NPASS Compound

Natural Product: NPC242840

Natural Product ID	NPC242840
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gypsogenin 3-O-Beta-D-Glucuronopyranosyl-28-O-Beta-D-Glucopyranoside
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4-formyl-4,6a,6b,11,11,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2043373
PubChem CID	70692466
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 -7.6085 -3.5429 -2.3161 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7945 -2.4540 -3.1723 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4195 -1.1902 -2.4436 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0830 -1.2466 -2.0472 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7661 0.0392 -1.5809 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8388 -0.0288 -0.5413 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0954 0.3932 0.7558 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2513 0.8540 0.9367 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0865 0.3109 1.8575 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6278 -1.0713 2.1143 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4993 -1.5610 1.2836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3695 -0.5638 1.1604 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8560 0.7976 0.8583 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3506 1.6257 -0.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1674 1.2568 -0.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5198 0.1747 -0.1497 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3846 -1.0004 0.0811 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2747 -1.1970 -1.1580 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2965 -2.2815 0.3551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7512 -2.3082 0.5737 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4818 -1.0241 0.4212 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9001 -0.1857 -0.6565 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8935 -0.7642 -2.0213 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6643 1.1408 -0.7295 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1223 0.9260 -0.9277 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7695 -0.0202 0.0515 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9715 -1.2275 0.3988 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3807 -2.4372 -0.4197 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3279 -1.6042 1.7974 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0798 -0.9011 2.4278 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9834 -0.3984 -0.5538 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0992 0.1081 0.0874 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7815 1.0396 -0.6834 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1042 0.7200 -0.8873 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7833 1.6694 -1.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2090 2.6488 -2.3301 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1345 1.4352 -2.0819 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2772 -0.7113 -1.3720 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9235 -1.6163 -0.2418 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9359 -0.9758 0.6668 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5006 -0.5336 1.8645 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5607 -2.8977 -0.6612 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6500 -0.8427 -1.6698 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0238 1.3318 1.6341 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5445 1.8967 2.9777 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6155 2.8299 3.5009 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9872 2.2335 3.1922 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8214 0.7493 3.1383 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4932 4.2212 2.9182 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5419 2.9722 5.0089 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6360 -0.5594 2.4984 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3854 0.8632 -2.7525 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5106 0.7461 -3.7764 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7196 0.0489 -3.2175 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5429 0.9501 -2.5071 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0980 0.0464 -4.9127 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3095 2.2344 -2.4160 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3163 -3.2367 -1.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0992 -2.6161 -4.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8307 -2.4234 -3.5098 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0072 -1.1544 -1.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7031 0.4885 -1.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4853 -1.7599 1.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3256 -1.1532 3.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1220 -2.4837 1.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9061 -1.8809 0.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7704 2.6139 -0.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4573 1.0115 -1.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4919 2.1671 -0.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7156 0.6134 0.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1872 -0.6057 -1.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7701 -0.9960 -2.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5893 -2.2812 -1.2011 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1871 -2.7305 1.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0536 -3.0638 -0.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2706 -3.0592 -0.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0277 -2.6958 1.6038 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2800 -0.4456 1.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9411 -0.6875 -2.4397 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4931 -1.7778 -2.1137 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3334 -0.0283 -2.6751 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2815 1.6184 -1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4797 1.7811 0.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6240 1.9177 -0.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4056 0.6380 -1.9831 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0456 0.5939 0.9336 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4615 -2.3387 -0.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8249 -2.6051 -1.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3067 -3.3884 0.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9438 -2.4894 2.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7106 0.7149 0.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6325 0.7943 0.0851 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7570 2.1790 -2.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7048 -0.9052 -2.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8685 -1.7570 0.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2225 -1.7989 0.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8887 -1.3194 2.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4519 -3.4408 0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7657 -1.1307 -2.5986 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5051 2.2003 1.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4270 1.0926 3.7317 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6291 2.4852 2.8358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3910 2.6090 2.2397 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7167 2.4593 3.9974 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3118 0.3605 4.0367 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8126 0.2705 3.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4807 4.7198 3.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1644 4.2197 1.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7252 4.7608 3.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3459 1.9647 5.4673 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5266 3.3772 5.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7329 3.6792 5.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3251 0.4753 2.7528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2865 -0.9795 3.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2759 -1.1671 2.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4707 0.5312 -3.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8537 1.7459 -4.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3464 -0.2515 -4.1056 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0341 0.4654 -1.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6184 0.3611 -5.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1972 2.6233 -2.2846 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 2 0 9 7 1 6 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 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 6 27 29 1 0 29 30 2 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 34 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 13 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 46 50 1 0 12 51 1 1 5 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 54 3 1 0 48 9 1 0 44 9 1 0 17 12 1 0 27 21 1 0 40 32 1 0 22 16 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 1 5 62 1 1 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 14 67 1 0 15 68 1 0 15 69 1 0 16 70 1 1 18 71 1 0 18 72 1 0 18 73 1 0 19 74 1 0 19 75 1 0 20 76 1 0 20 77 1 0 21 78 1 1 23 79 1 0 23 80 1 0 23 81 1 0 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 1 28 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 32 91 1 1 34 92 1 1 37 93 1 0 38 94 1 6 39 95 1 1 40 96 1 1 41 97 1 0 42 98 1 0 43 99 1 0 44100 1 6 45101 1 0 45102 1 0 47103 1 0 47104 1 0 48105 1 0 48106 1 0 49107 1 0 49108 1 0 49109 1 0 50110 1 0 50111 1 0 50112 1 0 51113 1 0 51114 1 0 51115 1 0 52116 1 6 53117 1 6 54118 1 6 55119 1 0 56120 1 0 57121 1 0 M END

