NPASS Compound

Natural Product: NPC475277

Natural Product ID	NPC475277
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LLBHSZVLXQBXRK-OAGHFIFOSA-N
IUPAC Name	n.a.
Synonyms	Ingol-3,7,8,12-Diacetate,Ditiglate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502625
PubChem CID	44559780
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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 90 93 0 0 0 0 0 0 0 0999 V2000 1.9948 6.9859 -0.4265 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4930 5.6029 -0.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 4.9160 -1.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6430 3.5554 -1.1392 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2890 2.9016 -2.1792 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5637 2.9870 0.1009 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0696 1.6242 0.2183 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2202 1.8024 1.0204 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9160 2.3487 2.2500 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3311 3.5689 2.7298 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0661 4.2602 1.9662 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9110 3.9967 4.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0152 0.5379 1.0595 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9070 -0.3742 0.1126 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6432 -1.6708 0.0688 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0672 -2.7059 -0.6962 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0458 -2.7218 0.6989 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7199 -2.6631 1.3417 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7404 -2.5433 2.5785 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5481 -2.7385 0.6896 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1397 -1.4739 0.0513 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4369 -0.4258 1.0125 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0933 0.9350 1.0331 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4533 0.6048 0.5433 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8198 0.7923 -0.8836 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6493 0.7426 1.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4496 -1.9930 -0.3639 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7389 -2.2058 -1.6966 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8878 -1.9630 -2.5887 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0476 -2.7166 -2.0560 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -2.9815 -1.1401 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3171 -3.5059 -1.4663 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3915 -2.9549 -3.4623 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6054 -3.3604 1.6214 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1227 -3.5739 1.3579 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4025 -2.8833 1.0239 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1239 -1.7452 0.0929 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6520 -2.0047 -1.2191 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5898 -1.1788 -1.7876 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9725 -0.1712 -1.1014 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1882 -1.3585 -3.1180 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4269 -3.8510 0.4785 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0121 0.4063 2.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1938 5.4979 -2.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6383 7.0624 -1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5507 7.3000 0.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1418 7.6830 -0.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4427 5.1758 0.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1510 1.2972 -0.7652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8737 2.5349 0.4713 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3186 3.3707 4.8880 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1893 4.0892 4.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3237 5.0359 4.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2810 -0.2230 -0.7784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5150 -3.4753 -0.1762 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6538 -1.2911 -0.8845 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6707 -0.8923 2.0493 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1762 1.4594 2.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0169 1.9111 -0.9985 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0516 0.5823 -1.6207 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8272 0.3542 -1.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9569 1.8111 1.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2930 0.5159 2.5168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4525 0.0854 1.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6638 -2.7888 -0.1038 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0513 -2.7619 -1.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4160 -4.4929 -0.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3755 -3.5846 -2.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2710 -2.2910 -3.7031 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5712 -2.6255 -4.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6221 -4.0085 -3.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7905 -4.4198 1.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2158 -3.2482 2.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5516 -2.8005 1.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0629 -4.5751 0.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9106 -3.6217 2.4439 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7960 -2.4482 1.9821 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6244 -0.8277 0.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6738 -0.7235 -3.8869 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2474 -2.4255 -3.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2384 -0.9955 -3.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1099 -4.8769 0.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5792 -3.7664 -0.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4035 -3.6799 0.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9744 0.9416 1.9141 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2733 -0.6173 2.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6666 0.8874 3.0936 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1994 5.9466 -2.9570 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4643 6.3388 -2.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 4.7761 -3.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 8 13 1 0 13 14 2 0 14 15 1 0 15 16 1 6 17 16 1 6 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 21 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 30 31 2 0 31 32 1 0 30 33 1 0 20 34 1 0 17 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 36 42 1 0 13 43 1 0 3 44 1 0 23 7 1 0 37 15 1 0 17 15 1 0 24 22 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 7 49 1 6 8 50 1 6 12 51 1 0 12 52 1 0 12 53 1 0 14 54 1 0 20 55 1 6 21 56 1 6 22 57 1 1 23 58 1 1 25 59 1 0 25 60 1 0 25 61 1 0 26 62 1 0 26 63 1 0 26 64 1 0 31 65 1 0 32 66 1 0 32 67 1 0 32 68 1 0 33 69 1 0 33 70 1 0 33 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 35 75 1 0 35 76 1 0 36 77 1 1 37 78 1 1 41 79 1 0 41 80 1 0 41 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 43 85 1 0 43 86 1 0 43 87 1 0 44 88 1 0 44 89 1 0 44 90 1 0 M END

