NPASS Compound

Natural Product: NPC475208

Natural Product ID	NPC475208
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Glucopyranosyl-28-O-Alpha-L-Rhamnopyranosyl-16Alpha-Hydrox Yprotobassic Acid
IUPAC Name	[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501038
PubChem CID	44575353
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 125131 0 0 0 0 0 0 0 0999 V2000 8.7397 2.9533 1.5929 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7332 1.9690 1.5729 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3840 0.6079 1.3837 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4996 -0.4354 1.3617 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7945 -0.5953 0.1709 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7580 0.2978 0.0451 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4906 -0.2746 0.0537 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8806 0.0607 1.3957 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3138 1.2847 1.8981 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4052 -0.1454 1.4634 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6487 0.5268 0.3510 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2353 0.1518 -0.9837 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7072 0.1593 -1.1115 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2409 1.4838 -1.6852 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0478 -0.8111 -2.2636 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7436 -2.1158 -1.9666 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5256 1.0031 -1.9915 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0429 0.9260 -1.9732 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6373 0.4609 -0.7530 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2671 -0.0680 0.3252 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4510 -0.1329 1.6246 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6996 -0.9186 1.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2050 -1.1502 0.1573 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5968 -0.6591 -1.1072 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8647 -1.8330 -1.7659 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6613 -0.1908 -2.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8550 -1.0525 -2.1770 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4156 -1.6191 -0.9110 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4451 -1.9819 0.1358 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9657 -3.4129 0.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2051 -4.2926 0.2596 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7365 -5.7116 0.3979 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1088 -3.9041 1.3775 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8547 -4.1225 -1.1245 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3417 -2.7481 -1.3235 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3583 -0.5747 -0.3340 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5844 -0.8565 -0.1047 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9953 0.7062 -0.0227 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8408 1.6844 0.5066 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9982 2.8006 -0.2660 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9610 3.9962 0.4038 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5156 5.0600 -0.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7984 4.0491 1.6429 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6295 2.8151 2.5091 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4357 2.0572 1.9384 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1439 0.9158 2.6490 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7877 2.0360 2.2939 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3585 5.1424 2.4045 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7395 -2.0633 -3.1590 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5129 1.5725 -0.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6220 1.9868 0.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6582 -0.6096 -1.0509 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1473 -0.4952 -0.7160 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3598 0.6328 0.2341 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6963 0.5645 0.6707 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8025 -0.2835 -1.9192 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4764 -1.8308 -1.7543 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7691 3.4758 0.7579 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1263 2.1643 0.6619 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1780 2.0604 2.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0075 0.4657 2.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3119 -1.6173 0.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6803 -1.3897 0.0848 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3140 -0.6863 2.1319 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8719 1.7567 1.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0490 0.1887 2.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2261 -1.2603 1.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9032 -0.9081 -1.1800 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2520 2.2992 -0.9767 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7384 1.7037 -2.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3031 1.2695 -1.9597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1328 -0.7302 -2.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5597 -0.4581 -3.2058 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3460 -2.3062 -1.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8693 2.0805 -1.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9244 0.6924 -3.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3323 1.9796 -2.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2812 0.3890 -2.9152 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4567 -1.1561 0.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6337 0.7978 2.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1566 -0.7740 2.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1876 -1.3017 2.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5666 -2.3372 -2.4949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4650 -2.5434 -1.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0195 -1.5176 -2.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9689 0.8518 -1.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2048 -0.1748 -3.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6814 -0.3967 -2.6046 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9865 -1.8579 1.1287 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2947 -3.5236 1.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4902 -3.7327 -0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2223 -6.0527 -0.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5539 -6.3946 0.7280 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9905 -5.7281 1.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9153 -3.2152 1.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 -3.4732 2.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6128 -4.8199 1.8078 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1327 -4.4926 -1.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7245 -4.8067 -1.1129 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5799 -2.6146 -2.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3571 -2.6536 -0.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8550 1.2069 0.6191 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9352 4.3274 0.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7879 5.3442 -1.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8597 5.8957 0.0741 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4283 4.5944 -1.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8753 4.2396 1.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5027 3.0367 3.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5938 2.7739 1.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9855 0.4786 2.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9710 1.4256 3.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0849 4.8795 3.3186 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4944 -1.6213 -4.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4207 1.1507 0.3126 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0129 2.1228 0.6573 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8775 2.2711 -0.9601 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6380 2.4085 0.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1390 2.1309 1.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1434 2.6239 -0.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4467 0.2386 -1.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4507 -1.4593 -0.2601 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2505 1.6126 -0.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7886 0.8744 1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0790 -1.1544 -2.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8064 -1.6688 -2.6778 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 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 31 34 1 0 34 35 1 0 28 36 1 1 36 37 2 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 27 49 1 0 19 50 1 1 11 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 13 7 1 0 24 19 1 0 35 28 1 0 45 39 1 0 20 11 1 0 29 23 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 1 5 62 1 1 7 63 1 6 8 64 1 1 9 65 1 0 10 66 1 0 10 67 1 0 12 68 1 6 14 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 16 74 1 0 17 75 1 0 17 76 1 0 18 77 1 0 18 78 1 0 20 79 1 6 21 80 1 0 21 81 1 0 22 82 1 0 25 83 1 0 25 84 1 0 25 85 1 0 26 86 1 0 26 87 1 0 27 88 1 6 29 89 1 1 30 90 1 0 30 91 1 0 32 92 1 0 32 93 1 0 32 94 1 0 33 95 1 0 33 96 1 0 33 97 1 0 34 98 1 0 34 99 1 0 35100 1 0 35101 1 0 39102 1 1 41103 1 1 42104 1 0 42105 1 0 42106 1 0 43107 1 6 44108 1 1 45109 1 6 46110 1 0 47111 1 0 48112 1 0 49113 1 0 50114 1 0 50115 1 0 50116 1 0 51117 1 0 51118 1 0 51119 1 0 52120 1 6 53121 1 1 54122 1 6 55123 1 0 56124 1 0 57125 1 0 M END

