NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.07
Volume:	162.698
LogP:	1.338
LogD:	1.295
LogS:	-0.713
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	2.046
Fsp3:	0.111
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:	-4.401
MDCK Permeability:	1.774885276972782e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.175

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.169
Plasma Protein Binding (PPB):	66.24515533447266%
Volume Distribution (VD):	2.199
Pgp-substrate:	33.93693161010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.685
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.856
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	13.33
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.716
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.954
Carcinogencity:	0.278
Eye Corrosion:	0.607
Eye Irritation:	0.992
Respiratory Toxicity:	0.27

Download Data

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

Natural Product: NPC104216

Natural Product ID:	NPC104216
*Common Name:**	4-((E)-3-Hydroxy-Propenyl)-Phenol
IUPAC Name:	4-[(E)-3-hydroxyprop-1-enyl]phenol
Synonyms:
Standard InCHIKey:	PTNLHDGQWUGONS-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
SMILES:	C(=Cc1ccc(cc1)O)/CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL109034
PubChem CID:	5280535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002754] Cinnamyl alcohols

*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
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1596	Taraxacum borealisinense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13668	Taraxacum platycarpum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23327	Taraxacum coreanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23327	Taraxacum coreanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13668	Taraxacum platycarpum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	14

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5
Organism	6
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	2.0	%	PMID[448936]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[448937]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	24.0	%	PMID[448937]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-3.4	%	PMID[448938]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-2.8	%	PMID[448938]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[448938]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	35.8	%	PMID[448938]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	46.9	%	PMID[448938]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	98.9	%	PMID[448938]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	98.4	%	PMID[448938]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	116.2	%	PMID[448938]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	110.2	%	PMID[448938]
NPT2	Others	Unspecified		Inhibition	=	-4.7	%	PMID[448938]
NPT2	Others	Unspecified		Inhibition	=	-9.1	%	PMID[448938]
NPT2	Others	Unspecified		Inhibition	=	4.5	%	PMID[448938]
NPT2	Others	Unspecified		Inhibition	=	9.2	%	PMID[448938]

