NPASS Compound

Natural Product: NPC119583

Natural Product ID	NPC119583
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Murucoidin Iii
IUPAC Name	n.a.
Synonyms	Murucoidin III
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504724
PubChem CID	11506346
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 176181 0 0 0 0 0 0 0 0999 V2000 -5.9977 2.2188 4.2625 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0464 3.2094 3.7697 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 4.2211 2.8558 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8101 3.9130 1.6208 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2504 3.4181 0.3477 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9861 2.1592 0.1096 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3758 2.2245 0.7132 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0651 0.9498 0.8891 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2035 0.3846 2.2788 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6246 -1.1185 2.1828 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3971 -1.8766 1.8827 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4337 -3.3052 1.5151 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9730 -3.8514 1.5474 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0617 -2.8266 0.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5936 -3.2920 0.9984 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7468 -2.0873 0.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2990 -1.3610 1.6137 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4623 -1.7588 -0.5885 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7124 -0.6204 -0.9914 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2865 -0.7278 -0.6388 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7523 0.2163 0.4007 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5495 1.4488 0.5828 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1512 1.5892 1.9731 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4340 1.6271 -0.4408 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4172 0.6600 -0.6023 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2530 1.1795 -1.5804 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3420 0.4343 -1.9553 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1120 -0.2661 -3.2928 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2173 0.0634 -4.2383 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5889 -0.1591 -3.6543 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1250 -1.5321 -3.9684 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5941 0.0822 -2.2783 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6397 1.1475 -2.0573 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0721 2.0462 -1.2460 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1163 -0.9420 -5.2652 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9707 -1.6527 -3.1566 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5518 0.5989 -0.0020 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5540 0.0852 0.7986 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5465 -0.6071 -0.1112 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8042 -0.9620 0.6329 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3634 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3.5695 -1.9139 1.6236 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2696 -3.0892 1.5271 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2300 -3.3314 2.6890 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0980 -4.5229 2.3348 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2937 -5.6403 1.7576 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8322 -5.3257 2.0384 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0357 -6.5032 1.5100 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4095 -4.1897 1.3972 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6010 -6.8653 2.3436 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1475 -4.1856 1.5133 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0867 -2.2710 2.8903 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0354 -1.7041 -0.7956 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9186 -1.7340 -2.1880 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3194 -0.6751 -2.7891 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3928 -2.8231 -2.9954 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2321 -2.3462 -4.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3978 -3.9461 -3.0687 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6753 -4.4430 -1.6769 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0260 -2.0322 -0.1409 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5554 1.4112 4.7849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3231 1.8849 3.4739 H 0 0 0 0 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2.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2073 6.0353 -0.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0424 5.0428 -1.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1079 4.1963 -2.5001 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5233 5.9406 -2.7789 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1693 6.6747 -1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8195 6.0035 -3.0673 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2062 8.6375 -2.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2066 7.7718 -3.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7677 7.7750 -1.6887 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0792 3.9739 -2.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9467 0.9007 -2.8061 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9043 -3.0610 0.6259 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6450 -3.5697 3.5948 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5571 -4.8908 3.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4695 -5.7309 0.6628 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7139 -5.3125 3.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4938 -6.8050 0.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2172 -7.3725 2.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9540 -6.2914 1.4557 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5358 -6.8819 2.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8110 -4.9254 1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8904 -2.6174 3.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3994 -3.2036 -2.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3176 -2.7777 -4.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0995 -1.2385 -4.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1253 -2.5878 -5.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3270 -3.4941 -3.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0568 -4.7704 -3.7359 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6069 -3.9424 -1.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7496 -5.5562 -1.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8541 -4.0936 -1.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6552 -2.6946 -0.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 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 30 32 1 0 32 33 1 0 33 34 1 0 29 35 1 0 28 36 1 0 21 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 41 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 49 53 1 0 53 54 1 0 54 55 2 0 54 56 1 0 56 57 1 0 56 58 1 0 58 59 1 0 48 60 1 0 47 61 1 0 40 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 67 69 1 0 66 70 1 0 65 71 1 0 64 72 1 0 39 73 1 0 73 74 1 0 74 75 2 0 74 76 1 0 76 77 1 0 76 78 1 0 78 79 1 0 20 80 1 0 34 6 1 0 44 38 1 0 52 46 1 0 69 63 1 0 25 19 1 0 33 27 1 0 1 81 1 0 1 82 1 0 1 83 1 0 2 84 1 0 2 85 1 0 3 86 1 0 3 87 1 0 4 88 1 0 4 89 1 0 5 90 1 0 5 91 1 0 6 92 1 1 7 93 1 0 7 94 1 0 8 95 1 0 8 96 1 0 9 97 1 0 9 98 1 0 10 99 1 0 10100 1 0 11101 1 0 11102 1 0 12103 1 0 12104 1 0 13105 1 0 13106 1 0 14107 1 0 14108 1 0 15109 1 0 15110 1 0 19111 1 6 20112 1 6 21113 1 1 22114 1 6 23115 1 0 23116 1 0 23117 1 0 25118 1 1 27119 1 1 28120 1 6 29121 1 6 30122 1 6 31123 1 0 31124 1 0 31125 1 0 33126 1 6 35127 1 0 36128 1 0 38129 1 1 39130 1 6 40131 1 6 41132 1 1 42133 1 1 43134 1 0 43135 1 0 43136 1 0 46137 1 1 47138 1 6 48139 1 1 49140 1 6 50141 1 1 51142 1 0 51143 1 0 51144 1 0 56145 1 1 57146 1 0 57147 1 0 57148 1 0 58149 1 0 58150 1 0 59151 1 0 59152 1 0 59153 1 0 60154 1 0 61155 1 0 63156 1 6 64157 1 1 65158 1 1 66159 1 6 67160 1 1 68161 1 0 68162 1 0 68163 1 0 70164 1 0 71165 1 0 72166 1 0 76167 1 1 77168 1 0 77169 1 0 77170 1 0 78171 1 0 78172 1 0 79173 1 0 79174 1 0 79175 1 0 80176 1 0 M END

