NPASS Compound

Structure

CID177731 OpenBabel06191715552D 43 47 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 0.8660 -1.5000 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 -6.0622 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 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 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 -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 3.4641 4.0000 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 2.5981 4.5000 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 4.0000 0.0000 C 0 0 2 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 3.0000 0.0000 C 0 0 3 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 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 -4.3301 -1.5000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 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 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 38 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 18 2 0 0 0 0 8 15 1 0 0 0 0 8 17 1 0 0 0 0 9 29 1 0 0 0 0 10 1 1 6 0 0 0 10 21 1 0 0 0 0 10 39 1 0 0 0 0 12 40 1 0 0 0 0 13 16 2 0 0 0 0 13 30 1 0 0 0 0 14 20 2 0 0 0 0 14 31 1 0 0 0 0 15 20 1 0 0 0 0 15 32 2 0 0 0 0 16 38 1 0 0 0 0 17 11 1 1 0 0 0 17 41 1 0 0 0 0 18 20 1 0 0 0 0 18 41 1 0 0 0 0 19 9 1 1 0 0 0 19 22 1 0 0 0 0 19 42 1 0 0 0 0 21 23 1 0 0 0 0 21 33 1 1 0 0 0 22 24 1 0 0 0 0 22 34 1 6 0 0 0 23 25 1 0 0 0 0 23 35 1 6 0 0 0 24 26 1 0 0 0 0 24 36 1 1 0 0 0 25 27 1 0 0 0 0 25 37 1 6 0 0 0 26 28 1 0 0 0 0 26 43 1 6 0 0 0 27 39 1 0 0 0 0 27 43 1 0 0 0 0 28 40 1 1 0 0 0 28 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.19
Volume:	563.46
LogP:	0.523
LogD:	0.113
LogS:	-3.776
# Rotatable Bonds:	7
TPSA:	234.29
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.185
Synthetic Accessibility Score:	4.812
Fsp3:	0.536
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.679
MDCK Permeability:	4.995832932763733e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.863
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	72.16246795654297%
Volume Distribution (VD):	0.489
Pgp-substrate:	21.375202178955078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.173
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.29
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	2.859
Half-life (T1/2):	0.513

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.553
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.698
Carcinogencity:	0.399
Eye Corrosion:	0.003
Eye Irritation:	0.067
Respiratory Toxicity:	0.608

Download Data

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

Natural Product: NPC177731

Natural Product ID:	NPC177731
*Common Name:**	(2S)-7-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(Hydroxymethyl)-3-[(3R,4R,5R,6S)-3,4,5-Trihydroxy-6-Methyloxan-2-Yl]Oxyoxan-2-Yl]Oxy-5-Hydroxy-2-(3-Hydroxy-4-Methoxyphenyl)-2,3-Dihydrochromen-4-One
IUPAC Name:	(2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	ARGKVCXINMKCAZ-QGFYHPQASA-N
Standard InCHI:	InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27?,28+/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H](C(O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2C(=O)C[C@@H](c3ccc(c(c3)O)OC)Oc2c1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1885559
PubChem CID:	73395
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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	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
Potency	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	15003.0	nM	PMID[456557]

