NPASS Compound

Structure

CID64141 OpenBabel06191715402D 44 47 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 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 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 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 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -10.3923 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 5 2 0 0 0 0 2 14 1 0 0 0 0 3 6 2 0 0 0 0 3 15 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 40 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 41 1 0 0 0 0 13 1 1 1 0 0 0 13 22 1 0 0 0 0 13 42 1 0 0 0 0 16 18 2 0 0 0 0 16 30 1 0 0 0 0 17 19 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 12 1 1 0 0 0 20 23 1 0 0 0 0 20 43 1 0 0 0 0 21 34 2 0 0 0 0 21 41 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 27 1 0 0 0 0 23 36 1 6 0 0 0 24 25 1 0 0 0 0 24 37 1 1 0 0 0 25 29 1 0 0 0 0 25 38 1 1 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 39 1 6 0 0 0 27 44 1 1 0 0 0 28 40 1 1 0 0 0 28 43 1 0 0 0 0 29 42 1 0 0 0 0 29 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.21
Volume:	586.676
LogP:	0.871
LogD:	-0.045
LogS:	-2.286
# Rotatable Bonds:	11
TPSA:	245.29
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.087
Synthetic Accessibility Score:	4.708
Fsp3:	0.483
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.562
MDCK Permeability:	2.545528332120739e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.982
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	95.25917053222656%
Volume Distribution (VD):	0.306
Pgp-substrate:	6.672189235687256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.551
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.063
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.366
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.56
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.973
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.247
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC64141

Natural Product ID:	NPC64141
*Common Name:**	Isoacteoside
IUPAC Name:	[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Isoacetoside; Isoacteoside; Isoverbascoside
Standard InCHIKey:	FNMHEHXNBNCPCI-QEOJJFGVSA-N
Standard InCHI:	InChI=1S/C29H36O15/c1-13-22(35)24(37)25(38)29(42-13)44-27-23(36)20(12-41-21(34)7-4-14-2-5-16(30)18(32)10-14)43-28(26(27)39)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
SMILES:	O=C(OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504873
PubChem CID:	6476333
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473417]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	stem	n.a.	PMID[12575075]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12575075]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15577255]
NPO21591	Psorothamnus polydenius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679330]
NPO21591	Psorothamnus polydenius	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679330]
NPO21591	Psorothamnus polydenius	Species	Fabaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679330]
NPO21591	Psorothamnus polydenius	Species	Fabaceae	Eukaryota	n.a.	flower	n.a.	PMID[15679330]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO1939	Swartzia langsdorffii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124782]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[16124783]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	aerial parts	Morocco	n.a.	PMID[16124783]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093848]
NPO982	Phlomis brunneogaleata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361168]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO21509	Laurencia similis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20961755]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276742]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO40812	Castilleja linariaefolia	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[2380718]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25900014]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26110519]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562611]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28290701]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30188125]
