NPASS Compound

Natural Product: NPC251263

Natural Product ID	NPC251263
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)-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-4,5-dihydroxyoxan-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	CHEMBL448368
PubChem CID	11766614
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 160168 0 0 0 0 0 0 0 0999 V2000 5.9724 -0.7154 1.0963 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9279 -0.2221 2.0737 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5343 0.6165 3.1842 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0135 2.0236 3.0601 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4900 1.9820 3.0266 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9598 0.8107 2.2029 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9801 0.5057 1.3107 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7892 -0.2734 3.0099 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4700 -0.6451 3.2609 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3581 -1.0371 4.6857 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3735 -2.1780 4.8873 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0734 -3.2467 3.8718 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2018 -2.7617 2.5363 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1540 -1.8960 2.3671 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0945 -2.3763 2.5541 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1217 -1.9850 1.7835 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2237 -3.0551 0.6379 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2608 -2.5522 -0.3509 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5934 -2.6110 0.3111 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9837 -4.0525 0.4732 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6154 -1.8537 1.6169 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9018 -2.2395 2.2799 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1233 -2.0781 1.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0057 -1.9833 -0.0105 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7157 -3.1505 -0.7123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5936 -1.8703 -0.5347 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5088 -2.0240 -1.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5967 -1.2088 -2.6017 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5929 -0.6379 -1.9420 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5742 0.1383 -2.7774 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1282 1.5657 -2.8884 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1019 2.4068 -3.6486 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6730 3.8694 -3.4967 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1701 2.1087 -5.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4514 2.3101 -2.9619 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9363 0.9038 -2.9572 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9682 -0.0908 -2.3426 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1329 -0.0227 -0.8617 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1941 -0.8758 -0.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7391 -0.7337 -0.4675 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2094 0.5270 0.1551 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4198 -1.4189 -2.8849 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8880 -2.3436 -2.2136 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2881 -1.5961 -4.2569 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4270 -1.8797 2.4774 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4433 -2.9642 3.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4061 -0.5609 3.2776 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3806 -2.6500 6.1773 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1331 -1.5202 5.0860 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9592 3.1889 2.5711 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4763 2.4876 1.8415 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9510 3.7668 1.8184 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4764 3.8654 1.9017 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1773 3.5262 0.6374 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1543 2.9251 -0.3628 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0898 3.9246 -0.4814 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0053 3.5330 -1.4522 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1442 2.5681 -0.9577 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5500 4.4183 0.7110 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8277 2.6897 -1.5574 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1844 1.3561 -1.7740 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5660 0.8830 -3.0479 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1769 -0.4668 -3.4724 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6310 -0.2270 -3.6611 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2745 0.6099 -2.6190 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2172 1.5972 -3.3712 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3493 2.4771 -4.0341 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5521 1.3536 -1.7883 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3112 -1.4655 -3.6923 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6068 -0.7665 -4.7184 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2241 0.5891 -2.8062 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2168 2.6046 0.8552 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6908 5.2337 2.2366 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4378 0.0652 4.4326 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9988 -0.4496 1.4277 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8029 -0.2942 0.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8626 -1.8177 0.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4336 -1.0895 2.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6351 0.6859 2.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2293 2.7017 3.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1228 1.8409 4.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0041 1.1533 1.7355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8268 0.1561 2.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6949 -0.1994 5.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3619 -1.7000 4.7100 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8855 -4.0064 3.9572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1007 -3.7260 4.0236 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2002 -1.4079 1.