NPASS Compound

Natural Product: NPC129417

Natural Product ID	NPC129417
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Olivil 4''-O-Beta-D-Glucopyranoside
IUPAC Name	(2S,3R,4S,5S,6R)-2-[4-[[(3R,4S,5R)-3-hydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1911056
PubChem CID	57395552
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan 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 72 75 0 0 0 0 0 0 0 0999 V2000 3.0614 -2.4620 0.6180 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2640 -1.3179 0.9632 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0983 -0.1444 0.5845 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4244 -0.1588 -0.9045 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4138 1.1613 -1.3123 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3674 1.7518 -0.5717 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6190 1.2097 0.8478 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7828 1.9639 1.2738 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5175 1.5381 1.7490 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1622 1.0295 1.4879 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6873 1.7117 0.5976 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9716 1.3031 0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5028 0.2056 0.9384 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -0.4913 1.8183 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4130 -0.0754 2.0739 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2153 -1.6342 2.4611 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4345 -2.3772 3.3695 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7769 -0.2687 0.7349 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7620 0.2546 -0.0964 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8628 0.5604 0.7017 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9154 1.1191 0.0419 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2230 0.5420 0.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2744 -0.8343 0.4370 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8898 1.0564 -1.4383 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1922 -0.1200 -2.0266 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2642 -0.8105 -1.0835 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1957 -1.4291 -1.7224 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0805 -1.0325 -2.6375 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4161 2.2765 -1.9673 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7656 -0.7340 -1.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9625 -1.9914 -1.6578 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2543 -2.4307 -1.8179 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3582 -1.6771 -1.4669 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1666 -0.4246 -0.9303 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8765 0.0224 -0.7668 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2641 0.3269 -0.5804 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2184 1.6109 -0.0270 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6377 -2.1798 -1.6546 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8011 -2.5428 1.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3535 -1.4604 0.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2039 -1.3658 2.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1072 -0.3343 1.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6422 -0.7474 -1.4417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3937 1.4607 -0.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5027 2.8321 -0.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5595 2.8950 1.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4217 2.6836 1.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7892 1.3871 2.8456 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2770 2.6164 0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5926 1.8647 -0.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1707 -0.6375 2.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4363 -2.5799 2.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9373 -3.3338 3.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2453 -1.7806 4.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4578 1.1491 -0.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9511 2.2100 0.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0606 1.0296 0.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3171 0.8038 1.6778 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7223 -1.2426 1.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9633 1.0071 -1.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5628 0.2644 -2.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8062 -1.5926 -0.5301 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4127 -1.3569 -1.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4706 -1.6890 -3.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5954 2.1616 -2.4910 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1018 -2.5648 -1.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4422 -3.4084 -2.2360 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7633 1.0104 -0.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4069 1.6726 0.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0775 2.3582 -0.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1895 1.8173 0.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4521 -1.6369 -1.4337 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 1 7 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 14 16 1 0 16 17 1 0 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 4 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 36 37 1 0 33 38 1 0 7 3 1 0 15 10 1 0 26 19 1 0 35 30 1 0 1 39 1 0 2 40 1 0 2 41 1 0 3 42 1 1 4 43 1 6 6 44 1 0 6 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 11 49 1 0 12 50 1 0 15 51 1 0 17 52 1 0 17 53 1 0 17 54 1 0 19 55 1 6 21 56 1 6 22 57 1 0 22 58 1 0 23 59 1 0 24 60 1 6 25 61 1 6 26 62 1 1 27 63 1 0 28 64 1 0 29 65 1 0 31 66 1 0 32 67 1 0 35 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 38 72 1 0 M END

Standard InCHIKey	SXGSYHDLSPXCMU-QMFIMPQNSA-N
Standard InCHI	InChI=1S/C26H34O12/c1-34-18-8-14(4-5-16(18)29)24-15(10-27)26(33,12-36-24)9-13-3-6-17(19(7-13)35-2)37-25-23(32)22(31)21(30)20(11-28)38-25/h3-8,15,20-25,27-33H,9-12H2,1-2H3/t15-,20+,21+,22-,23+,24-,25+,26-/m0/s1
SMILES	OC[C@H]1[C@@H](OC[C@@]1(O)Cc1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	538.21	Volume:	513.69 ? Van der Waals volume.
Dense:	1.048	LogP:	-0.392 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.182 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.452 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	187.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.212	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.491	Fsp³:	0.538
MCE-18:	96.6 ? 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:	0
Colloidal aggregators:	0.452	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.058 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.109 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.069	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.299	MDCK Permeability:	-5.367
Pgp-inhibitor:	0.0	Pgp-substrate:	0.861
PAMPA:	0.937 ? 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):	0.776
20% Bioavailability (F20%):	0.279	30% Bioavailability (F30%):	0.928
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.08
Plasma Protein Binding (PPB):	69.023%	Volume Distribution (VD):	-0.173
Fu:	31.012% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.118
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.123	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.009
HLM stability:	0.003 ? 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):

