NPASS Compound

Natural Product: NPC488632

Natural Product ID	NPC488632
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OGJFDIKXSQSEIB-JXZNRZJISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44559053
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 107108 0 0 0 0 0 0 0 0999 V2000 12.2654 -0.7952 -0.5460 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6851 -1.7342 0.5343 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6388 -2.5503 1.1294 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5676 -2.0731 1.9907 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6173 -1.0004 1.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1228 0.3839 1.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0529 1.4114 1.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5698 1.1882 -0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5115 2.2012 -0.4421 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3352 2.0324 0.4897 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2845 3.0393 0.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0522 2.9559 0.9091 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2913 1.6751 0.9123 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7882 1.2964 -0.4641 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8111 0.5907 -1.3206 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8911 -0.1665 -2.3009 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6722 -0.3481 -1.4738 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3933 0.1339 -2.1045 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7441 -0.2271 -1.1904 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0798 0.2346 -1.7614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1386 -0.1993 -0.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5154 0.1992 -1.1966 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5139 -0.2596 -0.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5939 -1.7258 0.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9579 -2.5963 -1.0677 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2296 -2.5330 -1.7911 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5046 -2.7549 -1.1095 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9579 -1.7575 -0.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2009 -0.4131 -0.6437 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5907 0.6223 0.3383 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7990 0.4405 1.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8521 1.2758 0.9847 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8961 0.8421 1.9113 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.2787 2.0015 2.8046 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3763 -0.1972 2.6740 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0936 -0.4967 2.1936 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3455 -1.4091 2.6142 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3294 -0.4838 -1.5517 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8610 -2.6616 -1.9963 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8921 0.3988 0.4866 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4498 1.5102 -2.2339 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8736 0.2273 -0.2482 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1291 1.9615 1.7206 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1749 -0.7639 -0.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6493 0.2274 -0.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7077 -1.1614 -1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5499 -2.3373 0.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1627 -1.1095 1.3497 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2050 -3.4067 1.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1823 -3.2280 0.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0611 -1.7598 2.9935 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9059 -2.9776 2.2830 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1679 -1.2606 0.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7022 -1.0471 2.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2940 0.6173 2.8427 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0198 0.6462 1.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2147 1.2059 2.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4771 2.4111 1.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0096 0.2028 -0.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3643 1.1917 -0.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1847 1.8901 -1.4708 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9049 3.2387 -0.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6921 2.3591 1.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0289 0.9929 0.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7644 4.0480 0.4003 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1467 3.1687 -0.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2605 3.3150 1.9591 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3400 3.7304 0.4758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7780 0.8248 1.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3584 2.1200 -1.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3032 -0.1711 -0.6776 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4789 1.2321 -1.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3786 -1.1210 -2.5986 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6528 0.4932 -3.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5391 -1.4642 -1.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 -0.3562 -3.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6492 0.1992 -0.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7228 -1.3324 -1.0764 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3263 -0.2836 -2.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0949 1.3241 -1.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9874 -1.2795 -0.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5412 1.3282 -1.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7680 -0.1665 -2.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0419 0.1295 0.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4515 0.2973 -0.1924 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1338 -1.8930 1.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5258 -2.0359 0.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9099 -3.6736 -0.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3439 -1.5972 -2.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1665 -3.3291 -2.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3004 -2.9212 -1.8671 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4427 -3.7376 -0.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0154 -2.1508 0.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3992 -1.8249 0.8533 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4045 -0.0445 -1.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7023 0.8147 1.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6101 1.6280 -0.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9140 2.0986 0.3137 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7598 0.5092 1.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6775 2.8769 2.5395 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0361 1.7406 3.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3652 2.1719 2.6820 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0226 -0.7906 -2.4338 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.3651 -2.6456 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0609 -0.2529 1.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0082 1.9049 -1.4347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3320 1.5705 1.2799 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 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 2 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 2 0 29 38 1 0 25 39 1 0 21 40 1 0 18 41 1 0 17 42 1 0 13 43 1 0 42 14 1 0 36 31 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 8 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 12 67 1 0 12 68 1 0 13 69 1 1 14 70 1 6 15 71 1 0 15 72 1 0 16 73 1 0 16 74 1 0 17 75 1 1 18 76 1 6 19 77 1 0 19 78 1 0 20 79 1 0 20 80 1 0 21 81 1 0 22 82 1 0 22 83 1 0 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 25 88 1 0 26 89 1 0 26 90 1 0 27 91 1 0 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 6 30 96 1 0 30 97 1 0 32 98 1 0 33 99 1 6 34100 1 0 34101 1 0 34102 1 0 38103 1 0 39104 1 0 40105 1 0 41106 1 0 43107 1 0 M END

