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD9491	Approved
0.696	Remote Similarity	NPD3685	Discontinued
0.696	Remote Similarity	NPD5327	Phase 3
0.696	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6583	Phase 3
0.696	Remote Similarity	NPD1669	Approved
0.696	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6582	Phase 2
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9267	Approved
0.6953	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1184	Approved
0.6947	Remote Similarity	NPD447	Suspended
0.694	Remote Similarity	NPD1471	Phase 3
0.694	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3705	Approved
0.6935	Remote Similarity	NPD1611	Approved
0.6935	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD9257	Approved
0.6923	Remote Similarity	NPD4870	Approved
0.6923	Remote Similarity	NPD9259	Approved
0.6917	Remote Similarity	NPD4308	Phase 3
0.6917	Remote Similarity	NPD6387	Discontinued
0.6912	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4110	Phase 3
0.6912	Remote Similarity	NPD3750	Approved
0.6905	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3225	Approved
0.6899	Remote Similarity	NPD5746	Approved
0.6899	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD74	Approved
0.6897	Remote Similarity	NPD9266	Approved
0.6891	Remote Similarity	NPD594	Approved
0.6891	Remote Similarity	NPD592	Approved
0.6889	Remote Similarity	NPD5958	Discontinued
0.6889	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2897	Discontinued
0.6884	Remote Similarity	NPD6143	Clinical (unspecified phase)

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