NPASS Compound

Structure

CID29830 OpenBabel06191715352D 32 35 0 0 1 0 0 0 0 0999 V2000 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 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 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 1 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 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 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 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 10 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 15 2 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 22 1 0 0 0 0 9 30 1 0 0 0 0 10 11 2 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 26 2 0 0 0 0 14 8 1 6 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 7 1 6 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 30 1 6 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.12
Volume:	415.784
LogP:	0.353
LogD:	0.078
LogS:	-4.235
# Rotatable Bonds:	4
TPSA:	186.37
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	4.123
Fsp3:	0.381
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.546
MDCK Permeability:	1.2530628737295046e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.826
Human Intestinal Absorption (HIA):	0.304
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	88.9935073852539%
Volume Distribution (VD):	0.732
Pgp-substrate:	12.827070236206055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.067
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.239
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	9.455
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.71
Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.928
Carcinogencity:	0.734
Eye Corrosion:	0.003
Eye Irritation:	0.602
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC29830

Natural Product ID:	NPC29830
*Common Name:**	Eriodictyol-7-O-Glucoside
IUPAC Name:	(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	RAFHNDRXYHOLSH-SFTVRKLSSA-N
Standard InCHI:	InChI=1S/C21H22O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-5,14,16,18-25,27-29H,6-7H2/t14-,16+,18+,19-,20+,21+/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc3O[C@@H](CC(=O)c3c(c2)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509624
PubChem CID:	13254473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00231-5]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087602]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12377236]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932124]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	stem	n.a.	PMID[12932124]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19499937]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121165]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20932762]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8	Buphthalmum salicifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14062	Oophaga speciosa	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4578	Cystoseira fimbriata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3676	Fusarium sambucinum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27239	Maclura tinctoria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO539	Picea vulgaris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	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
NPO17752	NPC29830	n.a.	n.a.	80.25148	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

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

Biological Activity

Activity Type	# Activity
EC50	4
ED50	1
IC50	6
Others	4

Activity Type	# Activity
Cell Line	3
Individual Protein	2
NON-MOLECULAR	3
Others	2
SINGLE PROTEIN	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	41200.0	nM	PMID[560269]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	100.0	%	PMID[560269]
NPT1635	Cell Line	H9c2	Rattus norvegicus	EC50	=	38230.0	nM	PMID[560270]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	25.44	%	PMID[560271]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.263	mM	PMID[560267]
NPT1	Others	Radical scavenging activity		ED50	=	63.3	uM	PMID[560269]
NPT1	Others	Radical scavenging activity		EC50	=	15600.0	nM	PMID[560270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	212900000.0	nM	PMID[560270]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	7260.0	nM	PMID[560270]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-9.51	%	PMID[560271]
NPT21995	SINGLE PROTEIN	Synaptojanin-2	Homo sapiens	IC50	=	874.0	nM	PMID[560272]
NPT21994	SINGLE PROTEIN	Synaptojanin-1	Homo sapiens	IC50	<=	15900.0	nM	PMID[560272]
NPT21995	SINGLE PROTEIN	Synaptojanin-2	Homo sapiens	IC50	=	874.0	nM	PMID[560273]
NPT21994	SINGLE PROTEIN	Synaptojanin-1	Homo sapiens	IC50	<=	15900.0	nM	PMID[560273]
NPT21995	SINGLE PROTEIN	Synaptojanin-2	Homo sapiens	IC50	=	874.0	nM	PMID[560274]

