NPASS Compound

Natural Product: NPC307583

Natural Product ID	NPC307583
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	XUBYZJHAYIWTHA-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
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:0000334] Flavonoids [CHEMONTID:0001615] Flavones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 34 36 0 0 0 0 0 0 0 0999 V2000 5.1220 -1.0116 -0.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0004 -0.1289 0.2926 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6939 -0.5113 0.0421 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6081 0.2828 0.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8821 1.5182 0.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1570 1.9413 1.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2221 1.1021 0.8743 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5245 1.5137 1.1381 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2333 -0.1211 0.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1271 -1.3175 -0.4901 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4390 -1.6691 -0.7267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7945 -2.7416 -1.2427 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4165 -0.7586 -0.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0114 0.4251 0.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9903 1.3453 0.5795 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3240 1.0612 0.3728 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6927 -0.1414 -0.2041 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7443 -1.0610 -0.5757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0783 -2.2846 -1.1603 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0356 -0.4229 -0.4100 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3190 1.9735 0.7385 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7378 0.6979 0.4073 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9389 -1.4459 -1.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2927 -1.8229 0.6965 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0801 -0.4580 -0.1369 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5636 -1.4818 -0.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0256 2.1526 1.1795 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3063 2.9093 1.6581 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8566 1.3498 2.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6453 -2.0220 -0.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6714 2.2748 1.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0506 -3.1477 -0.6197 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5172 -0.9197 0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2029 2.9199 0.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 4 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 16 21 1 0 14 22 1 0 7 2 1 0 22 9 1 0 18 13 1 0 1 23 1 0 1 24 1 0 1 25 1 0 3 26 1 0 5 27 1 0 6 28 1 0 8 29 1 0 10 30 1 0 15 31 1 0 19 32 1 0 20 33 1 0 21 34 1 0 M END

Standard InCHIKey	XUBYZJHAYIWTHA-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C16H12O6/c1-7-4-8(2-3-9(7)17)12-5-10(18)14-13(22-12)6-11(19)15(20)16(14)21/h2-6,17,19-21H,1H3
SMILES	Cc1cc(ccc1O)c1cc(=O)c2c(cc(c(c2O)O)O)o1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	300.06	Volume:	291.273 ? Van der Waals volume.
Dense:	1.03	LogP:	2.493 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.043 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.526 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	18.0
TPSA:	111.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.514	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.518	Fsp³:	0.062
MCE-18:	19.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.907	Fluc inhibitor:	0.826 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.974 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.593 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.6	Promiscuous compounds:	0.732

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919	MDCK Permeability:	-4.75
Pgp-inhibitor:	0.052	Pgp-substrate:	0.111
PAMPA:	0.798 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.715	30% Bioavailability (F30%):	0.862
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.977
Plasma Protein Binding (PPB):	97.622%	Volume Distribution (VD):	-0.486
Fu:	1.931% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.969
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.928
BSEP inhibitor:	0.864

ADMET: Metabolism

CYP1A2-inhibitor:	0.023	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.096	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.944	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.011
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.295 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.313

Half-life (T1/2):

1.281

ADMET: Toxicity

hERG Blockers:	0.078	hERG Blockers (10um):	0.693
Human Hepatotoxicity (H-HT):	0.368	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.685	Rat Oral Acute Toxicity:	0.463
Maximum Recommended Daily Dose:	0.848	Skin Sensitization:	0.989
Carcinogencity:	0.636	Eye Corrosion:	0.554
Eye Irritation:	0.997	Respiratory Toxicity:	0.684
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.374
Hematotoxicity:	0.036	Drug-induced Nephrotoxicity:	0.01
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.012
A549 Cytotoxicity:	0.826	Hek293 Cytotoxicity:	0.529
BCF:	1.026 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.789 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.629 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.19 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[19093848]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
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]
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]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
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]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	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]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15806	Rhododendron campylocarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15513	Pseudocyphellaria rubella	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26381	Bombus pascuorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10527	Cyathula tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8556	Eucalyptus kitsoniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27134	Euphrasia rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2667	Acacia lasiopetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15718	Lindera sericea	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO255	Solanum pseudopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13225	Spergula japonica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22101	Himantoglossum hircinum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29322	Rhodanthe maryonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21851	Chaetomella raphigera	Species	Chaetomellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11243	Exochorda giraldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26951	Gymnopus androsaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1777	Toddalia aculeata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13460	Asphodeline damascena	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	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]

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	Organism Name	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

Molecular-level activity

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

In vitro activity

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

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC307583 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	30910
0.1-0.2	16319
0.2-0.3	2085
0.3-0.4	423
0.4-0.5	105
0.5-0.6	12
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.74	Intermediate Similarity	NPC130230
0.74	Intermediate Similarity	NPC275772
0.6863	Remote Similarity	NPC239312
0.6429	Remote Similarity	NPC184136
0.5357	Remote Similarity	NPC77858
0.5345	Remote Similarity	NPC201395
0.5303	Remote Similarity	NPC59210
0.5303	Remote Similarity	NPC301217
0.5263	Remote Similarity	NPC195351
0.5172	Remote Similarity	NPC279121
0.5167	Remote Similarity	NPC482122
0.5088	Remote Similarity	NPC50898
0.5082	Remote Similarity	NPC100887
0.5082	Remote Similarity	NPC214138
0.5077	Remote Similarity	NPC172986
0.5077	Remote Similarity	NPC3825

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC307583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5729
0.1-0.2	3352
0.2-0.3	63
0.3-0.4	4
0.4-0.5	1
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5172	Remote Similarity	NPD1511	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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