NPASS Compound

Structure

NPC473000 OpenBabel07101718332D 94 99 0 0 1 0 0 0 0 0999 V2000 7.2333 -4.9162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4723 1.9432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6343 -5.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7683 -4.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8713 -7.8822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5865 -7.6411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5094 -7.1809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4430 -8.5458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1735 -3.2201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4113 0.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2339 -4.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9424 1.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3664 -7.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5003 -7.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2324 -7.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6856 -0.0610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7157 -9.7063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2620 -9.7989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5003 -6.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2324 -6.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6638 -0.2689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2555 -8.8645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3074 -9.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3441 -0.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1362 0.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1856 -0.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7483 -9.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8403 -8.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5003 -4.2634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5201 -6.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3664 -4.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3308 0.9203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2784 -2.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2868 0.9580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6343 -4.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6593 -7.2665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5822 -7.5555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7040 -4.1030 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4119 0.2123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3664 -5.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5357 1.5268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6010 -1.4064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2324 -4.2634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5003 -3.2634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5930 -5.9016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6958 -2.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7683 -1.2634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6216 -8.0910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2958 -8.5010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9997 -0.0233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8794 0.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7942 -6.9398 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7046 -4.1379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8820 -0.6358 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.0984 -4.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1793 -2.2222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3664 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8574 -4.9372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6343 -1.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4441 -7.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9671 -0.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6232 -5.1346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6468 -2.