NPASS Compound

Structure

NPC257025 OpenBabel07101718292D 21 23 0 0 0 0 0 0 0 0999 V2000 -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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.0000 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 1.7321 1.0000 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 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 4.3301 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 4.0000 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 0.8660 -1.5000 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 7 1 0 0 0 0 2 10 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.78
LogD:	2.471
LogS:	-3.573
# Rotatable Bonds:	1
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	2.528
Fsp3:	0.0
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:	-5.007
MDCK Permeability:	9.38007087825099e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.378
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	96.25093841552734%
Volume Distribution (VD):	0.497
Pgp-substrate:	4.281348705291748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.561
CYP2D6-substrate:	0.416
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	9.175
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.218
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.952
Carcinogencity:	0.088
Eye Corrosion:	0.027
Eye Irritation:	0.944
Respiratory Toxicity:	0.179

Download Data

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

Natural Product: NPC257025

Natural Product ID:	NPC257025
*Common Name:**	Thunberginol B
IUPAC Name:	3-(3,4-dihydroxyphenyl)-6,8-dihydroxyisochromen-1-one
Synonyms:	thunberginol B
Standard InCHIKey:	NHFGEHLUROYMEB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-9-3-8-5-13(7-1-2-10(17)11(18)4-7)21-15(20)14(8)12(19)6-9/h1-6,16-19H
SMILES:	Oc1cc(O)c2c(c1)cc(oc2=O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL70501
PubChem CID:	5473310
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins 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
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11549443]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17609121]
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9871657]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
EC50	1
IC50	8
Others	7
Potency	30

Activity Type	# Activity
Cell Line	6
Individual Protein	31
NON-MOLECULAR	1
Others	6
PROTEIN-PROTEIN INTERACTION	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-3.8	%	PMID[537658]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-7.8	%	PMID[537658]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	7.2	%	PMID[537658]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	54.1	%	PMID[537658]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-8.0	%	PMID[537658]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[537659]
NPT62	Individual Protein	6-phospho-1-fructokinase	Trypanosoma brucei	Potency	n.a.	37933.0	nM	PMID[537659]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[537659]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	8196.1	nM	PMID[537659]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	14575.0	nM	PMID[537659]
NPT585	Individual Protein	Nuclear receptor subfamily 0 group B member 1	Homo sapiens	IC50	>	67547.0	nM	PMID[537659]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	67547.0	nM	PMID[537659]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[537659]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[537659]
NPT1852	Individual Protein	Rac GTPase-activating protein 1	Homo sapiens	IC50	n.a.	20440.0	nM	PMID[537659]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[537659]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[537659]
NPT1417	Individual Protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[537659]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[537659]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[537659]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	67015.8	nM	PMID[537659]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[537659]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[537659]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	39810.7	nM	PMID[537659]
NPT798	Individual Protein	Alkaline phosphatase placental-like	Homo sapiens	EC50	>	100000.0	nM	PMID[537659]
NPT799	Individual Protein	Intestinal alkaline phosphatase	Mus musculus	IC50	=	7570.0	nM	PMID[537659]
NPT801	Individual Protein	Intestinal alkaline phosphatase	Homo sapiens	IC50	=	2170.0	nM	PMID[537659]
NPT801	Individual Protein	Intestinal alkaline phosphatase	Homo sapiens	IC50	=	565.0	nM	PMID[537659]
NPT2	Others	Unspecified		Potency	n.a.	29092.9	nM	PMID[537659]
NPT802	Individual Protein	Alkaline phosphatase, tissue-nonspecific isozyme	Homo sapiens	IC50	=	19500.0	nM	PMID[537659]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	112201.8	nM	PMID[537659]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[537659]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[537659]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	10000.0	nM	PMID[537659]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[537659]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	19952.6	nM	PMID[537659]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[537659]
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PMID[537659]
NPT2	Others	Unspecified		IC50	n.a.	23010.0	nM	PMID[537659]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[537659]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[537659]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	n.a.	100000.0	nM	PMID[537659]
NPT22445	SINGLE PROTEIN	Fibroblast growth factor 22	Homo sapiens	AbsAC1	=	4.66	uM	PMID[537659]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[537659]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	53581.8	nM	PMID[537659]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[537659]

