NPASS Compound

Natural Product: NPC255447

Natural Product ID	NPC255447
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Microtoenin B
IUPAC Name	(3S,9S,12S,15S,18S,21S,24S)-3,15,18-tribenzyl-9,12-dimethyl-21-propan-2-yl-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Synonyms	microtoenin B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502053
PubChem CID	11434381
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 117121 0 0 0 0 0 0 0 0999 V2000 5.2327 3.6768 -1.8171 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5711 2.3926 -1.6732 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3032 1.4427 -1.7034 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5021 0.0672 -1.6484 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9651 -0.2741 -1.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5424 0.2222 -0.1850 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5516 -0.4867 1.0143 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1226 0.0509 2.1422 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7060 1.2936 2.1556 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7127 2.0201 0.9842 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1316 1.4658 -0.1512 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5512 -0.6929 -0.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5505 -0.0698 -0.2882 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5203 -2.0190 -0.4118 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3857 -3.1391 -0.5632 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4007 -3.9123 0.7683 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2420 -3.2836 1.5098 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4356 -2.6252 0.3857 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3354 -1.9099 0.8667 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0659 -2.1908 0.5458 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7313 -3.2794 -0.3369 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7996 -4.6202 0.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2109 -4.6359 1.5471 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5021 -5.7283 -0.5680 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6951 -3.1743 -0.7331 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4942 -2.2015 -0.4235 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8778 -2.2407 -0.8766 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6179 -0.9964 -0.7993 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1751 0.1490 -0.3906 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0689 1.2800 -0.3795 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3368 2.5521 -0.4513 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2094 3.3442 0.5029 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6329 4.5605 0.7994 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2714 4.7868 0.2593 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6557 3.9092 -0.3741 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6447 3.9552 -0.9592 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6796 3.6260 0.0488 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7582 2.9848 -0.2033 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0874 2.5121 -1.5102 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4849 4.0349 1.3575 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 5.2576 -1.6722 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7433 6.0564 0.5192 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5080 4.6819 2.3419 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7459 2.8926 -1.6722 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0250 1.1408 0.7694 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0149 2.2606 0.8796 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8647 3.2875 1.7718 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 4.3032 1.8054 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8779 4.3168 0.9604 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0167 3.2724 0.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1048 2.2576 0.0198 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9796 -0.9811 -1.2076 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6142 -3.3201 -0.0719 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0147 -3.4058 -0.4609 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3913 -4.1175 -1.5678 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7302 -4.2464 -1.9245 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7173 -3.6670 -1.1814 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3556 -2.9488 -0.0655 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0447 -2.8213 0.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2423 -4.2022 -1.5097 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4136 -0.8273 1.7384 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2105 3.7462 -1.5447 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2933 -0.3392 -2.6938 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1940 -1.2683 -1.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4796 0.3745 -2.2484 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0963 -1.4822 1.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1108 -0.5290 3.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1588 1.7211 3.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1746 2.9962 1.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1690 2.0938 -1.0490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4182 -3.0029 -0.8089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9111 -3.8546 -1.3202 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3420 -3.7345 1.2809 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1790 -4.9891 0.5846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5425 -2.5500 2.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6380 -4.0692 1.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0888 -3.4590 -0.3232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3425 -3.2931 -1.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7586 -4.8331 0.8661 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1109 -5.4327 2.2517 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2118 -4.9559 1.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1950 -3.6859 2.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6667 -5.4258 -1.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5279 -6.1287 -0.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2186 -6.5821 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8912 -2.6295 -1.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6762 1.2432 -1.3417 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3274 5.3862 0.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 3.1637 -1.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7852 3.3676 -2.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5004 1.6736 -1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1528 3.9675 2.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6481 5.8884 -1.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1425 5.1019 -2.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0806 5.8399 -1.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2209 6.2759 0.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2877 3.7060 2.7774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6520 5.3640 2.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 5.1569 2.7270 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7787 3.8695 -2.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6074 0.2151 0.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4973 1.0937 1.7508 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0242 3.2966 2.4764 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6715 5.1239 2.5191 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5907 5.1335 1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8728 3.2767 -0.6038 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2130 1.4265 -0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3937 -0.3824 -1.8627 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5640 -2.9974 1.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0693 -4.2732 -0.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6653 -4.6075 -2.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9875 -4.8204 -2.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7432 -3.7836 -1.4799 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1583 -2.4927 0.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8002 -2.2481 1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7830 -4.1123 -2.3286 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6499 -0.5759 2.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 4 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 3 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 21 25 1 0 25 26 2 3 26 27 1 0 27 28 1 0 28 29 2 3 29 30 1 0 30 31 1 0 31 32 2 3 32 33 1 0 33 34 1 0 34 35 2 3 35 36 1 0 36 37 1 0 37 38 2 3 38 39 1 0 37 40 1 0 36 41 1 0 34 42 1 0 33 43 1 0 31 44 1 0 30 45 1 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 28 52 1 0 27 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 25 60 1 0 19 61 1 0 39 2 1 0 51 46 1 0 59 54 1 0 11 6 1 0 18 14 1 0 1 62 1 0 4 63 1 6 5 64 1 0 5 65 1 0 7 66 1 0 8 67 1 0 9 68 1 0 10 69 1 0 11 70 1 0 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 0 17 76 1 0 18 77 1 6 21 78 1 6 22 79 1 0 23 80 1 0 23 81 1 0 23 82 1 0 24 83 1 0 24 84 1 0 24 85 1 0 27 86 1 6 30 87 1 6 33 88 1 6 36 89 1 6 39 90 1 0 39 91 1 0 40 92 1 0 41 93 1 0 41 94 1 0 41 95 1 0 42 96 1 0 43 97 1 0 43 98 1 0 43 99 1 0 44100 1 0 45101 1 0 45102 1 0 47103 1 0 48104 1 0 49105 1 0 50106 1 0 51107 1 0 52108 1 0 53109 1 0 53110 1 0 55111 1 0 56112 1 0 57113 1 0 58114 1 0 59115 1 0 60116 1 0 61117 1 0 M END