Standard InCHIKey	GYBGSCDMWAFIBP-UGXGVDMZSA-N
Standard InCHI	InChI=1S/C56H96O24/c1-11-14-20-23-33-24-21-18-16-15-17-19-22-25-34(57)74-47-42(65)44(31(9)71-55(47)79-46-38(61)36(59)29(7)69-54(46)73-33)77-56-49(76-51(67)27(5)13-3)48(80-52-40(63)37(60)35(58)28(6)68-52)45(32(10)72-56)78-53-41(64)39(62)43(30(8)70-53)75-50(66)26(4)12-2/h26-33,35-49,52-56,58-65H,11-25H2,1-10H3/t26-,27-,28-,29+,30-,31-,32-,33-,35-,36-,37+,38-,39-,40+,41+,42+,43-,44-,45-,46+,47+,48+,49+,52-,53-,54-,55-,56-/m0/s1
SMILES	CCCCC[C@H]1CCCCCCCCCC(=O)O[C@@H]2[C@@H]([C@H]([C@H](C)O[C@H]2O[C@@H]2[C@H]([C@H]([C@@H](C)O[C@H]2O1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)OC(=O)[C@@H](C)CC)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)OC(=O)[C@@H](C)CC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1152.63	Volume:	1128.849 ? Van der Waals volume.
Dense:	1.021	LogP:	3.565 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.554 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.9 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	49.0
TPSA:	333.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.229	Fsp³:	0.946
MCE-18:	129.468 ? 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:	0.99	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.561	Promiscuous compounds:	0.04

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.07	MDCK Permeability:	-5.077
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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.77

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	75.543%	Volume Distribution (VD):	-0.245
Fu:	16.499% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.0
BSEP inhibitor:	0.033

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:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.908 ? 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):

0.444

Half-life (T1/2):

2.865

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.131
Human Hepatotoxicity (H-HT):	0.29	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.591	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.678	Drug-induced Nephrotoxicity:	0.952
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.671
A549 Cytotoxicity:	0.898	Hek293 Cytotoxicity:	0.168
BCF:	0.749 ? 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:	3.433 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.195 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.239 ? 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
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	Roots	Ixpantepec, in the state of Oaxaca, Mexico	1996-DEC	PMID[16124750]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643033]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18500841]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
MIC	4
ED50	4

Activity Type	# Activity
Cell line	4
Organism	4

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
NPT165	Cell line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[18313805]
NPT91	Cell line	KB	Homo sapiens	ED50	=	15.4	ug ml-1	PMID[26000707]
NPT1171	Cell line	HEp-2	Homo sapiens	ED50	=	10.7	ug ml-1	PMID[18316521]
NPT1171	Cell line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[26034885]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512.0	ug.mL-1	PMID[23855338]

