NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.1
Volume:	264.668
LogP:	3.616
LogD:	4.587
LogS:	-4.479
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	1.54
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.616
MDCK Permeability:	2.2300360797089525e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.694
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797
Plasma Protein Binding (PPB):	96.45186614990234%
Volume Distribution (VD):	0.652
Pgp-substrate:	3.32141375541687%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.379
CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	10.227
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.8
AMES Toxicity:	0.527
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.939
Carcinogencity:	0.663
Eye Corrosion:	0.384
Eye Irritation:	0.99
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC119631

Natural Product ID:	NPC119631
*Common Name:**	Benzyl Cinnamate
IUPAC Name:	benzyl (E)-3-phenylprop-2-enoate
Synonyms:	Benzyl (E)-Cinnamate; Benzyl Cinnamate; Benzyltrans Cinnamate
Standard InCHIKey:	NGHOLYJTSCBCGC-VAWYXSNFSA-N
Standard InCHI:	InChI=1S/C16H14O2/c17-16(12-11-14-7-3-1-4-8-14)18-13-15-9-5-2-6-10-15/h1-12H,13H2/b12-11+
SMILES:	O=C(/C=C/c1ccccc1)OCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL361197
PubChem CID:	5273469
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	resin	n.a.	n.a.	PMID[16724846]
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]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
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.	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]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[29140705]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12588	Cornus officinalis	Species	Cornaceae	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]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11291	Styrax benzoin	Species	Styracaceae	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]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	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]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31091	Comus officinalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2830	Bassia longifolia	Species	Abylidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11729	Eugenia exsucca	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	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]
NPO13986	Anemone coronaria	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16476	Astroloma humifusum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12830	Styrax tonkinensis	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6528	Myroxylon pereirae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	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]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18877	Asplenium ruprechtii	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12588	Cornus officinalis	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	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
EC50	1
IC50	4
Others	3
Potency	5

Activity Type	# Activity
Cell Line	4
Individual Protein	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4364	Individual Protein	17-beta-hydroxysteroid-dehydrogenase	Cochliobolus lunatus	IC50	=	700.0	nM	PMID[570154]
NPT4364	Individual Protein	17-beta-hydroxysteroid-dehydrogenase	Cochliobolus lunatus	IC50	=	7000.0	nM	PMID[570154]
