NPASS Compound

Structure

CID246469 OpenBabel06191716052D 41 45 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 -6.0622 2.5000 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 -6.9282 3.0000 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 -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 3 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 -7.7942 2.5000 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 -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 -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 3 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 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 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 3 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 3.0000 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 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 1 10 1 0 0 0 0 2 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 17 2 0 0 0 0 8 15 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 9 28 1 0 0 0 0 10 20 1 0 0 0 0 10 37 1 0 0 0 0 12 29 1 0 0 0 0 13 38 1 0 0 0 0 14 19 2 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 15 31 2 0 0 0 0 16 11 1 1 0 0 0 16 39 1 0 0 0 0 17 19 1 0 0 0 0 17 39 1 0 0 0 0 18 21 1 0 0 0 0 18 40 1 0 0 0 0 20 22 1 0 0 0 0 20 32 1 0 0 0 0 21 23 1 0 0 0 0 21 33 1 0 0 0 0 22 24 1 0 0 0 0 22 34 1 0 0 0 0 23 25 1 0 0 0 0 23 35 1 0 0 0 0 24 26 1 0 0 0 0 24 36 1 0 0 0 0 25 27 1 0 0 0 0 25 41 1 0 0 0 0 26 37 1 0 0 0 0 26 41 1 0 0 0 0 27 38 1 0 0 0 0 27 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.18
Volume:	537.374
LogP:	-0.514
LogD:	0.883
LogS:	-3.709
# Rotatable Bonds:	6
TPSA:	225.06
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	4.738
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.487
MDCK Permeability:	9.148591925622895e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.857
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	66.58226013183594%
Volume Distribution (VD):	0.369
Pgp-substrate:	27.712873458862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.109
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	1.57
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.445
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.036
Carcinogencity:	0.766
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.114

Download Data

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

Natural Product: NPC246469

Natural Product ID:	NPC246469
*Common Name:**	(2S)-7-[4,5-Dihydroxy-6-(Hydroxymethyl)-3-(3,4,5-Trihydroxy-6-Methyloxan-2-Yl)Oxyoxan-2-Yl]Oxy-5-Hydroxy-2-(4-Hydroxyphenyl)-2,3-Dihydrochromen-4-One
IUPAC Name:	(2S)-7-[4,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	DFPMSGMNTNDNHN-NPDMSNFISA-N
Standard InCHI:	InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10?,16-,18?,20?,21?,22?,23?,24?,25?,26?,27?/m0/s1
SMILES:	CC1C(C(C(C(O1)OC1C(C(C(CO)OC1Oc1cc(c2C(=O)C[C@@H](c3ccc(cc3)O)Oc2c1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1970019
PubChem CID:	5351463
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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1007/BF02329610]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np50075a009]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270561]
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[15763368]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17253088]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377852]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25068786]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25844502]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562741]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517238]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30758201]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31625751]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	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]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	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]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Herb	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	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]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4640	Portulaca oleracea	Species	Portulacaceae	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	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
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]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	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]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	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]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	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]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24846	Astragalus membranaceus	Species	Fabaceae	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]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20846	Sophora japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15715	Astragalus mongholicus	Species	Fabaceae	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]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	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]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28024	Rheum palmatum	Species	Polygonaceae	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]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4640	Portulaca oleracea	Species	Portulacaceae	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]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20881	Rheum officinale	Species	Polygonaceae	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]
NPO28265	Morus alba	Species	Moraceae	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]
NPO6792	Hedysarum polybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15715	Astragalus mongholicus	Species	Fabaceae	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]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	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]
NPO5270	Citrus natsudaidai	Species	Rutaceae	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]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25238	Rheum coreanum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21072	Rhododendron dauricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24846	Astragalus membranaceus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	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]
NPO6792	Hedysarum polybotrys	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15715	Astragalus mongholicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28679	Prunus mume	Species	Rosaceae	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]

☑ 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
GI50	57

Activity Type	# Activity
Cell Line	57

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[552615]

