NPASS Compound

Structure

NPC475188 OpenBabel07101719522D 117121 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1340 10.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6340 14.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6340 13.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 6.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.8301 6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 11.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 10.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1340 9.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2679 9.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 14.2583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 13.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7321 8.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2321 8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7679 12.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 12.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6340 10.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6340 9.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6962 10.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 10.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6340 5.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.5622 9.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6340 11.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 5.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.8301 9.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 10.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6340 6.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1340 15.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6340 14.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.5622 8.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 12.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3660 5.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1340 13.8923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 6.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6340 16.4904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1340 13.8923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 7.8301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 18.6962 7.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6340 13.0263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3660 6.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.8301 8.5622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6340 11.2942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.5000 7.0622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1340 15.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 15.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 7.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6340 13.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9641 8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 11.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 9.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6340 11.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 14.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6340 9.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2321 7.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 13.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 10.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1340 10.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 14.7583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2321 8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6340 13.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.6340 9.5622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1340 13.8923 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6340 16.4904 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 8.6962 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.9641 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.1340 12.1603 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 15.6244 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 10.4282 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 16.0981 8.5622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.6340 8.5622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 13.8923 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.1340 10.4282 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 18.6962 8.0622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 12.1603 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.3660 6.5622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 19.5622 6.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6340 14.7583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6340 14.7583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 8.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1340 12.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 5.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.9641 7.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 12.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3660 8.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 9.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6340 11.2942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 15.6244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1340 8.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0981 6.5622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 13.8923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 50 1 0 0 0 0 4 50 1 0 0 0 0 5 51 1 0 0 0 0 6 51 1 0 0 0 0 7 52 1 0 0 0 0 8 52 1 0 0 0 0 10 54 1 0 0 0 0 11 77 1 0 0 0 0 12 77 1 0 0 0 0 13 78 1 0 0 0 0 14 78 1 0 0 0 0 15 79 1 0 0 0 0 16 79 1 0 0 0 0 17 80 1 0 0 0 0 18 80 1 0 0 0 0 19 81 1 0 0 0 0 20 81 1 0 0 0 0 23 82 1 0 0 0 0 24 83 1 0 0 0 0 25 28 1 0 0 0 0 25 33 1 0 0 0 0 26 29 1 0 0 0 0 26 34 1 0 0 0 0 27 30 1 0 0 0 0 27 35 1 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 44 1 0 0 0 0 31 36 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 32 41 1 0 0 0 0 33 58 1 0 0 0 0 34 59 1 0 0 0 0 35 60 1 0 0 0 0 36 63 1 0 0 0 0 37 38 1 0 0 0 0 37 61 1 0 0 0 0 38 84 1 0 0 0 0 39 97 1 0 0 0 0 40 97 1 0 0 0 0 41 98 1 0 0 0 0 42 99 1 0 0 0 0 43100 1 0 0 0 0 44101 1 0 0 0 0 45 50 1 0 0 0 0 46 51 1 0 0 0 0 47 52 1 0 0 0 0 48 62 1 0 0 0 0 48 85 1 0 0 0 0 49 55 1 0 0 0 0 49 98 1 0 0 0 0 53 9 1 1 0 0 0 53 64 1 0 0 0 0 53 86 1 0 0 0 0 54 99 1 0 0 0 0 54102 2 0 0 0 0 55 45 1 6 0 0 0 55 87 1 0 0 0 0 56 46 1 6 0 0 0 56 65 1 0 0 0 0 56 89 1 0 0 0 0 57 47 1 1 0 0 0 57 66 1 0 0 0 0 57 88 1 0 0 0 0 58 67 1 6 0 0 0 58 99 1 0 0 0 0 59 68 1 1 0 0 0 59100 1 0 0 0 0 60 69 1 1 0 0 0 60101 1 0 0 0 0 61 85 2 3 0 0 0 61103 1 0 0 0 0 62 90 2 3 0 0 0 62104 1 0 0 0 0 63 97 2 0 0 0 0 63 98 1 0 0 0 0 64 88 2 3 0 0 0 64105 1 0 0 0 0 65 84 2 3 0 0 0 65106 1 0 0 0 0 66 93 2 3 0 0 0 66107 1 0 0 0 0 67 92 2 3 0 0 0 67108 1 0 0 0 0 68 91 2 3 0 0 0 68109 1 0 0 0 0 69 94 2 3 0 0 0 69110 1 0 0 0 0 70 77 1 0 0 0 0 70 86 2 3 0 0 0 70111 1 0 0 0 0 71 78 1 0 0 0 0 71 89 2 3 0 0 0 71112 1 0 0 0 0 72 79 1 0 0 0 0 72 95 2 3 0 0 0 72113 1 0 0 0 0 73 82 1 0 0 0 0 73 87 2 3 0 0 0 73114 1 0 0 0 0 74 83 1 0 0 0 0 74 96 2 3 0 0 0 74115 1 0 0 0 0 75 80 1 0 0 0 0 75101 1 0 0 0 0 75116 2 0 0 0 0 76 81 1 0 0 0 0 76100 1 0 0 0 0 76117 2 0 0 0 0 77 91 1 0 0 0 0 78 96 1 0 0 0 0 79 90 1 0 0 0 0 80 92 1 0 0 0 0 81 95 1 0 0 0 0 82 21 1 1 0 0 0 82 93 1 0 0 0 0 83 22 1 1 0 0 0 83 94 1 0 0 0 0 M CHG 1 97 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	1648.09
Volume:	1696.425
LogP:	2.67
LogD:	3.047
LogS:	-2.694
# Rotatable Bonds:	45
TPSA:	480.38
# H-Bond Aceptor:	34
# H-Bond Donor:	13
# Rings:	5
# Heavy Atoms:	34