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9464 -1.0802 1.1410 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3820 -4.0442 1.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2479 -3.0044 0.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1926 -3.1488 -1.2508 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0136 -1.4708 -0.5010 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9794 -4.2307 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8728 -4.5588 -0.5011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2803 -4.6034 1.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7594 -0.7630 1.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9578 -1.5818 3.2042 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8774 -3.2711 2.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8114 -2.9624 1.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7154 -1.2304 1.9265 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3300 -2.7785 -1.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3967 -3.6939 -0.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9809 -3.8313 -1.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3397 -0.7688 -0.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5496 -3.0197 -2.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5297 -1.5839 -2.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5329 -1.0922 -3.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5261 -0.2560 -3.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1778 1.5716 -3.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9308 2.0760 -1.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8967 4.1633 -4.2179 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5986 4.4807 -3.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3001 4.0139 -2.4588 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4125 1.0529 -5.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1963 2.4224 -5.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9240 2.8117 -5.5450 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1545 2.9228 -3.5747 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4123 2.7943 -1.9808 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9315 0.8183 -2.4958 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0611 0.5926 -4.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9825 1.0312 -0.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1606 -0.3155 -0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4937 -1.9544 -0.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2787 -0.5053 0.9843 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4166 0.9815 -0.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8105 0.4089 1.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0652 1.2545 0.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8288 -2.2926 -4.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4094 -3.3326 3.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0478 -3.8282 3.3321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8134 -2.5550 4.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4443 -0.7304 4.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3478 0.0358 3.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.1058 2.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4783 -2.6010 6.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0402 -1.3395 6.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0729 3.2581 1.5851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6380 4.2482 2.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9005 3.2966 2.7329 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6495 4.4363 0.2227 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9362 1.9459 0.0823 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5630 4.8507 -0.9527 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4591 3.1428 -2.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4333 4.4457 -1.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2625 1.6682 -1.3043 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7748 0.7048 -0.9462 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6343 1.6217 -3.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9628 -1.1989 -2.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7562 0.2668 -4.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0183 -0.0123 -2.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7902 1.0571 -4.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8224 2.1788 -2.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6245 2.5718 -5.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1575 -1.3759 -3.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9541 -1.6357 -5.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9807 -0.3365 -2.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7873 1.7675 1.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3258 5.8318 1.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8142 0.6784 5.0814 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 8 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 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 1 37 42 1 6 42 43 2 0 42 44 1 0 21 45 1 0 45 46 1 0 45 47 1 0 11 48 1 0 10 49 1 0 5 50 1 0 4 51 1 0 51 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 56 59 1 0 55 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 65 68 1 0 64 69 1 0 63 70 1 0 62 71 1 0 54 72 1 0 53 73 1 0 3 74 1 0 7 2 1 0 14 9 1 0 45 16 1 0 59 52 1 0 68 61 1 0 26 19 1 0 40 29 1 0 40 24 1 0 37 30 1 0 1 75 1 0 1 76 1 0 1 77 1 0 2 78 1 1 3 79 1 6 4 80 1 1 5 81 1 1 6 82 1 6 9 83 1 6 10 84 1 1 11 85 1 6 12 86 1 0 12 87 1 0 14 88 1 6 16 89 1 6 17 90 1 0 17 91 1 0 18 92 1 0 18 93 1 0 20 94 1 0 20 95 1 0 20 96 1 0 21 97 1 6 22 98 1 0 22 99 1 0 23100 1 0 23101 1 0 25102 1 0 25103 1 0 25104 1 0 26105 1 6 27106 1 0 27107 1 0 28108 1 0 30109 1 6 31110 1 0 31111 1 0 33112 1 0 33113 1 0 33114 1 0 34115 1 0 34116 1 0 34117 1 0 35118 1 0 35119 1 0 36120 1 0 36121 1 0 38122 1 0 38123 1 0 39124 1 0 39125 1 0 41126 1 0 41127 1 0 41128 1 0 44129 1 0 46130 1 0 46131 1 0 46132 1 0 47133 1 0 47134 1 0 47135 1 0 48136 1 0 49137 1 0 50138 1 0 52139 1 1 53140 1 1 54141 1 6 55142 1 1 56143 1 6 57144 1 0 57145 1 0 58146 1 0 61147 1 1 62148 1 6 63149 1 1 64150 1 6 65151 1 1 66152 1 0 66153 1 0 67154 1 0 69155 1 0 70156 1 0 71157 1 0 72158 1 0 73159 1 0 74160 1 0 M END

