NPASS Compound

Structure

NPC472268 OpenBabel07101718282D 114125 0 0 1 0 0 0 0 0999 V2000 -3.2691 11.8573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9375 1.8988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2143 4.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7104 3.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4960 -3.8353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9921 -2.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3109 9.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 -0.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7183 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8592 0.4960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3109 11.6005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8391 9.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5406 8.7257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 0.9921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8592 -1.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 -2.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0959 10.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 -1.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8592 -0.4960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 4.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8592 1.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8592 2.4802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 2.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3256 7.5107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9168 0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0141 -0.4960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7324 -4.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5973 1.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6451 6.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2958 -4.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9793 1.6420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2838 7.7675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 1.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 2.4802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6183 -0.1369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1549 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7324 -3.4722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2988 0.7525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3883 5.6630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4366 -4.9603 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8592 -0.4960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8592 -3.4722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.3615 -1.0952 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2958 -0.4960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8732 -2.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4366 -5.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0898 4.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5775 -6.4484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8330 4.0033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7642 0.4270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4033 -1.3519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2958 -1.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7183 -5.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0627 1.1285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0837 -0.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7225 0.6837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0420 -0.2057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0141 -3.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8748 3.7465 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9853 7.0660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7018 -0.6504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1549 -1.9841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3823 0.2390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3195 2.0867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7183 -4.9603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0141 -4.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1733 4.4480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9583 3.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 3.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0541 10.6423 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8592 -1.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9921 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0688 6.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5765 0.1198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1549 0.9921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5915 -2.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2570 1.0093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0630 -1.7967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4366 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8732 -1.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2958 -6.4484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0481 5.2183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5775 -7.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5345 3.3018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5075 -0.5313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1465 -2.3102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4366 -1.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 -6.4484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1045 0.8717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8270 -1.4207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7286 6.1077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6598 2.5315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0124 10.3855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9436 7.3228 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9585 0.3078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0141 -1.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6390 1.1973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8732 -4.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1549 -4.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2778 2.3435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5775 -4.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4300 5.4062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 -4.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4240 -0.0178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7435 -0.9072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1549 -2.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6180 2.7882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2150 4.1912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 3 72 1 0 0 0 0 4 72 1 0 0 0 0 5 73 1 0 0 0 0 6 73 1 0 0 0 0 7 74 1 0 0 0 0 9 76 1 0 0 0 0 11 74 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 34 2 0 0 0 0 14 15 1 0 0 0 0 14 35 2 0 0 0 0 15 44 1 0 0 0 0 16 20 1 0 0 0 0 16 43 1 0 0 0 0 17 19 1 0 0 0 0 17 45 1 0 0 0 0 18 74 1 0 0 0 0 19 75 1 0 0 0 0 20 77 1 0 0 0 0 21 23 1 0 0 0 0 21 72 1 0 0 0 0 22 24 1 0 0 0 0 22 76 1 0 0 0 0 23 78 1 0 0 0 0 24 78 1 0 0 0 0 25 36 1 0 0 0 0 25 72 1 0 0 0 0 26 34 1 0 0 0 0 26 79 1 0 0 0 0 27 37 1 0 0 0 0 27101 1 0 0 0 0 28 38 1 0 0 0 0 28102 1 0 0 0 0 29 39 1 0 0 0 0 29104 1 0 0 0 0 30 40 1 0 0 0 0 30103 1 0 0 0 0 31100 1 0 0 0 0 32105 1 0 0 0 0 33 2 1 6 0 0 0 33 59 1 0 0 0 0 33106 1 0 0 