NPO40190	Lippia rubella	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817148]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO6610	Markhamia lutea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599250]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4838	Phlomis umbrosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO982	Phlomis brunneogaleata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20106	Polygala sabulosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO151	Pedicularis striata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30076	Lippia dulcis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18558	Abies alba	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO77	Brandisia hancei	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO982	Phlomis brunneogaleata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4838	Phlomis umbrosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23388	Phyla dulcis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18558	Abies alba	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18116	Dregea volubilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20106	Polygala sabulosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18120	Radix rehmanniae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO151	Pedicularis striata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	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]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	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]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3734	Vigna umbellata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4838	Phlomis umbrosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5565	Harpagophytum procumbens	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13460	Asphodeline damascena	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO77	Brandisia hancei	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15513	Pseudocyphellaria rubella	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11243	Exochorda giraldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15806	Rhododendron campylocarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25577	Samuela carnerosana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23170	Orobanche coerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4203	Phlomoides rotata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26951	Gymnopus androsaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3828	Cereus pachanoi	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO151	Pedicularis striata	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1777	Toddalia aculeata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12751	Ajuga japonica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO13153	Callicarpa macrophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1939	Swartzia langsdorffii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6610	Markhamia lutea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9299.3	Hordeum vulgare var. distichon	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2667	Acacia lasiopetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4838	Phlomis umbrosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23388	Phyla dulcis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8142	Pinus pumilio	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18116	Dregea volubilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4129	Veronica persica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27134	Euphrasia rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10680	Cistanche deserticola	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3734	Vigna umbellata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13225	Spergula japonica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29463	Pogostemon cablin	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15718	Lindera sericea	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21851	Chaetomella raphigera	Species	Chaetomellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8918	Plantago depressa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20856	Pyrethrum santolinoides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4039	Verbascum pseudonobile	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8556	Eucalyptus kitsoniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20437	Chrysothamnus stylosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21509	Laurencia similis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19048	Pinellia ternata	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20106	Polygala sabulosa	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14003	Crotalaria lachnosema	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO255	Solanum pseudopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20303	Artemisia kulbadica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20240	Discodermia calyx	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO982	Phlomis brunneogaleata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17830	Adonis aleppica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10527	