NPASS Compound

Structure

CID174486 OpenBabel06191715552D 38 43 0 0 1 0 0 0 0 0999 V2000 5.4781 -2.8060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4781 0.6581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9781 1.5241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 -2.8060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 3.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 -2.8060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 1.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.4945 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 34 1 0 0 0 0 2 35 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 5 9 1 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 6 14 2 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 26 1 0 0 0 0 9 22 2 0 0 0 0 10 15 1 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 27 2 0 0 0 0 13 19 1 0 0 0 0 13 34 1 0 0 0 0 14 24 1 0 0 0 0 14 36 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 23 2 0 0 0 0 21 31 1 0 0 0 0 22 37 1 0 0 0 0 23 38 1 0 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 4 1 1 0 0 0 26 37 1 0 0 0 0 26 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.08
Volume:	480.759
LogP:	3.142
LogD:	1.592
LogS:	-4.325
# Rotatable Bonds:	3
TPSA:	179.03
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	4.828
Fsp3:	0.231
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.067
MDCK Permeability:	2.44957918766886e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.876
20% Bioavailability (F20%):	0.362
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	91.9117660522461%
Volume Distribution (VD):	0.374
Pgp-substrate:	5.925468921661377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.569
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.178
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.78
CYP2C9-substrate:	0.627
CYP2D6-inhibitor:	0.251
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.482
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	1.263
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.607
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.477
Carcinogencity:	0.49
Eye Corrosion:	0.003
Eye Irritation:	0.081
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: NPC174486

Natural Product ID:	NPC174486
*Common Name:**	Gamma-Rubromycin
IUPAC Name:	methyl (2S)-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
Synonyms:
Standard InCHIKey:	CKLKRRFSZZUFKT-SANMLTNESA-N
Standard InCHI:	InChI=1S/C26H18O12/c1-34-13-7-12(27)16-17(19(13)29)21(31)23-11(18(16)28)8-26(38-23)4-3-9-5-10-6-14(24(32)35-2)36-25(33)15(10)20(30)22(9)37-26/h5-7,28,30-31H,3-4,8H2,1-2H3/t26-/m0/s1
SMILES:	COC(=O)c1cc2cc3CC[C@@]4(Oc3c(c2c(=O)o1)O)Cc1c(O4)c(O)c2c(c1O)C(=O)C=C(C2=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3347482
PubChem CID:	5464075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1002/hlca.201300170.]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141877]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12735688]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14575429]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23510022]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31465225]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23431	Aconitum umbrosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17801	Drimia altissima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26544	Bolboschoenus maritimus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23981	Maytenus disticha	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24063	Evasterias retifera	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6439	Lithospermum carolinense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23431	Aconitum umbrosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23175	Streptomyces antibioticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19539	Uperoleia rugosa	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23686	Selinum tenuifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.2	Narcissus pseudonarcissus subsp. radinganorum	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18919	Helenium amarum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23781	