NPASS Compound

Natural Product: NPC126685

Natural Product ID	NPC126685
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Murucoidin V
IUPAC Name	n.a.
Synonyms	Murucoidin V
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505000
PubChem CID	11607781
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 177182 0 0 0 0 0 0 0 0999 V2000 -9.9105 -1.4708 -5.9190 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6131 -0.7142 -4.8399 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6568 0.2332 -4.0768 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5872 -0.6357 -3.5009 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5110 -0.1093 -2.7236 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6468 0.5675 -1.3791 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4457 1.7518 -1.2844 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4899 2.7987 -0.2598 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4427 3.7903 -0.1065 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1101 3.7003 0.4347 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9481 3.5102 1.9119 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4961 3.7438 2.3820 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4255 3.6779 3.8799 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5602 2.3039 4.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3781 1.4428 4.5111 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4973 1.2252 3.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5638 2.0961 3.1189 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4400 0.2225 2.4719 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7111 -0.1148 1.4102 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6135 -0.6822 0.3300 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7621 0.3242 0.3536 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9325 -0.2026 -0.0351 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9991 -0.2122 0.8066 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1259 -1.0645 0.2812 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0268 -0.4464 -0.4581 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8324 -1.5249 1.4217 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2561 -2.5827 2.0588 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0627 -2.9133 3.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8550 -2.1152 2.4273 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8148 -0.5804 2.2266 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9693 -0.1563 2.9610 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6798 -2.3310 3.7851 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2832 1.4559 -0.2506 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 1.6411 -0.3223 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7225 3.1768 -0.2466 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0192 1.0068 0.6150 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0176 0.3780 -0.1785 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1616 0.1536 0.4782 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9440 1.3496 0.4311 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9948 1.1128 1.3490 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4889 0.6858 2.6809 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9733 0.2415 0.6919 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3964 -0.8764 -0.1723 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8965 -0.9117 -0.1833 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4469 -2.1562 0.3820 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8738 -3.1677 -0.3679 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7575 -2.9564 -1.6114 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4002 -4.4546 0.1661 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3572 -5.1718 1.0577 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6935 -4.3515 2.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0596 -5.4043 -0.9740 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8056 -2.1350 0.2780 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6861 -2.8472 -0.4315 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0205 -3.9202 -1.1386 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9093 -4.7218 -1.7970 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6167 -6.2172 -1.5971 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3310 -6.4925 -2.1180 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3554 -4.3924 -1.6813 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8466 -4.0985 -0.3079 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7010 -3.5002 0.4748 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1968 -2.6028 1.3902 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3090 -5.2220 0.3706 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6806 -3.4047 -2.6137 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8284 1.1110 -0.0242 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1223 0.7088 -0.1347 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8334 1.4181 0.8866 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1946 1.4828 0.6332 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8859 0.1480 0.6882 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5465 2.2923 -0.5540 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3499 2.4066 -1.4784 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6382 1.0595 -1.4736 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5365 0.1060 -1.9126 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7843 2.6905 -2.7768 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9713 3.5739 -0.1141 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1395 4.1316 -0.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8042 3.4801 -1.3875 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6416 5.4385 -0.0939 C 0 0 2 0 0 0 0 0 0 0 0 0 11.6868 5.9247 -1.0922 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9767 6.1018 -2.4288 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2618 5.3004 1.2884 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9524 -1.9806 0.4640 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2370 -0.7822 -6.4634 H 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0 0 0 0 0 0 0 0 0 0 5.8239 1.0962 -2.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0550 -0.6352 -2.4105 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4811 3.3683 -2.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8674 6.2054 -0.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0991 6.8638 -0.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4340 5.1071 -1.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1003 6.7765 -2.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6349 5.1781 -2.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7232 6.5988 -3.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6360 4.5434 1.8266 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1141 6.2453 1.8336 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2979 4.9674 1.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2134 -2.4085 -0.3903 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 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 21 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 43 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 55 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 59 62 1 0 58 63 1 0 42 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 67 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 70 73 1 0 69 74 1 0 74 75 1 0 75 76 2 0 75 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 20 81 1 0 25 6 1 0 44 38 1 0 60 53 1 0 71 65 1 0 36 19 1 0 30 23 1 0 1 82 1 0 1 83 1 0 1 84 1 0 2 85 1 0 2 86 1 0 3 87 1 0 3 88 1 0 4 89 1 0 4 90 1 0 5 91 1 0 5 92 1 0 6 93 1 1 7 94 1 0 7 95 1 0 8 96 1 0 8 97 1 0 9 98 1 0 9 99 1 0 10100 1 0 10101 1 0 11102 1 0 11103 1 0 12104 1 0 12105 1 0 13106 1 0 13107 1 0 14108 1 0 14109 1 0 15110 1 0 15111 1 0 19112 1 1 20113 1 6 21114 1 1 23115 1 1 24116 1 6 27117 1 6 28118 1 0 28119 1 0 28120 1 0 29121 1 6 30122 1 1 31123 1 0 32124 1 0 34125 1 6 35126 1 0 35127 1 0 35128 1 0 36129 1 1 38130 1 1 40131 1 1 41132 1 0 41133 1 0 41134 1 0 42135 1 1 43136 1 6 44137 1 6 48138 1 1 49139 1 0 49140 1 0 50141 1 0 50142 1 0 50143 1 0 51144 1 0 51145 1 0 51146 1 0 53147 1 6 55148 1 6 56149 1 0 56150 1 0 57151 1 0 58152 1 6 59153 1 6 60154 1 1 61155 1 0 62156 1 0 63157 1 0 65158 1 1 67159 1 1 68160 1 0 68161 1 0 68162 1 0 69163 1 6 70164 1 1 71165 1 6 72166 1 0 73167 1 0 77168 1 1 78169 1 0 78170 1 0 79171 1 0 79172 1 0 79173 1 0 80174 1 0 80175 1 0 80176 1 0 81177 1 0 M END

