NPASS Compound

Structure

CID260952 OpenBabel06191716062D 21 22 0 0 0 0 0 0 0 0999 V2000 10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 2 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.11
Volume:	305.414
LogP:	3.647
LogD:	4.167
LogS:	-3.786
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	2.066
Fsp3:	0.056
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:	-4.748
MDCK Permeability:	1.8069378711516038e-05
Pgp-inhibitor:	0.53
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.17
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.647
Plasma Protein Binding (PPB):	98.59046173095703%
Volume Distribution (VD):	0.585
Pgp-substrate:	2.013028621673584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.899
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.591
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	10.683
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.471
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.867
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.199
Skin Sensitization:	0.963
Carcinogencity:	0.436
Eye Corrosion:	0.01
Eye Irritation:	0.817
Respiratory Toxicity:	0.192

Download Data

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

Natural Product: NPC260952

Natural Product ID:	NPC260952
*Common Name:**	(E)-Cinnamyl (E)-P-Coumarate
IUPAC Name:	[(E)-3-phenylprop-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	JDBSEUVQZVQSCN-NJPWYCGFSA-N
Standard InCHI:	InChI=1S/C18H16O3/c19-17-11-8-16(9-12-17)10-13-18(20)21-14-4-7-15-5-2-1-3-6-15/h1-13,19H,14H2/b7-4+,13-10+
SMILES:	c1ccc(cc1)/C=C/COC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452208
PubChem CID:	11288990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric 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
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.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO33094	korean propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24928402]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
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]
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]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	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]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	7
Others	3

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	143000.0	nM	PMID[552624]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	160000.0	nM	PMID[552624]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	120000.0	nM	PMID[552624]
NPT3887	Cell Line	CNE	Homo sapiens	IC50	=	162000.0	nM	PMID[552624]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[552624]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	38.2	uM	PMID[552625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[552624]
NPT2	Others	Unspecified		IC50	=	65000.0	nM	PMID[552624]
NPT2	Others	Unspecified		Ratio IC50	>	500.0	n.a.	PMID[552626]

