NPASS Compound

Natural Product: NPC223791

Natural Product ID	NPC223791
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Phakellistatin 15
IUPAC Name	n.a.
Synonyms	phakellistatin 15
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1099230
PubChem CID	46209786
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 137142 0 0 0 0 0 0 0 0999 V2000 3.6917 -5.3479 -2.4548 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9405 -5.8489 -1.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0652 -4.7695 -0.0414 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3148 -5.4001 1.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8851 -3.8159 0.0071 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6313 -4.5046 0.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2838 -5.4803 -0.3601 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6935 -4.2204 1.3378 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6670 -3.2104 2.2943 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1209 -3.8135 3.4601 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5630 -5.1733 2.9882 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4916 -5.0274 1.5032 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7222 -4.2834 1.0471 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8522 -3.9187 -0.1487 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7912 -3.2432 -0.9218 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1150 -3.8993 -1.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0729 -3.1391 -1.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4073 -3.8878 -2.0780 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5524 -2.9984 -3.3855 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9291 -1.8258 -0.3952 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9766 -1.3506 0.0264 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5884 -0.2274 0.5653 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4505 -0.2043 2.0634 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0322 -0.3446 2.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0699 0.9048 2.6377 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1933 1.0091 -0.1042 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2422 0.9812 -0.9130 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7397 2.3048 0.0088 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8721 2.7847 0.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4752 3.7765 -0.3442 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2260 4.4606 -0.8490 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1248 3.4359 -0.6649 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0175 3.9888 0.1580 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8819 4.2831 -0.2433 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2031 4.2423 -1.4774 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2310 5.5490 -2.2271 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6641 6.7275 -1.5441 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7802 6.5700 -1.2053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7377 7.8961 -2.5458 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1436 3.6562 -1.3357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9150 3.6763 -2.3092 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6981 3.0470 -0.1985 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1050 2.8286 1.0577 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2076 2.3663 2.0163 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4729 2.7094 1.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0303 2.5418 -0.1924 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1484 1.1010 -0.6071 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1708 0.4966 -0.2349 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6914 -0.7972 -0.3750 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1051 -0.8875 -0.9100 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1093 -0.2062 -0.0984 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9589 -0.8209 0.7936 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6995 0.1574 1.3365 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3634 1.3663 0.8338 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8301 2.6476 1.0668 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3268 3.7278 0.4196 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3192 3.5465 -0.4993 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8540 2.2674 -0.7307 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3513 1.1485 -0.0822 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5024 -1.6076 0.8419 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1785 -2.8129 0.9540 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7249 -0.9222 2.0580 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1534 0.5177 -1.3607 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3274 4.1846 1.5268 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7464 -1.1027 -0.4338 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7219 -4.0001 1.9558 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3203 -5.9145 -3.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6362 -5.6135 -2.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8767 -4.2680 -2.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2428 -6.6665 -0.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9525 -6.3546 -1.0914 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -4.1674 -0.2694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8586 -6.4170 1.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7564 -4.7958 2.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3732 -5.3735 1.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7668 -3.4194 -1.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6404 -2.8462 2.6939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1270 -2.2788 1.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5839 -3.9970 4.3173 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9748 -3.1862 3.7568 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6152 -5.3935 3.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1258 -5.9822 3.3368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4145 -6.0009 0.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3390 -3.0576 -1.9632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6151 -4.0225 -0.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0239 -4.9179 -1.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3250 -2.1296 -1.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5545 -4.4047 -1.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2396 -3.2079 -2.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2944 -4.7074 -2.8315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3840 -2.4745 -3.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6211 -2.4283 -3.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4538 -4.0361 -3.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7192 -0.3627 0.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0085 -1.0944 2.4415 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9977 -0.2922 3.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5159 -1.2473 2.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5035 0.5931 2.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9848 0.7143 2.9211 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6840 2.0405 0.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6649 3.3834 1.5819 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1474 4.4468 0.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9894 3.2095 -1.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3828 4.7367 -1.9039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0639 5.3487 -0.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7453 3.1958 -1.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8214 3.5082 -2.1360 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6695 5.3469 -3.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2830 5.7110 -2.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2755 7.0214 -0.6532 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2248 7.5356 -0.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9770 5.7625 -0.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3747 6.3458 -2.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6474 7.8244 -3.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5720 8.8607 -2.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1394 7.7219 -3.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6644 2.0066 0.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3902 3.7481 1.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1679 3.0026 2.9237 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1358 1.2846 2.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8542 3.7118 1.4623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2655 1.9506 1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6963 3.1819 -0.8105 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0659 -1.3178 -1.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3773 -1.9499 -1.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0587 -0.4840 -1.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0375 -1.8860 1.0328 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4594 0.0501 2.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6183 2.7689 1.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6841 4.7434 0.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8543 4.3439 -1.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0625 2.0987 -1.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6370 -1.3982 2.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2857 -0.3869 -1.8417 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5993 4.3186 2.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4046 -0.4814 0.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4848 -3.3640 1.8495 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 3 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 15 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 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 3 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 0 35 40 1 0 40 41 2 0 40 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 2 3 48 49 1 0 49 50 1 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 1 0 54 55 2 0 55 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 49 60 1 0 60 61 2 3 60 62 1 0 47 63 1 0 33 64 1 0 20 65 1 0 13 66 1 0 61 5 1 0 12 8 1 0 32 28 1 0 46 42 1 0 59 51 1 0 59 54 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 6 4 73 1 0 4 74 1 0 4 75 1 0 5 76 1 6 9 77 1 0 9 78 1 0 10 79 1 0 10 80 1 0 11 81 1 0 11 82 1 0 12 83 1 6 15 84 1 6 16 85 1 0 16 86 1 0 17 87 1 0 18 88 1 0 18 89 1 0 18 90 1 0 19 91 1 0 19 92 1 0 19 93 1 0 22 94 1 1 23 95 1 1 24 96 1 0 24 97 1 0 24 98 1 0 25 99 1 0 29100 1 0 29101 1 0 30102 1 0 30103 1 0 31104 1 0 31105 1 0 32106 1 6 35107 1 6 36108 1 0 36109 1 0 37110 1 0 38111 1 0 38112 1 0 38113 1 0 39114 1 0 39115 1 0 39116 1 0 43117 1 0 43118 1 0 44119 1 0 44120 1 0 45121 1 0 45122 1 0 46123 1 6 49124 1 6 50125 1 0 50126 1 0 52127 1 0 53128 1 0 55129 1 0 56130 1 0 57131 1 0 58132 1 0 62133 1 0 63134 1 0 64135 1 0 65136 1 0 66137 1 0 M END

