NPASS Compound

Structure

CID183672 OpenBabel06191715562D 38 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -7.7942 1.5000 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 -2.5981 1.5000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -3.4641 -0.0000 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 -2.5981 -0.5000 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 -4.3301 -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 2 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 0.0000 -2.0000 0.0000 C 0 0 1 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 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -1.7321 1.0000 0.0000 C 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 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 -5.1962 -3.0000 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 -6.9282 -2.0000 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 -1.2321 0.1340 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 26 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 27 1 0 0 0 0 11 23 1 0 0 0 0 12 28 1 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 36 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 37 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 18 30 1 1 0 0 0 19 21 1 0 0 0 0 19 31 2 0 0 0 0 20 22 1 0 0 0 0 20 32 1 6 0 0 0 21 23 2 0 0 0 0 21 33 1 0 0 0 0 22 25 1 0 0 0 0 22 34 1 1 0 0 0 23 38 1 0 0 0 0 24 38 1 0 0 0 0 25 36 1 6 0 0 0 25 37 1 0 0 0 0 26 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.17
Volume:	508.417
LogP:	0.947
LogD:	0.369
LogS:	-3.834
# Rotatable Bonds:	7
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	4.256
Fsp3:	0.423
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.227
MDCK Permeability:	1.5973062545526773e-05
Pgp-inhibitor:	0.081
Pgp-substrate:	0.718
Human Intestinal Absorption (HIA):	0.558
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	90.36312103271484%
Volume Distribution (VD):	0.931
Pgp-substrate:	9.434487342834473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.257
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	2.835
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.848
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.25
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.016

Download Data

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

Natural Product: NPC183672

Natural Product ID:	NPC183672
*Common Name:**	Amurensin
IUPAC Name:	3,5-dihydroxy-8-(3-hydroxy-3-methylbutyl)-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:	Amurensin
Standard InCHIKey:	UNHHWEHQUUGKEE-MLLLWRCASA-N
Standard InCHI:	InChI=1S/C26H30O12/c1-26(2,35)8-7-13-15(36-25-22(34)20(32)18(30)16(10-27)37-25)9-14(29)17-19(31)21(33)23(38-24(13)17)11-3-5-12(28)6-4-11/h3-6,9,16,18,20,22,25,27-30,32-35H,7-8,10H2,1-2H3/t16-,18-,20+,22-,25-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2CCC(O)(C)C)oc(c(c3=O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454069
PubChem CID:	5318156
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[14510598]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO24476.1	Phellodendron amurense var. wilsonii	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3690	Vitis amurensis	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	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
Others	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	88300.0	nM	PMID[487745]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	15.4	%	PMID[487745]

