NPASS Compound

Natural Product: NPC475500

Natural Product ID	NPC475500
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NHELFTYSELEEFD-BDZIUULGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506822
PubChem CID	44559850
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane 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 2D 84 89 0 0 0 0 0 0 0 0999 V2000 7.0478 15.3050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9482 14.2847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8486 13.2645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7491 12.2442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6495 11.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5499 10.2037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8837 8.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7841 7.7211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1179 6.2587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0183 5.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1974 3.7491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1636 3.1186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1839 4.2182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4534 5.5283 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0836 5.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5729 5.2393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4941 6.7977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6463 3.8844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0884 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5989 2.5992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6058 1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6058 -1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0682 -1.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7190 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 -0.2013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4732 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1523 -2.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9510 -3.8745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8247 -2.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0812 -0.2218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2566 -3.0367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4120 -1.9894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2569 -3.2287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4232 3.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 5.3825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0559 6.0668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3159 5.2530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1306 7.5650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0275 16.4046 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0681 14.2054 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1474 16.3253 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9685 13.1852 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9280 15.3843 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8284 14.3641 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8689 12.1649 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7693 11.1446 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7288 13.3438 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6292 12.3235 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6697 10.1244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1166 10.6458 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3171 8.2992 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6492 8.1632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5513 5.8165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8225 4.5793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7363 6.1861 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7411 4.2983 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7912 7.5509 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0131 6.5594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9045 8.1770 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1346 4.0709 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9941 1.2553 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2370 2.2988 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5567 1.8771 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5558 -2.7564 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2460 -1.4044 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2420 0.8828 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1739 -3.6795 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4755 -0.9766 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1761 -2.9789 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5831 -0.1470 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4116 -4.2760 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7151 -2.9791 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6513 -1.1444 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7528 -3.1166 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4458 4.6352 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1075 1.8005 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7580 3.8197 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6288 7.4902 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6528 7.8218 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 9.0631 0.0000 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 2 0 7 8 1 0 8 9 2 0 10 9 1 6 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 6 15 16 2 0 15 17 1 0 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 27 34 1 1 26 35 1 0 25 36 1 1 36 37 1 0 19 38 1 0 18 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 14 10 1 0 28 20 1 0 21 10 1 0 25 23 1 0 31 27 1 0 22 12 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 7 55 1 0 8 56 1 0 9 57 1 0 12 58 1 1 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 17 63 1 0 18 64 1 6 19 65 1 1 22 66 1 1 23 67 1 1 26 68 1 6 28 69 1 6 29 70 1 0 33 71 1 0 33 72 1 0 33 73 1 0 34 74 1 0 35 75 1 0 36 76 1 0 36 77 1 0 37 78 1 0 38 79 1 0 38 80 1 0 38 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 M END

Standard InCHIKey	NHELFTYSELEEFD-BDZIUULGSA-N
Standard InCHI	InChI=1S/C32H42O10/c1-7-8-9-10-11-12-13-14-29-40-26-22-25-28(16-33,39-25)27(36)30(37)21(15-18(4)23(30)35)32(22,42-29)19(5)24(38-20(6)34)31(26,41-29)17(2)3/h11-15,19,21-22,24-27,33,36-37H,2,7-10,16H2,1,3-6H3/b12-11+,14-13+/t19-,21-,22+,24-,25+,26-,27-,28+,29-,30-,31-,32+/m1/s1
SMILES	CCCCC/C=C/C=C/[C@@]12O[C@H]3[C@@](O1)(C(=C)C)[C@@H]([C@H]([C@@]1(O2)[C@H]3[C@@H]2O[C@@]2([C@H]([C@]2([C@H]1C=C(C2=O)C)O)O)CO)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	586.28	Volume:	582.773 ? Van der Waals volume.
Dense:	1.006	LogP:	3.51 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.535 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.975 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	29.0
TPSA:	144.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.121	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.862	Fsp³:	0.688
MCE-18:	107.556 ? 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:	0.531	Fluc inhibitor:	0.075 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.177	Promiscuous compounds:	0.286

