NPASS Compound

Structure

CID56379 OpenBabel06191715392D 27 29 0 0 0 0 0 0 0 0999 V2000 2.5981 -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 -0.0000 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 -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 -2.5981 0.5000 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 -1.7321 -1.0000 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 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 -1.7321 -0.0000 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 -0.8660 0.5000 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 4.3301 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 Cl 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 14 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 10 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 9 16 2 0 0 0 0 10 14 2 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 17 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	481.86
Volume:	388.124
LogP:	7.162
LogD:	2.6
LogS:	-6.131
# Rotatable Bonds:	3
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	2.564
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.2
MDCK Permeability:	5.855529707332607e-06
Pgp-inhibitor:	0.067
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	105.97874450683594%
Volume Distribution (VD):	2.54
Pgp-substrate:	1.2163262367248535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.779
CYP1A2-substrate:	0.207
CYP2C19-inhibitor:	0.79
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.731
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.429
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	3.644
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.847
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.918
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.477
Respiratory Toxicity:	0.233

Download Data

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

Natural Product: NPC56379

Natural Product ID:	NPC56379
*Common Name:**	Ambigol A
IUPAC Name:	3,5-dichloro-2-(3,5-dichloro-2-hydroxyphenyl)-6-(2,4-dichlorophenoxy)phenol
Synonyms:
Standard InCHIKey:	AHLSIYMTIQLHAO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H8Cl6O3/c19-7-1-2-14(10(21)4-7)27-18-13(24)6-11(22)15(17(18)26)9-3-8(20)5-12(23)16(9)25/h1-6,25-26H
SMILES:	Clc1ccc(c(c1)Cl)Oc1c(Cl)cc(c(c1O)c1cc(Cl)cc(c1O)Cl)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479907
PubChem CID:	475341
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives [CHEMONTID:0000500] Chlorinated biphenyls [CHEMONTID:0003030] Polychlorinated biphenyls

*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
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15787461]
NPO12573	Hypericum annulatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17260692]
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19371071]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15556	Vernonia guineensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12573	Hypericum annulatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9797	Aconitum toxicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17468	Hortia brasiliensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15556	Vernonia guineensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14019	Paraphaeosphaeria sporulosa	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO420	Eucheuma muricatum	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13801	Artemisia chamaemelifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14060	Fischerella ambigua	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12573	Hypericum annulatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
MIC	4
Others	6

Activity Type	# Activity
Cell Line	1
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	33.0	ug.mL-1	PMID[550466]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	8.0	mm	PMID[550466]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	7.0	mm	PMID[550466]
NPT1232	Organism	Eurotium repens	Eurotium repens	IZ	=	7.0	mm	PMID[550466]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IZ	=	8.0	mm	PMID[550466]
NPT1233	Organism	Mycotypha microspora	Mycotypha microspora	IZ	=	4.0	mm	PMID[550466]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	3.0	mm	PMID[550466]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	MIC	=	33.0	ug.mL-1	PMID[550466]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	MIC	=	33.0	ug.mL-1	PMID[550466]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.846	ug.mL-1	PMID[550466]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.623	ug.mL-1	PMID[550466]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	64.0	ug.mL-1	PMID[550466]

