NPASS Compound

Structure

CID155209 OpenBabel06191715522D 28 29 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -6.0622 -3.5000 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 -3.4641 -2.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -6.9282 -3.0000 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 -6.9282 -2.0000 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 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 27 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 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 17 1 0 0 0 0 11 13 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 11 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.12
Volume:	383.957
LogP:	2.616
LogD:	1.95
LogS:	-2.568
# Rotatable Bonds:	9
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	2.945
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.115
MDCK Permeability:	1.3931080502516124e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	97.37694549560547%
Volume Distribution (VD):	0.39
Pgp-substrate:	2.183281183242798%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.642
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.493
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.548
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	16.298
Half-life (T1/2):	0.95

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.304
Rat Oral Acute Toxicity:	0.372
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.96
Carcinogencity:	0.199
Eye Corrosion:	0.005
Eye Irritation:	0.906
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC155209

Natural Product ID:	NPC155209
*Common Name:**	Ethyl Rosmarinate
IUPAC Name:	ethyl (2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxypropanoate
Synonyms:
Standard InCHIKey:	ROJRNQOAUDCMES-KRZKXXONSA-N
Standard InCHI:	InChI=1S/C20H20O8/c1-2-27-20(26)18(11-13-4-7-15(22)17(24)10-13)28-19(25)8-5-12-3-6-14(21)16(23)9-12/h3-10,18,21-24H,2,11H2,1H3/b8-5+/t18-/m1/s1
SMILES:	CCOC(=O)[C@@H](Cc1ccc(c(c1)O)O)OC(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241613
PubChem CID:	44437692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO11472.1	Glechoma hederacea	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21530248]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21508	Tilia tomentosa	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6135	Ehretia philippinensis	Species	Ehretiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20297	Arnebia guttata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21508	Tilia tomentosa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11816.1	Vigna unguiculata subsp. unguiculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11115	Aspilia mossambicensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21453	Variolaria amara	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14650	Lobelia chinensis	Species	Campanulaceae	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	3

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	22.7	%	PMID[506187]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4300.0	nM	PMID[506189]
NPT2	Others	Unspecified		IC50	=	91000.0	nM	PMID[506187]
NPT35	Others	n.a.		LogP	=	1.499	n.a.	PMID[506187]
NPT2	Others	Unspecified		Inhibition	=	57.0	%	PMID[506188]

☑ 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 NPC155209 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	290
0.1-0.2	1188
0.2-0.3	3138
0.3-0.4	7198
0.4-0.5	10970
0.5-0.6	4797
0.6-0.7	9593
0.7-0.8	5031
0.8-0.85	359
0.85-0.9	116
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC168799
0.9921	High Similarity	NPC5419
0.9921	High Similarity	NPC61
0.9921	High Similarity	NPC25581
0.9921	High Similarity	NPC18074
0.9841	High Similarity	NPC198388