☑ 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 NPC257025 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	514
0.1-0.2	2234
0.2-0.3	5187
0.3-0.4	11116
0.4-0.5	5945
0.5-0.6	3997
0.6-0.7	5305
0.7-0.8	5024
0.8-0.85	2169
0.85-0.9	1090
0.9-0.95	111
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9635	High Similarity	NPC134969
0.9507	High Similarity	NPC476463
0.9214	High Similarity	NPC471819
0.9167	High Similarity	NPC138978
0.9161	High Similarity	NPC279121
0.913	High Similarity	NPC175943
0.9128	High Similarity	NPC227062
0.9116	High Similarity	NPC204350
0.9097	High Similarity	NPC70136
0.9091	High Similarity	NPC175013
0.9078	High Similarity	NPC247409
0.9071	High Similarity	NPC62907
0.9034	High Similarity	NPC20791
0.9034	High Similarity	NPC179271
0.9014	High Similarity	NPC155205
0.9	High Similarity	NPC223836
0.8973	High Similarity	NPC74881
0.8973	High Similarity	NPC108406
0.8973	High Similarity	NPC239312
0.8973	High Similarity	NPC51443
0.8973	High Similarity	NPC130230
0.8973	High Similarity	NPC275772
0.8933	High Similarity	NPC80534
0.8933	High Similarity	NPC56786
0.8933	High Similarity	NPC20541
0.8926	High Similarity	NPC295646
0.8919	High Similarity	NPC85131
0.8912	High Similarity	NPC118726
0.8912	High Similarity	NPC12367
0.8912	High Similarity	NPC119059
0.8904	High Similarity	NPC169749
0.8897	High Similarity	NPC38065
0.8897	High Similarity	NPC242893
0.8889	High Similarity	NPC314271
0.8881	High Similarity	NPC290664
0.8874	High Similarity	NPC54928
0.8874	High Similarity	NPC153512
0.8865	High Similarity	NPC50455
0.8859	High Similarity	NPC202157
0.8851	High Similarity	NPC87125
0.8851	High Similarity	NPC287101
0.8851	High Similarity	NPC52005
0.8851	High Similarity	NPC195351
0.8851	High Similarity	NPC259713
0.8851	High Similarity	NPC137062
0.8851	High Similarity	NPC270465
0.8851	High Similarity	NPC17286
0.8851	High Similarity	NPC296197
0.8851	High Similarity	NPC183950
0.8851	High Similarity	NPC216318
0.8851	High Similarity	NPC223579
0.8844	High Similarity	NPC168803
0.8836	High Similarity	NPC262282
0.8828	High Similarity	NPC470130
0.8819	High Similarity	NPC91546
0.8819	High Similarity	NPC220106
0.8819	High Similarity	NPC158634
0.8816	High Similarity	NPC273843
0.8811	High Similarity	NPC32360
0.8811	High Similarity	NPC268052
0.8808	High Similarity	NPC38898
0.8808	High Similarity	NPC67396
0.8803	High Similarity	NPC261292
0.8803	High Similarity	NPC301915
0.8792	High Similarity	NPC188871
0.8792	High Similarity	NPC295036
0.8792	High Similarity	NPC184136
0.8792	High Similarity	NPC45873
0.8792	High Similarity	NPC88804
0.8792	High Similarity	NPC77858
0.8792	High Similarity	NPC3825
0.8792	High Similarity	NPC96501
0.8792	High Similarity	NPC149127
0.8792	High Similarity	NPC151473
0.8792	High Similarity	NPC286342
0.8786	High Similarity	NPC153783
0.8784	High Similarity	NPC188679
0.8784	High Similarity	NPC120464
0.8784	High Similarity	NPC276930
0.8784	High Similarity	NPC218490
0.8784	High Similarity	NPC294852
0.8784	High Similarity	NPC321011
0.8777	High Similarity	NPC219892
0.8777	High Similarity	NPC189823
0.8759	High Similarity	NPC322112
0.8759	High Similarity	NPC284556
0.8759	High Similarity	NPC82913
0.8759	High Similarity	NPC105648
0.8759	High Similarity	NPC301178
0.8759	High Similarity	NPC250755
0.8758	High Similarity	NPC238381
0.8758	High Similarity	NPC280680
0.875	High Similarity	NPC475799
0.875	High Similarity	NPC158472
0.875	High Similarity	NPC24640