☑ 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 NPC177731 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	416
0.1-0.2	1625
0.2-0.3	3554
0.3-0.4	8646
0.4-0.5	9174
0.5-0.6	4818
0.6-0.7	4998
0.7-0.8	6088
0.8-0.85	2106
0.85-0.9	844
0.9-0.95	412
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC79056
1.0	High Similarity	NPC105095
1.0	High Similarity	NPC44328
0.9937	High Similarity	NPC293629
0.9937	High Similarity	NPC43587
0.9812	High Similarity	NPC209296
0.9812	High Similarity	NPC105283
0.9812	High Similarity	NPC195257
0.9811	High Similarity	NPC5778
0.9811	High Similarity	NPC236934
0.9753	High Similarity	NPC239549
0.9753	High Similarity	NPC51774
0.9753	High Similarity	NPC236191
0.9753	High Similarity	NPC208668
0.9752	High Similarity	NPC51326
0.9752	High Similarity	NPC231194
0.9693	High Similarity	NPC198199
0.9693	High Similarity	NPC102028
0.9693	High Similarity	NPC142996
0.9691	High Similarity	NPC267254
0.9691	High Similarity	NPC256760
0.9691	High Similarity	NPC301683
0.9691	High Similarity	NPC261254
0.9691	High Similarity	NPC180918
0.9689	High Similarity	NPC86008
0.9689	High Similarity	NPC229687
0.9689	High Similarity	NPC61791
0.9688	High Similarity	NPC210073
0.9688	High Similarity	NPC115674
0.9686	High Similarity	NPC29830
0.9634	High Similarity	NPC255799
0.9632	High Similarity	NPC204693
0.963	High Similarity	NPC150767
0.963	High Similarity	NPC183357
0.963	High Similarity	NPC22195
0.963	High Similarity	NPC21190
0.963	High Similarity	NPC293004
0.963	High Similarity	NPC78734
0.9627	High Similarity	NPC229729
0.9627	High Similarity	NPC477502
0.9627	High Similarity	NPC45400
0.9625	High Similarity	NPC284277
0.9625	High Similarity	NPC311830
0.9625	High Similarity	NPC22832
0.9625	High Similarity	NPC475366
0.9625	High Similarity	NPC475497
0.9623	High Similarity	NPC127782
0.9623	High Similarity	NPC300537
0.9576	High Similarity	NPC120952
0.9576	High Similarity	NPC89052
0.9576	High Similarity	NPC251417
0.9573	High Similarity	NPC476472
0.9573	High Similarity	NPC220173
0.9573	High Similarity	NPC16194
0.9573	High Similarity	NPC473327
0.9573	High Similarity	NPC19108
0.9573	High Similarity	NPC294815
0.9571	High Similarity	NPC156977
0.9568	High Similarity	NPC95855
0.9568	High Similarity	NPC170675
0.9568	High Similarity	NPC52382
0.9568	High Similarity	NPC270578
0.9568	High Similarity	NPC472381
0.9568	High Similarity	NPC210042
0.9568	High Similarity	NPC472383
0.9568	High Similarity	NPC112755
0.9568	High Similarity	NPC471457
0.9565	High Similarity	NPC8856
0.9565	High Similarity	NPC70441
0.9563	High Similarity	NPC222936
0.9563	High Similarity	NPC270335
0.9563	High Similarity	NPC284960
0.9563	High Similarity	NPC88023
0.9563	High Similarity	NPC243930
0.9563	High Similarity	NPC309025
0.9563	High Similarity	NPC191306
0.9563	High Similarity	NPC19709
0.9518	High Similarity	NPC192539
0.9515	High Similarity	NPC292019
0.9515	High Similarity	NPC202908
0.9515	High Similarity	NPC122467
0.9515	High Similarity	NPC48984
0.9515	High Similarity	NPC219043
0.9515	High Similarity	NPC14187
0.9512	High Similarity	NPC25724
0.9509	High Similarity	NPC44558
0.9509	High Similarity	NPC34287
0.9509	High Similarity	NPC95866
0.9509	High Similarity	NPC471416
0.9509	High Similarity	NPC67105
0.9509	High Similarity	NPC285197
0.9509	High Similarity	NPC218488
0.9509	High Similarity	NPC474434
0.9509	High Similarity	NPC52353
0.9509	High Similarity	NPC194483
0.9506	High Similarity	NPC93099
