NPASS Compound

Natural Product: NPC116075

Natural Product ID	NPC116075
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cheiranthoside
IUPAC Name	(3S,5S,8R,9S,10S,13R,14S,17R)-3-[(2R,3R,4S,5R,6R)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3122164
PubChem CID	11735184
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 102108 0 0 0 0 0 0 0 0999 V2000 8.9610 -2.1719 -2.2181 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3610 -0.9491 -1.9784 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0201 -0.2340 -0.8149 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4201 0.9779 -0.5825 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5991 1.0108 0.5276 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4208 0.2693 0.3510 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2872 1.0661 0.3681 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5805 0.8823 -0.9578 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4702 -0.5797 -1.2943 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4077 1.5792 -1.0674 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4951 1.4091 -0.0609 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1164 1.6215 1.3057 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3228 0.6900 1.4714 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9164 0.9428 2.6843 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5597 2.9248 1.3902 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8322 0.1894 -0.0809 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4557 0.3263 -0.2258 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0590 -0.4615 -1.4580 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3990 -0.5266 -1.6798 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2527 -0.7476 -0.4854 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7359 -0.1831 0.7944 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2576 -0.3228 0.9365 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2952 -0.8920 1.8845 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1908 1.2576 0.8894 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6807 1.2809 1.1389 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4023 0.1766 0.4100 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6425 -0.1880 -0.8207 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4236 -1.0893 -1.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6395 -1.6986 -1.1275 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5277 -0.7546 -0.3430 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8140 0.5113 0.0567 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4102 1.0215 1.2288 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0067 1.4976 -1.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3662 1.1607 -1.5763 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6879 -0.2724 -1.1453 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9986 -0.3155 -0.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0023 -1.0554 -0.9252 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1629 -0.9134 -0.0635 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3008 -1.4891 -0.2239 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8032 -0.0499 0.9453 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4807 0.3636 0.7394 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9231 -1.4682 0.9311 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4072 -2.2357 -0.2828 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8854 -3.0335 -1.0217 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3047 0.6605 1.8101 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4647 -0.2816 1.5774 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0886 -1.1429 0.3672 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1555 -2.0562 0.2141 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6682 -1.1358 2.6533 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8414 1.8129 2.4083 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2298 -2.2771 -3.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3071 -1.1624 -1.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3067 -0.3086 -2.8760 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0793 -0.0380 -1.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2707 2.0853 0.6373 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5956 2.1037 0.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2833 1.3248 -1.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9544 -1.1715 -0.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4268 -0.8766 -1.4133 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -0.8454 -2.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7396 2.2428 -0.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4039 1.3323 2.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0043 -0.3687 1.4024 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2494 0.1241 3.1343 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9844 3.1130 2.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2261 1.3921 -0.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5852 -1.4361 -1.4460 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5145 0.0988 -2.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6140 -1.3258 -2.4176 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7382 0.4268 -2.1797 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0136 -1.4062 0.9001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0808 0.0469 1.9180 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4469 -0.2330 2.6091 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6381 1.7300 1.7269 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9099 1.7736 -0.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0719 2.2486 0.7621 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8225 1.2500 2.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4670 -0.7618 1.0387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4468 0.7705 -1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6304 -0.6474 -2.7350 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7312 -1.9500 -1.9689 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2790 -2.0675 -1.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3953 -2.6185 -0.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8292 0.9742 2.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2954 1.4711 -1.8584 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0437 2.5564 -0.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3812 1.2646 -2.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1348 1.8598 -1.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7132 -0.8704 -2.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0091 -1.6938 -1.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4033 1.4769 0.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9282 0.0511 1.6747 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9057 -1.9438 0.8874 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2005 -2.3281 1.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7440 -0.8407 1.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0136 -2.5362 0.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5792 0.1922 2.5187 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3778 0.2730 1.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1347 -1.6627 0.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8103 -2.8988 -0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3562 -0.7267 3.2371 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1960 2.4498 1.7522 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 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 11 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 21 23 1 1 21 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 1 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 30 42 1 1 20 43 1 1 43 44 2 0 5 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 47 3 1 0 13 7 1 0 22 17 1 0 31 26 1 0 41 36 1 0 27 20 1 0 35 30 1 0 1 51 1 0 2 52 1 0 2 53 1 0 3 54 1 6 5 55 1 1 7 56 1 1 8 57 1 6 9 58 1 0 9 59 1 0 9 60 1 0 11 61 1 6 12 62 1 1 13 63 1 1 14 64 1 0 15 65 1 0 17 66 1 6 18 67 1 0 18 68 1 0 19 69 1 0 19 70 1 0 22 71 1 0 22 72 1 0 23 73 1 0 24 74 1 0 24 75 1 0 25 76 1 0 25 77 1 0 26 78 1 1 27 79 1 6 28 80 1 0 28 81 1 0 29 82 1 0 29 83 1 0 32 84 1 0 33 85 1 0 33 86 1 0 34 87 1 0 34 88 1 0 35 89 1 6 37 90 1 0 41 91 1 0 41 92 1 0 42 93 1 0 42 94 1 0 42 95 1 0 43 96 1 0 45 97 1 1 46 98 1 6 47 99 1 1 48100 1 0 49101 1 0 50102 1 0 M END

