NPASS Compound

Natural Product: NPC266265

Natural Product ID	NPC266265
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FCQBGPOADKWYEG-MNRUEBDGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL387145
PubChem CID	16109787
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 88 93 0 0 0 0 0 0 0 0999 V2000 -4.2882 1.1863 2.1056 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8892 0.8356 2.3424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3096 1.3166 3.3494 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1561 -0.0103 1.5129 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8112 -0.3292 1.8010 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8528 -1.7992 2.1876 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8141 -2.4602 1.4217 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4131 -2.5218 2.2135 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5991 -1.9158 1.5419 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4826 -0.4649 1.2211 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0788 -0.1012 0.6587 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2928 -1.1231 -0.4139 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6438 -0.9241 -0.7887 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2542 -1.7244 -1.7515 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5359 -2.6259 -2.2566 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6293 -1.5862 -2.1955 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4663 -0.6105 -1.6970 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7845 -0.4983 -2.1346 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3001 -1.3569 -3.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4648 -2.3363 -3.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1581 -2.4367 -3.1403 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0894 1.2185 -0.0027 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1386 1.7926 -0.2734 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7263 2.0183 -1.4998 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9876 1.6026 -2.4359 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0067 2.6401 -1.7459 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7688 3.1613 -0.7395 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0020 3.7362 -1.0123 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4651 3.7840 -2.3095 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7121 3.2645 -3.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4884 2.6989 -3.0334 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1124 2.2088 0.5097 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3957 1.5730 0.9737 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4916 0.1397 0.4025 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7416 -0.3294 0.2209 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4990 -0.5955 -0.8654 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8461 -0.3299 -1.8785 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8622 -1.1105 -0.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5654 -1.3962 0.2599 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8517 -1.8810 0.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4822 -2.0986 -1.0479 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7476 -1.8011 -2.1901 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4621 -1.3164 -2.1011 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2591 1.2828 2.4520 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4775 0.1835 2.4905 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6076 1.1194 3.1245 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5926 2.4101 3.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1445 -2.7665 0.4135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9384 0.5146 2.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6505 1.0923 1.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5119 2.2482 2.4023 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4643 0.2405 2.7183 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3437 -1.7649 3.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1287 -3.2640 1.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6178 -2.8289 3.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2805 -3.5450 1.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4216 -1.9623 2.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3269 -0.9022 -1.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1585 -2.1503 -0.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0718 0.0599 -0.9656 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4379 0.2653 -1.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3270 -1.2715 -3.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8826 -3.0024 -4.3254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5065 -3.2047 -3.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4589 1.0238 -1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3916 3.1297 0.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5644 4.1309 -0.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4240 4.2308 -2.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0889 3.3082 -4.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8985 2.2913 -3.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4336 2.9075 -0.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6740 2.9126 1.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2910 2.1519 0.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1708 0.2658 -0.6467 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0826 -1.2295 1.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4170 -2.1107 1.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4884 -2.4774 -1.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1938 -1.9527 -3.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9026 -1.0888 -3.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4399 1.2274 4.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0696 0.1346 2.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3360 1.8846 2.8379 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0026 3.4039 2.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8776 2.3166 4.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4991 2.3745 3.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5763 -3.7388 0.3329 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1695 -2.2430 -0.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2033 -3.1006 0.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 11 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 22 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 33 44 1 0 44 45 1 0 44 46 1 0 44 47 1 0 9 48 1 0 11 5 1 0 21 16 1 0 31 26 1 0 43 38 1 0 10 45 1 1 34 10 1 0 1 49 1 0 1 50 1 0 1 51 1 0 5 52 1 1 6 53 1 1 7 54 1 0 8 55 1 0 8 56 1 0 9 57 1 1 12 58 1 0 12 59 1 0 17 60 1 0 18 61 1 0 19 62 1 0 20 63 1 0 21 64 1 0 22 65 1 6 27 66 1 0 28 67 1 0 29 68 1 0 30 69 1 0 31 70 1 0 32 71 1 0 32 72 1 0 33 73 1 1 34 74 1 6 39 75 1 0 40 76 1 0 41 77 1 0 42 78 1 0 43 79 1 0 46 80 1 0 46 81 1 0 46 82 1 0 47 83 1 0 47 84 1 0 47 85 1 0 48 86 1 0 48 87 1 0 48 88 1 0 M END

