NPASS Compound

Natural Product: NPC565798

Natural Product ID	NPC565798
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},4~{R})-2-[(2~{S},4~{S},5~{R})-2-[(3~{R},4~{R},6~{R})-4,5-dihydroxy-2-(hydroxymethyl)-6-[(5'~{S},7~{S},9~{S},13~{S},15~{R},18~{S})-15-hydroxy-5',7,9,13-tetramethyl-spiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2~{S},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
IUPAC Name	(3~{S},4~{R})-2-[(2~{S},4~{S},5~{R})-2-[(3~{R},4~{R},6~{R})-4,5-dihydroxy-2-(hydroxymethyl)-6-[(5'~{S},7~{S},9~{S},13~{S},15~{R},18~{S})-15-hydroxy-5',7,9,13-tetramethyl-spiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2~{S},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 155164 0 0 0 0 0 0 0 0999 V2000 12.9979 0.5254 3.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6389 0.2235 2.8984 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0030 1.5181 2.4231 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1836 1.5989 0.9150 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3498 0.4968 0.3088 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7382 -0.6894 0.8764 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8547 -0.6428 1.6717 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 0.8004 0.6002 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6385 1.7091 -0.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1517 1.7410 -0.6175 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0196 1.4705 -2.0939 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6392 1.0694 -2.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2126 1.3785 -3.8301 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6774 1.2841 -3.8993 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1370 0.5026 -2.7514 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6801 0.1513 -3.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9872 -0.3130 -1.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0492 -1.2861 -2.0719 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1729 -1.0361 -1.5133 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3333 -2.0589 -0.5325 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1967 -1.6114 0.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4127 -1.0946 1.6183 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5853 -0.0164 1.2757 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2596 -0.7100 -0.0749 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3868 -0.8496 0.7181 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8589 0.3774 1.1679 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5393 0.4172 2.5495 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8874 1.6528 3.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6488 2.5372 3.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7742 1.9298 4.1646 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8511 2.4436 2.2861 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3410 3.1153 1.1992 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9737 1.5086 1.8035 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6552 0.9975 2.8787 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9107 1.5779 3.0533 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7320 2.3846 4.2208 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7305 3.3311 4.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0627 2.6700 4.4570 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0596 3.5994 4.1812 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2777 1.4241 3.6739 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.1847 0.6237 4.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0255 0.6509 3.3347 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7288 -0.1211 4.4696 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3523 0.4269 0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8019 -0.8533 1.3057 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4569 -1.4996 0.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6787 -2.5270 -0.2602 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3393 -3.2296 -1.2398 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5983 -2.3742 -2.4462 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2509 -3.1469 -3.4324 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6474 -3.8469 -0.7840 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7325 -3.3739 -1.5144 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9001 -3.5166 0.6775 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9931 -4.1138 1.5200 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7633 -1.9834 0.7566 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8096 -1.3622 0.0888 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5910 -1.2825 -1.4634 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7823 -2.6448 -1.2683 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3686 -1.0458 -2.3776 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3757 -2.0419 -3.3221 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0138 -0.8463 -0.8159 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4032 0.1489 0.0983 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 -1.5456 -1.4323 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9315 -0.7551 -2.4707 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9813 -1.5832 -3.7146 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2869 -0.3123 -1.9588 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3292 -1.2508 -2.4249 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7226 -0.8866 -1.9396 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1262 0.4875 -2.3658 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4997 0.5108 -3.8622 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2414 1.1174 -1.6630 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4281 0.4716 -1.2151 C 0 0 2 0 0 0 0 0 0 0 0 0 10.7576 -0.9279 -1.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3009 -0.2959 4.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9556 1.4725 4.1182 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7620 0.6556 2.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9882 -0.3385 3.5995 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9136 1.4224 2.5920 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4820 2.3614 2.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2474 1.5858 0.6079 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8262 2.6269 0.