NPASS Compound

Natural Product: NPC55615

Natural Product ID	NPC55615
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3',4'-Diisovalerylkhellactone
IUPAC Name	[(9S,10S)-8,8-dimethyl-9-(3-methylbutanoyloxy)-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] 3-methylbutanoate
Synonyms	Cis-3',4'-Diisovalerylkhellactone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL477694
PubChem CID	44584701
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 61 63 0 0 0 0 0 0 0 0999 V2000 3.0990 -2.4801 -0.8347 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8603 -2.2105 0.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2772 -3.0408 1.5662 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8569 -0.7458 0.8080 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5122 -0.2074 1.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9348 -0.3881 2.1406 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7869 0.5023 0.0771 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4880 1.0066 0.3198 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5725 2.4873 0.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6672 2.9146 -1.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7475 4.2752 -1.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7330 5.1608 -0.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6383 4.7234 0.9488 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6206 5.5862 2.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5239 5.0919 3.3199 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4475 3.7260 3.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3578 3.2581 4.6341 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4635 2.8983 2.4350 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5557 3.3557 1.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6755 1.9634 -2.1873 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1121 0.7697 -2.1030 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3331 1.0104 -2.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6096 -0.4210 -2.6445 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5260 0.4913 -0.6789 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8153 -0.8824 -0.4936 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0807 -1.3406 -0.1589 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9734 -0.4346 -0.0284 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4024 -2.7751 0.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8683 -2.8963 0.3872 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7458 -2.3392 -0.7247 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2462 -4.3532 0.5557 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5128 -3.4216 -1.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0239 -2.5782 -0.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3928 -1.6757 -1.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9015 -2.5570 0.2848 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1866 -3.1969 1.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5287 -2.5053 2.5171 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7403 -4.0653 1.6092 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4625 -0.1981 0.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4372 -0.6755 1.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1010 0.7927 1.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8233 4.6101 -2.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7953 6.2148 -0.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6824 6.6504 1.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5044 5.7102 4.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0199 1.3900 -3.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0016 1.7912 -2.5389 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9105 0.0699 -3.1196 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7118 -0.3043 -2.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2641 -0.6745 -3.6888 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3663 -1.3043 -2.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4626 1.0612 -0.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8385 -3.2265 0.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2335 -3.3681 -0.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1249 -2.3826 1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0867 -1.3055 -0.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6797 -2.9500 -0.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2361 -2.4457 -1.7002 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1630 -4.4042 1.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4506 -4.9555 0.9947 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5520 -4.8020 -0.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 10 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 24 8 1 0 19 9 1 0 19 13 2 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 8 41 1 1 11 42 1 0 12 43 1 0 14 44 1 0 15 45 1 0 22 46 1 0 22 47 1 0 22 48 1 0 23 49 1 0 23 50 1 0 23 51 1 0 24 52 1 1 28 53 1 0 28 54 1 0 29 55 1 0 30 56 1 0 30 57 1 0 30 58 1 0 31 59 1 0 31 60 1 0 31 61 1 0 M END

Standard InCHIKey	LJYPJWICCCIAKW-GOTSBHOMSA-N
Standard InCHI	InChI=1S/C24H30O7/c1-13(2)11-18(26)29-22-20-16(9-7-15-8-10-17(25)28-21(15)20)31-24(5,6)23(22)30-19(27)12-14(3)4/h7-10,13-14,22-23H,11-12H2,1-6H3/t22-,23-/m0/s1
SMILES	CC(C)CC(=O)O[C@H]1c2c(ccc3ccc(=O)oc23)OC(C)(C)[C@H]1OC(=O)CC(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	430.2	Volume:	441.067 ? Van der Waals volume.
Dense:	0.975	LogP:	3.927 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.471 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.627 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	19.0
TPSA:	92.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.49	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.672	Fsp³:	0.542
MCE-18:	72.73 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.836	Fluc inhibitor:	0.027 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.85 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.735 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.261	Promiscuous compounds:	0.056

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.659	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.293 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.061	30% Bioavailability (F30%):	0.111
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.996
Plasma Protein Binding (PPB):	91.219%	Volume Distribution (VD):	0.172
Fu:	7.118% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.029	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.488	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

6.081

Half-life (T1/2):

0.599

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.329
Human Hepatotoxicity (H-HT):	0.672	Drug-induced Liver Injury (DILI):	0.808
AMES Toxicity:	0.503	Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.341	Skin Sensitization:	0.594
Carcinogencity:	0.835	Eye Corrosion:	0.153
Eye Irritation:	0.712	Respiratory Toxicity:	0.327
Drug-induced Neurotoxicity:	0.188	Ototoxicity:	0.481
Hematotoxicity:	0.49	Drug-induced Nephrotoxicity:	0.579
Genotoxicity:	0.319	RPMI-8226 Immunitoxicity:	0.093
A549 Cytotoxicity:	0.062	Hek293 Cytotoxicity:	0.135
BCF:	1.629 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.403 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.641 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.046 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1453177]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24813739]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16675	Peucedanum japonicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8874	Glehnia littoralis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15394	Angelica decursiva	Species	Apiaceae	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	Organism Name	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
Activity	5
IC50	1

Activity Type	# Activity
Cell line	2
Non-molecular	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	7400.0	nM	PMID[24813739]
NPT113	Cell line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[24813739]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	8.8	%	PMID[1453177]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	49.8	%	PMID[1453177]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	39.3	%	PMID[1453177]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[1453177]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC55615 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	9627
0.1-0.2	38515
0.2-0.3	1509
0.3-0.4	122
0.4-0.5	42
0.5-0.6	12
0.6-0.7	2
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9492	High Similarity	NPC149320
0.9492	High Similarity	NPC160727
0.9492	High Similarity	NPC177281
0.9333	High Similarity	NPC128529
0.8615	High Similarity	NPC283019
0.8226	Intermediate Similarity	NPC166672
0.8	Intermediate Similarity	NPC167111
0.8	Intermediate Similarity	NPC318400
0.7937	Intermediate Similarity	NPC86892
0.7937	Intermediate Similarity	NPC471909
0.7846	Intermediate Similarity	NPC476455
0.75	Intermediate Similarity	NPC471625
0.75	Intermediate Similarity	NPC476457
0.7429	Intermediate Similarity	NPC471630
0.7424	Intermediate Similarity	NPC195343
0.7424	Intermediate Similarity	NPC267412
0.7424	Intermediate Similarity	NPC74655
0.7424	Intermediate Similarity	NPC471910
0.7313	Intermediate Similarity	NPC84894
0.7313	Intermediate Similarity	NPC18804
0.7313	Intermediate Similarity	NPC319859
0.7313	Intermediate Similarity	NPC296624
0.7313	Intermediate Similarity	NPC164269
0.7313	Intermediate Similarity	NPC198381
0.7313	Intermediate Similarity	NPC287182
0.7313	Intermediate Similarity	NPC127888
0.6901	Remote Similarity	NPC100986
0.6143	Remote Similarity	NPC484113
0.5758	Remote Similarity	NPC199204
0.5479	Remote Similarity	NPC129572
0.5352	Remote Similarity	NPC472424
0.5352	Remote Similarity	NPC281241
0.5342	Remote Similarity	NPC287286
0.5263	Remote Similarity	NPC307412
0.5263	Remote Similarity	NPC606124
0.5205	Remote Similarity	NPC469675
0.5135	Remote Similarity	NPC260265
0.5132	Remote Similarity	NPC312881
0.507	Remote Similarity	NPC153818
0.507	Remote Similarity	NPC232246

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC55615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2259
0.1-0.2	6792
0.2-0.3	99
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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