NPASS Compound

Natural Product: NPC605329

Natural Product ID	NPC605329
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JTEDVYBZBROSJT-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL582878
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

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 28 29 0 0 0 0 0 0 0 0999 V2000 4.5491 0.4452 1.1433 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3529 0.6598 1.3944 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9639 1.8558 1.9421 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3363 -0.3649 1.1083 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0518 -0.3300 -0.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0250 -1.3298 -0.8040 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2824 -1.1274 -0.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7979 -1.8873 0.8846 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0082 -1.3982 1.2257 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3096 -0.3394 0.4598 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.5265 0.3647 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3840 1.5401 -0.5502 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3152 1.7195 -1.4064 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2464 0.8693 -1.3277 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2323 -0.1622 -0.4001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5508 2.6736 1.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4383 -0.1991 1.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8026 -1.3551 1.3803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7446 0.6898 -0.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0003 -0.5430 -0.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4101 -2.3598 -0.6449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9321 -1.2281 -1.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3516 -2.7329 1.3632 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6563 -1.7576 1.9725 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2517 0.4264 1.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2223 2.2137 -0.6179 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3368 2.5270 -2.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3877 0.9681 -1.9740 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 7 1 0 15 10 1 0 3 16 1 0 4 17 1 0 4 18 1 0 5 19 1 0 5 20 1 0 6 21 1 0 6 22 1 0 8 23 1 0 9 24 1 0 11 25 1 0 12 26 1 0 13 27 1 0 14 28 1 0 M END

Standard InCHIKey	JTEDVYBZBROSJT-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)
SMILES	O=C(O)CCCc1c[nH]c2ccccc12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	203.09	Volume:	214.39 ? Van der Waals volume.
Dense:	0.947	LogP:	2.121 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.983 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.265 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	11.0
TPSA:	53.09 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.802	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.749	Fsp³:	0.25
MCE-18:	10.0 ? 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:	0.005	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.083 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.235 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.054	Promiscuous compounds:	0.577

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.703	MDCK Permeability:	-4.624
Pgp-inhibitor:	0.0	Pgp-substrate:	0.012
PAMPA:	0.995 ? 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):	0.018
20% Bioavailability (F20%):	0.004	30% Bioavailability (F30%):	0.015
50% Bioavailability (F50%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096	MRP1:	0.8
Plasma Protein Binding (PPB):	92.166%	Volume Distribution (VD):	-0.803
Fu:	5.472% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.533
OATP1B3 inhibitor:	0.868	BCRP inhibitor:	0.004
BSEP inhibitor:	0.387

ADMET: Metabolism

CYP1A2-inhibitor:	0.027	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.995	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.506	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.089
CYP2B6-substrate:	0.678	CYP2C8-inhibitor:	0.893
HLM stability:	0.031 ? 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):

5.641

Half-life (T1/2):

0.734

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.158
Human Hepatotoxicity (H-HT):	0.562	Drug-induced Liver Injury (DILI):	0.474
AMES Toxicity:	0.424	Rat Oral Acute Toxicity:	0.356
Maximum Recommended Daily Dose:	0.352	Skin Sensitization:	0.264
Carcinogencity:	0.49	Eye Corrosion:	0.192
Eye Irritation:	0.981	Respiratory Toxicity:	0.627
Drug-induced Neurotoxicity:	0.483	Ototoxicity:	0.543
Hematotoxicity:	0.497	Drug-induced Nephrotoxicity:	0.56
Genotoxicity:	0.224	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.047
BCF:	0.181 ? 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:	2.851 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.941 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.253 ? 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
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89267-5]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98060-9]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/bst0160071]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12882150]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15286289]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15666542]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[20947202]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253552]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36500609]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[556731]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Wax	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	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

Activity Type	# Activity
Inhibition	10
IC50	10
Kd	4
Ratio	1
Potency	10
Activity	1

