NPASS Compound

Natural Product: NPC220060

Natural Product ID	NPC220060
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(R)-3-((2S,5S,8S,11R,12S,15S,18S,21R)-15-(3-(Amino(Iminio)Methylamino)Propyl)-2-Sec-Butyl-5-(3-Chloro-4-Hydroxybenzyl)-21-Hydroxy-8-Isopropyl-4,11-Dimethyl-3,6,9,13,16,22-Hexaoxo-10-Oxa-1,4,7,14,17-Pentaazabicyclo[16.3.1]Docosan-12-Ylamino)-3-Oxopropane-1,2-Diyl Disulfate
IUPAC Name	[(2R)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-2-[(2S)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-15-[3-(diaminomethylideneamino)propyl]-21-hydroxy-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]-1-oxo-3-sulfooxypropan-2-yl] hydrogen sulfate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1078913
PubChem CID	44254976
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 129131 0 0 0 0 0 0 0 0999 V2000 -4.6853 4.0007 3.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5123 3.5150 1.8417 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4904 2.0346 1.6914 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0650 1.4578 2.9757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1174 1.4998 1.4278 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1221 0.0101 1.3439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8179 -0.5836 2.3935 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4058 -0.8938 0.3411 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9497 -0.4229 -0.8604 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1584 -2.3196 0.5041 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3647 -3.1634 0.6361 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3657 -3.1959 -0.4064 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3088 -4.1087 -1.4236 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2920 -4.1095 -2.3903 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3481 -3.2219 -2.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3722 -2.3074 -1.3295 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4028 -2.2996 -0.3687 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7189 -1.1555 -1.2977 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -9.3472 -3.2142 -3.3548 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1310 -2.7664 -0.4857 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9586 -2.8992 -0.2665 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6861 -3.0013 0.1221 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2497 -4.3886 0.6498 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 -4.7645 1.8561 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3167 -5.3917 -0.4563 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2256 -2.7732 -1.0699 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2565 -2.7064 -2.2294 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5852 -2.6336 -0.9249 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4617 -2.4257 -1.9961 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4553 -3.5527 -2.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2136 -1.1136 -1.9642 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2765 -0.0206 -2.2555 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0486 1.0048 -1.5928 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5283 1.5482 -0.3790 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5634 2.6329 -0.7010 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1083 3.2194 0.5663 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1517 4.2896 0.2838 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2711 3.7787 -0.4595 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3704 4.6191 -0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6142 5.6619 -0.0724 N 0 0 0 0 0 0 0 0 0 0 0 0 8.2251 4.3450 -1.8852 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3644 2.1675 0.3676 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3113 2.3995 -0.2843 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8947 2.9861 0.2813 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4074 3.9732 -0.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8678 4.2606 -0.4744 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6377 2.9234 -0.7196 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3544 2.1194 0.4317 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9065 1.9392 0.4414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6615 0.7741 0.5978 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 2.3802 -1.9004 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4196 2.4815 1.7085 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5461 -0.1900 -3.4722 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0322 -0.9658 -0.8117 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2150 -0.4619 -0.8221 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1040 -0.2852 0.3231 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6158 -0.9611 1.5995 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4935 -0.7008 2.6453 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3451 -1.7801 3.8947 S 0 0 0 0 0 0 0 0 0 0 0 0 7.6234 -1.8346 4.7245 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2468 -1.3483 4.8181 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9604 -3.3214 3.3378 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3579 -0.8105 0.0327 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5824 0.3069 0.0552 S 0 0 0 0 0 0 0 0 0 0 0 0 8.2723 1.4273 1.0316 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7819 0.9728 -1.2859 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0336 -0.4514 0.4446 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6955 -0.0366 -2.0664 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5983 -3.0466 -1.7939 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4585 5.0901 2.8466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2587 3.9564 3.9426 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7229 3.5223 3.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5862 3.8002 2.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2888 4.1139 0.9595 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2243 1.7473 0.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8168 0.3687 3.0964 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8014 2.0292 3.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1667 1.4909 2.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5961 1.6962 2.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0953 -1.3199 -1.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1968 0.1617 -1.4724 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8973 0.1389 -0.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6392 -2.4895 1.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8319 -2.8973 1.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0464 -4.2438 0.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5176 -4.8614 -1.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2705 -4.8333 -3.2235 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4949 -1.5462 0.4318 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2233 -3.8549 -4.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2841 -2.2541 0.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8016 -4.3090 0.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4466 -5.3443 2.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9931 -5.2739 1.5410 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3136 -3.8008 2.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6829 -5.8663 -0.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0587 -6.1653 -0.1659 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6276 -4.8808 -1.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8402 -2.4094 -2.9316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9330 -4.3601 -2.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2965 -3.1830 -2.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8104 -3.9546 -1.1877 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9430 -1.1347 -2.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9309 0.8030 0.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3825 2.2522 -1.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0713 3.4264 -1.3409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5742 2.4518 1.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2727 3.6580 1.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5079 4.7512 1.2066 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6516 5.0941 -0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3070 2.7950 -0.7796 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4025 6.2905 -0.2826 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8938 3.9402 -2.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2310 4.5627 -1.7863 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6992 3.5335 1.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3146 3.4377 -1.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 4.9052 -0.8076 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2232 5.0251 -1.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9581 4.4854 0.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6504 3.1778 -0.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2999 2.9854 -2.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1027 3.3712 2.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1197 0.5954 -3.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2865 0.8080 0.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6248 -0.5493 1.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4898 -2.0383 1.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5105 -3.5375 2.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8511 -1.3605 0.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1264 0.4751 -2.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9933 -3.5741 -2.4023 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 3 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 15 19 1 0 10 20 1 0 20 21 2 3 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 2 3 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 2 3 39 41 1 0 34 42 1 0 42 43 2 3 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 47 51 1 0 42 52 1 0 32 53 1 0 31 54 1 0 54 55 2 3 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 2 0 59 61 2 0 59 62 1 0 56 63 1 0 63 64 1 0 64 65 2 0 64 66 2 0 64 67 1 0 55 68 1 0 20 69 1 0 48 5 1 0 17 12 1 0 49 44 1 0 1 70 1 0 1 71 1 0 1 72 1 0 2 73 1 0 2 74 1 0 3 75 1 6 4 76 1 0 4 77 1 0 4 78 1 0 5 79 1 1 9 80 1 0 9 81 1 0 9 82 1 0 10 83 1 1 11 84 1 0 11 85 1 0 13 86 1 0 14 87 1 0 17 88 1 0 19 89 1 0 22 90 1 1 23 91 1 0 24 92 1 0 24 93 1 0 24 94 1 0 25 95 1 0 25 96 1 0 25 97 1 0 29 98 1 6 30 99 1 0 30100 1 0 30101 1 0 31102 1 6 34103 1 1 35104 1 0 35105 1 0 36106 1 0 36107 1 0 37108 1 0 37109 1 0 38110 1 0 40111 1 0 41112 1 0 41113 1 0 44114 1 1 45115 1 0 45116 1 0 46117 1 0 46118 1 0 47119 1 6 51120 1 0 52121 1 0 53122 1 0 56123 1 1 57124 1 0 57125 1 0 62126 1 0 67127 1 0 68128 1 0 69129 1 0 M END

