NPASS Compound

Structure

CID57105 OpenBabel06191715392D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 8 1 0 0 0 0 2 13 1 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 15 1 0 0 0 0 7 19 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 20 2 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 3 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.07
Volume:	287.18
LogP:	1.631
LogD:	1.785
LogS:	-6.114
# Rotatable Bonds:	4
TPSA:	107.89
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.254
Synthetic Accessibility Score:	2.722
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	3.0387609513127245e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.957
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	91.91448211669922%
Volume Distribution (VD):	0.51
Pgp-substrate:	10.28032112121582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.499
CYP2C9-substrate:	0.857
CYP2D6-inhibitor:	0.254
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	2.975
Half-life (T1/2):	0.563

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.624
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.946
Carcinogencity:	0.125
Eye Corrosion:	0.004
Eye Irritation:	0.549
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: NPC57105

Natural Product ID:	NPC57105
*Common Name:**	Chandrananimycin D
IUPAC Name:	2-hydroxy-N-[8-(hydroxymethyl)-3-oxophenoxazin-2-yl]acetamide
Synonyms:	Chandrananimycin D; Chandrananomycin D
Standard InCHIKey:	OQMHQWLKGNKBET-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H12N2O5/c18-6-8-1-2-13-10(3-8)16-11-4-9(17-15(21)7-19)12(20)5-14(11)22-13/h1-5,18-19H,6-7H2,(H,17,21)
SMILES:	c1cc2c(cc1CO)nc1-c(cc(=O)c(c1)N=C(CO)O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224595
PubChem CID:	46939591
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001396] Benzoxazines [CHEMONTID:0001855] Phenoxazines

*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
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11720530]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724858]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880174]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800631]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[21774474]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22050382]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[23164710]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26203536]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1937	Andropogon nardus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2805	Distolasterias nipon	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO729	Espeletia marcana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9320	Weddellina squamulosa	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5219	Dendrobium rotundatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18350	Culcitium canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6787	Neoalsomitra integrifolia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9937	Piptolepis leptospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1526	Ratibida latipalearis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8416	Picrorhiza kurrooa	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9603	Croton sparsiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10867	Graphis elongata	Species	Aclididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11355	Homarus americanus	Species	Nephropidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9020	Eriostemon fitzgeraldii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12481	Croton californicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8547	Petasites niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12309	Malva crispa	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7365	Clibadium pentaneuron	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12535	Solanum toxicarium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3900	Phellinus xeranticus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3202	0lina erumpens	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7883	Albugo candida	Species	Albuginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9227	Xylaria berteri	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24849	Rhinella paracnemis	Species	Bufonidae	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
