NPASS Compound

Natural Product: NPC482267

Natural Product ID	NPC482267
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CFGMCKRDNHXTBH-LDHUFNJZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 91 93 0 0 0 0 0 0 0 0999 V2000 2.9005 -2.9023 -2.7238 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9167 -2.3447 -1.2943 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7732 -3.0247 -0.5648 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7512 -2.3047 -0.1629 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4469 -2.7889 0.5607 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1170 -3.8097 -0.2869 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0650 -3.4965 1.8202 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3256 -1.6650 1.0289 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8664 -0.7099 0.0717 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1925 0.4800 -0.4422 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3760 1.3341 0.4132 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9243 2.5160 0.7597 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9751 1.1354 0.9843 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0172 1.1400 -0.0939 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7819 2.4432 -0.1614 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0733 2.0706 -0.8402 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2360 2.9135 -0.2944 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3047 0.6171 -0.5669 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9559 0.0040 -0.1545 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6123 -0.8910 -1.3271 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 -0.4062 -2.2875 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1067 -0.8217 0.9391 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5846 -0.5724 2.1818 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9797 0.5695 2.4358 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6703 -1.5787 3.2741 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9446 3.0930 1.0304 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2059 2.2040 1.8957 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3338 2.1034 3.2436 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2388 0.9602 3.7778 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 3.3135 4.0927 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2793 1.2952 -1.0147 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3315 1.6103 -2.3441 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4215 1.1943 -3.1299 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3950 2.4153 -2.9311 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4293 2.9138 -2.1596 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4337 3.6843 -2.7492 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4334 3.9719 -4.0942 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4056 3.4775 -4.8663 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4230 2.7190 -4.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5932 -1.4199 -0.9495 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9465 -1.4568 -1.0911 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6506 -0.8316 -0.2835 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5232 -2.2480 -2.2117 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4849 -2.2773 1.6827 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7396 -2.1526 3.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9614 -1.4923 3.7194 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9383 -2.7914 3.6572 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9044 -2.9238 -3.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5366 -3.9545 -2.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -2.3132 -3.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8635 -2.6169 -0.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8928 -4.0877 -0.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7756 -1.2506 -0.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2039 -3.8775 -0.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9115 -3.7037 -1.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7206 -4.8379 -0.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7810 -2.8510 2.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7813 -3.8354 2.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6366 -4.4157 1.5555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8213 -1.1619 1.8448 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 -0.2430 0.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5769 0.2848 -1.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3699 3.1800 1.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9141 2.8268 0.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0133 0.1789 1.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4052 1.1634 -1.0718 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2763 3.1840 -0.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0421 2.3050 -1.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3770 3.8302 -0.8714 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0197 3.2034 0.7516 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1456 2.2984 -0.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7021 0.1500 -1.4848 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0734 0.4309 0.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7346 -1.8681 3.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3603 -1.0918 4.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0095 -2.4330 3.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5131 3.9727 1.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7021 3.0491 5.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5260 3.7718 3.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7809 4.0795 3.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4567 2.7074 -1.1139 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2505 4.0761 -2.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2375 4.5827 -4.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4016 3.7025 -5.9314 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6305 2.3504 -4.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3388 -1.6430 -2.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8289 -3.2637 -1.9065 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7600 -2.3553 -3.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7126 -1.9898 3.7448 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6769 -3.2655 4.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3564 -3.5379 2.9601 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 5 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 19 22 1 1 22 23 1 0 23 24 2 0 23 25 1 0 15 26 1 0 13 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 10 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 9 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 8 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 20 2 1 0 39 34 1 0 19 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 1 3 52 1 0 4 53 1 0 6 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 7 59 1 0 8 60 1 1 9 61 1 1 10 62 1 6 12 63 1 0 12 64 1 0 13 65 1 1 14 66 1 6 15 67 1 6 16 68 1 6 17 69 1 0 17 70 1 0 17 71 1 0 18 72 1 0 18 73 1 0 25 74 1 0 25 75 1 0 25 76 1 0 26 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 35 81 1 0 36 82 1 0 37 83 1 0 38 84 1 0 39 85 1 0 43 86 1 0 43 87 1 0 43 88 1 0 47 89 1 0 47 90 1 0 47 91 1 0 M END

