NPASS Compound

Natural Product: NPC482219

Natural Product ID	NPC482219
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MXLZHQOOQIUQGO-FGQBBZSKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	134751194
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 89 92 0 0 0 0 0 0 0 0999 V2000 6.8674 -1.5670 -3.8173 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9516 -0.4593 -2.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2288 -0.7011 -1.5324 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7487 -0.9247 -1.7266 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0403 -1.1647 -0.4077 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2238 0.0140 0.4707 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1806 0.7318 0.9336 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4858 1.8654 1.7864 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5232 2.6040 2.2699 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1322 2.3793 2.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3594 3.2371 2.5991 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4385 1.4812 1.3174 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9759 1.3914 1.1589 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5196 0.2696 1.9949 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3971 0.7693 3.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2095 -0.8560 1.3664 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7249 -2.1642 1.8818 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2887 -2.3697 1.9940 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0642 -3.6841 2.0087 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2705 -4.3343 2.1144 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3676 -4.3895 1.8861 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6491 -5.5026 2.3270 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1581 -3.3751 1.1102 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6135 -3.5592 1.0977 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1377 -2.6893 -0.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5949 -1.5826 -0.5178 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3246 -0.8669 -0.1253 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2297 0.4210 -0.8210 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8847 0.8625 -1.3819 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8550 1.5934 -2.7277 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1448 -0.2089 -1.2974 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4949 1.5384 -0.2041 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1477 2.7623 -0.5745 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6241 4.0017 -0.5816 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4489 4.0972 -0.2334 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3774 5.1999 -0.9757 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5600 5.3253 -0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5251 6.4511 -0.8327 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4178 -3.1832 -0.6054 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2667 -4.4770 -1.1376 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5809 -0.8322 1.7868 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1699 -1.1357 -4.8164 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6448 -2.3653 -3.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8956 -2.0406 -3.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0439 -0.3576 -2.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6970 0.5428 -3.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7097 -1.5959 -1.0545 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4380 0.1674 -0.8737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6184 -1.8125 -2.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3356 -0.0669 -2.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9782 -1.3521 -0.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4513 -2.0944 0.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2080 0.3078 0.7485 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2376 0.3881 0.6222 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5316 2.1153 2.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8769 3.4424 2.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3440 2.2956 1.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6455 -0.1364 2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4148 0.0307 3.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4113 1.0150 2.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9195 1.7026 3.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1568 -2.3208 2.9201 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5255 -1.6642 2.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1519 -5.4211 2.2539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8145 -4.1908 1.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8880 -3.8720 2.9137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7659 -3.4445 0.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1419 -3.2711 2.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9240 -4.5897 0.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1715 -1.1485 -1.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5143 -1.5256 -0.5113 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0380 0.5804 -1.5843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0663 2.1641 -2.8327 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0127 0.8155 -3.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7699 2.2492 -2.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1350 0.2696 -1.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0183 -1.0014 -2.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2892 -0.6346 -0.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6897 5.0618 -2.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1347 6.2229 -0.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1677 4.3866 -0.1277 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1580 5.3443 0.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1735 7.3421 -0.8941 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7033 6.4577 -1.5794 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0309 6.3742 0.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8488 -2.4943 -1.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1680 -3.3028 0.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9270 -4.5162 -1.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6507 -1.0254 2.7431 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 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 19 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 6 33 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 36 38 1 0 25 39 1 0 39 40 1 0 16 41 1 1 32 13 1 0 27 16 1 0 32 28 1 0 23 17 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 0 2 46 1 0 3 47 1 0 3 48 1 0 4 49 1 0 4 50 1 0 5 51 1 0 5 52 1 0 6 53 1 0 7 54 1 0 8 55 1 0 9 56 1 0 13 57 1 1 14 58 1 1 15 59 1 0 15 60 1 0 15 61 1 0 17 62 1 1 18 63 1 0 20 64 1 0 20 65 1 0 20 66 1 0 23 67 1 6 24 68 1 0 24 69 1 0 26 70 1 0 27 71 1 6 28 72 1 6 30 73 1 0 30 74 1 0 30 75 1 0 31 76 1 0 31 77 1 0 31 78 1 0 36 79 1 0 37 80 1 0 37 81 1 0 37 82 1 0 38 83 1 0 38 84 1 0 38 85 1 0 39 86 1 0 39 87 1 0 40 88 1 0 41 89 1 0 M END

