NPASS Compound

Structure

CID324815 OpenBabel06191716172D 106112 0 0 1 0 0 0 0 0999 V2000 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4207 -13.5424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3718 -13.2334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2128 -14.5205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5797 -12.2552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5411 0.5878 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 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8045 -10.8867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8923 -8.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -7.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.1244 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9955 -10.2989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8923 -8.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 1 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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0444 -10.6079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -5.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.3045 -9.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2617 -14.8295 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.5388 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.8365 -11.5861 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 0.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.3045 -9.3479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.5833 -7.5878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3013 -9.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6135 -10.2989 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 11.2013 -7.5878 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 60 1 0 0 0 0 8 68 1 0 0 0 0 9 30 1 0 0 0 0 10 27 1 0 0 0 0 10 31 1 0 0 0 0 11 22 1 0 0 0 0 11 69 1 0 0 0 0 12 24 2 0 0 0 0 12 67 1 0 0 0 0 13 79 1 0 0 0 0 14 80 1 0 0 0 0 15 25 2 0 0 0 0 15105 1 0 0 0 0 16 26 2 0 0 0 0 16106 1 0 0 0 0 17 67 2 0 0 0 0 17 70 1 0 0 0 0 18 33 2 0 0 0 0 18 46 1 0 0 0 0 19 2 1 1 0 0 0 19 27 1 0 0 0 0 19 71 1 0 0 0 0 20 3 1 6 0 0 0 20 34 1 0 0 0 0 20 81 1 0 0 0 0 21 4 1 6 0 0 0 21 32 1 0 0 0 0 21 98 1 0 0 0 0 22 47 1 0 0 0 0 22 61 1 6 0 0 0 23 9 1 1 0 0 0 23 48 1 0 0 0 0 23 69 1 0 0 0 0 24 43 1 0 0 0 0 24 70 1 0 0 0 0 25 49 1 0 0 0 0 25 72 1 0 0 0 0 26 54 1 0 0 0 0 26 73 1 0 0 0 0 27 82 1 6 0 0 0 28 13 1 6 0 0 0 28 36 1 0 0 0 0 28100 1 0 0 0 0 29 14 1 1 0 0 0 29 37 1 0 0 0 0 29 99 1 0 0 0 0 30 62 2 0 0 0 0 30 83 1 0 0 0 0 31 74 2 3 0 0 0 31 84 1 0 0 0 0 32 38 1 0 0 0 0 32 63 1 6 0 0 0 33 50 1 0 0 0 0 33 75 1 0 0 0 0 34 51 1 6 0 0 0 34 74 1 0 0 0 0 35 43 1 0 0 0 0 35 52 1 6 0 0 0 35 76 1 0 0 0 0 36 39 1 0 0 0 0 36 85 1 6 0 0 0 37 44 1 0 0 0 0 37 86 1 6 0 0 0 38 40 1 0 0 0 0 38 87 1 6 0 0 0 39 45 1 0 0 0 0 39 88 1 1 0 0 0 40 56 1 0 0 0 0 40 89 1 6 0 0 0 41 44 1 0 0 0 0 41 57 1 0 0 0 0 41 90 1 1 0 0 0 42 53 1 0 0 0 0 42 55 1 0 0 0 0 42 91 1 0 0 0 0 43101 1 1 0 0 0 44103 1 1 0 0 0 45 58 1 0 0 0 0 45102 1 1 0 0 0 46 64 2 0 0 0 0 46 77 1 0 0 0 0 47 65 2 0 0 0 0 47 92 1 0 0 0 0 48 75 2 0 0 0 0 48 77 1 0 0 0 0 49 68 2 3 0 0 0 49 93 1 0 0 0 0 50 76 2 3 0 0 0 50 94 1 0 0 0 0 51 78 2 3 0 0 0 51 95 1 0 0 0 0 52 71 2 3 0 0 0 52 96 1 0 0 0 0 53 78 1 0 0 0 0 53104 1 0 0 0 0 54 72 2 0 0 0 0 54105 1 0 0 0 0 55 73 2 0 0 0 0 55106 1 0 0 0 0 56 98 1 0 0 0 0 56104 1 1 0 0 0 57 99 1 0 0 0 0 57102 1 6 0 0 0 58100 1 0 0 0 0 58101 1 1 0 0 0 59 66 2 0 0 0 0 59 97 1 0 0 0 0 59103 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1545.58
Volume:	1398.807
LogP:	-6.11
LogD:	-1.783
LogS:	-0.505
# Rotatable Bonds:	41
TPSA:	768.94
# H-Bond Aceptor:	45
# H-Bond Donor:	32
# Rings:	7
# Heavy Atoms:	47

