NPASS Compound

Structure

NPC133678 OpenBabel07101719162D 109121 0 0 1 0 0 0 0 0999 V2000 -4.4347 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5249 -9.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -7.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9781 -1.5241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6589 -2.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.8551 -7.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9781 -3.2562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6230 -4.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0827 -0.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9781 -1.5241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4781 -2.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 3.6720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.7211 -5.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6589 -11.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5249 -5.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0608 -3.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.2570 -5.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1730 0.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -3.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6589 -10.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7929 -6.7266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4781 -0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.7929 -2.7266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 19.9890 -6.7266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4781 -2.3902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3007 -4.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -4.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7929 -11.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -4.2266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 16.5249 -6.7266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4781 1.0739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -1.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.6589 -5.2266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 18.2570 -6.7266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5686 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7929 -9.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -11.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -10.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4781 2.8060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 1.0739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4781 1.0739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.7929 -3.7266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.6589 -7.2266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9781 1.9400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4781 2.8060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4781 -0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 19.9890 -5.7266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.4781 -2.3902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9706 -0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -3.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7929 -8.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 1.0739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4781 1.0739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9781 1.9400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4781 -0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 19.1230 -5.2266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9781 -1.5241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.0608 -2.7266 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.0608 -11.7266 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 19.6230 -4.3605 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -5.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7929 -12.7266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -5.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0608 -9.7266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9781 3.6720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9781 1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9781 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -8.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 19.1230 -3.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 20.6230 -4.3605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4781 -0.6581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9781 -1.5241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 3.6720 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 20.8551 -5.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5797 -0.3254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1785 0.4836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -1.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7929 -5.7266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 19.1230 -7.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9781 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9781 -1.5241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 17.3910 -7.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 1.0739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6589 -4.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6589 -8.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9781 1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9781 0.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9268 -2.2266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 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 12.1473 -3.1333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9563 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 10 85 1 0 0 0 0 11 86 1 0 0 0 0 12 87 1 0 0 0 0 13 88 1 0 0 0 0 14 24 2 0 0 0 0 14 31 1 0 0 0 0 15 25 2 0 0 0 0 15 33 1 0 0 0 0 16 31 2 0 0 0 0 16 32 1 0 0 0 0 17 35 1 0 0 0 0 17 39 1 0 0 0 0 18 34 1 0 0 0 0 19 40 1 0 0 0 0 19 66 1 0 0 0 0 20 85 1 0 0 0 0 21 89 1 0 0 0 0 22 37 1 0 0 0 0 22 92 1 0 0 0 0 23 90 1 0 0 0 0 23 91 1 0 0 0 0 24 41 1 0 0 0 0 25 42 1 0 0 0 0 26 3 1 1 0 0 0 26 49 1 0 0 0 0 26 93 1 0 0 0 0 27 4 1 1 0 0 0 27 50 1 0 0 0 0 27 95 1 0 0 0 0 28 5 1 6 0 0 0 28 48 1 0 0 0 0 28105 1 0 0 0 0 29 6 1 6 0 0 0 29 57 1 0 0 0 0 29 94 1 0 0 0 0 30 7 1 1 0 0 0 30 58 1 0 0 0 0 30 96 1 0 0 0 0 31 72 1 0 0 0 0 32 41 2 0 0 0 0 32 73 1 0 0 0 0 33 43 2 0 0 0 0 33 74 1 0 0 0 0 34 48 1 0 0 0 0 34 75 1 6 0 0 0 35 49 1 0 0 0 0 35 97 1 1 0 0 0 36 20 1 1 0 0 0 36 51 1 0 0 0 0 36 99 1 0 0 0 0 37 53 1 0 0 0 0 37 98 1 1 0 0 0 38 21 1 6 0 0 0 38 52 1 0 0 0 0 38106 1 0 0 0 0 39 93 1 0 0 0 0 39100 1 1 0 0 0 40 94 1 0 0 0 0 40 97 1 1 0 0 0 41 60 1 0 0 0 0 42 44 2 0 0 0 0 42 61 1 0 0 0 0 43 44 1 0 0 0 0 43 70 1 0 0 0 0 44 76 1 0 0 0 0 45 51 1 0 0 0 0 45 55 1 0 0 0 0 45 77 1 1 0 0 0 46 52 1 0 0 0 0 46 62 1 0 0 0 0 46 78 1 1 0 0 0 47 54 1 0 0 0 0 47 63 1 0 0 0 0 47 79 1 6 0 0 0 48100 1 1 0 0 0 49101 1 6 0 0 0 50 54 1 0 0 0 0 50 86 1 1 0 0 0 51102 1 6 0 0 0 52107 1 1 0 0 0 53 59 1 0 0 0 0 53 90 1 6 0 0 0 54103 1 1 0 0 0 55 64 1 0 0 0 0 55 87 1 1 0 0 0 56 65 1 0 0 0 0 56 67 1 1 0 0 0 56 80 1 0 0 0 0 57 66 1 1 0 0 0 57 88 1 0 0 0 0 58 67 1 6 0 0 0 58108 1 0 0 0 0 59 69 1 1 0 0 0 59 91 1 0 0 0 0 60 81 2 0 0 0 0 60 98 1 0 0 0 0 61 82 2 0 0 0 0 61101 1 0 0 0 0 62 89 1 0 0 0 0 62104 1 6 0 0 0 63 95 1 0 0 0 0 63102 1 1 0 0 0 64 99 1 0 0 0 0 64104 1 1 0 0 0 65 96 1 0 0 0 0 65103 1 1 0 0 0 66 8 1 1 0 0 0 66 71 1 0 0 0 0 67 9 1 6 0 0 0 67109 1 0 0 0 0 68 18 1 1 0 0 0 68105 1 0 0 0 0 68108 1 0 0 0 0 68109 1 0 0 0 0 69 92 1 1 0 0 0 69106 1 0 0 0 0 69107 1 0 0 0 0 71 83 2 0 0 0 0 71 84 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1581.53
Volume:	1427.254
LogP:	4.022
LogD:	2.473
LogS:	-3.267
# Rotatable Bonds:	22
TPSA:	490.1
# H-Bond Aceptor:	39
# H-Bond Donor:	9
# Rings:	13
# Heavy Atoms:	40

