NPASS Compound

Structure

CID174140 OpenBabel06191715542D 132147 0 0 1 0 0 0 0 0999 V2000 -12.0424 -2.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1823 -4.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7416 -6.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4619 -6.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0212 -1.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3009 -1.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1310 1.8617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3691 -1.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7722 -4.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8293 -1.2206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6406 2.6294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 4.8369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8602 -0.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5935 -0.5077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4050 -1.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1823 -3.4764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6017 -5.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1610 -1.9865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6905 1.0410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8096 -0.6003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0521 -3.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8907 -1.5455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6528 2.7332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4008 4.0334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7203 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9026 -3.4764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0424 -4.9662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7416 -7.4493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4619 -7.4493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0212 -0.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5620 2.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3595 -1.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4576 -5.1457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5799 -1.8711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2244 3.4329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2210 5.7443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8602 -1.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3009 -0.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7416 -1.4899 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8602 -0.4966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6810 1.1153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2405 0.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0173 -3.2396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7027 -2.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2488 3.6406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3886 4.1372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9026 -4.4696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6017 -7.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1610 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5524 2.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7905 -0.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 -4.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3920 -2.8464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8204 4.3403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2088 5.8481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7203 -1.9865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1119 2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2310 0.3688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7027 -3.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4534 -3.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8326 4.4441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7926 5.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5805 -1.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5805 -0.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2596 0.1462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8191 -0.6745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6017 -1.9865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7203 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6017 -2.9797 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7203 0.9932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7416 -3.4764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8602 1.4899 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3221 -2.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6017 -4.9662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1610 -2.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1134 -3.1489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5215 -0.6234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4463 1.7617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6627 3.3688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7203 0.9932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8814 -2.9797 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.7628 -2.9797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0424 -5.9595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8814 -7.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3221 -7.