Standard InCHIKey	OIBCXMKASWTFQZ-YKAIXMTBSA-N
Standard InCHI	InChI=1S/C56H96O25/c1-10-13-19-22-32-23-20-17-15-14-16-18-21-24-34(58)75-46-42(66)54(80-47-38(62)35(59)28(6)69-55(47)73-32)71-30(8)44(46)79-56-49(77-51(68)27(5)12-3)48(81-53-40(64)37(61)36(60)33(25-57)74-53)45(31(9)72-56)78-52-41(65)39(63)43(29(7)70-52)76-50(67)26(4)11-2/h26-33,35-49,52-57,59-66H,10-25H2,1-9H3/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](O[C@H]3[C@H](O1)O[C@H](C)[C@@H]([C@@H]3O)O)O[C@@H](C)[C@@H]2O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)[C@H](CC)C)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)OC(=O)[C@H](CC)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1168.62	Volume:	1137.639 ? Van der Waals volume.
Dense:	1.027	LogP:	2.645 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.005 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.775 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	49.0
TPSA:	353.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.056	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.948	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:	0.986	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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.546	Promiscuous compounds:	0.122

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.14	MDCK Permeability:	-5.043
Pgp-inhibitor:	0.0	Pgp-substrate:	0.981
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%):	0.712
50% Bioavailability (F50%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.95
Plasma Protein Binding (PPB):	69.92%	Volume Distribution (VD):	-0.31
Fu:	20.002% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.009

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:	0.03
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.956 ? 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):

0.511

Half-life (T1/2):

3.081

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.036
Human Hepatotoxicity (H-HT):	0.468	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.829	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:	0.819	Drug-induced Nephrotoxicity:	0.974
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.638
A549 Cytotoxicity:	0.961	Hek293 Cytotoxicity:	0.232
BCF:	0.435 ? 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:	3.345 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.241 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.127 ? 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
Ratio IC50	4
Inhibition	1
IC50	1

Activity Type	# Activity
Cell line	5
Organism	4
Others	5

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
NPT91	Cell line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[19715320]
NPT1171	Cell line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[23347584]
NPT165	Cell line	HeLa	Homo sapiens	ED50	=	13.2	ug ml-1	PMID[19711986]
NPT83	Cell line	MCF7	Homo sapiens	Inhibition	=	30.0	%	PMID[23153007]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	256.0	ug.mL-1	DrugMatrix in vivo data: Biochemistry
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512.0	ug.mL-1	PMID[19715320]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[20022253]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[18316521]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	255.0	n.a.	PMID[23398362]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	7.8	n.a.	PMID[23398362]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	47.0	n.a.	PMID[27046397]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	142.5	n.a.	PMID[1375626]
NPT2	Others	Unspecified	n.a.	IC50	=	4.0	nM	PMID[7853002]