GI50	7
IC50	6
Others	1

Activity Type	# Activity
Cell Line	12
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	=	16600.0	nM	PMID[496057]
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	=	5300.0	nM	PMID[496057]
NPT1970	Cell Line	THP-1	Homo sapiens	GI50	=	27600.0	nM	PMID[496057]
NPT80	Cell Line	Raji	Homo sapiens	GI50	=	9600.0	nM	PMID[496057]
NPT71	Cell Line	HEK293	Homo sapiens	GI50	=	10300.0	nM	PMID[496057]
NPT65	Cell Line	HepG2	Homo sapiens	GI50	=	6600.0	nM	PMID[496057]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	1300.0	nM	PMID[496057]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	90600.0	nM	PMID[496057]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[496058]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[496058]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[496058]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	30.0	ug.mL-1	PMID[496058]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30.0	ug.mL-1	PMID[496058]

☑ 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 NPC57105 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	520
0.1-0.2	3998
0.2-0.3	12631
0.3-0.4	4078
0.4-0.5	13161
0.5-0.6	7542
0.6-0.7	709
0.7-0.8	40
0.8-0.85	10
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC231862
0.9167	High Similarity	NPC314861
0.8795	High Similarity	NPC313886
0.8773	High Similarity	NPC315631
0.8322	Intermediate Similarity	NPC297584
0.8315	Intermediate Similarity	NPC214368
0.8133	Intermediate Similarity	NPC208022
0.8121	Intermediate Similarity	NPC127362
0.8059	Intermediate Similarity	NPC316161
0.8034	Intermediate Similarity	NPC108847
0.8	Intermediate Similarity	NPC314113
0.7947	Intermediate Similarity	NPC313466
0.7718	Intermediate Similarity	NPC315632
0.7697	Intermediate Similarity	NPC10875
0.7697	Intermediate Similarity	NPC10730
0.763	Intermediate Similarity	NPC8467
0.756	Intermediate Similarity	NPC306366
0.7532	Intermediate Similarity	NPC473987
0.7531	Intermediate Similarity	NPC473769
0.7529	Intermediate Similarity	NPC204179
0.75	Intermediate Similarity	NPC478049
0.744	Intermediate Similarity	NPC70549
0.7405	Intermediate Similarity	NPC314948
0.7381	Intermediate Similarity	NPC112766
0.7088	Intermediate Similarity	NPC469829
0.7039	Intermediate Similarity	NPC168153
0.6954	Remote Similarity	NPC235628
0.6946	Remote Similarity	NPC473874
0.6879	Remote Similarity	NPC62101
0.6879	Remote Similarity	NPC95733
0.6848	Remote Similarity	NPC469831
0.6842	Remote Similarity	NPC258992
0.6815	Remote Similarity	NPC211218
0.679	Remote Similarity	NPC471953
0.6786	Remote Similarity	NPC178466
0.6786	Remote Similarity	NPC260601
0.6786	Remote Similarity	NPC63628
0.6772	Remote Similarity	NPC475411
0.6769	Remote Similarity	NPC311357
0.6768	Remote Similarity	NPC138365
0.6755	Remote Similarity	NPC264782
0.6744	Remote Similarity	NPC182119
0.673	Remote Similarity	NPC29477
0.6725	Remote Similarity	NPC277857
0.6725	Remote Similarity	NPC115144
0.6721	Remote Similarity	NPC9475
0.6707	Remote Similarity	NPC29650
0.6706	Remote Similarity	NPC313414
0.6705	Remote Similarity	NPC184161
0.6703	Remote Similarity	NPC116096
0.6702	Remote Similarity	NPC469830
0.6687	Remote Similarity	NPC470392
0.6686	Remote Similarity	NPC56635
0.6667	Remote Similarity	NPC245974
0.6667	Remote Similarity	NPC476462
0.6667	Remote Similarity	NPC263835
0.665	Remote Similarity	NPC66191
0.665	Remote Similarity	NPC314817
0.665	Remote Similarity	NPC316297
0.6649	Remote Similarity	NPC262725
0.6649	Remote Similarity	NPC294244
0.6648	Remote Similarity	NPC225381
0.6647	Remote Similarity	NPC299583
0.6647	Remote Similarity	NPC161155
0.6647	Remote Similarity	NPC47986
0.6647	Remote Similarity	NPC97004
0.6647	Remote Similarity	NPC136951
0.6647	Remote Similarity	NPC314252
0.6647	Remote Similarity	NPC36434
0.6631	Remote Similarity	NPC477392
0.6631	Remote Similarity	NPC315934
0.663	Remote Similarity	NPC477888
0.6627	Remote Similarity	NPC126637
0.6613	Remote Similarity	NPC260118
0.6609	Remote Similarity	NPC219383