Lemaireocereus stellatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21915	Diospyros chloroxylon	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23688	Lonicera nitida	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22028	Ligularia lankongensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23363	0dulisporium hinnuleum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23113	Garcinia neglecta	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23268	Xanthorrhoea reflexa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21747	Sideritis glacialis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4378	Uvariastrum zenkeri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16976	Phebalium rotundifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20290	Vernonia arkansana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17888	Myxococcus xanthus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21175	Senecio retrorsus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12747	Peronia verruculata	Species	Onchidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23611	Conyza pallidiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13151.1	Pulsatilla vulgaris subsp. grandis	Subspecies	Ranunculaceae	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
EC50	2
IC50	1
MIC	7

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	IC50	=	3000.0	nM	PMID[535653]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	100000.0	nM	PMID[535654]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	>	100000.0	nM	PMID[535654]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.075	ug.mL-1	PMID[535654]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.15	ug.mL-1	PMID[535654]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.02	ug.mL-1	PMID[535654]
NPT5246	Organism	Mycobacterium aurum	Mycobacterium aurum	MIC	=	12.0	ug.mL-1	PMID[535654]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	24.0	ug.mL-1	PMID[535654]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	24.0	ug.mL-1	PMID[535654]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3.0	ug.mL-1	PMID[535654]

☑ 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 NPC174486 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	469
0.1-0.2	2106
0.2-0.3	4706
0.3-0.4	10519
0.4-0.5	7517
0.5-0.6	4215
0.6-0.7	5615
0.7-0.8	5078
0.8-0.85	2069
0.85-0.9	392
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC314020
0.9213	High Similarity	NPC295436
0.92	High Similarity	NPC265795
0.9191	High Similarity	NPC245975
0.9075	High Similarity	NPC158226
0.9017	High Similarity	NPC124470
0.9017	High Similarity	NPC109827
0.8977	High Similarity	NPC207467
0.896	High Similarity	NPC49487
0.896	High Similarity	NPC165979
0.896	High Similarity	NPC163130
0.896	High Similarity	NPC99613
0.8927	High Similarity	NPC212290
0.8927	High Similarity	NPC244903
0.8902	High Similarity	NPC76482
0.8889	High Similarity	NPC105591
0.8876	High Similarity	NPC170203
0.8876	High Similarity	NPC6709
0.887	High Similarity	NPC168584
0.887	High Similarity	NPC67302
0.8844	High Similarity	NPC37870
0.8844	High Similarity	NPC29160
0.884	High Similarity	NPC205721
0.8837	High Similarity	NPC236132
0.8837	High Similarity	NPC270837
0.8837	High Similarity	NPC474350
0.8827	High Similarity	NPC36138
0.882	High Similarity	NPC473785
0.8814	High Similarity	NPC472385
0.8814	High Similarity	NPC156635
0.8814	High Similarity	NPC198324
0.8807	High Similarity	NPC470942
0.88	High Similarity	NPC101107
0.8793	High Similarity	NPC234331
0.8793	High Similarity	NPC126204
0.8791	High Similarity	NPC314672
0.8786	High Similarity	NPC326520
0.8786	High Similarity	NPC88243
0.8786	High Similarity	NPC472450
0.8786	High Similarity	NPC239752
0.8786	High Similarity	NPC275780
0.8779	High Similarity	NPC294965
0.8778	High Similarity	NPC470416
0.8778	High Similarity	NPC148710
0.8772	High Similarity	NPC14353
0.8772	High Similarity	NPC56085
0.8772	High Similarity	NPC246478
0.8772	High Similarity	NPC228785
0.8771	High Similarity	NPC47883
0.8771	High Similarity	NPC97523
0.8771	High Similarity	NPC473071
0.8771	High Similarity	NPC473073
0.8764	High Similarity	NPC23553
0.8764	High Similarity	NPC77179
0.8757	High Similarity	NPC472607