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3001 -8.5940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0912 -7.6510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0984 -5.7634 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6628 -1.2606 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8501 -0.7459 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.2324 -3.2634 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6343 -2.7634 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1132 -6.7791 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8923 -3.9378 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3142 -6.0857 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5539 -3.1494 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8547 -1.6702 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6902 -8.4548 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2432 -8.1810 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 0.5589 2.5265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6714 1.8882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8304 0.6010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9644 -4.2634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0567 -1.7425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3664 -1.7634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8460 -5.0879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5003 -1.2634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1046 -8.2731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3309 0.6550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6037 -5.3311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3900 -3.3175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2768 -9.5937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7160 -8.4318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2982 0.7395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 36 1 0 0 0 0 7 37 1 0 0 0 0 8 37 1 0 0 0 0 11 38 1 0 0 0 0 12 39 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 22 1 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 28 1 0 0 0 0 19 40 2 0 0 0 0 20 40 1 0 0 0 0 21 47 1 0 0 0 0 24 25 1 0 0 0 0 25 51 1 0 0 0 0 26 76 1 0 0 0 0 27 77 1 0 0 0 0 28 78 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 0 0 0 0 33 46 2 0 0 0 0 33 68 1 0 0 0 0 34 41 1 0 0 0 0 34 79 1 0 0 0 0 38 9 1 1 0 0 0 39 10 1 1 0 0 0 41 80 1 6 0 0 0 42 24 1 1 0 0 0 42 56 1 0 0 0 0 42 69 1 0 0 0 0 43 31 1 1 0 0 0 43 55 1 0 0 0 0 43 70 1 0 0 0 0 44 29 1 1 0 0 0 44 57 1 0 0 0 0 44 71 1 0 0 0 0 45 30 1 1 0 0 0 45 58 1 0 0 0 0 45 72 1 0 0 0 0 46 63 1 0 0 0 0 46 73 1 0 0 0 0 47 59 1 6 0 0 0 47 76 1 0 0 0 0 48 22 1 1 0 0 0 48 60 1 0 0 0 0 48 77 1 0 0 0 0 49 23 1 1 0 0 0 49 64 1 0 0 0 0 49 78 1 0 0 0 0 50 32 1 1 0 0 0 50 61 1 0 0 0 0 50 79 1 0 0 0 0 51 81 2 0 0 0 0 51 82 1 0 0 0 0 52 37 1 1 0 0 0 52 65 1 0 0 0 0 52 74 1 0 0 0 0 53 38 1 1 0 0 0 53 62 1 0 0 0 0 53 75 1 0 0 0 0 54 39 1 1 0 0 0 54 66 1 0 0 0 0 54 68 1 0 0 0 0 55 67 2 0 0 0 0 55 83 1 0 0 0 0 56 75 2 3 0 0 0 56 84 1 0 0 0 0 57 70 2 3 0 0 0 57 85 1 0 0 0 0 58 73 2 3 0 0 0 58 86 1 0 0 0 0 59 71 2 3 0 0 0 59 87 1 0 0 0 0 60 72 2 3 0 0 0 60 88 1 0 0 0 0 61 69 2 3 0 0 0 61 89 1 0 0 0 0 62 74 2 3 0 0 0 62 90 1 0 0 0 0 63 76 1 0 0 0 0 63 91 2 0 0 0 0 64 77 1 0 0 0 0 64 92 2 0 0 0 0 65 78 1 0 0 0 0 65 93 2 0 0 0 0 66 79 1 0 0 0 0 66 94 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1315.75
Volume:	1328.744
LogP:	2.152
LogD:	1.383
LogS:	-2.507
# Rotatable Bonds:	23
TPSA:	412.54
# H-Bond Aceptor:	28
# H-Bond Donor:	12
# Rings:	6
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	7.575
Fsp3:	0.682
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:	-5.43
MDCK Permeability:	0.0002345851535210386
Pgp-inhibitor:	0.018
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.846
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	50.55813217163086%
Volume Distribution (VD):	0.708
Pgp-substrate:	35.250587463378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.232
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.334
Carcinogencity:	0.263
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC473000

Natural Product ID:	NPC473000
*Common Name:**	WSNONXGZAQRQBF-ZYXJJOLVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WSNONXGZAQRQBF-ZYXJJOLVSA-N