NPT1222	Individual Protein	Type-1A angiotensin II receptor	Mus musculus	IC50	=	47.2	ug.mL-1	PMID[570155]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[570157]
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	35.5	nM	PMID[570158]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[570158]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[570158]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	50.0	%	PMID[570159]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	70.0	ug.mL-1	PMID[570159]
NPT737	Cell Line	HUVEC	Homo sapiens	MTD	=	70.0	ug ml-1	PMID[570159]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	14381.8	nM	PMID[570158]
NPT2557	Organism	Dermatophagoides pteronyssinus	Dermatophagoides pteronyssinus	EC50	=	0.18	g/m2	PMID[570156]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	19011.5	nM	PMID[570158]

☑ 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 NPC119631 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	225
0.1-0.2	1637
0.2-0.3	4319
0.3-0.4	12229
0.4-0.5	10449
0.5-0.6	11216
0.6-0.7	2253
0.7-0.8	290
0.8-0.85	55
0.85-0.9	19
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9425	High Similarity	NPC240108
0.9425	High Similarity	NPC213156
0.931	High Similarity	NPC173443
0.907	High Similarity	NPC58616
0.9032	High Similarity	NPC118343
0.8936	High Similarity	NPC42211
0.8864	High Similarity	NPC89377
0.8837	High Similarity	NPC208183
0.8837	High Similarity	NPC243289
0.8824	High Similarity	NPC165212
0.8764	High Similarity	NPC304760
0.8763	High Similarity	NPC269457
0.8667	High Similarity	NPC220893
0.8632	High Similarity	NPC472318
0.8632	High Similarity	NPC98911
0.8617	High Similarity	NPC276775
0.8617	High Similarity	NPC270654
0.8617	High Similarity	NPC92754
0.8617	High Similarity	NPC249912
0.8526	High Similarity	NPC225060
0.8526	High Similarity	NPC78701
0.8526	High Similarity	NPC35448
0.85	High Similarity	NPC206341
0.8471	Intermediate Similarity	NPC176228
0.8438	Intermediate Similarity	NPC146351
0.8409	Intermediate Similarity	NPC324835
0.8409	Intermediate Similarity	NPC308619
0.8409	Intermediate Similarity	NPC127491
0.8404	Intermediate Similarity	NPC130398
0.8372	Intermediate Similarity	NPC78517
0.8372	Intermediate Similarity	NPC167577
0.8367	Intermediate Similarity	NPC474365
0.8367	Intermediate Similarity	NPC234305
0.8367	Intermediate Similarity	NPC301943
0.8351	Intermediate Similarity	NPC70624
0.8283	Intermediate Similarity	NPC85977
0.8247	Intermediate Similarity	NPC325497
0.8242	Intermediate Similarity	NPC96625
0.8218	Intermediate Similarity	NPC260952
0.8211	Intermediate Similarity	NPC5472
0.8182	Intermediate Similarity	NPC303245
0.8182	Intermediate Similarity	NPC89950
0.8173	Intermediate Similarity	NPC265002
0.8172	Intermediate Similarity	NPC185501
0.8161	Intermediate Similarity	NPC170484
0.8155	Intermediate Similarity	NPC183700
0.814	Intermediate Similarity	NPC287790
0.814	Intermediate Similarity	NPC3672
0.8119	Intermediate Similarity	NPC475203
0.8119	Intermediate Similarity	NPC474376
0.8119	Intermediate Similarity	NPC472315
0.8119	Intermediate Similarity	NPC472316
0.8105	Intermediate Similarity	NPC23453
0.8105	Intermediate Similarity	NPC261181
0.81	Intermediate Similarity	NPC280616
0.81	Intermediate Similarity	NPC242913
0.81	Intermediate Similarity	NPC171831
0.809	Intermediate Similarity	NPC106313
0.8081	Intermediate Similarity	NPC188895
0.8077	Intermediate Similarity	NPC234376
0.8077	Intermediate Similarity	NPC158282
0.8077	Intermediate Similarity	NPC79496
0.8068	Intermediate Similarity	NPC121800
0.8065	Intermediate Similarity	NPC9822
0.8061	Intermediate Similarity	NPC203925
