NPASS Compound

Natural Product: NPC139418

Natural Product ID	NPC139418
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Donnaienin C
IUPAC Name	[(2R,8R,13R)-8,13-dihydroxy-1-[(5S)-5-hydroxy-5-methyl-2-oxofuran-3-yl]-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecan-2-yl] acetate
Synonyms	Donnaienin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500505
PubChem CID	44559052
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 112113 0 0 0 0 0 0 0 0999 V2000 13.7246 1.3558 -2.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3847 -0.0599 -2.6666 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2659 -0.6293 -1.7821 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0142 0.1963 -1.9525 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8569 -0.2874 -1.1404 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2003 -0.2717 0.3173 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0720 -0.7406 1.1921 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8166 0.1553 1.0526 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1395 1.5216 1.4561 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1957 2.6206 1.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9531 2.6332 2.2122 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8924 1.6288 1.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3676 1.7139 0.5073 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3044 0.6592 0.3171 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9188 -0.6855 0.2907 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9238 -1.5160 1.0670 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1658 -0.5058 1.8464 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3894 0.7566 1.3493 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6742 -0.7632 1.8880 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0945 -0.4331 0.5241 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 -0.7360 0.6655 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1353 -0.4296 -0.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6341 -0.7227 -0.4058 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 -2.1504 -0.1205 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1336 -2.7341 0.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2358 -2.7010 -0.8271 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8408 -1.3860 -1.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9785 -1.7119 -2.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7003 -0.4962 -2.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3316 0.2912 -1.5046 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3080 -0.5534 -0.7605 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9812 0.0881 0.3791 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8899 -0.3191 1.6487 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6815 0.5350 2.5588 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3103 1.4520 1.7271 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8878 1.2192 0.4297 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2536 1.9087 -0.5706 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6529 -0.3610 3.3059 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8427 1.2070 3.4724 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8902 1.4864 -1.9710 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3487 2.7333 -1.6306 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3384 2.7203 -0.8882 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9034 4.0120 -2.0972 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0622 -2.9228 -1.0534 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3635 -2.0232 2.3407 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2979 1.5742 -0.4929 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3771 2.0397 -3.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1861 1.7121 -1.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8011 1.5091 -2.1181 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0391 -0.1236 -3.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3060 -0.6677 -2.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5846 -0.7224 -0.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0542 -1.6432 -2.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2154 1.2569 -1.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6880 0.2150 -3.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4804 -1.2770 -1.4747 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0084 0.4244 -1.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6511 0.6732 0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0057 -1.0553 0.4665 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8152 -1.7713 0.9438 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4046 -0.6820 2.2404 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0800 -0.3939 1.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5132 0.0410 -0.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6752 1.4413 2.4649 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0192 1.8426 0.7956 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9358 2.9539 0.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7846 3.5485 1.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4596 3.6392 2.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 2.6751 3.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9842 1.9117 2.5570 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0763 0.5997 2.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8160 2.6950 0.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8185 0.8583 -0.6755 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9145 -1.0811 -0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9174 -0.7729 0.7189 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3123 -2.1573 0.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5048 -2.2035 1.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5163 -0.5688 2.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2500 -0.0521 2.6561 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4720 -1.1477 -0.2301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2576 0.6005 0.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4043 -1.8350 0.9150 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7861 -0.1135 1.4928 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9894 0.6388 -0.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7223 -1.0264 -1.4345 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0598 -0.3763 -1.3772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9491 -0.0435 0.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2274 -2.3438 0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9337 -3.8496 0.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5515 -2.4078 1.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0480 -3.3307 -1.7517 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0995 -3.2811 -0.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2026 -0.6290 -1.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2900 -0.9360 -0.2692 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6142 -2.4940 -1.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4747 -2.1615 -3.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0054 0.1485 -3.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5438 -0.8575 -3.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4899 0.5623 -0.8434 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7234 -1.4475 -0.3897 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0713 -0.9891 -1.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2870 -1.1943 1.9513 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4372 -0.6582 2.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0139 0.0935 4.2469 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0793 -1.2691 3.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6770 0.5914 4.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7037 4.4135 -1.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1113 4.7865 -2.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4050 3.8893 -3.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1322 -3.8687 -0.7056 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6017 -2.7264 1.6841 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9717 1.0688 -1.2864 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 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 2 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 34 38 1 0 34 39 1 1 30 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 24 44 1 0 19 45 1 0 13 46 1 0 18 14 1 0 36 32 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 8 62 1 0 8 63 1 0 9 64 1 0 9 65 1 0 10 66 1 0 10 67 1 0 11 68 1 0 11 69 1 0 12 70 1 0 12 71 1 0 13 72 1 1 14 73 1 6 15 74 1 0 15 75 1 0 16 76 1 0 16 77 1 0 17 78 1 1 19 79 1 1 20 80 1 0 20 81 1 0 21 82 1 0 21 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 24 88 1 1 25 89 1 0 25 90 1 0 26 91 1 0 26 92 1 0 27 93 1 0 27 94 1 0 28 95 1 0 28 96 1 0 29 97 1 0 29 98 1 0 30 99 1 1 31100 1 0 31101 1 0 33102 1 0 38103 1 0 38104 1 0 38105 1 0 39106 1 0 43107 1 0 43108 1 0 43109 1 0 44110 1 0 45111 1 0 46112 1 0 M END

