NPASS Compound

Natural Product: NPC302715

Natural Product ID	NPC302715
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Micropeptin 90
IUPAC Name	[(2S)-3-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-benzyl-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-2-hydroxy-3-oxopropyl] hydrogen sulfate
Synonyms	Micropeptin 90
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL552944
PubChem CID	45269517
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

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 126129 0 0 0 0 0 0 0 0999 V2000 -3.0474 -0.3991 -3.4873 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5511 -0.5660 -3.6278 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2137 -1.0770 -5.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9930 -1.5613 -2.6184 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4484 -1.7314 -2.7563 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0135 -1.2486 -3.8045 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3142 -2.3647 -1.8835 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7083 -2.4282 -2.1500 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0632 -3.8694 -2.5856 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5764 -2.0987 -0.9788 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0560 -0.8247 -0.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8103 0.1987 -0.3477 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3725 1.4651 0.2492 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5281 2.2545 0.8067 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5787 2.6263 -0.1790 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6829 3.3841 0.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1880 4.5833 1.1518 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7605 5.6707 0.3608 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4816 5.5674 -0.8801 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6432 6.9450 0.9956 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6322 2.1935 -0.7972 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4662 2.6294 -0.7391 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5555 2.5321 0.3499 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6508 3.8567 1.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 3.9874 2.0576 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8246 3.9403 1.3094 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9682 2.7086 0.6068 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2419 2.0269 0.6438 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2600 2.7708 -0.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5808 2.1660 -0.1978 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4245 2.3853 0.8771 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7122 1.8934 0.8842 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1937 1.1592 -0.2012 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3614 0.9356 -1.2762 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0790 1.4403 -1.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2362 0.5905 0.4838 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0145 0.0326 -0.2559 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4030 -0.3536 1.1115 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5902 0.2452 2.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3532 -1.7483 0.8971 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4490 -2.6056 1.4045 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8091 -2.4349 0.9847 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3321 -3.0070 -0.1544 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6537 -2.8793 -0.5165 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5083 -2.1540 0.2777 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0257 -1.5730 1.4123 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6970 -1.7131 1.7572 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8619 -1.9956 -0.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8801 -2.2036 -0.4306 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4872 -1.3845 -1.2921 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8877 -3.5580 -0.6806 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 2.3489 -0.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0758 1.8557 -1.1915 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9889 5.0509 0.4673 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3954 2.3888 -1.9965 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8107 -0.7488 0.2358 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4202 -3.1046 0.0741 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3097 -3.9211 0.4487 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0017 -4.8778 1.5260 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9703 -4.6114 2.6749 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2546 -4.8679 2.2106 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3408 -4.6134 3.4535 S 0 0 0 0 0 0 0 0 0 0 0 0 6.6144 -4.0705 4.6423 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3897 -3.5861 3.0666 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0580 -6.0762 3.8413 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0716 -6.1884 1.0799 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5486 -3.9279 -0.1304 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5771 -0.7580 -4.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4607 -1.0574 -2.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3368 0.6430 -3.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0763 0.4014 -3.4849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8010 -2.1057 -5.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1622 -1.1645 -5.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4879 -0.4277 -5.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4474 -2.5525 -2.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -1.8288 -3.0310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3090 -4.1931 -3.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0375 -3.7792 -3.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0899 -4.5360 -1.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6443 -2.0259 -1.2017 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7220 1.2395 1.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9578 1.7124 1.6854 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0729 3.2001 1.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1689 3.2571 -0.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0524 1.6991 -0.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4812 3.6710 -0.1811 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1715 2.7621 1.3085 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1373 4.6671 2.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1700 6.3900 -1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8214 7.1395 1.5950 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3756 7.6923 0.8661 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8658 1.7596 1.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5621 3.8066 1.7493 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7440 4.6833 0.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4845 3.1885 2.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4160 4.9936 2.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6448 4.0450 2.0762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6241 2.1857 1.7317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8114 2.8822 -1.2046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3976 3.8137 0.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1034 2.9525 1.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3528 2.0779 1.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2130 0.7869 -0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7658 0.3616 -2.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4784 1.2430 -2.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5442 0.0783 1.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8262 1.2694 2.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6776 -0.4377 3.0537 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4583 -2.0891 1.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1497 -3.6710 1.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3505 -2.6199 2.5442 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7047 -3.5825 -0.8061 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0548 -3.3368 -1.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7199 -0.9982 2.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3794 -1.2242 2.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5783 -1.9172 0.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7869 -3.9806 -1.5714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7676 5.8876 0.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9994 2.9875 -2.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6495 -0.4042 1.1772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9660 -4.7289 1.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6841 -5.2140 3.5386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9026 -3.5231 2.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7620 -6.8260 3.2962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0660 -6.1907 0.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6741 -3.7641 -1.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 2 3 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 2 3 18 20 1 0 13 21 1 0 21 22 2 3 22 23 1 0 23 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 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 28 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 45 48 1 0 40 49 1 0 49 50 2 3 49 51 1 0 27 52 1 0 52 53 2 0 26 54 1 0 21 55 1 0 11 56 1 0 10 57 1 0 57 58 2 3 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 2 0 62 64 2 0 62 65 1 0 59 66 1 0 58 67 1 0 50 4 1 0 52 23 1 0 35 30 1 0 47 42 1 0 1 68 1 0 1 69 1 0 1 70 1 0 2 71 1 0 3 72 1 0 3 73 1 0 3 74 1 0 4 75 1 6 8 76 1 6 9 77 1 0 9 78 1 0 9 79 1 0 10 80 1 6 13 81 1 1 14 82 1 0 14 83 1 0 15 84 1 0 15 85 1 0 16 86 1 0 16 87 1 0 17 88 1 0 19 89 1 0 20 90 1 0 20 91 1 0 23 92 1 1 24 93 1 0 24 94 1 0 25 95 1 0 25 96 1 0 26 97 1 1 28 98 1 1 29 99 1 0 29100 1 0 31101 1 0 32102 1 0 33103 1 0 34104 1 0 35105 1 0 39106 1 0 39107 1 0 39108 1 0 40109 1 1 41110 1 0 41111 1 0 43112 1 0 44113 1 0 46114 1 0 47115 1 0 48116 1 0 51117 1 0 54118 1 0 55119 1 0 56120 1 0 59121 1 1 60122 1 0 60123 1 0 65124 1 0 66125 1 0 67126 1 0 M END