Cyathula tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21591	Psorothamnus polydenius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16786	Fagus pumilio	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18558	Abies alba	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8446	Alnus mandshurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28240	0tholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12103	Salvia ballotiflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29322	Rhodanthe maryonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16365	Ageratum tomentosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15817	Alternaria scirpicola	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26381	Bombus pascuorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22101	Himantoglossum hircinum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1009	Stentor coeruleus	Species	Stentoridae	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
EC50	4
ED50	1
IC50	17
MIC	1
Others	28

Activity Type	# Activity
Cell Line	16
Individual Protein	10
NON-MOLECULAR	4
Organism	8
Others	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	10.0	ug ml-1	PMID[545429]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	101.5	pg/ml	PMID[545433]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	175.5	pg/ml	PMID[545433]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[545433]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	43.7	%	PMID[545435]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	57.3	%	PMID[545435]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	101.2	%	PMID[545435]
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	5300.0	nM	PMID[545435]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	-4.6	%	PMID[545435]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	19.0	%	PMID[545435]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	61.9	%	PMID[545435]
NPT1460	Cell Line	L929	Mus musculus	Inhibition	=	102.4	%	PMID[545435]
NPT1460	Cell Line	L929	Mus musculus	IC50	=	22.7	ug.mL-1	PMID[545435]
NPT568	Individual Protein	Matrix metalloproteinase-2	Homo sapiens	IC50	=	8960.0	nM	PMID[545436]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	IC50	=	91410.0	nM	PMID[545436]
NPT280	Individual Protein	Matrix metalloproteinase 9	Homo sapiens	IC50	=	14280.0	nM	PMID[545436]
NPT1089	Individual Protein	Matrix metalloproteinase 12	Homo sapiens	IC50	=	8220.0	nM	PMID[545436]
NPT1090	Individual Protein	Matrix metalloproteinase 13	Homo sapiens	IC50	=	11090.0	nM	PMID[545436]
NPT568	Individual Protein	Matrix metalloproteinase-2	Homo sapiens	Inhibition	>	30.0	%	PMID[545436]
NPT567	Individual Protein	Matrix metalloproteinase 3	Homo sapiens	Inhibition	>	30.0	%	PMID[545436]
NPT280	Individual Protein	Matrix metalloproteinase 9	Homo sapiens	Inhibition	>	30.0	%	PMID[545436]
NPT1089	Individual Protein	Matrix metalloproteinase 12	Homo sapiens	Inhibition	>	30.0	%	PMID[545436]
NPT1090	Individual Protein	Matrix metalloproteinase 13	Homo sapiens	Inhibition	>	30.0	%	PMID[545436]
NPT1	Others	Radical scavenging activity		IC50	=	1300.0	nM	PMID[545430]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.228	n.a.	PMID[545430]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	24.6	n.a.	PMID[545430]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	7.2	n.a.	PMID[545430]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	0.17	ug.mL-1	PMID[545431]
NPT27	Others	Unspecified		IC50	=	125.0	ug.mL-1	PMID[545431]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	735.0	n.a.	PMID[545431]
NPT1	Others	Radical scavenging activity		IC50	=	20000.0	nM	PMID[545432]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	1.1	ug.mL-1	PMID[545431]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	EC50	=	0.62	ug.mL-1	PMID[545431]
NPT27	Others	Unspecified		IC50	=	51.4	ug.mL-1	PMID[545431]
NPT27	Others	Unspecified		IC50	=	75.0	ug.mL-1	PMID[545431]
NPT27	Others	Unspecified		IC50	=	89.0	ug.mL-1	PMID[545431]
NPT27	Others	Unspecified		IC50	=	30.0	ug.mL-1	PMID[545431]
NPT27	Others	Unspecified		IC50	=	27.0	ug.mL-1	PMID[545431]
NPT2	Others	Unspecified		Ratio IC50/EC50	=	84.0	n.a.	PMID[545431]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	1200.0	nM	PMID[545434]
NPT35	Others	n.a.		Ratio	=	0.07	n.a.	PMID[545434]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	46.1	%	PMID[545435]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	70.9	%	PMID[545435]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	40.2	%	PMID[545435]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	58.7	%	PMID[545435]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[545435]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	125.0	ug.mL-1	PMID[545437]

