NPASS Compound

Natural Product: NPC473538

Natural Product ID	NPC473538
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2',3',4'-Tri-O-Acetyl-3-O-Alpha-L-Arabinopyranosyl Oleanolic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444931
PubChem CID	44559264
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 114119 0 0 0 0 0 0 0 0999 V2000 11.0194 0.9417 -2.9097 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6213 1.2341 -2.5517 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1775 2.4161 -2.7183 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7865 0.2320 -2.0352 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4743 0.5861 -1.7199 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4492 -0.1816 -2.5352 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2311 0.4678 -2.3376 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8079 0.3958 -1.0061 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7556 1.0692 -0.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1163 0.3772 -0.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9055 -0.9893 0.0330 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5260 -1.6526 1.0598 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3340 -1.0216 1.7880 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2755 -3.1073 1.3469 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8946 2.4464 -0.3298 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6542 3.3645 0.6649 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3116 2.9806 1.8039 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7816 4.8356 0.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5164 0.8414 -0.9646 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5636 -0.1564 -0.6664 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8037 -0.4228 -1.9169 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3088 -0.4501 -1.8266 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1957 -1.0384 -0.4955 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3355 -0.0796 0.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 0.0925 0.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0023 1.6145 0.8506 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4973 -0.5297 1.7666 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6651 -1.9064 1.6700 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3332 -0.1839 1.8658 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 -0.1776 1.7664 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3786 -1.1766 0.7649 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6965 -1.0073 -0.5691 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1875 0.2130 -1.2998 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6208 0.5110 -1.1357 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3927 -0.0643 -0.2579 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8564 -1.0915 0.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3879 -0.6869 2.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8725 -0.5569 2.0988 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3642 0.4948 1.1772 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8152 0.3294 -0.1911 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7211 -0.5752 -0.9999 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0048 0.2076 -1.3174 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3701 1.1140 -0.1720 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8993 0.4668 1.0859 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8329 1.0309 -2.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1598 -0.7445 -1.5422 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9879 1.8378 1.6952 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4211 1.9525 2.8017 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2624 2.9783 0.9544 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4881 -2.4019 0.2079 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0628 -2.5436 1.3320 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3811 -2.4096 -0.4716 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7563 1.4171 -2.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1923 -0.1526 -2.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2696 1.2634 -3.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2565 1.6745 -1.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4024 -1.2106 -2.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6596 -0.1888 -3.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8272 -0.7072 -0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4488 0.9180 0.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8374 0.8568 0.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2354 -3.6597 1.1713 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0192 -3.2734 2.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5406 -3.5315 0.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5601 5.1344 -0.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 5.4038 1.1233 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8215 5.1052 0.7642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2163 -1.0729 -0.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1108 -1.3512 -2.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0341 0.3717 -2.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0146 0.6079 -1.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1160 -1.0619 -2.6271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0832 0.9184 0.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0899 1.7727 0.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4137 2.2036 0.1347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7466 1.8329 1.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9673 -0.3534 2.7179 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5164 -0.1153 1.9188 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4815 -2.3870 2.5127 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0717 0.7734 2.4123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0289 -0.9840 2.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1322 0.8627 1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2022 -0.4893 2.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0018 -1.8874 -1.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0382 0.0846 -2.3975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6731 1.1657 -0.9537 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0689 1.2800 -1.8107 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9916 -1.4077 2.7932 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 0.3245 2.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1010 -0.2009 3.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4135 -1.5193 2.0236 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9261 1.3456 -0.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0641 -1.4686 -0.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2808 -0.7876 -1.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4801 1.1668 -0.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0186 2.1530 -0.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2616 -0.5642 1.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2985 1.0170 1.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3692 0.3630 -3.3507 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2230 1.9423 -2.4062 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8478 1.2672 -2.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8568 -1.7633 -1.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3985 -0.8691 -2.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0645 -0.4673 -1.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9471 3.9071 1.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7707 -3.2403 0.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2864 -2.7560 0.8858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8693 -2.3217 -0.8549 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8502 -3.3179 0.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9409 -2.9262 1.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2417 -2.5297 2.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3800 -2.4964 -0.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4609 -2.9162 0.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2818 -3.0309 -1.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 0 12 13 2 0 12 14 1 0 9 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 8 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 24 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 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 43 44 1 0 42 45 1 0 42 46 1 0 39 47 1 0 47 48 2 0 47 49 1 0 36 50 1 0 31 51 1 0 23 52 1 0 10 5 1 0 25 20 1 0 32 23 1 0 36 31 1 0 40 35 1 0 44 39 1 0 1 53 1 0 1 54 1 0 1 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 8 59 1 0 9 60 1 0 10 61 1 0 14 62 1 0 14 63 1 0 14 64 1 0 18 65 1 0 18 66 1 0 18 67 1 0 20 68 1 0 21 69 1 0 21 70 1 0 22 71 1 0 22 72 1 0 24 73 1 0 26 74 1 0 26 75 1 0 26 76 1 0 27 77 1 0 27 78 1 0 28 79 1 0 29 80 1 0 29 81 1 0 30 82 1 0 30 83 1 0 32 84 1 0 33 85 1 0 33 86 1 0 34 87 1 0 37 88 1 0 37 89 1 0 38 90 1 0 38 91 1 0 40 92 1 0 41 93 1 0 41 94 1 0 43 95 1 0 43 96 1 0 44 97 1 0 44 98 1 0 45 99 1 0 45100 1 0 45101 1 0 46102 1 0 46103 1 0 46104 1 0 49105 1 0 50106 1 0 50107 1 0 50108 1 0 51109 1 0 51110 1 0 51111 1 0 52112 1 0 52113 1 0 52114 1 0 M END