☑ 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 NPC29830 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	420
0.1-0.2	1682
0.2-0.3	3893
0.3-0.4	9495
0.4-0.5	8706
0.5-0.6	3956
0.6-0.7	4887
0.7-0.8	5923
0.8-0.85	2434
0.85-0.9	988
0.9-0.95	275
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC5778
0.9872	High Similarity	NPC236934
0.9809	High Similarity	NPC92565
0.9809	High Similarity	NPC45400
0.9809	High Similarity	NPC160156
0.9806	High Similarity	NPC127782
0.9806	High Similarity	NPC300537
0.9806	High Similarity	NPC77660
0.9806	High Similarity	NPC189142
0.9747	High Similarity	NPC43587
0.9747	High Similarity	NPC112755
0.9747	High Similarity	NPC52382
0.9747	High Similarity	NPC229687
0.9747	High Similarity	NPC105283
0.9747	High Similarity	NPC170675
0.9747	High Similarity	NPC270578
0.9747	High Similarity	NPC471457
0.9745	High Similarity	NPC8856
0.9745	High Similarity	NPC115674
0.9745	High Similarity	NPC210073
0.9744	High Similarity	NPC270335
0.9744	High Similarity	NPC168822
0.9744	High Similarity	NPC19709
0.9744	High Similarity	NPC191306
0.9686	High Similarity	NPC51326
0.9686	High Similarity	NPC183357
0.9686	High Similarity	NPC105095
0.9686	High Similarity	NPC150767
0.9686	High Similarity	NPC44328
0.9686	High Similarity	NPC34287
0.9686	High Similarity	NPC21190
0.9686	High Similarity	NPC177731
0.9686	High Similarity	NPC218488
0.9686	High Similarity	NPC471416
0.9686	High Similarity	NPC79056
0.9686	High Similarity	NPC78734
0.9686	High Similarity	NPC22195
0.9686	High Similarity	NPC231194
0.9684	High Similarity	NPC229729
0.9684	High Similarity	NPC477502
0.9682	High Similarity	NPC277205
0.9682	High Similarity	NPC311830
0.9682	High Similarity	NPC165720
0.9682	High Similarity	NPC22832
0.9679	High Similarity	NPC473043
0.9625	High Similarity	NPC261254
0.9625	High Similarity	NPC301683
0.9625	High Similarity	NPC256760
0.9625	High Similarity	NPC47140
0.9625	High Similarity	NPC67134
0.9623	High Similarity	NPC195257
0.9623	High Similarity	NPC472383
0.9623	High Similarity	NPC86008
0.9623	High Similarity	NPC210042
0.9623	High Similarity	NPC95855
0.9623	High Similarity	NPC209296
0.9623	High Similarity	NPC293629
0.9623	High Similarity	NPC472381
0.962	High Similarity	NPC56077
0.962	High Similarity	NPC21100
0.962	High Similarity	NPC145038
0.962	High Similarity	NPC281131
0.962	High Similarity	NPC253662
0.962	High Similarity	NPC88789
0.962	High Similarity	NPC308404
0.962	High Similarity	NPC197285
0.962	High Similarity	NPC118284
0.962	High Similarity	NPC179950
0.962	High Similarity	NPC274618
0.962	High Similarity	NPC276222
0.9618	High Similarity	NPC88043
0.9618	High Similarity	NPC222936
0.9618	High Similarity	NPC88023
0.9618	High Similarity	NPC243930
0.9618	High Similarity	NPC284960
0.9618	High Similarity	NPC309025
0.9565	High Similarity	NPC239549
0.9565	High Similarity	NPC236191
0.9565	High Similarity	NPC208668
0.9565	High Similarity	NPC51774
0.9563	High Similarity	NPC255157
0.9563	High Similarity	NPC67105
0.9563	High Similarity	NPC474434
0.9563	High Similarity	NPC285197
0.9563	High Similarity	NPC254855
0.9563	High Similarity	NPC44558
0.9563	High Similarity	NPC67326
0.9563	High Similarity	NPC29958
0.9563	High Similarity	NPC156869
0.9563	High Similarity	NPC259896
0.9563	High Similarity	NPC136042
0.9563	High Similarity	NPC95866
0.956	High Similarity	NPC45618
0.956	High Similarity	NPC275454
0.956	High Similarity	NPC84362