☑ 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 NPC246469 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	381
0.1-0.2	1477
0.2-0.3	3405
0.3-0.4	8422
0.4-0.5	9627
0.5-0.6	5056
0.6-0.7	5430
0.7-0.8	5956
0.8-0.85	1882
0.85-0.9	802
0.9-0.95	236
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271270
1.0	High Similarity	NPC97285
1.0	High Similarity	NPC142860
0.9869	High Similarity	NPC190450
0.9803	High Similarity	NPC473634
0.9803	High Similarity	NPC22062
0.9803	High Similarity	NPC138811
0.9801	High Similarity	NPC206378
0.974	High Similarity	NPC475382
0.9739	High Similarity	NPC473623
0.9737	High Similarity	NPC473512
0.9737	High Similarity	NPC129827
0.9737	High Similarity	NPC65003
0.9737	High Similarity	NPC44931
0.9735	High Similarity	NPC39351
0.9735	High Similarity	NPC26195
0.9735	High Similarity	NPC169248
0.9735	High Similarity	NPC72649
0.9735	High Similarity	NPC97052
0.9679	High Similarity	NPC70441
0.9677	High Similarity	NPC311850
0.9677	High Similarity	NPC124155
0.9677	High Similarity	NPC473644
0.9677	High Similarity	NPC257566
0.9675	High Similarity	NPC101636
0.9675	High Similarity	NPC303913
0.9671	High Similarity	NPC295613
0.9671	High Similarity	NPC170475
0.9671	High Similarity	NPC473657
0.9669	High Similarity	NPC106625
0.9615	High Similarity	NPC287889
0.9615	High Similarity	NPC135358
0.9613	High Similarity	NPC298171
0.9613	High Similarity	NPC240306
0.9613	High Similarity	NPC44947
0.961	High Similarity	NPC153342
0.961	High Similarity	NPC187379
0.9605	High Similarity	NPC95090
0.9605	High Similarity	NPC99233
0.9605	High Similarity	NPC27408
0.9603	High Similarity	NPC121001
0.9603	High Similarity	NPC259182
0.9557	High Similarity	NPC293629
0.9557	High Similarity	NPC43587
0.9554	High Similarity	NPC12013
0.9554	High Similarity	NPC189564
0.9554	High Similarity	NPC476470
0.9554	High Similarity	NPC298666
0.9554	High Similarity	NPC32641
0.9554	High Similarity	NPC256188
0.9554	High Similarity	NPC142142
0.9554	High Similarity	NPC11432
0.9554	High Similarity	NPC68592
0.9554	High Similarity	NPC477613
0.9554	High Similarity	NPC186816
0.9554	High Similarity	NPC262222
0.9554	High Similarity	NPC203145
0.9554	High Similarity	NPC221342
0.9548	High Similarity	NPC476215
0.9548	High Similarity	NPC249281
0.9548	High Similarity	NPC116458
0.9548	High Similarity	NPC246943
0.9548	High Similarity	NPC173582
0.9548	High Similarity	NPC253788
0.9548	High Similarity	NPC139320
0.9548	High Similarity	NPC47923
0.9548	High Similarity	NPC276377
0.9548	High Similarity	NPC163242
0.9548	High Similarity	NPC181465
0.9548	High Similarity	NPC215710
0.9548	High Similarity	NPC473438
0.9548	High Similarity	NPC265885
0.9545	High Similarity	NPC308265
0.9545	High Similarity	NPC73511
0.9542	High Similarity	NPC127406
0.9539	High Similarity	NPC210003
0.9539	High Similarity	NPC39360
0.9539	High Similarity	NPC29763
0.9539	High Similarity	NPC83283
0.9539	High Similarity	NPC143851
0.9497	High Similarity	NPC79056
0.9497	High Similarity	NPC44328
0.9497	High Similarity	NPC105095
0.9497	High Similarity	NPC199079
0.9497	High Similarity	NPC177731
0.9497	High Similarity	NPC210808
0.949	High Similarity	NPC76831
0.949	High Similarity	NPC289667
0.949	High Similarity	NPC292929
0.9487	High Similarity	NPC259834
0.9487	High Similarity	NPC244875
0.9487	High Similarity	NPC472876
0.9484	High Similarity	NPC271479
0.9484	High Similarity	NPC200708
0.9484	High Similarity	NPC471079
0.9484	High Similarity	NPC472320