0.9545	High Similarity	NPC288452
0.9545	High Similarity	NPC289690
0.9328	High Similarity	NPC38473
0.9313	High Similarity	NPC106406
0.9254	High Similarity	NPC179505
0.9254	High Similarity	NPC156709
0.9185	High Similarity	NPC477279
0.9124	High Similarity	NPC160378
0.9118	High Similarity	NPC477278
0.9118	High Similarity	NPC477277
0.9111	High Similarity	NPC274891
0.9111	High Similarity	NPC303683
0.9111	High Similarity	NPC26241
0.9111	High Similarity	NPC476819
0.9111	High Similarity	NPC474875
0.9111	High Similarity	NPC476820
0.9111	High Similarity	NPC295492
0.9111	High Similarity	NPC205751
0.9104	High Similarity	NPC67349
0.9104	High Similarity	NPC279676
0.9084	High Similarity	NPC318799
0.9051	High Similarity	NPC277315
0.9051	High Similarity	NPC319628
0.9051	High Similarity	NPC43158
0.9051	High Similarity	NPC220664
0.9051	High Similarity	NPC192831
0.9051	High Similarity	NPC37331
0.9051	High Similarity	NPC472016
0.9051	High Similarity	NPC284948
0.9051	High Similarity	NPC303090
0.9051	High Similarity	NPC258469
0.9048	High Similarity	NPC147654
0.9048	High Similarity	NPC472271
0.9037	High Similarity	NPC152942
0.9037	High Similarity	NPC219428
0.9037	High Similarity	NPC37250
0.9037	High Similarity	NPC302857
0.9037	High Similarity	NPC278068
0.9037	High Similarity	NPC142703
0.9	High Similarity	NPC471076
0.9	High Similarity	NPC192568
0.8978	High Similarity	NPC35702
0.8978	High Similarity	NPC477335
0.8978	High Similarity	NPC297517
0.8978	High Similarity	NPC471027
0.8978	High Similarity	NPC206095
0.8978	High Similarity	NPC224389
0.8978	High Similarity	NPC13818
0.8968	High Similarity	NPC470849
0.8968	High Similarity	NPC470848
0.8929	High Similarity	NPC299090
0.8929	High Similarity	NPC229264
0.8929	High Similarity	NPC283081
0.8929	High Similarity	NPC221383
0.8929	High Similarity	NPC143892
0.8897	High Similarity	NPC284409
0.8864	High Similarity	NPC329344
0.8864	High Similarity	NPC32626
0.8864	High Similarity	NPC217052
0.8864	High Similarity	NPC237506
0.8837	High Similarity	NPC85565
0.8837	High Similarity	NPC288945
0.8815	High Similarity	NPC70680
0.8815	High Similarity	NPC182217
0.8815	High Similarity	NPC233350
0.8811	High Similarity	NPC300329
0.881	High Similarity	NPC263386
0.881	High Similarity	NPC141791
0.8806	High Similarity	NPC471749
0.8794	High Similarity	NPC322660
0.8786	High Similarity	NPC53884
0.8786	High Similarity	NPC258671
0.8786	High Similarity	NPC477333
0.8759	High Similarity	NPC283560
0.8759	High Similarity	NPC24295
0.875	High Similarity	NPC246566
0.875	High Similarity	NPC95498
0.8741	High Similarity	NPC32197
0.8741	High Similarity	NPC221091
0.8741	High Similarity	NPC135127
0.8741	High Similarity	NPC259576
0.8741	High Similarity	NPC68517
0.8732	High Similarity	NPC98009
0.873	High Similarity	NPC309434
0.8723	High Similarity	NPC98356
0.8714	High Similarity	NPC304956
0.869	High Similarity	NPC44730
0.8667	High Similarity	NPC475468
0.8657	High Similarity	NPC108553
0.8643	High Similarity	NPC285550
0.8633	High Similarity	NPC9218
0.8615	High Similarity	NPC14141
0.8613	High Similarity	NPC90431
0.8611	High Similarity	NPC306343
0.8603	High Similarity	NPC34293
0.8603	High Similarity	NPC248150
0.8603	High Similarity	NPC886
0.8603	High Similarity	NPC474895
0.8603	High Similarity	NPC287597
0.8601	High Similarity	NPC472969
0.8593	High Similarity	NPC323379
0.8593	High Similarity	NPC327204
0.8583	High Similarity	NPC63126
0.8583	High Similarity	NPC203124
0.8583	High Similarity	NPC275519
0.8582	High Similarity	NPC285361
0.8582	High Similarity	NPC474692
0.8582	High Similarity	NPC183824
0.8571	High Similarity	NPC281277
0.8571	High Similarity	NPC253722
0.8571	High Similarity	NPC31751
0.8571	High Similarity	NPC110313
0.8571	High Similarity	NPC253481
