NPASS Compound

Natural Product: NPC147545

Natural Product ID	NPC147545
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BJVYIZFKHTVRIM-LAVATZBFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10996873
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 186195 0 0 0 0 0 0 0 0999 V2000 11.9555 0.9355 -1.6183 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4522 1.0844 -0.1991 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5167 -0.0256 0.1863 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3442 0.0040 -0.7639 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3437 -1.0517 -0.5199 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1965 -0.9478 -1.5087 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5315 -1.1194 -2.9245 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2882 -1.9662 -0.9032 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6079 -1.7639 0.5931 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2652 -1.3106 1.1893 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3415 -2.0913 0.3371 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8776 -1.7804 0.4441 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4424 -2.0892 1.8881 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9777 -2.0804 1.9645 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1722 -2.2729 0.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3075 -2.2485 1.0950 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1052 -3.0633 0.1826 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3772 -3.9001 -0.7963 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0845 -3.8461 -0.8766 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6878 -2.5249 -0.4298 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3180 -1.4103 -1.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1714 -2.7417 -0.4387 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6922 -2.7484 -1.8562 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1671 -2.7027 -2.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8188 -1.7266 -1.0610 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4348 -0.3382 -1.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0739 -2.3518 -0.5398 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3676 -2.7359 -0.2731 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1776 -1.6219 0.3645 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3861 -1.2731 -0.4126 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8529 -1.2374 -1.8907 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7173 -2.7355 -2.2073 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3950 -2.9553 -3.6550 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3339 -2.3054 -4.4677 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6793 -2.5601 -4.5219 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1697 -3.4473 -3.8024 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5368 -1.7712 -5.4409 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8823 -3.3603 -1.3436 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7914 -0.7159 -2.7269 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9184 -0.0695 -0.1000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3012 -0.0669 0.0750 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8174 0.5239 1.2986 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1852 1.1046 1.2627 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6004 1.5014 -0.1103 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3352 1.7727 -0.8837 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5953 2.4192 -2.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7391 0.5524 -1.1118 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4656 2.5896 -0.1178 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6697 2.1778 -0.6985 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.7909 2.1777 0.3204 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.9675 3.0158 -0.1576 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.3756 4.3507 -0.5691 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.5094 4.0880 -1.7753 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.4775 5.1830 -1.9664 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5309 5.0594 -0.9646 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9761 2.8451 -1.8570 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4353 5.2066 -0.8731 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.8851 3.1831 0.8564 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.2890 0.9009 0.5630 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1603 0.2487 1.7740 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8851 -0.4763 2.2987 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3519 -1.8494 1.7237 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5804 -1.0438 2.5600 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4463 -0.0523 3.3001 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6967 -0.5959 4.6963 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3250 -0.5819 5.3740 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2747 -1.1626 4.4799 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2283 -0.0956 4.2040 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7325 -1.7588 3.3425 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3847 -1.2268 6.6101 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4937 0.3129 5.4189 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7212 1.1481 3.4972 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5659 -0.7389 0.6429 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7818 -2.3130 -0.2946 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5487 -2.9607 -1.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6581 1.1590 0.7109 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4039 2.2670 0.3065 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5498 2.4341 1.0453 C 0 0 1 0 0 0 0 0 0 0 0 0 15.7117 2.2198 0.0648 C 0 0 1 0 0 0 0 0 0 0 0 0 17.0371 2.4204 0.7580 C 0 0 2 0 0 0 0 0 0 0 0 0 17.0419 3.7526 1.4711 C 0 0 1 0 0 0 0 0 0 0 0 0 15.7671 3.9602 2.2678 C 0 0 1 0 0 0 0 0 0 0 0 0 15.7323 5.4110 2.6965 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5872 5.6383 3.4561 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6193 3.7234 1.5097 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0927 3.7056 2.3911 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0231 2.4749 -0.2263 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6370 1.0060 -0.5721 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0587 0.9651 -1.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6916 -0.1177 -1.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5340 1.6764 -2.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9157 2.0428 -0.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9779 -0.9931 0.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1164 0.2713 1.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6614 -0.0208 -1.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8234 1.0012 -0.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7388 0.0646 -1.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 -2.0617 -3.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0193 -0.3054 -3.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5871 -1.0184 -3.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5212 -2.9983 -1.1877 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9624 -2.6887 1.