NPASS Compound

Natural Product: NPC307125

Natural Product ID	NPC307125
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OBNYZGVKISJJRK-UAMYCEOTSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	100913914
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

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 67 70 0 0 0 0 0 0 0 0999 V2000 7.0508 -1.1581 0.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3825 -1.4785 0.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2957 -0.8591 -0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8196 0.1258 -1.5892 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4580 0.4638 -1.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5610 -0.1545 -0.7646 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1541 0.1852 -0.7473 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6542 1.1105 -1.5177 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2279 1.4065 -1.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7695 2.3003 -2.2036 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3549 0.7560 -0.6116 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9783 1.0096 -0.5187 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3975 0.0842 0.5167 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0838 0.3089 0.7350 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2698 0.7109 2.1510 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4453 -0.3995 3.1106 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6930 -1.6052 2.7077 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8035 -1.9095 1.3887 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8962 -0.9372 0.3703 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2198 -0.6522 0.1849 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7310 -0.9225 -1.0446 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9055 -1.8625 -1.0548 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0037 -1.4119 -0.1158 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8243 0.0689 0.1216 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2962 0.7973 -1.0681 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1622 2.2592 -0.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8736 3.0674 -1.7749 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1573 0.2741 -1.6211 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0913 0.5868 0.4339 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9440 -2.0499 1.1026 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4427 -1.8392 -2.3451 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1013 1.3266 2.4805 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0072 0.2711 1.8681 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3308 0.6651 1.8392 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2034 2.5474 1.8599 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6443 -1.2354 0.0825 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6388 -1.1894 -0.7662 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3366 -1.6516 0.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7681 -2.2593 0.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4834 0.6706 -2.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1341 1.2428 -2.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5060 -0.3786 -0.0443 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2616 1.6598 -2.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5341 0.7172 -1.5084 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7218 2.0624 -0.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4503 1.1531 0.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0479 1.4982 2.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3583 -0.1711 4.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8201 -2.4185 3.4482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3932 -1.3616 -0.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9687 -1.3493 -1.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6611 -2.8950 -0.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0092 -1.5625 -0.5478 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2053 0.2390 1.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1008 0.7548 -1.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3518 2.3361 0.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0916 2.5686 -0.1782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1802 2.5939 -2.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7996 -0.0997 0.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6227 -2.7421 1.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9927 -2.5534 -2.8651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2418 1.3633 3.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 -0.6607 2.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8769 -0.1773 1.8229 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6816 2.9520 1.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.2393 -0.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1861 -0.9527 0.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 15 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 13 36 1 6 3 37 1 0 6 1 1 0 33 13 1 0 19 14 1 0 28 21 1 0 1 38 1 0 2 39 1 0 4 40 1 0 5 41 1 0 7 42 1 0 8 43 1 0 12 44 1 0 12 45 1 0 14 46 1 6 15 47 1 6 16 48 1 0 17 49 1 0 19 50 1 6 21 51 1 6 22 52 1 1 23 53 1 6 24 54 1 1 25 55 1 6 26 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 30 60 1 0 31 61 1 0 32 62 1 1 33 63 1 1 34 64 1 0 35 65 1 0 36 66 1 0 37 67 1 0 M END

Standard InCHIKey	OBNYZGVKISJJRK-UAMYCEOTSA-N
Standard InCHI	InChI=1S/C24H30O13/c25-9-14-18(29)19(30)20(31)23(36-14)37-22-16-13(7-8-34-22)17(28)21(32)24(16,33)10-35-15(27)6-3-11-1-4-12(26)5-2-11/h1-8,13-14,16-23,25-26,28-33H,9-10H2/b6-3+/t13-,14-,16-,17+,18-,19+,20-,21+,22+,23+,24+/m1/s1
SMILES	c1cc(ccc1/C=C/C(=O)OC[C@@]1([C@@H]2[C@@H](C=CO[C@H]2O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@@H]([C@@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	526.17	Volume:	487.888 ? Van der Waals volume.
Dense:	1.078	LogP:	-0.242 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.528 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.731 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	24.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.135	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.003	Fsp³:	0.542
MCE-18:	100.649 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.669	Fluc inhibitor:	0.664 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.233 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.11 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.301	Promiscuous compounds:	0.355

