NPASS Compound

Natural Product: NPC229620

Natural Product ID	NPC229620
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Alpha-chaconine
IUPAC Name	(2S,3R,4R,5R,6S)-2-[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]oxy-6-methyloxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	442971
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 133141 0 0 0 0 0 0 0 0999 V2000 -11.6567 2.2208 0.0720 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4228 3.0256 0.3453 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1177 3.1797 1.8253 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6340 1.8669 2.4446 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0855 1.0238 1.3389 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0789 -0.0094 1.7531 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3527 -0.2886 0.4561 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2922 1.1295 -0.1367 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2738 1.9178 0.5074 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.2252 2.5294 -0.4344 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8631 1.5464 0.2693 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1645 0.3097 -0.0974 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9589 -0.7747 0.6225 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6181 -2.0460 -0.1074 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1400 -2.2881 -0.1522 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3026 -1.0896 -0.5004 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7413 0.1289 0.3385 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8630 1.2724 -0.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4561 0.9090 0.3412 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0258 -0.2951 0.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8599 -1.3509 -0.5199 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2638 -1.4589 -1.9420 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1402 -0.5112 -2.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9416 -0.4319 -1.1594 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4201 -0.6453 0.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0407 -1.1527 -1.5030 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2043 -0.3866 -1.5145 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4505 -1.0716 -1.1755 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5433 -0.6783 -2.1428 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4885 0.8616 -2.2784 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1410 1.2633 -2.7808 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3144 0.1095 -2.8620 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2598 1.9905 -4.0746 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0703 3.1373 -3.9464 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7729 1.4454 -1.0673 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0413 2.1166 -1.1343 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8035 3.5504 -0.7198 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8920 3.9445 0.2790 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2378 3.4413 -0.2716 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1550 1.9281 -0.1599 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8867 1.4309 -0.3036 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1144 1.2237 -1.1031 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2716 3.9265 0.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9158 5.2681 0.5875 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9182 4.3784 -1.8165 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2418 -1.2607 -3.3709 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8448 -1.0725 0.1461 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0057 -2.3367 0.6819 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3385 -2.5197 1.3692 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1814 -3.2709 2.6726 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1670 -4.3601 2.5995 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8684 -3.8148 2.0676 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0356 -2.5231 1.6618 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3872 -4.6347 0.8717 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0333 -4.9355 3.8616 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4202 -3.8493 2.9812 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2079 -3.2152 0.5486 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4984 -2.7060 0.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5810 -0.9088 2.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8449 -1.2026 2.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5079 2.8690 -0.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0636 1.7234 0.9942 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4959 1.4747 -0.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6194 4.0705 -0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3033 3.9611 1.8610 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9919 3.6027 2.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7841 2.1436 3.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4554 1.4144 3.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8611 0.5165 0.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4255 0.4458 2.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9872 -0.9386 -0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3345 1.1200 -1.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7570 3.3233 -1.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5382 1.7319 -1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8715 1.8095 1.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5367 2.4337 -0.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2907 0.1146 -1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0883 -2.0100 -1.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0968 -2.8837 0.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9929 -3.0287 -0.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 -2.8078 0.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6121 -0.8131 -1.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6894 -0.0426 1.4096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9211 1.4644 -1.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1664 2.2277 0.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7941 1.6284 0.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0163 -2.4788 -2.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0955 -1.1339 -2.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3650 -0.8761 -3.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5030 0.5214 -2.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2891 0.6550 -1.1054 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8521 0.0493 0.9940 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6153 -1.6555 0.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9823 0.5984 -0.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2994 -2.1804 -1.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5606 -0.8891 -1.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2583 1.1052 -3.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6669 1.9091 -2.0282 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6258 1.3416 -4.9150 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2746 2.3997 -4.4377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4616 3.3401 -4.8322 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3317 2.0924 -2.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8332 3.6884 -0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7286 3.3539 1.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3657 3.7713 -1.3231 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5660 1.7021 0.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8115 0.1487 -1.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1569 1.2760 -0.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0363 1.5657 -2.1302 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8312 3.2642 0.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3824 5.8760 -0.0062 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3803 5.2045 -1.6533 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2573 -2.2572 -3.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8262 -3.1490 -0.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8387 -1.5477 1.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9450 -2.5883 3.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5276 -5.1026 1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1301 -3.8816 2.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2701 -5.0486 0.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8948 -3.9299 0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6759 -5.4379 1.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0796 -5.9296 3.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3934 -4.8149 3.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7320 -3.8790 -0.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5053 -3.0190 -0.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3986 -2.6524 1.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1996 -3.4894 -0.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7118 -1.5895 2.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4351 -1.4307 2.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3477 0.0459 2.5738 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9446 -1.0915 2.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6933 -1.2361 3.3801 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5696 -2.1573 1.7666 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 8 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 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 30 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 0 40 42 1 0 39 43 1 0 38 44 1 0 37 45 1 0 29 46 1 0 28 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 52 54 1 0 51 55 1 0 50 56 1 0 49 57 1 0 21 58 1 1 13 59 1 1 6 60 1 0 10 2 1 0 9 5 1 0 13 7 1 0 17 12 1 0 21 16 1 0 25 20 1 0 32 27 1 0 41 36 1 0 53 48 1 0 1 61 1 0 1 62 1 0 1 63 1 0 2 64 1 6 3 65 1 0 3 66 1 0 4 67 1 0 4 68 1 0 5 69 1 6 6 70 1 1 7 71 1 6 8 72 1 6 10 73 1 0 10 74 1 0 11 75 1 0 11 76 1 0 12 77 1 6 14 78 1 0 14 79 1 0 15 80 1 0 15 81 1 0 16 82 1 6 17 83 1 1 18 84 1 0 18 85 1 0 19 86 1 0 22 87 1 0 22 88 1 0 23 89 1 0 23 90 1 0 24 91 1 1 25 92 1 0 25 93 1 0 27 94 1 1 28 95 1 6 29 96 1 1 30 97 1 6 31 98 1 1 33 99 1 0 33100 1 0 34101 1 0 36102 1 6 37103 1 1 38104 1 1 39105 1 6 40106 1 1 42107 1 0 42108 1 0 42109 1 0 43110 1 0 44111 1 0 45112 1 0 46113 1 0 48114 1 6 49115 1 1 50116 1 1 51117 1 6 52118 1 1 54119 1 0 54120 1 0 54121 1 0 55122 1 0 56123 1 0 57124 1 0 58125 1 0 58126 1 0 58127 1 0 59128 1 0 59129 1 0 59130 1 0 60131 1 0 60132 1 0 60133 1 0 M END