0.8058	Intermediate Similarity	NPC273837
0.8043	Intermediate Similarity	NPC286608
0.8043	Intermediate Similarity	NPC169050
0.8041	Intermediate Similarity	NPC325499
0.8039	Intermediate Similarity	NPC277788
0.8023	Intermediate Similarity	NPC175393
0.8022	Intermediate Similarity	NPC475710
0.8	Intermediate Similarity	NPC89886
0.8	Intermediate Similarity	NPC179686
0.8	Intermediate Similarity	NPC60679
0.8	Intermediate Similarity	NPC128368
0.8	Intermediate Similarity	NPC82426
0.8	Intermediate Similarity	NPC91820
0.7978	Intermediate Similarity	NPC71795
0.7961	Intermediate Similarity	NPC474364
0.7961	Intermediate Similarity	NPC469636
0.7961	Intermediate Similarity	NPC10251
0.7961	Intermediate Similarity	NPC17417
0.7944	Intermediate Similarity	NPC473507
0.7941	Intermediate Similarity	NPC136962
0.7941	Intermediate Similarity	NPC326447
0.7941	Intermediate Similarity	NPC37115
0.7941	Intermediate Similarity	NPC119271
0.7921	Intermediate Similarity	NPC114594
0.7889	Intermediate Similarity	NPC323103
0.7889	Intermediate Similarity	NPC103387
0.7889	Intermediate Similarity	NPC99240
0.7885	Intermediate Similarity	NPC196246
0.7885	Intermediate Similarity	NPC251854
0.7885	Intermediate Similarity	NPC214067
0.7885	Intermediate Similarity	NPC93084
0.7864	Intermediate Similarity	NPC151530
0.7864	Intermediate Similarity	NPC157473
0.7864	Intermediate Similarity	NPC56493
0.7843	Intermediate Similarity	NPC209632
0.7843	Intermediate Similarity	NPC128730
0.7826	Intermediate Similarity	NPC53299
0.7822	Intermediate Similarity	NPC304638
0.7812	Intermediate Similarity	NPC77273
0.781	Intermediate Similarity	NPC474157
0.781	Intermediate Similarity	NPC210089
0.781	Intermediate Similarity	NPC476003
0.781	Intermediate Similarity	NPC167504
0.781	Intermediate Similarity	NPC1082
0.781	Intermediate Similarity	NPC305912
0.7802	Intermediate Similarity	NPC270507
0.7798	Intermediate Similarity	NPC469574
0.7788	Intermediate Similarity	NPC83628
0.7788	Intermediate Similarity	NPC265407
0.7778	Intermediate Similarity	NPC475954
0.7767	Intermediate Similarity	NPC176971
0.7745	Intermediate Similarity	NPC109637
0.7745	Intermediate Similarity	NPC269644
0.7745	Intermediate Similarity	NPC31786
0.7742	Intermediate Similarity	NPC318107
0.7736	Intermediate Similarity	NPC82899
0.7736	Intermediate Similarity	NPC270699
0.7727	Intermediate Similarity	NPC275519
0.7723	Intermediate Similarity	NPC45613
0.7714	Intermediate Similarity	NPC79543
0.7714	Intermediate Similarity	NPC149545
0.7714	Intermediate Similarity	NPC174099
0.7708	Intermediate Similarity	NPC472319
0.7685	Intermediate Similarity	NPC210092
0.767	Intermediate Similarity	NPC472919
0.767	Intermediate Similarity	NPC139891
0.767	Intermediate Similarity	NPC227255
0.7664	Intermediate Similarity	NPC272524
0.7664	Intermediate Similarity	NPC474176
0.7664	Intermediate Similarity	NPC161611
0.7642	Intermediate Similarity	NPC260818
0.7636	Intermediate Similarity	NPC45104
0.7634	Intermediate Similarity	NPC294134
0.7624	Intermediate Similarity	NPC253746
0.7619	Intermediate Similarity	NPC99846
0.7619	Intermediate Similarity	NPC281604
0.7619	Intermediate Similarity	NPC269023
0.7615	Intermediate Similarity	NPC296526
0.7596	Intermediate Similarity	NPC30594
0.7596	Intermediate Similarity	NPC37622
0.7593	Intermediate Similarity	NPC153053
0.7593	Intermediate Similarity	NPC308744
0.7593	Intermediate Similarity	NPC307651
0.7573	Intermediate Similarity	NPC2518
0.757	Intermediate Similarity	NPC474314
0.757	Intermediate Similarity	NPC321852
0.757	Intermediate Similarity	NPC185840
