NPASS Compound

Natural Product: NPC106197

Natural Product ID	NPC106197
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DZMMTSZAYZRIIY-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46850205
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001753] Benzoylindoles

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 -4.5086 1.8293 -1.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0892 0.9081 -0.3752 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7367 0.6103 -0.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6812 1.0643 -0.9734 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5003 0.5100 -0.5374 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 -0.3144 0.4646 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1093 -1.1687 1.2727 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7364 -1.9536 2.2477 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0910 -1.9100 2.4410 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8102 -1.0612 1.6325 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2221 -0.2728 0.6594 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2059 -0.9502 1.7573 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7486 0.7585 -1.1328 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 1.4958 -2.2307 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0722 0.3746 -0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9313 -0.0423 -1.8162 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2572 -0.3317 -1.5901 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7945 -0.2208 -0.3300 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9691 0.1871 0.6929 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6537 0.4699 0.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1498 -0.5151 -0.0884 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8053 1.2409 -2.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4111 2.4052 -1.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6891 2.5238 -1.6624 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7518 1.7753 -1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9370 -1.2576 1.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1090 -2.6006 2.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6184 -2.4931 3.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7455 -1.0931 0.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5573 -0.1469 -2.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9137 -0.6509 -2.3787 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4014 0.2753 1.7007 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0128 0.8057 1.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5386 -0.2512 0.8083 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 5 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 18 21 1 0 11 3 1 0 20 15 1 0 11 6 1 0 1 22 1 0 1 23 1 0 1 24 1 0 4 25 1 0 7 26 1 0 8 27 1 0 9 28 1 0 12 29 1 0 16 30 1 0 17 31 1 0 19 32 1 0 20 33 1 0 21 34 1 0 M END

Standard InCHIKey	DZMMTSZAYZRIIY-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C16H13NO4/c1-21-14-9-17(12-3-2-4-13(19)15(12)14)16(20)10-5-7-11(18)8-6-10/h2-9,18-19H,1H3
SMILES	COc1cn(c2cccc(c12)O)C(=O)c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	283.08	Volume:	284.689 ? Van der Waals volume.
Dense:	0.994	LogP:	2.253 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.496 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.026 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	17.0
TPSA:	71.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.758	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.324	Fsp³:	0.062
MCE-18:	17.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.232	Fluc inhibitor:	0.481 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.454 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.445 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.026	Promiscuous compounds:	0.6

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847	MDCK Permeability:	-4.787
Pgp-inhibitor:	0.047	Pgp-substrate:	0.187
PAMPA:	0.462 ? 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):	0.003
20% Bioavailability (F20%):	0.236	30% Bioavailability (F30%):	0.391
50% Bioavailability (F50%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.583
Plasma Protein Binding (PPB):	95.638%	Volume Distribution (VD):	-0.093
Fu:	4.255% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.416
BSEP inhibitor:	0.596

ADMET: Metabolism

CYP1A2-inhibitor:	0.18	CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.032	CYP2C19-substrate:	0.348
CYP2C9-inhibitor:	0.525	CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.937	CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.058
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.761
HLM stability:	0.919 ? 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):

7.464

Half-life (T1/2):

0.922

ADMET: Toxicity

hERG Blockers:	0.138	hERG Blockers (10um):	0.542
Human Hepatotoxicity (H-HT):	0.607	Drug-induced Liver Injury (DILI):	0.627
AMES Toxicity:	0.572	Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.639	Skin Sensitization:	0.47
Carcinogencity:	0.617	Eye Corrosion:	0.002
Eye Irritation:	0.887	Respiratory Toxicity:	0.776
Drug-induced Neurotoxicity:	0.675	Ototoxicity:	0.389
Hematotoxicity:	0.246	Drug-induced Nephrotoxicity:	0.485
Genotoxicity:	0.932	RPMI-8226 Immunitoxicity:	0.116
A549 Cytotoxicity:	0.309	Hek293 Cytotoxicity:	0.713
BCF:	0.991 ? 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:	3.853 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.621 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.308 ? 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
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1007/s11418-005-0009-z]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691704]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378371]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643065]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257536]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	Sunan County, Gansu Province, China	2006-JUN	PMID[20684529]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[22032651]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22032651]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	whole plant	Guide County, Qinghai Province, China	2008-AUG	PMID[22775441]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30219526]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32705864]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36599374]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4901	Arnica mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2439	Diplopterygium glaucum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4123	Trididemnum cyanophorum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3151	Solanum lanceolatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2670	Maytenus chuchuhuasha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6807	Ranunculus asiaticus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3838	Chrysosporum ovalisporum	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8025	Aaptos ciliata	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO593	Wikstroemia viridiflora	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13474	Euphrasia genargentea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3344	Bryonia alba	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8938	Halobacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO784	Sinapis alba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8790	Cyanostegia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6065	Brassica carinata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2131	Dactylorhiza viridis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9594	Lysimachia fordiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO373	Viburnum erubescens	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1473	Xanthorhiza simplicissima	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9737	Ampelocera edentula	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8257	Carpha glomerata	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5086	Alternaria macrospora	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1086	Botrytis cinerea	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7032	Marasmiellus troyanus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4536	Remirea maritima	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21472	Pterolobium hexapetalum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9998	Abies excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5608	Croton gratissimus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10038.1	Abies pinsapo var. marocana	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9091	Orthosiphon spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5857	Achlya heterosexualis	Species	Saprolegniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1293	Streptomyces matensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7418	Eucalyptus resinifera	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10132	Schizophyllum lobatum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7845	Tephrosia elata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2765	Oxytropis falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9867	Ixeris debilis	Species	Asteraceae	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 NPC106197 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	24683
0.1-0.2	21212
0.2-0.3	3938
0.3-0.4	26
0.4-0.5	0
0.5-0.6	0
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC106197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3459
0.1-0.2	5542
0.2-0.3	148
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
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
		NPD

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