NPASS Compound

Natural Product: NPC54636

Natural Product ID	NPC54636
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Oleanolic Acid 3-O-{O-Beta-D-Glucopyranosyl-(1->4)-O-Beta-D-Glucopyranosyl-(1->3)-O-Alpha-L-Rhamnopyranosyl-(1->2)-O-Beta-D-Glucopyranosyl-(1->4)-Alpha-L-Arabinopyranoside}
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL524336
PubChem CID	10820194
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 181190 0 0 0 0 0 0 0 0999 V2000 0.1519 -8.7186 2.6444 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4516 -8.9026 2.1921 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4060 -9.1300 0.7070 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8623 -8.1028 -0.0212 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6084 -6.9241 -0.0131 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5030 -6.2574 1.1997 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8626 -5.0362 1.0176 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4247 -4.9847 1.8440 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6958 -3.6627 2.1786 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4400 -2.8849 0.9852 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9827 -2.5840 1.0104 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6979 -3.8781 1.5082 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7381 -3.8624 2.8898 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5119 -2.4101 -0.2650 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3521 -1.3017 -0.3268 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9575 -0.4763 -1.3386 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2004 -0.9848 -2.6061 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4627 -0.0893 -3.6095 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6820 -0.9437 -2.9476 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4445 -0.8977 -1.6364 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7314 -1.8441 -0.6715 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4564 -1.9258 0.5126 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5154 0.3597 -1.0827 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8437 0.7328 -0.8807 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1384 0.9115 0.4548 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5377 1.0596 0.5397 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9791 0.8207 1.9601 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6024 -0.4816 2.3150 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8421 2.5143 0.1767 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7601 3.0081 -0.7443 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2064 1.9570 -1.6522 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1865 1.6714 -2.6075 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7769 3.6354 0.0371 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0579 2.6198 -0.4516 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9725 3.3890 0.2304 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3022 4.5746 -0.4330 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1678 5.2925 0.4041 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2010 6.7176 -0.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6658 6.7144 -1.4008 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5399 4.7033 0.2614 C 0 0 2 0 0 0 0 0 0 0 0 0 12.4646 3.2107 0.0835 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1869 2.6108 0.6294 C 0 0 1 0 0 0 0 0 0 0 0 0 11.3380 2.5167 2.0095 O 0 0 0 0 0 0 0 0 0 0 0 0 12.6760 2.8214 -1.2342 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3684 5.0456 1.3364 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -2.0974 -3.6154 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3215 -1.7975 1.1386 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -1.9290 0.2987 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6686 -2.2284 1.1188 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7392 -1.2202 1.1513 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2600 0.2259 0.9089 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6728 0.1471 -0.4758 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5832 -0.8390 -0.6818 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8257 -1.4672 -2.0783 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2317 -0.1535 -0.8332 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3540 1.5537 -0.9244 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 2.1876 -1.1696 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4757 2.3460 0.1415 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4946 1.0603 0.8638 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0871 1.3218 2.2227 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4496 1.8429 1.9865 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8533 2.5125 0.9352 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8925 2.7914 -0.1324 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2831 2.2770 -1.4867 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9523 4.3216 -0.2904 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3503 4.7468 -0.6294 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3787 4.3249 0.3693 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2728 2.9523 0.8950 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1728 1.9014 0.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4470 2.3682 -0.2988 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4681 2.3611 -1.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6355 1.4712 0.1005 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8025 3.7250 0.2649 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7325 4.6696 -0.2099 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2102 5.2776 1.5378 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3723 6.1833 1.5733 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0500 5.1207 2.6353 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7969 3.4767 0.8726 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2919 0.5176 1.9860 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0327 -7.1678 -0.4495 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1249 -8.6206 -0.9307 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7473 -9.5856 0.1560 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6493 -10.8509 -0.4553 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3726 -8.9160 -1.4497 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3706 -6.4038 -1.5867 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3861 -8.3291 1.9221 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9076 -9.8330 2.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0855 -8.0817 2.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7051 -10.0068 0.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1498 -6.2998 -0.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6373 -4.9423 -0.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2484 -5.5195 1.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1867 -5.5162 2.8128 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7617 -3.5592 0.1925 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2994 -1.7531 1.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6981 -3.9675 1.