NPASS Compound

Natural Product: NPC477017

Natural Product ID	NPC477017
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(1R)-1,13-dihydroxy-1-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-15-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]-8-oxopentadecan-3-yl] acetate
IUPAC Name	[(1R)-1,13-dihydroxy-1-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-15-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]-8-oxopentadecan-3-yl] acetate
Synonyms	Plagioneurin E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583897
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 116117 0 0 0 0 0 0 0 0999 V2000 -10.6311 2.4374 -3.9441 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9289 1.7185 -2.6459 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7538 0.7939 -2.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1642 0.1374 -0.9835 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2051 -0.8232 -0.3854 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8710 -0.2179 -0.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9668 -1.2572 0.6066 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4821 -1.8885 1.8137 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8999 -1.2161 3.0098 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1234 -0.3703 3.9131 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4876 0.8884 3.5827 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3497 1.0355 2.6676 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1113 0.3160 3.0960 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0047 0.5123 2.1030 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7479 -0.0520 2.7564 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7734 -1.4573 2.2373 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6217 -1.3814 0.9728 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1857 -0.1394 0.9133 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7564 -1.6474 -0.2330 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7706 -0.5411 -0.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1864 -0.7766 -1.5864 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0706 0.4210 -1.5774 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1282 0.5348 -2.6104 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1846 -0.5201 -2.5618 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8979 -0.5220 -1.2186 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6035 0.7553 -0.9739 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7175 1.5505 -1.8806 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1526 1.0282 0.3791 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8597 2.3174 0.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9653 2.6275 -0.4126 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1992 1.7715 -0.4303 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0438 0.4281 -0.9628 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2215 -0.5019 -1.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8460 -0.7971 0.2672 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7390 0.1922 0.8951 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2160 1.3134 0.4285 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0635 1.9584 1.4407 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0527 1.1010 2.5556 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2621 0.0171 2.2813 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9924 -0.9674 3.0213 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4892 2.1661 0.9082 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6188 0.5985 -2.3308 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6687 -1.9980 -1.6070 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9027 -3.1943 -1.9789 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3397 -3.5761 -3.0718 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7561 -4.2016 -1.2851 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1850 -2.9057 -0.1865 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2476 -1.0403 3.3399 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1301 1.9235 -4.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8633 3.5109 -3.9201 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5349 2.3298 -4.1468 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8219 1.0563 -2.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1386 2.4210 -1.8270 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6186 0.0116 -3.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8706 1.4218 -2.2252 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1176 -0.4124 -1.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4783 0.9286 -0.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0024 -1.6311 -1.1376 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6798 -1.3453 0.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9576 0.7082 0.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3913 0.0714 -0.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9253 -2.0600 -0.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9440 -0.9080 0.6209 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7281 -2.7020 2.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3343 -2.5950 1.4450 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9387 -0.7019 2.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2905 -2.0776 3.7179 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8539 -0.1667 4.8073 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3940 -1.0664 4.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1506 1.3842 4.5768 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2476 1.6883 3.2474 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4928 0.9748 1.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0162 2.1665 2.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6935 0.8151 4.0499 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8477 1.6052 1.9177 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8664 -0.0516 3.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8642 0.5391 2.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7560 -1.8403 1.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2083 -2.1769 2.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3719 -2.2266 0.9766 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4486 -1.6603 -1.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1096 -0.4262 0.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2846 0.4150 -0.5761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5207 -0.6259 -2.4834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3941 1.3213 -1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5555 0.5830 -0.5779 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6029 1.5364 -2.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6639 0.5765 -3.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9059 -1.5146 -2.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9910 -0.1732 -3.2912 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6766 -1.3277 -1.2943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1957 -0.7906 -0.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6798 0.2106 0.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1913 1.1129 1.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0380 3.1183 0.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1412 2.4873 1.5777 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6360 2.7801 -1.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3399 3.7144 -0.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9757 2.3737 -0.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5822 1.7538 0.6499 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2099 -0.1445 -0.4649 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8470 -1.4357 -1.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9586 -0.0445 -1.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4415 -1.7591 0.2509 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0268 -1.0524 1.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0718 1.7527 -0.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6506 2.9638 1.7140 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0228 1.1895 1.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4254 2.4763 -0.1630 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0056 2.9613 1.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3159 -0.2936 -2.6859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8510 -5.0847 -1.9334 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1621 -4.4975 -0.3776 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7511 -3.7598 -1.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5311 -3.4406 0.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7959 -1.5172 2.7108 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 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 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 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 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 37 41 1 0 32 42 1 0 21 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 19 47 1 0 13 48 1 0 18 14 1 0 39 35 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 0 2 53 1 0 3 54 1 0 3 55 1 0 4 56 1 0 4 57 1 0 5 58 1 0 5 59 1 0 6 60 1 0 6 61 1 0 7 62 1 0 7 63 1 0 8 64 1 0 8 65 1 0 9 66 1 0 9 67 1 0 10 68 1 0 10 69 1 0 11 70 1 0 11 71 1 0 12 72 1 0 12 73 1 0 13 74 1 1 14 75 1 6 15 76 1 0 15 77 1 0 16 78 1 0 16 79 1 0 17 80 1 1 19 81 1 6 20 82 1 0 20 83 1 0 21 84 1 0 22 85 1 0 22 86 1 0 23 87 1 0 23 88 1 0 24 89 1 0 24 90 1 0 25 91 1 0 25 92 1 0 28 93 1 0 28 94 1 0 29 95 1 0 29 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 33102 1 0 33103 1 0 34104 1 0 34105 1 0 36106 1 0 37107 1 1 41108 1 0 41109 1 0 41110 1 0 42111 1 0 46112 1 0 46113 1 0 46114 1 0 47115 1 0 48116 1 0 M END