MedChem Properties

QED Drug-Likeness Score:	0.011
Synthetic Accessibility Score:	7.072
Fsp3:	0.644
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.453
MDCK Permeability:	0.002185090444982052
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	24.208324432373047%
Volume Distribution (VD):	0.029
Pgp-substrate:	41.730045318603516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-0.347
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.301
Carcinogencity:	0.071
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.73

Download Data

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

Natural Product: NPC324815

Natural Product ID:	NPC324815
*Common Name:**	[(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1R,2S)-2-[[6-Amino-2-[(1S)-3-Amino-1-[[(2S)-2,3-Diamino-3-Oxopropyl]Amino]-3-Oxopropyl]-5-Methylpyrimidine-4-Carbonyl]Amino]-3-[[(2R,3S)-5-[[(2S,3R)-1-[[2-[4-[4-(4-Aminobutylcarbamoyl)-1,3-Thiazol-2-Yl]-1,3-Thiazol-2-Yl]-1-[(2S,3R,4R,5S,6S)-5-Amino-3,4-Dihydroxy-6-Methyloxan-2-Yl]Oxy-2-Hydroxyethyl]Amino]-3-Hydroxy-1-Oxobutan-2-Yl]Amino]-3-Hydroxy-5-Oxopentan-2-Yl]Amino]-1-(1H-Imidazol-5-Yl)-3-Oxopropoxy]-4,5-Dihydroxy-6-(Hydroxymethyl)Oxan-3-Yl]Oxy-3,5-Dihydroxy-6-(Hydroxymethyl)Oxan-4-Yl] Carbamate
IUPAC Name:	[(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1R,2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2R,3S)-5-[[(2S,3R)-1-[[2-[4-[4-(4-aminobutylcarbamoyl)-1,3-thiazol-2-yl]-1,3-thiazol-2-yl]-1-[(2S,3R,4R,5S,6S)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy-2-hydroxyethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate
Synonyms:
Standard InCHIKey:	MCUABSGWIRKSSZ-IZQRLZLVSA-N
Standard InCHI:	InChI=1S/C59H91N19O26S2/c1-18-33(75-48(77-46(18)64)23(9-30(62)83)69-11-22(61)47(65)92)50(94)76-35(43(24-12-67-17-70-24)101-58-45(39(88)36(85)28(13-79)100-58)102-57-41(90)44(103-59(66)97)37(86)29(14-80)99-57)52(96)71-19(2)27(82)10-31(84)74-34(20(3)81)51(95)78-53(104-56-40(89)38(87)32(63)21(4)98-56)42(91)55-73-26(16-106-55)54-72-25(15-105-54)49(93)68-8-6-5-7-60/h12,15-17,19-23,27-29,32,34-45,53,56-58,69,79-82,85-91H,5-11,13-14,60-61,63H2,1-4H3,(H2,62,83)(H2,65,92)(H2,66,97)(H,67,70)(H,68,93)(H,71,96)(H,74,84)(H,76,94)(H,78,95)(H2,64,75,77)/t19-,20-,21+,22+,23+,27+,28+,29-,32-,34+,35+,36-,37-,38-,39+,40-,41+,42?,43+,44+,45+,53?,56+,57-,58+/m1/s1
SMILES:	CC1C(C(C(C(O1)OC(C(C2=NC(=CS2)C3=NC(=CS3)C(=O)NCCCCN)O)NC(=O)C(C(C)O)NC(=O)CC(C(C)NC(=O)C(C(C4=CN=CN4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)OC(=O)N)O)NC(=O)C7=C(C(=NC(=N7)C(CC(=O)N)NCC(C(=O)N)N)N)C)O)O)O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3391937
PubChem CID:	70697950
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0002010] Hybrid peptides [CHEMONTID:0002009] Hybrid glycopeptides

*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	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18584	Streptoalloteichus hindustanus	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21210656]
NPO18584	Streptoalloteichus hindustanus	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29792433]
NPO18584	Streptoalloteichus hindustanus	Species	Pseudonocardiaceae	Bacteria	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	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
GI50	59

