NPASS Compound

Natural Product: NPC114441

Natural Product ID	NPC114441
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-L-Rhamnopyranoside(1->3)-Beta-D-Glucopyranosiduronic Acid]Oleanolic Acid
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452390
PubChem CID	44566867
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 121127 0 0 0 0 0 0 0 0999 V2000 10.9601 -1.5589 -0.8365 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7312 -1.1647 -0.0315 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1173 -1.2230 1.4368 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6725 0.0200 2.1648 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2734 0.3565 1.6812 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2117 0.5523 0.1966 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4100 0.1563 -0.3987 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1873 -0.1897 -0.3711 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2729 0.6025 -1.0646 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2585 0.1063 -2.4927 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8959 0.2565 -3.1277 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2187 -1.0420 -3.2953 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0351 -1.1760 -2.9376 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8978 -2.1015 -3.8470 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1107 1.2261 -2.5644 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8197 1.0717 -1.2290 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9196 0.3446 -0.4733 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8545 0.5731 0.8870 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5670 0.5344 -0.9944 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 1.3750 -0.3368 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5501 1.8192 -1.2525 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3367 0.6723 -1.6179 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9218 -0.0228 -0.3970 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5380 -1.4591 -0.4653 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 0.6799 0.8212 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9531 0.1018 2.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4366 0.4935 2.0853 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0991 -0.0634 0.8612 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2969 -1.5388 1.0993 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4072 0.2471 -0.4179 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1420 -0.2979 -1.5771 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5670 -0.5497 -1.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 -0.1582 -0.2329 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6940 -0.4940 -0.0981 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4345 -0.0023 -1.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8766 -0.4921 -1.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9423 -1.9994 -1.3599 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5518 0.0416 -2.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5853 -0.0414 -0.0716 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6563 0.6951 0.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3573 -0.0321 1.1329 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5815 0.9178 2.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1346 0.6260 2.1404 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4780 0.6138 0.7868 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3559 2.0264 0.2871 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7409 -1.1798 2.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9278 -1.3889 2.3809 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8029 -2.0775 2.5326 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0956 0.7963 0.9123 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3441 1.8388 2.0223 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7940 -0.4548 1.3704 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2692 0.7220 -3.2484 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8594 1.4932 2.3926 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5557 1.0808 1.9571 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4684 -2.3049 2.0298 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8235 -1.1256 -1.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0897 -2.6509 -0.8607 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8214 -1.0262 -0.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8854 -1.8537 -0.2313 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2196 -1.3165 1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6383 -0.1907 3.2378 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6097 -0.4648 1.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1086 1.6342 -0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5861 1.6634 -0.9954 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4819 -0.9829 -2.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1040 0.6182 -4.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5420 -3.0501 -3.9039 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8057 2.1158 -0.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7125 -0.7494 -0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8781 1.5106 1.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2698 2.3322 -0.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0547 2.1529 -2.1916 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0359 2.6829 -0.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1169 1.0558 -2.2985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2781 -0.0314 -2.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9356 -1.8989 -1.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7785 -2.0520 0.4364 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -1.4707 -0.6483 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7904 1.7357 0.7680 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8562 -0.9846 2.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4558 0.5702 2.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8882 -0.0159 2.9682 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4968 1.5765 2.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3401 -1.7369 1.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6586 -1.9404 1.9146 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1546 -2.1443 0.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4599 1.3768 -0.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1410 0.4126 -2.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7339 -1.2341 -2.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1180 -1.1367 -2.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7730 -1.6158 -0.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4573 1.0843 -1.4178 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9943 -0.5197 -2.2239 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2252 -2.4161 -0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9647 -2.4577 -1.6704 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7000 -2.3842 -2.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9796 0.8761 -3.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5988 -0.7656 -3.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6166 0.3154 -2.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3805 0.6864 -0.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0830 -0.8575 0.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4322 1.6985 0.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1372 0.8772 1.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0246 0.8627 3.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8065 1.9605 1.6918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9774 -0.2994 2.7101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6729 1.4476 2.7247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2580 2.6104 0.5646 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3384 2.0834 -0.8414 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5046 2.5795 0.7353 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8043 -2.3744 3.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4950 2.5400 2.1050 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2459 2.4351 1.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5004 1.3311 2.9769 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0989 -1.2574 1.6998 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4600 -0.2822 2.2688 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5189 -0.8494 0.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9386 0.0859 -3.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2599 1.4431 3.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2564 1.8812 2.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7636 -3.1284 1.5456 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 11 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 36 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 6 41 46 1 1 46 47 2 0 46 48 1 0 25 49 1 0 49 50 1 0 49 51 1 0 10 52 1 0 5 53 1 0 4 54 1 0 3 55 1 0 7 2 1 0 17 9 1 0 49 20 1 0 30 23 1 0 44 33 1 0 44 28 1 0 41 34 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 1 3 60 1 6 4 61 1 1 5 62 1 6 6 63 1 1 9 64 1 6 10 65 1 1 11 66 1 6 14 67 1 0 16 68 1 1 17 69 1 1 18 70 1 0 20 71 1 1 21 72 1 0 21 73 1 0 22 74 1 0 22 75 1 0 24 76 1 0 24 77 1 0 24 78 1 0 25 79 1 6 26 80 1 0 26 81 1 0 27 82 1 0 27 83 1 0 29 84 1 0 29 85 1 0 29 86 1 0 30 87 1 6 31 88 1 0 31 89 1 0 32 90 1 0 34 91 1 1 35 92 1 0 35 93 1 0 37 94 1 0 37 95 1 0 37 96 1 0 38 97 1 0 38 98 1 0 38 99 1 0 39100 1 0 39101 1 0 40102 1 0 40103 1 0 42104 1 0 42105 1 0 43106 1 0 43107 1 0 45108 1 0 45109 1 0 45110 1 0 48111 1 0 50112 1 0 50113 1 0 50114 1 0 51115 1 0 51116 1 0 51117 1 0 52118 1 0 53119 1 0 54120 1 0 55121 1 0 M END

