NPASS Compound

Natural Product: NPC142117

Natural Product ID	NPC142117
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asitrocin
IUPAC Name	(2S)-2-methyl-4-[(2R,10R,13S)-2,10,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Synonyms	Asitrocin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499095
PubChem CID	10393746
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 106107 0 0 0 0 0 0 0 0999 V2000 -9.5168 -3.5333 1.9514 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8677 -3.3263 0.4759 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7847 -3.9499 -0.3203 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4312 -3.4314 -0.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1001 -2.0557 -0.4846 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8518 -0.9191 0.0813 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1958 0.4083 -0.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2193 0.5117 -1.8299 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6433 1.8400 -2.3183 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1851 2.0101 -1.8654 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7005 3.3147 -2.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3434 3.7657 -2.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1464 3.0185 -2.4916 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9718 1.6268 -2.0057 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4712 1.2330 -2.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1274 1.5304 -0.8900 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9779 2.0471 -0.0295 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9023 1.4760 1.3834 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2570 2.2939 2.3978 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1217 2.7402 2.3375 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2185 1.6877 2.3754 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1863 0.8788 3.6321 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1640 -0.1954 3.7132 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6232 0.0025 3.6487 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2698 0.5167 2.4340 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7979 0.5716 2.5754 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4006 -0.7692 2.8213 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1191 -1.7614 1.7295 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6316 -1.3335 0.3737 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2600 -2.4632 -0.5925 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7218 -2.1209 -1.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5809 -2.7707 -2.7354 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7569 -2.0817 -4.0236 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1969 -1.6196 -4.1356 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9103 -0.9749 -3.9463 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2786 -0.9663 -2.7146 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4624 -0.0797 -2.3574 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9946 -1.1715 0.3366 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4374 1.0012 1.2302 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7010 0.1227 1.3525 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0971 1.5447 -0.6389 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0155 3.7938 -2.0465 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6504 -2.9469 2.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2270 -4.6163 2.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3677 -3.2672 2.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7937 -3.9791 0.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0950 -2.3186 0.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0803 -3.8273 -1.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7849 -5.0651 -0.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1514 -3.5141 1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6570 -4.1730 -0.5220 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1269 -2.0063 -1.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9728 -1.9377 -0.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0587 -0.9435 1.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8353 -0.8475 -0.5240 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7053 1.2186 0.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1689 0.3562 0.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6235 -0.3130 -2.2899 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2382 0.4362 -2.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6222 1.7884 -3.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2910 2.6404 -1.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1106 1.9978 -0.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5923 1.1823 -2.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4082 4.1382 -2.0062 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7954 3.3554 -3.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2452 4.8622 -2.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3354 3.8912 -0.9076 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0194 3.0556 -3.6115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4867 0.8451 -2.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3919 0.1689 -2.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0206 1.9054 -2.9760 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0028 2.2163 -0.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4388 0.5302 -0.4720 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0802 3.1496 0.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0424 1.5266 1.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9095 3.2121 2.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3703 1.7227 3.3868 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3629 3.4056 3.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3892 3.3928 1.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1797 2.3373 2.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1650 0.4335 3.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3796 1.6109 4.4724 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9381 -1.0183 2.9289 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9188 -0.7841 4.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9477 0.6718 4.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 -0.9707 3.9539 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0055 -0.1325 1.5454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0063 1.5281 2.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9884 1.2226 3.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1794 1.0772 1.6710 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5204 -0.6132 2.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1859 -1.1398 3.8205 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0477 -1.9986 1.6062 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6494 -2.7157 1.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0888 -0.4351 0.0193 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1629 -2.5971 -0.5799 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7911 -3.4010 -0.2683 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0762 -3.6887 -2.4341 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5406 -2.7414 -4.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2237 -0.5049 -4.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7894 -2.0176 -3.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6427 -1.9543 -5.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2410 -0.2686 0.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3912 0.0337 1.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0600 -0.2380 1.8221 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0961 4.6501 -2.5199 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 21 39 1 0 18 40 1 0 17 41 1 0 13 42 1 0 41 14 1 0 36 31 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 6 14 69 1 6 15 70 1 0 15 71 1 0 16 72 1 0 16 73 1 0 17 74 1 1 18 75 1 1 19 76 1 0 19 77 1 0 20 78 1 0 20 79 1 0 21 80 1 1 22 81 1 0 22 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 25 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 42106 1 0 M END

