NPASS Compound

Structure

NPC473002 OpenBabel07101718332D 91 97 0 0 1 0 0 0 0 0999 V2000 -13.5815 -5.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7329 -7.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3868 -5.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0496 -6.9647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2563 -1.2398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2019 0.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4518 -4.1715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6000 -6.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0151 -4.9172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1634 -6.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2927 -10.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4374 -0.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -9.6086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2841 -10.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4459 -0.5262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0461 -1.1891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -9.1346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4382 -2.1098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2736 -0.0242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0666 -8.6847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6668 -9.3475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0632 -1.4501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6635 -2.1129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -8.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2315 -2.7186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2859 0.1322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -8.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6141 -2.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4301 -1.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3324 -6.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4407 -7.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2893 -3.1674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0391 -5.2638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7174 -7.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2563 -6.3559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3324 -0.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0182 -4.9956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5970 -6.1336 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0580 -8.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6720 -2.2435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -6.1298 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8320 -6.8369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2979 -3.2979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2979 -4.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.5958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8977 -3.6612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8320 -0.7588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.7144 -7.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5877 -5.8982 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0275 -5.2310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0391 -5.2638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -7.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4641 -4.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1541 -6.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0391 -2.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0244 -5.1526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 -7.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0391 -2.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2893 -4.4284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.1449 -6.4870 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -6.1298 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -13.1510 -6.6439 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 -6.8369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2979 -4.2979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2979 -3.2979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8320 -0.7588 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.4611 -4.4069 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.5908 -5.9767 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -7.5958 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8981 -3.6350 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -1.4659 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -15.2808 -8.2137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9629 -5.6465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3486 -8.2608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3486 0.6651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0336 -5.3879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7236 -7.6249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9629 -1.9493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4549 -4.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3486 -8.2608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9629 -1.9493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6720 -5.3523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3486 0.6651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 38 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 39 1 0 0 0 0 9 40 1 0 0 0 0 10 41 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 17 25 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 0 0 0 0 19 31 1 0 0 0 0 20 28 1 0 0 0 0 20 32 1 0 0 0 0 21 42 2 0 0 0 0 22 42 1 0 0 0 0 23 43 2 0 0 0 0 24 43 1 0 0 0 0 26 49 1 0 0 0 0 29 76 1 0 0 0 0 30 77 1 0 0 0 0 31 78 1 0 0 0 0 32 79 1 0 0 0 0 33 38 1 0 0 0 0 34 42 1 0 0 0 0 35 43 1 0 0 0 0 36 47 2 0 0 0 0 36 68 1 0 0 0 0 37 52 1 0 0 0 0 37 69 1 0 0 0 0 40 7 1 6 0 0 0 40 54 1 0 0 0 0 41 8 1 1 0 0 0 41 55 1 0 0 0 0 44 33 1 6 0 0 0 44 56 1 0 0 0 0 44 70 1 0 0 0 0 45 34 1 6 0 0 0 45 63 1 0 0 0 0 45 68 1 0 0 0 0 46 35 1 6 0 0 0 46 64 1 0 0 0 0 46 71 1 0 0 0 0 47 65 1 0 0 0 0 47 72 1 0 0 0 0 48 25 1 6 0 0 0 48 57 1 0 0 0 0 48 76 1 0 0 0 0 49 59 1 6 0 0 0 49 77 1 0 0 0 0 50 27 1 6 0 0 0 50 58 1 0 0 0 0 50 78 1 0 0 0 0 51 28 1 6 0 0 0 51 66 1 0 0 0 0 51 79 1 0 0 0 0 52 67 2 0 0 0 0 52 80 1 0 0 0 0 53 39 1 6 0 0 0 53 61 1 0 0 0 0 53 73 1 0 0 0 0 54 60 1 6 0 0 0 54 75 1 0 0 0 0 55 62 1 1 0 0 0 55 74 1 0 0 0 0 56 71 2 3 0 0 0 56 81 1 0 0 0 0 57 70 2 3 0 0 0 57 82 1 0 0 0 0 58 73 2 3 0 0 0 58 83 1 0 0 0 0 59 74 2 3 0 0 0 59 84 1 0 0 0 0 60 69 2 3 0 0 0 60 85 1 0 0 0 0 61 72 2 3 0 0 0 61 86 1 0 0 0 0 62 75 2 3 0 0 0 62 87 1 0 0 0 0 63 76 1 0 0 0 0 63 88 2 0 0 0 0 64 79 1 0 0 0 0 64 89 2 0 0 0 0 65 77 1 0 0 0 0 65 90 2 0 0 0 0 66 78 1 0 0 0 0 66 91 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1261.72
Volume:	1288.544
LogP:	3.69
LogD:	3.596
LogS:	-2.978
# Rotatable Bonds:	20
TPSA:	355.01
# H-Bond Aceptor:	25
# H-Bond Donor:	10
# Rings:	7
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.061
Synthetic Accessibility Score:	7.333
Fsp3:	0.606
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.468
MDCK Permeability:	0.00015522413013968617
Pgp-inhibitor:	0.18
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.105
Plasma Protein Binding (PPB):	57.888797760009766%
Volume Distribution (VD):	0.731
Pgp-substrate:	27.095348358154297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.382
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	0.828
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.574
Carcinogencity:	0.188
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC473002

Natural Product ID:	NPC473002
*Common Name:**	JUWGVTIMYSVRDI-KONYCJQDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JUWGVTIMYSVRDI-KONYCJQDSA-N
Standard InCHI:	InChI=1S/C66H95N13O12/c1-9-40(7)54(60(85)69-37-52(67)80)75-62(87)55(41(8)10-2)74-59(84)49-26-18-30-77(49)65(90)47-36-68-45(34-42-21-13-11-14-22-42)63(88)76-29-17-25-48(76)57(82)70-44(33-38(3)4)56(81)71-46(35-43-23-15-12-16-24-43)64(89)79-32-20-28-51(79)66(91)78-31-19-27-50(78)58(83)73-53(39(5)6)61(86)72-47/h11-16,21-24,36,38-41,44-46,48-51,53-55,68H,9-10,17-20,25-35,37H2,1-8H3,(H2,67,80)(H,69,85)(H,70,82)(H,71,81)(H,72,86)(H,73,83)(H,74,84)(H,75,87)/b47-36-/t40-,41-,44-,45-,46-,48-,49-,50-,51-,53-,54-,55-/m0/s1
