NPASS Compound

Structure

CID136840 OpenBabel06191715492D 21 23 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 3.4641 -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 -1.7321 -2.0000 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 3.4641 1.0000 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 -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 -2.0000 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 -1.5000 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	3.027
LogD:	2.718
LogS:	-3.638
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	2.126
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.661
MDCK Permeability:	1.3462999049806967e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.099
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.249

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	95.49042510986328%
Volume Distribution (VD):	0.537
Pgp-substrate:	4.854471683502197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.879
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.558
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.764
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.879
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	6.718
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.071
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.525
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.179
Skin Sensitization:	0.544
Carcinogencity:	0.514
Eye Corrosion:	0.004
Eye Irritation:	0.904
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC136840

Natural Product ID:	NPC136840
*Common Name:**	4',7-Dihydroxy-3-Methoxyflavone
IUPAC Name:	7-hydroxy-2-(4-hydroxyphenyl)-3-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	BKGQDASNGPWTDI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-16-14(19)12-7-6-11(18)8-13(12)21-15(16)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
SMILES:	COc1c(oc2c(c1=O)ccc(c2)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL351942
PubChem CID:	14804705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002588] 3-O-methylated flavonoids

*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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	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
Others	10

Activity Type	# Activity
Cell Line	2
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CyD50	=	15.0	ug ml-1	PMID[458266]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[458267]
NPT1048	Organism	Poliovirus	Human enterovirus C	Max non-toxic dose	=	5.0	ug ml-1	PMID[458266]
NPT1048	Organism	Poliovirus	Human enterovirus C	Reduction factor	=	100000.0	n.a.	PMID[458266]
NPT1048	Organism	Poliovirus	Human enterovirus C	Minimal dose	=	4.0	ug ml-1	PMID[458266]
NPT1048	Organism	Poliovirus	Human enterovirus C	ED99	=	1.0	ug ml-1	PMID[458266]
NPT1538	Organism	Human rhinovirus sp.	Human rhinovirus sp.	CyD50	=	25.0	ug ml-1	PMID[458266]
NPT1538	Organism	Human rhinovirus sp.	Human rhinovirus sp.	ED99	=	25.0	ug ml-1	PMID[458266]
NPT27	Others	Unspecified		Therapeutic index 99	=	15.0	n.a.	PMID[458266]
NPT27	Others	Unspecified		Therapeutic index 99	=	1.0	n.a.	PMID[458266]

