NPASS Compound

Structure

NPC475447 OpenBabel07101719142D 100110 0 0 1 0 0 0 0 0999 V2000 -6.8658 -4.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7316 -2.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5822 -5.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2987 -4.9550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6214 1.6541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5747 0.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4031 1.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 -5.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7240 -9.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2987 -1.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8734 -7.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 5.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5747 5.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 5.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5747 4.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 4.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 2.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5747 2.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7164 -1.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 -0.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8582 -1.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5250 0.4955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9425 -0.3062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 -1.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 -3.4685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0076 -7.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1569 -4.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7164 0.9910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.0227 -4.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4480 -1.9820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0076 -4.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.8734 -3.4685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7240 -6.4414 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2987 -5.9459 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6789 1.9603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4329 3.9640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5747 -1.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 -1.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2911 -4.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8658 -7.9279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1569 -3.4685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -18.0227 -3.4685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.5898 -1.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7164 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8582 1.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7164 2.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1493 -2.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0076 -6.4414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.0151 -4.9550 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.8809 -2.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.5898 -0.4955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -18.8809 -1.9820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.7316 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.0227 -1.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.8734 -0.4955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2987 -7.9279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1493 -4.9550 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.0151 -2.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7240 -7.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1569 -6.4414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1569 -7.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -17.1645 -1.9820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.8734 -1.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4405 -7.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5747 -0.4955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9425 1.2972 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8582 -0.4955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.8809 -4.9550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4729 2.9297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7164 3.9640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -19.7391 -3.4685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4480 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -19.7391 -1.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7316 0.9910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.0227 -0.4955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0151 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2987 -8.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7364 2.2666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8582 -1.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4031 -0.9053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4329 -4.9550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8658 -8.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2987 -2.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0151 -7.9279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.3062 -1.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0076 -3.4685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8658 -5.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8734 -4.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4405 -6.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1493 -1.9820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.1645 -2.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7316 -1.9820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8582 2.4775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1493 -5.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0151 -5.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0151 -1.9820 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5822 -7.9279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 67 1 0 0 0 0 8 84 1 0 0 0 0 9 85 1 0 0 0 0 10 86 1 0 0 0 0 11 87 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 37 2 0 0 0 0 16 37 1 0 0 0 0 17 18 2 0 0 0 0 17 37 1 0 0 0 0 18 47 1 0 0 0 0 19 22 1 0 0 0 0 19 38 2 0 0 0 0 20 21 1 0 0 0 0 20 39 1 0 0 0 0 21 66 1 0 0 0 0 22 69 1 0 0 0 0 23 24 1 0 0 0 0 23 68 1 0 0 0 0 24 70 1 0 0 0 0 25 38 1 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 26 48 1 0 0 0 0 27 41 1 0 0 0 0 27 49 1 0 0 0 0 28 42 1 0 0 0 0 28 50 1 0 0 0 0 29 45 1 0 0 0 0 29 46 1 0 0 0 0 30 71 1 0 0 0 0 31 88 1 0 0 0 0 32 1 1 1 0 0 0 32 58 1 0 0 0 0 32 89 1 0 0 0 0 33 2 1 6 0 0 0 33 59 1 0 0 0 0 33 91 1 0 0 0 0 34 3 1 1 0 0 0 34 60 1 0 0 0 0 34 90 1 0 0 0 0 35 4 1 1 0 0 0 35 61 1 0 0 0 0 35 92 1 0 0 0 0 36 5 1 1 0 0 0 36 68 1 0 0 0 0 36 72 1 0 0 0 0 38 66 1 0 0 0 0 39 93 1 1 0 0 0 40 58 1 0 0 0 0 40 84 1 6 0 0 0 41 60 1 0 0 0 0 41 85 1 6 0 0 0 42 59 1 0 0 0 0 42 86 1 6 0 0 0 43 30 1 6 0 0 0 43 51 1 0 0 0 0 43 94 1 0 0 0 0 44 31 1 6 0 0 0 44 52 1 0 0 0 0 44 95 1 0 0 0 0 45 66 1 1 0 0 0 45 69 1 0 0 0 0 46 67 1 1 0 0 0 46 96 1 0 0 0 0 47 73 2 0 0 0 0 47 96 1 0 0 0 0 48 89 1 0 0 0 0 48 93 1 1 0 0 0 49 90 1 0 0 0 0 49 97 1 1 0 0 0 50 91 1 0 0 0 0 50 98 1 6 0 0 0 51 53 1 0 0 0 0 51 74 1 1 0 0 0 52 54 1 0 0 0 0 52 75 1 1 0 0 0 53 55 1 0 0 0 0 53 76 1 6 0 0 0 54 56 1 0 0 0 0 54 77 1 6 0 0 0 55 63 1 0 0 0 0 55 78 1 1 0 0 0 56 64 1 0 0 0 0 56 79 1 1 0 0 0 57 62 1 0 0 0 0 57 65 1 0 0 0 0 57 80 1 6 0 0 0 58 97 1 6 0 0 0 59 99 1 1 0 0 0 60100 1 6 0 0 0 61 62 1 0 0 0 0 61 98 1 1 0 0 0 62 87 1 1 0 0 0 63 88 1 6 0 0 0 63 94 1 0 0 0 0 64 95 1 0 0 0 0 64 99 1 6 0 0 0 65 92 1 0 0 0 0 65100 1 1 0 0 0 66 6 1 1 0 0 0 67 68 1 6 0 0 0 68 81 1 6 0 0 0 69 70 1 6 0 0 0 69 82 1 0 0 0 0 70 67 1 1 0 0 0 70 83 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1428.69
Volume:	1373.042
LogP:	2.462
LogD:	1.846
LogS:	-3.472
# Rotatable Bonds:	23
TPSA:	416.74
# H-Bond Aceptor:	30
# H-Bond Donor:	12
# Rings:	11
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.04
Synthetic Accessibility Score:	7.944
Fsp3:	0.843
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.338
MDCK Permeability:	0.0004084817774128169
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.843
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.26