SMILES:	CC[C@@H]([C@@H](C(=N[C@H](C(=NCC(=N)O)O)[C@H](CC)C)O)N=C([C@@H]1CCCN1C(=O)/C/1=C/N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@H]2C(=N[C@@H](CC(C)C)C(=N[C@H](C(=O)N2[C@H](C(=O)N3[C@H](C(=N[C@H](C(=N1)O)C(C)C)O)CCC3)CCC2)Cc1ccccc1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597658
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0003297] Organic Polymers [CHEMONTID:0003298] Polypeptides

*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
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26213786]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	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	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[470916]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	10000.0	nM	PMID[470916]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	100000.0	nM	PMID[470916]

☑ 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 NPC473002 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	234
0.1-0.2	1461
0.2-0.3	11641
0.3-0.4	20610
0.4-0.5	6319
0.5-0.6	1839
0.6-0.7	455
0.7-0.8	121
0.8-0.85	5
0.85-0.9	6
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC469902
0.9658	High Similarity	NPC473003
0.9384	High Similarity	NPC469903
0.9276	High Similarity	NPC469904
0.9067	High Similarity	NPC469898
0.8924	High Similarity	NPC473001
0.8882	High Similarity	NPC469901
0.8662	High Similarity	NPC473000
0.8625	High Similarity	NPC469900
0.8582	High Similarity	NPC200589
0.8242	Intermediate Similarity	NPC472999
0.8014	Intermediate Similarity	NPC255447
0.7973	Intermediate Similarity	NPC141050
0.7943	Intermediate Similarity	NPC200964
0.7925	Intermediate Similarity	NPC324850
0.7891	Intermediate Similarity	NPC130309
0.7877	Intermediate Similarity	NPC473322
0.7805	Intermediate Similarity	NPC141957
0.7762	Intermediate Similarity	NPC71684
0.7742	Intermediate Similarity	NPC262077
0.7697	Intermediate Similarity	NPC132636
0.7669	Intermediate Similarity	NPC241794
0.7662	Intermediate Similarity	NPC77905
0.7643	Intermediate Similarity	NPC240848
0.7635	Intermediate Similarity	NPC111428
0.759	Intermediate Similarity	NPC302597
0.7582	Intermediate Similarity	NPC89489
0.7564	Intermediate Similarity	NPC315266
0.7562	Intermediate Similarity	NPC122590
0.7552	Intermediate Similarity	NPC470546
0.755	Intermediate Similarity	NPC287401
0.7535	Intermediate Similarity	NPC239357
0.7529	Intermediate Similarity	NPC307396
0.75	Intermediate Similarity	NPC476978
0.75	Intermediate Similarity	NPC52748
0.7483	Intermediate Similarity	NPC470545
0.7453	Intermediate Similarity	NPC5194
0.7453	Intermediate Similarity	NPC261934
0.7453	Intermediate Similarity	NPC202198
0.7432	Intermediate Similarity	NPC101719
0.7415	Intermediate Similarity	NPC6975
0.7413	Intermediate Similarity	NPC315276
0.7413	Intermediate Similarity	NPC285926
0.7413	Intermediate Similarity	NPC14672
0.7413	Intermediate Similarity	NPC470544
0.7375	Intermediate Similarity	NPC2501
0.7368	Intermediate Similarity	NPC477462
0.7368	Intermediate Similarity	NPC136797
0.7365	Intermediate Similarity	NPC222466
0.7365	Intermediate Similarity	NPC22746
0.7351	Intermediate Similarity	NPC300315
0.7342	Intermediate Similarity	NPC316008
0.7342	Intermediate Similarity	NPC209509
0.7342	Intermediate Similarity	NPC313867
0.7329	Intermediate Similarity	NPC475168
0.7329	Intermediate Similarity	NPC7817
0.7325	Intermediate Similarity	NPC161069
0.7318	Intermediate Similarity	NPC276430
0.7312	Intermediate Similarity	NPC471820
0.7312	Intermediate Similarity	NPC471821
0.7296	Intermediate Similarity	NPC314358
0.7279	Intermediate Similarity	NPC202521
0.7278	Intermediate Similarity	NPC315283
0.7278	Intermediate Similarity	NPC314388
0.7244	Intermediate Similarity	NPC178662
0.7244	Intermediate Similarity	NPC476133
0.7244	Intermediate Similarity	NPC470884
0.7244	Intermediate Similarity	NPC92784
0.7244	Intermediate Similarity	NPC98424
0.7211	Intermediate Similarity	NPC476990
0.7209	Intermediate Similarity	NPC475532
0.7195	Intermediate Similarity	NPC470902
