NPASS Compound

Structure

CID321939 OpenBabel06191716162D 117122 0 0 1 0 0 0 0 0999 V2000 -10.4146 2.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9332 7.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3778 5.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.7451 -3.5822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5408 3.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9187 -2.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7777 -2.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9268 -1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9268 2.7098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0678 2.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1776 2.2239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9187 1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3982 5.6188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1353 6.2824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4553 -0.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5550 9.4437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4206 -1.2220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6045 4.6486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0787 5.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4634 -0.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6077 9.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4773 -0.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8941 -4.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2513 -6.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9239 -4.8195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2811 -6.4999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4142 2.8338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0347 1.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9512 -1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1274 8.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4206 -2.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4553 2.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7976 7.4044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9377 3.5396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9919 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.0725 -5.0564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6764 6.5521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4386 -4.5255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2461 4.0899 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.5578 -5.3504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9512 3.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6174 -5.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5478 4.3421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2849 5.0057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9675 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9512 1.7180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0614 6.9085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4878 0.8590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8104 3.6207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5947 8.1578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.8943 -1.7180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6385 1.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7976 8.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7184 6.2954 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9919 3.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.8345 -4.2008 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -13.5280 -5.1442 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -10.4146 -0.8590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4309 0.8590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -15.4684 -4.7317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9756 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4553 0.