0.6608	Remote Similarity	NPC97282
0.6607	Remote Similarity	NPC83289
0.6607	Remote Similarity	NPC189724
0.6607	Remote Similarity	NPC298821
0.6607	Remote Similarity	NPC212850
0.6603	Remote Similarity	NPC256369
0.6596	Remote Similarity	NPC28425
0.6593	Remote Similarity	NPC83241
0.659	Remote Similarity	NPC470935
0.659	Remote Similarity	NPC471032
0.6587	Remote Similarity	NPC312770
0.6587	Remote Similarity	NPC204848
0.6587	Remote Similarity	NPC41473
0.6587	Remote Similarity	NPC14600
0.6587	Remote Similarity	NPC160607
0.6578	Remote Similarity	NPC192939
0.6578	Remote Similarity	NPC215747
0.6573	Remote Similarity	NPC19023
0.6568	Remote Similarity	NPC123761
0.6568	Remote Similarity	NPC195814
0.6561	Remote Similarity	NPC41801
0.6559	Remote Similarity	NPC265383
0.6554	Remote Similarity	NPC8302
0.655	Remote Similarity	NPC247298
0.6546	Remote Similarity	NPC470023
0.6545	Remote Similarity	NPC105541
0.6545	Remote Similarity	NPC169766
0.6543	Remote Similarity	NPC119579
0.6543	Remote Similarity	NPC259098
0.6543	Remote Similarity	NPC197680
0.6533	Remote Similarity	NPC473422
0.6526	Remote Similarity	NPC232872
0.6524	Remote Similarity	NPC472163
0.6524	Remote Similarity	NPC314025
0.6522	Remote Similarity	NPC95412
0.6519	Remote Similarity	NPC83279
0.6519	Remote Similarity	NPC19555
0.6513	Remote Similarity	NPC470021
0.6508	Remote Similarity	NPC477391
0.6503	Remote Similarity	NPC310894
0.65	Remote Similarity	NPC139506
0.65	Remote Similarity	NPC292143
0.6497	Remote Similarity	NPC187028
0.6497	Remote Similarity	NPC197741
0.6497	Remote Similarity	NPC10221
0.6497	Remote Similarity	NPC140915
0.6497	Remote Similarity	NPC18249
0.6497	Remote Similarity	NPC305700
0.6491	Remote Similarity	NPC323798
0.649	Remote Similarity	NPC255721
0.6489	Remote Similarity	NPC314656
0.6489	Remote Similarity	NPC314213
0.6489	Remote Similarity	NPC311936
0.6485	Remote Similarity	NPC274732
0.6482	Remote Similarity	NPC159101
0.6474	Remote Similarity	NPC315829
0.6474	Remote Similarity	NPC323948
0.6457	Remote Similarity	NPC139699
0.6457	Remote Similarity	NPC114659
0.6455	Remote Similarity	NPC315913
0.6452	Remote Similarity	NPC474902
0.6444	Remote Similarity	NPC69360
0.6442	Remote Similarity	NPC224774
0.6442	Remote Similarity	NPC258567
0.6442	Remote Similarity	NPC121740
0.644	Remote Similarity	NPC180253
0.644	Remote Similarity	NPC219170
0.6433	Remote Similarity	NPC168750
0.6429	Remote Similarity	NPC301735
0.6429	Remote Similarity	NPC472191
0.6425	Remote Similarity	NPC291359
0.6425	Remote Similarity	NPC301163
0.6425	Remote Similarity	NPC70340
0.6424	Remote Similarity	NPC113098
0.6421	Remote Similarity	NPC276060
0.6416	Remote Similarity	NPC9373
0.6406	Remote Similarity	NPC22928
0.6402	Remote Similarity	NPC469453
0.6398	Remote Similarity	NPC290069
0.6392	Remote Similarity	NPC43275
0.6391	Remote Similarity	NPC476420
0.6391	Remote Similarity	NPC471316
0.6391	Remote Similarity	NPC87043
0.6387	Remote Similarity	NPC235250
0.6387	Remote Similarity	NPC161696
0.6386	Remote Similarity	NPC267336
0.6386	Remote Similarity	NPC29734
0.6386	Remote Similarity	NPC130595
0.6386	Remote Similarity	NPC93882
0.6386	Remote Similarity	NPC272650
0.6383	Remote Similarity	NPC98416
0.638	Remote Similarity	NPC291609
0.6379	Remote Similarity	NPC132771
0.6374	Remote Similarity	NPC71205
0.6373	Remote Similarity	NPC296742
0.6373	Remote Similarity	NPC112676
0.6369	Remote Similarity	NPC204353
0.6369	Remote Similarity	NPC326600
0.6369	Remote Similarity	NPC50896
0.6368	Remote Similarity	NPC62069
0.6364	Remote Similarity	NPC220560
0.6364	Remote Similarity	NPC295970
0.6359	Remote Similarity	NPC279401
0.6359	Remote Similarity	NPC257354
0.6359	Remote Similarity	NPC79293
0.6358	Remote Similarity	NPC251306
0.6354	Remote Similarity	NPC69213
0.6353	Remote Similarity	NPC294456
0.6353	Remote Similarity	NPC212124
0.6353	Remote Similarity	NPC281014
0.6353	Remote Similarity	NPC184861
0.6353	Remote Similarity	NPC225106
0.6352	Remote Similarity	NPC160120
0.6352	Remote Similarity	NPC17388
0.6352	Remote Similarity	NPC471308
0.6352	Remote Similarity	NPC289330
0.6352	Remote Similarity	NPC53596
0.6347	Remote Similarity	NPC6854
0.6347	Remote Similarity	NPC313737
0.6347	Remote Similarity	NPC285078
0.6346	Remote Similarity	NPC303370