Standard InCHIKey	KFNNEUAROQLUQS-ZJDNFKTFSA-N
Standard InCHI	InChI=1S/C42H64O15/c1-37(2)13-15-42(36(53)57-34-30(49)27(46)26(45)22(18-43)54-34)16-14-40(5)20(21(42)17-37)7-8-24-38(3)11-10-25(39(4,19-44)23(38)9-12-41(24,40)6)55-35-31(50)28(47)29(48)32(56-35)33(51)52/h7,19,21-32,34-35,43,45-50H,8-18H2,1-6H3,(H,51,52)/t21-,22+,23+,24+,25-,26+,27-,28-,29-,30+,31+,32-,34-,35+,38-,39-,40+,41+,42-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@]23CC[C@@]4(C(=CC[C@H]5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H]([C@@]4(C)C=O)O[C@@H]4O[C@H](C(=O)O)[C@H]([C@@H]([C@H]4O)O)O)[C@@H]3CC(CC2)(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	808.42	Volume:	796.4 ? Van der Waals volume.
Dense:	1.015	LogP:	1.487 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.28 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.576 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	41.0
TPSA:	249.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.079	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.94	Fsp³:	0.881
MCE-18:	154.532 ? 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:	0.883	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.177	Promiscuous compounds:	0.066

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.055	MDCK Permeability:	-5.154
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
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):	0.009
20% Bioavailability (F20%):	0.023	30% Bioavailability (F30%):	0.286
50% Bioavailability (F50%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.592
Plasma Protein Binding (PPB):	71.482%	Volume Distribution (VD):	-0.494
Fu:	23.007% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.641	BCRP inhibitor:	0.002
BSEP inhibitor:	0.014

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:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.057
HLM stability:	0.023 ? 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):

0.241

Half-life (T1/2):

3.325

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.702	Drug-induced Liver Injury (DILI):	0.925
AMES Toxicity:	0.92	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.023	Skin Sensitization:	1.0
Carcinogencity:	0.26	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.996
Hematotoxicity:	0.748	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.234	Hek293 Cytotoxicity:	0.13
BCF:	0.558 ? 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:	3.57 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.278 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.371 ? 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
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16276965]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652051]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25076	Salicornia herbacea	Species	Chenopodiaceae	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
IC50	3