0.8757	High Similarity	NPC470454
0.8757	High Similarity	NPC477848
0.8757	High Similarity	NPC199533
0.8757	High Similarity	NPC210094
0.8757	High Similarity	NPC237435
0.8757	High Similarity	NPC49344
0.8757	High Similarity	NPC43211
0.8757	High Similarity	NPC264735
0.8757	High Similarity	NPC146803
0.8757	High Similarity	NPC68381
0.8757	High Similarity	NPC101191
0.8757	High Similarity	NPC115760
0.8757	High Similarity	NPC135277
0.875	High Similarity	NPC475825
0.875	High Similarity	NPC223375
0.8743	High Similarity	NPC475805
0.8743	High Similarity	NPC321046
0.8743	High Similarity	NPC476637
0.8743	High Similarity	NPC280493
0.8736	High Similarity	NPC472452
0.8736	High Similarity	NPC170245
0.8736	High Similarity	NPC39091
0.8736	High Similarity	NPC472449
0.8728	High Similarity	NPC41301
0.8728	High Similarity	NPC470459
0.8728	High Similarity	NPC152659
0.8728	High Similarity	NPC189473
0.8728	High Similarity	NPC236521
0.8728	High Similarity	NPC23298
0.8728	High Similarity	NPC207690
0.8728	High Similarity	NPC248638
0.8722	High Similarity	NPC470445
0.8722	High Similarity	NPC473072
0.8722	High Similarity	NPC475656
0.8722	High Similarity	NPC228209
0.8722	High Similarity	NPC470449
0.8722	High Similarity	NPC182693
0.8722	High Similarity	NPC475148
0.8722	High Similarity	NPC470447
0.8722	High Similarity	NPC470446
0.8721	High Similarity	NPC66288
0.8721	High Similarity	NPC40491
0.8721	High Similarity	NPC61010
0.8721	High Similarity	NPC278052
0.8715	High Similarity	NPC84494
0.8715	High Similarity	NPC113446
0.8715	High Similarity	NPC245059
0.8713	High Similarity	NPC100123
0.8708	High Similarity	NPC475233
0.8708	High Similarity	NPC8127
0.8708	High Similarity	NPC49667
0.8708	High Similarity	NPC211532
0.8708	High Similarity	NPC472380
0.8708	High Similarity	NPC233994
0.8708	High Similarity	NPC472384
0.8708	High Similarity	NPC268533
0.8708	High Similarity	NPC472382
0.8701	High Similarity	NPC24043
0.8701	High Similarity	NPC101026
0.8701	High Similarity	NPC45522
0.8701	High Similarity	NPC42773
0.8701	High Similarity	NPC4390
0.8701	High Similarity	NPC169977
0.8701	High Similarity	NPC476152
0.8701	High Similarity	NPC21666
0.8693	High Similarity	NPC72696
0.8693	High Similarity	NPC17219
0.8693	High Similarity	NPC224462
0.8678	High Similarity	NPC470457
0.8674	High Similarity	NPC470455
0.8674	High Similarity	NPC470451
0.8671	High Similarity	NPC329760
0.8671	High Similarity	NPC472448
0.8671	High Similarity	NPC229632
0.8671	High Similarity	NPC470694
0.8671	High Similarity	NPC25152
0.8671	High Similarity	NPC81679
0.8671	High Similarity	NPC108767
0.8671	High Similarity	NPC83922
0.8667	High Similarity	NPC477860
0.8667	High Similarity	NPC470452
0.8667	High Similarity	NPC470453
0.8667	High Similarity	NPC208069
0.8667	High Similarity	NPC164047
0.8667	High Similarity	NPC470448
0.8667	High Similarity	NPC475161
0.8663	High Similarity	NPC119224
0.8663	High Similarity	NPC84571
0.8663	High Similarity	NPC130955
0.8663	High Similarity	NPC320359
0.8659	High Similarity	NPC267680
0.8659	High Similarity	NPC35167
0.8659	High Similarity	NPC297807
0.8659	High Similarity	NPC221820
0.8659	High Similarity	NPC217387
0.8659	High Similarity	NPC477683
0.8659	High Similarity	NPC293626
0.8659	High Similarity	NPC258044
0.8659	High Similarity	NPC196127
0.8659	High Similarity	NPC139571
0.8659	High Similarity	NPC98546
0.8659	High Similarity	NPC217520
0.8659	High Similarity	NPC246877
0.8659	High Similarity	NPC477682
0.8656	High Similarity	NPC3474
0.8655	High Similarity	NPC78302
0.8655	High Similarity	NPC262286
0.8655	High Similarity	NPC472438
0.8655	High Similarity	NPC29841
0.8655	High Similarity	NPC36852
0.8655	High Similarity	NPC235215
0.8655	High Similarity	NPC165977
0.8655	High Similarity	NPC7973
0.8655	High Similarity	NPC217677
0.8655	High Similarity	NPC300727
0.8655	High Similarity	NPC241904
0.8652	High Similarity	NPC294629
0.8652	High Similarity	NPC108202
0.8652	High Similarity	NPC139350
0.8644	High Similarity	NPC117260
0.8644	High Similarity	NPC307518
0.8644	High Similarity	NPC190003
0.8644	High Similarity	NPC111536
0.8644	High Similarity	NPC211594
0.8644	High Similarity	NPC271385
0.8644	High Similarity	NPC121333
0.8644	High Similarity	NPC172807
0.8644	High Similarity	NPC175107