☑ 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 NPC56379 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	915
0.1-0.2	3324
0.2-0.3	13023
0.3-0.4	6980
0.4-0.5	5615
0.5-0.6	9614
0.6-0.7	3109
0.7-0.8	115
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8067	Intermediate Similarity	NPC139335
0.7867	Intermediate Similarity	NPC246991
0.7806	Intermediate Similarity	NPC475423
0.774	Intermediate Similarity	NPC205213
0.7667	Intermediate Similarity	NPC8058
0.7569	Intermediate Similarity	NPC39409
0.7568	Intermediate Similarity	NPC42644
0.7547	Intermediate Similarity	NPC131379
0.7532	Intermediate Similarity	NPC193334
0.7484	Intermediate Similarity	NPC252901
0.7432	Intermediate Similarity	NPC471807
0.7417	Intermediate Similarity	NPC235370
0.7377	Intermediate Similarity	NPC471805
0.7377	Intermediate Similarity	NPC121100
0.7377	Intermediate Similarity	NPC471813
0.7337	Intermediate Similarity	NPC471806
0.7337	Intermediate Similarity	NPC471810
0.7329	Intermediate Similarity	NPC244403
0.7322	Intermediate Similarity	NPC471812
0.7322	Intermediate Similarity	NPC471803
0.7322	Intermediate Similarity	NPC471804
0.732	Intermediate Similarity	NPC134431
0.732	Intermediate Similarity	NPC156854
0.729	Intermediate Similarity	NPC210655
0.7278	Intermediate Similarity	NPC256307
0.7278	Intermediate Similarity	NPC66840
0.7278	Intermediate Similarity	NPC103967
0.7273	Intermediate Similarity	NPC21563
0.7261	Intermediate Similarity	NPC202762
0.7261	Intermediate Similarity	NPC73656
0.7261	Intermediate Similarity	NPC86655
0.7233	Intermediate Similarity	NPC261873
0.7233	Intermediate Similarity	NPC283009
0.7226	Intermediate Similarity	NPC46274
0.7226	Intermediate Similarity	NPC226331
0.7222	Intermediate Similarity	NPC28160
0.7205	Intermediate Similarity	NPC22517
0.7192	Intermediate Similarity	NPC91452
0.719	Intermediate Similarity	NPC33402
0.7188	Intermediate Similarity	NPC77861
0.7188	Intermediate Similarity	NPC248727
0.7188	Intermediate Similarity	NPC270456
0.7188	Intermediate Similarity	NPC265433
0.7188	Intermediate Similarity	NPC162659
0.7179	Intermediate Similarity	NPC185313
0.717	Intermediate Similarity	NPC49603
0.717	Intermediate Similarity	NPC141023
0.717	Intermediate Similarity	NPC193026
0.717	Intermediate Similarity	NPC106215
0.717	Intermediate Similarity	NPC478085
0.717	Intermediate Similarity	NPC187616
0.7161	Intermediate Similarity	NPC250432
0.7161	Intermediate Similarity	NPC50368
0.7161	Intermediate Similarity	NPC5447
0.716	Intermediate Similarity	NPC61783
0.716	Intermediate Similarity	NPC22317
0.716	Intermediate Similarity	NPC20520
0.7158	Intermediate Similarity	NPC195675
0.7158	Intermediate Similarity	NPC471808
0.7158	Intermediate Similarity	NPC471814
0.7152	Intermediate Similarity	NPC218884
0.7152	Intermediate Similarity	NPC127624
0.7152	Intermediate Similarity	NPC228843