Standard InCHIKey	ADJGVADBICKKNW-DSLSCRDMSA-N
Standard InCHI	InChI=1S/C41H62O11/c1-23(43)49-28-21-48-34(33(51-25(3)45)32(28)50-24(2)44)52-31-13-14-37(6)29(38(31,7)22-42)12-15-40(9)30(37)11-10-26-27-20-36(4,5)16-18-41(27,35(46)47)19-17-39(26,40)8/h10,27-34,42H,11-22H2,1-9H3,(H,46,47)/t27-,28-,29+,30+,31-,32-,33+,34-,37-,38-,39+,40+,41-/m0/s1
SMILES	CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)OC2CCC3(C(C2(C)CO)CCC4(C3CC=C5C4(CCC6(C5CC(CC6)(C)C)C(=O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	730.43	Volume:	749.863 ? Van der Waals volume.
Dense:	0.974	LogP:	3.331 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.39 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.802 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.466	Fsp³:	0.854
MCE-18:	130.237 ? 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:	0.035	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.043 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.199	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.281	MDCK Permeability:	-4.903
Pgp-inhibitor:	0.0	Pgp-substrate:	0.169
PAMPA:	0.999 ? 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):	0.037
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.032
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	1.0
Plasma Protein Binding (PPB):	73.07%	Volume Distribution (VD):	-0.471
Fu:	18.862% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.004
OATP1B3 inhibitor:	0.488	BCRP inhibitor:	0.0
BSEP inhibitor:	0.739

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.213	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.492	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.012	CYP2C8-inhibitor:	0.996
HLM stability:	0.986 ? 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):

1.134

Half-life (T1/2):

1.549

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.063
Human Hepatotoxicity (H-HT):	0.468	Drug-induced Liver Injury (DILI):	0.319
AMES Toxicity:	0.126	Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.52	Skin Sensitization:	0.447
Carcinogencity:	0.133	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.068
Drug-induced Neurotoxicity:	0.153	Ototoxicity:	0.968
Hematotoxicity:	0.119	Drug-induced Nephrotoxicity:	0.085
Genotoxicity:	0.023	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.027	Hek293 Cytotoxicity:	0.168
BCF:	0.63 ? 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:	4.451 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.395 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.058 ? 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
NPO16143.1	Phyllanthus polyphyllus	Under-species	n.a.	n.a.	leaves	n.a.	n.a.	PMID[16038539]
NPO16143.1	Phyllanthus polyphyllus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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
IC50	2

Activity Type	# Activity
Cell line	1
Non-molecular	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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	3.2	ug.mL-1	PMID[23398362]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3.3	ug.mL-1	PMID[16038539]