Standard InCHIKey	LLBHSZVLXQBXRK-OAGHFIFOSA-N
Standard InCHI	InChI=1S/C34H46O10/c1-12-16(3)30(38)42-26-20(7)28(37)33-15-19(6)29(41-22(9)36)34(33,44-33)14-18(5)25(40-21(8)35)27(24-23(26)32(24,10)11)43-31(39)17(4)13-2/h12-14,19-20,23-27,29H,15H2,1-11H3/b16-12+,17-13+,18-14+/t19-,20+,23-,24+,25+,26-,27-,29-,33-,34-/m0/s1
SMILES	C/C=C(/C(=O)O[C@@H]1[C@H](OC(=O)C)/C(=C/[C@]23O[C@]3(C(=O)[C@@H]([C@@H]([C@@H]3[C@H]1C3(C)C)OC(=O)/C(=C/C)/C)C)C[C@@H]([C@@H]2OC(=O)C)C)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	614.31	Volume:	629.205 ? Van der Waals volume.
Dense:	0.976	LogP:	3.221 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.263 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.762 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	26.0
TPSA:	134.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.06	Fsp³:	0.676
MCE-18:	89.579 ? 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:	0.84	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.359	Promiscuous compounds:	0.568

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.106	MDCK Permeability:	-4.803
Pgp-inhibitor:	0.992	Pgp-substrate:	0.168
PAMPA:	0.76 ? 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):	0.11
20% Bioavailability (F20%):	0.988	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	90.944%	Volume Distribution (VD):	-0.01
Fu:	6.813% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.72	BCRP inhibitor:	0.001
BSEP inhibitor:	0.988

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.049	CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.031	CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.248
CYP3A4-inhibitor:	0.194	CYP3A4-substrate:	0.562
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):

8.555

Half-life (T1/2):

0.87

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.184
Human Hepatotoxicity (H-HT):	0.566	Drug-induced Liver Injury (DILI):	0.879
AMES Toxicity:	0.858	Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.602	Skin Sensitization:	0.999
Carcinogencity:	0.56	Eye Corrosion:	0.006
Eye Irritation:	0.143	Respiratory Toxicity:	0.735
Drug-induced Neurotoxicity:	0.385	Ototoxicity:	0.381
Hematotoxicity:	0.972	Drug-induced Nephrotoxicity:	0.856
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.273
A549 Cytotoxicity:	0.599	Hek293 Cytotoxicity:	0.665
BCF:	0.759 ? 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:	3.635 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.046 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.602 ? 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
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	latices	South African	n.a.	PMID[3236005]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25960	Euphorbia triangularis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32447	euphorbia ledienii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19062	Euphorbia coerulescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25960	Euphorbia triangularis	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
Activity	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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	>	1000.0	ug	PMID[19877653]

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 NPC475277 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	23303
0.1-0.2	24925
0.2-0.3	1584
0.3-0.4	1
0.4-0.5	8
0.5-0.6	14
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC475495
0.8966	High Similarity	NPC482193
0.8852	High Similarity	NPC473522
0.8644	High Similarity	NPC477093
0.85	High Similarity	NPC482192
0.7742	Intermediate Similarity	NPC482185
0.746	Intermediate Similarity	NPC482184
0.7344	Intermediate Similarity	NPC482179
0.7188	Intermediate Similarity	NPC482178
0.7188	Intermediate Similarity	NPC482177
0.7121	Intermediate Similarity	NPC482176
0.7077	Intermediate Similarity	NPC81761
0.7015	Intermediate Similarity	NPC482180
0.6986	Remote Similarity	NPC477094
0.6912	Remote Similarity	NPC482174
0.6818	Remote Similarity	NPC189556
0.6818	Remote Similarity	NPC477092
0.6667	Remote Similarity	NPC475401
0.6528	Remote Similarity	NPC29922
0.6479	Remote Similarity	NPC475305
0.6301	Remote Similarity	NPC477096
0.6104	Remote Similarity	NPC482402
0.6026	Remote Similarity	NPC482400
0.597	Remote Similarity	NPC479266
0.5867	Remote Similarity	NPC477095
0.5634	Remote Similarity	NPC29905
0.5634	Remote Similarity	NPC482194
0.5634	Remote Similarity	NPC482190
0.5634	Remote Similarity	NPC482186
0.5634	Remote Similarity	NPC482191
0.5432	Remote Similarity	NPC272004
0.5432	Remote Similarity	NPC477101
0.5432	Remote Similarity	NPC477099
0.5432	Remote Similarity	NPC477097
0.5211	Remote Similarity	NPC482187
0.5172	Remote Similarity	NPC482195
0.5122	Remote Similarity	NPC482175

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7160
0.1-0.2	1979
0.2-0.3	11
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