NPASS Compound

Natural Product: NPC551246

Natural Product ID	NPC551246
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{R},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 93 98 0 0 0 0 0 0 0 0999 V2000 7.5415 3.3384 -1.4236 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5744 2.7571 -0.4337 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5350 2.1206 -1.1215 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7415 1.4591 -0.1402 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5095 0.9140 0.8171 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5542 -0.4133 1.0177 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2912 -1.1328 1.4174 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3506 -1.0488 0.4484 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6960 -2.3262 0.2753 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6353 -2.2899 -0.5621 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3144 -2.0911 -0.5460 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7138 -2.9808 -0.4402 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5494 -4.4239 -0.3174 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6169 -5.2076 -0.6829 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 -6.5749 -0.5788 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5264 -7.1880 -0.0709 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4982 -8.5913 0.0599 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5528 -6.4259 0.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5460 -5.0214 0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9754 -2.5201 -0.4574 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 -1.2702 -0.5670 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6199 -0.8660 -0.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9911 0.4819 -0.6946 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3424 0.7725 -0.6940 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9049 2.0198 -0.7772 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7385 2.2069 0.3484 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6081 3.2747 0.1895 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2106 3.5256 1.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1059 4.5677 1.5843 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7674 2.9016 -0.7106 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2511 4.0588 -1.2982 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2237 1.9523 -1.7539 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3799 0.6202 -1.4124 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7498 2.2213 -2.0264 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6415 3.5542 -2.4342 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9980 1.4284 -0.8028 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6710 1.0504 -0.7954 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6617 1.9969 -0.9038 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3482 -0.2852 -0.6786 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0517 -0.7278 -0.6650 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8318 0.1764 -0.7684 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8065 -3.1787 -0.2748 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4367 -4.1937 -1.1069 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6109 -3.6085 0.9355 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9928 -4.7431 1.4782 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7106 -2.4894 1.8916 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9700 -2.7956 3.0354 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8727 2.5603 0.4498 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6170 2.5576 -0.1145 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4978 3.9144 0.2192 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9201 4.8516 1.0606 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9919 3.8382 0.4262 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2573 3.5994 1.7879 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2320 2.5496 -1.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2175 4.0419 -0.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0050 3.8441 -2.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0682 2.0180 0.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1559 0.7255 -0.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9211 -0.8719 0.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4029 -0.7146 1.7220 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9071 -0.5324 2.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4721 -2.5794 1.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 -4.7319 -1.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5262 -7.1120 -0.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3144 -9.0478 0.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4260 -6.9434 0.7010 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4166 -4.5450 0.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4035 -1.6047 -0.4936 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1526 2.8224 -0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1354 4.1884 -0.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6267 2.5467 1.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3778 3.7590 2.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0363 5.0889 2.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5346 2.4014 -0.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9263 4.1740 -2.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7451 2.1515 -2.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2163 0.5052 -0.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4533 1.5946 -2.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7623 3.8775 -2.1118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2760 2.4773 -0.8956 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9153 2.8960 -1.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4593 -2.4967 -0.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6113 -4.0102 -2.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6112 -3.8984 0.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4564 -5.5507 1.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7879 -2.4432 2.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2635 -3.7236 3.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8086 2.3832 1.5460 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5866 2.3039 -1.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3125 4.2488 -0.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0254 4.6116 2.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4707 4.8245 0.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4165 4.4461 2.2379 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 12 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 23 36 2 0 36 37 1 0 37 38 1 0 37 39 2 0 39 40 1 0 40 41 2 0 9 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 4 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 2 1 0 46 7 1 0 40 11 1 0 19 13 1 0 39 21 1 0 34 25 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 4 58 1 6 6 59 1 0 6 60 1 0 7 61 1 1 9 62 1 1 14 63 1 0 15 64 1 0 17 65 1 0 18 66 1 0 19 67 1 0 22 68 1 0 25 69 1 1 27 70 1 6 28 71 1 0 28 72 1 0 29 73 1 0 30 74 1 1 31 75 1 0 32 76 1 6 33 77 1 0 34 78 1 6 35 79 1 0 36 80 1 0 38 81 1 0 42 82 1 6 43 83 1 0 44 84 1 6 45 85 1 0 46 86 1 1 47 87 1 0 48 88 1 1 49 89 1 0 50 90 1 6 51 91 1 0 52 92 1 6 53 93 1 0 M END

