NPASS Compound

Natural Product: NPC81778

Natural Product ID	NPC81778
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	10-Hydroxytrilobacin
IUPAC Name	(2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(2S,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Synonyms	10-Hydroxytrilobacin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509800
PubChem CID	9986592
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 -14.1326 1.8650 -0.5840 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5582 0.8646 0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0555 1.0464 0.4740 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4569 0.0483 1.4546 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7053 -1.3553 1.0852 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2887 -1.9010 -0.2052 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8705 -1.9468 -0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1690 -0.6450 -0.8066 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7362 -0.8970 -1.3150 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9881 -1.7086 -0.3197 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5474 -1.9767 -0.7715 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8465 -0.6721 -0.9411 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7236 0.1191 0.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4628 0.9577 0.0662 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 0.4183 -1.2544 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5209 0.4399 -1.4633 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9612 1.8195 -1.4221 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0406 1.7060 -0.2850 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4522 0.2233 -0.4049 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0787 -0.0462 -1.7227 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5549 -0.1401 -1.8190 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4481 0.9378 -1.3992 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5455 1.2321 0.0645 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0699 -0.0509 0.7101 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2424 0.1124 2.2039 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2049 1.1925 2.5619 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5934 0.9488 2.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1562 -0.3401 2.5256 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5243 -0.6074 2.0040 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5735 -0.7137 0.5176 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9618 -1.0145 -0.0220 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9592 0.0308 0.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3317 -0.2489 -0.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4332 -0.4168 0.5258 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5912 -0.6738 -0.3294 C 0 0 2 0 0 0 0 0 0 0 0 0 15.5983 0.4525 -0.0727 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0868 -0.6248 -1.6306 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7212 -0.3771 -1.5803 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9629 -0.2832 -2.6079 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8380 -1.1488 -1.3903 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9855 0.4292 2.7572 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -1.4623 -1.9521 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8783 -0.2903 -0.4864 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4973 -0.9024 -1.3014 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5380 -2.7178 -1.9426 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.4772 1.3646 -1.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9739 2.3822 -0.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3381 2.5843 -0.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9529 1.0319 1.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8347 -0.1500 0.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6006 0.9672 -0.5297 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8520 2.0742 0.8382 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4389 0.2966 1.7268 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0800 0.2095 2.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8238 -1.5614 1.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2565 -1.9828 1.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7575 -2.9528 -0.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8375 -1.3817 -1.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3098 -2.5721 0.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8326 -2.5583 -1.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0783 -0.0104 0.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7022 -0.0188 -1.5906 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8004 -1.3503 -2.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2264 0.1098 -1.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9294 -1.1469 0.6243 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4046 -2.7327 -0.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0719 -2.6138 0.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2817 -0.0612 -1.7579 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6050 0.7725 0.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5537 -0.5258 1.1941 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7596 0.8048 0.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8076 2.0218 -0.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4741 0.9624 -2.0899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3207 -0.0416 -2.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 2.5965 -1.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4775 2.1601 -2.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4698 1.8211 0.6673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8601 2.4039 -0.3939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9150 -0.1756 0.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5935 0.4700 -2.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8531 -1.1291 -1.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7557 -0.3904 -2.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3284 1.8821 -2.0019 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5062 0.6178 -1.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2622 2.0725 0.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6438 1.4887 0.6052 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2686 -0.8075 0.5888 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9677 -0.4088 0.2164 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4971 -0.8821 2.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3185 1.1794 3.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7959 2.1598 2.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2338 1.8035 2.2836 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5707 0.8931 0.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4666 -1.1994 2.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2344 -0.3169 3.6520 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1880 0.2285 2.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9130 -1.5125 2.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2679 0.2750 0.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8840 -1.4809 0.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2512 -2.0104 0.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6446 1.0233 -0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9827 0.1263 1.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4163 -0.3589 1.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0696 -1.6463 -0.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 16.5853 0.2226 -0.5133 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1462 1.3847 -0.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6732 0.5121 1.0441 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0341 -0.6765 -1.7442 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1438 0.5329 3.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2236 -1.9522 -1.2608 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1365 -3.6170 -1.8379 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 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 31 40 1 0 25 41 1 0 20 42 1 0 19 43 1 0 15 44 1 0 11 45 1 0 44 12 1 0 43 16 1 0 38 33 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 1 12 68 1 6 13 69 1 0 13 70 1 0 14 71 1 0 14 72 1 0 15 73 1 6 16 74 1 6 17 75 1 0 17 76 1 0 18 77 1 0 18 78 1 0 19 79 1 1 20 80 1 6 21 81 1 0 21 82 1 0 22 83 1 0 22 84 1 0 23 85 1 0 23 86 1 0 24 87 1 0 24 88 1 0 25 89 1 1 26 90 1 0 26 91 1 0 27 92 1 0 27 93 1 0 28 94 1 0 28 95 1 0 29 96 1 0 29 97 1 0 30 98 1 0 30 99 1 0 31100 1 1 32101 1 0 32102 1 0 34103 1 0 35104 1 1 36105 1 0 36106 1 0 36107 1 0 40108 1 0 41109 1 0 42110 1 0 45111 1 0 M END

