NPASS Compound

Natural Product: NPC210218

Natural Product ID	NPC210218
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mosin C
IUPAC Name	(2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5S)-5-[(1S)-1-hydroxytridecyl]oxolan-2-yl]-7-oxotridecyl]-2-methyl-2H-furan-5-one
Synonyms	Mosin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505178
PubChem CID	44593341
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 104105 0 0 0 0 0 0 0 0999 V2000 13.9601 0.3880 0.7836 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6350 0.1291 0.0918 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1864 1.3780 -0.6344 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8915 1.2220 -1.3528 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7170 0.8701 -0.5053 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4129 1.8761 0.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2123 1.5084 1.3989 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9625 1.3849 0.5970 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7774 1.0329 1.4283 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8581 -0.2600 2.1657 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0538 -1.4457 1.2467 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9735 -1.5885 0.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6002 -1.7693 0.7865 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6219 -1.8896 -0.3652 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6547 -0.6162 -1.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3246 -0.7770 -1.9496 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4997 -1.4800 -0.9425 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3262 -2.0971 -0.0063 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4145 -0.5628 -0.1631 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2752 0.3216 -0.9991 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1800 1.1854 -0.2173 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2162 0.5824 0.6419 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3081 -0.2160 0.0517 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0399 -1.4632 -0.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3498 -2.0500 -1.1360 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2699 -3.0740 -1.7862 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6791 -1.4271 -0.8246 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7103 -2.2801 -1.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1374 -1.9841 -1.3044 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7513 -0.7756 -1.8365 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3562 0.5649 -1.3904 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4698 0.9747 0.0059 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7591 1.0252 0.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2302 2.2045 1.1557 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5377 1.9970 1.7744 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.8335 0.6448 1.6746 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7674 0.0669 1.0022 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7495 -1.1500 0.7496 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4881 2.3382 3.2721 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1251 1.5546 -2.1457 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1363 -1.3566 0.7059 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5554 -2.9579 1.5081 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7980 0.0109 0.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0381 -0.1132 1.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0541 1.4750 0.9661 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8992 -0.0578 0.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7515 -0.7122 -0.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1681 2.2616 0.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9662 1.5889 -1.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6635 2.1985 -1.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9449 0.4857 -2.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8255 0.7521 -1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9055 -0.1490 -0.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2836 1.9539 1.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2116 2.8448 0.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0633 2.3426 2.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3979 0.5799 1.9702 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7539 2.4016 0.1622 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0400 0.6560 -0.2503 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6767 1.8453 2.2089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8464 1.1121 0.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7368 -0.2136 2.8416 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9705 -0.3580 2.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1453 -2.3512 1.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0306 -1.3392 0.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0618 -0.7399 -0.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2069 -2.5072 -0.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2698 -0.9019 1.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9292 -2.7054 -1.0584 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5057 -0.6478 -1.9285 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5794 0.2946 -0.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5134 -1.4990 -2.8154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9758 0.1819 -2.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1187 -2.2978 -1.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2860 0.0794 0.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5064 1.0942 -1.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6928 -0.1044 -1.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5614 1.8564 0.4809 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6853 1.9423 -0.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6633 1.4822 1.2246 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7764 -0.0023 1.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8739 0.4670 -0.6848 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0469 -0.4048 0.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4375 -1.4097 -1.5933 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5986 -2.2092 0.0317 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5898 -0.3977 -1.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6982 -1.4308 0.3108 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5538 -3.3225 -0.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3936 -2.4552 -2.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5192 -2.1900 -0.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6643 -2.8570 -1.8469 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8767 -0.8929 -1.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6691 -0.8464 -2.9922 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3454 0.7940 -1.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9488 1.9609 0.1152 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8015 0.3133 0.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7508 3.1783 1.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3458 2.6086 1.3174 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5206 2.3376 3.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9567 3.2746 3.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9322 1.5388 3.8206 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7270 2.4038 -1.8956 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6204 -1.6018 1.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9374 -3.6278 1.1209 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 2 0 25 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 2 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 35 39 1 0 31 40 1 0 19 41 1 0 13 42 1 0 18 14 1 0 37 33 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 1 14 69 1 6 15 70 1 0 15 71 1 0 16 72 1 0 16 73 1 0 17 74 1 6 19 75 1 1 20 76 1 0 20 77 1 0 21 78 1 0 21 79 1 0 22 80 1 0 22 81 1 0 23 82 1 0 23 83 1 0 24 84 1 0 24 85 1 0 27 86 1 0 27 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 30 93 1 0 31 94 1 6 32 95 1 0 32 96 1 0 34 97 1 0 35 98 1 6 39 99 1 0 39100 1 0 39101 1 0 40102 1 0 41103 1 0 42104 1 0 M END