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8814 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0024 3.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9190 -2.1674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1778 -6.0987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5186 -1.5462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2122 3.3291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6372 6.5479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7628 -4.9662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6017 -8.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1610 0.9932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9834 3.7257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7810 -0.3776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1083 -5.6303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1426 -3.4968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4042 5.1439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6128 6.7555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7203 -2.9797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1024 2.0844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6619 1.2637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6680 -3.7243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -4.1465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0246 6.2589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7804 5.1484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4407 -1.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3221 -1.9865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4619 -4.4696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3009 -3.4764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5373 -3.9580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3023 -0.0094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3064 1.2651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1975 3.8654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5805 1.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2691 0.2204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4995 -2.3682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4407 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8814 -1.9865 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 -9.5263 -1.6236 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7125 -0.0473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4619 -3.4764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7081 1.0971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7416 -4.4696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4562 2.3972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0212 -3.4764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8602 1.4899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 1 26 1 0 0 0 0 2 16 1 0 0 0 0 2 27 2 0 0 0 0 3 17 2 0 0 0 0 3 28 1 0 0 0 0 4 17 1 0 0 0 0 4 29 2 0 0 0 0 5 18 2 0 0 0 0 5 30 1 0 0 0 0 6 18 1 0 0 0 0 6 38 2 0 0 0 0 7 19 2 0 0 0 0 7 31 1 0 0 0 0 8 20 2 0 0 0 0 8 32 1 0 0 0 0 9 21 2 0 0 0 0 9 33 1 0 0 0 0 10 22 2 0 0 0 0 10 34 1 0 0 0 0 11 23 2 0 0 0 0 11 35 1 0 0 0 0 12 24 2 0 0 0 0 12 36 1 0 0 0 0 13 25 2 0 0 0 0 13 37 1 0 0 0 0 14120 1 0 0 0 0 15121 1 0 0 0 0 16 73 1 0 0 0 0 17 74 1 0 0 0 0 18 75 1 0 0 0 0 19 41 1 0 0 0 0 19 65 1 0 0 0 0 20 42 1 0 0 0 0 20 66 1 0 0 0 0 21 43 1 0 0 0 0 21 76 1 0 0 0 0 22 44 1 0 0 0 0 22 77 1 0 0 0 0 23 45 1 0 0 0 0 23 78 1 0 0 0 0 24 46 1 0 0 0 0 24 79 1 0 0 0 0 25 64 1 0 0 0 0 25 80 1 0 0 0 0 26 47 2 0 0 0 0 26 83 1 0 0 0 0 27 47 1 0 0 0 0 27 84 1 0 0 0 0 28 48 2 0 0 0 0 28 85 1 0 0 0 0 29 48 1 0 0 0 0 29 86 1 0 0 0 0 30 49 2 0 0 0 0 30 87 1 0 0 0 0 31 50 2 0 0 0 0 31 88 1 0 0 0 0 32 51 2 0 0 0 0 32 89 1 0 0 0 0 33 52 2 0 0 0 0 33 90 1 0 0 0 0 34 53 2 0 0 0 0 34 91 1 0 0 0 0 35 54 2 0 0 0 0 35 92 1 0 0 0 0 36 55 2 0 0 0 0 36 93 1 0 0 0 0 37 56 2 0 0 0 0 37 94 1 0 0 0 0 38 49 1 0 0 0 0 38122 1 0 0 0 0 39 14 1 1 0 0 0 39 67 1 0 0 0 0 39123 1 0 0 0 0 40 15 1 1 0 0 0 40 68 1 0 0 0 0 40124 1 0 0 0 0 41 42 1 0 0 0 0 41 57 2 0 0 0 0 42 58 2 0 0 0 0 43 44 1 0 0 0 0 43 59 2 0 0 0 0 44 60 2 0 0 0 0 45 46 1 0 0 0 0 45 61 2 0 0 0 0 46 62 2 0 0 0 0 47 95 1 0 0 0 0 48 96 1 0 0 0 0 49 97 1 0 0 0 0 50 57 1 0 0 0 0 50 98 1 0 0 0 0 51 58 1 0 0 0 0 51 99 1 0 0 0 0 52 59 1 0 0 0 0 52100 1 0 0 0 0 53 60 1 0 0 0 0 53101 1 0 0 0 0 54 61 1 0 0 0 0 54102 1 0 0 0 0 55 62 1 0 0 0 0 55103 1 0 0 0 0 56 63 1 0 0 0 0 56104 1 0 0 0 0 57105 1 0 0 0 0 58106 1 0 0 0 0 59107 1 0 0 0 0 60108 1 0 0 0 0 61109 1 0 0 0 0 62110 1 0 0 0 0 63 64 2 0 0 0 0 63111 1 0 0 0 0 64122 1 0 0 0 0 65 66 2 0 0 0 0 65120 1 0 0 0 0 66125 1 0 0 0 0 67 69 1 0 0 0 0 67125 1 6 0 0 0 68 70 1 0 0 0 0 68126 1 6 0 0 0 69 71 1 0 0 0 0 69127 1 1 0 0 0 70 72 1 0 0 0 0 70128 1 1 0 0 0 71 81 1 0 0 0 0 71129 1 6 0 0 0 72 82 1 0 0 0 0 72130 1 6 0 0 0 73112 2 0 0 0 0 73127 1 0 0 0 0 74113 2 0 0 0 0 74129 1 0 0 0 0 75114 2 0 0 0 0 75131 1 0 0 0 0 76115 2 0 0 0 0 76121 1 0 0 0 0 77116 2 0 0 0 0 77126 1 0 0 0 0 78117 2 0 0 0 0 78128 1 0 0 0 0 79118 2 0 0 0 0 79130 1 0 0 0 0 80119 2 0 0 0 0 80132 1 0 0 0 0 81123 1 0 0 0 0 81131 1 6 0 0 0 82124 1 0 0 0 0 82132 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1840.18
Volume:	1626.613
LogP:	3.927
LogD:	1.435
LogS:	-4.93
# Rotatable Bonds:	14
TPSA:	843.22
# H-Bond Aceptor:	50
# H-Bond Donor:	29
# Rings:	16
# Heavy Atoms:	50

