NPASS Compound

Natural Product: NPC65262

Natural Product ID	NPC65262
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Specnuezhenide
IUPAC Name	methyl (4S,5Z,6S)-5-ethylidene-4-[2-oxo-2-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy]ethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3289607
PubChem CID	11146840
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

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 90 93 0 0 0 0 0 0 0 0999 V2000 -7.8615 0.2498 4.0144 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2925 -0.8531 3.2748 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7412 -0.8879 1.8830 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3814 -0.9365 1.8200 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8629 -0.9356 0.5365 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4860 -1.0345 0.5099 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9399 0.0716 -0.0986 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3077 -0.3472 -1.3494 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4010 0.5376 -1.8988 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4227 1.0756 -1.1154 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4960 0.5922 0.2761 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9309 0.7904 0.7095 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2362 1.5520 1.7134 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6534 1.7896 2.1680 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4916 0.9720 1.2456 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8680 0.5183 0.9999 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8379 1.2828 1.2150 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1839 -0.7703 0.5284 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5276 -1.1209 0.3399 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2161 -0.3647 -0.7278 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5745 -0.6729 -0.8333 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2365 -0.0239 -1.8476 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5042 -0.5811 -1.9301 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5607 0.2226 -1.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7246 0.8747 -0.3808 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8688 -0.0271 0.7740 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8924 -0.4627 1.6064 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1227 -1.3301 2.6623 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3896 -1.7922 2.9091 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4098 -1.3703 2.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1610 -0.5080 1.0384 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6420 -2.6703 3.9726 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5374 -0.0093 -3.1765 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0461 0.2057 -3.0826 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5308 -0.7306 -2.0445 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1701 -0.6594 -1.9009 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 -0.0146 -4.2956 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0160 1.0625 -3.9671 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5137 2.0300 -1.6845 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6577 2.3255 -2.9229 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5107 2.6772 -1.0425 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3817 3.6104 -1.6287 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5123 -2.0103 -0.3273 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0167 -1.8774 -0.3194 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4582 -1.9863 1.1294 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8255 -1.6304 1.1353 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6358 -2.7829 -1.1439 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0719 -1.8403 -1.6446 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2680 1.0847 3.6636 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4103 -0.7267 3.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1509 -1.8018 3.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0728 0.0692 1.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1606 0.0157 0.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7491 0.7743 -0.3606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4069 0.8457 -2.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3806 -0.5763 0.1470 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4033 2.0436 2.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3487 1.8645 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8936 1.0464 2.9260 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6407 2.8109 2.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4473 2.1053 1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7997 0.5921 2.2573 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1052 -1.0982 1.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5667 -2.2208 0.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1193 0.7104 -0.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3582 1.0480 -1.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7198 0.9975 -2.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4854 -0.4290 -1.8346 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6794 1.4786 -0.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9533 1.6480 -0.1596 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8855 -0.1064 1.4427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3067 -1.6518 3.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4005 -1.7528 2.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0107 -0.2192 0.4316 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6118 -2.8620 4.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7023 -0.9225 -3.7726 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8504 1.2455 -2.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7774 -1.7954 -2.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6583 -0.8099 -2.7134 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.6502 -4.4209 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4265 1.8336 -3.9552 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4383 3.3347 -1.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0283 3.8487 -2.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2331 4.5727 -1.0546 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2303 -3.0079 0.0162 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2330 -0.8119 -0.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3114 -2.9767 1.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3319 -2.0952 1.8291 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1630 -3.4061 -0.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7324 -1.3031 -2.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 11 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 22 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 10 39 1 0 39 40 2 0 39 41 1 0 41 42 1 0 5 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 45 3 1 0 12 7 1 0 35 20 1 0 31 26 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 6 5 53 1 6 7 54 1 6 9 55 1 0 11 56 1 6 13 57 1 0 14 58 1 0 14 59 1 0 14 60 1 0 15 61 1 0 15 62 1 0 19 63 1 0 19 64 1 0 20 65 1 1 22 66 1 1 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 27 71 1 0 28 72 1 0 30 73 1 0 31 74 1 0 32 75 1 0 33 76 1 6 34 77 1 1 35 78 1 6 36 79 1 0 37 80 1 0 38 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 43 85 1 1 44 86 1 6 45 87 1 1 46 88 1 0 47 89 1 0 48 90 1 0 M END