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	52.348365783691406%
Volume Distribution (VD):	-0.332
Pgp-substrate:	16.057634353637695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.085
CYP3A4-substrate:	0.395

ADMET: Excretion

Clearance (CL):	-0.361
Half-life (T1/2):	0.721

ADMET: Toxicity

hERG Blockers:	0.642
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.334
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.816
Skin Sensitization:	0.919
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.333

Download Data

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

Natural Product: NPC475447

Natural Product ID:	NPC475447
*Common Name:**	[(3S,8S,9R,10R,12R,13R,14R,17R)-8,14,17-Trihydroxy-17-[(1S)-1-Hydroxyethyl]-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-Hydroxy-4-Methoxy-5-[(2S,4R,5R,6R)-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxymethyl]Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-12-Yl] (E)-3-Phenylprop-2-Enoate
IUPAC Name:	[(3S,8S,9R,10R,12R,13R,14R,17R)-8,14,17-trihydroxy-17-[(1S)-1-hydroxyethyl]-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-hydroxy-4-methoxy-5-[(2S,4R,5R,6R)-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	FDIFPSKNROPADH-VRQPUNOPSA-N
Standard InCHI:	InChI=1S/C70H108O30/c1-32-58(40(84-8)26-48(89-32)93-39-20-21-66(6)38(25-39)19-22-69(82)45(66)29-46(96-47(73)18-17-37-15-13-12-14-16-37)67(7)68(81,36(5)72)23-24-70(67,69)83)97-49-27-41(85-9)60(34(3)90-49)100-65-57(80)62(87-11)61(35(4)92-65)98-50-28-42(86-10)59(33(2)91-50)99-64-56(79)54(77)52(75)44(95-64)31-88-63-55(78)53(76)51(74)43(30-71)94-63/h12-19,32-36,39-46,48-65,71-72,74-83H,20-31H2,1-11H3/b18-17+/t32-,33-,34-,35-,36+,39+,40+,41+,42-,43-,44-,45-,46-,48+,49+,50+,51-,52-,53+,54+,55-,56-,57-,58-,59-,60-,61+,62-,63-,64+,65+,66+,67-,68+,69+,70-/m1/s1
SMILES:	CC1C(C(CC(O1)OC2CCC3(C4CC(C5(C(CCC5(C4(CC=C3C2)O)O)(C(C)O)O)C)OC(=O)C=CC6=CC=CC=C6)C)OC)OC7CC(C(C(O7)C)OC8C(C(C(C(O8)C)OC9CC(C(C(O9)C)OC1C(C(C(C(O1)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505832
PubChem CID:	44575236
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO32487	leptadenia pyrotechnica	Species	Apocynaceae	Eukaryota	whole plant	Dogon region, Mali	2002-Apr	PMID[16643040]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	880.0	nM	PMID[526629]