0.8644	High Similarity	NPC5029
0.8644	High Similarity	NPC254540
0.8644	High Similarity	NPC153755
0.8644	High Similarity	NPC48773
0.8644	High Similarity	NPC76128
0.8644	High Similarity	NPC30432
0.8644	High Similarity	NPC476405
0.8644	High Similarity	NPC260263
0.8644	High Similarity	NPC205076
0.8636	High Similarity	NPC152477
0.8636	High Similarity	NPC177480
0.8636	High Similarity	NPC138927
0.8636	High Similarity	NPC471287
0.8636	High Similarity	NPC473095
0.8636	High Similarity	NPC473096
0.8636	High Similarity	NPC242395
0.8629	High Similarity	NPC207575

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 NPC174486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	1059
0.2-0.3	2102
0.3-0.4	2715
0.4-0.5	1717
0.5-0.6	760
0.6-0.7	243
0.7-0.8	122
0.8-0.85	24
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD4338	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD3818	Discontinued
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8436	Intermediate Similarity	NPD6797	Phase 2
0.8418	Intermediate Similarity	NPD7473	Discontinued
0.8389	Intermediate Similarity	NPD7251	Discontinued
0.8382	Intermediate Similarity	NPD3882	Suspended
0.8372	Intermediate Similarity	NPD2801	Approved
0.837	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8324	Intermediate Similarity	NPD5844	Phase 1
0.8324	Intermediate Similarity	NPD7054	Approved
0.8324	Intermediate Similarity	NPD3817	Phase 2
0.8278	Intermediate Similarity	NPD7472	Approved
0.8278	Intermediate Similarity	NPD7074	Phase 3
0.8258	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6166	Phase 2
0.8239	Intermediate Similarity	NPD5494	Approved
0.8229	Intermediate Similarity	NPD7075	Discontinued
0.8222	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD1465	Phase 2
0.8108	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD1934	Approved
0.8087	Intermediate Similarity	NPD6559	Discontinued
0.8057	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7819	Suspended
0.8041	Intermediate Similarity	NPD7435	Discontinued
0.8033	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD2534	Approved
0.8011	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6801	Discontinued
0.7989	Intermediate Similarity	NPD6959	Discontinued
0.7978	Intermediate Similarity	NPD6234	Discontinued
0.7967	Intermediate Similarity	NPD7228	Approved
0.7967	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD1512	Approved
0.7907	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD1247	Approved
0.7887	Intermediate Similarity	NPD6776	Approved
0.7887	Intermediate Similarity	NPD6780	Approved
0.7887	Intermediate Similarity	NPD6781	Approved
0.7887	Intermediate Similarity	NPD6778	Approved
0.7887	Intermediate Similarity	NPD6777	Approved
0.7887	Intermediate Similarity	NPD6779	Approved
0.7887	Intermediate Similarity	NPD6782	Approved
0.7886	Intermediate Similarity	NPD6599	Discontinued
0.7886	Intermediate Similarity	NPD4380	Phase 2
0.7877	Intermediate Similarity	NPD919	Approved
0.7849	Intermediate Similarity	NPD1511	Approved
0.7807	Intermediate Similarity	NPD8313	Approved
0.7807	Intermediate Similarity	NPD8312	Approved
0.78	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7874	Approved
0.7797	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD4965	Approved
0.7765	Intermediate Similarity	NPD4967	Phase 2
0.7765	Intermediate Similarity	NPD4966	Approved
0.775	Intermediate Similarity	NPD8151	Discontinued
0.7746	Intermediate Similarity	NPD6799	Approved
0.774	Intermediate Similarity	NPD7411	Suspended
0.7727	Intermediate Similarity	NPD3226	Approved
0.7722	Intermediate Similarity	NPD3749	Approved
0.772	Intermediate Similarity	NPD6534	Approved
0.772	Intermediate Similarity	NPD6535	Approved
0.7714	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD3926	Phase 2
0.7701	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7684	Intermediate Similarity	NPD8150	Discontinued
0.7677	Intermediate Similarity	NPD7696	Phase 3
0.7677	Intermediate Similarity	NPD7698	Approved
0.7677	Intermediate Similarity	NPD7697	Approved
0.7674	Intermediate Similarity	NPD3750	Approved
0.7663	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD3787	Discontinued
0.7638	Intermediate Similarity	NPD7870	Phase 2
0.7638	Intermediate Similarity	NPD7871	Phase 2