Standard InCHIKey	QFFLFGFTHVFFDL-LYCOMLBHSA-N
Standard InCHI	InChI=1S/C37H66O8/c1-3-4-5-6-7-8-9-13-19-31(40)33-21-23-35(44-33)36-24-22-34(45-36)32(41)20-15-14-17-29(38)16-11-10-12-18-30(39)26-28-25-27(2)43-37(28)42/h25,27,29-36,38-41H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+,35-,36+/m0/s1
SMILES	CCCCCCCCCC[C@H]([C@H]1CC[C@@H]([C@H]2CC[C@H]([C@@H](CCCC[C@@H](CCCCC[C@H](CC3=C[C@H](C)OC3=O)O)O)O)O2)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.48	Volume:	687.887 ? Van der Waals volume.
Dense:	0.928	LogP:	4.168 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.273 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.236 ? 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:	4.943	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:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.889	Fluc inhibitor:	0.026 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.589	Promiscuous compounds:	0.337

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.226	MDCK Permeability:	-4.862
Pgp-inhibitor:	0.007	Pgp-substrate:	0.992
PAMPA:	0.314 ? 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):	0.0
20% Bioavailability (F20%):	0.914	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.582
Plasma Protein Binding (PPB):	93.103%	Volume Distribution (VD):	0.256
Fu:	6.367% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.38
OATP1B3 inhibitor:	0.636	BCRP inhibitor:	0.887
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.996	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.054	CYP2D6-substrate:	0.969
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
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):

7.811

Half-life (T1/2):

1.167

ADMET: Toxicity

hERG Blockers:	0.485	hERG Blockers (10um):	0.78
Human Hepatotoxicity (H-HT):	0.719	Drug-induced Liver Injury (DILI):	0.111
AMES Toxicity:	0.358	Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.93	Skin Sensitization:	1.0
Carcinogencity:	0.508	Eye Corrosion:	0.034
Eye Irritation:	0.79	Respiratory Toxicity:	0.964
Drug-induced Neurotoxicity:	0.073	Ototoxicity:	0.779
Hematotoxicity:	0.104	Drug-induced Nephrotoxicity:	0.955
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.116
A549 Cytotoxicity:	0.992	Hek293 Cytotoxicity:	0.464
BCF:	1.374 ? 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:	4.855 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.97 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.288 ? 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	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
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	3.78	10'-1 ug/ml	PMID[11473410]
NPT376	Cell line	A498	Homo sapiens	ED50	=	1.0	10'-2 ug/ml	PMID[15921418]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.39	ug ml-1	PMID[22530813]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	1.88	10'-8 ug/ml	PMID[23819871]
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.0	10'-8 ug/ml	PMID[18070958]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.96	10'-1 ug/ml	PMID[22703109]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	3.8	10'-1 ug/ml	DOI[10.6019/CHEMBL1201861]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	2.0	10'-1 ug/ml	PMID[8133298]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	1.9	10'-8 ug/ml	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.4	10'-1 ug/ml	PMID[18359631]

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	=	2.6	10'-13 ug/ml	PMID[20187635]
-	Artemia salina	LC50	=	2.6	10'-1ppm	PMID[1431942]