☑ 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 NPC260952 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	234
0.1-0.2	1450
0.2-0.3	4371
0.3-0.4	11738
0.4-0.5	7039
0.5-0.6	8406
0.6-0.7	7961
0.7-0.8	1335
0.8-0.85	115
0.85-0.9	38
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC183700
0.9703	High Similarity	NPC206341
0.94	High Similarity	NPC304638
0.92	High Similarity	NPC253746
0.91	High Similarity	NPC171843
0.9057	High Similarity	NPC139946
0.9048	High Similarity	NPC79543
0.9029	High Similarity	NPC127676
0.9	High Similarity	NPC201967
0.8919	High Similarity	NPC263386
0.8919	High Similarity	NPC141791
0.8911	High Similarity	NPC130193
0.8889	High Similarity	NPC81010
0.8889	High Similarity	NPC32977
0.8829	High Similarity	NPC275519
0.8818	High Similarity	NPC128249
0.8785	High Similarity	NPC63345
0.8761	High Similarity	NPC470848
0.8761	High Similarity	NPC470849
0.8738	High Similarity	NPC94343
0.8727	High Similarity	NPC296526
0.8692	High Similarity	NPC75272
0.8692	High Similarity	NPC471954
0.8684	High Similarity	NPC147654
0.8654	High Similarity	NPC68269
0.8649	High Similarity	NPC281277
0.8636	High Similarity	NPC328593
0.8636	High Similarity	NPC261453
0.8636	High Similarity	NPC33749
0.8614	High Similarity	NPC286006
0.8585	High Similarity	NPC92623
0.8585	High Similarity	NPC326447
0.8585	High Similarity	NPC135464
0.8571	High Similarity	NPC122117
0.8571	High Similarity	NPC2518
0.8559	High Similarity	NPC233669
0.8559	High Similarity	NPC474967
0.8545	High Similarity	NPC95381
0.8505	High Similarity	NPC157473
0.8505	High Similarity	NPC151530
0.8496	Intermediate Similarity	NPC309434
0.8496	Intermediate Similarity	NPC203124
0.8491	Intermediate Similarity	NPC233396
0.8491	Intermediate Similarity	NPC154899
0.8476	Intermediate Similarity	NPC179686
0.8476	Intermediate Similarity	NPC135784
0.8468	Intermediate Similarity	NPC217472
0.8462	Intermediate Similarity	NPC246704
0.8431	Intermediate Similarity	NPC246679
0.8431	Intermediate Similarity	NPC257182
0.8426	Intermediate Similarity	NPC31274
0.8416	Intermediate Similarity	NPC181709
0.8411	Intermediate Similarity	NPC69332
0.8411	Intermediate Similarity	NPC176971
0.8411	Intermediate Similarity	NPC29989
0.8411	Intermediate Similarity	NPC95178
0.839	Intermediate Similarity	NPC289459
0.8365	Intermediate Similarity	NPC132078
0.8365	Intermediate Similarity	NPC216468
0.8365	Intermediate Similarity	NPC51333
0.8365	Intermediate Similarity	NPC78119
0.8364	Intermediate Similarity	NPC226250
0.8349	Intermediate Similarity	NPC306045
0.8349	Intermediate Similarity	NPC265211
0.8333	Intermediate Similarity	NPC311091
0.8333	Intermediate Similarity	NPC471033
0.8333	Intermediate Similarity	NPC151715
0.8319	Intermediate Similarity	NPC120225
0.8319	Intermediate Similarity	NPC213552
0.8319	Intermediate Similarity	NPC118584
0.8319	Intermediate Similarity	NPC19290
0.8318	Intermediate Similarity	NPC243677
0.8318	Intermediate Similarity	NPC128730
0.8318	Intermediate Similarity	NPC303141
0.8305	Intermediate Similarity	NPC265413
0.8305	Intermediate Similarity	NPC10154
0.8305	Intermediate Similarity	NPC474532
0.8304	Intermediate Similarity	NPC41851
0.8302	Intermediate Similarity	NPC470202
0.8291	Intermediate Similarity	NPC52097
0.8288	Intermediate Similarity	NPC131530
0.8288	Intermediate Similarity	NPC228988
0.8286	Intermediate Similarity	NPC213730
0.8276	Intermediate Similarity	NPC476872
0.8269	Intermediate Similarity	NPC140619
0.8261	Intermediate Similarity	NPC264976
0.8252	Intermediate Similarity	NPC26244
0.825	Intermediate Similarity	NPC288416
0.8246	Intermediate Similarity	NPC65791
0.8246	Intermediate Similarity	NPC145023
0.8246	Intermediate Similarity	NPC610
0.8246	Intermediate Similarity	NPC200988
0.8246	Intermediate Similarity	NPC175799
0.8241	Intermediate Similarity	NPC70843
0.8241	Intermediate Similarity	NPC113457
0.8235	Intermediate Similarity	NPC83218
0.8235	Intermediate Similarity	NPC137416
0.8235	Intermediate Similarity	NPC126991
0.8235	Intermediate Similarity	NPC67951
0.823	Intermediate Similarity	NPC23402