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9919 1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4644 4.3664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6050 8.0929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9024 -1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9187 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4390 0.8590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9311 3.1171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2797 7.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1708 -3.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2574 5.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4390 -2.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9187 -1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9268 1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6472 -5.9690 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.6219 1.2600 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.4309 -2.5770 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9431 -3.4359 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9431 -1.7180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.1439 4.5098 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -17.1023 -5.2626 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4634 0.8590 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9431 1.7180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7154 7.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4797 0.8590 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7832 5.3056 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -14.8047 -3.9946 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -11.4065 -0.8590 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.9268 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9208 3.1820 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5339 7.8389 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -13.4773 -2.5204 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -18.7362 -5.7935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2589 0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6566 8.8922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0614 8.8922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.1917 -5.8813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.1619 -5.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4797 -0.8590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9512 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4878 2.5770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3234 3.8705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3483 9.0510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4065 -2.5770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4146 0.8590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9431 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8016 2.1337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0666 7.7888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2006 -3.6700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2408 6.0987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9919 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1926 4.9795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 37 1 0 0 0 0 3 37 1 0 0 0 0 6 74 1 0 0 0 0 7 74 1 0 0 0 0 8 74 1 0 0 0 0 9 75 1 0 0 0 0 10 75 1 0 0 0 0 11 92 1 0 0 0 0 12 75 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 31 1 0 0 0 0 18 43 2 0 0 0 0 19 44 2 0 0 0 0 22 51 1 0 0 0 0 23 25 1 0 0 0 0 23 40 2 0 0 0 0 24 26 2 0 0 0 0 24 40 1 0 0 0 0 25 42 2 0 0 0 0 26 42 1 0 0 0 0 27 28 1 0 0 0 0 28 52 1 0 0 0 0 29 80 1 0 0 0 0 30 93 1 0 0 0 0 31 94 1 0 0 0 0 32 41 1 0 0 0 0 33 53 1 0 0 0 0 34 41 2 0 0 0 0 34 81 1 0 0 0 0 35117 1 0 0 0 0 36 82 2 3 0 0 0 36 95 1 0 0 0 0 38 4 1 6 0 0 0 38 60 1 0 0 0 0 38 82 1 0 0 0 0 39 5 1 1 0 0 0 39 55 1 0 0 0 0 39116 1 0 0 0 0 40 57 1 0 0 0 0 41 43 1 0 0 0 0 42 76 1 0 0 0 0 43 44 1 0 0 0 0 44 81 1 0 0 0 0 45 20 1 6 0 0 0 45 61 1 0 0 0 0 45 83 1 0 0 0 0 46 32 