Standard InCHIKey	CDNBDTGIQPIOQU-JJSZTCTISA-N
Standard InCHI	InChI=1S/C39H60ClN9O18S2/c1-7-19(4)31-37(57)48(6)25(16-21-10-12-26(50)22(40)15-21)33(53)46-29(18(2)3)38(58)66-20(5)30(47-34(54)27(67-69(62,63)64)17-65-68(59,60)61)35(55)44-23(9-8-14-43-39(41)42)32(52)45-24-11-13-28(51)49(31)36(24)56/h10,12,15,18-20,23-25,27-31,50-51H,7-9,11,13-14,16-17H2,1-6H3,(H,44,55)(H,45,52)(H,46,53)(H,47,54)(H4,41,42,43)(H,59,60,61)(H,62,63,64)/t19-,20+,23-,24-,25-,27+,28+,29-,30-,31-/m0/s1
SMILES	CC[C@H](C)[C@H]1C(=O)N(C)[C@@H](Cc2ccc(c(c2)Cl)O)C(=N[C@@H](C(C)C)C(=O)O[C@H](C)[C@@H](C(=N[C@@H](CCCNC(=N)N)C(=N[C@H]2CC[C@H](N1C2=O)O)O)O)N=C([C@@H](COS(=O)(=O)O)OS(=O)(=O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1041.32	Volume:	937.854 ? Van der Waals volume.
Dense:	1.11	LogP:	-2.345 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.056 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.667 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	38.0
TPSA:	426.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	27.0
H-Bond Donor:	12.0	Rings:	3.0
Heavy Atoms:	30.0