Standard InCHIKey	VDRZQZWUCOHKED-BXROMGGZSA-N
Standard InCHI	InChI=1S/C53H86O21/c1-23-32(57)41(73-44-38(63)36(61)40(28(21-55)70-44)72-43-37(62)35(60)34(59)27(20-54)69-43)39(64)45(68-23)74-42-33(58)26(56)22-67-46(42)71-31-12-13-50(6)29(49(31,4)5)11-14-52(8)30(50)10-9-24-25-19-48(2,3)15-17-53(25,47(65)66)18-16-51(24,52)7/h9,23,25-46,54-64H,10-22H2,1-8H3,(H,65,66)/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,40+,41+,42+,43-,44-,45-,46-,50-,51+,52+,53-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1058.57	Volume:	1027.557 ? Van der Waals volume.
Dense:	1.03	LogP:	1.021 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.908 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.234 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	51.0
TPSA:	333.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	12.0	Rings:	9.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.097	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.687	Fsp³:	0.943
MCE-18:	194.369 ? 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:	0.901	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:	0.26	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.525	MDCK Permeability:	-5.081
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
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):	0.945
20% Bioavailability (F20%):	0.245	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.02
Plasma Protein Binding (PPB):	71.165%	Volume Distribution (VD):	-0.433
Fu:	19.338% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
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:	0.983	CYP3A4-substrate:	0.509
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.261
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):

-0.464

Half-life (T1/2):

4.231

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.844	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.929	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.092	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.768	Drug-induced Nephrotoxicity:	0.99
Genotoxicity:	0.273	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.843	Hek293 Cytotoxicity:	0.454
BCF:	1.324 ? 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:	3.759 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.381 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.432 ? 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	=	2.6	ug.mL-1	PMID[10514313]
NPT1083	Cell line	A-375	Homo sapiens	IC50	=	5900.0	nM	PMID[23639650]
NPT81	Cell line	A549	Homo sapiens	IC50	=	7900.0	nM	PMID[23639650]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	3500.0	nM	PMID[23639650]

