NPASS Compound

Structure

NPC476084 OpenBabel07101718202D 98102 0 0 1 0 0 0 0 0999 V2000 8.0612 -10.6944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4575 3.5837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2265 0.1951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4547 -8.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2156 -1.5682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7849 -5.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4547 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3648 -6.1551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4636 -3.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7036 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5138 0.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9535 -6.1551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8376 -4.9001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9188 -2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7381 1.0844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2075 3.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3630 -9.8450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3199 3.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2407 -9.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7609 3.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 -9.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7916 -9.9614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8222 3.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6974 -9.3735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0253 2.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8593 -1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3208 -6.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7944 -10.0361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7972 3.2706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7902 -1.0519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3208 -5.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5634 -8.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2435 1.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1357 -2.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9188 -4.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8222 -9.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7916 3.2706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4230 -2.6642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1868 -4.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3452 1.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -7.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3173 -1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8777 -3.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7665 -9.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8913 2.6828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0775 -0.7938 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.4547 -7.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2847 -1.9336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.9188 -5.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5887 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4339 -5.7898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.4664 -3.8454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7286 -1.8565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3648 -0.5356 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0226 -5.7898 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7972 -9.9614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7944 3.3454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7665 3.0481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8913 -9.3735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5634 2.1828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2435 -8.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5720 -1.6754 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 14.1868 -5.1907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2048 -3.2877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.0528 -3.6907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0226 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7286 -4.8342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.4664 -2.8454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8777 -2.8454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0254 0.8262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -6.6907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3452 -8.