NPASS Compound

Natural Product: NPC218488

Natural Product ID	NPC218488
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Isoorientin 6''-O-Glucoside
IUPAC Name	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]chromen-4-one
Synonyms	Isoorientin 6'-O-Glucoside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL498858
PubChem CID	180730
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-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 73 77 0 0 0 0 0 0 0 0999 V2000 -8.2243 0.4662 2.7367 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4358 -0.4583 2.0487 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6797 0.2129 0.9220 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9225 -0.7669 0.2889 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0190 -0.1500 -0.6292 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1886 -1.0660 -1.0743 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8682 -1.1133 -1.0583 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0643 -1.2722 0.1714 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6913 -1.3347 -0.1100 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0639 -0.4585 0.6070 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5276 0.9358 0.3956 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7494 0.9685 1.3052 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4030 -0.3813 1.2881 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1040 -1.0341 2.5475 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5901 2.0068 0.9388 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3823 1.9223 0.7982 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4774 -0.5072 0.1868 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9129 -0.8357 -1.0753 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9642 -1.1459 -2.0275 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2712 -0.8617 -1.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2222 -0.5506 -0.4538 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7922 -0.2196 0.8166 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4482 -0.2018 1.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0929 0.1426 2.4231 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7535 0.0868 1.7525 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4089 0.3898 2.9066 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1017 0.0441 1.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4514 -0.2929 0.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4937 -0.5725 -0.7568 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8522 -0.3317 -0.3041 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1908 -0.6801 -1.6208 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4968 -0.7339 -2.0456 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5462 -0.4480 -1.1994 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2382 -0.1035 0.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9067 -0.0489 0.5300 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2786 0.1891 0.9699 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8717 -0.5006 -1.6232 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9236 0.3356 -1.8064 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9339 1.2935 -1.2465 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7063 0.6989 -0.0843 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5374 1.6754 0.4254 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8419 1.6438 -2.2156 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0682 1.0442 -2.6468 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6539 0.8703 3.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1140 -1.2460 1.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7303 -0.8994 2.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0984 1.0506 1.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6648 0.7897 -0.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4577 -0.2203 -1.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5507 -1.9872 -1.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2842 -2.3349 0.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0237 -0.6436 1.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7584 1.1160 -0.6551 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3668 1.1776 2.3439 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4916 -0.2492 1.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2243 -1.9915 2.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9246 2.4482 1.7433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3732 2.7000 0.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8570 -2.1143 -2.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 -1.1224 -2.4051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7469 -0.6268 2.9987 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8242 0.2854 2.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3748 -0.9027 -2.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7621 -1.0029 -3.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7252 0.2231 1.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8293 1.0225 0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0712 0.0088 -2.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3958 -0.5174 -2.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4469 2.2060 -0.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2803 -0.1905 -0.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4939 1.4083 0.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1000 0.8261 -2.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8765 1.9303 -2.2713 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 11 16 1 0 10 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 22 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 28 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 5 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 40 3 1 0 13 8 1 0 23 17 1 0 35 30 1 0 29 21 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 1 5 48 1 1 7 49 1 0 7 50 1 0 8 51 1 1 10 52 1 1 11 53 1 6 12 54 1 1 13 55 1 1 14 56 1 0 15 57 1 0 16 58 1 0 19 59 1 0 20 60 1 0 24 61 1 0 27 62 1 0 31 63 1 0 32 64 1 0 35 65 1 0 36 66 1 0 37 67 1 0 38 68 1 6 39 69 1 1 40 70 1 6 41 71 1 0 42 72 1 0 43 73 1 0 M END

Standard InCHIKey	WJLJMQTUQORVBM-KETMJRJWSA-N
Standard InCHI	InChI=1S/C27H30O16/c28-6-15-19(33)23(37)25(39)27(43-15)40-7-16-20(34)22(36)24(38)26(42-16)18-12(32)5-14-17(21(18)35)11(31)4-13(41-14)8-1-2-9(29)10(30)3-8/h1-5,15-16,19-20,22-30,32-39H,6-7H2/t15-,16-,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@H]([C@@H]([C@H]([C@@H]2O)O)O)c2c(O)cc3c(c2O)c(=O)cc(o3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.15 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.467 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.952 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	280.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.821	Fsp³:	0.444
MCE-18:	122.949 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.637	Fluc inhibitor:	0.167 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.898 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.568 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.205	Promiscuous compounds:	0.454

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.498	MDCK Permeability:	-5.063
Pgp-inhibitor:	0.0	Pgp-substrate:	0.694
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):	0.829
20% Bioavailability (F20%):	0.766	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.523
Plasma Protein Binding (PPB):	84.268%	Volume Distribution (VD):	-0.059
Fu:	12.236% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.028
BSEP inhibitor:	0.0

