NPASS Compound

Structure

CID113098 OpenBabel06191715462D 24 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -0.0000 -2.0000 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 -6.0622 2.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -4.3301 2.5000 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 -6.0622 1.5000 0.0000 C 0 0 2 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 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 8 1 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 14 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	348.2
LogP:	2.603
LogD:	2.406
LogS:	-3.351
# Rotatable Bonds:	7
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	3.11
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	1.8863958757719956e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.741
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.343
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	96.31266021728516%
Volume Distribution (VD):	0.606
Pgp-substrate:	3.788515090942383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.441
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.49
CYP2C19-substrate:	0.206
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.282
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	10.163
Half-life (T1/2):	0.378

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.394
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.544
Carcinogencity:	0.128
Eye Corrosion:	0.003
Eye Irritation:	0.228
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC113098

Natural Product ID:	NPC113098
*Common Name:**	R-(+)-Marmin
IUPAC Name:	7-[(E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]chromen-2-one
Synonyms:	Marmin; R-(+)-Marmin
Standard InCHIKey:	QYYKWTUUCOTGNS-JIIJFUIFSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-13(4-8-17(20)19(2,3)22)10-11-23-15-7-5-14-6-9-18(21)24-16(14)12-15/h5-7,9-10,12,17,20,22H,4,8,11H2,1-3H3/b13-10+/t17-/m1/s1
SMILES:	C/C(=CCOc1ccc2c(c1)oc(=O)cc2)/CC[C@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078441
PubChem CID:	6450230
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4109	Exocarpium citri grandis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1117	Hypholoma capnoides	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2629	Cystoseira caespitosa	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9366	Rosa transmorrisonensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24248.1	Lactarius deliciosus var. deterrimus	Varieties	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1
Potency	8

Activity Type	# Activity
Individual Protein	5
Organism	2
Others	2
PROTEIN COMPLEX	100

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[493458]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	1635.3	nM	PMID[493458]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[493458]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	11582.1	nM	PMID[493458]
NPT2	Others	Unspecified		Potency	=	29092.9	nM	PMID[493458]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4653.5	nM	PMID[493458]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[493458]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	31622.8	nM	PMID[493458]
NPT2	Others	Unspecified		Inhibition	=	20.0	%	PMID[493459]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	>	30000.0	nM	PMID[493459]

☑ 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 NPC113098 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	335
0.1-0.2	1394
0.2-0.3	3746
0.3-0.4	8703
0.4-0.5	10072
0.5-0.6	4045
0.6-0.7	6080
0.7-0.8	5213
0.8-0.85	2153
0.85-0.9	783
0.9-0.95	145
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC272650
0.9919	High Similarity	NPC267336
0.9919	High Similarity	NPC29734
