NPASS Compound

Structure

CID134975 OpenBabel06191715492D 23 24 0 0 0 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 -3.4641 1.0000 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 -1.5000 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 -3.4641 -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 -5.1962 -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 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 -5.1962 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 0.0000 -3.0000 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 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -6.0622 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 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 1 5 2 0 0 0 0 1 9 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 6 1 0 0 0 0 3 8 2 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.03
Volume:	291.608
LogP:	1.352
LogD:	1.328
LogS:	-2.54
# Rotatable Bonds:	4
TPSA:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	2.435
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.063
MDCK Permeability:	5.208274615142727e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.19
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	90.72511291503906%
Volume Distribution (VD):	0.524
Pgp-substrate:	8.282737731933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.029
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.013

ADMET: Excretion

Clearance (CL):	8.182
Half-life (T1/2):	0.97

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.811
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.931
Carcinogencity:	0.018
Eye Corrosion:	0.058
Eye Irritation:	0.907
Respiratory Toxicity:	0.54

Download Data

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

Natural Product: NPC134975

Natural Product ID:	NPC134975
*Common Name:**	Digallic Acid
IUPAC Name:	3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoic acid
Synonyms:	digallic acid; NSC-59263
Standard InCHIKey:	COVFEVWNJUOYRL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21)
SMILES:	O=C(c1cc(O)c(c(c1)O)O)Oc1cc(cc(c1O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL366356
PubChem CID:	341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32031812]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7352	Acacia arabica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7352	Acacia arabica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28369	Vachellia nilotica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30994	Melaphis chinensis	Species	Pemphigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7352	Acacia arabica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4075	Rhus punjabensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18685	Schlechtendalia chinensis	Species	Pemphigidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6185	Rhus potaninii	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24360	Centaurea squarrosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7352	Acacia arabica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25381	Litsea rotundifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14827	Rhus chinensis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25023	Lactarius camphoratus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28369	Vachellia nilotica	Species	Fabaceae	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	8
Ki	3
Others	5

Activity Type	# Activity
Individual Protein	12
Others	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	600.0	nM	PMID[532505]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	Inhibition	=	90.2	%	PMID[532506]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	Inhibition	=	89.5	%	PMID[532506]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	900.0	nM	PMID[532506]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	1500.0	nM	PMID[532506]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	600.0	nM	PMID[532506]
NPT4537	Individual Protein	Human immunodeficiency virus type 2 integrase	Human immunodeficiency virus 2	IC50	=	2500.0	nM	PMID[532506]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	2200.0	nM	PMID[532506]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	Inhibition	>	90.0	%	PMID[532507]
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	Ki	=	830.0	nM	PMID[532507]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Ki	=	390.0	nM	PMID[532507]
NPT2	Others	Unspecified		Inhibition	=	70.0	%	PMID[532507]
NPT2	Others	Unspecified		Ki	=	580.0	nM	PMID[532507]
NPT22562	SINGLE PROTEIN	Anthrax toxin receptor 2	Homo sapiens	IC50	=	50000.0	nM	PMID[532508]

