NPASS Compound

Natural Product: NPC187400

Natural Product ID	NPC187400
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mogroside Ii B
IUPAC Name	(2R,3R,4S,5S,6R)-2-[[(3S,8S,9R,10R,11R,13R,14S,17R)-11-hydroxy-17-[(2R,5R)-5-hydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms	mogroside II B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL228083
PubChem CID	44423068
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

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 128133 0 0 0 0 0 0 0 0999 V2000 2.6717 2.4751 -0.0328 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0100 1.0214 0.2101 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1103 0.6357 -0.7574 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7388 0.7901 -2.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8827 0.3981 -3.0855 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1220 1.1988 -2.9381 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6873 2.6778 -3.0549 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9713 0.9783 -4.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8510 1.1137 -1.8029 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4183 -0.1012 -1.4950 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9295 0.1363 -1.5158 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3714 0.7345 -0.2043 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1658 -0.2736 0.8977 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0463 -1.2107 0.4468 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4578 -1.8009 1.7188 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4868 -2.5257 2.3566 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0736 -0.4811 -0.2232 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3351 -0.9528 1.1953 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6552 1.8945 0.1013 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6588 -0.9967 -1.7674 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4022 0.6275 -4.4251 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8224 0.1005 0.0893 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3324 -1.3158 0.3418 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2712 -2.0078 1.2074 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0537 -1.0821 1.0048 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3987 -1.3087 -0.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9730 -1.2677 2.0679 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8365 -2.4728 1.7566 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9830 -2.1670 0.9061 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5485 -1.0042 0.9228 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0922 0.1018 1.7922 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2346 0.4364 2.7143 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5821 -0.0822 2.1930 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7242 0.1630 0.7083 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7150 -0.7369 0.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3557 -2.0691 -0.3743 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2231 -0.1033 -1.2761 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9855 -0.2236 0.3409 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7333 0.7657 -0.2836 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1003 0.4805 -1.6902 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5065 0.9696 -2.0278 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5176 0.3687 -1.0670 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8622 0.2773 0.2962 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5658 -1.1235 0.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2154 -1.2028 2.0665 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8173 1.1739 0.4478 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7114 1.0449 -1.0658 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7973 0.4882 -3.3006 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2447 1.1829 -2.5663 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7792 -0.0794 2.4583 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0494 -0.2105 3.9722 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0234 1.2225 2.3600 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1568 1.3224 1.1250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8220 0.2281 1.1925 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5628 0.2611 2.4959 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9280 2.2815 2.3139 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6066 3.0682 0.8844 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4909 2.9734 -0.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7877 2.5217 -0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4940 0.9989 1.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4278 -0.4201 -0.6003 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9703 1.2784 -0.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9164 0.0492 -2.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3199 1.7820 -2.4425 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0208 -0.6996 -3.0315 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9843 2.8335 -3.8691 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6388 3.2208 -3.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4130 3.0536 -2.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6040 1.8696 -4.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5295 0.0417 -4.1601 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2596 0.9278 -5.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1506 -0.9059 -2.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1766 0.9089 -2.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4578 1.0167 -0.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8360 0.2644 1.8142 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4339 -2.0768 -0.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6801 -2.5267 1.4572 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1475 -0.9933 2.3888 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7804 -2.0530 3.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1167 -0.3555 0.9746 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5729 2.5112 -0.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9030 -1.0902 -2.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6952 -0.0602 -4.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4247 0.2465 -0.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4612 -1.8279 -0.6370 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2643 -1.3335 0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5677 -2.0567 2.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0437 -2.9676 0.7298 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9458 -2.2818 -0.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9196 -0.4842 -0.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5030 -1.5302 -1.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3720 -1.6092 2.9705 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1739 -3.2618 1.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2325 -2.8585 2.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3553 -2.9475 0.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0469 0.9905 1.0864 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3624 1.5315 2.8348 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1828 0.0148 3.7165 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3555 0.4600 2.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7194 -1.1501 2.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4710 1.2085 0.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5001 -2.7406 0.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3591 -1.8179 -0.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7314 -2.4934 -1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3042 1.0025 -1.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9155 -0.4299 -2.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2303 -0.4828 -1.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0314 1.6577 -0.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0984 -0.5963 -1.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5948 2.0664 -2.0076 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7024 -0.6699 -1.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6620 0.6492 1.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8360 -1.6132 0.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5452 -1.6878 0.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8040 -2.1011 2.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7135 1.8595 -0.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0784 0.6787 -3.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2902 2.1403 -2.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4182 0.7108 4.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0456 -0.3861 4.4160 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6093 -1.1360 4.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3579 1.4036 3.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3677 2.2969 1.2154 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7513 1.3715 0.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7098 1.3436 2.7632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5506 -0.2441 2.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0256 -0.1748 3.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8662 2.7941 1.4637 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 6 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 5 21 1 0 2 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 28 29 1 0 29 30 2 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 35 37 1 0 34 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 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 31 50 1 0 50 51 1 1 50 52 1 0 52 53 1 0 53 54 1 0 54 55 1 1 52 56 1 0 17 10 1 0 54 22 1 0 54 25 1 0 50 27 1 0 35 30 1 0 46 39 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 1 3 61 1 0 3 62 1 0 4 63 1 0 4 64 1 0 5 65 1 6 7 66 1 0 7 67 1 0 7 68 1 0 8 69 1 0 8 70 1 0 8 71 1 0 10 72 1 6 11 73 1 6 12 74 1 6 13 75 1 1 14 76 1 6 15 77 1 0 15 78 1 0 16 79 1 0 18 80 1 0 19 81 1 0 20 82 1 0 21 83 1 0 22 84 1 6 23 85 1 0 23 86 1 0 24 87 1 0 24 88 1 0 26 89 1 0 26 90 1 0 26 91 1 0 27 92 1 1 28 93 1 0 28 94 1 0 29 95 1 0 31 96 1 6 32 97 1 0 32 98 1 0 33 99 1 0 33100 1 0 34101 1 1 36102 1 0 36103 1 0 36104 1 0 37105 1 0 37106 1 0 37107 1 0 39108 1 6 40109 1 6 41110 1 6 42111 1 6 43112 1 1 44113 1 0 44114 1 0 45115 1 0 47116 1 0 48117 1 0 49118 1 0 51119 1 0 51120 1 0 51121 1 0 52122 1 1 53123 1 0 53124 1 0 55125 1 0 55126 1 0 55127 1 0 56128 1 0 M END