0.9506	High Similarity	NPC160156
0.9506	High Similarity	NPC92565
0.9503	High Similarity	NPC15358
0.9503	High Similarity	NPC165720
0.95	High Similarity	NPC77660
0.95	High Similarity	NPC189142
0.95	High Similarity	NPC473043
0.9497	High Similarity	NPC271270
0.9497	High Similarity	NPC246469
0.9497	High Similarity	NPC142860
0.9497	High Similarity	NPC97285
0.9458	High Similarity	NPC173837
0.9458	High Similarity	NPC241196
0.9455	High Similarity	NPC294629
0.9451	High Similarity	NPC471725
0.9451	High Similarity	NPC3583
0.9451	High Similarity	NPC26230
0.9451	High Similarity	NPC155877
0.9451	High Similarity	NPC307518
0.9451	High Similarity	NPC259152
0.9451	High Similarity	NPC134532
0.9451	High Similarity	NPC60735
0.9451	High Similarity	NPC47140
0.9451	High Similarity	NPC48773
0.9451	High Similarity	NPC472386
0.9451	High Similarity	NPC203259
0.9451	High Similarity	NPC475155
0.9451	High Similarity	NPC33054
0.9451	High Similarity	NPC471748
0.9451	High Similarity	NPC235575
0.9451	High Similarity	NPC67134
0.9451	High Similarity	NPC176740
0.9451	High Similarity	NPC205076
0.9448	High Similarity	NPC226294
0.9448	High Similarity	NPC203050
0.9448	High Similarity	NPC219904
0.9448	High Similarity	NPC58053
0.9448	High Similarity	NPC186807
0.9448	High Similarity	NPC475942
0.9448	High Similarity	NPC105025
0.9448	High Similarity	NPC223747
0.9448	High Similarity	NPC227508
0.9448	High Similarity	NPC183036
0.9448	High Similarity	NPC469931
0.9448	High Similarity	NPC45638
0.9448	High Similarity	NPC120099
0.9448	High Similarity	NPC225434
0.9448	High Similarity	NPC201292
0.9448	High Similarity	NPC93337
0.9444	High Similarity	NPC197285
0.9444	High Similarity	NPC21100
0.9441	High Similarity	NPC88043
0.9441	High Similarity	NPC168822
0.9437	High Similarity	NPC182045
0.9401	High Similarity	NPC110941
0.9401	High Similarity	NPC126784
0.9401	High Similarity	NPC473682
0.9401	High Similarity	NPC470444
0.9401	High Similarity	NPC470443
0.9401	High Similarity	NPC241423
0.9401	High Similarity	NPC473571
0.9398	High Similarity	NPC169733
0.9398	High Similarity	NPC471669
0.9398	High Similarity	NPC89127
0.9394	High Similarity	NPC472993
0.939	High Similarity	NPC210808
0.939	High Similarity	NPC29958
0.939	High Similarity	NPC254855
0.939	High Similarity	NPC105511
0.939	High Similarity	NPC136042
0.939	High Similarity	NPC156869
0.939	High Similarity	NPC199079
0.939	High Similarity	NPC67326
0.939	High Similarity	NPC255157
0.939	High Similarity	NPC206123
0.939	High Similarity	NPC259896
0.939	High Similarity	NPC224462
0.939	High Similarity	NPC212748
0.9387	High Similarity	NPC173637
0.9387	High Similarity	NPC84362
0.9387	High Similarity	NPC275454
0.9387	High Similarity	NPC226304
0.9387	High Similarity	NPC116745
0.9387	High Similarity	NPC325555
0.9387	High Similarity	NPC223424
0.9387	High Similarity	NPC127546
0.9387	High Similarity	NPC58716
0.9387	High Similarity	NPC45618
0.9387	High Similarity	NPC265530
0.9387	High Similarity	NPC146792
0.9387	High Similarity	NPC317489
0.9387	High Similarity	NPC52550
0.9383	High Similarity	NPC277205
0.9379	High Similarity	NPC190450
0.9379	High Similarity	NPC148273
0.9375	High Similarity	NPC110349
0.9349	High Similarity	NPC148710
0.9341	High Similarity	NPC476619
0.9341	High Similarity	NPC476623
0.9341	High Similarity	NPC476622
0.9341	High Similarity	NPC475261
0.9341	High Similarity	NPC476618
0.9341	High Similarity	NPC472387
0.9341	High Similarity	NPC476620