Standard InCHIKey	CAYUJEAJKPLCAV-XXCZCDTISA-N
Standard InCHI	InChI=1S/C35H52O15/c1-16-29(50-31-27(42)25(40)24(39)22(13-36)49-31)26(41)28(43)30(47-16)48-18-3-8-33(15-37)20-4-7-32(2)19(17-11-23(38)46-14-17)6-10-35(32,45)21(20)5-9-34(33,44)12-18/h11,15-16,18-22,24-31,36,39-45H,3-10,12-14H2,1-2H3/t16-,18+,19-,20+,21-,22-,24-,25+,26+,27-,28-,29+,30+,31+,32-,33+,34+,35+/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](C)O[C@H]([C@@H]([C@@H]2O)O)O[C@H]2CC[C@]3([C@](C2)(O)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C=O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	712.33	Volume:	677.965 ? Van der Waals volume.
Dense:	1.051	LogP:	-0.859 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.167 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.654 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	39.0
TPSA:	242.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.781	Fsp³:	0.886
MCE-18:	139.576 ? 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:	0.681	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.147	Promiscuous compounds:	0.232

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.839	MDCK Permeability:	-5.134
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
PAMPA:	1.0 ? 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):	0.097
20% Bioavailability (F20%):	0.207	30% Bioavailability (F30%):	0.913
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.063
Plasma Protein Binding (PPB):	46.461%	Volume Distribution (VD):	-0.551
Fu:	55.095% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.881	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.178
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):

0.552

Half-life (T1/2):

4.705

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.378
Human Hepatotoxicity (H-HT):	0.887	Drug-induced Liver Injury (DILI):	0.778
AMES Toxicity:	0.918	Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.837	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.836
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.962
Hematotoxicity:	0.366	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.848
A549 Cytotoxicity:	0.691	Hek293 Cytotoxicity:	0.981
BCF:	0.54 ? 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:	3.203 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.681 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.813 ? 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
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20553004]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	latex	Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Yunnan Province, China	2011-Mar	PMID[24033101]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	trunk bark	Yunnan, China	n.a.	PMID[24582402]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8100	Erysimum cheiranthoides	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8369	Antiaris toxicaria	Species	Moraceae	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	10

Activity Type	# Activity
Cell line	7
Non-molecular	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
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	0.16	ug ml-1	PMID[24582402]
NPT308	Cell line	CAKI-1	Homo sapiens	ED50	=	0.51	ug ml-1	PMID[24582402]
NPT309	Cell line	1A9	Homo sapiens	ED50	=	0.53	ug ml-1	PMID[24582402]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	0.6	ug ml-1	PMID[24582402]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	0.58	ug ml-1	PMID[24582402]
NPT81	Cell line	A549	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[24582402]
NPT91	Cell line	KB	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.94	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	1.9	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	1.7	ug ml-1	PMID[24582402]