Standard InCHIKey	QCICHLFBIUXRKT-WOHTVGPXSA-N
Standard InCHI	InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(36)19-16-17-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,30-34,37-39H,3-24,26H2,1-2H3/t27-,30+,31-,32+,33-,34+/m0/s1
SMILES	CCCCCCCCCCCC[C@@H]([C@@H]1CC[C@@H](O1)[C@@H](CCCCCC(=O)CCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.45	Volume:	650.425 ? Van der Waals volume.
Dense:	0.914	LogP:	5.315 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.654 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.483 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	12.0
TPSA:	113.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.071	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.501	Fsp³:	0.886
MCE-18:	32.273 ? 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:	0.852	Fluc inhibitor:	0.058 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.09 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.563	Promiscuous compounds:	0.438

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.193	MDCK Permeability:	-4.85
Pgp-inhibitor:	0.002	Pgp-substrate:	0.98
PAMPA:	0.132 ? 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):	0.057
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	96.432%	Volume Distribution (VD):	0.388
Fu:	3.273% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.091
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.312
BSEP inhibitor:	0.911

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.985
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.133 ? 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):

5.657

Half-life (T1/2):

1.039

ADMET: Toxicity

hERG Blockers:	0.52	hERG Blockers (10um):	0.797
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.238
AMES Toxicity:	0.296	Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.914	Skin Sensitization:	1.0
Carcinogencity:	0.448	Eye Corrosion:	0.068
Eye Irritation:	0.777	Respiratory Toxicity:	0.943
Drug-induced Neurotoxicity:	0.224	Ototoxicity:	0.53
Hematotoxicity:	0.189	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.119
A549 Cytotoxicity:	0.936	Hek293 Cytotoxicity:	0.433
BCF:	1.091 ? 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:	4.819 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.113 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.794 ? 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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	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	12

Activity Type	# Activity
Cell line	12

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	=	6.0	10'-1 ug/ml	PMID[17958396]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[17958396]
NPT139	Cell line	HT-29	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[17958396]
NPT376	Cell line	A498	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[17958396]
NPT306	Cell line	PC-3	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[17958396]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.2	10'-4 ug/ml	PMID[19738026]

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	=	0.15	ug.mL-1	PMID[17958396]