MedChem Properties

QED Drug-Likeness Score:	0.036	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.647	Fsp³:	0.641
MCE-18:	129.188 ? 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:	0.428	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.063 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.596 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.003	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.824	MDCK Permeability:	-5.077
Pgp-inhibitor:	0.163	Pgp-substrate:	0.825
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):	0.991
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:	0.233
Plasma Protein Binding (PPB):	56.059%	Volume Distribution (VD):	-0.561
Fu:	44.513% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

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:	0.852	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):

0.748

Half-life (T1/2):

2.099

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:	0.276	Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.602	Skin Sensitization:	1.0
Carcinogencity:	0.576	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.072
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.473	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.399 ? 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:	3.24 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.055 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.289 ? 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
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	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
IC50	2

Activity Type	# Activity
Others	2

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	=	1200.0	nM	PMID[22245048]
NPT2	Others	Unspecified	n.a.	IC50	>	100000.0	nM	PMID[25668560]

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 NPC220060 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	13242
0.1-0.2	35528
0.2-0.3	950
0.3-0.4	73
0.4-0.5	30
0.5-0.6	12
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC60516
0.8067	Intermediate Similarity	NPC25539
0.7913	Intermediate Similarity	NPC63040
0.7302	Intermediate Similarity	NPC489838
0.712	Intermediate Similarity	NPC277306
0.7025	Intermediate Similarity	NPC194699
0.6917	Remote Similarity	NPC5719
0.686	Remote Similarity	NPC22883
0.6694	Remote Similarity	NPC15068
0.6667	Remote Similarity	NPC102959
0.6587	Remote Similarity	NPC302715
0.6417	Remote Similarity	NPC62104
0.6212	Remote Similarity	NPC473404
0.6183	Remote Similarity	NPC61332
0.6119	Remote Similarity	NPC489835
0.6119	Remote Similarity	NPC489836
0.6094	Remote Similarity	NPC471526
0.6047	Remote Similarity	NPC473407
0.6047	Remote Similarity	NPC219350
0.6	Remote Similarity	NPC240130
0.6	Remote Similarity	NPC489837
0.5926	Remote Similarity	NPC489834
0.5891	Remote Similarity	NPC210377
0.5891	Remote Similarity	NPC217804
0.5816	Remote Similarity	NPC64216
0.563	Remote Similarity	NPC65714
0.563	Remote Similarity	NPC473371
0.5606	Remote Similarity	NPC248822
0.553	Remote Similarity	NPC45037
0.5435	Remote Similarity	NPC471592
0.5426	Remote Similarity	NPC1390
0.5154	Remote Similarity	NPC306804
0.507	Remote Similarity	NPC163961

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC220060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2622
0.1-0.2	6355
0.2-0.3	168
0.3-0.4	4
0.4-0.5	1
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