NPASS Compound

Structure

NPC469904 OpenBabel07101719122D 90 98 0 0 1 0 0 0 0 0999 V2000 7.4095 -2.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6806 -2.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8684 6.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1522 4.9691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1917 5.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7276 7.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6558 1.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3257 5.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.1917 4.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5936 6.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8616 6.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.6558 2.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.7898 0.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1808 5.4336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7100 -3.3468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1588 5.9940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 -1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 2.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4596 5.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3257 3.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5936 5.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8616 5.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.7898 2.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9237 1.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1590 5.2257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5527 -2.8085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6332 5.1433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0242 -1.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3235 1.9210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6808 4.5676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9376 -2.7117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1303 5.7569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9556 -0.2948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8698 3.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6348 -0.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5306 5.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5936 3.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7276 4.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0577 2.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7437 3.4317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5750 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5171 5.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4596 4.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7276 5.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9237 2.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8002 -0.3475 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.5936 2.7312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8616 3.7312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1792 4.6415 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.1917 2.2312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1910 2.5373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2635 4.2312 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3011 -1.8406 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2798 4.3805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5756 -0.8177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3240 1.9509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2206 0.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8616 2.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4596 2.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1295 3.7312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2726 -1.6035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2010 4.8494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1420 2.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3667 -1.4294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5073 3.7454 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 15.1917 1.2312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0526 4.1545 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.7276 2.2312 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1311 -1.0906 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.9955 4.2312 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.3257 2.7312 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3548 1.5508 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3499 3.8245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.3029 -1.7808 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2051 4.7597 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 -0.0435 2.9108 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.1804 0.2794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9955 2.2312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4596 1.2312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1295 2.7312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6518 -2.5288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2608 5.8476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8852 2.1772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8797 -2.3029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2358 4.4145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2955 0.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.0577 0.7312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3257 0.7312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 41 1 0 0 0 0 2 41 1 0 0 0 0 3 42 1 0 0 0 0 4 42 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 25 1 0 0 0 0 14 30 1 0 0 0 0 15 26 1 0 0 0 0 15 31 1 0 0 0 0 16 27 1 0 0 0 0 16 32 1 0 0 0 0 17 28 1 0 0 0 0 17 33 1 0 0 0 0 18 29 1 0 0 0 0 18 34 1 0 0 0 0 19 43 2 0 0 0 0 20 43 1 0 0 0 0 21 44 2 0 0 0 0 22 44 1 0 0 0 0 23 45 2 0 0 0 0 24 45 1 0 0 0 0 25 52 1 0 0 0 0 30 74 1 0 0 0 0 31 75 1 0 0 0 0 32 76 1 0 0 0 0 33 77 1 0 0 0 0 34 78 1 0 0 0 0 35 41 1 0 0 0 0 36 42 1 0 0 0 0 37 43 1 0 0 0 0 38 44 1 0 0 0 0 39 45 1 0 0 0 0 40 51 2 0 0 0 0 40 68 1 0 0 0 0 46 35 1 6 0 0 0 46 57 1 0 0 0 0 46 70 1 0 0 0 0 47 37 1 1 0 0 0 47 59 1 0 0 0 0 47 69 1 0 0 0 0 48 38 1 1 0 0 0 48 58 1 0 0 0 0 48 71 1 0 0 0 0 49 36 1 6 0 0 0 49 62 1 0 0 0 0 49 68 1 0 0 0 0 50 39 1 1 0 0 0 50 67 1 0 0 0 0 50 72 1 0 0 0 0 51 63 1 0 0 0 0 51 73 1 0 0 0 0 52 60 1 1 0 0 0 52 74 1 0 0 0 0 53 26 1 6 0 0 0 53 61 1 0 0 0 0 53 75 1 0 0 0 0 54 27 1 6 0 0 0 54 65 1 0 0 0 0 54 76 1 0 0 0 0 55 28 1 1 0 0 0 55 64 1 0 0 0 0 55 77 1 0 0 0 0 56 29 1 6 0 0 0 56 66 1 0 0 0 0 56 78 1 0 0 0 0 57 73 2 3 0 0 0 57 79 1 0 0 0 0 58 69 2 3 0 0 0 58 80 1 0 0 0 0 59 72 2 3 0 0 0 59 81 1 0 0 0 0 60 71 2 3 0 0 0 60 82 1 0 0 0 0 61 70 2 3 0 0 0 61 83 1 0 0 0 0 62 76 1 0 0 0 0 62 84 2 0 0 0 0 63 74 1 0 0 0 0 63 85 2 0 0 0 0 64 75 1 0 0 0 0 64 86 2 0 0 0 0 65 78 1 0 0 0 0 65 87 2 0 0 0 0 66 77 1 0 0 0 0 66 88 2 0 0 0 0 67 89 2 0 0 0 0 67 90 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1237.65
Volume:	1261.461
LogP:	4.788
LogD:	4.188
LogS:	-3.295
# Rotatable Bonds:	22
TPSA:	303.36
# H-Bond Aceptor:	23
# H-Bond Donor:	7
# Rings:	9
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	6.614
Fsp3:	0.537
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:	-6.593
MDCK Permeability:	3.0183440685505047e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.877
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	72.50391387939453%
Volume Distribution (VD):	0.52
Pgp-substrate:	17.118568420410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.554
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.167
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.558
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.659
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.461
Carcinogencity:	0.156
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.577

Download Data

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

Natural Product: NPC469904

Natural Product ID:	NPC469904
*Common Name:**	Callyaerin G
IUPAC Name:	n.a.
Synonyms:	Callyaerin G
Standard InCHIKey:	DYTFXINNOGEETQ-KUIQLQJMSA-N