☑ 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 NPC475447 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	345
0.1-0.2	1253
0.2-0.3	2923
0.3-0.4	6120
0.4-0.5	12651
0.5-0.6	13157
0.6-0.7	4673
0.7-0.8	1448
0.8-0.85	74
0.85-0.9	19
0.9-0.95	23
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476092
1.0	High Similarity	NPC70236
1.0	High Similarity	NPC475218
0.9929	High Similarity	NPC474564
0.9272	High Similarity	NPC473641
0.9272	High Similarity	NPC475300
0.9272	High Similarity	NPC475505
0.9272	High Similarity	NPC475464
0.9272	High Similarity	NPC475437
0.9272	High Similarity	NPC473797
0.9205	High Similarity	NPC165234
0.9205	High Similarity	NPC475536
0.9091	High Similarity	NPC475198
0.9091	High Similarity	NPC475531
0.9091	High Similarity	NPC475175
0.9026	High Similarity	NPC473468
0.9026	High Similarity	NPC475567
0.9026	High Similarity	NPC473557
0.8882	High Similarity	NPC476784
0.8828	High Similarity	NPC473755
0.8828	High Similarity	NPC475513
0.8649	High Similarity	NPC264270
0.8649	High Similarity	NPC40085
0.8616	High Similarity	NPC477488
0.8609	High Similarity	NPC478123
0.8581	High Similarity	NPC111466
0.8476	Intermediate Similarity	NPC475613
0.8456	Intermediate Similarity	NPC471139
0.8452	Intermediate Similarity	NPC477474
0.8452	Intermediate Similarity	NPC477472
0.8452	Intermediate Similarity	NPC477470
0.8428	Intermediate Similarity	NPC477491
0.8418	Intermediate Similarity	NPC269668
0.8397	Intermediate Similarity	NPC477467
0.8369	Intermediate Similarity	NPC476972
0.8369	Intermediate Similarity	NPC476971
0.8366	Intermediate Similarity	NPC62792
0.8366	Intermediate Similarity	NPC298072
0.831	Intermediate Similarity	NPC230331
0.8298	Intermediate Similarity	NPC470158
0.8298	Intermediate Similarity	NPC476970
0.8298	Intermediate Similarity	NPC475933
0.828	Intermediate Similarity	NPC319404
0.8258	Intermediate Similarity	NPC69425
0.8247	Intermediate Similarity	NPC329657
0.8228	Intermediate Similarity	NPC477623
0.8207	Intermediate Similarity	NPC476976
0.8205	Intermediate Similarity	NPC471176
0.8187	Intermediate Similarity	NPC478125
0.8182	Intermediate Similarity	NPC476173
0.8138	Intermediate Similarity	NPC476977
0.8133	Intermediate Similarity	NPC325078
0.8125	Intermediate Similarity	NPC478124
0.8101	Intermediate Similarity	NPC318447
0.8101	Intermediate Similarity	NPC322048
0.8099	Intermediate Similarity	NPC471758
0.8089	Intermediate Similarity	NPC469398
0.8085	Intermediate Similarity	NPC473871
0.8085	Intermediate Similarity	NPC473870
0.8065	Intermediate Similarity	NPC475417
0.8065	Intermediate Similarity	NPC475561
0.8056	Intermediate Similarity	NPC58061
0.8049	Intermediate Similarity	NPC477471
0.8049	Intermediate Similarity	NPC477469
0.8049	Intermediate Similarity	NPC477466