1 6 0 0 0 46 62 1 0 0 0 0 46 84 1 0 0 0 0 47 33 1 1 0 0 0 47 72 1 0 0 0 0 47 85 1 0 0 0 0 48 35 1 1 0 0 0 48 63 1 0 0 0 0 48 86 1 0 0 0 0 49 27 1 6 0 0 0 49 64 1 0 0 0 0 49 92 1 0 0 0 0 50 21 1 6 0 0 0 50 65 1 0 0 0 0 50 93 1 0 0 0 0 51 66 1 1 0 0 0 51 94 1 0 0 0 0 52 77 2 0 0 0 0 52 96 1 0 0 0 0 53 97 2 0 0 0 0 53 98 1 0 0 0 0 54 37 1 1 0 0 0 54 70 1 0 0 0 0 54 87 1 0 0 0 0 55 69 1 0 0 0 0 55 88 1 1 0 0 0 56 57 1 0 0 0 0 56 71 1 0 0 0 0 56 89 1 0 0 0 0 57 99 1 0 0 0 0 58 67 1 1 0 0 0 58 74 1 0 0 0 0 58 90 1 0 0 0 0 59 68 1 1 0 0 0 59 75 1 0 0 0 0 59 91 1 0 0 0 0 60 89 2 3 0 0 0 60100 1 0 0 0 0 61 86 2 3 0 0 0 61101 1 0 0 0 0 62 83 2 3 0 0 0 62102 1 0 0 0 0 63 88 2 3 0 0 0 63103 1 0 0 0 0 64 87 2 3 0 0 0 64104 1 0 0 0 0 65 85 2 3 0 0 0 65105 1 0 0 0 0 66 90 2 3 0 0 0 66106 1 0 0 0 0 67 91 2 3 0 0 0 67107 1 0 0 0 0 68 84 2 3 0 0 0 68108 1 0 0 0 0 69 92 1 0 0 0 0 69109 2 0 0 0 0 70 93 1 0 0 0 0 70110 2 0 0 0 0 71 94 1 0 0 0 0 71111 2 0 0 0 0 72112 2 0 0 0 0 72116 1 0 0 0 0 73 78 2 0 0 0 0 73 79 1 0 0 0 0 73 80 1 0 0 0 0 113117 1 0 0 0 0 114117 2 0 0 0 0 115117 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1724.69
Volume:	1620.261
LogP:	0.824
LogD:	1.09
LogS:	-0.751
# Rotatable Bonds:	40
TPSA:	636.33
# H-Bond Aceptor:	40
# H-Bond Donor:	20
# Rings:	6
# Heavy Atoms:	42

MedChem Properties

QED Drug-Likeness Score:	0.013
Synthetic Accessibility Score:	7.771
Fsp3:	0.587
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:	-5.329
MDCK Permeability:	0.0005635503330267966
Pgp-inhibitor:	0.001
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):	0.984
Plasma Protein Binding (PPB):	43.027076721191406%
Volume Distribution (VD):	0.639
Pgp-substrate:	38.0972785949707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.393
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.0
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.334
Skin Sensitization:	0.476
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC321939

Natural Product ID:	NPC321939
*Common Name:**	Microspinosamide
IUPAC Name:	2-[(3R,6S,9S,10R,13R,16S)-6-(3-amino-3-oxopropyl)-9-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-1-[3-(4-bromophenyl)-2-[[(2R)-2-formamidopropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]-3,3-dimethylbutanoyl]amino]-3,3-dimethylpentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-sulfopropanoyl]amino]-7,10-dimethyl-2,5,8,12,15-pentaoxo-3-propan-2-yl-11-oxa-1,4,7,14-tetrazabicyclo[14.3.0]nonadecan-13-yl]acetic acid
Synonyms:	Microspinosamide
Standard InCHIKey:	GUGALNGMVNRENE-DPOFQXJLSA-N
Standard InCHI:	InChI=1S/C75H109BrN18O22S/c1-12-75(9,10)59(91-67(107)58(74(6,7)8)90-66(106)51-22-17-31-94(51)71(111)56(89-60(100)38(4)82-36-95)57(99)40-23-25-42(76)26-24-40)68(108)84-46(32-41-34-81-44-19-14-13-18-43(41)44)62(102)83-45(20-15-29-80-73(78)79)61(101)86-48(35-117(113,114)115)63(103)88-55-39(5)116-72(112)47(33-53(97)98)85-65(105)50-21-16-30-93(50)70(110)54(37(2)3)87-64(104)49(27-28-52(77)96)92(11)69(55)109/h13-14,18-19,23-26,34,36-39,45-51,54-59,81,99H,12,15-17,20-22,27-33,35H2,1-11H3,(H2,77,96)(H,82,95)(H,83,102)(H,84,108)(H,85,105)(H,86,101)(H,87,104)(H,88,103)(H,89,100)(H,90,106)(H,91,107)(H,97,98)(H4,78,79,80)(H,113,114,115)/t38-,39-,45+,46-,47-,48-,49+,50+,51+,54-,55+,56?,57?,58+,59-/m1/s1
SMILES:	OC=N[C@@H](C(=NC(C(c1ccc(cc1)Br)O)C(=O)N1CCC[C@H]1C(=N[C@H](C(C)(C)C)C(=N[C@@H](C(CC)(C)C)C(=N[C@@H](C(=N[C@H](C(=N[C@@H](C(=N[C@H]1[C@@H](C)OC(=O)[C@@H](CC(=O)O)N=C(O)[C@@H]2CCCN2C(=O)[C@H](N=C([C@@H](N(C1=O)C)CCC(=N)O)O)C(C)C)O)CS(=O)(=O)O)O)CCCNC(=N)N)O)Cc1c[nH]c2c1cccc2)O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502040
PubChem CID:	25076067
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO28323	Sidonops microspinosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11170684]
NPO28323	Sidonops microspinosa	n.a.	n.a.	n.a.	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
EC50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[449436]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.2	ug.mL-1	PMID[449436]