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 NPC251263 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	24877
0.1-0.2	21034
0.2-0.3	2512
0.3-0.4	833
0.4-0.5	393
0.5-0.6	120
0.6-0.7	50
0.7-0.8	0
0.8-0.85	5
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9327	High Similarity	NPC133818
0.9208	High Similarity	NPC324875
0.9208	High Similarity	NPC292677
0.8889	High Similarity	NPC54636
0.8829	High Similarity	NPC161717
0.8704	High Similarity	NPC219180
0.8558	High Similarity	NPC276093
0.8218	Intermediate Similarity	NPC127056
0.819	Intermediate Similarity	NPC481082
0.819	Intermediate Similarity	NPC164419
0.8174	Intermediate Similarity	NPC471385
0.8036	Intermediate Similarity	NPC166422
0.7982	Intermediate Similarity	NPC475486
0.7767	Intermediate Similarity	NPC56713
0.7596	Intermediate Similarity	NPC59804
0.757	Intermediate Similarity	NPC114304
0.7478	Intermediate Similarity	NPC323341
0.7456	Intermediate Similarity	NPC475287
0.7411	Intermediate Similarity	NPC488564
0.7364	Intermediate Similarity	NPC257468
0.7264	Intermediate Similarity	NPC174679
0.7264	Intermediate Similarity	NPC279554
0.7143	Intermediate Similarity	NPC164194
0.7143	Intermediate Similarity	NPC79718
0.7103	Intermediate Similarity	NPC25605
0.7064	Intermediate Similarity	NPC80843
0.7037	Intermediate Similarity	NPC109079
0.7027	Intermediate Similarity	NPC180550
0.7027	Intermediate Similarity	NPC35405
0.6972	Remote Similarity	NPC488561
0.6911	Remote Similarity	NPC41061
0.6911	Remote Similarity	NPC227551
0.6909	Remote Similarity	NPC22956
0.6891	Remote Similarity	NPC471384
0.6863	Remote Similarity	NPC606107
0.6822	Remote Similarity	NPC270667
0.6818	Remote Similarity	NPC472949
0.6814	Remote Similarity	NPC139044
0.68	Remote Similarity	NPC305981
0.6746	Remote Similarity	NPC261506
0.6746	Remote Similarity	NPC4328
0.6726	Remote Similarity	NPC104400
0.6726	Remote Similarity	NPC10320
0.6581	Remote Similarity	NPC323359
0.6555	Remote Similarity	NPC62725
0.6545	Remote Similarity	NPC12288
0.6512	Remote Similarity	NPC220160
0.6406	Remote Similarity	NPC236638
0.6406	Remote Similarity	NPC294453
0.6387	Remote Similarity	NPC488209
0.6357	Remote Similarity	NPC298034
0.6357	Remote Similarity	NPC71065
0.6333	Remote Similarity	NPC481078
0.6325	Remote Similarity	NPC275668
0.6325	Remote Similarity	NPC475504
0.6299	Remote Similarity	NPC110633
0.6286	Remote Similarity	NPC204407
0.6283	Remote Similarity	NPC114441
0.6271	Remote Similarity	NPC119794
0.6261	Remote Similarity	NPC469945
0.626	Remote Similarity	NPC79643
0.625	Remote Similarity	NPC136877
0.6239	Remote Similarity	NPC471383
0.623	Remote Similarity	NPC288205
0.623	Remote Similarity	NPC51465
0.623	Remote Similarity	NPC476992
0.6226	Remote Similarity	NPC283849
0.6212	Remote Similarity	NPC250247
0.6202	Remote Similarity	NPC43550
0.616	Remote Similarity	NPC135904
0.6148	Remote Similarity	NPC280941
0.6148	Remote Similarity	NPC235772
0.6087	Remote Similarity	NPC6377
0.6087	Remote Similarity	NPC208381
0.6032	Remote Similarity	NPC123199
0.6031	Remote Similarity	NPC136768
0.6031	Remote Similarity	NPC202828
0.6031	Remote Similarity	NPC119592
0.6016	Remote Similarity	NPC481080
0.5957	Remote Similarity	NPC40085
0.592	Remote Similarity	NPC60557
0.592	Remote Similarity	NPC67857
0.5868	Remote Similarity	NPC488515
0.5847	Remote Similarity	NPC112352
0.5833	Remote Similarity	NPC293330
0.5833	Remote Similarity	NPC258885
0.5833	Remote Similarity	NPC65105
0.5833	Remote Similarity	NPC91838
0.5818	Remote Similarity	NPC31839
0.5789	Remote Similarity	NPC111466
0.5785	Remote Similarity	NPC73829
0.578	Remote Similarity	NPC28198
0.578	Remote Similarity	NPC476123
0.5769	Remote Similarity	NPC488211
0.5764	Remote Similarity	NPC264270
0.576	Remote Similarity	NPC480939
0.5752	Remote Similarity	NPC191410
