NPASS Compound

Natural Product: NPC146857

Natural Product ID	NPC146857
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-Dihydroxy-3-[(2R,4S,5R,6R)-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-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
IUPAC Name	(3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-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	NSC-4320
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL540506
PubChem CID	20055294
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 104110 0 0 0 0 0 0 0 0999 V2000 -4.0549 3.1779 0.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7140 1.7047 0.4577 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9225 1.0371 1.1192 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3614 0.1110 2.1750 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2495 -0.6871 1.4850 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1344 0.3021 1.1988 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5953 1.6324 1.3177 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0202 0.0777 1.9729 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1295 -0.2003 1.2110 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1949 0.8207 1.4215 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3290 0.2463 2.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9661 -0.9856 1.5394 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6275 -1.6471 2.7212 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3659 -2.7642 3.1130 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0923 -0.5902 0.6275 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4300 -1.1284 1.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4653 -1.1480 0.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2934 -0.3440 -1.1873 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0690 -0.9825 -2.3444 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7408 1.0675 -0.9489 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9689 1.8718 -2.0088 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5898 1.2330 -1.7895 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8782 -0.1997 -1.6650 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9358 -0.9876 -0.7923 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5396 -0.9471 -1.2885 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7305 -1.9205 -0.4780 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9567 -1.8952 0.9801 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6098 -1.5475 1.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1870 -3.2343 1.3833 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7432 -0.7648 -2.9556 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1780 1.3461 -0.9375 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8035 1.8225 0.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2142 2.0153 -0.0899 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0504 2.4507 0.7657 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4276 1.6440 -1.3848 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2193 1.2189 -1.9504 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3114 -0.7227 2.7303 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3340 -0.5207 4.0972 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5104 0.2351 0.1358 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8329 0.5627 -0.1002 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9234 1.0800 -1.5312 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3746 -0.0006 -2.4897 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6366 -0.6775 -2.0344 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9041 -0.2644 -0.6007 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9850 -1.1625 -0.0423 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1940 -0.8950 1.3163 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7094 -0.4975 0.1063 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7287 -0.3956 -2.8565 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3701 -0.9181 -2.6957 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7333 2.2092 -1.6201 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1070 3.7176 0.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7008 3.3052 -0.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5379 3.4910 1.2345 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4490 1.2246 -0.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6253 1.7836 1.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8462 0.7376 2.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7020 -1.0759 0.5468 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9181 -1.5289 2.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8483 0.2044 0.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2024 -0.1568 0.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4750 1.3875 0.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7572 1.6182 2.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9811 0.0334 3.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1095 1.0499 2.2985 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3895 -1.1154 3.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1894 0.5316 0.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2271 -2.1299 1.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8294 -0.5186 1.9496 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5671 -2.2285 -0.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4725 -0.9451 0.4978 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3620 -1.7697 -2.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3018 -0.2806 -3.1485 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9291 -1.5727 -1.9928 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2644 1.4492 0.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9751 2.9456 -1.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2672 1.6135 -3.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1741 1.7446 -0.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9106 1.5007 -2.6338 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2802 -2.0613 -0.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5703 -1.3240 -2.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1021 0.0544 -1.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6525 -1.7461 -0.7759 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9393 -2.9379 -0.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1106 -2.3001 1.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6787 -1.5985 2.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6508 -3.7480 0.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1838 -0.1295 -3.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3182 2.0330 1.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4104 0.1775 -2.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0179 1.8109 -2.8722 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1029 -1.1938 4.5550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3430 -0.8338 4.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5526 0.5028 4.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1886 1.4075 0.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9011 1.3980 -1.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5911 0.4971 -3.4498 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4871 -1.7735 -2.0491 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2277 0.7816 -0.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9399 -0.9721 -0.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7318 -2.2253 -0.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1494 0.1072 1.4299 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9491 -1.1652 -3.4652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5803 -1.7700 -2.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3302 2.1553 -2.4041 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 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 27 29 1 1 23 30 1 6 20 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 1 0 4 37 1 0 37 38 1 0 3 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 42 49 1 0 41 50 1 0 7 2 1 0 28 9 1 0 36 31 1 0 47 40 1 0 27 12 1 0 24 15 1 0 23 18 1 0 1 51 1 0 1 52 1 0 1 53 1 0 2 54 1 6 3 55 1 1 4 56 1 1 5 57 1 0 5 58 1 0 6 59 1 6 9 60 1 6 10 61 1 0 10 62 1 0 11 63 1 0 11 64 1 0 13 65 1 0 15 66 1 6 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 19 71 1 0 19 72 1 0 19 73 1 0 20 74 1 1 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 24 79 1 1 25 80 1 0 25 81 1 0 26 82 1 0 26 83 1 0 28 84 1 0 28 85 1 0 29 86 1 0 30 87 1 0 32 88 1 0 36 89 1 0 36 90 1 0 38 91 1 0 38 92 1 0 38 93 1 0 40 94 1 1 41 95 1 6 42 96 1 6 43 97 1 1 44 98 1 6 45 99 1 0 45100 1 0 46101 1 0 48102 1 0 49103 1 0 50104 1 0 M END

