NPASS Compound

Structure

CID49173 OpenBabel06191715382D 38 40 0 0 1 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 4.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 5.7024 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 -2.5981 1.5000 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 3.7195 3.1151 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 3.5116 4.0933 0.0000 C 0 0 2 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 2.5981 4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7026 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6706 2.8061 0.0000 C 0 0 0 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 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9595 6.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4137 3.4752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8785 1.8280 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 4 1 0 0 0 0 3 7 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 36 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 19 1 0 0 0 0 11 37 1 0 0 0 0 12 10 1 6 0 0 0 12 14 1 0 0 0 0 13 24 1 0 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 15 26 2 0 0 0 0 16 20 2 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 28 1 0 0 0 0 18 11 1 1 0 0 0 18 21 1 0 0 0 0 18 38 1 0 0 0 0 19 29 2 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 25 1 0 0 0 0 23 34 1 6 0 0 0 24 35 2 0 0 0 0 24 37 1 0 0 0 0 25 36 1 1 0 0 0 25 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.18
Volume:	511.104
LogP:	-0.041
LogD:	-0.316
LogS:	-2.285
# Rotatable Bonds:	12
TPSA:	220.51
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	4.548
Fsp3:	0.56
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.035
MDCK Permeability:	1.2703791071544401e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.903
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	93.40996551513672%
Volume Distribution (VD):	0.273
Pgp-substrate:	3.9885764122009277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	6.771
Half-life (T1/2):	0.974

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.823
Carcinogencity:	0.198
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC49173

Natural Product ID:	NPC49173
*Common Name:**	(1' R,5' R)-5-(5-Carboxymethyl-2-Oxocyclopentyl)-3 Z-Pentenylbeta-D-(6-O-Galloyl)Glucopyranoside
IUPAC Name:	2-[(1R,2R)-3-oxo-2-[(Z)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-2-yl]oxypent-2-enyl]cyclopentyl]acetic acid
Synonyms:
Standard InCHIKey:	YNGJOPKAULIOQY-QUZKLYMESA-N
Standard InCHI:	InChI=1S/C25H32O13/c26-15-6-5-12(10-19(29)30)14(15)4-2-1-3-7-36-25-23(34)22(33)21(32)18(38-25)11-37-24(35)13-8-16(27)20(31)17(28)9-13/h1-2,8-9,12,14,18,21-23,25,27-28,31-34H,3-7,10-11H2,(H,29,30)/b2-1-/t12-,14-,18-,21-,22+,23-,25-/m1/s1
SMILES:	C(=CC[C@@H]1[C@H](CCC1=O)CC(=O)O)CCO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463850
PubChem CID:	24879474
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869193]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Berries	n.a.	n.a.	PMID[18314960]
NPO15339	Artemisia afra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15243	Pimenta dioica	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8843	Epipactis palustris	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15050	Rumex obtusifolius	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2373	Popillia japonica	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15339	Artemisia afra	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	11200.0	nM	PMID[522740]

☑ 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 NPC49173 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	357
0.1-0.2	1322
0.2-0.3	3016
0.3-0.4	6828
0.4-0.5	10701
0.5-0.6	6340
0.6-0.7	7512
0.7-0.8	6173
0.8-0.85	380
0.85-0.9	57