0.7152	Intermediate Similarity	NPC131128
0.7152	Intermediate Similarity	NPC474134
0.7143	Intermediate Similarity	NPC201145
0.7143	Intermediate Similarity	NPC272157
0.7143	Intermediate Similarity	NPC73535
0.7143	Intermediate Similarity	NPC90615
0.7143	Intermediate Similarity	NPC6262
0.7143	Intermediate Similarity	NPC25111
0.7143	Intermediate Similarity	NPC48956
0.7134	Intermediate Similarity	NPC143483
0.7134	Intermediate Similarity	NPC91291
0.7125	Intermediate Similarity	NPC112246
0.7125	Intermediate Similarity	NPC474206
0.7125	Intermediate Similarity	NPC112939
0.7125	Intermediate Similarity	NPC121812
0.7125	Intermediate Similarity	NPC94750
0.7125	Intermediate Similarity	NPC470356
0.712	Intermediate Similarity	NPC471811
0.712	Intermediate Similarity	NPC471809
0.7117	Intermediate Similarity	NPC178054
0.7115	Intermediate Similarity	NPC72529
0.7115	Intermediate Similarity	NPC472968
0.7114	Intermediate Similarity	NPC86947
0.7107	Intermediate Similarity	NPC168059
0.7107	Intermediate Similarity	NPC229442
0.7099	Intermediate Similarity	NPC127218
0.7099	Intermediate Similarity	NPC105847
0.7099	Intermediate Similarity	NPC218131
0.7099	Intermediate Similarity	NPC70682
0.7099	Intermediate Similarity	NPC260741
0.7099	Intermediate Similarity	NPC245207
0.7099	Intermediate Similarity	NPC232164
0.7099	Intermediate Similarity	NPC236306
0.7099	Intermediate Similarity	NPC25966
0.7099	Intermediate Similarity	NPC243759
0.7099	Intermediate Similarity	NPC55947
0.7099	Intermediate Similarity	NPC473739
0.7099	Intermediate Similarity	NPC319647
0.7097	Intermediate Similarity	NPC178284
0.7097	Intermediate Similarity	NPC58607
0.7097	Intermediate Similarity	NPC17837
0.7097	Intermediate Similarity	NPC191037
0.7097	Intermediate Similarity	NPC304630
0.7081	Intermediate Similarity	NPC476639
0.7081	Intermediate Similarity	NPC10737
0.7081	Intermediate Similarity	NPC300846
0.7081	Intermediate Similarity	NPC302701
0.7081	Intermediate Similarity	NPC16435
0.7081	Intermediate Similarity	NPC209985
0.7081	Intermediate Similarity	NPC54743
0.7081	Intermediate Similarity	NPC263367
0.7081	Intermediate Similarity	NPC177160
0.7081	Intermediate Similarity	NPC29799
0.7081	Intermediate Similarity	NPC474639
0.7081	Intermediate Similarity	NPC227503
0.7081	Intermediate Similarity	NPC269091
0.7081	Intermediate Similarity	NPC230734
0.7081	Intermediate Similarity	NPC477939
0.7081	Intermediate Similarity	NPC143139
0.7081	Intermediate Similarity	NPC202846
0.7081	Intermediate Similarity	NPC114155
0.7081	Intermediate Similarity	NPC156502
0.7081	Intermediate Similarity	NPC306441
0.7078	Intermediate Similarity	NPC122792
0.7078	Intermediate Similarity	NPC228972
0.707	Intermediate Similarity	NPC5851
0.707	Intermediate Similarity	NPC86030
0.7066	Intermediate Similarity	NPC275125