Standard InCHIKey	FHIREUBIEIPPMC-SADZTDHOSA-N
Standard InCHI	InChI=1S/C36H54O14/c1-18-31(50-32-30(42)29(41)28(40)25(15-37)49-32)24(45-3)13-27(47-18)48-20-4-9-34(17-38)22-5-8-33(2)21(19-12-26(39)46-16-19)7-11-36(33,44)23(22)6-10-35(34,43)14-20/h12,17-18,20-25,27-32,37,40-44H,4-11,13-16H2,1-3H3/t18-,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31-,32+,33-,34+,35+,36+/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]1CC[C@]2(C=O)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)C1=CC(=O)OC1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.35	Volume:	686.471 ? Van der Waals volume.
Dense:	1.035	LogP:	-0.15 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.759 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.432 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	39.0
TPSA:	210.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.113	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.784	Fsp³:	0.889
MCE-18:	135.529 ? 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:	0.76	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.165	Promiscuous compounds:	0.322

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.0	MDCK Permeability:	-5.335
Pgp-inhibitor:	0.0	Pgp-substrate:	0.96
PAMPA:	0.999 ? 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):	0.083
20% Bioavailability (F20%):	0.093	30% Bioavailability (F30%):	0.646
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062	MRP1:	0.19
Plasma Protein Binding (PPB):	53.687%	Volume Distribution (VD):	-0.496
Fu:	47.531% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.016
BSEP inhibitor:	0.013

ADMET: Metabolism

CYP1A2-inhibitor:	0.389	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.01	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.008
HLM stability:	0.002 ? 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):

1.421

Half-life (T1/2):

4.197

ADMET: Toxicity

hERG Blockers:	0.089	hERG Blockers (10um):	0.462
Human Hepatotoxicity (H-HT):	0.882	Drug-induced Liver Injury (DILI):	0.93
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.942	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.956
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.95
Hematotoxicity:	0.635	Drug-induced Nephrotoxicity:	0.978
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.879
A549 Cytotoxicity:	0.967	Hek293 Cytotoxicity:	0.994
BCF:	0.568 ? 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:	3.278 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.84 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.039 ? 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
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np8006342]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1021/np8006342]
NPO4040	Kunzea ericifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543906]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	fruit	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	leaf	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	flower	n.a.	PMID[19405508]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	twig	n.a.	PMID[19405508]
NPO3290	Agathosma puberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27978	Crossosoma bigelovii	Species	Crossosomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO813	Streptomyces longisporus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4040	Kunzea ericifolia	Species	Myrtaceae	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
GI50	59