0.9484	High Similarity	NPC136761
0.9484	High Similarity	NPC304741
0.9484	High Similarity	NPC470405
0.9481	High Similarity	NPC313163
0.9481	High Similarity	NPC161749
0.9481	High Similarity	NPC197896
0.9481	High Similarity	NPC108831
0.9481	High Similarity	NPC258035
0.9481	High Similarity	NPC23817
0.9481	High Similarity	NPC6985
0.9481	High Similarity	NPC182634
0.9481	High Similarity	NPC43638
0.9481	High Similarity	NPC156457
0.9481	High Similarity	NPC60966
0.9474	High Similarity	NPC88484
0.9474	High Similarity	NPC259767
0.9437	High Similarity	NPC257011
0.9437	High Similarity	NPC137871
0.9437	High Similarity	NPC288152
0.9437	High Similarity	NPC9002
0.9434	High Similarity	NPC105283
0.9434	High Similarity	NPC5319
0.943	High Similarity	NPC64425
0.9423	High Similarity	NPC297987
0.9423	High Similarity	NPC135846
0.9423	High Similarity	NPC170052
0.9423	High Similarity	NPC64305
0.9419	High Similarity	NPC41121
0.9419	High Similarity	NPC472459
0.9419	High Similarity	NPC111929
0.9419	High Similarity	NPC320283
0.9416	High Similarity	NPC203500
0.9416	High Similarity	NPC323593
0.9416	High Similarity	NPC45165
0.9416	High Similarity	NPC307938
0.9363	High Similarity	NPC131745
0.9355	High Similarity	NPC135391
0.9355	High Similarity	NPC133671
0.9355	High Similarity	NPC77672
0.9355	High Similarity	NPC197304
0.9355	High Similarity	NPC78263
0.9355	High Similarity	NPC54802
0.9355	High Similarity	NPC122809
0.9346	High Similarity	NPC166067
0.9342	High Similarity	NPC191154
0.9342	High Similarity	NPC477240
0.9342	High Similarity	NPC213723
0.9342	High Similarity	NPC214454
0.9342	High Similarity	NPC106025
0.9338	High Similarity	NPC199335
0.9321	High Similarity	NPC102028
0.9317	High Similarity	NPC301683
0.9317	High Similarity	NPC267254
0.9313	High Similarity	NPC61791
0.9313	High Similarity	NPC209296
0.9313	High Similarity	NPC195257
0.9308	High Similarity	NPC210073
0.9308	High Similarity	NPC236934
0.9308	High Similarity	NPC5778
0.9308	High Similarity	NPC115674
0.9304	High Similarity	NPC183672
0.9304	High Similarity	NPC66087
0.9304	High Similarity	NPC29830
0.9304	High Similarity	NPC179198
0.9304	High Similarity	NPC278419
0.9299	High Similarity	NPC48093
0.9299	High Similarity	NPC477629
0.9299	High Similarity	NPC270675
0.9299	High Similarity	NPC470125
0.9299	High Similarity	NPC224530
0.9299	High Similarity	NPC129217
0.9299	High Similarity	NPC216496
0.9299	High Similarity	NPC159579
0.9299	High Similarity	NPC195685
0.9299	High Similarity	NPC85707
0.9299	High Similarity	NPC210961
0.9299	High Similarity	NPC472994
0.9299	High Similarity	NPC259957
0.9299	High Similarity	NPC477628
0.9295	High Similarity	NPC43761
0.929	High Similarity	NPC265480
0.929	High Similarity	NPC261866
0.929	High Similarity	NPC149368
0.9286	High Similarity	NPC211158
0.9286	High Similarity	NPC87304
0.9286	High Similarity	NPC78021
0.9286	High Similarity	NPC268950
0.9286	High Similarity	NPC108706
0.9281	High Similarity	NPC134819
0.9281	High Similarity	NPC325429
0.9281	High Similarity	NPC190217
0.9272	High Similarity	NPC23084
0.9259	High Similarity	NPC239549
0.9259	High Similarity	NPC51774
0.9259	High Similarity	NPC236191
0.9259	High Similarity	NPC208668
0.9259	High Similarity	NPC168789
0.9255	High Similarity	NPC209550
0.9255	High Similarity	NPC51326
0.9255	High Similarity	NPC150767
0.9255	High Similarity	NPC293004
0.9255	High Similarity	NPC138990
0.9255	High Similarity	NPC277532
0.9255	High Similarity	NPC175429