MedChem Properties

QED Drug-Likeness Score:	0.049
Synthetic Accessibility Score:	8.252
Fsp3:	0.797
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.235
MDCK Permeability:	0.0006948160589672625
Pgp-inhibitor:	0.001
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.88
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.281

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.319
Plasma Protein Binding (PPB):	77.1731185913086%
Volume Distribution (VD):	-0.317
Pgp-substrate:	5.846022605895996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.771

ADMET: Excretion

Clearance (CL):	-0.121
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.42
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.889
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.058

Download Data

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

Natural Product: NPC133678

Natural Product ID:	NPC133678
*Common Name:**	[(2R,3R,4R,6S)-6-[(2R,2'r,3's,3Ar,4R,4'r,6S,7S,7Ar)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3Ar,3'as,4R,6's,7R,7'r,7As,7'as)-7-(2,4-Dihydroxy-6-Methylbenzoyl)Oxy-7'-Hydroxyspiro[3A,6,7,7A-Tetrahydro-[1,3]Dioxolo[4,5-C]Pyran-4,2'-4,6,7,7A-Tetrahydro-3Ah-[1,3]Dioxolo[4,5-C]Pyran]-6'-Yl]Oxy-4-Hydroxy-5-Methoxy-2-(Methoxymethyl)Oxan-3-Yl]Oxy-3-Hydroxy-5-Methoxy-6-Methyloxan-4-Yl]Oxy-4',7-Dihydroxy-2',4,7A-Trimethylspiro[3A,4,6,7-Tetrahydro-[1,3]Dioxolo[4,5-C]Pyran-2,6'-Oxane]-3'-Yl]Oxy-4-[(2S,4S,5R,6S)-5-Methoxy-4,6-Dimethyl-4-Nitrooxan-2-Yl]Oxy-2-Methyloxan-3-Yl] 3-Chloro-2,4-Dihydroxy-6-Methylbenzoate
IUPAC Name:	[(2R,3R,4R,6S)-6-[(2R,2'R,3'S,3aR,4R,4'R,6S,7S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(3aR,3'aS,4R,6'S,7R,7'R,7aS,7'aS)-7-(2,4-dihydroxy-6-methylbenzoyl)oxy-7'-hydroxyspiro[3a,6,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4,2'-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6'-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4',7-dihydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-[(2S,4S,5R,6S)-5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl]oxy-2-methyloxan-3-yl] 3-chloro-2,4-dihydroxy-6-methylbenzoate
Synonyms:	SCH-58769
Standard InCHIKey:	QOLCQSMNOVLBMK-DJELFNRCSA-N
Standard InCHI:	InChI=1S/C69H96ClNO38/c1-24-14-31(72)16-32(73)41(24)60(81)98-37-22-92-69(59-53(37)90-23-91-59)106-38-21-89-62(46(78)52(38)107-69)104-64-55(87-12)45(77)51(36(99-64)20-85-10)102-63-47(79)54(50(86-11)27(4)95-63)103-65-56(80)67(9)58(30(7)96-65)108-68(109-67)18-34(75)48(28(5)105-68)100-39-17-35(97-40-19-66(8,71(83)84)57(88-13)29(6)94-40)49(26(3)93-39)101-61(82)42-25(2)15-33(74)43(70)44(42)76/h14-16,26-30,34-40,45-59,62-65,72-80H,17-23H2,1-13H3/t26-,27-,28-,29+,30-,34-,35-,36-,37-,38+,39+,40+,45+,46-,47-,48-,49-,50+,51-,52-,53+,54-,55+,56-,57+,58-,59-,62+,63+,64+,65+,66+,67-,68-,69-/m1/s1
SMILES:	Cc1cc(cc(c1C(=O)O[C@@H]1CO[C@]2([C@H]3[C@H]1OCO3)O[C@H]1CO[C@H]([C@@H]([C@@H]1O2)O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](COC)O1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](C)O1)OC)O[C@H]1[C@H]([C@]2(C)[C@@H]([C@@H](C)O1)O[C@]1(C[C@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@H]([C@@H]([C@@H](C)O1)OC(=O)c1c(C)cc(c(c1O)Cl)O)O[C@H]1C[C@@](C)([C@H]([C@H](C)O1)OC)N(=O)=O)O)O2)O)O)O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506440
PubChem CID:	44575973
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO21710.1	Micromonospora carbonacea	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12444681]

☑ 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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	18.0	mm	PMID[526799]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	16.0	mm	PMID[526799]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	22.0	mm	PMID[526799]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	17.0	mm	PMID[526799]