Standard InCHIKey	MULMKVZTRRCCJX-VFHXHHDVSA-N
Standard InCHI	InChI=1S/C37H66O9/c1-4-5-6-7-8-9-10-11-12-16-22-32(40)34-24-25-35(45-34)33(41)23-18-17-20-30(39)19-14-13-15-21-31(44-28(2)38)26-29-27-37(3,43)46-36(29)42/h27,30-35,39-41,43H,4-26H2,1-3H3/t30-,31-,32-,33-,34-,35-,37+/m1/s1
SMILES	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCC[C@@H](CCCCC[C@H](CC1=C[C@@](OC1=O)(C)O)OC(=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.47	Volume:	702.598 ? Van der Waals volume.
Dense:	0.932	LogP:	5.671 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.909 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.284 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	28.0	Rigid Bonds:	12.0
TPSA:	142.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.055	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.851	Fsp³:	0.892
MCE-18:	38.571 ? 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:	0.679	Fluc inhibitor:	0.021 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.457	Promiscuous compounds:	0.564

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.296	MDCK Permeability:	-4.846
Pgp-inhibitor:	0.261	Pgp-substrate:	0.886
PAMPA:	0.09 ? 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):	0.786
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.918
Plasma Protein Binding (PPB):	93.965%	Volume Distribution (VD):	0.332
Fu:	4.799% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.626
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.957
BSEP inhibitor:	0.961

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.532	CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

4.831

Half-life (T1/2):

1.117

ADMET: Toxicity

hERG Blockers:	0.408	hERG Blockers (10um):	0.68
Human Hepatotoxicity (H-HT):	0.639	Drug-induced Liver Injury (DILI):	0.015
AMES Toxicity:	0.029	Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.915	Skin Sensitization:	1.0
Carcinogencity:	0.316	Eye Corrosion:	0.011
Eye Irritation:	0.837	Respiratory Toxicity:	0.958
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.649
Hematotoxicity:	0.046	Drug-induced Nephrotoxicity:	0.874
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	0.974	Hek293 Cytotoxicity:	0.499
BCF:	1.136 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.152 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.456 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.47 ? 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
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	roots	Mudan, Pingtung County, Taiwan	2009-APR	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	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
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT91	Cell line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[10096871]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[10096871]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	7.1	ug.mL-1	PMID[10096871]