☑ 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 NPC321939 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	415
0.1-0.2	2465
0.2-0.3	14831
0.3-0.4	18075
0.4-0.5	3000
0.5-0.6	2967
0.6-0.7	779
0.7-0.8	137
0.8-0.85	20
0.85-0.9	1
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC242872
0.9706	High Similarity	NPC263117
0.9706	High Similarity	NPC125181
0.7869	Intermediate Similarity	NPC64216
0.7849	Intermediate Similarity	NPC478029
0.7811	Intermediate Similarity	NPC478013
0.7795	Intermediate Similarity	NPC477109
0.7795	Intermediate Similarity	NPC477108
0.7795	Intermediate Similarity	NPC477107
0.7792	Intermediate Similarity	NPC54744
0.7782	Intermediate Similarity	NPC477635
0.7782	Intermediate Similarity	NPC320968
0.7782	Intermediate Similarity	NPC477630
0.7769	Intermediate Similarity	NPC478028
0.7756	Intermediate Similarity	NPC17487
0.7756	Intermediate Similarity	NPC201831
0.7722	Intermediate Similarity	NPC153400
0.772	Intermediate Similarity	NPC89987
0.7701	Intermediate Similarity	NPC477633
0.7698	Intermediate Similarity	NPC314056
0.7692	Intermediate Similarity	NPC314882
0.768	Intermediate Similarity	NPC14288
0.7649	Intermediate Similarity	NPC321592
0.7649	Intermediate Similarity	NPC165743
0.7649	Intermediate Similarity	NPC54803
0.764	Intermediate Similarity	NPC223409
0.764	Intermediate Similarity	NPC95240
0.7625	Intermediate Similarity	NPC478158
0.7625	Intermediate Similarity	NPC162860
0.7619	Intermediate Similarity	NPC63279
0.7613	Intermediate Similarity	NPC478157
0.761	Intermediate Similarity	NPC475969
0.761	Intermediate Similarity	NPC474877
0.761	Intermediate Similarity	NPC475859
0.7603	Intermediate Similarity	NPC75634
0.76	Intermediate Similarity	NPC100547
0.7592	Intermediate Similarity	NPC281049
0.759	Intermediate Similarity	NPC319232
0.759	Intermediate Similarity	NPC24370
0.7589	Intermediate Similarity	NPC245055
0.7589	Intermediate Similarity	NPC297642
0.757	Intermediate Similarity	NPC470730
0.757	Intermediate Similarity	NPC477176
0.757	Intermediate Similarity	NPC477175
0.757	Intermediate Similarity	NPC322135
0.757	Intermediate Similarity	NPC470729
0.756	Intermediate Similarity	NPC304307
0.756	Intermediate Similarity	NPC261251
0.756	Intermediate Similarity	NPC34580
0.756	Intermediate Similarity	NPC124920
0.756	Intermediate Similarity	NPC118559
0.7552	Intermediate Similarity	NPC107077
0.7552	Intermediate Similarity	NPC223791
0.755	Intermediate Similarity	NPC474196
0.7542	Intermediate Similarity	NPC54420
0.754	Intermediate Similarity	NPC477177
0.7531	Intermediate Similarity	NPC473376
0.7521	Intermediate Similarity	NPC155143
0.752	Intermediate Similarity	NPC214142
0.752	Intermediate Similarity	NPC325976
0.7509	Intermediate Similarity	NPC478006
0.75	Intermediate Similarity	NPC478011
0.75	Intermediate Similarity	NPC478012
0.748	Intermediate Similarity	NPC125597
0.748	Intermediate Similarity	NPC284888
0.748	Intermediate Similarity	NPC323752
0.7479	Intermediate Similarity	NPC475506
0.7473	Intermediate Similarity	NPC314176
0.746	Intermediate Similarity	NPC474195
0.7451	Intermediate Similarity	NPC33064
0.7449	Intermediate Similarity	NPC475736
0.7448	Intermediate Similarity	NPC476874
0.7441	Intermediate Similarity	NPC63031
0.7431	Intermediate Similarity	NPC326363
0.7412	Intermediate Similarity	NPC220852
0.7409	Intermediate Similarity	NPC477634
0.7407	Intermediate Similarity	NPC315467
0.7393	Intermediate Similarity	NPC28945
0.7388	Intermediate Similarity	NPC31385
0.7388	Intermediate Similarity	NPC75726
0.7388	Intermediate Similarity	NPC110602
0.7364	Intermediate Similarity	NPC82472
0.736	Intermediate Similarity	NPC473317
0.7353	Intermediate Similarity	NPC473640
0.7326	Intermediate Similarity	NPC285343
0.7322	Intermediate Similarity	NPC293917
0.7322	Intermediate Similarity	NPC100321
0.7321	Intermediate Similarity	NPC471536
0.7316	Intermediate Similarity	NPC478010
0.7316	Intermediate Similarity	NPC478009
0.7269	Intermediate Similarity	NPC477114
0.7247	Intermediate Similarity	NPC207020
