NPASS Compound

Natural Product: NPC239517

Natural Product ID	NPC239517
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asimitrin
IUPAC Name	(2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2S,3R,5R)-3-hydroxy-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms	Asimitrin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446217
PubChem CID	11422308
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 111113 0 0 0 0 0 0 0 0999 V2000 -12.4557 -2.4720 -0.6778 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4386 -2.6234 0.3768 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7874 -1.4562 0.9726 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9441 -0.5378 0.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6361 0.1522 -0.9112 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8888 1.0704 -1.8098 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2214 2.2792 -1.3177 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0962 2.2045 -0.3730 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9017 1.3966 -0.8652 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3222 1.9732 -2.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1562 1.2322 -2.6485 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9626 1.1239 -1.7596 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3200 2.4549 -1.4666 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1104 2.4591 0.0092 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3995 1.0387 0.4049 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1168 0.4512 -0.5911 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0509 0.3630 0.6744 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3028 0.4325 -0.4565 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6497 -0.7334 -0.6972 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4456 -1.8019 -0.0039 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2146 -1.0681 1.0560 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2876 -2.4826 -0.8862 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8066 -0.7103 -0.2871 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0324 -0.3088 1.1384 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5527 -0.3177 1.4646 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6525 0.0673 2.8858 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9616 0.2196 3.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9175 -0.8819 3.6134 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4945 -1.5012 2.4213 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2503 -0.5551 1.5156 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7829 -1.3725 0.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5607 -0.5342 -0.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7433 0.1475 0.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7104 -0.8096 0.6200 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8575 -0.0875 1.2393 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6695 0.6378 0.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6052 0.6715 -1.0496 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6668 1.5737 -1.5826 C 0 0 1 0 0 0 0 0 0 0 0 0 13.3437 2.0869 -0.4683 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7791 1.5379 0.6509 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1443 1.7635 1.8197 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6013 0.6790 -2.4152 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2303 -1.6657 -0.3823 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3416 -1.9591 -0.5880 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7168 1.9560 -3.7918 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1239 -2.6598 -1.7214 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1043 -1.5814 -0.5528 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2050 -3.3307 -0.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9226 -3.1915 1.2452 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6751 -3.4067 0.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1125 -1.8608 1.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5044 -0.8128 1.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6413 0.2704 0.9305 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9528 -0.9748 -0.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2971 -0.5230 -1.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4271 0.8209 -0.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6842 1.4370 -2.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1739 0.4141 -2.4148 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0297 2.8957 -0.7690 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9884 3.0028 -2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7313 3.2925 -0.2649 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3512 1.9047 0.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1701 0.3334 -1.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1584 1.4399 -0.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1318 1.9188 -2.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1319 3.0620 -1.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4533 0.2135 -2.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1908 0.5483 -2.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9475 3.3084 -1.8127 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3418 2.5817 -1.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8428 3.1382 0.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1059 2.8065 0.2835 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9865 1.0197 1.3565 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6212 0.8929 1.5696 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6475 -0.9998 -1.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7752 -2.5319 0.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8801 -1.3026 2.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2916 -1.3778 0.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0178 -3.4342 -0.8885 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3013 0.0077 -1.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6762 0.7555 1.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4636 -0.9122 1.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0080 0.3417 0.7317 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7993 -1.3983 1.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0529 -0.6984 3.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0759 1.0202 3.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4700 1.2064 3.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7179 0.4915 4.6191 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7851 -0.5216 4.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4662 -1.6864 4.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3211 -2.2039 2.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8857 -2.1665 1.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6029 0.2286 1.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0754 -0.1409 2.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3451 -2.2425 0.7206 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9109 -1.7900 -0.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8859 -1.1962 -1.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8979 0.2337 -1.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2782 0.8074 0.8149 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1821 0.8424 -0.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2338 -1.5140 1.3416 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5129 -0.7893 1.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4924 0.6401 2.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9489 0.1411 -1.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2379 2.3679 -2.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6216 -0.3064 -1.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6200 1.1245 -2.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1344 0.5540 -3.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5676 -2.3875 -0.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6801 -2.0102 -1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9112 1.4681 -4.6215 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 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 19 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 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 38 42 1 0 34 43 1 0 23 44 1 0 11 45 1 0 16 12 1 0 21 17 1 0 40 36 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 6 12 68 1 6 13 69 1 0 13 70 1 0 14 71 1 0 14 72 1 0 15 73 1 1 17 74 1 1 19 75 1 6 20 76 1 1 21 77 1 0 21 78 1 0 22 79 1 0 23 80 1 6 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 0 27 88 1 0 28 89 1 0 28 90 1 0 29 91 1 0 29 92 1 0 30 93 1 0 30 94 1 0 31 95 1 0 31 96 1 0 32 97 1 0 32 98 1 0 33 99 1 0 33100 1 0 34101 1 1 35102 1 0 35103 1 0 37104 1 0 38105 1 6 42106 1 0 42107 1 0 42108 1 0 43109 1 0 44110 1 0 45111 1 0 M END