Standard InCHI:	InChI=1S/C66H101N13O15/c1-11-38(9)53-62(90)74-52(37(7)8)65(93)78-28-18-23-49(78)64(92)77-27-17-22-48(77)60(88)72-45(30-36(5)6)58(86)73-46(33-68-54(39(10)12-2)66(94)79-34-41(80)32-50(79)61(89)69-42(56(84)75-53)24-25-51(81)82)63(91)76-26-16-21-47(76)59(87)71-44(29-35(3)4)57(85)70-43(55(67)83)31-40-19-14-13-15-20-40/h13-15,19-20,33,35-39,41-45,47-50,52-54,68,80H,11-12,16-18,21-32,34H2,1-10H3,(H2,67,83)(H,69,89)(H,70,85)(H,71,87)(H,72,88)(H,73,86)(H,74,90)(H,75,84)(H,81,82)/b46-33-/t38-,39-,41+,42-,43-,44-,45-,47-,48-,49-,50-,52-,53-,54-/m0/s1
SMILES:	CCC(C)C1C(=O)NC(C(=O)N2CCCC2C(=O)N3CCCC3C(=O)NC(C(=O)NC(=CNC(C(=O)N4CC(CC4C(=O)NC(C(=O)N1)CCC(=O)O)O)C(C)CC)C(=O)N5CCCC5C(=O)NC(CC(C)C)C(=O)NC(CC6=CC=CC=C6)C(=O)N)CC(C)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597656
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[493397]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	10000.0	nM	PMID[493397]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	100000.0	nM	PMID[493397]

☑ 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 NPC473000 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	180
0.1-0.2	1025
0.2-0.3	5811
0.3-0.4	25028
0.4-0.5	7880
0.5-0.6	2099
0.6-0.7	490
0.7-0.8	166
0.8-0.85	8
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC469898
0.9313	High Similarity	NPC469900
0.9226	High Similarity	NPC469901
0.8981	High Similarity	NPC469902
0.8726	High Similarity	NPC469903
0.8683	High Similarity	NPC472999
0.8662	High Similarity	NPC473002
0.865	High Similarity	NPC469904
0.8625	High Similarity	NPC473003
0.8563	High Similarity	NPC473001
0.8269	Intermediate Similarity	NPC315266
0.8258	Intermediate Similarity	NPC77905
0.8049	Intermediate Similarity	NPC324850
0.7987	Intermediate Similarity	NPC141050
0.795	Intermediate Similarity	NPC2501
0.7922	Intermediate Similarity	NPC287401
0.7908	Intermediate Similarity	NPC130309
0.7901	Intermediate Similarity	NPC7817
0.7901	Intermediate Similarity	NPC475168
0.7866	Intermediate Similarity	NPC470902
0.7862	Intermediate Similarity	NPC476978
0.7862	Intermediate Similarity	NPC52748
0.7805	Intermediate Similarity	NPC473341
0.7805	Intermediate Similarity	NPC122590
0.7803	Intermediate Similarity	NPC477462
0.7778	Intermediate Similarity	NPC240848
0.7764	Intermediate Similarity	NPC314358
0.7725	Intermediate Similarity	NPC297145
0.7725	Intermediate Similarity	NPC197743
0.7702	Intermediate Similarity	NPC313867
0.7702	Intermediate Similarity	NPC316008
0.7679	Intermediate Similarity	NPC24617
0.7673	Intermediate Similarity	NPC163392
0.7673	Intermediate Similarity	NPC239762
0.7669	Intermediate Similarity	NPC471821
0.7669	Intermediate Similarity	NPC471820
0.764	Intermediate Similarity	NPC315283
0.764	Intermediate Similarity	NPC314388
0.7636	Intermediate Similarity	NPC300443
0.7633	Intermediate Similarity	NPC114806
0.7574	Intermediate Similarity	NPC1390
0.7574	Intermediate Similarity	NPC62104
0.7547	Intermediate Similarity	NPC471265
0.7547	Intermediate Similarity	NPC471264
0.7514	Intermediate Similarity	NPC302597
0.7453	Intermediate Similarity	NPC476259
0.7451	Intermediate Similarity	NPC6975
0.7451	Intermediate Similarity	NPC46427
0.7439	Intermediate Similarity	NPC262077
0.7427	Intermediate Similarity	NPC471527
0.7407	Intermediate Similarity	NPC263493
0.7407	Intermediate Similarity	NPC269398
0.7399	Intermediate Similarity	NPC22883
0.7399	Intermediate Similarity	NPC210377
0.7399	Intermediate Similarity	NPC217804
0.7399	Intermediate Similarity	NPC5719
0.7391	Intermediate Similarity	NPC178662
0.7391	Intermediate Similarity	NPC98424
0.7391	Intermediate Similarity	NPC470884
0.7391	Intermediate Similarity	NPC476133
0.7391	Intermediate Similarity	NPC92784
0.7389	Intermediate Similarity	NPC200589
0.7386	Intermediate Similarity	NPC252878
0.7378	Intermediate Similarity	NPC209509
0.7378	Intermediate Similarity	NPC5620
0.7372	Intermediate Similarity	NPC319766
0.733	Intermediate Similarity	NPC475123
0.733	Intermediate Similarity	NPC475204
0.733	Intermediate Similarity	NPC46009
0.732	Intermediate Similarity	NPC202521
0.7314	Intermediate Similarity	NPC63040
0.7301	Intermediate Similarity	NPC168113