Activity Type	# Activity
Individual protein	14
Single protein	9
Unchecked	2
Organism	8
Non-molecular	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	19952.6	nM	PubChem BioAssay data set
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT22584	Single protein	OXA-48	Klebsiella pneumoniae	IC50	=	480000.0	nM	PMID[27165692]
NPT22584	Single protein	OXA-48	Klebsiella pneumoniae	Kd	=	430000.0	nM	PMID[27165692]
NPT5475	Individual protein	Beta-lactamase VIM-2	Pseudomonas aeruginosa	Kd	=	274000.0	nM	PMID[26477515]
NPT5475	Individual protein	Beta-lactamase VIM-2	Pseudomonas aeruginosa	IC50	=	757000.0	nM	PMID[26477515]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	-5.54	%	PMID[23062825]
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	-2.0	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT99	Individual protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT692	Individual protein	Histone deacetylase 6	Homo sapiens	Inhibition	=	-15.75	%	HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators
NPT20556	Single protein	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.767	%	Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen
NPT5475	Individual protein	Beta-lactamase VIM-2	Pseudomonas aeruginosa	Inhibition	>	15.0	%	PMID[26477515]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	-10.87	%	PMID[23062825]
NPT26331	Single protein	Beta-lactamase NDM-1	Klebsiella pneumoniae	Inhibition	>	20.0	%	PMID[26976213]
NPT26331	Single protein	Beta-lactamase NDM-1	Klebsiella pneumoniae	IC50	=	1946000.0	nM	PMID[26976213]
NPT26331	Single protein	Beta-lactamase NDM-1	Klebsiella pneumoniae	Ratio	=	1.5	n.a.	PMID[26976213]
NPT26331	Single protein	Beta-lactamase NDM-1	Klebsiella pneumoniae	Kd	=	794328.23	nM	PMID[26976213]
NPT26331	Single protein	Beta-lactamase NDM-1	Klebsiella pneumoniae	IC50	=	1949844.6	nM	PMID[26976213]
NPT26331	Single protein	Beta-lactamase NDM-1	Klebsiella pneumoniae	Kd	=	806000.0	nM	PMID[26976213]
NPT546	Individual protein	Retinoid X receptor alpha	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28438	Unchecked	Unchecked	n.a.	IC50	>	1000000.0	nM	PMID[19817384]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	16.23	%	Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	IC50	=	576.0	ug.mL-1	DOI[10.1584/jpestics.G09-66]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	IC50	=	644.0	ug.mL-1	DOI[10.1584/jpestics.G09-66]
NPT28438	Unchecked	Unchecked	n.a.	IC50	=	17820.0	nM	PMID[30108915]
NPT4303	Organism	Vigna mungo	Vigna mungo	Activity	=	100.0	%	PMID[18685200]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.05	%	Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Potency	n.a.	59.5	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Potency	n.a.	15.0	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Potency	n.a.	13.3	nM	PubChem BioAssay data set
NPT29749	Organism	Globisporangium debaryanum	Globisporangium debaryanum	IC50	=	249.0	ug.mL-1	DOI[10.1584/jpestics.G09-66]
NPT4304	Organism	Macrophomina phaseolina	Macrophomina phaseolina	IC50	=	699.0	ug.mL-1	DOI[10.1584/jpestics.G09-66]

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
-	Rattus norvegicus	LOEL	=	25.0	mg/L	ToxVal
-	Rattus norvegicus	LOEL	=	250.0	mg/kg-day	ToxVal
-	Mus musculus	LD50	=	3.308011323	mg/kg	TOXRIC
-	Mus musculus	LD50	=	1925.0	mg/kg-day	ToxVal
-	Mus musculus	LD50	=	100.0	mg/kg	ToxVal

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 NPC605329 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	34309
0.1-0.2	13840
0.2-0.3	1260
0.3-0.4	296
0.4-0.5	114
0.5-0.6	26
0.6-0.7	11
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
0.7391	Intermediate Similarity	NPC78020
0.6667	Remote Similarity	NPC480316
0.6531	Remote Similarity	NPC315555
0.6531	Remote Similarity	NPC55772
0.64	Remote Similarity	NPC149155
0.64	Remote Similarity	NPC203468
0.64	Remote Similarity	NPC110500
0.6275	Remote Similarity	NPC480318
0.62	Remote Similarity	NPC600736
0.6154	Remote Similarity	NPC248041
0.6038	Remote Similarity	NPC480317
0.6038	Remote Similarity	NPC200214
0.5926	Remote Similarity	NPC267885
0.5918	Remote Similarity	NPC310665
0.5909	Remote Similarity	NPC601214
0.5745	Remote Similarity	NPC279081
0.5714	Remote Similarity	NPC283219
0.5714	Remote Similarity	NPC213468
0.5714	Remote Similarity	NPC111275
0.5532	Remote Similarity	NPC96102
0.5417	Remote Similarity	NPC230869
0.537	Remote Similarity	NPC14113
0.537	Remote Similarity	NPC145885
0.537	Remote Similarity	NPC84827
0.5333	Remote Similarity	NPC602969
0.5306	Remote Similarity	NPC29886
0.5294	Remote Similarity	NPC605863
0.5283	Remote Similarity	NPC59269
0.5263	Remote Similarity	NPC602670
0.5246	Remote Similarity	NPC605102
0.52	Remote Similarity	NPC84911
0.5185	Remote Similarity	NPC190296
0.5179	Remote Similarity	NPC471957
0.5179	Remote Similarity	NPC608269
0.5161	Remote Similarity	NPC321708
0.5139	Remote Similarity	NPC605408
0.5098	Remote Similarity	NPC73767
0.5079	Remote Similarity	NPC606272

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4222
0.1-0.2	4582
0.2-0.3	263
0.3-0.4	67
0.4-0.5	6
0.5-0.6	8
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	Drug ID	Developmental Stage
0.64	Remote Similarity	NPD482	Phase 4
0.6275	Remote Similarity	NPD749	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD2096	Phase 3
0.5532	Remote Similarity	NPD198	Clinical (unspecified phase)
0.5294	Remote Similarity	NPD786	Pre-clinical
0.5238	Remote Similarity	NPD2094	Phase 2
0.5238	Remote Similarity	NPD2095	Phase 2
0.5179	Remote Similarity	NPD1722	Phase 4
0.5156	Remote Similarity	NPD2092	Phase 2
0.5075	Remote Similarity	NPD2091	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