0.8562	High Similarity	NPC475216
0.8562	High Similarity	NPC475595
0.8562	High Similarity	NPC266084
0.8562	High Similarity	NPC83663
0.8562	High Similarity	NPC475145
0.8562	High Similarity	NPC475162
0.8562	High Similarity	NPC473544
0.8561	High Similarity	NPC322021
0.8561	High Similarity	NPC120225
0.8561	High Similarity	NPC118584
0.8561	High Similarity	NPC213552
0.8552	High Similarity	NPC477334
0.8542	High Similarity	NPC42464
0.854	High Similarity	NPC123988
0.8529	High Similarity	NPC19719
0.8529	High Similarity	NPC477281
0.8529	High Similarity	NPC477280
0.8516	High Similarity	NPC70084
0.8514	High Similarity	NPC473275
0.8514	High Similarity	NPC470896
0.8507	High Similarity	NPC64111
0.8507	High Similarity	NPC94810
0.8507	High Similarity	NPC83062
0.8507	High Similarity	NPC241354
0.8507	High Similarity	NPC226855
0.8504	High Similarity	NPC200988
0.8504	High Similarity	NPC145023
0.8504	High Similarity	NPC175799
0.8504	High Similarity	NPC610
0.8503	High Similarity	NPC477299
0.8496	Intermediate Similarity	NPC5018
0.8496	Intermediate Similarity	NPC151167
0.8496	Intermediate Similarity	NPC123722
0.8496	Intermediate Similarity	NPC276466
0.8496	Intermediate Similarity	NPC123228
0.8493	Intermediate Similarity	NPC163883
0.8493	Intermediate Similarity	NPC93498
0.8492	Intermediate Similarity	NPC233669
0.8489	Intermediate Similarity	NPC476383
0.8489	Intermediate Similarity	NPC472350
0.8489	Intermediate Similarity	NPC64141
0.8489	Intermediate Similarity	NPC81515
0.8489	Intermediate Similarity	NPC68092
0.8489	Intermediate Similarity	NPC197316
0.8489	Intermediate Similarity	NPC89105
0.8485	Intermediate Similarity	NPC197832
0.8485	Intermediate Similarity	NPC280767
0.8485	Intermediate Similarity	NPC289459
0.8485	Intermediate Similarity	NPC132921
0.8485	Intermediate Similarity	NPC67951
0.8473	Intermediate Similarity	NPC212541
0.8472	Intermediate Similarity	NPC1580
0.8472	Intermediate Similarity	NPC43123
0.8467	Intermediate Similarity	NPC471110
0.8462	Intermediate Similarity	NPC322332
0.8451	Intermediate Similarity	NPC50221
0.8451	Intermediate Similarity	NPC114242
0.8451	Intermediate Similarity	NPC22176
0.8451	Intermediate Similarity	NPC190587
0.8451	Intermediate Similarity	NPC121573
0.8451	Intermediate Similarity	NPC473090
0.8451	Intermediate Similarity	NPC470130
0.8451	Intermediate Similarity	NPC226738
0.8444	Intermediate Similarity	NPC172673
0.8438	Intermediate Similarity	NPC86198
0.8435	Intermediate Similarity	NPC146277
0.8435	Intermediate Similarity	NPC19380
0.8433	Intermediate Similarity	NPC217431
0.8433	Intermediate Similarity	NPC167463
0.8433	Intermediate Similarity	NPC46192
0.8429	Intermediate Similarity	NPC475530
0.8429	Intermediate Similarity	NPC191280
0.8429	Intermediate Similarity	NPC473799
0.8425	Intermediate Similarity	NPC243891
0.8425	Intermediate Similarity	NPC277394
0.8425	Intermediate Similarity	NPC299252
0.8425	Intermediate Similarity	NPC61062
0.8421	Intermediate Similarity	NPC475695
0.8421	Intermediate Similarity	NPC147192
0.8421	Intermediate Similarity	NPC90128
0.8421	Intermediate Similarity	NPC168653

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 NPC155209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	767
0.2-0.3	1568
0.3-0.4	2570
0.4-0.5	2065
0.5-0.6	1182
0.6-0.7	640
0.7-0.8	102
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9051	High Similarity	NPD6190	Approved
0.8489	Intermediate Similarity	NPD7266	Discontinued
0.8129	Intermediate Similarity	NPD230	Phase 1
0.806	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD8166	Discontinued
0.7987	Intermediate Similarity	NPD3455	Phase 2
0.7931	Intermediate Similarity	NPD4628	Phase 3
0.7914	Intermediate Similarity	NPD6798	Discontinued
0.7908	Intermediate Similarity	NPD3882	Suspended
