NPASS Compound

Structure

CID207574 OpenBabel06191715592D 54 59 0 0 1 0 0 0 0 0999 V2000 4.1882 5.3197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6753 -2.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.8361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 -2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 5.8033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8376 -3.3852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 -0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0258 3.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5129 -1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 3.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 -1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1882 4.3525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6753 -1.9344 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 3.8689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 -1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 5.3197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 0.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8376 2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0258 2.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5129 -0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 0.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8376 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1882 2.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1882 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6753 0.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 1.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 3.8689 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8376 -1.4508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3505 2.9016 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8376 -0.4836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8376 3.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3505 -0.9672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 5.8033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 -3.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1882 -0.4836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6753 2.9016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8634 2.4180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3505 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0258 0.9672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5129 1.4508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8376 3.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6753 -0.9672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 4.3525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 2.4180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 9 2 0 0 0 0 7 21 1 0 0 0 0 8 10 2 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 26 1 0 0 0 0 13 49 1 0 0 0 0 14 50 1 0 0 0 0 15 1 1 6 0 0 0 15 35 1 0 0 0 0 16 2 1 6 0 0 0 16 36 1 0 0 0 0 17 39 2 0 0 0 0 17 49 1 0 0 0 0 18 40 2 0 0 0 0 18 50 1 0 0 0 0 19 41 2 0 0 0 0 19 51 1 0 0 0 0 20 42 2 0 0 0 0 20 52 1 0 0 0 0 21 22 1 0 0 0 0 21 33 2 0 0 0 0 22 34 2 0 0 0 0 23 27 2 0 0 0 0 23 43 1 0 0 0 0 24 28 2 0 0 0 0 24 44 1 0 0 0 0 25 29 2 0 0 0 0 25 45 1 0 0 0 0 26 30 2 0 0 0 0 26 46 1 0 0 0 0 27 31 1 0 0 0 0 27 33 1 0 0 0 0 28 32 1 0 0 0 0 28 34 1 0 0 0 0 29 31 1 0 0 0 0 29 37 1 0 0 0 0 30 32 1 0 0 0 0 30 38 1 0 0 0 0 31 47 2 0 0 0 0 32 48 2 0 0 0 0 33 53 1 0 0 0 0 34 54 1 0 0 0 0 35 37 1 6 0 0 0 35 51 1 0 0 0 0 36 38 1 6 0 0 0 36 52 1 0 0 0 0 37 13 1 1 0 0 0 37 53 1 0 0 0 0 38 14 1 1 0 0 0 38 54 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	750.22
Volume:	718.198
LogP:	2.925
LogD:	1.247
LogS:	-4.423
# Rotatable Bonds:	11
TPSA:	232.4
# H-Bond Aceptor:	16
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	5.597
Fsp3:	0.474
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:	-5.348
MDCK Permeability:	3.122730413451791e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.278
Human Intestinal Absorption (HIA):	0.678
20% Bioavailability (F20%):	0.279
30% Bioavailability (F30%):	0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	78.6646957397461%
Volume Distribution (VD):	0.418
Pgp-substrate:	19.919784545898438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.21
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.795
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.607
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.696
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	1.746
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.623
Skin Sensitization:	0.02
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC207574

Natural Product ID:	NPC207574
*Common Name:**	Phomoxanthone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OHHXJWHRQGZQJM-ACMZUNAXSA-N