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 NPC210218 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	16263
0.1-0.2	30221
0.2-0.3	3046
0.3-0.4	91
0.4-0.5	28
0.5-0.6	27
0.6-0.7	82
0.7-0.8	0
0.8-0.85	24
0.85-0.9	1
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473687
1.0	High Similarity	NPC204686
1.0	High Similarity	NPC219498
1.0	High Similarity	NPC308412
1.0	High Similarity	NPC134885
1.0	High Similarity	NPC488247
1.0	High Similarity	NPC488248
0.9362	High Similarity	NPC134807
0.8667	High Similarity	NPC606043
0.8478	Intermediate Similarity	NPC107986
0.8478	Intermediate Similarity	NPC223871
0.8478	Intermediate Similarity	NPC231009
0.8478	Intermediate Similarity	NPC103284
0.8478	Intermediate Similarity	NPC110710
0.8478	Intermediate Similarity	NPC1083
0.8478	Intermediate Similarity	NPC82795
0.8478	Intermediate Similarity	NPC286338
0.8478	Intermediate Similarity	NPC603931
0.8478	Intermediate Similarity	NPC604237
0.8298	Intermediate Similarity	NPC488253
0.8298	Intermediate Similarity	NPC473669
0.8298	Intermediate Similarity	NPC488251
0.8235	Intermediate Similarity	NPC130359
0.8235	Intermediate Similarity	NPC14901
0.82	Intermediate Similarity	NPC477010
0.8125	Intermediate Similarity	NPC232555
0.8125	Intermediate Similarity	NPC171174
0.8125	Intermediate Similarity	NPC114694
0.8125	Intermediate Similarity	NPC485248
0.8125	Intermediate Similarity	NPC142117
0.8125	Intermediate Similarity	NPC480249
0.8125	Intermediate Similarity	NPC485249
0.8125	Intermediate Similarity	NPC240695
0.7959	Intermediate Similarity	NPC488632
0.7959	Intermediate Similarity	NPC134865
0.7959	Intermediate Similarity	NPC103523
0.7959	Intermediate Similarity	NPC144415
0.7959	Intermediate Similarity	NPC488627
0.7959	Intermediate Similarity	NPC488631
0.7959	Intermediate Similarity	NPC608157
0.78	Intermediate Similarity	NPC280621
0.78	Intermediate Similarity	NPC48338
0.78	Intermediate Similarity	NPC488628
0.7755	Intermediate Similarity	NPC81045
0.7755	Intermediate Similarity	NPC39754
0.7755	Intermediate Similarity	NPC171135
0.7755	Intermediate Similarity	NPC182383
0.7755	Intermediate Similarity	NPC61257
0.7755	Intermediate Similarity	NPC320569
0.7755	Intermediate Similarity	NPC133730
0.7755	Intermediate Similarity	NPC191929
0.7755	Intermediate Similarity	NPC100454
0.7755	Intermediate Similarity	NPC242364
0.7755	Intermediate Similarity	NPC172821
0.7755	Intermediate Similarity	NPC274446
0.7755	Intermediate Similarity	NPC485251
0.7755	Intermediate Similarity	NPC151403
0.7755	Intermediate Similarity	NPC261952
0.7755	Intermediate Similarity	NPC605171
0.7647	Intermediate Similarity	NPC178215
0.76	Intermediate Similarity	NPC93794
0.76	Intermediate Similarity	NPC473504
0.76	Intermediate Similarity	NPC81778
0.76	Intermediate Similarity	NPC40066
0.75	Intermediate Similarity	NPC20621
0.75	Intermediate Similarity	NPC318963
0.75	Intermediate Similarity	NPC488250
0.75	Intermediate Similarity	NPC605101
0.7358	Intermediate Similarity	NPC69082
0.7358	Intermediate Similarity	NPC11456
0.7358	Intermediate Similarity	NPC488249
0.7358	Intermediate Similarity	NPC477012
0.7308	Intermediate Similarity	NPC42598
0.7255	Intermediate Similarity	NPC47937
0.7255	Intermediate Similarity	NPC477011
0.7241	Intermediate Similarity	NPC482766
0.717	Intermediate Similarity	NPC602738
0.717	Intermediate Similarity	NPC605396
0.7091	Intermediate Similarity	NPC488623
0.7091	Intermediate Similarity	NPC488624
0.7091	Intermediate Similarity	NPC488629
0.7037	Intermediate Similarity	NPC473478
0.7037	Intermediate Similarity	NPC473651
0.7037	Intermediate Similarity	NPC66346
0.7	Intermediate Similarity	NPC100921
0.7	Intermediate Similarity	NPC475159
0.7	Intermediate Similarity	NPC131002
0.7	Intermediate Similarity	NPC473780
0.7	Intermediate Similarity	NPC477018
0.7	Intermediate Similarity	NPC604521
0.6957	Remote Similarity	NPC608138
0.6949	Remote Similarity	NPC477017
0.6949	Remote Similarity	NPC477016
