NPASS Compound

Natural Product: NPC476087

Natural Product ID	NPC476087
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Orizabin Xxi
IUPAC Name	n.a.
Synonyms	Orizabin XXI
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL525270
PubChem CID	11007682
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

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 172176 0 0 0 0 0 0 0 0999 V2000 -10.6590 -4.9474 0.3257 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6477 -3.8284 0.4651 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2873 -4.3597 0.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3024 -3.2441 0.1787 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9052 -3.7092 -0.2353 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9248 -2.5946 -0.0939 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.9979 -0.4707 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7377 -3.7793 0.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2067 -5.1038 0.9484 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1652 -5.6800 1.9165 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8044 -5.6037 1.2767 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7541 -6.3412 0.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4423 -6.0935 -0.8551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7734 -6.2491 -0.2645 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2466 -5.2813 0.7471 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3250 -3.8622 0.2487 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1410 -3.6488 -0.9600 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5892 -2.8096 1.0715 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6927 -1.4500 0.7099 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2746 -0.6146 1.8128 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3885 0.3154 2.5331 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0677 0.0289 2.2716 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7704 0.1436 0.9315 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4123 -0.9616 0.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5819 -0.4242 -1.1811 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9252 -0.8149 -2.3108 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0801 -1.7340 -2.2241 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2511 -0.1259 -3.5842 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4567 -0.6342 -4.7403 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1980 1.3727 -3.4917 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1586 1.9288 -2.4796 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6149 0.1754 0.7914 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 1.3730 0.3254 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4631 2.2684 1.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5933 3.6394 0.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5970 3.5960 -0.1905 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8160 2.4939 -0.9032 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2040 1.3140 -0.6617 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1612 0.4367 -0.1618 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4336 0.7093 -0.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6566 0.7918 -2.0493 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0781 1.3375 -2.2466 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0279 0.4830 -1.4773 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6725 0.2307 -0.1692 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4142 -0.3413 -0.0494 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2739 -1.4703 -0.8552 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3596 1.2429 -1.4096 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1002 2.6792 -1.8682 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6113 -0.4713 -2.6352 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2427 4.7188 -1.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0026 5.9486 -0.5484 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9342 6.6421 0.1972 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0853 6.1652 0.3361 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5513 7.9503 0.8237 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1181 8.9214 -0.2324 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7665 8.4944 1.5532 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3509 9.8142 2.1722 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8845 8.5918 0.7594 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3124 3.9579 0.3946 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5058 2.1932 2.4912 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7456 1.7711 2.4255 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5206 -0.0951 1.5035 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5991 -0.5642 2.1420 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4789 -1.2929 1.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8312 -1.6269 1.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5527 -0.3398 2.0804 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5233 0.7148 2.3085 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3604 0.2958 2.8562 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1154 1.8162 3.1772 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3584 0.0555 0.9856 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7352 0.2082 1.0722 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2744 -0.0145 2.1650 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5665 0.6224 -0.0847 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1647 1.9789 -0.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5807 -0.4490 -1.1556 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1998 -0.7485 -1.6827 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6830 -2.4700 2.8203 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6375 -0.5714 -0.0175 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1708 -5.8826 -0.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1957 -5.1201 1.2791 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4361 -4.6814 -0.4371 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9369 -2.9713 -0.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5783 -3.5543 1.5513 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3740 -4.6565 -1.0269 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9941 -5.2091 0.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5991 -2.3554 -0.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2339 -2.9154 1.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0115 -3.8516 -1.3753 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6610 -4.6815 0.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8597 -2.2761 1.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9279 -2.1322 -0.8446 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6752 -3.6926 -1.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6941 -3.9017 0.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4869 -3.1780 1.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1160 -5.0201 1.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4201 -5.7691 0.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1330 -5.0667 2.8376 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4400 -6.7193 2.2043 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0855 -6.1487 2.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4491 -4.5727 1.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6714 -6.2013 -0.6286 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7056 -7.4510 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H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9948 7.8028 2.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2504 9.7535 2.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5189 10.6279 1.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8939 9.9631 3.1138 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8605 9.3767 0.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0095 4.7447 0.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3153 3.1217 2.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7995 1.8611 2.7864 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5645 2.2519 1.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1375 2.2941 3.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2527 -1.3644 2.8678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9750 -2.2574 0.8502 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4510 -2.1382 0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2238 -0.4897 2.9557 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3151 1.2101 1.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2693 2.4266 3.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6796 1.3795 4.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8099 2.4523 2.6017 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6113 0.7257 0.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2813 1.9597 -1.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0575 2.4208 -1.1082 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9109 2.6081 0.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2215 -0.1155 -1.9826 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0619 -1.3417 -0.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5000 0.1016 -1.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8255 -1.6427 -1.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2354 -1.0249 -2.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8644 -3.3865 2.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7719 -0.4784 -0.4983 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 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 23 32 1 0 32 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 39 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 43 47 1 0 42 48 1 0 41 49 1 0 36 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 52 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 56 58 1 0 35 59 1 0 34 60 1 0 21 61 1 0 20 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 70 71 1 0 71 72 2 0 71 73 1 0 73 74 1 0 73 75 1 0 75 76 1 0 65 77 1 0 64 78 1 0 46 6 1 0 24 19 1 0 38 33 1 0 45 40 1 0 68 63 1 0 1 79 1 0 1 80 1 0 1 81 1 0 2 82 1 0 2 83 1 0 3 84 1 0 3 85 1 0 4 86 1 0 4 87 1 0 5 88 1 0 5 89 1 0 6 90 1 0 7 91 1 0 7 92 1 0 8 93 1 0 8 94 1 0 9 95 1 0 9 96 1 0 10 97 1 0 10 98 1 0 11 99 1 0 11100 1 0 12101 1 0 12102 1 0 13103 1 0 13104 1 0 14105 1 0 14106 1 0 15107 1 0 15108 1 0 19109 1 0 20110 1 0 21111 1 0 23112 1 0 24113 1 0 28114 1 0 29115 1 0 29116 1 0 29117 1 0 30118 1 0 30119 1 0 31120 1 0 31121 1 0 31122 1 0 33123 1 0 34124 1 0 35125 1 0 36126 1 0 38127 1 0 40128 1 0 41129 1 0 42130 1 0 43131 1 0 45132 1 0 47133 1 0 47134 1 0 47135 1 0 48136 1 0 49137 1 0 50138 1 0 50139 1 0 54140 1 0 55141 1 0 55142 1 0 55143 1 0 56144 1 0 57145 1 0 57146 1 0 57147 1 0 58148 1 0 59149 1 0 60150 1 0 61151 1 0 61152 1 0 61153 1 0 63154 1 0 64155 1 0 65156 1 0 66157 1 0 67158 1 0 69159 1 0 69160 1 0 69161 1 0 73162 1 0 74163 1 0 74164 1 0 74165 1 0 75166 1 0 75167 1 0 76168 1 0 76169 1 0 76170 1 0 77171 1 0 78172 1 0 M END