0.7181	Intermediate Similarity	NPC46427
0.7168	Intermediate Similarity	NPC165285
0.7143	Intermediate Similarity	NPC16188
0.7143	Intermediate Similarity	NPC138775
0.7134	Intermediate Similarity	NPC56685
0.7125	Intermediate Similarity	NPC5620
0.7114	Intermediate Similarity	NPC252878
0.7083	Intermediate Similarity	NPC276085
0.7076	Intermediate Similarity	NPC328649
0.7073	Intermediate Similarity	NPC233702
0.7067	Intermediate Similarity	NPC474082
0.7067	Intermediate Similarity	NPC175726
0.7066	Intermediate Similarity	NPC197743
0.7066	Intermediate Similarity	NPC297145
0.7059	Intermediate Similarity	NPC189116
0.7053	Intermediate Similarity	NPC54420
0.7051	Intermediate Similarity	NPC248283
0.7044	Intermediate Similarity	NPC263493
0.7044	Intermediate Similarity	NPC269398
0.7039	Intermediate Similarity	NPC477937
0.7037	Intermediate Similarity	NPC311658
0.7035	Intermediate Similarity	NPC129486
0.7034	Intermediate Similarity	NPC33742
0.703	Intermediate Similarity	NPC262166
0.6994	Remote Similarity	NPC198254
0.6994	Remote Similarity	NPC274198
0.6993	Remote Similarity	NPC319766
0.6989	Remote Similarity	NPC171317
0.6982	Remote Similarity	NPC471527
0.6981	Remote Similarity	NPC239762
0.6981	Remote Similarity	NPC163392
0.6979	Remote Similarity	NPC162860
0.6971	Remote Similarity	NPC17698
0.6962	Remote Similarity	NPC471264
0.6962	Remote Similarity	NPC471265
0.6959	Remote Similarity	NPC220698
0.6959	Remote Similarity	NPC63931
0.6951	Remote Similarity	NPC129666
0.6941	Remote Similarity	NPC68650
0.6928	Remote Similarity	NPC473341
0.6923	Remote Similarity	NPC62104
0.6923	Remote Similarity	NPC1390
0.6901	Remote Similarity	NPC471051
0.6901	Remote Similarity	NPC471052
0.6901	Remote Similarity	NPC471053
0.6897	Remote Similarity	NPC276506
0.6882	Remote Similarity	NPC469243
0.6855	Remote Similarity	NPC127741
0.6851	Remote Similarity	NPC96016
0.6849	Remote Similarity	NPC35850
0.6849	Remote Similarity	NPC276949
0.6848	Remote Similarity	NPC283783
0.6836	Remote Similarity	NPC196243
0.6832	Remote Similarity	NPC476989
0.6829	Remote Similarity	NPC329761
0.6829	Remote Similarity	NPC225648
0.6824	Remote Similarity	NPC24617
0.6821	Remote Similarity	NPC61004
0.6818	Remote Similarity	NPC242269
0.681	Remote Similarity	NPC477217
0.681	Remote Similarity	NPC322878
0.681	Remote Similarity	NPC201244
0.6804	Remote Similarity	NPC107077
0.6804	Remote Similarity	NPC223791
0.6792	Remote Similarity	NPC314835
0.6784	Remote Similarity	NPC475544
0.6784	Remote Similarity	NPC114806
0.6781	Remote Similarity	NPC474584
0.6763	Remote Similarity	NPC217804
0.6763	Remote Similarity	NPC223207
0.6763	Remote Similarity	NPC5719
0.6763	Remote Similarity	NPC22883
0.6763	Remote Similarity	NPC210377
0.676	Remote Similarity	NPC269750
0.676	Remote Similarity	NPC194671
0.6747	Remote Similarity	NPC254798
0.6743	Remote Similarity	NPC280022
0.6734	Remote Similarity	NPC238945
0.6727	Remote Similarity	NPC135121
0.6727	Remote Similarity	NPC145113
0.6725	Remote Similarity	NPC244336
0.6724	Remote Similarity	NPC471771
0.6724	Remote Similarity	NPC304074
0.6724	Remote Similarity	NPC290755
0.6724	Remote Similarity	NPC15068
0.6723	Remote Similarity	NPC137627
0.6722	Remote Similarity	NPC91179
0.6707	Remote Similarity	NPC473491
0.6687	Remote Similarity	NPC139326
0.6687	Remote Similarity	NPC105717
0.6687	Remote Similarity	NPC197682
0.6686	Remote Similarity	NPC63040
0.6685	Remote Similarity	NPC279871
0.6685	Remote Similarity	NPC318930
0.6685	Remote Similarity	NPC326407
0.6685	Remote Similarity	NPC317362
0.6685	Remote Similarity	NPC317725
0.6685	Remote Similarity	NPC26108
0.6667	Remote Similarity	NPC300443
0.6667	Remote Similarity	NPC314114
0.6667	Remote Similarity	NPC307357
0.6667	Remote Similarity	NPC476259
0.6667	Remote Similarity	NPC326349
0.6667	Remote Similarity	NPC162104
0.6667	Remote Similarity	NPC46098
0.6667	Remote Similarity	NPC323336
0.6667	Remote Similarity	NPC268841
0.6647	Remote Similarity	NPC473580
0.6645	Remote Similarity	NPC27833
0.6644	Remote Similarity	NPC319579
0.663	Remote Similarity	NPC153554
0.6629	Remote Similarity	NPC306804
0.6628	Remote Similarity	NPC104345
0.6628	Remote Similarity	NPC222029