☑ 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 NPC133678 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	449
0.1-0.2	1987
0.2-0.3	5070
0.3-0.4	11328
0.4-0.5	10501
0.5-0.6	10749
0.6-0.7	2564
0.7-0.8	45
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC85735
0.9366	High Similarity	NPC83933
0.9272	High Similarity	NPC167027
0.7931	Intermediate Similarity	NPC136411
0.7876	Intermediate Similarity	NPC69868
0.772	Intermediate Similarity	NPC257309
0.7413	Intermediate Similarity	NPC249977
0.7313	Intermediate Similarity	NPC7752
0.7313	Intermediate Similarity	NPC99216
0.7304	Intermediate Similarity	NPC288152
0.7304	Intermediate Similarity	NPC137871
0.7304	Intermediate Similarity	NPC257011
0.7304	Intermediate Similarity	NPC9002
0.7277	Intermediate Similarity	NPC262222
0.7277	Intermediate Similarity	NPC68592
0.7277	Intermediate Similarity	NPC298666
0.7255	Intermediate Similarity	NPC199079
0.7255	Intermediate Similarity	NPC210808
0.7246	Intermediate Similarity	NPC120952
0.7246	Intermediate Similarity	NPC241196
0.7243	Intermediate Similarity	NPC470194
0.7243	Intermediate Similarity	NPC282474
0.7243	Intermediate Similarity	NPC470198
0.7243	Intermediate Similarity	NPC470196
0.7243	Intermediate Similarity	NPC314687
0.7243	Intermediate Similarity	NPC470200
0.7243	Intermediate Similarity	NPC470193
0.7243	Intermediate Similarity	NPC316274
0.7243	Intermediate Similarity	NPC470195
0.7243	Intermediate Similarity	NPC470197
0.7235	Intermediate Similarity	NPC314941
0.7233	Intermediate Similarity	NPC63105
0.7215	Intermediate Similarity	NPC315889
0.7198	Intermediate Similarity	NPC176246
0.7178	Intermediate Similarity	NPC311850
0.7177	Intermediate Similarity	NPC470453
0.7177	Intermediate Similarity	NPC470448
0.7177	Intermediate Similarity	NPC470452
0.7177	Intermediate Similarity	NPC469371
0.7177	Intermediate Similarity	NPC164047
0.7164	Intermediate Similarity	NPC472405
0.7156	Intermediate Similarity	NPC470103
0.7156	Intermediate Similarity	NPC475352
0.7156	Intermediate Similarity	NPC229817
0.7156	Intermediate Similarity	NPC221140
0.7156	Intermediate Similarity	NPC473686
0.7156	Intermediate Similarity	NPC475220
0.715	Intermediate Similarity	NPC470199
0.715	Intermediate Similarity	NPC198199
0.715	Intermediate Similarity	NPC314459
0.7143	Intermediate Similarity	NPC35924
0.7143	Intermediate Similarity	NPC199172
0.7143	Intermediate Similarity	NPC316461
0.7136	Intermediate Similarity	NPC13989
0.7136	Intermediate Similarity	NPC477617
0.7136	Intermediate Similarity	NPC470099
0.7129	Intermediate Similarity	NPC245059
0.7129	Intermediate Similarity	NPC298171
0.7129	Intermediate Similarity	NPC473696
0.7129	Intermediate Similarity	NPC475382
0.7129	Intermediate Similarity	NPC84494
0.7129	Intermediate Similarity	NPC195114