0.7066	Intermediate Similarity	NPC97937
0.7066	Intermediate Similarity	NPC170239
0.7063	Intermediate Similarity	NPC317380
0.7063	Intermediate Similarity	NPC160697
0.7055	Intermediate Similarity	NPC291101
0.7055	Intermediate Similarity	NPC295719
0.7055	Intermediate Similarity	NPC266197
0.7055	Intermediate Similarity	NPC308768
0.7055	Intermediate Similarity	NPC34431
0.7055	Intermediate Similarity	NPC309124
0.7055	Intermediate Similarity	NPC12668
0.7055	Intermediate Similarity	NPC184797
0.7055	Intermediate Similarity	NPC73505
0.7055	Intermediate Similarity	NPC165026
0.7055	Intermediate Similarity	NPC55793
0.7051	Intermediate Similarity	NPC26576
0.7051	Intermediate Similarity	NPC118787
0.7051	Intermediate Similarity	NPC470699
0.7051	Intermediate Similarity	NPC163332
0.7051	Intermediate Similarity	NPC147821
0.7051	Intermediate Similarity	NPC41706
0.7051	Intermediate Similarity	NPC319625
0.7051	Intermediate Similarity	NPC292056
0.7051	Intermediate Similarity	NPC183181
0.7051	Intermediate Similarity	NPC111247
0.7051	Intermediate Similarity	NPC266555
0.7044	Intermediate Similarity	NPC78770
0.7044	Intermediate Similarity	NPC15658
0.7044	Intermediate Similarity	NPC261619
0.7044	Intermediate Similarity	NPC126029
0.7044	Intermediate Similarity	NPC61477
0.7044	Intermediate Similarity	NPC185604
0.7044	Intermediate Similarity	NPC219876
0.7044	Intermediate Similarity	NPC303144
0.7044	Intermediate Similarity	NPC189482
0.7037	Intermediate Similarity	NPC176051
0.7037	Intermediate Similarity	NPC211549
0.7037	Intermediate Similarity	NPC474390
0.7037	Intermediate Similarity	NPC102904
0.7037	Intermediate Similarity	NPC266453
0.7037	Intermediate Similarity	NPC276490
0.7037	Intermediate Similarity	NPC151656
0.7037	Intermediate Similarity	NPC103976
0.7037	Intermediate Similarity	NPC107551
0.7037	Intermediate Similarity	NPC200935
0.7037	Intermediate Similarity	NPC230919
0.7037	Intermediate Similarity	NPC474282
0.7037	Intermediate Similarity	NPC326797
0.7032	Intermediate Similarity	NPC194519
0.703	Intermediate Similarity	NPC469630
0.7019	Intermediate Similarity	NPC93783
0.7019	Intermediate Similarity	NPC151224
0.7019	Intermediate Similarity	NPC69029
0.7019	Intermediate Similarity	NPC201357
0.7019	Intermediate Similarity	NPC234333
0.7019	Intermediate Similarity	NPC108198
0.7019	Intermediate Similarity	NPC158142
0.7019	Intermediate Similarity	NPC134968
0.7019	Intermediate Similarity	NPC255147
0.7019	Intermediate Similarity	NPC61946
0.7019	Intermediate Similarity	NPC281521
0.7019	Intermediate Similarity	NPC294884
0.7019	Intermediate Similarity	NPC164787
0.7019	Intermediate Similarity	NPC111655
0.7019	Intermediate Similarity	NPC47398
0.7019	Intermediate Similarity	NPC260898
0.7019	Intermediate Similarity	NPC10314
0.7019	Intermediate Similarity	NPC200557
0.7012	Intermediate Similarity	NPC35216