0.6626	Remote Similarity	NPC168113
0.6625	Remote Similarity	NPC474473
0.6615	Remote Similarity	NPC472538
0.661	Remote Similarity	NPC475123
0.661	Remote Similarity	NPC475204
0.6605	Remote Similarity	NPC122553
0.6597	Remote Similarity	NPC106118
0.6595	Remote Similarity	NPC17059
0.6585	Remote Similarity	NPC468984
0.6585	Remote Similarity	NPC176226
0.6582	Remote Similarity	NPC475259
0.6582	Remote Similarity	NPC471945
0.6582	Remote Similarity	NPC471950
0.6582	Remote Similarity	NPC470491

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 NPC473002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	418
0.2-0.3	867
0.3-0.4	2369
0.4-0.5	4003
0.5-0.6	1163
0.6-0.7	158
0.7-0.8	24
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
0.831	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5263	Approved
0.7415	Intermediate Similarity	NPD3072	Approved
0.7415	Intermediate Similarity	NPD3073	Approved
0.7415	Intermediate Similarity	NPD3071	Approved
0.7389	Intermediate Similarity	NPD5341	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6901	Phase 3
0.7351	Intermediate Similarity	NPD4676	Approved
0.7347	Intermediate Similarity	NPD4761	Approved
0.7347	Intermediate Similarity	NPD4762	Approved
0.7325	Intermediate Similarity	NPD8076	Discontinued
0.7325	Intermediate Similarity	NPD7720	Phase 2
0.7318	Intermediate Similarity	NPD8240	Discontinued
0.7317	Intermediate Similarity	NPD7267	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6073	Approved
0.7255	Intermediate Similarity	NPD3632	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8630	Approved
0.7179	Intermediate Similarity	NPD5725	Approved
0.7179	Intermediate Similarity	NPD8173	Phase 2
0.7179	Intermediate Similarity	NPD8172	Phase 2
0.7171	Intermediate Similarity	NPD4175	Approved
0.7171	Intermediate Similarity	NPD4177	Approved
0.7126	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8643	Discontinued
0.7114	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5301	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2584	Suspended
0.7066	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6368	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4126	Approved
0.702	Intermediate Similarity	NPD4677	Discontinued
0.7006	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3908	Approved
0.6987	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6088	Approved
0.6944	Remote Similarity	NPD6557	Phase 2
0.6923	Remote Similarity	NPD5581	Approved
0.6914	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4125	Approved
0.6903	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5747	Discontinued
0.6839	Remote Similarity	NPD3040	Approved
0.6835	Remote Similarity	NPD6623	Phase 3
0.6835	Remote Similarity	NPD8416	Discontinued
0.6821	Remote Similarity	NPD8303	Discontinued
0.6813	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5265	Approved
0.681	Remote Similarity	NPD5264	Approved
0.6776	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4151	Approved
0.6772	Remote Similarity	NPD941	Approved
0.6747	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5323	Approved
0.6727	Remote Similarity	NPD8323	Discontinued
0.6709	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1330	Phase 2
0.6708	Remote Similarity	NPD6295	Approved
0.6708	Remote Similarity	NPD6294	Approved
0.6708	Remote Similarity	NPD6852	Discontinued
0.6707	Remote Similarity	NPD979	Approved
0.6707	Remote Similarity	NPD5024	Approved
0.6687	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD951	Approved
0.6667	Remote Similarity	NPD7613	Discontinued
0.6667	Remote Similarity	NPD1968	Approved
0.6667	Remote Similarity	NPD1967	Approved
0.6667	Remote Similarity	NPD5748	Phase 2
0.6646	Remote Similarity	NPD4794	Discontinued
0.6625	Remote Similarity	NPD4153	Approved
0.6625	Remote Similarity	NPD5296	Approved
0.6624	Remote Similarity	NPD1781	Discontinued
0.6624	Remote Similarity	NPD5759	Approved
0.6613	Remote Similarity	NPD7617	Discontinued
0.6604	Remote Similarity	NPD5299	Approved
0.6604	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3510	Approved
0.6587	Remote Similarity	NPD3509	Approved
0.6585	Remote Similarity	NPD2087	Approved