Standard InCHIKey	NSJVFPXRIPXFLW-RWTBGSELSA-N
Standard InCHI	InChI=1S/C42H66O13/c1-20-26(43)27(44)28(45)34(52-20)54-31-29(46)32(33(48)49)55-35(30(31)47)53-25-12-13-39(6)23(38(25,4)5)11-14-41(8)24(39)10-9-21-22-19-37(2,3)15-17-42(22,36(50)51)18-16-40(21,41)7/h9,20,22-32,34-35,43-47H,10-19H2,1-8H3,(H,48,49)(H,50,51)/t20-,22-,23-,24+,25-,26-,27+,28+,29-,30+,31-,32-,34-,35+,39-,40+,41+,42-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]1[C@@H]([C@@H](C(=O)O)O[C@H]([C@@H]1O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	778.45	Volume:	781.456 ? Van der Waals volume.
Dense:	0.996	LogP:	2.548 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.75 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.343 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	40.0
TPSA:	212.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.766	Fsp³:	0.905
MCE-18:	154.0 ? 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:	0.959	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.215	Promiscuous compounds:	0.124

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.877	MDCK Permeability:	-5.206
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
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):	0.086
20% Bioavailability (F20%):	0.226	30% Bioavailability (F30%):	0.387
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.668
Plasma Protein Binding (PPB):	80.195%	Volume Distribution (VD):	-0.568
Fu:	14.39% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

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:	0.991	CYP3A4-substrate:	0.881
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.038
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):

0.333

Half-life (T1/2):

3.886

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.633	Drug-induced Liver Injury (DILI):	0.969
AMES Toxicity:	0.206	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.036	Skin Sensitization:	0.989
Carcinogencity:	0.107	Eye Corrosion:	0.0
Eye Irritation:	0.012	Respiratory Toxicity:	0.11
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.984
Hematotoxicity:	0.389	Drug-induced Nephrotoxicity:	0.948
Genotoxicity:	0.54	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.031	Hek293 Cytotoxicity:	0.071
BCF:	0.986 ? 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:	3.902 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.692 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.777 ? 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
NPO6683	Salacia petenensis	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[11270725]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19167901]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38435667]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5192	Cistus albidus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6683	Salacia petenensis	Species	Celastraceae	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	1

Activity Type	# Activity
Organism	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
NPT3469	Organism	Biomphalaria glabrata	Biomphalaria glabrata	Activity	=	4.0	ppm	DOI[10.1021/np9604137]