Standard InCHIKey	OMJOQOVMHUWPCF-VHLOEOCYSA-N
Standard InCHI	InChI=1S/C42H72O14/c1-20(9-13-27(45)39(4,5)56-37-35(52)33(50)31(48)25(19-44)54-37)21-15-16-40(6)26-12-10-22-23(42(26,8)28(46)17-41(21,40)7)11-14-29(38(22,2)3)55-36-34(51)32(49)30(47)24(18-43)53-36/h10,20-21,23-37,43-52H,9,11-19H2,1-8H3/t20-,21-,23-,24-,25-,26+,27-,28-,29+,30-,31-,32+,33+,34-,35-,36+,37+,40+,41-,42+/m1/s1
SMILES	C[C@H](CC[C@H](C(C)(C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)[C@H]1CC[C@@]2(C)[C@@H]3CC=C4[C@@H](CC[C@@H](C4(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)[C@]3(C)[C@@H](C[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	800.49	Volume:	804.076 ? Van der Waals volume.
Dense:	0.996	LogP:	3.305 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.6 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.226 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	32.0
TPSA:	239.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.132	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.111	Fsp³:	0.952
MCE-18:	133.098 ? 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:	0.73	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:	0.258	Promiscuous compounds:	0.049

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.135	MDCK Permeability:	-5.136
Pgp-inhibitor:	0.0	Pgp-substrate:	0.928
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):	0.018
20% Bioavailability (F20%):	0.183	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127	MRP1:	0.115
Plasma Protein Binding (PPB):	67.645%	Volume Distribution (VD):	-0.326
Fu:	24.186% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.078
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.981	CYP3A4-substrate:	0.542
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.902
HLM stability:	0.047 ? 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):

1.237

Half-life (T1/2):

3.151

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.75	Drug-induced Liver Injury (DILI):	0.918
AMES Toxicity:	0.959	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	1.0
Carcinogencity:	0.321	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.998
Hematotoxicity:	0.675	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.744	RPMI-8226 Immunitoxicity:	0.19
A549 Cytotoxicity:	0.916	Hek293 Cytotoxicity:	0.682
BCF:	1.202 ? 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:	3.405 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.803 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.972 ? 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
NPO32612	siraitia gros venorii	Species	Cucurbitaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17477572]

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	5
Ratio	1

Activity Type	# Activity
Cell line	1
Organism	4
Others	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PubChem BioAssay data set
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	7.2	%	PMID[20384315]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	26.0	%	DrugMatrix in vivo data: Pathology
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	76.0	%	PMID[24673739]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	100.0	%	PMID[9526564]
NPT2	Others	Unspecified	n.a.	Ratio	=	1.5	n.a.	PMID[26200396]

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 NPC187400 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	18694
0.1-0.2	25492
0.2-0.3	4675
0.3-0.4	931
0.4-0.5	47
0.5-0.6	11
0.6-0.7	5
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
0.8133	Intermediate Similarity	NPC75608
0.8026	Intermediate Similarity	NPC221562
0.7093	Intermediate Similarity	NPC190395
0.663	Remote Similarity	NPC302057
0.6353	Remote Similarity	NPC154856
0.6092	Remote Similarity	NPC74727
0.6092	Remote Similarity	NPC130427
0.6047	Remote Similarity	NPC52241
0.5761	Remote Similarity	NPC309448
0.5699	Remote Similarity	NPC485581
0.5638	Remote Similarity	NPC485578
0.5521	Remote Similarity	NPC279638
0.5306	Remote Similarity	NPC474265
0.5263	Remote Similarity	NPC606839
0.5196	Remote Similarity	NPC485582
0.5196	Remote Similarity	NPC485579
0.5146	Remote Similarity	NPC485583
0.51	Remote Similarity	NPC474557
0.5048	Remote Similarity	NPC485584

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC187400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6924
0.1-0.2	2150
0.2-0.3	72
0.3-0.4	4
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