Standard InCHIKey	OJFDGOAJDAPKNG-QZBJIPNWSA-N
Standard InCHI	InChI=1S/C39H68O9/c1-4-5-6-7-8-9-10-11-12-13-22-35(43)37-25-26-38(48-37)36(44)28-34(47-30(3)40)21-17-16-19-32(41)18-14-15-20-33(42)24-23-31-27-29(2)46-39(31)45/h27,29,33-38,42-44H,4-26,28H2,1-3H3/t29-,33?,34?,35+,36+,37+,38+/m0/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CC(CCCCC(=O)CCCCC(CCC2=C[C@@H](OC2=O)C)O)OC(=O)C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	680.49	Volume:	734.553 ? Van der Waals volume.
Dense:	0.926	LogP:	5.229 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.775 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.038 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	30.0	Rigid Bonds:	13.0
TPSA:	139.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.054	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.859	Fsp³:	0.872
MCE-18:	36.329 ? 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:	0.909	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.058 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.452	Promiscuous compounds:	0.258

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.283	MDCK Permeability:	-4.792
Pgp-inhibitor:	0.011	Pgp-substrate:	0.927
PAMPA:	0.106 ? 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):	0.39
20% Bioavailability (F20%):	0.941	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.987
Plasma Protein Binding (PPB):	94.532%	Volume Distribution (VD):	0.371
Fu:	5.304% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.032
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.104
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.982
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.42 ? 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):

5.364

Half-life (T1/2):

1.132

ADMET: Toxicity

hERG Blockers:	0.585	hERG Blockers (10um):	0.843
Human Hepatotoxicity (H-HT):	0.548	Drug-induced Liver Injury (DILI):	0.192
AMES Toxicity:	0.234	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.921	Skin Sensitization:	1.0
Carcinogencity:	0.222	Eye Corrosion:	0.001
Eye Irritation:	0.231	Respiratory Toxicity:	0.877
Drug-induced Neurotoxicity:	0.051	Ototoxicity:	0.861
Hematotoxicity:	0.123	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.137
A549 Cytotoxicity:	0.843	Hek293 Cytotoxicity:	0.364
BCF:	1.015 ? 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:	4.958 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.29 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.021 ? 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
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	leaves	Tam Kim, Cao Bang Province, in North Vietnam	2000-JUN	PMID[16989521]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22123	Disepalum plagioneurum	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
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
NPT91	Cell line	KB	Homo sapiens	IC50	=	2.6	nM	PMID[16989521]