0.7123	Intermediate Similarity	NPC294863
0.7123	Intermediate Similarity	NPC282636
0.7114	Intermediate Similarity	NPC328093
0.7108	Intermediate Similarity	NPC28669
0.7108	Intermediate Similarity	NPC70441
0.7101	Intermediate Similarity	NPC213052
0.7101	Intermediate Similarity	NPC65118
0.7095	Intermediate Similarity	NPC477860
0.7095	Intermediate Similarity	NPC475161
0.7094	Intermediate Similarity	NPC470081
0.7094	Intermediate Similarity	NPC470563
0.7094	Intermediate Similarity	NPC473644
0.7087	Intermediate Similarity	NPC138990
0.7087	Intermediate Similarity	NPC209550
0.7087	Intermediate Similarity	NPC175429
0.7087	Intermediate Similarity	NPC470272
0.7087	Intermediate Similarity	NPC298778
0.7087	Intermediate Similarity	NPC277532
0.7083	Intermediate Similarity	NPC42286
0.7081	Intermediate Similarity	NPC80360
0.7081	Intermediate Similarity	NPC471802
0.7079	Intermediate Similarity	NPC101636
0.7079	Intermediate Similarity	NPC298401
0.7075	Intermediate Similarity	NPC33083
0.7075	Intermediate Similarity	NPC241847
0.7073	Intermediate Similarity	NPC311389
0.7073	Intermediate Similarity	NPC470271
0.7065	Intermediate Similarity	NPC279732
0.7062	Intermediate Similarity	NPC473631
0.7062	Intermediate Similarity	NPC293227
0.7062	Intermediate Similarity	NPC473717
0.7062	Intermediate Similarity	NPC475662
0.7059	Intermediate Similarity	NPC478026
0.7059	Intermediate Similarity	NPC173352
0.7059	Intermediate Similarity	NPC287889
0.7059	Intermediate Similarity	NPC58653
0.7059	Intermediate Similarity	NPC135358
0.7056	Intermediate Similarity	NPC470100
0.7053	Intermediate Similarity	NPC261254
0.7053	Intermediate Similarity	NPC183441
0.7053	Intermediate Similarity	NPC180918
0.7051	Intermediate Similarity	NPC313541
0.7051	Intermediate Similarity	NPC313274
0.7048	Intermediate Similarity	NPC187441
0.7048	Intermediate Similarity	NPC192539
0.7048	Intermediate Similarity	NPC72783
0.7048	Intermediate Similarity	NPC283980
0.7044	Intermediate Similarity	NPC291957
0.7044	Intermediate Similarity	NPC14030
0.7044	Intermediate Similarity	NPC470561
0.7044	Intermediate Similarity	NPC474096
0.7041	Intermediate Similarity	NPC221352
0.7039	Intermediate Similarity	NPC105283
0.7039	Intermediate Similarity	NPC473202
0.7039	Intermediate Similarity	NPC293629
0.7039	Intermediate Similarity	NPC43587
0.7033	Intermediate Similarity	NPC475233
0.7033	Intermediate Similarity	NPC89127
0.7033	Intermediate Similarity	NPC202908
0.7033	Intermediate Similarity	NPC471669
0.7033	Intermediate Similarity	NPC312630
0.7033	Intermediate Similarity	NPC324220
0.7033	Intermediate Similarity	NPC122467
0.7033	Intermediate Similarity	NPC48984
0.7033	Intermediate Similarity	NPC14187
0.7033	Intermediate Similarity	NPC46958
