NPASS Compound

Natural Product: NPC603171

Natural Product ID	NPC603171
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RCINICONZNJXQF-VAZQATRQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL48
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 113119 0 0 0 0 0 0 0 0999 V2000 -0.4191 6.5010 0.5938 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0097 5.1186 0.8969 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9467 4.8977 1.6624 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6907 4.0661 0.3291 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3970 2.7373 0.5394 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5308 1.9237 1.1555 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0871 1.1119 1.9469 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0293 1.8663 1.0390 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3970 3.3417 1.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5508 1.2837 -0.2118 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8545 0.3672 -1.0815 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6760 -0.8585 -0.3840 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1813 -2.0810 -0.6523 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9370 -2.2019 -1.6708 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9052 -3.2679 0.1610 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4907 -4.4805 -0.1272 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2144 -5.6194 0.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3436 -5.5628 1.6873 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -4.3576 1.9849 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0415 -3.2323 1.2197 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 0.5585 -1.8857 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9044 0.2321 -3.2161 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5740 -0.4257 -1.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8310 0.0414 -1.3791 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5230 -0.9624 -0.6116 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5619 -1.7139 -1.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9161 -1.4999 -2.2773 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2063 -2.7187 -0.2179 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6557 -2.6839 1.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7015 -2.5714 -0.2544 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1696 -1.3291 0.3106 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8931 -0.4271 -0.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0976 -0.7606 -1.7398 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4177 0.8416 -0.0852 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1330 1.6217 -0.9576 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6373 2.8540 -0.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4170 3.2768 0.7607 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7056 2.5003 1.6270 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1976 1.2651 1.2012 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3749 -3.7428 0.4133 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5378 -3.7965 1.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1614 -4.8877 2.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6243 -5.9313 1.6229 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4763 -5.9038 0.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8511 -4.8066 -0.3241 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8518 1.3418 -0.6361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9484 1.8442 0.1908 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2441 2.0638 -0.7545 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0393 1.9527 -2.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0661 1.9868 -3.1857 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9709 3.0643 -2.2144 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9625 0.6665 -0.0179 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4543 0.2486 -1.2801 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6535 -0.3653 -1.5115 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0384 -0.7383 -2.8865 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3977 -0.5951 -0.5396 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0035 1.6089 0.5330 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1387 0.7741 1.6098 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1411 -0.1343 1.1599 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0802 -0.1348 2.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5105 1.2254 2.3112 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4827 1.9976 2.9903 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3813 6.7653 1.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3654 7.1975 0.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6037 6.5435 -0.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4436 2.6527 1.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1507 3.5047 2.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7703 3.8078 0.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5254 3.9275 1.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9017 2.1846 -0.8186 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6496 0.0478 -1.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1825 -4.5871 -0.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6865 -6.5660 0.3852 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1289 -6.4659 2.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0701 -4.3205 2.8177 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5384 -2.3267 1.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6741 0.7510 -3.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8982 -0.9173 -0.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5401 -1.3357 -2.1418 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3342 0.0272 -2.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9260 -3.7304 -0.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8131 -1.7999 1.4817 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9846 -2.5909 -1.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0018 -1.0592 1.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3499 1.3604 -1.9842 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2049 3.4862 -1.1955 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8170 4.2383 1.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5536 2.8655 2.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6481 0.7220 1.9542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1926 -3.0072 2.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2876 -4.9268 3.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1088 -6.7759 2.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8399 -6.7260 -0.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7497 -4.8150 -1.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0343 1.4239 1.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8877 1.4455 -0.3178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1110 2.9418 0.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3325 2.8179 -3.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9591 2.2762 -2.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1276 1.0904 -3.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8684 2.7541 -2.8336 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5037 3.8178 -2.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1954 3.7154 -1.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5673 0.0282 -3.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5738 -1.7008 -3.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1348 -0.7198 -3.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0058 1.5965 -0.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7665 2.6511 0.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5620 -1.1706 1.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3720 -0.9527 2.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6591 -0.2983 3.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6805 1.1541 3.0843 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5825 1.6073 3.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 6 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 11 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 30 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 24 46 1 0 46 47 1 0 46 48 2 0 48 49 1 0 49 50 1 0 49 51 1 0 10 52 1 0 52 53 1 6 53 54 1 0 54 55 1 0 54 56 2 0 52 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 48 5 1 0 59 52 1 0 61 8 1 0 20 15 1 0 49 21 1 0 39 34 1 0 45 40 1 0 1 63 1 0 1 64 1 0 1 65 1 0 5 66 1 1 9 67 1 0 9 68 1 0 9 69 1 0 10 70 1 0 11 71 1 6 16 72 1 0 17 73 1 0 18 74 1 0 19 75 1 0 20 76 1 0 22 77 1 0 23 78 1 0 23 79 1 0 24 80 1 6 28 81 1 6 29 82 1 0 30 83 1 6 31 84 1 0 35 85 1 0 36 86 1 0 37 87 1 0 38 88 1 0 39 89 1 0 41 90 1 0 42 91 1 0 43 92 1 0 44 93 1 0 45 94 1 0 47 95 1 0 47 96 1 0 47 97 1 0 50 98 1 0 50 99 1 0 50100 1 0 51101 1 0 51102 1 0 51103 1 0 55104 1 0 55105 1 0 55106 1 0 57107 1 0 57108 1 0 59109 1 6 60110 1 0 60111 1 0 61112 1 1 62113 1 0 M END