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3468 -3.0115 3.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3415 -0.8366 0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8584 -2.0177 -2.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7871 -0.7023 -4.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2047 0.3979 -4.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8690 0.6834 -3.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9195 -0.0805 -3.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4661 -1.3186 -1.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6836 -2.8267 -1.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.5184 1.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4949 -0.1109 -1.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0752 0.3944 -0.1349 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0751 0.9412 2.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5171 1.5157 2.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2247 -1.1215 1.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7924 3.0738 1.1356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2247 3.8281 -1.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3053 2.4103 -2.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9555 2.1439 -3.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0719 4.5460 0.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4502 3.7285 1.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8219 5.2316 1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8332 7.3536 0.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1526 7.1054 -0.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6393 7.6172 -1.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0089 5.1200 -0.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3057 2.7700 0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1297 1.5741 0.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3014 2.4176 2.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9633 3.5576 -1.8071 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3207 5.1121 1.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -2.8240 -3.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2513 -2.8946 -0.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1676 -3.2034 0.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3339 -2.4201 2.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4721 -1.4217 0.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3127 -1.3137 2.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5497 -0.1809 -1.1022 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6942 -2.1215 -2.0155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9370 -0.5943 -2.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9202 -2.0566 -2.3115 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7008 -0.4971 -1.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2754 0.9316 -0.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5678 -0.3809 0.0279 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9076 1.4835 -1.9457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7592 2.1280 -0.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5442 3.1197 -1.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2215 1.3973 -1.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2723 0.4269 0.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0798 0.4252 2.8737 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4738 2.0781 2.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1714 1.6222 2.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2227 1.2090 -1.6425 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2889 2.5879 -1.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6046 2.7909 -2.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7065 4.8196 0.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3182 4.6439 -1.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6422 4.5701 -1.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3130 5.8842 -0.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6520 3.0021 1.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4814 1.1423 1.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6173 1.2134 -0.4188 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4128 1.3007 -2.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4462 2.7495 -2.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6112 2.8812 -2.2758 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5549 1.1636 1.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5472 0.5596 -0.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5809 2.0365 -0.1051 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8302 3.6170 1.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7675 4.0407 -0.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0683 5.7038 0.0754 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7417 4.6622 -1.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7971 5.5172 3.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3058 3.8267 1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7491 3.2906 1.1208 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7790 4.3484 0.1530 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6066 1.3983 2.5757 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2588 0.7233 1.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1825 -0.3067 2.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7808 -6.9349 0.3059 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3832 -8.7366 -1.7577 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5111 -9.6651 0.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6698 -11.0641 -0.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0402 -9.1284 -0.7659 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8785 -6.7310 -2.3850 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 19 46 1 0 10 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 53 55 1 0 52 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 2 0 62 63 1 0 63 64 1 6 63 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 70 72 1 0 70 73 1 0 73 74 1 0 67 75 1 1 75 76 2 0 75 77 1 0 58 78 1 1 51 79 1 1 5 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 81 84 1 0 80 85 1 0 82 3 1 0 12 7 1 0 21 15 1 0 31 24 1 0 42 35 1 0 53 48 1 0 63 58 1 0 74 67 1 0 59 51 1 0 68 62 1 0 1 86 1 0 2 87 1 0 2 88 1 0 3 89 1 1 5 90 1 6 7 91 1 6 8 92 1 0 8 93 1 0 10 94 1 6 11 95 1 1 12 96 1 6 13 97 1 0 15 98 1 1 17 99 1 1 18100 1 0 18101 1 0 18102 1 0 19103 1 6 20104 1 6 21105 1 6 22106 1 0 24107 1 6 26108 1 6 27109 1 0 27110 1 0 28111 1 0 29112 1 1 30113 1 6 31114 1 6 32115 1 0 33116 1 0 35117 1 1 37118 1 1 38119 1 0 38120 1 0 39121 1 0 40122 1 6 41123 1 1 42124 1 6 43125 1 0 44126 1 0 45127 1 0 46128 1 0 48129 1 6 49130 1 0 49131 1 0 50132 1 0 50133 1 0 52134 1 6 54135 1 0 54136 1 0 54137 1 0 55138 1 0 55139 1 0 55140 1 0 56141 1 0 56142 1 0 57143 1 0 57144 1 0 59145 1 6 60146 1 0 60147 1 0 61148 1 0 64149 1 0 64150 1 0 64151 1 0 65152 1 0 65153 1 0 66154 1 0 66155 1 0 68156 1 1 69157 1 0 69158 1 0 71159 1 0 71160 1 0 71161 1 0 72162 1 0 72163 1 0 72164 1 0 73165 1 0 73166 1 0 74167 1 0 74168 1 0 77169 1 0 78170 1 0 78171 1 0 78172 1 0 79173 1 0 79174 1 0 79175 1 0 80176 1 1 81177 1 6 82178 1 1 83179 1 0 84180 1 0 85181 1 0 M END