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC140151
0.9195	High Similarity	NPC108455
0.9128	High Similarity	NPC229036
0.9103	High Similarity	NPC4747
0.9103	High Similarity	NPC104275
0.9097	High Similarity	NPC156624
0.9097	High Similarity	NPC172920
0.9079	High Similarity	NPC92117
0.9013	High Similarity	NPC248257
0.9013	High Similarity	NPC120621
0.9007	High Similarity	NPC473867
0.8981	High Similarity	NPC187205
0.8954	High Similarity	NPC75945
0.8861	High Similarity	NPC472860
0.8859	High Similarity	NPC225036
0.8859	High Similarity	NPC12218
0.8859	High Similarity	NPC75763
0.8859	High Similarity	NPC105525
0.8846	High Similarity	NPC61152
0.8846	High Similarity	NPC3746
0.8846	High Similarity	NPC16024
0.8846	High Similarity	NPC44260
0.8846	High Similarity	NPC205037
0.8834	High Similarity	NPC476017
0.878	High Similarity	NPC475058
0.8765	High Similarity	NPC475738
0.8758	High Similarity	NPC145847
0.875	High Similarity	NPC239966
0.875	High Similarity	NPC203020
0.875	High Similarity	NPC138993
0.875	High Similarity	NPC22176
0.875	High Similarity	NPC190587
0.875	High Similarity	NPC226738
0.875	High Similarity	NPC121573
0.8735	High Similarity	NPC171706
0.8734	High Similarity	NPC203757
0.8734	High Similarity	NPC475484
0.8726	High Similarity	NPC310661
0.8726	High Similarity	NPC105827
0.8704	High Similarity	NPC109990
0.8688	High Similarity	NPC160780
0.8688	High Similarity	NPC74319
0.8688	High Similarity	NPC287872
0.8688	High Similarity	NPC289811
0.8667	High Similarity	NPC239943
0.8642	High Similarity	NPC14030
0.8642	High Similarity	NPC291957
0.8642	High Similarity	NPC476011
0.8642	High Similarity	NPC41009
0.8634	High Similarity	NPC289346
0.8631	High Similarity	NPC469418
0.8625	High Similarity	NPC1913
0.8625	High Similarity	NPC226759
0.8625	High Similarity	NPC135222
0.8625	High Similarity	NPC474010
0.8625	High Similarity	NPC172419
0.8625	High Similarity	NPC238419
0.8589	High Similarity	NPC470898
0.858	High Similarity	NPC25389
0.858	High Similarity	NPC472859
0.858	High Similarity	NPC311803
0.8571	High Similarity	NPC141331
0.8571	High Similarity	NPC473713
0.8571	High Similarity	NPC179914
0.8571	High Similarity	NPC104222
0.8571	High Similarity	NPC210501
0.8571	High Similarity	NPC114791
0.8571	High Similarity	NPC318826
0.8562	High Similarity	NPC247629
0.8562	High Similarity	NPC239019
0.8562	High Similarity	NPC471405
0.8545	High Similarity	NPC116745
0.8537	High Similarity	NPC180586
0.8535	High Similarity	NPC205054
0.8533	High Similarity	NPC156892
0.8528	High Similarity	NPC90905
0.8528	High Similarity	NPC285108
0.8528	High Similarity	NPC4013
0.8528	High Similarity	NPC33298
0.8528	High Similarity	NPC148273
0.8526	High Similarity	NPC142528
0.8521	High Similarity	NPC260300
0.8521	High Similarity	NPC80360
0.8519	High Similarity	NPC119125
0.8519	High Similarity	NPC474936
0.8519	High Similarity	NPC166277
0.8512	High Similarity	NPC469354
0.8506	High Similarity	NPC114242
0.8506	High Similarity	NPC473281
0.8506	High Similarity	NPC77922
0.8506	High Similarity	NPC50221
0.8503	High Similarity	NPC470685
0.85	High Similarity	NPC10205
0.8497	Intermediate Similarity	NPC296643
0.8494	Intermediate Similarity	NPC21956
0.8491	Intermediate Similarity	NPC157898
0.8485	Intermediate Similarity	NPC301910
0.8485	Intermediate Similarity	NPC130730
0.8481	Intermediate Similarity	NPC289021
0.8481	Intermediate Similarity	NPC158546
0.8476	Intermediate Similarity	NPC88043
0.8471	Intermediate Similarity	NPC42464
0.8471	Intermediate Similarity	NPC198902
0.8471	Intermediate Similarity	NPC478236
0.8471	Intermediate Similarity	NPC195114
0.8467	Intermediate Similarity	NPC18646
0.8462	Intermediate Similarity	NPC268366
0.8443	Intermediate Similarity	NPC204937
0.8443	Intermediate Similarity	NPC470272
0.8443	Intermediate Similarity	NPC149011
0.8442	Intermediate Similarity	NPC478250
0.8438	Intermediate Similarity	NPC327032