Standard InCHIKey	SCEPATPTKMFDSR-OXAXHLCBSA-N
Standard InCHI	InChI=1S/C33H40O20/c1-10-19(37)23(41)26(44)31(48-10)47-9-17-21(39)25(43)28(46)33(52-17)53-30-22(40)18-14(36)6-13(49-32-27(45)24(42)20(38)16(8-34)51-32)7-15(18)50-29(30)11-2-4-12(35)5-3-11/h2-7,10,16-17,19-21,23-28,31-39,41-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21+,23-,24-,25+,26+,27+,28+,31+,32+,33-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(C4=CC=C(O)C=C4)OC4=CC(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=CC(O)=C4C3=O)[C@H](O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.21	Volume:	682.698 ? Van der Waals volume.
Dense:	1.108	LogP:	-0.089 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.881 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.782 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	328.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.305	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.623	Fluc inhibitor:	0.268 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.672 ? 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:	0.182	Promiscuous compounds:	0.538

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.924	MDCK Permeability:	-4.845
Pgp-inhibitor:	0.0	Pgp-substrate:	0.973
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):	0.993
20% Bioavailability (F20%):	0.273	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	78.908%	Volume Distribution (VD):	-0.089
Fu:	20.058% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.093
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.879
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):

0.737

Half-life (T1/2):