0.8224	Intermediate Similarity	NPC109637
0.822	Intermediate Similarity	NPC14141
0.822	Intermediate Similarity	NPC285345
0.8218	Intermediate Similarity	NPC119631
0.8208	Intermediate Similarity	NPC91461
0.8208	Intermediate Similarity	NPC40258
0.8208	Intermediate Similarity	NPC7686
0.8205	Intermediate Similarity	NPC11724
0.82	Intermediate Similarity	NPC104216
0.819	Intermediate Similarity	NPC233282
0.8182	Intermediate Similarity	NPC88141
0.8182	Intermediate Similarity	NPC2596
0.8182	Intermediate Similarity	NPC225307
0.8182	Intermediate Similarity	NPC110313
0.8174	Intermediate Similarity	NPC277460
0.8174	Intermediate Similarity	NPC94298
0.8174	Intermediate Similarity	NPC86198
0.8174	Intermediate Similarity	NPC27633
0.8173	Intermediate Similarity	NPC283711
0.8173	Intermediate Similarity	NPC292730
0.8173	Intermediate Similarity	NPC216520
0.8173	Intermediate Similarity	NPC132271
0.8173	Intermediate Similarity	NPC473388
0.8173	Intermediate Similarity	NPC82664
0.8167	Intermediate Similarity	NPC471157
0.8151	Intermediate Similarity	NPC288945
0.8148	Intermediate Similarity	NPC288760
0.8148	Intermediate Similarity	NPC227255
0.8142	Intermediate Similarity	NPC285350
0.8137	Intermediate Similarity	NPC45040
0.8125	Intermediate Similarity	NPC42911
0.8125	Intermediate Similarity	NPC199462
0.8125	Intermediate Similarity	NPC153795
0.8125	Intermediate Similarity	NPC17693
0.8125	Intermediate Similarity	NPC290353
0.812	Intermediate Similarity	NPC204466
0.812	Intermediate Similarity	NPC131868
0.8119	Intermediate Similarity	NPC240108
0.8119	Intermediate Similarity	NPC213156
0.8115	Intermediate Similarity	NPC83062
0.8108	Intermediate Similarity	NPC116842
0.8103	Intermediate Similarity	NPC70084
0.8103	Intermediate Similarity	NPC470215
0.8103	Intermediate Similarity	NPC109371
0.8103	Intermediate Similarity	NPC470214
0.8091	Intermediate Similarity	NPC201959
0.8091	Intermediate Similarity	NPC470039
0.8083	Intermediate Similarity	NPC197832
0.8073	Intermediate Similarity	NPC1786
0.8073	Intermediate Similarity	NPC294902
0.8073	Intermediate Similarity	NPC1075
0.807	Intermediate Similarity	NPC51345
0.8067	Intermediate Similarity	NPC306100
0.8067	Intermediate Similarity	NPC212541
0.8056	Intermediate Similarity	NPC261573
0.8056	Intermediate Similarity	NPC120693
0.8056	Intermediate Similarity	NPC474603
0.8056	Intermediate Similarity	NPC12987
0.8056	Intermediate Similarity	NPC8931
0.8053	Intermediate Similarity	NPC176730
0.8053	Intermediate Similarity	NPC123175
0.8051	Intermediate Similarity	NPC251259
0.8051	Intermediate Similarity	NPC70752
0.8051	Intermediate Similarity	NPC7830
0.8049	Intermediate Similarity	NPC32626
0.8049	Intermediate Similarity	NPC329344
0.8049	Intermediate Similarity	NPC237506
0.8049	Intermediate Similarity	NPC217052
0.8039	Intermediate Similarity	NPC300017
0.8037	Intermediate Similarity	NPC472585
0.8036	Intermediate Similarity	NPC470355
0.8036	Intermediate Similarity	NPC297657
0.8036	Intermediate Similarity	NPC266932
0.8034	Intermediate Similarity	NPC202474
0.8033	Intermediate Similarity	NPC219923
0.8019	Intermediate Similarity	NPC245561
0.8017	Intermediate Similarity	NPC252114
0.8017	Intermediate Similarity	NPC61181
0.8	Intermediate Similarity	NPC131192
0.8	Intermediate Similarity	NPC146886
0.8	Intermediate Similarity	NPC60517
0.8	Intermediate Similarity	NPC20443
0.7984	Intermediate Similarity	NPC46137
0.7984	Intermediate Similarity	NPC198388
0.7984	Intermediate Similarity	NPC225384
0.7984	Intermediate Similarity	NPC108553
0.7984	Intermediate Similarity	NPC246869
0.7984	Intermediate Similarity	NPC478255
0.7984	Intermediate Similarity	NPC235294
0.7984	Intermediate Similarity	NPC138777
0.7983	Intermediate Similarity	NPC296202
0.7982	Intermediate Similarity	NPC473855
0.7981	Intermediate Similarity	NPC128062
0.798	Intermediate Similarity	NPC265146
0.7967	Intermediate Similarity	NPC86257
0.7967	Intermediate Similarity	NPC30174
0.7967	Intermediate Similarity	NPC214246
0.7967	Intermediate Similarity	NPC288290
0.7966	Intermediate Similarity	NPC224814
0.7966	Intermediate Similarity	NPC189844