Standard InCHIKey	OIIUKDNESXXGGA-JNYGYAQVSA-N
Standard InCHI	InChI=1S/C59H96O26/c1-24-34(63)46(84-50-43(72)40(69)45(29(22-62)80-50)83-49-42(71)39(68)36(65)28(21-61)79-49)44(73)51(77-24)85-47-37(66)30(81-48-41(70)38(67)35(64)27(20-60)78-48)23-76-52(47)82-33-12-13-56(6)31(55(33,4)5)11-14-58(8)32(56)10-9-25-26-19-54(2,3)15-17-59(26,53(74)75)18-16-57(25,58)7/h9,24,26-52,60-73H,10-23H2,1-8H3,(H,74,75)/t24-,26-,27+,28+,29+,30-,31-,32+,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+,43+,44+,45+,46+,47+,48-,49-,50-,51-,52-,56-,57+,58+,59-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CO[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1220.62	Volume:	1166.728 ? Van der Waals volume.
Dense:	1.046	LogP:	0.113 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.32 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.951 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	57.0
TPSA:	412.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	15.0	Rings:	10.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.066	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.189	Fsp³:	0.949
MCE-18:	217.043 ? 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:	0.854	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.366	Promiscuous compounds:	0.143

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.944	MDCK Permeability:	-5.118
Pgp-inhibitor:	0.0	Pgp-substrate:	0.032
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):	0.975
20% Bioavailability (F20%):	0.181	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.006
Plasma Protein Binding (PPB):	66.389%	Volume Distribution (VD):	-0.311
Fu:	23.413% ? 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:	0.0
CYP3A4-inhibitor:	0.931	CYP3A4-substrate:	0.008
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.163
HLM stability:	0.0 ? 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):

-0.971

Half-life (T1/2):

5.028

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.865	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.986	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.043	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.777	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.165	RPMI-8226 Immunitoxicity:	0.188
A549 Cytotoxicity:	0.935	Hek293 Cytotoxicity:	0.512
BCF:	1.07 ? 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:	3.543 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.102 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.046 ? 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
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	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	4

Activity Type	# Activity
Cell line	4

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	2.7	ug.mL-1	PMID[16933872]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	3500.0	nM	PMID[17846127]
NPT81	Cell line	A549	Homo sapiens	IC50	=	6200.0	nM	PMID[23249297]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	3100.0	nM	PMID[22316191]

