NPASS Compound

Structure

NPC43357 OpenBabel06302215322D 56 63 0 0 1 0 0 0 0 0999 V2000 0.7269 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5539 0.1733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6539 -0.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0548 -1.5326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9502 -1.0189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8430 -1.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7335 -1.0333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6335 -1.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5289 -1.0336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7417 -0.1563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6416 0.7408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3685 1.2760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1955 0.9141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2956 0.0170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5687 -0.5182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6830 -1.5434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2405 -0.3966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0261 1.5257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2408 1.5496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0714 2.1612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5875 2.1725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7605 2.5344 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8597 2.5916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9936 2.3373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2667 1.8021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7667 1.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8217 1.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4588 3.4004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9588 4.1520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8597 4.0947 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2605 3.2859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2900 3.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4310 4.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5007 5.0762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5182 0.0048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6365 0.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7411 0.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8442 0.5170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9537 0.0061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1147 0.4939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6413 1.4925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3579 0.4914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6197 -2.5782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4562 -3.0702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7292 -3.0890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8426 -2.5746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9471 -3.0882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0521 -2.5715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2110 -3.0556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9458 -4.0587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9270 -1.2590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1001 -0.8971 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 -0.9450 0.4136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7306 -1.5087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0414 -2.2842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 53 2 0 0 0 0 1 2 1 0 0 0 0 2 26 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 51 1 0 0 0 0 4 48 2 0 0 0 0 4 5 1 0 0 0 0 5 39 1 0 0 0 0 5 6 2 0 0 0 0 6 46 1 0 0 0 0 6 7 1 0 0 0 0 7 37 2 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 8 43 1 0 0 0 0 9 10 1 0 0 0 0 9 35 1 0 0 0 0 10 15 2 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 22 21 1 6 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 6 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 27 2 0 0 0 0 28 29 1 0 0 0 0 29 30 1 0 0 0 0 29 34 1 1 0 0 0 30 31 1 0 0 0 0 30 33 1 1 0 0 0 31 32 1 1 0 0 0 35 36 2 0 0 0 0 35 42 1 0 0 0 0 36 37 1 0 0 0 0 36 41 1 0 0 0 0 37 38 1 0 0 0 0 38 39 1 0 0 0 0 39 40 2 0 0 0 0 43 44 2 0 0 0 0 43 45 1 0 0 0 0 45 46 1 0 0 0 0 46 47 2 0 0 0 0 47 48 1 0 0 0 0 47 50 1 0 0 0 0 48 49 1 0 0 0 0 51 52 2 0 0 0 0 51 56 1 0 0 0 0 52 53 1 0 0 0 0 52 55 1 0 0 0 0 53 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	246.17
Volume:	259.281
LogP:	1.533
LogD:	1.943
LogS:	-1.399
# Rotatable Bonds:	0
TPSA:	23.55
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	4.108
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.763
MDCK Permeability:	8.60588170326082e-06
Pgp-inhibitor:	0.025
Pgp-substrate:	0.125
Human Intestinal Absorption (HIA):	0.22
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.114

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.517
Plasma Protein Binding (PPB):	50.335453033447266%
Volume Distribution (VD):	1.427
Pgp-substrate:	51.98757553100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.601
CYP2D6-substrate:	0.725
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.568

ADMET: Excretion

Clearance (CL):	3.116
Half-life (T1/2):	0.704

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.498
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.837
Maximum Recommended Daily Dose:	0.2
Skin Sensitization:	0.942
Carcinogencity:	0.69
Eye Corrosion:	0.822
Eye Irritation:	0.806
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC43357

Natural Product ID:	NPC43357
*Common Name:**	IQHIEHIKNWLKFB-YRUXTXJMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IQHIEHIKNWLKFB-YRUXTXJMSA-N
Standard InCHI:	InChI=1S/C34H22O22/c35-6-1-4-9(19(39)17(6)37)11-15-13-14-16(33(50)56-28(13)23(43)21(11)41)12(22(42)24(44)29(14)55-32(15)49)10-5(2-7(36)18(38)20(10)40)31(48)54-27-8(3-52-30(4)47)53-34(51)26(46)25(27)45/h1-2,8,25-27,34-46,51H,3H2/t8-,25+,26-,27+,34+/m0/s1
SMILES:	c1c2c(-c3c4c5c6c(c(-c7c(cc(c(c7O)O)O)C(=O)O[C@@H]7[C@H](COC2=O)O[C@H]([C@H]([C@H]7O)O)O)c(c(c6oc4=O)O)O)c(=O)oc5c(c3O)O)c(c(c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
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]
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]
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]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
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]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	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]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22976	Ruta microcarpa	Species	Rutaceae	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]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO12088	Conyza canadensis	Species	Asteraceae	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]
NPO21349	Punica granatum	Species	Lythraceae	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]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	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]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21282	Aplidium orthium	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21991	Modiolus demissus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22509	Syncolostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22250	Parastrephia lepidophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21420	Phormia regina	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12362	Coreopsis fasciculata	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]
NPO22315	Phlogacanthus thyrsiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23953	Zanthoxylum monophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22635	Penstemon secundiflorus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21859	Centaurea nigrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21730	Pouzolzia occidentalis	Species	Urticaceae	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]
NPO23010	Crinum defixum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22893	Apterostigma dentigerum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20096	Cirsium japonicum	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]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22829	Ozoroa insignis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21227	Aglaia elaeagnoidea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20209	Dorstenia lindeniana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20332	Dioscoreophyllum cumminsii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20972	Oscillatoria princeps	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13355	Selinum carvifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21473	Urtica triangularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	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 NPC43357 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	500
0.1-0.2	2180
0.2-0.3	4812
0.3-0.4	10187
0.4-0.5	7982
0.5-0.6	4708
0.6-0.7	5750
0.7-0.8	5189
0.8-0.85	868
0.85-0.9	479
0.9-0.95	31
0.95-1	11

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 NPC43357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	1117
0.2-0.3	2274
0.3-0.4	2657
0.4-0.5	1680
0.5-0.6	678
0.6-0.7	195
0.7-0.8	97
0.8-0.85	12
0.85-0.9	9
0.9-0.95	0
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