NPASS Compound

Structure

CID10097 OpenBabel06191715332D 25 27 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 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 2.5981 -1.5000 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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -2.5981 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 -1.5000 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 2.5981 1.5000 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 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 5 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 17 1 0 0 0 0 5 24 1 0 0 0 0 6 10 1 0 0 0 0 6 18 2 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 24 1 0 0 0 0 9 4 1 6 0 0 0 9 12 1 0 0 0 0 9 25 1 0 0 0 0 10 13 1 0 0 0 0 11 13 2 0 0 0 0 12 14 1 0 0 0 0 12 20 1 1 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 23 1 1 0 0 0 16 11 1 6 0 0 0 16 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.1
Volume:	325.553
LogP:	-0.301
LogD:	-0.479
LogS:	-1.988
# Rotatable Bonds:	2
TPSA:	160.82
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	4.013
Fsp3:	0.438
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:	-5.977
MDCK Permeability:	8.681291546963621e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.858
20% Bioavailability (F20%):	0.595
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	71.07427215576172%
Volume Distribution (VD):	0.972
Pgp-substrate:	31.90191650390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.212
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.548
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	2.336
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.887
AMES Toxicity:	0.617
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.465
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.099
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC10097

Natural Product ID:	NPC10097
*Common Name:**	Biflorin
IUPAC Name:	5,7-dihydroxy-2-methyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Synonyms:
Standard InCHIKey:	XTZWWMZDVUKEDJ-SPEJKDPOSA-N
Standard InCHI:	InChI=1S/C16H18O9/c1-5-2-6(18)10-8(24-5)3-7(19)11(13(10)21)16-15(23)14(22)12(20)9(4-17)25-16/h2-3,9,12,14-17,19-23H,4H2,1H3/t9-,12-,14+,15-,16+/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463312
PubChem CID:	441959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	leaf	n.a.	PMID[28135851]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[31301930]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964790]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24356	Fructus xanthii sibirici	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6072	Andinobates bombetes	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2395	Siphonaria australis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10319	Calycodendron milnei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1032	Piper attenuatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12409	Artemisia jacutica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1934	Strychnos triplinervia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25680	Ramalina siliquosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5834	Pellicularia sasakii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4504	Cassia jahnii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6041	Lithocolletis coryli	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9612	Dryopteris dilatata	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9718	Cyphelium chrysocephalum	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO577	Lactifluus subvellereus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9456	Rubus sanctus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8622	Stauntonia hexaphylla	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6783	Avrainvillea rawsonii	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15735	Galeocerdo arcticus	Species	Carcharhinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO173	Aconitum sajanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1456	Bersama abyssinica	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7383	Puccinia lagenophorae	Species	Pucciniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	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	3
