NPASS Compound

Structure

CID122467 OpenBabel06191715472D 53 58 0 0 1 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 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 -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 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 1 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 -0.8660 -4.5000 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 -4.3301 0.5000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 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 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 2 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 3.4641 0.0000 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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -2.5000 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 -1.7321 -0.0000 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 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 16 2 0 0 0 0 8 47 1 0 0 0 0 9 1 1 6 0 0 0 9 19 1 0 0 0 0 9 48 1 0 0 0 0 10 2 1 6 0 0 0 10 20 1 0 0 0 0 10 49 1 0 0 0 0 11 28 1 0 0 0 0 12 34 1 0 0 0 0 13 14 2 0 0 0 0 13 35 1 0 0 0 0 14 36 1 0 0 0 0 15 18 2 0 0 0 0 15 37 1 0 0 0 0 16 18 1 0 0 0 0 16 50 1 0 0 0 0 17 8 1 1 0 0 0 17 21 1 0 0 0 0 17 51 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 38 1 1 0 0 0 20 24 1 0 0 0 0 20 39 1 1 0 0 0 21 25 1 0 0 0 0 21 40 1 1 0 0 0 22 29 1 0 0 0 0 22 41 2 0 0 0 0 23 26 1 0 0 0 0 23 42 1 6 0 0 0 24 27 1 0 0 0 0 24 43 1 6 0 0 0 25 30 1 0 0 0 0 25 44 1 1 0 0 0 26 31 1 0 0 0 0 26 45 1 6 0 0 0 27 32 1 0 0 0 0 27 46 1 6 0 0 0 28 29 2 0 0 0 0 28 50 1 0 0 0 0 29 52 1 0 0 0 0 30 33 1 0 0 0 0 30 53 1 6 0 0 0 31 47 1 1 0 0 0 31 48 1 0 0 0 0 32 49 1 0 0 0 0 32 53 1 1 0 0 0 33 51 1 0 0 0 0 33 52 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	756.21
Volume:	682.698
LogP:	-0.149
LogD:	-0.293
LogS:	-3.531
# Rotatable Bonds:	8
TPSA:	328.35
# H-Bond Aceptor:	20
# H-Bond Donor:	12
# Rings:	6
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.103
Synthetic Accessibility Score:	5.398
Fsp3:	0.545
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.523
MDCK Permeability:	4.148770676692948e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.961
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	82.68636322021484%
Volume Distribution (VD):	0.618
Pgp-substrate:	21.704076766967773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.684
Half-life (T1/2):	0.638

ADMET: Toxicity

hERG Blockers:	0.213
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.822
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.947
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.318
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC122467

Natural Product ID:	NPC122467
*Common Name:**	Alcesefoliside
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,7-dihydroxychromen-4-one
Synonyms:
Standard InCHIKey:	HKNBJSRIYRDSLB-MIORVHIISA-N
Standard InCHI:	InChI=1S/C33H40O20/c1-9-19(38)23(42)26(45)31(48-9)47-8-17-21(40)25(44)30(53-32-27(46)24(43)20(39)10(2)49-32)33(51-17)52-29-22(41)18-15(37)6-12(34)7-16(18)50-28(29)11-3-4-13(35)14(36)5-11/h3-7,9-10,17,19-21,23-27,30-40,42-46H,8H2,1-2H3/t9-,10-,17+,19-,20-,21-,23+,24+,25-,26+,27+,30+,31+,32-,33-/m0/s1
SMILES:	Oc1cc(O)c2c(c1)oc(c(c2=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444468
PubChem CID:	11828754
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252914]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19251412]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO11296	Arthrinium arundinis	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25626143]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO40038	Astragalus monspessulanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26558405]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO22524	Ranunculus sceleratus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22524	Ranunculus sceleratus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22409	Cyanostegia microphylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3369	Anemone narcissiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20567	