NPASS Compound

Natural Product: NPC482359

Natural Product ID	NPC482359
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MGQBTBLHNLYVIS-FRUPGSIESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	71450237
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane 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 91 93 0 0 0 0 0 0 0 0999 V2000 -0.8072 -2.6698 -3.3952 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3193 -1.7613 -2.2202 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6159 -1.4306 -1.5377 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9035 -1.8886 -0.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2122 -1.4971 0.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2400 -1.8436 -0.8313 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6031 -2.2660 1.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2497 0.0133 0.4038 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9541 0.6013 0.8513 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1088 -0.0322 1.8334 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3975 0.1487 1.7651 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6858 1.4712 2.6406 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1188 0.3673 0.6096 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5613 -0.4581 -0.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3728 -0.1836 -1.5552 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2087 -1.4093 -1.7050 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1827 -2.0252 -3.0822 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8457 -2.3205 -0.5922 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3690 -1.8860 -0.2684 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6371 -2.5073 -1.4023 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8072 -3.6842 -1.7096 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1854 -2.4369 0.9806 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0218 -3.7030 1.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0247 -4.6198 0.5458 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8306 -4.0909 2.8349 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 0.8724 -1.1981 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3951 2.0316 -1.9178 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6332 2.2035 -2.9118 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3532 3.0564 -1.5259 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1734 2.8436 -0.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0697 3.8107 -0.0805 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1300 4.9863 -0.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2992 5.2050 -1.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4069 4.2238 -2.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8637 -0.7887 2.7247 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4742 0.3635 3.1456 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8288 -0.4445 4.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8486 -1.6812 4.0206 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1956 0.1658 5.4932 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0595 2.0092 0.9321 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5830 2.9193 0.0397 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9768 2.4851 -0.9774 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7040 4.3897 0.1405 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6090 0.5455 -0.8537 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8092 1.1967 -1.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6083 1.3163 -0.1258 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1330 1.7324 -2.4087 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4679 -2.0052 -3.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4342 -3.4784 -3.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0205 -2.9926 -4.0196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0070 -0.8556 -2.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2721 -0.7852 -2.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3139 -2.5823 0.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2518 -1.9385 -0.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2105 -1.1165 -1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9484 -2.8284 -1.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8255 -2.9986 1.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9672 -1.6076 2.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5010 -2.9384 1.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1010 0.2343 1.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3310 0.5114 -0.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3108 -1.1660 1.9092 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1373 2.3017 2.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3558 1.2791 3.6536 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7476 1.6791 2.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3991 1.4280 0.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8326 0.1273 -2.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3134 -1.1770 -1.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8092 -1.3377 -3.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2075 -2.2115 -3.5070 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7734 -2.9586 -3.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8429 -3.3605 -0.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4553 -2.2246 0.3181 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -5.1049 2.8943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8260 -4.0153 3.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1535 -3.4070 3.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1572 1.9278 0.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7468 3.7215 0.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8167 5.7689 -0.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3191 6.1080 -2.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7302 4.3384 -3.0952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6295 -0.5550 3.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2802 0.0590 5.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9767 1.2512 5.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5857 -0.2638 6.3202 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9493 4.9233 -0.4637 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7591 4.6482 -0.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6235 4.6877 1.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1811 2.0373 -2.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6342 0.9124 -2.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7809 2.6341 -2.3319 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 1 0 11 13 1 0 13 14 2 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 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 11 35 1 1 10 36 1 0 36 37 1 0 37 38 2 0 37 39 1 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 34 29 1 0 19 14 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 6 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 6 10 62 1 1 12 63 1 0 12 64 1 0 12 65 1 0 13 66 1 0 15 67 1 6 16 68 1 1 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 30 77 1 0 31 78 1 0 32 79 1 0 33 80 1 0 34 81 1 0 35 82 1 0 39 83 1 0 39 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	MGQBTBLHNLYVIS-FRUPGSIESA-N
Standard InCHI	InChI=1S/C35H44O12/c1-19-15-16-33(7,8)30(44-22(4)37)28(43-21(3)36)31(45-23(5)38)34(9,42)18-26-27(46-32(41)25-13-11-10-12-14-25)20(2)17-35(26,29(19)40)47-24(6)39/h10-16,18-20,27-28,30-31,42H,17H2,1-9H3/b16-15+,26-18-/t19-,20+,27-,28+,30+,31-,34-,35+/m0/s1
SMILES	C[C@H]1/C=C/C(C)(C)[C@@H]([C@H]([C@@H]([C@](C)(/C=C2/[C@H]([C@H](C)C[C@@]2(C1=O)OC(=O)C)OC(=O)c1ccccc1)O)OC(=O)C)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:	2.872 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.973 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.533 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	28.0
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:	0.267	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.683	Fsp³:	0.543
MCE-18:	107.852 ? 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:	0.561	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.018 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.292	Promiscuous compounds:	0.369

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.342	MDCK Permeability:	-4.855
Pgp-inhibitor:	1.0	Pgp-substrate:	0.185
PAMPA:	0.246 ? 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):	0.012
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	89.384%	Volume Distribution (VD):	-0.031
Fu:	10.929% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.432
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.991
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.434	CYP3A4-substrate:	0.981
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):

5.919

Half-life (T1/2):

0.489

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.053
Human Hepatotoxicity (H-HT):	0.659	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.683	Rat Oral Acute Toxicity:	0.508
Maximum Recommended Daily Dose:	0.456	Skin Sensitization:	0.996
Carcinogencity:	0.856	Eye Corrosion:	0.0
Eye Irritation:	0.058	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.186	Ototoxicity:	0.247
Hematotoxicity:	0.31	Drug-induced Nephrotoxicity:	0.886
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.165
A549 Cytotoxicity:	0.471	Hek293 Cytotoxicity:	0.48
BCF:	0.559 ? 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:	3.523 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.257 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.771 ? 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
NPO17435	Euphorbia mellifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23098168]
NPO17435	Euphorbia mellifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17435	Euphorbia mellifera	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
Ratio	6
Activity	3

Activity Type	# Activity
Cell line	2
Individual protein	6
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	3.0	n.a.	PMID[23098168]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.7	n.a.	PMID[23098168]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	43.4	n.a.	PMID[23098168]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	10.1	n.a.	PMID[23098168]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.4	n.a.	PMID[23098168]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.9	n.a.	PMID[23098168]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2641	Cell line	COLO 320	Homo sapiens	Activity	=	4.6	%	PMID[23098168]
NPT2641	Cell line	COLO 320	Homo sapiens	Activity	=	4.4	%	PMID[23098168]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.9	%	PMID[23098168]

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 NPC482359 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	8813
0.1-0.2	37675
0.2-0.3	2766
0.3-0.4	525
0.4-0.5	57
0.5-0.6	17
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472247
0.5814	Remote Similarity	NPC482267
0.5765	Remote Similarity	NPC290833
0.5765	Remote Similarity	NPC482249
0.5632	Remote Similarity	NPC482268
0.5581	Remote Similarity	NPC265459
0.5581	Remote Similarity	NPC475262
0.5581	Remote Similarity	NPC482304
0.5581	Remote Similarity	NPC482265
0.5455	Remote Similarity	NPC482269
0.5393	Remote Similarity	NPC482255
0.5341	Remote Similarity	NPC482251
0.5287	Remote Similarity	NPC482266
0.5169	Remote Similarity	NPC482248
0.5169	Remote Similarity	NPC285221
0.5169	Remote Similarity	NPC482254
0.5111	Remote Similarity	NPC475660
0.5056	Remote Similarity	NPC482247

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3463
0.1-0.2	5547
0.2-0.3	140
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