0.9606	High Similarity	NPC469449
0.9597	High Similarity	NPC224774
0.9597	High Similarity	NPC258567
0.9597	High Similarity	NPC121740
0.9531	High Similarity	NPC62366
0.9531	High Similarity	NPC224475
0.9531	High Similarity	NPC180716
0.9531	High Similarity	NPC213173
0.952	High Similarity	NPC469453
0.9462	High Similarity	NPC155963
0.9457	High Similarity	NPC472525
0.9389	High Similarity	NPC151946
0.9385	High Similarity	NPC26954
0.9385	High Similarity	NPC38099
0.938	High Similarity	NPC204353
0.938	High Similarity	NPC326600
0.938	High Similarity	NPC50896
0.9318	High Similarity	NPC312881
0.9313	High Similarity	NPC232246
0.9313	High Similarity	NPC471068
0.9313	High Similarity	NPC471069
0.9313	High Similarity	NPC153818
0.9302	High Similarity	NPC2363
0.9302	High Similarity	NPC31849
0.9248	High Similarity	NPC287286
0.9248	High Similarity	NPC152771
0.9248	High Similarity	NPC195357
0.9242	High Similarity	NPC471070
0.9242	High Similarity	NPC279573
0.9242	High Similarity	NPC471072
0.9242	High Similarity	NPC471071
0.9237	High Similarity	NPC224543
0.9237	High Similarity	NPC78746
0.9237	High Similarity	NPC188380
0.9231	High Similarity	NPC253574
0.9231	High Similarity	NPC98179
0.9213	High Similarity	NPC185066
0.9187	High Similarity	NPC235190
0.9187	High Similarity	NPC163200
0.9187	High Similarity	NPC180006
0.9167	High Similarity	NPC184861
0.9167	High Similarity	NPC212124
0.9167	High Similarity	NPC281014
0.9167	High Similarity	NPC294456
0.9167	High Similarity	NPC225106
0.916	High Similarity	NPC33986
0.912	High Similarity	NPC273772
0.912	High Similarity	NPC109675
0.9104	High Similarity	NPC300611
0.9098	High Similarity	NPC211110
0.9077	High Similarity	NPC14248
0.9077	High Similarity	NPC194277
0.9048	High Similarity	NPC201667
0.9048	High Similarity	NPC73413
0.9048	High Similarity	NPC27671
0.9024	High Similarity	NPC281356
0.9024	High Similarity	NPC298796
0.9023	High Similarity	NPC131198
0.9008	High Similarity	NPC207002
0.9008	High Similarity	NPC167111
0.9008	High Similarity	NPC318400
0.9008	High Similarity	NPC222036
0.9008	High Similarity	NPC471910
0.9008	High Similarity	NPC7526
0.9008	High Similarity	NPC133956
0.9008	High Similarity	NPC296624
0.8992	High Similarity	NPC168710
0.8984	High Similarity	NPC243688
0.8978	High Similarity	NPC469701
0.8978	High Similarity	NPC85624
0.8968	High Similarity	NPC472518
0.8963	High Similarity	NPC215512
0.8963	High Similarity	NPC476442
0.8947	High Similarity	NPC103409
0.8943	High Similarity	NPC152306
0.8943	High Similarity	NPC265547
0.8939	High Similarity	NPC47163
0.8939	High Similarity	NPC267412
0.8939	High Similarity	NPC55149
0.8939	High Similarity	NPC74655
0.8939	High Similarity	NPC18804
0.8939	High Similarity	NPC319859
0.8939	High Similarity	NPC100986
0.8939	High Similarity	NPC260265
0.8939	High Similarity	NPC287182
0.8939	High Similarity	NPC84894
0.8939	High Similarity	NPC164269
0.8939	High Similarity	NPC127888
0.8939	High Similarity	NPC166672
0.8939	High Similarity	NPC198381
0.8939	High Similarity	NPC195343
0.8939	High Similarity	NPC307412
0.8923	High Similarity	NPC80170
0.8915	High Similarity	NPC472519
0.8913	High Similarity	NPC205361
0.8905	High Similarity	NPC471824
0.8889	High Similarity	NPC248429
0.8889	High Similarity	NPC96286
0.888	High Similarity	NPC302107
0.8872	High Similarity	NPC281241
0.8872	High Similarity	NPC472424
0.8872	High Similarity	NPC86892
0.8872	High Similarity	NPC471909
0.8872	High Similarity	NPC471625
0.8872	High Similarity	NPC469675
0.8864	High Similarity	NPC141822
0.8864	High Similarity	NPC142563
0.8864	High Similarity	NPC241165
0.8864	High Similarity	NPC1220
0.8864	High Similarity	NPC163557
0.8864	High Similarity	NPC205797
0.8864	High Similarity	NPC291551
0.8855	High Similarity	NPC250727
0.8849	High Similarity	NPC87950