☑ 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 NPC183672 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	427
0.1-0.2	1678
0.2-0.3	3727
0.3-0.4	9167
0.4-0.5	9189
0.5-0.6	4550
0.6-0.7	5461
0.7-0.8	4731
0.8-0.85	2343
0.85-0.9	925
0.9-0.95	464
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC131745
0.9871	High Similarity	NPC179198
0.9871	High Similarity	NPC278419
0.9871	High Similarity	NPC66087
0.9806	High Similarity	NPC259834
0.9679	High Similarity	NPC44947
0.9675	High Similarity	NPC108831
0.9675	High Similarity	NPC182634
0.9623	High Similarity	NPC5319
0.9618	High Similarity	NPC257566
0.9618	High Similarity	NPC124155
0.9615	High Similarity	NPC47923
0.9613	High Similarity	NPC41121
0.9613	High Similarity	NPC320283
0.9613	High Similarity	NPC111929
0.9613	High Similarity	NPC472459
0.9613	High Similarity	NPC73511
0.961	High Similarity	NPC307938
0.961	High Similarity	NPC203500
0.961	High Similarity	NPC323593
0.9554	High Similarity	NPC150164
0.9551	High Similarity	NPC187379
0.9551	High Similarity	NPC153342
0.9551	High Similarity	NPC472320
0.9548	High Similarity	NPC156457
0.9548	High Similarity	NPC313163
0.9548	High Similarity	NPC258035
0.9548	High Similarity	NPC197896
0.9548	High Similarity	NPC161749
0.9548	High Similarity	NPC23817
0.9548	High Similarity	NPC78263
0.9548	High Similarity	NPC133671
0.9548	High Similarity	NPC77672
0.9548	High Similarity	NPC54802
0.9548	High Similarity	NPC135391
0.9548	High Similarity	NPC197304
0.9548	High Similarity	NPC6985
0.9545	High Similarity	NPC304207
0.9545	High Similarity	NPC48579
0.9545	High Similarity	NPC470603
0.9545	High Similarity	NPC95090
0.9545	High Similarity	NPC217706
0.9545	High Similarity	NPC470604
0.9545	High Similarity	NPC207809
0.9545	High Similarity	NPC259710
0.9545	High Similarity	NPC27408
0.9545	High Similarity	NPC304745
0.9545	High Similarity	NPC111341
0.9545	High Similarity	NPC470605
0.9494	High Similarity	NPC121703
0.949	High Similarity	NPC116458
0.949	High Similarity	NPC476215
0.949	High Similarity	NPC224530
0.949	High Similarity	NPC246943
0.949	High Similarity	NPC265885
0.949	High Similarity	NPC215710
0.949	High Similarity	NPC85707
0.949	High Similarity	NPC139320
0.949	High Similarity	NPC216496
0.949	High Similarity	NPC129217
0.949	High Similarity	NPC259957
0.949	High Similarity	NPC249281
0.949	High Similarity	NPC303913
0.949	High Similarity	NPC181465
0.949	High Similarity	NPC473438
0.949	High Similarity	NPC159579
0.949	High Similarity	NPC48093
0.949	High Similarity	NPC163242
0.949	High Similarity	NPC276377
0.949	High Similarity	NPC173582
0.949	High Similarity	NPC253788
0.9487	High Similarity	NPC470607
0.9484	High Similarity	NPC206378
0.9484	High Similarity	NPC45165
0.9481	High Similarity	NPC108706
0.9481	High Similarity	NPC78021
0.9481	High Similarity	NPC87304
0.9481	High Similarity	NPC143851
0.9481	High Similarity	NPC211158
0.9481	High Similarity	NPC29763
0.9481	High Similarity	NPC210003
0.9481	High Similarity	NPC180301
0.9481	High Similarity	NPC106625
0.9481	High Similarity	NPC248793
0.9481	High Similarity	NPC268193
0.9481	High Similarity	NPC83283
0.9481	High Similarity	NPC268950
0.9481	High Similarity	NPC39360
0.9434	High Similarity	NPC72016
0.943	High Similarity	NPC27942
0.943	High Similarity	NPC240306
0.943	High Similarity	NPC190450
0.9427	High Similarity	NPC304741
0.9427	High Similarity	NPC136761
0.9427	High Similarity	NPC470405
0.9427	High Similarity	NPC471079