0.7227	Intermediate Similarity	NPC69843
0.7218	Intermediate Similarity	NPC14812
0.7218	Intermediate Similarity	NPC229348
0.7208	Intermediate Similarity	NPC171317
0.7184	Intermediate Similarity	NPC323927
0.7171	Intermediate Similarity	NPC477714
0.716	Intermediate Similarity	NPC470731
0.716	Intermediate Similarity	NPC74969
0.716	Intermediate Similarity	NPC193761
0.716	Intermediate Similarity	NPC470732
0.7154	Intermediate Similarity	NPC181081
0.7154	Intermediate Similarity	NPC474896
0.7126	Intermediate Similarity	NPC31097
0.7115	Intermediate Similarity	NPC272174
0.7101	Intermediate Similarity	NPC117980
0.7063	Intermediate Similarity	NPC477715
0.7029	Intermediate Similarity	NPC243716
0.7023	Intermediate Similarity	NPC272549
0.7017	Intermediate Similarity	NPC213629
0.7004	Intermediate Similarity	NPC235885
0.7004	Intermediate Similarity	NPC277350
0.6996	Remote Similarity	NPC238945
0.6988	Remote Similarity	NPC56109
0.6988	Remote Similarity	NPC191382
0.6988	Remote Similarity	NPC33949
0.6953	Remote Similarity	NPC2395
0.6947	Remote Similarity	NPC323198
0.6926	Remote Similarity	NPC155444
0.6926	Remote Similarity	NPC474389
0.6923	Remote Similarity	NPC156003
0.6911	Remote Similarity	NPC300183
0.6908	Remote Similarity	NPC328924
0.689	Remote Similarity	NPC204491
0.689	Remote Similarity	NPC203614
0.6885	Remote Similarity	NPC262898
0.6885	Remote Similarity	NPC476491
0.6877	Remote Similarity	NPC267965
0.6873	Remote Similarity	NPC19170
0.687	Remote Similarity	NPC214428
0.6865	Remote Similarity	NPC82370
0.6863	Remote Similarity	NPC79386
0.6862	Remote Similarity	NPC94752
0.686	Remote Similarity	NPC304187
0.686	Remote Similarity	NPC473342
0.686	Remote Similarity	NPC477166
0.686	Remote Similarity	NPC477167
0.6853	Remote Similarity	NPC469743
0.6846	Remote Similarity	NPC472762
0.6844	Remote Similarity	NPC179701
0.6838	Remote Similarity	NPC87856
0.6838	Remote Similarity	NPC151976
0.6836	Remote Similarity	NPC475746
0.6824	Remote Similarity	NPC132211
0.6824	Remote Similarity	NPC36405
0.682	Remote Similarity	NPC57690
0.6818	Remote Similarity	NPC70155
0.6813	Remote Similarity	NPC127677
0.6813	Remote Similarity	NPC258062
0.6809	Remote Similarity	NPC315804
0.6809	Remote Similarity	NPC313804
0.6805	Remote Similarity	NPC321708
0.6802	Remote Similarity	NPC23420
0.6802	Remote Similarity	NPC303820
0.6802	Remote Similarity	NPC106771
0.6802	Remote Similarity	NPC205254
0.6802	Remote Similarity	NPC470497
0.6794	Remote Similarity	NPC297862
0.6787	Remote Similarity	NPC98715
0.6786	Remote Similarity	NPC271862
0.6774	Remote Similarity	NPC52909
0.6774	Remote Similarity	NPC94211
0.6774	Remote Similarity	NPC475935
0.6773	Remote Similarity	NPC46225
0.6773	Remote Similarity	NPC225821
0.6769	Remote Similarity	NPC147446
0.6766	Remote Similarity	NPC171393
0.6766	Remote Similarity	NPC295452
0.6763	Remote Similarity	NPC17059
0.6758	Remote Similarity	NPC471192
0.6756	Remote Similarity	NPC323244
0.6743	Remote Similarity	NPC141428
0.6742	Remote Similarity	NPC15801
0.674	Remote Similarity	NPC476516
0.6732	Remote Similarity	NPC472285
0.6731	Remote Similarity	NPC253987
0.6731	Remote Similarity	NPC312942
0.6731	Remote Similarity	NPC327095
0.6719	Remote Similarity	NPC474412
0.6719	Remote Similarity	NPC313640
0.6706	Remote Similarity	NPC153980
0.6706	Remote Similarity	NPC6865
0.6705	Remote Similarity	NPC40455
0.6705	Remote Similarity	NPC266192
0.6702	Remote Similarity	NPC77101
0.6694	Remote Similarity	NPC88315
0.6693	Remote Similarity	NPC470505
0.6693	Remote Similarity	NPC234999
0.6692	Remote Similarity	NPC244536
0.6692	Remote Similarity	NPC475258
0.668	Remote Similarity	NPC477610
0.668	Remote Similarity	NPC473763
0.668	Remote Similarity	NPC117244
0.668	Remote Similarity	NPC473761
0.6667	Remote Similarity	NPC72956
0.6667	Remote Similarity	NPC54981
0.6667	Remote Similarity	NPC16352
0.6667	Remote Similarity	NPC82053
0.6654	Remote Similarity	NPC475338

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 NPC321939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	597
0.2-0.3	1038