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 NPC119583 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	22100
0.1-0.2	24466
0.2-0.3	3027
0.3-0.4	134
0.4-0.5	13
0.5-0.6	15
0.6-0.7	53
0.7-0.8	0
0.8-0.85	5
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC115013
0.9359	High Similarity	NPC483170
0.9333	High Similarity	NPC89843
0.9125	High Similarity	NPC184915
0.9125	High Similarity	NPC224953
0.8902	High Similarity	NPC44782
0.8537	High Similarity	NPC169345
0.8537	High Similarity	NPC477317
0.8537	High Similarity	NPC477318
0.8293	Intermediate Similarity	NPC143421
0.8171	Intermediate Similarity	NPC477319
0.8095	Intermediate Similarity	NPC290012
0.8072	Intermediate Similarity	NPC307400
0.8072	Intermediate Similarity	NPC27289
0.7927	Intermediate Similarity	NPC109887
0.7907	Intermediate Similarity	NPC472200
0.7901	Intermediate Similarity	NPC478734
0.7711	Intermediate Similarity	NPC478733
0.7701	Intermediate Similarity	NPC123204
0.7654	Intermediate Similarity	NPC22742
0.7654	Intermediate Similarity	NPC477346
0.759	Intermediate Similarity	NPC477344
0.7586	Intermediate Similarity	NPC126685
0.7529	Intermediate Similarity	NPC297768
0.747	Intermediate Similarity	NPC477331
0.7412	Intermediate Similarity	NPC146992
0.7412	Intermediate Similarity	NPC85759
0.7412	Intermediate Similarity	NPC267592
0.7407	Intermediate Similarity	NPC281563
0.7386	Intermediate Similarity	NPC183888
0.7386	Intermediate Similarity	NPC259294
0.7356	Intermediate Similarity	NPC476087
0.7356	Intermediate Similarity	NPC475667
0.7273	Intermediate Similarity	NPC478732
0.7241	Intermediate Similarity	NPC472204
0.7241	Intermediate Similarity	NPC294748
0.7229	Intermediate Similarity	NPC113745
0.7229	Intermediate Similarity	NPC477320
0.7229	Intermediate Similarity	NPC477323
0.7229	Intermediate Similarity	NPC477325
0.7229	Intermediate Similarity	NPC609436
0.7216	Intermediate Similarity	NPC10883
0.7191	Intermediate Similarity	NPC475270
0.7191	Intermediate Similarity	NPC475327
0.7159	Intermediate Similarity	NPC238264
0.7159	Intermediate Similarity	NPC477345
0.7126	Intermediate Similarity	NPC173328
0.7097	Intermediate Similarity	NPC475241
0.7079	Intermediate Similarity	NPC238056
0.7	Intermediate Similarity	NPC606819
0.6977	Remote Similarity	NPC158302
0.6977	Remote Similarity	NPC600446
0.6977	Remote Similarity	NPC605013
0.6869	Remote Similarity	NPC290276
0.6854	Remote Similarity	NPC186992
0.6848	Remote Similarity	NPC269318
0.679	Remote Similarity	NPC478729
0.6778	Remote Similarity	NPC478726
0.6774	Remote Similarity	NPC475164
0.6747	Remote Similarity	NPC146380
0.6739	Remote Similarity	NPC163409
0.67	Remote Similarity	NPC10121
0.67	Remote Similarity	NPC198918
0.6667	Remote Similarity	NPC478730
0.6667	Remote Similarity	NPC477332
0.6627	Remote Similarity	NPC477350
0.6591	Remote Similarity	NPC477326
0.6588	Remote Similarity	NPC477329
0.6556	Remote Similarity	NPC472205
0.6526	Remote Similarity	NPC473605
0.6526	Remote Similarity	NPC475375
0.6471	Remote Similarity	NPC477328
0.6471	Remote Similarity	NPC477330
0.6444	Remote Similarity	NPC478722
0.6421	Remote Similarity	NPC478728
0.6396	Remote Similarity	NPC147032
0.6374	Remote Similarity	NPC478724
0.6373	Remote Similarity	NPC611287
0.6364	Remote Similarity	NPC604005
0.6364	Remote Similarity	NPC605014
0.6354	Remote Similarity	NPC478727
0.6344	Remote Similarity	NPC478731
0.63	Remote Similarity	NPC63404
0.6264	Remote Similarity	NPC479061
0.6264	Remote Similarity	NPC60849
0.6264	Remote Similarity	NPC478725
0.625	Remote Similarity	NPC477349
0.6238	Remote Similarity	NPC28069
0.6238	Remote Similarity	NPC77651
0.6222	Remote Similarity	NPC479059
0.6211	Remote Similarity	NPC475525
0.6211	Remote Similarity	NPC475540
0.6196	Remote Similarity	NPC478723
0.6196	Remote Similarity	NPC479060
0.6154	Remote Similarity	NPC610996
0.6146	Remote Similarity	NPC476066
0.6139	Remote Similarity	NPC35338
0.6139	Remote Similarity	NPC204214
0.6139	Remote Similarity	NPC92283
0.6075	Remote Similarity	NPC600940
0.6055	Remote Similarity	NPC471024
0.6019	Remote Similarity	NPC472352
0.6	Remote Similarity	NPC600672
0.5816	Remote Similarity	NPC477347
0.578	Remote Similarity	NPC610997
0.5773	Remote Similarity	NPC479057
0.5741	Remote Similarity	NPC600721
0.5741	Remote Similarity	NPC605872
0.5728	Remote Similarity	NPC124878
0.5728	Remote Similarity	NPC231888
0.5727	Remote Similarity	NPC471026
0.5684	Remote Similarity	NPC479058
0.5648	Remote Similarity	NPC471025
0.5644	Remote Similarity	NPC477348
0.5376	Remote Similarity	NPC87153
0.5361	Remote Similarity	NPC44682
0.5354	Remote Similarity	NPC162925
0.5275	Remote Similarity	NPC475425

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC119583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7299
0.1-0.2	1779
0.2-0.3	72
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data