NPASS Compound

Natural Product: NPC477617

Natural Product ID	NPC477617
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S,3S,5S,6R,8S)-3-[(2S,3R,4R,5S,6R)-6-(benzoyloxymethyl)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl 4-hydroxybenzoate
IUPAC Name	[(2S,3S,5S,6R,8S)-3-[(2S,3R,4R,5S,6R)-6-(benzoyloxymethyl)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.02,5.03,8]decan-2-yl]methyl 4-hydroxybenzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	76331994
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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 2D 96103 0 0 0 0 0 0 0 0999 V2000 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4138 -2.8518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1147 -3.6018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3647 -2.3027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6638 -1.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0641 -1.0152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4645 -0.4776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6991 1.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5334 1.9479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0995 1.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3342 3.0230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7345 3.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9003 2.6166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6656 1.1350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2652 0.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3006 3.1541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8010 -3.2467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5664 -4.7282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0661 -4.7021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8387 -5.9878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1115 -7.2997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6117 -7.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1609 -6.0402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7887 -7.8635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1890 -8.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3548 -7.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1201 -5.9755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7551 -7.9946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9209 -7.0506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3212 -7.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5559 -9.0697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3902 -10.0137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9898 -9.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8768 -8.7813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4764 -9.3188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2490 -10.6046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5218 -11.9165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9780 -11.9427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7505 -10.6569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0233 -9.3450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9163 -9.7130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0820 -8.7690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3784 -12.4802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2871 -13.3980 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4147 -11.5486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0044 -6.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4665 -4.1645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4028 -3.7960 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8808 -2.0120 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9266 -3.1519 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7580 -0.8169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8045 -3.4137 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0358 -4.6438 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8647 -4.9008 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9888 0.1828 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7684 -2.3396 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7013 0.4403 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1685 3.9670 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9692 5.0421 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8313 0.1910 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0306 -0.8841 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4663 2.2101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9279 -4.5976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3267 -3.2249 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0823 -5.1491 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4596 -7.9573 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5331 -8.8239 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9716 -9.3523 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3262 -6.4631 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6862 -5.5691 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4869 -6.6442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9563 -9.6073 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6248 -11.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9478 -10.5552 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1576 -7.9594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3811 -9.6205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8700 -12.5741 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8734 -13.4390 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 -11.4957 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8602 -10.8787 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2824 -8.3535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3107 -9.6294 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7379 -11.8464 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0373 -14.1023 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3624 -13.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9521 -8.4309 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7386 -4.9594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 9 11 1 0 8 12 1 6 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 19 22 1 0 7 23 1 1 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 27 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 44 49 1 0 43 50 1 0 42 51 1 0 26 52 1 0 25 53 1 0 4 54 1 1 7 2 1 0 10 2 1 0 11 4 1 0 8 5 1 0 21 16 1 0 29 24 1 0 39 34 1 0 46 41 1 0 1 55 1 0 1 56 1 0 1 57 1 0 3 58 1 0 3 59 1 0 5 60 1 6 6 61 1 0 6 62 1 0 9 63 1 0 12 64 1 0 12 65 1 0 17 66 1 0 18 67 1 0 20 68 1 0 21 69 1 0 22 70 1 0 24 71 1 6 25 72 1 1 26 73 1 6 27 74 1 1 28 75 1 6 30 76 1 0 30 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 38 81 1 0 39 82 1 0 41 83 1 6 42 84 1 1 43 85 1 6 44 86 1 1 45 87 1 6 47 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 50 92 1 0 51 93 1 0 52 94 1 0 53 95 1 0 54 96 1 0 M END