Standard InCHIKey	XYLRPTCPMWMQJO-UJRYMIDGSA-N
Standard InCHI	InChI=1S/C42H59N9O15S/c1-22(2)33-41(61)66-23(3)34(49-37(57)31(53)21-65-67(62,63)64)38(58)46-27(11-8-18-45-42(43)44)35(55)47-28-16-17-32(54)51(39(28)59)30(20-24-9-6-5-7-10-24)40(60)50(4)29(36(56)48-33)19-25-12-14-26(52)15-13-25/h5-7,9-10,12-15,22-23,27-34,52-54H,8,11,16-21H2,1-4H3,(H,46,58)(H,47,55)(H,48,56)(H,49,57)(H4,43,44,45)(H,62,63,64)/t23-,27+,28+,29+,30+,31+,32-,33+,34+/m1/s1
SMILES	CC(C)[C@H]1C(=O)O[C@H](C)[C@@H](C(=N[C@@H](CCCNC(=N)N)C(=N[C@H]2CC[C@H](N([C@@H](Cc3ccccc3)C(=O)N(C)[C@@H](Cc3ccc(cc3)O)C(=N1)O)C2=O)O)O)O)N=C([C@H](COS(=O)(=O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	961.39	Volume:	913.185 ? Van der Waals volume.
Dense:	1.053	LogP:	-1.292 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.183 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.881 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	42.0
TPSA:	383.47 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	12.0	Rings:	4.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.041	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.313	Fsp³:	0.524
MCE-18:	125.875 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.457	Fluc inhibitor:	0.02 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.039 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.862 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.227	MDCK Permeability:	-5.245
Pgp-inhibitor:	0.466	Pgp-substrate:	1.0
PAMPA:	0.965 ? 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):	0.87
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.089
Plasma Protein Binding (PPB):	45.057%	Volume Distribution (VD):	-0.512
Fu:	49.281% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.661