☑ 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 NPC104216 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	260
0.1-0.2	2460
0.2-0.3	7798
0.3-0.4	11753
0.4-0.5	7180
0.5-0.6	8953
0.6-0.7	3264
0.7-0.8	800
0.8-0.85	151
0.85-0.9	55
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9765	High Similarity	NPC300017
0.954	High Similarity	NPC138117
0.954	High Similarity	NPC325292
0.9535	High Similarity	NPC300478
0.9518	High Similarity	NPC265146
0.9405	High Similarity	NPC175313
0.9405	High Similarity	NPC248817
0.9326	High Similarity	NPC313650
0.9294	High Similarity	NPC197783
0.9286	High Similarity	NPC124436
0.9186	High Similarity	NPC23167
0.9186	High Similarity	NPC184169
0.9111	High Similarity	NPC286006
0.9091	High Similarity	NPC47950
0.9091	High Similarity	NPC312304
0.908	High Similarity	NPC25493
0.908	High Similarity	NPC113460
0.9022	High Similarity	NPC131587
0.9022	High Similarity	NPC128723
0.9022	High Similarity	NPC216468
0.9022	High Similarity	NPC132078
0.9022	High Similarity	NPC78119
0.9022	High Similarity	NPC51333
0.8989	High Similarity	NPC270547
0.8989	High Similarity	NPC45040
0.8977	High Similarity	NPC318325
0.8977	High Similarity	NPC258219
0.8977	High Similarity	NPC280347
0.8977	High Similarity	NPC98772
0.8977	High Similarity	NPC242240
0.8977	High Similarity	NPC177420
0.8977	High Similarity	NPC123273
0.8925	High Similarity	NPC213730
0.8889	High Similarity	NPC181709
0.8876	High Similarity	NPC55561
0.8851	High Similarity	NPC155393
0.883	High Similarity	NPC40258
0.883	High Similarity	NPC91461
0.883	High Similarity	NPC7686
0.883	High Similarity	NPC101025
0.883	High Similarity	NPC110764
0.883	High Similarity	NPC471578
0.8817	High Similarity	NPC171843
0.8791	High Similarity	NPC32977
0.8791	High Similarity	NPC81010
0.8791	High Similarity	NPC128062
0.8791	High Similarity	NPC151715
0.8778	High Similarity	NPC155908
0.8778	High Similarity	NPC204210
0.8778	High Similarity	NPC304541
0.875	High Similarity	NPC407
0.875	High Similarity	NPC307235
0.8736	High Similarity	NPC150837
0.8736	High Similarity	NPC286904
0.871	High Similarity	NPC474073
0.8696	High Similarity	NPC274678
0.8696	High Similarity	NPC26244
0.8652	High Similarity	NPC27974
0.8646	High Similarity	NPC12278
0.8617	High Similarity	NPC100870
0.8602	High Similarity	NPC473388
0.8602	High Similarity	NPC82664
0.8602	High Similarity	NPC283711
0.8602	High Similarity	NPC216520
0.8602	High Similarity	NPC292730
0.8602	High Similarity	NPC132271
0.8587	High Similarity	NPC316301
0.8587	High Similarity	NPC27323
0.8557	High Similarity	NPC233396
0.8557	High Similarity	NPC154899
0.8556	High Similarity	NPC70436
0.8542	High Similarity	NPC62351
0.8542	High Similarity	NPC305205
0.8542	High Similarity	NPC304638
0.8526	High Similarity	NPC174911
0.8526	High Similarity	NPC253746
0.8526	High Similarity	NPC294741
0.8526	High Similarity	NPC130103
0.8511	High Similarity	NPC109955
0.8511	High Similarity	NPC201967
0.8511	High Similarity	NPC107619
0.8511	High Similarity	NPC88420
0.8511	High Similarity	NPC260000
0.8495	Intermediate Similarity	NPC107522
0.8495	Intermediate Similarity	NPC8392
0.8469	Intermediate Similarity	NPC92623
0.8469	Intermediate Similarity	NPC135464
0.8462	Intermediate Similarity	NPC151764
0.8462	Intermediate Similarity	NPC192
0.8444	Intermediate Similarity	NPC19680
0.8438	Intermediate Similarity	NPC51633
0.8421	Intermediate Similarity	NPC245561
0.8421	Intermediate Similarity	NPC80027
0.8421	Intermediate Similarity	NPC275104
0.8421	Intermediate Similarity	NPC280869
0.8421	Intermediate Similarity	NPC92730
0.8421	Intermediate Similarity	NPC130193
0.8404	Intermediate Similarity	NPC202986
0.8372	Intermediate Similarity	NPC117180
0.837	Intermediate Similarity	NPC306074
0.837	Intermediate Similarity	NPC231150
0.8367	Intermediate Similarity	NPC8302
0.8351	Intermediate Similarity	NPC477801
0.8351	Intermediate Similarity	NPC192596
0.8351	Intermediate Similarity	NPC235762