Standard InCHIKey	VPVGENHRANUECH-BUNNSMRTSA-N
Standard InCHI	InChI=1S/C36H42O18/c1-33-14-35(46)21-11-36(33,34(21,32(53-33)54-35)15-48-29(45)17-7-9-18(38)10-8-17)52-31-26(43)24(41)27(51-30-25(42)23(40)22(39)19(12-37)49-30)20(50-31)13-47-28(44)16-5-3-2-4-6-16/h2-10,19-27,30-32,37-43,46H,11-15H2,1H3/t19-,20-,21+,22-,23+,24-,25-,26-,27-,30+,31+,32?,33+,34+,35-,36-/m1/s1
SMILES	C[C@]12C[C@@]3([C@H]4C[C@@]1([C@@]4(C(O2)O3)COC(=O)C5=CC=C(C=C5)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC(=O)C7=CC=CC=C7)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	762.24	Volume:	699.893 ? Van der Waals volume.
Dense:	1.089	LogP:	0.562 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.36 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.507 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	39.0
TPSA:	269.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	8.0	Rings:	10.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.741	Fsp³:	0.611
MCE-18:	191.897 ? 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:	0.66	Fluc inhibitor:	0.044 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.276 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.159	Promiscuous compounds:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.467	MDCK Permeability:	-5.289
Pgp-inhibitor:	0.003	Pgp-substrate:	0.254
PAMPA:	0.981 ? 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):	0.154
20% Bioavailability (F20%):	0.783	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.47
Plasma Protein Binding (PPB):	72.919%	Volume Distribution (VD):	-0.504
Fu:	36.247% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.01
BSEP inhibitor:	0.069

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.867
HLM stability:	0.379 ? 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):

1.359

Half-life (T1/2):

4.034

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.169
Human Hepatotoxicity (H-HT):	0.064	Drug-induced Liver Injury (DILI):	0.809
AMES Toxicity:	0.907	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.032	Skin Sensitization:	1.0
Carcinogencity:	0.26	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.078	Ototoxicity:	0.97
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.611
Genotoxicity:	0.05	RPMI-8226 Immunitoxicity:	0.173
A549 Cytotoxicity:	0.767	Hek293 Cytotoxicity:	0.835
BCF:	0.428 ? 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:	3.364 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.295 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.206 ? 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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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	6

Activity Type	# Activity
Others	6

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
NPT2	Others	Unspecified	n.a.	Activity	=	89.29	%	PMID[24377852]
NPT2	Others	Unspecified	n.a.	Activity	=	80.12	%	PMID[24377852]
NPT2	Others	Unspecified	n.a.	Activity	<	10	%	PMID[24377852]

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 NPC477617 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	12960
0.1-0.2	31941
0.2-0.3	4772
0.3-0.4	143
0.4-0.5	8
0.5-0.6	13
0.6-0.7	8
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.814	Intermediate Similarity	NPC293568
0.814	Intermediate Similarity	NPC161626
0.7802	Intermediate Similarity	NPC469396
0.7802	Intermediate Similarity	NPC469458
0.7802	Intermediate Similarity	NPC149002
0.7791	Intermediate Similarity	NPC303429
0.7791	Intermediate Similarity	NPC56594
0.7363	Intermediate Similarity	NPC88176
0.7234	Intermediate Similarity	NPC469398
0.7033	Intermediate Similarity	NPC34066
0.7033	Intermediate Similarity	NPC190862
0.6837	Remote Similarity	NPC195114
0.6768	Remote Similarity	NPC148185
0.6735	Remote Similarity	NPC80360
0.6702	Remote Similarity	NPC120012
0.6699	Remote Similarity	NPC469421
0.6667	Remote Similarity	NPC188217
0.6095	Remote Similarity	NPC478828
0.6055	Remote Similarity	NPC469397
0.596	Remote Similarity	NPC117943
0.5872	Remote Similarity	NPC478826
0.5872	Remote Similarity	NPC478827
0.578	Remote Similarity	NPC478829
0.5686	Remote Similarity	NPC469419
0.5657	Remote Similarity	NPC222102
0.5472	Remote Similarity	NPC265600
0.5385	Remote Similarity	NPC469415
0.5377	Remote Similarity	NPC469438
0.5333	Remote Similarity	NPC469420
0.5146	Remote Similarity	NPC469422
0.51	Remote Similarity	NPC133430
0.5098	Remote Similarity	NPC469417

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4270
0.1-0.2	4786
0.2-0.3	94
0.3-0.4	0
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