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0735 -1.6842 2.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7733 -0.2876 1.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9756 2.7383 -0.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7010 0.9782 0.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7282 2.7408 -0.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2591 2.4434 -2.5975 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9924 1.7537 -1.7828 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4502 2.4538 -4.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5992 0.7184 -4.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3287 0.8905 -4.8595 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2201 2.3132 -3.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0802 1.1840 -1.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7018 -0.5764 -3.8752 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2216 1.0889 -3.4525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5177 0.5433 -1.2674 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1027 -0.0533 -0.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7302 -2.5414 0.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 -1.9109 2.0963 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0762 -0.7109 2.4166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3892 0.4917 2.0772 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9324 0.3428 -0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2706 1.1605 0.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3037 1.4683 4.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0607 3.4760 3.7700 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2078 2.8640 2.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8464 2.0398 3.8320 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2784 3.2281 2.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9975 3.7315 0.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6644 2.1905 1.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1293 2.3324 2.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5394 4.0963 4.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7528 3.8037 3.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0790 2.4942 5.5620 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6756 4.4930 4.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7211 1.7231 2.6873 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9622 0.4566 3.7955 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2859 -0.0188 2.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4966 -0.7439 4.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5624 0.6588 -0.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5396 -0.7524 -0.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6855 -4.0867 -1.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2745 -1.5152 -2.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6767 -1.9657 -2.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6489 -3.8503 -3.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6043 -4.9394 -0.8625 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5573 -3.6811 -1.0310 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9326 -3.7537 0.9241 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3512 -3.4089 1.8350 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9047 -1.7760 1.8457 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6476 -1.5109 0.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5133 -0.8576 -1.8788 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2236 -3.1945 -1.8915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 -0.0355 -2.8023 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9296 -1.7498 -4.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4583 -1.5947 -0.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7611 0.8731 0.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7995 -2.5258 -1.8209 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8793 -1.7953 -0.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7603 -2.4005 -3.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9875 -1.0331 -4.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0222 -2.1854 -3.7487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1886 -0.2868 -0.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1177 -2.2679 -2.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3801 -1.1878 -3.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7412 -0.9708 -0.8513 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3740 -1.6126 -2.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6065 0.4936 -3.9870 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1554 1.4502 -4.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1369 -0.4044 -4.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5097 2.0352 -2.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3532 1.0836 -1.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2180 -1.6805 -0.9512 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7211 -1.1664 -2.6660 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8389 -1.1008 -1.3043 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 5 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 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 33 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 24 57 1 0 57 58 1 0 57 59 1 0 59 60 1 0 17 61 1 0 61 62 1 0 61 63 1 0 63 64 1 0 64 65 1 6 64 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 6 69 71 1 0 71 72 1 0 72 73 1 0 7 2 1 0 71 9 1 0 72 5 1 0 69 11 1 0 66 12 1 0 64 15 1 0 59 19 1 0 44 26 1 0 55 46 1 0 42 35 1 0 1 74 1 0 1 75 1 0 1 76 1 0 2 77 1 1 3 78 1 0 3 79 1 0 4 80 1 0 4 81 1 0 7 82 1 0 7 83 1 0 9 84 1 0 10 85 1 0 10 86 1 0 11 87 1 0 12 88 1 0 13 89 1 0 13 90 1 0 14 91 1 0 14 92 1 0 15 93 1 1 16 94 1 0 16 95 1 0 17 96 1 0 19 97 1 1 21 98 1 0 22 99 1 0 22100 1 0 23101 1 0 24102 1 6 26103 1 6 28104 1 0 29105 1 0 29106 1 0 30107 1 0 31108 1 1 32109 1 0 33110 1 6 35111 1 6 37112 1 0 37113 1 0 38114 1 1 39115 1 0 40116 1 6 41117 1 0 42118 1 0 43119 1 0 44120 1 0 46121 1 0 48122 1 0 49123 1 0 49124 1 0 50125 1 0 51126 1 0 52127 1 0 53128 1 1 54129 1 0 55130 1 1 56131 1 0 57132 1 6 58133 1 0 59134 1 0 60135 1 0 61136 1 1 62137 1 0 63138 1 0 63139 1 0 65140 1 0 65141 1 0 65142 1 0 66143 1 0 67144 1 0 67145 1 0 68146 1 0 68147 1 0 70148 1 0 70149 1 0 70150 1 0 71151 1 0 72152 1 1 73153 1 0 73154 1 0 73155 1 0 M END