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 NPC54636 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	24884
0.1-0.2	21036
0.2-0.3	2547
0.3-0.4	793
0.4-0.5	430
0.5-0.6	98
0.6-0.7	41
0.7-0.8	0
0.8-0.85	8
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	NPC251263
0.8839	High Similarity	NPC471385
0.8716	High Similarity	NPC166422
0.8411	Intermediate Similarity	NPC488564
0.8381	Intermediate Similarity	NPC257468
0.8348	Intermediate Similarity	NPC161717
0.8288	Intermediate Similarity	NPC133818
0.8214	Intermediate Similarity	NPC219180
0.8148	Intermediate Similarity	NPC324875
0.8148	Intermediate Similarity	NPC292677
0.8125	Intermediate Similarity	NPC323341
0.7778	Intermediate Similarity	NPC139044
0.7568	Intermediate Similarity	NPC276093
0.75	Intermediate Similarity	NPC471384
0.75	Intermediate Similarity	NPC323359
0.7431	Intermediate Similarity	NPC114304
0.7232	Intermediate Similarity	NPC481082
0.7232	Intermediate Similarity	NPC164419
0.7222	Intermediate Similarity	NPC127056
0.7143	Intermediate Similarity	NPC471383
0.7069	Intermediate Similarity	NPC475486
0.7016	Intermediate Similarity	NPC43550
0.7009	Intermediate Similarity	NPC164194
0.6972	Remote Similarity	NPC25605
0.6903	Remote Similarity	NPC180550
0.6903	Remote Similarity	NPC35405
0.6818	Remote Similarity	NPC56713
0.6807	Remote Similarity	NPC476992
0.6757	Remote Similarity	NPC109079
0.6744	Remote Similarity	NPC250247
0.6731	Remote Similarity	NPC606107
0.6697	Remote Similarity	NPC270667
0.6696	Remote Similarity	NPC472949
0.6667	Remote Similarity	NPC59804
0.6614	Remote Similarity	NPC65105
0.6612	Remote Similarity	NPC475287
0.6581	Remote Similarity	NPC79718
0.6577	Remote Similarity	NPC136877
0.6562	Remote Similarity	NPC136768
0.6549	Remote Similarity	NPC488561
0.6535	Remote Similarity	NPC41061
0.6535	Remote Similarity	NPC227551
0.6491	Remote Similarity	NPC22956
0.6466	Remote Similarity	NPC104400
0.6466	Remote Similarity	NPC10320
0.6441	Remote Similarity	NPC119794
0.6434	Remote Similarity	NPC305981
0.6429	Remote Similarity	NPC12288
0.6385	Remote Similarity	NPC261506
0.6385	Remote Similarity	NPC4328
0.6372	Remote Similarity	NPC174679
0.6372	Remote Similarity	NPC279554
0.6311	Remote Similarity	NPC62725
0.6207	Remote Similarity	NPC80843
0.6174	Remote Similarity	NPC114441
0.6168	Remote Similarity	NPC204407
0.6165	Remote Similarity	NPC220160
0.6148	Remote Similarity	NPC488209
0.6061	Remote Similarity	NPC236638
0.6061	Remote Similarity	NPC294453
0.6047	Remote Similarity	NPC481080
0.6032	Remote Similarity	NPC151543
0.6015	Remote Similarity	NPC298034
0.6015	Remote Similarity	NPC71065
0.5954	Remote Similarity	NPC110633
0.5909	Remote Similarity	NPC258617
0.5906	Remote Similarity	NPC79643
0.5882	Remote Similarity	NPC469945
0.5873	Remote Similarity	NPC288205
0.5873	Remote Similarity	NPC51465
0.5818	Remote Similarity	NPC283849
0.5814	Remote Similarity	NPC135904
0.5794	Remote Similarity	NPC280941
0.5794	Remote Similarity	NPC235772
0.5764	Remote Similarity	NPC40085
0.5758	Remote Similarity	NPC476068
0.5746	Remote Similarity	NPC293330
0.5738	Remote Similarity	NPC258885
0.5714	Remote Similarity	NPC31839