Standard InCHIKey	STQISEBYTPHEPL-YIGUUSMJSA-N
Standard InCHI	InChI=1S/C42H68O15/c1-19-27(47)29(49)31(51)34(54-19)57-36(53)42-13-12-37(2,3)14-21(42)20-8-9-25-38(4)15-22(45)33(56-35-32(52)30(50)28(48)23(17-43)55-35)39(5,18-44)24(38)10-11-40(25,6)41(20,7)16-26(42)46/h8,19,21-35,43-52H,9-18H2,1-7H3/t19-,21-,22-,23+,24+,25+,26+,27-,28+,29+,30-,31+,32+,33-,34-,35-,38-,39-,40+,41+,42+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	812.46	Volume:	801.673 ? Van der Waals volume.
Dense:	1.013	LogP:	1.775 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.393 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.921 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	39.0
TPSA:	256.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.098	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.074	Fsp³:	0.929
MCE-18:	156.222 ? 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:	0.711	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.197	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.336	MDCK Permeability:	-5.2
Pgp-inhibitor:	0.0	Pgp-substrate:	0.206
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):	0.46
20% Bioavailability (F20%):	0.284	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.516	MRP1:	0.031
Plasma Protein Binding (PPB):	72.489%	Volume Distribution (VD):	-0.339
Fu:	16.59% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.054
BSEP inhibitor:	0.0

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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.488
HLM stability:	0.094 ? 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):

0.523

Half-life (T1/2):

3.544

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.664	Drug-induced Liver Injury (DILI):	0.743
AMES Toxicity:	0.884	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	0.999
Carcinogencity:	0.178	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.69	Drug-induced Nephrotoxicity:	0.973
Genotoxicity:	0.205	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.853	Hek293 Cytotoxicity:	0.273
BCF:	1.217 ? 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:	3.513 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.016 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.102 ? 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
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[10543897]
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	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
MIC	2

Activity Type	# Activity
Organism	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
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	1250.0	ug.mL-1	PMID[15679326]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	78.0	ug.mL-1	PMID[19332371]