☑ 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 NPC136840 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	480
0.1-0.2	2020
0.2-0.3	5337
0.3-0.4	11409
0.4-0.5	5724
0.5-0.6	4410
0.6-0.7	5608
0.7-0.8	3889
0.8-0.85	2151
0.85-0.9	1243
0.9-0.95	388
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
0.9926	High Similarity	NPC230285
0.9926	High Similarity	NPC184536
0.9926	High Similarity	NPC146679
0.9926	High Similarity	NPC269652
0.9926	High Similarity	NPC59951
0.9926	High Similarity	NPC103342
0.9926	High Similarity	NPC281207
0.9926	High Similarity	NPC103904
0.9853	High Similarity	NPC90582
0.9853	High Similarity	NPC262094
0.9852	High Similarity	NPC143799
0.9852	High Similarity	NPC241838
0.9852	High Similarity	NPC152042
0.971	High Similarity	NPC470216
0.9704	High Similarity	NPC266597
0.9704	High Similarity	NPC250266
0.9704	High Similarity	NPC299379
0.9632	High Similarity	NPC276905
0.963	High Similarity	NPC473887
0.963	High Similarity	NPC29353
0.963	High Similarity	NPC124784
0.963	High Similarity	NPC47815
0.963	High Similarity	NPC127447
0.963	High Similarity	NPC216361
0.963	High Similarity	NPC256042
0.963	High Similarity	NPC281917
0.963	High Similarity	NPC194281
0.963	High Similarity	NPC116775
0.963	High Similarity	NPC231772
0.963	High Similarity	NPC234133
0.963	High Similarity	NPC187432
0.9571	High Similarity	NPC306488
0.9571	High Similarity	NPC5820
0.9571	High Similarity	NPC178343
0.9568	High Similarity	NPC158874
0.95	High Similarity	NPC216538
0.95	High Similarity	NPC273538
0.9496	High Similarity	NPC200694
0.9496	High Similarity	NPC473042
0.9489	High Similarity	NPC99333
0.9489	High Similarity	NPC280284
0.9489	High Similarity	NPC188947
0.9485	High Similarity	NPC61546
0.9485	High Similarity	NPC13408
0.9485	High Similarity	NPC72452
0.9481	High Similarity	NPC248872
0.9481	High Similarity	NPC172262
0.9433	High Similarity	NPC470458
0.9433	High Similarity	NPC124729
0.9433	High Similarity	NPC153758
0.9429	High Similarity	NPC293053
0.9429	High Similarity	NPC212932
0.9429	High Similarity	NPC9117
0.9429	High Similarity	NPC190637
0.9429	High Similarity	NPC24821
0.9424	High Similarity	NPC110969
0.942	High Similarity	NPC78913
0.942	High Similarity	NPC18260
0.9416	High Similarity	NPC228661
0.9416	High Similarity	NPC254841
0.9416	High Similarity	NPC290291
0.9416	High Similarity	NPC275055
0.9416	High Similarity	NPC188879
0.9407	High Similarity	NPC274121
0.9407	High Similarity	NPC213216
0.9407	High Similarity	NPC50898
0.9407	High Similarity	NPC78540
0.9407	High Similarity	NPC57601
0.9375	High Similarity	NPC260895
0.9371	High Similarity	NPC470461
0.9366	High Similarity	NPC259632
0.9362	High Similarity	NPC326500
0.9362	High Similarity	NPC71210
0.9357	High Similarity	NPC11561
0.9357	High Similarity	NPC226636
0.9353	High Similarity	NPC172986
0.9353	High Similarity	NPC261227
0.9353	High Similarity	NPC159275
0.9353	High Similarity	NPC270883
0.9353	High Similarity	NPC241100
0.9348	High Similarity	NPC201395
0.9348	High Similarity	NPC124269
0.9343	High Similarity	NPC240593
0.9333	High Similarity	NPC129132
0.9333	High Similarity	NPC128216
0.9333	High Similarity	NPC87231
0.9333	High Similarity	NPC257756
0.9333	High Similarity	NPC212631
0.9333	High Similarity	NPC205468
0.9306	High Similarity	NPC61258
0.9306	High Similarity	NPC188871
0.9306	High Similarity	NPC149127
0.9306	High Similarity	NPC286342
0.9301	High Similarity	NPC244407
0.9301	High Similarity	NPC470460