MedChem Properties

QED Drug-Likeness Score:	0.015
Synthetic Accessibility Score:	7.1
Fsp3:	0.795
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-2.544
MDCK Permeability:	0.00016699738625902683
Pgp-inhibitor:	0.324
Pgp-substrate:	0.948
Human Intestinal Absorption (HIA):	0.991
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0
Plasma Protein Binding (PPB):	43.449729919433594%
Volume Distribution (VD):	0.241
Pgp-substrate:	36.140380859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.034
Half-life (T1/2):	0.13

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.949
Carcinogencity:	0.334
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.869

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC475188

Natural Product ID:	NPC475188
*Common Name:**	Efrapeptin G
IUPAC Name:	(2S)-1-acetyl-N-[1-[(2S)-2-[[(2S)-1-[[1-[[(2S)-1-[[3-[[2-[[1-[[1-[(2S)-2-[[1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-(2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidin-5-ium-1-yl)-4-methylpentan-2-yl]amino]-2-methyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]carbamoyl]piperidin-1-yl]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-oxopropyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxobutan-2-yl]carbamoyl]piperidin-1-yl]-2-methyl-1-oxopropan-2-yl]piperidine-2-carboxamide
Synonyms:	Efrapeptin G
Standard InCHIKey:	MYYCGBYRWZBSPN-CUYPNCLMSA-O
Standard InCHI:	InChI=1S/C83H142N18O16/c1-23-82(21,73(114)87-55(45-50(3)4)49-98-41-32-40-97-39-31-36-63(97)98)93-66(107)57(47-52(7)8)88-64(105)53(9)86-70(111)77(11,12)91-68(109)59-34-26-29-43-100(59)76(117)81(19,20)95-72(113)79(15,16)90-62(104)48-85-61(103)37-38-84-65(106)56(46-51(5)6)89-71(112)78(13,14)96-74(115)83(22,24-2)94-69(110)60-35-27-30-44-101(60)75(116)80(17,18)92-67(108)58-33-25-28-42-99(58)54(10)102/h50-53,55-60H,23-49H2,1-22H3,(H12-,84,85,86,87,88,89,90,91,92,93,94,95,96,103,104,105,106,107,108,109,110,111,112,113,114,115)/p+1/t53-,55-,56-,57-,58-,59-,60-,82-,83-/m0/s1
SMILES:	CCC(C)(C(=O)NC(CC(C)C)CN1CCC[N+]2=C1CCC2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C3CCCCN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)CNC(=O)CCNC(=O)C(CC(C)C)NC(=O)C(C)(C)NC(=O)C(C)(CC)NC(=O)C4CCCCN4C(=O)C(C)(C)NC(=O)C5CCCCN5C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500537
PubChem CID:	44566255
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0002010] Hybrid peptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ 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	NP ID	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	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	Activity	=	3300.0	n.a.	PMID[550491]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	80.0	ug.mL-1	PMID[550491]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC475188 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	17645