MIC	4
Others	14

Activity Type	# Activity
Cell Line	5
CELL-LINE	5
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	51.3	%	PMID[463136]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	75.0	%	PMID[463136]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	140000.0	nM	PMID[463136]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	37100.0	nM	PMID[463136]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	51700.0	nM	PMID[463136]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	625.0	ug.mL-1	PMID[463135]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	625.0	ug.mL-1	PMID[463135]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	2500.0	ug.mL-1	PMID[463135]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	>	2500.0	ug.mL-1	PMID[463135]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	74.67	%	PMID[463136]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	44.52	%	PMID[463136]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	33.36	%	PMID[463136]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	60.0	%	PMID[463136]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	48.0	%	PMID[463136]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	26.0	%	PMID[463136]
NPT32	Organism	Mus musculus	Mus musculus	mortality	=	40.0	%	PMID[463136]
NPT21752	CELL-LINE	Peritoneal macrophage cells	n.a.	Activity	=	90.36	%	PMID[463136]
NPT21752	CELL-LINE	Peritoneal macrophage cells	n.a.	Inhibition	=	61.1	%	PMID[463136]
NPT21752	CELL-LINE	Peritoneal macrophage cells	n.a.	Inhibition	=	77.5	%	PMID[463136]
NPT21752	CELL-LINE	Peritoneal macrophage cells	n.a.	Inhibition	=	42.2	%	PMID[463136]
NPT21752	CELL-LINE	Peritoneal macrophage cells	n.a.	Inhibition	=	55.9	%	PMID[463136]

☑ 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 NPC10097 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	389
0.1-0.2	1573
0.2-0.3	3597
0.3-0.4	9251
0.4-0.5	9620
0.5-0.6	3907
0.6-0.7	5632
0.7-0.8	4435
0.8-0.85	2696
0.85-0.9	1461
0.9-0.95	127
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC139966
0.993	High Similarity	NPC307052
0.9789	High Similarity	NPC85773
0.9724	High Similarity	NPC244583
0.9724	High Similarity	NPC56232
0.9724	High Similarity	NPC161881
0.9724	High Similarity	NPC10807
0.9724	High Similarity	NPC150123
0.9718	High Similarity	NPC474302
0.9655	High Similarity	NPC328740
0.9655	High Similarity	NPC477897
0.9655	High Similarity	NPC209846
0.9655	High Similarity	NPC289774
0.965	High Similarity	NPC473133
0.965	High Similarity	NPC47388
0.965	High Similarity	NPC470670
0.965	High Similarity	NPC91902
0.9592	High Similarity	NPC470604
0.9592	High Similarity	NPC111341
0.9592	High Similarity	NPC304745
0.9592	High Similarity	NPC470605
0.9592	High Similarity	NPC470603
0.9589	High Similarity	NPC256141
0.9524	High Similarity	NPC326592
0.9524	High Similarity	NPC109594
0.9524	High Similarity	NPC268193
0.9524	High Similarity	NPC87304
0.9524	High Similarity	NPC78021
0.9524	High Similarity	NPC268950
0.9524	High Similarity	NPC112701
0.9524	High Similarity	NPC108706
0.9524	High Similarity	NPC223701
0.9524	High Similarity	NPC472583
0.9524	High Similarity	NPC7989
0.9524	High Similarity	NPC211158
0.9524	High Similarity	NPC469405
0.9521	High Similarity	NPC319910
0.9521	High Similarity	NPC262039
0.9521	High Similarity	NPC471677
0.9521	High Similarity	NPC471676
0.9521	High Similarity	NPC278476
0.9521	High Similarity	NPC472422
0.9521	High Similarity	NPC474023
0.9521	High Similarity	NPC472420
0.9521	High Similarity	NPC262038
0.9521	High Similarity	NPC263384
0.9521	High Similarity	NPC254412
0.9521	High Similarity	NPC244577
0.9521	High Similarity	NPC474021
0.9517	High Similarity	NPC89442
0.9514	High Similarity	NPC202494
0.951	High Similarity	NPC224714
0.951	High Similarity	NPC470890
0.951	High Similarity	NPC297788
0.9463	High Similarity	NPC470606
0.9459	High Similarity	NPC48579
0.9459	High Similarity	NPC259710
0.9459	High Similarity	NPC304207
0.9459	High Similarity	NPC207809
0.9459	High Similarity	NPC217706