0.7568	Intermediate Similarity	NPC277460
0.7549	Intermediate Similarity	NPC84325
0.7549	Intermediate Similarity	NPC94343
0.7545	Intermediate Similarity	NPC128249
0.7527	Intermediate Similarity	NPC95429
0.7525	Intermediate Similarity	NPC171843
0.7524	Intermediate Similarity	NPC472314
0.7524	Intermediate Similarity	NPC475465
0.7524	Intermediate Similarity	NPC156648
0.7523	Intermediate Similarity	NPC306740
0.7523	Intermediate Similarity	NPC474685
0.7522	Intermediate Similarity	NPC229600
0.75	Intermediate Similarity	NPC473855
0.75	Intermediate Similarity	NPC127676
0.75	Intermediate Similarity	NPC206800
0.75	Intermediate Similarity	NPC263386
0.75	Intermediate Similarity	NPC32203
0.75	Intermediate Similarity	NPC141791
0.75	Intermediate Similarity	NPC238115
0.75	Intermediate Similarity	NPC288760
0.75	Intermediate Similarity	NPC289201
0.7477	Intermediate Similarity	NPC473809
0.7477	Intermediate Similarity	NPC228318
0.7476	Intermediate Similarity	NPC255676
0.7455	Intermediate Similarity	NPC149691
0.7455	Intermediate Similarity	NPC100353
0.7453	Intermediate Similarity	NPC40178
0.7453	Intermediate Similarity	NPC85493
0.7451	Intermediate Similarity	NPC13755
0.7451	Intermediate Similarity	NPC316797
0.7434	Intermediate Similarity	NPC233282
0.7434	Intermediate Similarity	NPC473243
0.7431	Intermediate Similarity	NPC474363
0.7429	Intermediate Similarity	NPC51174
0.7429	Intermediate Similarity	NPC477251
0.7426	Intermediate Similarity	NPC175298
0.7423	Intermediate Similarity	NPC62765
0.7419	Intermediate Similarity	NPC288903
0.7407	Intermediate Similarity	NPC139946
0.7404	Intermediate Similarity	NPC283546
0.74	Intermediate Similarity	NPC246679
0.7387	Intermediate Similarity	NPC190298
0.7368	Intermediate Similarity	NPC470848
0.7368	Intermediate Similarity	NPC470849
0.7364	Intermediate Similarity	NPC474408
0.7364	Intermediate Similarity	NPC87563
0.7358	Intermediate Similarity	NPC47536
0.7358	Intermediate Similarity	NPC20485

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 NPC119631 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1039
0.2-0.3	1054
0.3-0.4	3117
0.4-0.5	2223
0.5-0.6	1160
0.6-0.7	314
0.7-0.8	43
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD1238	Approved
0.8105	Intermediate Similarity	NPD1202	Approved
0.8043	Intermediate Similarity	NPD1282	Approved
0.7961	Intermediate Similarity	NPD2182	Approved
0.7959	Intermediate Similarity	NPD5926	Approved
0.7941	Intermediate Similarity	NPD3134	Approved
0.781	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD164	Approved
0.7742	Intermediate Similarity	NPD9259	Approved
0.7742	Intermediate Similarity	NPD9257	Approved
0.7692	Intermediate Similarity	NPD1358	Approved
0.767	Intermediate Similarity	NPD9697	Approved
0.7576	Intermediate Similarity	NPD1989	Approved
0.7547	Intermediate Similarity	NPD5236	Approved
0.7547	Intermediate Similarity	NPD5240	Approved
0.7547	Intermediate Similarity	NPD5239	Approved
0.7547	Intermediate Similarity	NPD5235	Approved
0.7547	Intermediate Similarity	NPD5237	Approved
0.75	Intermediate Similarity	NPD689	Discontinued
0.75	Intermediate Similarity	NPD9716	Approved
0.7451	Intermediate Similarity	NPD2549	Approved
0.7451	Intermediate Similarity	NPD2555	Approved
0.7451	Intermediate Similarity	NPD2558	Approved
0.7451	Intermediate Similarity	NPD2553	Approved
0.7451	Intermediate Similarity	NPD2552	Approved
0.7451	Intermediate Similarity	NPD2550	Approved
0.7423	Intermediate Similarity	NPD9256	Approved
0.7423	Intermediate Similarity	NPD9258	Approved
0.7407	Intermediate Similarity	NPD969	Suspended
