NPASS Compound

Structure

NPC475531 OpenBabel07101719522D 97107 0 0 1 0 0 0 0 0999 V2000 7.7221 3.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4381 4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4381 6.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5861 7.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7425 -1.4428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 2.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4403 1.2969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0121 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7281 5.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7281 10.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9812 -4.2995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0390 -3.9933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7175 -3.6365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 3.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8330 -3.0242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5115 -2.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3633 -1.3922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4210 -1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5740 0.4954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5740 3.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 2.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7160 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1913 -1.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2060 -0.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4320 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4381 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0121 4.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3021 6.4398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8641 2.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4381 3.4676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2961 5.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7281 7.9259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5365 -0.4737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5693 -2.3613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 3.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5740 1.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4320 2.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0060 1.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2961 1.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0121 5.9444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3021 7.4306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8580 1.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8580 1.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2150 -0.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1480 2.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5801 1.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1541 4.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.1601 7.9259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 17.1601 8.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3021 9.4120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0121 8.9167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8641 1.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2961 2.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1541 6.4398 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7281 8.9167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8701 9.4120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7160 2.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4441 8.9167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0121 7.9259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7160 1.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8580 0.4954 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5943 -0.1676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8580 0.4954 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 17.1601 5.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9513 0.5460 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0181 7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0181 9.4120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3021 10.