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1375 -0.2327 1.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2299 -1.6519 2.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5072 -3.1704 0.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6624 -0.7255 0.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8363 -3.1270 2.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8983 -1.3373 2.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4757 -1.9073 2.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6827 -1.1951 1.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4608 -2.6330 2.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6881 -3.8077 0.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 -5.0178 -0.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7810 -3.7450 -1.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5828 -4.6253 -0.2489 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4203 -4.0706 -1.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6932 -1.0492 -1.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9943 -0.5566 -1.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2019 -1.7518 -2.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3868 -3.7766 -0.0269 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2103 -1.9786 -2.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3680 -3.7336 -2.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6598 -3.7009 -1.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3998 -2.3994 -3.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3478 -0.3823 -1.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4913 0.4006 -0.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9740 -0.0458 -2.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2881 -3.5307 0.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4755 -0.7323 0.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1085 -2.1199 -0.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9035 -0.7175 -1.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7412 -3.1450 -2.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4923 -4.0438 -3.8542 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3716 -2.5880 -3.9133 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5258 -0.7085 -5.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5902 -2.1359 -5.4019 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1620 -1.9232 -6.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4659 0.0141 -3.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6499 -1.1117 -0.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1098 1.2925 1.6931 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2261 2.0231 1.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0655 0.5792 -0.5723 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7049 2.4509 -0.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5835 3.5235 -2.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7438 2.1731 -2.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5016 2.0322 -2.7011 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5834 1.0844 -1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4159 2.5554 1.2985 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4500 2.5224 -1.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7551 4.7376 0.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2063 4.1974 -2.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9647 6.1775 -1.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0491 5.0780 -2.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4719 5.9193 -0.4472 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.5881 5.7693 -0.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1741 2.3056 1.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0507 0.2457 -0.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8202 -0.6769 1.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6615 -1.3658 1.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9569 -0.4028 1.8659 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3378 0.2338 2.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1191 -1.6109 4.6962 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1040 0.4827 5.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7845 -2.0041 5.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2307 -0.5136 4.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2001 0.1444 3.1280 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3661 0.8090 4.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6499 -2.1809 6.4313 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4483 0.2133 5.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3561 1.7727 3.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0577 -3.1078 -2.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5990 -2.6443 -1.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6333 -4.0285 -0.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2330 0.2161 0.6022 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3892 1.2387 1.7831 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6735 1.6570 1.8278 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6024 3.0165 -0.6989 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2989 1.5738 1.4248 H 0 0 0 0 0 0 0 0 0 0 0 0 17.2102 4.5376 0.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8389 3.2882 3.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6504 6.0276 1.7530 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6520 5.7320 3.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8006 5.2751 4.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 18.9560 3.9706 2.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 17.7536 2.9798 -1.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4482 1.1018 -1.5353 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 27 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 1 0 35 36 2 0 35 37 1 0 32 38 1 0 31 39 1 0 30 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 45 47 1 0 44 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 54 55 1 0 53 56 1 0 52 57 1 0 51 58 1 0 50 59 1 0 43 60 1 0 42 61 1 0 29 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 67 69 1 0 66 70 1 0 65 71 1 0 64 72 1 0 9 73 1 0 5 74 1 1 74 75 1 0 2 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 82 85 1 0 81 86 1 0 80 87 1 0 79 88 1 0 73 5 1 0 85 78 1 0 25 8 1 0 38 28 1 0 47 41 1 0 56 49 1 0 69 63 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 89 1 0 1 90 1 0 1 91 1 0 2 92 1 6 3 93 1 0 3 94 1 0 4 95 1 0 4 96 1 0 6 97 1 6 7 98 1 0 7 99 1 0 7100 1 0 8101 1 6 9102 1 1 10103 1 0 10104 1 0 11105 1 1 12106 1 6 13107 1 0 13108 1 0 14109 1 0 16110 1 0 16111 1 0 17112 1 1 18113 1 0 18114 1 0 19115 1 0 19116 1 0 21117 1 0 21118 1 0 21119 1 0 22120 1 1 23121 1 0 23122 1 0 24123 1 0 24124 1 0 26125 1 0 26126 1 0 26127 1 0 28128 1 1 29129 1 1 30130 1 6 31131 1 1 32132 1 6 33133 1 0 33134 1 0 37135 1 0 37136 1 0 37137 1 0 39138 1 0 41139 1 6 42140 1 1 43141 1 1 44142 1 6 45143 1 1 46144 1 0 46145 1 0 46146 1 0 49147 1 6 50148 1 1 51149 1 6 52150 1 1 53151 1 6 54152 1 0 54153 1 0 55154 1 0 57155 1 0 58156 1 0 59157 1 0 60158 1 0 61159 1 0 63160 1 6 64161 1 6 65162 1 6 66163 1 1 67164 1 1 68165 1 0 68166 1 0 68167 1 0 70168 1 0 71169 1 0 72170 1 0 75171 1 0 75172 1 0 75173 1 0 76174 1 0 76175 1 0 78176 1 1 79177 1 6 80178 1 1 81179 1 6 82180 1 1 83181 1 0 83182 1 0 84183 1 0 86184 1 0 87185 1 0 88186 1 0 M END