0.6939	Remote Similarity	NPC112685
0.6909	Remote Similarity	NPC283085
0.6909	Remote Similarity	NPC169511
0.6909	Remote Similarity	NPC287164
0.6909	Remote Similarity	NPC234077
0.6909	Remote Similarity	NPC488244
0.6842	Remote Similarity	NPC488630
0.6842	Remote Similarity	NPC488625
0.6842	Remote Similarity	NPC488626
0.6842	Remote Similarity	NPC280612
0.6735	Remote Similarity	NPC73310
0.6735	Remote Similarity	NPC473529
0.6735	Remote Similarity	NPC180363
0.6735	Remote Similarity	NPC94875
0.6735	Remote Similarity	NPC11332
0.6735	Remote Similarity	NPC145914
0.6735	Remote Similarity	NPC601174
0.6735	Remote Similarity	NPC601403
0.6735	Remote Similarity	NPC603568
0.6735	Remote Similarity	NPC604330
0.6735	Remote Similarity	NPC608300
0.6735	Remote Similarity	NPC611200
0.6735	Remote Similarity	NPC611571
0.6731	Remote Similarity	NPC156804
0.6724	Remote Similarity	NPC477015
0.6667	Remote Similarity	NPC239517
0.6607	Remote Similarity	NPC231096
0.6607	Remote Similarity	NPC475581
0.6607	Remote Similarity	NPC62118
0.6607	Remote Similarity	NPC132496
0.6607	Remote Similarity	NPC107717
0.6607	Remote Similarity	NPC488252
0.6604	Remote Similarity	NPC163093
0.6552	Remote Similarity	NPC91067
0.6491	Remote Similarity	NPC233551
0.6491	Remote Similarity	NPC40376
0.6491	Remote Similarity	NPC21208
0.6429	Remote Similarity	NPC20339
0.6346	Remote Similarity	NPC329829
0.6333	Remote Similarity	NPC473663
0.6333	Remote Similarity	NPC473723
0.6333	Remote Similarity	NPC475173
0.6316	Remote Similarity	NPC606740
0.6316	Remote Similarity	NPC608614
0.6296	Remote Similarity	NPC473649
0.6296	Remote Similarity	NPC473156
0.6296	Remote Similarity	NPC154097
0.6296	Remote Similarity	NPC159750
0.6296	Remote Similarity	NPC73248
0.6296	Remote Similarity	NPC282815
0.6296	Remote Similarity	NPC470401
0.6296	Remote Similarity	NPC600956
0.6296	Remote Similarity	NPC610454
0.6271	Remote Similarity	NPC480081
0.625	Remote Similarity	NPC309211
0.625	Remote Similarity	NPC329838
0.623	Remote Similarity	NPC488245
0.6182	Remote Similarity	NPC473671
0.6182	Remote Similarity	NPC475268
0.6182	Remote Similarity	NPC470400
0.6182	Remote Similarity	NPC77871
0.6182	Remote Similarity	NPC9678
0.6182	Remote Similarity	NPC319036
0.6182	Remote Similarity	NPC604764
0.6182	Remote Similarity	NPC605867
0.6071	Remote Similarity	NPC478998
0.6071	Remote Similarity	NPC132940
0.6038	Remote Similarity	NPC25764
0.6038	Remote Similarity	NPC235809
0.6038	Remote Similarity	NPC39279
0.6038	Remote Similarity	NPC39167
0.6038	Remote Similarity	NPC292809
0.6038	Remote Similarity	NPC202055
0.6038	Remote Similarity	NPC606804
0.6038	Remote Similarity	NPC607425
0.6038	Remote Similarity	NPC608574
0.6034	Remote Similarity	NPC258068
0.6034	Remote Similarity	NPC476583
0.6	Remote Similarity	NPC607439
0.5965	Remote Similarity	NPC20533
0.5932	Remote Similarity	NPC477014
0.5932	Remote Similarity	NPC477013
0.5893	Remote Similarity	NPC241360
0.5893	Remote Similarity	NPC293136
0.5893	Remote Similarity	NPC480079
0.5873	Remote Similarity	NPC279267
0.5789	Remote Similarity	NPC473699
0.5789	Remote Similarity	NPC51249
0.5789	Remote Similarity	NPC473904
0.5763	Remote Similarity	NPC120398
0.5763	Remote Similarity	NPC471567
0.5714	Remote Similarity	NPC488246
0.5714	Remote Similarity	NPC480080
0.5714	Remote Similarity	NPC600524
0.5714	Remote Similarity	NPC608355
0.5667	Remote Similarity	NPC89001
0.5614	Remote Similarity	NPC219652
0.5614	Remote Similarity	NPC473840
0.5593	Remote Similarity	NPC473707
0.5517	Remote Similarity	NPC65930
0.5424	Remote Similarity	NPC485250
0.5424	Remote Similarity	NPC600188
0.5397	Remote Similarity	NPC475206
0.5345	Remote Similarity	NPC25703
0.5246	Remote Similarity	NPC473995
0.5172	Remote Similarity	NPC482767

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC210218 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6119
0.1-0.2	2963
0.2-0.3	67
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