Standard InCHI:	InChI=1S/C38H38O16/c1-15-11-25(45)29-31(47)27-23(43)9-7-21(33(27)53-37(29,13-49-17(3)39)35(15)51-19(5)41)22-8-10-24(44)28-32(48)30-26(46)12-16(2)36(52-20(6)42)38(30,54-34(22)28)14-50-18(4)40/h7-10,15-16,35-36,43-46H,11-14H2,1-6H3/t15-,16-,35-,36-,37+,38+/m1/s1
SMILES:	C[C@@H]1CC(=C2C(=O)c3c(ccc(c4ccc(c5C(=O)C6=C(C[C@@H](C)[C@H]([C@@]6(COC(=O)C)Oc45)OC(=O)C)O)O)c3O[C@]2(COC(=O)C)[C@@H]1OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504079
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO30162	Phomopsis	Genus	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520217]

☑ 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	34
MIC	1
Others	43

Activity Type	# Activity
Cell Line	70
NON-MOLECULAR	1
Organism	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.99	ug.mL-1	PMID[519472]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.4	ug.mL-1	PMID[519472]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	580.0	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1380.38	nM	PMID[519473]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3700.0	nM	PMID[519473]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	4370.0	nM	PMID[519473]
NPT2290	Cell Line	CAL-27	Homo sapiens	IC50	=	5250.0	nM	PMID[519473]
NPT2396	Cell Line	KYSE-510	Homo sapiens	IC50	=	760.0	nM	PMID[519473]
NPT2396	Cell Line	KYSE-510	Homo sapiens	IC50	=	790.0	nM	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	3230.0	nM	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	2040.0	nM	PMID[519473]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1860.0	nM	PMID[519473]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1820.0	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Ratio IC50	=	7.0	n.a.	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Ratio IC50	=	9.0	n.a.	PMID[519473]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Ratio IC50	=	2.0	n.a.	PMID[519473]
NPT2290	Cell Line	CAL-27	Homo sapiens	Ratio IC50	=	2.0	n.a.	PMID[519473]
NPT2396	Cell Line	KYSE-510	Homo sapiens	Ratio IC50	=	2.0	n.a.	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Ratio IC50	=	4.0	n.a.	PMID[519473]
NPT111	Cell Line	K562	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[519473]
NPT393	Cell Line	HCT-116	Homo sapiens	Ratio IC50	=	2.0	n.a.	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1440.0	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1880.0	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1180.0	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1180.0	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Ratio IC50	=	2.5	n.a.	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	63.3	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	75.9	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	78.9	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	72.7	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	83.3	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	81.1	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	65.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	68.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	70.9	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	76.3	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	79.3	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	81.2	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	70.0	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	42.0	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	70.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	53.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	35.0	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1010.0	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	750.0	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1250.0	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	860.0	nM	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	3750.0	nM	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	3340.0	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	73.0	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	73.0	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	50.0	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	50.0	%	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	83.0	%	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	Activity	=	71.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	90.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	60.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	3120.0	nM	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	2750.0	nM	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Activity	=	100.0	%	PMID[519473]
NPT1505	Cell Line	J82	Homo sapiens	Ratio IC50	=	1.6	n.a.	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1445.44	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1862.09	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1174.9	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1174.9	nM	PMID[519473]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	575.44	nM	PMID[519473]