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 NPC475208 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	21279
0.1-0.2	23315
0.2-0.3	3853
0.3-0.4	904
0.4-0.5	356
0.5-0.6	113
0.6-0.7	25
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	Natural Product ID
0.7955	Intermediate Similarity	NPC238935
0.6979	Remote Similarity	NPC150400
0.6979	Remote Similarity	NPC480420
0.697	Remote Similarity	NPC164389
0.6915	Remote Similarity	NPC1046
0.6634	Remote Similarity	NPC305267
0.6604	Remote Similarity	NPC815
0.6522	Remote Similarity	NPC48249
0.6442	Remote Similarity	NPC64715
0.6379	Remote Similarity	NPC144644
0.6379	Remote Similarity	NPC170407
0.6364	Remote Similarity	NPC139894
0.6364	Remote Similarity	NPC475899
0.6327	Remote Similarity	NPC179434
0.6316	Remote Similarity	NPC473452
0.6271	Remote Similarity	NPC142151
0.6262	Remote Similarity	NPC69811
0.6228	Remote Similarity	NPC237191
0.6228	Remote Similarity	NPC21691
0.6176	Remote Similarity	NPC473343
0.6167	Remote Similarity	NPC68767
0.6126	Remote Similarity	NPC123522
0.6121	Remote Similarity	NPC475514
0.6116	Remote Similarity	NPC153673
0.6116	Remote Similarity	NPC51099
0.6	Remote Similarity	NPC220160
0.5968	Remote Similarity	NPC275225
0.5957	Remote Similarity	NPC237503
0.5914	Remote Similarity	NPC167383
0.5909	Remote Similarity	NPC104137
0.5909	Remote Similarity	NPC26626
0.5897	Remote Similarity	NPC286457
0.5888	Remote Similarity	NPC488517
0.5865	Remote Similarity	NPC76497
0.5856	Remote Similarity	NPC11242
0.5847	Remote Similarity	NPC470876
0.5833	Remote Similarity	NPC302543
0.5833	Remote Similarity	NPC37860
0.5826	Remote Similarity	NPC283417
0.5826	Remote Similarity	NPC200049
0.581	Remote Similarity	NPC112352
0.5776	Remote Similarity	NPC25663
0.5769	Remote Similarity	NPC295371
0.5738	Remote Similarity	NPC267694
0.5726	Remote Similarity	NPC4749
0.569	Remote Similarity	NPC480423
0.5664	Remote Similarity	NPC213952
0.5645	Remote Similarity	NPC293031
0.5644	Remote Similarity	NPC214484
0.56	Remote Similarity	NPC110385
0.5591	Remote Similarity	NPC480421
0.5588	Remote Similarity	NPC29069
0.5556	Remote Similarity	NPC46665
0.5536	Remote Similarity	NPC481030
0.5536	Remote Similarity	NPC241909
0.5534	Remote Similarity	NPC48499
0.551	Remote Similarity	NPC604133
0.5472	Remote Similarity	NPC473884
0.5472	Remote Similarity	NPC39211
0.5462	Remote Similarity	NPC85154
0.5447	Remote Similarity	NPC476991
0.5446	Remote Similarity	NPC481079
0.5446	Remote Similarity	NPC209894
0.5429	Remote Similarity	NPC475516
0.5424	Remote Similarity	NPC100639
0.5413	Remote Similarity	NPC488526
0.5413	Remote Similarity	NPC102439
0.5408	Remote Similarity	NPC306746
0.5357	Remote Similarity	NPC114484
0.5354	Remote Similarity	NPC68419
0.5351	Remote Similarity	NPC207738
0.5345	Remote Similarity	NPC76972
0.5345	Remote Similarity	NPC469782
0.5345	Remote Similarity	NPC204414
0.5326	Remote Similarity	NPC488520
0.5321	Remote Similarity	NPC104071
0.5315	Remote Similarity	NPC475504
0.53	Remote Similarity	NPC110139
0.53	Remote Similarity	NPC108709
0.5299	Remote Similarity	NPC192600
0.5285	Remote Similarity	NPC293330
0.5285	Remote Similarity	NPC65105
0.5283	Remote Similarity	NPC235405
0.5281	Remote Similarity	NPC488519
0.5278	Remote Similarity	NPC469946
0.5273	Remote Similarity	NPC473401
0.5273	Remote Similarity	NPC473383
0.5263	Remote Similarity	NPC96641
0.5263	Remote Similarity	NPC163183
0.5254	Remote Similarity	NPC481031
0.5253	Remote Similarity	NPC199457
0.5238	Remote Similarity	NPC51564
0.5234	Remote Similarity	NPC473373
0.5234	Remote Similarity	NPC249848
0.5234	Remote Similarity	NPC107966
0.5229	Remote Similarity	NPC192791
0.5229	Remote Similarity	NPC223301
0.5229	Remote Similarity	NPC171544
0.5225	Remote Similarity	NPC63159
0.5213	Remote Similarity	NPC488522
0.521	Remote Similarity	NPC155410
0.521	Remote Similarity	NPC135904
0.52	Remote Similarity	NPC309223
0.52	Remote Similarity	NPC298034
0.52	Remote Similarity	NPC71065
0.5182	Remote Similarity	NPC309714
0.5179	Remote Similarity	NPC222580
0.5179	Remote Similarity	NPC123796
0.5167	Remote Similarity	NPC475160
0.5167	Remote Similarity	NPC473714
0.5138	Remote Similarity	NPC471547
0.5135	Remote Similarity	NPC251768
0.513	Remote Similarity	NPC295823
0.513	Remote Similarity	NPC174720
0.513	Remote Similarity	NPC475467
0.5109	Remote Similarity	NPC485564
0.5104	Remote Similarity	NPC488524
0.5089	Remote Similarity	NPC235438
0.5089	Remote Similarity	NPC162574
0.5088	Remote Similarity	NPC104372
0.5086	Remote Similarity	NPC481078
0.5051	Remote Similarity	NPC473123
0.5049	Remote Similarity	NPC256798
0.5048	Remote Similarity	NPC189884
0.5048	Remote Similarity	NPC90856
0.5048	Remote Similarity	NPC138334
0.5046	Remote Similarity	NPC157868
0.5045	Remote Similarity	NPC471548
0.5045	Remote Similarity	NPC30735
0.5045	Remote Similarity	NPC117714
0.5045	Remote Similarity	NPC30289
0.5044	Remote Similarity	NPC297263
0.5042	Remote Similarity	NPC79643
0.5041	Remote Similarity	NPC476068
0.5041	Remote Similarity	NPC471550
0.5039	Remote Similarity	NPC102505
0.5039	Remote Similarity	NPC488514
0.5038	Remote Similarity	NPC33012
0.5036	Remote Similarity	NPC124828

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7371
0.1-0.2	1710
0.2-0.3	63
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