Standard InCHIKey	OGJFDIKXSQSEIB-JXZNRZJISA-N
Standard InCHI	InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-12-19-31(39)33-22-23-34(43-33)32(40)21-20-29(37)17-13-15-28(36)16-14-18-30(38)25-27-24-26(2)42-35(27)41/h24,26,28-34,36-40H,3-23,25H2,1-2H3/t26-,28?,29?,30+,31+,32+,33+,34+/m0/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@H]([C@@H](CCC(CCCC(CCC[C@H](CC2=C[C@H](C)OC2=O)O)O)O)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	612.46	Volume:	661.852 ? Van der Waals volume.
Dense:	0.925	LogP:	4.022 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.088 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.044 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	11.0
TPSA:	136.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.059	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.82	Fsp³:	0.914
MCE-18:	34.388 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.74	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.074 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.548	Promiscuous compounds:	0.146

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.239	MDCK Permeability:	-4.851
Pgp-inhibitor:	0.001	Pgp-substrate:	0.996
PAMPA:	0.89 ? 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):	0.002
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.555
Plasma Protein Binding (PPB):	92.21%	Volume Distribution (VD):	0.14
Fu:	6.767% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.142
OATP1B3 inhibitor:	0.909	BCRP inhibitor:	0.845
BSEP inhibitor:	0.968

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.05	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.166
HLM stability:	0.0 ? 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):

7.832

Half-life (T1/2):

1.153

ADMET: Toxicity

hERG Blockers:	0.446	hERG Blockers (10um):	0.784
Human Hepatotoxicity (H-HT):	0.687	Drug-induced Liver Injury (DILI):	0.092
AMES Toxicity:	0.12	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.915	Skin Sensitization:	1.0
Carcinogencity:	0.182	Eye Corrosion:	0.002
Eye Irritation:	0.481	Respiratory Toxicity:	0.943
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.983
Hematotoxicity:	0.098	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.907	Hek293 Cytotoxicity:	0.183
BCF:	1.359 ? 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:	4.799 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.972 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.993 ? 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
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473425]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975482]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[17401878]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7494150]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673926]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673935]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[7673936]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[8946744]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[8991944]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[9584396]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26234	Annona muricata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26234	Annona muricata	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	13

Activity Type	# Activity
Cell line	12
Organism	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
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.93	10'-1 ug/ml	PMID[9584396]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	1.9	ug ml-1	PMID[9584396]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	7.1	10'-2 ug/ml	PMID[9584396]
NPT376	Cell line	A498	Homo sapiens	ED50	=	1.72	ug ml-1	PMID[9584396]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	4.5	10'-1 ug/ml	PMID[9584396]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	5.03	10'-2 ug/ml	PMID[9584396]
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.9	10'-1 ug/ml	PMID[10096871]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	4.5	10'-1 ug/ml	PMID[10096871]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	5.0	10'-2 ug/ml	PMID[10096871]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	1.9	ug ml-1	PMID[10096871]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	7.1	10'-2 ug/ml	PMID[10096871]
NPT376	Cell line	A498	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[10096871]
NPT176	Organism	Artemia salina	Artemia salina	ED50	=	1.86	ug ml-1	PMID[9584396]

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	=	1.8	ug.mL-1	PMID[10096871]