Standard InCHIKey	FCQBGPOADKWYEG-MNRUEBDGSA-N
Standard InCHI	InChI=1S/C38H40O10/c1-23-20-29(40)32(45-24(2)39)37(22-44-33(41)25-14-8-5-9-15-25)30(46-34(42)26-16-10-6-11-17-26)21-28-31(38(23,37)48-36(28,3)4)47-35(43)27-18-12-7-13-19-27/h5-19,23,28-32,40H,20-22H2,1-4H3/t23-,28-,29+,30+,31-,32+,37-,38-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H](O)C[C@H]([C@@]23[C@]1(COC(=O)c1ccccc1)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3OC(=O)c1ccccc1)C(O2)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	656.26	Volume:	668.093 ? Van der Waals volume.
Dense:	0.982	LogP:	4.539 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.787 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.381 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	36.0
TPSA:	134.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.255	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.724	Fsp³:	0.421
MCE-18:	176.296 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.899	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.326 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.062	Promiscuous compounds:	0.039

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.393	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.988	Pgp-substrate:	0.107
PAMPA:	0.215 ? 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%):	0.001	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.822

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965	MRP1:	1.0
Plasma Protein Binding (PPB):	95.101%	Volume Distribution (VD):	-0.456
Fu:	5.846% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.974	BCRP inhibitor:	0.009
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.993
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.384	CYP3A4-substrate:	0.983
CYP2B6-substrate:	0.0	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):

1.847

Half-life (T1/2):

1.224

ADMET: Toxicity

hERG Blockers:	0.169	hERG Blockers (10um):	0.701
Human Hepatotoxicity (H-HT):	0.046	Drug-induced Liver Injury (DILI):	0.916
AMES Toxicity:	0.249	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.337	Skin Sensitization:	0.981
Carcinogencity:	0.645	Eye Corrosion:	0.0
Eye Irritation:	0.077	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.78	Ototoxicity:	0.376
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.503
Genotoxicity:	0.049	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.388	Hek293 Cytotoxicity:	0.701
BCF:	0.889 ? 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:	4.107 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.335 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.079 ? 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
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22423	Microtropis fokienensis	Species	Celastraceae	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
MIC	1

Activity Type	# Activity
Organism	1

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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	19500.0	nM	PMID[17315960]

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 NPC266265 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	8398
0.1-0.2	37867
0.2-0.3	2857
0.3-0.4	568
0.4-0.5	119
0.5-0.6	35
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8358	Intermediate Similarity	NPC41481
0.7391	Intermediate Similarity	NPC246480
0.7042	Intermediate Similarity	NPC67777
0.7042	Intermediate Similarity	NPC177340
0.6901	Remote Similarity	NPC48017
0.6667	Remote Similarity	NPC96903
0.6622	Remote Similarity	NPC92293
0.6575	Remote Similarity	NPC139067
0.6575	Remote Similarity	NPC43241
0.6216	Remote Similarity	NPC191082
0.6081	Remote Similarity	NPC17877
0.6056	Remote Similarity	NPC283375
0.6056	Remote Similarity	NPC183122
0.5867	Remote Similarity	NPC163087
0.5844	Remote Similarity	NPC171207
0.5811	Remote Similarity	NPC607964
0.5789	Remote Similarity	NPC4341
0.5789	Remote Similarity	NPC479047
0.5789	Remote Similarity	NPC291638
0.5753	Remote Similarity	NPC200592
0.5753	Remote Similarity	NPC270498
0.5753	Remote Similarity	NPC610542
0.5714	Remote Similarity	NPC27377
0.5696	Remote Similarity	NPC252314
0.5641	Remote Similarity	NPC473673
0.5625	Remote Similarity	NPC95265
0.5616	Remote Similarity	NPC474608
0.557	Remote Similarity	NPC479044
0.5513	Remote Similarity	NPC473871
0.5432	Remote Similarity	NPC70716
0.5432	Remote Similarity	NPC97667
0.5432	Remote Similarity	NPC184747
0.5385	Remote Similarity	NPC483883
0.5385	Remote Similarity	NPC151585
0.5375	Remote Similarity	NPC306146
0.5375	Remote Similarity	NPC483841
0.5333	Remote Similarity	NPC473081
0.5333	Remote Similarity	NPC195647
0.5316	Remote Similarity	NPC270590
0.5301	Remote Similarity	NPC479042
0.5287	Remote Similarity	NPC75600
0.5287	Remote Similarity	NPC483884
0.5181	Remote Similarity	NPC475652
0.5128	Remote Similarity	NPC475759
0.5128	Remote Similarity	NPC470152
0.5125	Remote Similarity	NPC147217
0.5125	Remote Similarity	NPC158663
0.506	Remote Similarity	NPC210591

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC266265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2884
0.1-0.2	6041
0.2-0.3	224
0.3-0.4	1
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