0.7908	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD9545	Approved
0.7872	Intermediate Similarity	NPD6355	Discontinued
0.7857	Intermediate Similarity	NPD6233	Phase 2
0.7857	Intermediate Similarity	NPD4062	Phase 3
0.7843	Intermediate Similarity	NPD3817	Phase 2
0.7742	Intermediate Similarity	NPD7075	Discontinued
0.7714	Intermediate Similarity	NPD3027	Phase 3
0.7676	Intermediate Similarity	NPD4060	Phase 1
0.766	Intermediate Similarity	NPD3764	Approved
0.7651	Intermediate Similarity	NPD6799	Approved
0.7597	Intermediate Similarity	NPD3021	Approved
0.7597	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD3022	Approved
0.7589	Intermediate Similarity	NPD7095	Approved
0.758	Intermediate Similarity	NPD6234	Discontinued
0.7571	Intermediate Similarity	NPD9494	Approved
0.7562	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6166	Phase 2
0.7561	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD826	Approved
0.7552	Intermediate Similarity	NPD825	Approved
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6797	Phase 2
0.7546	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD5536	Phase 2
0.753	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD4340	Discontinued
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.7484	Intermediate Similarity	NPD6801	Discontinued
0.7464	Intermediate Similarity	NPD9269	Phase 2
0.745	Intermediate Similarity	NPD4110	Phase 3
0.745	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD2629	Approved
0.7436	Intermediate Similarity	NPD2801	Approved
0.7434	Intermediate Similarity	NPD1512	Approved
0.7432	Intermediate Similarity	NPD4534	Discontinued
0.7431	Intermediate Similarity	NPD943	Approved
0.7415	Intermediate Similarity	NPD2935	Discontinued
0.7413	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD555	Phase 2
0.7372	Intermediate Similarity	NPD37	Approved
0.7368	Intermediate Similarity	NPD5401	Approved
0.7362	Intermediate Similarity	NPD3818	Discontinued
0.7355	Intermediate Similarity	NPD6599	Discontinued
0.7349	Intermediate Similarity	NPD7808	Phase 3
0.7348	Intermediate Similarity	NPD228	Approved
0.7342	Intermediate Similarity	NPD4967	Phase 2
0.7342	Intermediate Similarity	NPD4965	Approved
0.7342	Intermediate Similarity	NPD4966	Approved
0.7338	Intermediate Similarity	NPD1653	Approved
0.7338	Intermediate Similarity	NPD1608	Approved
0.7317	Intermediate Similarity	NPD7054	Approved
0.7315	Intermediate Similarity	NPD5958	Discontinued
0.731	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1613	Approved
0.7308	Intermediate Similarity	NPD6385	Approved
0.7308	Intermediate Similarity	NPD6386	Approved
0.7303	Intermediate Similarity	NPD1511	Approved
0.7273	Intermediate Similarity	NPD7472	Approved
0.7273	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD8127	Discontinued
0.7256	Intermediate Similarity	NPD7228	Approved
0.7255	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3146	Approved
0.7254	Intermediate Similarity	NPD257	Approved
0.7254	Intermediate Similarity	NPD258	Approved
0.7244	Intermediate Similarity	NPD4380	Phase 2
0.7241	Intermediate Similarity	NPD259	Phase 1
0.7241	Intermediate Similarity	NPD6663	Approved
0.7226	Intermediate Similarity	NPD1894	Discontinued
0.7222	Intermediate Similarity	NPD6232	Discontinued
0.7215	Intermediate Similarity	NPD1465	Phase 2
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7203	Intermediate Similarity	NPD5736	Approved
0.7197	Intermediate Similarity	NPD2067	Discontinued
0.7193	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2438	Suspended
0.7181	Intermediate Similarity	NPD9570	Approved
0.7176	Intermediate Similarity	NPD1358	Approved
0.7176	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9268	Approved
0.7171	Intermediate Similarity	NPD3887	Approved