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 NPC488632 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	16391
0.1-0.2	30231
0.2-0.3	2909
0.3-0.4	91
0.4-0.5	28
0.5-0.6	22
0.6-0.7	46
0.7-0.8	0
0.8-0.85	28
0.85-0.9	10
0.9-0.95	11
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC232555
0.9767	High Similarity	NPC171174
0.9767	High Similarity	NPC114694
0.9767	High Similarity	NPC485248
0.9767	High Similarity	NPC142117
0.9767	High Similarity	NPC480249
0.9767	High Similarity	NPC485249
0.9767	High Similarity	NPC240695
0.9535	High Similarity	NPC488253
0.9535	High Similarity	NPC473669
0.9535	High Similarity	NPC488251
0.9302	High Similarity	NPC107986
0.9302	High Similarity	NPC223871
0.9302	High Similarity	NPC231009
0.9302	High Similarity	NPC103284
0.9302	High Similarity	NPC110710
0.9302	High Similarity	NPC1083
0.9302	High Similarity	NPC82795
0.9302	High Similarity	NPC286338
0.9302	High Similarity	NPC603931
0.9302	High Similarity	NPC604237
0.907	High Similarity	NPC606043
0.8913	High Similarity	NPC280621
0.8913	High Similarity	NPC48338
0.8913	High Similarity	NPC488628
0.8723	High Similarity	NPC178215
0.8723	High Similarity	NPC42598
0.8696	High Similarity	NPC134865
0.8696	High Similarity	NPC103523
0.8696	High Similarity	NPC488627
0.8696	High Similarity	NPC47937
0.8696	High Similarity	NPC488631
0.8478	Intermediate Similarity	NPC182383
0.8367	Intermediate Similarity	NPC69082
0.8367	Intermediate Similarity	NPC488249
0.8298	Intermediate Similarity	NPC93794
0.8298	Intermediate Similarity	NPC473504
0.8298	Intermediate Similarity	NPC81778
0.8298	Intermediate Similarity	NPC40066
0.8298	Intermediate Similarity	NPC477011
0.8163	Intermediate Similarity	NPC20621
0.8163	Intermediate Similarity	NPC318963
0.8163	Intermediate Similarity	NPC488250
0.8163	Intermediate Similarity	NPC605101
0.8085	Intermediate Similarity	NPC81045
0.8085	Intermediate Similarity	NPC39754
0.8085	Intermediate Similarity	NPC171135
0.8085	Intermediate Similarity	NPC61257
0.8085	Intermediate Similarity	NPC320569
0.8085	Intermediate Similarity	NPC133730
0.8085	Intermediate Similarity	NPC191929
0.8085	Intermediate Similarity	NPC100454
0.8085	Intermediate Similarity	NPC242364
0.8085	Intermediate Similarity	NPC172821
0.8085	Intermediate Similarity	NPC156804
0.8085	Intermediate Similarity	NPC274446
0.8085	Intermediate Similarity	NPC485251
0.8085	Intermediate Similarity	NPC151403
0.8085	Intermediate Similarity	NPC261952
0.8085	Intermediate Similarity	NPC605171
0.7959	Intermediate Similarity	NPC473687
0.7959	Intermediate Similarity	NPC204686
0.7959	Intermediate Similarity	NPC219498
0.7959	Intermediate Similarity	NPC308412
0.7959	Intermediate Similarity	NPC134885
0.7959	Intermediate Similarity	NPC488247
0.7959	Intermediate Similarity	NPC210218
0.7959	Intermediate Similarity	NPC488248
0.7674	Intermediate Similarity	NPC608138
0.766	Intermediate Similarity	NPC100921
0.766	Intermediate Similarity	NPC475159
0.766	Intermediate Similarity	NPC131002
0.766	Intermediate Similarity	NPC473780
0.766	Intermediate Similarity	NPC477018
0.766	Intermediate Similarity	NPC604521
0.7647	Intermediate Similarity	NPC20339
0.75	Intermediate Similarity	NPC130359
0.75	Intermediate Similarity	NPC14901
0.7451	Intermediate Similarity	NPC329838
0.7451	Intermediate Similarity	NPC20533
0.7451	Intermediate Similarity	NPC134807
0.7451	Intermediate Similarity	NPC602738
0.7358	Intermediate Similarity	NPC488623
0.7358	Intermediate Similarity	NPC488624
0.7358	Intermediate Similarity	NPC488629
0.7308	Intermediate Similarity	NPC473478
0.7308	Intermediate Similarity	NPC473651
0.7308	Intermediate Similarity	NPC66346
0.7255	Intermediate Similarity	NPC132940
0.7234	Intermediate Similarity	NPC112685
0.717	Intermediate Similarity	NPC231096
0.717	Intermediate Similarity	NPC475581
0.717	Intermediate Similarity	NPC283085
0.717	Intermediate Similarity	NPC169511
0.717	Intermediate Similarity	NPC62118
0.717	Intermediate Similarity	NPC258068