MedChem Properties

QED Drug-Likeness Score:	0.038
Synthetic Accessibility Score:	7.323
Fsp3:	0.146
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-8.034
MDCK Permeability:	2.502497181922081e-06
Pgp-inhibitor:	0.059
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.845
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	98.6027603149414%
Volume Distribution (VD):	-0.641
Pgp-substrate:	1709.306884765625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.0
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	14.063
Half-life (T1/2):	0.976

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	1.0
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.138
Skin Sensitization:	0.993
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.98
Respiratory Toxicity:	0.0

Download Data

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

Natural Product: NPC174140

Natural Product ID:	NPC174140
*Common Name:**	Gemin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NYVCMROWMXMBDJ-KGLDGZCVSA-N
Standard InCHI:	InChI=1S/C82H56O50/c83-26-1-16(2-27(84)47(26)95)73(112)127-69-67-39(14-120-65-19-7-31(88)50(98)57(105)41(19)42-20(66(65)125-67)8-32(89)51(99)58(42)106)123-81(71(69)129-74(113)17-3-28(85)48(96)29(86)4-17)131-75(114)18-5-30(87)49(97)38(6-18)122-64-25(13-37(94)56(104)63(64)111)80(119)132-82-72-70(128-78(117)23-11-35(92)54(102)61(109)45(23)46-24(79(118)130-72)12-36(93)55(103)62(46)110)68-40(124-82)15-121-76(115)21-9-33(90)52(100)59(107)43(21)44-22(77(116)126-68)10-34(91)53(101)60(44)108/h1-13,39-40,67-72,81-111H,14-15H2/t39-,40-,67-,68-,69+,70+,71-,72-,81-,82+/m1/s1
SMILES:	c1c(cc(c(c1O)O)O)C(=O)O[C@H]1[C@H]2[C@@H](COc3c4cc(c(c(c4c4c(cc(c(c4O)O)O)c3O2)O)O)O)O[C@@H]([C@@H]1OC(=O)c1cc(c(c(c1)O)O)O)OC(=O)c1cc(c(c(c1)Oc1c(cc(c(c1O)O)O)C(=O)O[C@H]1[C@H]2[C@H]([C@H]3[C@@H](COC(=O)c4cc(c(c(c4-c4c(cc(c(c4O)O)O)C(=O)O3)O)O)O)O1)OC(=O)c1cc(c(c(c1-c1c(cc(c(c1O)O)O)C(=O)O2)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449414
PubChem CID:	44575173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1021/np50028a032]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[10993241]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643063]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989532]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256496]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	leaves and vine stems	Xishuangbanna Tropical Botanical Garden (XTBG), Chinese Academy of Science (CAS), Mengla County, Yunnan Province, China	2009-OCT	PMID[26103517]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222693]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[8759159]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834152]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28301	Clerodendron cyrtophyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO28301	Clerodendron cyrtophyllum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3129	Geum japonicum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21995	Gelsemium elegans	Species	Gelsemiaceae	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	11

Activity Type	# Activity
Cell Line	1
Others	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	40400.0	nM	PMID[497458]
NPT2	Others	Unspecified		Activity	=	106.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	1.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	3.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	16.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	19.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	70.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	60.0	%	PMID[497457]
NPT2	Others	Unspecified		Activity	=	6.0	%	PMID[497457]
NPT2	Others	Unspecified		Inhibition	=	70.0	%	PMID[497457]
NPT2	Others	Unspecified		IC50	=	210.0	nM	PMID[497458]