0.6585	Remote Similarity	NPD2088	Approved
0.6564	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3588	Discontinued
0.6561	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD8125	Discontinued
0.6543	Remote Similarity	NPD5004	Approved
0.6541	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6792	Phase 3
0.6538	Remote Similarity	NPD5367	Discontinued
0.6536	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7965	Phase 2
0.6531	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD8322	Phase 2
0.6519	Remote Similarity	NPD3626	Phase 3
0.6519	Remote Similarity	NPD7828	Discontinued
0.6509	Remote Similarity	NPD4432	Discontinued
0.6509	Remote Similarity	NPD5941	Approved
0.6509	Remote Similarity	NPD5942	Approved
0.6503	Remote Similarity	NPD4214	Discontinued
0.6497	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7599	Phase 2
0.6491	Remote Similarity	NPD8315	Phase 1
0.6491	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7771	Discontinued
0.6474	Remote Similarity	NPD7105	Phase 1
0.6471	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD747	Discontinued
0.6457	Remote Similarity	NPD7600	Phase 2
0.6446	Remote Similarity	NPD6681	Discovery
0.6437	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2031	Discontinued
0.6429	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3508	Approved
0.6391	Remote Similarity	NPD3519	Discontinued
0.6387	Remote Similarity	NPD5187	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2022	Approved
0.6374	Remote Similarity	NPD6144	Discontinued
0.637	Remote Similarity	NPD7130	Phase 3
0.6369	Remote Similarity	NPD7484	Phase 3
0.6369	Remote Similarity	NPD7485	Phase 3
0.6364	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3989	Phase 3
0.6353	Remote Similarity	NPD2016	Approved
0.6353	Remote Similarity	NPD2013	Approved
0.6353	Remote Similarity	NPD2014	Approved
0.6343	Remote Similarity	NPD7011	Discontinued
0.6331	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7683	Discontinued
0.6325	Remote Similarity	NPD7512	Approved
0.6325	Remote Similarity	NPD7511	Approved
0.6324	Remote Similarity	NPD3990	Phase 3
0.631	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3625	Discontinued
0.6286	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4091	Approved
0.6279	Remote Similarity	NPD5230	Approved
0.6279	Remote Similarity	NPD5229	Approved
0.6278	Remote Similarity	NPD6304	Approved
0.6278	Remote Similarity	NPD6303	Approved
0.6271	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8124	Phase 3
0.6258	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3988	Approved
0.6257	Remote Similarity	NPD3282	Phase 1
0.6257	Remote Similarity	NPD3283	Phase 3
0.6257	Remote Similarity	NPD3987	Approved
0.6257	Remote Similarity	NPD5614	Approved
0.6257	Remote Similarity	NPD5613	Approved
0.6256	Remote Similarity	NPD7780	Approved
0.6256	Remote Similarity	NPD7781	Approved
0.6256	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2437	Approved
0.625	Remote Similarity	NPD2436	Approved
0.625	Remote Similarity	NPD4092	Approved
0.6243	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD8351	Phase 2
0.6235	Remote Similarity	NPD2046	Approved
0.6235	Remote Similarity	NPD2043	Approved
0.6235	Remote Similarity	NPD2044	Approved
0.6235	Remote Similarity	NPD2047	Approved
0.6235	Remote Similarity	NPD2048	Approved
0.6235	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD2045	Approved
0.6235	Remote Similarity	NPD2051	Approved
0.6235	Remote Similarity	NPD21	Approved
0.6235	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7450	Phase 2
0.6226	Remote Similarity	NPD5578	Approved
0.6226	Remote Similarity	NPD3125	Approved
0.6226	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD7970	Approved
0.6225	Remote Similarity	NPD480	Approved
0.6221	Remote Similarity	NPD4682	Phase 2
0.622	Remote Similarity	NPD5272	Discontinued
0.6215	Remote Similarity	NPD4557	Approved
0.6215	Remote Similarity	NPD4566	Approved
0.6215	Remote Similarity	NPD4567	Approved
0.6211	Remote Similarity	NPD5851	Approved
0.6211	Remote Similarity	NPD5852	Approved
0.6209	Remote Similarity	NPD1348	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