NPASS Compound

Natural Product: NPC111466

Natural Product ID	NPC111466
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pachyelaside-A
IUPAC Name	(3S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-3-[(E)-3-phenylprop-2-enoyl]oxy-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	CHEMBL2252212
PubChem CID	76326371
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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

Chemical Representations

RDKit 3D 182191 0 0 0 0 0 0 0 0999 V2000 -3.6136 -5.7942 1.5826 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1441 -5.4926 0.3080 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0583 -3.9845 0.0743 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7045 -3.6693 0.1515 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5109 -2.2695 0.2601 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2229 -2.0320 -0.1444 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3519 -1.6254 0.8669 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5451 -2.7899 1.1386 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9939 -2.6027 0.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3188 -1.6457 -0.2023 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7229 -0.3371 0.2047 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2762 -0.3465 0.5412 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1271 0.5493 1.8005 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4953 0.4541 -0.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1053 0.7102 -0.7990 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5404 0.8124 -1.1356 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3701 -0.4164 -1.0329 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8259 -1.4626 -0.1092 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6115 -2.7188 -0.1646 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0458 -2.3982 -0.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5797 -1.1956 -0.3305 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7245 -0.0037 -0.4688 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5526 0.5522 0.9484 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3216 1.0839 -1.2955 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8063 1.1152 -1.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4972 -0.2039 -1.4181 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0671 -1.1050 -0.3156 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5795 -0.6036 0.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0787 -0.4608 0.9727 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4754 0.2138 2.2703 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7319 -1.8324 0.9677 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5685 0.4014 -0.1525 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9936 0.0179 -1.4845 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9570 0.4331 -0.1107 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7176 1.5546 0.1090 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1426 2.6404 0.2837 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1975 1.4957 0.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9058 2.5855 0.3505 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3465 2.6283 0.4010 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1268 1.5359 0.2497 C 0 0 0 0 0 0 0 0 0 0 0 0 18.5181 1.6900 0.3182 C 0 0 0 0 0 0 0 0 0 0 0 0 19.1233 2.9081 0.5334 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3107 4.0213 0.6870 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9482 3.8661 0.6193 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1644 -0.8471 -2.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6260 -1.9537 -2.8611 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4941 -0.1313 -3.8826 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5618 -1.0410 -2.3776 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8548 -2.2219 -1.4806 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4837 -1.6536 -0.6863 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6998 -2.5669 -1.8681 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5465 -3.7340 -1.3408 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8924 -3.3684 -1.3500 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4847 -3.0472 -2.3135 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6835 -1.2926 -0.0799 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8917 0.0826 -0.0905 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1577 0.5920 1.1575 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0636 1.9600 1.1440 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7567 2.5693 2.3698 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1559 2.0953 3.5493 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6906 2.5791 -0.0791 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7387 1.6363 -0.6122 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0472 0.3610 -1.0364 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5751 0.4673 -2.3536 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5764 1.2800 0.4523 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9005 1.6546 0.2013 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3164 2.5186 1.1695 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0372 1.9966 2.2046 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8489 2.8662 3.4260 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2815 4.1724 3.2007 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6374 0.5895 2.5784 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6624 -0.3406 1.3950 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7110 0.3881 0.0823 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0247 0.6118 -0.2604 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3981 0.0442 -1.4639 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.8327 0.9779 -2.3769 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8358 1.8072 -1.9699 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.2678 3.1602 -1.6035 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6345 3.7127 -2.7113 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6040 1.2931 -0.7762 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.7305 -0.2007 -0.7746 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.5117 -0.9381 -1.2085 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.8031 -1.5558 -2.4473 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.0272 -0.5849 0.5456 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.8918 1.8277 -0.8555 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5046 -1.1531 1.4310 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5696 0.1238 3.5034 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7172 2.7611 -1.0853 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6830 -6.0938 1.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4703 -6.0161 -0.4204 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1757 -5.8712 0.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6351 -3.4562 0.8334 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7068 -2.0638 1.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0297 -1.5667 1.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4386 -3.1559 2.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2289 -3.7060 0.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4604 -3.5774 0.6832 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4926 -2.2541 1.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 -0.0518 1.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4344 1.5561 1.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8735 0.2158 2.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9044 0.4934 2.1725 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4862 0.6667 0.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7448 -0.1333 -1.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0908 1.4446 -0.6975 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8241 1.6961 -0.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4851 0.6760 -1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0147 1.6929 -0.6005 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6086 1.1557 -2.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9807 -1.0685 0.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3467 -3.4420 -0.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4582 -3.2942 0.8048 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7235 -3.2702 -0.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1385 1.5137 1.0574 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5192 0.8518 1.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8563 -0.1803 1.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0221 2.0714 -0.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8985 1.1891 -2.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0861 1.6546 -2.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2477 1.7970 -0.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5269 -2.0995 -0.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1764 0.3382 1.3484 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3483 -1.3755 1.7575 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5321 0.0527 2.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7903 -0.1115 3.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3114 1.3092 2.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3741 -2.3502 1.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4687 -2.4058 0.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8158 -1.6858 1.0910 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2153 1.4488 0.0418 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1543 0.8528 -2.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4345 -0.9425 -1.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6999 0.5635 -0.0029 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3042 3.4992 0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6911 0.5644 0.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 19.1071 0.7996 0.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 20.1862 3.0386 0.5885 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7890 4.9962 0.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 16.3264 4.7506 0.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0526 -0.2831 -4.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5952 -0.9419 -2.9637 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8866 -2.1029 -2.3557 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3030 -0.5380 -3.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0541 -2.9866 -1.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4050 -1.5180 -2.1870 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6659 -2.8491 -1.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0419 -0.7147 -1.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3119 -2.0951 -2.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3303 -4.6178 -1.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3953 -4.0267 -0.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6924 -3.7445 -3.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0019 0.5760 -0.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9963 2.3116 1.1443 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7209 3.6737 2.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8130 2.2722 2.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1177 1.1114 3.4552 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1479 3.5636 0.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3253 2.1088 -1.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7973 -0.4779 -0.9835 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3190 0.3052 -2.9832 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8715 2.1970 -0.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1407 2.0156 1.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7619 2.9197 3.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3131 2.4212 4.3302 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8901 4.4731 2.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6509 0.5770 3.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5066 -1.0710 1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2198 -0.2239 -0.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5711 -0.5201 -1.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5614 1.9763 -2.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5206 3.0402 -0.7969 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0580 3.8337 -1.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6139 4.7033 -2.6260 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1748 1.6714 0.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6347 -0.5309 -1.3654 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2081 -1.7441 -0.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7115 -0.8455 -3.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7285 -1.5133 0.7137 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.5918 1.1810 -0.5749 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6396 -1.7923 0.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4823 0.3258 3.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0384 3.3865 -0.6846 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 12 14 1 0 11 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 2 0 21 22 1 0 22 23 1 1 22 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 29 31 1 0 29 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 26 45 1 6 45 46 2 0 45 47 1 0 17 48 1 6 10 49 1 6 5 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 50 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 68 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 81 84 1 0 80 85 1 0 72 86 1 0 71 87 1 0 61 88 1 0 52 3 1 0 63 56 1 0 73 66 1 0 82 75 1 0 12 7 1 0 22 17 1 0 33 26 1 0 44 39 1 0 18 10 1 0 27 21 1 0 1 89 1 0 2 90 1 0 2 91 1 0 3 92 1 1 5 93 1 1 7 94 1 1 8 95 1 0 8 96 1 0 9 97 1 0 9 98 1 0 11 99 1 1 13100 1 0 13101 1 0 13102 1 0 14103 1 0 14104 1 0 14105 1 0 15106 1 0 15107 1 0 16108 1 0 16109 1 0 18110 1 1 19111 1 0 19112 1 0 20113 1 0 23114 1 0 23115 1 0 23116 1 0 24117 1 0 24118 1 0 25119 1 0 25120 1 0 27121 1 6 28122 1 0 28123 1 0 30124 1 0 30125 1 0 30126 1 0 31127 1 0 31128 1 0 31129 1 0 32130 1 1 33131 1 0 33132 1 0 37133 1 0 38134 1 0 40135 1 0 41136 1 0 42137 1 0 43138 1 0 44139 1 0 47140 1 0 48141 1 0 48142 1 0 48143 1 0 49144 1 0 49145 1 0 49146 1 0 50147 1 6 51148 1 6 52149 1 6 53150 1 0 54151 1 0 56152 1 6 58153 1 1 59154 1 0 59155 1 0 60156 1 0 61157 1 1 62158 1 6 63159 1 6 64160 1 0 66161 1 6 68162 1 6 69163 1 0 69164 1 0 70165 1 0 71166 1 1 72167 1 1 73168 1 6 75169 1 6 77170 1 6 78171 1 0 78172 1 0 79173 1 0 80174 1 1 81175 1 6 82176 1 1 83177 1 0 84178 1 0 85179 1 0 86180 1 0 87181 1 0 88182 1 0 M END