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1466 -1.1591 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.3173 -4.8342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5887 -6.6907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6481 -10.9502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7944 4.3454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9535 -0.5356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7036 -5.0567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4636 -2.7706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8749 -2.7706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0254 -8.9831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2185 1.4497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9975 -2.1479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2923 -5.0567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0557 -4.2766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.0528 -2.6907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8072 1.4497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.1907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5029 -1.3101 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.0528 -5.6907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6974 2.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0253 -8.8735 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0254 -7.5170 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 1 45 1 0 0 0 0 2 46 1 0 0 0 0 13 89 1 0 0 0 0 14 90 1 0 0 0 0 15 91 1 0 0 0 0 16 92 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 23 29 1 0 0 0 0 23 45 2 0 0 0 0 24 30 1 0 0 0 0 24 46 2 0 0 0 0 25 33 2 0 0 0 0 25 45 1 0 0 0 0 26 34 2 0 0 0 0 26 46 1 0 0 0 0 27 31 1 0 0 0 0 27 47 1 0 0 0 0 28 32 1 0 0 0 0 28 48 1 0 0 0 0 29 57 1 0 0 0 0 30 58 1 0 0 0 0 33 73 1 0 0 0 0 34 74 1 0 0 0 0 35 49 1 0 0 0 0 35 65 1 0 0 0 0 36 50 1 0 0 0 0 36 66 1 0 0 0 0 37 57 1 0 0 0 0 37 60 1 0 0 0 0 38 58 1 0 0 0 0 38 59 1 0 0 0 0 39 63 1 0 0 0 0 39 65 1 0 0 0 0 40 64 1 0 0 0 0 40 66 1 0 0 0 0 41 61 1 0 0 0 0 41 71 1 0 0 0 0 42 62 1 0 0 0 0 42 72 1 0 0 0 0 43 67 1 0 0 0 0 43 69 1 0 0 0 0 44 68 1 0 0 0 0 44 70 1 0 0 0 0 47 3 1 6 0 0 0 47 75 1 0 0 0 0 48 4 1 6 0 0 0 49 5 1 6 0 0 0 49 93 1 0 0 0 0 50 6 1 6 0 0 0 50 94 1 0 0 0 0 51 7 1 1 0 0 0 51 67 1 0 0 0 0 51 71 1 0 0 0 0 52 8 1 1 0 0 0 52 68 1 0 0 0 0 52 72 1 0 0 0 0 53 9 1 6 0 0 0 53 69 1 0 0 0 0 53 76 1 0 0 0 0 54 10 1 6 0 0 0 54 70 1 0 0 0 0 54 78 1 0 0 0 0 55 11 1 6 0 0 0 55 75 1 0 0 0 0 56 12 1 1 0 0 0 56 76 1 0 0 0 0 56 77 1 0 0 0 0 57 79 1 6 0 0 0 58 80 1 6 0 0 0 59 19 1 6 0 0 0 59 95 1 0 0 0 0 60 20 1 6 0 0 0 60 96 1 0 0 0 0 61 21 1 6 0 0 0 61 95 1 0 0 0 0 62 22 1 6 0 0 0 62 96 1 0 0 0 0 63 31 1 1 0 0 0 63 93 1 0 0 0 0 64 32 1 1 0 0 0 64 94 1 0 0 0 0 65 89 1 6 0 0 0 66 90 1 6 0 0 0 67 81 1 1 0 0 0 68 82 1 1 0 0 0 69 83 1 1 0 0 0 70 84 1 1 0 0 0 71 91 1 6 0 0 0 72 92 1 6 0 0 0 73 85 2 0 0 0 0 73 97 1 0 0 0 0 74 86 2 0 0 0 0 74 98 1 0 0 0 0 75 87 1 1 0 0 0 76 88 1 6 0 0 0 77 48 1 6 0 0 0 77 97 1 0 0 0 0 78 55 1 1 0 0 0 78 98 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1390.95
Volume:	1472.21
LogP:	7.744
LogD:	4.676
LogS:	-5.75
# Rotatable Bonds:	14
TPSA:	288.28
# H-Bond Aceptor:	20
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	8.403
Fsp3:	0.846
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.029
MDCK Permeability:	0.00028144530369900167
Pgp-inhibitor:	1.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.84
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.337

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	76.25041961669922%
Volume Distribution (VD):	0.521
Pgp-substrate:	18.481042861938477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	4.167
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.892
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.229
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.996
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.522

Download Data

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

Natural Product: NPC476084

Natural Product ID:	NPC476084