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 NPC116075 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	16881
0.1-0.2	27774
0.2-0.3	4239
0.3-0.4	765
0.4-0.5	63
0.5-0.6	49
0.6-0.7	59
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32793
0.8588	High Similarity	NPC59288
0.7931	Intermediate Similarity	NPC188234
0.7927	Intermediate Similarity	NPC17896
0.7927	Intermediate Similarity	NPC469755
0.7927	Intermediate Similarity	NPC284406
0.7927	Intermediate Similarity	NPC197707
0.7927	Intermediate Similarity	NPC251866
0.7865	Intermediate Similarity	NPC469749
0.7805	Intermediate Similarity	NPC84987
0.7778	Intermediate Similarity	NPC146857
0.764	Intermediate Similarity	NPC264336
0.7614	Intermediate Similarity	NPC236973
0.7614	Intermediate Similarity	NPC32177
0.7614	Intermediate Similarity	NPC469756
0.7614	Intermediate Similarity	NPC275901
0.7582	Intermediate Similarity	NPC247190
0.7579	Intermediate Similarity	NPC329675
0.7528	Intermediate Similarity	NPC475556
0.7528	Intermediate Similarity	NPC311706
0.7444	Intermediate Similarity	NPC475629
0.7381	Intermediate Similarity	NPC219085
0.7216	Intermediate Similarity	NPC194716
0.7143	Intermediate Similarity	NPC608063
0.7011	Intermediate Similarity	NPC480914
0.6897	Remote Similarity	NPC157376
0.6897	Remote Similarity	NPC142066
0.6897	Remote Similarity	NPC603972
0.686	Remote Similarity	NPC99728
0.686	Remote Similarity	NPC87250
0.686	Remote Similarity	NPC244402
0.686	Remote Similarity	NPC50305
0.6809	Remote Similarity	NPC125077
0.6737	Remote Similarity	NPC232785
0.6737	Remote Similarity	NPC486139
0.6705	Remote Similarity	NPC5311
0.6705	Remote Similarity	NPC77299
0.6705	Remote Similarity	NPC480906
0.6522	Remote Similarity	NPC480907
0.6517	Remote Similarity	NPC6108
0.6517	Remote Similarity	NPC89514
0.6484	Remote Similarity	NPC9499
0.6484	Remote Similarity	NPC471360
0.6484	Remote Similarity	NPC469751
0.6484	Remote Similarity	NPC471361
0.6484	Remote Similarity	NPC86159
0.6484	Remote Similarity	NPC469752
0.6484	Remote Similarity	NPC469754
0.6484	Remote Similarity	NPC70542
0.6458	Remote Similarity	NPC486143
0.6458	Remote Similarity	NPC486135
0.6458	Remote Similarity	NPC486142
0.6458	Remote Similarity	NPC486137
0.6458	Remote Similarity	NPC486149
0.6444	Remote Similarity	NPC10823
0.6374	Remote Similarity	NPC180079
0.6364	Remote Similarity	NPC158344
0.6264	Remote Similarity	NPC243196
0.6263	Remote Similarity	NPC486138
0.6263	Remote Similarity	NPC276838
0.6211	Remote Similarity	NPC30483
0.6211	Remote Similarity	NPC470897
0.6186	Remote Similarity	NPC486127
0.6162	Remote Similarity	NPC329986
0.6162	Remote Similarity	NPC140092
0.6154	Remote Similarity	NPC469750
0.6117	Remote Similarity	NPC120390
0.6087	Remote Similarity	NPC76572
0.6087	Remote Similarity	NPC193382
0.6082	Remote Similarity	NPC480910
0.6082	Remote Similarity	NPC240070
0.6082	Remote Similarity	NPC480909
0.6082	Remote Similarity	NPC486130
0.6078	Remote Similarity	NPC486144
0.6078	Remote Similarity	NPC486145
0.6078	Remote Similarity	NPC329636
0.6078	Remote Similarity	NPC486147
0.6078	Remote Similarity	NPC475590
0.6078	Remote Similarity	NPC486136
0.6078	Remote Similarity	NPC486148
0.6044	Remote Similarity	NPC309034
0.6022	Remote Similarity	NPC146456
0.602	Remote Similarity	NPC610296
0.6	Remote Similarity	NPC486146
0.5979	Remote Similarity	NPC292467
0.5934	Remote Similarity	NPC99620
0.5851	Remote Similarity	NPC77319
0.5851	Remote Similarity	NPC471351
0.5851	Remote Similarity	NPC471355
0.5849	Remote Similarity	NPC486150
0.5825	Remote Similarity	NPC486128
0.5824	Remote Similarity	NPC474418
0.5816	Remote Similarity	NPC40749
0.581	Remote Similarity	NPC74259
0.5789	Remote Similarity	NPC471359
0.5729	Remote Similarity	NPC471354
0.5729	Remote Similarity	NPC27507
0.5728	Remote Similarity	NPC486132
0.5728	Remote Similarity	NPC486131
0.5714	Remote Similarity	NPC603497
0.5647	Remote Similarity	NPC72772
0.5644	Remote Similarity	NPC208193
0.5607	Remote Similarity	NPC486134
0.5607	Remote Similarity	NPC486141
0.5596	Remote Similarity	NPC474423
0.5514	Remote Similarity	NPC475419
0.5474	Remote Similarity	NPC34390
0.5474	Remote Similarity	NPC480915
0.5463	Remote Similarity	NPC486140
0.5463	Remote Similarity	NPC474908
0.5429	Remote Similarity	NPC476221
0.5429	Remote Similarity	NPC477709
0.5413	Remote Similarity	NPC486133
0.5392	Remote Similarity	NPC231518
0.5392	Remote Similarity	NPC488944
0.5368	Remote Similarity	NPC196429
0.5361	Remote Similarity	NPC83287
0.5283	Remote Similarity	NPC475219
0.5253	Remote Similarity	NPC469753
0.5234	Remote Similarity	NPC488943
0.5234	Remote Similarity	NPC488942
0.5208	Remote Similarity	NPC484211
0.52	Remote Similarity	NPC72260
0.5175	Remote Similarity	NPC486152
0.5152	Remote Similarity	NPC179412
0.5152	Remote Similarity	NPC471356
0.5152	Remote Similarity	NPC471353
0.5102	Remote Similarity	NPC604978
0.5093	Remote Similarity	NPC479360
0.5093	Remote Similarity	NPC479359
0.5051	Remote Similarity	NPC250556
0.5045	Remote Similarity	NPC117445
0.5045	Remote Similarity	NPC308262

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC116075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6398
0.1-0.2	2637
0.2-0.3	90
0.3-0.4	12
0.4-0.5	7
0.5-0.6	5
0.6-0.7	0
0.7-0.8	1
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
0.7927	Intermediate Similarity	NPD7319	Approved
0.5392	Remote Similarity	NPD8033	Approved
0.5361	Remote Similarity	NPD7327	Approved
0.5361	Remote Similarity	NPD7328	Phase 4
0.52	Remote Similarity	NPD8294	Phase 4
0.5051	Remote Similarity	NPD7507	Pre-clinical

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