0.9459	High Similarity	NPC470681
0.9456	High Similarity	NPC216035
0.9456	High Similarity	NPC138288
0.9456	High Similarity	NPC475790
0.9456	High Similarity	NPC217149
0.9456	High Similarity	NPC171651
0.9456	High Similarity	NPC243171
0.9456	High Similarity	NPC35567
0.9452	High Similarity	NPC177308
0.9452	High Similarity	NPC105136
0.9452	High Similarity	NPC180351
0.9452	High Similarity	NPC124478
0.9444	High Similarity	NPC472629
0.9441	High Similarity	NPC18886
0.9433	High Similarity	NPC139554
0.9433	High Similarity	NPC471697
0.94	High Similarity	NPC470607
0.9396	High Similarity	NPC215917
0.9396	High Similarity	NPC10754
0.9396	High Similarity	NPC20530
0.9392	High Similarity	NPC248793
0.9392	High Similarity	NPC180301
0.9392	High Similarity	NPC293286
0.9388	High Similarity	NPC471675
0.9388	High Similarity	NPC472636
0.9384	High Similarity	NPC472628
0.9379	High Similarity	NPC472627
0.9375	High Similarity	NPC87486
0.9375	High Similarity	NPC124780
0.9329	High Similarity	NPC477958
0.9324	High Similarity	NPC476238
0.9324	High Similarity	NPC285623
0.9324	High Similarity	NPC473996
0.9324	High Similarity	NPC31627
0.9324	High Similarity	NPC327269
0.932	High Similarity	NPC191154
0.932	High Similarity	NPC38775
0.931	High Similarity	NPC24136
0.931	High Similarity	NPC187282
0.931	High Similarity	NPC290133
0.9306	High Similarity	NPC112749
0.9306	High Similarity	NPC242100
0.9306	High Similarity	NPC255133
0.9301	High Similarity	NPC166689
0.9301	High Similarity	NPC96408
0.9301	High Similarity	NPC258630
0.9301	High Similarity	NPC156190
0.9301	High Similarity	NPC17170
0.9301	High Similarity	NPC279650
0.9276	High Similarity	NPC26326
0.9272	High Similarity	NPC53545
0.9272	High Similarity	NPC117418
0.9267	High Similarity	NPC17521
0.9267	High Similarity	NPC78492
0.9267	High Similarity	NPC208152
0.9262	High Similarity	NPC244250
0.9262	High Similarity	NPC236756
0.9262	High Similarity	NPC311579
0.9262	High Similarity	NPC20907
0.9257	High Similarity	NPC190217
0.9257	High Similarity	NPC472423
0.9257	High Similarity	NPC474744
0.9257	High Similarity	NPC474772
0.9257	High Similarity	NPC134819
0.9257	High Similarity	NPC472580
0.9252	High Similarity	NPC5173
0.9247	High Similarity	NPC40086
0.9247	High Similarity	NPC3779
0.9247	High Similarity	NPC176869
0.9247	High Similarity	NPC476182
0.9247	High Similarity	NPC296998
0.9247	High Similarity	NPC122828
0.9247	High Similarity	NPC473077
0.9247	High Similarity	NPC51070
0.9247	High Similarity	NPC211466
0.9247	High Similarity	NPC222298
0.9247	High Similarity	NPC44721
0.9236	High Similarity	NPC227579
0.9236	High Similarity	NPC223500
0.9236	High Similarity	NPC1089
0.9236	High Similarity	NPC37496
0.9236	High Similarity	NPC166934
0.9236	High Similarity	NPC276565
0.9236	High Similarity	NPC40833
0.9236	High Similarity	NPC32739
0.9236	High Similarity	NPC76338
0.9236	High Similarity	NPC306829
0.9236	High Similarity	NPC194432
0.9236	High Similarity	NPC125855
0.9236	High Similarity	NPC265040
0.9236	High Similarity	NPC76372
0.9236	High Similarity	NPC296917
0.9236	High Similarity	NPC324436
0.9236	High Similarity	NPC66515
0.9236	High Similarity	NPC161506
0.9236	High Similarity	NPC228504
0.9236	High Similarity	NPC148757
0.9236	High Similarity	NPC78
0.9236	High Similarity	NPC166482
0.9236	High Similarity	NPC10937
0.9236	High Similarity	NPC220998
0.9236	High Similarity	NPC328164
0.9236	High Similarity	NPC177354
0.9236	High Similarity	NPC324134
0.9236	High Similarity	NPC64915
0.9236	High Similarity	NPC182852
0.9236	High Similarity	NPC167624
0.9236	High Similarity	NPC107572
0.9225	High Similarity	NPC131130
0.922	High Similarity	NPC174999
0.9216	High Similarity	NPC44947
0.9216	High Similarity	NPC131745
0.9211	High Similarity	NPC472631
0.9211	High Similarity	NPC470326
0.9211	High Similarity	NPC472630
0.9211	High Similarity	NPC475784
0.9205	High Similarity	NPC474055
0.9205	High Similarity	NPC23817
0.9205	High Similarity	NPC472598
0.92	High Similarity	NPC321779
0.92	High Similarity	NPC470327
0.92	High Similarity	NPC45849
0.92	High Similarity	NPC200761
0.92	High Similarity	NPC476169
0.92	High Similarity	NPC477503
0.92	High Similarity	NPC477530
0.9195	High Similarity	NPC210597