0.6344	Remote Similarity	NPC474953
0.6341	Remote Similarity	NPC471532
0.6341	Remote Similarity	NPC251571
0.6341	Remote Similarity	NPC101372

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 NPC57105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	772
0.2-0.3	1082
0.3-0.4	1814
0.4-0.5	3060
0.5-0.6	1774
0.6-0.7	325
0.7-0.8	14
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
0.8025	Intermediate Similarity	NPD3778	Approved
0.7914	Intermediate Similarity	NPD980	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD1898	Discontinued
0.7353	Intermediate Similarity	NPD3560	Approved
0.7353	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3557	Approved
0.7353	Intermediate Similarity	NPD3556	Approved
0.7353	Intermediate Similarity	NPD3558	Approved
0.7305	Intermediate Similarity	NPD4003	Phase 3
0.7299	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6104	Discontinued
0.7241	Intermediate Similarity	NPD2247	Approved
0.7241	Intermediate Similarity	NPD2249	Approved
0.7219	Intermediate Similarity	NPD4604	Approved
0.7219	Intermediate Similarity	NPD4605	Approved
0.7169	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7083	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3236	Phase 3
0.7076	Intermediate Similarity	NPD3237	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2216	Approved
0.7062	Intermediate Similarity	NPD2215	Approved
0.702	Intermediate Similarity	NPD254	Approved
0.7018	Intermediate Similarity	NPD3296	Phase 1
0.7011	Intermediate Similarity	NPD3154	Approved
0.7011	Intermediate Similarity	NPD3153	Approved
0.7	Intermediate Similarity	NPD3965	Phase 1
0.6973	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3453	Discontinued
0.6962	Remote Similarity	NPD4993	Discontinued
0.6959	Remote Similarity	NPD5811	Approved
0.6954	Remote Similarity	NPD1012	Discontinued
0.6943	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6184	Discontinued
0.6914	Remote Similarity	NPD9694	Discovery
0.689	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2366	Approved
0.6854	Remote Similarity	NPD2821	Approved
0.6824	Remote Similarity	NPD4123	Phase 3
0.6802	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4083	Discontinued
0.6774	Remote Similarity	NPD6045	Phase 3
0.6755	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD756	Suspended
0.6748	Remote Similarity	NPD1393	Approved
0.6739	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7546	Discontinued
0.6717	Remote Similarity	NPD6296	Discontinued
0.6717	Remote Similarity	NPD7263	Phase 2
0.6705	Remote Similarity	NPD6283	Phase 2
0.6705	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2525	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5481	Discontinued
0.6684	Remote Similarity	NPD6034	Phase 2
0.6683	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7256	Discontinued
0.6667	Remote Similarity	NPD2339	Phase 3
0.6667	Remote Similarity	NPD6063	Approved
0.6648	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1422	Approved
0.6633	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7043	Discontinued
0.6632	Remote Similarity	NPD4259	Approved
0.6632	Remote Similarity	NPD4258	Approved
0.6631	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3538	Suspended
0.6629	Remote Similarity	NPD4675	Approved
0.6629	Remote Similarity	NPD4678	Approved
0.6628	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7125	Discontinued
0.6611	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3656	Approved
0.6575	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7318	Phase 3
0.6568	Remote Similarity	NPD7153	Discontinued
0.6566	Remote Similarity	NPD3802	Phase 3
0.6557	Remote Similarity	NPD3952	Approved
0.6557	Remote Similarity	NPD3951	Phase 3
0.6557	Remote Similarity	NPD3953	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7476	Discontinued
0.6546	Remote Similarity	NPD6550	Discontinued
0.6543	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD1557	Discontinued
0.6522	Remote Similarity	NPD5938	Phase 3
0.6519	Remote Similarity	NPD2341	Discontinued
0.6513	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2388	Discontinued
0.6497	Remote Similarity	NPD6072	Discontinued
0.6494	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5800	Discontinued