Activity Type	# Activity
Others	1
Non-molecular	2

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	7100.0	nM	PMID[22652051]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1400.0	nM	PMID[22652051]
NPT1	Others	Radical scavenging activity	n.a.	IC50	>	500000.0	nM	PMID[20232858]

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 NPC242840 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	19688
0.1-0.2	25447
0.2-0.3	3524
0.3-0.4	739
0.4-0.5	294
0.5-0.6	109
0.6-0.7	28
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC473884
0.8889	High Similarity	NPC157868
0.8526	High Similarity	NPC31193
0.7576	Intermediate Similarity	NPC251768
0.7576	Intermediate Similarity	NPC159309
0.7576	Intermediate Similarity	NPC11551
0.7576	Intermediate Similarity	NPC86222
0.74	Intermediate Similarity	NPC40775
0.7374	Intermediate Similarity	NPC75417
0.7282	Intermediate Similarity	NPC114484
0.7273	Intermediate Similarity	NPC475171
0.7212	Intermediate Similarity	NPC301449
0.7212	Intermediate Similarity	NPC601290
0.72	Intermediate Similarity	NPC192791
0.7157	Intermediate Similarity	NPC475591
0.7157	Intermediate Similarity	NPC236870
0.6952	Remote Similarity	NPC281148
0.6875	Remote Similarity	NPC209894
0.6759	Remote Similarity	NPC187290
0.6739	Remote Similarity	NPC167383
0.6735	Remote Similarity	NPC214484
0.6634	Remote Similarity	NPC235405
0.66	Remote Similarity	NPC48499
0.6596	Remote Similarity	NPC237503
0.6569	Remote Similarity	NPC249848
0.6569	Remote Similarity	NPC107966
0.6531	Remote Similarity	NPC294112
0.6471	Remote Similarity	NPC475516
0.6356	Remote Similarity	NPC258617
0.6346	Remote Similarity	NPC295371
0.6346	Remote Similarity	NPC39211
0.6321	Remote Similarity	NPC30735
0.6239	Remote Similarity	NPC64715
0.6226	Remote Similarity	NPC223301
0.6226	Remote Similarity	NPC171544
0.6224	Remote Similarity	NPC224121
0.6207	Remote Similarity	NPC470218
0.6204	Remote Similarity	NPC235438
0.62	Remote Similarity	NPC480937
0.6132	Remote Similarity	NPC469946
0.6094	Remote Similarity	NPC475368
0.6078	Remote Similarity	NPC90856
0.6075	Remote Similarity	NPC112352
0.6019	Remote Similarity	NPC29069
0.5965	Remote Similarity	NPC11242
0.5963	Remote Similarity	NPC10607
0.5963	Remote Similarity	NPC46665
0.5929	Remote Similarity	NPC480473
0.5909	Remote Similarity	NPC63159
0.5893	Remote Similarity	NPC104372
0.5856	Remote Similarity	NPC222580
0.5856	Remote Similarity	NPC297263
0.5794	Remote Similarity	NPC473373
0.5794	Remote Similarity	NPC150400
0.57	Remote Similarity	NPC306746
0.57	Remote Similarity	NPC199457
0.5676	Remote Similarity	NPC44716
0.5676	Remote Similarity	NPC473459
0.5676	Remote Similarity	NPC480475
0.5652	Remote Similarity	NPC80986
0.5652	Remote Similarity	NPC480474
0.5644	Remote Similarity	NPC68419
0.5625	Remote Similarity	NPC118440
0.5603	Remote Similarity	NPC31838
0.5603	Remote Similarity	NPC481078
0.5588	Remote Similarity	NPC286347
0.5575	Remote Similarity	NPC609763
0.5574	Remote Similarity	NPC4749
0.5565	Remote Similarity	NPC481079
0.5528	Remote Similarity	NPC21691
0.549	Remote Similarity	NPC604133