0.8049	Intermediate Similarity	NPC477473
0.8042	Intermediate Similarity	NPC473110
0.8042	Intermediate Similarity	NPC45821
0.8042	Intermediate Similarity	NPC473111
0.8038	Intermediate Similarity	NPC323001
0.8038	Intermediate Similarity	NPC326235
0.8028	Intermediate Similarity	NPC470815
0.8026	Intermediate Similarity	NPC284957
0.8025	Intermediate Similarity	NPC472657
0.8025	Intermediate Similarity	NPC471135
0.8025	Intermediate Similarity	NPC77310
0.8025	Intermediate Similarity	NPC472658
0.8014	Intermediate Similarity	NPC70973
0.8014	Intermediate Similarity	NPC473889
0.8	Intermediate Similarity	NPC309991
0.8	Intermediate Similarity	NPC93632
0.8	Intermediate Similarity	NPC326328
0.8	Intermediate Similarity	NPC323356
0.8	Intermediate Similarity	NPC471138
0.7975	Intermediate Similarity	NPC469422
0.7975	Intermediate Similarity	NPC34066
0.7975	Intermediate Similarity	NPC469456
0.7974	Intermediate Similarity	NPC204644
0.7972	Intermediate Similarity	NPC145287
0.7972	Intermediate Similarity	NPC284022
0.7972	Intermediate Similarity	NPC114927
0.7972	Intermediate Similarity	NPC473083
0.7958	Intermediate Similarity	NPC12016
0.7949	Intermediate Similarity	NPC469448
0.7943	Intermediate Similarity	NPC37641
0.7943	Intermediate Similarity	NPC311175
0.7925	Intermediate Similarity	NPC475548
0.7925	Intermediate Similarity	NPC290683
0.7925	Intermediate Similarity	NPC475638
0.7902	Intermediate Similarity	NPC472373
0.7898	Intermediate Similarity	NPC469415
0.7892	Intermediate Similarity	NPC286809
0.7879	Intermediate Similarity	NPC102465
0.7877	Intermediate Similarity	NPC471024
0.7862	Intermediate Similarity	NPC198918
0.7862	Intermediate Similarity	NPC290276
0.7862	Intermediate Similarity	NPC276047
0.7862	Intermediate Similarity	NPC63404
0.7862	Intermediate Similarity	NPC92283
0.7862	Intermediate Similarity	NPC204214
0.7862	Intermediate Similarity	NPC10121
0.7862	Intermediate Similarity	NPC124878
0.7862	Intermediate Similarity	NPC10883
0.7862	Intermediate Similarity	NPC267733
0.7862	Intermediate Similarity	NPC35338
0.7862	Intermediate Similarity	NPC231888
0.7857	Intermediate Similarity	NPC135369
0.7857	Intermediate Similarity	NPC473566
0.7857	Intermediate Similarity	NPC475358
0.7853	Intermediate Similarity	NPC295408
0.7853	Intermediate Similarity	NPC329960
0.7853	Intermediate Similarity	NPC150893
0.7834	Intermediate Similarity	NPC222102
0.7834	Intermediate Similarity	NPC303429
0.7832	Intermediate Similarity	NPC179261
0.7829	Intermediate Similarity	NPC473440
0.7826	Intermediate Similarity	NPC469399
0.7823	Intermediate Similarity	NPC475138
0.7821	Intermediate Similarity	NPC320734
0.7817	Intermediate Similarity	NPC300827
0.7817	Intermediate Similarity	NPC473439
0.7817	Intermediate Similarity	NPC117445
0.7817	Intermediate Similarity	NPC208193