☑ 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 NPC64141 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	301
0.1-0.2	1303
0.2-0.3	3109
0.3-0.4	7603
0.4-0.5	10013
0.5-0.6	7802
0.6-0.7	8593
0.7-0.8	3443
0.8-0.85	332
0.85-0.9	109
0.9-0.95	66
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472350
1.0	High Similarity	NPC197316
1.0	High Similarity	NPC81515
1.0	High Similarity	NPC89105
1.0	High Similarity	NPC476383
1.0	High Similarity	NPC68092
0.9924	High Similarity	NPC260425
0.985	High Similarity	NPC476385
0.985	High Similarity	NPC476377
0.985	High Similarity	NPC47471
0.985	High Similarity	NPC134405
0.9848	High Similarity	NPC205195
0.9776	High Similarity	NPC265648
0.9776	High Similarity	NPC222433
0.9774	High Similarity	NPC475530
0.9774	High Similarity	NPC473799
0.9773	High Similarity	NPC78363
0.9704	High Similarity	NPC96795
0.9704	High Similarity	NPC264632
0.9704	High Similarity	NPC476397
0.9704	High Similarity	NPC119537
0.9704	High Similarity	NPC298257
0.9704	High Similarity	NPC476381
0.9704	High Similarity	NPC476380
0.9704	High Similarity	NPC175214
0.9704	High Similarity	NPC269141
0.9704	High Similarity	NPC476384
0.9704	High Similarity	NPC76406
0.9704	High Similarity	NPC476378
0.9704	High Similarity	NPC476375
0.9704	High Similarity	NPC247032
0.9704	High Similarity	NPC112
0.9704	High Similarity	NPC205864
0.9695	High Similarity	NPC287597
0.9695	High Similarity	NPC886
0.9695	High Similarity	NPC34293
0.9632	High Similarity	NPC296954
0.9632	High Similarity	NPC196063
0.9632	High Similarity	NPC64195
0.9632	High Similarity	NPC300894
0.9632	High Similarity	NPC141455
0.9624	High Similarity	NPC476376
0.9562	High Similarity	NPC34927
0.9562	High Similarity	NPC476382
0.9562	High Similarity	NPC252292
0.9562	High Similarity	NPC34587
0.9562	High Similarity	NPC100998
0.9559	High Similarity	NPC105005
0.9552	High Similarity	NPC321638
0.9552	High Similarity	NPC171134
0.9552	High Similarity	NPC328273
0.9552	High Similarity	NPC321184
0.9542	High Similarity	NPC473285
0.9493	High Similarity	NPC229505
0.9474	High Similarity	NPC476870
0.9466	High Similarity	NPC46137
0.9466	High Similarity	NPC235294
0.9424	High Similarity	NPC232992
0.9343	High Similarity	NPC140502
0.9318	High Similarity	NPC225384
0.9318	High Similarity	NPC246869
0.9318	High Similarity	NPC138777
0.9313	High Similarity	NPC477294
0.9313	High Similarity	NPC477293
0.9313	High Similarity	NPC229784
0.9291	High Similarity	NPC470933
0.9291	High Similarity	NPC471062
0.9291	High Similarity	NPC306890
0.9291	High Similarity	NPC94871
0.9291	High Similarity	NPC476398
0.9291	High Similarity	NPC259347
0.9291	High Similarity	NPC473427
0.9291	High Similarity	NPC476386
0.9275	High Similarity	NPC40305
0.9254	High Similarity	NPC471883
0.9248	High Similarity	NPC254275
0.9237	High Similarity	NPC232880
0.9225	High Similarity	NPC470934
0.9225	High Similarity	NPC257970
0.9225	High Similarity	NPC188393
0.9225	High Similarity	NPC470927
0.9214	High Similarity	NPC476865
0.9209	High Similarity	NPC476867
0.9185	High Similarity	NPC263829
0.9179	High Similarity	NPC254398
0.9173	High Similarity	NPC219677
0.9167	High Similarity	NPC184092
0.916	High Similarity	NPC476873
0.916	High Similarity	NPC288416
0.9143	High Similarity	NPC476864
0.9143	High Similarity	NPC476866
0.9143	High Similarity	NPC476868
0.9143	High Similarity	NPC476869
0.9137	High Similarity	NPC478239
0.913	High Similarity	NPC186406
0.9104	High Similarity	NPC473924
0.9097	High Similarity	NPC106818
0.9084	High Similarity	NPC471157
0.9071	High Similarity	NPC110063
0.9065	High Similarity	NPC157816
0.9065	High Similarity	NPC296643
0.9034	High Similarity	NPC87403
0.903	High Similarity	NPC478255
0.9021	High Similarity	NPC106138
0.9015	High Similarity	NPC106677
0.9015	High Similarity	NPC264900
0.9015	High Similarity	NPC108659
0.9015	High Similarity	NPC231607
0.9015	High Similarity	NPC79715
0.9008	High Similarity	NPC126991
0.9008	High Similarity	NPC83218
0.9007	High Similarity	NPC216819
0.9007	High Similarity	NPC262182
0.9007	High Similarity	NPC287615
0.9007	High Similarity	NPC83743
0.8978	High Similarity	NPC157554
0.8966	High Similarity	NPC478268
0.8951	High Similarity	NPC199311
0.8951	High Similarity	NPC192763
0.8951	High Similarity	NPC3460
0.8951	High Similarity	NPC215095
0.8951	High Similarity	NPC261122
0.8951	High Similarity	NPC210611
0.8951	High Similarity	NPC300262
0.8951	High Similarity	NPC28776
0.8951	High Similarity	NPC201148
0.8951	High Similarity	NPC23677
0.8951	High Similarity	NPC80732
0.8951	High Similarity	NPC473138
0.8951	High Similarity	NPC28651
0.8947	High Similarity	NPC225307
0.8944	High Similarity	NPC199928
0.8939	High Similarity	NPC94179
0.8936	High Similarity	NPC292443
0.8936	High Similarity	NPC232228
0.8921	High Similarity	NPC202700
