NPASS Compound

Natural Product: NPC229409

Natural Product ID	NPC229409
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RNDGJCZQVKFBPI-ASDZUOGYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5281669
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 60 63 0 0 0 0 0 0 0 0999 V2000 -7.8333 -0.2403 -0.6251 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9174 -1.0932 -0.4076 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7466 -2.3197 0.1815 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4681 -2.6893 0.5549 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4072 -1.8373 0.3341 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5656 -0.5979 -0.2589 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4268 0.2891 -0.4833 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5055 1.5291 -1.0647 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4187 2.3453 -1.2651 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4791 3.4725 -1.7918 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1789 1.8822 -0.8541 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0384 2.6236 -1.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8335 2.1153 -0.5857 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7337 0.8726 0.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9165 0.1495 0.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1380 0.6315 -0.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2345 -0.1054 -0.1115 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4426 0.3328 0.4361 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7265 0.8779 0.3868 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1743 1.0761 1.8190 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6507 0.8653 1.9784 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3226 1.2390 0.6913 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8299 0.3748 -0.4466 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7000 -0.8615 -0.4877 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0750 -0.5072 -0.6527 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0556 -1.4845 -0.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7342 -2.6930 -0.6203 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4764 -1.0902 -0.8842 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3252 -2.3033 -0.9043 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5710 -2.9052 0.1610 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8266 -2.7389 -2.1160 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5298 -0.0358 -0.2875 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0963 2.5886 0.4536 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9660 -0.4223 2.3981 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8988 2.4020 2.2213 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1496 3.8862 -1.6088 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2983 -3.9277 1.1492 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8190 -3.1891 0.4083 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0297 0.7126 -1.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9049 -0.7902 -0.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4219 -2.1373 0.6286 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4725 1.8924 -1.3864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0532 2.7457 -0.7324 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8805 -0.8476 0.6063 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6959 1.8599 -0.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6040 0.4311 2.5327 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0371 1.5555 2.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4260 1.1083 0.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9966 0.9271 -1.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6180 -1.4815 0.4262 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4136 -1.5383 -1.3317 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7972 -0.4139 -0.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6083 -0.5125 -1.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6755 -3.3210 -2.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7450 3.0819 1.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1707 -1.0015 2.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9841 2.6581 1.9071 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8021 4.6880 -1.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9769 -4.3579 1.7681 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6296 -2.8651 0.9171 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 23 32 1 0 22 33 1 0 21 34 1 0 20 35 1 0 12 36 1 0 4 37 1 0 3 38 1 0 6 1 1 0 17 7 1 0 32 19 1 0 16 11 1 0 1 39 1 0 2 40 1 0 5 41 1 0 8 42 1 0 13 43 1 0 15 44 1 0 19 45 1 6 20 46 1 1 21 47 1 1 22 48 1 1 23 49 1 6 24 50 1 0 24 51 1 0 28 52 1 0 28 53 1 0 31 54 1 0 33 55 1 0 34 56 1 0 35 57 1 0 36 58 1 0 37 59 1 0 38 60 1 0 M END

Standard InCHIKey	RNDGJCZQVKFBPI-ASDZUOGYSA-N
Standard InCHI	InChI=1S/C24H22O14/c25-11-2-1-9(3-12(11)26)15-6-14(28)20-13(27)4-10(5-16(20)37-15)36-24-23(34)22(33)21(32)17(38-24)8-35-19(31)7-18(29)30/h1-6,17,21-27,32-34H,7-8H2,(H,29,30)/t17-,21-,22+,23-,24-/m1/s1
SMILES	c1cc(c(cc1c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)CC(=O)O)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.1	Volume:	486.133 ? Van der Waals volume.
Dense:	1.099	LogP:	0.348 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.415 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	26.0
TPSA:	233.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.118	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.131	Fsp³:	0.292
MCE-18:	93.032 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.521	Fluc inhibitor:	0.319 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.98 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.888 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.083	Promiscuous compounds:	0.563

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.471	MDCK Permeability:	-5.128
Pgp-inhibitor:	0.0	Pgp-substrate:	0.014
PAMPA:	1.0 ? 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):	0.123
20% Bioavailability (F20%):	0.35	30% Bioavailability (F30%):	0.912
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.604
Plasma Protein Binding (PPB):	79.196%	Volume Distribution (VD):	-0.118
Fu:	18.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.039
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.981
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	0.002 ? 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):

1.689

Half-life (T1/2):

3.305

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.06
Human Hepatotoxicity (H-HT):	0.349	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.647	Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.137	Skin Sensitization:	0.991
Carcinogencity:	0.103	Eye Corrosion:	0.0
Eye Irritation:	0.808	Respiratory Toxicity:	0.038
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.802
Hematotoxicity:	0.079	Drug-induced Nephrotoxicity:	0.41
Genotoxicity:	0.977	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.128	Hek293 Cytotoxicity:	0.061
BCF:	0.276 ? 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:	2.806 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.274 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.503 ? 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
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO20197	Boletinus asiaticus	Species	Gyrodontaceae	Eukaryota	Fruiting Bodies	n.a.	n.a.	PMID[31244141]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[32991171]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34885954]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO20197	Boletinus asiaticus	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21283	Stahlianthus campanulatus	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19308	Ficus formosa	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20731	Pometia ridleyi	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21355	Elsholtzia ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20197	Boletinus asiaticus	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11696	Pachylaena atriplicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21283	Stahlianthus campanulatus	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18215	Ficus benjamina	Species	Moraceae	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
NPO20440	Chrysanthemum x morifolium	n.a.	Flowers	1.02	n.a.	n.a.	mg/g of FW	DOI[10.3136/fstr.15.499]
NPO26721	Apium graveolens	Other	n.a.	92	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO26721	Apium graveolens	Raw	n.a.	6.660000483	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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	1
Activity	3

