NPASS Compound

Natural Product: NPC14499

Natural Product ID	NPC14499
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Orbiculin E
IUPAC Name	n.a.
Synonyms	Orbiculin E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500858
PubChem CID	10745604
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 77 81 0 0 0 0 0 0 0 0999 V2000 4.3572 -2.2509 0.8107 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1354 -1.9027 0.0686 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1792 -1.7881 -1.1701 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9390 -1.6949 0.6620 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7359 -1.3533 0.0064 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2269 -2.5145 -0.0455 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4387 -3.7122 0.3840 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5627 -4.7942 -0.4352 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0765 -4.7265 -1.5945 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2615 -6.0369 0.0309 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4602 -2.3986 0.7805 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1749 -1.0745 0.6443 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3193 -0.0981 -0.0825 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1250 -0.0549 0.4195 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2004 0.0676 1.9324 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7817 1.1747 -0.0900 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1806 1.0664 -0.0978 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9994 1.9030 0.6526 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4023 2.7806 1.3742 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4342 1.8932 0.7075 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2102 1.0539 -0.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5868 1.0494 0.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2464 1.8971 0.8687 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4853 2.7500 1.6441 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1024 2.7425 1.5595 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2844 1.6723 -1.4108 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2205 1.6819 -1.5175 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8116 1.2996 -0.1412 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2241 1.4007 -0.2049 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8376 2.3484 0.6019 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0984 3.0748 1.3552 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2822 2.5416 0.6193 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1730 1.8205 -0.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4538 2.2955 0.1504 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2466 3.2894 1.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9563 3.3934 1.3303 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6047 0.4149 -2.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2422 -0.5644 -1.4046 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7870 0.3779 -3.5695 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0424 0.4146 -2.6898 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7681 -0.5864 1.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2689 -1.8006 0.4014 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1751 -1.9518 1.8850 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4875 -3.3719 0.8831 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0515 -1.2149 -1.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5453 -2.7331 -1.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3688 -5.8483 0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0744 -6.8807 -0.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9231 -6.2860 1.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1415 -3.2299 0.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3299 -2.7136 1.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0577 -1.2580 -0.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3319 -0.6665 2.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1384 1.0828 2.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3124 0.0815 2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5845 2.0580 0.6162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6668 0.3985 -0.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1506 0.3749 -0.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3457 1.9094 0.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0019 3.4113 2.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5465 3.4288 2.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7424 1.0677 -2.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5988 2.7216 -1.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6544 2.5897 -1.9220 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 2.0102 0.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0274 1.0336 -0.8552 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4096 1.9917 -0.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0177 3.8844 1.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0410 -0.3408 -3.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4554 1.4163 -3.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4150 0.0507 -4.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7369 -0.0357 -1.9922 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3612 1.4672 -2.8582 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1622 -0.0980 -3.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6177 -1.3320 2.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8961 -0.4965 1.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4375 0.4271 2.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 6 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 16 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 27 37 1 0 37 38 1 0 37 39 1 0 37 40 1 0 12 41 1 0 14 5 1 0 25 20 1 0 36 32 1 0 13 38 1 6 28 13 1 0 1 42 1 0 1 43 1 0 1 44 1 0 5 45 1 6 6 46 1 6 10 47 1 0 10 48 1 0 10 49 1 0 11 50 1 0 11 51 1 0 12 52 1 6 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 1 21 57 1 0 22 58 1 0 23 59 1 0 24 60 1 0 25 61 1 0 26 62 1 0 26 63 1 0 27 64 1 6 28 65 1 1 33 66 1 0 34 67 1 0 35 68 1 0 39 69 1 0 39 70 1 0 39 71 1 0 40 72 1 0 40 73 1 0 40 74 1 0 41 75 1 0 41 76 1 0 41 77 1 0 M END

Standard InCHIKey	CEKCSANPFZSVKO-ICWAWGCGSA-N
Standard InCHI	InChI=1S/C31H36O10/c1-17-15-23(37-18(2)32)26(38-19(3)33)30(6)24(39-27(34)20-11-8-7-9-12-20)16-21-25(31(17,30)41-29(21,4)5)40-28(35)22-13-10-14-36-22/h7-14,17,21,23-26H,15-16H2,1-6H3/t17-,21-,23+,24+,25-,26+,30-,31-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H](OC(=O)C)C[C@H]([C@@]23[C@]1(C)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3OC(=O)c1ccco1)C(O2)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	568.23	Volume:	566.124 ? Van der Waals volume.
Dense:	1.004	LogP:	3.415 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.243 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.895 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	29.0
TPSA:	127.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.363	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.79	Fsp³:	0.548
MCE-18:	160.5 ? 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:	0.447	Fluc inhibitor:	0.168 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.015 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.265	Promiscuous compounds:	0.063