0.7033	Intermediate Similarity	NPC255799
0.7033	Intermediate Similarity	NPC473862
0.7033	Intermediate Similarity	NPC292019
0.703	Intermediate Similarity	NPC97285
0.703	Intermediate Similarity	NPC246469
0.703	Intermediate Similarity	NPC142860
0.703	Intermediate Similarity	NPC271270
0.7028	Intermediate Similarity	NPC275977
0.7028	Intermediate Similarity	NPC249560
0.7028	Intermediate Similarity	NPC223860
0.7028	Intermediate Similarity	NPC106700
0.7024	Intermediate Similarity	NPC474061
0.7024	Intermediate Similarity	NPC189564
0.7024	Intermediate Similarity	NPC256188
0.7024	Intermediate Similarity	NPC469459
0.7024	Intermediate Similarity	NPC221342
0.7024	Intermediate Similarity	NPC64425
0.7024	Intermediate Similarity	NPC12013
0.7024	Intermediate Similarity	NPC477613
0.7024	Intermediate Similarity	NPC175793
0.7024	Intermediate Similarity	NPC32641
0.7024	Intermediate Similarity	NPC186816
0.7024	Intermediate Similarity	NPC142142
0.7024	Intermediate Similarity	NPC476470
0.7024	Intermediate Similarity	NPC203145
0.7024	Intermediate Similarity	NPC11432
0.7023	Intermediate Similarity	NPC48474
0.7023	Intermediate Similarity	NPC264302
0.7019	Intermediate Similarity	NPC25724
0.7015	Intermediate Similarity	NPC478226
0.701	Intermediate Similarity	NPC470898
0.7005	Intermediate Similarity	NPC105095
0.7005	Intermediate Similarity	NPC177731
0.7005	Intermediate Similarity	NPC477571
0.7005	Intermediate Similarity	NPC48822
0.7005	Intermediate Similarity	NPC79056
0.7005	Intermediate Similarity	NPC477573
0.7005	Intermediate Similarity	NPC44328
0.7005	Intermediate Similarity	NPC477572
0.7	Intermediate Similarity	NPC89052
0.7	Intermediate Similarity	NPC469418
0.7	Intermediate Similarity	NPC251417
0.7	Intermediate Similarity	NPC260300
0.7	Intermediate Similarity	NPC173837
0.6995	Remote Similarity	NPC473554
0.6995	Remote Similarity	NPC87583
0.6995	Remote Similarity	NPC470719
0.6995	Remote Similarity	NPC295625
0.699	Remote Similarity	NPC261411
0.699	Remote Similarity	NPC190204
0.699	Remote Similarity	NPC298847
0.699	Remote Similarity	NPC43918
0.6986	Remote Similarity	NPC131405
0.6986	Remote Similarity	NPC68381
0.6986	Remote Similarity	NPC199533
0.6986	Remote Similarity	NPC470454
0.6986	Remote Similarity	NPC474345
0.6986	Remote Similarity	NPC102028
0.6981	Remote Similarity	NPC241781
0.6981	Remote Similarity	NPC156785
0.6981	Remote Similarity	NPC162394
0.698	Remote Similarity	NPC138811
0.698	Remote Similarity	NPC22062
0.698	Remote Similarity	NPC53139
0.698	Remote Similarity	NPC473634
0.6978	Remote Similarity	NPC315253
0.6977	Remote Similarity	NPC472724
0.6977	Remote Similarity	NPC472721
0.6977	Remote Similarity	NPC469652
0.6977	Remote Similarity	NPC187632
0.6977	Remote Similarity	NPC472720
0.6977	Remote Similarity	NPC93065