0.7817	Intermediate Similarity	NPC308262
0.7808	Intermediate Similarity	NPC175333
0.7808	Intermediate Similarity	NPC471025
0.7806	Intermediate Similarity	NPC472575
0.7806	Intermediate Similarity	NPC200471
0.7806	Intermediate Similarity	NPC177940
0.7806	Intermediate Similarity	NPC174982
0.7806	Intermediate Similarity	NPC472572
0.7806	Intermediate Similarity	NPC96447
0.7806	Intermediate Similarity	NPC470157
0.7806	Intermediate Similarity	NPC476973
0.7806	Intermediate Similarity	NPC472571
0.7806	Intermediate Similarity	NPC473088
0.7806	Intermediate Similarity	NPC184817
0.7806	Intermediate Similarity	NPC471104
0.7806	Intermediate Similarity	NPC29704
0.7806	Intermediate Similarity	NPC158663
0.7806	Intermediate Similarity	NPC171525
0.7806	Intermediate Similarity	NPC469349
0.7806	Intermediate Similarity	NPC70403
0.7806	Intermediate Similarity	NPC470159
0.7806	Intermediate Similarity	NPC472568
0.7806	Intermediate Similarity	NPC96903
0.7801	Intermediate Similarity	NPC470814
0.7793	Intermediate Similarity	NPC473082
0.7793	Intermediate Similarity	NPC28069
0.7793	Intermediate Similarity	NPC77651
0.7785	Intermediate Similarity	NPC96308
0.7778	Intermediate Similarity	NPC291599
0.7778	Intermediate Similarity	NPC118080
0.7778	Intermediate Similarity	NPC41481
0.7778	Intermediate Similarity	NPC27377
0.7778	Intermediate Similarity	NPC16912
0.7778	Intermediate Similarity	NPC97947
0.7778	Intermediate Similarity	NPC87448
0.7778	Intermediate Similarity	NPC472576
0.7771	Intermediate Similarity	NPC475121
0.7771	Intermediate Similarity	NPC301556
0.7771	Intermediate Similarity	NPC92293
0.7771	Intermediate Similarity	NPC471101
0.7771	Intermediate Similarity	NPC266265
0.7771	Intermediate Similarity	NPC270590
0.7771	Intermediate Similarity	NPC476067
0.7762	Intermediate Similarity	NPC473749
0.7762	Intermediate Similarity	NPC475328
0.7756	Intermediate Similarity	NPC478263
0.7756	Intermediate Similarity	NPC312393
0.7756	Intermediate Similarity	NPC474935
0.7756	Intermediate Similarity	NPC473602
0.775	Intermediate Similarity	NPC5115
0.7746	Intermediate Similarity	NPC474423
0.7746	Intermediate Similarity	NPC193893
0.7746	Intermediate Similarity	NPC264336
0.7746	Intermediate Similarity	NPC74259
0.7742	Intermediate Similarity	NPC57628
0.7742	Intermediate Similarity	NPC470152
0.7742	Intermediate Similarity	NPC25768
0.7742	Intermediate Similarity	NPC95265
0.7742	Intermediate Similarity	NPC163719
0.7742	Intermediate Similarity	NPC475122
0.7742	Intermediate Similarity	NPC472569
0.7742	Intermediate Similarity	NPC11685
0.7742	Intermediate Similarity	NPC70716
0.7742	Intermediate Similarity	NPC188865
0.7742	Intermediate Similarity	NPC125106
0.7742	Intermediate Similarity	NPC95810
0.7742	Intermediate Similarity	NPC475759