0.956	High Similarity	NPC58716
0.956	High Similarity	NPC317489
0.956	High Similarity	NPC93099
0.956	High Similarity	NPC52550
0.956	High Similarity	NPC223424
0.956	High Similarity	NPC173637
0.956	High Similarity	NPC127546
0.956	High Similarity	NPC146792
0.9557	High Similarity	NPC240431
0.9557	High Similarity	NPC55786
0.9557	High Similarity	NPC19388
0.9545	High Similarity	NPC26195
0.9545	High Similarity	NPC39351
0.9545	High Similarity	NPC72649
0.9545	High Similarity	NPC97052
0.9545	High Similarity	NPC169248
0.9506	High Similarity	NPC294629
0.9503	High Similarity	NPC26230
0.9503	High Similarity	NPC307518
0.9503	High Similarity	NPC259152
0.9503	High Similarity	NPC33054
0.9503	High Similarity	NPC176740
0.9503	High Similarity	NPC471748
0.9503	High Similarity	NPC203259
0.9503	High Similarity	NPC472386
0.9503	High Similarity	NPC235575
0.9503	High Similarity	NPC180918
0.9503	High Similarity	NPC205076
0.9503	High Similarity	NPC155877
0.9503	High Similarity	NPC60735
0.9503	High Similarity	NPC48773
0.9503	High Similarity	NPC267254
0.9503	High Similarity	NPC3583
0.9503	High Similarity	NPC134532
0.9503	High Similarity	NPC471725
0.95	High Similarity	NPC186807
0.95	High Similarity	NPC223747
0.95	High Similarity	NPC183036
0.95	High Similarity	NPC225434
0.95	High Similarity	NPC45638
0.95	High Similarity	NPC227508
0.95	High Similarity	NPC475942
0.95	High Similarity	NPC93337
0.95	High Similarity	NPC120099
0.95	High Similarity	NPC203050
0.95	High Similarity	NPC58053
0.95	High Similarity	NPC201292
0.95	High Similarity	NPC219904
0.95	High Similarity	NPC469931
0.95	High Similarity	NPC226294
0.95	High Similarity	NPC105025
0.9497	High Similarity	NPC328940
0.9497	High Similarity	NPC113968
0.9497	High Similarity	NPC277174
0.9497	High Similarity	NPC73855
0.9497	High Similarity	NPC135599
0.949	High Similarity	NPC182045
0.9487	High Similarity	NPC308265
0.9484	High Similarity	NPC261866
0.9484	High Similarity	NPC206378
0.9484	High Similarity	NPC170475
0.9448	High Similarity	NPC268533
0.9444	High Similarity	NPC204693
0.9444	High Similarity	NPC25724
0.9441	High Similarity	NPC20505
0.9441	High Similarity	NPC206123
0.9441	High Similarity	NPC105511
0.9441	High Similarity	NPC155763
0.9441	High Similarity	NPC282987
0.9441	High Similarity	NPC245014
0.9441	High Similarity	NPC212748
0.9441	High Similarity	NPC244776
0.9441	High Similarity	NPC204937
0.9441	High Similarity	NPC224462
0.9441	High Similarity	NPC84265
0.9441	High Similarity	NPC116864
0.9441	High Similarity	NPC149011
0.9441	High Similarity	NPC235260
0.9437	High Similarity	NPC265530
0.9437	High Similarity	NPC149244
0.9437	High Similarity	NPC325555
0.9437	High Similarity	NPC226304
0.9437	High Similarity	NPC48640
0.9437	High Similarity	NPC116745
0.9434	High Similarity	NPC284277
0.9434	High Similarity	NPC475366
0.9434	High Similarity	NPC475497
0.9427	High Similarity	NPC472320
0.9427	High Similarity	NPC110349
0.9427	High Similarity	NPC271479
0.9423	High Similarity	NPC161749
0.9423	High Similarity	NPC197896
0.9423	High Similarity	NPC313163
0.9423	High Similarity	NPC258035
0.9423	High Similarity	NPC156457
0.9416	High Similarity	NPC121001
0.9416	High Similarity	NPC259182
0.939	High Similarity	NPC476620
0.939	High Similarity	NPC476621
0.939	High Similarity	NPC476619
0.939	High Similarity	NPC241196
0.939	High Similarity	NPC476622
0.939	High Similarity	NPC476618
0.939	High Similarity	NPC476623
0.9387	High Similarity	NPC294815