Standard InCHIKey	IYKPELJBFODWHJ-FWMZTCOGSA-N
Standard InCHI	InChI=1S/C63H94O25/c1-58(2)23-31-30-14-15-37-60(5)19-18-38(59(3,4)36(60)17-20-62(37,7)61(30,6)21-22-63(31,57(78)79)24-39(58)84-40(68)16-13-29-11-9-8-10-12-29)85-55-51(46(74)42(70)33(26-65)82-55)88-54-49(77)50(44(72)35(28-67)81-54)86-56-52(47(75)43(71)34(27-66)83-56)87-53-48(76)45(73)41(69)32(25-64)80-53/h8-14,16,31-39,41-56,64-67,69-77H,15,17-28H2,1-7H3,(H,78,79)/b16-13+/t31-,32+,33+,34+,35+,36-,37+,38-,39-,41+,42+,43+,44+,45-,46-,47-,48+,49+,50-,51+,52+,53-,54-,55-,56-,60-,61+,62+,63+/m0/s1
SMILES	OC[C@H]1O[C@@H](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)[C@H](C2)OC(=O)/C=C/c2ccccc2)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1250.61	Volume:	1213.939 ? Van der Waals volume.
Dense:	1.03	LogP:	1.198 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.3 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.745 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	59.0
TPSA:	400.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.044	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.137	Fsp³:	0.81
MCE-18:	285.035 ? 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:	0.955	Fluc inhibitor:	0.316 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.066 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.089 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.256	Promiscuous compounds:	0.02