0.6492	Remote Similarity	NPD3490	Discontinued
0.6485	Remote Similarity	NPD7477	Discontinued
0.6484	Remote Similarity	NPD2680	Approved
0.6484	Remote Similarity	NPD2681	Approved
0.6477	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4597	Approved
0.6471	Remote Similarity	NPD3823	Discontinued
0.6471	Remote Similarity	NPD4598	Approved
0.6471	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2434	Approved
0.6467	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7317	Phase 3
0.6458	Remote Similarity	NPD2845	Phase 2
0.6458	Remote Similarity	NPD2843	Phase 2
0.6448	Remote Similarity	NPD5847	Phase 1
0.6447	Remote Similarity	NPD6874	Approved
0.6444	Remote Similarity	NPD4871	Phase 2
0.6436	Remote Similarity	NPD3037	Phase 1
0.6436	Remote Similarity	NPD2514	Approved
0.6436	Remote Similarity	NPD5845	Phase 2
0.6432	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3251	Approved
0.6429	Remote Similarity	NPD1559	Discontinued
0.6425	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5871	Discontinued
0.6422	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4502	Phase 2
0.642	Remote Similarity	NPD3567	Approved
0.642	Remote Similarity	NPD3568	Approved
0.642	Remote Similarity	NPD5267	Discontinued
0.6412	Remote Similarity	NPD521	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6590	Discontinued
0.6407	Remote Similarity	NPD654	Phase 3
0.6406	Remote Similarity	NPD3398	Discontinued
0.6406	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1891	Discontinued
0.6398	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2415	Discontinued
0.6386	Remote Similarity	NPD2674	Phase 3
0.6378	Remote Similarity	NPD5512	Phase 3
0.6378	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1769	Discontinued
0.6369	Remote Similarity	NPD3052	Approved
0.6369	Remote Similarity	NPD3054	Approved
0.6369	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3627	Approved
0.6364	Remote Similarity	NPD6974	Phase 3
0.6364	Remote Similarity	NPD7131	Phase 3
0.6364	Remote Similarity	NPD821	Approved
0.6364	Remote Similarity	NPD711	Discontinued
0.6359	Remote Similarity	NPD4466	Phase 1
0.6354	Remote Similarity	NPD4587	Phase 3
0.635	Remote Similarity	NPD7316	Discontinued
0.6348	Remote Similarity	NPD3684	Discontinued
0.6346	Remote Similarity	NPD9342	Approved
0.6343	Remote Similarity	NPD2335	Discontinued
0.6343	Remote Similarity	NPD3536	Discontinued
0.6337	Remote Similarity	NPD2460	Phase 3
0.6337	Remote Similarity	NPD2458	Approved
0.6337	Remote Similarity	NPD2459	Approved
0.6333	Remote Similarity	NPD5772	Approved
0.6333	Remote Similarity	NPD5773	Approved
0.6331	Remote Similarity	NPD696	Discontinued
0.6328	Remote Similarity	NPD2883	Discontinued
0.6327	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3145	Approved
0.6325	Remote Similarity	NPD3144	Approved
0.6325	Remote Similarity	NPD1048	Approved
0.6321	Remote Similarity	NPD2792	Approved
0.6316	Remote Similarity	NPD7883	Discontinued
0.631	Remote Similarity	NPD3909	Discontinued
0.6308	Remote Similarity	NPD4740	Approved
0.6301	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4129	Approved
0.6296	Remote Similarity	NPD1505	Phase 2
0.6296	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3685	Discontinued
0.6294	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4005	Discontinued
0.629	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7891	Discontinued
0.6287	Remote Similarity	NPD5745	Approved
0.6287	Remote Similarity	NPD1423	Approved
0.6286	Remote Similarity	NPD4357	Discontinued
0.6281	Remote Similarity	NPD7811	Phase 3
0.6281	Remote Similarity	NPD7810	Phase 3
0.6276	Remote Similarity	NPD5150	Phase 2
0.6271	Remote Similarity	NPD2122	Discontinued
0.6269	Remote Similarity	NPD4515	Suspended
0.6269	Remote Similarity	NPD2498	Approved
0.6268	Remote Similarity	NPD6719	Approved
0.6265	Remote Similarity	NPD3179	Approved
0.6265	Remote Similarity	NPD3180	Approved
0.6264	Remote Similarity	NPD7773	Phase 2
0.6263	Remote Similarity	NPD6988	Phase 1
0.6263	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5872	Discontinued
0.6262	Remote Similarity	NPD5416	Discontinued
0.6262	Remote Similarity	NPD7468	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