☑ 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 NPC174140 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	497
0.1-0.2	2097
0.2-0.3	4434
0.3-0.4	9777
0.4-0.5	8269
0.5-0.6	4852
0.6-0.7	6175
0.7-0.8	5295
0.8-0.85	936
0.85-0.9	315
0.9-0.95	27
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9665	High Similarity	NPC471091
0.9665	High Similarity	NPC97924
0.9665	High Similarity	NPC40078
0.9553	High Similarity	NPC240200
0.9553	High Similarity	NPC158214
0.9553	High Similarity	NPC223534
0.9553	High Similarity	NPC290289
0.95	High Similarity	NPC469652
0.95	High Similarity	NPC160543
0.95	High Similarity	NPC472720
0.95	High Similarity	NPC472724
0.95	High Similarity	NPC31208
0.95	High Similarity	NPC93065
0.95	High Similarity	NPC187632
0.95	High Similarity	NPC472721
0.9497	High Similarity	NPC260521
0.9497	High Similarity	NPC469649
0.9348	High Similarity	NPC189312
0.9344	High Similarity	NPC477082
0.9333	High Similarity	NPC261623
0.9333	High Similarity	NPC111490
0.9333	High Similarity	NPC469650
0.9243	High Similarity	NPC3474
0.9235	High Similarity	NPC264302
0.9231	High Similarity	NPC269046
0.9231	High Similarity	NPC477081
0.9231	High Similarity	NPC477083
0.9176	High Similarity	NPC65489
0.9176	High Similarity	NPC237202
0.9167	High Similarity	NPC8940
0.9111	High Similarity	NPC472725
0.9111	High Similarity	NPC472726
0.9071	High Similarity	NPC179947
0.9066	High Similarity	NPC231254
0.9022	High Similarity	NPC473618
0.9016	High Similarity	NPC112380
0.9016	High Similarity	NPC473686
0.9016	High Similarity	NPC475220
0.9016	High Similarity	NPC221140
0.9016	High Similarity	NPC229817
0.9016	High Similarity	NPC475352
0.9011	High Similarity	NPC123259
0.9011	High Similarity	NPC129533
0.9006	High Similarity	NPC80956
0.8973	High Similarity	NPC201814
0.8967	High Similarity	NPC105591
0.8962	High Similarity	NPC49690
0.8956	High Similarity	NPC125352
0.8956	High Similarity	NPC470453
0.8956	High Similarity	NPC470448
0.8956	High Similarity	NPC164047
0.8956	High Similarity	NPC470452
0.893	High Similarity	NPC476358
0.8913	High Similarity	NPC87583
0.8907	High Similarity	NPC476203
0.8907	High Similarity	NPC473631
0.8907	High Similarity	NPC293227
0.8907	High Similarity	NPC475662
0.8907	High Similarity	NPC473717
0.8901	High Similarity	NPC84494
0.8901	High Similarity	NPC245059
0.8895	High Similarity	NPC472723
0.8895	High Similarity	NPC297574
0.8883	High Similarity	NPC47521
0.8865	High Similarity	NPC269625
0.8846	High Similarity	NPC476622
0.8846	High Similarity	NPC476621
0.8846	High Similarity	NPC265380
0.8846	High Similarity	NPC476623
0.8846	High Similarity	NPC476620
0.8846	High Similarity	NPC476619
0.8846	High Similarity	NPC476618
0.8833	High Similarity	NPC100251
0.8824	High Similarity	NPC321046
0.8817	High Similarity	NPC119094
0.8817	High Similarity	NPC7839
0.8817	High Similarity	NPC173872
0.8817	High Similarity	NPC142291
0.8811	High Similarity	NPC241847
0.8804	High Similarity	NPC132111
0.8798	High Similarity	NPC185275
0.8798	High Similarity	NPC212290
0.8791	High Similarity	NPC67629
0.8791	High Similarity	NPC79736
0.8785	High Similarity	NPC98583
0.8771	High Similarity	NPC190204
0.8771	High Similarity	NPC43918
0.8771	High Similarity	NPC261411
0.8757	High Similarity	NPC318119
0.875	High Similarity	NPC477860
0.875	High Similarity	NPC53680
0.875	High Similarity	NPC117668
0.875	High Similarity	NPC475161
0.875	High Similarity	NPC208797
0.8743	High Similarity	NPC267549
0.8743	High Similarity	NPC471789