Activity Type	# Activity
Individual protein	1
Cell line	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2797	Individual protein	Pancreatic lipase	Homo sapiens	Inhibition	=	65.8	%	PMID[37099836]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[37099836]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	61.5	%	PMID[37099836]
NPT65	Cell line	HepG2	Homo sapiens	Activity	=	57.1	%	PMID[37099836]

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 NPC229409 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	18532
0.1-0.2	28152
0.2-0.3	2236
0.3-0.4	583
0.4-0.5	256
0.5-0.6	56
0.6-0.7	31
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9036	High Similarity	NPC64051
0.8588	High Similarity	NPC46202
0.7333	Intermediate Similarity	NPC210073
0.7159	Intermediate Similarity	NPC190003
0.7097	Intermediate Similarity	NPC65711
0.6941	Remote Similarity	NPC19709
0.686	Remote Similarity	NPC189142
0.686	Remote Similarity	NPC77660
0.6818	Remote Similarity	NPC20505
0.6771	Remote Similarity	NPC479766
0.6771	Remote Similarity	NPC270675
0.6771	Remote Similarity	NPC195685
0.6701	Remote Similarity	NPC479765
0.6667	Remote Similarity	NPC44931
0.663	Remote Similarity	NPC254540
0.6566	Remote Similarity	NPC472994
0.6421	Remote Similarity	NPC22062
0.6421	Remote Similarity	NPC473634
0.6421	Remote Similarity	NPC138811
0.6333	Remote Similarity	NPC27942
0.6327	Remote Similarity	NPC209296
0.6311	Remote Similarity	NPC472993
0.63	Remote Similarity	NPC101636
0.63	Remote Similarity	NPC298171
0.6275	Remote Similarity	NPC121703
0.6264	Remote Similarity	NPC282169
0.625	Remote Similarity	NPC331652
0.618	Remote Similarity	NPC39360
0.618	Remote Similarity	NPC29763
0.618	Remote Similarity	NPC210003
0.6162	Remote Similarity	NPC473623
0.61	Remote Similarity	NPC488089
0.6067	Remote Similarity	NPC473043
0.6044	Remote Similarity	NPC181712
0.6022	Remote Similarity	NPC608742
0.6	Remote Similarity	NPC172807
0.5979	Remote Similarity	NPC67105
0.5938	Remote Similarity	NPC606546
0.5934	Remote Similarity	NPC95090
0.5934	Remote Similarity	NPC27408
0.5922	Remote Similarity	NPC253685
0.5851	Remote Similarity	NPC22832
0.5851	Remote Similarity	NPC601144
0.5833	Remote Similarity	NPC211594
0.5789	Remote Similarity	NPC311830
0.5784	Remote Similarity	NPC486577
0.5773	Remote Similarity	NPC8856
0.5741	Remote Similarity	NPC277532
0.5652	Remote Similarity	NPC261866
0.5652	Remote Similarity	NPC238376
0.5591	Remote Similarity	NPC277205
0.5591	Remote Similarity	NPC37919
0.5591	Remote Similarity	NPC136042
0.5577	Remote Similarity	NPC80068
0.5545	Remote Similarity	NPC115674
0.5545	Remote Similarity	NPC186816
0.5532	Remote Similarity	NPC271692
0.5521	Remote Similarity	NPC243930
0.5514	Remote Similarity	NPC11468
0.551	Remote Similarity	NPC116864
0.551	Remote Similarity	NPC244776
0.5488	Remote Similarity	NPC108406
0.5472	Remote Similarity	NPC484301
0.5464	Remote Similarity	NPC607707
0.5429	Remote Similarity	NPC477629
0.5426	Remote Similarity	NPC168822
0.5368	Remote Similarity	NPC58716
0.5368	Remote Similarity	NPC84362
0.5368	Remote Similarity	NPC45638
0.5347	Remote Similarity	NPC275454
0.5347	Remote Similarity	NPC227508
0.5327	Remote Similarity	NPC179862
0.5312	Remote Similarity	NPC201292
0.5306	Remote Similarity	NPC605784
0.5294	Remote Similarity	NPC473512
0.5294	Remote Similarity	NPC233994
0.5268	Remote Similarity	NPC488087
0.5263	Remote Similarity	NPC298666
0.5243	Remote Similarity	NPC204693
0.5175	Remote Similarity	NPC488086
0.5158	Remote Similarity	NPC249281
0.5146	Remote Similarity	NPC129827
0.5143	Remote Similarity	NPC211532
0.5143	Remote Similarity	NPC488364
0.5135	Remote Similarity	NPC480796
0.5135	Remote Similarity	NPC473278
0.5104	Remote Similarity	NPC297987
0.51	Remote Similarity	NPC276377
0.5094	Remote Similarity	NPC483707
0.5052	Remote Similarity	NPC46420
0.5046	Remote Similarity	NPC223426
0.5043	Remote Similarity	NPC68592

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3902
0.1-0.2	5157
0.2-0.3	81
0.3-0.4	4
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
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
0.6327	Remote Similarity	NPD7054	Phase 4
0.5577	Remote Similarity	NPD7251	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