NPASS Compound

Natural Product: NPC10607

Natural Product ID	NPC10607
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	{28-O-Beta-D-Glucopyranosyloleanolic Acid 3-O-Beta-D-Glucopyranosyl(1->2)-[Beta-D-Galactopyranosyl(1->3)]-Beta-D-Glucuronopyranoside-6-O-Methyl Ester}
IUPAC Name	methyl (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-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-hydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505078
PubChem CID	16099400
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 167175 0 0 0 0 0 0 0 0999 V2000 8.7576 0.2015 -2.6341 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3395 -0.0763 -2.1566 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4734 0.1536 -3.3950 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2379 -1.5226 -1.8265 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1990 -1.8903 -0.8366 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1671 -0.9926 0.3632 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1342 -1.4368 1.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0314 -0.4855 1.6387 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4136 -0.0558 0.3641 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7927 -1.2326 -0.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4746 0.6377 -0.4322 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0467 1.4904 -1.3890 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6428 1.8076 -1.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6988 1.1860 -0.7605 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3077 1.7852 -0.7426 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2433 3.2559 -0.5758 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2663 1.4885 -2.1376 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7371 1.7850 -2.2045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5213 1.0083 -1.1650 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9647 1.1166 0.2009 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4595 2.3410 0.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4621 -0.0943 0.9933 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4706 0.9953 0.2389 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0571 1.2177 1.6278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4271 0.5259 1.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3338 1.0215 0.5636 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9987 2.2807 1.0706 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8382 1.4538 -1.2754 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6114 0.4642 -1.7722 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8134 0.1204 -0.8997 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0473 -1.3336 -1.1264 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0882 -1.5146 -2.6362 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0353 -0.2531 -3.4354 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3803 0.3010 -3.7702 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5428 1.5402 -3.6742 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4462 -0.4755 -4.1767 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6717 0.1636 -4.4689 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1504 0.7118 -3.0412 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0345 -2.3357 -3.0652 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1440 -1.7823 -0.4895 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9501 -2.8753 0.3464 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3612 -2.7479 1.7460 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2811 -4.1470 2.3879 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3527 -4.9945 1.7456 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5533 -4.6115 0.3256 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9099 -3.9622 0.0513 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9387 -4.6436 0.6741 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5870 -3.9116 -0.2917 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5526 -4.7393 2.4514 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3458 -4.0877 3.7566 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4765 -1.9969 2.5348 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5310 0.5201 0.3820 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3697 1.5334 0.8359 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0263 1.3121 2.1368 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1855 2.6061 2.9071 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4749 3.8009 2.0342 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6219 3.7896 0.7816 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8914 5.0896 0.5983 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0106 5.3468 1.6591 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6666 2.7655 0.8521 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8225 3.9298 1.7716 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9977 2.9019 3.6131 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3199 0.7874 2.0075 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8813 0.3961 -0.1226 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8977 0.8683 -1.