0.7171	Intermediate Similarity	NPD2354	Approved
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7153	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7143	Intermediate Similarity	NPD447	Suspended
0.7133	Intermediate Similarity	NPD5763	Approved
0.7133	Intermediate Similarity	NPD5762	Approved
0.7132	Intermediate Similarity	NPD4198	Discontinued
0.7122	Intermediate Similarity	NPD17	Approved
0.7114	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1283	Approved
0.7111	Intermediate Similarity	NPD5283	Phase 1
0.7107	Intermediate Similarity	NPD7819	Suspended
0.7105	Intermediate Similarity	NPD3750	Approved
0.7092	Intermediate Similarity	NPD1481	Phase 2
0.7091	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7038	Approved
0.7083	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9569	Approved
0.7083	Intermediate Similarity	NPD7039	Approved
0.7081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9493	Approved
0.7071	Intermediate Similarity	NPD3847	Discontinued
0.7067	Intermediate Similarity	NPD1551	Phase 2
0.7063	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD919	Approved
0.7034	Intermediate Similarity	NPD6832	Phase 2
0.7032	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3536	Discontinued
0.702	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD2799	Discontinued
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5049	Phase 3
0.6987	Remote Similarity	NPD6273	Approved
0.6985	Remote Similarity	NPD1241	Discontinued
0.6984	Remote Similarity	NPD2934	Approved
0.6984	Remote Similarity	NPD2933	Approved
0.6982	Remote Similarity	NPD6559	Discontinued
0.6981	Remote Similarity	NPD7411	Suspended
0.698	Remote Similarity	NPD6653	Approved
0.6977	Remote Similarity	NPD8150	Discontinued
0.6974	Remote Similarity	NPD1549	Phase 2
0.697	Remote Similarity	NPD3134	Approved
0.6968	Remote Similarity	NPD4357	Discontinued
0.6959	Remote Similarity	NPD2979	Phase 3
0.6959	Remote Similarity	NPD1558	Phase 1
0.6959	Remote Similarity	NPD1240	Approved
0.6959	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5405	Approved
0.6954	Remote Similarity	NPD5408	Approved
0.6954	Remote Similarity	NPD5404	Approved
0.6954	Remote Similarity	NPD5406	Approved
0.6953	Remote Similarity	NPD9495	Approved
0.695	Remote Similarity	NPD3496	Discontinued
0.6946	Remote Similarity	NPD3751	Discontinued
0.6944	Remote Similarity	NPD1203	Approved
0.6939	Remote Similarity	NPD3268	Approved
0.6929	Remote Similarity	NPD5585	Approved
0.6929	Remote Similarity	NPD2859	Approved
0.6929	Remote Similarity	NPD2860	Approved
0.6923	Remote Similarity	NPD2983	Phase 2
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2982	Phase 2
0.6918	Remote Similarity	NPD4972	Discontinued
0.6914	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD274	Approved
0.6913	Remote Similarity	NPD275	Approved
0.6913	Remote Similarity	NPD1933	Approved
0.6908	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2353	Approved
0.6908	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1281	Approved
0.6901	Remote Similarity	NPD422	Phase 1
0.6901	Remote Similarity	NPD3705	Approved
0.6899	Remote Similarity	NPD3020	Approved
0.6899	Remote Similarity	NPD3686	Approved
0.6899	Remote Similarity	NPD3687	Approved
0.6897	Remote Similarity	NPD5647	Approved
0.6894	Remote Similarity	NPD8455	Phase 2
0.6883	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3019	Approved
0.6879	Remote Similarity	NPD4626	Approved
0.6879	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD3225	Approved
0.6871	Remote Similarity	NPD9536	Phase 1
0.6871	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD9537	Phase 1
0.6867	Remote Similarity	NPD1607	Approved
0.6867	Remote Similarity	NPD5242	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data