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.408	MDCK Permeability:	-5.243
Pgp-inhibitor:	0.0	Pgp-substrate:	0.889
PAMPA:	1.0 ? 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):	0.778
20% Bioavailability (F20%):	0.916	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	69.526%	Volume Distribution (VD):	-0.362
Fu:	32.462% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.025 ? 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):

1.415

Half-life (T1/2):

2.678

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.631	Drug-induced Liver Injury (DILI):	0.803
AMES Toxicity:	0.977	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.103	Skin Sensitization:	1.0
Carcinogencity:	0.316	Eye Corrosion:	0.0
Eye Irritation:	0.088	Respiratory Toxicity:	0.012
Drug-induced Neurotoxicity:	0.061	Ototoxicity:	0.942
Hematotoxicity:	0.469	Drug-induced Nephrotoxicity:	0.891
Genotoxicity:	0.59	RPMI-8226 Immunitoxicity:	0.198
A549 Cytotoxicity:	0.552	Hek293 Cytotoxicity:	0.644
BCF:	0.451 ? 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:	3.137 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.862 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.957 ? 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
NPO23522	Croton argyrophylloides	Species	Euphorbiaceae	Eukaryota	bark	Crato, Cear State, Brazil	2005-JAN	PMID[19780590]
NPO21027	Daphnia magna	Species	Daphniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20117838]
NPO15656	Fusarium equiseti	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO25014	Achillea millefolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36905473]
NPO21027	Daphnia magna	Species	Daphniidae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO24762	Sporothrix flocculosa	Species	Ophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4722	Peumus boldus	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24125	Guatteria subsessilis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15656	Fusarium equiseti	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24801	Fagraea ceilanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24648	Dryopteris sieboldii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23522	Croton argyrophylloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24851	Aniba gigantifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21027	Daphnia magna	Species	Daphniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25014	Achillea millefolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4722	Peumus boldus	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25014	Achillea millefolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4722	Peumus boldus	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25014	Achillea millefolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25014	Achillea millefolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24851	Aniba gigantifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15656	Fusarium equiseti	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24762	Sporothrix flocculosa	Species	Ophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4722	Peumus boldus	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24648	Dryopteris sieboldii	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23522	Croton argyrophylloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24125	Guatteria subsessilis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24801	Fagraea ceilanica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25014	Achillea millefolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21027	Daphnia magna	Species	Daphniidae	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 NPC307125 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	12605
0.1-0.2	32059
0.2-0.3	4325
0.3-0.4	730
0.4-0.5	115
0.5-0.6	20
0.6-0.7	2
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	Natural Product ID
0.6867	Remote Similarity	NPC254819
0.6092	Remote Similarity	NPC46644
0.5844	Remote Similarity	NPC52097
0.5778	Remote Similarity	NPC486495
0.5753	Remote Similarity	NPC11724
0.573	Remote Similarity	NPC49597
0.5604	Remote Similarity	NPC479970
0.5568	Remote Similarity	NPC145287
0.5543	Remote Similarity	NPC202391
0.5543	Remote Similarity	NPC296659
0.5455	Remote Similarity	NPC77922
0.5455	Remote Similarity	NPC473281
0.5385	Remote Similarity	NPC18789
0.5269	Remote Similarity	NPC31745
0.5269	Remote Similarity	NPC220936
0.5208	Remote Similarity	NPC229548
0.5161	Remote Similarity	NPC96599
0.5109	Remote Similarity	NPC476869
0.5065	Remote Similarity	NPC232880
0.5059	Remote Similarity	NPC477293
0.5051	Remote Similarity	NPC184464
0.5051	Remote Similarity	NPC251062

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC307125 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5124
0.1-0.2	3948
0.2-0.3	75
0.3-0.4	2
0.4-0.5	1
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