*Common Name:**	Isoswinholide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ABDPMKYIGSFOOE-SCJHHIAVSA-N
Standard InCHI:	InChI=1S/C78H134O20/c1-45-23-29-57(79)37-60-20-18-22-62(96-60)42-72(92-16)52(8)68(82)44-70(84)54(10)78(55(11)75(87)47(3)27-31-63-39-65(89-13)35-49(5)93-63)98-74(86)34-26-46(2)24-30-58(80)38-59-19-17-21-61(95-59)41-71(91-15)51(7)67(81)43-69(83)53(9)76(88)56(12)77(97-73(85)33-25-45)48(4)28-32-64-40-66(90-14)36-50(6)94-64/h18,20,23-26,33-34,47-72,75-84,87-88H,17,19,21-22,27-32,35-44H2,1-16H3/b33-25+,34-26+,45-23+,46-24+/t47-,48-,49-,50-,51-,52-,53-,54-,55-,56+,57-,58-,59-,60-,61+,62+,63-,64-,65+,66+,67-,68-,69+,70+,71-,72-,75-,76-,77-,78-/m0/s1
SMILES:	CC1CC(CC(O1)CCC(C)C2C(C(C(C(CC(C(C(CC3CCCC(O3)CC(CC=C(C=CC(=O)OC(C(C(CC(C(C(CC4CC=CC(O4)CC(CC=C(C=CC(=O)O2)C)O)OC)C)O)O)C)C(C)C(C(C)CCC5CC(CC(O5)C)OC)O)C)O)OC)C)O)O)C)O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525226
PubChem CID:	44576170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421754]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193024]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[15679329]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16441091]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125225]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318032]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[19961178]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	palau	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078073]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428459]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23830699]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27213234]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27548648]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29989811]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30346758]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[32191460]
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[557265]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	35.0	nM	PMID[557266]
NPT65	Cell Line	HepG2	Homo sapiens	Efficacy	=	16.28	%	PMID[557266]

☑ 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 NPC476084 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	195
0.1-0.2	1078
0.2-0.3	3993
0.3-0.4	8593
0.4-0.5	15243
0.5-0.6	8879
0.6-0.7	4352
0.7-0.8	322
0.8-0.85	12
0.85-0.9	22
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476075
0.9767	High Similarity	NPC206679
0.9767	High Similarity	NPC114172
0.9767	High Similarity	NPC471324
0.9655	High Similarity	NPC109406
0.9655	High Similarity	NPC159092
0.9231	High Similarity	NPC475332
0.908	High Similarity	NPC199382
0.8824	High Similarity	NPC8538
0.8824	High Similarity	NPC184208
0.875	High Similarity	NPC197736
0.8737	High Similarity	NPC475157
0.8737	High Similarity	NPC471637
0.8737	High Similarity	NPC57586
0.8737	High Similarity	NPC2313
0.8737	High Similarity	NPC475655
0.8737	High Similarity	NPC154132
0.8652	High Similarity	NPC316138
0.8652	High Similarity	NPC313658
0.8605	High Similarity	NPC315731
0.8602	High Similarity	NPC300710
0.8588	High Similarity	NPC139712
0.8511	High Similarity	NPC255410
0.8421	Intermediate Similarity	NPC120299
0.8384	Intermediate Similarity	NPC315070
0.8333	Intermediate Similarity	NPC475653
0.8235	Intermediate Similarity	NPC469880
0.8172	Intermediate Similarity	NPC177668
0.8132	Intermediate Similarity	NPC47220
0.8132	Intermediate Similarity	NPC186332
0.8125	Intermediate Similarity	NPC288350
0.8125	Intermediate Similarity	NPC173329
0.8118	Intermediate Similarity	NPC285840
0.8118	Intermediate Similarity	NPC327041
0.8081	Intermediate Similarity	NPC473596
0.8065	Intermediate Similarity	NPC133450
0.8039	Intermediate Similarity	NPC193765
0.7979	Intermediate Similarity	NPC3952
0.7931	Intermediate Similarity	NPC477203
0.7917	Intermediate Similarity	NPC159698
0.7917	Intermediate Similarity	NPC256368
0.7882	Intermediate Similarity	NPC329914
0.7882	Intermediate Similarity	NPC185186
0.7882	Intermediate Similarity	NPC327383
0.7843	Intermediate Similarity	NPC476740
0.7843	Intermediate Similarity	NPC476738
0.7826	Intermediate Similarity	NPC471494
0.7826	Intermediate Similarity	NPC242233
0.7822	Intermediate Similarity	NPC475367
0.7822	Intermediate Similarity	NPC474581
0.7822	Intermediate Similarity	NPC473816
0.7816	Intermediate Similarity	NPC477202
0.7812	Intermediate Similarity	NPC238090