Activity Type	# Activity
Cell line	59

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
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	0.01052	nM	PubChem BioAssay data set
NPT367	Cell line	MDA-N	Homo sapiens	GI50	n.a.	0.03945	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	0.009162	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	0.00787	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	0.05834	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	0.03491	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT90	Cell line	DU-145	Homo sapiens	GI50	n.a.	0.006339	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	0.02028	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	0.02624	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	0.02704	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	0.05808	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	0.007674	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	0.00542	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	0.01259	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	0.01151	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	0.04074	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	0.03342	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	0.03516	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	0.08933	nM	PubChem BioAssay data set
NPT82	Cell line	MDA-MB-231	Homo sapiens	GI50	n.a.	0.1726	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	0.02483	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	0.03155	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	0.09099	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	0.006871	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	0.04732	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	0.01574	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	0.03698	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	0.00863	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	0.02612	nM	PubChem BioAssay data set
NPT457	Cell line	BT-549	Homo sapiens	GI50	n.a.	0.01216	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	0.0826	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	0.004457	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	0.05105	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	0.03945	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	0.009727	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	0.01186	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	0.006998	nM	PubChem BioAssay data set
NPT306	Cell line	PC-3	Homo sapiens	GI50	n.a.	0.02056	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	0.04227	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	0.009036	nM	PubChem BioAssay data set
NPT396	Cell line	T47D	Homo sapiens	GI50	n.a.	0.05534	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	0.01337	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	0.06166	nM	PubChem BioAssay data set
NPT400	Cell line	MDA-MB-435	Homo sapiens	GI50	n.a.	0.04613	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	0.02042	nM	PubChem BioAssay data set
NPT402	Cell line	Hs-578T	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	0.08222	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	10.0	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	0.03034	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	0.07852	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	0.06427	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	0.01507	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	0.1096	nM	PubChem BioAssay data set