0 0 34 63 1 0 0 0 0 35 36 1 0 0 0 0 35 76 1 0 0 0 0 36 78 1 1 0 0 0 37 46 1 0 0 0 0 37 80 1 6 0 0 0 38 47 1 0 0 0 0 38 81 1 6 0 0 0 39 48 1 0 0 0 0 39 82 1 1 0 0 0 40 60 1 0 0 0 0 40 83 1 6 0 0 0 41 31 1 1 0 0 0 41 50 1 0 0 0 0 41108 1 0 0 0 0 42 32 1 6 0 0 0 42 49 1 0 0 0 0 42107 1 0 0 0 0 43 73 1 0 0 0 0 43 75 1 6 0 0 0 44 75 1 6 0 0 0 44 77 1 0 0 0 0 45 73 1 0 0 0 0 45109 1 6 0 0 0 46 54 1 0 0 0 0 46 84 1 1 0 0 0 47 55 1 0 0 0 0 47 85 1 1 0 0 0 48 61 1 0 0 0 0 48 86 1 1 0 0 0 49 51 1 0 0 0 0 49 87 1 1 0 0 0 50 52 1 0 0 0 0 50 88 1 6 0 0 0 51 56 1 0 0 0 0 51 89 1 6 0 0 0 52 62 1 0 0 0 0 52 90 1 1 0 0 0 53 57 1 0 0 0 0 53 59 1 0 0 0 0 53 91 1 6 0 0 0 54 64 1 0 0 0 0 54 92 1 6 0 0 0 55 65 1 0 0 0 0 55 93 1 6 0 0 0 56 68 1 0 0 0 0 56 94 1 1 0 0 0 57 67 1 0 0 0 0 57 95 1 6 0 0 0 58 60 1 0 0 0 0 58 66 1 0 0 0 0 58 96 1 6 0 0 0 59110 1 1 0 0 0 60111 1 1 0 0 0 61 69 1 0 0 0 0 61112 1 6 0 0 0 62 70 1 0 0 0 0 62113 1 6 0 0 0 63 97 2 0 0 0 0 63100 1 0 0 0 0 64101 1 0 0 0 0 64111 1 1 0 0 0 65102 1 0 0 0 0 65112 1 1 0 0 0 66103 1 0 0 0 0 66110 1 1 0 0 0 67106 1 0 0 0 0 67113 1 1 0 0 0 68107 1 0 0 0 0 68109 1 6 0 0 0 69104 1 0 0 0 0 69105 1 1 0 0 0 70108 1 0 0 0 0 70114 1 1 0 0 0 71 98 2 0 0 0 0 71114 1 0 0 0 0 74 99 1 0 0 0 0 75 8 1 6 0 0 0 76 77 1 6 0 0 0 77 10 1 6 0 0 0 78 71 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1636.79
Volume:	1558.232
LogP:	1.847
LogD:	1.145
LogS:	-2.651
# Rotatable Bonds:	25
TPSA:	556.96
# H-Bond Aceptor:	36
# H-Bond Donor:	19
# Rings:	12
# Heavy Atoms:	36

MedChem Properties

QED Drug-Likeness Score:	0.026
Synthetic Accessibility Score:	7.595
Fsp3:	0.897
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:	-6.13
MDCK Permeability:	0.00034226637217216194
Pgp-inhibitor:	0.842
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	49.284202575683594%
Volume Distribution (VD):	-0.455
Pgp-substrate:	15.670600891113281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-1.407
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.169
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC472268

Natural Product ID:	NPC472268
*Common Name:**	Gleditsioside B
IUPAC Name:	[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-[[(2E)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:
Standard InCHIKey:	ORMLQCLBYVIXAG-VNWVVGBMSA-N
Standard InCHI:	InChI=1S/C78H124O36/c1-11-74(7,99)18-12-13-34(26-79)63(97)100-31-41-50(88)52(90)62(113-67-57(95)53(91)59(33(2)106-67)110-66-58(96)60(40(83)30-103-66)111-64-54(92)46(84)37(80)27-101-64)70(108-41)114-71(98)78-23-21-72(3,4)25-36(78)35-14-15-44-75(8)19-17-45(73(5,6)43(75)16-20-77(44,10)76(35,9)22-24-78)109-68-56(94)51(89)49(87)42(107-68)32-105-69-61(48(86)39(82)29-104-69)112-65-55(93)47(85)38(81)28-102-65/h11,13-14,33,36-62,64-70,79-96,99H,1,12,15-32H2,2-10H3/b34-13+/t33-,36-,37+,38+,39-,40+,41+,42+,43-,44+,45-,46-,47-,48-,49+,50+,51-,52-,53-,54+,55+,56+,57+,58+,59-,60-,61+,62+,64-,65-,66-,67-,68-,69-,70-,74?,75-,76+,77+,78-/m0/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(C(OC2OC(=O)C34CCC(CC3C5=CCC6C7(CCC(C(C7CCC6(C5(CC4)C)C)(C)C)OC8C(C(C(C(O8)COC9C(C(C(CO9)O)O)OC1C(C(C(CO1)O)O)O)O)O)O)C)(C)C)COC(=O)C(=CCCC(C)(C=C)O)CO)O)O)O)O)OC1C(C(C(CO1)O)OC1C(C(C(CO1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357149
PubChem CID:	10701743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	anomalous fruits	n.a.	n.a.	PMID[25442304]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	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
IC50	2
Others	2

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	Activity	=	32.94	%	PMID[519172]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	22.21	%	PMID[519172]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	44460.0	nM	PMID[519172]
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	31680.0	nM	PMID[519172]