0.8438	Intermediate Similarity	NPC472128
0.8438	Intermediate Similarity	NPC472127
0.8438	Intermediate Similarity	NPC194095
0.8438	Intermediate Similarity	NPC191046
0.8434	Intermediate Similarity	NPC470271
0.8434	Intermediate Similarity	NPC311389
0.8428	Intermediate Similarity	NPC75695
0.8428	Intermediate Similarity	NPC203664
0.8428	Intermediate Similarity	NPC478235
0.8424	Intermediate Similarity	NPC165720
0.8421	Intermediate Similarity	NPC102367
0.8418	Intermediate Similarity	NPC306343
0.8415	Intermediate Similarity	NPC76687
0.8412	Intermediate Similarity	NPC267549
0.8408	Intermediate Similarity	NPC43123
0.8397	Intermediate Similarity	NPC474465
0.8387	Intermediate Similarity	NPC194938
0.8387	Intermediate Similarity	NPC202391
0.8387	Intermediate Similarity	NPC296659
0.8383	Intermediate Similarity	NPC658
0.8383	Intermediate Similarity	NPC197708
0.8375	Intermediate Similarity	NPC137813
0.8375	Intermediate Similarity	NPC229354
0.8373	Intermediate Similarity	NPC175793
0.8364	Intermediate Similarity	NPC168822
0.8364	Intermediate Similarity	NPC469651
0.8355	Intermediate Similarity	NPC84789
0.8355	Intermediate Similarity	NPC310252
0.8355	Intermediate Similarity	NPC302583
0.8355	Intermediate Similarity	NPC100558
0.8354	Intermediate Similarity	NPC478242
0.8354	Intermediate Similarity	NPC478234
0.8354	Intermediate Similarity	NPC96599
0.8353	Intermediate Similarity	NPC79736
0.8353	Intermediate Similarity	NPC67629
0.8344	Intermediate Similarity	NPC469384
0.8343	Intermediate Similarity	NPC88560
0.8343	Intermediate Similarity	NPC172033
0.8343	Intermediate Similarity	NPC175230
0.8333	Intermediate Similarity	NPC1321
0.8333	Intermediate Similarity	NPC304929
0.8333	Intermediate Similarity	NPC155763
0.8333	Intermediate Similarity	NPC235260
0.8333	Intermediate Similarity	NPC114116
0.8333	Intermediate Similarity	NPC72249
0.8333	Intermediate Similarity	NPC212748
0.8333	Intermediate Similarity	NPC20505
0.8333	Intermediate Similarity	NPC156124
0.8323	Intermediate Similarity	NPC287504
0.8323	Intermediate Similarity	NPC190204
0.8323	Intermediate Similarity	NPC125487
0.8323	Intermediate Similarity	NPC45400
0.8323	Intermediate Similarity	NPC149244
0.8323	Intermediate Similarity	NPC261411
0.8323	Intermediate Similarity	NPC43918
0.8323	Intermediate Similarity	NPC281703
0.8323	Intermediate Similarity	NPC25127
0.8323	Intermediate Similarity	NPC48640
0.8314	Intermediate Similarity	NPC170203
0.8313	Intermediate Similarity	NPC36130
0.8313	Intermediate Similarity	NPC134905
0.8313	Intermediate Similarity	NPC194705
0.8313	Intermediate Similarity	NPC227485
0.8313	Intermediate Similarity	NPC289438
0.8303	Intermediate Similarity	NPC77660
0.8303	Intermediate Similarity	NPC206815
0.8303	Intermediate Similarity	NPC300537
0.8303	Intermediate Similarity	NPC189142
0.8303	Intermediate Similarity	NPC127782
0.8302	Intermediate Similarity	NPC473091
0.8302	Intermediate Similarity	NPC240592
0.8302	Intermediate Similarity	NPC117346
0.8302	Intermediate Similarity	NPC69367
0.8301	Intermediate Similarity	NPC220942
0.8294	Intermediate Similarity	NPC84482
0.8294	Intermediate Similarity	NPC169645
0.8291	Intermediate Similarity	NPC81835
0.8289	Intermediate Similarity	NPC471345
0.8289	Intermediate Similarity	NPC470572
0.8284	Intermediate Similarity	NPC102851
0.8284	Intermediate Similarity	NPC175107
0.8284	Intermediate Similarity	NPC254540
0.8284	Intermediate Similarity	NPC172807
0.8284	Intermediate Similarity	NPC47140
0.8284	Intermediate Similarity	NPC190003
0.8284	Intermediate Similarity	NPC211594
0.8284	Intermediate Similarity	NPC67134
0.8284	Intermediate Similarity	NPC5786

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 NPC49173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	788
0.2-0.3	1838
0.3-0.4	2727
0.4-0.5	2115
0.5-0.6	1008
0.6-0.7	297