Standard InCHIKey	DRFBUADSYRWIKE-HOSDBOMYSA-N
Standard InCHI	InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-14-17-20-31(38)33-23-24-34(42-33)32(39)22-21-29(36)18-15-12-11-13-16-19-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32-,33+,34+/m0/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@H]([C@H](CC[C@@H](CCCCCCC[C@H](CC2=C[C@H](C)OC2=O)O)O)O)O1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.47	Volume:	653.062 ? Van der Waals volume.
Dense:	0.913	LogP:	4.757 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.292 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.257 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	26.0	Rigid Bonds:	11.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.617	Fsp³:	0.914
MCE-18:	32.239 ? 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:	0.825	Fluc inhibitor:	0.05 ? 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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.581	Promiscuous compounds:	0.278

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.193	MDCK Permeability:	-4.866
Pgp-inhibitor:	0.0	Pgp-substrate:	0.927
PAMPA:	0.273 ? 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):	0.001
20% Bioavailability (F20%):	0.919	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.786
Plasma Protein Binding (PPB):	96.387%	Volume Distribution (VD):	0.502
Fu:	3.53% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.961
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.56
BSEP inhibitor:	0.916

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.962
CYP3A4-inhibitor:	0.008	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.017 ? 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):

6.278

Half-life (T1/2):

1.124

ADMET: Toxicity

hERG Blockers:	0.515	hERG Blockers (10um):	0.809
Human Hepatotoxicity (H-HT):	0.757	Drug-induced Liver Injury (DILI):	0.215
AMES Toxicity:	0.236	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.949	Skin Sensitization:	1.0
Carcinogencity:	0.548	Eye Corrosion:	0.013
Eye Irritation:	0.78	Respiratory Toxicity:	0.979
Drug-induced Neurotoxicity:	0.076	Ototoxicity:	0.818
Hematotoxicity:	0.118	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	0.993	Hek293 Cytotoxicity:	0.402
BCF:	1.279 ? 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:	4.97 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.138 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.954 ? 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	=	0.118	ug ml-1	PMID[8254344]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	3.28	ug ml-1	PMID[23701598]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	0.00299	ug ml-1	PMID[8254344]
NPT376	Cell line	A498	Homo sapiens	ED50	=	0.0792	ug ml-1	PMID[15165152]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	0.00122	ug ml-1	PMID[15974630]
NPT783	Cell line	MIA PaCa-2	Homo sapiens	ED50	=	1.48e-05	ug ml-1	PMID[14575438]

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	=	0.063	ug.mL-1	PMID[17850214]