0.3-0.4	2396
0.4-0.5	2757
0.5-0.6	1874
0.6-0.7	279
0.7-0.8	17
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
0.7833	Intermediate Similarity	NPD7970	Approved
0.7833	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD7470	Discontinued
0.7469	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7711	Discontinued
0.7322	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD8272	Phase 2
0.7206	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8072	Approved
0.7171	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD8073	Approved
0.7028	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7824	Approved
0.7011	Intermediate Similarity	NPD7789	Approved
0.7011	Intermediate Similarity	NPD7790	Approved
0.7011	Intermediate Similarity	NPD7950	Approved
0.7011	Intermediate Similarity	NPD7953	Approved
0.7011	Intermediate Similarity	NPD7791	Approved
0.7011	Intermediate Similarity	NPD7951	Approved
0.7011	Intermediate Similarity	NPD7952	Approved
0.6988	Remote Similarity	NPD7781	Approved
0.6988	Remote Similarity	NPD7780	Approved
0.6984	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7730	Approved
0.695	Remote Similarity	NPD7731	Approved
0.6905	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7717	Approved
0.6899	Remote Similarity	NPD7716	Approved
0.6877	Remote Similarity	NPD8094	Discontinued
0.6873	Remote Similarity	NPD7271	Approved
0.6867	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8322	Phase 2
0.684	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8093	Discontinued
0.6825	Remote Similarity	NPD8247	Approved
0.6825	Remote Similarity	NPD8246	Approved
0.681	Remote Similarity	NPD8284	Discontinued
0.6805	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7944	Discontinued
0.68	Remote Similarity	NPD7001	Phase 3
0.68	Remote Similarity	NPD7957	Phase 1
0.68	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8075	Discontinued
0.6782	Remote Similarity	NPD7603	Discontinued
0.678	Remote Similarity	NPD8119	Discontinued
0.6746	Remote Similarity	NPD2510	Approved
0.6746	Remote Similarity	NPD2509	Approved
0.6742	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8255	Phase 2
0.6732	Remote Similarity	NPD8271	Discontinued
0.6729	Remote Similarity	NPD7576	Discontinued
0.6718	Remote Similarity	NPD8289	Discontinued
0.6718	Remote Similarity	NPD1996	Discontinued
0.6711	Remote Similarity	NPD8421	Discontinued
0.6706	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8169	Discontinued
0.6692	Remote Similarity	NPD4086	Phase 1
0.6692	Remote Similarity	NPD8292	Phase 2
0.668	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.668	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2095	Phase 2
0.6667	Remote Similarity	NPD2092	Phase 2
0.6667	Remote Similarity	NPD2094	Phase 2
0.6667	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD2091	Phase 2
0.6639	Remote Similarity	NPD2096	Phase 2
0.663	Remote Similarity	NPD8375	Approved
0.6629	Remote Similarity	NPD8430	Approved
0.6627	Remote Similarity	NPD8098	Approved
0.6627	Remote Similarity	NPD8261	Discontinued
0.6613	Remote Similarity	NPD5003	Discontinued
0.6603	Remote Similarity	NPD8356	Approved
0.6602	Remote Similarity	NPD8257	Approved
0.6602	Remote Similarity	NPD8256	Approved
0.6602	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7619	Phase 3
0.6599	Remote Similarity	NPD7618	Phase 3
0.6587	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD7778	Approved
0.6586	Remote Similarity	NPD7777	Approved
0.6586	Remote Similarity	NPD53	Approved
0.6582	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8097	Phase 3
0.6576	Remote Similarity	NPD8096	Phase 3
0.6573	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6164	Phase 2
0.6566	Remote Similarity	NPD6165	Phase 2
0.6561	Remote Similarity	NPD5426	Phase 3
0.6538	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD484	Approved
0.6533	Remote Similarity	NPD7967	Discontinued
0.6533	Remote Similarity	NPD8253	Phase 3
0.653	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8524	Approved
0.6518	Remote Similarity	NPD6665	Discontinued