Standard InCHIKey	STKUCSFEBXPTAY-GSUVRYNNSA-N
Standard InCHI	InChI=1S/C31H42O17/c1-3-16-17(18(28(41)42-2)12-45-29(16)48-31-27(40)24(37)22(35)19(11-32)46-31)10-21(34)44-13-20-23(36)25(38)26(39)30(47-20)43-9-8-14-4-6-15(33)7-5-14/h3-7,12,17,19-20,22-27,29-33,35-40H,8-11,13H2,1-2H3/b16-3-/t17-,19+,20+,22+,23+,24-,25-,26+,27+,29-,30+,31-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H](/C/2=C/C)CC(=O)OC[C@H]2O[C@@H](OCCc3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	686.24	Volume:	641.485 ? Van der Waals volume.
Dense:	1.07	LogP:	-0.123 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.636 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.749 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	27.0
TPSA:	260.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.083	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.235	Fsp³:	0.613
MCE-18:	104.4 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.413	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.062 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.308 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.079	Promiscuous compounds:	0.158

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.072	MDCK Permeability:	-5.233
Pgp-inhibitor:	0.0	Pgp-substrate:	0.936
PAMPA:	0.998 ? 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):	0.894
20% Bioavailability (F20%):	0.543	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.102
Plasma Protein Binding (PPB):	74.954%	Volume Distribution (VD):	-0.286
Fu:	24.39% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.144
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.336
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	0.071 ? 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):

1.233

Half-life (T1/2):

2.605

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.145
Human Hepatotoxicity (H-HT):	0.872	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.072	Skin Sensitization:	1.0
Carcinogencity:	0.212	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.031	Ototoxicity:	0.994
Hematotoxicity:	0.259	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.25
A549 Cytotoxicity:	0.577	Hek293 Cytotoxicity:	0.451
BCF:	0.409 ? 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:	3.065 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.827 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.806 ? 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
NPO16259.1	Syringa reticulata subsp. amurensis	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16259.1	Syringa reticulata subsp. amurensis	Subspecies	Oleaceae	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
Kd	2
IC50	1

Activity Type	# Activity
Individual protein	1
Cell line	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2956	Individual protein	Interleukin-2	Homo sapiens	Kd	=	2.59	nM	PMID[24974349]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[24974349]
NPT2	Others	Unspecified	n.a.	Kd	=	2.4	nM	PMID[24974349]

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 NPC65262 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	8757
0.1-0.2	35663
0.2-0.3	4695
0.3-0.4	640
0.4-0.5	78
0.5-0.6	4
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC84429
1.0	High Similarity	NPC101686
0.9136	High Similarity	NPC469364
0.9136	High Similarity	NPC609284
0.8916	High Similarity	NPC198577
0.8864	High Similarity	NPC488387
0.8764	High Similarity	NPC488386
0.8659	High Similarity	NPC488383
0.8608	High Similarity	NPC169398
0.8452	Intermediate Similarity	NPC23677
0.7619	Intermediate Similarity	NPC296643
0.7619	Intermediate Similarity	NPC299576
0.7191	Intermediate Similarity	NPC488388
0.6914	Remote Similarity	NPC469543
0.6889	Remote Similarity	NPC488384
0.6742	Remote Similarity	NPC600692
0.6275	Remote Similarity	NPC488389
0.6203	Remote Similarity	NPC303451
0.6203	Remote Similarity	NPC72358
0.604	Remote Similarity	NPC488385
0.6	Remote Similarity	NPC246893
0.5405	Remote Similarity	NPC488390
0.5385	Remote Similarity	NPC157338
0.5341	Remote Similarity	NPC288416
0.5146	Remote Similarity	NPC469367

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC65262 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3990
0.1-0.2	5050
0.2-0.3	106
0.3-0.4	4
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