NPASS Compound

Natural Product: NPC469749

Natural Product ID	NPC469749
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Glucostrophalloside
IUPAC Name	(3S,5S,8R,9S,10S,13R,14S,17R)-3-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-6-methyl-4-[(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	Glucostrophalloside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1169678
PubChem CID	49799515
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 8.9648 -4.0680 -1.1241 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7729 -3.4200 -0.7648 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9657 -1.9026 -0.8513 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7695 -1.3330 -0.4891 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7632 0.0502 -0.5074 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1493 0.5103 0.6504 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0178 1.2123 0.3229 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7851 0.5566 0.9260 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8977 0.4033 2.3057 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6016 1.4319 0.5802 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4494 0.8264 1.0448 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5672 0.5452 0.0080 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3016 -0.9242 -0.1674 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1091 -1.0389 -0.7614 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0575 -0.7082 0.3672 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7360 0.6276 1.0139 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6940 1.3583 0.1551 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1322 0.4269 2.2503 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9167 1.5363 1.1075 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1660 0.9045 1.6636 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3229 -0.5256 1.2024 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4912 -0.6667 -0.0495 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9664 -1.8468 -0.8174 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3563 -1.4796 -1.3549 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2939 -1.1003 -0.2676 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7090 -1.0214 1.1046 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7704 -2.3376 1.6277 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7267 -0.2024 1.8710 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6451 0.4355 0.8422 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9245 0.2548 -0.4791 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8869 0.2851 -1.6123 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1546 0.6106 -1.4510 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8404 0.5497 -2.7318 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0565 0.7912 -2.9866 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9049 0.1694 -3.6591 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6781 -0.0061 -3.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4036 -2.1585 -0.2288 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9211 -1.8238 1.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5715 -1.6810 2.5017 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7410 2.6385 1.2616 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8286 3.3740 0.7985 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1120 2.6140 0.8468 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6437 2.5892 2.1448 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5479 3.9437 -0.5881 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1482 0.6432 -0.6516 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1623 -0.0425 0.2087 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0096 -1.5466 0.1725 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2063 -2.1567 -0.2320 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9785 0.3515 1.5481 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4811 0.6391 -1.9937 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2627 -3.7320 -2.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9152 -3.7424 -1.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5728 -3.7100 0.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2801 -1.6869 -1.8860 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1780 0.3720 -1.3753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8310 1.2666 -0.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5976 -0.4483 0.4619 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0233 0.6538 2.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6083 1.5767 -0.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0488 0.8979 -0.9501 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0464 -1.4440 -0.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2799 -1.4709 0.8187 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3102 -2.0886 -1.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1569 -0.3349 -1.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4255 2.2820 0.7114 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1452 1.5477 -0.8186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2103 1.2007 2.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0903 2.0206 0.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6341 2.3712 1.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9969 1.5607 1.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0736 0.9504 2.7886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7859 -1.1363 1.9901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6231 0.2339 -0.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3081 -1.9878 -1.7054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0954 -2.7674 -0.2356 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1734 -0.5549 -1.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6723 -2.3236 -1.9817 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2388 -2.3870 2.4608 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2892 0.5127 2.5714 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3844 -0.8655 2.5025 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5992 -0.1577 0.7587 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9114 1.4673 1.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1261 0.9955 -0.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6948 0.8987 -0.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3873 -1.0823 -3.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9595 0.6799 -3.5236 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7351 -2.3336 0.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2874 -1.7466 -0.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0660 -3.1216 -0.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1607 -2.8204 1.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9237 4.2505 1.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8392 3.1555 0.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0492 3.1232 2.7180 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7144 3.1997 -1.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2179 4.8105 -0.7263 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4847 4.2471 -0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1122 1.7109 -0.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1741 0.2237 -0.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7118 -1.9679 1.1412 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9614 -1.8591 0.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1779 -0.0949 1.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1006 1.3663 -2.1708 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 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 1 16 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 1 26 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 2 0 33 35 1 0 35 36 1 0 25 37 1 1 15 38 1 1 38 39 2 0 10 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 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 42 7 1 0 17 12 1 0 26 21 1 0 36 31 1 0 22 15 1 0 30 25 1 0 1 51 1 0 2 52 1 0 2 53 1 0 3 54 1 6 5 55 1 6 7 56 1 6 8 57 1 6 9 58 1 0 10 59 1 6 12 60 1 6 13 61 1 0 13 62 1 0 14 63 1 0 14 64 1 0 17 65 1 0 17 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 20 70 1 0 20 71 1 0 21 72 1 1 22 73 1 6 23 74 1 0 23 75 1 0 24 76 1 0 24 77 1 0 27 78 1 0 28 79 1 0 28 80 1 0 29 81 1 0 29 82 1 0 30 83 1 6 32 84 1 0 36 85 1 0 36 86 1 0 37 87 1 0 37 88 1 0 37 89 1 0 38 90 1 0 41 91 1 1 42 92 1 6 43 93 1 0 44 94 1 0 44 95 1 0 44 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	KZTRRNWHCITOHG-BEIGQCAMSA-N
Standard InCHI	InChI=1S/C35H52O15/c1-16-24(39)29(50-30-27(42)26(41)25(40)22(13-36)49-30)28(43)31(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](O)[C@@H](O[C@H]3CC[C@]4([C@](C3)(O)CC[C@@H]3[C@@H]4CC[C@]4([C@]3(O)CC[C@@H]4C3=CC(=O)OC3)C)C=O)O[C@@H]([C@H]2O)C)[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:	-1.472 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.191 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.359 ? 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:	5.789	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:	0.685	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.145	Promiscuous compounds:	0.231