0.2-0.3	19308
0.3-0.4	4539
0.4-0.5	861
0.5-0.6	148
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.6698	Remote Similarity	NPC301010
0.6636	Remote Similarity	NPC280066
0.6633	Remote Similarity	NPC31756
0.6566	Remote Similarity	NPC476156
0.6566	Remote Similarity	NPC476243
0.6566	Remote Similarity	NPC476137
0.6566	Remote Similarity	NPC476117
0.65	Remote Similarity	NPC476302
0.6346	Remote Similarity	NPC477539
0.6289	Remote Similarity	NPC266888
0.6289	Remote Similarity	NPC256312
0.6289	Remote Similarity	NPC161774
0.6275	Remote Similarity	NPC84128
0.6275	Remote Similarity	NPC53858
0.625	Remote Similarity	NPC214532
0.625	Remote Similarity	NPC76297
0.625	Remote Similarity	NPC196007
0.6122	Remote Similarity	NPC209156
0.6055	Remote Similarity	NPC477538
0.6019	Remote Similarity	NPC470783
0.6	Remote Similarity	NPC472351
0.598	Remote Similarity	NPC312315
0.5929	Remote Similarity	NPC47076
0.5929	Remote Similarity	NPC134504
0.5895	Remote Similarity	NPC128005
0.5895	Remote Similarity	NPC84182
0.5872	Remote Similarity	NPC275715
0.5865	Remote Similarity	NPC23984
0.5755	Remote Similarity	NPC315551
0.5714	Remote Similarity	NPC128303
0.5701	Remote Similarity	NPC124359
0.569	Remote Similarity	NPC220234
0.5676	Remote Similarity	NPC475801
0.5676	Remote Similarity	NPC474593
0.5667	Remote Similarity	NPC241394
0.566	Remote Similarity	NPC184473
0.5659	Remote Similarity	NPC315188
0.5649	Remote Similarity	NPC477518
0.5644	Remote Similarity	NPC126186
0.563	Remote Similarity	NPC476877
0.5625	Remote Similarity	NPC474576
0.5607	Remote Similarity	NPC235078
0.56	Remote Similarity	NPC470781
0.56	Remote Similarity	NPC63191
0.56	Remote Similarity	NPC471202

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	1491
0.2-0.3	5565
0.3-0.4	1694
0.4-0.5	271
0.5-0.6	38
0.6-0.7	4
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
0.66	Remote Similarity	NPD2683	Discontinued
0.6396	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5366	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7759	Phase 2
0.619	Remote Similarity	NPD7760	Phase 2
0.6176	Remote Similarity	NPD7763	Phase 2
0.6176	Remote Similarity	NPD7762	Phase 2
0.6174	Remote Similarity	NPD6122	Discontinued
0.6017	Remote Similarity	NPD6937	Approved
0.5888	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD322	Phase 1
0.5741	Remote Similarity	NPD5791	Phase 2
0.5714	Remote Similarity	NPD3155	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3628	Phase 3
0.5702	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD3176	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD8038	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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