NPASS Compound

Natural Product: NPC202667

Natural Product ID	NPC202667
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GOECIRGMYVJNBS-ZUKOONMSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102118407
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 62 63 0 0 0 0 0 0 0 0999 V2000 3.6458 -0.9036 -0.0508 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7555 0.1434 -0.6777 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7431 -0.4557 -1.6236 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8186 -1.4254 -0.9823 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0999 -0.9238 0.0751 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1084 0.0963 -0.2970 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3271 0.2454 -1.7868 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7809 1.4725 0.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7467 2.5251 -0.2432 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1662 2.1022 -0.3284 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4797 0.8137 0.3466 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9337 1.1791 1.7807 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7952 0.3063 -0.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4466 -0.2215 0.3987 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8711 -1.5762 -0.0922 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9689 -2.5811 0.5289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6290 -2.0784 0.9212 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2944 -3.3034 0.7854 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5241 -1.7917 2.3037 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6671 1.0268 -1.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6678 1.6225 -0.5996 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2997 2.5400 0.1787 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9966 1.2178 -0.5559 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8724 1.8587 0.3635 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4614 -0.3445 0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1547 -1.5318 0.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1292 -1.5355 -0.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2641 0.7488 0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2694 0.4099 -2.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3643 -0.9606 -2.4219 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5289 -2.1275 -0.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3287 -2.1203 -1.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6166 -0.4086 0.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4329 0.1620 -2.0200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9629 1.2100 -2.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8849 -0.5392 -2.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2353 1.8115 0.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9110 1.4078 1.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4508 2.9469 -1.2484 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6076 3.4017 0.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7792 2.9265 0.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5741 2.1493 -1.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 0.3086 2.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2493 1.9601 2.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9422 1.6114 1.7668 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6423 -0.2457 -1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4151 1.2150 -0.4260 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3493 -0.2965 0.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1419 -0.3652 1.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8140 -1.6404 -1.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9217 -1.8185 0.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9212 -3.4631 -0.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4497 -3.0115 1.4545 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2416 -4.0868 1.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2921 -3.7174 -0.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2503 -3.1673 1.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1117 -1.0362 2.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2398 0.3106 -2.1759 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1204 1.7719 -2.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3425 2.1229 1.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1965 2.8046 -0.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7369 1.2486 0.6372 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 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 1 2 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 17 5 1 0 14 6 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 1 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 1 7 34 1 0 7 35 1 0 7 36 1 0 8 37 1 0 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 12 43 1 0 12 44 1 0 12 45 1 0 13 46 1 0 13 47 1 0 13 48 1 0 14 49 1 1 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 18 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 M END

Standard InCHIKey	GOECIRGMYVJNBS-ZUKOONMSSA-N
Standard InCHI	InChI=1S/C21H38O3/c1-15(14-18(22)24-6)8-9-17-20(4)12-7-11-19(2,3)16(20)10-13-21(17,5)23/h15-17,23H,7-14H2,1-6H3/t15-,16-,17+,20-,21+/m1/s1
SMILES	C[C@H](CC[C@H]1[C@]2(C)CCCC(C)(C)[C@H]2CC[C@]1(C)O)CC(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	338.28	Volume:	378.393 ? Van der Waals volume.
Dense:	0.894	LogP:	4.285 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.737 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.673 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	12.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.721	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.076	Fsp³:	0.952
MCE-18:	47.268 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.092	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.939	Promiscuous compounds:	0.636

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708	MDCK Permeability:	-4.683
Pgp-inhibitor:	0.003	Pgp-substrate:	0.011
PAMPA:	0.776 ? 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%):	0.082	30% Bioavailability (F30%):	0.018
50% Bioavailability (F50%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039	MRP1:	0.527
Plasma Protein Binding (PPB):	97.133%	Volume Distribution (VD):	-0.113
Fu:	4.003% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.979
OATP1B3 inhibitor:	0.969	BCRP inhibitor:	0.206
BSEP inhibitor:	0.959

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.813
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.975
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
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):

9.821

Half-life (T1/2):

0.832

ADMET: Toxicity

hERG Blockers:	0.076	hERG Blockers (10um):	0.317
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.136
AMES Toxicity:	0.33	Rat Oral Acute Toxicity:	0.565
Maximum Recommended Daily Dose:	0.508	Skin Sensitization:	0.984
Carcinogencity:	0.781	Eye Corrosion:	0.459
Eye Irritation:	0.879	Respiratory Toxicity:	0.73
Drug-induced Neurotoxicity:	0.414	Ototoxicity:	0.379
Hematotoxicity:	0.31	Drug-induced Nephrotoxicity:	0.832
Genotoxicity:	0.078	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.338	Hek293 Cytotoxicity:	0.301
BCF:	2.009 ? 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:	4.417 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.807 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.229 ? 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
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[10579879]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844943]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16394535]
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456578]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379417]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4087921]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6061704]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8991954]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8991954]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461656]
NPO17291	Dodonaea lobulata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20945	Uncaria callophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20945	Uncaria callophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8805	Clavularia frankliniana	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17291	Dodonaea lobulata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18553	Heliopsis helianthoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20123	Actinidia polygama	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9861	Ophiostoma minus	Species	Ophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19334	Rosa polyantha	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21066	Penicillium corylophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20945	Uncaria callophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20063	Euonymus tanakae	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

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 NPC202667 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	17392
0.1-0.2	27912
0.2-0.3	4137
0.3-0.4	364
0.4-0.5	31
0.5-0.6	15
0.6-0.7	4
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	NPC41542
0.7551	Intermediate Similarity	NPC485098
0.7059	Intermediate Similarity	NPC485097
0.6735	Remote Similarity	NPC217714
0.6444	Remote Similarity	NPC135438
0.64	Remote Similarity	NPC485095
0.6226	Remote Similarity	NPC485096
0.5741	Remote Similarity	NPC292329
0.5714	Remote Similarity	NPC201048
0.5714	Remote Similarity	NPC378624
0.5714	Remote Similarity	NPC476366
0.5625	Remote Similarity	NPC64123
0.5532	Remote Similarity	NPC88454
0.5532	Remote Similarity	NPC101307
0.5532	Remote Similarity	NPC117607
0.551	Remote Similarity	NPC22134
0.551	Remote Similarity	NPC479668
0.549	Remote Similarity	NPC19311
0.5385	Remote Similarity	NPC230047
0.5294	Remote Similarity	NPC484735
0.5294	Remote Similarity	NPC351233
0.52	Remote Similarity	NPC476431

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC202667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6563
0.1-0.2	2440
0.2-0.3	146
0.3-0.4	1
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