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 NPC473538 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	17704
0.1-0.2	27237
0.2-0.3	3871
0.3-0.4	729
0.4-0.5	212
0.5-0.6	84
0.6-0.7	13
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
0.8554	High Similarity	NPC475611
0.7273	Intermediate Similarity	NPC284807
0.6897	Remote Similarity	NPC28198
0.6897	Remote Similarity	NPC476123
0.6591	Remote Similarity	NPC204407
0.6543	Remote Similarity	NPC120840
0.6458	Remote Similarity	NPC174679
0.6458	Remote Similarity	NPC279554
0.6458	Remote Similarity	NPC59804
0.6354	Remote Similarity	NPC136877
0.6176	Remote Similarity	NPC139044
0.6176	Remote Similarity	NPC471383
0.6154	Remote Similarity	NPC283849
0.6129	Remote Similarity	NPC100383
0.602	Remote Similarity	NPC12288
0.5979	Remote Similarity	NPC22676
0.5979	Remote Similarity	NPC270667
0.5978	Remote Similarity	NPC606107
0.5938	Remote Similarity	NPC191410
0.59	Remote Similarity	NPC127056
0.5851	Remote Similarity	NPC286347
0.5849	Remote Similarity	NPC276093
0.5833	Remote Similarity	NPC294112
0.5833	Remote Similarity	NPC158141
0.58	Remote Similarity	NPC56713
0.5783	Remote Similarity	NPC480946
0.5783	Remote Similarity	NPC130577
0.5783	Remote Similarity	NPC142415
0.5783	Remote Similarity	NPC102683
0.5769	Remote Similarity	NPC104400
0.5769	Remote Similarity	NPC10320
0.5747	Remote Similarity	NPC296164
0.5745	Remote Similarity	NPC177246
0.5714	Remote Similarity	NPC270768
0.5714	Remote Similarity	NPC59263
0.5714	Remote Similarity	NPC210106
0.5686	Remote Similarity	NPC488561
0.5682	Remote Similarity	NPC96580
0.566	Remote Similarity	NPC257468
0.5657	Remote Similarity	NPC164194
0.5648	Remote Similarity	NPC323359
0.5631	Remote Similarity	NPC22956
0.5607	Remote Similarity	NPC119794
0.5588	Remote Similarity	NPC109079
0.5581	Remote Similarity	NPC298554
0.5577	Remote Similarity	NPC469945
0.5575	Remote Similarity	NPC323341
0.5556	Remote Similarity	NPC475472
0.5534	Remote Similarity	NPC472949
0.5534	Remote Similarity	NPC6377
0.5534	Remote Similarity	NPC208381
0.5529	Remote Similarity	NPC156981
0.5514	Remote Similarity	NPC73829
0.5495	Remote Similarity	NPC280941
0.5495	Remote Similarity	NPC62725
0.5495	Remote Similarity	NPC235772
0.549	Remote Similarity	NPC25605
0.5474	Remote Similarity	NPC57362
0.5465	Remote Similarity	NPC110308
0.5463	Remote Similarity	NPC79718
0.5455	Remote Similarity	NPC488564
0.5444	Remote Similarity	NPC474727
0.5439	Remote Similarity	NPC133818
0.5402	Remote Similarity	NPC200752
0.5393	Remote Similarity	NPC488521
0.537	Remote Similarity	NPC481082
0.537	Remote Similarity	NPC164419
0.5364	Remote Similarity	NPC324875
0.5364	Remote Similarity	NPC292677
0.5349	Remote Similarity	NPC275809
0.5327	Remote Similarity	NPC180550
0.5327	Remote Similarity	NPC35405
0.5326	Remote Similarity	NPC23241
0.5301	Remote Similarity	NPC604575
0.5288	Remote Similarity	NPC114441
0.5287	Remote Similarity	NPC231063
0.5287	Remote Similarity	NPC282395
0.5234	Remote Similarity	NPC114304
0.5233	Remote Similarity	NPC198664
0.5207	Remote Similarity	NPC471385
0.5196	Remote Similarity	NPC127853
0.5172	Remote Similarity	NPC182797
0.5172	Remote Similarity	NPC282616
0.5172	Remote Similarity	NPC84319
0.5172	Remote Similarity	NPC52021
0.5172	Remote Similarity	NPC52169
0.5172	Remote Similarity	NPC488562
0.5172	Remote Similarity	NPC599947
0.5169	Remote Similarity	NPC485589
0.5161	Remote Similarity	NPC481362
0.5128	Remote Similarity	NPC166422
0.5128	Remote Similarity	NPC219180
0.5114	Remote Similarity	NPC481360
0.5111	Remote Similarity	NPC608622
0.5109	Remote Similarity	NPC485588
0.5098	Remote Similarity	NPC171007
0.5098	Remote Similarity	NPC190849
0.5054	Remote Similarity	NPC230151
0.5042	Remote Similarity	NPC54636

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5425
0.1-0.2	3671
0.2-0.3	44
0.3-0.4	10
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