0.8849	High Similarity	NPC471764
0.8849	High Similarity	NPC296377
0.8846	High Similarity	NPC474289
0.8832	High Similarity	NPC138212
0.8828	High Similarity	NPC471828
0.8828	High Similarity	NPC93219
0.8828	High Similarity	NPC232692
0.8828	High Similarity	NPC471827
0.8828	High Similarity	NPC244495
0.8828	High Similarity	NPC202594
0.8824	High Similarity	NPC138149
0.8819	High Similarity	NPC50720
0.8819	High Similarity	NPC154176
0.8819	High Similarity	NPC315807
0.8819	High Similarity	NPC173350
0.8819	High Similarity	NPC290605
0.8815	High Similarity	NPC35501
0.8815	High Similarity	NPC144512
0.8815	High Similarity	NPC37428
0.8815	High Similarity	NPC43500
0.8815	High Similarity	NPC164148
0.8815	High Similarity	NPC137262
0.8815	High Similarity	NPC278600
0.8815	High Similarity	NPC47040
0.881	High Similarity	NPC187868
0.881	High Similarity	NPC144418
0.881	High Similarity	NPC52247
0.8806	High Similarity	NPC177281
0.8806	High Similarity	NPC476455
0.8806	High Similarity	NPC128529
0.8806	High Similarity	NPC471630
0.8806	High Similarity	NPC55615
0.8806	High Similarity	NPC160727
0.8806	High Similarity	NPC283019
0.8806	High Similarity	NPC149320
0.8806	High Similarity	NPC283331
0.88	High Similarity	NPC247553
0.879	High Similarity	NPC96705
0.8786	High Similarity	NPC169510
0.878	High Similarity	NPC128633
0.8779	High Similarity	NPC32463
0.8779	High Similarity	NPC19242
0.8769	High Similarity	NPC199204
0.8768	High Similarity	NPC471763
0.876	High Similarity	NPC471826
0.876	High Similarity	NPC234109
0.876	High Similarity	NPC188327
0.8759	High Similarity	NPC20631
0.8759	High Similarity	NPC93640
0.875	High Similarity	NPC291899
0.874	High Similarity	NPC150214
0.874	High Similarity	NPC13007
0.874	High Similarity	NPC257188
0.8722	High Similarity	NPC469965
0.8705	High Similarity	NPC226722
0.8686	High Similarity	NPC472520
0.8686	High Similarity	NPC279851
0.8682	High Similarity	NPC168259
0.8657	High Similarity	NPC131950
0.8657	High Similarity	NPC92830
0.8651	High Similarity	NPC193193
0.8647	High Similarity	NPC469956
0.8636	High Similarity	NPC474491
0.8626	High Similarity	NPC293642
0.8626	High Similarity	NPC157212
0.8626	High Similarity	NPC139595
0.8626	High Similarity	NPC60704
0.8626	High Similarity	NPC219923
0.8615	High Similarity	NPC101894
0.8605	High Similarity	NPC111347
0.8603	High Similarity	NPC474886
0.8603	High Similarity	NPC14697
0.8593	High Similarity	NPC61499
0.8583	High Similarity	NPC319378
0.8582	High Similarity	NPC241341
0.8582	High Similarity	NPC469955
0.8582	High Similarity	NPC233018
0.8582	High Similarity	NPC469952
0.8582	High Similarity	NPC36437
0.8582	High Similarity	NPC15577
0.8582	High Similarity	NPC476347
0.8571	High Similarity	NPC476450
0.8561	High Similarity	NPC229916

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 NPC113098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	862
0.2-0.3	1737
0.3-0.4	2566
0.4-0.5	1960
0.5-0.6	1162
0.6-0.7	398
0.7-0.8	116
0.8-0.85	47
0.85-0.9	13
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD5123	Clinical (unspecified phase)
0.8864	High Similarity	NPD5124	Phase 1
0.881	High Similarity	NPD422	Phase 1
0.8686	High Similarity	NPD1652	Phase 2
0.8358	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1653	Approved
0.8074	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD1548	Phase 1
0.8056	Intermediate Similarity	NPD6799	Approved
0.7987	Intermediate Similarity	NPD6801	Discontinued
0.7956	Intermediate Similarity	NPD1296	Phase 2
0.7955	Intermediate Similarity	NPD1091	Approved
0.7941	Intermediate Similarity	NPD4908	Phase 1
0.7933	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD3225	Approved
0.7903	Intermediate Similarity	NPD1358	Approved
0.7903	Intermediate Similarity	NPD290	Approved
0.7891	Intermediate Similarity	NPD5403	Approved