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5171 -1.1021 1.0054 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5617 -1.4898 2.1997 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6701 -0.8145 0.3812 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9663 -0.9069 0.9449 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6753 -2.0177 0.1586 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0921 -2.2038 0.6493 C 0 0 2 0 0 0 0 0 0 0 0 0 12.7857 -0.8706 0.5492 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9505 0.2092 1.2408 C 0 0 1 0 0 0 0 0 0 0 0 0 12.6408 1.5354 0.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9653 2.5697 1.4877 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6592 0.2669 0.7791 O 0 0 0 0 0 0 0 0 0 0 0 0 14.0051 -0.9658 1.2114 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7144 -3.0860 -0.2491 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9095 -3.1616 0.2771 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3552 0.7481 -1.8517 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3186 -0.7367 -2.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8045 0.8092 -3.5343 H 0 0 0 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-1.4317 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1620 0.3906 -2.2595 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2445 2.0327 -2.9280 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0891 1.4137 -3.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9916 2.8632 -2.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4277 -0.0718 -1.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6235 2.8658 1.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0009 3.0439 0.2823 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1831 2.0751 1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0419 -0.7897 0.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6383 -0.6347 1.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1861 0.2255 1.7746 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2540 -0.0929 0.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2826 2.2748 1.8742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5397 0.7848 2.4258 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2802 -0.5478 1.7060 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8564 0.8394 2.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0947 2.2112 1.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5083 2.5971 2.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8398 3.1375 0.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0040 -0.4592 -1.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 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0.6738 2.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9863 2.5506 3.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1623 4.7097 2.6175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3196 3.6561 -0.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2577 4.9831 -0.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5875 5.9516 0.5350 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7403 6.2854 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4015 3.5606 2.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9150 3.8605 3.8140 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6686 0.4457 2.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0700 1.0154 0.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6439 1.8898 -1.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8417 1.0851 -0.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8853 -1.2521 1.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7300 -1.7154 -0.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1367 -2.6184 1.6786 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8823 -0.5929 -0.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0437 0.0392 2.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6014 1.6509 -0.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7171 1.5231 1.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9966 2.3851 2.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8947 -1.5448 2.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1470 -3.9052 -0.3741 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2184 -3.7762 0.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 28 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 34 36 1 0 36 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 45 48 1 0 44 49 1 0 43 50 1 0 42 51 1 0 30 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 56 61 1 0 55 62 1 0 54 63 1 0 11 64 1 0 64 65 1 0 6 66 1 1 66 67 2 0 66 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 73 76 1 0 72 77 1 0 71 78 1 0 70 79 1 0 65 2 1 0 76 69 1 0 64 6 1 0 26 9 1 0 38 29 1 0 48 41 1 0 60 53 1 0 26 14 1 0 23 15 1 0 1 80 1 0 1 81 1 0 1 82 1 0 3 83 1 0 3 84 1 0 3 85 1 0 4 86 1 0 4 87 1 0 5 88 1 0 5 89 1 0 7 90 1 0 7 91 1 0 8 92 1 0 8 93 1 0 10 94 1 0 10 95 1 0 10 96 1 0 12 97 1 0 13 98 1 0 13 99 1 0 14100 1 6 16101 1 0 16102 1 0 16103 1 0 17104 1 0 17105 1 0 18106 1 0 18107 1 0 19108 1 6 21109 1 0 21110 1 0 21111 1 0 22112 1 0 22113 1 0 22114 1 0 23115 1 6 24116 1 0 24117 1 0 25118 1 0 25119 1 0 27120 1 0 27121 1 0 27122 1 0 29123 1 6 30124 1 6 31125 1 1 32126 1 1 33127 1 6 37128 1 0 37129 1 0 37130 1 0 39131 1 0 41132 1 1 42133 1 6 43134 1 1 44135 1 6 45136 1 6 46137 1 0 46138 1 0 47139 1 0 49140 1 0 50141 1 0 51142 1 0 53143 1 6 54144 1 1 55145 1 1 56146 1 1 57147 1 6 58148 1 0 58149 1 0 59150 1 0 61151 1 0 62152 1 0 63153 1 0 64154 1 1 65155 1 0 65156 1 0 69157 1 1 70158 1 6 71159 1 1 72160 1 6 73161 1 1 74162 1 0 74163 1 0 75164 1 0 77165 1 0 78166 1 0 79167 1 0 M END