0.7278	Intermediate Similarity	NPC261934
0.7278	Intermediate Similarity	NPC5194
0.7257	Intermediate Similarity	NPC15068
0.7257	Intermediate Similarity	NPC61004
0.7256	Intermediate Similarity	NPC176226
0.7256	Intermediate Similarity	NPC161069
0.7256	Intermediate Similarity	NPC197682
0.7255	Intermediate Similarity	NPC476990
0.7234	Intermediate Similarity	NPC477632
0.7234	Intermediate Similarity	NPC477638
0.7219	Intermediate Similarity	NPC162104
0.7207	Intermediate Similarity	NPC136797
0.7202	Intermediate Similarity	NPC129666
0.7191	Intermediate Similarity	NPC328494
0.7184	Intermediate Similarity	NPC241794
0.7178	Intermediate Similarity	NPC132636
0.7176	Intermediate Similarity	NPC56685
0.7176	Intermediate Similarity	NPC262166
0.7171	Intermediate Similarity	NPC469899
0.7169	Intermediate Similarity	NPC322878
0.7143	Intermediate Similarity	NPC471053
0.7143	Intermediate Similarity	NPC200964
0.7143	Intermediate Similarity	NPC471051
0.7143	Intermediate Similarity	NPC471052
0.7128	Intermediate Similarity	NPC477631
0.7125	Intermediate Similarity	NPC255447
0.7119	Intermediate Similarity	NPC141957
0.7111	Intermediate Similarity	NPC471165
0.7104	Intermediate Similarity	NPC477637
0.7104	Intermediate Similarity	NPC473404
0.7097	Intermediate Similarity	NPC71684
0.7088	Intermediate Similarity	NPC194671
0.7088	Intermediate Similarity	NPC269750
0.7083	Intermediate Similarity	NPC225648
0.7083	Intermediate Similarity	NPC329761
0.7083	Intermediate Similarity	NPC138775
0.7073	Intermediate Similarity	NPC89489
0.707	Intermediate Similarity	NPC22746
0.7063	Intermediate Similarity	NPC300315
0.7048	Intermediate Similarity	NPC139326
0.7021	Intermediate Similarity	NPC477636
0.702	Intermediate Similarity	NPC107077
0.702	Intermediate Similarity	NPC223791
0.7012	Intermediate Similarity	NPC127741
0.7012	Intermediate Similarity	NPC68865
0.7006	Intermediate Similarity	NPC63931
0.7006	Intermediate Similarity	NPC175726
0.7006	Intermediate Similarity	NPC474082
0.7	Intermediate Similarity	NPC111428
0.7	Intermediate Similarity	NPC473322
0.6994	Remote Similarity	NPC248283
0.6994	Remote Similarity	NPC244509
0.6993	Remote Similarity	NPC239357
0.6989	Remote Similarity	NPC307396
0.6989	Remote Similarity	NPC73655
0.6988	Remote Similarity	NPC469427
0.6988	Remote Similarity	NPC469426
0.6982	Remote Similarity	NPC135121
0.6982	Remote Similarity	NPC145113
0.6982	Remote Similarity	NPC311658
0.6978	Remote Similarity	NPC50016
0.6964	Remote Similarity	NPC201244
0.6964	Remote Similarity	NPC477217
0.6961	Remote Similarity	NPC137627
0.6961	Remote Similarity	NPC306804
0.6927	Remote Similarity	NPC107938
0.6927	Remote Similarity	NPC294516
0.6927	Remote Similarity	NPC477639
0.6923	Remote Similarity	NPC279871
0.6918	Remote Similarity	NPC101719
0.6914	Remote Similarity	NPC326349
0.6914	Remote Similarity	NPC323336
0.691	Remote Similarity	NPC472923
0.6903	Remote Similarity	NPC470546
0.6898	Remote Similarity	NPC299806
0.6875	Remote Similarity	NPC244336
0.6868	Remote Similarity	NPC273755
0.6868	Remote Similarity	NPC248670
0.6855	Remote Similarity	NPC222466
0.6851	Remote Similarity	NPC40234
0.6848	Remote Similarity	NPC314835
0.6842	Remote Similarity	NPC61332
0.6842	Remote Similarity	NPC240130
0.6839	Remote Similarity	NPC470545
0.6833	Remote Similarity	NPC328649
0.6831	Remote Similarity	NPC473402
0.6831	Remote Similarity	NPC317362
0.6831	Remote Similarity	NPC26108
0.6831	Remote Similarity	NPC318930
0.6826	Remote Similarity	NPC268841
0.6826	Remote Similarity	NPC307357
0.6826	Remote Similarity	NPC46098
0.6813	Remote Similarity	NPC230611
0.6811	Remote Similarity	NPC45037
0.6796	Remote Similarity	NPC129486
0.6795	Remote Similarity	NPC314992
0.6791	Remote Similarity	NPC470903
0.6791	Remote Similarity	NPC167763
0.6791	Remote Similarity	NPC470112
0.6782	Remote Similarity	NPC202198
0.678	Remote Similarity	NPC238945
0.6774	Remote Similarity	NPC470544
0.6768	Remote Similarity	NPC246079
0.6766	Remote Similarity	NPC162860
0.6753	Remote Similarity	NPC329295
0.6744	Remote Similarity	NPC105717
0.6739	Remote Similarity	NPC326407
0.6739	Remote Similarity	NPC155506
0.6739	Remote Similarity	NPC317725
0.6739	Remote Similarity	NPC476227
0.6739	Remote Similarity	NPC159767