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 NPC133678 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	898
0.2-0.3	2190
0.3-0.4	3327
0.4-0.5	1918
0.5-0.6	443
0.6-0.7	71
0.7-0.8	2
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
0.7235	Intermediate Similarity	NPD8319	Approved
0.7235	Intermediate Similarity	NPD8320	Phase 1
0.7195	Intermediate Similarity	NPD7783	Phase 2
0.7195	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7700	Phase 2
0.7037	Intermediate Similarity	NPD7699	Phase 2
0.7027	Intermediate Similarity	NPD8151	Discontinued
0.7005	Intermediate Similarity	NPD7074	Phase 3
0.7005	Intermediate Similarity	NPD7472	Approved
0.6986	Remote Similarity	NPD7808	Phase 3
0.6957	Remote Similarity	NPD7054	Approved
0.6955	Remote Similarity	NPD7696	Phase 3
0.6955	Remote Similarity	NPD7698	Approved
0.6955	Remote Similarity	NPD7697	Approved
0.6938	Remote Similarity	NPD7251	Discontinued
0.6906	Remote Similarity	NPD7701	Phase 2
0.6898	Remote Similarity	NPD6535	Approved
0.6898	Remote Similarity	NPD6534	Approved
0.689	Remote Similarity	NPD6797	Phase 2
0.6875	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7930	Approved
0.6849	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7871	Phase 2
0.6847	Remote Similarity	NPD7870	Phase 2
0.6844	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD7874	Approved
0.6827	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD6781	Approved
0.6818	Remote Similarity	NPD6779	Approved
0.6818	Remote Similarity	NPD6778	Approved
0.6818	Remote Similarity	NPD6780	Approved
0.6818	Remote Similarity	NPD6782	Approved
0.6818	Remote Similarity	NPD6777	Approved
0.6818	Remote Similarity	NPD6776	Approved
0.6806	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7435	Discontinued
0.6682	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7801	Approved
0.6636	Remote Similarity	NPD8313	Approved
0.6636	Remote Similarity	NPD8312	Approved
0.6621	Remote Similarity	NPD6213	Phase 3
0.6621	Remote Similarity	NPD6212	Phase 3
0.6621	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6559	Discontinued
0.662	Remote Similarity	NPD8150	Discontinued
0.662	Remote Similarity	NPD7240	Approved
0.6553	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7819	Suspended
0.652	Remote Similarity	NPD7999	Approved
0.6493	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6166	Phase 2
0.6493	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6234	Discontinued
0.6473	Remote Similarity	NPD4965	Approved
0.6473	Remote Similarity	NPD4967	Phase 2
0.6473	Remote Similarity	NPD4966	Approved
0.6471	Remote Similarity	NPD4380	Phase 2
0.646	Remote Similarity	NPD5006	Approved
0.646	Remote Similarity	NPD5005	Approved
0.6447	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7075	Discontinued
0.6441	Remote Similarity	NPD4360	Phase 2
0.6441	Remote Similarity	NPD4363	Phase 3
0.6429	Remote Similarity	NPD6959	Discontinued
0.6419	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5710	Approved
0.6398	Remote Similarity	NPD5711	Approved
0.6394	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7585	Approved
0.6389	Remote Similarity	NPD7685	Pre-registration
0.636	Remote Similarity	NPD7680	Approved
0.6355	Remote Similarity	NPD7799	Discontinued
0.6351	Remote Similarity	NPD7199	Phase 2
0.6349	Remote Similarity	NPD8059	Phase 3
0.6349	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7583	Approved
0.6348	Remote Similarity	NPD7584	Approved
0.6347	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4361	Phase 2
0.6339	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD2403	Approved
0.6332	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD37	Approved
0.6329	Remote Similarity	NPD1934	Approved
0.6321	Remote Similarity	NPD6232	Discontinued
0.6308	Remote Similarity	NPD7473	Discontinued
0.6305	Remote Similarity	NPD2532	Approved
0.6305	Remote Similarity	NPD2534	Approved
0.6305	Remote Similarity	NPD2533	Approved
0.6298	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8455	Phase 2
0.6298	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4420	Approved