0.7404	Intermediate Similarity	NPD5909	Discontinued
0.7379	Intermediate Similarity	NPD4188	Approved
0.7379	Intermediate Similarity	NPD4189	Approved
0.7339	Intermediate Similarity	NPD5535	Approved
0.7333	Intermediate Similarity	NPD9294	Approved
0.7304	Intermediate Similarity	NPD6287	Discontinued
0.7297	Intermediate Similarity	NPD4198	Discontinued
0.7257	Intermediate Similarity	NPD1894	Discontinued
0.7238	Intermediate Similarity	NPD1237	Approved
0.7238	Intermediate Similarity	NPD3046	Approved
0.7238	Intermediate Similarity	NPD3047	Approved
0.7238	Intermediate Similarity	NPD3048	Approved
0.7234	Intermediate Similarity	NPD3971	Phase 1
0.7222	Intermediate Similarity	NPD2067	Discontinued
0.7193	Intermediate Similarity	NPD5585	Approved
0.7174	Intermediate Similarity	NPD9490	Approved
0.7168	Intermediate Similarity	NPD2347	Approved
0.7156	Intermediate Similarity	NPD2201	Approved
0.7143	Intermediate Similarity	NPD6647	Phase 2
0.7129	Intermediate Similarity	NPD9260	Approved
0.7119	Intermediate Similarity	NPD2198	Approved
0.7119	Intermediate Similarity	NPD2199	Approved
0.7117	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD9545	Approved
0.7103	Intermediate Similarity	NPD3524	Approved
0.7103	Intermediate Similarity	NPD968	Approved
0.7103	Intermediate Similarity	NPD3526	Approved
0.7103	Intermediate Similarity	NPD2551	Approved
0.7103	Intermediate Similarity	NPD2559	Approved
0.7087	Intermediate Similarity	NPD9495	Approved
0.7071	Intermediate Similarity	NPD3672	Approved
0.7071	Intermediate Similarity	NPD3673	Approved
0.7065	Intermediate Similarity	NPD227	Approved
0.7065	Intermediate Similarity	NPD225	Approved
0.7054	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD9491	Approved
0.7043	Intermediate Similarity	NPD5691	Approved
0.7025	Intermediate Similarity	NPD6832	Phase 2
0.7021	Intermediate Similarity	NPD9250	Approved
0.7019	Intermediate Similarity	NPD7798	Approved
0.7019	Intermediate Similarity	NPD2066	Phase 3
0.7009	Intermediate Similarity	NPD4480	Approved
0.7	Intermediate Similarity	NPD1239	Approved
0.6981	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1929	Approved
0.6981	Remote Similarity	NPD1930	Approved
0.6972	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5705	Approved
0.6944	Remote Similarity	NPD5704	Approved
0.6944	Remote Similarity	NPD5706	Approved
0.6937	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5291	Approved
0.693	Remote Similarity	NPD9493	Approved
0.693	Remote Similarity	NPD694	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5292	Approved
0.6923	Remote Similarity	NPD3496	Discontinued
0.6903	Remote Similarity	NPD5951	Approved
0.6903	Remote Similarity	NPD2629	Approved
0.6891	Remote Similarity	NPD4359	Approved
0.687	Remote Similarity	NPD5536	Phase 2
0.6864	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1563	Approved
0.6842	Remote Similarity	NPD226	Approved
0.6833	Remote Similarity	NPD5667	Approved
0.6833	Remote Similarity	NPD3225	Approved
0.6829	Remote Similarity	NPD7008	Discontinued
0.68	Remote Similarity	NPD3373	Approved
0.6796	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2934	Approved
0.6796	Remote Similarity	NPD2933	Approved
0.6786	Remote Similarity	NPD4573	Approved
0.6786	Remote Similarity	NPD4571	Approved
0.6786	Remote Similarity	NPD4572	Approved
0.678	Remote Similarity	NPD3847	Discontinued
0.6777	Remote Similarity	NPD1203	Approved
0.6777	Remote Similarity	NPD3267	Approved
0.6777	Remote Similarity	NPD3266	Approved
0.6777	Remote Similarity	NPD2797	Approved
0.6768	Remote Similarity	NPD1087	Approved