0.5725	Remote Similarity	NPC57484
0.5672	Remote Similarity	NPC481081
0.5641	Remote Similarity	NPC475296
0.5639	Remote Similarity	NPC258617
0.5606	Remote Similarity	NPC21691
0.5591	Remote Similarity	NPC475119
0.5573	Remote Similarity	NPC47995
0.5547	Remote Similarity	NPC76972
0.5547	Remote Similarity	NPC469782
0.5547	Remote Similarity	NPC204414
0.5547	Remote Similarity	NPC488212
0.5536	Remote Similarity	NPC286347
0.5515	Remote Similarity	NPC302543
0.5489	Remote Similarity	NPC476068
0.5487	Remote Similarity	NPC100383
0.5476	Remote Similarity	NPC187618
0.5462	Remote Similarity	NPC165204
0.5448	Remote Similarity	NPC286457
0.5447	Remote Similarity	NPC63159
0.5431	Remote Similarity	NPC475472
0.5426	Remote Similarity	NPC473824
0.5417	Remote Similarity	NPC488516
0.5414	Remote Similarity	NPC181066
0.5414	Remote Similarity	NPC4749
0.5414	Remote Similarity	NPC85154
0.541	Remote Similarity	NPC160415
0.5397	Remote Similarity	NPC291903
0.5391	Remote Similarity	NPC284807
0.5385	Remote Similarity	NPC151543
0.5385	Remote Similarity	NPC211798
0.5385	Remote Similarity	NPC469778
0.5379	Remote Similarity	NPC475160
0.5379	Remote Similarity	NPC283417
0.5379	Remote Similarity	NPC200049
0.5379	Remote Similarity	NPC473714
0.5378	Remote Similarity	NPC474589
0.5372	Remote Similarity	NPC263756
0.5372	Remote Similarity	NPC213674
0.5366	Remote Similarity	NPC164389
0.5351	Remote Similarity	NPC242611
0.5325	Remote Similarity	NPC469776
0.5321	Remote Similarity	NPC32723
0.5312	Remote Similarity	NPC104137
0.5312	Remote Similarity	NPC26626
0.5294	Remote Similarity	NPC475514
0.5287	Remote Similarity	NPC481323
0.5283	Remote Similarity	NPC481324
0.5263	Remote Similarity	NPC475140
0.5247	Remote Similarity	NPC295941
0.5242	Remote Similarity	NPC480475
0.5238	Remote Similarity	NPC302887
0.5234	Remote Similarity	NPC480474
0.5224	Remote Similarity	NPC473918
0.5224	Remote Similarity	NPC488560
0.5221	Remote Similarity	NPC265841
0.5221	Remote Similarity	NPC488308
0.522	Remote Similarity	NPC135334
0.5211	Remote Similarity	NPC489209
0.52	Remote Similarity	NPC475591
0.52	Remote Similarity	NPC236870
0.5194	Remote Similarity	NPC187290
0.5191	Remote Similarity	NPC313110
0.5182	Remote Similarity	NPC312650
0.5182	Remote Similarity	NPC470876
0.5156	Remote Similarity	NPC301449
0.5156	Remote Similarity	NPC23275
0.5156	Remote Similarity	NPC601290
0.5143	Remote Similarity	NPC70809
0.5143	Remote Similarity	NPC120840
0.512	Remote Similarity	NPC44716
0.512	Remote Similarity	NPC251768
0.512	Remote Similarity	NPC473383
0.512	Remote Similarity	NPC46665
0.5116	Remote Similarity	NPC295823
0.5116	Remote Similarity	NPC174720
0.5116	Remote Similarity	NPC480473
0.5116	Remote Similarity	NPC160452
0.5116	Remote Similarity	NPC475467
0.5109	Remote Similarity	NPC473452
0.5106	Remote Similarity	NPC488309
0.5088	Remote Similarity	NPC57362
0.5081	Remote Similarity	NPC192791
0.5079	Remote Similarity	NPC148417
0.5078	Remote Similarity	NPC114484
0.5077	Remote Similarity	NPC469947
0.5077	Remote Similarity	NPC480948
0.5074	Remote Similarity	NPC71391
0.5072	Remote Similarity	NPC271610
0.5062	Remote Similarity	NPC469777
0.504	Remote Similarity	NPC124296
0.504	Remote Similarity	NPC117714
0.504	Remote Similarity	NPC30289
0.504	Remote Similarity	NPC605226
0.5039	Remote Similarity	NPC218954
0.5039	Remote Similarity	NPC75318
0.5038	Remote Similarity	NPC123522
0.5038	Remote Similarity	NPC480936
0.5037	Remote Similarity	NPC100639
0.5037	Remote Similarity	NPC191827
0.5036	Remote Similarity	NPC484061
0.5036	Remote Similarity	NPC484062
0.5032	Remote Similarity	NPC469775

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC251263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7140
0.1-0.2	1942
0.2-0.3	59
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