☑ 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 NPC134975 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	414
0.1-0.2	2097
0.2-0.3	5723
0.3-0.4	11043
0.4-0.5	5514
0.5-0.6	3976
0.6-0.7	5494
0.7-0.8	6826
0.8-0.85	1349
0.85-0.9	235
0.9-0.95	24
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC262282
0.9489	High Similarity	NPC207516
0.9371	High Similarity	NPC107636
0.931	High Similarity	NPC75695
0.9275	High Similarity	NPC110899
0.9275	High Similarity	NPC112068
0.9275	High Similarity	NPC95679
0.9275	High Similarity	NPC25305
0.9275	High Similarity	NPC125417
0.9214	High Similarity	NPC326065
0.9172	High Similarity	NPC473091
0.906	High Similarity	NPC54928
0.9058	High Similarity	NPC155098
0.9054	High Similarity	NPC178134
0.9034	High Similarity	NPC472969
0.9	High Similarity	NPC247713
0.9	High Similarity	NPC1913
0.8986	High Similarity	NPC289968
0.8986	High Similarity	NPC310661
0.8986	High Similarity	NPC105827
0.894	High Similarity	NPC87317
0.894	High Similarity	NPC37502
0.894	High Similarity	NPC160780
0.894	High Similarity	NPC267627
0.894	High Similarity	NPC40702
0.894	High Similarity	NPC289811
0.8936	High Similarity	NPC239943
0.8933	High Similarity	NPC104983
0.8933	High Similarity	NPC300845
0.8933	High Similarity	NPC88803
0.8933	High Similarity	NPC291948
0.8933	High Similarity	NPC318432
0.8933	High Similarity	NPC250436
0.8904	High Similarity	NPC168803
0.8889	High Similarity	NPC22176
0.8889	High Similarity	NPC190587
0.8889	High Similarity	NPC121573
0.8889	High Similarity	NPC226738
0.8882	High Similarity	NPC24164
0.8882	High Similarity	NPC119125
0.8882	High Similarity	NPC166277
0.8882	High Similarity	NPC203020
0.8882	High Similarity	NPC239966
0.8882	High Similarity	NPC53889
0.8874	High Similarity	NPC114179
0.8874	High Similarity	NPC156818
0.8874	High Similarity	NPC68324
0.8874	High Similarity	NPC160512
0.8874	High Similarity	NPC38779
0.8874	High Similarity	NPC289322
0.8873	High Similarity	NPC225036
0.8873	High Similarity	NPC12218
0.8873	High Similarity	NPC105525
0.8873	High Similarity	NPC75763
0.8867	High Similarity	NPC145425
0.8857	High Similarity	NPC208760
0.8851	High Similarity	NPC45873
0.8849	High Similarity	NPC1321
0.8849	High Similarity	NPC283823
0.8849	High Similarity	NPC304929
0.8849	High Similarity	NPC159418
0.8849	High Similarity	NPC156124
0.8844	High Similarity	NPC43669
0.8844	High Similarity	NPC98809
0.8844	High Similarity	NPC272721
0.8844	High Similarity	NPC476394
0.8844	High Similarity	NPC196277
0.8841	High Similarity	NPC264145
0.8832	High Similarity	NPC94810
0.8824	High Similarity	NPC25389
0.8824	High Similarity	NPC311803
0.8824	High Similarity	NPC472859
0.8819	High Similarity	NPC312256
0.8816	High Similarity	NPC287872
0.8816	High Similarity	NPC74319
0.88	High Similarity	NPC475895
0.8792	High Similarity	NPC251110
0.8784	High Similarity	NPC17286
0.8784	High Similarity	NPC216318
0.8784	High Similarity	NPC296197
0.8784	High Similarity	NPC259713
0.8777	High Similarity	NPC111888
0.8776	High Similarity	NPC139839
0.8776	High Similarity	NPC77378
0.8774	High Similarity	NPC142614
0.8768	High Similarity	NPC299010
0.8767	High Similarity	NPC287275
0.8767	High Similarity	NPC70136
0.8766	High Similarity	NPC285108
0.8766	High Similarity	NPC33298
0.8759	High Similarity	NPC50221
0.8759	High Similarity	NPC114242
0.8759	High Similarity	NPC175013
0.8759	High Similarity	NPC473090
0.8758	High Similarity	NPC289346
0.8758	High Similarity	NPC200594
