NPASS Compound

Natural Product: NPC239556

Natural Product ID	NPC239556
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KPDOJFFZKAUIOE-BIYZDVJRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46783795
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

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 71 76 0 0 0 0 0 0 0 0999 V2000 -1.4540 -0.2242 -4.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5664 -0.7570 -3.3133 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0320 -1.8445 -2.9694 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2562 -0.1091 -2.3097 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3953 -0.5507 -0.9983 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7792 -0.9868 -0.6393 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6924 0.0685 -0.1916 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8722 0.0403 -0.6193 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4819 1.1658 0.6746 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4497 1.2990 1.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9712 2.6558 1.8918 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0847 0.7743 2.9234 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3935 0.2547 1.3025 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6140 0.0494 2.5736 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5574 -0.9474 2.2284 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5334 -2.0831 2.6428 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4369 -0.3379 1.3164 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9894 0.8745 2.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2129 0.0415 0.0335 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6809 1.0690 -0.5952 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0748 0.5037 -0.7785 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3605 -0.8057 -0.1810 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1377 -1.9003 -1.2333 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8593 -0.8781 0.1518 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7107 -0.1293 -0.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3111 1.0980 -0.4277 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0493 1.5173 -1.5140 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9177 0.6182 -2.4364 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1333 -0.3780 -2.0273 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1425 -2.2694 0.2119 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1495 -3.0508 0.8205 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3030 -4.3058 0.7089 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9928 -2.4448 1.5489 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6228 -1.2063 1.0347 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4177 -1.3154 2.2944 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6843 0.3368 0.0334 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8069 1.7056 -0.6667 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6492 0.5001 -4.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3631 -1.0705 -5.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4239 0.2639 -4.9292 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8012 -1.5164 -0.9478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2094 -1.3408 -1.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8323 -1.9334 -0.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2861 3.0414 2.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3285 3.4642 1.2146 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8537 2.6400 1.9816 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2026 -0.3056 2.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0497 1.3333 3.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4385 1.1668 3.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0348 -0.6869 1.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2161 0.9762 3.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2201 -0.4257 3.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0172 0.6006 3.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3713 1.7600 2.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0682 1.0399 1.8320 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0712 -0.8680 -0.6286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8086 1.9883 0.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3835 1.4444 -1.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8599 1.2390 -0.4204 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3448 0.4170 -1.8797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0606 -2.3802 -1.5578 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4495 -2.6823 -0.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6843 -1.4430 -2.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9381 -0.5084 1.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1985 1.6155 0.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6207 2.4441 -1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8776 -1.2343 -2.6137 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4175 -3.2083 2.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5967 1.5809 -1.7509 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8436 2.0844 -0.6657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1319 2.4561 -0.2878 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 2 0 7 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 24 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 34 35 1 1 19 36 1 0 36 37 1 6 36 5 1 0 36 13 1 0 34 17 1 0 34 22 1 0 29 25 2 0 35 33 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 11 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 12 49 1 0 13 50 1 6 14 51 1 0 14 52 1 0 18 53 1 0 18 54 1 0 18 55 1 0 19 56 1 6 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 23 61 1 0 23 62 1 0 23 63 1 0 24 64 1 1 26 65 1 0 27 66 1 0 29 67 1 0 33 68 1 1 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	KPDOJFFZKAUIOE-BIYZDVJRSA-N
Standard InCHI	InChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3/t16-,17+,19?,21+,22-,25+,26-,27+,28-/m1/s1
SMILES	CC(=O)OC1CC(=O)OC(C)(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)[C@@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	514.22	Volume:	504.799 ? Van der Waals volume.
Dense:	1.019	LogP:	1.474 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.774 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.434 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	33.0
TPSA:	121.64 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.33	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.642	Fsp³:	0.714
MCE-18:	197.083 ? 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:	0.283	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.009 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.101	Promiscuous compounds:	0.133

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.241	MDCK Permeability:	-4.832
Pgp-inhibitor:	0.99	Pgp-substrate:	0.07
PAMPA:	0.77 ? 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):	0.004
20% Bioavailability (F20%):	0.053	30% Bioavailability (F30%):	0.305
50% Bioavailability (F50%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.994
Plasma Protein Binding (PPB):	81.377%	Volume Distribution (VD):	-0.152
Fu:	18.472% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.115
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.581	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.026	CYP3A4-substrate:	0.044
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.851
HLM stability:	0.863 ? 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):

5.37

Half-life (T1/2):

0.75

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.219
Human Hepatotoxicity (H-HT):	0.74	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.626	Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.959	Skin Sensitization:	0.985
Carcinogencity:	0.713	Eye Corrosion:	0.014
Eye Irritation:	0.916	Respiratory Toxicity:	0.753
Drug-induced Neurotoxicity:	0.389	Ototoxicity:	0.607
Hematotoxicity:	0.417	Drug-induced Nephrotoxicity:	0.938
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.161
A549 Cytotoxicity:	0.039	Hek293 Cytotoxicity:	0.036
BCF:	0.612 ? 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:	3.389 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.248 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.729 ? 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
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	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

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

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 NPC239556 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	13851
0.1-0.2	34159
0.2-0.3	1605
0.3-0.4	176
0.4-0.5	30
0.5-0.6	17
0.6-0.7	15
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	NPC237155
0.7722	Intermediate Similarity	NPC476853
0.7403	Intermediate Similarity	NPC470939
0.7037	Intermediate Similarity	NPC305016
0.679	Remote Similarity	NPC263265
0.6456	Remote Similarity	NPC604270
0.6322	Remote Similarity	NPC25255
0.631	Remote Similarity	NPC611370
0.6296	Remote Similarity	NPC60973
0.6296	Remote Similarity	NPC605384
0.6235	Remote Similarity	NPC472653
0.6235	Remote Similarity	NPC476861
0.6235	Remote Similarity	NPC476850
0.6111	Remote Similarity	NPC472651
0.6092	Remote Similarity	NPC476856
0.6047	Remote Similarity	NPC126723
0.6024	Remote Similarity	NPC107646
0.6023	Remote Similarity	NPC476858
0.6	Remote Similarity	NPC123088
0.5904	Remote Similarity	NPC602263
0.5851	Remote Similarity	NPC472652
0.5765	Remote Similarity	NPC134254
0.5765	Remote Similarity	NPC39986
0.5747	Remote Similarity	NPC475381
0.573	Remote Similarity	NPC193798
0.5667	Remote Similarity	NPC604177
0.5632	Remote Similarity	NPC209364
0.5632	Remote Similarity	NPC605015
0.5581	Remote Similarity	NPC335761
0.5556	Remote Similarity	NPC117986
0.5517	Remote Similarity	NPC302369
0.5506	Remote Similarity	NPC23387
0.5326	Remote Similarity	NPC271235
0.5319	Remote Similarity	NPC469846
0.5222	Remote Similarity	NPC609366
0.5169	Remote Similarity	NPC470941

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC239556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3946
0.1-0.2	5173
0.2-0.3	31
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