Standard InCHIKey	DMGSPHMUQXHMLD-FGEZWTBKSA-N
Standard InCHI	InChI=1S/C55H94O23/c1-11-14-20-23-34-24-21-18-16-15-17-19-22-25-36(57)73-47-44(76-52-42(63)41(62)43(32(9)69-52)74-49(64)27(4)12-2)33(10)70-55(48(47)75-50(65)28(5)13-3)78-46-40(61)38(59)35(26-67-51(66)29(6)30(7)56)72-54(46)77-45-39(60)37(58)31(8)68-53(45)71-34/h27-35,37-48,52-56,58-63H,11-26H2,1-10H3/t27-,28-,29-,30-,31+,32+,33-,34-,35+,37+,38+,39-,40-,41+,42+,43+,44-,45+,46+,47+,48+,52-,53-,54-,55-/m0/s1
SMILES	CCCCCC1CCCCCCCCCC(=O)OC2C(C(OC(C2OC(=O)C(C)CC)OC3C(C(C(OC3OC4C(C(C(OC4O1)C)O)O)COC(=O)C(C)C(C)O)O)O)C)OC5C(C(C(C(O5)C)OC(=O)C(C)CC)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1122.62	Volume:	1108.683 ? Van der Waals volume.
Dense:	1.013	LogP:	5.353 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.175 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.347 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	46.0
TPSA:	320.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.066	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.822	Fsp³:	0.927
MCE-18:	112.906 ? 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:	0.309	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.062 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.546	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.114	MDCK Permeability:	-4.873
Pgp-inhibitor:	0.0	Pgp-substrate:	0.994
PAMPA:	0.997 ? 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):	0.911
20% Bioavailability (F20%):	0.684	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064	MRP1:	1.0
Plasma Protein Binding (PPB):	75.066%	Volume Distribution (VD):	-0.225
Fu:	14.552% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.001
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.081	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.026
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.656 ? 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):

0.932

Half-life (T1/2):

3.276

ADMET: Toxicity

hERG Blockers:	0.103	hERG Blockers (10um):	0.561
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.822
AMES Toxicity:	0.084	Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.244	Skin Sensitization:	0.663
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.284	Ototoxicity:	1.0
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.037
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.334
A549 Cytotoxicity:	0.251	Hek293 Cytotoxicity:	0.619
BCF:	0.409 ? 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:	3.426 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.549 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.511 ? 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
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	Roots	Mexican	n.a.	PMID[10479311]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19009	Ipomoea orizabensis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	4
IC50	1
ED50	1

Activity Type	# Activity
Cell line	2
Organism	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1.5	ug.mL-1	PMID[21865038]
NPT91	Cell line	KB	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[29126728]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[18316525]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[19743809]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[18611050]