0.875	High Similarity	NPC13779
0.8742	High Similarity	NPC125487
0.8742	High Similarity	NPC281477
0.8742	High Similarity	NPC281703
0.8742	High Similarity	NPC89474
0.8733	High Similarity	NPC200740
0.8733	High Similarity	NPC252933
0.8733	High Similarity	NPC260895
0.8733	High Similarity	NPC54394
0.8733	High Similarity	NPC225731
0.8733	High Similarity	NPC125062
0.8732	High Similarity	NPC235115
0.8732	High Similarity	NPC156307
0.8725	High Similarity	NPC177298
0.8725	High Similarity	NPC48479
0.8725	High Similarity	NPC1612
0.8725	High Similarity	NPC183959
0.8716	High Similarity	NPC95864
0.8716	High Similarity	NPC12200
0.8716	High Similarity	NPC188074
0.8716	High Similarity	NPC125449
0.8707	High Similarity	NPC32470
0.8705	High Similarity	NPC233056
0.8705	High Similarity	NPC26697
0.8701	High Similarity	NPC139036
0.8701	High Similarity	NPC200594
0.8699	High Similarity	NPC471417
0.8699	High Similarity	NPC287722
0.8684	High Similarity	NPC82592
0.8684	High Similarity	NPC16286
0.8684	High Similarity	NPC16082
0.8684	High Similarity	NPC199926
0.8684	High Similarity	NPC471800
0.8681	High Similarity	NPC191280
0.8681	High Similarity	NPC92655
0.8675	High Similarity	NPC275836
0.8675	High Similarity	NPC71334
0.8675	High Similarity	NPC63187
0.8675	High Similarity	NPC37684
0.8675	High Similarity	NPC82325
0.8675	High Similarity	NPC100887
0.8675	High Similarity	NPC256283
0.8675	High Similarity	NPC57030
0.8675	High Similarity	NPC198826
0.8675	High Similarity	NPC241498
0.8675	High Similarity	NPC120163
0.8675	High Similarity	NPC188203
0.8675	High Similarity	NPC55205
0.8675	High Similarity	NPC39732
0.8675	High Similarity	NPC27208
0.8675	High Similarity	NPC162313
0.8675	High Similarity	NPC293183
0.8675	High Similarity	NPC222830
0.8675	High Similarity	NPC184284
0.8675	High Similarity	NPC167903
0.8675	High Similarity	NPC76041
0.8675	High Similarity	NPC239128
0.8675	High Similarity	NPC187498
0.8675	High Similarity	NPC212678
0.8675	High Similarity	NPC279989
0.8675	High Similarity	NPC131624
0.8675	High Similarity	NPC83508
0.8675	High Similarity	NPC157784
0.8675	High Similarity	NPC289968
0.8675	High Similarity	NPC115249
0.8675	High Similarity	NPC301323
0.8675	High Similarity	NPC25270
0.8675	High Similarity	NPC60972
0.8675	High Similarity	NPC275722
0.8675	High Similarity	NPC156222
0.8671	High Similarity	NPC135837
0.8671	High Similarity	NPC290030
0.8667	High Similarity	NPC62042
0.8667	High Similarity	NPC61620
0.8667	High Similarity	NPC470107
0.8667	High Similarity	NPC10467
0.8667	High Similarity	NPC472891
0.8662	High Similarity	NPC182496
0.8662	High Similarity	NPC180905
0.8658	High Similarity	NPC19545
0.8658	High Similarity	NPC272721
0.8658	High Similarity	NPC43669
0.8658	High Similarity	NPC194653
0.8658	High Similarity	NPC194856
0.8658	High Similarity	NPC139364
0.8658	High Similarity	NPC254702
0.8658	High Similarity	NPC203747
0.8658	High Similarity	NPC80710
0.8658	High Similarity	NPC3036
0.8658	High Similarity	NPC107636
0.8658	High Similarity	NPC195202
0.8658	High Similarity	NPC196277
0.8649	High Similarity	NPC267509
0.8649	High Similarity	NPC268366
0.8643	High Similarity	NPC34070
0.8643	High Similarity	NPC469526
0.8639	High Similarity	NPC280404
0.8639	High Similarity	NPC86373
0.8639	High Similarity	NPC95123
0.8639	High Similarity	NPC66404
0.8639	High Similarity	NPC210425
0.8639	High Similarity	NPC277426
0.8636	High Similarity	NPC315157
0.8636	High Similarity	NPC46736
0.8636	High Similarity	NPC197856