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.773	MDCK Permeability:	-5.171
Pgp-inhibitor:	0.0	Pgp-substrate:	0.983
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):	0.293
20% Bioavailability (F20%):	0.531	30% Bioavailability (F30%):	0.95
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041	MRP1:	0.398
Plasma Protein Binding (PPB):	52.076%	Volume Distribution (VD):	-0.541
Fu:	49.298% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.245	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.224
HLM stability:	0.011 ? 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):

0.651

Half-life (T1/2):

3.791

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.16
Human Hepatotoxicity (H-HT):	0.855	Drug-induced Liver Injury (DILI):	0.662
AMES Toxicity:	0.987	Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.997	Skin Sensitization:	1.0
Carcinogencity:	0.902	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.9
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.962
Hematotoxicity:	0.796	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.902
A549 Cytotoxicity:	0.982	Hek293 Cytotoxicity:	0.996
BCF:	0.601 ? 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:	3.181 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.489 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.725 ? 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]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8369	Antiaris toxicaria	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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
Activity	4
Ratio	2
ED50	10

Activity Type	# Activity
Cell line	7
Non-molecular	9

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	=	0.12	ug ml-1	PMID[18838581]
NPT308	Cell line	CAKI-1	Homo sapiens	ED50	=	0.065	ug ml-1	PMID[20585132]
NPT309	Cell line	1A9	Homo sapiens	ED50	=	0.057	ug ml-1	PMID[20585132]
NPT306	Cell line	PC-3	Homo sapiens	ED50	=	0.084	ug ml-1	PMID[20585132]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	0.096	ug ml-1	PMID[20585132]
NPT81	Cell line	A549	Homo sapiens	ED50	=	0.038	ug ml-1	PMID[23558238]
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[18500841]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.25	uM	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	1.0	uM	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	489.0	%	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	350.0	%	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Ratio	=	10.0	n.a.	PMID[20553004]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.13	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.15	ug ml-1	PMID[24582402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.083	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 NPC469749 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	17929
0.1-0.2	27207
0.2-0.3	3776
0.3-0.4	734
0.4-0.5	76
0.5-0.6	61
0.6-0.7	48
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8072	Intermediate Similarity	NPC17896
0.8072	Intermediate Similarity	NPC469755
0.8072	Intermediate Similarity	NPC284406
0.8072	Intermediate Similarity	NPC197707
0.8072	Intermediate Similarity	NPC251866
0.7865	Intermediate Similarity	NPC32793
0.7865	Intermediate Similarity	NPC116075
0.7529	Intermediate Similarity	NPC84987
0.7527	Intermediate Similarity	NPC146857
0.7527	Intermediate Similarity	NPC247190
0.7172	Intermediate Similarity	NPC194716
0.7126	Intermediate Similarity	NPC219085
0.7097	Intermediate Similarity	NPC480910
0.7097	Intermediate Similarity	NPC480909
0.7045	Intermediate Similarity	NPC157376
0.7045	Intermediate Similarity	NPC142066
0.7045	Intermediate Similarity	NPC603972
0.7021	Intermediate Similarity	NPC475629
0.7011	Intermediate Similarity	NPC99728
0.7011	Intermediate Similarity	NPC87250
0.7011	Intermediate Similarity	NPC244402
0.7011	Intermediate Similarity	NPC50305
0.7	Intermediate Similarity	NPC329675
0.6778	Remote Similarity	NPC480914
0.6771	Remote Similarity	NPC59288
0.6703	Remote Similarity	NPC180079
0.6667	Remote Similarity	NPC6108