0.7812	Intermediate Similarity	NPC472196
0.7812	Intermediate Similarity	NPC472195
0.7778	Intermediate Similarity	NPC203627
0.7742	Intermediate Similarity	NPC61527
0.7708	Intermediate Similarity	NPC110072
0.7692	Intermediate Similarity	NPC473807
0.7692	Intermediate Similarity	NPC477385
0.7692	Intermediate Similarity	NPC477390
0.7692	Intermediate Similarity	NPC123908
0.7692	Intermediate Similarity	NPC10080
0.7684	Intermediate Similarity	NPC285588
0.7674	Intermediate Similarity	NPC329890
0.7674	Intermediate Similarity	NPC477085
0.7667	Intermediate Similarity	NPC133226
0.7667	Intermediate Similarity	NPC470147
0.7647	Intermediate Similarity	NPC476012
0.7647	Intermediate Similarity	NPC309398
0.7629	Intermediate Similarity	NPC476049
0.7619	Intermediate Similarity	NPC133625
0.7614	Intermediate Similarity	NPC188860
0.7609	Intermediate Similarity	NPC16488
0.7609	Intermediate Similarity	NPC44261
0.76	Intermediate Similarity	NPC65700
0.7586	Intermediate Similarity	NPC477204
0.7558	Intermediate Similarity	NPC477086
0.7558	Intermediate Similarity	NPC477087
0.7558	Intermediate Similarity	NPC316185
0.7556	Intermediate Similarity	NPC470149
0.7556	Intermediate Similarity	NPC470148
0.7556	Intermediate Similarity	NPC180725
0.7553	Intermediate Similarity	NPC315395
0.7553	Intermediate Similarity	NPC316426
0.7553	Intermediate Similarity	NPC311163
0.7551	Intermediate Similarity	NPC469491
0.7549	Intermediate Similarity	NPC201191
0.7529	Intermediate Similarity	NPC101622
0.7528	Intermediate Similarity	NPC474026
0.7528	Intermediate Similarity	NPC315394
0.7528	Intermediate Similarity	NPC84360
0.7528	Intermediate Similarity	NPC233071
0.7527	Intermediate Similarity	NPC78673
0.7527	Intermediate Similarity	NPC160517
0.7527	Intermediate Similarity	NPC186155
0.7475	Intermediate Similarity	NPC272050
0.7474	Intermediate Similarity	NPC86005
0.7474	Intermediate Similarity	NPC477959
0.7444	Intermediate Similarity	NPC248775
0.7442	Intermediate Similarity	NPC476037
0.7442	Intermediate Similarity	NPC4299
0.7429	Intermediate Similarity	NPC109376
0.7426	Intermediate Similarity	NPC161855
0.7426	Intermediate Similarity	NPC308567
0.7426	Intermediate Similarity	NPC255592
0.7426	Intermediate Similarity	NPC261377
0.74	Intermediate Similarity	NPC473291
0.7386	Intermediate Similarity	NPC107654
0.7386	Intermediate Similarity	NPC315843
0.7368	Intermediate Similarity	NPC208473
0.7368	Intermediate Similarity	NPC477389
0.7368	Intermediate Similarity	NPC477387
0.7368	Intermediate Similarity	NPC164393
0.7363	Intermediate Similarity	NPC477088
0.7363	Intermediate Similarity	NPC471537
0.7358	Intermediate Similarity	NPC470024
0.7358	Intermediate Similarity	NPC224660
0.7353	Intermediate Similarity	NPC475053
0.734	Intermediate Similarity	NPC266718
0.7333	Intermediate Similarity	NPC172867
0.7333	Intermediate Similarity	NPC29389
0.7333	Intermediate Similarity	NPC93026
0.7333	Intermediate Similarity	NPC469960
0.7333	Intermediate Similarity	NPC265502
0.7333	Intermediate Similarity	NPC475711
0.7326	Intermediate Similarity	NPC151481
0.732	Intermediate Similarity	NPC212598
0.7315	Intermediate Similarity	NPC126897
0.7315	Intermediate Similarity	NPC297945
0.7312	Intermediate Similarity	NPC224455
0.7292	Intermediate Similarity	NPC471055
0.7292	Intermediate Similarity	NPC477388
0.7292	Intermediate Similarity	NPC118077
0.7292	Intermediate Similarity	NPC471056
0.7292	Intermediate Similarity	NPC475186
0.7292	Intermediate Similarity	NPC477386
0.729	Intermediate Similarity	NPC313668
0.729	Intermediate Similarity	NPC315836
0.7282	Intermediate Similarity	NPC477717
0.7273	Intermediate Similarity	NPC162615
0.7273	Intermediate Similarity	NPC320552
0.7273	Intermediate Similarity	NPC205034
0.7273	Intermediate Similarity	NPC152778
0.7264	Intermediate Similarity	NPC108682
0.7264	Intermediate Similarity	NPC469957
0.7264	Intermediate Similarity	NPC469959
0.7264	Intermediate Similarity	NPC472263
0.7263	Intermediate Similarity	NPC92633
0.7255	Intermediate Similarity	NPC83895
0.7255	Intermediate Similarity	NPC187761
0.7245	Intermediate Similarity	NPC202886
0.7245	Intermediate Similarity	NPC327253
0.7245	Intermediate Similarity	NPC313670
0.7241	Intermediate Similarity	NPC179261
0.7234	Intermediate Similarity	NPC185949
0.7234	Intermediate Similarity	NPC2379
0.7234	Intermediate Similarity	NPC263087
0.7234	Intermediate Similarity	NPC27314