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 NPC476087 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	22237
0.1-0.2	25107
0.2-0.3	2338
0.3-0.4	48
0.4-0.5	21
0.5-0.6	41
0.6-0.7	36
0.7-0.8	0
0.8-0.85	6
0.85-0.9	4
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475667
0.987	High Similarity	NPC478732
0.9744	High Similarity	NPC475270
0.9744	High Similarity	NPC475327
0.9146	High Similarity	NPC475164
0.9114	High Similarity	NPC478730
0.881	High Similarity	NPC473605
0.881	High Similarity	NPC475375
0.8659	High Similarity	NPC478731
0.8519	High Similarity	NPC173328
0.8452	Intermediate Similarity	NPC475525
0.8452	Intermediate Similarity	NPC475540
0.8353	Intermediate Similarity	NPC476066
0.8293	Intermediate Similarity	NPC297768
0.8193	Intermediate Similarity	NPC186992
0.8025	Intermediate Similarity	NPC478734
0.7831	Intermediate Similarity	NPC478733
0.7711	Intermediate Similarity	NPC477344
0.7471	Intermediate Similarity	NPC238264
0.7471	Intermediate Similarity	NPC477345
0.7391	Intermediate Similarity	NPC475241
0.7356	Intermediate Similarity	NPC119583
0.7294	Intermediate Similarity	NPC158302
0.7191	Intermediate Similarity	NPC115013
0.7159	Intermediate Similarity	NPC143421
0.7125	Intermediate Similarity	NPC606819
0.7111	Intermediate Similarity	NPC224953
0.7079	Intermediate Similarity	NPC483170
0.7045	Intermediate Similarity	NPC477319
0.7	Intermediate Similarity	NPC290012
0.6966	Remote Similarity	NPC307400
0.6966	Remote Similarity	NPC27289
0.6957	Remote Similarity	NPC269318
0.6932	Remote Similarity	NPC60849
0.6923	Remote Similarity	NPC126685
0.6854	Remote Similarity	NPC479058
0.6782	Remote Similarity	NPC89843
0.6744	Remote Similarity	NPC22742
0.6744	Remote Similarity	NPC477346
0.6739	Remote Similarity	NPC183888
0.6739	Remote Similarity	NPC184915
0.6667	Remote Similarity	NPC123204
0.6596	Remote Similarity	NPC44782
0.6452	Remote Similarity	NPC238056
0.6383	Remote Similarity	NPC259294
0.6374	Remote Similarity	NPC267592
0.6333	Remote Similarity	NPC479059
0.6277	Remote Similarity	NPC169345
0.6277	Remote Similarity	NPC477317
0.6277	Remote Similarity	NPC477318
0.625	Remote Similarity	NPC610996
0.6237	Remote Similarity	NPC472204
0.6196	Remote Similarity	NPC146992
0.6196	Remote Similarity	NPC85759
0.618	Remote Similarity	NPC113745
0.618	Remote Similarity	NPC477320
0.618	Remote Similarity	NPC477323
0.618	Remote Similarity	NPC477325
0.618	Remote Similarity	NPC609436
0.6154	Remote Similarity	NPC611287
0.6146	Remote Similarity	NPC472200
0.6136	Remote Similarity	NPC281563
0.6132	Remote Similarity	NPC600721
0.6132	Remote Similarity	NPC605872
0.6087	Remote Similarity	NPC109887
0.6064	Remote Similarity	NPC294748
0.5978	Remote Similarity	NPC477326
0.5963	Remote Similarity	NPC472352
0.5957	Remote Similarity	NPC472205
0.5833	Remote Similarity	NPC478726
0.5806	Remote Similarity	NPC600446
0.5806	Remote Similarity	NPC605013
0.5795	Remote Similarity	NPC477350
0.5794	Remote Similarity	NPC600672
0.573	Remote Similarity	NPC146380
0.5727	Remote Similarity	NPC600940
0.5727	Remote Similarity	NPC610997
0.5699	Remote Similarity	NPC477331
0.5684	Remote Similarity	NPC479061
0.5652	Remote Similarity	NPC477349
0.5625	Remote Similarity	NPC479060
0.56	Remote Similarity	NPC477347
0.5545	Remote Similarity	NPC478728
0.5532	Remote Similarity	NPC477332
0.549	Remote Similarity	NPC478727
0.5472	Remote Similarity	NPC63404
0.5426	Remote Similarity	NPC604005
0.5426	Remote Similarity	NPC605014
0.5413	Remote Similarity	NPC10121
0.5413	Remote Similarity	NPC198918
0.5413	Remote Similarity	NPC290276
0.5413	Remote Similarity	NPC10883
0.5385	Remote Similarity	NPC475425
0.5361	Remote Similarity	NPC478722
0.5361	Remote Similarity	NPC478725
0.5349	Remote Similarity	NPC479056
0.5327	Remote Similarity	NPC35338
0.5327	Remote Similarity	NPC204214
0.5327	Remote Similarity	NPC92283
0.5306	Remote Similarity	NPC478723
0.5306	Remote Similarity	NPC478724
0.5248	Remote Similarity	NPC479057
0.5196	Remote Similarity	NPC163409
0.5152	Remote Similarity	NPC44682
0.5143	Remote Similarity	NPC477348
0.5124	Remote Similarity	NPC147032
0.5055	Remote Similarity	NPC478729

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7150
0.1-0.2	1947
0.2-0.3	52
0.3-0.4	1
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