Standard InCHIKey	RCINICONZNJXQF-VAZQATRQSA-N
Standard InCHI	InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38?,40-,45+,46-,47+/m0/s1
SMILES	CC(=O)O[C@H]1C(=O)[C@@]2(C)C([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	853.33	Volume:	853.449 ? Van der Waals volume.
Dense:	1.0	LogP:	2.85 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.885 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.133 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	44.0
TPSA:	221.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.916	Fsp³:	0.447
MCE-18:	175.882 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.961	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.057 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.471 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.005	Promiscuous compounds:	0.084

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.895	MDCK Permeability:	-5.25
Pgp-inhibitor:	0.645	Pgp-substrate:	0.989
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):	0.0
20% Bioavailability (F20%):	0.913	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	92.695%	Volume Distribution (VD):	0.049
Fu:	6.809% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.49

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.952
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.864 ? 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):

3.303

Half-life (T1/2):

2.606

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.145
Human Hepatotoxicity (H-HT):	0.958	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.898
Maximum Recommended Daily Dose:	0.998	Skin Sensitization:	1.0
Carcinogencity:	0.058	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.085
Drug-induced Neurotoxicity:	1.0	Ototoxicity:	0.909
Hematotoxicity:	0.827	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.934
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.989
BCF:	0.537 ? 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:	3.518 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.143 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.41 ? 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
NPO63140	Unknown-fungus sp.	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3374	Pestalotiopsis guepinii	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3374	Pestalotiopsis guepinii	Species	Sporocadaceae	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	2

Activity Type	# Activity
Organism	2

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
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity

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 NPC603171 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	12673
0.1-0.2	35352
0.2-0.3	1696
0.3-0.4	68
0.4-0.5	14
0.5-0.6	23
0.6-0.7	26
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9362	High Similarity	NPC471606
0.8351	Intermediate Similarity	NPC473400
0.7451	Intermediate Similarity	NPC208553
0.7451	Intermediate Similarity	NPC181964
0.7451	Intermediate Similarity	NPC307628
0.732	Intermediate Similarity	NPC603140
0.6981	Remote Similarity	NPC487360
0.6952	Remote Similarity	NPC471623
0.6923	Remote Similarity	NPC473300
0.6923	Remote Similarity	NPC36607
0.6887	Remote Similarity	NPC33372
0.6887	Remote Similarity	NPC67246
0.6887	Remote Similarity	NPC324251
0.6887	Remote Similarity	NPC206211
0.6852	Remote Similarity	NPC275170
0.6822	Remote Similarity	NPC479182
0.6822	Remote Similarity	NPC479180
0.6822	Remote Similarity	NPC471629
0.6822	Remote Similarity	NPC306001
0.6792	Remote Similarity	NPC317882
0.6727	Remote Similarity	NPC487361
0.6636	Remote Similarity	NPC486061
0.6636	Remote Similarity	NPC486060
0.6392	Remote Similarity	NPC155329
0.6392	Remote Similarity	NPC114357
0.6182	Remote Similarity	NPC453588
0.6091	Remote Similarity	NPC321072
0.6091	Remote Similarity	NPC215892
0.6091	Remote Similarity	NPC242662
0.6091	Remote Similarity	NPC473490
0.6036	Remote Similarity	NPC473558
0.6036	Remote Similarity	NPC191193
0.596	Remote Similarity	NPC605573
0.5946	Remote Similarity	NPC327699
0.5752	Remote Similarity	NPC453583
0.5664	Remote Similarity	NPC102167
0.5664	Remote Similarity	NPC488127
0.5652	Remote Similarity	NPC478329
0.5565	Remote Similarity	NPC471754
0.5565	Remote Similarity	NPC479183
0.5565	Remote Similarity	NPC479181
0.5537	Remote Similarity	NPC116862
0.5481	Remote Similarity	NPC259144
0.5481	Remote Similarity	NPC219419
0.541	Remote Similarity	NPC472392
0.5259	Remote Similarity	NPC478328
0.5243	Remote Similarity	NPC197037
0.5243	Remote Similarity	NPC229545
0.5243	Remote Similarity	NPC248265
0.5243	Remote Similarity	NPC134685
0.5197	Remote Similarity	NPC479184
0.5096	Remote Similarity	NPC91730
0.5079	Remote Similarity	NPC472391
0.5048	Remote Similarity	NPC217918
0.5039	Remote Similarity	NPC479185

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC603171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3654
0.1-0.2	5424
0.2-0.3	59
0.3-0.4	0
0.4-0.5	5
0.5-0.6	4
0.6-0.7	3
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
0.7451	Intermediate Similarity	NPD8485	Phase 4
0.6697	Remote Similarity	NPD8486	Phase 1
0.6273	Remote Similarity	NPD8368	Phase 2
0.6033	Remote Similarity	NPD8462	Phase 2
0.5804	Remote Similarity	NPD8424	Phase 3
0.5664	Remote Similarity	NPD8360	Approved
0.5664	Remote Similarity	NPD8361	Phase 4
0.5345	Remote Similarity	NPD8435	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