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 NPC114441 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	23119
0.1-0.2	23119
0.2-0.3	2446
0.3-0.4	741
0.4-0.5	306
0.5-0.6	70
0.6-0.7	38
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
0.8352	Intermediate Similarity	NPC6377
0.8352	Intermediate Similarity	NPC208381
0.7727	Intermediate Similarity	NPC286347
0.75	Intermediate Similarity	NPC606107
0.7188	Intermediate Similarity	NPC25605
0.7188	Intermediate Similarity	NPC56713
0.7143	Intermediate Similarity	NPC22956
0.7041	Intermediate Similarity	NPC472949
0.6931	Remote Similarity	NPC180550
0.6931	Remote Similarity	NPC35405
0.6923	Remote Similarity	NPC283849
0.6875	Remote Similarity	NPC270667
0.6832	Remote Similarity	NPC114304
0.6827	Remote Similarity	NPC114484
0.6813	Remote Similarity	NPC204407
0.6762	Remote Similarity	NPC324875
0.6762	Remote Similarity	NPC292677
0.6737	Remote Similarity	NPC294112
0.6701	Remote Similarity	NPC164194
0.6635	Remote Similarity	NPC481082
0.6635	Remote Similarity	NPC164419
0.6635	Remote Similarity	NPC257468
0.6566	Remote Similarity	NPC12288
0.65	Remote Similarity	NPC174679
0.65	Remote Similarity	NPC279554
0.6442	Remote Similarity	NPC159309
0.6442	Remote Similarity	NPC86222
0.6436	Remote Similarity	NPC127056
0.6436	Remote Similarity	NPC109079
0.6286	Remote Similarity	NPC104400
0.6286	Remote Similarity	NPC10320
0.6283	Remote Similarity	NPC166422
0.6283	Remote Similarity	NPC219180
0.6283	Remote Similarity	NPC251263
0.6263	Remote Similarity	NPC480938
0.625	Remote Similarity	NPC31839
0.6211	Remote Similarity	NPC28198
0.6211	Remote Similarity	NPC476123
0.6204	Remote Similarity	NPC276093
0.6186	Remote Similarity	NPC161717
0.6174	Remote Similarity	NPC54636
0.6078	Remote Similarity	NPC136877
0.6075	Remote Similarity	NPC139044
0.6075	Remote Similarity	NPC471383
0.6058	Remote Similarity	NPC488561
0.602	Remote Similarity	NPC100383
0.5963	Remote Similarity	NPC79718
0.5943	Remote Similarity	NPC469945
0.5865	Remote Similarity	NPC59804
0.5856	Remote Similarity	NPC323359
0.5843	Remote Similarity	NPC120840
0.5842	Remote Similarity	NPC191410
0.5841	Remote Similarity	NPC480936
0.5818	Remote Similarity	NPC119794
0.5804	Remote Similarity	NPC488564
0.5798	Remote Similarity	NPC21691
0.5784	Remote Similarity	NPC475472
0.5776	Remote Similarity	NPC323341
0.5776	Remote Similarity	NPC133818
0.5752	Remote Similarity	NPC475486
0.5743	Remote Similarity	NPC284807
0.5727	Remote Similarity	NPC73829
0.5702	Remote Similarity	NPC11242
0.5702	Remote Similarity	NPC62725
0.57	Remote Similarity	NPC242611
0.5664	Remote Similarity	NPC488209
0.5607	Remote Similarity	NPC488516
0.5565	Remote Similarity	NPC480939
0.5506	Remote Similarity	NPC480946
0.5506	Remote Similarity	NPC130577
0.5506	Remote Similarity	NPC142415
0.5506	Remote Similarity	NPC102683
0.5472	Remote Similarity	NPC603870
0.5437	Remote Similarity	NPC480937
0.5431	Remote Similarity	NPC280941
0.5431	Remote Similarity	NPC235772
0.5421	Remote Similarity	NPC108748
0.5413	Remote Similarity	NPC80843
0.5403	Remote Similarity	NPC471385
0.54	Remote Similarity	NPC57362
0.5391	Remote Similarity	NPC477193
0.5366	Remote Similarity	NPC478596
0.5357	Remote Similarity	NPC258885
0.5345	Remote Similarity	NPC477194
0.5328	Remote Similarity	NPC4749
0.5328	Remote Similarity	NPC478597
0.5328	Remote Similarity	NPC488211
0.5321	Remote Similarity	NPC157868
0.5294	Remote Similarity	NPC478600
0.5294	Remote Similarity	NPC478599
0.5288	Remote Similarity	NPC473538
0.5278	Remote Similarity	NPC309780
0.5275	Remote Similarity	NPC270768
0.5275	Remote Similarity	NPC59263
0.5275	Remote Similarity	NPC210106
0.5275	Remote Similarity	NPC275809
0.5273	Remote Similarity	NPC482746
0.5263	Remote Similarity	NPC488515
0.5254	Remote Similarity	NPC476992
0.5253	Remote Similarity	NPC484195
0.525	Remote Similarity	NPC471384
0.5238	Remote Similarity	NPC480943
0.5161	Remote Similarity	NPC478598
0.5161	Remote Similarity	NPC298554
0.5133	Remote Similarity	NPC44716
0.5118	Remote Similarity	NPC111466
0.5104	Remote Similarity	NPC96580
0.5091	Remote Similarity	NPC173583
0.5088	Remote Similarity	NPC475591
0.5088	Remote Similarity	NPC236870
0.5086	Remote Similarity	NPC281148
0.5078	Remote Similarity	NPC302543
0.5054	Remote Similarity	NPC158141
0.5047	Remote Similarity	NPC473481
0.5047	Remote Similarity	NPC475611
0.5043	Remote Similarity	NPC477075

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC114441 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6908
0.1-0.2	2190
0.2-0.3	45
0.3-0.4	5
0.4-0.5	1
0.5-0.6	1
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
0.5865	Remote Similarity	NPD8295	Clinical (unspecified phase)

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