Standard InCHIKey	AULWDENWMBJIIQ-NGTUJAPCSA-N
Standard InCHI	InChI=1S/C50H82O23/c1-19-7-10-50(65-17-19)20(2)32-28(73-50)12-24-22-6-5-21-11-27(25(54)13-49(21,4)23(22)8-9-48(24,32)3)66-45-40(63)37(60)41(31(16-53)69-45)70-47-43(72-46-39(62)36(59)34(57)29(14-51)67-46)42(35(58)30(15-52)68-47)71-44-38(61)33(56)26(55)18-64-44/h19-47,51-63H,5-18H2,1-4H3/t19-,20-,21-,22?,23?,24?,25+,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?/m0/s1
SMILES	C[C@H]1CCC2(OC1)OC1CC3C4CC[C@H]5CC(O[C@@H]6OC(CO)[C@H](O[C@@H]7OC(CO)[C@@H](O)[C@H](O[C@@H]8OC[C@@H](O)[C@H](O)C8O)C7OC7OC(CO)C(O)[C@@H](O)[C@@H]7O)[C@H](O)C6O)[C@H](O)C[C@]5(C)C4CC[C@]3(C)C1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1050.52	Volume:	989.966 ? Van der Waals volume.
Dense:	1.061	LogP:	-0.293 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.621 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.341 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	54.0
TPSA:	355.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	10.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.09	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.24	Fsp³:	1.0
MCE-18:	262.48 ? 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:	0.341	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.388	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.838	MDCK Permeability:	-5.08
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.008
20% Bioavailability (F20%):	0.945	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.986
Plasma Protein Binding (PPB):	45.666%	Volume Distribution (VD):	-0.382
Fu:	37.579% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.047	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.009
HLM stability:	0.007 ? 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):