0.7234	Intermediate Similarity	NPC107498
0.7234	Intermediate Similarity	NPC474809
0.7234	Intermediate Similarity	NPC31019
0.7234	Intermediate Similarity	NPC106912
0.7228	Intermediate Similarity	NPC16967
0.7228	Intermediate Similarity	NPC472995
0.7222	Intermediate Similarity	NPC316708
0.7217	Intermediate Similarity	NPC219804
0.7204	Intermediate Similarity	NPC112868
0.7204	Intermediate Similarity	NPC475944
0.7204	Intermediate Similarity	NPC474894
0.72	Intermediate Similarity	NPC238264
0.72	Intermediate Similarity	NPC477345
0.72	Intermediate Similarity	NPC477348
0.72	Intermediate Similarity	NPC294293
0.7196	Intermediate Similarity	NPC475263
0.7188	Intermediate Similarity	NPC122502
0.7184	Intermediate Similarity	NPC477716
0.7184	Intermediate Similarity	NPC227865
0.7184	Intermediate Similarity	NPC477721
0.7174	Intermediate Similarity	NPC1180
0.7174	Intermediate Similarity	NPC86971
0.7174	Intermediate Similarity	NPC226226
0.7174	Intermediate Similarity	NPC55304
0.7172	Intermediate Similarity	NPC477749
0.717	Intermediate Similarity	NPC82251
0.717	Intermediate Similarity	NPC218158
0.7159	Intermediate Similarity	NPC477084
0.7159	Intermediate Similarity	NPC475762
0.7158	Intermediate Similarity	NPC473308
0.7157	Intermediate Similarity	NPC477719
0.7157	Intermediate Similarity	NPC51499
0.7157	Intermediate Similarity	NPC40812
0.7157	Intermediate Similarity	NPC477718
0.7156	Intermediate Similarity	NPC475608
0.7156	Intermediate Similarity	NPC470026
0.7156	Intermediate Similarity	NPC21713
0.7156	Intermediate Similarity	NPC17791
0.7143	Intermediate Similarity	NPC45897
0.7143	Intermediate Similarity	NPC477748
0.7129	Intermediate Similarity	NPC170204

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 NPC476084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1162
0.2-0.3	3575
0.3-0.4	2778
0.4-0.5	1082
0.5-0.6	311
0.6-0.7	67
0.7-0.8	8
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
0.8172	Intermediate Similarity	NPD7838	Discovery
0.8144	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD46	Approved
0.7604	Intermediate Similarity	NPD6698	Approved
0.7315	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7983	Approved
0.7059	Intermediate Similarity	NPD7839	Suspended
0.7043	Intermediate Similarity	NPD8513	Phase 3
0.7019	Intermediate Similarity	NPD6648	Approved
0.6979	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5344	Discontinued
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6897	Remote Similarity	NPD8516	Approved
0.6897	Remote Similarity	NPD8515	Approved
0.6897	Remote Similarity	NPD7503	Approved
0.6897	Remote Similarity	NPD8517	Approved
0.6881	Remote Similarity	NPD6686	Approved
0.6832	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7638	Approved
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6639	Remote Similarity	NPD7829	Approved
0.6639	Remote Similarity	NPD7830	Approved
0.661	Remote Similarity	NPD8378	Approved
0.661	Remote Similarity	NPD8379	Approved
0.661	Remote Similarity	NPD8033	Approved
0.661	Remote Similarity	NPD8296	Approved
0.661	Remote Similarity	NPD8380	Approved
0.661	Remote Similarity	NPD8335	Approved
0.6531	Remote Similarity	NPD7154	Phase 3
0.6491	Remote Similarity	NPD6053	Discontinued
0.6486	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD4250	Approved
0.6436	Remote Similarity	NPD4251	Approved
0.6408	Remote Similarity	NPD5785	Approved
0.6392	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD6695	Phase 3
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6341	Remote Similarity	NPD8074	Phase 3
0.6337	Remote Similarity	NPD4249	Approved
0.6303	Remote Similarity	NPD7516	Approved
0.63	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7750	Discontinued
0.6271	Remote Similarity	NPD7115	Discovery
0.6263	Remote Similarity	NPD5209	Approved
0.6238	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5363	Approved
0.6224	Remote Similarity	NPD4822	Approved
0.6224	Remote Similarity	NPD7332	Phase 2
0.6224	Remote Similarity	NPD4821	Approved
0.6224	Remote Similarity	NPD4820	Approved
0.6224	Remote Similarity	NPD7514	Phase 3
0.6224	Remote Similarity	NPD4819	Approved
0.6211	Remote Similarity	NPD8264	Approved
0.621	Remote Similarity	NPD8448	Approved
0.62	Remote Similarity	NPD5362	Discontinued
0.6198	Remote Similarity	NPD8444	Approved
0.619	Remote Similarity	NPD8391	Approved
0.619	Remote Similarity	NPD8390	Approved