Standard InCHIKey	TYNQWWGVEGFKRU-AJDPQWBVSA-N
Standard InCHI	InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33-,34+,35+,36+,37+,38-,39+,40+,41-,42-,43+,44-,45-/m0/s1
SMILES	C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O[C@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	851.5	Volume:	841.291 ? Van der Waals volume.
Dense:	1.012	LogP:	1.768 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.559 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.357 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	47.0
TPSA:	220.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.169	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.243	Fsp³:	0.956
MCE-18:	166.273 ? 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:	0.825	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:	0.016	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.13	MDCK Permeability:	-4.996
Pgp-inhibitor:	0.0	Pgp-substrate:	0.998
PAMPA:	0.996 ? 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):	0.0
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.778
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159	MRP1:	0.354
Plasma Protein Binding (PPB):	65.04%	Volume Distribution (VD):	-0.32
Fu:	26.641% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.87	BCRP inhibitor:	0.015
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.118	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.174
HLM stability:	0.389 ? 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):

0.324

Half-life (T1/2):

2.708

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.231
Human Hepatotoxicity (H-HT):	0.277	Drug-induced Liver Injury (DILI):	0.758
AMES Toxicity:	0.806	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	0.999
Carcinogencity:	0.04	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.996
Hematotoxicity:	0.265	Drug-induced Nephrotoxicity:	0.622
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.224
A549 Cytotoxicity:	0.806	Hek293 Cytotoxicity:	0.623
BCF:	2.099 ? 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:	3.601 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.676 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.2 ? 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
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1007/BF00232372]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	Granola: the 1999 growing season	DOI[10.1016/S0956-7135(03)00077-X]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	seeds	n.a.	n.a.	PMID[12105963]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[2831703]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]

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
NPO16501.2	Capsicum annuum	n.a.	n.a.	0.7 to 1.93	n.a.	n.a.	mg/kg of FW	DOI[10.1016/S0956-7135(03)00077-X]

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 NPC229620 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	22355
0.1-0.2	24474
0.2-0.3	2558
0.3-0.4	377
0.4-0.5	45
0.5-0.6	33
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC265275
0.8387	Intermediate Similarity	NPC600116
0.7959	Intermediate Similarity	NPC48886
0.7959	Intermediate Similarity	NPC94881
0.6562	Remote Similarity	NPC165439
0.6408	Remote Similarity	NPC94272
0.6111	Remote Similarity	NPC470433
0.6111	Remote Similarity	NPC46190
0.6111	Remote Similarity	NPC171073
0.6091	Remote Similarity	NPC475182
0.6055	Remote Similarity	NPC248746
0.6055	Remote Similarity	NPC122819
0.6	Remote Similarity	NPC42171
0.5946	Remote Similarity	NPC480555
0.5946	Remote Similarity	NPC150372
0.5893	Remote Similarity	NPC73243
0.5893	Remote Similarity	NPC244086
0.5893	Remote Similarity	NPC84956
0.5789	Remote Similarity	NPC247037
0.5789	Remote Similarity	NPC269297
0.5789	Remote Similarity	NPC222202
0.5739	Remote Similarity	NPC475333
0.5739	Remote Similarity	NPC224098
0.5739	Remote Similarity	NPC208383
0.569	Remote Similarity	NPC194207
0.569	Remote Similarity	NPC22779
0.5641	Remote Similarity	NPC249265
0.5641	Remote Similarity	NPC480554
0.5593	Remote Similarity	NPC23808
0.5593	Remote Similarity	NPC87998
0.5575	Remote Similarity	NPC124677
0.5546	Remote Similarity	NPC480553
0.55	Remote Similarity	NPC308140
0.55	Remote Similarity	NPC287885
0.549	Remote Similarity	NPC486114
0.5484	Remote Similarity	NPC91604
0.5455	Remote Similarity	NPC232054
0.5403	Remote Similarity	NPC224314
0.5385	Remote Similarity	NPC486386
0.5339	Remote Similarity	NPC13193
0.5323	Remote Similarity	NPC480556
0.5294	Remote Similarity	NPC254255
0.5089	Remote Similarity	NPC470432
0.5089	Remote Similarity	NPC230507
0.5089	Remote Similarity	NPC15249
0.5089	Remote Similarity	NPC25455

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6956
0.1-0.2	2127
0.2-0.3	61
0.3-0.4	4
0.4-0.5	1
0.5-0.6	0
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
0.6055	Remote Similarity	NPD8449	Approved

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