Standard InCHI:	InChI=1S/C67H87N11O12/c1-41(2)35-46-57(79)73-51(40-68-49(36-42(3)4)62(84)76-32-16-27-54(76)65(87)78-34-18-29-56(78)66(88)77-33-17-28-55(77)64(86)75-31-15-26-53(75)61(83)70-46)63(85)74-30-14-25-52(74)60(82)71-48(38-44-21-10-6-11-22-44)58(80)69-47(37-43-19-8-5-9-20-43)59(81)72-50(67(89)90)39-45-23-12-7-13-24-45/h5-13,19-24,40-42,46-50,52-56,68H,14-18,25-39H2,1-4H3,(H,69,80)(H,70,83)(H,71,82)(H,72,81)(H,73,79)(H,89,90)/b51-40+/t46-,47-,48-,49-,50-,52-,53-,54-,55+,56-/m0/s1
SMILES:	CC(C[C@@H]1N=C(O)[C@@H]2CCCN2C(=O)[C@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H]2N(C(=O)[C@@H](N/C=C(/N=C1O)C(=O)N1CCC[C@H]1C(=N[C@H](C(=N[C@H](C(=N[C@H](C(=O)O)Cc1ccccc1)O)Cc1ccccc1)O)Cc1ccccc1)O)CC(C)C)CCC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1253754
PubChem CID:	52941213
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
ED50	3
IC50	2
Others	1

Activity Type	# Activity
Cell Line	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	>	8.0	uM	PMID[537288]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	4.43	uM	PMID[537288]
NPT1864	Cell Line	L5178Y	Mus musculus	ED50	=	0.41	uM	PMID[537288]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[537289]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	10000.0	nM	PMID[537289]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	100000.0	nM	PMID[537289]

☑ 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 NPC469904 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	238
0.1-0.2	1270
0.2-0.3	8869
0.3-0.4	22939
0.4-0.5	7039
0.5-0.6	1761
0.6-0.7	475
0.7-0.8	93
0.8-0.85	3
0.85-0.9	4
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9605	High Similarity	NPC473003
0.9605	High Similarity	NPC469902
0.9342	High Similarity	NPC469903
0.9276	High Similarity	NPC473002
0.9255	High Similarity	NPC473001
0.8957	High Similarity	NPC469900
0.8679	High Similarity	NPC469898
0.865	High Similarity	NPC473000
0.8625	High Similarity	NPC469901
0.8035	Intermediate Similarity	NPC472999
0.8026	Intermediate Similarity	NPC255447
0.7961	Intermediate Similarity	NPC200589
0.7939	Intermediate Similarity	NPC324850
0.7895	Intermediate Similarity	NPC473322
0.7824	Intermediate Similarity	NPC141957
0.7722	Intermediate Similarity	NPC132636
0.7662	Intermediate Similarity	NPC111428
0.7593	Intermediate Similarity	NPC315266
0.759	Intermediate Similarity	NPC122590
0.7564	Intermediate Similarity	NPC130309
0.7546	Intermediate Similarity	NPC262077
0.7531	Intermediate Similarity	NPC476978
0.7469	Intermediate Similarity	NPC77905
0.7455	Intermediate Similarity	NPC240848
0.7434	Intermediate Similarity	NPC71684
0.7421	Intermediate Similarity	NPC141050
0.741	Intermediate Similarity	NPC2501
0.7401	Intermediate Similarity	NPC477462
0.7401	Intermediate Similarity	NPC136797
0.7384	Intermediate Similarity	NPC241794
0.7378	Intermediate Similarity	NPC313867
0.7378	Intermediate Similarity	NPC209509
0.7378	Intermediate Similarity	NPC316008
0.7368	Intermediate Similarity	NPC200964
0.7365	Intermediate Similarity	NPC7817
0.7365	Intermediate Similarity	NPC475168
0.7363	Intermediate Similarity	NPC307396
0.7362	Intermediate Similarity	NPC161069
0.7351	Intermediate Similarity	NPC276430
0.7333	Intermediate Similarity	NPC314358
0.7317	Intermediate Similarity	NPC52748
0.7317	Intermediate Similarity	NPC314388
0.7317	Intermediate Similarity	NPC315283
0.7314	Intermediate Similarity	NPC302597
0.725	Intermediate Similarity	NPC287401
0.7237	Intermediate Similarity	NPC470546
0.7235	Intermediate Similarity	NPC470902
0.7186	Intermediate Similarity	NPC138775
0.7176	Intermediate Similarity	NPC5194
0.7176	Intermediate Similarity	NPC261934
0.7176	Intermediate Similarity	NPC202198
0.7171	Intermediate Similarity	NPC470545
0.7169	Intermediate Similarity	NPC5620
0.7167	Intermediate Similarity	NPC196243
0.7143	Intermediate Similarity	NPC471821
0.7143	Intermediate Similarity	NPC471820
0.7134	Intermediate Similarity	NPC101719
0.7126	Intermediate Similarity	NPC471527
0.7119	Intermediate Similarity	NPC328649
0.7118	Intermediate Similarity	NPC233702
0.7115	Intermediate Similarity	NPC6975
0.711	Intermediate Similarity	NPC297145
0.711	Intermediate Similarity	NPC197743
0.7105	Intermediate Similarity	NPC470544
0.7102	Intermediate Similarity	NPC223207
0.7102	Intermediate Similarity	NPC189116
0.7091	Intermediate Similarity	NPC269398
0.7091	Intermediate Similarity	NPC263493
