NPASS Compound

Natural Product: NPC194671

Natural Product ID	NPC194671
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Somamide B
IUPAC Name	(2S)-N-[(2S,5S,8S,11R,12S,15Z,18S,21R)-2-benzyl-15-ethylidene-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]-2-(butanoylamino)pentanediamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL399107
PubChem CID	23657292
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 128131 0 0 0 0 0 0 0 0999 V2000 -7.1873 0.1365 4.4337 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1783 0.6831 3.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4164 1.3587 2.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4816 0.4701 1.5968 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6230 0.2189 0.3641 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8232 -0.5983 -0.4561 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6433 -1.3502 -1.4593 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3743 -0.3658 -2.3328 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1770 -1.0964 -3.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4404 -0.9900 -3.4231 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.4923 -1.9020 -4.2733 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7506 0.1238 -1.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7747 -0.5381 -1.5693 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5646 -0.6305 -2.1924 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7323 0.5846 -2.4326 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3509 1.4827 -3.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3954 1.3213 -1.3112 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0706 1.5453 -0.9762 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8361 1.0535 -1.7099 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3487 2.3479 0.2200 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0597 3.8015 -0.0885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5561 3.8541 -0.2856 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5913 4.1942 -1.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7484 2.2195 0.3875 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5455 2.7967 1.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0121 2.4650 1.1376 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8316 3.5843 0.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6836 4.8586 1.2867 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6759 5.7148 0.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4758 6.9136 1.5383 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2808 7.2767 2.6002 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2832 6.4302 3.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4668 5.2474 2.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1324 8.4778 3.3072 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2311 1.1862 0.4673 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9907 1.1401 -0.9175 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6571 0.0626 1.1355 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7797 0.3432 2.3613 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9865 -1.3246 0.8104 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6339 -1.4501 -0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0556 -2.7865 -0.9602 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2582 -3.2927 -0.5052 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7043 -4.5043 -0.9629 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9841 -5.2480 -1.8758 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7874 -4.7528 -2.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3333 -3.5247 -1.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9274 -2.2231 1.1791 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1887 -3.4439 1.8521 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6561 -4.6172 1.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4434 -4.2482 0.2641 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6407 -3.1477 0.9949 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5429 -2.0058 1.0381 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2544 -0.8628 0.9718 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3909 -2.9462 0.3612 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5058 -3.8420 0.3615 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8048 -3.7179 -0.2599 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6751 -4.7494 -0.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0289 -4.6524 -0.8381 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2151 -2.5731 -0.9249 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6997 -1.7687 -1.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4005 -1.8718 -2.1518 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2482 -5.0676 1.0109 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5395 -3.5786 2.1914 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0413 3.7516 2.0630 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8548 1.4726 -1.5655 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4281 -0.0997 2.2869 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7959 -0.1163 5.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7620 -0.7991 4.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4405 0.8870 4.7234 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7754 1.4685 3.9772 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9037 -0.0500 3.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8298 2.2390 2.7205 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1498 1.8036 1.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2671 -1.3891 0.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0188 -2.0541 -2.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4400 -1.9126 -0.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6397 0.3046 -2.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0825 0.2568 -1.7638 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0234 -0.4146 -2.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0017 -2.2708 -5.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7847 -1.0152 -3.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 0.2623 -2.9021 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1977 0.9542 -3.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6306 1.6835 -4.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5889 2.4673 -3.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2760 2.0595 1.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3091 4.4723 0.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 3.8909 -1.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9809 4.7655 0.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0345 2.9664 0.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7251 5.3118 -1.3724 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6038 3.7562 -1.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0614 3.9553 -2.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2899 2.4150 2.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5500 3.7411 -0.5454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9068 3.3274 0.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0160 5.4620 0.0450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6939 7.6062 1.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9398 6.6930 3.8401 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2573 4.5847 2.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5657 9.3249 2.9231 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9275 1.2285 -1.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4033 2.0744 -1.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3382 0.3271 -1.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8737 -1.5603 1.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0744 -1.0258 -1.3763 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5754 -0.8049 -0.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8327 -2.7245 0.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6419 -4.9568 -0.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3605 -6.2183 -2.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1701 -5.2671 -3.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3999 -3.1029 -2.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6741 -3.4923 2.8623 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4583 -4.9680 0.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4168 -5.4780 1.7713 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8169 -5.1030 -0.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7512 -3.7579 -0.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5284 -3.5934 2.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3914 -5.6550 0.3046 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7509 -4.5604 -0.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2645 -5.6424 -1.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0948 -3.8216 -1.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0428 -2.7610 -2.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3296 -5.1447 1.8370 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7537 -3.1056 3.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1880 3.5810 2.6005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0560 2.0580 -1.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6197 -0.5084 1.8636 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 2 3 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 3 9 11 1 0 6 12 1 0 12 13 2 3 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 24 25 2 3 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 31 34 1 0 26 35 1 0 35 36 1 0 35 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 39 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 2 0 51 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 57 58 1 0 56 59 1 0 59 60 2 0 60 61 1 0 55 62 1 0 48 63 1 0 25 64 1 0 12 65 1 0 4 66 1 0 60 14 1 0 33 28 1 0 46 41 1 0 52 47 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 0 2 71 1 0 3 72 1 0 3 73 1 0 6 74 1 1 7 75 1 0 7 76 1 0 8 77 1 0 8 78 1 0 10 79 1 0 11 80 1 0 14 81 1 6 15 82 1 6 16 83 1 0 16 84 1 0 16 85 1 0 20 86 1 1 21 87 1 0 22 88 1 0 22 89 1 0 22 90 1 0 23 91 1 0 23 92 1 0 23 93 1 0 26 94 1 1 27 95 1 0 27 96 1 0 29 97 1 0 30 98 1 0 32 99 1 0 33100 1 0 34101 1 0 36102 1 0 36103 1 0 36104 1 0 39105 1 1 40106 1 0 40107 1 0 42108 1 0 43109 1 0 44110 1 0 45111 1 0 46112 1 0 48113 1 1 49114 1 0 49115 1 0 50116 1 0 50117 1 0 51118 1 1 57119 1 0 58120 1 0 58121 1 0 58122 1 0 61123 1 0 62124 1 0 63125 1 0 64126 1 0 65127 1 0 66128 1 0 M END