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

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 NPC139418 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	18233
0.1-0.2	28449
0.2-0.3	2846
0.3-0.4	107
0.4-0.5	68
0.5-0.6	144
0.6-0.7	4
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	Natural Product ID
0.6429	Remote Similarity	NPC473904
0.6271	Remote Similarity	NPC477014
0.6271	Remote Similarity	NPC477013
0.6207	Remote Similarity	NPC11456
0.5862	Remote Similarity	NPC478998
0.5833	Remote Similarity	NPC258068
0.5833	Remote Similarity	NPC476583
0.5818	Remote Similarity	NPC107986
0.5818	Remote Similarity	NPC223871
0.5818	Remote Similarity	NPC231009
0.5818	Remote Similarity	NPC103284
0.5818	Remote Similarity	NPC100921
0.5818	Remote Similarity	NPC110710
0.5818	Remote Similarity	NPC1083
0.5818	Remote Similarity	NPC475159
0.5818	Remote Similarity	NPC82795
0.5818	Remote Similarity	NPC131002
0.5818	Remote Similarity	NPC286338
0.5818	Remote Similarity	NPC473780
0.5818	Remote Similarity	NPC477018
0.5818	Remote Similarity	NPC603931
0.5818	Remote Similarity	NPC604237
0.5818	Remote Similarity	NPC604521
0.5763	Remote Similarity	NPC20621
0.5763	Remote Similarity	NPC318963
0.5763	Remote Similarity	NPC605101
0.5714	Remote Similarity	NPC488253
0.5714	Remote Similarity	NPC473669
0.5714	Remote Similarity	NPC488251
0.5692	Remote Similarity	NPC477017
0.5692	Remote Similarity	NPC477016
0.5636	Remote Similarity	NPC606043
0.5614	Remote Similarity	NPC232555
0.5614	Remote Similarity	NPC171174
0.5614	Remote Similarity	NPC182383
0.5614	Remote Similarity	NPC114694
0.5614	Remote Similarity	NPC485248
0.5614	Remote Similarity	NPC142117
0.5614	Remote Similarity	NPC480249
0.5614	Remote Similarity	NPC156804
0.5614	Remote Similarity	NPC485249
0.5614	Remote Similarity	NPC240695
0.5593	Remote Similarity	NPC178215
0.5517	Remote Similarity	NPC488632
0.5517	Remote Similarity	NPC163093
0.5517	Remote Similarity	NPC477011
0.5424	Remote Similarity	NPC241360
0.5424	Remote Similarity	NPC293136
0.541	Remote Similarity	NPC473478
0.541	Remote Similarity	NPC473651
0.541	Remote Similarity	NPC66346
0.5345	Remote Similarity	NPC488234
0.5323	Remote Similarity	NPC283085
0.5323	Remote Similarity	NPC169511
0.5323	Remote Similarity	NPC287164
0.5323	Remote Similarity	NPC234077
0.5312	Remote Similarity	NPC488630
0.5312	Remote Similarity	NPC488625
0.5312	Remote Similarity	NPC488626
0.5273	Remote Similarity	NPC73310
0.5273	Remote Similarity	NPC473529
0.5273	Remote Similarity	NPC180363
0.5273	Remote Similarity	NPC94875
0.5273	Remote Similarity	NPC11332
0.5273	Remote Similarity	NPC145914
0.5273	Remote Similarity	NPC601174
0.5273	Remote Similarity	NPC601403
0.5273	Remote Similarity	NPC603568
0.5273	Remote Similarity	NPC604330
0.5273	Remote Similarity	NPC608300
0.5273	Remote Similarity	NPC611200
0.5273	Remote Similarity	NPC611571
0.5254	Remote Similarity	NPC93794
0.5254	Remote Similarity	NPC482767
0.5254	Remote Similarity	NPC473649
0.5254	Remote Similarity	NPC473156
0.5254	Remote Similarity	NPC134865
0.5254	Remote Similarity	NPC154097
0.5254	Remote Similarity	NPC473504
0.5254	Remote Similarity	NPC103523
0.5254	Remote Similarity	NPC475260
0.5254	Remote Similarity	NPC159750
0.5254	Remote Similarity	NPC73248
0.5254	Remote Similarity	NPC282815
0.5254	Remote Similarity	NPC488621
0.5254	Remote Similarity	NPC81778
0.5254	Remote Similarity	NPC40066
0.5254	Remote Similarity	NPC473775
0.5254	Remote Similarity	NPC488627
0.5254	Remote Similarity	NPC47937
0.5254	Remote Similarity	NPC488622
0.5254	Remote Similarity	NPC488631
0.5254	Remote Similarity	NPC470401
0.5254	Remote Similarity	NPC600956
0.5254	Remote Similarity	NPC610454
0.5246	Remote Similarity	NPC309211
0.5246	Remote Similarity	NPC329838
0.5246	Remote Similarity	NPC488250
0.5246	Remote Similarity	NPC477010
0.5231	Remote Similarity	NPC477015
0.5167	Remote Similarity	NPC280621
0.5167	Remote Similarity	NPC473671
0.5167	Remote Similarity	NPC475268
0.5167	Remote Similarity	NPC470400
0.5167	Remote Similarity	NPC77871
0.5167	Remote Similarity	NPC48338
0.5167	Remote Similarity	NPC9678
0.5167	Remote Similarity	NPC319036
0.5167	Remote Similarity	NPC488628
0.5167	Remote Similarity	NPC604764
0.5167	Remote Similarity	NPC605867
0.5161	Remote Similarity	NPC69082
0.5161	Remote Similarity	NPC488249
0.5085	Remote Similarity	NPC81045
0.5085	Remote Similarity	NPC39754
0.5085	Remote Similarity	NPC171135
0.5085	Remote Similarity	NPC61257
0.5085	Remote Similarity	NPC320569
0.5085	Remote Similarity	NPC133730
0.5085	Remote Similarity	NPC191929
0.5085	Remote Similarity	NPC100454
0.5085	Remote Similarity	NPC242364
0.5085	Remote Similarity	NPC172821
0.5085	Remote Similarity	NPC274446
0.5085	Remote Similarity	NPC485251
0.5085	Remote Similarity	NPC151403
0.5085	Remote Similarity	NPC261952
0.5085	Remote Similarity	NPC605171
0.5082	Remote Similarity	NPC480251
0.5082	Remote Similarity	NPC42598
0.5082	Remote Similarity	NPC473687
0.5082	Remote Similarity	NPC204686
0.5082	Remote Similarity	NPC219498
0.5082	Remote Similarity	NPC480250
0.5082	Remote Similarity	NPC65930
0.5082	Remote Similarity	NPC308412
0.5082	Remote Similarity	NPC134885
0.5082	Remote Similarity	NPC488247
0.5082	Remote Similarity	NPC132940
0.5082	Remote Similarity	NPC210218
0.5082	Remote Similarity	NPC488248
0.5079	Remote Similarity	NPC231096
0.5079	Remote Similarity	NPC475581
0.5079	Remote Similarity	NPC62118
0.5079	Remote Similarity	NPC132496
0.5079	Remote Similarity	NPC107717
0.5079	Remote Similarity	NPC488252
0.5077	Remote Similarity	NPC91067

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC139418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6768
0.1-0.2	2317
0.2-0.3	65
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