0.9423	High Similarity	NPC44931
0.9423	High Similarity	NPC129827
0.9423	High Similarity	NPC60966
0.9423	High Similarity	NPC122809
0.9423	High Similarity	NPC470606
0.9423	High Similarity	NPC65003
0.9423	High Similarity	NPC473512
0.9419	High Similarity	NPC169248
0.9419	High Similarity	NPC99233
0.9419	High Similarity	NPC97052
0.9419	High Similarity	NPC39351
0.9419	High Similarity	NPC72649
0.9419	High Similarity	NPC26195
0.9416	High Similarity	NPC244583
0.9416	High Similarity	NPC56232
0.9416	High Similarity	NPC121001
0.9416	High Similarity	NPC150123
0.9416	High Similarity	NPC161881
0.9416	High Similarity	NPC10807
0.9416	High Similarity	NPC259182
0.9387	High Similarity	NPC294629
0.9367	High Similarity	NPC64305
0.9367	High Similarity	NPC470125
0.9367	High Similarity	NPC135846
0.9367	High Similarity	NPC170052
0.9367	High Similarity	NPC297987
0.9367	High Similarity	NPC282169
0.9363	High Similarity	NPC104677
0.9363	High Similarity	NPC138811
0.9363	High Similarity	NPC308265
0.9363	High Similarity	NPC22062
0.9363	High Similarity	NPC473634
0.9363	High Similarity	NPC43761
0.9359	High Similarity	NPC261866
0.9359	High Similarity	NPC127406
0.9359	High Similarity	NPC20530
0.9359	High Similarity	NPC170475
0.9359	High Similarity	NPC10754
0.9359	High Similarity	NPC17521
0.9359	High Similarity	NPC215917
0.9355	High Similarity	NPC236756
0.9355	High Similarity	NPC223701
0.9355	High Similarity	NPC7989
0.9355	High Similarity	NPC311579
0.9355	High Similarity	NPC472583
0.9351	High Similarity	NPC319910
0.9351	High Similarity	NPC328740
0.9351	High Similarity	NPC209846
0.9351	High Similarity	NPC262038
0.9351	High Similarity	NPC278476
0.9351	High Similarity	NPC262039
0.9351	High Similarity	NPC477897
0.9351	High Similarity	NPC289774
0.9351	High Similarity	NPC254412
0.9321	High Similarity	NPC78734
0.9321	High Similarity	NPC76047
0.9321	High Similarity	NPC150767
0.9317	High Similarity	NPC173637
0.9317	High Similarity	NPC127546
0.9317	High Similarity	NPC52550
0.9317	High Similarity	NPC84362
0.9317	High Similarity	NPC317489
0.9317	High Similarity	NPC223424
0.9313	High Similarity	NPC135358
0.9313	High Similarity	NPC139060
0.9313	High Similarity	NPC277205
0.9313	High Similarity	NPC287889
0.9308	High Similarity	NPC93215
0.9304	High Similarity	NPC200708
0.9304	High Similarity	NPC142860
0.9304	High Similarity	NPC246469
0.9304	High Similarity	NPC271270
0.9304	High Similarity	NPC97285
0.9304	High Similarity	NPC473623
0.9304	High Similarity	NPC306978
0.9304	High Similarity	NPC271479
0.9299	High Similarity	NPC210048
0.9299	High Similarity	NPC288084
0.9299	High Similarity	NPC43638
0.9295	High Similarity	NPC476169
0.9295	High Similarity	NPC92395
0.9295	High Similarity	NPC470681
0.9295	High Similarity	NPC87404
0.929	High Similarity	NPC475790
0.929	High Similarity	NPC88484
0.929	High Similarity	NPC243171
0.929	High Similarity	NPC259767
0.929	High Similarity	NPC138288
0.929	High Similarity	NPC217149
0.929	High Similarity	NPC216035
0.929	High Similarity	NPC35567
0.929	High Similarity	NPC171651
0.9286	High Similarity	NPC105136
0.9286	High Similarity	NPC191154
0.9286	High Similarity	NPC38775
0.9273	High Similarity	NPC168584
0.9268	High Similarity	NPC108202
0.9264	High Similarity	NPC245452
0.9264	High Similarity	NPC256760
0.9259	High Similarity	NPC52382
0.9259	High Similarity	NPC259905
0.9259	High Similarity	NPC219904
0.9259	High Similarity	NPC120099
0.9259	High Similarity	NPC203050