Standard InCHIKey	DQGMAYONHHBQRD-MYCAWPNHSA-N
Standard InCHI	InChI=1S/C55H88O24/c1-50(2)15-17-55(49(70)79-47-39(67)36(64)33(61)27(22-58)74-47)18-16-53(6)23(24(55)19-50)9-10-29-52(5)13-12-30(51(3,4)28(52)11-14-54(29,53)7)75-48-43(78-46-38(66)35(63)32(60)26(21-57)73-46)41(40(68)42(77-48)44(69)71-8)76-45-37(65)34(62)31(59)25(20-56)72-45/h9,24-43,45-48,56-68H,10-22H2,1-8H3/t24-,25+,26+,27+,28-,29+,30-,31-,32+,33+,34-,35-,36-,37+,38+,39+,40-,41-,42-,43+,45-,46-,47-,48+,52-,53+,54+,55-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C(=O)OC)O3)O)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1132.57	Volume:	1085.884 ? Van der Waals volume.
Dense:	1.043	LogP:	0.679 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.66 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.092 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	52.0
TPSA:	380.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	9.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.058	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.848	Fsp³:	0.927
MCE-18:	198.34 ? 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:	0.915	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.262	Promiscuous compounds:	0.131

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.435	MDCK Permeability:	-5.15
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.99
20% Bioavailability (F20%):	0.908	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027	MRP1:	0.009
Plasma Protein Binding (PPB):	66.204%	Volume Distribution (VD):	-0.292
Fu:	23.405% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
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:	0.001
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.11 ? 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):

-0.494

Half-life (T1/2):

3.923

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.79	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.978	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.058	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.778	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.273	RPMI-8226 Immunitoxicity:	0.254
A549 Cytotoxicity:	0.915	Hek293 Cytotoxicity:	0.582
BCF:	1.029 ? 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:	3.849 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.683 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.621 ? 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
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Activity	8
IC50	1
ID50	1

Activity Type	# Activity
Cell line	4
Organism	1
Others	5

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	%	DOI[10.6019/CHEMBL1201861]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[25368960]
NPT2	Others	Unspecified	n.a.	Activity	=	16.0	%	PMID[19405528]
NPT2	Others	Unspecified	n.a.	Activity	=	53.6	%	PMID[10411485]
NPT2	Others	Unspecified	n.a.	Activity	=	77.8	%	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	Open TG-GATES in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	IC50	=	487.0	molar ratio	PMID[24689881]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.06	mg	PMID[11754608]