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:	0.539	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.001 ? 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):

0.362

Half-life (T1/2):

2.385

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.023	Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.822	Skin Sensitization:	1.0
Carcinogencity:	0.626	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.96
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.998
Hematotoxicity:	0.028	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.002
BCF:	0.355 ? 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:	3.228 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.072 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.177 ? 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
NPO33392	cyanobacterium microcystis aeruginosa nies-88	Species	Cyanobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15679310]

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
IC50	3

Activity Type	# Activity
Others	3

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
NPT2	Others	Unspecified	n.a.	IC50	=	2080.0	nM	PMID[20627740]
NPT2	Others	Unspecified	n.a.	IC50	>	100000.0	nM	DOI[10.1016/j.indcrop.2012.05.026]
NPT2	Others	Unspecified	n.a.	IC50	=	20000000.0	nM	DOI[10.1016/j.indcrop.2012.05.026]

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 NPC302715 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	14768
0.1-0.2	33445
0.2-0.3	1404
0.3-0.4	172
0.4-0.5	11
0.5-0.6	29
0.6-0.7	22
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8304	Intermediate Similarity	NPC102959
0.7928	Intermediate Similarity	NPC22883
0.7845	Intermediate Similarity	NPC61332
0.7583	Intermediate Similarity	NPC240130
0.7273	Intermediate Similarity	NPC163961
0.7143	Intermediate Similarity	NPC60516
0.7094	Intermediate Similarity	NPC217804
0.6991	Remote Similarity	NPC306804
0.6891	Remote Similarity	NPC63040
0.6842	Remote Similarity	NPC62104
0.678	Remote Similarity	NPC5719
0.672	Remote Similarity	NPC473404
0.6587	Remote Similarity	NPC220060
0.6587	Remote Similarity	NPC277306
0.6364	Remote Similarity	NPC137627
0.632	Remote Similarity	NPC159767
0.629	Remote Similarity	NPC294951
0.627	Remote Similarity	NPC155506
0.626	Remote Similarity	NPC194671
0.621	Remote Similarity	NPC471526
0.6198	Remote Similarity	NPC50016
0.6167	Remote Similarity	NPC1390
0.616	Remote Similarity	NPC269750
0.616	Remote Similarity	NPC15068
0.6129	Remote Similarity	NPC210377
0.6063	Remote Similarity	NPC487289
0.6047	Remote Similarity	NPC488263
0.6	Remote Similarity	NPC45037
0.6	Remote Similarity	NPC473305
0.5952	Remote Similarity	NPC194699
0.5887	Remote Similarity	NPC471052
0.584	Remote Similarity	NPC279871
0.5789	Remote Similarity	NPC25539
0.5778	Remote Similarity	NPC489838
0.5772	Remote Similarity	NPC273755
0.5703	Remote Similarity	NPC471050
0.5659	Remote Similarity	NPC473407
0.5625	Remote Similarity	NPC471053
0.5603	Remote Similarity	NPC163392
0.5591	Remote Similarity	NPC489102
0.5504	Remote Similarity	NPC471051
0.5455	Remote Similarity	NPC40234
0.542	Remote Similarity	NPC219350
0.5417	Remote Similarity	NPC239762
0.5414	Remote Similarity	NPC46009
0.5338	Remote Similarity	NPC471048
0.5328	Remote Similarity	NPC489834
0.5312	Remote Similarity	NPC248670
0.5303	Remote Similarity	NPC107938
0.5263	Remote Similarity	NPC294516
0.5263	Remote Similarity	NPC230611
0.5245	Remote Similarity	NPC64216
0.5224	Remote Similarity	NPC476227
0.5211	Remote Similarity	NPC281049
0.5156	Remote Similarity	NPC471165
0.5147	Remote Similarity	NPC65714
0.5147	Remote Similarity	NPC473371
0.5111	Remote Similarity	NPC487290

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC302715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3134
0.1-0.2	5702
0.2-0.3	296
0.3-0.4	16
0.4-0.5	2
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