Standard InCHIKey	WOEWBNNGDMOZJK-YMMDSMMCSA-N
Standard InCHI	InChI=1S/C48H71N9O9/c1-8-28(6)39-47(65)56-20-12-17-37(56)44(62)50-33(22-26(2)3)41(59)54-40(29(7)58)48(66)57-21-13-18-38(57)45(63)52-35(23-27(4)5)46(64)55-19-11-16-36(55)43(61)51-34(42(60)53-39)24-30-25-49-32-15-10-9-14-31(30)32/h9-10,14-15,25-29,33-40,49,58H,8,11-13,16-24H2,1-7H3,(H,50,62)(H,51,61)(H,52,63)(H,53,60)(H,54,59)/t28-,29+,33-,34-,35-,36-,37-,38-,39-,40-/m0/s1
SMILES	CC[C@H](C)[C@H]1C(=O)N2CCC[C@H]2C(=N[C@@H](CC(C)C)C(=N[C@@H]([C@@H](C)O)C(=O)N2CCC[C@H]2C(=N[C@@H](CC(C)C)C(=O)N2CCC[C@H]2C(=N[C@@H](Cc2c[nH]c3ccccc23)C(=N1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	917.54	Volume:	933.87 ? Van der Waals volume.
Dense:	0.983	LogP:	1.598 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.247 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.223 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	49.0
TPSA:	259.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.585	Fsp³:	0.667
MCE-18:	150.7 ? 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:	0.621	Fluc inhibitor:	0.114 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.074 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.763 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.33