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	1370.0	nM	PMID[519473]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.11	ug.mL-1	PMID[519472]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	0.5	ug.mL-1	PMID[519472]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.51	ug.mL-1	PMID[519472]
NPT2	Others	Unspecified		IC50	=	5620.0	nM	PMID[519473]
NPT2	Others	Unspecified		Ratio IC50	=	2.0	n.a.	PMID[519473]
NPT2	Others	Unspecified		Ratio IC50	=	1.4	n.a.	PMID[519473]
NPT2	Others	Unspecified		Ratio IC50	=	3.0	n.a.	PMID[519473]

☑ 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 NPC207574 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	363
0.1-0.2	1476
0.2-0.3	3296
0.3-0.4	7867
0.4-0.5	10877
0.5-0.6	4004
0.6-0.7	6016
0.7-0.8	6596
0.8-0.85	1829
0.85-0.9	341
0.9-0.95	22
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC297195
1.0	High Similarity	NPC291795
0.9812	High Similarity	NPC241387
0.9812	High Similarity	NPC251144
0.9573	High Similarity	NPC469345
0.9512	High Similarity	NPC98667
0.9512	High Similarity	NPC86809
0.9512	High Similarity	NPC232412
0.9167	High Similarity	NPC477682
0.9167	High Similarity	NPC477683
0.9146	High Similarity	NPC178173
0.9048	High Similarity	NPC294149
0.9023	High Similarity	NPC48474
0.8982	High Similarity	NPC241874
0.8929	High Similarity	NPC472620
0.8902	High Similarity	NPC197972
0.8882	High Similarity	NPC312630
0.8882	High Similarity	NPC324220
0.8876	High Similarity	NPC154986
0.8848	High Similarity	NPC473961
0.8848	High Similarity	NPC473022
0.881	High Similarity	NPC472619
0.878	High Similarity	NPC186113
0.878	High Similarity	NPC474373
0.8765	High Similarity	NPC476139
0.875	High Similarity	NPC225419
0.875	High Similarity	NPC472622
0.8728	High Similarity	NPC470453
0.8728	High Similarity	NPC164047
0.8728	High Similarity	NPC470452
0.8728	High Similarity	NPC470448
0.8698	High Similarity	NPC102810
0.869	High Similarity	NPC120593
0.869	High Similarity	NPC469394
0.869	High Similarity	NPC251336
0.869	High Similarity	NPC472621
0.8683	High Similarity	NPC472053
0.8675	High Similarity	NPC3629
0.8671	High Similarity	NPC245059
0.8671	High Similarity	NPC84494
0.8659	High Similarity	NPC146636
0.8659	High Similarity	NPC164427
0.8655	High Similarity	NPC476229
0.8655	High Similarity	NPC476152
0.8642	High Similarity	NPC209142
0.8642	High Similarity	NPC46564
0.8642	High Similarity	NPC312549
0.8642	High Similarity	NPC207346
0.8634	High Similarity	NPC473016
0.8631	High Similarity	NPC473010
0.8623	High Similarity	NPC15374
0.8623	High Similarity	NPC472059
0.8623	High Similarity	NPC472402
0.8621	High Similarity	NPC208069
0.8621	High Similarity	NPC477860
0.8621	High Similarity	NPC475161
0.8614	High Similarity	NPC195136
0.8614	High Similarity	NPC471976
0.8613	High Similarity	NPC476199
0.8613	High Similarity	NPC476210
0.8606	High Similarity	NPC318527
0.8606	High Similarity	NPC323627
0.8606	High Similarity	NPC324358
0.8606	High Similarity	NPC1796
0.8606	High Similarity	NPC322459
0.8605	High Similarity	NPC63105
0.8598	High Similarity	NPC477958
0.8596	High Similarity	NPC9002
0.8596	High Similarity	NPC288152
0.8596	High Similarity	NPC477529
0.8596	High Similarity	NPC475669
0.8596	High Similarity	NPC257011
0.8596	High Similarity	NPC137871
0.8589	High Similarity	NPC475790
0.8588	High Similarity	NPC177480
0.8588	High Similarity	NPC476216
0.858	High Similarity	NPC29777
0.858	High Similarity	NPC475352
0.858	High Similarity	NPC229817
0.858	High Similarity	NPC475220
0.858	High Similarity	NPC87583
0.858	High Similarity	NPC473686
0.858	High Similarity	NPC471115
0.858	High Similarity	NPC221140
0.8571	High Similarity	NPC145467
0.8571	High Similarity	NPC191634
0.8571	High Similarity	NPC473009
0.8563	High Similarity	NPC18380
0.8563	High Similarity	NPC137232
0.8563	High Similarity	NPC97812
0.8563	High Similarity	NPC92589
0.8562	High Similarity	NPC473132
0.8562	High Similarity	NPC473135
0.8562	High Similarity	NPC470676
0.8556	High Similarity	NPC470198
0.8556	High Similarity	NPC316274
0.8556	High Similarity	NPC470196
0.8556	High Similarity	NPC470193
0.8556	High Similarity	NPC282474
0.8556	High Similarity	NPC470194
0.8556	High Similarity	NPC470195
0.8556	High Similarity	NPC470197
0.8556	High Similarity	NPC470200
0.8554	High Similarity	NPC105584
0.8554	High Similarity	NPC51247
0.8554	High Similarity	NPC51760
0.8547	High Similarity	NPC476311
0.8547	High Similarity	NPC213052
0.8545	High Similarity	NPC10754
0.8545	High Similarity	NPC69531
0.8545	High Similarity	NPC215917
0.8545	High Similarity	NPC20530
0.8538	High Similarity	NPC210808
0.8538	High Similarity	NPC199079
0.8538	High Similarity	NPC193698
0.8538	High Similarity	NPC477571
0.8538	High Similarity	NPC477572
0.8538	High Similarity	NPC313304
0.8538	High Similarity	NPC477573
0.8538	High Similarity	NPC103307
0.8537	High Similarity	NPC472799
0.8537	High Similarity	NPC326592
0.8537	High Similarity	NPC135522