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 NPC177731 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	917
0.2-0.3	1846
0.3-0.4	2646
0.4-0.5	1877
0.5-0.6	952
0.6-0.7	378
0.7-0.8	129
0.8-0.85	23
0.85-0.9	7
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7074	Phase 3
0.9812	High Similarity	NPD7054	Approved
0.9752	High Similarity	NPD7472	Approved
0.9512	High Similarity	NPD7251	Discontinued
0.9455	High Similarity	NPD7808	Phase 3
0.9451	High Similarity	NPD6797	Phase 2
0.9268	High Similarity	NPD3818	Discontinued
0.9264	High Similarity	NPD6166	Phase 2
0.9264	High Similarity	NPD6167	Clinical (unspecified phase)
0.9264	High Similarity	NPD6168	Clinical (unspecified phase)
0.913	High Similarity	NPD4381	Clinical (unspecified phase)
0.9119	High Similarity	NPD1934	Approved
0.9107	High Similarity	NPD4338	Clinical (unspecified phase)
0.9096	High Similarity	NPD7804	Clinical (unspecified phase)
0.8944	High Similarity	NPD2393	Clinical (unspecified phase)
0.8712	High Similarity	NPD2801	Approved
0.8606	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD3817	Phase 2
0.8528	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD1511	Approved
0.8497	Intermediate Similarity	NPD6559	Discontinued
0.8494	Intermediate Similarity	NPD3882	Suspended
0.8443	Intermediate Similarity	NPD7075	Discontinued
0.8439	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD1512	Approved
0.8343	Intermediate Similarity	NPD5494	Approved
0.8266	Intermediate Similarity	NPD7228	Approved
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8155	Intermediate Similarity	NPD1465	Phase 2
0.8155	Intermediate Similarity	NPD7819	Suspended
0.8114	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7473	Discontinued
0.8095	Intermediate Similarity	NPD6801	Discontinued
0.809	Intermediate Similarity	NPD8313	Approved
0.809	Intermediate Similarity	NPD8312	Approved
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD1653	Approved
0.8036	Intermediate Similarity	NPD7411	Suspended
0.8035	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.7978	Intermediate Similarity	NPD7685	Pre-registration
0.7977	Intermediate Similarity	NPD7199	Phase 2
0.7967	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2796	Approved
0.7939	Intermediate Similarity	NPD6799	Approved
0.7904	Intermediate Similarity	NPD5403	Approved
0.7901	Intermediate Similarity	NPD7266	Discontinued
0.7892	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1510	Phase 2
0.7862	Intermediate Similarity	NPD1613	Approved
0.7862	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6234	Discontinued
0.7853	Intermediate Similarity	NPD3751	Discontinued
0.7841	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD8455	Phase 2
0.7829	Intermediate Similarity	NPD3787	Discontinued
0.7824	Intermediate Similarity	NPD8151	Discontinued
0.7802	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD7240	Approved
0.7778	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD6599	Discontinued
0.775	Intermediate Similarity	NPD1240	Approved
0.7746	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4967	Phase 2
0.7746	Intermediate Similarity	NPD4965	Approved
0.7744	Intermediate Similarity	NPD7783	Phase 2
0.7744	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7584	Approved
0.7684	Intermediate Similarity	NPD6776	Approved
0.7684	Intermediate Similarity	NPD6782	Approved
0.7684	Intermediate Similarity	NPD6781	Approved
0.7684	Intermediate Similarity	NPD6780	Approved
0.7684	Intermediate Similarity	NPD6778	Approved
0.7684	Intermediate Similarity	NPD6779	Approved
0.7684	Intermediate Similarity	NPD6777	Approved
0.7673	Intermediate Similarity	NPD3027	Phase 3
0.7656	Intermediate Similarity	NPD7698	Approved
0.7656	Intermediate Similarity	NPD7696	Phase 3
0.7656	Intermediate Similarity	NPD7697	Approved
0.7656	Intermediate Similarity	NPD7435	Discontinued
0.7654	Intermediate Similarity	NPD1607	Approved
0.7644	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD943	Approved
0.761	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1933	Approved
0.759	Intermediate Similarity	NPD7701	Phase 2
0.7584	Intermediate Similarity	NPD3926	Phase 2
0.7557	Intermediate Similarity	NPD919	Approved
0.7547	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7545	Intermediate Similarity	NPD3750	Approved
0.753	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7870	Phase 2
0.7526	Intermediate Similarity	NPD7871	Phase 2
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD3749	Approved
0.7487	Intermediate Similarity	NPD7699	Phase 2
0.7487	Intermediate Similarity	NPD7700	Phase 2
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7472	Intermediate Similarity	NPD1247	Approved
0.7448	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD8319	Approved
0.7436	Intermediate Similarity	NPD8320	Phase 1
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6535	Approved
0.7421	Intermediate Similarity	NPD6534	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7409	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7458	Discontinued
0.7396	Intermediate Similarity	NPD6190	Approved
0.7387	Intermediate Similarity	NPD7801	Approved
0.7385	Intermediate Similarity	NPD7680	Approved
0.7381	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6674	Discontinued
0.7378	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD2533	Approved
0.7368	Intermediate Similarity	NPD2534	Approved
0.7368	Intermediate Similarity	NPD2532	Approved
0.7344	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7585	Approved
0.7305	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD6099	Approved
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD2800	Approved
0.7273	Intermediate Similarity	NPD7583	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3748	Approved
0.7243	Intermediate Similarity	NPD5953	Discontinued
0.7229	Intermediate Similarity	NPD6651	Approved
0.7228	Intermediate Similarity	NPD7286	Phase 2
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.72	Intermediate Similarity	NPD3226	Approved
0.7196	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD6212	Phase 3
0.7188	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6213	Phase 3
0.7184	Intermediate Similarity	NPD920	Approved
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.7178	Intermediate Similarity	NPD6832	Phase 2
0.717	Intermediate Similarity	NPD1091	Approved
0.7166	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4363	Phase 3
0.715	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9494	Approved
0.7095	Intermediate Similarity	NPD5353	Approved
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD8127	Discontinued
0.7081	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6844	Discontinued
0.7076	Intermediate Similarity	NPD1243	Approved
0.7069	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6842	Approved
0.7068	Intermediate Similarity	NPD6841	Approved
0.7068	Intermediate Similarity	NPD6843	Phase 3
0.7067	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7055	Intermediate Similarity	NPD2798	Approved
0.7052	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7024	Intermediate Similarity	NPD7930	Approved
0.7022	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5242	Approved
0.7006	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD6798	Discontinued
0.6988	Remote Similarity	NPD2313	Discontinued
0.6985	Remote Similarity	NPD5005	Approved
0.6985	Remote Similarity	NPD5006	Approved
0.6982	Remote Similarity	NPD7097	Phase 1
0.6977	Remote Similarity	NPD1652	Phase 2
0.6973	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6355	Discontinued
0.6964	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5124	Phase 1
0.6964	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD5710	Approved
0.6957	Remote Similarity	NPD5711	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