0.6722	Remote Similarity	NPC189116
0.6717	Remote Similarity	NPC155143
0.6709	Remote Similarity	NPC478016
0.6709	Remote Similarity	NPC478015
0.6709	Remote Similarity	NPC478014
0.6702	Remote Similarity	NPC102959
0.6685	Remote Similarity	NPC475532
0.6684	Remote Similarity	NPC171317
0.6667	Remote Similarity	NPC294951
0.6667	Remote Similarity	NPC60516
0.6667	Remote Similarity	NPC2265
0.6667	Remote Similarity	NPC274198
0.6667	Remote Similarity	NPC54420
0.6667	Remote Similarity	NPC473491
0.6667	Remote Similarity	NPC198254
0.6667	Remote Similarity	NPC475506
0.6649	Remote Similarity	NPC165285

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 NPC473000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	368
0.2-0.3	735
0.3-0.4	2775
0.4-0.5	3930
0.5-0.6	1058
0.6-0.7	151
0.7-0.8	10
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
0.7578	Intermediate Similarity	NPD8076	Discontinued
0.75	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD8172	Phase 2
0.7438	Intermediate Similarity	NPD8173	Phase 2
0.7312	Intermediate Similarity	NPD8416	Discontinued
0.731	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3072	Approved
0.7226	Intermediate Similarity	NPD3071	Approved
0.7226	Intermediate Similarity	NPD3073	Approved
0.7222	Intermediate Similarity	NPD5725	Approved
0.7215	Intermediate Similarity	NPD4177	Approved
0.7215	Intermediate Similarity	NPD4175	Approved
0.7202	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6901	Phase 3
0.717	Intermediate Similarity	NPD4676	Approved
0.7161	Intermediate Similarity	NPD4761	Approved
0.7161	Intermediate Similarity	NPD4762	Approved
0.7134	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6073	Approved
0.7117	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5263	Approved
0.7037	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1330	Phase 2
0.6966	Remote Similarity	NPD8303	Discontinued
0.6951	Remote Similarity	NPD8643	Discontinued
0.6951	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5747	Discontinued
0.6899	Remote Similarity	NPD2584	Suspended
0.6898	Remote Similarity	NPD6557	Phase 2
0.689	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4126	Approved
0.6864	Remote Similarity	NPD5265	Approved
0.6864	Remote Similarity	NPD5264	Approved
0.6857	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4794	Discontinued
0.6795	Remote Similarity	NPD2218	Phase 2
0.6795	Remote Similarity	NPD2217	Approved
0.679	Remote Similarity	NPD3040	Approved
0.6788	Remote Similarity	NPD4153	Approved
0.6788	Remote Similarity	NPD5323	Approved
0.6776	Remote Similarity	NPD8124	Phase 3
0.6776	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6852	Discontinued
0.6748	Remote Similarity	NPD4125	Approved
0.6743	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3588	Discontinued
0.6724	Remote Similarity	NPD7613	Discontinued
0.6719	Remote Similarity	NPD5077	Approved
0.6719	Remote Similarity	NPD5076	Approved
0.6705	Remote Similarity	NPD6088	Approved
0.6686	Remote Similarity	NPD8323	Discontinued
0.6685	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7965	Phase 2
0.6685	Remote Similarity	NPD8630	Approved
0.6667	Remote Similarity	NPD5299	Approved
0.6649	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4557	Approved
0.6647	Remote Similarity	NPD2087	Approved
0.6647	Remote Similarity	NPD2088	Approved
0.6646	Remote Similarity	NPD4677	Discontinued
0.6646	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8240	Discontinued
0.6627	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5367	Discontinued
0.6605	Remote Similarity	NPD3125	Approved
0.6587	Remote Similarity	NPD6623	Phase 3
0.6587	Remote Similarity	NPD5296	Approved
0.6584	Remote Similarity	NPD8322	Phase 2
0.6575	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7720	Phase 2
0.6548	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1968	Approved
0.6532	Remote Similarity	NPD1967	Approved
0.6524	Remote Similarity	NPD4151	Approved
0.6512	Remote Similarity	NPD6681	Discovery
0.6482	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7683	Discontinued
0.6471	Remote Similarity	NPD6295	Approved
0.6471	Remote Similarity	NPD4214	Discontinued
0.6471	Remote Similarity	NPD6294	Approved
0.6467	Remote Similarity	NPD5581	Approved