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 NPC81778 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	16446
0.1-0.2	30148
0.2-0.3	2933
0.3-0.4	97
0.4-0.5	22
0.5-0.6	19
0.6-0.7	49
0.7-0.8	0
0.8-0.85	29
0.85-0.9	18
0.9-0.95	0
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC93794
1.0	High Similarity	NPC473504
1.0	High Similarity	NPC40066
0.9767	High Similarity	NPC81045
0.9767	High Similarity	NPC39754
0.9767	High Similarity	NPC171135
0.9767	High Similarity	NPC61257
0.9767	High Similarity	NPC320569
0.9767	High Similarity	NPC133730
0.9767	High Similarity	NPC191929
0.9767	High Similarity	NPC100454
0.9767	High Similarity	NPC242364
0.9767	High Similarity	NPC172821
0.9767	High Similarity	NPC274446
0.9767	High Similarity	NPC485251
0.9767	High Similarity	NPC151403
0.9767	High Similarity	NPC261952
0.9767	High Similarity	NPC605171
0.9556	High Similarity	NPC42598
0.8936	High Similarity	NPC602738
0.8864	High Similarity	NPC107986
0.8864	High Similarity	NPC223871
0.8864	High Similarity	NPC231009
0.8864	High Similarity	NPC103284
0.8864	High Similarity	NPC110710
0.8864	High Similarity	NPC1083
0.8864	High Similarity	NPC82795
0.8864	High Similarity	NPC286338
0.8864	High Similarity	NPC603931
0.8864	High Similarity	NPC604237
0.8667	High Similarity	NPC488253
0.8667	High Similarity	NPC473669
0.8667	High Similarity	NPC488251
0.8636	High Similarity	NPC606043
0.8571	High Similarity	NPC169511
0.8571	High Similarity	NPC287164
0.8571	High Similarity	NPC234077
0.8478	Intermediate Similarity	NPC232555
0.8478	Intermediate Similarity	NPC171174
0.8478	Intermediate Similarity	NPC114694
0.8478	Intermediate Similarity	NPC485248
0.8478	Intermediate Similarity	NPC142117
0.8478	Intermediate Similarity	NPC480249
0.8478	Intermediate Similarity	NPC485249
0.8478	Intermediate Similarity	NPC240695
0.8298	Intermediate Similarity	NPC488632
0.8298	Intermediate Similarity	NPC473649
0.8298	Intermediate Similarity	NPC473156
0.8298	Intermediate Similarity	NPC154097
0.8298	Intermediate Similarity	NPC159750
0.8298	Intermediate Similarity	NPC73248
0.8298	Intermediate Similarity	NPC282815
0.8298	Intermediate Similarity	NPC470401
0.8298	Intermediate Similarity	NPC600956
0.8298	Intermediate Similarity	NPC610454
0.8235	Intermediate Similarity	NPC239517
0.8125	Intermediate Similarity	NPC473671
0.8125	Intermediate Similarity	NPC475268
0.8125	Intermediate Similarity	NPC470400
0.8125	Intermediate Similarity	NPC77871
0.8125	Intermediate Similarity	NPC9678
0.8125	Intermediate Similarity	NPC319036
0.8125	Intermediate Similarity	NPC604764
0.8125	Intermediate Similarity	NPC605867
0.8085	Intermediate Similarity	NPC182383
0.8077	Intermediate Similarity	NPC91067
0.7959	Intermediate Similarity	NPC178215
0.7959	Intermediate Similarity	NPC132940
0.7917	Intermediate Similarity	NPC134865
0.7917	Intermediate Similarity	NPC103523
0.7917	Intermediate Similarity	NPC488627
0.7917	Intermediate Similarity	NPC488631
0.78	Intermediate Similarity	NPC20533
0.78	Intermediate Similarity	NPC488250
0.7778	Intermediate Similarity	NPC473663
0.7778	Intermediate Similarity	NPC473723
0.7778	Intermediate Similarity	NPC475173
0.7755	Intermediate Similarity	NPC280621
0.7755	Intermediate Similarity	NPC48338
0.7755	Intermediate Similarity	NPC488628
0.7674	Intermediate Similarity	NPC608138
0.766	Intermediate Similarity	NPC25764
0.766	Intermediate Similarity	NPC235809
0.766	Intermediate Similarity	NPC39279
0.766	Intermediate Similarity	NPC39167
0.766	Intermediate Similarity	NPC292809
0.766	Intermediate Similarity	NPC202055
0.766	Intermediate Similarity	NPC606804
0.766	Intermediate Similarity	NPC607425
0.766	Intermediate Similarity	NPC608574
0.7647	Intermediate Similarity	NPC69082
0.7647	Intermediate Similarity	NPC488249
0.76	Intermediate Similarity	NPC473687
0.76	Intermediate Similarity	NPC204686
0.76	Intermediate Similarity	NPC219498