0.8743	High Similarity	NPC472387
0.8736	High Similarity	NPC470454
0.8736	High Similarity	NPC63105
0.8736	High Similarity	NPC199533
0.8729	High Similarity	NPC65333
0.8722	High Similarity	NPC149300
0.8717	High Similarity	NPC205721
0.8703	High Similarity	NPC150977
0.8703	High Similarity	NPC321916
0.8698	High Similarity	NPC470450
0.8696	High Similarity	NPC471030
0.8696	High Similarity	NPC114257
0.8696	High Similarity	NPC299149
0.8696	High Similarity	NPC324742
0.8696	High Similarity	NPC277710
0.8696	High Similarity	NPC153578
0.8689	High Similarity	NPC472992
0.8689	High Similarity	NPC92403
0.8689	High Similarity	NPC66820
0.8689	High Similarity	NPC170018
0.8689	High Similarity	NPC216307
0.8689	High Similarity	NPC76112
0.8689	High Similarity	NPC46958
0.8689	High Similarity	NPC472991
0.8681	High Similarity	NPC473550
0.8667	High Similarity	NPC31034
0.8667	High Similarity	NPC217781
0.8667	High Similarity	NPC470271
0.8667	High Similarity	NPC311389
0.8663	High Similarity	NPC475179
0.8656	High Similarity	NPC472722
0.8649	High Similarity	NPC469371
0.8649	High Similarity	NPC265795
0.8634	High Similarity	NPC68381
0.8634	High Similarity	NPC3718
0.8634	High Similarity	NPC146803
0.8626	High Similarity	NPC102851
0.8626	High Similarity	NPC81332
0.8626	High Similarity	NPC212038
0.8626	High Similarity	NPC477836
0.8626	High Similarity	NPC5786
0.8626	High Similarity	NPC47140
0.8626	High Similarity	NPC262580
0.8626	High Similarity	NPC67134
0.8626	High Similarity	NPC271848
0.8626	High Similarity	NPC289396
0.8619	High Similarity	NPC198125
0.8619	High Similarity	NPC95421
0.8611	High Similarity	NPC49983
0.8611	High Similarity	NPC26536
0.8611	High Similarity	NPC142707
0.8611	High Similarity	NPC317671
0.8611	High Similarity	NPC175793
0.861	High Similarity	NPC474093
0.861	High Similarity	NPC104910
0.8602	High Similarity	NPC297503
0.8602	High Similarity	NPC97119
0.8602	High Similarity	NPC470718
0.8602	High Similarity	NPC135831
0.8595	High Similarity	NPC58538
0.8595	High Similarity	NPC473785
0.8587	High Similarity	NPC475246
0.8587	High Similarity	NPC102053
0.8587	High Similarity	NPC255799
0.8579	High Similarity	NPC25724
0.8579	High Similarity	NPC213052
0.8579	High Similarity	NPC219600
0.8579	High Similarity	NPC34436
0.8579	High Similarity	NPC263119
0.8579	High Similarity	NPC88560
0.8579	High Similarity	NPC166674
0.8579	High Similarity	NPC46640
0.8579	High Similarity	NPC175230
0.8579	High Similarity	NPC172033
0.8571	High Similarity	NPC52598
0.8571	High Similarity	NPC181778
0.8571	High Similarity	NPC34287
0.8571	High Similarity	NPC149011
0.8571	High Similarity	NPC314672
0.8571	High Similarity	NPC471416
0.8571	High Similarity	NPC204937
0.8571	High Similarity	NPC298778
0.8571	High Similarity	NPC476365
0.8571	High Similarity	NPC470272
0.8564	High Similarity	NPC30011
0.8564	High Similarity	NPC97817
0.8564	High Similarity	NPC64755
0.8564	High Similarity	NPC473818
0.8564	High Similarity	NPC72554
0.8556	High Similarity	NPC148710
0.8556	High Similarity	NPC470451
0.8556	High Similarity	NPC470455
0.8556	High Similarity	NPC470713
0.8556	High Similarity	NPC460984
0.8556	High Similarity	NPC470416
0.8556	High Similarity	NPC25946
0.8556	High Similarity	NPC162169
0.8556	High Similarity	NPC470720
0.8556	High Similarity	NPC470717
0.8556	High Similarity	NPC166851
0.8556	High Similarity	NPC224557
0.8556	High Similarity	NPC21359
0.8556	High Similarity	NPC292706
0.8541	High Similarity	NPC207467