Montipora mollis	Species	Acroporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2175	Hyperbaena columbica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16652	Centipeda cunninghami	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22006	Maytenus aquifolium	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8349	Uga sinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11296	Arthrinium arundinis	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20702	Discodermia dissoluta	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2217	Valeriana wolgensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26375	Viburnum grandifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1118	Elymus repens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22524	Ranunculus sceleratus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22806	Euphorbia leuconeura	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22409	Cyanostegia microphylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13457	Acacia pachyphloia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19626	Lavandula dentata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21358	Pyrus ussuriensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22593	Graphis rikuzensis	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9876	Isocoma pluriflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT984	Cell Line	Hepatocyte		Activity	=	195.0	%	PMID[448529]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[448528]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	Inhibition	=	40.0	%	PMID[448528]

☑ 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 NPC122467 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	476
0.1-0.2	1818
0.2-0.3	4119
0.3-0.4	9503
0.4-0.5	8326
0.5-0.6	5219
0.6-0.7	5822
0.7-0.8	5018
0.8-0.85	1399
0.85-0.9	492
0.9-0.95	418
0.95-1	87

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202908
1.0	High Similarity	NPC292019
1.0	High Similarity	NPC14187
0.9939	High Similarity	NPC89052
0.9939	High Similarity	NPC251417
0.9879	High Similarity	NPC192539
0.9878	High Similarity	NPC48984
0.9878	High Similarity	NPC219043
0.9817	High Similarity	NPC16194
0.9817	High Similarity	NPC476472
0.9817	High Similarity	NPC473327
0.9817	High Similarity	NPC220173
0.9817	High Similarity	NPC294815
0.9817	High Similarity	NPC19108
0.9816	High Similarity	NPC471725
0.9816	High Similarity	NPC203259
0.9816	High Similarity	NPC134532
0.9816	High Similarity	NPC176740
0.9816	High Similarity	NPC33054
0.9816	High Similarity	NPC155877
0.9816	High Similarity	NPC471748
0.9758	High Similarity	NPC473862
0.9758	High Similarity	NPC471669
0.9758	High Similarity	NPC89127
0.9755	High Similarity	NPC29958
0.9755	High Similarity	NPC67105
0.9755	High Similarity	NPC259896
0.9755	High Similarity	NPC136042
0.9755	High Similarity	NPC67326
0.9755	High Similarity	NPC156869
0.9755	High Similarity	NPC254855
0.9755	High Similarity	NPC255157
0.9755	High Similarity	NPC95866
0.9702	High Similarity	NPC275977
0.9702	High Similarity	NPC249560
0.9702	High Similarity	NPC223860
0.9699	High Similarity	NPC173837
0.9697	High Similarity	NPC198199
0.9695	High Similarity	NPC26230
0.9695	High Similarity	NPC180918
0.9695	High Similarity	NPC60735
0.9693	High Similarity	NPC227508
0.9645	High Similarity	NPC295625
0.9645	High Similarity	NPC470719
0.9645	High Similarity	NPC33083
0.9645	High Similarity	NPC473554
0.9643	High Similarity	NPC162394
0.9643	High Similarity	NPC241781
0.9643	High Similarity	NPC156785
0.9641	High Similarity	NPC110941
0.9641	High Similarity	NPC470443
0.9641	High Similarity	NPC126784
0.9641	High Similarity	NPC473682
0.9641	High Similarity	NPC473571
0.9641	High Similarity	NPC241423
0.9641	High Similarity	NPC470444
0.9639	High Similarity	NPC65563
0.9639	High Similarity	NPC470949
0.9634	High Similarity	NPC285197
0.9632	High Similarity	NPC275454
0.9632	High Similarity	NPC52550
0.9632	High Similarity	NPC84362
0.9632	High Similarity	NPC223424
0.9632	High Similarity	NPC317489
0.9632	High Similarity	NPC173637
0.9632	High Similarity	NPC127546
