NPASS Compound

Natural Product: NPC489593

Natural Product ID	NPC489593
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IKNYDQPOUFINIU-TXEVMWFESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46882533
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 2.8609 -5.6612 3.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0172 -4.9074 2.7992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8906 -4.0163 1.9110 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8853 -4.8288 1.1502 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 -3.1530 1.0177 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9569 -2.3040 0.1754 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0283 -1.0943 0.4134 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6934 0.0398 -0.0382 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6100 -0.2198 -1.1862 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3072 1.0141 -1.6893 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8686 1.6890 -2.7919 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4921 2.8497 -3.2486 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5826 3.3399 -2.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0407 2.6768 -1.4673 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4163 1.5379 -1.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9133 1.3078 -0.1312 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4845 1.7797 -1.2279 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7544 2.9568 -1.4121 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1248 2.8276 -2.8356 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3734 3.9397 -3.1017 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7136 3.3343 -0.4503 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0907 2.5198 0.2069 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3355 4.6657 -0.1852 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9460 5.8273 -0.7404 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2734 6.6543 -1.1131 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0980 6.4677 0.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6799 5.1077 0.7041 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8947 4.2459 0.8081 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0052 3.3193 1.6264 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9559 2.3462 1.9926 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0652 2.8450 2.8366 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4685 3.4328 4.1480 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1248 1.9161 3.2690 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8815 1.3363 2.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2757 1.4716 0.8553 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8345 0.2878 0.8888 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9256 -0.8226 0.0077 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5055 -0.4569 -1.4058 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5647 -1.5511 -2.3742 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7437 -1.7996 -3.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8263 -2.8092 -4.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7038 -3.5936 -4.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5162 -3.3671 -3.5515 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4631 -2.3449 -2.6207 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9716 -1.8390 0.5767 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -1.4208 1.2034 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0588 -3.2242 0.4933 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0191 -4.0860 -0.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7201 -5.4688 0.4450 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6280 -5.3167 1.4653 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9663 -4.0295 1.0793 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0719 -4.2981 0.0666 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2689 -3.9201 0.0867 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3645 -5.0717 -1.0393 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0147 1.8070 -0.2654 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9335 4.5366 -0.0808 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6141 2.0425 1.0185 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6896 -2.9214 -0.8141 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1868 -5.9893 4.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3114 -6.5859 3.3725 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6155 -4.9948 4.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5156 -5.6525 2.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3120 -4.2758 3.3683 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4359 -3.3403 2.6017 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1799 -5.7291 1.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5107 -5.0888 0.1530 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8374 -4.2707 1.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3987 -2.5275 1.6558 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4586 0.2746 0.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4871 -0.8222 -0.7735 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1907 -0.8104 -1.9980 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0386 1.3508 -3.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1150 3.3682 -4.1388 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0879 4.2615 -2.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8965 3.0665 -0.9474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7541 1.0047 -0.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4544 3.8484 -1.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9369 2.6546 -3.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5070 1.8918 -2.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9437 4.5626 -3.6305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4824 6.3587 0.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6682 5.6994 -1.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0546 7.6929 -1.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7536 6.3289 -2.0318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1559 6.4160 -0.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9719 7.2654 0.8844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2883 5.2574 1.7544 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3619 1.6604 2.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4955 3.7710 2.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3491 3.6723 4.7760 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8123 4.2750 3.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9492 2.5624 4.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7512 1.1172 3.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9014 2.4387 3.9112 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1388 2.1339 1.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4632 0.4666 1.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9249 0.9974 2.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9131 -1.2983 -0.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0016 0.4359 -1.7962 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4156 -0.1630 -1.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6117 -1.1692 -2.8856 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7125 -3.0334 -4.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7647 -4.3869 -4.9794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6318 -3.9767 -3.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5603 -2.1491 -2.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0204 -3.8097 0.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2115 -4.0358 -1.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3712 -6.0729 -0.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6146 -5.9676 0.9042 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1114 -5.2581 2.4685 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9035 -6.1562 1.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6073 -3.4759 1.9509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2782 -5.2316 -1.8168 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8234 1.2558 -0.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9175 4.4275 0.1428 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6100 3.0625 1.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6684 -2.9039 -0.9580 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 3 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 8 16 1 0 16 17 2 3 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 21 22 2 0 21 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 2 3 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 30 35 1 0 35 36 2 3 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 37 45 1 0 45 46 2 0 45 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 3 52 54 1 0 35 55 1 0 28 56 1 0 16 57 1 0 6 58 1 0 53 5 1 0 15 10 1 0 27 23 1 0 44 39 1 0 51 47 1 0 1 59 1 0 1 60 1 0 1 61 1 0 2 62 1 0 2 63 1 0 3 64 1 1 4 65 1 0 4 66 1 0 4 67 1 0 5 68 1 1 8 69 1 1 9 70 1 0 9 71 1 0 11 72 1 0 12 73 1 0 13 74 1 0 14 75 1 0 15 76 1 0 18 77 1 6 19 78 1 0 19 79 1 0 20 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 26 85 1 0 26 86 1 0 27 87 1 1 30 88 1 1 31 89 1 6 32 90 1 0 32 91 1 0 32 92 1 0 33 93 1 0 33 94 1 0 34 95 1 0 34 96 1 0 34 97 1 0 37 98 1 6 38 99 1 0 38100 1 0 40101 1 0 41102 1 0 42103 1 0 43104 1 0 44105 1 0 48106 1 0 48107 1 0 49108 1 0 49109 1 0 50110 1 0 50111 1 0 51112 1 1 54113 1 0 55114 1 0 56115 1 0 57116 1 0 58117 1 0 M END

