NPASS Compound

Natural Product: NPC482766

Natural Product ID	NPC482766
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CZAWTGJMUZROEX-MTKKOKBRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44559000
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 109111 0 0 0 0 0 0 0 0999 V2000 12.7923 4.2231 -0.4180 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5927 3.3353 -0.0067 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9004 1.9072 -0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9545 0.8724 0.1187 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5498 0.8778 -0.3404 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6747 1.9640 0.1201 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2654 1.7871 -0.4702 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7239 0.4633 -0.0113 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2895 0.3614 -0.5289 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6242 -0.9245 -0.1710 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5677 -1.2252 1.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8643 -0.2096 2.1202 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4529 0.0282 1.7823 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0832 0.9136 1.0289 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4226 -0.8369 2.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.3757 2.0325 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9191 -1.3675 2.6983 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1277 -2.3755 1.5721 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0906 -1.4469 0.3777 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4916 -0.9288 0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6193 0.0155 -0.9892 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2108 -0.5976 -2.3021 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0525 -1.8154 -2.6371 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7827 -2.2738 -4.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0624 -2.9347 -4.4550 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0434 -2.5453 -3.3167 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2131 -3.7545 -2.5010 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0975 -3.8706 -1.3609 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0805 -3.1074 -0.1326 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3452 -1.6403 -0.1149 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3196 -1.1461 1.3615 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5847 0.3139 1.4351 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9255 0.6441 0.8616 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1903 2.1292 0.9503 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4077 3.0409 1.4486 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0480 4.3605 1.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2646 4.8869 2.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2734 4.0979 0.7060 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3952 2.7491 0.4618 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3723 2.1361 -0.0881 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6166 1.0222 0.7358 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3849 -1.4895 -2.7001 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3784 0.3720 -3.2815 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2810 -0.3973 0.7060 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3267 -3.0465 1.6988 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3502 3.6654 -1.1856 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4358 4.4373 0.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4233 5.1624 -0.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7896 3.6588 -0.7359 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2463 3.5405 0.9920 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1820 1.7965 -1.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8902 1.6659 0.2276 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8886 0.8831 1.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3466 -0.1750 -0.1403 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5289 0.8270 -1.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0905 -0.1129 -0.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9281 2.9944 -0.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5545 1.8641 1.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3325 1.7834 -1.5898 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5961 2.5955 -0.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8044 0.3904 1.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2559 -0.3774 -0.5499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6753 1.2128 -0.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4058 0.3575 -1.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5872 -0.8843 -0.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1000 -1.8078 -0.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5764 -1.4293 1.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0326 -2.2087 1.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3951 0.7839 2.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8945 -0.4861 3.1969 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5317 -0.9641 3.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5098 -1.8844 1.9673 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1723 0.6532 2.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8884 -0.9115 3.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4257 -1.8436 3.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2407 -3.0354 1.5680 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7245 -1.9917 -0.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2375 -1.7557 0.1164 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7756 -0.3672 1.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6185 0.4446 -1.0012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9141 0.8754 -0.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1397 -0.8652 -2.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8573 -2.6383 -1.9340 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6336 -1.3530 -4.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9055 -2.9520 -4.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4450 -2.5889 -5.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8872 -4.0277 -4.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9661 -2.2083 -3.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1567 -4.1397 -2.2689 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5559 -4.5703 -3.2541 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9957 -4.9969 -1.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2020 -3.9346 -1.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8998 -3.5455 0.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1611 -3.3439 0.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3935 -1.4736 -0.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6027 -0.9914 -0.5912 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2832 -1.3401 1.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0161 -1.7507 1.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4895 0.6678 2.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7390 0.1672 1.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9131 0.4402 -0.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4106 2.8678 1.8930 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4170 5.0716 0.7603 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4471 5.6153 2.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2437 4.0573 3.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2334 5.4240 2.8488 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8802 1.2314 -0.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8565 1.1855 -3.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4766 -3.5572 0.8638 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 4 5 1 0 5 6 1 0 6 7 1 0 7 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 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 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 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 2 0 32 41 1 0 26 42 1 0 22 43 1 0 19 44 1 0 18 45 1 0 44 16 1 0 42 23 1 0 39 34 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 2 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 7 60 1 0 8 61 1 0 8 62 1 0 9 63 1 0 9 64 1 0 10 65 1 0 10 66 1 0 11 67 1 0 11 68 1 0 12 69 1 0 12 70 1 0 15 71 1 0 15 72 1 0 16 73 1 1 17 74 1 0 17 75 1 0 18 76 1 6 19 77 1 6 20 78 1 0 20 79 1 0 21 80 1 0 21 81 1 0 22 82 1 1 23 83 1 1 24 84 1 0 24 85 1 0 25 86 1 0 25 87 1 0 26 88 1 6 27 89 1 0 27 90 1 0 28 91 1 0 28 92 1 0 29 93 1 0 29 94 1 0 30 95 1 0 30 96 1 0 31 97 1 0 31 98 1 0 32 99 1 0 33100 1 0 33101 1 0 35102 1 0 36103 1 0 37104 1 0 37105 1 0 37106 1 0 41107 1 0 43108 1 0 45109 1 0 M END