0.5714	Remote Similarity	NPC6377
0.5714	Remote Similarity	NPC208381
0.5704	Remote Similarity	NPC202828
0.5704	Remote Similarity	NPC119592
0.5704	Remote Similarity	NPC111466
0.5702	Remote Similarity	NPC204392
0.5693	Remote Similarity	NPC488212
0.5692	Remote Similarity	NPC123199
0.5691	Remote Similarity	NPC73829
0.5652	Remote Similarity	NPC191410
0.5649	Remote Similarity	NPC475160
0.5649	Remote Similarity	NPC475140
0.5649	Remote Similarity	NPC473714
0.5645	Remote Similarity	NPC488515
0.5591	Remote Similarity	NPC481078
0.5581	Remote Similarity	NPC60557
0.5581	Remote Similarity	NPC67857
0.5578	Remote Similarity	NPC264270
0.5565	Remote Similarity	NPC275668
0.5565	Remote Similarity	NPC284807
0.5565	Remote Similarity	NPC475504
0.5565	Remote Similarity	NPC123796
0.5556	Remote Similarity	NPC475514
0.5474	Remote Similarity	NPC481081
0.5462	Remote Similarity	NPC473824
0.5455	Remote Similarity	NPC488516
0.5439	Remote Similarity	NPC286347
0.5426	Remote Similarity	NPC480939
0.5403	Remote Similarity	NPC473383
0.5398	Remote Similarity	NPC28198
0.5398	Remote Similarity	NPC476123
0.5397	Remote Similarity	NPC471435
0.5397	Remote Similarity	NPC471434
0.536	Remote Similarity	NPC148417
0.5339	Remote Similarity	NPC475472
0.5312	Remote Similarity	NPC291903
0.5308	Remote Similarity	NPC75287
0.5299	Remote Similarity	NPC470218
0.5299	Remote Similarity	NPC191827
0.5294	Remote Similarity	NPC211798
0.5267	Remote Similarity	NPC475119
0.5263	Remote Similarity	NPC470911
0.5259	Remote Similarity	NPC47995
0.5259	Remote Similarity	NPC488560
0.5242	Remote Similarity	NPC240734
0.5234	Remote Similarity	NPC78034
0.5227	Remote Similarity	NPC76972
0.5227	Remote Similarity	NPC469782
0.5227	Remote Similarity	NPC204414
0.5227	Remote Similarity	NPC610204
0.52	Remote Similarity	NPC309714
0.5182	Remote Similarity	NPC57484
0.5161	Remote Similarity	NPC76497
0.5159	Remote Similarity	NPC173859
0.5159	Remote Similarity	NPC148603
0.5156	Remote Similarity	NPC484832
0.5154	Remote Similarity	NPC295823
0.5154	Remote Similarity	NPC174720
0.5154	Remote Similarity	NPC475467
0.5149	Remote Similarity	NPC165204
0.5128	Remote Similarity	NPC100383
0.5125	Remote Similarity	NPC481323
0.5125	Remote Similarity	NPC469778
0.512	Remote Similarity	NPC112352
0.5118	Remote Similarity	NPC63159
0.5118	Remote Similarity	NPC91838
0.5116	Remote Similarity	NPC37134
0.5115	Remote Similarity	NPC609281
0.5109	Remote Similarity	NPC181066
0.5109	Remote Similarity	NPC488211
0.5106	Remote Similarity	NPC302543
0.5091	Remote Similarity	NPC295941
0.5081	Remote Similarity	NPC470512
0.5079	Remote Similarity	NPC124296
0.5077	Remote Similarity	NPC606145
0.5074	Remote Similarity	NPC100639
0.5063	Remote Similarity	NPC469776
0.5062	Remote Similarity	NPC32723
0.5047	Remote Similarity	NPC120840
0.5042	Remote Similarity	NPC473538
0.5039	Remote Similarity	NPC251768
0.5035	Remote Similarity	NPC135849
0.5031	Remote Similarity	NPC481324

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC54636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7155
0.1-0.2	1930
0.2-0.3	56
0.3-0.4	8
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