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 NPC174140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	1053
0.2-0.3	2165
0.3-0.4	2690
0.4-0.5	1769
0.5-0.6	718
0.6-0.7	206
0.7-0.8	101
0.8-0.85	13
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD8397	Clinical (unspecified phase)
0.8689	High Similarity	NPD8313	Approved
0.8689	High Similarity	NPD8312	Approved
0.8424	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD5844	Phase 1
0.8384	Intermediate Similarity	NPD8151	Discontinued
0.837	Intermediate Similarity	NPD7074	Phase 3
0.837	Intermediate Similarity	NPD7472	Approved
0.8368	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD7054	Approved
0.8287	Intermediate Similarity	NPD6959	Discontinued
0.8268	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8235	Intermediate Similarity	NPD7808	Phase 3
0.8207	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD7251	Discontinued
0.8162	Intermediate Similarity	NPD3818	Discontinued
0.8128	Intermediate Similarity	NPD6797	Phase 2
0.8065	Intermediate Similarity	NPD7228	Approved
0.8056	Intermediate Similarity	NPD1465	Phase 2
0.8054	Intermediate Similarity	NPD6166	Phase 2
0.8054	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD7783	Phase 2
0.8021	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7956	Intermediate Similarity	NPD8455	Phase 2
0.7923	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7435	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7838	Intermediate Similarity	NPD5494	Approved
0.7824	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7870	Phase 2
0.7822	Intermediate Similarity	NPD7871	Phase 2
0.7802	Intermediate Similarity	NPD1934	Approved
0.7784	Intermediate Similarity	NPD6234	Discontinued
0.7772	Intermediate Similarity	NPD7698	Approved
0.7772	Intermediate Similarity	NPD7768	Phase 2
0.7772	Intermediate Similarity	NPD7696	Phase 3
0.7772	Intermediate Similarity	NPD7697	Approved
0.776	Intermediate Similarity	NPD2801	Approved
0.773	Intermediate Similarity	NPD7075	Discontinued
0.7718	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7874	Approved
0.7711	Intermediate Similarity	NPD6776	Approved
0.7711	Intermediate Similarity	NPD6779	Approved
0.7711	Intermediate Similarity	NPD6781	Approved
0.7711	Intermediate Similarity	NPD6777	Approved
0.7711	Intermediate Similarity	NPD6782	Approved
0.7711	Intermediate Similarity	NPD6780	Approved
0.7711	Intermediate Similarity	NPD6778	Approved
0.7708	Intermediate Similarity	NPD7240	Approved
0.7707	Intermediate Similarity	NPD7701	Phase 2
0.7622	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD7699	Phase 2
0.7612	Intermediate Similarity	NPD7700	Phase 2
0.7609	Intermediate Similarity	NPD37	Approved
0.7596	Intermediate Similarity	NPD4380	Phase 2
0.7581	Intermediate Similarity	NPD4965	Approved
0.7581	Intermediate Similarity	NPD4966	Approved
0.7581	Intermediate Similarity	NPD4967	Phase 2
0.7568	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD7411	Suspended
0.7549	Intermediate Similarity	NPD6823	Phase 2
0.754	Intermediate Similarity	NPD3749	Approved
0.7527	Intermediate Similarity	NPD3817	Phase 2
0.7523	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7199	Phase 2
0.7512	Intermediate Similarity	NPD7801	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7487	Intermediate Similarity	NPD3882	Suspended
0.7486	Intermediate Similarity	NPD1653	Approved
0.7476	Intermediate Similarity	NPD8320	Phase 1
0.7476	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD3787	Discontinued
0.7463	Intermediate Similarity	NPD6535	Approved
0.7463	Intermediate Similarity	NPD6534	Approved
0.7459	Intermediate Similarity	NPD7390	Discontinued
0.7436	Intermediate Similarity	NPD7685	Pre-registration
0.7435	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD5402	Approved
0.7424	Intermediate Similarity	NPD8150	Discontinued
0.7418	Intermediate Similarity	NPD2532	Approved
0.7418	Intermediate Similarity	NPD2534	Approved
0.7418	Intermediate Similarity	NPD2533	Approved
0.7363	Intermediate Similarity	NPD1511	Approved
