NPASS Compound

Natural Product: NPC126958

Natural Product ID	NPC126958
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DHWHIUKSBPWEHK-QPBLYYNVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101615131
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 107112 0 0 0 0 0 0 0 0999 V2000 1.4284 -5.7070 1.2693 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7455 -4.2384 1.1266 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6785 -3.7478 2.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2259 -2.4714 2.7912 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7970 -1.4169 1.7546 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2173 -0.3182 2.5632 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2948 0.6028 1.8651 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8313 -0.1008 1.1438 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7099 -0.7620 2.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2050 -1.1201 0.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6009 -1.3470 -0.9997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7079 -0.6404 -1.6938 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5068 0.0425 -0.6059 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7532 0.7170 -1.0722 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5707 1.8666 -1.9998 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5517 -0.3316 -1.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9591 0.0668 -2.1111 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7157 0.5593 -0.9271 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9384 1.4861 -0.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1126 2.9229 -0.3843 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5981 1.3007 1.3521 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5191 1.0317 0.1731 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7789 1.9064 1.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3101 1.9362 1.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6113 0.8641 0.2754 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5504 1.5386 -0.6131 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8450 1.2434 -1.3744 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6180 -1.1098 -2.5524 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9226 -1.9907 0.7044 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4668 -3.3864 1.0819 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4222 -4.0337 0.0644 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2023 -3.4453 2.2960 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0962 -0.9314 1.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2165 -1.3372 1.5170 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0882 0.0551 0.1720 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2872 0.5414 -0.4049 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3659 0.2115 -1.8821 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2256 1.2828 -2.5076 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4068 1.6506 -1.6067 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9213 2.0685 -0.2382 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2565 3.4654 0.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5425 3.7598 0.2742 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5029 3.6651 -0.6419 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4959 1.8917 -0.2164 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2840 0.5783 -1.5854 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4834 2.4477 -2.6947 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8717 -1.0641 -2.0123 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5858 -5.9108 1.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3330 -6.1794 1.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3081 -6.2117 0.2735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1853 -4.1070 0.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6792 -3.6019 1.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7195 -4.5041 2.9960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4900 -2.5618 3.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 -2.0050 3.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7499 -0.6998 3.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0717 0.3180 2.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8882 1.2482 1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0746 1.3120 2.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2106 -1.0303 3.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5599 -0.0912 2.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2240 -1.6662 1.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0945 -2.1049 -1.5958 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3153 -1.4218 -2.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3497 0.0441 -2.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8686 -0.8068 0.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1210 2.7664 -1.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5622 2.0551 -2.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9283 1.5131 -2.8472 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0729 -0.6021 -2.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5855 -1.2247 -1.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0689 0.7735 -2.9626 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1010 -0.3326 -0.3524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9096 2.9562 -1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5787 3.5358 0.4458 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2190 3.4730 -0.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2333 0.3405 1.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3327 2.1364 2.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6960 1.2494 1.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6255 0.0270 0.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1215 1.6764 2.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2060 2.9482 0.9968 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9999 2.9544 0.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9003 1.9593 2.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9234 1.8314 -1.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3307 0.9148 -0.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1721 2.4794 -0.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0482 1.0341 -2.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4266 -1.2978 -2.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5756 -2.1475 -0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0910 -4.3707 -0.8496 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7693 -4.9960 0.5528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3726 -3.4889 -0.1122 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9510 -4.0774 2.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1189 -0.0026 0.0892 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3743 0.2747 -2.3758 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6533 0.9064 -3.4557 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8835 2.5005 -2.1061 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3145 1.3665 0.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8401 4.1690 -0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7260 3.7142 1.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5142 4.0614 -0.2286 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3934 4.2430 -1.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8412 2.6105 -0.9108 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4539 0.3536 -0.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5997 2.7084 -3.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5760 -1.2147 -1.3534 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 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 0 17 28 1 0 10 29 1 0 29 30 1 0 30 31 1 0 30 32 1 1 5 33 1 6 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 37 47 1 0 30 2 1 0 44 36 1 0 29 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 9 60 1 0 9 61 1 0 9 62 1 0 11 63 1 0 12 64 1 0 12 65 1 0 13 66 1 1 15 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 17 72 1 6 18 73 1 1 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 21 78 1 0 21 79 1 0 22 80 1 1 23 81 1 0 23 82 1 0 24 83 1 0 24 84 1 0 26 85 1 0 26 86 1 0 26 87 1 0 27 88 1 0 28 89 1 0 29 90 1 6 31 91 1 0 31 92 1 0 31 93 1 0 32 94 1 0 36 95 1 1 37 96 1 6 38 97 1 6 39 98 1 6 40 99 1 1 41100 1 0 41101 1 0 43102 1 0 43103 1 0 43104 1 0 45105 1 0 46106 1 0 47107 1 0 M END