0.9588	High Similarity	NPC30011
0.9588	High Similarity	NPC72554
0.9588	High Similarity	NPC97817
0.9586	High Similarity	NPC470720
0.9586	High Similarity	NPC470713
0.9586	High Similarity	NPC470717
0.9586	High Similarity	NPC460984
0.9586	High Similarity	NPC25946
0.9586	High Similarity	NPC470455
0.9586	High Similarity	NPC21359
0.9586	High Similarity	NPC470451
0.9581	High Similarity	NPC120952
0.9578	High Similarity	NPC294629
0.9578	High Similarity	NPC253685
0.9573	High Similarity	NPC120099
0.9573	High Similarity	NPC105283
0.9573	High Similarity	NPC219904
0.9573	High Similarity	NPC195257
0.9573	High Similarity	NPC270578
0.9573	High Similarity	NPC86008
0.9573	High Similarity	NPC209296
0.9573	High Similarity	NPC52382
0.9573	High Similarity	NPC203050
0.9573	High Similarity	NPC43587
0.9573	High Similarity	NPC225434
0.9573	High Similarity	NPC223747
0.9571	High Similarity	NPC308404
0.9571	High Similarity	NPC476470
0.9571	High Similarity	NPC189564
0.9571	High Similarity	NPC113968
0.9571	High Similarity	NPC135599
0.9571	High Similarity	NPC32641
0.9571	High Similarity	NPC256188
0.9571	High Similarity	NPC142142
0.9571	High Similarity	NPC210073
0.9571	High Similarity	NPC73855
0.9571	High Similarity	NPC274618
0.9571	High Similarity	NPC145038
0.9571	High Similarity	NPC88789
0.9571	High Similarity	NPC118284
0.9571	High Similarity	NPC281131
0.9571	High Similarity	NPC8856
0.9571	High Similarity	NPC56077
0.9571	High Similarity	NPC203145
0.9571	High Similarity	NPC115674
0.9571	High Similarity	NPC11432
0.9571	High Similarity	NPC277174
0.9571	High Similarity	NPC12013
0.9571	High Similarity	NPC276222
0.9571	High Similarity	NPC221342
0.9571	High Similarity	NPC179950
0.9571	High Similarity	NPC477613
0.9571	High Similarity	NPC253662
0.9571	High Similarity	NPC328940
0.9571	High Similarity	NPC186816
0.9527	High Similarity	NPC470449
0.9527	High Similarity	NPC470447
0.9527	High Similarity	NPC470718
0.9527	High Similarity	NPC470446
0.9527	High Similarity	NPC473072
0.9527	High Similarity	NPC470445
0.9521	High Similarity	NPC8573
0.9521	High Similarity	NPC169733
0.9521	High Similarity	NPC255799
0.9518	High Similarity	NPC25724
0.9515	High Similarity	NPC79056
0.9515	High Similarity	NPC244776
0.9515	High Similarity	NPC105095
0.9515	High Similarity	NPC44328
0.9515	High Similarity	NPC116864
0.9515	High Similarity	NPC206123
0.9515	High Similarity	NPC177731
0.9512	High Similarity	NPC265530
0.9512	High Similarity	NPC325555
0.9512	High Similarity	NPC226304
0.9512	High Similarity	NPC160156
0.9512	High Similarity	NPC92565
0.9509	High Similarity	NPC277205
0.9509	High Similarity	NPC289667
0.9509	High Similarity	NPC55786
0.9509	High Similarity	NPC19388
0.9509	High Similarity	NPC135358
0.9509	High Similarity	NPC76831
0.9509	High Similarity	NPC287889
0.9509	High Similarity	NPC292929
0.9509	High Similarity	NPC240431
0.9474	High Similarity	NPC64755
0.9471	High Similarity	NPC148710
0.9467	High Similarity	NPC473071
0.9467	High Similarity	NPC473073
0.9458	High Similarity	NPC245452
0.9458	High Similarity	NPC175107
0.9458	High Similarity	NPC190003
0.9458	High Similarity	NPC153755
0.9455	High Similarity	NPC293629
0.9451	High Similarity	NPC197285
0.9451	High Similarity	NPC21100
0.9448	High Similarity	NPC19709
0.9415	High Similarity	NPC104910
0.9415	High Similarity	NPC474093
0.9401	High Similarity	NPC24043
0.9401	High Similarity	NPC21666
0.9401	High Similarity	NPC208668
0.9401	High Similarity	NPC204693
0.9401	High Similarity	NPC169977
0.9401	High Similarity	NPC4390
0.9401	High Similarity	NPC45522
0.9401	High Similarity	NPC101026
0.9401	High Similarity	NPC42773
0.9398	High Similarity	NPC235260
0.9398	High Similarity	NPC218488
0.9398	High Similarity	NPC78734
0.9398	High Similarity	NPC231194
0.9398	High Similarity	NPC155763
0.9398	High Similarity	NPC20505
0.9398	High Similarity	NPC51326
0.9398	High Similarity	NPC150767
0.939	High Similarity	NPC475366
0.939	High Similarity	NPC22832
0.939	High Similarity	NPC284277
0.939	High Similarity	NPC15358
0.939	High Similarity	NPC311830
0.939	High Similarity	NPC475497
0.9387	High Similarity	NPC473043
0.9387	High Similarity	NPC244875