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 NPC475447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	791
0.2-0.3	1988
0.3-0.4	3462
0.4-0.5	1928
0.5-0.6	597
0.6-0.7	93
0.7-0.8	18
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
0.7676	Intermediate Similarity	NPD8033	Approved
0.7676	Intermediate Similarity	NPD8379	Approved
0.7676	Intermediate Similarity	NPD8296	Approved
0.7676	Intermediate Similarity	NPD8378	Approved
0.7676	Intermediate Similarity	NPD8380	Approved
0.7676	Intermediate Similarity	NPD8335	Approved
0.7606	Intermediate Similarity	NPD8294	Approved
0.7606	Intermediate Similarity	NPD8377	Approved
0.7574	Intermediate Similarity	NPD7799	Discontinued
0.7552	Intermediate Similarity	NPD7503	Approved
0.7535	Intermediate Similarity	NPD7516	Approved
0.7465	Intermediate Similarity	NPD7327	Approved
0.7465	Intermediate Similarity	NPD7328	Approved
0.7326	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7236	Approved
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7134	Intermediate Similarity	NPD7239	Suspended
0.7123	Intermediate Similarity	NPD7741	Discontinued
0.6987	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5126	Approved
0.6913	Remote Similarity	NPD5125	Phase 3
0.691	Remote Similarity	NPD8368	Discontinued
0.6889	Remote Similarity	NPD8407	Phase 2
0.6887	Remote Similarity	NPD7507	Approved
0.6871	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7319	Approved
0.6851	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8133	Approved
0.6816	Remote Similarity	NPD7685	Pre-registration
0.6782	Remote Similarity	NPD8127	Discontinued
0.678	Remote Similarity	NPD7228	Approved
0.6744	Remote Similarity	NPD7058	Phase 2
0.6744	Remote Similarity	NPD7057	Phase 3
0.6725	Remote Similarity	NPD8455	Phase 2
0.6722	Remote Similarity	NPD7240	Approved
0.6712	Remote Similarity	NPD7094	Approved
0.6712	Remote Similarity	NPD6858	Approved
0.6649	Remote Similarity	NPD8361	Approved
0.6649	Remote Similarity	NPD8360	Approved
0.6649	Remote Similarity	NPD8435	Approved
0.6648	Remote Similarity	NPD8313	Approved
0.6648	Remote Similarity	NPD8312	Approved
0.6643	Remote Similarity	NPD6685	Approved
0.6626	Remote Similarity	NPD5763	Approved
0.6626	Remote Similarity	NPD5762	Approved
0.6606	Remote Similarity	NPD8166	Discontinued
0.6604	Remote Similarity	NPD7961	Discontinued
0.6582	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4198	Discontinued
0.6545	Remote Similarity	NPD6674	Discontinued
0.6541	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8434	Phase 2
0.6538	Remote Similarity	NPD3094	Phase 2
0.6536	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8516	Approved
0.6513	Remote Similarity	NPD8515	Approved
0.6513	Remote Similarity	NPD8517	Approved
0.651	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD37	Approved
0.6474	Remote Similarity	NPD7736	Approved
0.646	Remote Similarity	NPD4140	Approved
0.6457	Remote Similarity	NPD4967	Phase 2
0.6457	Remote Similarity	NPD4966	Approved
0.6457	Remote Similarity	NPD4965	Approved
0.6456	Remote Similarity	NPD5736	Approved
0.6453	Remote Similarity	NPD7028	Phase 2
0.645	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5765	Approved
0.6419	Remote Similarity	NPD6912	Phase 3
0.641	Remote Similarity	NPD7497	Discontinued
0.6405	Remote Similarity	NPD8513	Phase 3
0.6404	Remote Similarity	NPD7199	Phase 2
0.6384	Remote Similarity	NPD6234	Discontinued
0.6378	Remote Similarity	NPD8320	Phase 1
0.6378	Remote Similarity	NPD8319	Approved
0.637	Remote Similarity	NPD6686	Approved
0.6364	Remote Similarity	NPD8150	Discontinued
0.6354	Remote Similarity	NPD8485	Approved
0.6341	Remote Similarity	NPD7097	Phase 1
0.6337	Remote Similarity	NPD1653	Approved
0.6323	Remote Similarity	NPD8328	Phase 3
0.6321	Remote Similarity	NPD7700	Phase 2
0.6321	Remote Similarity	NPD7699	Phase 2
0.6319	Remote Similarity	NPD5735	Approved
0.6319	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6273	Approved
0.631	Remote Similarity	NPD7625	Phase 1
0.6301	Remote Similarity	NPD6412	Phase 2
0.6296	Remote Similarity	NPD6663	Approved
0.6282	Remote Similarity	NPD3092	Approved