☑ 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 NPC472268 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	289
0.1-0.2	1685
0.2-0.3	4378
0.3-0.4	7758
0.4-0.5	12464
0.5-0.6	8277
0.6-0.7	4698
0.7-0.8	2135
0.8-0.85	428
0.85-0.9	413
0.9-0.95	143
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472270
1.0	High Similarity	NPC472269
1.0	High Similarity	NPC23020
1.0	High Similarity	NPC112492
0.9829	High Similarity	NPC297950
0.975	High Similarity	NPC475177
0.975	High Similarity	NPC324933
0.975	High Similarity	NPC233223
0.975	High Similarity	NPC183816
0.975	High Similarity	NPC319719
0.975	High Similarity	NPC475444
0.975	High Similarity	NPC473679
0.975	High Similarity	NPC322904
0.975	High Similarity	NPC196874
0.9667	High Similarity	NPC43589
0.9667	High Similarity	NPC222951
0.9667	High Similarity	NPC300655
0.9667	High Similarity	NPC311178
0.95	High Similarity	NPC220838
0.95	High Similarity	NPC45606
0.9417	High Similarity	NPC470516
0.9153	High Similarity	NPC470915
0.9153	High Similarity	NPC471577
0.9153	High Similarity	NPC470911
0.9153	High Similarity	NPC470517
0.9145	High Similarity	NPC475514
0.9145	High Similarity	NPC85154
0.9145	High Similarity	NPC69811
0.9145	High Similarity	NPC473452
0.9145	High Similarity	NPC8524
0.9145	High Similarity	NPC470876
0.9145	High Similarity	NPC286457
0.9145	High Similarity	NPC475209
0.9145	High Similarity	NPC123522
0.9145	High Similarity	NPC220160
0.9145	High Similarity	NPC309223
0.9145	High Similarity	NPC102505
0.9145	High Similarity	NPC191827
0.9145	High Similarity	NPC33012
0.9145	High Similarity	NPC104137
0.9113	High Similarity	NPC312650
0.9113	High Similarity	NPC476776
0.9106	High Similarity	NPC47995
0.9106	High Similarity	NPC265841
0.9076	High Similarity	NPC476127
0.9076	High Similarity	NPC268184
0.9076	High Similarity	NPC476150
0.9076	High Similarity	NPC476991
0.9068	High Similarity	NPC470515
0.9068	High Similarity	NPC471548
0.9068	High Similarity	NPC237191
0.906	High Similarity	NPC75287
0.906	High Similarity	NPC305267
0.906	High Similarity	NPC288205
0.906	High Similarity	NPC51465
0.906	High Similarity	NPC476992
0.906	High Similarity	NPC26626
0.9048	High Similarity	NPC279915
0.9048	High Similarity	NPC110700
0.904	High Similarity	NPC225791
0.904	High Similarity	NPC476779
0.9032	High Similarity	NPC476780
0.9032	High Similarity	NPC476775
0.9032	High Similarity	NPC271610
0.9032	High Similarity	NPC476774
0.9024	High Similarity	NPC470476
0.9024	High Similarity	NPC470475
0.9	High Similarity	NPC275225
0.9	High Similarity	NPC51099
0.9	High Similarity	NPC293031
0.9	High Similarity	NPC68767
0.8992	High Similarity	NPC473386
0.8992	High Similarity	NPC25663
0.8992	High Similarity	NPC51564
0.8992	High Similarity	NPC135849
0.8983	High Similarity	NPC471580
0.8983	High Similarity	NPC471547
0.8983	High Similarity	NPC473824
0.8983	High Similarity	NPC473405
0.8983	High Similarity	NPC475119
0.8974	High Similarity	NPC298034
0.8974	High Similarity	NPC100639
0.8974	High Similarity	NPC4328
0.8974	High Similarity	NPC43550
0.8974	High Similarity	NPC164389
0.8974	High Similarity	NPC236638
0.8974	High Similarity	NPC309907
0.8974	High Similarity	NPC294453
0.8974	High Similarity	NPC161717
0.8974	High Similarity	NPC475486
0.8974	High Similarity	NPC476068
0.8974	High Similarity	NPC473714
0.8974	High Similarity	NPC60557
0.8974	High Similarity	NPC65105
0.8974	High Similarity	NPC123199
0.8974	High Similarity	NPC475160
0.8974	High Similarity	NPC224381
0.8974	High Similarity	NPC79643
0.8974	High Similarity	NPC204414
0.8974	High Similarity	NPC227551
0.8974	High Similarity	NPC471550
0.8974	High Similarity	NPC76972
0.8974	High Similarity	NPC475140
0.8974	High Similarity	NPC71065
0.8974	High Similarity	NPC293330
0.8974	High Similarity	NPC471385