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 NPC10607 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	21718
0.1-0.2	23599
0.2-0.3	3293
0.3-0.4	716
0.4-0.5	323
0.5-0.6	123
0.6-0.7	54
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8763	High Similarity	NPC80986
0.8242	Intermediate Similarity	NPC214484
0.7938	Intermediate Similarity	NPC223301
0.7938	Intermediate Similarity	NPC171544
0.7812	Intermediate Similarity	NPC249848
0.7812	Intermediate Similarity	NPC107966
0.7778	Intermediate Similarity	NPC46665
0.7778	Intermediate Similarity	NPC2370
0.77	Intermediate Similarity	NPC475591
0.77	Intermediate Similarity	NPC236870
0.7624	Intermediate Similarity	NPC297263
0.7526	Intermediate Similarity	NPC235405
0.75	Intermediate Similarity	NPC30735
0.7282	Intermediate Similarity	NPC222580
0.7264	Intermediate Similarity	NPC187290
0.7228	Intermediate Similarity	NPC112352
0.72	Intermediate Similarity	NPC39211
0.7143	Intermediate Similarity	NPC48499
0.7059	Intermediate Similarity	NPC192791
0.7019	Intermediate Similarity	NPC63159
0.7019	Intermediate Similarity	NPC235438
0.7	Intermediate Similarity	NPC475516
0.6981	Remote Similarity	NPC104372
0.6961	Remote Similarity	NPC213674
0.6961	Remote Similarity	NPC469946
0.6923	Remote Similarity	NPC251768
0.6789	Remote Similarity	NPC31838
0.6699	Remote Similarity	NPC157868
0.6667	Remote Similarity	NPC281148
0.6636	Remote Similarity	NPC481078
0.6607	Remote Similarity	NPC475287
0.6604	Remote Similarity	NPC40775
0.6604	Remote Similarity	NPC159309
0.6604	Remote Similarity	NPC86222
0.6596	Remote Similarity	NPC167383
0.6579	Remote Similarity	NPC135904
0.6555	Remote Similarity	NPC481081
0.6549	Remote Similarity	NPC79643
0.6476	Remote Similarity	NPC263756
0.6476	Remote Similarity	NPC161674
0.6458	Remote Similarity	NPC237503
0.6455	Remote Similarity	NPC301449
0.6455	Remote Similarity	NPC601290
0.6449	Remote Similarity	NPC480475
0.6436	Remote Similarity	NPC90856
0.6389	Remote Similarity	NPC68175
0.6387	Remote Similarity	NPC41061
0.6387	Remote Similarity	NPC227551
0.6364	Remote Similarity	NPC114484
0.6355	Remote Similarity	NPC309714
0.6355	Remote Similarity	NPC30289
0.6316	Remote Similarity	NPC60557
0.6316	Remote Similarity	NPC67857
0.6293	Remote Similarity	NPC123199
0.6283	Remote Similarity	NPC62725
0.6281	Remote Similarity	NPC305981
0.6239	Remote Similarity	NPC100639
0.6239	Remote Similarity	NPC470218
0.6238	Remote Similarity	NPC209894
0.623	Remote Similarity	NPC261506
0.623	Remote Similarity	NPC4328
0.6218	Remote Similarity	NPC57484
0.6198	Remote Similarity	NPC43550
0.6182	Remote Similarity	NPC475504
0.6161	Remote Similarity	NPC481079
0.6134	Remote Similarity	NPC481080
0.6132	Remote Similarity	NPC473373
0.6116	Remote Similarity	NPC258617
0.6106	Remote Similarity	NPC295823
0.6106	Remote Similarity	NPC174720
0.6106	Remote Similarity	NPC475467
0.6102	Remote Similarity	NPC475160
0.6102	Remote Similarity	NPC473714
0.6083	Remote Similarity	NPC476068
0.6075	Remote Similarity	NPC295371
0.6075	Remote Similarity	NPC473884
0.5981	Remote Similarity	NPC150400
0.5981	Remote Similarity	NPC109079
0.598	Remote Similarity	NPC128925
0.5965	Remote Similarity	NPC96641
0.5965	Remote Similarity	NPC480473
0.5965	Remote Similarity	NPC163183
0.5965	Remote Similarity	NPC480474
0.5963	Remote Similarity	NPC242840
0.5952	Remote Similarity	NPC250247
0.5909	Remote Similarity	NPC160415
0.5909	Remote Similarity	NPC117714
0.5905	Remote Similarity	NPC1046
0.5905	Remote Similarity	NPC29069
0.59	Remote Similarity	NPC199457
0.5887	Remote Similarity	NPC236638
0.5887	Remote Similarity	NPC294453
0.5856	Remote Similarity	NPC44716
0.5818	Remote Similarity	NPC256133
0.581	Remote Similarity	NPC204458
0.5806	Remote Similarity	NPC293330
0.5776	Remote Similarity	NPC36831