Standard InCHIKey	NNTXABWKPQWPML-SDNTZQKYSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-5-6-7-11-14-17-20-30(39)33-22-23-34(44-33)35-26-32(41)36(45-35)31(40)21-18-15-12-9-8-10-13-16-19-29(38)25-28-24-27(2)43-37(28)42/h24,27,29-36,38-41H,3-23,25-26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+,35+,36-/m0/s1
SMILES	CCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H]1O[C@H]([C@@H](C1)O)[C@@H](CCCCCCCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	5.106 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.54 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.879 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	25.0	Rigid Bonds:	16.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.918	Fsp³:	0.919
MCE-18:	45.07 ? 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:	0.937	Fluc inhibitor:	0.021 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.427	Promiscuous compounds:	0.304

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.197	MDCK Permeability:	-4.85
Pgp-inhibitor:	0.0	Pgp-substrate:	0.951
PAMPA:	0.213 ? 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):	0.029
20% Bioavailability (F20%):	0.969	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.928
Plasma Protein Binding (PPB):	97.356%	Volume Distribution (VD):	0.547
Fu:	2.834% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.979
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.474
BSEP inhibitor:	0.706

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.844	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.209	CYP2D6-substrate:	0.834
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.006 ? 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):

5.488

Half-life (T1/2):

1.305

ADMET: Toxicity

hERG Blockers:	0.454	hERG Blockers (10um):	0.713
Human Hepatotoxicity (H-HT):	0.646	Drug-induced Liver Injury (DILI):	0.445
AMES Toxicity:	0.433	Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.918	Skin Sensitization:	1.0
Carcinogencity:	0.572	Eye Corrosion:	0.005
Eye Irritation:	0.589	Respiratory Toxicity:	0.928
Drug-induced Neurotoxicity:	0.091	Ototoxicity:	0.741
Hematotoxicity:	0.162	Drug-induced Nephrotoxicity:	0.9
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.133
A549 Cytotoxicity:	0.987	Hek293 Cytotoxicity:	0.441
BCF:	1.354 ? 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:	5.073 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.17 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.172 ? 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
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11087592]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15730242]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1593281]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30028612]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8676130]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946743]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7697	Asimina triloba	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7697	Asimina triloba	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	=	1.19	ug ml-1	PMID[15332862]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	2.12	ug ml-1	PMID[10395501]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.19	10'-4 ug/ml	PMID[18177012]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	1.72	10'-6 ug/ml	PMID[18177012]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	2.11	10'-4 ug/ml	PMID[25127165]
NPT376	Cell line	A498	Homo sapiens	ED50	=	7.5	10'-1 ug/ml	PMID[25152999]

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
-	Artemia	LC50	=	0.0207	ug.mL-1	PMID[18271554]

