NPASS Compound

Structure

NPC289196 OpenBabel06302215342D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.6617 -0.2196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1884 0.6000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6617 1.4197 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1884 2.2393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2420 2.2393 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7687 1.4197 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2420 0.6000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8223 1.4197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0026 0.9465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8212 1.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6399 0.9496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4490 -0.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4561 -1.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2748 -1.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0920 -1.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0960 -0.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2773 0.0043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2673 0.9484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4531 1.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4534 2.3638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9156 0.0025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9128 -1.8736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6335 -1.8815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6285 -2.8268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8193 -1.4114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8187 -0.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8180 -0.4738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2896 -1.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7687 3.0590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6617 3.0590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6081 1.4197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 0 0 0 2 3 1 0 0 0 0 2 7 1 0 0 0 0 3 4 1 0 0 0 0 3 33 1 6 0 0 0 4 5 1 0 0 0 0 4 32 1 1 0 0 0 5 6 1 0 0 0 0 5 31 1 1 0 0 0 6 7 1 0 0 0 0 6 8 1 6 0 0 0 8 9 1 0 0 0 0 9 28 2 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 20 1 0 0 0 0 11 12 1 0 0 0 0 12 27 2 0 0 0 0 12 13 1 0 0 0 0 13 18 2 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 2 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.08
Volume:	413.381
LogP:	0.604
LogD:	0.181
LogS:	-5.142
# Rotatable Bonds:	3
TPSA:	189.26
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.157
Synthetic Accessibility Score:	4.287
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.283
MDCK Permeability:	3.3871598134282976e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.578
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	74.04927825927734%
Volume Distribution (VD):	0.967
Pgp-substrate:	29.758346557617188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.29
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.007

ADMET: Excretion

Clearance (CL):	1.748
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.381
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.728
Carcinogencity:	0.039
Eye Corrosion:	0.004
Eye Irritation:	0.047
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC289196

Natural Product ID:	NPC289196
*Common Name:**	LPXGCZRQLILWOH-UKZWKHHHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LPXGCZRQLILWOH-UKZWKHHHSA-N
Standard InCHI:	InChI=1S/C21H18O12/c1-5-12(23)14(25)15(26)21(30-5)31-9-4-7-11-10-6(19(27)33-18(11)16(9)29-2)3-8(22)13(24)17(10)32-20(7)28/h3-5,12,14-15,21-26H,1-2H3/t5-,12-,14+,15+,21-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc2c3c4c(cc(c(c4oc2=O)O)O)c(=O)oc3c1OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16720461
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861494]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21899269]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25050371]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607351]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33170684]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5391291]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21730	Pouzolzia occidentalis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12362	Coreopsis fasciculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23010	Crinum defixum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22635	Penstemon secundiflorus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22568	Aristolochia elegans	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23698	Gardneria insularis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21603	Eskemukerjea megacarpum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23975	Osteophloeum platyspermum	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24230	Petriella sordida	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21227	Aglaia elaeagnoidea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14279.1	Ficus sarmentosa var. thunbergii	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22829	Ozoroa insignis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20209	Dorstenia lindeniana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22315	Phlogacanthus thyrsiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226.1	Ficus cordata subsp. salicifolia	Subspecies	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20332	Dioscoreophyllum cumminsii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24605	Monochaetia compta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20972	Oscillatoria princeps	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22893	Apterostigma dentigerum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22144	Daphne lancifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6157	Dahlstedtia araripensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21473	Urtica triangularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25647	Taraxacum bicorne	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21967	Astragalus asper	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13355	Selinum carvifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25862	Lafoensia glyptocarpa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22250	Parastrephia lepidophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22447	Sidastrum acuminatum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21282	Aplidium orthium	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21991	Modiolus demissus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23953	Zanthoxylum monophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22509	Syncolostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21859	Centaurea nigrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5064	Derris uliginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21420	Phormia regina	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC289196 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	454
0.1-0.2	2025
0.2-0.3	4449
0.3-0.4	9791
0.4-0.5	8306
0.5-0.6	4551
0.6-0.7	5594
0.7-0.8	5237
0.8-0.85	1441
0.85-0.9	668
0.9-0.95	172
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID

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 NPC289196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	1048
0.2-0.3	2209
0.3-0.4	2644
0.4-0.5	1727
0.5-0.6	743
0.6-0.7	227
0.7-0.8	114
0.8-0.85	19
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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