NPASS Compound

Natural Product: NPC475296

Natural Product ID	NPC475296
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Alpha-Rhamnopyranosyl-(1->2)-Alpha-Arabinopyranosylmesembryanthemoidigenic Acid
IUPAC Name	(2R,4aR,6aS,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(hydroxymethyl)-2,6a,9,9,12a-pentamethyl-3,4,5,6,6a,6b,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503120
PubChem CID	44559150
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 116122 0 0 0 0 0 0 0 0999 V2000 -8.9190 -0.6221 3.2961 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6999 -0.0754 2.8413 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9529 0.6395 1.4915 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0052 1.7049 1.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6926 -0.2912 0.6307 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8453 -0.9317 -0.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1275 0.0884 -1.1867 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3145 1.0867 -0.3918 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7100 1.2737 1.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8615 0.8765 -0.6539 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1354 1.9467 -0.8912 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7027 2.0544 -1.1827 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0591 0.8403 -0.6212 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7720 -0.3752 -1.1257 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2081 -0.4584 -0.6709 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0374 -1.2620 -1.6812 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1861 -0.5222 -2.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2633 -1.2254 0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9528 -1.5926 -0.8573 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7981 -1.4502 0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0088 -0.1944 -0.0924 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5757 0.7753 -1.0512 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3716 0.5359 -2.4834 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0858 2.1163 -0.7190 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5476 2.0805 -0.7112 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2430 0.8579 -0.2313 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4935 -0.4235 -0.2210 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8411 -1.2352 1.0517 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8874 -1.3184 -1.3704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4678 0.6499 -0.9172 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5743 0.8192 -0.1001 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3568 1.9021 -0.4862 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8237 1.8298 -1.7856 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7192 0.6223 -1.9844 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9189 -0.5931 -1.5632 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4067 -0.4264 -0.1381 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5315 -0.3768 0.6545 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7383 -1.3720 1.5460 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9332 -0.7578 2.8099 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7637 0.3279 2.6068 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7863 1.2663 3.7930 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1781 -0.1899 2.4349 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1936 -1.0402 1.1848 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0698 -2.0498 1.1834 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3289 -3.0644 2.0776 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3911 -1.7538 1.1809 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 0.8936 2.2243 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9535 -0.9363 -2.4715 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0702 0.4823 -3.3018 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1817 0.7631 -2.0322 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1780 0.5926 -3.2800 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1090 1.5481 -1.3889 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9036 -1.6111 3.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9243 -0.8413 2.7608 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3851 0.6555 3.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0006 1.2612 1.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7702 2.0909 2.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9970 2.5175 1.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6505 0.1008 0.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0602 -1.1514 1.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4530 -1.5358 -1.1237 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1289 -1.6529 0.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6283 2.0657 -0.8958 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8239 2.3908 1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8905 1.0548 1.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7071 2.9157 -0.8606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6095 2.1220 -2.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3094 2.9834 -0.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0625 0.9118 0.4884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8093 -0.2556 -2.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3624 -1.4975 -2.5531 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3621 -2.2349 -1.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8162 -1.2194 -2.8169 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9175 0.3071 -2.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3709 -2.3193 0.3273 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4123 -1.0562 1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1640 -1.0804 1.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5368 -2.4671 -0.4359 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5604 -2.0763 -1.8050 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1308 -1.6287 1.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1003 -2.3052 -0.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0701 0.3228 0.9216 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4081 1.2349 -2.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2906 0.7965 -3.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1165 -0.4896 -2.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3240 2.8353 -1.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3664 2.4256 0.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8919 2.2400 -1.7793 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9156 2.9915 -0.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5518 1.0832 0.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8776 -2.3045 0.8632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1567 -0.9607 1.8812 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8461 -0.8749 1.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1759 -2.1030 -1.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2195 -0.7241 -2.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8212 -1.8742 -1.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1924 1.0711 0.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9774 1.7523 -2.4775 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4550 2.7283 -1.9549 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5904 0.6659 -1.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6435 -1.4451 -1.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8455 -1.3352 0.1118 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0093 -2.1803 1.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5273 0.9225 1.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7977 1.2867 4.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0374 2.3041 3.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5878 0.9734 4.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5601 -0.7273 3.3127 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1825 -0.4020 0.2727 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9814 -2.4564 0.1583 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0269 -2.7436 2.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2536 -2.7239 1.0370 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1502 1.1322 1.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7961 -1.9139 -2.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3823 -0.1106 -3.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5256 2.3153 -1.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 1 14 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 26 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 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 40 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 35 48 1 0 34 49 1 0 7 50 1 6 50 51 2 0 50 52 1 0 9 3 1 0 15 10 1 0 27 21 1 0 36 31 1 0 44 38 1 0 17 7 1 0 22 13 1 0 1 53 1 0 2 54 1 0 2 55 1 0 4 56 1 0 4 57 1 0 4 58 1 0 5 59 1 0 5 60 1 0 6 61 1 0 6 62 1 0 8 63 1 6 9 64 1 0 9 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 1 14 70 1 6 16 71 1 0 16 72 1 0 17 73 1 0 17 74 1 0 18 75 1 0 18 76 1 0 18 77 1 0 19 78 1 0 19 79 1 0 20 80 1 0 20 81 1 0 21 82 1 1 23 83 1 0 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 25 88 1 0 25 89 1 0 26 90 1 1 28 91 1 0 28 92 1 0 28 93 1 0 29 94 1 0 29 95 1 0 29 96 1 0 31 97 1 1 33 98 1 0 33 99 1 0 34100 1 1 35101 1 1 36102 1 1 38103 1 1 40104 1 6 41105 1 0 41106 1 0 41107 1 0 42108 1 1 43109 1 6 44110 1 6 45111 1 0 46112 1 0 47113 1 0 48114 1 0 49115 1 0 52116 1 0 M END