Standard InCHIKey	BJVYIZFKHTVRIM-LAVATZBFSA-N
Standard InCHI	InChI=1S/C60H98O28/c1-23(21-78-53-46(72)43(69)39(65)34(19-61)82-53)11-16-60(76-8)24(2)37-33(88-60)18-32-30-10-9-28-17-29(12-14-58(28,6)31(30)13-15-59(32,37)7)81-57-52(87-54-47(73)42(68)38(64)25(3)79-54)51(41(67)36(84-57)22-77-27(5)63)86-55-49(75)45(71)50(26(4)80-55)85-56-48(74)44(70)40(66)35(20-62)83-56/h9,23-26,29-57,61-62,64-75H,10-22H2,1-8H3/t23-,24-,25-,26-,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46+,47+,48+,49+,50-,51-,52+,53+,54-,55-,56-,57+,58-,59-,60+/m0/s1
SMILES	C[C@@H](CC[C@@]1([C@@H](C)[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]23C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)C)O2)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O1)OC)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1266.62	Volume:	1201.604 ? Van der Waals volume.
Dense:	1.054	LogP:	0.781 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.597 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.047 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	55.0
TPSA:	420.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	28.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	28.0

MedChem Properties

QED Drug-Likeness Score:	0.045	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.411	Fsp³:	0.95
MCE-18:	201.128 ? 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:	0.653	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.371	Promiscuous compounds:	0.157

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.545	MDCK Permeability:	-5.112
Pgp-inhibitor:	0.0	Pgp-substrate:	0.934
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):	0.162
20% Bioavailability (F20%):	0.095	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	52.765%	Volume Distribution (VD):	-0.411
Fu:	32.358% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.001

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:	0.984	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.977
HLM stability:	0.036 ? 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):

-0.573

Half-life (T1/2):

3.85

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.007
Human Hepatotoxicity (H-HT):	0.285	Drug-induced Liver Injury (DILI):	0.949
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.009	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.528	Drug-induced Nephrotoxicity:	0.949
Genotoxicity:	0.017	RPMI-8226 Immunitoxicity:	0.34
A549 Cytotoxicity:	0.927	Hek293 Cytotoxicity:	0.807
BCF:	1.163 ? 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:	3.44 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.902 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.014 ? 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
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[10230514]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	rhizomes	SiMao City, Yunnan Province, China	1996-OCT	PMID[11908966]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[12350150]
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12956064]
NPO12186	Oplopanax chironium	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104479]
NPO11157	Corydalis saxicola	Species	Papaveraceae	Eukaryota	n.a.	root	n.a.	PMID[17611928]
NPO11157	Corydalis saxicola	Species	Papaveraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18649321]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20715765]
NPO7143	Acacia jacquemontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21894904]
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25608854]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33253561]
NPO1133	Zieria laevigata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12268	Aloe littoralis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11396	Metzgeria furcata	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6266	Anzia hypoleucoides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8399	Psiadia trinervia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14634	Artemisia balchanorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11157	Corydalis saxicola	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12093	Papaver orientale	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10695	Pelargonium zonale	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13831	Cephalotaxus oliveri	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13426	Lemmaphyllum microphyllum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12093	Papaver orientale	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13831	Cephalotaxus oliveri	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10695	Pelargonium zonale	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13426	Lemmaphyllum microphyllum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10695	Pelargonium zonale	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13527	Solanum ecuadorense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3227	Androsace umbellata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10094	Daphne gnidioides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13426	Lemmaphyllum microphyllum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6266	Anzia hypoleucoides	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13332	Tacca chantrieri	Species	Taccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12268	Aloe littoralis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14308	Coleonema pulchrum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14018	Pleurotus salmoneostramineus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13831	Cephalotaxus oliveri	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9487	Penicillium flexuosum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12093	Papaver orientale	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8399	Psiadia trinervia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1576	Anthriscus sylvestris	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7143	Acacia jacquemontii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14634	Artemisia balchanorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11753	Sideroxylon foetidissimum	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5551	Podocarpus sylvestris	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11396	Metzgeria furcata	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1133	Zieria laevigata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11157	Corydalis saxicola	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11909	Othonna arborescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9126	Stevia maimarensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11585	Geijera salicifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10695	Pelargonium zonale	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13723	Salvia eriophora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12186	Oplopanax chironium	Species	Araliaceae	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