Standard InCHIKey	IKNYDQPOUFINIU-TXEVMWFESA-N
Standard InCHI	InChI=1S/C43H59N7O8/c1-5-26(3)35-40(55)44-30(23-28-15-9-7-10-16-28)37(52)46-32(25-51)43(58)50-22-14-20-34(50)39(54)48-36(27(4)6-2)41(56)45-31(24-29-17-11-8-12-18-29)42(57)49-21-13-19-33(49)38(53)47-35/h7-12,15-18,26-27,30-36,51H,5-6,13-14,19-25H2,1-4H3,(H,44,55)(H,45,56)(H,46,52)(H,47,53)(H,48,54)/t26-,27-,30+,31+,32+,33+,34+,35+,36+/m1/s1
SMILES	CC[C@@H](C)[C@H]1C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](CO)C(=O)N2CCC[C@H]2C(=N[C@@H]([C@H](C)CC)C(=N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@H]2C(=N1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	801.44	Volume:	822.527 ? Van der Waals volume.
Dense:	0.974	LogP:	1.334 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.11 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.883 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	43.0
TPSA:	223.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.198	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.103	Fsp³:	0.558
MCE-18:	118.582 ? 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:	0.357	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.912 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.002	Promiscuous compounds:	0.016

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.438	MDCK Permeability:	-5.06
Pgp-inhibitor:	1.0	Pgp-substrate:	1.0
PAMPA:	0.028 ? 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):	0.834
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:	0.546
Plasma Protein Binding (PPB):	66.013%	Volume Distribution (VD):	-0.302
Fu:	29.179% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.465	BCRP inhibitor:	0.405
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.1	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.005	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:	0.013 ? 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):

1.497

Half-life (T1/2):

1.838

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:	0.002	Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.229	Skin Sensitization:	1.0
Carcinogencity:	0.08	Eye Corrosion:	0.0
Eye Irritation:	0.018	Respiratory Toxicity:	0.946
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	1.0
Hematotoxicity:	0.189	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.413 ? 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:	3.375 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.956 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.948 ? 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

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
Activity	4

Activity Type	# Activity
Cell line	4

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
NPT455	Cell line	NCI-H522	Homo sapiens	Activity	=	94.6	%	PMID[19743810]
NPT390	Cell line	LOX IMVI	Homo sapiens	Activity	=	87.6	%	PMID[19743810]
NPT458	Cell line	IGROV-1	Homo sapiens	Activity	=	100.0	%	PMID[19743810]
NPT371	Cell line	UO-31	Homo sapiens	Activity	=	82.7	%	PMID[19743810]

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 NPC489593 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	13063
0.1-0.2	34703
0.2-0.3	1637
0.3-0.4	291
0.4-0.5	105
0.5-0.6	38
0.6-0.7	16
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
0.7432	Intermediate Similarity	NPC489824
0.7397	Intermediate Similarity	NPC489557
0.6883	Remote Similarity	NPC479072
0.6883	Remote Similarity	NPC489592
0.6757	Remote Similarity	NPC224315
0.6711	Remote Similarity	NPC287401
0.6622	Remote Similarity	NPC242482
0.6543	Remote Similarity	NPC479074
0.6447	Remote Similarity	NPC485876
0.6364	Remote Similarity	NPC255447
0.6349	Remote Similarity	NPC285926
0.6349	Remote Similarity	NPC14672
0.6282	Remote Similarity	NPC200964
0.6145	Remote Similarity	NPC130309
0.6076	Remote Similarity	NPC252878
0.6022	Remote Similarity	NPC54420
0.6	Remote Similarity	NPC262077
0.6	Remote Similarity	NPC489829
0.5976	Remote Similarity	NPC6975
0.5946	Remote Similarity	NPC200589
0.593	Remote Similarity	NPC241794
0.5914	Remote Similarity	NPC489590
0.5875	Remote Similarity	NPC479068
0.5814	Remote Similarity	NPC489825
0.5814	Remote Similarity	NPC489826
0.573	Remote Similarity	NPC302597
0.5698	Remote Similarity	NPC136797
0.5679	Remote Similarity	NPC202198
0.5618	Remote Similarity	NPC489165
0.561	Remote Similarity	NPC202521
0.5568	Remote Similarity	NPC141957
0.5517	Remote Similarity	NPC479070
0.55	Remote Similarity	NPC486664
0.5422	Remote Similarity	NPC485094
0.5412	Remote Similarity	NPC489822
0.5397	Remote Similarity	NPC25565
0.5397	Remote Similarity	NPC475439
0.5376	Remote Similarity	NPC489828
0.5366	Remote Similarity	NPC489591
0.5294	Remote Similarity	NPC88267
0.5286	Remote Similarity	NPC242159
0.5263	Remote Similarity	NPC328649
0.5165	Remote Similarity	NPC479069
0.5143	Remote Similarity	NPC175726
0.5143	Remote Similarity	NPC224610
0.5143	Remote Similarity	NPC113326
0.5143	Remote Similarity	NPC474082
0.5119	Remote Similarity	NPC16188
0.5119	Remote Similarity	NPC248283
0.5114	Remote Similarity	NPC5194
0.5111	Remote Similarity	NPC101679
0.5111	Remote Similarity	NPC261934
0.5057	Remote Similarity	NPC473322
0.5056	Remote Similarity	NPC322878
0.5051	Remote Similarity	NPC110602
0.5051	Remote Similarity	NPC479071

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2069
0.1-0.2	6494
0.2-0.3	532
0.3-0.4	51
0.4-0.5	3
0.5-0.6	1
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
0.5366	Remote Similarity	NPD4791	Clinical (unspecified phase)

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