0.8974	High Similarity	NPC119592
0.8974	High Similarity	NPC250247
0.8974	High Similarity	NPC57484
0.8974	High Similarity	NPC54636
0.8974	High Similarity	NPC202828
0.8974	High Similarity	NPC67857
0.8974	High Similarity	NPC70809
0.8974	High Similarity	NPC41061
0.8974	High Similarity	NPC305981
0.8974	High Similarity	NPC469782
0.8974	High Similarity	NPC261506
0.8968	High Similarity	NPC476777
0.8968	High Similarity	NPC476778
0.896	High Similarity	NPC277212
0.896	High Similarity	NPC71391
0.896	High Similarity	NPC46823
0.896	High Similarity	NPC178264
0.896	High Similarity	NPC30279
0.896	High Similarity	NPC473918
0.896	High Similarity	NPC192765
0.8952	High Similarity	NPC244296
0.8952	High Similarity	NPC305793
0.8952	High Similarity	NPC252657
0.8952	High Similarity	NPC280029
0.8952	High Similarity	NPC472267
0.8952	High Similarity	NPC477196
0.8952	High Similarity	NPC1314
0.8952	High Similarity	NPC82380
0.8952	High Similarity	NPC88311
0.8952	High Similarity	NPC273878
0.8952	High Similarity	NPC9470
0.8952	High Similarity	NPC252289
0.8952	High Similarity	NPC269484
0.8952	High Similarity	NPC107536
0.8952	High Similarity	NPC141600
0.8952	High Similarity	NPC97918
0.8952	High Similarity	NPC11577
0.8952	High Similarity	NPC115656
0.8952	High Similarity	NPC470518
0.8917	High Similarity	NPC267694
0.8917	High Similarity	NPC142151
0.8917	High Similarity	NPC110385
0.8917	High Similarity	NPC144644
0.8917	High Similarity	NPC37860
0.8917	High Similarity	NPC153673
0.8908	High Similarity	NPC36831
0.8908	High Similarity	NPC473459
0.8898	High Similarity	NPC37134
0.8898	High Similarity	NPC291903
0.8889	High Similarity	NPC155410
0.8889	High Similarity	NPC174720
0.8889	High Similarity	NPC192600
0.8889	High Similarity	NPC295823
0.8889	High Similarity	NPC251263
0.8889	High Similarity	NPC114304
0.8889	High Similarity	NPC323341
0.8889	High Similarity	NPC114287
0.8889	High Similarity	NPC166422
0.8889	High Similarity	NPC241909
0.8889	High Similarity	NPC46665
0.8889	High Similarity	NPC475287
0.8889	High Similarity	NPC475467
0.8889	High Similarity	NPC309714
0.8889	High Similarity	NPC219180
0.8889	High Similarity	NPC151543
0.8889	High Similarity	NPC133818
0.8889	High Similarity	NPC473826
0.888	High Similarity	NPC477197
0.8871	High Similarity	NPC477194
0.8871	High Similarity	NPC477191
0.8871	High Similarity	NPC477192
0.8871	High Similarity	NPC477193
0.8843	High Similarity	NPC476204
0.8843	High Similarity	NPC170084
0.8833	High Similarity	NPC477464
0.8833	High Similarity	NPC207738
0.8824	High Similarity	NPC110633
0.8824	High Similarity	NPC323359
0.8824	High Similarity	NPC185466
0.8824	High Similarity	NPC148417
0.8824	High Similarity	NPC474483
0.8824	High Similarity	NPC136768
0.8824	High Similarity	NPC300419
0.8824	High Similarity	NPC68175
0.881	High Similarity	NPC478154
0.881	High Similarity	NPC477195
0.8803	High Similarity	NPC109079
0.8803	High Similarity	NPC10320
0.8803	High Similarity	NPC324875
0.8803	High Similarity	NPC1046
0.8803	High Similarity	NPC276093
0.8803	High Similarity	NPC475516
0.8803	High Similarity	NPC80843
0.8803	High Similarity	NPC104400

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 NPC472268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	1875
0.2-0.3	3670
0.3-0.4	2146
0.4-0.5	720
0.5-0.6	310
0.6-0.7	121
0.7-0.8	24
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8548	High Similarity	NPD8328	Phase 3
0.8264	Intermediate Similarity	NPD8133	Approved
0.824	Intermediate Similarity	NPD8516	Approved
0.824	Intermediate Similarity	NPD8515	Approved
0.824	Intermediate Similarity	NPD8517	Approved
0.816	Intermediate Similarity	NPD8377	Approved
0.816	Intermediate Similarity	NPD8294	Approved
0.8151	Intermediate Similarity	NPD6686	Approved
0.8095	Intermediate Similarity	NPD8296	Approved
0.8095	Intermediate Similarity	NPD8335	Approved