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 NPC146857 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	15996
0.1-0.2	28868
0.2-0.3	4342
0.3-0.4	438
0.4-0.5	69
0.5-0.6	70
0.6-0.7	51
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9213	High Similarity	NPC329675
0.9213	High Similarity	NPC194716
0.8022	Intermediate Similarity	NPC329986
0.8022	Intermediate Similarity	NPC140092
0.7826	Intermediate Similarity	NPC247190
0.7778	Intermediate Similarity	NPC32793
0.7778	Intermediate Similarity	NPC116075
0.7527	Intermediate Similarity	NPC469749
0.75	Intermediate Similarity	NPC329636
0.75	Intermediate Similarity	NPC475629
0.7356	Intermediate Similarity	NPC17896
0.7356	Intermediate Similarity	NPC469755
0.7356	Intermediate Similarity	NPC284406
0.7356	Intermediate Similarity	NPC197707
0.7356	Intermediate Similarity	NPC251866
0.7241	Intermediate Similarity	NPC84987
0.7204	Intermediate Similarity	NPC475556
0.7204	Intermediate Similarity	NPC311706
0.7191	Intermediate Similarity	NPC180079
0.7172	Intermediate Similarity	NPC475419
0.6893	Remote Similarity	NPC474423
0.6854	Remote Similarity	NPC219085
0.6842	Remote Similarity	NPC608063
0.6804	Remote Similarity	NPC232785
0.6804	Remote Similarity	NPC486139
0.6701	Remote Similarity	NPC59288
0.6667	Remote Similarity	NPC74259
0.6667	Remote Similarity	NPC486138
0.6667	Remote Similarity	NPC276838
0.6602	Remote Similarity	NPC474908
0.6538	Remote Similarity	NPC329784
0.6531	Remote Similarity	NPC486143
0.6531	Remote Similarity	NPC125077
0.6531	Remote Similarity	NPC486135
0.6531	Remote Similarity	NPC486142
0.6531	Remote Similarity	NPC486137
0.6531	Remote Similarity	NPC486149
0.6522	Remote Similarity	NPC10823
0.6522	Remote Similarity	NPC480914
0.6505	Remote Similarity	NPC120390
0.6413	Remote Similarity	NPC6108
0.6413	Remote Similarity	NPC157376
0.6413	Remote Similarity	NPC89514
0.6413	Remote Similarity	NPC142066
0.6413	Remote Similarity	NPC603972
0.64	Remote Similarity	NPC486146
0.6374	Remote Similarity	NPC99728
0.6374	Remote Similarity	NPC87250
0.6374	Remote Similarity	NPC244402
0.6374	Remote Similarity	NPC50305
0.6263	Remote Similarity	NPC486127
0.6237	Remote Similarity	NPC5311
0.6237	Remote Similarity	NPC77299
0.6237	Remote Similarity	NPC34390
0.6237	Remote Similarity	NPC480906
0.6226	Remote Similarity	NPC486150
0.6211	Remote Similarity	NPC9499
0.6211	Remote Similarity	NPC471360
0.6211	Remote Similarity	NPC469751
0.6211	Remote Similarity	NPC471361
0.6211	Remote Similarity	NPC86159
0.6211	Remote Similarity	NPC469752
0.6211	Remote Similarity	NPC469754
0.6211	Remote Similarity	NPC70542
0.6162	Remote Similarity	NPC188234
0.6162	Remote Similarity	NPC486130
0.6154	Remote Similarity	NPC486144
0.6154	Remote Similarity	NPC486145
0.6154	Remote Similarity	NPC486147
0.6154	Remote Similarity	NPC486136
0.6154	Remote Similarity	NPC486148
0.5981	Remote Similarity	NPC486134
0.5981	Remote Similarity	NPC486141
0.5941	Remote Similarity	NPC264336
0.5918	Remote Similarity	NPC480907
0.5914	Remote Similarity	NPC158344
0.5914	Remote Similarity	NPC474418
0.5905	Remote Similarity	NPC486128
0.59	Remote Similarity	NPC236973
0.59	Remote Similarity	NPC32177
0.59	Remote Similarity	NPC469756
0.59	Remote Similarity	NPC275901
0.5849	Remote Similarity	NPC475590
0.5842	Remote Similarity	NPC480910
0.5842	Remote Similarity	NPC240070
0.5842	Remote Similarity	NPC480909
0.5833	Remote Similarity	NPC243196
0.5833	Remote Similarity	NPC117445
0.5833	Remote Similarity	NPC308262
0.581	Remote Similarity	NPC486132
0.581	Remote Similarity	NPC486131
0.58	Remote Similarity	NPC30483
0.58	Remote Similarity	NPC470897
0.5784	Remote Similarity	NPC610296
0.5773	Remote Similarity	NPC146456
0.5743	Remote Similarity	NPC292467
0.5729	Remote Similarity	NPC469750
0.567	Remote Similarity	NPC76572
0.567	Remote Similarity	NPC193382
0.5625	Remote Similarity	NPC309034
0.5612	Remote Similarity	NPC77319
0.5612	Remote Similarity	NPC484212
0.5612	Remote Similarity	NPC471351
0.5612	Remote Similarity	NPC471355
0.5556	Remote Similarity	NPC471359
0.5556	Remote Similarity	NPC483822
0.5545	Remote Similarity	NPC486140
0.5521	Remote Similarity	NPC99620
0.55	Remote Similarity	NPC469753
0.55	Remote Similarity	NPC471354
0.55	Remote Similarity	NPC27507
0.5495	Remote Similarity	NPC486133
0.5481	Remote Similarity	NPC231518
0.5481	Remote Similarity	NPC488944
0.5429	Remote Similarity	NPC208193
0.5393	Remote Similarity	NPC72772
0.5354	Remote Similarity	NPC84949
0.5354	Remote Similarity	NPC480562
0.5354	Remote Similarity	NPC74945
0.5354	Remote Similarity	NPC31354
0.5354	Remote Similarity	NPC69576
0.5321	Remote Similarity	NPC488943
0.5321	Remote Similarity	NPC488938
0.5321	Remote Similarity	NPC488937
0.5321	Remote Similarity	NPC488942
0.5306	Remote Similarity	NPC484211
0.5259	Remote Similarity	NPC486152
0.5253	Remote Similarity	NPC480915
0.5229	Remote Similarity	NPC476221
0.5229	Remote Similarity	NPC477709
0.5182	Remote Similarity	NPC479360
0.5182	Remote Similarity	NPC479359
0.5149	Remote Similarity	NPC250556
0.5146	Remote Similarity	NPC72260
0.5098	Remote Similarity	NPC484202
0.5098	Remote Similarity	NPC305574
0.5091	Remote Similarity	NPC475219
0.5051	Remote Similarity	NPC471633
0.505	Remote Similarity	NPC604978
0.5043	Remote Similarity	NPC488945
0.5043	Remote Similarity	NPC488946

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC146857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6143
0.1-0.2	2900
0.2-0.3	90
0.3-0.4	4
0.4-0.5	5
0.5-0.6	4
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
0.7356	Intermediate Similarity	NPD7319	Approved
0.5481	Remote Similarity	NPD8033	Approved
0.5248	Remote Similarity	NPD7516	Pre-clinical
0.5149	Remote Similarity	NPD7507	Pre-clinical
0.5146	Remote Similarity	NPD8294	Phase 4

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