0.8351	Intermediate Similarity	NPC471228
0.8351	Intermediate Similarity	NPC477802
0.8333	Intermediate Similarity	NPC161571
0.8333	Intermediate Similarity	NPC223393
0.8333	Intermediate Similarity	NPC248573
0.8333	Intermediate Similarity	NPC66655
0.8333	Intermediate Similarity	NPC52472
0.8333	Intermediate Similarity	NPC275053
0.8316	Intermediate Similarity	NPC32674
0.8316	Intermediate Similarity	NPC225464
0.8316	Intermediate Similarity	NPC77492
0.83	Intermediate Similarity	NPC262365
0.83	Intermediate Similarity	NPC317305
0.8298	Intermediate Similarity	NPC246679
0.8298	Intermediate Similarity	NPC257182
0.8283	Intermediate Similarity	NPC19149
0.828	Intermediate Similarity	NPC210497
0.828	Intermediate Similarity	NPC29373
0.828	Intermediate Similarity	NPC3358
0.828	Intermediate Similarity	NPC162314
0.828	Intermediate Similarity	NPC55903
0.828	Intermediate Similarity	NPC306884
0.828	Intermediate Similarity	NPC94139
0.828	Intermediate Similarity	NPC147284
0.828	Intermediate Similarity	NPC271440
0.8276	Intermediate Similarity	NPC87299
0.8276	Intermediate Similarity	NPC99394
0.8276	Intermediate Similarity	NPC103326
0.8276	Intermediate Similarity	NPC329319
0.8265	Intermediate Similarity	NPC475225
0.8265	Intermediate Similarity	NPC108875
0.8265	Intermediate Similarity	NPC474603
0.8265	Intermediate Similarity	NPC38079
0.8265	Intermediate Similarity	NPC323810
0.8265	Intermediate Similarity	NPC12987
0.8247	Intermediate Similarity	NPC472585
0.8229	Intermediate Similarity	NPC125732
0.8229	Intermediate Similarity	NPC122005
0.8229	Intermediate Similarity	NPC252821
0.8218	Intermediate Similarity	NPC145638
0.8218	Intermediate Similarity	NPC55617
0.8218	Intermediate Similarity	NPC290566
0.8218	Intermediate Similarity	NPC326187
0.8218	Intermediate Similarity	NPC62258
0.82	Intermediate Similarity	NPC251306
0.82	Intermediate Similarity	NPC260952
0.8193	Intermediate Similarity	NPC100980
0.8191	Intermediate Similarity	NPC245187
0.8191	Intermediate Similarity	NPC152415
0.8191	Intermediate Similarity	NPC76938
0.8182	Intermediate Similarity	NPC470393
0.8182	Intermediate Similarity	NPC127676
0.8182	Intermediate Similarity	NPC471350
0.8163	Intermediate Similarity	NPC196479
0.8163	Intermediate Similarity	NPC470202
0.8163	Intermediate Similarity	NPC168829
0.8163	Intermediate Similarity	NPC178902
0.8163	Intermediate Similarity	NPC68269
0.8163	Intermediate Similarity	NPC135784
0.8152	Intermediate Similarity	NPC99886
0.8152	Intermediate Similarity	NPC177844
0.8152	Intermediate Similarity	NPC8002
0.8152	Intermediate Similarity	NPC259134
0.8144	Intermediate Similarity	NPC155847
0.8144	Intermediate Similarity	NPC225506
0.8144	Intermediate Similarity	NPC289381
0.8137	Intermediate Similarity	NPC475018
0.8137	Intermediate Similarity	NPC252544
0.8137	Intermediate Similarity	NPC174096
0.8137	Intermediate Similarity	NPC226401
0.8137	Intermediate Similarity	NPC147634
0.8137	Intermediate Similarity	NPC120982
0.8137	Intermediate Similarity	NPC79793
0.8137	Intermediate Similarity	NPC63345
0.8137	Intermediate Similarity	NPC321252
0.8137	Intermediate Similarity	NPC44732
0.8125	Intermediate Similarity	NPC291789
0.8125	Intermediate Similarity	NPC475078
0.8125	Intermediate Similarity	NPC152097
0.8125	Intermediate Similarity	NPC140619
0.8119	Intermediate Similarity	NPC31274
0.8119	Intermediate Similarity	NPC206341
0.8105	Intermediate Similarity	NPC144682
0.8105	Intermediate Similarity	NPC32714
0.81	Intermediate Similarity	NPC113457
0.809	Intermediate Similarity	NPC304538
0.8085	Intermediate Similarity	NPC295295
0.8081	Intermediate Similarity	NPC8931
0.8081	Intermediate Similarity	NPC119860
0.8081	Intermediate Similarity	NPC288411
0.8081	Intermediate Similarity	NPC120719
0.8081	Intermediate Similarity	NPC130817
0.8081	Intermediate Similarity	NPC52087
0.8081	Intermediate Similarity	NPC471511
0.8081	Intermediate Similarity	NPC120693