0.8537	High Similarity	NPC109594
0.8537	High Similarity	NPC112701
0.8537	High Similarity	NPC209760
0.8537	High Similarity	NPC100134
0.8531	High Similarity	NPC294863
0.8531	High Similarity	NPC282636
0.8529	High Similarity	NPC76647
0.8528	High Similarity	NPC78835
0.8528	High Similarity	NPC204561
0.8528	High Similarity	NPC309512
0.8528	High Similarity	NPC470675
0.8528	High Similarity	NPC316960
0.8528	High Similarity	NPC474021
0.8528	High Similarity	NPC474023
0.8528	High Similarity	NPC471677
0.8528	High Similarity	NPC148945
0.8528	High Similarity	NPC317715
0.8528	High Similarity	NPC473131
0.8528	High Similarity	NPC178484
0.8523	High Similarity	NPC106700
0.8521	High Similarity	NPC472051
0.8521	High Similarity	NPC472057
0.8521	High Similarity	NPC293319
0.8521	High Similarity	NPC475979
0.8521	High Similarity	NPC25361
0.8519	High Similarity	NPC104236
0.8519	High Similarity	NPC164205
0.8519	High Similarity	NPC164299
0.8512	High Similarity	NPC473012
0.8512	High Similarity	NPC52204
0.8509	High Similarity	NPC308200
0.8506	High Similarity	NPC233978
0.8503	High Similarity	NPC292863
0.8503	High Similarity	NPC472055
0.8503	High Similarity	NPC42965
0.8503	High Similarity	NPC226462
0.8503	High Similarity	NPC184326
0.8503	High Similarity	NPC472618
0.8503	High Similarity	NPC98023
0.8503	High Similarity	NPC299436
0.8497	Intermediate Similarity	NPC470454
0.8497	Intermediate Similarity	NPC162248
0.8497	Intermediate Similarity	NPC199533
0.8494	Intermediate Similarity	NPC257166
0.8494	Intermediate Similarity	NPC271741
0.8494	Intermediate Similarity	NPC475184
0.8494	Intermediate Similarity	NPC287789
0.8492	Intermediate Similarity	NPC264302
0.8488	Intermediate Similarity	NPC477836
0.8488	Intermediate Similarity	NPC315619
0.8488	Intermediate Similarity	NPC476159
0.8488	Intermediate Similarity	NPC81332
0.8488	Intermediate Similarity	NPC262580
0.8488	Intermediate Similarity	NPC212038
0.8488	Intermediate Similarity	NPC271848
0.8488	Intermediate Similarity	NPC289396
0.8488	Intermediate Similarity	NPC118128
0.8485	Intermediate Similarity	NPC476169
0.8485	Intermediate Similarity	NPC300668
0.8485	Intermediate Similarity	NPC55662
0.8485	Intermediate Similarity	NPC166054
0.8485	Intermediate Similarity	NPC134171
0.848	Intermediate Similarity	NPC217378
0.848	Intermediate Similarity	NPC47634
0.848	Intermediate Similarity	NPC41598
0.848	Intermediate Similarity	NPC75141
0.848	Intermediate Similarity	NPC286074
0.848	Intermediate Similarity	NPC246274
0.848	Intermediate Similarity	NPC326877
0.848	Intermediate Similarity	NPC158329
0.848	Intermediate Similarity	NPC54903
0.848	Intermediate Similarity	NPC40089
0.848	Intermediate Similarity	NPC55422
0.848	Intermediate Similarity	NPC476146
0.8476	Intermediate Similarity	NPC210597
0.8476	Intermediate Similarity	NPC87708
0.8476	Intermediate Similarity	NPC56232

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 NPC207574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	932
0.2-0.3	1769
0.3-0.4	2537
0.4-0.5	1951
0.5-0.6	1068
0.6-0.7	395
0.7-0.8	158
0.8-0.85	25
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8563	High Similarity	NPD6959	Discontinued
0.8537	High Similarity	NPD7819	Suspended
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD7473	Discontinued
0.8343	Intermediate Similarity	NPD8313	Approved
0.8343	Intermediate Similarity	NPD8312	Approved
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4380	Phase 2
0.8204	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD5494	Approved
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8125	Intermediate Similarity	NPD6559	Discontinued
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7472	Approved
0.8114	Intermediate Similarity	NPD7074	Phase 3
0.8111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7808	Phase 3
0.8059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7054	Approved
0.8049	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD1934	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8023	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8150	Discontinued
0.7966	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6797	Phase 2
0.7953	Intermediate Similarity	NPD3749	Approved
0.795	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD1549	Phase 2
0.7901	Intermediate Similarity	NPD8434	Phase 2
0.7882	Intermediate Similarity	NPD2801	Approved
0.7882	Intermediate Similarity	NPD8455	Phase 2
0.7882	Intermediate Similarity	NPD1465	Phase 2
0.7877	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5403	Approved
0.7836	Intermediate Similarity	NPD3817	Phase 2
0.7831	Intermediate Similarity	NPD2532	Approved
0.7831	Intermediate Similarity	NPD2534	Approved
0.7831	Intermediate Similarity	NPD2533	Approved
0.7811	Intermediate Similarity	NPD6599	Discontinued
0.7805	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7783	Phase 2
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7772	Intermediate Similarity	NPD8151	Discontinued