0.8095	Intermediate Similarity	NPD8378	Approved
0.8095	Intermediate Similarity	NPD8380	Approved
0.8095	Intermediate Similarity	NPD8379	Approved
0.8095	Intermediate Similarity	NPD8513	Phase 3
0.8077	Intermediate Similarity	NPD7319	Approved
0.8065	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD7507	Approved
0.7953	Intermediate Similarity	NPD8033	Approved
0.7812	Intermediate Similarity	NPD7503	Approved
0.7787	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7736	Approved
0.7717	Intermediate Similarity	NPD7327	Approved
0.7717	Intermediate Similarity	NPD7328	Approved
0.7661	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7516	Approved
0.7638	Intermediate Similarity	NPD7115	Discovery
0.748	Intermediate Similarity	NPD6412	Phase 2
0.7348	Intermediate Similarity	NPD6370	Approved
0.7288	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7259	Intermediate Similarity	NPD8293	Discontinued
0.725	Intermediate Similarity	NPD7902	Approved
0.7239	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6054	Approved
0.7197	Intermediate Similarity	NPD6319	Approved
0.719	Intermediate Similarity	NPD7638	Approved
0.719	Intermediate Similarity	NPD4225	Approved
0.7185	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD8074	Phase 3
0.7132	Intermediate Similarity	NPD7078	Approved
0.7119	Intermediate Similarity	NPD7515	Phase 2
0.7054	Intermediate Similarity	NPD6882	Approved
0.7054	Intermediate Similarity	NPD8297	Approved
0.7049	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6016	Approved
0.7015	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7900	Approved
0.697	Remote Similarity	NPD6009	Approved
0.6963	Remote Similarity	NPD5988	Approved
0.694	Remote Similarity	NPD6059	Approved
0.687	Remote Similarity	NPD4632	Approved
0.68	Remote Similarity	NPD5344	Discontinued
0.6797	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.675	Remote Similarity	NPD46	Approved
0.675	Remote Similarity	NPD6698	Approved
0.6746	Remote Similarity	NPD7632	Discontinued
0.6744	Remote Similarity	NPD6899	Approved
0.6744	Remote Similarity	NPD6881	Approved
0.6718	Remote Similarity	NPD6650	Approved
0.6718	Remote Similarity	NPD8130	Phase 1
0.6718	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6642	Remote Similarity	NPD6921	Approved
0.6641	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7102	Approved
0.6641	Remote Similarity	NPD6883	Approved
0.6641	Remote Similarity	NPD7290	Approved
0.6641	Remote Similarity	NPD6371	Approved
0.6641	Remote Similarity	NPD4634	Approved
0.6591	Remote Similarity	NPD6847	Approved
0.6591	Remote Similarity	NPD6869	Approved
0.6591	Remote Similarity	NPD6617	Approved
0.6589	Remote Similarity	NPD6675	Approved
0.6589	Remote Similarity	NPD7128	Approved
0.6589	Remote Similarity	NPD6402	Approved
0.6589	Remote Similarity	NPD5739	Approved
0.6565	Remote Similarity	NPD6012	Approved
0.6565	Remote Similarity	NPD6014	Approved
0.6565	Remote Similarity	NPD6373	Approved
0.6565	Remote Similarity	NPD6013	Approved
0.6565	Remote Similarity	NPD6372	Approved
0.6557	Remote Similarity	NPD7983	Approved
0.6547	Remote Similarity	NPD7604	Phase 2
0.6547	Remote Similarity	NPD6067	Discontinued
0.6538	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8448	Approved
0.6522	Remote Similarity	NPD5983	Phase 2
0.6513	Remote Similarity	NPD7625	Phase 1
0.6504	Remote Similarity	NPD5779	Approved
0.6504	Remote Similarity	NPD5778	Approved
0.6503	Remote Similarity	NPD8390	Approved
0.6503	Remote Similarity	NPD8392	Approved
0.6503	Remote Similarity	NPD8391	Approved
0.65	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD6011	Approved
0.6489	Remote Similarity	NPD7320	Approved
0.6484	Remote Similarity	NPD5211	Phase 2
0.6479	Remote Similarity	NPD6033	Approved
0.6475	Remote Similarity	NPD7838	Discovery
0.6457	Remote Similarity	NPD6648	Approved