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 NPC142117 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	16123
0.1-0.2	30320
0.2-0.3	3075
0.3-0.4	105
0.4-0.5	25
0.5-0.6	20
0.6-0.7	47
0.7-0.8	0
0.8-0.85	39
0.85-0.9	4
0.9-0.95	6
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232555
1.0	High Similarity	NPC171174
1.0	High Similarity	NPC114694
1.0	High Similarity	NPC485248
1.0	High Similarity	NPC480249
1.0	High Similarity	NPC485249
1.0	High Similarity	NPC240695
0.9767	High Similarity	NPC488632
0.9762	High Similarity	NPC473669
0.9524	High Similarity	NPC107986
0.9524	High Similarity	NPC223871
0.9524	High Similarity	NPC231009
0.9524	High Similarity	NPC103284
0.9524	High Similarity	NPC110710
0.9524	High Similarity	NPC1083
0.9524	High Similarity	NPC82795
0.9524	High Similarity	NPC286338
0.9524	High Similarity	NPC603931
0.9524	High Similarity	NPC604237
0.9302	High Similarity	NPC488253
0.9302	High Similarity	NPC488251
0.9286	High Similarity	NPC606043
0.9111	High Similarity	NPC280621
0.9111	High Similarity	NPC48338
0.9111	High Similarity	NPC488628
0.8913	High Similarity	NPC42598
0.8889	High Similarity	NPC47937
0.8667	High Similarity	NPC182383
0.8511	High Similarity	NPC178215
0.8478	Intermediate Similarity	NPC93794
0.8478	Intermediate Similarity	NPC134865
0.8478	Intermediate Similarity	NPC473504
0.8478	Intermediate Similarity	NPC103523
0.8478	Intermediate Similarity	NPC81778
0.8478	Intermediate Similarity	NPC40066
0.8478	Intermediate Similarity	NPC488627
0.8478	Intermediate Similarity	NPC488631
0.8333	Intermediate Similarity	NPC20621
0.8333	Intermediate Similarity	NPC318963
0.8333	Intermediate Similarity	NPC488250
0.8333	Intermediate Similarity	NPC605101
0.8261	Intermediate Similarity	NPC81045
0.8261	Intermediate Similarity	NPC39754
0.8261	Intermediate Similarity	NPC171135
0.8261	Intermediate Similarity	NPC61257
0.8261	Intermediate Similarity	NPC320569
0.8261	Intermediate Similarity	NPC133730
0.8261	Intermediate Similarity	NPC191929
0.8261	Intermediate Similarity	NPC100454
0.8261	Intermediate Similarity	NPC242364
0.8261	Intermediate Similarity	NPC172821
0.8261	Intermediate Similarity	NPC156804
0.8261	Intermediate Similarity	NPC274446
0.8261	Intermediate Similarity	NPC485251
0.8261	Intermediate Similarity	NPC151403
0.8261	Intermediate Similarity	NPC261952
0.8261	Intermediate Similarity	NPC605171
0.8163	Intermediate Similarity	NPC69082
0.8163	Intermediate Similarity	NPC488249
0.8125	Intermediate Similarity	NPC473687
0.8125	Intermediate Similarity	NPC204686
0.8125	Intermediate Similarity	NPC219498
0.8125	Intermediate Similarity	NPC308412
0.8125	Intermediate Similarity	NPC134885
0.8125	Intermediate Similarity	NPC488247
0.8125	Intermediate Similarity	NPC210218
0.8125	Intermediate Similarity	NPC488248
0.8085	Intermediate Similarity	NPC477011
0.7857	Intermediate Similarity	NPC608138
0.7826	Intermediate Similarity	NPC100921
0.7826	Intermediate Similarity	NPC475159
0.7826	Intermediate Similarity	NPC131002
0.7826	Intermediate Similarity	NPC473780
0.7826	Intermediate Similarity	NPC477018
0.7826	Intermediate Similarity	NPC604521
0.78	Intermediate Similarity	NPC20339
0.7647	Intermediate Similarity	NPC130359
0.7647	Intermediate Similarity	NPC14901
0.76	Intermediate Similarity	NPC134807
0.76	Intermediate Similarity	NPC602738
0.75	Intermediate Similarity	NPC488623
0.75	Intermediate Similarity	NPC488624
0.75	Intermediate Similarity	NPC488629
0.7451	Intermediate Similarity	NPC473478
0.7451	Intermediate Similarity	NPC473651
0.7451	Intermediate Similarity	NPC66346
0.74	Intermediate Similarity	NPC132940
0.7391	Intermediate Similarity	NPC112685
0.7308	Intermediate Similarity	NPC231096
0.7308	Intermediate Similarity	NPC475581
0.7308	Intermediate Similarity	NPC283085
0.7308	Intermediate Similarity	NPC169511
0.7308	Intermediate Similarity	NPC62118
0.7308	Intermediate Similarity	NPC287164
0.7308	Intermediate Similarity	NPC234077
0.7308	Intermediate Similarity	NPC132496