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 NPC104216 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	1627
0.3-0.4	2912
0.4-0.5	1845
0.5-0.6	971
0.6-0.7	367
0.7-0.8	60
0.8-0.85	11
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD111	Approved
0.8791	High Similarity	NPD2934	Approved
0.8791	High Similarity	NPD2933	Approved
0.8696	High Similarity	NPD2859	Approved
0.8696	High Similarity	NPD2860	Approved
0.8587	High Similarity	NPD1432	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD3020	Approved
0.8333	Intermediate Similarity	NPD1242	Phase 1
0.8333	Intermediate Similarity	NPD9294	Approved
0.8247	Intermediate Similarity	NPD940	Approved
0.8247	Intermediate Similarity	NPD846	Approved
0.8218	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD9087	Approved
0.8105	Intermediate Similarity	NPD844	Approved
0.8105	Intermediate Similarity	NPD1809	Phase 2
0.8085	Intermediate Similarity	NPD845	Approved
0.8023	Intermediate Similarity	NPD9088	Approved
0.8021	Intermediate Similarity	NPD288	Approved
0.7959	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD968	Approved
0.79	Intermediate Similarity	NPD9608	Approved
0.79	Intermediate Similarity	NPD9610	Approved
0.7767	Intermediate Similarity	NPD2684	Approved
0.7755	Intermediate Similarity	NPD9273	Approved
0.7714	Intermediate Similarity	NPD228	Approved
0.7692	Intermediate Similarity	NPD3022	Approved
0.7692	Intermediate Similarity	NPD3021	Approved
0.767	Intermediate Similarity	NPD290	Approved
0.7667	Intermediate Similarity	NPD9089	Approved
0.7615	Intermediate Similarity	NPD318	Approved
0.7615	Intermediate Similarity	NPD317	Approved
0.7615	Intermediate Similarity	NPD856	Approved
0.7615	Intermediate Similarity	NPD16	Approved
0.76	Intermediate Similarity	NPD3028	Approved
0.7556	Intermediate Similarity	NPD9093	Approved
0.7547	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3091	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9614	Approved
0.75	Intermediate Similarity	NPD9618	Approved
0.7477	Intermediate Similarity	NPD9377	Approved
0.7477	Intermediate Similarity	NPD7843	Approved
0.7477	Intermediate Similarity	NPD821	Approved
0.7477	Intermediate Similarity	NPD9379	Approved
0.7474	Intermediate Similarity	NPD9295	Approved
0.7451	Intermediate Similarity	NPD9500	Approved
0.7411	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD9381	Approved
0.7411	Intermediate Similarity	NPD9384	Approved
0.7407	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2228	Approved
0.7407	Intermediate Similarity	NPD2229	Approved
0.7407	Intermediate Similarity	NPD2234	Approved
0.7404	Intermediate Similarity	NPD3134	Approved
0.7404	Intermediate Similarity	NPD1444	Approved
0.7404	Intermediate Similarity	NPD1445	Approved
0.7387	Intermediate Similarity	NPD1548	Phase 1
0.7387	Intermediate Similarity	NPD9545	Approved
0.7333	Intermediate Similarity	NPD1358	Approved
0.7321	Intermediate Similarity	NPD1357	Approved
0.732	Intermediate Similarity	NPD9365	Approved
0.7297	Intermediate Similarity	NPD9616	Approved
0.7297	Intermediate Similarity	NPD9615	Approved
0.7297	Intermediate Similarity	NPD9613	Approved
0.729	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD3092	Approved
0.7273	Intermediate Similarity	NPD256	Approved
0.7273	Intermediate Similarity	NPD7157	Approved
0.7273	Intermediate Similarity	NPD255	Approved
0.7234	Intermediate Similarity	NPD9073	Approved
0.7232	Intermediate Similarity	NPD316	Approved
0.7228	Intermediate Similarity	NPD9495	Approved
0.7217	Intermediate Similarity	NPD2561	Approved
0.7217	Intermediate Similarity	NPD2562	Approved
0.7207	Intermediate Similarity	NPD9568	Approved
0.7196	Intermediate Similarity	NPD4750	Phase 3
0.7196	Intermediate Similarity	NPD1792	Phase 2
0.7193	Intermediate Similarity	NPD3421	Phase 3
0.7188	Intermediate Similarity	NPD9094	Approved
0.7174	Intermediate Similarity	NPD9250	Approved
0.717	Intermediate Similarity	NPD2342	Discontinued
0.7155	Intermediate Similarity	NPD9622	Approved
0.7155	Intermediate Similarity	NPD4659	Approved
0.713	Intermediate Similarity	NPD1610	Phase 2
0.7105	Intermediate Similarity	NPD3095	Discontinued
0.7103	Intermediate Similarity	NPD9266	Approved
0.7103	Intermediate Similarity	NPD74	Approved
0.71	Intermediate Similarity	NPD9296	Approved
0.7059	Intermediate Similarity	NPD9609	Approved
0.7059	Intermediate Similarity	NPD9611	Approved
0.7059	Intermediate Similarity	NPD9612	Approved
0.7054	Intermediate Similarity	NPD9493	Approved