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.981	MDCK Permeability:	-5.15
Pgp-inhibitor:	0.0	Pgp-substrate:	0.061
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):	0.803
20% Bioavailability (F20%):	0.075	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.034
Plasma Protein Binding (PPB):	74.776%	Volume Distribution (VD):	-0.539
Fu:	18.126% ? 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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

-0.625

Half-life (T1/2):

3.95

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.896	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.983	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.055	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.761	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.682	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.832	Hek293 Cytotoxicity:	0.299
BCF:	0.513 ? 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:	3.473 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.177 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.156 ? 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
NPO5418	Pachyelasma tessmannii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15686409]
NPO5418	Pachyelasma tessmannii	Species	Fabaceae	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
-	Biomphalaria glabrata	LD50	=	2.0	ug ml-1	PMID[19928832]

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 NPC111466 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	15290
0.1-0.2	29408
0.2-0.3	3821
0.3-0.4	893
0.4-0.5	377
0.5-0.6	56
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.879	High Similarity	NPC40085
0.8217	Intermediate Similarity	NPC264270
0.775	Intermediate Similarity	NPC488211
0.7402	Intermediate Similarity	NPC488212
0.7193	Intermediate Similarity	NPC114304
0.6791	Remote Similarity	NPC488210
0.6491	Remote Similarity	NPC164194
0.6348	Remote Similarity	NPC488215
0.6325	Remote Similarity	NPC25605
0.616	Remote Similarity	NPC324875
0.616	Remote Similarity	NPC292677
0.6016	Remote Similarity	NPC180550
0.6016	Remote Similarity	NPC35405
0.5966	Remote Similarity	NPC488214
0.595	Remote Similarity	NPC488561
0.5868	Remote Similarity	NPC127056
0.5833	Remote Similarity	NPC12288
0.5798	Remote Similarity	NPC270667
0.5797	Remote Similarity	NPC329657
0.5794	Remote Similarity	NPC257468
0.5789	Remote Similarity	NPC166422
0.5789	Remote Similarity	NPC219180
0.5789	Remote Similarity	NPC251263
0.5738	Remote Similarity	NPC109079
0.5734	Remote Similarity	NPC120667
0.5734	Remote Similarity	NPC278272
0.5704	Remote Similarity	NPC54636
0.5703	Remote Similarity	NPC276093
0.5691	Remote Similarity	NPC472949
0.5652	Remote Similarity	NPC606107
0.554	Remote Similarity	NPC475513
0.5504	Remote Similarity	NPC79718
0.5496	Remote Similarity	NPC488564
0.5481	Remote Similarity	NPC471384
0.5455	Remote Similarity	NPC171007
0.5455	Remote Similarity	NPC475486
0.5455	Remote Similarity	NPC190849
0.5448	Remote Similarity	NPC69425
0.5426	Remote Similarity	NPC481082
0.5426	Remote Similarity	NPC164419
0.5403	Remote Similarity	NPC56713
0.5403	Remote Similarity	NPC59804
0.5378	Remote Similarity	NPC485587
0.5373	Remote Similarity	NPC476992
0.5368	Remote Similarity	NPC323341
0.5368	Remote Similarity	NPC133818
0.5354	Remote Similarity	NPC469945
0.5349	Remote Similarity	NPC139044
0.5303	Remote Similarity	NPC323359
0.5299	Remote Similarity	NPC62725
0.5276	Remote Similarity	NPC22956
0.5267	Remote Similarity	NPC119794
0.525	Remote Similarity	NPC482013
0.5185	Remote Similarity	NPC480939
0.5185	Remote Similarity	NPC480936
0.5182	Remote Similarity	NPC151543
0.5177	Remote Similarity	NPC473755
0.5175	Remote Similarity	NPC161717
0.5169	Remote Similarity	NPC204407
0.5161	Remote Similarity	NPC22676
0.5156	Remote Similarity	NPC80843
0.5122	Remote Similarity	NPC191410
0.5118	Remote Similarity	NPC114441
0.5115	Remote Similarity	NPC258885
0.5079	Remote Similarity	NPC172311
0.5078	Remote Similarity	NPC610795
0.5069	Remote Similarity	NPC471385
0.5039	Remote Similarity	NPC174679
0.5039	Remote Similarity	NPC279554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC111466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4382
0.1-0.2	4704
0.2-0.3	60
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data