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:	0.023
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.021 ? 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):

2.207

Half-life (T1/2):

5.783

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.062
Human Hepatotoxicity (H-HT):	0.396	Drug-induced Liver Injury (DILI):	0.919
AMES Toxicity:	0.91	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.063	Skin Sensitization:	0.999
Carcinogencity:	0.048	Eye Corrosion:	0.0
Eye Irritation:	0.305	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.972
Hematotoxicity:	0.035	Drug-induced Nephrotoxicity:	0.092
Genotoxicity:	0.946	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.868	Hek293 Cytotoxicity:	0.452
BCF:	0.356 ? 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:	2.83 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.371 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.527 ? 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
NPO7339	Crataegus monogyna	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21648406]
NPO19505	Swartzia polyphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623042]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	Whole Plant	Yu Shieh, Chiayi Hsieh, Taiwan	1994-APR	PMID[9287421]
NPO8163	Aristotelia serrata	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18254	Hypselodoris zebra	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11804	Potentilla erecta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19505	Swartzia polyphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7339	Crataegus monogyna	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18590	Sophora fraseri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18337	Helminthosporium sativum	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18015	Leptopsammia pruvoti	Species	Dendrophylliidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7339	Crataegus monogyna	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19157	Senecio eremophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19425	Lysimachia foenum-graecum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19756	Artemisia mongolica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19157	Senecio eremophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19425	Lysimachia foenum-graecum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7339	Crataegus monogyna	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19756	Artemisia mongolica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19756	Artemisia mongolica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7339	Crataegus monogyna	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11058	Ficus lutea	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16297	Gentiana arisanensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18590	Sophora fraseri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19505	Swartzia polyphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19157	Senecio eremophilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19425	Lysimachia foenum-graecum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18015	Leptopsammia pruvoti	Species	Dendrophylliidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18254	Hypselodoris zebra	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17307	Thermomyces dupontii	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5093	Centaurea hermannii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18337	Helminthosporium sativum	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12636	Eperua purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28375	Pygeum topengii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8163	Aristotelia serrata	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18912	Centaurea nervosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11804	Potentilla erecta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16518	Coryphantha calipensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13284	Lomatia polymorpha	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17081	Dicranopteris ampla	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19756	Artemisia mongolica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16042	Diplazium nipponicum	Species	Athyriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7339	Crataegus monogyna	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11550	Tournefortia argentea	Species	Heliotropiaceae	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
Activity	4

Activity Type	# Activity
Cell line	4

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
NPT20967	Cell line	Platelet	n.a.	Activity	=	85.7	%	PMID[9287421]
NPT20967	Cell line	Platelet	n.a.	Activity	=	83.3	%	PMID[9287421]
NPT20967	Cell line	Platelet	n.a.	Activity	=	85.4	%	PMID[9287421]
NPT20967	Cell line	Platelet	n.a.	Activity	=	83.5	%	PMID[9287421]

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 NPC218488 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	23435
0.1-0.2	22230
0.2-0.3	3408
0.3-0.4	563
0.4-0.5	189
0.5-0.6	20
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8875	High Similarity	NPC47923
0.7821	Intermediate Similarity	NPC53545
0.6829	Remote Similarity	NPC328740
0.6829	Remote Similarity	NPC289774
0.6593	Remote Similarity	NPC78734
0.6506	Remote Similarity	NPC289771
0.6484	Remote Similarity	NPC603300
0.6264	Remote Similarity	NPC294629
0.6264	Remote Similarity	NPC131407
0.6222	Remote Similarity	NPC111249
0.6064	Remote Similarity	NPC604854
0.6	Remote Similarity	NPC607513
0.5747	Remote Similarity	NPC268193
0.5506	Remote Similarity	NPC117418
0.5417	Remote Similarity	NPC190393
0.5361	Remote Similarity	NPC8856
0.5354	Remote Similarity	NPC210073
0.5354	Remote Similarity	NPC156869
0.534	Remote Similarity	NPC256760
0.5248	Remote Similarity	NPC488073
0.5238	Remote Similarity	NPC10097
0.5204	Remote Similarity	NPC472607
0.5161	Remote Similarity	NPC189142
0.5161	Remote Similarity	NPC77660
0.5146	Remote Similarity	NPC150767
0.5109	Remote Similarity	NPC112701
0.5106	Remote Similarity	NPC58716
0.5106	Remote Similarity	NPC45638
0.5053	Remote Similarity	NPC201292
0.5052	Remote Similarity	NPC326592
0.505	Remote Similarity	NPC3583
0.5049	Remote Similarity	NPC65711

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC218488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6027
0.1-0.2	3041
0.2-0.3	72
0.3-0.4	5
0.4-0.5	5
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