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 9.4120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5740 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3305 0.4954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8580 -1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9853 -0.1036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0060 0.4954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8701 6.4398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8701 10.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0060 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5801 2.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2961 4.9537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8701 7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2728 0.1892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2900 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4441 7.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 1.9815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7221 1.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 3.4676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1541 7.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5861 9.4120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 68 1 0 0 0 0 8 82 1 0 0 0 0 9 83 1 0 0 0 0 10 84 1 0 0 0 0 11 85 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 41 2 0 0 0 0 19 41 1 0 0 0 0 20 42 2 0 0 0 0 21 42 1 0 0 0 0 22 23 2 0 0 0 0 22 41 1 0 0 0 0 23 51 1 0 0 0 0 24 27 1 0 0 0 0 24 43 2 0 0 0 0 25 26 1 0 0 0 0 25 44 1 0 0 0 0 26 67 1 0 0 0 0 27 70 1 0 0 0 0 28 29 1 0 0 0 0 28 69 1 0 0 0 0 29 71 1 0 0 0 0 30 43 1 0 0 0 0 30 44 1 0 0 0 0 31 45 1 0 0 0 0 31 52 1 0 0 0 0 32 46 1 0 0 0 0 32 53 1 0 0 0 0 33 47 1 0 0 0 0 33 54 1 0 0 0 0 34 49 1 0 0 0 0 34 50 1 0 0 0 0 35 72 1 0 0 0 0 36 1 1 6 0 0 0 36 59 1 0 0 0 0 36 86 1 0 0 0 0 37 2 1 6 0 0 0 37 60 1 0 0 0 0 37 87 1 0 0 0 0 38 3 1 6 0 0 0 38 61 1 0 0 0 0 38 88 1 0 0 0 0 39 4 1 1 0 0 0 39 62 1 0 0 0 0 39 89 1 0 0 0 0 40 5 1 6 0 0 0 40 69 1 0 0 0 0 40 90 1 0 0 0 0 42 64 1 0 0 0 0 43 67 1 0 0 0 0 44 91 1 6 0 0 0 45 59 1 0 0 0 0 45 82 1 1 0 0 0 46 60 1 0 0 0 0 46 83 1 1 0 0 0 47 61 1 0 0 0 0 47 84 1 1 0 0 0 48 35 1 1 0 0 0 48 55 1 0 0 0 0 48 92 1 0 0 0 0 49 67 1 6 0 0 0 49 70 1 0 0 0 0 50 68 1 6 0 0 0 50 93 1 0 0 0 0 51 73 2 0 0 0 0 51 90 1 0 0 0 0 52 86 1 0 0 0 0 52 91 1 6 0 0 0 53 87 1 0 0 0 0 53 94 1 6 0 0 0 54 88 1 0 0 0 0 54 95 1 6 0 0 0 55 56 1 0 0 0 0 55 74 1 6 0 0 0 56 57 1 0 0 0 0 56 75 1 1 0 0 0 57 65 1 0 0 0 0 57 76 1 6 0 0 0 58 63 1 0 0 0 0 58 66 1 0 0 0 0 58 77 1 6 0 0 0 59 94 1 1 0 0 0 60 95 1 1 0 0 0 61 96 1 1 0 0 0 62 63 1 0 0 0 0 62 97 1 6 0 0 0 63 85 1 1 0 0 0 64 78 2 0 0 0 0 64 93 1 0 0 0 0 65 92 1 0 0 0 0 65 97 1 1 0 0 0 66 89 1 0 0 0 0 66 96 1 1 0 0 0 67 6 1 6 0 0 0 68 69 1 1 0 0 0 69 79 1 6 0 0 0 70 71 1 1 0 0 0 70 80 1 0 0 0 0 71 68 1 6 0 0 0 71 81 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1370.67
Volume:	1344.632
LogP:	4.356
LogD:	3.137
LogS:	-4.184
# Rotatable Bonds:	23
TPSA:	343.66
# H-Bond Aceptor:	26
# H-Bond Donor:	8
# Rings:	11
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.05
Synthetic Accessibility Score:	7.634
Fsp3:	0.746
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:	-6.065
MDCK Permeability:	0.00023312776465900242
Pgp-inhibitor:	0.004
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.134
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	72.25436401367188%
Volume Distribution (VD):	0.04
Pgp-substrate:	12.610934257507324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.217
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	0.876
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.779
Human Hepatotoxicity (H-HT):	0.177
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.551
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.876
Carcinogencity:	0.231
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC475531

Natural Product ID:	NPC475531
*Common Name:**	[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-Trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-Hydroxy-4-Methoxy-6-Methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-10,13-Dimethyl-17-[(1S)-1-[(E)-3-Phenylprop-2-Enoyl]Oxyethyl]-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-12-Yl] Benzoate