Standard InCHIKey	CFGMCKRDNHXTBH-LDHUFNJZSA-N
Standard InCHI	InChI=1S/C35H44O12/c1-18-15-16-34(8,9)32(45-23(6)38)30(44-22(5)37)29(46-33(42)25-13-11-10-12-14-25)20(3)28(43-21(4)36)26-27(40)19(2)17-35(26,31(18)41)47-24(7)39/h10-16,18-19,26-30,32,40H,3,17H2,1-2,4-9H3/b16-15+/t18-,19+,26-,27+,28+,29+,30-,32-,35-/m1/s1
SMILES	C[C@@H]1/C=C/C(C)(C)[C@@H]([C@@H]([C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)OC(=O)C)O)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	656.28	Volume:	664.728 ? Van der Waals volume.
Dense:	0.987	LogP:	2.713 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.851 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.497 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	29.0
TPSA:	168.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.268	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.644	Fsp³:	0.543
MCE-18:	105.63 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.905	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.081 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.11

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203	MDCK Permeability:	-4.725
Pgp-inhibitor:	1.0	Pgp-substrate:	0.005
PAMPA:	0.203 ? 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%):	0.913	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	87.425%	Volume Distribution (VD):	-0.022
Fu:	14.232% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.006
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.302
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.024
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

5.384

Half-life (T1/2):

0.58

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.042
Human Hepatotoxicity (H-HT):	0.378	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.541	Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.107	Skin Sensitization:	0.994
Carcinogencity:	0.527	Eye Corrosion:	0.0
Eye Irritation:	0.098	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.233	Ototoxicity:	0.367
Hematotoxicity:	0.419	Drug-induced Nephrotoxicity:	0.838
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.67	Hek293 Cytotoxicity:	0.562
BCF:	0.622 ? 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:	3.516 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.29 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.851 ? 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
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27447736]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233482]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	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
IC50	1

Activity Type	# Activity
Cell line	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
NPT25056	Cell line	BMDM	n.a.	IC50	=	2300.0	nM	PMID[32233482]

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 NPC482267 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	8180
0.1-0.2	37701
0.2-0.3	3368
0.3-0.4	507
0.4-0.5	58
0.5-0.6	21
0.6-0.7	17
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
0.8148	Intermediate Similarity	NPC482260
0.7179	Intermediate Similarity	NPC265459
0.7179	Intermediate Similarity	NPC482304
0.7179	Intermediate Similarity	NPC482265
0.7	Intermediate Similarity	NPC482268
0.6962	Remote Similarity	NPC482249
0.6875	Remote Similarity	NPC482248
0.6875	Remote Similarity	NPC285221
0.679	Remote Similarity	NPC475660
0.675	Remote Similarity	NPC475262
0.6667	Remote Similarity	NPC482251
0.6625	Remote Similarity	NPC482266
0.6543	Remote Similarity	NPC290833
0.6506	Remote Similarity	NPC482255
0.6463	Remote Similarity	NPC482254
0.6386	Remote Similarity	NPC482269
0.6207	Remote Similarity	NPC482155
0.6207	Remote Similarity	NPC482250
0.6145	Remote Similarity	NPC194769
0.6136	Remote Similarity	NPC482204
0.6047	Remote Similarity	NPC482201
0.6	Remote Similarity	NPC482258
0.5814	Remote Similarity	NPC472247
0.5814	Remote Similarity	NPC482359
0.5806	Remote Similarity	NPC482261
0.573	Remote Similarity	NPC482202
0.5591	Remote Similarity	NPC482259
0.5581	Remote Similarity	NPC482247
0.5568	Remote Similarity	NPC482252
0.5465	Remote Similarity	NPC86772
0.5465	Remote Similarity	NPC482315
0.5402	Remote Similarity	NPC482270
0.5376	Remote Similarity	NPC482154
0.5333	Remote Similarity	NPC482253
0.5312	Remote Similarity	NPC482262
0.5287	Remote Similarity	NPC482300
0.5281	Remote Similarity	NPC482310
0.5281	Remote Similarity	NPC482302
0.5281	Remote Similarity	NPC482272
0.5227	Remote Similarity	NPC482231
0.5172	Remote Similarity	NPC228674
0.5114	Remote Similarity	NPC482314
0.5111	Remote Similarity	NPC482301

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3131
0.1-0.2	5870
0.2-0.3	148
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