0.7351	Intermediate Similarity	NPD7458	Discontinued
0.7343	Intermediate Similarity	NPD7680	Approved
0.7337	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7322	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1512	Approved
0.7258	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6212	Phase 3
0.7241	Intermediate Similarity	NPD6213	Phase 3
0.7228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6599	Discontinued
0.7182	Intermediate Similarity	NPD1549	Phase 2
0.7167	Intermediate Similarity	NPD5405	Approved
0.7167	Intermediate Similarity	NPD5406	Approved
0.7167	Intermediate Similarity	NPD5404	Approved
0.7167	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7135	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD3750	Approved
0.7088	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6799	Approved
0.7079	Intermediate Similarity	NPD8434	Phase 2
0.7072	Intermediate Similarity	NPD2935	Discontinued
0.7062	Intermediate Similarity	NPD1247	Approved
0.7059	Intermediate Similarity	NPD5403	Approved
0.7047	Intermediate Similarity	NPD919	Approved
0.7043	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD8059	Phase 3
0.7033	Intermediate Similarity	NPD7266	Discontinued
0.7033	Intermediate Similarity	NPD2346	Discontinued
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5710	Approved
0.7026	Intermediate Similarity	NPD5711	Approved
0.7011	Intermediate Similarity	NPD4628	Phase 3
0.7011	Intermediate Similarity	NPD7003	Approved
0.699	Remote Similarity	NPD3926	Phase 2
0.698	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1551	Phase 2
0.6974	Remote Similarity	NPD8127	Discontinued
0.6973	Remote Similarity	NPD6190	Approved
0.6971	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7177	Discontinued
0.6957	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5401	Approved
0.6944	Remote Similarity	NPD230	Phase 1
0.6939	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1510	Phase 2
0.6919	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7584	Approved
0.6906	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2796	Approved
0.6851	Remote Similarity	NPD1933	Approved
0.6849	Remote Similarity	NPD7930	Approved
0.6831	Remote Similarity	NPD2799	Discontinued
0.6831	Remote Similarity	NPD3748	Approved
0.6828	Remote Similarity	NPD8166	Discontinued
0.6828	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD8285	Discontinued
0.6813	Remote Similarity	NPD1607	Approved
0.6806	Remote Similarity	NPD7585	Approved
0.6796	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1613	Approved
0.6796	Remote Similarity	NPD943	Approved
0.6793	Remote Similarity	NPD8153	Approved
0.6793	Remote Similarity	NPD8152	Approved
0.6789	Remote Similarity	NPD920	Approved
0.6782	Remote Similarity	NPD5953	Discontinued
0.6772	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7286	Phase 2
0.6763	Remote Similarity	NPD4287	Approved
0.6759	Remote Similarity	NPD7583	Approved
0.6758	Remote Similarity	NPD447	Suspended
0.6739	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7549	Discontinued
0.6704	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1240	Approved
0.6703	Remote Similarity	NPD6100	Approved
0.6703	Remote Similarity	NPD6099	Approved
0.6685	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2800	Approved
0.6684	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8067	Phase 3
0.6651	Remote Similarity	NPD5006	Approved
0.6651	Remote Similarity	NPD5005	Approved
0.6649	Remote Similarity	NPD6273	Approved
0.6636	Remote Similarity	NPD7999	Approved
0.6634	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5353	Approved
0.6595	Remote Similarity	NPD7097	Phase 1
0.6593	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD2313	Discontinued
0.6567	Remote Similarity	NPD5242	Approved
0.6564	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6841	Approved
0.6555	Remote Similarity	NPD6843	Phase 3
0.6555	Remote Similarity	NPD6842	Approved
0.6542	Remote Similarity	NPD4420	Approved
0.6538	Remote Similarity	NPD3027	Phase 3

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