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 NPC56379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	681
0.1-0.2	1089
0.2-0.3	2526
0.3-0.4	2470
0.4-0.5	1508
0.5-0.6	785
0.6-0.7	81
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.774	Intermediate Similarity	NPD915	Approved
0.7394	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4536	Approved
0.7233	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4538	Approved
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1184	Approved
0.7188	Intermediate Similarity	NPD5588	Approved
0.7188	Intermediate Similarity	NPD5960	Phase 3
0.7171	Intermediate Similarity	NPD1157	Approved
0.7169	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4873	Discontinued
0.7044	Intermediate Similarity	NPD1613	Approved
0.7044	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5058	Phase 3
0.6868	Remote Similarity	NPD3303	Discontinued
0.6786	Remote Similarity	NPD6815	Approved
0.6766	Remote Similarity	NPD4535	Phase 3
0.6753	Remote Similarity	NPD4589	Approved
0.6753	Remote Similarity	NPD5846	Approved
0.6753	Remote Similarity	NPD6516	Phase 2
0.675	Remote Similarity	NPD3027	Phase 3
0.673	Remote Similarity	NPD2861	Phase 2
0.6685	Remote Similarity	NPD3365	Discontinued
0.6647	Remote Similarity	NPD7041	Phase 2
0.6647	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4625	Phase 3
0.6626	Remote Similarity	NPD1558	Phase 1
0.66	Remote Similarity	NPD228	Approved
0.6584	Remote Similarity	NPD4908	Phase 1
0.6561	Remote Similarity	NPD1610	Phase 2
0.6548	Remote Similarity	NPD5958	Discontinued
0.6548	Remote Similarity	NPD4534	Discontinued
0.6536	Remote Similarity	NPD6671	Approved
0.6527	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD454	Approved
0.6512	Remote Similarity	NPD1578	Phase 2
0.6503	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1972	Approved
0.6494	Remote Similarity	NPD1969	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1973	Approved
0.6478	Remote Similarity	NPD4749	Approved
0.645	Remote Similarity	NPD2808	Discontinued
0.6441	Remote Similarity	NPD1934	Approved
0.642	Remote Similarity	NPD4972	Discontinued
0.641	Remote Similarity	NPD1548	Phase 1
0.6407	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5283	Phase 1
0.6358	Remote Similarity	NPD5451	Approved
0.6358	Remote Similarity	NPD1511	Approved
0.6333	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3620	Phase 2
0.6325	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4060	Phase 1
0.6316	Remote Similarity	NPD1416	Approved
0.6313	Remote Similarity	NPD2801	Approved
0.6302	Remote Similarity	NPD5800	Discontinued
0.6294	Remote Similarity	NPD2378	Approved
0.6294	Remote Similarity	NPD2377	Approved
0.6294	Remote Similarity	NPD2376	Approved
0.6294	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD1512	Approved
0.6273	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6166	Phase 2
0.627	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD968	Approved
0.6258	Remote Similarity	NPD6584	Phase 3
0.6257	Remote Similarity	NPD2170	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3022	Approved
0.625	Remote Similarity	NPD3021	Approved
0.6243	Remote Similarity	NPD2354	Approved
0.6242	Remote Similarity	NPD9501	Approved
0.6242	Remote Similarity	NPD7095	Approved
0.6237	Remote Similarity	NPD5880	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6696	Suspended
0.6225	Remote Similarity	NPD9552	Approved
0.6222	Remote Similarity	NPD1465	Phase 2
0.6222	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD6674	Discontinued
0.6221	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1608	Approved
0.6205	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD958	Approved
0.6196	Remote Similarity	NPD987	Approved
0.6183	Remote Similarity	NPD2403	Approved
0.618	Remote Similarity	NPD6056	Approved
0.618	Remote Similarity	NPD4017	Approved
0.618	Remote Similarity	NPD6057	Approved
0.6178	Remote Similarity	NPD3337	Discontinued
0.6174	Remote Similarity	NPD9500	Approved
0.6171	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1091	Approved
0.6145	Remote Similarity	NPD1715	Phase 1
0.6145	Remote Similarity	NPD1714	Approved