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 NPC260952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	928
0.2-0.3	1289
0.3-0.4	2776
0.4-0.5	2065
0.5-0.6	1237
0.6-0.7	572
0.7-0.8	70
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8585	High Similarity	NPD3134	Approved
0.8333	Intermediate Similarity	NPD2934	Approved
0.8333	Intermediate Similarity	NPD1358	Approved
0.8333	Intermediate Similarity	NPD2933	Approved
0.8252	Intermediate Similarity	NPD2859	Approved
0.8252	Intermediate Similarity	NPD2860	Approved
0.8174	Intermediate Similarity	NPD9545	Approved
0.8019	Intermediate Similarity	NPD3020	Approved
0.7909	Intermediate Similarity	NPD968	Approved
0.7863	Intermediate Similarity	NPD1894	Discontinued
0.7807	Intermediate Similarity	NPD5535	Approved
0.78	Intermediate Similarity	NPD111	Approved
0.7769	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9493	Approved
0.7679	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3847	Discontinued
0.7658	Intermediate Similarity	NPD9697	Approved
0.7619	Intermediate Similarity	NPD3764	Approved
0.7615	Intermediate Similarity	NPD1242	Phase 1
0.7603	Intermediate Similarity	NPD422	Phase 1
0.7603	Intermediate Similarity	NPD1535	Discovery
0.7583	Intermediate Similarity	NPD4626	Approved
0.7557	Intermediate Similarity	NPD7266	Discontinued
0.7541	Intermediate Similarity	NPD1481	Phase 2
0.7523	Intermediate Similarity	NPD1238	Approved
0.7521	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.7479	Intermediate Similarity	NPD5536	Phase 2
0.7477	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2684	Approved
0.7442	Intermediate Similarity	NPD4340	Discontinued
0.7436	Intermediate Similarity	NPD1241	Discontinued
0.7419	Intermediate Similarity	NPD3225	Approved
0.7417	Intermediate Similarity	NPD1548	Phase 1
0.7402	Intermediate Similarity	NPD5163	Phase 2
0.7391	Intermediate Similarity	NPD3022	Approved
0.7391	Intermediate Similarity	NPD3021	Approved
0.7381	Intermediate Similarity	NPD5736	Approved
0.7355	Intermediate Similarity	NPD5585	Approved
0.7348	Intermediate Similarity	NPD2935	Discontinued
0.7344	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6798	Discontinued
0.7339	Intermediate Similarity	NPD6582	Phase 2
0.7339	Intermediate Similarity	NPD6583	Phase 3
0.7333	Intermediate Similarity	NPD6190	Approved
0.7313	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1282	Approved
0.7304	Intermediate Similarity	NPD74	Approved
0.7304	Intermediate Similarity	NPD9266	Approved
0.7297	Intermediate Similarity	NPD3028	Approved
0.7287	Intermediate Similarity	NPD6233	Phase 2
0.7287	Intermediate Similarity	NPD4062	Phase 3
0.7259	Intermediate Similarity	NPD8166	Discontinued
0.7259	Intermediate Similarity	NPD4628	Phase 3
0.7257	Intermediate Similarity	NPD5909	Discontinued
0.7241	Intermediate Similarity	NPD5451	Approved
0.7232	Intermediate Similarity	NPD940	Approved
0.7232	Intermediate Similarity	NPD846	Approved
0.7222	Intermediate Similarity	NPD1164	Approved
0.7217	Intermediate Similarity	NPD9264	Approved
0.7217	Intermediate Similarity	NPD9267	Approved
0.7217	Intermediate Similarity	NPD9263	Approved
0.7209	Intermediate Similarity	NPD3268	Approved
0.7203	Intermediate Similarity	NPD821	Approved
0.7203	Intermediate Similarity	NPD7843	Approved
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7177	Intermediate Similarity	NPD1610	Phase 2
0.7176	Intermediate Similarity	NPD6355	Discontinued
0.717	Intermediate Similarity	NPD689	Discontinued
0.7165	Intermediate Similarity	NPD6584	Phase 3
0.7154	Intermediate Similarity	NPD5846	Approved
0.7154	Intermediate Similarity	NPD6516	Phase 2
0.7154	Intermediate Similarity	NPD1778	Approved
0.7154	Intermediate Similarity	NPD6663	Approved
0.7153	Intermediate Similarity	NPD7440	Discontinued
0.7143	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7132	Intermediate Similarity	NPD7095	Approved
0.712	Intermediate Similarity	NPD9717	Approved
0.712	Intermediate Similarity	NPD3972	Approved
0.7119	Intermediate Similarity	NPD228	Approved
0.7117	Intermediate Similarity	NPD5926	Approved
0.7109	Intermediate Similarity	NPD2861	Phase 2
0.7099	Intermediate Similarity	NPD4140	Approved
0.7091	Intermediate Similarity	NPD1809	Phase 2
0.7091	Intermediate Similarity	NPD844	Approved
0.709	Intermediate Similarity	NPD1551	Phase 2
0.7069	Intermediate Similarity	NPD290	Approved