0.76	Intermediate Similarity	NPC308412
0.76	Intermediate Similarity	NPC134885
0.76	Intermediate Similarity	NPC488247
0.76	Intermediate Similarity	NPC210218
0.76	Intermediate Similarity	NPC488248
0.7551	Intermediate Similarity	NPC47937
0.7551	Intermediate Similarity	NPC477011
0.7451	Intermediate Similarity	NPC20621
0.7451	Intermediate Similarity	NPC318963
0.7451	Intermediate Similarity	NPC605101
0.74	Intermediate Similarity	NPC480079
0.7358	Intermediate Similarity	NPC89001
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
0.7292	Intermediate Similarity	NPC100921
0.7292	Intermediate Similarity	NPC475159
0.7292	Intermediate Similarity	NPC131002
0.7292	Intermediate Similarity	NPC473780
0.7292	Intermediate Similarity	NPC477018
0.7292	Intermediate Similarity	NPC604521
0.7234	Intermediate Similarity	NPC112685
0.72	Intermediate Similarity	NPC600524
0.72	Intermediate Similarity	NPC608355
0.717	Intermediate Similarity	NPC120398
0.717	Intermediate Similarity	NPC283085
0.717	Intermediate Similarity	NPC130359
0.717	Intermediate Similarity	NPC14901
0.717	Intermediate Similarity	NPC471567
0.7115	Intermediate Similarity	NPC134807
0.7059	Intermediate Similarity	NPC219652
0.7059	Intermediate Similarity	NPC473840
0.7	Intermediate Similarity	NPC156804
0.6981	Remote Similarity	NPC473707
0.6981	Remote Similarity	NPC20339
0.6852	Remote Similarity	NPC231096
0.6852	Remote Similarity	NPC475581
0.6852	Remote Similarity	NPC62118
0.6852	Remote Similarity	NPC132496
0.6852	Remote Similarity	NPC107717
0.6852	Remote Similarity	NPC488252
0.6792	Remote Similarity	NPC485250
0.6792	Remote Similarity	NPC605396
0.6786	Remote Similarity	NPC488630
0.6786	Remote Similarity	NPC488625
0.6786	Remote Similarity	NPC488626
0.6731	Remote Similarity	NPC25703
0.6727	Remote Similarity	NPC233551
0.6727	Remote Similarity	NPC40376
0.6727	Remote Similarity	NPC21208
0.6667	Remote Similarity	NPC73310
0.6667	Remote Similarity	NPC473529
0.6667	Remote Similarity	NPC180363
0.6667	Remote Similarity	NPC94875
0.6667	Remote Similarity	NPC11332
0.6667	Remote Similarity	NPC145914
0.6667	Remote Similarity	NPC601174
0.6667	Remote Similarity	NPC601403
0.6667	Remote Similarity	NPC603568
0.6667	Remote Similarity	NPC604330
0.6667	Remote Similarity	NPC608300
0.6667	Remote Similarity	NPC611200
0.6667	Remote Similarity	NPC611571
0.6545	Remote Similarity	NPC473995
0.6545	Remote Similarity	NPC606740
0.6545	Remote Similarity	NPC608614
0.6538	Remote Similarity	NPC163093
0.6491	Remote Similarity	NPC480081
0.6481	Remote Similarity	NPC309211
0.6481	Remote Similarity	NPC329838
0.6481	Remote Similarity	NPC477010
0.6275	Remote Similarity	NPC329829
0.625	Remote Similarity	NPC258068
0.625	Remote Similarity	NPC476583
0.6226	Remote Similarity	NPC488246
0.6226	Remote Similarity	NPC480080
0.6207	Remote Similarity	NPC473520
0.614	Remote Similarity	NPC477014
0.614	Remote Similarity	NPC477013
0.6102	Remote Similarity	NPC473905
0.6066	Remote Similarity	NPC482766
0.6066	Remote Similarity	NPC279267
0.5926	Remote Similarity	NPC144415
0.5926	Remote Similarity	NPC607439
0.5926	Remote Similarity	NPC608157
0.5818	Remote Similarity	NPC241360
0.5818	Remote Similarity	NPC293136
0.5789	Remote Similarity	NPC480076
0.5789	Remote Similarity	NPC480077
0.5769	Remote Similarity	NPC480072
0.5714	Remote Similarity	NPC473904
0.5714	Remote Similarity	NPC65930
0.5667	Remote Similarity	NPC280612
0.5556	Remote Similarity	NPC477017
0.5556	Remote Similarity	NPC477016
0.5517	Remote Similarity	NPC11456
0.5517	Remote Similarity	NPC477012
0.5424	Remote Similarity	NPC488244
0.5357	Remote Similarity	NPC480078
0.5357	Remote Similarity	NPC480071
0.5345	Remote Similarity	NPC329615

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC81778 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6373
0.1-0.2	2719
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