0.5763	Remote Similarity	NPC76972
0.5763	Remote Similarity	NPC469782
0.5763	Remote Similarity	NPC204414
0.5755	Remote Similarity	NPC78046
0.5743	Remote Similarity	NPC306746
0.5714	Remote Similarity	NPC298034
0.5714	Remote Similarity	NPC71065
0.5702	Remote Similarity	NPC283417
0.5702	Remote Similarity	NPC79718
0.5702	Remote Similarity	NPC64715
0.5702	Remote Similarity	NPC200049
0.5688	Remote Similarity	NPC58448
0.5686	Remote Similarity	NPC68419
0.568	Remote Similarity	NPC65105
0.5656	Remote Similarity	NPC488560
0.5625	Remote Similarity	NPC480947
0.562	Remote Similarity	NPC155410
0.5596	Remote Similarity	NPC139894
0.5591	Remote Similarity	NPC302543
0.5586	Remote Similarity	NPC473343
0.5575	Remote Similarity	NPC164389
0.5575	Remote Similarity	NPC473459
0.5575	Remote Similarity	NPC180550
0.5575	Remote Similarity	NPC35405
0.5556	Remote Similarity	NPC241909
0.5547	Remote Similarity	NPC70809
0.5536	Remote Similarity	NPC75417
0.5536	Remote Similarity	NPC478066
0.5534	Remote Similarity	NPC604133
0.5526	Remote Similarity	NPC148417
0.5508	Remote Similarity	NPC104137
0.5508	Remote Similarity	NPC26626
0.55	Remote Similarity	NPC268184
0.5487	Remote Similarity	NPC104071
0.5447	Remote Similarity	NPC471550
0.5446	Remote Similarity	NPC22956
0.5439	Remote Similarity	NPC102439
0.5435	Remote Similarity	NPC162107
0.5435	Remote Similarity	NPC46912
0.5431	Remote Similarity	NPC302887
0.5424	Remote Similarity	NPC160452
0.541	Remote Similarity	NPC165204
0.54	Remote Similarity	NPC191763
0.5391	Remote Similarity	NPC202828
0.5391	Remote Similarity	NPC119592
0.5391	Remote Similarity	NPC162574
0.5377	Remote Similarity	NPC256798
0.5351	Remote Similarity	NPC109588
0.5345	Remote Similarity	NPC470913
0.5328	Remote Similarity	NPC192600
0.531	Remote Similarity	NPC76497
0.5294	Remote Similarity	NPC470477
0.5294	Remote Similarity	NPC475368
0.528	Remote Similarity	NPC47995
0.5278	Remote Similarity	NPC47063
0.5267	Remote Similarity	NPC220160
0.5243	Remote Similarity	NPC46388
0.5243	Remote Similarity	NPC605954
0.5229	Remote Similarity	NPC189884
0.5229	Remote Similarity	NPC269095
0.5229	Remote Similarity	NPC138334
0.5217	Remote Similarity	NPC605226
0.5214	Remote Similarity	NPC609763
0.5195	Remote Similarity	NPC295941
0.5192	Remote Similarity	NPC116794
0.5172	Remote Similarity	NPC11551
0.5167	Remote Similarity	NPC481030
0.5166	Remote Similarity	NPC135334
0.5161	Remote Similarity	NPC475899
0.5143	Remote Similarity	NPC37739
0.5143	Remote Similarity	NPC606107
0.5133	Remote Similarity	NPC173583
0.5133	Remote Similarity	NPC127056
0.5133	Remote Similarity	NPC469778
0.5118	Remote Similarity	NPC85154
0.5116	Remote Similarity	NPC470876
0.5116	Remote Similarity	NPC475514
0.5094	Remote Similarity	NPC137917
0.5094	Remote Similarity	NPC310014
0.5094	Remote Similarity	NPC269315
0.5091	Remote Similarity	NPC473481
0.5088	Remote Similarity	NPC470512
0.5085	Remote Similarity	NPC31193
0.5082	Remote Similarity	NPC11242
0.5082	Remote Similarity	NPC75287
0.5081	Remote Similarity	NPC123522
0.5079	Remote Similarity	NPC191827
0.5078	Remote Similarity	NPC484061
0.5078	Remote Similarity	NPC21691
0.5078	Remote Similarity	NPC484062
0.5068	Remote Similarity	NPC469776
0.5067	Remote Similarity	NPC32723
0.5047	Remote Similarity	NPC271138
0.5047	Remote Similarity	NPC110139
0.5047	Remote Similarity	NPC108709
0.5045	Remote Similarity	NPC164194
0.5044	Remote Similarity	NPC281939
0.5043	Remote Similarity	NPC488526
0.5042	Remote Similarity	NPC486563
0.5041	Remote Similarity	NPC25998
0.5039	Remote Similarity	NPC110633
0.5039	Remote Similarity	NPC286457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC10607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7444
0.1-0.2	1643
0.2-0.3	58
0.3-0.4	5
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