0.7068	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD845	Approved
0.7063	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4359	Approved
0.7054	Intermediate Similarity	NPD2614	Approved
0.7054	Intermediate Similarity	NPD4908	Phase 1
0.7045	Intermediate Similarity	NPD230	Phase 1
0.7025	Intermediate Similarity	NPD4198	Discontinued
0.7025	Intermediate Similarity	NPD7157	Approved
0.7025	Intermediate Similarity	NPD255	Approved
0.7025	Intermediate Similarity	NPD6671	Approved
0.7025	Intermediate Similarity	NPD256	Approved
0.7018	Intermediate Similarity	NPD6647	Phase 2
0.7016	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3750	Approved
0.7007	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD2234	Approved
0.7	Intermediate Similarity	NPD2228	Approved
0.7	Intermediate Similarity	NPD2229	Approved
0.6992	Remote Similarity	NPD3091	Approved
0.6984	Remote Similarity	NPD1608	Approved
0.6977	Remote Similarity	NPD9494	Approved
0.6975	Remote Similarity	NPD969	Suspended
0.6972	Remote Similarity	NPD3455	Phase 2
0.697	Remote Similarity	NPD9716	Approved
0.697	Remote Similarity	NPD1240	Approved
0.6967	Remote Similarity	NPD9568	Approved
0.6967	Remote Similarity	NPD3596	Phase 2
0.6963	Remote Similarity	NPD4476	Approved
0.6963	Remote Similarity	NPD4477	Approved
0.696	Remote Similarity	NPD3421	Phase 3
0.6957	Remote Similarity	NPD1237	Approved
0.6949	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2313	Discontinued
0.6947	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9258	Approved
0.6944	Remote Similarity	NPD9256	Approved
0.694	Remote Similarity	NPD7097	Phase 1
0.6935	Remote Similarity	NPD1357	Approved
0.6934	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3971	Phase 1
0.6917	Remote Similarity	NPD5124	Phase 1
0.6917	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1202	Approved
0.6905	Remote Similarity	NPD1281	Approved
0.6905	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2798	Approved
0.6894	Remote Similarity	NPD520	Approved
0.6891	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4308	Phase 3
0.6889	Remote Similarity	NPD1510	Phase 2
0.6889	Remote Similarity	NPD7033	Discontinued
0.688	Remote Similarity	NPD2932	Approved
0.688	Remote Similarity	NPD2667	Approved
0.688	Remote Similarity	NPD2668	Approved
0.688	Remote Similarity	NPD3019	Approved
0.6879	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD288	Approved
0.6875	Remote Similarity	NPD1876	Approved
0.687	Remote Similarity	NPD9261	Approved
0.687	Remote Similarity	NPD3027	Phase 3
0.6869	Remote Similarity	NPD9087	Approved
0.6866	Remote Similarity	NPD1607	Approved
0.6864	Remote Similarity	NPD2182	Approved
0.6861	Remote Similarity	NPD1549	Phase 2
0.6861	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4534	Discontinued
0.6861	Remote Similarity	NPD5958	Discontinued
0.6857	Remote Similarity	NPD6799	Approved
0.6857	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6581	Approved
0.6855	Remote Similarity	NPD1182	Approved
0.6855	Remote Similarity	NPD6580	Approved
0.6852	Remote Similarity	NPD9295	Approved
0.685	Remote Similarity	NPD2235	Phase 2
0.685	Remote Similarity	NPD2562	Approved
0.685	Remote Similarity	NPD2561	Approved
0.685	Remote Similarity	NPD2231	Phase 2
0.6846	Remote Similarity	NPD4993	Discontinued
0.6846	Remote Similarity	NPD454	Approved
0.6842	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2979	Phase 3
0.6833	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD9294	Approved
0.6829	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3267	Approved
0.6822	Remote Similarity	NPD3266	Approved
0.6814	Remote Similarity	NPD9495	Approved
0.681	Remote Similarity	NPD9608	Approved
0.681	Remote Similarity	NPD9610	Approved
0.6809	Remote Similarity	NPD3536	Discontinued
0.6803	Remote Similarity	NPD9281	Approved
0.6803	Remote Similarity	NPD2629	Approved
0.68	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1651	Approved
0.68	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4659	Approved
0.6797	Remote Similarity	NPD3685	Discontinued
0.6791	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2344	Approved
0.6788	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6667	Approved
0.6786	Remote Similarity	NPD6666	Approved
0.678	Remote Similarity	NPD2342	Discontinued

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