0.7614	Intermediate Similarity	NPD5403	Approved
0.7612	Intermediate Similarity	NPD7701	Phase 2
0.7602	Intermediate Similarity	NPD7699	Phase 2
0.7602	Intermediate Similarity	NPD2346	Discontinued
0.7602	Intermediate Similarity	NPD7700	Phase 2
0.7592	Intermediate Similarity	NPD8434	Phase 2
0.7558	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5710	Approved
0.7554	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD2800	Approved
0.7513	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD7801	Approved
0.7472	Intermediate Similarity	NPD1653	Approved
0.7463	Intermediate Similarity	NPD8319	Approved
0.7463	Intermediate Similarity	NPD8320	Phase 1
0.7442	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7685	Pre-registration
0.7384	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3748	Approved
0.7377	Intermediate Similarity	NPD7768	Phase 2
0.7363	Intermediate Similarity	NPD6823	Phase 2
0.7356	Intermediate Similarity	NPD1549	Phase 2
0.7345	Intermediate Similarity	NPD7390	Discontinued
0.7345	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD920	Approved
0.7314	Intermediate Similarity	NPD1243	Approved
0.731	Intermediate Similarity	NPD6212	Phase 3
0.731	Intermediate Similarity	NPD6213	Phase 3
0.731	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1510	Phase 2
0.7277	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1607	Approved
0.7264	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2796	Approved
0.7238	Intermediate Similarity	NPD7458	Discontinued
0.7232	Intermediate Similarity	NPD6190	Approved
0.7214	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1933	Approved
0.7209	Intermediate Similarity	NPD230	Phase 1
0.7207	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5953	Discontinued
0.7184	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD8366	Approved
0.7175	Intermediate Similarity	NPD4628	Phase 3
0.7151	Intermediate Similarity	NPD1240	Approved
0.7151	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7135	Intermediate Similarity	NPD2313	Discontinued
0.7128	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD447	Suspended
0.7103	Intermediate Similarity	NPD7907	Approved
0.7095	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2799	Discontinued
0.7073	Intermediate Similarity	NPD7680	Approved
0.7051	Intermediate Similarity	NPD8491	Approved
0.7049	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6099	Approved
0.7045	Intermediate Similarity	NPD5406	Approved
0.7045	Intermediate Similarity	NPD6100	Approved
0.7045	Intermediate Similarity	NPD5404	Approved
0.7045	Intermediate Similarity	NPD5408	Approved
0.7045	Intermediate Similarity	NPD5405	Approved
0.7044	Intermediate Similarity	NPD8285	Discontinued
0.7022	Intermediate Similarity	NPD6674	Discontinued
0.7006	Intermediate Similarity	NPD2344	Approved
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD8067	Phase 3
0.7	Intermediate Similarity	NPD7229	Phase 3
0.6995	Remote Similarity	NPD7286	Phase 2
0.6989	Remote Similarity	NPD8455	Phase 2
0.6985	Remote Similarity	NPD4287	Approved
0.6971	Remote Similarity	NPD7584	Approved
0.6971	Remote Similarity	NPD6651	Approved
0.6959	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4060	Phase 1
0.6941	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8059	Phase 3
0.6939	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.693	Remote Similarity	NPD4665	Approved
0.693	Remote Similarity	NPD4111	Phase 1
0.6927	Remote Similarity	NPD2403	Approved
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2493	Approved
0.6893	Remote Similarity	NPD2494	Approved
0.6889	Remote Similarity	NPD7003	Approved
0.6862	Remote Similarity	NPD4288	Approved
0.686	Remote Similarity	NPD5005	Approved
0.686	Remote Similarity	NPD5006	Approved
0.6859	Remote Similarity	NPD8127	Discontinued
0.6857	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1613	Approved
0.6853	Remote Similarity	NPD7549	Discontinued
0.6851	Remote Similarity	NPD2309	Approved
0.6839	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8404	Phase 2
0.6816	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7266	Discontinued
0.6812	Remote Similarity	NPD3452	Approved
0.6812	Remote Similarity	NPD3450	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