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 NPC239517 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	18847
0.1-0.2	28955
0.2-0.3	1772
0.3-0.4	62
0.4-0.5	32
0.5-0.6	42
0.6-0.7	97
0.7-0.8	0
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.84	Intermediate Similarity	NPC81045
0.84	Intermediate Similarity	NPC39754
0.84	Intermediate Similarity	NPC171135
0.84	Intermediate Similarity	NPC61257
0.84	Intermediate Similarity	NPC320569
0.84	Intermediate Similarity	NPC133730
0.84	Intermediate Similarity	NPC191929
0.84	Intermediate Similarity	NPC100454
0.84	Intermediate Similarity	NPC242364
0.84	Intermediate Similarity	NPC172821
0.84	Intermediate Similarity	NPC274446
0.84	Intermediate Similarity	NPC485251
0.84	Intermediate Similarity	NPC151403
0.84	Intermediate Similarity	NPC261952
0.84	Intermediate Similarity	NPC605171
0.8235	Intermediate Similarity	NPC93794
0.8235	Intermediate Similarity	NPC473504
0.8235	Intermediate Similarity	NPC81778
0.8235	Intermediate Similarity	NPC40066
0.7925	Intermediate Similarity	NPC42598
0.7778	Intermediate Similarity	NPC602738
0.7586	Intermediate Similarity	NPC473905
0.75	Intermediate Similarity	NPC169511
0.75	Intermediate Similarity	NPC287164
0.75	Intermediate Similarity	NPC234077
0.7451	Intermediate Similarity	NPC606043
0.7321	Intermediate Similarity	NPC20339
0.7308	Intermediate Similarity	NPC107986
0.7308	Intermediate Similarity	NPC223871
0.7308	Intermediate Similarity	NPC231009
0.7308	Intermediate Similarity	NPC103284
0.7308	Intermediate Similarity	NPC110710
0.7308	Intermediate Similarity	NPC1083
0.7308	Intermediate Similarity	NPC82795
0.7308	Intermediate Similarity	NPC286338
0.7308	Intermediate Similarity	NPC603931
0.7308	Intermediate Similarity	NPC604237
0.717	Intermediate Similarity	NPC488253
0.717	Intermediate Similarity	NPC473669
0.717	Intermediate Similarity	NPC488251
0.7119	Intermediate Similarity	NPC91067
0.7037	Intermediate Similarity	NPC232555
0.7037	Intermediate Similarity	NPC171174
0.7037	Intermediate Similarity	NPC114694
0.7037	Intermediate Similarity	NPC485248
0.7037	Intermediate Similarity	NPC142117
0.7037	Intermediate Similarity	NPC480249
0.7037	Intermediate Similarity	NPC485249
0.7037	Intermediate Similarity	NPC240695
0.6909	Remote Similarity	NPC488632
0.6909	Remote Similarity	NPC473649
0.6909	Remote Similarity	NPC473156
0.6909	Remote Similarity	NPC134865
0.6909	Remote Similarity	NPC154097
0.6909	Remote Similarity	NPC103523
0.6909	Remote Similarity	NPC159750
0.6909	Remote Similarity	NPC73248
0.6909	Remote Similarity	NPC282815
0.6909	Remote Similarity	NPC488627
0.6909	Remote Similarity	NPC488631
0.6909	Remote Similarity	NPC470401
0.6909	Remote Similarity	NPC600956
0.6909	Remote Similarity	NPC610454
0.6885	Remote Similarity	NPC473663
0.6885	Remote Similarity	NPC473723
0.6885	Remote Similarity	NPC475173
0.6786	Remote Similarity	NPC280621
0.6786	Remote Similarity	NPC473671
0.6786	Remote Similarity	NPC475268
0.6786	Remote Similarity	NPC470400
0.6786	Remote Similarity	NPC77871
0.6786	Remote Similarity	NPC48338
0.6786	Remote Similarity	NPC9678
0.6786	Remote Similarity	NPC319036
0.6786	Remote Similarity	NPC488628
0.6786	Remote Similarity	NPC604764
0.6786	Remote Similarity	NPC605867
0.6727	Remote Similarity	NPC182383
0.6667	Remote Similarity	NPC25764
0.6667	Remote Similarity	NPC235809
0.6667	Remote Similarity	NPC178215
0.6667	Remote Similarity	NPC473687
0.6667	Remote Similarity	NPC39279
0.6667	Remote Similarity	NPC204686
0.6667	Remote Similarity	NPC219498
0.6667	Remote Similarity	NPC39167
0.6667	Remote Similarity	NPC292809
0.6667	Remote Similarity	NPC308412
0.6667	Remote Similarity	NPC134885