Standard InCHIKey	CZAWTGJMUZROEX-MTKKOKBRSA-N
Standard InCHI	InChI=1S/C37H64O8/c1-3-4-5-6-7-8-9-10-11-13-17-30(39)25-32-26-34(41)36(45-32)22-20-33(40)35-21-19-31(44-35)18-15-12-14-16-29(38)24-28-23-27(2)43-37(28)42/h23,27,29,31-36,38,40-41H,3-22,24-26H2,1-2H3/t27?,29?,31-,32-,33+,34-,35+,36-/m1/s1
SMILES	CCCCCCCCCCCCC(=O)C[C@@H]1C[C@H]([C@@H](CC[C@@H]([C@@H]2CC[C@@H](CCCCCC(CC3=CC(C)OC3=O)O)O2)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	636.46	Volume:	685.251 ? Van der Waals volume.
Dense:	0.929	LogP:	5.305 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.099 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.452 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	17.0
TPSA:	122.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.072	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.88	Fsp³:	0.892
MCE-18:	45.143 ? 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:	0.879	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.041 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.009 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.474	Promiscuous compounds:	0.287

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166	MDCK Permeability:	-4.826
Pgp-inhibitor:	0.0	Pgp-substrate:	0.384
PAMPA:	0.184 ? 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):	0.042
20% Bioavailability (F20%):	0.903	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.967
Plasma Protein Binding (PPB):	95.408%	Volume Distribution (VD):	0.462
Fu:	4.391% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.662
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.078
BSEP inhibitor:	0.698

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.329	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.013	CYP3A4-substrate:	0.34
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.948
HLM stability:	0.014 ? 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):

5.434

Half-life (T1/2):

0.961

ADMET: Toxicity

hERG Blockers:	0.486	hERG Blockers (10um):	0.796
Human Hepatotoxicity (H-HT):	0.563	Drug-induced Liver Injury (DILI):	0.52
AMES Toxicity:	0.155	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.828	Skin Sensitization:	1.0
Carcinogencity:	0.081	Eye Corrosion:	0.01
Eye Irritation:	0.643	Respiratory Toxicity:	0.891
Drug-induced Neurotoxicity:	0.093	Ototoxicity:	0.905
Hematotoxicity:	0.328	Drug-induced Nephrotoxicity:	0.941
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.981	Hek293 Cytotoxicity:	0.517
BCF:	0.913 ? 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:	4.83 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.218 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.493 ? 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
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	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
ED50	6

Activity Type	# Activity
Cell line	6

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.3	10'-2 ug/ml	PMID[9917277]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	3.3	10'-3 ug/ml	PMID[9917277]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.2	10'-3 ug/ml	PMID[9917277]
NPT376	Cell line	A498	Homo sapiens	ED50	=	1.1	10'-3 ug/ml	PMID[9917277]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	2.6	10'-1 ug/ml	PMID[9917277]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[9917277]

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
-	Aedes aegypti	LC50	=	3.6	ug.mL-1	PMID[9917277]
-	Artemia	LC50	=	2.7	ug.mL-1	PMID[9917277]