0.7089	Intermediate Similarity	NPC477937
0.7083	Intermediate Similarity	NPC311658
0.7076	Intermediate Similarity	NPC473341
0.7073	Intermediate Similarity	NPC98424
0.7073	Intermediate Similarity	NPC470884
0.7073	Intermediate Similarity	NPC178662
0.7073	Intermediate Similarity	NPC92784
0.7073	Intermediate Similarity	NPC476133
0.7073	Intermediate Similarity	NPC89489
0.707	Intermediate Similarity	NPC22746
0.707	Intermediate Similarity	NPC222466
0.7063	Intermediate Similarity	NPC300315
0.7062	Intermediate Similarity	NPC304074
0.7062	Intermediate Similarity	NPC290755
0.7062	Intermediate Similarity	NPC471771
0.7045	Intermediate Similarity	NPC471052
0.7045	Intermediate Similarity	NPC471053
0.7045	Intermediate Similarity	NPC471051
0.7039	Intermediate Similarity	NPC198254
0.7039	Intermediate Similarity	NPC274198
0.703	Intermediate Similarity	NPC163392
0.703	Intermediate Similarity	NPC239762
0.7017	Intermediate Similarity	NPC326407
0.7017	Intermediate Similarity	NPC317725
0.7012	Intermediate Similarity	NPC471265
0.7012	Intermediate Similarity	NPC471264
0.7006	Intermediate Similarity	NPC63931
0.7	Intermediate Similarity	NPC129666
0.6993	Remote Similarity	NPC239357
0.6987	Remote Similarity	NPC202521
0.6971	Remote Similarity	NPC62104
0.6971	Remote Similarity	NPC1390
0.6961	Remote Similarity	NPC475532
0.6944	Remote Similarity	NPC276506
0.6932	Remote Similarity	NPC469243
0.6923	Remote Similarity	NPC165285
0.6923	Remote Similarity	NPC476990
0.6919	Remote Similarity	NPC54420
0.6909	Remote Similarity	NPC127741
0.6902	Remote Similarity	NPC194671
0.6902	Remote Similarity	NPC269750
0.6899	Remote Similarity	NPC46427
0.6883	Remote Similarity	NPC14672
0.6883	Remote Similarity	NPC285926
0.6883	Remote Similarity	NPC315276
0.6882	Remote Similarity	NPC16188
0.6882	Remote Similarity	NPC329761
0.6882	Remote Similarity	NPC225648
0.6879	Remote Similarity	NPC56685
0.6875	Remote Similarity	NPC24617
0.6872	Remote Similarity	NPC61004
0.6868	Remote Similarity	NPC137627
0.6864	Remote Similarity	NPC322878
0.685	Remote Similarity	NPC162860
0.6848	Remote Similarity	NPC314835
0.6842	Remote Similarity	NPC474584
0.6836	Remote Similarity	NPC475544
0.6836	Remote Similarity	NPC114806
0.6835	Remote Similarity	NPC252878
0.6831	Remote Similarity	NPC279871
0.6824	Remote Similarity	NPC314114
0.6816	Remote Similarity	NPC5719
0.6816	Remote Similarity	NPC217804
0.6816	Remote Similarity	NPC22883
0.6816	Remote Similarity	NPC210377
0.6802	Remote Similarity	NPC254798
0.6796	Remote Similarity	NPC129486
0.6788	Remote Similarity	NPC248283
0.6784	Remote Similarity	NPC145113
0.6782	Remote Similarity	NPC262166
0.6778	Remote Similarity	NPC15068
0.6776	Remote Similarity	NPC306804
0.6769	Remote Similarity	NPC171317
0.6755	Remote Similarity	NPC294951
0.6753	Remote Similarity	NPC33742
0.6749	Remote Similarity	NPC75634
0.6746	Remote Similarity	NPC139326
0.6746	Remote Similarity	NPC197682
0.6744	Remote Similarity	NPC478028
0.6744	Remote Similarity	NPC105717
0.6742	Remote Similarity	NPC276085
0.674	Remote Similarity	NPC63040
0.6739	Remote Similarity	NPC17698
0.6739	Remote Similarity	NPC318930
0.6739	Remote Similarity	NPC26108
0.6739	Remote Similarity	NPC317362
0.6728	Remote Similarity	NPC105114
0.6728	Remote Similarity	NPC239990
0.6728	Remote Similarity	NPC152850
0.6728	Remote Similarity	NPC89923
0.6728	Remote Similarity	NPC71933
0.6728	Remote Similarity	NPC319766
0.6726	Remote Similarity	NPC476259
0.6724	Remote Similarity	NPC300443
0.6724	Remote Similarity	NPC162104
0.6721	Remote Similarity	NPC89831
0.6711	Remote Similarity	NPC319579
0.6705	Remote Similarity	NPC473580
0.6704	Remote Similarity	NPC68650
0.6686	Remote Similarity	NPC168113
0.6686	Remote Similarity	NPC135121
0.6685	Remote Similarity	NPC242269
0.6684	Remote Similarity	NPC153554
0.6682	Remote Similarity	NPC478029
0.6667	Remote Similarity	NPC475204
0.6667	Remote Similarity	NPC477217
0.6667	Remote Similarity	NPC475123
0.6667	Remote Similarity	NPC136453
0.6667	Remote Similarity	NPC201244
0.6649	Remote Similarity	NPC155506
0.6649	Remote Similarity	NPC159767
0.6649	Remote Similarity	NPC94862
0.6647	Remote Similarity	NPC176226
0.6647	Remote Similarity	NPC468984
0.6631	Remote Similarity	NPC45037
0.663	Remote Similarity	NPC230611