0.7886	Intermediate Similarity	NPD9697	Approved
0.7877	Intermediate Similarity	NPD5401	Approved
0.7872	Intermediate Similarity	NPD7033	Discontinued
0.7852	Intermediate Similarity	NPD6599	Discontinued
0.7852	Intermediate Similarity	NPD2797	Approved
0.7847	Intermediate Similarity	NPD4628	Phase 3
0.7847	Intermediate Similarity	NPD3750	Approved
0.7842	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1613	Approved
0.784	Intermediate Similarity	NPD2684	Approved
0.7826	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6798	Discontinued
0.7823	Intermediate Similarity	NPD3134	Approved
0.782	Intermediate Similarity	NPD1610	Phase 2
0.7817	Intermediate Similarity	NPD2796	Approved
0.7778	Intermediate Similarity	NPD7075	Discontinued
0.7754	Intermediate Similarity	NPD3027	Phase 3
0.7746	Intermediate Similarity	NPD3748	Approved
0.7734	Intermediate Similarity	NPD7843	Approved
0.7734	Intermediate Similarity	NPD5535	Approved
0.7724	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1549	Phase 2
0.7708	Intermediate Similarity	NPD2424	Discontinued
0.7698	Intermediate Similarity	NPD3268	Approved
0.7692	Intermediate Similarity	NPD1551	Phase 2
0.7682	Intermediate Similarity	NPD7411	Suspended
0.7662	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4340	Discontinued
0.766	Intermediate Similarity	NPD6355	Discontinued
0.7655	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD9717	Approved
0.7616	Intermediate Similarity	NPD4380	Phase 2
0.7612	Intermediate Similarity	NPD3496	Discontinued
0.7603	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4060	Phase 1
0.7582	Intermediate Similarity	NPD7819	Suspended
0.7574	Intermediate Similarity	NPD4749	Approved
0.7571	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7157	Approved
0.7554	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6832	Phase 2
0.7537	Intermediate Similarity	NPD1778	Approved
0.7532	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.7518	Intermediate Similarity	NPD8651	Approved
0.7518	Intermediate Similarity	NPD6233	Phase 2
0.7517	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5763	Approved
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7484	Intermediate Similarity	NPD7768	Phase 2
0.7482	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1240	Approved
0.7464	Intermediate Similarity	NPD3267	Approved
0.7464	Intermediate Similarity	NPD1203	Approved
0.7464	Intermediate Similarity	NPD3266	Approved
0.7463	Intermediate Similarity	NPD5691	Approved
0.7453	Intermediate Similarity	NPD5844	Phase 1
0.7451	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7097	Phase 1
0.7417	Intermediate Similarity	NPD920	Approved
0.7415	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD4626	Approved
0.7403	Intermediate Similarity	NPD1934	Approved
0.7394	Intermediate Similarity	NPD4062	Phase 3
0.7383	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7095	Approved
0.7376	Intermediate Similarity	NPD4625	Phase 3
0.7361	Intermediate Similarity	NPD1607	Approved
0.7343	Intermediate Similarity	NPD4307	Phase 2
0.7343	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD7213	Phase 3
0.7333	Intermediate Similarity	NPD7212	Phase 2
0.7324	Intermediate Similarity	NPD1048	Approved
0.7297	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7199	Phase 2
0.7292	Intermediate Similarity	NPD230	Phase 1
0.7286	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1019	Discontinued
0.7285	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3818	Discontinued
0.7279	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6004	Phase 3
0.7279	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6005	Phase 3
0.7279	Intermediate Similarity	NPD6002	Phase 3
0.7273	Intermediate Similarity	NPD7549	Discontinued