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 NPC477017 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	18781
0.1-0.2	28601
0.2-0.3	2169
0.3-0.4	81
0.4-0.5	29
0.5-0.6	120
0.6-0.7	65
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477016
0.8772	High Similarity	NPC477015
0.8364	Intermediate Similarity	NPC477010
0.8246	Intermediate Similarity	NPC477014
0.8246	Intermediate Similarity	NPC477013
0.7273	Intermediate Similarity	NPC100921
0.7273	Intermediate Similarity	NPC477018
0.7193	Intermediate Similarity	NPC144415
0.7193	Intermediate Similarity	NPC608157
0.6949	Remote Similarity	NPC473687
0.6949	Remote Similarity	NPC204686
0.6949	Remote Similarity	NPC219498
0.6949	Remote Similarity	NPC308412
0.6949	Remote Similarity	NPC134885
0.6949	Remote Similarity	NPC488247
0.6949	Remote Similarity	NPC210218
0.6949	Remote Similarity	NPC488248
0.6825	Remote Similarity	NPC280612
0.6721	Remote Similarity	NPC477012
0.6667	Remote Similarity	NPC482766
0.6667	Remote Similarity	NPC475159
0.6667	Remote Similarity	NPC131002
0.6667	Remote Similarity	NPC473780
0.6667	Remote Similarity	NPC604521
0.6613	Remote Similarity	NPC258068
0.6613	Remote Similarity	NPC476583
0.661	Remote Similarity	NPC473649
0.661	Remote Similarity	NPC154097
0.661	Remote Similarity	NPC159750
0.661	Remote Similarity	NPC73248
0.661	Remote Similarity	NPC470401
0.6557	Remote Similarity	NPC309211
0.6557	Remote Similarity	NPC134807
0.6557	Remote Similarity	NPC605396
0.6508	Remote Similarity	NPC89001
0.65	Remote Similarity	NPC604764
0.6441	Remote Similarity	NPC156804
0.6333	Remote Similarity	NPC163093
0.623	Remote Similarity	NPC241360
0.623	Remote Similarity	NPC293136
0.614	Remote Similarity	NPC73310
0.614	Remote Similarity	NPC473529
0.614	Remote Similarity	NPC180363
0.614	Remote Similarity	NPC94875
0.614	Remote Similarity	NPC11332
0.614	Remote Similarity	NPC145914
0.614	Remote Similarity	NPC601174
0.614	Remote Similarity	NPC601403
0.614	Remote Similarity	NPC603568
0.614	Remote Similarity	NPC604330
0.614	Remote Similarity	NPC608300
0.614	Remote Similarity	NPC611200
0.614	Remote Similarity	NPC611571
0.6102	Remote Similarity	NPC107986
0.6102	Remote Similarity	NPC223871
0.6102	Remote Similarity	NPC231009
0.6102	Remote Similarity	NPC103284
0.6102	Remote Similarity	NPC110710
0.6102	Remote Similarity	NPC1083
0.6102	Remote Similarity	NPC82795
0.6102	Remote Similarity	NPC286338
0.6102	Remote Similarity	NPC603931
0.6102	Remote Similarity	NPC604237
0.6066	Remote Similarity	NPC473156
0.6066	Remote Similarity	NPC282815
0.6066	Remote Similarity	NPC600956
0.6066	Remote Similarity	NPC610454
0.6032	Remote Similarity	NPC329838
0.6032	Remote Similarity	NPC20621
0.6032	Remote Similarity	NPC318963
0.6032	Remote Similarity	NPC605101
0.6	Remote Similarity	NPC488253
0.6	Remote Similarity	NPC473669
0.6	Remote Similarity	NPC488251
0.5968	Remote Similarity	NPC473671
0.5968	Remote Similarity	NPC475268
0.5968	Remote Similarity	NPC470400
0.5968	Remote Similarity	NPC77871
0.5968	Remote Similarity	NPC9678
0.5968	Remote Similarity	NPC319036
0.5968	Remote Similarity	NPC605867
0.5932	Remote Similarity	NPC606043
0.5902	Remote Similarity	NPC232555
0.5902	Remote Similarity	NPC171174
0.5902	Remote Similarity	NPC182383
0.5902	Remote Similarity	NPC114694
0.5902	Remote Similarity	NPC485248
0.5902	Remote Similarity	NPC142117
0.5902	Remote Similarity	NPC480249
0.5902	Remote Similarity	NPC485249
0.5902	Remote Similarity	NPC240695
0.5873	Remote Similarity	NPC178215
0.5873	Remote Similarity	NPC65930
0.5873	Remote Similarity	NPC132940
0.5846	Remote Similarity	NPC120398
0.5846	Remote Similarity	NPC130359