0.7-0.8	76
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8343	Intermediate Similarity	NPD7685	Pre-registration
0.8333	Intermediate Similarity	NPD230	Phase 1
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7054	Approved
0.8118	Intermediate Similarity	NPD7074	Phase 3
0.8118	Intermediate Similarity	NPD7472	Approved
0.811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7266	Discontinued
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.7975	Intermediate Similarity	NPD6190	Approved
0.7965	Intermediate Similarity	NPD6797	Phase 2
0.7952	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7228	Approved
0.7874	Intermediate Similarity	NPD7808	Phase 3
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD1653	Approved
0.7759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD9269	Phase 2
0.7711	Intermediate Similarity	NPD1934	Approved
0.7711	Intermediate Similarity	NPD37	Approved
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7679	Intermediate Similarity	NPD3882	Suspended
0.7679	Intermediate Similarity	NPD4967	Phase 2
0.7679	Intermediate Similarity	NPD4966	Approved
0.7679	Intermediate Similarity	NPD4965	Approved
0.7665	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6559	Discontinued
0.759	Intermediate Similarity	NPD4380	Phase 2
0.7572	Intermediate Similarity	NPD6166	Phase 2
0.7572	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2801	Approved
0.756	Intermediate Similarity	NPD1465	Phase 2
0.7543	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD3817	Phase 2
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD943	Approved
0.745	Intermediate Similarity	NPD9268	Approved
0.7443	Intermediate Similarity	NPD5844	Phase 1
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1511	Approved
0.7432	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7240	Approved
0.7412	Intermediate Similarity	NPD5353	Approved
0.7375	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4628	Phase 3
0.7356	Intermediate Similarity	NPD6232	Discontinued
0.7353	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7819	Suspended
0.7349	Intermediate Similarity	NPD1512	Approved
0.7346	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD5494	Approved
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.731	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD9545	Approved
0.7235	Intermediate Similarity	NPD7411	Suspended
0.7229	Intermediate Similarity	NPD6799	Approved
0.7228	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6801	Discontinued
0.7186	Intermediate Similarity	NPD2533	Approved
0.7186	Intermediate Similarity	NPD2534	Approved
0.7186	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD3027	Phase 3
0.7134	Intermediate Similarity	NPD1549	Phase 2
0.7134	Intermediate Similarity	NPD9494	Approved
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7125	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7107	Intermediate Similarity	NPD3764	Approved
0.7105	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5403	Approved
0.7098	Intermediate Similarity	NPD8319	Approved
0.7098	Intermediate Similarity	NPD8320	Phase 1
0.7095	Intermediate Similarity	NPD3751	Discontinued
0.7079	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6599	Discontinued
0.7073	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1510	Phase 2
0.7052	Intermediate Similarity	NPD8455	Phase 2
0.7048	Intermediate Similarity	NPD3750	Approved
0.7047	Intermediate Similarity	NPD7680	Approved
0.7047	Intermediate Similarity	NPD7435	Discontinued
0.7027	Intermediate Similarity	NPD8434	Phase 2
0.7022	Intermediate Similarity	NPD5242	Approved
0.7019	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1613	Approved
0.7018	Intermediate Similarity	NPD3455	Phase 2
0.7018	Intermediate Similarity	NPD7458	Discontinued