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 NPC482766 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	18347
0.1-0.2	29546
0.2-0.3	1678
0.3-0.4	61
0.4-0.5	54
0.5-0.6	65
0.6-0.7	78
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
0.7414	Intermediate Similarity	NPC20621
0.7414	Intermediate Similarity	NPC318963
0.7414	Intermediate Similarity	NPC605101
0.7288	Intermediate Similarity	NPC473478
0.7288	Intermediate Similarity	NPC473651
0.7288	Intermediate Similarity	NPC66346
0.7241	Intermediate Similarity	NPC473687
0.7241	Intermediate Similarity	NPC204686
0.7241	Intermediate Similarity	NPC219498
0.7241	Intermediate Similarity	NPC308412
0.7241	Intermediate Similarity	NPC134885
0.7241	Intermediate Similarity	NPC488247
0.7241	Intermediate Similarity	NPC210218
0.7241	Intermediate Similarity	NPC488248
0.7167	Intermediate Similarity	NPC231096
0.7167	Intermediate Similarity	NPC475581
0.7167	Intermediate Similarity	NPC283085
0.7167	Intermediate Similarity	NPC62118
0.7167	Intermediate Similarity	NPC107717
0.7167	Intermediate Similarity	NPC488252
0.6885	Remote Similarity	NPC169511
0.6885	Remote Similarity	NPC287164
0.6885	Remote Similarity	NPC234077
0.6885	Remote Similarity	NPC132496
0.6833	Remote Similarity	NPC134807
0.6825	Remote Similarity	NPC480081
0.6667	Remote Similarity	NPC477017
0.6667	Remote Similarity	NPC477016
0.6613	Remote Similarity	NPC606740
0.6613	Remote Similarity	NPC608614
0.6562	Remote Similarity	NPC91067
0.6508	Remote Similarity	NPC233551
0.6508	Remote Similarity	NPC40376
0.6508	Remote Similarity	NPC21208
0.6491	Remote Similarity	NPC606043
0.6462	Remote Similarity	NPC477015
0.6441	Remote Similarity	NPC182383
0.6418	Remote Similarity	NPC279267
0.6379	Remote Similarity	NPC107986
0.6379	Remote Similarity	NPC223871
0.6379	Remote Similarity	NPC231009
0.6379	Remote Similarity	NPC103284
0.6379	Remote Similarity	NPC110710
0.6379	Remote Similarity	NPC1083
0.6379	Remote Similarity	NPC82795
0.6379	Remote Similarity	NPC286338
0.6379	Remote Similarity	NPC603931
0.6379	Remote Similarity	NPC604237
0.6364	Remote Similarity	NPC473663
0.6364	Remote Similarity	NPC473723
0.6364	Remote Similarity	NPC475173
0.6349	Remote Similarity	NPC130359
0.6349	Remote Similarity	NPC14901
0.6333	Remote Similarity	NPC47937
0.6308	Remote Similarity	NPC488630
0.6308	Remote Similarity	NPC488625
0.6308	Remote Similarity	NPC488626
0.629	Remote Similarity	NPC602738
0.6271	Remote Similarity	NPC488253
0.6271	Remote Similarity	NPC473669
0.6271	Remote Similarity	NPC488251
0.6167	Remote Similarity	NPC81045
0.6167	Remote Similarity	NPC232555
0.6167	Remote Similarity	NPC39754
0.6167	Remote Similarity	NPC171135
0.6167	Remote Similarity	NPC171174
0.6167	Remote Similarity	NPC114694
0.6167	Remote Similarity	NPC61257
0.6167	Remote Similarity	NPC320569
0.6167	Remote Similarity	NPC485248
0.6167	Remote Similarity	NPC133730
0.6167	Remote Similarity	NPC191929
0.6167	Remote Similarity	NPC142117
0.6167	Remote Similarity	NPC100454
0.6167	Remote Similarity	NPC242364
0.6167	Remote Similarity	NPC480249
0.6167	Remote Similarity	NPC172821
0.6167	Remote Similarity	NPC485249