0.9195	High Similarity	NPC477957
0.9195	High Similarity	NPC106976
0.9189	High Similarity	NPC61258
0.9189	High Similarity	NPC477240
0.9189	High Similarity	NPC472633
0.9189	High Similarity	NPC37348
0.9189	High Similarity	NPC472421
0.9189	High Similarity	NPC214454
0.9189	High Similarity	NPC106025
0.9184	High Similarity	NPC472345
0.9184	High Similarity	NPC168085
0.9184	High Similarity	NPC199335
0.9184	High Similarity	NPC470460

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 NPC10097 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	875
0.2-0.3	1729
0.3-0.4	2648
0.4-0.5	1932
0.5-0.6	1085
0.6-0.7	359
0.7-0.8	119
0.8-0.85	42
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9452	High Similarity	NPD4380	Phase 2
0.9133	High Similarity	NPD2393	Clinical (unspecified phase)
0.911	High Similarity	NPD4378	Clinical (unspecified phase)
0.9079	High Similarity	NPD4381	Clinical (unspecified phase)
0.9079	High Similarity	NPD7075	Discontinued
0.894	High Similarity	NPD1934	Approved
0.894	High Similarity	NPD6801	Discontinued
0.8924	High Similarity	NPD7804	Clinical (unspecified phase)
0.8889	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD1550	Clinical (unspecified phase)
0.8882	High Similarity	NPD7096	Clinical (unspecified phase)
0.8828	High Similarity	NPD1549	Phase 2
0.8824	High Similarity	NPD8443	Clinical (unspecified phase)
0.8734	High Similarity	NPD6168	Clinical (unspecified phase)
0.8734	High Similarity	NPD6166	Phase 2
0.8734	High Similarity	NPD6167	Clinical (unspecified phase)
0.8725	High Similarity	NPD7410	Clinical (unspecified phase)
0.869	High Similarity	NPD2796	Approved
0.8636	High Similarity	NPD2801	Approved
0.8627	High Similarity	NPD7411	Suspended
0.8621	High Similarity	NPD1510	Phase 2
0.8571	High Similarity	NPD7054	Approved
0.8544	High Similarity	NPD6959	Discontinued
0.8533	High Similarity	NPD1511	Approved
0.8519	High Similarity	NPD7472	Approved
0.8519	High Similarity	NPD7074	Phase 3
0.8516	High Similarity	NPD7819	Suspended
0.8509	High Similarity	NPD3818	Discontinued
0.8466	Intermediate Similarity	NPD6797	Phase 2
0.8462	Intermediate Similarity	NPD3817	Phase 2
0.8421	Intermediate Similarity	NPD1512	Approved
0.8415	Intermediate Similarity	NPD6559	Discontinued
0.8415	Intermediate Similarity	NPD7251	Discontinued
0.8411	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2800	Approved
0.8366	Intermediate Similarity	NPD5403	Approved
0.8364	Intermediate Similarity	NPD7808	Phase 3
0.8345	Intermediate Similarity	NPD1240	Approved
0.8291	Intermediate Similarity	NPD3882	Suspended
0.8272	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5494	Approved
0.8235	Intermediate Similarity	NPD5401	Approved
0.8231	Intermediate Similarity	NPD1607	Approved
0.8231	Intermediate Similarity	NPD6651	Approved
0.8228	Intermediate Similarity	NPD5402	Approved
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2532	Approved
0.8117	Intermediate Similarity	NPD2534	Approved
0.8117	Intermediate Similarity	NPD2533	Approved
0.8063	Intermediate Similarity	NPD7768	Phase 2
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8026	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1243	Approved
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD920	Approved
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7974	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD4628	Phase 3
0.7974	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2935	Discontinued
0.7829	Intermediate Similarity	NPD1551	Phase 2
0.7811	Intermediate Similarity	NPD5953	Discontinued
0.78	Intermediate Similarity	NPD5124	Phase 1
0.78	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3749	Approved
0.7784	Intermediate Similarity	NPD4363	Phase 3
0.7784	Intermediate Similarity	NPD4360	Phase 2
0.7758	Intermediate Similarity	NPD1247	Approved
0.7744	Intermediate Similarity	NPD919	Approved
0.7733	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1613	Approved
0.7727	Intermediate Similarity	NPD2424	Discontinued
0.7718	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2313	Discontinued
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7712	Intermediate Similarity	NPD6099	Approved