0.7011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6535	Approved
0.6984	Remote Similarity	NPD6534	Approved
0.6982	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5401	Approved
0.6966	Remote Similarity	NPD3787	Discontinued
0.6963	Remote Similarity	NPD7699	Phase 2
0.6963	Remote Similarity	NPD7700	Phase 2
0.6946	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6386	Approved
0.6936	Remote Similarity	NPD6385	Approved
0.6933	Remote Similarity	NPD6653	Approved
0.6932	Remote Similarity	NPD3749	Approved
0.6914	Remote Similarity	NPD1240	Approved
0.691	Remote Similarity	NPD1247	Approved
0.6906	Remote Similarity	NPD7799	Discontinued
0.6893	Remote Similarity	NPD919	Approved
0.6891	Remote Similarity	NPD6781	Approved
0.6891	Remote Similarity	NPD6782	Approved
0.6891	Remote Similarity	NPD6780	Approved
0.6891	Remote Similarity	NPD6778	Approved
0.6891	Remote Similarity	NPD6779	Approved
0.6891	Remote Similarity	NPD6777	Approved
0.6891	Remote Similarity	NPD6776	Approved
0.6882	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD447	Suspended
0.6855	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7874	Approved
0.6833	Remote Similarity	NPD3926	Phase 2
0.6829	Remote Similarity	NPD1607	Approved
0.6816	Remote Similarity	NPD6959	Discontinued
0.6807	Remote Similarity	NPD1551	Phase 2
0.6807	Remote Similarity	NPD2935	Discontinued
0.6807	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD7698	Approved
0.6786	Remote Similarity	NPD7696	Phase 3
0.6786	Remote Similarity	NPD7697	Approved
0.678	Remote Similarity	NPD7768	Phase 2
0.6778	Remote Similarity	NPD5710	Approved
0.6778	Remote Similarity	NPD5711	Approved
0.6772	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.677	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6355	Discontinued
0.6754	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6213	Phase 3
0.6754	Remote Similarity	NPD6212	Phase 3
0.6752	Remote Similarity	NPD1091	Approved
0.6751	Remote Similarity	NPD7871	Phase 2
0.6751	Remote Similarity	NPD7870	Phase 2
0.675	Remote Similarity	NPD5647	Approved
0.6747	Remote Similarity	NPD3748	Approved
0.6746	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4110	Phase 3
0.6744	Remote Similarity	NPD6273	Approved
0.6735	Remote Similarity	NPD6823	Phase 2
0.6734	Remote Similarity	NPD7701	Phase 2
0.6734	Remote Similarity	NPD7585	Approved
0.6724	Remote Similarity	NPD3226	Approved
0.6718	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7801	Approved
0.6716	Remote Similarity	NPD7783	Phase 2
0.6708	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6100	Approved
0.6707	Remote Similarity	NPD6099	Approved
0.6705	Remote Similarity	NPD920	Approved
0.67	Remote Similarity	NPD7930	Approved
0.6687	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2800	Approved
0.6686	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7028	Phase 2
0.6685	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7583	Approved
0.6683	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD8368	Discontinued
0.6649	Remote Similarity	NPD8407	Phase 2
0.6647	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3705	Approved
0.6646	Remote Similarity	NPD6663	Approved
0.6644	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6843	Phase 3
0.6632	Remote Similarity	NPD6841	Approved
0.6632	Remote Similarity	NPD6842	Approved
0.6629	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6651	Approved
0.6613	Remote Similarity	NPD5953	Discontinued
0.6611	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5736	Approved
0.6604	Remote Similarity	NPD1608	Approved
0.6603	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD7286	Phase 2
0.6593	Remote Similarity	NPD7229	Phase 3
0.659	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.659	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6674	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