0.8758	High Similarity	NPC476373
0.875	High Similarity	NPC472860
0.875	High Similarity	NPC110419
0.8742	High Similarity	NPC208197
0.8742	High Similarity	NPC20541
0.8733	High Similarity	NPC39732
0.8733	High Similarity	NPC101996
0.8733	High Similarity	NPC27208
0.8733	High Similarity	NPC60972
0.8725	High Similarity	NPC248102
0.8725	High Similarity	NPC29231
0.8725	High Similarity	NPC61620
0.8725	High Similarity	NPC260582
0.8723	High Similarity	NPC274613
0.8723	High Similarity	NPC18646
0.8716	High Similarity	NPC118726
0.8716	High Similarity	NPC12367
0.8716	High Similarity	NPC194856
0.8716	High Similarity	NPC120464
0.8714	High Similarity	NPC288743
0.871	High Similarity	NPC67959
0.8707	High Similarity	NPC169749
0.8707	High Similarity	NPC165389
0.8699	High Similarity	NPC113397
0.8699	High Similarity	NPC207732
0.8699	High Similarity	NPC279121
0.8693	High Similarity	NPC238381
0.8693	High Similarity	NPC168616
0.8693	High Similarity	NPC83763
0.8675	High Similarity	NPC250822
0.8675	High Similarity	NPC191046
0.8675	High Similarity	NPC88645
0.8675	High Similarity	NPC75279
0.8675	High Similarity	NPC194095
0.8675	High Similarity	NPC292214
0.8675	High Similarity	NPC167091
0.8675	High Similarity	NPC271779
0.8675	High Similarity	NPC327032
0.8675	High Similarity	NPC206238
0.8675	High Similarity	NPC276409
0.8667	High Similarity	NPC93498
0.8667	High Similarity	NPC163883
0.8667	High Similarity	NPC50403
0.8667	High Similarity	NPC31363
0.8667	High Similarity	NPC133953
0.8667	High Similarity	NPC225731
0.8667	High Similarity	NPC28274
0.8667	High Similarity	NPC171010
0.8662	High Similarity	NPC473818
0.8662	High Similarity	NPC156892
0.8658	High Similarity	NPC183950
0.8658	High Similarity	NPC285527
0.8658	High Similarity	NPC287101
0.8658	High Similarity	NPC106334
0.8658	High Similarity	NPC52005
0.8658	High Similarity	NPC223579
0.8658	High Similarity	NPC137062
0.8658	High Similarity	NPC177298
0.8658	High Similarity	NPC48479
0.8654	High Similarity	NPC8070
0.8652	High Similarity	NPC237330
0.8652	High Similarity	NPC111635
0.8649	High Similarity	NPC48366
0.8649	High Similarity	NPC275772
0.8649	High Similarity	NPC61871
0.8649	High Similarity	NPC142528
0.8649	High Similarity	NPC51443
0.8649	High Similarity	NPC130230
0.8649	High Similarity	NPC43123
0.8649	High Similarity	NPC120621
0.8649	High Similarity	NPC30647
0.8649	High Similarity	NPC207729
0.8649	High Similarity	NPC74881
0.8649	High Similarity	NPC55557
0.8649	High Similarity	NPC239312
0.8649	High Similarity	NPC248257
0.8645	High Similarity	NPC90905
0.8645	High Similarity	NPC476371
0.8645	High Similarity	NPC476372
0.8645	High Similarity	NPC4013
0.8639	High Similarity	NPC287495
0.8639	High Similarity	NPC9370
0.8639	High Similarity	NPC131766
0.8636	High Similarity	NPC24627
0.8636	High Similarity	NPC155101
0.8636	High Similarity	NPC130955
0.8633	High Similarity	NPC285776
0.863	High Similarity	NPC229036
0.8618	High Similarity	NPC201136
0.8618	High Similarity	NPC471800
0.8618	High Similarity	NPC256612
0.8618	High Similarity	NPC92659
0.8618	High Similarity	NPC128863
0.8618	High Similarity	NPC4455
0.8618	High Similarity	NPC2476
0.8618	High Similarity	NPC146165
0.8618	High Similarity	NPC280339
0.8618	High Similarity	NPC227325
0.8618	High Similarity	NPC138360
0.8618	High Similarity	NPC163780
0.8618	High Similarity	NPC50715
0.8618	High Similarity	NPC20830
0.8618	High Similarity	NPC183597
0.8618	High Similarity	NPC2928