Standard InCHIKey	IQYCTFZPKCGQBS-CMHDGEJMSA-N
Standard InCHI	InChI=1S/C40H64O12/c1-20-28(43)30(45)31(46)33(50-20)52-32-29(44)25(42)18-49-34(32)51-27-11-12-39(6)22-7-8-23-24-17-37(4,19-41)13-15-40(24,35(47)48)16-14-38(23,5)21(22)9-10-26(39)36(27,2)3/h8,20-22,24-34,41-46H,7,9-19H2,1-6H3,(H,47,48)/t20-,21+,22-,24-,25-,26-,27-,28-,29-,30+,31+,32+,33-,34-,37+,38-,39+,40-/m0/s1
SMILES	OC[C@]1(C)CC[C@]2([C@@H](C1)C1=CC[C@H]3[C@H]([C@@]1(CC2)C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	736.44	Volume:	740.71 ? Van der Waals volume.
Dense:	0.994	LogP:	2.707 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.314 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.509 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	39.0
TPSA:	195.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.156	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.854	Fsp³:	0.925
MCE-18:	144.519 ? 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:	0.956	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.191	Promiscuous compounds:	0.098

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.064	MDCK Permeability:	-5.115
Pgp-inhibitor:	0.0	Pgp-substrate:	0.292
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):	0.188
20% Bioavailability (F20%):	0.905	30% Bioavailability (F30%):	0.952
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117	MRP1:	0.38
Plasma Protein Binding (PPB):	73.896%	Volume Distribution (VD):	-0.494
Fu:	19.623% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.02
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.969	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.5

Half-life (T1/2):

2.683

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.774	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.623	Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.037	Skin Sensitization:	1.0
Carcinogencity:	0.492	Eye Corrosion:	0.0
Eye Irritation:	0.048	Respiratory Toxicity:	0.453
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.967
Hematotoxicity:	0.656	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.569	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.453	Hek293 Cytotoxicity:	0.318
BCF:	1.357 ? 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:	3.798 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.422 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.611 ? 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
NPO31494	Acanthopanax senticosus	n.a.	n.a.	n.a.	n.a.	leaf	n.a.	PMID[11816040]
NPO31494	Acanthopanax senticosus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17125224]
NPO31494	Acanthopanax senticosus	n.a.	n.a.	n.a.	Barks	Iksan, Chunbuk, Korea	n.a.	PMID[3127544]
NPO31494	Acanthopanax senticosus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31494	Acanthopanax senticosus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31494	Acanthopanax senticosus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2797	Individual protein	Pancreatic lipase	Homo sapiens	Inhibition	=	33.0	%	PMID[11908979]

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 NPC475296 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	21762
0.1-0.2	23685
0.2-0.3	3326
0.3-0.4	836
0.4-0.5	204
0.5-0.6	34
0.6-0.7	6
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
0.8636	High Similarity	NPC474589
0.6907	Remote Similarity	NPC56713
0.64	Remote Similarity	NPC174679
0.64	Remote Similarity	NPC279554
0.6337	Remote Similarity	NPC127056
0.6055	Remote Similarity	NPC324875
0.6055	Remote Similarity	NPC292677
0.578	Remote Similarity	NPC481082
0.578	Remote Similarity	NPC164419
0.578	Remote Similarity	NPC257468
0.5769	Remote Similarity	NPC25605
0.5769	Remote Similarity	NPC59804
0.5641	Remote Similarity	NPC219180
0.5641	Remote Similarity	NPC251263
0.5607	Remote Similarity	NPC80843
0.5596	Remote Similarity	NPC104400
0.5596	Remote Similarity	NPC10320
0.5574	Remote Similarity	NPC161717
0.5536	Remote Similarity	NPC276093
0.5508	Remote Similarity	NPC475209
0.55	Remote Similarity	NPC488211
0.5495	Remote Similarity	NPC275668
0.5391	Remote Similarity	NPC475486
0.5378	Remote Similarity	NPC309907
0.537	Remote Similarity	NPC488561
0.5333	Remote Similarity	NPC164194
0.5268	Remote Similarity	NPC139044
0.5268	Remote Similarity	NPC471383
0.525	Remote Similarity	NPC166422
0.5234	Remote Similarity	NPC12288
0.5225	Remote Similarity	NPC204392
0.5214	Remote Similarity	NPC280941
0.5214	Remote Similarity	NPC235772
0.5167	Remote Similarity	NPC133818
0.5156	Remote Similarity	NPC488212
0.5135	Remote Similarity	NPC469945
0.5091	Remote Similarity	NPC472949
0.5089	Remote Similarity	NPC114304
0.5086	Remote Similarity	NPC323359
0.5043	Remote Similarity	NPC488564
0.5043	Remote Similarity	NPC79718

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6195
0.1-0.2	2894
0.2-0.3	55
0.3-0.4	6
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