0.6517	Remote Similarity	NPD8374	Phase 3
0.6515	Remote Similarity	NPD6595	Phase 3
0.6513	Remote Similarity	NPD7878	Phase 2
0.6509	Remote Similarity	NPD8359	Phase 2
0.6508	Remote Similarity	NPD7817	Phase 1
0.6507	Remote Similarity	NPD8460	Approved
0.6507	Remote Similarity	NPD8459	Approved
0.65	Remote Similarity	NPD3394	Approved
0.65	Remote Similarity	NPD3393	Approved
0.65	Remote Similarity	NPD3389	Approved
0.6496	Remote Similarity	NPD5901	Discontinued
0.6493	Remote Similarity	NPD7688	Phase 1
0.6485	Remote Similarity	NPD482	Approved
0.6475	Remote Similarity	NPD8525	Approved
0.6475	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8325	Phase 3
0.6475	Remote Similarity	NPD8326	Phase 3
0.646	Remote Similarity	NPD7770	Phase 3
0.646	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7689	Approved
0.6458	Remote Similarity	NPD5891	Approved
0.6458	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6176	Phase 1
0.6453	Remote Similarity	NPD6752	Phase 1
0.6453	Remote Similarity	NPD6753	Phase 1
0.6453	Remote Similarity	NPD6173	Approved
0.6449	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD3917	Approved
0.6448	Remote Similarity	NPD3918	Approved
0.6448	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD8106	Phase 2
0.6426	Remote Similarity	NPD8465	Approved
0.6426	Remote Similarity	NPD8428	Approved
0.6426	Remote Similarity	NPD8427	Approved
0.6426	Remote Similarity	NPD8429	Approved
0.6426	Remote Similarity	NPD8466	Approved
0.6426	Remote Similarity	NPD8467	Approved
0.6423	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD8329	Phase 3
0.6414	Remote Similarity	NPD7948	Phase 1
0.6414	Remote Similarity	NPD7655	Discontinued
0.6412	Remote Similarity	NPD5818	Discontinued
0.6409	Remote Similarity	NPD3915	Approved
0.6406	Remote Similarity	NPD4904	Approved
0.6403	Remote Similarity	NPD5043	Discontinued
0.6403	Remote Similarity	NPD4601	Approved
0.6403	Remote Similarity	NPD4600	Approved
0.6395	Remote Similarity	NPD4520	Approved
0.6389	Remote Similarity	NPD8364	Approved
0.6389	Remote Similarity	NPD8363	Approved
0.6384	Remote Similarity	NPD7415	Suspended
0.638	Remote Similarity	NPD7769	Phase 3
0.6375	Remote Similarity	NPD750	Phase 2
0.6375	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7465	Suspended
0.637	Remote Similarity	NPD8370	Discontinued
0.6367	Remote Similarity	NPD8282	Approved
0.6367	Remote Similarity	NPD8283	Approved
0.6367	Remote Similarity	NPD8250	Phase 2
0.6367	Remote Similarity	NPD56	Approved
0.6367	Remote Similarity	NPD4906	Approved
0.6367	Remote Similarity	NPD4905	Approved
0.6367	Remote Similarity	NPD4903	Approved
0.6364	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6999	Discontinued
0.6357	Remote Similarity	NPD7981	Discontinued
0.6357	Remote Similarity	NPD7665	Phase 2
0.6357	Remote Similarity	NPD7666	Phase 3
0.6354	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.635	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.635	Remote Similarity	NPD6154	Approved
0.6349	Remote Similarity	NPD6664	Approved
0.6345	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8426	Approved
0.6339	Remote Similarity	NPD8425	Approved
0.6337	Remote Similarity	NPD8386	Phase 2
0.6326	Remote Similarity	NPD3354	Phase 2
0.6325	Remote Similarity	NPD8489	Phase 1
0.6325	Remote Similarity	NPD8484	Phase 2
0.6324	Remote Similarity	NPD7946	Pre-registration
0.6321	Remote Similarity	NPD5482	Discontinued
0.6318	Remote Similarity	NPD7928	Approved
0.6318	Remote Similarity	NPD7929	Approved
0.6318	Remote Similarity	NPD7834	Approved
0.6311	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.631	Remote Similarity	NPD8317	Phase 2
0.631	Remote Similarity	NPD8316	Phase 2
0.6308	Remote Similarity	NPD8321	Discontinued
0.6305	Remote Similarity	NPD2564	Approved
0.6305	Remote Similarity	NPD2565	Phase 2
0.6304	Remote Similarity	NPD8114	Approved
0.6304	Remote Similarity	NPD8115	Approved
0.63	Remote Similarity	NPD8349	Phase 1
0.6298	Remote Similarity	NPD7393	Clinical (unspecified phase)

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