0.5481	Remote Similarity	NPC128925
0.5481	Remote Similarity	NPC256798
0.5478	Remote Similarity	NPC114692
0.5478	Remote Similarity	NPC247315
0.5478	Remote Similarity	NPC482728
0.5472	Remote Similarity	NPC204458
0.5472	Remote Similarity	NPC189884
0.5472	Remote Similarity	NPC138334
0.5446	Remote Similarity	NPC309714
0.5421	Remote Similarity	NPC1046
0.5417	Remote Similarity	NPC79643
0.541	Remote Similarity	NPC475160
0.541	Remote Similarity	NPC283417
0.541	Remote Similarity	NPC200049
0.541	Remote Similarity	NPC473714
0.5391	Remote Similarity	NPC95437
0.5385	Remote Similarity	NPC295823
0.5385	Remote Similarity	NPC187618
0.5385	Remote Similarity	NPC174720
0.5385	Remote Similarity	NPC160452
0.5385	Remote Similarity	NPC241909
0.5385	Remote Similarity	NPC475467
0.5377	Remote Similarity	NPC47063
0.5377	Remote Similarity	NPC480943
0.5364	Remote Similarity	NPC482748
0.5354	Remote Similarity	NPC191763
0.5347	Remote Similarity	NPC46388
0.5345	Remote Similarity	NPC236657
0.5328	Remote Similarity	NPC135904
0.5328	Remote Similarity	NPC123199
0.5327	Remote Similarity	NPC480938
0.5323	Remote Similarity	NPC481080
0.5315	Remote Similarity	NPC472949
0.5304	Remote Similarity	NPC475504
0.5304	Remote Similarity	NPC131469
0.5294	Remote Similarity	NPC204407
0.5294	Remote Similarity	NPC75287
0.5285	Remote Similarity	NPC100639
0.5285	Remote Similarity	NPC191827
0.528	Remote Similarity	NPC476068
0.5278	Remote Similarity	NPC78046
0.5273	Remote Similarity	NPC139894
0.5273	Remote Similarity	NPC309780
0.5259	Remote Similarity	NPC302887
0.5254	Remote Similarity	NPC120116
0.5254	Remote Similarity	NPC481030
0.5246	Remote Similarity	NPC284449
0.5243	Remote Similarity	NPC37739
0.5243	Remote Similarity	NPC606107
0.5238	Remote Similarity	NPC100383
0.5225	Remote Similarity	NPC58448
0.5185	Remote Similarity	NPC473481
0.5185	Remote Similarity	NPC269095
0.5175	Remote Similarity	NPC104071
0.5169	Remote Similarity	NPC323359
0.5164	Remote Similarity	NPC192600
0.5156	Remote Similarity	NPC476779
0.5143	Remote Similarity	NPC124828
0.5133	Remote Similarity	NPC473343
0.513	Remote Similarity	NPC102439
0.5124	Remote Similarity	NPC213952
0.5106	Remote Similarity	NPC485564
0.5082	Remote Similarity	NPC60557
0.5082	Remote Similarity	NPC76972
0.5082	Remote Similarity	NPC313110
0.5082	Remote Similarity	NPC469782
0.5082	Remote Similarity	NPC67857
0.5082	Remote Similarity	NPC204414
0.5081	Remote Similarity	NPC470476
0.5079	Remote Similarity	NPC487505
0.5078	Remote Similarity	NPC41061
0.5078	Remote Similarity	NPC227551
0.5077	Remote Similarity	NPC302543
0.5049	Remote Similarity	NPC605954
0.5048	Remote Similarity	NPC137917
0.5048	Remote Similarity	NPC310014
0.5048	Remote Similarity	NPC269315
0.5043	Remote Similarity	NPC611191
0.5042	Remote Similarity	NPC218954
0.5039	Remote Similarity	NPC293330
0.5039	Remote Similarity	NPC65105
0.5039	Remote Similarity	NPC43550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC242840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6417
0.1-0.2	2656
0.2-0.3	71
0.3-0.4	5
0.4-0.5	1
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