0.6272	Remote Similarity	NPD6190	Approved
0.625	Remote Similarity	NPD7074	Phase 3
0.6243	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7458	Discontinued
0.62	Remote Similarity	NPD969	Suspended
0.6196	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD2629	Approved
0.6169	Remote Similarity	NPD7610	Discontinued
0.6166	Remote Similarity	NPD6534	Approved
0.6166	Remote Similarity	NPD6535	Approved
0.6162	Remote Similarity	NPD7435	Discontinued
0.6162	Remote Similarity	NPD7680	Approved
0.6162	Remote Similarity	NPD7472	Approved
0.6159	Remote Similarity	NPD3620	Phase 2
0.6159	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD5760	Phase 2
0.6158	Remote Similarity	NPD5761	Phase 2
0.6154	Remote Similarity	NPD6370	Approved
0.6154	Remote Similarity	NPD7638	Approved
0.6154	Remote Similarity	NPD3095	Discontinued
0.615	Remote Similarity	NPD7808	Phase 3
0.6144	Remote Similarity	NPD7115	Discovery
0.6141	Remote Similarity	NPD3751	Discontinued
0.6129	Remote Similarity	NPD3091	Approved
0.6127	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6010	Discontinued
0.6118	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD7055	Discontinued
0.6111	Remote Similarity	NPD7639	Approved
0.6108	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD5844	Phase 1
0.6108	Remote Similarity	NPD7783	Phase 2
0.6108	Remote Similarity	NPD7054	Approved
0.6107	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD8293	Discontinued
0.6096	Remote Similarity	NPD6647	Phase 2
0.6096	Remote Similarity	NPD6559	Discontinued
0.6096	Remote Similarity	NPD6764	Approved
0.6096	Remote Similarity	NPD6765	Approved
0.6096	Remote Similarity	NPD7251	Discontinued
0.6093	Remote Similarity	NPD8297	Approved
0.6093	Remote Similarity	NPD6882	Approved
0.6089	Remote Similarity	NPD8151	Discontinued
0.6084	Remote Similarity	NPD6653	Approved
0.6084	Remote Similarity	NPD6353	Approved
0.608	Remote Similarity	NPD7697	Approved
0.608	Remote Similarity	NPD7696	Phase 3
0.608	Remote Similarity	NPD7698	Approved
0.6076	Remote Similarity	NPD7492	Approved
0.6069	Remote Similarity	NPD5344	Discontinued
0.6069	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD7874	Approved
0.6056	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD7084	Phase 3
0.6043	Remote Similarity	NPD6797	Phase 2
0.604	Remote Similarity	NPD7701	Phase 2
0.6039	Remote Similarity	NPD6009	Approved
0.6039	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6616	Approved
0.6036	Remote Similarity	NPD6002	Phase 3
0.6036	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6004	Phase 3
0.6036	Remote Similarity	NPD6005	Phase 3
0.6036	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.603	Remote Similarity	NPD6823	Phase 2
0.6026	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6319	Approved
0.6026	Remote Similarity	NPD7009	Phase 2
0.6026	Remote Similarity	NPD6054	Approved
0.6024	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5124	Phase 1
0.6023	Remote Similarity	NPD4628	Phase 3
0.6023	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD3787	Discontinued
0.601	Remote Similarity	NPD6776	Approved
0.601	Remote Similarity	NPD6781	Approved
0.601	Remote Similarity	NPD6779	Approved
0.601	Remote Similarity	NPD6780	Approved
0.601	Remote Similarity	NPD6778	Approved
0.601	Remote Similarity	NPD6777	Approved
0.601	Remote Similarity	NPD6782	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD8462	Phase 1
0.6	Remote Similarity	NPD5327	Phase 3
0.6	Remote Similarity	NPD7078	Approved
0.5988	Remote Similarity	NPD4624	Approved
0.5979	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD8450	Suspended
0.5976	Remote Similarity	NPD7008	Discontinued
0.597	Remote Similarity	NPD7870	Phase 2
0.597	Remote Similarity	NPD7871	Phase 2
0.5969	Remote Similarity	NPD6785	Approved
0.5969	Remote Similarity	NPD6784	Approved
0.5957	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7801	Approved
0.5948	Remote Similarity	NPD4632	Approved
0.5939	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD8449	Approved
0.5915	Remote Similarity	NPD8171	Discontinued

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