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 NPC257025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	1053
0.2-0.3	1905
0.3-0.4	2649
0.4-0.5	1690
0.5-0.6	920
0.6-0.7	305
0.7-0.8	103
0.8-0.85	39
0.85-0.9	12
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD1511	Approved
0.9034	High Similarity	NPD1512	Approved
0.8811	High Similarity	NPD970	Clinical (unspecified phase)
0.8618	High Similarity	NPD2801	Approved
0.8582	High Similarity	NPD943	Approved
0.8553	High Similarity	NPD1934	Approved
0.8521	High Similarity	NPD230	Phase 1
0.8497	Intermediate Similarity	NPD1465	Phase 2
0.8497	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6232	Discontinued
0.8442	Intermediate Similarity	NPD3817	Phase 2
0.8345	Intermediate Similarity	NPD1510	Phase 2
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8311	Intermediate Similarity	NPD3750	Approved
0.8269	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3882	Suspended
0.8148	Intermediate Similarity	NPD3818	Discontinued
0.8141	Intermediate Similarity	NPD7819	Suspended
0.8129	Intermediate Similarity	NPD9269	Phase 2
0.8121	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD1240	Approved
0.8065	Intermediate Similarity	NPD4380	Phase 2
0.8054	Intermediate Similarity	NPD1549	Phase 2
0.8049	Intermediate Similarity	NPD7472	Approved
0.8025	Intermediate Similarity	NPD6166	Phase 2
0.8025	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD3749	Approved
0.7974	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD2534	Approved
0.7974	Intermediate Similarity	NPD2533	Approved
0.7973	Intermediate Similarity	NPD3748	Approved
0.7973	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1607	Approved
0.7952	Intermediate Similarity	NPD7251	Discontinued
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7919	Intermediate Similarity	NPD1551	Phase 2
0.7908	Intermediate Similarity	NPD6799	Approved
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD7075	Discontinued
0.7875	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD9268	Approved
0.7808	Intermediate Similarity	NPD3764	Approved
0.78	Intermediate Similarity	NPD2935	Discontinued
0.7799	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7808	Phase 3
0.7793	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6190	Approved
0.777	Intermediate Similarity	NPD447	Suspended
0.775	Intermediate Similarity	NPD5402	Approved
0.7742	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6801	Discontinued
0.7724	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6599	Discontinued
0.7708	Intermediate Similarity	NPD1203	Approved
0.7682	Intermediate Similarity	NPD5408	Approved
0.7682	Intermediate Similarity	NPD2796	Approved
0.7682	Intermediate Similarity	NPD5406	Approved
0.7682	Intermediate Similarity	NPD5404	Approved
0.7682	Intermediate Similarity	NPD5405	Approved
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7390	Discontinued
0.7676	Intermediate Similarity	NPD1201	Approved
0.7673	Intermediate Similarity	NPD7411	Suspended
0.7658	Intermediate Similarity	NPD3226	Approved
0.7643	Intermediate Similarity	NPD5403	Approved
0.7628	Intermediate Similarity	NPD5401	Approved
0.7622	Intermediate Similarity	NPD6959	Discontinued
0.7607	Intermediate Similarity	NPD919	Approved
0.7607	Intermediate Similarity	NPD6234	Discontinued
0.7597	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7768	Phase 2
0.7586	Intermediate Similarity	NPD1470	Approved
0.7584	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1613	Approved
0.7568	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5494	Approved
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD9545	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD9493	Approved
0.7485	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1164	Approved
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2313	Discontinued
0.7431	Intermediate Similarity	NPD422	Phase 1