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 NPC29830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	896
0.2-0.3	1861
0.3-0.4	2662
0.4-0.5	1812
0.5-0.6	976
0.6-0.7	393
0.7-0.8	135
0.8-0.85	22
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9686	High Similarity	NPD7074	Phase 3
0.9623	High Similarity	NPD7054	Approved
0.9563	High Similarity	NPD7472	Approved
0.9503	High Similarity	NPD6797	Phase 2
0.9444	High Similarity	NPD7251	Discontinued
0.9437	High Similarity	NPD3818	Discontinued
0.9423	High Similarity	NPD4381	Clinical (unspecified phase)
0.9268	High Similarity	NPD7808	Phase 3
0.9268	High Similarity	NPD4338	Clinical (unspecified phase)
0.9193	High Similarity	NPD6166	Phase 2
0.9193	High Similarity	NPD6168	Clinical (unspecified phase)
0.9193	High Similarity	NPD6167	Clinical (unspecified phase)
0.9167	High Similarity	NPD1934	Approved
0.9108	High Similarity	NPD2393	Clinical (unspecified phase)
0.9024	High Similarity	NPD7804	Clinical (unspecified phase)
0.8875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8797	High Similarity	NPD4380	Phase 2
0.8774	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD2801	Approved
0.8662	High Similarity	NPD1512	Approved
0.8639	High Similarity	NPD6559	Discontinued
0.858	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD7993	Clinical (unspecified phase)
0.8528	High Similarity	NPD3882	Suspended
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8373	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD1465	Phase 2
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5402	Approved
0.8242	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6801	Discontinued
0.8214	Intermediate Similarity	NPD6959	Discontinued
0.821	Intermediate Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8171	Intermediate Similarity	NPD7411	Suspended
0.8148	Intermediate Similarity	NPD5403	Approved
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.814	Intermediate Similarity	NPD5844	Phase 1
0.8117	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1613	Approved
0.8114	Intermediate Similarity	NPD8313	Approved
0.8114	Intermediate Similarity	NPD8312	Approved
0.8089	Intermediate Similarity	NPD2796	Approved
0.8081	Intermediate Similarity	NPD7228	Approved
0.8075	Intermediate Similarity	NPD6799	Approved
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5401	Approved
0.8025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD3751	Discontinued
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.7925	Intermediate Similarity	NPD7266	Discontinued
0.7898	Intermediate Similarity	NPD7685	Pre-registration
0.7892	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD943	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD6234	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8455	Phase 2
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD37	Approved
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7765	Intermediate Similarity	NPD4965	Approved
0.7765	Intermediate Similarity	NPD4966	Approved
0.7765	Intermediate Similarity	NPD4967	Phase 2
0.7749	Intermediate Similarity	NPD8151	Discontinued
0.7744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7584	Approved
0.7722	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3749	Approved
0.7701	Intermediate Similarity	NPD6779	Approved
0.7701	Intermediate Similarity	NPD6778	Approved
0.7701	Intermediate Similarity	NPD6777	Approved
0.7701	Intermediate Similarity	NPD6776	Approved
0.7701	Intermediate Similarity	NPD6782	Approved
0.7701	Intermediate Similarity	NPD6781	Approved
0.7701	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7669	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD6190	Approved
0.761	Intermediate Similarity	NPD1933	Approved
0.761	Intermediate Similarity	NPD230	Phase 1
0.76	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD7240	Approved
0.7579	Intermediate Similarity	NPD7435	Discontinued
0.7579	Intermediate Similarity	NPD7696	Phase 3
0.7579	Intermediate Similarity	NPD7697	Approved
0.7579	Intermediate Similarity	NPD7698	Approved
0.7577	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7783	Phase 2
0.7572	Intermediate Similarity	NPD919	Approved
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2935	Discontinued
0.7513	Intermediate Similarity	NPD7701	Phase 2
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7469	Intermediate Similarity	NPD3748	Approved
0.7448	Intermediate Similarity	NPD7870	Phase 2
0.7448	Intermediate Similarity	NPD7871	Phase 2
0.7435	Intermediate Similarity	NPD6823	Phase 2
0.7433	Intermediate Similarity	NPD6534	Approved
0.7433	Intermediate Similarity	NPD6535	Approved
0.7407	Intermediate Similarity	NPD7699	Phase 2
0.7407	Intermediate Similarity	NPD7700	Phase 2
0.7403	Intermediate Similarity	NPD1091	Approved
0.7394	Intermediate Similarity	NPD2800	Approved
0.7391	Intermediate Similarity	NPD447	Suspended
0.7362	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7347	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7585	Approved
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD7801	Approved
0.731	Intermediate Similarity	NPD3226	Approved
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7296	Intermediate Similarity	NPD4908	Phase 1
0.7294	Intermediate Similarity	NPD920	Approved
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6674	Discontinued
0.7282	Intermediate Similarity	NPD7583	Approved
0.7278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8319	Approved
0.7268	Intermediate Similarity	NPD8320	Phase 1
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7239	Intermediate Similarity	NPD6651	Approved
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD7390	Discontinued
0.7216	Intermediate Similarity	NPD7680	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7204	Intermediate Similarity	NPD8434	Phase 2
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7196	Intermediate Similarity	NPD6213	Phase 3
0.7196	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6212	Phase 3
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7186	Intermediate Similarity	NPD1243	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.717	Intermediate Similarity	NPD2798	Approved
0.7169	Intermediate Similarity	NPD2344	Approved
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD9494	Approved
0.7099	Intermediate Similarity	NPD6798	Discontinued
0.7089	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD1652	Phase 2
0.7076	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5124	Phase 1
0.7056	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.703	Intermediate Similarity	NPD7930	Approved
0.7029	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7019	Intermediate Similarity	NPD2861	Phase 2
0.7017	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD5353	Approved
0.7005	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD2309	Approved
0.6994	Remote Similarity	NPD3268	Approved
0.699	Remote Similarity	NPD5006	Approved
0.699	Remote Similarity	NPD5005	Approved
0.699	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6842	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