0.9387	High Similarity	NPC77660
0.9387	High Similarity	NPC240306
0.9387	High Similarity	NPC189142
0.9387	High Similarity	NPC475382
0.936	High Similarity	NPC475179
0.9349	High Similarity	NPC267680
0.9349	High Similarity	NPC293626
0.9349	High Similarity	NPC113836
0.9349	High Similarity	NPC217387

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 NPC122467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	960
0.2-0.3	2077
0.3-0.4	2716
0.4-0.5	1794
0.5-0.6	804
0.6-0.7	256
0.7-0.8	93
0.8-0.85	21
0.85-0.9	5
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9877	High Similarity	NPD7251	Discontinued
0.9817	High Similarity	NPD7808	Phase 3
0.9816	High Similarity	NPD6797	Phase 2
0.9634	High Similarity	NPD7472	Approved
0.9573	High Similarity	NPD7054	Approved
0.9515	High Similarity	NPD7074	Phase 3
0.9337	High Similarity	NPD7804	Clinical (unspecified phase)
0.9231	High Similarity	NPD4338	Clinical (unspecified phase)
0.9042	High Similarity	NPD6168	Clinical (unspecified phase)
0.9042	High Similarity	NPD6166	Phase 2
0.9042	High Similarity	NPD6167	Clinical (unspecified phase)
0.8935	High Similarity	NPD3818	Discontinued
0.8909	High Similarity	NPD4381	Clinical (unspecified phase)
0.8675	High Similarity	NPD3817	Phase 2
0.8667	High Similarity	NPD1934	Approved
0.8614	High Similarity	NPD2393	Clinical (unspecified phase)
0.8563	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD1512	Approved
0.8512	High Similarity	NPD3882	Suspended
0.8503	High Similarity	NPD2801	Approved
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8405	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8294	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5402	Approved
0.8225	Intermediate Similarity	NPD6801	Discontinued
0.8202	Intermediate Similarity	NPD6559	Discontinued
0.8197	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5403	Approved
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6799	Approved
0.8024	Intermediate Similarity	NPD5401	Approved
0.8023	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD8313	Approved
0.8011	Intermediate Similarity	NPD8312	Approved
0.7978	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD7819	Suspended
0.7955	Intermediate Similarity	NPD3787	Discontinued
0.7943	Intermediate Similarity	NPD5494	Approved
0.7927	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7685	Pre-registration
0.7898	Intermediate Similarity	NPD6959	Discontinued
0.7882	Intermediate Similarity	NPD1653	Approved
0.7879	Intermediate Similarity	NPD1549	Phase 2
0.7877	Intermediate Similarity	NPD7228	Approved
0.7791	Intermediate Similarity	NPD6599	Discontinued
0.7759	Intermediate Similarity	NPD1465	Phase 2
0.7759	Intermediate Similarity	NPD8455	Phase 2
0.7758	Intermediate Similarity	NPD2796	Approved
0.7755	Intermediate Similarity	NPD8151	Discontinued
0.7746	Intermediate Similarity	NPD7411	Suspended
0.7735	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7473	Discontinued
0.7711	Intermediate Similarity	NPD7266	Discontinued
0.7709	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.768	Intermediate Similarity	NPD7435	Discontinued
0.768	Intermediate Similarity	NPD7698	Approved
0.768	Intermediate Similarity	NPD7696	Phase 3
0.768	Intermediate Similarity	NPD7697	Approved
0.7667	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7617	Intermediate Similarity	NPD6776	Approved
0.7617	Intermediate Similarity	NPD6781	Approved
0.7617	Intermediate Similarity	NPD6779	Approved
0.7617	Intermediate Similarity	NPD6780	Approved
0.7617	Intermediate Similarity	NPD6782	Approved
0.7617	Intermediate Similarity	NPD6778	Approved
0.7617	Intermediate Similarity	NPD6777	Approved
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7701	Phase 2
0.7598	Intermediate Similarity	NPD7199	Phase 2
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD919	Approved
0.7563	Intermediate Similarity	NPD7584	Approved
0.7561	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1613	Approved
0.7552	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8320	Phase 1
0.7551	Intermediate Similarity	NPD7870	Phase 2
0.7551	Intermediate Similarity	NPD8319	Approved
