NPASS Compound

Natural Product: NPC253482

Natural Product ID	NPC253482
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Alatamine
IUPAC Name	n.a.
Synonyms	Alatamine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503871
PubChem CID	21763826
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 105110 0 0 0 0 0 0 0 0999 V2000 -5.4677 -1.8592 3.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0077 -1.7265 3.5692 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3452 -1.7771 4.6228 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3256 -1.5380 2.3740 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8817 -1.4064 2.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3812 -1.2098 0.9827 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0167 0.0297 0.3919 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4931 0.9462 1.3383 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8039 1.4063 1.3828 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6036 0.9524 0.4978 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2787 2.3717 2.3905 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0657 0.8010 -0.5322 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8232 1.9597 -0.8970 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2442 2.2040 -2.1872 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9542 1.3727 -3.0848 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0045 3.4072 -2.4646 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3016 4.2913 -1.4584 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0344 5.4507 -1.7256 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4671 5.7196 -3.0033 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1715 4.8303 -4.0305 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4354 3.6757 -3.7349 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0699 1.2684 0.2950 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6591 0.2145 1.2228 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1330 -1.1436 0.8704 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5473 -1.3463 -0.4516 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8822 -2.6283 -0.6845 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4115 -3.3975 0.5614 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0351 -3.5895 0.3718 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5172 -4.7289 0.3641 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8920 -2.3885 0.1919 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1746 -2.7647 0.6507 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3109 -2.7629 -0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1513 -2.3915 -1.3462 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6599 -3.1579 0.3469 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7277 -2.2874 1.5865 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1545 -2.2242 1.6406 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7960 -2.5471 2.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0794 -2.8868 3.8107 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2738 -2.5146 2.9881 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0783 -3.1186 -1.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2927 -2.9703 -0.9402 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2216 -1.9556 -0.8107 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5704 -2.0413 -1.0145 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0281 -3.1767 -1.3669 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5478 -0.9858 -0.8747 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7812 -1.3221 -0.2950 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7798 -0.3976 -0.1165 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5762 0.9050 -0.5152 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3954 1.2116 -1.0664 N 0 0 0 0 0 0 0 0 0 0 0 0 5.3938 0.3231 -1.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1500 0.7944 -1.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9335 2.2711 -1.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6039 2.6554 -2.2473 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5072 1.8322 -1.6420 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9988 0.9718 -2.3847 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.9922 -0.3608 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2720 4.0955 -2.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7620 2.3470 -3.5941 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 0.6204 2.6496 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0439 0.2390 0.9278 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9418 -1.3922 2.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8872 -1.3192 4.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7898 -2.9327 3.5724 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.6078 3.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5748 -2.3682 2.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8914 -0.2154 -0.2638 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4127 3.0273 2.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1018 2.9538 1.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6561 1.7893 3.2530 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8638 0.1983 -1.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9599 4.0786 -0.4500 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2753 6.1544 -0.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0403 6.6182 -3.2348 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5201 5.0652 -5.0104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2316 3.0144 -4.5725 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3875 2.0334 1.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9877 -4.2966 0.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0335 -2.1033 -0.8642 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3352 -2.3038 0.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5407 -3.6775 1.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0814 -3.9113 -0.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3065 -2.5973 2.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7543 -1.7298 2.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7056 -3.5224 2.8236 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4714 -2.2546 4.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7561 -3.6475 -2.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3103 -2.2662 -2.4969 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6574 -3.8838 -1.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6399 -3.8080 -0.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4583 -3.4169 -1.9672 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9543 -2.3531 0.0253 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7382 -0.6569 0.3334 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3480 1.6655 -0.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3014 0.2454 -1.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2644 0.7054 -2.9689 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7485 2.8608 -2.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8802 2.5212 -0.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6411 4.4239 -2.9720 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6613 4.2725 -1.2005 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1915 4.7132 -2.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6433 2.6044 -3.9246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4617 1.2516 2.9514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2805 1.3072 2.8655 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6384 -0.2354 3.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4511 1.0808 1.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 6 5 1 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 7 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 12 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 27 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 26 40 1 6 26 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 2 0 54 56 1 0 53 57 1 0 53 58 1 0 23 59 1 0 23 60 1 6 30 6 1 0 50 45 1 0 24 6 1 0 21 16 1 0 56 22 1 0 35 24 1 0 1 61 1 0 1 62 1 0 1 63 1 0 5 64 1 0 5 65 1 0 7 66 1 6 11 67 1 0 11 68 1 0 11 69 1 0 12 70 1 6 17 71 1 0 18 72 1 0 19 73 1 0 20 74 1 0 21 75 1 0 22 76 1 1 27 77 1 1 30 78 1 6 34 79 1 0 34 80 1 0 34 81 1 0 35 82 1 1 39 83 1 0 39 84 1 0 39 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 41 90 1 0 46 91 1 0 47 92 1 0 48 93 1 0 51 94 1 0 51 95 1 0 52 96 1 0 52 97 1 0 57 98 1 0 57 99 1 0 57100 1 0 58101 1 0 59102 1 0 59103 1 0 59104 1 0 60105 1 0 M END