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109	MDCK Permeability:	-4.706
Pgp-inhibitor:	0.98	Pgp-substrate:	0.157
PAMPA:	0.194 ? 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%):	0.29	30% Bioavailability (F30%):	0.375
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.579	MRP1:	0.999
Plasma Protein Binding (PPB):	90.882%	Volume Distribution (VD):	-0.35
Fu:	8.098% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.945	BCRP inhibitor:	0.101
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.383
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.095	CYP3A4-substrate:	0.86
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):

4.482

Half-life (T1/2):

0.551

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.462
Human Hepatotoxicity (H-HT):	0.129	Drug-induced Liver Injury (DILI):	0.956
AMES Toxicity:	0.506	Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.244	Skin Sensitization:	0.964
Carcinogencity:	0.784	Eye Corrosion:	0.001
Eye Irritation:	0.372	Respiratory Toxicity:	0.088
Drug-induced Neurotoxicity:	0.308	Ototoxicity:	0.191
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.377
Genotoxicity:	0.627	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.328	Hek293 Cytotoxicity:	0.411
BCF:	0.686 ? 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:	3.608 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.089 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.685 ? 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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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	5
Ratio IC50	4

Activity Type	# Activity
Cell line	2
Non-molecular	3
Others	4

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	300000.0	nM	PMID[11809076]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	28300.0	nM	PMID[10346948]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	33100.0	nM	PMID[10346948]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	500.0	nM	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	66.2	n.a.	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	1.8	n.a.	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	1.6	n.a.	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	2.6	n.a.	PMID[10346948]

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 NPC14499 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	18699
0.1-0.2	29479
0.2-0.3	1338
0.3-0.4	214
0.4-0.5	72
0.5-0.6	33
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC88593
0.7733	Intermediate Similarity	NPC475039
0.7714	Intermediate Similarity	NPC159520
0.7647	Intermediate Similarity	NPC200592
0.7647	Intermediate Similarity	NPC610542
0.7391	Intermediate Similarity	NPC195647
0.7273	Intermediate Similarity	NPC476035
0.7143	Intermediate Similarity	NPC270498
0.6901	Remote Similarity	NPC473081
0.6829	Remote Similarity	NPC483870
0.6375	Remote Similarity	NPC607428
0.6282	Remote Similarity	NPC473673
0.6203	Remote Similarity	NPC472574
0.6184	Remote Similarity	NPC1408
0.6173	Remote Similarity	NPC473112
0.6154	Remote Similarity	NPC177340
0.6118	Remote Similarity	NPC483874
0.6092	Remote Similarity	NPC483869
0.6067	Remote Similarity	NPC483868
0.5949	Remote Similarity	NPC43241
0.5823	Remote Similarity	NPC479047
0.5823	Remote Similarity	NPC291638
0.575	Remote Similarity	NPC67777
0.5682	Remote Similarity	NPC75600
0.5682	Remote Similarity	NPC483884
0.5658	Remote Similarity	NPC283375
0.5632	Remote Similarity	NPC483872
0.5625	Remote Similarity	NPC191082
0.5595	Remote Similarity	NPC473613
0.5595	Remote Similarity	NPC473085
0.5581	Remote Similarity	NPC608007
0.5556	Remote Similarity	NPC139067
0.5513	Remote Similarity	NPC481047
0.5513	Remote Similarity	NPC481045
0.5506	Remote Similarity	NPC483871
0.5465	Remote Similarity	NPC483875
0.5455	Remote Similarity	NPC183122
0.5455	Remote Similarity	NPC474608
0.5432	Remote Similarity	NPC4341
0.5422	Remote Similarity	NPC479044
0.5393	Remote Similarity	NPC56953
0.5244	Remote Similarity	NPC483883
0.5244	Remote Similarity	NPC151585
0.5165	Remote Similarity	NPC483864
0.5122	Remote Similarity	NPC70973
0.5122	Remote Similarity	NPC163087
0.5116	Remote Similarity	NPC184747
0.5114	Remote Similarity	NPC483887
0.5114	Remote Similarity	NPC158020
0.5063	Remote Similarity	NPC481066
0.506	Remote Similarity	NPC246841
0.5057	Remote Similarity	NPC36021

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3376
0.1-0.2	5625
0.2-0.3	145
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