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.628	MDCK Permeability:	-5.266
Pgp-inhibitor:	1.0	Pgp-substrate:	1.0
PAMPA:	0.012 ? 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):	0.992
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:	0.89
Plasma Protein Binding (PPB):	70.944%	Volume Distribution (VD):	-0.199
Fu:	27.788% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.982	BCRP inhibitor:	0.186
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.753	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	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:	0.001 ? 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):

0.959

Half-life (T1/2):

2.349

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:	0.359
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.96	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.418
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	1.0
Hematotoxicity:	0.835	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.442 ? 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:	3.488 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.188 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.356 ? 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
NPO14341	Phakellia fusca	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20345147]
NPO14341	Phakellia fusca	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30844272]
NPO17477	Potentilla indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37765360]
NPO14751	Anisodoris nobilis	Species	Discodorididae	Eukaryota	n.a.	n.a.	n.a.	PMID[7241154]
NPO9435	Acacia georginae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14751	Anisodoris nobilis	Species	Discodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21698	Crinum augustum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12664	Haplanthus tentaculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6751	Clusia grandiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO757	Dorycnium graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14341	Phakellia fusca	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11799	Ursinia saxatilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17233	Picrodendron baccatum	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16836	Polyporus picipes	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16589	Clitocybe conglobata	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17477	Potentilla indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17233	Picrodendron baccatum	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14341	Phakellia fusca	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15034	Intsia bijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17695	Calyptranthes tricona	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17477	Potentilla indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17016	Cassinia aculeata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14751	Anisodoris nobilis	Species	Discodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21698	Crinum augustum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6751	Clusia grandiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11799	Ursinia saxatilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28868	Pardachirus pavoninus	Species	Soleidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17233	Picrodendron baccatum	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO757	Dorycnium graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11480	Haematomma puniceum	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13365	Helminthosporium euchlaenae	Species	Massarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13830	Alcaligenes faecalis	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16589	Clitocybe conglobata	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17935	Pedicularis lasiophrys	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12664	Haplanthus tentaculatus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16723	Gascardia madagascariensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17160	Dimerostemma lippioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16836	Polyporus picipes	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9435	Acacia georginae	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Cell line	1

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
NPT168	Cell line	P388	Mus musculus	IC50	=	8500.0	nM	PMID[20345147]

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 NPC223791 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	18855
0.1-0.2	29121
0.2-0.3	1390
0.3-0.4	355
0.4-0.5	101
0.5-0.6	17
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC107077
0.7204	Intermediate Similarity	NPC489625
0.6765	Remote Similarity	NPC479071
0.6635	Remote Similarity	NPC155143
0.6602	Remote Similarity	NPC110602
0.6569	Remote Similarity	NPC31385
0.6355	Remote Similarity	NPC479065
0.6321	Remote Similarity	NPC479075
0.6316	Remote Similarity	NPC483985
0.6286	Remote Similarity	NPC54420
0.6238	Remote Similarity	NPC293917
0.6182	Remote Similarity	NPC479066
0.6168	Remote Similarity	NPC162860
0.6147	Remote Similarity	NPC479073
0.6126	Remote Similarity	NPC75726
0.6105	Remote Similarity	NPC489556
0.6091	Remote Similarity	NPC479076
0.5922	Remote Similarity	NPC171317
0.5882	Remote Similarity	NPC479574
0.5842	Remote Similarity	NPC213629
0.5818	Remote Similarity	NPC482001
0.573	Remote Similarity	NPC17059
0.569	Remote Similarity	NPC100321
0.5583	Remote Similarity	NPC69843
0.5581	Remote Similarity	NPC49954
0.5566	Remote Similarity	NPC483341
0.5556	Remote Similarity	NPC487314
0.5537	Remote Similarity	NPC325976
0.5537	Remote Similarity	NPC326363
0.5243	Remote Similarity	NPC136797
0.5192	Remote Similarity	NPC261934
0.512	Remote Similarity	NPC489555
0.5094	Remote Similarity	NPC487596
0.5049	Remote Similarity	NPC5194

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC223791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3770
0.1-0.2	5101
0.2-0.3	232
0.3-0.4	37
0.4-0.5	7
0.5-0.6	2
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
0.6238	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5242	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5214	Remote Similarity	NPD7711	Discontinued

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