6.013

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.045
Human Hepatotoxicity (H-HT):	0.633	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.948	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.018	Eye Corrosion:	0.0
Eye Irritation:	0.024	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.992
Hematotoxicity:	0.143	Drug-induced Nephrotoxicity:	0.866
Genotoxicity:	0.7	RPMI-8226 Immunitoxicity:	0.239
A549 Cytotoxicity:	0.768	Hek293 Cytotoxicity:	0.451
BCF:	0.379 ? 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:	2.827 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.539 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.573 ? 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
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25126881]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28617598]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30649869]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	Whole Fruits	n.a.	n.a.	PMID[32159343]
NPO59893	Potentilla spp.	Genus	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO44984	Crocus spp.	Genus	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO44553	Hosta ventricosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO58706	Nicotiana spp.	Genus	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1042	Lycium halimifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO48299	Datura spp.	Genus	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49435	Limnanthes douglasii	Species	Limnanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49941	Equisetum telmateja	Genus	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45185	Macroptilium spp.	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29443	Equisetum palustre	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO869	Elaeagnus multiflora	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29443	Equisetum palustre	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29443	Equisetum palustre	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29443	Equisetum palustre	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11984	Tulipa gesneriana	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO869	Elaeagnus multiflora	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1042	Lycium halimifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29443	Equisetum palustre	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC551246 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	22086
0.1-0.2	23323
0.2-0.3	3334
0.3-0.4	558
0.4-0.5	266
0.5-0.6	98
0.6-0.7	70
0.7-0.8	2
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC186816
0.8587	High Similarity	NPC25523
0.8313	Intermediate Similarity	NPC116458
0.8313	Intermediate Similarity	NPC246943
0.7927	Intermediate Similarity	NPC297987
0.7812	Intermediate Similarity	NPC480441
0.764	Intermediate Similarity	NPC173582
0.764	Intermediate Similarity	NPC265885
0.764	Intermediate Similarity	NPC181465
0.764	Intermediate Similarity	NPC215710
0.764	Intermediate Similarity	NPC473438
0.764	Intermediate Similarity	NPC253788
0.759	Intermediate Similarity	NPC249281
0.7471	Intermediate Similarity	NPC605784
0.7444	Intermediate Similarity	NPC44931
0.7419	Intermediate Similarity	NPC32641
0.7419	Intermediate Similarity	NPC256188
0.7419	Intermediate Similarity	NPC35119
0.7412	Intermediate Similarity	NPC46420
0.7386	Intermediate Similarity	NPC276377
0.734	Intermediate Similarity	NPC142142
0.7174	Intermediate Similarity	NPC65563
0.7174	Intermediate Similarity	NPC470949
0.7174	Intermediate Similarity	NPC150164
0.7097	Intermediate Similarity	NPC473571
0.7097	Intermediate Similarity	NPC110941
0.7093	Intermediate Similarity	NPC136042
0.7071	Intermediate Similarity	NPC189564
0.7065	Intermediate Similarity	NPC67105
0.7041	Intermediate Similarity	NPC14187
0.7021	Intermediate Similarity	NPC240306
0.7021	Intermediate Similarity	NPC64425
0.6989	Remote Similarity	NPC203259
0.6989	Remote Similarity	NPC33054
0.6989	Remote Similarity	NPC210073
0.6989	Remote Similarity	NPC176740
0.6989	Remote Similarity	NPC471725
0.6989	Remote Similarity	NPC134532
0.6989	Remote Similarity	NPC156869
0.6989	Remote Similarity	NPC602582
0.6977	Remote Similarity	NPC289667
0.697	Remote Similarity	NPC203145
0.6848	Remote Similarity	NPC251417
0.6771	Remote Similarity	NPC470443
0.6768	Remote Similarity	NPC602448
0.6701	Remote Similarity	NPC72016
0.6634	Remote Similarity	NPC121703
0.6629	Remote Similarity	NPC84362
0.6629	Remote Similarity	NPC271692
0.6596	Remote Similarity	NPC471079
0.6566	Remote Similarity	NPC476472
0.6566	Remote Similarity	NPC294815
0.6566	Remote Similarity	NPC473073
0.6566	Remote Similarity	NPC16194
0.6538	Remote Similarity	NPC277532
0.6526	Remote Similarity	NPC39834
0.6526	Remote Similarity	NPC275454
0.6526	Remote Similarity	NPC227508
0.6505	Remote Similarity	NPC292019
0.6505	Remote Similarity	NPC202908
0.6495	Remote Similarity	NPC488073
0.6495	Remote Similarity	NPC126784
0.6495	Remote Similarity	NPC241423
0.6458	Remote Similarity	NPC22062
0.6458	Remote Similarity	NPC479405
0.6458	Remote Similarity	NPC473634
0.6458	Remote Similarity	NPC303913
0.6458	Remote Similarity	NPC138811
0.6404	Remote Similarity	NPC77672