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 NPC246469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	860
0.2-0.3	1664
0.3-0.4	2681
0.4-0.5	1998
0.5-0.6	1082
0.6-0.7	349
0.7-0.8	140
0.8-0.85	30
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9497	High Similarity	NPD7074	Phase 3
0.9481	High Similarity	NPD4381	Clinical (unspecified phase)
0.9434	High Similarity	NPD7804	Clinical (unspecified phase)
0.9313	High Similarity	NPD7054	Approved
0.9255	High Similarity	NPD7472	Approved
0.9141	High Similarity	NPD7251	Discontinued
0.9085	High Similarity	NPD7808	Phase 3
0.908	High Similarity	NPD6797	Phase 2
0.8846	High Similarity	NPD4380	Phase 2
0.878	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.875	High Similarity	NPD7075	Discontinued
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8631	High Similarity	NPD4338	Clinical (unspecified phase)
0.8618	High Similarity	NPD1549	Phase 2
0.8616	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD6559	Discontinued
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD7096	Clinical (unspecified phase)
0.8509	High Similarity	NPD8443	Clinical (unspecified phase)
0.85	High Similarity	NPD6801	Discontinued
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8408	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6799	Approved
0.8302	Intermediate Similarity	NPD5403	Approved
0.8291	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6959	Discontinued
0.8247	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD2801	Approved
0.8221	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8176	Intermediate Similarity	NPD5401	Approved
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8158	Intermediate Similarity	NPD1240	Approved
0.815	Intermediate Similarity	NPD8312	Approved
0.815	Intermediate Similarity	NPD8313	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8136	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1511	Approved
0.811	Intermediate Similarity	NPD8455	Phase 2
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5402	Approved
0.8052	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD3882	Suspended
0.8012	Intermediate Similarity	NPD1512	Approved
0.7976	Intermediate Similarity	NPD5494	Approved
0.7957	Intermediate Similarity	NPD7584	Approved
0.7908	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7768	Phase 2
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7228	Approved
0.7803	Intermediate Similarity	NPD3751	Discontinued
0.7789	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7783	Phase 2
0.7778	Intermediate Similarity	NPD8151	Discontinued
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.7751	Intermediate Similarity	NPD3749	Approved
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7473	Discontinued
0.773	Intermediate Similarity	NPD6779	Approved
0.773	Intermediate Similarity	NPD6780	Approved
0.773	Intermediate Similarity	NPD6776	Approved
0.773	Intermediate Similarity	NPD6781	Approved
0.773	Intermediate Similarity	NPD6778	Approved
0.773	Intermediate Similarity	NPD6782	Approved
0.773	Intermediate Similarity	NPD6777	Approved
0.7701	Intermediate Similarity	NPD7698	Approved
0.7701	Intermediate Similarity	NPD7696	Phase 3
0.7701	Intermediate Similarity	NPD7435	Discontinued
0.7701	Intermediate Similarity	NPD7697	Approved
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.7674	Intermediate Similarity	NPD6232	Discontinued
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7663	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7458	Discontinued
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7701	Phase 2
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.7595	Intermediate Similarity	NPD6651	Approved
0.759	Intermediate Similarity	NPD1653	Approved
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7871	Phase 2
0.7566	Intermediate Similarity	NPD7870	Phase 2
0.7557	Intermediate Similarity	NPD7286	Phase 2
0.7553	Intermediate Similarity	NPD6823	Phase 2
0.755	Intermediate Similarity	NPD1091	Approved
0.7548	Intermediate Similarity	NPD6832	Phase 2
0.7539	Intermediate Similarity	NPD7585	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD2800	Approved
0.7528	Intermediate Similarity	NPD7685	Pre-registration
0.7527	Intermediate Similarity	NPD7699	Phase 2
0.7527	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7700	Phase 2
0.7516	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7487	Intermediate Similarity	NPD7583	Approved
0.7474	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7874	Approved
0.7461	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6535	Approved
0.7459	Intermediate Similarity	NPD6534	Approved
0.7453	Intermediate Similarity	NPD2935	Discontinued
0.7436	Intermediate Similarity	NPD4908	Phase 1
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7240	Approved
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD7801	Approved
0.7412	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD2534	Approved
0.741	Intermediate Similarity	NPD2532	Approved
0.741	Intermediate Similarity	NPD2533	Approved
0.7399	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4966	Approved
0.7384	Intermediate Similarity	NPD4965	Approved
0.7384	Intermediate Similarity	NPD4967	Phase 2
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.7363	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1203	Approved
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6099	Approved
0.7346	Intermediate Similarity	NPD6100	Approved
0.7342	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD7097	Phase 1
0.7317	Intermediate Similarity	NPD1243	Approved
0.7317	Intermediate Similarity	NPD1652	Phase 2
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2799	Discontinued
0.725	Intermediate Similarity	NPD943	Approved
0.7246	Intermediate Similarity	NPD7390	Discontinued
0.7235	Intermediate Similarity	NPD3226	Approved
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7232	Intermediate Similarity	NPD3926	Phase 2
0.7228	Intermediate Similarity	NPD8150	Discontinued
0.7228	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6212	Phase 3
0.7219	Intermediate Similarity	NPD6213	Phase 3
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.72	Intermediate Similarity	NPD919	Approved
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.717	Intermediate Similarity	NPD3027	Phase 3
0.7169	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD2309	Approved
0.7119	Intermediate Similarity	NPD1247	Approved
0.711	Intermediate Similarity	NPD6844	Discontinued
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	Approved
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7094	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2346	Discontinued
0.7083	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD3225	Approved
0.705	Intermediate Similarity	NPD7930	Approved
0.7048	Intermediate Similarity	NPD2424	Discontinued
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6190	Approved
0.7006	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD2654	Approved
0.6994	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD447	Suspended
0.6983	Remote Similarity	NPD5711	Approved
0.6983	Remote Similarity	NPD5710	Approved
0.6974	Remote Similarity	NPD7680	Approved
0.697	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4308	Phase 3

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