0.8905	High Similarity	NPC123988
0.8904	High Similarity	NPC471874
0.8889	High Similarity	NPC478242
0.8849	High Similarity	NPC220942
0.8849	High Similarity	NPC226005
0.8849	High Similarity	NPC100389
0.8841	High Similarity	NPC52277
0.8841	High Similarity	NPC177035
0.8841	High Similarity	NPC199459
0.8841	High Similarity	NPC470572
0.8832	High Similarity	NPC35731
0.8832	High Similarity	NPC135127
0.8828	High Similarity	NPC476871
0.8806	High Similarity	NPC148982
0.8786	High Similarity	NPC106944
0.8779	High Similarity	NPC52097
0.8777	High Similarity	NPC470413
0.8777	High Similarity	NPC126206
0.8777	High Similarity	NPC138738
0.8777	High Similarity	NPC84789
0.8777	High Similarity	NPC310252
0.8777	High Similarity	NPC100558
0.8777	High Similarity	NPC302583
0.8767	High Similarity	NPC143480
0.8767	High Similarity	NPC7145
0.8767	High Similarity	NPC85192
0.8767	High Similarity	NPC125823
0.8759	High Similarity	NPC28637
0.8759	High Similarity	NPC283839
0.8759	High Similarity	NPC90896
0.8732	High Similarity	NPC113680
0.8732	High Similarity	NPC278961
0.8732	High Similarity	NPC204644
0.8731	High Similarity	NPC35288
0.8731	High Similarity	NPC45224
0.8731	High Similarity	NPC471882
0.8731	High Similarity	NPC173150
0.8731	High Similarity	NPC471881
0.8731	High Similarity	NPC156692
0.8725	High Similarity	NPC11411
0.8707	High Similarity	NPC169404
0.8707	High Similarity	NPC53587
0.8707	High Similarity	NPC472612
0.8707	High Similarity	NPC289967
0.8707	High Similarity	NPC472611
0.8707	High Similarity	NPC176186
0.8705	High Similarity	NPC471664
0.8705	High Similarity	NPC186418
0.8705	High Similarity	NPC471872
0.8705	High Similarity	NPC37468
0.8705	High Similarity	NPC471665
0.8705	High Similarity	NPC154485
0.8702	High Similarity	NPC147654
0.8702	High Similarity	NPC266045
0.8702	High Similarity	NPC11724
0.8699	High Similarity	NPC69367
0.869	High Similarity	NPC478237
0.8671	High Similarity	NPC297342
0.8662	High Similarity	NPC473873
0.8662	High Similarity	NPC473792
0.8658	High Similarity	NPC131532
0.8657	High Similarity	NPC252114
0.8657	High Similarity	NPC61181
0.8649	High Similarity	NPC150442

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 NPC64141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	777
0.2-0.3	1611
0.3-0.4	2910
0.4-0.5	2002
0.5-0.6	1184
0.6-0.7	369
0.7-0.8	41
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7266	Discontinued
0.8255	Intermediate Similarity	NPD1653	Approved
0.8219	Intermediate Similarity	NPD6190	Approved
0.795	Intermediate Similarity	NPD7054	Approved
0.7914	Intermediate Similarity	NPD7685	Pre-registration
0.7901	Intermediate Similarity	NPD7074	Phase 3
0.7901	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD7228	Approved
0.7817	Intermediate Similarity	NPD3027	Phase 3
0.7805	Intermediate Similarity	NPD7251	Discontinued
0.7744	Intermediate Similarity	NPD6797	Phase 2
0.7658	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1613	Approved
0.7651	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7808	Phase 3
0.7632	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6234	Discontinued
0.7561	Intermediate Similarity	NPD3818	Discontinued
0.755	Intermediate Similarity	NPD8166	Discontinued
0.7532	Intermediate Similarity	NPD8455	Phase 2
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6674	Discontinued
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD37	Approved
0.7438	Intermediate Similarity	NPD4965	Approved
0.7438	Intermediate Similarity	NPD4967	Phase 2
0.7438	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD7240	Approved
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1091	Approved
0.7333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3022	Approved
0.7313	Intermediate Similarity	NPD3021	Approved
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD8312	Approved
0.7294	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD6559	Discontinued
0.7267	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3705	Approved
0.725	Intermediate Similarity	NPD1934	Approved
0.7208	Intermediate Similarity	NPD4628	Phase 3
0.7205	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3455	Phase 2
0.7163	Intermediate Similarity	NPD1357	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD7097	Phase 1
0.7125	Intermediate Similarity	NPD4380	Phase 2
0.7124	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5125	Phase 3
0.7113	Intermediate Similarity	NPD5126	Approved
0.7102	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5844	Phase 1
0.7099	Intermediate Similarity	NPD1465	Phase 2
0.708	Intermediate Similarity	NPD228	Approved
0.7073	Intermediate Similarity	NPD7075	Discontinued
0.7067	Intermediate Similarity	NPD4060	Phase 1
0.7056	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3817	Phase 2
0.7048	Intermediate Similarity	NPD8127	Discontinued