Activity Type	# Activity
Cell Line	59

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	16481.62	nM	PMID[518255]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	5727.96	nM	PMID[518255]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	223.36	nM	PMID[518255]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	3784.43	nM	PMID[518255]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	12882.5	nM	PMID[518255]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	44157.04	nM	PMID[518255]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	311.17	nM	PMID[518255]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	27669.42	nM	PMID[518255]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	12589.25	nM	PMID[518255]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	48083.93	nM	PMID[518255]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	39902.49	nM	PMID[518255]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	1981.53	nM	PMID[518255]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	7888.6	nM	PMID[518255]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	12618.28	nM	PMID[518255]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	31.62	nM	PMID[518255]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	11246.05	nM	PMID[518255]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	49090.79	nM	PMID[518255]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	36897.76	nM	PMID[518255]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	2890.68	nM	PMID[518255]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	18706.82	nM	PMID[518255]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	6729.77	nM	PMID[518255]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	134.28	nM	PMID[518255]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	3863.67	nM	PMID[518255]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	32210.69	nM	PMID[518255]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	16106.46	nM	PMID[518255]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	39902.49	nM	PMID[518255]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	11939.88	nM	PMID[518255]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	144.54	nM	PMID[518255]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	5847.9	nM	PMID[518255]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	15995.58	nM	PMID[518255]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1142.88	nM	PMID[518255]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	18663.8	nM	PMID[518255]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	8590.14	nM	PMID[518255]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	215.77	nM	PMID[518255]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	50003.45	nM	PMID[518255]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	7673.61	nM	PMID[518255]

☑ 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 NPC324815 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	784
0.1-0.2	8747
0.2-0.3	24398
0.3-0.4	5627
0.4-0.5	2656
0.5-0.6	454
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC315126
0.9727	High Similarity	NPC314774
0.6438	Remote Similarity	NPC313514
0.6255	Remote Similarity	NPC21461
0.6227	Remote Similarity	NPC150447
0.6202	Remote Similarity	NPC107160
0.6192	Remote Similarity	NPC313504
0.6167	Remote Similarity	NPC197881
0.6147	Remote Similarity	NPC313897
0.6142	Remote Similarity	NPC235866
0.6055	Remote Similarity	NPC477633
0.6042	Remote Similarity	NPC314254
0.6042	Remote Similarity	NPC313966
0.5994	Remote Similarity	NPC470901
0.5974	Remote Similarity	NPC115282
0.5973	Remote Similarity	NPC195140
0.5944	Remote Similarity	NPC157821
0.5929	Remote Similarity	NPC239737
0.5926	Remote Similarity	NPC39092
0.5919	Remote Similarity	NPC477418
0.5919	Remote Similarity	NPC477420
0.5912	Remote Similarity	NPC478030
0.5904	Remote Similarity	NPC5802
0.5863	Remote Similarity	NPC276373
0.5847	Remote Similarity	NPC189261
0.5827	Remote Similarity	NPC160666
0.5822	Remote Similarity	NPC207633
0.5822	Remote Similarity	NPC328479
0.5819	Remote Similarity	NPC325906
0.5801	Remote Similarity	NPC41982
0.5792	Remote Similarity	NPC238945
0.5791	Remote Similarity	NPC216507
0.5788	Remote Similarity	NPC316756
0.5781	Remote Similarity	NPC477419
0.5781	Remote Similarity	NPC477417
0.5779	Remote Similarity	NPC477634
0.5776	Remote Similarity	NPC324484
0.5775	Remote Similarity	NPC314056
0.5774	Remote Similarity	NPC476492
0.5761	Remote Similarity	NPC471564
0.5744	Remote Similarity	NPC478012
0.5744	Remote Similarity	NPC478011
0.5738	Remote Similarity	NPC326529
0.5733	Remote Similarity	NPC323091
0.573	Remote Similarity	NPC69843
0.5724	Remote Similarity	NPC314176
0.5714	Remote Similarity	NPC324198
0.5714	Remote Similarity	NPC319100
0.5714	Remote Similarity	NPC478013
0.5704	Remote Similarity	NPC75609
0.5704	Remote Similarity	NPC140284
0.5704	Remote Similarity	NPC158055
0.5699	Remote Similarity	NPC476493
0.5692	Remote Similarity	NPC103388
0.5691	Remote Similarity	NPC470900
0.569	Remote Similarity	NPC14590
0.5689	Remote Similarity	NPC136349
0.5687	Remote Similarity	NPC250178
0.5638	Remote Similarity	NPC24589
0.5636	Remote Similarity	NPC470146
0.5636	Remote Similarity	NPC101980
0.5636	Remote Similarity	NPC97078
0.5633	Remote Similarity	NPC282458
0.5633	Remote Similarity	NPC78941
0.563	Remote Similarity	NPC89987
0.56	Remote Similarity	NPC309832
0.56	Remote Similarity	NPC219313