0.7037	Intermediate Similarity	NPD5451	Approved
0.7034	Intermediate Similarity	NPD3094	Phase 2
0.7034	Intermediate Similarity	NPD1129	Approved
0.7034	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1133	Approved
0.7034	Intermediate Similarity	NPD1134	Approved
0.7034	Intermediate Similarity	NPD1131	Approved
0.7034	Intermediate Similarity	NPD4103	Phase 2
0.7034	Intermediate Similarity	NPD1135	Approved
0.7027	Intermediate Similarity	NPD475	Phase 2
0.7027	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9267	Approved
0.7009	Intermediate Similarity	NPD9263	Approved
0.7009	Intermediate Similarity	NPD6583	Phase 3
0.7009	Intermediate Similarity	NPD9264	Approved
0.7009	Intermediate Similarity	NPD6582	Phase 2
0.7	Intermediate Similarity	NPD7635	Approved
0.6983	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9620	Approved
0.6975	Remote Similarity	NPD9621	Approved
0.6975	Remote Similarity	NPD9619	Approved
0.6964	Remote Similarity	NPD6671	Approved
0.6957	Remote Similarity	NPD6516	Phase 2
0.6957	Remote Similarity	NPD2932	Approved
0.6957	Remote Similarity	NPD5846	Approved
0.6957	Remote Similarity	NPD4059	Approved
0.6957	Remote Similarity	NPD3019	Approved
0.6957	Remote Similarity	NPD2286	Discontinued
0.6937	Remote Similarity	NPD1241	Discontinued
0.693	Remote Similarity	NPD5303	Approved
0.693	Remote Similarity	NPD1894	Discontinued
0.693	Remote Similarity	NPD5304	Approved
0.69	Remote Similarity	NPD9251	Approved
0.69	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1237	Approved
0.6875	Remote Similarity	NPD1791	Approved
0.6875	Remote Similarity	NPD1793	Approved
0.687	Remote Similarity	NPD4093	Discontinued
0.6864	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3685	Discontinued
0.6864	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD855	Approved
0.6857	Remote Similarity	NPD854	Approved
0.6857	Remote Similarity	NPD291	Approved
0.6838	Remote Similarity	NPD422	Phase 1
0.6838	Remote Similarity	NPD1535	Discovery
0.6838	Remote Similarity	NPD1091	Approved
0.6833	Remote Similarity	NPD6584	Phase 3
0.681	Remote Similarity	NPD1751	Approved
0.681	Remote Similarity	NPD2667	Approved
0.681	Remote Similarity	NPD4626	Approved
0.681	Remote Similarity	NPD4589	Approved
0.681	Remote Similarity	NPD2668	Approved
0.6803	Remote Similarity	NPD3136	Phase 2
0.6803	Remote Similarity	NPD3027	Phase 3
0.6792	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5283	Phase 1
0.6783	Remote Similarity	NPD1182	Approved
0.6783	Remote Similarity	NPD1759	Phase 1
0.678	Remote Similarity	NPD2235	Phase 2
0.678	Remote Similarity	NPD1481	Phase 2
0.678	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.678	Remote Similarity	NPD2231	Phase 2
0.6777	Remote Similarity	NPD5736	Approved
0.6777	Remote Similarity	NPD2861	Phase 2
0.6777	Remote Similarity	NPD9494	Approved
0.6754	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3847	Discontinued
0.6748	Remote Similarity	NPD601	Approved
0.6748	Remote Similarity	NPD598	Approved
0.6748	Remote Similarity	NPD597	Approved
0.6729	Remote Similarity	NPD310	Approved
0.6729	Remote Similarity	NPD311	Approved
0.6729	Remote Similarity	NPD315	Approved
0.6729	Remote Similarity	NPD9244	Approved
0.6729	Remote Similarity	NPD314	Approved
0.6729	Remote Similarity	NPD309	Approved
0.6729	Remote Similarity	NPD10	Approved
0.6724	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4908	Phase 1
0.6703	Remote Similarity	NPD9716	Approved
0.67	Remote Similarity	NPD9258	Approved
0.67	Remote Similarity	NPD9256	Approved
0.6697	Remote Similarity	NPD9532	Phase 3
0.6696	Remote Similarity	NPD5535	Approved
0.6696	Remote Similarity	NPD1758	Phase 1
0.6694	Remote Similarity	NPD1136	Approved
0.6694	Remote Similarity	NPD6407	Approved
0.6694	Remote Similarity	NPD6405	Approved
0.6694	Remote Similarity	NPD829	Discontinued
0.6694	Remote Similarity	NPD1130	Approved
0.6694	Remote Similarity	NPD3691	Phase 2
0.6694	Remote Similarity	NPD3690	Phase 2
0.6694	Remote Similarity	NPD1132	Approved
0.6667	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD9697	Approved
0.6667	Remote Similarity	NPD5311	Approved
0.6667	Remote Similarity	NPD9491	Approved
0.6667	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.664	Remote Similarity	NPD3062	Approved
0.664	Remote Similarity	NPD3059	Approved
0.664	Remote Similarity	NPD1613	Approved
0.664	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.664	Remote Similarity	NPD3061	Approved
0.6638	Remote Similarity	NPD2226	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