0.619	Remote Similarity	NPD8392	Approved
0.6186	Remote Similarity	NPD7145	Approved
0.6186	Remote Similarity	NPD4268	Approved
0.6186	Remote Similarity	NPD4271	Approved
0.618	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6371	Approved
0.6168	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6902	Approved
0.6154	Remote Similarity	NPD8133	Approved
0.6134	Remote Similarity	NPD7505	Discontinued
0.6129	Remote Similarity	NPD8451	Approved
0.6126	Remote Similarity	NPD7632	Discontinued
0.6122	Remote Similarity	NPD6929	Approved
0.6117	Remote Similarity	NPD7524	Approved
0.61	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7641	Discontinued
0.6082	Remote Similarity	NPD6925	Approved
0.6082	Remote Similarity	NPD6932	Approved
0.6082	Remote Similarity	NPD5776	Phase 2
0.6078	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6931	Approved
0.6061	Remote Similarity	NPD6930	Phase 2
0.604	Remote Similarity	NPD5332	Approved
0.604	Remote Similarity	NPD5331	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.6	Remote Similarity	NPD8273	Phase 1
0.5978	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8328	Phase 3
0.5965	Remote Similarity	NPD4211	Phase 1
0.5941	Remote Similarity	NPD6435	Approved
0.5941	Remote Similarity	NPD4270	Approved
0.5941	Remote Similarity	NPD4269	Approved
0.5929	Remote Similarity	NPD6647	Phase 2
0.5926	Remote Similarity	NPD5282	Discontinued
0.5922	Remote Similarity	NPD1694	Approved
0.592	Remote Similarity	NPD8299	Approved
0.592	Remote Similarity	NPD8340	Approved
0.592	Remote Similarity	NPD8341	Approved
0.592	Remote Similarity	NPD8342	Approved
0.5918	Remote Similarity	NPD4756	Discovery
0.5913	Remote Similarity	NPD6412	Phase 2
0.5909	Remote Similarity	NPD7902	Approved
0.5909	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7515	Phase 2
0.5888	Remote Similarity	NPD7087	Discontinued
0.5868	Remote Similarity	NPD7500	Approved
0.5865	Remote Similarity	NPD5786	Approved
0.5865	Remote Similarity	NPD5124	Phase 1
0.5865	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7319	Approved
0.5859	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD1695	Approved
0.5849	Remote Similarity	NPD6051	Approved
0.5847	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5369	Approved
0.5842	Remote Similarity	NPD6898	Phase 1
0.584	Remote Similarity	NPD7642	Approved
0.5833	Remote Similarity	NPD4732	Discontinued
0.5818	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6683	Phase 2
0.5798	Remote Similarity	NPD8297	Approved
0.5789	Remote Similarity	NPD7143	Approved
0.5789	Remote Similarity	NPD7144	Approved
0.5778	Remote Similarity	NPD4194	Approved
0.5778	Remote Similarity	NPD4191	Approved
0.5778	Remote Similarity	NPD4193	Approved
0.5778	Remote Similarity	NPD4192	Approved
0.5773	Remote Similarity	NPD6926	Approved
0.5773	Remote Similarity	NPD6924	Approved
0.5769	Remote Similarity	NPD6893	Approved
0.5766	Remote Similarity	NPD7266	Discontinued
0.5766	Remote Similarity	NPD6083	Phase 2
0.5766	Remote Similarity	NPD6084	Phase 2
0.5763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5368	Approved
0.5743	Remote Similarity	NPD4252	Approved
0.5729	Remote Similarity	NPD7151	Approved
0.5729	Remote Similarity	NPD7152	Approved
0.5729	Remote Similarity	NPD7150	Approved
0.5728	Remote Similarity	NPD6110	Phase 1
0.5726	Remote Similarity	NPD6899	Approved
0.5726	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD6422	Discontinued
0.5714	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5048	Discontinued
0.569	Remote Similarity	NPD6640	Phase 3
0.5688	Remote Similarity	NPD6399	Phase 3
0.5684	Remote Similarity	NPD6922	Approved
0.5684	Remote Similarity	NPD6923	Approved
0.5678	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6882	Approved
0.5657	Remote Similarity	NPD6933	Approved
0.5648	Remote Similarity	NPD7136	Phase 2
0.5644	Remote Similarity	NPD7645	Phase 2
0.5641	Remote Similarity	NPD6685	Approved
0.5641	Remote Similarity	NPD5697	Approved
0.5636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7900	Approved
0.563	Remote Similarity	NPD6883	Approved
0.563	Remote Similarity	NPD7102	Approved
0.563	Remote Similarity	NPD7290	Approved
0.561	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD6845	Suspended
0.5603	Remote Similarity	NPD5909	Discontinued
0.56	Remote Similarity	NPD7741	Discontinued
0.56	Remote Similarity	NPD6319	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