0.6404	Remote Similarity	NPC133671
0.6404	Remote Similarity	NPC135391
0.6404	Remote Similarity	NPC78263
0.6404	Remote Similarity	NPC250069
0.6392	Remote Similarity	NPC479404
0.6364	Remote Similarity	NPC209296
0.6364	Remote Similarity	NPC473327
0.6333	Remote Similarity	NPC323593
0.6333	Remote Similarity	NPC203500
0.6264	Remote Similarity	NPC24043
0.6263	Remote Similarity	NPC12013
0.6263	Remote Similarity	NPC11432
0.6263	Remote Similarity	NPC477613
0.6222	Remote Similarity	NPC39360
0.6222	Remote Similarity	NPC29763
0.6222	Remote Similarity	NPC210003
0.6176	Remote Similarity	NPC101636
0.6154	Remote Similarity	NPC158674
0.6147	Remote Similarity	NPC298666
0.6132	Remote Similarity	NPC164704
0.6129	Remote Similarity	NPC611303
0.6126	Remote Similarity	NPC209550
0.6111	Remote Similarity	NPC111929
0.6111	Remote Similarity	NPC320283
0.6111	Remote Similarity	NPC41121
0.61	Remote Similarity	NPC479403
0.6071	Remote Similarity	NPC192539
0.6044	Remote Similarity	NPC108831
0.6044	Remote Similarity	NPC182634
0.602	Remote Similarity	NPC67326
0.6019	Remote Similarity	NPC292929
0.6019	Remote Similarity	NPC221342
0.6019	Remote Similarity	NPC476470
0.5982	Remote Similarity	NPC138990
0.5978	Remote Similarity	NPC277205
0.5978	Remote Similarity	NPC37919
0.5962	Remote Similarity	NPC135358
0.5934	Remote Similarity	NPC331652
0.5918	Remote Similarity	NPC139320
0.5914	Remote Similarity	NPC488080
0.5914	Remote Similarity	NPC169977
0.5893	Remote Similarity	NPC470720
0.5872	Remote Similarity	NPC470716
0.5865	Remote Similarity	NPC470449
0.5859	Remote Similarity	NPC163242
0.5859	Remote Similarity	NPC272068
0.5833	Remote Similarity	NPC470715
0.5825	Remote Similarity	NPC486577
0.5806	Remote Similarity	NPC145038
0.5806	Remote Similarity	NPC8573
0.5806	Remote Similarity	NPC56077
0.5806	Remote Similarity	NPC281131
0.5806	Remote Similarity	NPC64305
0.5806	Remote Similarity	NPC253662
0.5806	Remote Similarity	NPC179950
0.5806	Remote Similarity	NPC88789
0.5806	Remote Similarity	NPC189142
0.5806	Remote Similarity	NPC77660
0.5806	Remote Similarity	NPC491374
0.5804	Remote Similarity	NPC470717
0.58	Remote Similarity	NPC65003
0.5789	Remote Similarity	NPC175429
0.5784	Remote Similarity	NPC65711
0.5769	Remote Similarity	NPC470447
0.5758	Remote Similarity	NPC480466
0.5728	Remote Similarity	NPC122467
0.5714	Remote Similarity	NPC288084
0.5714	Remote Similarity	NPC116864
0.5714	Remote Similarity	NPC244776
0.5714	Remote Similarity	NPC298171
0.5699	Remote Similarity	NPC238376
0.5686	Remote Similarity	NPC488074
0.5686	Remote Similarity	NPC64051
0.5684	Remote Similarity	NPC472459
0.5636	Remote Similarity	NPC311850
0.5625	Remote Similarity	NPC307938
0.5625	Remote Similarity	NPC488071
0.5619	Remote Similarity	NPC89127
0.56	Remote Similarity	NPC187379
0.5588	Remote Similarity	NPC129264
0.5577	Remote Similarity	NPC606657
0.5575	Remote Similarity	NPC198199
0.5546	Remote Similarity	NPC483159
0.5546	Remote Similarity	NPC483160
0.5545	Remote Similarity	NPC470405
0.5534	Remote Similarity	NPC470125
0.5532	Remote Similarity	NPC127546
0.5532	Remote Similarity	NPC261866
0.5532	Remote Similarity	NPC57625
0.5532	Remote Similarity	NPC19709
0.5532	Remote Similarity	NPC173637
0.5532	Remote Similarity	NPC317489
0.5532	Remote Similarity	NPC223424
0.5532	Remote Similarity	NPC600591
0.5521	Remote Similarity	NPC599850
0.549	Remote Similarity	NPC605592
0.5487	Remote Similarity	NPC68592
0.5472	Remote Similarity	NPC85751
0.5472	Remote Similarity	NPC76831
0.5472	Remote Similarity	NPC19240
0.5464	Remote Similarity	NPC285197
0.5463	Remote Similarity	NPC470455
0.5455	Remote Similarity	NPC203050
0.5455	Remote Similarity	NPC170052
0.5455	Remote Similarity	NPC225434
0.5455	Remote Similarity	NPC476215
0.5455	Remote Similarity	NPC135846
0.5437	Remote Similarity	NPC204693
0.5437	Remote Similarity	NPC115674
0.5437	Remote Similarity	NPC470444
0.5431	Remote Similarity	NPC120952
0.5429	Remote Similarity	NPC473623
0.5429	Remote Similarity	NPC270448
0.5417	Remote Similarity	NPC27640
0.5413	Remote Similarity	NPC89052
0.5408	Remote Similarity	NPC601144
0.5405	Remote Similarity	NPC303694
0.5392	Remote Similarity	NPC471748
0.5391	Remote Similarity	NPC474522
0.5385	Remote Similarity	NPC153755
0.5377	Remote Similarity	NPC270675
0.5377	Remote Similarity	NPC488089
0.5377	Remote Similarity	NPC195685
0.537	Remote Similarity	NPC470446
0.5368	Remote Similarity	NPC19388
0.5368	Remote Similarity	NPC240431
0.5368	Remote Similarity	NPC55786
0.5361	Remote Similarity	NPC42773
0.5361	Remote Similarity	NPC45522
0.5354	Remote Similarity	NPC311830
0.5351	Remote Similarity	NPC295625

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC551246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5722
0.1-0.2	3356
0.2-0.3	61
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
0.6-0.7	2
0.7-0.8	2
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
0.7826	Intermediate Similarity	NPD7251	Phase 2
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.6989	Remote Similarity	NPD6797	Phase 2
0.6364	Remote Similarity	NPD7054	Phase 4
0.5234	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5135	Remote Similarity	NPD7472	Pre-clinical

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