0.6454	Remote Similarity	NPD8451	Approved
0.6454	Remote Similarity	NPD6336	Discontinued
0.6423	Remote Similarity	NPD8035	Phase 2
0.6423	Remote Similarity	NPD6411	Approved
0.6423	Remote Similarity	NPD8034	Phase 2
0.6412	Remote Similarity	NPD5701	Approved
0.6407	Remote Similarity	NPD7799	Discontinued
0.6385	Remote Similarity	NPD5141	Approved
0.6383	Remote Similarity	NPD8340	Approved
0.6383	Remote Similarity	NPD8342	Approved
0.6383	Remote Similarity	NPD8341	Approved
0.6383	Remote Similarity	NPD8299	Approved
0.6351	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD4696	Approved
0.6328	Remote Similarity	NPD5285	Approved
0.6328	Remote Similarity	NPD5286	Approved
0.6312	Remote Similarity	NPD7642	Approved
0.6299	Remote Similarity	NPD6083	Phase 2
0.6299	Remote Similarity	NPD6084	Phase 2
0.6296	Remote Similarity	NPD6053	Discontinued
0.629	Remote Similarity	NPD6079	Approved
0.6286	Remote Similarity	NPD8444	Approved
0.6279	Remote Similarity	NPD8312	Approved
0.6279	Remote Similarity	NPD8313	Approved
0.6276	Remote Similarity	NPD5956	Approved
0.6272	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.626	Remote Similarity	NPD6101	Approved
0.6259	Remote Similarity	NPD7101	Approved
0.6259	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD8336	Approved
0.624	Remote Similarity	NPD6399	Phase 3
0.624	Remote Similarity	NPD8171	Discontinued
0.6239	Remote Similarity	NPD7645	Phase 2
0.6233	Remote Similarity	NPD7260	Phase 2
0.6231	Remote Similarity	NPD5224	Approved
0.6231	Remote Similarity	NPD5226	Approved
0.6231	Remote Similarity	NPD5225	Approved
0.6231	Remote Similarity	NPD4633	Approved
0.6222	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7839	Suspended
0.6218	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6008	Approved
0.6198	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD1694	Approved
0.619	Remote Similarity	NPD8338	Approved
0.6187	Remote Similarity	NPD6335	Approved
0.6183	Remote Similarity	NPD5175	Approved
0.6183	Remote Similarity	NPD5174	Approved
0.6179	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD4755	Approved
0.616	Remote Similarity	NPD7637	Suspended
0.6159	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD5223	Approved
0.6149	Remote Similarity	NPD8450	Suspended
0.6148	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD5328	Approved
0.6119	Remote Similarity	NPD4730	Approved
0.6119	Remote Similarity	NPD4729	Approved
0.6116	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD6317	Approved
0.6111	Remote Similarity	NPD4202	Approved
0.6107	Remote Similarity	NPD8415	Approved
0.6094	Remote Similarity	NPD5222	Approved
0.6094	Remote Similarity	NPD5221	Approved
0.6094	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD8449	Approved
0.608	Remote Similarity	NPD5785	Approved
0.6077	Remote Similarity	NPD4700	Approved
0.6071	Remote Similarity	NPD6313	Approved
0.6071	Remote Similarity	NPD6314	Approved
0.6069	Remote Similarity	NPD8368	Discontinued
0.6054	Remote Similarity	NPD6914	Discontinued
0.6047	Remote Similarity	NPD5173	Approved
0.6043	Remote Similarity	NPD6868	Approved
0.6037	Remote Similarity	NPD8455	Phase 2
0.6034	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5249	Phase 3
0.6029	Remote Similarity	NPD5251	Approved
0.6029	Remote Similarity	NPD5247	Approved
0.6029	Remote Similarity	NPD5248	Approved
0.6029	Remote Similarity	NPD5250	Approved
0.6016	Remote Similarity	NPD6409	Approved
0.6016	Remote Similarity	NPD5695	Phase 3
0.6016	Remote Similarity	NPD7334	Approved
0.6016	Remote Similarity	NPD7521	Approved
0.6016	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6684	Approved
0.6016	Remote Similarity	NPD7146	Approved
0.6016	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5330	Approved

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