0.6667	Remote Similarity	NPC202055
0.6667	Remote Similarity	NPC488247
0.6667	Remote Similarity	NPC132940
0.6667	Remote Similarity	NPC210218
0.6667	Remote Similarity	NPC488248
0.6667	Remote Similarity	NPC606804
0.6667	Remote Similarity	NPC607425
0.6667	Remote Similarity	NPC608574
0.661	Remote Similarity	NPC120398
0.661	Remote Similarity	NPC471567
0.6552	Remote Similarity	NPC20621
0.6552	Remote Similarity	NPC318963
0.6552	Remote Similarity	NPC20533
0.6552	Remote Similarity	NPC488250
0.6552	Remote Similarity	NPC605101
0.65	Remote Similarity	NPC89001
0.65	Remote Similarity	NPC488623
0.65	Remote Similarity	NPC488624
0.65	Remote Similarity	NPC488629
0.6441	Remote Similarity	NPC473478
0.6441	Remote Similarity	NPC69082
0.6441	Remote Similarity	NPC473651
0.6441	Remote Similarity	NPC488249
0.6441	Remote Similarity	NPC66346
0.6333	Remote Similarity	NPC283085
0.6333	Remote Similarity	NPC130359
0.6333	Remote Similarity	NPC14901
0.6316	Remote Similarity	NPC47937
0.6316	Remote Similarity	NPC477011
0.6316	Remote Similarity	NPC600524
0.6316	Remote Similarity	NPC608355
0.6296	Remote Similarity	NPC112685
0.6275	Remote Similarity	NPC608138
0.6271	Remote Similarity	NPC134807
0.623	Remote Similarity	NPC233551
0.623	Remote Similarity	NPC40376
0.623	Remote Similarity	NPC21208
0.6207	Remote Similarity	NPC219652
0.6207	Remote Similarity	NPC473840
0.6207	Remote Similarity	NPC480079
0.6071	Remote Similarity	NPC100921
0.6071	Remote Similarity	NPC475159
0.6071	Remote Similarity	NPC131002
0.6071	Remote Similarity	NPC473780
0.6071	Remote Similarity	NPC477018
0.6071	Remote Similarity	NPC604521
0.6066	Remote Similarity	NPC231096
0.6066	Remote Similarity	NPC475581
0.6066	Remote Similarity	NPC62118
0.6066	Remote Similarity	NPC132496
0.6066	Remote Similarity	NPC107717
0.6066	Remote Similarity	NPC488252
0.6032	Remote Similarity	NPC488630
0.6032	Remote Similarity	NPC488625
0.6032	Remote Similarity	NPC488626
0.6	Remote Similarity	NPC485250
0.6	Remote Similarity	NPC605396
0.5932	Remote Similarity	NPC25703
0.5902	Remote Similarity	NPC473707
0.5862	Remote Similarity	NPC156804
0.5818	Remote Similarity	NPC73310
0.5818	Remote Similarity	NPC473529
0.5818	Remote Similarity	NPC180363
0.5818	Remote Similarity	NPC94875
0.5818	Remote Similarity	NPC11332
0.5818	Remote Similarity	NPC145914
0.5818	Remote Similarity	NPC601174
0.5818	Remote Similarity	NPC601403
0.5818	Remote Similarity	NPC603568
0.5818	Remote Similarity	NPC604330
0.5818	Remote Similarity	NPC608300
0.5818	Remote Similarity	NPC611200
0.5818	Remote Similarity	NPC611571
0.5806	Remote Similarity	NPC473995
0.5806	Remote Similarity	NPC606740
0.5806	Remote Similarity	NPC608614
0.5781	Remote Similarity	NPC480081
0.5763	Remote Similarity	NPC163093
0.5672	Remote Similarity	NPC482766
0.5538	Remote Similarity	NPC473520
0.5517	Remote Similarity	NPC329829
0.5484	Remote Similarity	NPC309211
0.5484	Remote Similarity	NPC329838
0.5484	Remote Similarity	NPC477010
0.5469	Remote Similarity	NPC477014
0.5469	Remote Similarity	NPC477013
0.5441	Remote Similarity	NPC279267
0.5345	Remote Similarity	NPC480072
0.5312	Remote Similarity	NPC258068
0.5312	Remote Similarity	NPC476583
0.5246	Remote Similarity	NPC488246
0.5246	Remote Similarity	NPC144415
0.5246	Remote Similarity	NPC480080
0.5246	Remote Similarity	NPC607439
0.5246	Remote Similarity	NPC608157
0.5161	Remote Similarity	NPC241360
0.5161	Remote Similarity	NPC293136
0.5079	Remote Similarity	NPC473904
0.5079	Remote Similarity	NPC65930

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC239517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6745
0.1-0.2	2367
0.2-0.3	38
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