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 NPC183672 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	920
0.2-0.3	1811
0.3-0.4	2685
0.4-0.5	1936
0.5-0.6	952
0.6-0.7	290
0.7-0.8	129
0.8-0.85	27
0.85-0.9	10
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9623	High Similarity	NPD7804	Clinical (unspecified phase)
0.9548	High Similarity	NPD4381	Clinical (unspecified phase)
0.9161	High Similarity	NPD4380	Phase 2
0.9146	High Similarity	NPD6797	Phase 2
0.9091	High Similarity	NPD7251	Discontinued
0.9057	High Similarity	NPD7075	Discontinued
0.9036	High Similarity	NPD7808	Phase 3
0.9024	High Similarity	NPD7054	Approved
0.897	High Similarity	NPD7472	Approved
0.897	High Similarity	NPD7074	Phase 3
0.8961	High Similarity	NPD4378	Clinical (unspecified phase)
0.8924	High Similarity	NPD6801	Discontinued
0.8922	High Similarity	NPD4338	Clinical (unspecified phase)
0.8868	High Similarity	NPD7096	Clinical (unspecified phase)
0.8848	High Similarity	NPD3818	Discontinued
0.875	High Similarity	NPD6559	Discontinued
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8727	High Similarity	NPD6166	Phase 2
0.8727	High Similarity	NPD6168	Clinical (unspecified phase)
0.8727	High Similarity	NPD6167	Clinical (unspecified phase)
0.8599	High Similarity	NPD7410	Clinical (unspecified phase)
0.858	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD1934	Approved
0.8509	High Similarity	NPD7411	Suspended
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5403	Approved
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8418	Intermediate Similarity	NPD6799	Approved
0.8409	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD5401	Approved
0.8354	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD2796	Approved
0.8313	Intermediate Similarity	NPD1512	Approved
0.8293	Intermediate Similarity	NPD2801	Approved
0.8293	Intermediate Similarity	NPD7819	Suspended
0.8258	Intermediate Similarity	NPD1510	Phase 2
0.8221	Intermediate Similarity	NPD6599	Discontinued
0.8216	Intermediate Similarity	NPD7584	Approved
0.8214	Intermediate Similarity	NPD6959	Discontinued
0.8193	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1511	Approved
0.8176	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD6782	Approved
0.8087	Intermediate Similarity	NPD6780	Approved
0.8087	Intermediate Similarity	NPD6781	Approved
0.8087	Intermediate Similarity	NPD6776	Approved
0.8087	Intermediate Similarity	NPD6778	Approved
0.8087	Intermediate Similarity	NPD6777	Approved
0.8087	Intermediate Similarity	NPD6779	Approved
0.8047	Intermediate Similarity	NPD5494	Approved
0.8046	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8313	Approved
0.8011	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7977	Intermediate Similarity	NPD3751	Discontinued
0.7976	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD8455	Phase 2
0.7957	Intermediate Similarity	NPD7435	Discontinued
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.7931	Intermediate Similarity	NPD5844	Phase 1
0.7923	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1607	Approved
0.7888	Intermediate Similarity	NPD3750	Approved
0.7888	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7696	Phase 3
0.7861	Intermediate Similarity	NPD7698	Approved
0.7861	Intermediate Similarity	NPD7697	Approved
0.7849	Intermediate Similarity	NPD6232	Discontinued
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3749	Approved
0.7819	Intermediate Similarity	NPD7870	Phase 2
0.7819	Intermediate Similarity	NPD7871	Phase 2
0.7816	Intermediate Similarity	NPD7473	Discontinued
0.7814	Intermediate Similarity	NPD6534	Approved
0.7814	Intermediate Similarity	NPD6535	Approved
0.7789	Intermediate Similarity	NPD7701	Phase 2
0.7789	Intermediate Similarity	NPD7585	Approved
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7737	Intermediate Similarity	NPD7583	Approved
0.7716	Intermediate Similarity	NPD2800	Approved
0.7711	Intermediate Similarity	NPD920	Approved
0.7708	Intermediate Similarity	NPD7874	Approved
0.7708	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7699	Phase 2
0.7688	Intermediate Similarity	NPD7700	Phase 2
0.7674	Intermediate Similarity	NPD919	Approved
0.7668	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7783	Phase 2
0.7668	Intermediate Similarity	NPD7801	Approved
0.7665	Intermediate Similarity	NPD1653	Approved
0.7656	Intermediate Similarity	NPD8151	Discontinued
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD5953	Discontinued
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.7619	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD6823	Phase 2
0.761	Intermediate Similarity	NPD5124	Phase 1
0.761	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1243	Approved
0.7605	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7685	Pre-registration
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2534	Approved
0.7586	Intermediate Similarity	NPD1247	Approved
0.7586	Intermediate Similarity	NPD7199	Phase 2
0.7578	Intermediate Similarity	NPD7033	Discontinued
0.7578	Intermediate Similarity	NPD3748	Approved
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7228	Approved
0.7562	Intermediate Similarity	NPD6651	Approved
0.7544	Intermediate Similarity	NPD1465	Phase 2
0.7539	Intermediate Similarity	NPD8320	Phase 1
0.7539	Intermediate Similarity	NPD8319	Approved
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7528	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD37	Approved
0.7471	Intermediate Similarity	NPD6234	Discontinued
0.7469	Intermediate Similarity	NPD2799	Discontinued
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD4965	Approved
0.7438	Intermediate Similarity	NPD1613	Approved
0.7438	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6798	Discontinued
0.7412	Intermediate Similarity	NPD3226	Approved
0.7405	Intermediate Similarity	NPD4908	Phase 1
0.7403	Intermediate Similarity	NPD1091	Approved
0.7401	Intermediate Similarity	NPD3926	Phase 2
0.7391	Intermediate Similarity	NPD1933	Approved
0.7389	Intermediate Similarity	NPD2798	Approved
0.736	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2424	Discontinued
0.7327	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7305	Intermediate Similarity	NPD6190	Approved
0.7296	Intermediate Similarity	NPD6832	Phase 2
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1652	Phase 2
0.7287	Intermediate Similarity	NPD6212	Phase 3
0.7287	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6213	Phase 3
0.7284	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7246	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD943	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7213	Intermediate Similarity	NPD7240	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD7930	Approved
0.7195	Intermediate Similarity	NPD7097	Phase 1
0.7188	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.716	Intermediate Similarity	NPD5058	Phase 3
0.7158	Intermediate Similarity	NPD3823	Discontinued
0.7152	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7135	Intermediate Similarity	NPD5049	Phase 3
0.7125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD2797	Approved
0.7101	Intermediate Similarity	NPD3887	Approved
0.7101	Intermediate Similarity	NPD2309	Approved
0.7101	Intermediate Similarity	NPD2354	Approved
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7073	Intermediate Similarity	NPD230	Phase 1
0.7072	Intermediate Similarity	NPD2403	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