0.6281	Remote Similarity	NPD7266	Discontinued
0.6268	Remote Similarity	NPD3817	Phase 2
0.6268	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5844	Phase 1
0.6227	Remote Similarity	NPD8407	Phase 2
0.622	Remote Similarity	NPD1465	Phase 2
0.6215	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3749	Approved
0.6204	Remote Similarity	NPD3751	Discontinued
0.62	Remote Similarity	NPD1852	Discontinued
0.619	Remote Similarity	NPD5402	Approved
0.6186	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD8285	Discontinued
0.6175	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6801	Discontinued
0.6168	Remote Similarity	NPD3787	Discontinued
0.6161	Remote Similarity	NPD3882	Suspended
0.6154	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.615	Remote Similarity	NPD5494	Approved
0.6146	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD2801	Approved
0.6131	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7411	Suspended
0.6098	Remote Similarity	NPD6799	Approved
0.6098	Remote Similarity	NPD7390	Discontinued
0.6091	Remote Similarity	NPD8368	Discontinued
0.6087	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5403	Approved
0.6085	Remote Similarity	NPD7768	Phase 2
0.6063	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD3819	Phase 2
0.6044	Remote Similarity	NPD8360	Approved
0.6044	Remote Similarity	NPD8361	Approved
0.6042	Remote Similarity	NPD8404	Phase 2
0.604	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.604	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.603	Remote Similarity	NPD230	Phase 1
0.6027	Remote Similarity	NPD8434	Phase 2
0.6019	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1511	Approved
0.6017	Remote Similarity	NPD4914	Approved
0.6017	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.601	Remote Similarity	NPD1549	Phase 2
0.6009	Remote Similarity	NPD6312	Discontinued
0.6008	Remote Similarity	NPD8067	Phase 3
0.6	Remote Similarity	NPD6599	Discontinued
0.6	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6190	Approved
0.5991	Remote Similarity	NPD5242	Approved
0.5991	Remote Similarity	NPD7296	Approved
0.599	Remote Similarity	NPD5401	Approved
0.599	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD8435	Approved
0.5973	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD5058	Phase 3
0.5969	Remote Similarity	NPD8152	Approved
0.5969	Remote Similarity	NPD8153	Approved
0.5962	Remote Similarity	NPD1512	Approved
0.5962	Remote Similarity	NPD5353	Approved
0.5959	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD3750	Approved
0.5951	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD1510	Phase 2
0.5913	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD1653	Approved
0.5899	Remote Similarity	NPD8127	Discontinued
0.5897	Remote Similarity	NPD4387	Approved
0.5897	Remote Similarity	NPD4386	Approved
0.5896	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD3764	Approved
0.5878	Remote Similarity	NPD8366	Approved
0.5877	Remote Similarity	NPD3455	Phase 2
0.5877	Remote Similarity	NPD7458	Discontinued
0.5875	Remote Similarity	NPD7827	Phase 1
0.5874	Remote Similarity	NPD4628	Phase 3
0.5872	Remote Similarity	NPD7497	Discontinued
0.5862	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8491	Approved
0.5845	Remote Similarity	NPD3887	Approved
0.5845	Remote Similarity	NPD2354	Approved
0.5837	Remote Similarity	NPD5544	Approved
0.5833	Remote Similarity	NPD6625	Approved
0.5833	Remote Similarity	NPD2796	Approved
0.5833	Remote Similarity	NPD2935	Discontinued
0.5823	Remote Similarity	NPD8469	Approved
0.5821	Remote Similarity	NPD1240	Approved
0.5819	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.5819	Remote Similarity	NPD8485	Approved
0.5815	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.5815	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD4972	Discontinued
0.5771	Remote Similarity	NPD6784	Approved
0.5771	Remote Similarity	NPD6723	Discontinued
0.5771	Remote Similarity	NPD6785	Approved
0.5769	Remote Similarity	NPD7565	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