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7267	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD6667	Approved
0.7261	Intermediate Similarity	NPD3882	Suspended
0.726	Intermediate Similarity	NPD2799	Discontinued
0.7259	Intermediate Similarity	NPD9545	Approved
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7244	Intermediate Similarity	NPD2801	Approved
0.7239	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2861	Phase 2
0.7234	Intermediate Similarity	NPD3018	Phase 2
0.7226	Intermediate Similarity	NPD3847	Discontinued
0.7222	Intermediate Similarity	NPD846	Approved
0.7222	Intermediate Similarity	NPD940	Approved
0.7219	Intermediate Similarity	NPD1511	Approved
0.7215	Intermediate Similarity	NPD3749	Approved
0.7212	Intermediate Similarity	NPD6559	Discontinued
0.7211	Intermediate Similarity	NPD2935	Discontinued
0.7197	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2415	Discontinued
0.7194	Intermediate Similarity	NPD3685	Discontinued
0.7192	Intermediate Similarity	NPD4538	Approved
0.7192	Intermediate Similarity	NPD4536	Approved
0.7192	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD447	Suspended
0.7172	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7447	Phase 1
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD919	Approved
0.7164	Intermediate Similarity	NPD6671	Approved
0.7162	Intermediate Similarity	NPD7266	Discontinued
0.716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6166	Phase 2
0.716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5846	Approved
0.7153	Intermediate Similarity	NPD6516	Phase 2
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5058	Phase 3
0.7134	Intermediate Similarity	NPD8455	Phase 2
0.7134	Intermediate Similarity	NPD7054	Approved
0.7133	Intermediate Similarity	NPD3179	Approved
0.7133	Intermediate Similarity	NPD3180	Approved
0.7124	Intermediate Similarity	NPD1512	Approved
0.7123	Intermediate Similarity	NPD6653	Approved
0.7122	Intermediate Similarity	NPD1608	Approved
0.7099	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6100	Approved
0.7095	Intermediate Similarity	NPD6032	Approved
0.7095	Intermediate Similarity	NPD6099	Approved
0.7092	Intermediate Similarity	NPD6362	Approved
0.7092	Intermediate Similarity	NPD987	Approved
0.7091	Intermediate Similarity	NPD7472	Approved
0.7091	Intermediate Similarity	NPD7074	Phase 3
0.7089	Intermediate Similarity	NPD4288	Approved
0.7086	Intermediate Similarity	NPD6190	Approved
0.7083	Intermediate Similarity	NPD411	Approved
0.7083	Intermediate Similarity	NPD2313	Discontinued
0.7071	Intermediate Similarity	NPD2982	Phase 2
0.7071	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2983	Phase 2
0.707	Intermediate Similarity	NPD37	Approved
0.7068	Intermediate Similarity	NPD821	Approved
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3536	Discontinued
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7055	Intermediate Similarity	NPD1933	Approved
0.7048	Intermediate Similarity	NPD6797	Phase 2
0.7044	Intermediate Similarity	NPD4966	Approved
0.7044	Intermediate Similarity	NPD4965	Approved
0.7044	Intermediate Similarity	NPD4967	Phase 2
0.7042	Intermediate Similarity	NPD3691	Phase 2
0.7042	Intermediate Similarity	NPD5647	Approved
0.7042	Intermediate Similarity	NPD3690	Phase 2
0.7027	Intermediate Similarity	NPD5960	Phase 3
0.7027	Intermediate Similarity	NPD5588	Approved
0.7025	Intermediate Similarity	NPD1465	Phase 2
0.702	Intermediate Similarity	NPD3892	Phase 2
0.7014	Intermediate Similarity	NPD5163	Phase 2
0.7013	Intermediate Similarity	NPD6273	Approved
0.7013	Intermediate Similarity	NPD5049	Phase 3
0.7013	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7251	Discontinued
0.7	Intermediate Similarity	NPD968	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