0.6461	Remote Similarity	NPD4648	Approved
0.6461	Remote Similarity	NPD8315	Phase 1
0.6461	Remote Similarity	NPD4646	Approved
0.6461	Remote Similarity	NPD4647	Approved
0.6453	Remote Similarity	NPD2022	Approved
0.6444	Remote Similarity	NPD7105	Phase 1
0.6441	Remote Similarity	NPD5230	Approved
0.6441	Remote Similarity	NPD5229	Approved
0.6433	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD6304	Approved
0.6432	Remote Similarity	NPD6303	Approved
0.6429	Remote Similarity	NPD7600	Phase 2
0.6424	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4652	Approved
0.6398	Remote Similarity	NPD7342	Discontinued
0.6392	Remote Similarity	NPD1348	Approved
0.6386	Remote Similarity	NPD3626	Phase 3
0.6374	Remote Similarity	NPD7599	Phase 2
0.6364	Remote Similarity	NPD3519	Discontinued
0.6358	Remote Similarity	NPD7978	Discontinued
0.6354	Remote Similarity	NPD1663	Discontinued
0.6353	Remote Similarity	NPD3908	Approved
0.6335	Remote Similarity	NPD3989	Phase 3
0.6333	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD941	Approved
0.6329	Remote Similarity	NPD747	Discontinued
0.6328	Remote Similarity	NPD3987	Approved
0.6328	Remote Similarity	NPD3988	Approved
0.6328	Remote Similarity	NPD2013	Approved
0.6328	Remote Similarity	NPD2014	Approved
0.6328	Remote Similarity	NPD2016	Approved
0.631	Remote Similarity	NPD2046	Approved
0.631	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2047	Approved
0.631	Remote Similarity	NPD2043	Approved
0.631	Remote Similarity	NPD2044	Approved
0.631	Remote Similarity	NPD2048	Approved
0.631	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2045	Approved
0.631	Remote Similarity	NPD2051	Approved
0.631	Remote Similarity	NPD21	Approved
0.6307	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD3990	Phase 3
0.6298	Remote Similarity	NPD2891	Approved
0.6294	Remote Similarity	NPD6058	Phase 2
0.6292	Remote Similarity	NPD5942	Approved
0.6292	Remote Similarity	NPD979	Approved
0.6292	Remote Similarity	NPD5941	Approved
0.6287	Remote Similarity	NPD5759	Approved
0.6286	Remote Similarity	NPD5024	Approved
0.6284	Remote Similarity	NPD4566	Approved
0.6284	Remote Similarity	NPD4567	Approved
0.6281	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3510	Approved
0.6271	Remote Similarity	NPD3509	Approved
0.6268	Remote Similarity	NPD7605	Discovery
0.6265	Remote Similarity	NPD3606	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD951	Approved
0.6263	Remote Similarity	NPD6665	Discontinued
0.6263	Remote Similarity	NPD4091	Approved
0.6257	Remote Similarity	NPD7485	Phase 3
0.6257	Remote Similarity	NPD7484	Phase 3
0.625	Remote Similarity	NPD2097	Approved
0.625	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD8272	Phase 2
0.6236	Remote Similarity	NPD5613	Approved
0.6236	Remote Similarity	NPD5614	Approved
0.623	Remote Similarity	NPD3993	Approved
0.623	Remote Similarity	NPD3995	Approved
0.623	Remote Similarity	NPD3992	Approved
0.623	Remote Similarity	NPD3996	Approved
0.623	Remote Similarity	NPD4092	Approved
0.623	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3991	Approved
0.623	Remote Similarity	NPD3994	Approved
0.6229	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7523	Phase 3
0.6216	Remote Similarity	NPD8351	Phase 2
0.6209	Remote Similarity	NPD8417	Discontinued
0.6207	Remote Similarity	NPD7512	Approved
0.6207	Remote Similarity	NPD7511	Approved
0.6205	Remote Similarity	NPD6792	Phase 3
0.6198	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD3999	Approved
0.6198	Remote Similarity	NPD3998	Approved
0.6198	Remote Similarity	NPD3997	Approved
0.6193	Remote Similarity	NPD8292	Phase 2
0.6188	Remote Similarity	NPD7508	Discontinued
0.6183	Remote Similarity	NPD2098	Approved
0.6176	Remote Similarity	NPD7817	Phase 1
0.6169	Remote Similarity	NPD1040	Phase 2
0.6168	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD6676	Phase 2
0.6154	Remote Similarity	NPD2613	Approved
0.6149	Remote Similarity	NPD3480	Approved
0.6145	Remote Similarity	NPD3282	Phase 1
0.6145	Remote Similarity	NPD3283	Phase 3
0.6141	Remote Similarity	NPD7011	Discontinued
0.614	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD2436	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