0.6142	Remote Similarity	NPD6312	Discontinued
0.6136	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD8651	Approved
0.6131	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD1653	Approved
0.6121	Remote Similarity	NPD3018	Phase 2
0.6118	Remote Similarity	NPD290	Approved
0.6118	Remote Similarity	NPD2342	Discontinued
0.6108	Remote Similarity	NPD6798	Discontinued
0.6108	Remote Similarity	NPD7199	Phase 2
0.6089	Remote Similarity	NPD5894	Phase 2
0.6087	Remote Similarity	NPD6234	Discontinued
0.6085	Remote Similarity	NPD5844	Phase 1
0.6082	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2684	Approved
0.6075	Remote Similarity	NPD6232	Discontinued
0.6074	Remote Similarity	NPD6583	Phase 3
0.6074	Remote Similarity	NPD6582	Phase 2
0.6074	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD3882	Suspended
0.6057	Remote Similarity	NPD2677	Approved
0.6049	Remote Similarity	NPD3705	Approved
0.6049	Remote Similarity	NPD1611	Approved
0.6047	Remote Similarity	NPD6099	Approved
0.6047	Remote Similarity	NPD6100	Approved
0.6045	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD957	Approved
0.6034	Remote Similarity	NPD5177	Phase 3
0.6032	Remote Similarity	NPD3818	Discontinued
0.6025	Remote Similarity	NPD17	Approved
0.6013	Remote Similarity	NPD709	Approved
0.6013	Remote Similarity	NPD7157	Approved
0.6012	Remote Similarity	NPD5762	Approved
0.6012	Remote Similarity	NPD2353	Approved
0.6012	Remote Similarity	NPD5763	Approved
0.6012	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD3364	Phase 3
0.6	Remote Similarity	NPD5735	Approved
0.6	Remote Similarity	NPD3933	Discontinued
0.6	Remote Similarity	NPD6331	Phase 2
0.6	Remote Similarity	NPD2797	Approved
0.5979	Remote Similarity	NPD8054	Approved
0.5979	Remote Similarity	NPD7473	Discontinued
0.5979	Remote Similarity	NPD8053	Approved
0.5976	Remote Similarity	NPD4359	Approved
0.5976	Remote Similarity	NPD6542	Approved
0.5976	Remote Similarity	NPD2982	Phase 2
0.5976	Remote Similarity	NPD6539	Approved
0.5976	Remote Similarity	NPD6543	Approved
0.5976	Remote Similarity	NPD6540	Phase 3
0.5976	Remote Similarity	NPD2983	Phase 2
0.5969	Remote Similarity	NPD7074	Phase 3
0.5956	Remote Similarity	NPD8455	Phase 2
0.5955	Remote Similarity	NPD4123	Phase 3
0.5951	Remote Similarity	NPD422	Phase 1
0.5946	Remote Similarity	NPD4064	Discontinued
0.5939	Remote Similarity	NPD6538	Approved
0.5939	Remote Similarity	NPD6541	Approved
0.5939	Remote Similarity	NPD3225	Approved
0.5938	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD3274	Phase 2
0.5933	Remote Similarity	NPD1616	Discontinued
0.5928	Remote Similarity	NPD4577	Approved
0.5928	Remote Similarity	NPD4578	Approved
0.5926	Remote Similarity	NPD27	Approved
0.5926	Remote Similarity	NPD2489	Approved
0.5924	Remote Similarity	NPD7843	Approved
0.5924	Remote Similarity	NPD5535	Approved
0.5924	Remote Similarity	NPD3817	Phase 2
0.592	Remote Similarity	NPD7266	Discontinued
0.592	Remote Similarity	NPD1375	Discontinued
0.5916	Remote Similarity	NPD5096	Phase 3
0.5916	Remote Similarity	NPD7054	Approved
0.5916	Remote Similarity	NPD5095	Phase 3
0.5915	Remote Similarity	NPD2230	Approved
0.5915	Remote Similarity	NPD2235	Phase 2
0.5915	Remote Similarity	NPD2231	Phase 2
0.5915	Remote Similarity	NPD2232	Approved
0.5915	Remote Similarity	NPD2233	Approved
0.5915	Remote Similarity	NPD2981	Phase 2
0.5912	Remote Similarity	NPD3226	Approved
0.5912	Remote Similarity	NPD9685	Approved
0.5909	Remote Similarity	NPD3750	Approved
0.5906	Remote Similarity	NPD6355	Discontinued
0.5906	Remote Similarity	NPD447	Suspended
0.5904	Remote Similarity	NPD3051	Approved
0.5902	Remote Similarity	NPD37	Approved
0.5899	Remote Similarity	NPD1774	Approved
0.5896	Remote Similarity	NPD2154	Approved
0.5896	Remote Similarity	NPD2155	Approved
0.5896	Remote Similarity	NPD2156	Approved
0.5893	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5892	Remote Similarity	NPD4965	Approved
0.5892	Remote Similarity	NPD4966	Approved
0.5892	Remote Similarity	NPD4967	Phase 2
0.589	Remote Similarity	NPD3496	Discontinued
0.5886	Remote Similarity	NPD1398	Phase 1

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