0.6618	Remote Similarity	NPC238945
0.6607	Remote Similarity	NPC68865
0.6606	Remote Similarity	NPC157311
0.6602	Remote Similarity	NPC478157
0.6601	Remote Similarity	NPC107077
0.6601	Remote Similarity	NPC478158
0.6601	Remote Similarity	NPC223791
0.6595	Remote Similarity	NPC248670
0.6591	Remote Similarity	NPC286551
0.6588	Remote Similarity	NPC476989
0.6587	Remote Similarity	NPC49195
0.6584	Remote Similarity	NPC175726
0.6584	Remote Similarity	NPC474082
0.6582	Remote Similarity	NPC220698
0.6582	Remote Similarity	NPC329295
0.6581	Remote Similarity	NPC276949

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 NPC469904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	432
0.2-0.3	840
0.3-0.4	2465
0.4-0.5	4011
0.5-0.6	1076
0.6-0.7	168
0.7-0.8	15
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
0.7712	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5263	Approved
0.7453	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3072	Approved
0.7451	Intermediate Similarity	NPD3071	Approved
0.7451	Intermediate Similarity	NPD3073	Approved
0.7389	Intermediate Similarity	NPD4676	Approved
0.7386	Intermediate Similarity	NPD4761	Approved
0.7386	Intermediate Similarity	NPD4762	Approved
0.7362	Intermediate Similarity	NPD7720	Phase 2
0.7362	Intermediate Similarity	NPD8076	Discontinued
0.7351	Intermediate Similarity	NPD8240	Discontinued
0.7329	Intermediate Similarity	NPD6073	Approved
0.7305	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD8290	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5725	Approved
0.7215	Intermediate Similarity	NPD4177	Approved
0.7215	Intermediate Similarity	NPD4175	Approved
0.7179	Intermediate Similarity	NPD4677	Discontinued
0.7178	Intermediate Similarity	NPD6901	Phase 3
0.7168	Intermediate Similarity	NPD8630	Approved
0.7167	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8643	Discontinued
0.7125	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4782	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4791	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5581	Approved
0.7078	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4126	Approved
0.7037	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4125	Approved
0.6933	Remote Similarity	NPD5747	Discontinued
0.6928	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8173	Phase 2
0.6909	Remote Similarity	NPD8172	Phase 2
0.6905	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2584	Suspended
0.6894	Remote Similarity	NPD3040	Approved
0.689	Remote Similarity	NPD6623	Phase 3
0.689	Remote Similarity	NPD8416	Discontinued
0.6882	Remote Similarity	NPD8323	Discontinued
0.6872	Remote Similarity	NPD8303	Discontinued
0.6867	Remote Similarity	NPD6294	Approved
0.6867	Remote Similarity	NPD6295	Approved
0.6864	Remote Similarity	NPD5264	Approved
0.6864	Remote Similarity	NPD5265	Approved
0.6857	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3908	Approved
0.6832	Remote Similarity	NPD4151	Approved
0.6818	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6557	Phase 2
0.6802	Remote Similarity	NPD6088	Approved
0.6802	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5323	Approved
0.6768	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1330	Phase 2
0.6766	Remote Similarity	NPD6852	Discontinued
0.6765	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5024	Approved
0.6747	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8315	Phase 1
0.6725	Remote Similarity	NPD1967	Approved
0.6725	Remote Similarity	NPD1968	Approved
0.6687	Remote Similarity	NPD4153	Approved
0.6687	Remote Similarity	NPD5759	Approved
0.6687	Remote Similarity	NPD5296	Approved
0.6667	Remote Similarity	NPD5299	Approved
0.6647	Remote Similarity	NPD2087	Approved
0.6647	Remote Similarity	NPD2088	Approved
0.6631	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5367	Discontinued
0.659	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7828	Discontinued
0.6584	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5942	Approved
0.6571	Remote Similarity	NPD4432	Discontinued
0.6571	Remote Similarity	NPD5941	Approved
0.6568	Remote Similarity	NPD4214	Discontinued
0.6556	Remote Similarity	NPD7599	Phase 2
0.6554	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD747	Discontinued