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

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 NPC147545 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	22775
0.1-0.2	23241
0.2-0.3	2852
0.3-0.4	759
0.4-0.5	135
0.5-0.6	58
0.6-0.7	31
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8273	Intermediate Similarity	NPC309278
0.7414	Intermediate Similarity	NPC194207
0.7414	Intermediate Similarity	NPC22779
0.7345	Intermediate Similarity	NPC300557
0.7168	Intermediate Similarity	NPC602423
0.7107	Intermediate Similarity	NPC232054
0.6807	Remote Similarity	NPC269297
0.6807	Remote Similarity	NPC222202
0.6555	Remote Similarity	NPC480555
0.6555	Remote Similarity	NPC150372
0.6532	Remote Similarity	NPC477811
0.6471	Remote Similarity	NPC6806
0.6435	Remote Similarity	NPC470432
0.6435	Remote Similarity	NPC230507
0.6434	Remote Similarity	NPC477808
0.6364	Remote Similarity	NPC263359
0.6364	Remote Similarity	NPC102016
0.6364	Remote Similarity	NPC95051
0.6357	Remote Similarity	NPC224314
0.6325	Remote Similarity	NPC113044
0.6325	Remote Similarity	NPC283829
0.6325	Remote Similarity	NPC161676
0.6303	Remote Similarity	NPC470433
0.6303	Remote Similarity	NPC46190
0.6303	Remote Similarity	NPC171073
0.6216	Remote Similarity	NPC181845
0.621	Remote Similarity	NPC475333
0.621	Remote Similarity	NPC224098
0.621	Remote Similarity	NPC208383
0.619	Remote Similarity	NPC23808
0.619	Remote Similarity	NPC87998
0.6142	Remote Similarity	NPC480553
0.6111	Remote Similarity	NPC218571
0.6111	Remote Similarity	NPC487615
0.6094	Remote Similarity	NPC31896
0.608	Remote Similarity	NPC32361
0.605	Remote Similarity	NPC14704
0.5984	Remote Similarity	NPC480554
0.5984	Remote Similarity	NPC477809
0.5969	Remote Similarity	NPC308140
0.5952	Remote Similarity	NPC116756
0.5909	Remote Similarity	NPC480556
0.5859	Remote Similarity	NPC470864
0.5854	Remote Similarity	NPC248746
0.5806	Remote Similarity	NPC182900
0.5778	Remote Similarity	NPC210569
0.576	Remote Similarity	NPC475182
0.5748	Remote Similarity	NPC247037
0.5746	Remote Similarity	NPC477807
0.5714	Remote Similarity	NPC73243
0.5714	Remote Similarity	NPC244086
0.5714	Remote Similarity	NPC84956
0.568	Remote Similarity	NPC42171
0.5659	Remote Similarity	NPC232611
0.5645	Remote Similarity	NPC475643
0.5639	Remote Similarity	NPC470866
0.5573	Remote Similarity	NPC83137
0.5573	Remote Similarity	NPC470862
0.5565	Remote Similarity	NPC98696
0.5546	Remote Similarity	NPC206003
0.5546	Remote Similarity	NPC473610
0.554	Remote Similarity	NPC305771
0.554	Remote Similarity	NPC94072
0.554	Remote Similarity	NPC169816
0.5512	Remote Similarity	NPC150057
0.5512	Remote Similarity	NPC147753
0.5496	Remote Similarity	NPC249265
0.5484	Remote Similarity	NPC475351
0.5403	Remote Similarity	NPC305423
0.5385	Remote Similarity	NPC475550
0.5373	Remote Similarity	NPC287885
0.5349	Remote Similarity	NPC97700
0.5349	Remote Similarity	NPC30856
0.5324	Remote Similarity	NPC15918
0.5319	Remote Similarity	NPC244431
0.5312	Remote Similarity	NPC249553
0.5246	Remote Similarity	NPC107188
0.5227	Remote Similarity	NPC13193
0.52	Remote Similarity	NPC141433
0.5197	Remote Similarity	NPC161738
0.5122	Remote Similarity	NPC211354
0.512	Remote Similarity	NPC125324
0.512	Remote Similarity	NPC306991
0.512	Remote Similarity	NPC94272
0.512	Remote Similarity	NPC6295
0.5115	Remote Similarity	NPC184617
0.5078	Remote Similarity	NPC473601
0.5078	Remote Similarity	NPC486388
0.5077	Remote Similarity	NPC51172
0.5077	Remote Similarity	NPC49032
0.5076	Remote Similarity	NPC115165
0.5075	Remote Similarity	NPC254255
0.5074	Remote Similarity	NPC132080
0.5039	Remote Similarity	NPC160426
0.5038	Remote Similarity	NPC486386

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC147545 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7432
0.1-0.2	1652
0.2-0.3	55
0.3-0.4	7
0.4-0.5	3
0.5-0.6	1
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
0.5512	Remote Similarity	NPD8450	Suspended

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