0.9301	High Similarity	NPC296869
0.9296	High Similarity	NPC229190
0.9286	High Similarity	NPC282300
0.9286	High Similarity	NPC147688
0.9286	High Similarity	NPC64908
0.9286	High Similarity	NPC3188
0.9286	High Similarity	NPC103362
0.9286	High Similarity	NPC205006
0.9286	High Similarity	NPC156590
0.9286	High Similarity	NPC118840
0.9281	High Similarity	NPC220062
0.9281	High Similarity	NPC150648
0.9281	High Similarity	NPC329203
0.9281	High Similarity	NPC55018
0.9281	High Similarity	NPC222342
0.9281	High Similarity	NPC225153
0.9281	High Similarity	NPC265871
0.9281	High Similarity	NPC310135
0.9281	High Similarity	NPC53181
0.9281	High Similarity	NPC217186
0.9281	High Similarity	NPC274784
0.9281	High Similarity	NPC301217
0.9281	High Similarity	NPC303633
0.9281	High Similarity	NPC96565
0.9281	High Similarity	NPC216978
0.9281	High Similarity	NPC49242
0.9281	High Similarity	NPC20709
0.9281	High Similarity	NPC261234
0.9275	High Similarity	NPC7013
0.9275	High Similarity	NPC303644
0.9275	High Similarity	NPC162680
0.9275	High Similarity	NPC181124
0.9275	High Similarity	NPC209560
0.9275	High Similarity	NPC294409
0.9275	High Similarity	NPC116632
0.927	High Similarity	NPC9985
0.927	High Similarity	NPC239495
0.9265	High Similarity	NPC312318
0.9265	High Similarity	NPC192304
0.9265	High Similarity	NPC472365
0.9265	High Similarity	NPC188646
0.9265	High Similarity	NPC337373
0.9265	High Similarity	NPC242294
0.9265	High Similarity	NPC56031
0.9265	High Similarity	NPC175098
0.9265	High Similarity	NPC263670
0.9265	High Similarity	NPC139813
0.9259	High Similarity	NPC308037
0.9259	High Similarity	NPC64359
0.9259	High Similarity	NPC284424
0.9259	High Similarity	NPC31872
0.9259	High Similarity	NPC473584
0.9259	High Similarity	NPC278556
0.9259	High Similarity	NPC262359
0.9259	High Similarity	NPC113006
0.9259	High Similarity	NPC475589
0.9241	High Similarity	NPC236769
0.9236	High Similarity	NPC159103
0.9236	High Similarity	NPC477941
0.9236	High Similarity	NPC270465
0.9236	High Similarity	NPC87125
0.9231	High Similarity	NPC122828
0.9231	High Similarity	NPC166757
0.9231	High Similarity	NPC211466
0.9231	High Similarity	NPC476182
0.9231	High Similarity	NPC472918
0.9231	High Similarity	NPC44721
0.9231	High Similarity	NPC40086
0.9231	High Similarity	NPC176869
0.9231	High Similarity	NPC3779
0.9231	High Similarity	NPC14001
0.9225	High Similarity	NPC234629
0.9225	High Similarity	NPC184649
0.9225	High Similarity	NPC303185
0.9225	High Similarity	NPC311741
0.922	High Similarity	NPC471520
0.922	High Similarity	NPC202981
0.9214	High Similarity	NPC305355
0.9214	High Similarity	NPC129853
0.9214	High Similarity	NPC188243
0.9214	High Similarity	NPC6407
0.9214	High Similarity	NPC69769
0.9214	High Similarity	NPC475680
0.9214	High Similarity	NPC235239
0.9214	High Similarity	NPC150522
0.9214	High Similarity	NPC76445
0.9214	High Similarity	NPC284550
0.9214	High Similarity	NPC110228
0.9209	High Similarity	NPC472460
0.9209	High Similarity	NPC12175
0.9209	High Similarity	NPC309154
0.9209	High Similarity	NPC278323
0.9209	High Similarity	NPC55162
0.9209	High Similarity	NPC279668
0.9209	High Similarity	NPC329225
0.9209	High Similarity	NPC90665
0.9209	High Similarity	NPC147686
0.9209	High Similarity	NPC25427
0.9209	High Similarity	NPC118813
0.9203	High Similarity	NPC121243
0.9203	High Similarity	NPC240147
0.9197	High Similarity	NPC286336
0.9191	High Similarity	NPC101294
0.9191	High Similarity	NPC25937
0.9191	High Similarity	NPC473655