0.7771	Intermediate Similarity	NPD6799	Approved
0.7751	Intermediate Similarity	NPD3226	Approved
0.773	Intermediate Similarity	NPD2346	Discontinued
0.7725	Intermediate Similarity	NPD5401	Approved
0.7716	Intermediate Similarity	NPD2799	Discontinued
0.7716	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7697	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2796	Approved
0.7669	Intermediate Similarity	NPD1551	Phase 2
0.765	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2800	Approved
0.7633	Intermediate Similarity	NPD920	Approved
0.7607	Intermediate Similarity	NPD1510	Phase 2
0.7604	Intermediate Similarity	NPD7698	Approved
0.7604	Intermediate Similarity	NPD7696	Phase 3
0.7604	Intermediate Similarity	NPD7435	Discontinued
0.7604	Intermediate Similarity	NPD7697	Approved
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.7586	Intermediate Similarity	NPD3882	Suspended
0.756	Intermediate Similarity	NPD1511	Approved
0.7558	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7286	Phase 2
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7486	Intermediate Similarity	NPD4965	Approved
0.7486	Intermediate Similarity	NPD4967	Phase 2
0.7486	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7485	Intermediate Similarity	NPD6651	Approved
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7473	Intermediate Similarity	NPD5953	Discontinued
0.7472	Intermediate Similarity	NPD3787	Discontinued
0.7471	Intermediate Similarity	NPD1512	Approved
0.7469	Intermediate Similarity	NPD1240	Approved
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD6823	Phase 2
0.7456	Intermediate Similarity	NPD7390	Discontinued
0.7455	Intermediate Similarity	NPD6100	Approved
0.7455	Intermediate Similarity	NPD6099	Approved
0.7453	Intermediate Similarity	NPD2313	Discontinued
0.7453	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7701	Phase 2
0.7448	Intermediate Similarity	NPD6780	Approved
0.7448	Intermediate Similarity	NPD6778	Approved
0.7448	Intermediate Similarity	NPD6782	Approved
0.7448	Intermediate Similarity	NPD6781	Approved
0.7448	Intermediate Similarity	NPD6776	Approved
0.7448	Intermediate Similarity	NPD6779	Approved
0.7448	Intermediate Similarity	NPD6777	Approved
0.7442	Intermediate Similarity	NPD7458	Discontinued
0.7432	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD5124	Phase 1
0.7423	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD8319	Approved
0.7385	Intermediate Similarity	NPD8320	Phase 1
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7003	Approved
0.7374	Intermediate Similarity	NPD7229	Phase 3
0.7374	Intermediate Similarity	NPD5710	Approved
0.7374	Intermediate Similarity	NPD5711	Approved
0.7344	Intermediate Similarity	NPD7700	Phase 2
0.7344	Intermediate Similarity	NPD7699	Phase 2
0.7337	Intermediate Similarity	NPD7801	Approved
0.7333	Intermediate Similarity	NPD7097	Phase 1
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7329	Intermediate Similarity	NPD4908	Phase 1
0.7321	Intermediate Similarity	NPD1243	Approved
0.7303	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4625	Phase 3
0.7246	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD5408	Approved
0.7246	Intermediate Similarity	NPD5405	Approved
0.7246	Intermediate Similarity	NPD5406	Approved
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD1247	Approved
0.7216	Intermediate Similarity	NPD8285	Discontinued
0.7212	Intermediate Similarity	NPD6355	Discontinued
0.7207	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6534	Approved
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7188	Intermediate Similarity	NPD6535	Approved
0.7186	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD2438	Suspended
0.7143	Intermediate Similarity	NPD1203	Approved
0.7136	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7199	Phase 2
0.712	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD447	Suspended
0.7107	Intermediate Similarity	NPD1610	Phase 2
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2344	Approved
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7083	Intermediate Similarity	NPD4308	Phase 3
0.7076	Intermediate Similarity	NPD8166	Discontinued
0.7068	Intermediate Similarity	NPD4287	Approved
0.7049	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1613	Approved
0.7048	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6798	Discontinued
0.703	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6844	Discontinued
0.7019	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD1933	Approved
0.7006	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2798	Approved
0.6989	Remote Similarity	NPD1653	Approved
0.6988	Remote Similarity	NPD6233	Phase 2
0.6985	Remote Similarity	NPD7680	Approved
0.6983	Remote Similarity	NPD5761	Phase 2
0.6983	Remote Similarity	NPD5760	Phase 2
0.6976	Remote Similarity	NPD7930	Approved
0.6975	Remote Similarity	NPD1283	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