IUPAC Name:	[(3S,8S,9R,10R,12R,13R,14R,17S)-8,14,17-trihydroxy-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-[(1S)-1-[(E)-3-phenylprop-2-enoyl]oxyethyl]-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] benzoate
Synonyms:
Standard InCHIKey:	MDLPSLZTXRUNDJ-RBRNAYMRSA-N
Standard InCHI:	InChI=1S/C71H102O26/c1-36-59(94-53-32-46(83-9)60(37(2)87-53)95-54-33-47(84-10)61(38(3)88-54)96-66-58(77)63(85-11)62(39(4)89-66)97-65-57(76)56(75)55(74)48(35-72)92-65)45(82-8)31-52(86-36)91-44-25-26-67(6)43(30-44)24-27-70(80)49(67)34-50(93-64(78)42-20-16-13-17-21-42)68(7)69(79,28-29-71(68,70)81)40(5)90-51(73)23-22-41-18-14-12-15-19-41/h12-24,36-40,44-50,52-63,65-66,72,74-77,79-81H,25-35H2,1-11H3/b23-22+/t36-,37-,38-,39-,40+,44+,45+,46+,47+,48-,49-,50-,52+,53+,54+,55-,56+,57-,58-,59-,60-,61-,62-,63-,65+,66+,67+,68-,69-,70+,71-/m1/s1
SMILES:	CC1C(C(CC(O1)OC2CCC3(C4CC(C5(C(CCC5(C4(CC=C3C2)O)O)(C(C)OC(=O)C=CC6=CC=CC=C6)O)C)OC(=O)C7=CC=CC=C7)C)OC)OC8CC(C(C(O8)C)OC9CC(C(C(O9)C)OC1C(C(C(C(O1)C)OC1C(C(C(C(O1)CO)O)O)O)OC)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507437
PubChem CID:	44566876
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
NPO33108	leptadenia hastata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623046]
NPO33108	leptadenia hastata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8786361]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	13.0	%	PMID[473860]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	14.0	%	PMID[473860]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	16.0	%	PMID[473860]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	5.0	%	PMID[473860]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	4.0	%	PMID[473860]

☑ 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 NPC475531 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	366
0.1-0.2	1321
0.2-0.3	2713
0.3-0.4	5624
0.4-0.5	9959
0.5-0.6	14103
0.6-0.7	6827
0.7-0.8	1399
0.8-0.85	231
0.85-0.9	116
0.9-0.95	31
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475175
1.0	High Similarity	NPC475198
0.9935	High Similarity	NPC473557
0.9935	High Similarity	NPC473468
0.9935	High Similarity	NPC475567
0.9545	High Similarity	NPC476784
0.9375	High Similarity	NPC477488
0.9187	High Similarity	NPC477491
0.9091	High Similarity	NPC70236
0.9091	High Similarity	NPC475218
0.9091	High Similarity	NPC475447
0.9091	High Similarity	NPC476092
0.9062	High Similarity	NPC473641
0.9062	High Similarity	NPC475505
0.9062	High Similarity	NPC475300
0.9062	High Similarity	NPC475437
0.9062	High Similarity	NPC473797
0.9062	High Similarity	NPC475464
0.9051	High Similarity	NPC319404
0.9026	High Similarity	NPC474564
0.9	High Similarity	NPC165234
0.9	High Similarity	NPC475536
0.8994	High Similarity	NPC477623
0.8944	High Similarity	NPC478125
0.8902	High Similarity	NPC477471
0.8902	High Similarity	NPC477473
0.8902	High Similarity	NPC477466
0.8902	High Similarity	NPC477469
0.8882	High Similarity	NPC478124
0.8868	High Similarity	NPC322048
0.8868	High Similarity	NPC318447
0.8846	High Similarity	NPC476173
0.8805	High Similarity	NPC326235
0.8805	High Similarity	NPC323001
0.8797	High Similarity	NPC472658
0.8797	High Similarity	NPC472657
0.8758	High Similarity	NPC309991
0.8758	High Similarity	NPC323356
0.8758	High Similarity	NPC471138
0.8758	High Similarity	NPC326328
0.8742	High Similarity	NPC34066
0.8742	High Similarity	NPC469398
0.8742	High Similarity	NPC469422
0.8726	High Similarity	NPC469448
0.871	High Similarity	NPC472568
0.871	High Similarity	NPC171525
0.871	High Similarity	NPC158663
0.871	High Similarity	NPC70403
0.871	High Similarity	NPC96903
0.871	High Similarity	NPC470157
0.871	High Similarity	NPC473088
0.871	High Similarity	NPC472575
0.871	High Similarity	NPC29704
0.871	High Similarity	NPC476973
0.871	High Similarity	NPC471104
0.871	High Similarity	NPC184817
0.871	High Similarity	NPC469349
0.871	High Similarity	NPC177940
0.871	High Similarity	NPC472572
0.871	High Similarity	NPC470159
0.871	High Similarity	NPC200471
0.871	High Similarity	NPC472571
0.871	High Similarity	NPC174982
0.8679	High Similarity	NPC471135
0.8662	High Similarity	NPC301556
0.8662	High Similarity	NPC92293
0.8662	High Similarity	NPC270590
0.8662	High Similarity	NPC471101
0.8662	High Similarity	NPC266265
0.8647	High Similarity	NPC475613
0.8645	High Similarity	NPC241951