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 NPC136840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	452
0.1-0.2	1001
0.2-0.3	1743
0.3-0.4	2703
0.4-0.5	1767
0.5-0.6	1004
0.6-0.7	327
0.7-0.8	91
0.8-0.85	41
0.85-0.9	14
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.95	High Similarity	NPD4378	Clinical (unspecified phase)
0.9209	High Similarity	NPD1549	Phase 2
0.9137	High Similarity	NPD1552	Clinical (unspecified phase)
0.9137	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1510	Phase 2
0.9118	High Similarity	NPD1240	Approved
0.9028	High Similarity	NPD1512	Approved
0.9021	High Similarity	NPD6799	Approved
0.8986	High Similarity	NPD1607	Approved
0.8958	High Similarity	NPD7410	Clinical (unspecified phase)
0.8929	High Similarity	NPD2796	Approved
0.8889	High Similarity	NPD1511	Approved
0.8808	High Similarity	NPD7075	Discontinued
0.8792	High Similarity	NPD6801	Discontinued
0.8742	High Similarity	NPD3882	Suspended
0.8733	High Similarity	NPD2801	Approved
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD3817	Phase 2
0.8667	High Similarity	NPD1934	Approved
0.8658	High Similarity	NPD6599	Discontinued
0.8658	High Similarity	NPD4380	Phase 2
0.8609	High Similarity	NPD2393	Clinical (unspecified phase)
0.86	High Similarity	NPD7411	Suspended
0.8581	High Similarity	NPD5403	Approved
0.8571	High Similarity	NPD5401	Approved
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8552	High Similarity	NPD3750	Approved
0.8431	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1551	Phase 2
0.8366	Intermediate Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6797	Phase 2
0.8312	Intermediate Similarity	NPD5402	Approved
0.8298	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7251	Discontinued
0.8231	Intermediate Similarity	NPD2800	Approved
0.8231	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7808	Phase 3
0.8207	Intermediate Similarity	NPD3748	Approved
0.8205	Intermediate Similarity	NPD3749	Approved
0.8201	Intermediate Similarity	NPD1203	Approved
0.8176	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7768	Phase 2
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1243	Approved
0.8095	Intermediate Similarity	NPD2344	Approved
0.8092	Intermediate Similarity	NPD920	Approved
0.8086	Intermediate Similarity	NPD7054	Approved
0.805	Intermediate Similarity	NPD6959	Discontinued
0.8042	Intermediate Similarity	NPD2313	Discontinued
0.8037	Intermediate Similarity	NPD7472	Approved
0.8027	Intermediate Similarity	NPD2935	Discontinued
0.8015	Intermediate Similarity	NPD1548	Phase 1
0.7986	Intermediate Similarity	NPD9717	Approved
0.7961	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6651	Approved
0.7937	Intermediate Similarity	NPD1247	Approved
0.7927	Intermediate Similarity	NPD7074	Phase 3
0.7925	Intermediate Similarity	NPD919	Approved
0.7914	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD422	Phase 1
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6832	Phase 2
0.7881	Intermediate Similarity	NPD2309	Approved
0.7875	Intermediate Similarity	NPD5494	Approved
0.7866	Intermediate Similarity	NPD7286	Phase 2
0.7838	Intermediate Similarity	NPD2799	Discontinued
0.7808	Intermediate Similarity	NPD943	Approved
0.7793	Intermediate Similarity	NPD3268	Approved
0.7784	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7762	Intermediate Similarity	NPD2798	Approved
0.7756	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD3225	Approved
0.7744	Intermediate Similarity	NPD7473	Discontinued
0.773	Intermediate Similarity	NPD3926	Phase 2
0.7727	Intermediate Similarity	NPD2534	Approved
0.7727	Intermediate Similarity	NPD2532	Approved
0.7727	Intermediate Similarity	NPD2533	Approved
0.7725	Intermediate Similarity	NPD6559	Discontinued
0.7718	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7033	Discontinued
0.7718	Intermediate Similarity	NPD4308	Phase 3
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD2797	Approved
0.7667	Intermediate Similarity	NPD6100	Approved
0.7667	Intermediate Similarity	NPD6099	Approved
0.7665	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7657	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4908	Phase 1
0.7635	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1933	Approved
0.7632	Intermediate Similarity	NPD2654	Approved
0.7626	Intermediate Similarity	NPD9545	Approved
0.7616	Intermediate Similarity	NPD2346	Discontinued
0.7609	Intermediate Similarity	NPD9493	Approved
0.76	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3751	Discontinued
0.7576	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3267	Approved
0.7569	Intermediate Similarity	NPD3266	Approved
0.7562	Intermediate Similarity	NPD1465	Phase 2
0.7551	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6798	Discontinued
0.7545	Intermediate Similarity	NPD5844	Phase 1
0.7532	Intermediate Similarity	NPD2354	Approved
0.7518	Intermediate Similarity	NPD1241	Discontinued
0.7517	Intermediate Similarity	NPD1019	Discontinued
0.7517	Intermediate Similarity	NPD447	Suspended
0.7517	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD6233	Phase 2
0.75	Intermediate Similarity	NPD1471	Phase 3
0.7483	Intermediate Similarity	NPD3972	Approved
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4307	Phase 2
0.7443	Intermediate Similarity	NPD4360	Phase 2
0.7443	Intermediate Similarity	NPD4363	Phase 3
0.7436	Intermediate Similarity	NPD7390	Discontinued
0.7432	Intermediate Similarity	NPD1296	Phase 2
0.7432	Intermediate Similarity	NPD411	Approved
0.7415	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2353	Approved
0.7365	Intermediate Similarity	NPD2403	Approved
0.7361	Intermediate Similarity	NPD1608	Approved
0.7361	Intermediate Similarity	NPD1481	Phase 2
0.7349	Intermediate Similarity	NPD3787	Discontinued
0.7347	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.733	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD3887	Approved
0.7303	Intermediate Similarity	NPD4361	Phase 2
0.7303	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2296	Approved
0.7294	Intermediate Similarity	NPD1729	Discontinued
0.7292	Intermediate Similarity	NPD1535	Discovery
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD5124	Phase 1
0.7285	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6844	Discontinued
0.7233	Intermediate Similarity	NPD5049	Phase 3
0.7216	Intermediate Similarity	NPD4287	Approved
0.7211	Intermediate Similarity	NPD1470	Approved
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.7202	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6190	Approved
0.7181	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1652	Phase 2
0.7172	Intermediate Similarity	NPD1201	Approved
0.7171	Intermediate Similarity	NPD4340	Discontinued
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD17	Approved
0.7152	Intermediate Similarity	NPD7440	Discontinued
0.7152	Intermediate Similarity	NPD4062	Phase 3
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7133	Intermediate Similarity	NPD1894	Discontinued
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7117	Intermediate Similarity	NPD5889	Approved
0.7117	Intermediate Similarity	NPD5890	Approved
0.7108	Intermediate Similarity	NPD6971	Discontinued
0.7107	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3140	Approved
0.7105	Intermediate Similarity	NPD3142	Approved
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7099	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD7584	Approved
0.7095	Intermediate Similarity	NPD1164	Approved
0.7076	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4749	Approved
0.7063	Intermediate Similarity	NPD4661	Approved
0.7063	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD6585	Discontinued
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7229	Phase 3
0.7029	Intermediate Similarity	NPD9266	Approved
0.7029	Intermediate Similarity	NPD74	Approved
0.7025	Intermediate Similarity	NPD7003	Approved
0.702	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD9494	Approved
0.7	Intermediate Similarity	NPD7212	Phase 2
0.7	Intermediate Similarity	NPD2861	Phase 2
0.7	Intermediate Similarity	NPD7213	Phase 3
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)

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