0.6757	Remote Similarity	NPD5451	Approved
0.6746	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2860	Approved
0.6731	Remote Similarity	NPD2859	Approved
0.6729	Remote Similarity	NPD1932	Approved
0.6726	Remote Similarity	NPD2497	Approved
0.6726	Remote Similarity	NPD2496	Approved
0.6699	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD9712	Approved
0.6697	Remote Similarity	NPD5048	Discontinued
0.6697	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD17	Approved
0.6695	Remote Similarity	NPD4626	Approved
0.6695	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2988	Approved
0.6667	Remote Similarity	NPD1877	Discontinued
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD1564	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD1565	Approved
0.6667	Remote Similarity	NPD4006	Discontinued
0.6667	Remote Similarity	NPD2991	Approved
0.6667	Remote Similarity	NPD1566	Phase 3
0.6667	Remote Similarity	NPD2684	Approved
0.664	Remote Similarity	NPD2313	Discontinued
0.664	Remote Similarity	NPD3764	Approved
0.6639	Remote Similarity	NPD553	Approved
0.6639	Remote Similarity	NPD4136	Approved
0.6639	Remote Similarity	NPD4106	Approved
0.6639	Remote Similarity	NPD552	Approved
0.6639	Remote Similarity	NPD9567	Approved
0.6639	Remote Similarity	NPD4135	Approved
0.6636	Remote Similarity	NPD812	Approved
0.6636	Remote Similarity	NPD810	Approved
0.6636	Remote Similarity	NPD811	Approved
0.6634	Remote Similarity	NPD800	Approved
0.6614	Remote Similarity	NPD1933	Approved
0.6614	Remote Similarity	NPD4340	Discontinued
0.6607	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD9711	Approved
0.6604	Remote Similarity	NPD9710	Approved
0.66	Remote Similarity	NPD4793	Discontinued
0.6585	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1019	Discontinued
0.6583	Remote Similarity	NPD1281	Approved
0.6583	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1535	Discovery
0.6583	Remote Similarity	NPD1611	Approved
0.6583	Remote Similarity	NPD422	Phase 1
0.6579	Remote Similarity	NPD5277	Phase 2
0.6577	Remote Similarity	NPD290	Approved
0.6571	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1090	Approved
0.6569	Remote Similarity	NPD1089	Approved
0.6569	Remote Similarity	NPD1086	Approved
0.6562	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5163	Phase 2
0.656	Remote Similarity	NPD6039	Approved
0.6557	Remote Similarity	NPD1876	Approved
0.6555	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5306	Approved
0.6555	Remote Similarity	NPD5305	Approved
0.6555	Remote Similarity	NPD5126	Approved
0.6555	Remote Similarity	NPD5125	Phase 3
0.6555	Remote Similarity	NPD1778	Approved
0.6552	Remote Similarity	NPD2557	Approved
0.6542	Remote Similarity	NPD3020	Approved
0.6535	Remote Similarity	NPD531	Approved
0.6535	Remote Similarity	NPD4307	Phase 2
0.6529	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD1608	Approved
0.6529	Remote Similarity	NPD9717	Approved
0.6529	Remote Similarity	NPD1481	Phase 2
0.6522	Remote Similarity	NPD5283	Phase 1
0.6514	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6798	Discontinued
0.6508	Remote Similarity	NPD3268	Approved
0.6508	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1889	Phase 1
0.6496	Remote Similarity	NPD5500	Discontinued
0.6496	Remote Similarity	NPD3596	Phase 2
0.6495	Remote Similarity	NPD942	Approved
0.6491	Remote Similarity	NPD9508	Approved
0.6489	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3028	Approved
0.6476	Remote Similarity	NPD6048	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