0.7308	Intermediate Similarity	NPC107717
0.7308	Intermediate Similarity	NPC488252
0.7308	Intermediate Similarity	NPC606740
0.7308	Intermediate Similarity	NPC608614
0.7255	Intermediate Similarity	NPC329838
0.7255	Intermediate Similarity	NPC20533
0.7222	Intermediate Similarity	NPC488630
0.7222	Intermediate Similarity	NPC488625
0.7222	Intermediate Similarity	NPC488626
0.7174	Intermediate Similarity	NPC73310
0.7174	Intermediate Similarity	NPC473529
0.7174	Intermediate Similarity	NPC180363
0.7174	Intermediate Similarity	NPC94875
0.7174	Intermediate Similarity	NPC11332
0.7174	Intermediate Similarity	NPC145914
0.7174	Intermediate Similarity	NPC601174
0.7174	Intermediate Similarity	NPC601403
0.7174	Intermediate Similarity	NPC603568
0.7174	Intermediate Similarity	NPC604330
0.7174	Intermediate Similarity	NPC608300
0.7174	Intermediate Similarity	NPC611200
0.7174	Intermediate Similarity	NPC611571
0.717	Intermediate Similarity	NPC233551
0.717	Intermediate Similarity	NPC40376
0.717	Intermediate Similarity	NPC21208
0.7037	Intermediate Similarity	NPC239517
0.7	Intermediate Similarity	NPC473649
0.7	Intermediate Similarity	NPC473156
0.7	Intermediate Similarity	NPC154097
0.7	Intermediate Similarity	NPC163093
0.7	Intermediate Similarity	NPC159750
0.7	Intermediate Similarity	NPC73248
0.7	Intermediate Similarity	NPC282815
0.7	Intermediate Similarity	NPC470401
0.7	Intermediate Similarity	NPC600956
0.7	Intermediate Similarity	NPC610454
0.6981	Remote Similarity	NPC258068
0.6981	Remote Similarity	NPC476583
0.6923	Remote Similarity	NPC309211
0.6923	Remote Similarity	NPC477010
0.6909	Remote Similarity	NPC91067
0.6863	Remote Similarity	NPC473671
0.6863	Remote Similarity	NPC475268
0.6863	Remote Similarity	NPC470400
0.6863	Remote Similarity	NPC77871
0.6863	Remote Similarity	NPC9678
0.6863	Remote Similarity	NPC319036
0.6863	Remote Similarity	NPC604764
0.6863	Remote Similarity	NPC605867
0.6735	Remote Similarity	NPC329829
0.6667	Remote Similarity	NPC473663
0.6667	Remote Similarity	NPC473723
0.6667	Remote Similarity	NPC475173
0.6607	Remote Similarity	NPC480081
0.6545	Remote Similarity	NPC477014
0.6545	Remote Similarity	NPC477013
0.6538	Remote Similarity	NPC241360
0.6538	Remote Similarity	NPC293136
0.6538	Remote Similarity	NPC480079
0.6415	Remote Similarity	NPC473904
0.64	Remote Similarity	NPC25764
0.64	Remote Similarity	NPC235809
0.64	Remote Similarity	NPC39279
0.64	Remote Similarity	NPC39167
0.64	Remote Similarity	NPC292809
0.64	Remote Similarity	NPC202055
0.64	Remote Similarity	NPC606804
0.64	Remote Similarity	NPC607425
0.64	Remote Similarity	NPC608574
0.6346	Remote Similarity	NPC488246
0.6346	Remote Similarity	NPC144415
0.6346	Remote Similarity	NPC480080
0.6346	Remote Similarity	NPC607439
0.6346	Remote Similarity	NPC608157
0.625	Remote Similarity	NPC89001
0.6182	Remote Similarity	NPC473707
0.6167	Remote Similarity	NPC482766
0.6167	Remote Similarity	NPC279267
0.6071	Remote Similarity	NPC120398
0.6071	Remote Similarity	NPC471567
0.6038	Remote Similarity	NPC600524
0.6038	Remote Similarity	NPC608355
0.6034	Remote Similarity	NPC280612
0.5926	Remote Similarity	NPC219652
0.5926	Remote Similarity	NPC473840
0.5902	Remote Similarity	NPC477017
0.5902	Remote Similarity	NPC477016
0.5893	Remote Similarity	NPC11456
0.5893	Remote Similarity	NPC477012
0.5818	Remote Similarity	NPC480251
0.5818	Remote Similarity	NPC480250
0.5818	Remote Similarity	NPC65930
0.5714	Remote Similarity	NPC329615
0.5714	Remote Similarity	NPC485250
0.5714	Remote Similarity	NPC605396
0.5636	Remote Similarity	NPC25703
0.5614	Remote Similarity	NPC139418
0.5517	Remote Similarity	NPC473995
0.5517	Remote Similarity	NPC488244
0.5455	Remote Similarity	NPC482767
0.5455	Remote Similarity	NPC475260
0.5455	Remote Similarity	NPC488621
0.5455	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 NPC142117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6305
0.1-0.2	2784
0.2-0.3	61
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