0.7551	Intermediate Similarity	NPD7871	Phase 2
0.7538	Intermediate Similarity	NPD7874	Approved
0.7538	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6190	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.7513	Intermediate Similarity	NPD7699	Phase 2
0.7513	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD1247	Approved
0.7486	Intermediate Similarity	NPD6234	Discontinued
0.7472	Intermediate Similarity	NPD7768	Phase 2
0.7471	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1240	Approved
0.7418	Intermediate Similarity	NPD3926	Phase 2
0.7413	Intermediate Similarity	NPD7801	Approved
0.7401	Intermediate Similarity	NPD37	Approved
0.7374	Intermediate Similarity	NPD4965	Approved
0.7374	Intermediate Similarity	NPD4966	Approved
0.7374	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD1607	Approved
0.7358	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD6534	Approved
0.7349	Intermediate Similarity	NPD943	Approved
0.7341	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD8434	Phase 2
0.7316	Intermediate Similarity	NPD8150	Discontinued
0.7305	Intermediate Similarity	NPD230	Phase 1
0.7305	Intermediate Similarity	NPD1933	Approved
0.7283	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3027	Phase 3
0.7273	Intermediate Similarity	NPD6823	Phase 2
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7256	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD3749	Approved
0.7235	Intermediate Similarity	NPD1551	Phase 2
0.7178	Intermediate Similarity	NPD7585	Approved
0.7177	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7680	Approved
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD2935	Discontinued
0.7129	Intermediate Similarity	NPD7583	Approved
0.7121	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD2533	Approved
0.7102	Intermediate Similarity	NPD2532	Approved
0.7102	Intermediate Similarity	NPD2534	Approved
0.7101	Intermediate Similarity	NPD447	Suspended
0.7085	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3748	Approved
0.7035	Intermediate Similarity	NPD6100	Approved
0.7035	Intermediate Similarity	NPD6099	Approved
0.7028	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6798	Discontinued
0.7022	Intermediate Similarity	NPD920	Approved
0.7017	Intermediate Similarity	NPD6844	Discontinued
0.7016	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2800	Approved
0.7011	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.7	Intermediate Similarity	NPD5953	Discontinued
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD1091	Approved
0.6984	Remote Similarity	NPD7286	Phase 2
0.6982	Remote Similarity	NPD6233	Phase 2
0.6977	Remote Similarity	NPD7033	Discontinued
0.6959	Remote Similarity	NPD6651	Approved
0.6954	Remote Similarity	NPD6213	Phase 3
0.6954	Remote Similarity	NPD6212	Phase 3
0.6954	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7390	Discontinued
0.6944	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD1243	Approved
0.691	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4908	Phase 1
0.6893	Remote Similarity	NPD643	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7930	Approved
0.6886	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5353	Approved
0.6845	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD9494	Approved
0.6829	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1203	Approved
0.6824	Remote Similarity	NPD2313	Discontinued
0.6824	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5124	Phase 1
0.6802	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2346	Discontinued
0.68	Remote Similarity	NPD2344	Approved
0.6788	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2799	Discontinued
0.6776	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8059	Phase 3
0.6758	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD2163	Approved
0.6751	Remote Similarity	NPD6841	Approved
0.6751	Remote Similarity	NPD6843	Phase 3
0.6751	Remote Similarity	NPD6842	Approved
0.6748	Remote Similarity	NPD1548	Phase 1
0.6744	Remote Similarity	NPD4060	Phase 1
0.6737	Remote Similarity	NPD2403	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data