Standard InCHIKey	MXLZHQOOQIUQGO-FGQBBZSKSA-N
Standard InCHI	InChI=1S/C34H48O7/c1-8-9-10-11-12-13-14-15-27(36)40-30-22(5)33(39)25-16-21(4)28(37)24(25)17-23(19-35)18-26(33)29-32(6,7)34(29,30)41-31(38)20(2)3/h12-16,18,20,22,24-26,29-30,35,39H,8-11,17,19H2,1-7H3/b13-12+,15-14-/t22-,24+,25-,26+,29-,30-,33+,34-/m1/s1
SMILES	CCCCC/C=C/C=CC(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C(C)C)CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.34	Volume:	605.47 ? Van der Waals volume.
Dense:	0.939	LogP:	4.643 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.092 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.327 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	23.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.122	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.306	Fsp³:	0.676
MCE-18:	77.579 ? 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:	0.751	Fluc inhibitor:	0.064 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.048 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.281	Promiscuous compounds:	0.268

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109	MDCK Permeability:	-4.938
Pgp-inhibitor:	0.925	Pgp-substrate:	0.242
PAMPA:	0.45 ? 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):	0.04
20% Bioavailability (F20%):	0.982	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.871
Plasma Protein Binding (PPB):	94.499%	Volume Distribution (VD):	-0.091
Fu:	4.934% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.908
OATP1B3 inhibitor:	0.79	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.578
CYP2C19-inhibitor:	0.015	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.079	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.085	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.906 ? 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):

7.459

Half-life (T1/2):

0.678

ADMET: Toxicity

hERG Blockers:	0.263	hERG Blockers (10um):	0.513
Human Hepatotoxicity (H-HT):	0.769	Drug-induced Liver Injury (DILI):	0.398
AMES Toxicity:	0.775	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.672	Skin Sensitization:	0.999
Carcinogencity:	0.419	Eye Corrosion:	0.005
Eye Irritation:	0.293	Respiratory Toxicity:	0.78
Drug-induced Neurotoxicity:	0.264	Ototoxicity:	0.655
Hematotoxicity:	0.329	Drug-induced Nephrotoxicity:	0.859
Genotoxicity:	0.022	RPMI-8226 Immunitoxicity:	0.197
A549 Cytotoxicity:	0.694	Hek293 Cytotoxicity:	0.785
BCF:	1.348 ? 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:	4.379 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.973 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.448 ? 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
NPO4	Euphorbia dendroides	Species	Euphorbiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21707046]
NPO4	Euphorbia dendroides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29498278]
NPO4	Euphorbia dendroides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
EC50	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
NPT20632	Organism	Chikungunya virus	Chikungunya virus	EC50	=	900.0	nM	PMID[29498278]

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 NPC482219 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	18946
0.1-0.2	29379
0.2-0.3	1355
0.3-0.4	81
0.4-0.5	56
0.5-0.6	15
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC482221
0.9155	High Similarity	NPC482220
0.8472	Intermediate Similarity	NPC236918
0.8472	Intermediate Similarity	NPC156745
0.8267	Intermediate Similarity	NPC482222
0.7945	Intermediate Similarity	NPC608501
0.7763	Intermediate Similarity	NPC472759
0.7465	Intermediate Similarity	NPC482406
0.7162	Intermediate Similarity	NPC481520
0.716	Intermediate Similarity	NPC482199
0.716	Intermediate Similarity	NPC482197
0.7125	Intermediate Similarity	NPC329080
0.7067	Intermediate Similarity	NPC234858
0.7067	Intermediate Similarity	NPC179207
0.68	Remote Similarity	NPC472757
0.68	Remote Similarity	NPC481522
0.6753	Remote Similarity	NPC485737
0.6588	Remote Similarity	NPC482198
0.6456	Remote Similarity	NPC471127
0.6456	Remote Similarity	NPC481525
0.6456	Remote Similarity	NPC481531
0.6429	Remote Similarity	NPC482200
0.642	Remote Similarity	NPC10721
0.6364	Remote Similarity	NPC154363
0.625	Remote Similarity	NPC476111
0.6125	Remote Similarity	NPC475885
0.5976	Remote Similarity	NPC90814
0.5976	Remote Similarity	NPC189393
0.5882	Remote Similarity	NPC145238
0.5802	Remote Similarity	NPC482405
0.5765	Remote Similarity	NPC484333
0.5632	Remote Similarity	NPC481523
0.5542	Remote Similarity	NPC485734
0.5385	Remote Similarity	NPC140021
0.5333	Remote Similarity	NPC611138
0.5294	Remote Similarity	NPC481528
0.5269	Remote Similarity	NPC479001
0.5269	Remote Similarity	NPC479002
0.5125	Remote Similarity	NPC481521
0.5114	Remote Similarity	NPC478999
0.506	Remote Similarity	NPC472397

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6727
0.1-0.2	2387
0.2-0.3	36
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