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 NPC134975 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	991
0.2-0.3	2040
0.3-0.4	2631
0.4-0.5	1611
0.5-0.6	963
0.6-0.7	368
0.7-0.8	126
0.8-0.85	18
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9054	High Similarity	NPD1465	Phase 2
0.8933	High Similarity	NPD4868	Clinical (unspecified phase)
0.8849	High Similarity	NPD230	Phase 1
0.8699	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD1512	Approved
0.8553	High Similarity	NPD2801	Approved
0.8487	Intermediate Similarity	NPD1934	Approved
0.8456	Intermediate Similarity	NPD9269	Phase 2
0.8442	Intermediate Similarity	NPD3882	Suspended
0.8377	Intermediate Similarity	NPD3817	Phase 2
0.8322	Intermediate Similarity	NPD447	Suspended
0.8313	Intermediate Similarity	NPD3818	Discontinued
0.8272	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD9268	Approved
0.8075	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6166	Phase 2
0.8067	Intermediate Similarity	NPD6190	Approved
0.8063	Intermediate Similarity	NPD6232	Discontinued
0.8039	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5844	Phase 1
0.8037	Intermediate Similarity	NPD7054	Approved
0.8028	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD9494	Approved
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7988	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1653	Approved
0.7973	Intermediate Similarity	NPD1551	Phase 2
0.7972	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6799	Approved
0.7925	Intermediate Similarity	NPD7075	Discontinued
0.7914	Intermediate Similarity	NPD7473	Discontinued
0.7887	Intermediate Similarity	NPD1203	Approved
0.7881	Intermediate Similarity	NPD4628	Phase 3
0.7867	Intermediate Similarity	NPD1549	Phase 2
0.7831	Intermediate Similarity	NPD6797	Phase 2
0.7812	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD1510	Phase 2
0.7784	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD4380	Phase 2
0.7764	Intermediate Similarity	NPD919	Approved
0.7764	Intermediate Similarity	NPD6234	Discontinued
0.7755	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD1240	Approved
0.7755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7808	Phase 3
0.7736	Intermediate Similarity	NPD7819	Suspended
0.7736	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3749	Approved
0.7688	Intermediate Similarity	NPD5353	Approved
0.7679	Intermediate Similarity	NPD7685	Pre-registration
0.7677	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1608	Approved
0.7673	Intermediate Similarity	NPD6801	Discontinued
0.7671	Intermediate Similarity	NPD3027	Phase 3
0.7667	Intermediate Similarity	NPD3748	Approved
0.7658	Intermediate Similarity	NPD6599	Discontinued
0.7651	Intermediate Similarity	NPD1607	Approved
0.7622	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7411	Suspended
0.7607	Intermediate Similarity	NPD5494	Approved
0.7606	Intermediate Similarity	NPD422	Phase 1
0.7582	Intermediate Similarity	NPD1243	Approved
0.758	Intermediate Similarity	NPD5403	Approved
0.7576	Intermediate Similarity	NPD5242	Approved
0.7571	Intermediate Similarity	NPD9545	Approved
0.7564	Intermediate Similarity	NPD5401	Approved
0.7564	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD37	Approved
0.7561	Intermediate Similarity	NPD7199	Phase 2
0.7552	Intermediate Similarity	NPD9717	Approved
0.755	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD4965	Approved
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD6385	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD6386	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.747	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3926	Phase 2
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD920	Approved
0.7467	Intermediate Similarity	NPD1933	Approved
0.7465	Intermediate Similarity	NPD17	Approved
0.7455	Intermediate Similarity	NPD1247	Approved
0.7452	Intermediate Similarity	NPD2533	Approved
0.7452	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2534	Approved
0.7452	Intermediate Similarity	NPD2532	Approved
0.7448	Intermediate Similarity	NPD3225	Approved
0.744	Intermediate Similarity	NPD7228	Approved
0.7431	Intermediate Similarity	NPD1481	Phase 2
0.7419	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2796	Approved
0.7383	Intermediate Similarity	NPD411	Approved
0.7383	Intermediate Similarity	NPD3764	Approved
0.7368	Intermediate Similarity	NPD6559	Discontinued
0.7361	Intermediate Similarity	NPD1535	Discovery
0.7355	Intermediate Similarity	NPD2800	Approved
0.7351	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4308	Phase 3
0.7317	Intermediate Similarity	NPD7768	Phase 2
0.7308	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1296	Phase 2
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7261	Intermediate Similarity	NPD2354	Approved
0.7256	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6832	Phase 2
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7226	Intermediate Similarity	NPD7266	Discontinued
0.7209	Intermediate Similarity	NPD5953	Discontinued
0.7208	Intermediate Similarity	NPD2799	Discontinued
0.7168	Intermediate Similarity	NPD7039	Approved
0.7168	Intermediate Similarity	NPD7038	Approved
0.7162	Intermediate Similarity	NPD2797	Approved
0.7161	Intermediate Similarity	NPD6099	Approved
0.7161	Intermediate Similarity	NPD6100	Approved
0.7153	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4288	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7115	Intermediate Similarity	NPD2344	Approved
0.7115	Intermediate Similarity	NPD2346	Discontinued
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7097	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7286	Phase 2
0.7091	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1548	Phase 1
0.7075	Intermediate Similarity	NPD2981	Phase 2
0.7071	Intermediate Similarity	NPD228	Approved
0.7067	Intermediate Similarity	NPD3018	Phase 2
0.7066	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD1558	Phase 1
0.7059	Intermediate Similarity	NPD4307	Phase 2
0.7055	Intermediate Similarity	NPD3455	Phase 2
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7025	Intermediate Similarity	NPD1652	Phase 2
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2353	Approved
0.7	Intermediate Similarity	NPD1019	Discontinued
0.6981	Remote Similarity	NPD4110	Phase 3
0.6981	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.6971	Remote Similarity	NPD7240	Approved
0.6966	Remote Similarity	NPD8434	Phase 2
0.6966	Remote Similarity	NPD1894	Discontinued
0.6951	Remote Similarity	NPD824	Approved
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9493	Approved
0.6937	Remote Similarity	NPD2309	Approved
0.6933	Remote Similarity	NPD3266	Approved
0.6933	Remote Similarity	NPD3267	Approved
0.6928	Remote Similarity	NPD6798	Discontinued
0.6919	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3146	Approved
0.6914	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6355	Discontinued
0.6901	Remote Similarity	NPD7229	Phase 3
0.6901	Remote Similarity	NPD5710	Approved
0.6901	Remote Similarity	NPD3787	Discontinued
0.6901	Remote Similarity	NPD5711	Approved
0.6894	Remote Similarity	NPD7440	Discontinued
0.6893	Remote Similarity	NPD8312	Approved
0.6893	Remote Similarity	NPD8313	Approved
0.6883	Remote Similarity	NPD4062	Phase 3
0.6871	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD1778	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1283	Approved
0.6859	Remote Similarity	NPD6651	Approved
0.6853	Remote Similarity	NPD1241	Discontinued
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4060	Phase 1
0.6836	Remote Similarity	NPD7549	Discontinued
0.6832	Remote Similarity	NPD3887	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