0.8645	High Similarity	NPC188865
0.8645	High Similarity	NPC25768
0.8645	High Similarity	NPC472573
0.8645	High Similarity	NPC163719
0.8645	High Similarity	NPC475122
0.8645	High Similarity	NPC95265
0.8645	High Similarity	NPC475759
0.8645	High Similarity	NPC11685
0.8645	High Similarity	NPC70716
0.8645	High Similarity	NPC125106
0.8645	High Similarity	NPC57628
0.8645	High Similarity	NPC95810
0.8645	High Similarity	NPC472569
0.8645	High Similarity	NPC476974
0.8645	High Similarity	NPC470152
0.8645	High Similarity	NPC472570
0.8625	High Similarity	NPC469456
0.8599	High Similarity	NPC281717
0.8598	High Similarity	NPC150893
0.8598	High Similarity	NPC329960
0.8598	High Similarity	NPC295408
0.859	High Similarity	NPC40085
0.859	High Similarity	NPC264270
0.859	High Similarity	NPC472556
0.8581	High Similarity	NPC163087
0.858	High Similarity	NPC469399
0.8571	High Similarity	NPC475638
0.8571	High Similarity	NPC475548
0.8571	High Similarity	NPC290683
0.8553	High Similarity	NPC96308
0.8553	High Similarity	NPC478123
0.8553	High Similarity	NPC469415
0.8544	High Similarity	NPC476975
0.8535	High Similarity	NPC473602
0.8535	High Similarity	NPC474935
0.8526	High Similarity	NPC111466
0.8521	High Similarity	NPC469421
0.8503	High Similarity	NPC102465
0.8503	High Similarity	NPC469420
0.85	High Similarity	NPC477905
0.85	High Similarity	NPC472548
0.8491	Intermediate Similarity	NPC473214
0.8491	Intermediate Similarity	NPC222102
0.8491	Intermediate Similarity	NPC470245
0.8491	Intermediate Similarity	NPC303429
0.8462	Intermediate Similarity	NPC91703
0.8452	Intermediate Similarity	NPC41481
0.8452	Intermediate Similarity	NPC97947
0.8452	Intermediate Similarity	NPC472576
0.8452	Intermediate Similarity	NPC118080
0.8452	Intermediate Similarity	NPC87448
0.8452	Intermediate Similarity	NPC16912
0.8452	Intermediate Similarity	NPC291599
0.8452	Intermediate Similarity	NPC224491
0.8452	Intermediate Similarity	NPC27377
0.8438	Intermediate Similarity	NPC470153
0.8428	Intermediate Similarity	NPC76103
0.8428	Intermediate Similarity	NPC473215
0.8418	Intermediate Similarity	NPC312393
0.8418	Intermediate Similarity	NPC478263
0.8405	Intermediate Similarity	NPC469417
0.8397	Intermediate Similarity	NPC34012
0.8397	Intermediate Similarity	NPC475513
0.8397	Intermediate Similarity	NPC473755
0.8395	Intermediate Similarity	NPC5115
0.8395	Intermediate Similarity	NPC472549
0.8393	Intermediate Similarity	NPC40138
0.8387	Intermediate Similarity	NPC100913
0.8387	Intermediate Similarity	NPC472547
0.8387	Intermediate Similarity	NPC211137
0.8387	Intermediate Similarity	NPC48017
0.8387	Intermediate Similarity	NPC476094
0.8387	Intermediate Similarity	NPC473060
0.8387	Intermediate Similarity	NPC4341
0.8387	Intermediate Similarity	NPC275592
0.8387	Intermediate Similarity	NPC473613
0.8387	Intermediate Similarity	NPC90614
0.8387	Intermediate Similarity	NPC147880
0.8387	Intermediate Similarity	NPC473081
0.8387	Intermediate Similarity	NPC184747
0.8387	Intermediate Similarity	NPC473109
0.8387	Intermediate Similarity	NPC473085
0.8387	Intermediate Similarity	NPC473112
0.8387	Intermediate Similarity	NPC200592
0.8387	Intermediate Similarity	NPC43241
0.8387	Intermediate Similarity	NPC473758
0.8387	Intermediate Similarity	NPC171207
0.8387	Intermediate Similarity	NPC97667
0.8375	Intermediate Similarity	NPC475561
0.8375	Intermediate Similarity	NPC31829
0.8375	Intermediate Similarity	NPC475417
0.8365	Intermediate Similarity	NPC473760
0.8365	Intermediate Similarity	NPC327031
0.8364	Intermediate Similarity	NPC476077
0.8363	Intermediate Similarity	NPC477617
0.8363	Intermediate Similarity	NPC13989
0.8362	Intermediate Similarity	NPC475121
0.8362	Intermediate Similarity	NPC476067
0.8354	Intermediate Similarity	NPC477467
0.8354	Intermediate Similarity	NPC477736
0.8354	Intermediate Similarity	NPC478264
0.8344	Intermediate Similarity	NPC191082
0.8344	Intermediate Similarity	NPC139067
0.8344	Intermediate Similarity	NPC177340
0.8344	Intermediate Similarity	NPC475429
0.8344	Intermediate Similarity	NPC270498
0.8344	Intermediate Similarity	NPC147217
0.8344	Intermediate Similarity	NPC246480
0.8344	Intermediate Similarity	NPC473673
0.8333	Intermediate Similarity	NPC469477
0.8333	Intermediate Similarity	NPC133430
0.8323	Intermediate Similarity	NPC210591
0.8323	Intermediate Similarity	NPC475652