0.6167	Remote Similarity	NPC274446
0.6167	Remote Similarity	NPC485251
0.6167	Remote Similarity	NPC151403
0.6167	Remote Similarity	NPC240695
0.6167	Remote Similarity	NPC261952
0.6167	Remote Similarity	NPC605171
0.6094	Remote Similarity	NPC258068
0.6094	Remote Similarity	NPC476583
0.6066	Remote Similarity	NPC93794
0.6066	Remote Similarity	NPC488632
0.6066	Remote Similarity	NPC134865
0.6066	Remote Similarity	NPC473504
0.6066	Remote Similarity	NPC103523
0.6066	Remote Similarity	NPC81778
0.6066	Remote Similarity	NPC40066
0.6066	Remote Similarity	NPC488627
0.6066	Remote Similarity	NPC488631
0.6032	Remote Similarity	NPC477010
0.6	Remote Similarity	NPC477014
0.6	Remote Similarity	NPC477013
0.5968	Remote Similarity	NPC280621
0.5968	Remote Similarity	NPC48338
0.5968	Remote Similarity	NPC241360
0.5968	Remote Similarity	NPC293136
0.5968	Remote Similarity	NPC488628
0.5873	Remote Similarity	NPC178215
0.5873	Remote Similarity	NPC42598
0.5873	Remote Similarity	NPC65930
0.5806	Remote Similarity	NPC144415
0.5806	Remote Similarity	NPC608157
0.5781	Remote Similarity	NPC329615
0.5781	Remote Similarity	NPC488250
0.5758	Remote Similarity	NPC488623
0.5758	Remote Similarity	NPC488624
0.5758	Remote Similarity	NPC488629
0.5714	Remote Similarity	NPC608138
0.5692	Remote Similarity	NPC69082
0.5692	Remote Similarity	NPC488249
0.5672	Remote Similarity	NPC239517
0.5606	Remote Similarity	NPC488244
0.5556	Remote Similarity	NPC477011
0.5538	Remote Similarity	NPC605396
0.5522	Remote Similarity	NPC480082
0.55	Remote Similarity	NPC112685
0.5455	Remote Similarity	NPC11456
0.5455	Remote Similarity	NPC20339
0.5455	Remote Similarity	NPC477012
0.5362	Remote Similarity	NPC280612
0.5352	Remote Similarity	NPC488245
0.5323	Remote Similarity	NPC100921
0.5323	Remote Similarity	NPC475159
0.5323	Remote Similarity	NPC131002
0.5323	Remote Similarity	NPC473780
0.5323	Remote Similarity	NPC477018
0.5323	Remote Similarity	NPC604521
0.5294	Remote Similarity	NPC320458
0.5286	Remote Similarity	NPC253801
0.5224	Remote Similarity	NPC473707
0.5156	Remote Similarity	NPC156804
0.5147	Remote Similarity	NPC473995
0.5143	Remote Similarity	NPC473520
0.5143	Remote Similarity	NPC322529
0.5082	Remote Similarity	NPC73310
0.5082	Remote Similarity	NPC473529
0.5082	Remote Similarity	NPC180363
0.5082	Remote Similarity	NPC94875
0.5082	Remote Similarity	NPC11332
0.5082	Remote Similarity	NPC145914
0.5082	Remote Similarity	NPC601174
0.5082	Remote Similarity	NPC601403
0.5082	Remote Similarity	NPC603568
0.5082	Remote Similarity	NPC604330
0.5082	Remote Similarity	NPC608300
0.5082	Remote Similarity	NPC611200
0.5082	Remote Similarity	NPC611571
0.5077	Remote Similarity	NPC473649
0.5077	Remote Similarity	NPC473156
0.5077	Remote Similarity	NPC154097
0.5077	Remote Similarity	NPC163093
0.5077	Remote Similarity	NPC159750
0.5077	Remote Similarity	NPC73248
0.5077	Remote Similarity	NPC282815
0.5077	Remote Similarity	NPC470401
0.5077	Remote Similarity	NPC600956
0.5077	Remote Similarity	NPC610454

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6641
0.1-0.2	2465
0.2-0.3	44
0.3-0.4	0
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