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 NPC324815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1165
0.2-0.3	2508
0.3-0.4	2554
0.4-0.5	1987
0.5-0.6	664
0.6-0.7	22
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
0.6438	Remote Similarity	NPD7138	Phase 2
0.6336	Remote Similarity	NPD8421	Discontinued
0.6231	Remote Similarity	NPD5171	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD4495	Phase 1
0.6178	Remote Similarity	NPD5768	Phase 2
0.6154	Remote Similarity	NPD7929	Approved
0.6154	Remote Similarity	NPD7928	Approved
0.6154	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8250	Phase 2
0.6111	Remote Similarity	NPD4716	Approved
0.6104	Remote Similarity	NPD8260	Approved
0.6102	Remote Similarity	NPD1692	Approved
0.6079	Remote Similarity	NPD1122	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD1504	Discontinued
0.6064	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD5080	Phase 2
0.6008	Remote Similarity	NPD6381	Phase 2
0.6008	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5079	Phase 2
0.6	Remote Similarity	NPD8071	Approved
0.5984	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6417	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD8075	Discontinued
0.5976	Remote Similarity	NPD7981	Discontinued
0.5963	Remote Similarity	NPD5534	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD8442	Discontinued
0.5934	Remote Similarity	NPD2631	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD2632	Approved
0.5934	Remote Similarity	NPD2630	Approved
0.5929	Remote Similarity	NPD2624	Phase 2
0.5929	Remote Similarity	NPD2646	Discontinued
0.5911	Remote Similarity	NPD7241	Phase 3
0.5911	Remote Similarity	NPD7242	Phase 3
0.5895	Remote Similarity	NPD7227	Phase 3
0.5895	Remote Similarity	NPD7226	Phase 3
0.589	Remote Similarity	NPD5342	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5935	Discontinued
0.5887	Remote Similarity	NPD8284	Discontinued
0.5887	Remote Similarity	NPD2062	Phase 2
0.5885	Remote Similarity	NPD4187	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5047	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD5172	Phase 2
0.5873	Remote Similarity	NPD7834	Approved
0.5872	Remote Similarity	NPD3108	Clinical (unspecified phase)
0.5869	Remote Similarity	NPD534	Phase 2
0.5869	Remote Similarity	NPD537	Phase 2
0.5867	Remote Similarity	NPD1369	Phase 2
0.5861	Remote Similarity	NPD8375	Approved
0.5852	Remote Similarity	NPD2893	Phase 3
0.5833	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2876	Phase 3
0.583	Remote Similarity	NPD7816	Clinical (unspecified phase)
0.583	Remote Similarity	NPD703	Discontinued
0.5823	Remote Similarity	NPD1412	Clinical (unspecified phase)
0.5819	Remote Similarity	NPD1776	Approved
0.5819	Remote Similarity	NPD1777	Approved
0.5818	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD8484	Phase 2
0.5803	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4458	Phase 2
0.5788	Remote Similarity	NPD1941	Approved
0.5787	Remote Similarity	NPD2824	Phase 2
0.5787	Remote Similarity	NPD5687	Phase 2
0.5782	Remote Similarity	NPD6450	Phase 2
0.5774	Remote Similarity	NPD6170	Phase 2
0.5758	Remote Similarity	NPD2955	Approved
0.5758	Remote Similarity	NPD2954	Approved
0.5754	Remote Similarity	NPD6023	Discontinued
0.5752	Remote Similarity	NPD536	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD5627	Approved
0.5738	Remote Similarity	NPD207	Discontinued
0.5738	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5731	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD1750	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD2471	Approved
0.5725	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD2472	Approved
0.5721	Remote Similarity	NPD3697	Discontinued
0.572	Remote Similarity	NPD5920	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4171	Clinical (unspecified phase)
0.5704	Remote Similarity	NPD6840	Approved
0.5699	Remote Similarity	NPD3331	Phase 3
0.5696	Remote Similarity	NPD4074	Clinical (unspecified phase)
0.5689	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD796	Phase 2
0.5682	Remote Similarity	NPD549	Approved
0.5681	Remote Similarity	NPD8321	Discontinued
0.5678	Remote Similarity	NPD6992	Phase 2
0.5665	Remote Similarity	NPD245	Suspended
0.5654	Remote Similarity	NPD3848	Phase 2
0.5652	Remote Similarity	NPD1732	Phase 3
0.565	Remote Similarity	NPD4054	Clinical (unspecified phase)
0.565	Remote Similarity	NPD3474	Discovery
0.5649	Remote Similarity	NPD5461	Discontinued
0.5636	Remote Similarity	NPD6175	Phase 3
0.5623	Remote Similarity	NPD6036	Suspended
0.562	Remote Similarity	NPD412	Approved
0.5613	Remote Similarity	NPD4712	Clinical (unspecified phase)
0.561	Remote Similarity	NPD3343	Phase 3
0.5607	Remote Similarity	NPD5666	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