Standard InCHIKey	DHWHIUKSBPWEHK-QPBLYYNVSA-N
Standard InCHI	InChI=1S/C37H60O10/c1-19-11-14-37(31(43)47-30-27(41)26(40)25(39)22(46-30)18-45-8)16-15-34(5)20(28(37)36(19,7)44)9-10-24-33(4)17-21(38)29(42)32(2,3)23(33)12-13-35(24,34)6/h9,19,21-30,38-42,44H,10-18H2,1-8H3/t19-,21-,22-,23+,24-,25-,26+,27-,28-,29+,30+,33+,34-,35-,36-,37+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@]1(C)O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	664.42	Volume:	679.799 ? Van der Waals volume.
Dense:	0.977	LogP:	2.731 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.021 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.065 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	33.0
TPSA:	166.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.194	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.587	Fsp³:	0.919
MCE-18:	132.507 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.784	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.185	Promiscuous compounds:	0.221

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.772	MDCK Permeability:	-5.201
Pgp-inhibitor:	0.0	Pgp-substrate:	0.335
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):	0.142
20% Bioavailability (F20%):	0.969	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199	MRP1:	0.152
Plasma Protein Binding (PPB):	81.826%	Volume Distribution (VD):	-0.106
Fu:	15.845% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.044
BSEP inhibitor:	0.363

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.411
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.205
HLM stability:	0.256 ? 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):

1.092

Half-life (T1/2):

2.143

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.058
Human Hepatotoxicity (H-HT):	0.476	Drug-induced Liver Injury (DILI):	0.378
AMES Toxicity:	0.582	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.047	Skin Sensitization:	0.895
Carcinogencity:	0.431	Eye Corrosion:	0.0
Eye Irritation:	0.058	Respiratory Toxicity:	0.057
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.943
Hematotoxicity:	0.396	Drug-induced Nephrotoxicity:	0.97
Genotoxicity:	0.061	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.223	Hek293 Cytotoxicity:	0.105
BCF:	1.489 ? 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:	3.88 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.549 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.723 ? 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
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	Leaves	Huangshan, Anhui Province, China	2008-NOV	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21384845]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23632365]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3868	Senecio sinuatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11165	Spirographis spallanzani	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18564	Ligularia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7372	Rosa laevigata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1507	Cissus quinquefolia	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2663	Casimiroa tetrameria	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4855	Colchicum speciosum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9388	Heliomeris multiflora	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

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 NPC126958 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	19725
0.1-0.2	25511
0.2-0.3	3848
0.3-0.4	590
0.4-0.5	141
0.5-0.6	26
0.6-0.7	9
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
0.8272	Intermediate Similarity	NPC310014
0.8272	Intermediate Similarity	NPC269315
0.7326	Intermediate Similarity	NPC271138
0.7143	Intermediate Similarity	NPC259788
0.7143	Intermediate Similarity	NPC255589
0.686	Remote Similarity	NPC46388
0.6667	Remote Similarity	NPC605954
0.6444	Remote Similarity	NPC7870
0.6444	Remote Similarity	NPC75747
0.6333	Remote Similarity	NPC37739
0.6105	Remote Similarity	NPC47063
0.6042	Remote Similarity	NPC204458
0.6042	Remote Similarity	NPC189884
0.6042	Remote Similarity	NPC138334
0.587	Remote Similarity	NPC116794
0.5743	Remote Similarity	NPC58448
0.5684	Remote Similarity	NPC102914
0.5684	Remote Similarity	NPC110139
0.5684	Remote Similarity	NPC108709
0.5607	Remote Similarity	NPC134835
0.5579	Remote Similarity	NPC68419
0.5566	Remote Similarity	NPC68175
0.5556	Remote Similarity	NPC73318
0.5524	Remote Similarity	NPC160415
0.5464	Remote Similarity	NPC220984
0.5435	Remote Similarity	NPC191763
0.5429	Remote Similarity	NPC75417
0.5412	Remote Similarity	NPC136313
0.5349	Remote Similarity	NPC307335
0.5349	Remote Similarity	NPC74855
0.5347	Remote Similarity	NPC29069
0.5319	Remote Similarity	NPC167383
0.5312	Remote Similarity	NPC65590
0.5312	Remote Similarity	NPC125923
0.5294	Remote Similarity	NPC48499
0.5234	Remote Similarity	NPC104071
0.5189	Remote Similarity	NPC473343
0.5102	Remote Similarity	NPC604133
0.5094	Remote Similarity	NPC295371
0.5045	Remote Similarity	NPC601659

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC126958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7160
0.1-0.2	1949
0.2-0.3	40
0.3-0.4	1
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