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4288	Approved
0.7421	Intermediate Similarity	NPD920	Approved
0.7419	Intermediate Similarity	NPD2800	Approved
0.7407	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD9717	Approved
0.7379	Intermediate Similarity	NPD1608	Approved
0.7378	Intermediate Similarity	NPD4965	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7378	Intermediate Similarity	NPD4966	Approved
0.7375	Intermediate Similarity	NPD1653	Approved
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7365	Intermediate Similarity	NPD5711	Approved
0.7365	Intermediate Similarity	NPD5710	Approved
0.7326	Intermediate Similarity	NPD6559	Discontinued
0.7308	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1247	Approved
0.7303	Intermediate Similarity	NPD1933	Approved
0.7294	Intermediate Similarity	NPD7228	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7279	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7261	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9494	Approved
0.7247	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6099	Approved
0.7225	Intermediate Similarity	NPD7685	Pre-registration
0.7219	Intermediate Similarity	NPD3926	Phase 2
0.7219	Intermediate Similarity	NPD411	Approved
0.7219	Intermediate Similarity	NPD3268	Approved
0.7216	Intermediate Similarity	NPD8150	Discontinued
0.719	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2798	Approved
0.7179	Intermediate Similarity	NPD2344	Approved
0.7179	Intermediate Similarity	NPD7266	Discontinued
0.7174	Intermediate Similarity	NPD74	Approved
0.7174	Intermediate Similarity	NPD9266	Approved
0.7172	Intermediate Similarity	NPD17	Approved
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7118	Intermediate Similarity	NPD5242	Approved
0.7105	Intermediate Similarity	NPD1296	Phase 2
0.7101	Intermediate Similarity	NPD9264	Approved
0.7101	Intermediate Similarity	NPD9267	Approved
0.7101	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9263	Approved
0.7086	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1610	Phase 2
0.7069	Intermediate Similarity	NPD5953	Discontinued
0.7063	Intermediate Similarity	NPD3300	Phase 2
0.7059	Intermediate Similarity	NPD7229	Phase 3
0.7052	Intermediate Similarity	NPD7286	Phase 2
0.7051	Intermediate Similarity	NPD7033	Discontinued
0.7047	Intermediate Similarity	NPD1283	Approved
0.7045	Intermediate Similarity	NPD8312	Approved
0.7045	Intermediate Similarity	NPD8313	Approved
0.7039	Intermediate Similarity	NPD4287	Approved
0.7032	Intermediate Similarity	NPD6651	Approved
0.7027	Intermediate Similarity	NPD1481	Phase 2
0.7012	Intermediate Similarity	NPD3455	Phase 2
0.7012	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3266	Approved
0.7	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD2309	Approved
0.6989	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1535	Discovery
0.6947	Remote Similarity	NPD8151	Discontinued
0.6937	Remote Similarity	NPD7003	Approved
0.6928	Remote Similarity	NPD4625	Phase 3
0.6928	Remote Similarity	NPD6386	Approved
0.6928	Remote Similarity	NPD6385	Approved
0.6905	Remote Similarity	NPD5353	Approved
0.6903	Remote Similarity	NPD4307	Phase 2
0.6903	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD1652	Phase 2
0.6875	Remote Similarity	NPD9281	Approved
0.6863	Remote Similarity	NPD4908	Phase 1
0.6862	Remote Similarity	NPD7435	Discontinued
0.6855	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1281	Approved
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1019	Discontinued
0.6836	Remote Similarity	NPD7240	Approved
0.6833	Remote Similarity	NPD8434	Phase 2
0.6829	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD9261	Approved
0.6811	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7458	Discontinued
0.6793	Remote Similarity	NPD6535	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