0.7712	Intermediate Similarity	NPD6100	Approved
0.7705	Intermediate Similarity	NPD7584	Approved
0.7692	Intermediate Similarity	NPD7286	Phase 2
0.7677	Intermediate Similarity	NPD1652	Phase 2
0.767	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7647	Intermediate Similarity	NPD3748	Approved
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5711	Approved
0.7605	Intermediate Similarity	NPD5710	Approved
0.7595	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4908	Phase 1
0.7578	Intermediate Similarity	NPD3226	Approved
0.7572	Intermediate Similarity	NPD8313	Approved
0.7572	Intermediate Similarity	NPD8312	Approved
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD2344	Approved
0.7532	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7485	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6832	Phase 2
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7456	Intermediate Similarity	NPD3926	Phase 2
0.7452	Intermediate Similarity	NPD2654	Approved
0.7444	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4361	Phase 2
0.7436	Intermediate Similarity	NPD2346	Discontinued
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7417	Intermediate Similarity	NPD3027	Phase 3
0.7415	Intermediate Similarity	NPD9717	Approved
0.7396	Intermediate Similarity	NPD3787	Discontinued
0.7383	Intermediate Similarity	NPD1203	Approved
0.7377	Intermediate Similarity	NPD6782	Approved
0.7377	Intermediate Similarity	NPD6776	Approved
0.7377	Intermediate Similarity	NPD6778	Approved
0.7377	Intermediate Similarity	NPD6781	Approved
0.7377	Intermediate Similarity	NPD6779	Approved
0.7377	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6777	Approved
0.7377	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD3268	Approved
0.7368	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2309	Approved
0.7346	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8434	Phase 2
0.734	Intermediate Similarity	NPD8151	Discontinued
0.7338	Intermediate Similarity	NPD447	Suspended
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD2798	Approved
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD2403	Approved
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4966	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7299	Intermediate Similarity	NPD3823	Discontinued
0.7287	Intermediate Similarity	NPD7585	Approved
0.7267	Intermediate Similarity	NPD2797	Approved
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7435	Discontinued
0.7256	Intermediate Similarity	NPD7458	Discontinued
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4749	Approved
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD1729	Discontinued
0.7234	Intermediate Similarity	NPD7583	Approved
0.723	Intermediate Similarity	NPD1091	Approved
0.7229	Intermediate Similarity	NPD6844	Discontinued
0.7226	Intermediate Similarity	NPD1933	Approved
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7225	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD4661	Approved
0.7222	Intermediate Similarity	NPD4662	Approved
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7209	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6233	Phase 2
0.72	Intermediate Similarity	NPD8651	Approved
0.7197	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4308	Phase 3
0.7192	Intermediate Similarity	NPD9545	Approved
0.719	Intermediate Similarity	NPD4625	Phase 3
0.7173	Intermediate Similarity	NPD7783	Phase 2
0.7173	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7698	Approved
0.7166	Intermediate Similarity	NPD7696	Phase 3
0.7166	Intermediate Similarity	NPD7697	Approved
0.7159	Intermediate Similarity	NPD6104	Discontinued
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7134	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4536	Approved
0.7134	Intermediate Similarity	NPD4538	Approved
0.7128	Intermediate Similarity	NPD7871	Phase 2
0.7128	Intermediate Similarity	NPD7870	Phase 2
0.7125	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6823	Phase 2
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7105	Intermediate Similarity	NPD7701	Phase 2
0.7104	Intermediate Similarity	NPD6534	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