0.6536	Remote Similarity	NPD7105	Phase 1
0.6534	Remote Similarity	NPD5748	Phase 2
0.6534	Remote Similarity	NPD7613	Discontinued
0.6534	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7600	Phase 2
0.6506	Remote Similarity	NPD4794	Discontinued
0.65	Remote Similarity	NPD8019	Approved
0.6489	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8351	Phase 2
0.6477	Remote Similarity	NPD7683	Discontinued
0.6471	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD3509	Approved
0.6457	Remote Similarity	NPD3510	Approved
0.6453	Remote Similarity	NPD2022	Approved
0.645	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8322	Phase 2
0.642	Remote Similarity	NPD2016	Approved
0.642	Remote Similarity	NPD2013	Approved
0.642	Remote Similarity	NPD2014	Approved
0.6412	Remote Similarity	NPD5004	Approved
0.641	Remote Similarity	NPD7617	Discontinued
0.6409	Remote Similarity	NPD7011	Discontinued
0.6408	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6792	Phase 3
0.64	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7512	Approved
0.6395	Remote Similarity	NPD7511	Approved
0.6368	Remote Similarity	NPD7771	Discontinued
0.6359	Remote Similarity	NPD3790	Phase 2
0.6358	Remote Similarity	NPD3625	Discontinued
0.6348	Remote Similarity	NPD5229	Approved
0.6348	Remote Similarity	NPD5230	Approved
0.6344	Remote Similarity	NPD6304	Approved
0.6344	Remote Similarity	NPD6303	Approved
0.6335	Remote Similarity	NPD3989	Phase 3
0.6331	Remote Similarity	NPD3561	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD941	Approved
0.633	Remote Similarity	NPD7965	Phase 2
0.633	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3987	Approved
0.6328	Remote Similarity	NPD5614	Approved
0.6328	Remote Similarity	NPD3988	Approved
0.6328	Remote Similarity	NPD5613	Approved
0.6322	Remote Similarity	NPD2437	Approved
0.6322	Remote Similarity	NPD2436	Approved
0.6322	Remote Similarity	NPD6681	Discovery
0.6319	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8125	Discontinued
0.631	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.631	Remote Similarity	NPD2046	Approved
0.631	Remote Similarity	NPD2048	Approved
0.631	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7795	Phase 2
0.631	Remote Similarity	NPD2047	Approved
0.631	Remote Similarity	NPD2043	Approved
0.631	Remote Similarity	NPD2044	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
0.6308	Remote Similarity	NPD6632	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3125	Approved
0.6302	Remote Similarity	NPD3990	Phase 3
0.6301	Remote Similarity	NPD7450	Phase 2
0.6301	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7470	Discontinued
0.6296	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD979	Approved
0.6289	Remote Similarity	NPD1348	Approved
0.6286	Remote Similarity	NPD3508	Approved
0.6284	Remote Similarity	NPD4566	Approved
0.6284	Remote Similarity	NPD4567	Approved
0.6284	Remote Similarity	NPD4557	Approved
0.6282	Remote Similarity	NPD3642	Approved
0.6282	Remote Similarity	NPD3644	Approved
0.6282	Remote Similarity	NPD3643	Approved
0.6278	Remote Similarity	NPD4646	Approved
0.6278	Remote Similarity	NPD4647	Approved
0.6278	Remote Similarity	NPD4648	Approved
0.6276	Remote Similarity	NPD5851	Approved
0.6276	Remote Similarity	NPD5852	Approved
0.6273	Remote Similarity	NPD7951	Approved
0.6273	Remote Similarity	NPD7790	Approved
0.6273	Remote Similarity	NPD7791	Approved
0.6273	Remote Similarity	NPD7789	Approved
0.6273	Remote Similarity	NPD7952	Approved
0.6273	Remote Similarity	NPD7953	Approved
0.6273	Remote Similarity	NPD7950	Approved
0.6271	Remote Similarity	NPD3519	Discontinued
0.6264	Remote Similarity	NPD951	Approved
0.6263	Remote Similarity	NPD7570	Approved
0.6263	Remote Similarity	NPD7569	Approved
0.6263	Remote Similarity	NPD6665	Discontinued
0.6263	Remote Similarity	NPD4091	Approved
0.625	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5445	Approved
0.625	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8124	Phase 3
0.6239	Remote Similarity	NPD7780	Approved
0.6239	Remote Similarity	NPD7781	Approved
0.623	Remote Similarity	NPD7495	Discontinued
0.623	Remote Similarity	NPD4092	Approved
0.623	Remote Similarity	NPD3589	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data