Standard InCHIKey	WLMGYTNCKLQIDI-WUMUXXSDSA-N
Standard InCHI	InChI=1S/C41H45NO18/c1-20(43)53-19-40-31(56-22(3)45)28(47)27-30(55-21(2)44)41(40)39(7,52)32(29(33(40)57-23(4)46)58-34(48)24-12-9-8-10-13-24)59-36(50)37(5,51)16-15-26-25(14-11-17-42-26)35(49)54-18-38(27,6)60-41/h8-14,17,27,29-33,51-52H,15-16,18-19H2,1-7H3/t27-,29+,30-,31-,32+,33+,37?,38+,39+,40-,41+/m1/s1
SMILES	CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)c3ccccc3)[C@H]3[C@]([C@@]42O[C@@]([C@H](C(=O)[C@H]1OC(=O)C)[C@H]4OC(=O)C)(C)COC(=O)c1cccnc1CCC(C(=O)O3)(C)O)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	839.26	Volume:	798.664 ? Van der Waals volume.
Dense:	1.051	LogP:	0.854 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.371 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.221 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	44.0
TPSA:	263.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.29	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.535	Fsp³:	0.537
MCE-18:	222.222 ? 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:	0.114	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.276 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.013	Promiscuous compounds:	0.221

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.627	MDCK Permeability:	-4.857
Pgp-inhibitor:	0.097	Pgp-substrate:	0.108
PAMPA:	0.993 ? 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):	0.0
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.013
50% Bioavailability (F50%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	1.0
Plasma Protein Binding (PPB):	51.815%	Volume Distribution (VD):	-0.246
Fu:	45.599% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.0
BSEP inhibitor:	0.84

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.006	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.955
HLM stability:	0.008 ? 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):

0.591

Half-life (T1/2):

1.539

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.039
Human Hepatotoxicity (H-HT):	0.465	Drug-induced Liver Injury (DILI):	0.916
AMES Toxicity:	0.992	Rat Oral Acute Toxicity:	0.57
Maximum Recommended Daily Dose:	0.837	Skin Sensitization:	1.0
Carcinogencity:	0.796	Eye Corrosion:	0.0
Eye Irritation:	0.021	Respiratory Toxicity:	0.054
Drug-induced Neurotoxicity:	0.35	Ototoxicity:	0.674
Hematotoxicity:	0.873	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.635
A549 Cytotoxicity:	0.367	Hek293 Cytotoxicity:	0.213
BCF:	0.508 ? 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:	3.234 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.706 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.151 ? 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
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16795	Ramulus euonymi	Species	Phasmatidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1333	Maytenus chiapensis	Species	Celastraceae	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
EC50	1
Activity	2

Activity Type	# Activity
Organism	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
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	EC50	=	5.2	10'-3 ug/cm2	PMID[14738378]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	117.0	%	PMID[14738378]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Activity	=	118.0	%	PMID[14738378]

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 NPC253482 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	17705
0.1-0.2	30699
0.2-0.3	1177
0.3-0.4	189
0.4-0.5	30
0.5-0.6	29
0.6-0.7	17
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9579	High Similarity	NPC475648
0.8416	Intermediate Similarity	NPC601643
0.8137	Intermediate Similarity	NPC473689
0.8137	Intermediate Similarity	NPC292416
0.7885	Intermediate Similarity	NPC475406
0.7619	Intermediate Similarity	NPC483894
0.7453	Intermediate Similarity	NPC483893
0.729	Intermediate Similarity	NPC600607
0.7238	Intermediate Similarity	NPC122968
0.7238	Intermediate Similarity	NPC228377
0.7019	Intermediate Similarity	NPC146824
0.7019	Intermediate Similarity	NPC483892
0.6944	Remote Similarity	NPC13603
0.6818	Remote Similarity	NPC611166
0.6759	Remote Similarity	NPC328186
0.6635	Remote Similarity	NPC35208
0.6549	Remote Similarity	NPC319880
0.6549	Remote Similarity	NPC320324
0.6545	Remote Similarity	NPC316841
0.6491	Remote Similarity	NPC38959
0.646	Remote Similarity	NPC244839
0.6396	Remote Similarity	NPC475600
0.6348	Remote Similarity	NPC327904
0.633	Remote Similarity	NPC475601
0.6168	Remote Similarity	NPC250807
0.6168	Remote Similarity	NPC57797
0.6126	Remote Similarity	NPC53255
0.6126	Remote Similarity	NPC85879
0.6106	Remote Similarity	NPC87152
0.5982	Remote Similarity	NPC475362
0.5965	Remote Similarity	NPC475631
0.5946	Remote Similarity	NPC473833
0.5913	Remote Similarity	NPC476110
0.5882	Remote Similarity	NPC327769
0.5882	Remote Similarity	NPC471979
0.5877	Remote Similarity	NPC475303
0.5776	Remote Similarity	NPC475596
0.5763	Remote Similarity	NPC237702
0.569	Remote Similarity	NPC471977
0.568	Remote Similarity	NPC483854
0.563	Remote Similarity	NPC600583
0.5583	Remote Similarity	NPC477787
0.5512	Remote Similarity	NPC482915
0.5446	Remote Similarity	NPC473850
0.5424	Remote Similarity	NPC328154
0.5424	Remote Similarity	NPC470486
0.5398	Remote Similarity	NPC76565
0.5398	Remote Similarity	NPC601313
0.5392	Remote Similarity	NPC51602
0.5385	Remote Similarity	NPC326930
0.5372	Remote Similarity	NPC600546
0.5349	Remote Similarity	NPC483855
0.5333	Remote Similarity	NPC475644
0.5207	Remote Similarity	NPC30456
0.5207	Remote Similarity	NPC488904
0.512	Remote Similarity	NPC483853
0.512	Remote Similarity	NPC608314
0.5083	Remote Similarity	NPC475301

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3832
0.1-0.2	5261
0.2-0.3	55
0.3-0.4	2
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