0.5846	Remote Similarity	NPC14901
0.5846	Remote Similarity	NPC471567
0.5833	Remote Similarity	NPC329829
0.5806	Remote Similarity	NPC488632
0.5806	Remote Similarity	NPC477011
0.5781	Remote Similarity	NPC20533
0.5692	Remote Similarity	NPC473478
0.5692	Remote Similarity	NPC473651
0.5692	Remote Similarity	NPC139418
0.5692	Remote Similarity	NPC66346
0.5606	Remote Similarity	NPC283085
0.5606	Remote Similarity	NPC169511
0.5606	Remote Similarity	NPC287164
0.5606	Remote Similarity	NPC234077
0.5606	Remote Similarity	NPC473995
0.5588	Remote Similarity	NPC488630
0.5588	Remote Similarity	NPC488625
0.5588	Remote Similarity	NPC488626
0.5574	Remote Similarity	NPC25764
0.5574	Remote Similarity	NPC235809
0.5574	Remote Similarity	NPC39279
0.5574	Remote Similarity	NPC39167
0.5574	Remote Similarity	NPC292809
0.5574	Remote Similarity	NPC202055
0.5574	Remote Similarity	NPC606804
0.5574	Remote Similarity	NPC607425
0.5574	Remote Similarity	NPC608574
0.5556	Remote Similarity	NPC93794
0.5556	Remote Similarity	NPC134865
0.5556	Remote Similarity	NPC473504
0.5556	Remote Similarity	NPC103523
0.5556	Remote Similarity	NPC81778
0.5556	Remote Similarity	NPC40066
0.5556	Remote Similarity	NPC488627
0.5556	Remote Similarity	NPC47937
0.5556	Remote Similarity	NPC488631
0.5556	Remote Similarity	NPC600524
0.5556	Remote Similarity	NPC607439
0.5556	Remote Similarity	NPC608355
0.5538	Remote Similarity	NPC329615
0.5538	Remote Similarity	NPC488250
0.5469	Remote Similarity	NPC280621
0.5469	Remote Similarity	NPC48338
0.5469	Remote Similarity	NPC488628
0.5455	Remote Similarity	NPC69082
0.5455	Remote Similarity	NPC11456
0.5455	Remote Similarity	NPC488249
0.5397	Remote Similarity	NPC81045
0.5397	Remote Similarity	NPC39754
0.5397	Remote Similarity	NPC171135
0.5397	Remote Similarity	NPC61257
0.5397	Remote Similarity	NPC320569
0.5397	Remote Similarity	NPC133730
0.5397	Remote Similarity	NPC191929
0.5397	Remote Similarity	NPC100454
0.5397	Remote Similarity	NPC242364
0.5397	Remote Similarity	NPC172821
0.5397	Remote Similarity	NPC274446
0.5397	Remote Similarity	NPC485251
0.5397	Remote Similarity	NPC151403
0.5397	Remote Similarity	NPC261952
0.5397	Remote Similarity	NPC605171
0.5385	Remote Similarity	NPC473699
0.5385	Remote Similarity	NPC51249
0.5385	Remote Similarity	NPC42598
0.5385	Remote Similarity	NPC478998
0.5373	Remote Similarity	NPC231096
0.5373	Remote Similarity	NPC475581
0.5373	Remote Similarity	NPC62118
0.5373	Remote Similarity	NPC132496
0.5373	Remote Similarity	NPC107717
0.5373	Remote Similarity	NPC488252
0.5362	Remote Similarity	NPC473520
0.5362	Remote Similarity	NPC91067
0.5303	Remote Similarity	NPC602738
0.5294	Remote Similarity	NPC488623
0.5294	Remote Similarity	NPC320458
0.5294	Remote Similarity	NPC488624
0.5294	Remote Similarity	NPC233551
0.5294	Remote Similarity	NPC40376
0.5294	Remote Similarity	NPC480082
0.5294	Remote Similarity	NPC21208
0.5294	Remote Similarity	NPC488629
0.5286	Remote Similarity	NPC253801
0.5231	Remote Similarity	NPC219652
0.5231	Remote Similarity	NPC473840
0.5211	Remote Similarity	NPC473663
0.5211	Remote Similarity	NPC473723
0.5211	Remote Similarity	NPC475173
0.5143	Remote Similarity	NPC480081
0.5077	Remote Similarity	NPC482767
0.5077	Remote Similarity	NPC475260
0.5077	Remote Similarity	NPC488621
0.5077	Remote Similarity	NPC473775
0.5077	Remote Similarity	NPC488622
0.5075	Remote Similarity	NPC485250
0.5075	Remote Similarity	NPC600188
0.507	Remote Similarity	NPC475206

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6809
0.1-0.2	2302
0.2-0.3	38
0.3-0.4	1
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