0.8323	Intermediate Similarity	NPC298072
0.8323	Intermediate Similarity	NPC214550
0.8323	Intermediate Similarity	NPC62792
0.8305	Intermediate Similarity	NPC189704
0.8302	Intermediate Similarity	NPC48599
0.8302	Intermediate Similarity	NPC209592
0.8293	Intermediate Similarity	NPC477474
0.8293	Intermediate Similarity	NPC477735
0.8293	Intermediate Similarity	NPC477472
0.8293	Intermediate Similarity	NPC477470
0.8291	Intermediate Similarity	NPC51314
0.8291	Intermediate Similarity	NPC67777
0.8291	Intermediate Similarity	NPC34943
0.8282	Intermediate Similarity	NPC469730
0.8282	Intermediate Similarity	NPC473632
0.8282	Intermediate Similarity	NPC26033

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 NPC475531 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	822
0.2-0.3	1744
0.3-0.4	3122
0.4-0.5	2154
0.5-0.6	821
0.6-0.7	153
0.7-0.8	32
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8187	Intermediate Similarity	NPD7799	Discontinued
0.7931	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7236	Approved
0.7771	Intermediate Similarity	NPD7239	Suspended
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD8368	Discontinued
0.7473	Intermediate Similarity	NPD8407	Phase 2
0.7418	Intermediate Similarity	NPD8313	Approved
0.7418	Intermediate Similarity	NPD8312	Approved
0.7358	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7057	Phase 3
0.7356	Intermediate Similarity	NPD7058	Phase 2
0.7341	Intermediate Similarity	NPD8455	Phase 2
0.7337	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8360	Approved
0.7312	Intermediate Similarity	NPD8435	Approved
0.7312	Intermediate Similarity	NPD8361	Approved
0.724	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8434	Phase 2
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7182	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD6273	Approved
0.712	Intermediate Similarity	NPD7240	Approved
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7083	Intermediate Similarity	NPD8485	Approved
0.7063	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7041	Intermediate Similarity	NPD7497	Discontinued
0.7021	Intermediate Similarity	NPD8150	Discontinued
0.7011	Intermediate Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD8335	Approved
0.6987	Remote Similarity	NPD8296	Approved
0.6987	Remote Similarity	NPD8378	Approved
0.6987	Remote Similarity	NPD8380	Approved
0.6987	Remote Similarity	NPD8033	Approved
0.6987	Remote Similarity	NPD8379	Approved
0.6964	Remote Similarity	NPD7266	Discontinued
0.6951	Remote Similarity	NPD7961	Discontinued
0.6947	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD8377	Approved
0.6923	Remote Similarity	NPD8294	Approved
0.6923	Remote Similarity	NPD7741	Discontinued
0.6919	Remote Similarity	NPD7074	Phase 3
0.6909	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD37	Approved
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.6879	Remote Similarity	NPD7503	Approved
0.6872	Remote Similarity	NPD4967	Phase 2
0.6872	Remote Similarity	NPD4966	Approved
0.6872	Remote Similarity	NPD4965	Approved
0.6869	Remote Similarity	NPD7435	Discontinued
0.6865	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7516	Approved
0.6835	Remote Similarity	NPD5125	Phase 3
0.6835	Remote Similarity	NPD5126	Approved
0.6829	Remote Similarity	NPD7008	Discontinued
0.6828	Remote Similarity	NPD7472	Approved
0.6813	Remote Similarity	NPD7199	Phase 2
0.6813	Remote Similarity	NPD7507	Approved
0.6809	Remote Similarity	NPD7808	Phase 3
0.6796	Remote Similarity	NPD6234	Discontinued
0.6795	Remote Similarity	NPD7327	Approved
0.6795	Remote Similarity	NPD7328	Approved
0.6792	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7319	Approved
0.6784	Remote Similarity	NPD7698	Approved
0.6784	Remote Similarity	NPD7696	Phase 3
0.6784	Remote Similarity	NPD7697	Approved
0.6782	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8151	Discontinued
0.678	Remote Similarity	NPD7028	Phase 2
0.6774	Remote Similarity	NPD5844	Phase 1
0.6774	Remote Similarity	NPD7054	Approved
0.676	Remote Similarity	NPD5760	Phase 2
0.676	Remote Similarity	NPD5761	Phase 2
0.6755	Remote Similarity	NPD7251	Discontinued
0.6755	Remote Similarity	NPD6559	Discontinued
0.6753	Remote Similarity	NPD8133	Approved
0.6749	Remote Similarity	NPD7874	Approved
0.6749	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4628	Phase 3