0.717	Intermediate Similarity	NPC287164
0.717	Intermediate Similarity	NPC234077
0.717	Intermediate Similarity	NPC132496
0.717	Intermediate Similarity	NPC107717
0.717	Intermediate Similarity	NPC488252
0.717	Intermediate Similarity	NPC476583
0.717	Intermediate Similarity	NPC606740
0.717	Intermediate Similarity	NPC608614
0.7091	Intermediate Similarity	NPC488630
0.7091	Intermediate Similarity	NPC488625
0.7091	Intermediate Similarity	NPC488626
0.7059	Intermediate Similarity	NPC473671
0.7059	Intermediate Similarity	NPC475268
0.7059	Intermediate Similarity	NPC470400
0.7059	Intermediate Similarity	NPC77871
0.7059	Intermediate Similarity	NPC9678
0.7059	Intermediate Similarity	NPC319036
0.7059	Intermediate Similarity	NPC604764
0.7059	Intermediate Similarity	NPC605867
0.7037	Intermediate Similarity	NPC233551
0.7037	Intermediate Similarity	NPC40376
0.7037	Intermediate Similarity	NPC21208
0.7021	Intermediate Similarity	NPC73310
0.7021	Intermediate Similarity	NPC473529
0.7021	Intermediate Similarity	NPC180363
0.7021	Intermediate Similarity	NPC94875
0.7021	Intermediate Similarity	NPC11332
0.7021	Intermediate Similarity	NPC145914
0.7021	Intermediate Similarity	NPC601174
0.7021	Intermediate Similarity	NPC601403
0.7021	Intermediate Similarity	NPC603568
0.7021	Intermediate Similarity	NPC604330
0.7021	Intermediate Similarity	NPC608300
0.7021	Intermediate Similarity	NPC611200
0.7021	Intermediate Similarity	NPC611571
0.6909	Remote Similarity	NPC239517
0.6863	Remote Similarity	NPC473649
0.6863	Remote Similarity	NPC473156
0.6863	Remote Similarity	NPC154097
0.6863	Remote Similarity	NPC163093
0.6863	Remote Similarity	NPC159750
0.6863	Remote Similarity	NPC73248
0.6863	Remote Similarity	NPC282815
0.6863	Remote Similarity	NPC470401
0.6863	Remote Similarity	NPC600956
0.6863	Remote Similarity	NPC610454
0.6792	Remote Similarity	NPC309211
0.6792	Remote Similarity	NPC477010
0.6786	Remote Similarity	NPC91067
0.66	Remote Similarity	NPC329829
0.6552	Remote Similarity	NPC473663
0.6552	Remote Similarity	NPC473723
0.6552	Remote Similarity	NPC475173
0.6491	Remote Similarity	NPC480081
0.6429	Remote Similarity	NPC477014
0.6429	Remote Similarity	NPC477013
0.6415	Remote Similarity	NPC241360
0.6415	Remote Similarity	NPC293136
0.6415	Remote Similarity	NPC480079
0.6296	Remote Similarity	NPC473904
0.6275	Remote Similarity	NPC25764
0.6275	Remote Similarity	NPC235809
0.6275	Remote Similarity	NPC39279
0.6275	Remote Similarity	NPC39167
0.6275	Remote Similarity	NPC292809
0.6275	Remote Similarity	NPC202055
0.6275	Remote Similarity	NPC606804
0.6275	Remote Similarity	NPC607425
0.6275	Remote Similarity	NPC608574
0.6226	Remote Similarity	NPC488246
0.6226	Remote Similarity	NPC144415
0.6226	Remote Similarity	NPC480080
0.6226	Remote Similarity	NPC607439
0.6226	Remote Similarity	NPC608157
0.614	Remote Similarity	NPC89001
0.6111	Remote Similarity	NPC219652
0.6111	Remote Similarity	NPC473840
0.6071	Remote Similarity	NPC473707
0.6071	Remote Similarity	NPC477012
0.6066	Remote Similarity	NPC482766
0.6066	Remote Similarity	NPC279267
0.5965	Remote Similarity	NPC120398
0.5965	Remote Similarity	NPC471567
0.5932	Remote Similarity	NPC280612
0.5926	Remote Similarity	NPC600524
0.5926	Remote Similarity	NPC608355
0.5806	Remote Similarity	NPC477017
0.5806	Remote Similarity	NPC477016
0.5789	Remote Similarity	NPC11456
0.5714	Remote Similarity	NPC480251
0.5714	Remote Similarity	NPC480250
0.5714	Remote Similarity	NPC65930
0.5614	Remote Similarity	NPC329615
0.5614	Remote Similarity	NPC485250
0.5614	Remote Similarity	NPC605396
0.5536	Remote Similarity	NPC25703
0.5517	Remote Similarity	NPC139418
0.5424	Remote Similarity	NPC473995
0.5424	Remote Similarity	NPC488244
0.5357	Remote Similarity	NPC482767
0.5357	Remote Similarity	NPC475260
0.5357	Remote Similarity	NPC488621
0.5357	Remote Similarity	NPC473775

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6365
0.1-0.2	2727
0.2-0.3	58
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