-0.086

Half-life (T1/2):

2.814

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.037
Human Hepatotoxicity (H-HT):	0.778	Drug-induced Liver Injury (DILI):	0.648
AMES Toxicity:	0.814	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.066	Skin Sensitization:	0.999
Carcinogencity:	0.092	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	1.0
Hematotoxicity:	0.032	Drug-induced Nephrotoxicity:	0.505
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.306
A549 Cytotoxicity:	0.621	Hek293 Cytotoxicity:	0.825
BCF:	1.024 ? 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:	3.582 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.323 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.002 ? 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
NPO16985	Tribulus alatus	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16985	Tribulus alatus	Species	Muricidae	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 NPC565798 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	28499
0.1-0.2	18383
0.2-0.3	2471
0.3-0.4	318
0.4-0.5	66
0.5-0.6	60
0.6-0.7	33
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC115165
0.914	High Similarity	NPC473601
0.9082	High Similarity	NPC232611
0.8788	High Similarity	NPC473518
0.8529	High Similarity	NPC83137
0.8485	Intermediate Similarity	NPC97700
0.8485	Intermediate Similarity	NPC30856
0.802	Intermediate Similarity	NPC151134
0.8	Intermediate Similarity	NPC470862
0.7925	Intermediate Similarity	NPC132080
0.7879	Intermediate Similarity	NPC475351
0.785	Intermediate Similarity	NPC31896
0.7714	Intermediate Similarity	NPC116756
0.7642	Intermediate Similarity	NPC232037
0.7524	Intermediate Similarity	NPC51520
0.7524	Intermediate Similarity	NPC303069
0.7458	Intermediate Similarity	NPC330026
0.7368	Intermediate Similarity	NPC210569
0.7273	Intermediate Similarity	NPC233433
0.7264	Intermediate Similarity	NPC184617
0.7232	Intermediate Similarity	NPC470866
0.7232	Intermediate Similarity	NPC470867
0.7172	Intermediate Similarity	NPC206003
0.7172	Intermediate Similarity	NPC473610
0.7071	Intermediate Similarity	NPC250393
0.7027	Intermediate Similarity	NPC476112
0.7027	Intermediate Similarity	NPC307534
0.699	Remote Similarity	NPC195297
0.6942	Remote Similarity	NPC481190
0.6916	Remote Similarity	NPC51172
0.6916	Remote Similarity	NPC49032
0.6869	Remote Similarity	NPC294686
0.6838	Remote Similarity	NPC220836
0.6786	Remote Similarity	NPC470864
0.6768	Remote Similarity	NPC325828
0.6757	Remote Similarity	NPC475625
0.675	Remote Similarity	NPC263359
0.6746	Remote Similarity	NPC329820
0.6727	Remote Similarity	NPC475319
0.6607	Remote Similarity	NPC470861
0.6581	Remote Similarity	NPC94086
0.6581	Remote Similarity	NPC473817
0.6569	Remote Similarity	NPC222731
0.6505	Remote Similarity	NPC121453
0.6476	Remote Similarity	NPC107962
0.6475	Remote Similarity	NPC244431
0.6364	Remote Similarity	NPC79900
0.6348	Remote Similarity	NPC92710
0.6339	Remote Similarity	NPC98018
0.6339	Remote Similarity	NPC284104
0.6339	Remote Similarity	NPC103616
0.6262	Remote Similarity	NPC125324
0.625	Remote Similarity	NPC128572
0.6239	Remote Similarity	NPC477811
0.6183	Remote Similarity	NPC481189
0.6132	Remote Similarity	NPC107188
0.6077	Remote Similarity	NPC329807
0.6018	Remote Similarity	NPC300557
0.6015	Remote Similarity	NPC329727
0.6	Remote Similarity	NPC167183
0.5981	Remote Similarity	NPC54619
0.5966	Remote Similarity	NPC84111
0.5966	Remote Similarity	NPC287483
0.5966	Remote Similarity	NPC470865
0.5963	Remote Similarity	NPC6295
0.5952	Remote Similarity	NPC305771
0.5952	Remote Similarity	NPC94072
0.5952	Remote Similarity	NPC169816
0.595	Remote Similarity	NPC262050
0.5935	Remote Similarity	NPC473505
0.5935	Remote Similarity	NPC477807
0.5932	Remote Similarity	NPC108072
0.5877	Remote Similarity	NPC471464
0.5856	Remote Similarity	NPC160426
0.5841	Remote Similarity	NPC602423
0.581	Remote Similarity	NPC297348
0.581	Remote Similarity	NPC249204
0.581	Remote Similarity	NPC48339
0.581	Remote Similarity	NPC141769
0.581	Remote Similarity	NPC477547
0.5755	Remote Similarity	NPC234352
0.5714	Remote Similarity	NPC15918
0.5688	Remote Similarity	NPC211354
0.5688	Remote Similarity	NPC19400
0.5669	Remote Similarity	NPC32707
0.566	Remote Similarity	NPC177834
0.563	Remote Similarity	NPC309278
0.56	Remote Similarity	NPC248202
0.5574	Remote Similarity	NPC92297
0.5574	Remote Similarity	NPC256983
0.5556	Remote Similarity	NPC477451
0.5546	Remote Similarity	NPC470863
0.5517	Remote Similarity	NPC92890
0.5517	Remote Similarity	NPC477809
0.5512	Remote Similarity	NPC477808
0.55	Remote Similarity	NPC475333
0.55	Remote Similarity	NPC224098
0.55	Remote Similarity	NPC208383
0.5495	Remote Similarity	NPC264101
0.5429	Remote Similarity	NPC24960
0.5426	Remote Similarity	NPC208832
0.5398	Remote Similarity	NPC470432
0.5398	Remote Similarity	NPC230507
0.5378	Remote Similarity	NPC294129
0.5354	Remote Similarity	NPC480556
0.5339	Remote Similarity	NPC6806
0.5333	Remote Similarity	NPC481418
0.5328	Remote Similarity	NPC197003
0.5299	Remote Similarity	NPC475643
0.5271	Remote Similarity	NPC273002
0.5263	Remote Similarity	NPC485595
0.5246	Remote Similarity	NPC32361
0.5238	Remote Similarity	NPC232054
0.5185	Remote Similarity	NPC485594
0.5167	Remote Similarity	NPC480555
0.5167	Remote Similarity	NPC150372
0.5143	Remote Similarity	NPC277715
0.5085	Remote Similarity	NPC202898
0.5048	Remote Similarity	NPC88962
0.5039	Remote Similarity	NPC190939

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC565798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7856
0.1-0.2	1221
0.2-0.3	66
0.3-0.4	2
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.6768	Remote Similarity	NPD8171	Phase 2
0.5963	Remote Similarity	NPD8170	Phase 2

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