0.674	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6823	Phase 2
0.6733	Remote Similarity	NPD7701	Phase 2
0.6717	Remote Similarity	NPD6779	Approved
0.6717	Remote Similarity	NPD6776	Approved
0.6717	Remote Similarity	NPD6780	Approved
0.6717	Remote Similarity	NPD6781	Approved
0.6717	Remote Similarity	NPD6782	Approved
0.6717	Remote Similarity	NPD6777	Approved
0.6717	Remote Similarity	NPD6778	Approved
0.6716	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7783	Phase 2
0.6702	Remote Similarity	NPD6797	Phase 2
0.6702	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD7871	Phase 2
0.6667	Remote Similarity	NPD6765	Approved
0.6649	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6858	Approved
0.6645	Remote Similarity	NPD7094	Approved
0.6634	Remote Similarity	NPD7801	Approved
0.6609	Remote Similarity	NPD6190	Approved
0.6602	Remote Similarity	NPD8462	Phase 1
0.6593	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6213	Phase 3
0.6582	Remote Similarity	NPD6212	Phase 3
0.6575	Remote Similarity	NPD7819	Suspended
0.657	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2629	Approved
0.6552	Remote Similarity	NPD7003	Approved
0.6548	Remote Similarity	NPD6663	Approved
0.6545	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3751	Discontinued
0.6543	Remote Similarity	NPD3818	Discontinued
0.6541	Remote Similarity	NPD7610	Discontinued
0.6535	Remote Similarity	NPD7680	Approved
0.6528	Remote Similarity	NPD6785	Approved
0.6528	Remote Similarity	NPD6784	Approved
0.6519	Remote Similarity	NPD4198	Discontinued
0.6517	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5736	Approved
0.6505	Remote Similarity	NPD3787	Discontinued
0.65	Remote Similarity	NPD4380	Phase 2
0.65	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7097	Phase 1
0.6488	Remote Similarity	NPD3764	Approved
0.6484	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8404	Phase 2
0.6474	Remote Similarity	NPD5763	Approved
0.6474	Remote Similarity	NPD5762	Approved
0.6467	Remote Similarity	NPD7075	Discontinued
0.646	Remote Similarity	NPD8516	Approved
0.646	Remote Similarity	NPD8515	Approved
0.646	Remote Similarity	NPD8517	Approved
0.6457	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD5951	Approved
0.6444	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6166	Phase 2
0.6436	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7736	Approved
0.642	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7768	Phase 2
0.6402	Remote Similarity	NPD7473	Discontinued
0.64	Remote Similarity	NPD6674	Discontinued
0.6398	Remote Similarity	NPD5494	Approved
0.639	Remote Similarity	NPD7999	Approved
0.639	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.638	Remote Similarity	NPD8328	Phase 3
0.6379	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6002	Phase 3
0.6379	Remote Similarity	NPD6004	Phase 3
0.6379	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6005	Phase 3
0.6364	Remote Similarity	NPD6959	Discontinued
0.6364	Remote Similarity	NPD6685	Approved
0.6359	Remote Similarity	NPD5402	Approved
0.6359	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD8513	Phase 3
0.6354	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6232	Discontinued
0.6328	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD6686	Approved
0.6319	Remote Similarity	NPD6599	Discontinued
0.6319	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4140	Approved
0.6306	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7930	Approved
0.6296	Remote Similarity	NPD7009	Phase 2
0.6287	Remote Similarity	NPD3094	Phase 2
0.6284	Remote Similarity	NPD7411	Suspended
0.6282	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6355	Discontinued
0.6271	Remote Similarity	NPD3750	Approved
0.6263	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD6412	Phase 2
0.6257	Remote Similarity	NPD7714	Approved
0.6257	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7715	Approved
0.625	Remote Similarity	NPD6801	Discontinued
0.6243	Remote Similarity	NPD5403	Approved
0.6243	Remote Similarity	NPD6653	Approved
0.6229	Remote Similarity	NPD5404	Approved
0.6229	Remote Similarity	NPD5405	Approved
0.6229	Remote Similarity	NPD5408	Approved
0.6229	Remote Similarity	NPD5406	Approved
0.6222	Remote Similarity	NPD7422	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