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 NPC126685 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	23220
0.1-0.2	22829
0.2-0.3	3345
0.3-0.4	320
0.4-0.5	28
0.5-0.6	28
0.6-0.7	45
0.7-0.8	0
0.8-0.85	13
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC183888
0.9125	High Similarity	NPC143421
0.9125	High Similarity	NPC472204
0.9024	High Similarity	NPC259294
0.9	High Similarity	NPC477319
0.8902	High Similarity	NPC290012
0.8889	High Similarity	NPC307400
0.8889	High Similarity	NPC27289
0.8861	High Similarity	NPC477326
0.8471	Intermediate Similarity	NPC123204
0.8353	Intermediate Similarity	NPC224953
0.8272	Intermediate Similarity	NPC478734
0.8193	Intermediate Similarity	NPC267592
0.8148	Intermediate Similarity	NPC604005
0.8148	Intermediate Similarity	NPC605014
0.8095	Intermediate Similarity	NPC472205
0.8072	Intermediate Similarity	NPC478733
0.8025	Intermediate Similarity	NPC113745
0.8025	Intermediate Similarity	NPC477320
0.8025	Intermediate Similarity	NPC477323
0.8025	Intermediate Similarity	NPC477325
0.8025	Intermediate Similarity	NPC609436
0.7952	Intermediate Similarity	NPC477344
0.7882	Intermediate Similarity	NPC297768
0.7727	Intermediate Similarity	NPC184915
0.759	Intermediate Similarity	NPC22742
0.759	Intermediate Similarity	NPC477346
0.7586	Intermediate Similarity	NPC119583
0.7556	Intermediate Similarity	NPC44782
0.7531	Intermediate Similarity	NPC146380
0.75	Intermediate Similarity	NPC238264
0.75	Intermediate Similarity	NPC483170
0.75	Intermediate Similarity	NPC477345
0.7444	Intermediate Similarity	NPC472200
0.7442	Intermediate Similarity	NPC109887
0.7416	Intermediate Similarity	NPC115013
0.7326	Intermediate Similarity	NPC600446
0.7326	Intermediate Similarity	NPC605013
0.7159	Intermediate Similarity	NPC146992
0.7159	Intermediate Similarity	NPC85759
0.7011	Intermediate Similarity	NPC89843
0.7011	Intermediate Similarity	NPC477331
0.7	Intermediate Similarity	NPC294748
0.6939	Remote Similarity	NPC63404
0.6923	Remote Similarity	NPC476087
0.6923	Remote Similarity	NPC475667
0.6848	Remote Similarity	NPC238056
0.6848	Remote Similarity	NPC478732
0.6848	Remote Similarity	NPC477317
0.6848	Remote Similarity	NPC477318
0.6832	Remote Similarity	NPC10121
0.6832	Remote Similarity	NPC198918
0.6818	Remote Similarity	NPC147032
0.6774	Remote Similarity	NPC475270
0.6774	Remote Similarity	NPC475327
0.6768	Remote Similarity	NPC35338
0.6768	Remote Similarity	NPC204214
0.6768	Remote Similarity	NPC92283
0.6747	Remote Similarity	NPC606819
0.6744	Remote Similarity	NPC281563
0.6701	Remote Similarity	NPC475241
0.6667	Remote Similarity	NPC169345
0.6588	Remote Similarity	NPC477350
0.6505	Remote Similarity	NPC290276
0.6449	Remote Similarity	NPC472352
0.6392	Remote Similarity	NPC475164
0.6355	Remote Similarity	NPC600940
0.6353	Remote Similarity	NPC478729
0.6344	Remote Similarity	NPC173328
0.6337	Remote Similarity	NPC124878
0.6337	Remote Similarity	NPC231888
0.633	Remote Similarity	NPC471024
0.6321	Remote Similarity	NPC600721
0.6321	Remote Similarity	NPC605872
0.6277	Remote Similarity	NPC478730
0.6264	Remote Similarity	NPC477332
0.625	Remote Similarity	NPC477330
0.6222	Remote Similarity	NPC477349
0.6214	Remote Similarity	NPC77651
0.6211	Remote Similarity	NPC478726
0.6196	Remote Similarity	NPC158302
0.619	Remote Similarity	NPC611287
0.618	Remote Similarity	NPC477329
0.6162	Remote Similarity	NPC473605
0.6162	Remote Similarity	NPC475375
0.6105	Remote Similarity	NPC186992
0.6067	Remote Similarity	NPC477328
0.6038	Remote Similarity	NPC10883
0.5981	Remote Similarity	NPC600672
0.5979	Remote Similarity	NPC478731
0.5926	Remote Similarity	NPC471025
0.5905	Remote Similarity	NPC28069
0.59	Remote Similarity	NPC478728
0.5895	Remote Similarity	NPC478722
0.5895	Remote Similarity	NPC479061
0.5859	Remote Similarity	NPC475525
0.5859	Remote Similarity	NPC475540
0.5842	Remote Similarity	NPC478727
0.5833	Remote Similarity	NPC479060
0.5833	Remote Similarity	NPC610996
0.58	Remote Similarity	NPC476066
0.5729	Remote Similarity	NPC478725
0.567	Remote Similarity	NPC478723
0.567	Remote Similarity	NPC478724
0.5644	Remote Similarity	NPC269318
0.5625	Remote Similarity	NPC610997
0.5521	Remote Similarity	NPC479059
0.549	Remote Similarity	NPC477347
0.5439	Remote Similarity	NPC471026
0.5408	Remote Similarity	NPC60849
0.5392	Remote Similarity	NPC163409
0.5354	Remote Similarity	NPC479058
0.5333	Remote Similarity	NPC477348
0.5269	Remote Similarity	NPC475425
0.5196	Remote Similarity	NPC162925
0.5122	Remote Similarity	NPC206823

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC126685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7454
0.1-0.2	1620
0.2-0.3	73
0.3-0.4	3
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