0.6667	Remote Similarity	NPC89514
0.663	Remote Similarity	NPC9499
0.663	Remote Similarity	NPC471360
0.663	Remote Similarity	NPC469751
0.663	Remote Similarity	NPC471361
0.663	Remote Similarity	NPC86159
0.663	Remote Similarity	NPC469752
0.663	Remote Similarity	NPC469754
0.663	Remote Similarity	NPC70542
0.6562	Remote Similarity	NPC475556
0.6562	Remote Similarity	NPC311706
0.6484	Remote Similarity	NPC5311
0.6484	Remote Similarity	NPC77299
0.6484	Remote Similarity	NPC480906
0.6413	Remote Similarity	NPC10823
0.6364	Remote Similarity	NPC232785
0.6364	Remote Similarity	NPC486139
0.6344	Remote Similarity	NPC250556
0.6304	Remote Similarity	NPC469750
0.6277	Remote Similarity	NPC305574
0.6237	Remote Similarity	NPC76572
0.6237	Remote Similarity	NPC193382
0.6224	Remote Similarity	NPC188234
0.6224	Remote Similarity	NPC240070
0.6224	Remote Similarity	NPC608063
0.6196	Remote Similarity	NPC309034
0.6186	Remote Similarity	NPC30483
0.6186	Remote Similarity	NPC470897
0.6154	Remote Similarity	NPC158344
0.6146	Remote Similarity	NPC480907
0.61	Remote Similarity	NPC486143
0.61	Remote Similarity	NPC486135
0.61	Remote Similarity	NPC486142
0.61	Remote Similarity	NPC486137
0.61	Remote Similarity	NPC486149
0.6087	Remote Similarity	NPC99620
0.6064	Remote Similarity	NPC199428
0.6064	Remote Similarity	NPC109448
0.6064	Remote Similarity	NPC310341
0.6058	Remote Similarity	NPC329636
0.6	Remote Similarity	NPC77319
0.6	Remote Similarity	NPC264336
0.6	Remote Similarity	NPC471351
0.6	Remote Similarity	NPC471355
0.598	Remote Similarity	NPC329986
0.598	Remote Similarity	NPC140092
0.596	Remote Similarity	NPC236973
0.596	Remote Similarity	NPC32177
0.596	Remote Similarity	NPC292467
0.596	Remote Similarity	NPC469756
0.596	Remote Similarity	NPC275901
0.5941	Remote Similarity	NPC125077
0.5922	Remote Similarity	NPC486138
0.5922	Remote Similarity	NPC276838
0.5895	Remote Similarity	NPC243196
0.5876	Remote Similarity	NPC471354
0.5876	Remote Similarity	NPC27507
0.5842	Remote Similarity	NPC486127
0.5842	Remote Similarity	NPC610296
0.5833	Remote Similarity	NPC146456
0.5806	Remote Similarity	NPC474418
0.5789	Remote Similarity	NPC486126
0.5789	Remote Similarity	NPC34390
0.5773	Remote Similarity	NPC471359
0.5755	Remote Similarity	NPC486144
0.5755	Remote Similarity	NPC486145
0.5755	Remote Similarity	NPC486147
0.5755	Remote Similarity	NPC486136
0.5755	Remote Similarity	NPC486148
0.5743	Remote Similarity	NPC486130
0.5688	Remote Similarity	NPC486150
0.5684	Remote Similarity	NPC486129
0.5673	Remote Similarity	NPC486146
0.5625	Remote Similarity	NPC480915
0.5521	Remote Similarity	NPC196429
0.5514	Remote Similarity	NPC486128
0.551	Remote Similarity	NPC83287
0.5505	Remote Similarity	NPC120390
0.5505	Remote Similarity	NPC475419
0.5463	Remote Similarity	NPC475590
0.5455	Remote Similarity	NPC72772
0.5455	Remote Similarity	NPC474908
0.5455	Remote Similarity	NPC486134
0.5455	Remote Similarity	NPC486141
0.5421	Remote Similarity	NPC486132
0.5421	Remote Similarity	NPC486131
0.5364	Remote Similarity	NPC74259
0.5333	Remote Similarity	NPC55532
0.5315	Remote Similarity	NPC486140
0.531	Remote Similarity	NPC474423
0.53	Remote Similarity	NPC179412
0.53	Remote Similarity	NPC471356
0.53	Remote Similarity	NPC471353
0.5278	Remote Similarity	NPC476221
0.5278	Remote Similarity	NPC477709
0.5248	Remote Similarity	NPC469753
0.5204	Remote Similarity	NPC484211
0.52	Remote Similarity	NPC484212
0.5192	Remote Similarity	NPC27363
0.5149	Remote Similarity	NPC483822
0.5143	Remote Similarity	NPC486151
0.5133	Remote Similarity	NPC486133
0.5094	Remote Similarity	NPC231518
0.5094	Remote Similarity	NPC488944
0.5043	Remote Similarity	NPC486152

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6561
0.1-0.2	2481
0.2-0.3	88
0.3-0.4	11
0.4-0.5	4
0.5-0.6	3
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD7319	Approved
0.6344	Remote Similarity	NPD7507	Pre-clinical
0.551	Remote Similarity	NPD7327	Approved
0.551	Remote Similarity	NPD7328	Phase 4
0.5094	Remote Similarity	NPD8033	Approved

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