Standard InCHIKey	QNGONASSDVVIFN-UAMDCIPZSA-N
Standard InCHI	InChI=1S/C46H62N8O12/c1-7-12-36(57)48-31(19-21-35(47)56)41(60)52-39-26(5)66-46(65)38(25(3)4)51-42(61)33(23-28-15-17-29(55)18-16-28)53(6)45(64)34(24-27-13-10-9-11-14-27)54-37(58)22-20-32(44(54)63)50-40(59)30(8-2)49-43(39)62/h8-11,13-18,25-26,31-34,37-39,55,58H,7,12,19-24H2,1-6H3,(H2,47,56)(H,48,57)(H,49,62)(H,50,59)(H,51,61)(H,52,60)/b30-8-/t26-,31+,32+,33+,34+,37-,38+,39+/m1/s1
SMILES	CCCC(=N[C@@H](CCC(=N)O)C(=N[C@H]1[C@@H](C)OC(=O)[C@H](C(C)C)N=C([C@H](Cc2ccc(cc2)O)N(C)C(=O)[C@H](Cc2ccccc2)N2[C@@H](CC[C@@H](C2=O)N=C(/C(=C/C)/N=C1O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.45	Volume:	921.219 ? Van der Waals volume.
Dense:	0.997	LogP:	1.167 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.516 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.929 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	42.0
TPSA:	314.41 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.345	Fsp³:	0.5
MCE-18:	117.391 ? 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:	0.424	Fluc inhibitor:	0.186 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.836 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.034

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.912	MDCK Permeability:	-5.116
Pgp-inhibitor:	0.77	Pgp-substrate:	1.0
PAMPA:	0.865 ? 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):	0.539
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:	0.655
Plasma Protein Binding (PPB):	63.394%	Volume Distribution (VD):	-0.517
Fu:	33.386% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.0
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.017	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.002 ? 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):

0.871

Half-life (T1/2):

2.22

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.017	Rat Oral Acute Toxicity:	0.71
Maximum Recommended Daily Dose:	0.984	Skin Sensitization:	1.0
Carcinogencity:	0.784	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.278	Ototoxicity:	1.0
Hematotoxicity:	0.031	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.007
BCF:	0.194 ? 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:	2.88 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.574 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.588 ? 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
NPO32763	lyngbya spp.	Species	Oscillatoriaceae	Bacteria	n.a.	Floridian	n.a.	PMID[17910513]

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	5

Activity Type	# Activity
Protein family	1
Others	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2929	Protein family	Pancreatic elastase	Sus scrofa	IC50	=	4200.0	nM	PMID[12670149]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	9.5	nM	Open TG-GATES in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	IC50	=	4200.0	nM	PMID[22880631]
NPT2	Others	Unspecified	n.a.	IC50	>	30000.0	nM	PMID[12670149]

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 NPC194671 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	11747
0.1-0.2	36117
0.2-0.3	1785
0.3-0.4	135
0.4-0.5	31
0.5-0.6	23
0.6-0.7	14
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9604	High Similarity	NPC269750
0.8302	Intermediate Similarity	NPC279871
0.8288	Intermediate Similarity	NPC488263
0.7905	Intermediate Similarity	NPC306804
0.7522	Intermediate Similarity	NPC294951
0.7227	Intermediate Similarity	NPC163961
0.6807	Remote Similarity	NPC159767
0.675	Remote Similarity	NPC155506
0.6667	Remote Similarity	NPC487289
0.656	Remote Similarity	NPC240130
0.6471	Remote Similarity	NPC45037
0.6441	Remote Similarity	NPC137627
0.6417	Remote Similarity	NPC471050
0.6271	Remote Similarity	NPC50016
0.626	Remote Similarity	NPC302715
0.6239	Remote Similarity	NPC163392
0.6161	Remote Similarity	NPC239762
0.6111	Remote Similarity	NPC61332
0.6033	Remote Similarity	NPC489102
0.6	Remote Similarity	NPC471048
0.594	Remote Similarity	NPC281049
0.594	Remote Similarity	NPC473305
0.5873	Remote Similarity	NPC40234
0.5833	Remote Similarity	NPC273755
0.582	Remote Similarity	NPC471052
0.5714	Remote Similarity	NPC107938
0.5669	Remote Similarity	NPC294516
0.5649	Remote Similarity	NPC473404
0.5625	Remote Similarity	NPC476227
0.5581	Remote Similarity	NPC46009
0.5556	Remote Similarity	NPC471053
0.5504	Remote Similarity	NPC487290
0.5484	Remote Similarity	NPC248670
0.5462	Remote Similarity	NPC102959
0.5433	Remote Similarity	NPC471051
0.5426	Remote Similarity	NPC230611
0.5391	Remote Similarity	NPC471526
0.52	Remote Similarity	NPC471165
0.5152	Remote Similarity	NPC60516
0.5075	Remote Similarity	NPC65714
0.5075	Remote Similarity	NPC473371
0.504	Remote Similarity	NPC62104
0.5039	Remote Similarity	NPC5719

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC194671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2999
0.1-0.2	5898
0.2-0.3	246
0.3-0.4	7
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