0.7032	Intermediate Similarity	NPD1652	Phase 2
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.702	Intermediate Similarity	NPD4340	Discontinued
0.7006	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6995	Remote Similarity	NPD7680	Approved
0.6994	Remote Similarity	NPD2978	Approved
0.6994	Remote Similarity	NPD2801	Approved
0.6994	Remote Similarity	NPD2977	Approved
0.698	Remote Similarity	NPD7095	Approved
0.6972	Remote Similarity	NPD9545	Approved
0.6964	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2861	Phase 2
0.6957	Remote Similarity	NPD969	Suspended
0.6951	Remote Similarity	NPD5402	Approved
0.6933	Remote Similarity	NPD3764	Approved
0.6913	Remote Similarity	NPD4908	Phase 1
0.6912	Remote Similarity	NPD1358	Approved
0.6909	Remote Similarity	NPD3882	Suspended
0.6908	Remote Similarity	NPD5124	Phase 1
0.6908	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5314	Approved
0.6863	Remote Similarity	NPD6653	Approved
0.6857	Remote Similarity	NPD5283	Phase 1
0.6855	Remote Similarity	NPD1511	Approved
0.6852	Remote Similarity	NPD7458	Discontinued
0.6849	Remote Similarity	NPD9269	Phase 2
0.6846	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3062	Approved
0.6842	Remote Similarity	NPD3061	Approved
0.6842	Remote Similarity	NPD3059	Approved
0.6842	Remote Similarity	NPD3751	Discontinued
0.6842	Remote Similarity	NPD3620	Phase 2
0.6839	Remote Similarity	NPD2935	Discontinued
0.6832	Remote Similarity	NPD5403	Approved
0.6829	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3496	Discontinued
0.6824	Remote Similarity	NPD3094	Phase 2
0.6821	Remote Similarity	NPD6798	Discontinued
0.6821	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4536	Approved
0.6818	Remote Similarity	NPD4538	Approved
0.6815	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6232	Discontinued
0.6803	Remote Similarity	NPD2983	Phase 2
0.6803	Remote Similarity	NPD2982	Phase 2
0.6797	Remote Similarity	NPD1933	Approved
0.6797	Remote Similarity	NPD6355	Discontinued
0.6795	Remote Similarity	NPD5763	Approved
0.6795	Remote Similarity	NPD5762	Approved
0.679	Remote Similarity	NPD3686	Approved
0.679	Remote Similarity	NPD3687	Approved
0.6788	Remote Similarity	NPD7819	Suspended
0.6786	Remote Similarity	NPD7843	Approved
0.6784	Remote Similarity	NPD7473	Discontinued
0.6781	Remote Similarity	NPD422	Phase 1
0.678	Remote Similarity	NPD8150	Discontinued
0.6774	Remote Similarity	NPD8320	Phase 1
0.6774	Remote Similarity	NPD8319	Approved
0.677	Remote Similarity	NPD1512	Approved
0.677	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6385	Approved
0.6768	Remote Similarity	NPD6386	Approved
0.6761	Remote Similarity	NPD7157	Approved
0.6761	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9384	Approved
0.6759	Remote Similarity	NPD9381	Approved
0.6743	Remote Similarity	NPD7549	Discontinued
0.6742	Remote Similarity	NPD6841	Approved
0.6742	Remote Similarity	NPD6843	Phase 3
0.6742	Remote Similarity	NPD6842	Approved
0.6735	Remote Similarity	NPD2981	Phase 2
0.6733	Remote Similarity	NPD9494	Approved
0.6733	Remote Similarity	NPD3018	Phase 2
0.6732	Remote Similarity	NPD825	Approved
0.6732	Remote Similarity	NPD943	Approved
0.6732	Remote Similarity	NPD1558	Phase 1
0.6732	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD826	Approved
0.6731	Remote Similarity	NPD9570	Approved
0.6727	Remote Similarity	NPD6801	Discontinued
0.6721	Remote Similarity	NPD7700	Phase 2
0.6721	Remote Similarity	NPD7699	Phase 2
0.672	Remote Similarity	NPD7435	Discontinued
0.672	Remote Similarity	NPD8151	Discontinued
0.6718	Remote Similarity	NPD2934	Approved
0.6718	Remote Similarity	NPD2933	Approved
0.6715	Remote Similarity	NPD3134	Approved
0.6709	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3060	Approved
0.6708	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5401	Approved
0.6706	Remote Similarity	NPD3787	Discontinued
0.6689	Remote Similarity	NPD9622	Approved
0.6686	Remote Similarity	NPD7039	Approved
0.6686	Remote Similarity	NPD7038	Approved
0.6686	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD4108	Discontinued
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD5588	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD3092	Approved
0.6667	Remote Similarity	NPD5535	Approved
0.6667	Remote Similarity	NPD5960	Phase 3
0.6648	Remote Similarity	NPD6534	Approved
0.6648	Remote Similarity	NPD6535	Approved
0.6646	Remote Similarity	NPD6799	Approved
0.6646	Remote Similarity	NPD4357	Discontinued
0.6644	Remote Similarity	NPD4626	Approved
0.6644	Remote Similarity	NPD3225	Approved
0.6642	Remote Similarity	NPD3020	Approved
0.6623	Remote Similarity	NPD4140	Approved
0.6621	Remote Similarity	NPD1548	Phase 1
0.6619	Remote Similarity	NPD2684	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