3.166

Half-life (T1/2):

4.061

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.065
Human Hepatotoxicity (H-HT):	0.874	Drug-induced Liver Injury (DILI):	0.835
AMES Toxicity:	0.938	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	0.996
Carcinogencity:	0.176	Eye Corrosion:	0.0
Eye Irritation:	0.108	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.964
Hematotoxicity:	0.293	Drug-induced Nephrotoxicity:	0.83
Genotoxicity:	0.763	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.153	Hek293 Cytotoxicity:	0.179
BCF:	0.354 ? 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:	2.792 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.359 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.432 ? 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
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[17345316]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	red sea soft coral	n.a.	PMID[20420415]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[21070025]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO4579	Nepeta nuda	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31029727]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[32790311]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35481430]
NPO1300	Dacryodes edulis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235361]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7226	Centaurea kandavanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1445	Aplysina caissara	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4579	Nepeta nuda	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8946	Polyandrocarpa zorritensis	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO354	Capillaster multiradiatus	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22114	Cladiella pachyclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20855.1	Talaromyces flavus var. flavus	Varieties	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28260	Senna alexandrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8946	Polyandrocarpa zorritensis	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10271	Psammosilene tunicoides	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1300	Dacryodes edulis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4579	Nepeta nuda	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9873	Mertensia maritima	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10140	Genista raetam	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4133	Callicarpa pedunculata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1445	Aplysina caissara	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5025	Persicaria capitata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO354	Capillaster multiradiatus	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9601	Ptaeroxylon obliquum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7226	Centaurea kandavanensis	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

Activity Type	# Activity
EC50	2

Activity Type	# Activity
Others	1
Non-molecular	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	25280.0	nM	PMID[21955940]
NPT1	Others	Radical scavenging activity	n.a.	EC50	>	100000.0	nM	PMID[21955940]

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 NPC129417 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	14236
0.1-0.2	30302
0.2-0.3	4178
0.3-0.4	935
0.4-0.5	165
0.5-0.6	28
0.6-0.7	11
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
0.8933	High Similarity	NPC470235
0.7195	Intermediate Similarity	NPC46092
0.7195	Intermediate Similarity	NPC470950
0.6947	Remote Similarity	NPC475224
0.6835	Remote Similarity	NPC38041
0.6835	Remote Similarity	NPC22150
0.6706	Remote Similarity	NPC112861
0.6706	Remote Similarity	NPC283995
0.6625	Remote Similarity	NPC18979
0.6438	Remote Similarity	NPC277804
0.6395	Remote Similarity	NPC185307
0.6395	Remote Similarity	NPC163635
0.6207	Remote Similarity	NPC478055
0.6163	Remote Similarity	NPC39657
0.5977	Remote Similarity	NPC299706
0.5977	Remote Similarity	NPC115466
0.5977	Remote Similarity	NPC61604
0.5952	Remote Similarity	NPC471063
0.5904	Remote Similarity	NPC51328
0.5904	Remote Similarity	NPC286235
0.5904	Remote Similarity	NPC55158
0.5833	Remote Similarity	NPC279298
0.5778	Remote Similarity	NPC486548
0.5696	Remote Similarity	NPC276753
0.5696	Remote Similarity	NPC205796
0.5625	Remote Similarity	NPC246947
0.5604	Remote Similarity	NPC486549
0.5526	Remote Similarity	NPC472024
0.5526	Remote Similarity	NPC270849
0.5455	Remote Similarity	NPC26653
0.5455	Remote Similarity	NPC80600
0.5444	Remote Similarity	NPC245615
0.5393	Remote Similarity	NPC469586
0.5393	Remote Similarity	NPC44452
0.5376	Remote Similarity	NPC486546
0.5287	Remote Similarity	NPC227902
0.5275	Remote Similarity	NPC486545
0.5233	Remote Similarity	NPC158635
0.5233	Remote Similarity	NPC229882
0.5111	Remote Similarity	NPC605526
0.5065	Remote Similarity	NPC9912
0.506	Remote Similarity	NPC471988

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC129417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4285
0.1-0.2	4701
0.2-0.3	150
0.3-0.4	14
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