Standard InCHIKey	OQEDQPROIDLGAM-SRZLETEKSA-N
Standard InCHI	InChI=1S/C45H56N8O8/c1-27(2)38-44(60)51-34(24-31-17-10-6-11-18-31)42(58)50-33(23-30-15-8-5-9-16-30)41(57)48-29(4)40(56)47-28(3)39(55)46-26-37(54)49-35(25-32-19-12-7-13-20-32)45(61)53-22-14-21-36(53)43(59)52-38/h5-13,15-20,27-29,33-36,38H,14,21-26H2,1-4H3,(H,46,55)(H,47,56)(H,48,57)(H,49,54)(H,50,58)(H,51,60)(H,52,59)/t28-,29-,33-,34-,35-,36-,38-/m0/s1
SMILES	OC1=N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@H]2C(=N[C@@H](C(C)C)C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=NC1)O)C)O)C)O)Cc1ccccc1)O)Cc1ccccc1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	836.42	Volume:	857.57 ? Van der Waals volume.
Dense:	0.975	LogP:	0.927 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.804 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.942 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	47.0
TPSA:	248.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.102	Fsp³:	0.422
MCE-18:	117.031 ? 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:	0.431	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.968 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.006

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.905	MDCK Permeability:	-4.959
Pgp-inhibitor:	0.999	Pgp-substrate:	1.0
PAMPA:	0.745 ? 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):	0.632
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:	0.939
Plasma Protein Binding (PPB):	63.767%	Volume Distribution (VD):	-0.291
Fu:	32.494% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.827	BCRP inhibitor:	0.004
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.022	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	1.0 ? 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):

0.079

Half-life (T1/2):

1.971

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:	0.0	Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.99
Drug-induced Neurotoxicity:	0.438	Ototoxicity:	1.0
Hematotoxicity:	0.149	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.378 ? 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:	3.344 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.889 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.928 ? 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
NPO21245	Microtoena prainiana	Species	Lamiaceae	Eukaryota	stems	n.a.	n.a.	PMID[15217277]
NPO21245	Microtoena prainiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21245	Microtoena prainiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[15217277]

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 NPC255447 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	23072
0.1-0.2	25168
0.2-0.3	1149
0.3-0.4	322
0.4-0.5	104
0.5-0.6	25
0.6-0.7	14
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	Natural Product ID
0.68	Remote Similarity	NPC486664
0.6538	Remote Similarity	NPC287401
0.6456	Remote Similarity	NPC202521
0.6456	Remote Similarity	NPC485094
0.642	Remote Similarity	NPC6975
0.6364	Remote Similarity	NPC489593
0.6353	Remote Similarity	NPC141957
0.6329	Remote Similarity	NPC202198
0.6154	Remote Similarity	NPC285926
0.6154	Remote Similarity	NPC14672
0.6098	Remote Similarity	NPC479072
0.6047	Remote Similarity	NPC101679
0.6047	Remote Similarity	NPC300315
0.6	Remote Similarity	NPC479074
0.5882	Remote Similarity	NPC56685
0.5814	Remote Similarity	NPC130309
0.5783	Remote Similarity	NPC489824
0.5732	Remote Similarity	NPC248283
0.5732	Remote Similarity	NPC489557
0.573	Remote Similarity	NPC213629
0.5679	Remote Similarity	NPC485876
0.561	Remote Similarity	NPC489591
0.5542	Remote Similarity	NPC200964
0.5542	Remote Similarity	NPC252878
0.5465	Remote Similarity	NPC489822
0.5443	Remote Similarity	NPC262077
0.5432	Remote Similarity	NPC242482
0.5385	Remote Similarity	NPC200589
0.5366	Remote Similarity	NPC224315
0.5312	Remote Similarity	NPC328649
0.5222	Remote Similarity	NPC136797
0.5192	Remote Similarity	NPC473003
0.5176	Remote Similarity	NPC479068
0.5119	Remote Similarity	NPC223956
0.5111	Remote Similarity	NPC322878
0.5109	Remote Similarity	NPC241794
0.5059	Remote Similarity	NPC46427
0.5052	Remote Similarity	NPC275110
0.505	Remote Similarity	NPC238945

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC255447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2632
0.1-0.2	5998
0.2-0.3	461
0.3-0.4	53
0.4-0.5	6
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