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.364	MDCK Permeability:	-4.959
Pgp-inhibitor:	0.031	Pgp-substrate:	0.023
PAMPA:	0.078 ? 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):	0.028
20% Bioavailability (F20%):	0.405	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038	MRP1:	0.905
Plasma Protein Binding (PPB):	91.125%	Volume Distribution (VD):	-0.211
Fu:	6.705% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.087
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.026	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.334	CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.076	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.341 ? 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):

5.055

Half-life (T1/2):

1.154

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.209
Human Hepatotoxicity (H-HT):	0.477	Drug-induced Liver Injury (DILI):	0.373
AMES Toxicity:	0.918	Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.326	Skin Sensitization:	1.0
Carcinogencity:	0.31	Eye Corrosion:	0.014
Eye Irritation:	0.654	Respiratory Toxicity:	0.72
Drug-induced Neurotoxicity:	0.172	Ototoxicity:	0.756
Hematotoxicity:	0.712	Drug-induced Nephrotoxicity:	0.391
Genotoxicity:	0.052	RPMI-8226 Immunitoxicity:	0.224
A549 Cytotoxicity:	0.614	Hek293 Cytotoxicity:	0.691
BCF:	0.831 ? 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:	3.898 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.548 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.778 ? 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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	6
Survival	1

Activity Type	# Activity
Organism	7

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	=	0.27	nmol	DOI[10.1039/C3MD00097D]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.7	/nmol	PMID[15104505]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.0	%	PMID[22705001]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.0	%	PMID[22705001]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.0	n.a.	PMID[22705001]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.36	n.a.	PMID[22705001]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	88.0	%	PMID[22705001]

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 NPC475500 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	17942
0.1-0.2	29852
0.2-0.3	1958
0.3-0.4	32
0.4-0.5	17
0.5-0.6	11
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC223356
1.0	High Similarity	NPC298697
1.0	High Similarity	NPC100017
1.0	High Similarity	NPC481742
0.9859	High Similarity	NPC182266
0.9859	High Similarity	NPC475154
0.9859	High Similarity	NPC485700
0.9315	High Similarity	NPC75831
0.9315	High Similarity	NPC471137
0.9189	High Similarity	NPC471136
0.9189	High Similarity	NPC116727
0.9189	High Similarity	NPC39509
0.9167	High Similarity	NPC324104
0.9167	High Similarity	NPC473548
0.9067	High Similarity	NPC481744
0.9067	High Similarity	NPC481743
0.9041	High Similarity	NPC180902
0.7816	Intermediate Similarity	NPC101786
0.7792	Intermediate Similarity	NPC251564
0.7792	Intermediate Similarity	NPC477189
0.7692	Intermediate Similarity	NPC474508
0.7692	Intermediate Similarity	NPC473485
0.7692	Intermediate Similarity	NPC171411
0.7692	Intermediate Similarity	NPC485701
0.7674	Intermediate Similarity	NPC92598
0.7674	Intermediate Similarity	NPC43304
0.7674	Intermediate Similarity	NPC481753
0.7674	Intermediate Similarity	NPC477188
0.7674	Intermediate Similarity	NPC477190
0.764	Intermediate Similarity	NPC481773
0.7468	Intermediate Similarity	NPC475314
0.7468	Intermediate Similarity	NPC102997
0.7375	Intermediate Similarity	NPC485693
0.7191	Intermediate Similarity	NPC130886
0.7191	Intermediate Similarity	NPC486153
0.7045	Intermediate Similarity	NPC164150
0.7045	Intermediate Similarity	NPC481754
0.7033	Intermediate Similarity	NPC481774
0.701	Intermediate Similarity	NPC69240
0.6875	Remote Similarity	NPC162495
0.679	Remote Similarity	NPC475606
0.6465	Remote Similarity	NPC191992
0.6413	Remote Similarity	NPC68282
0.6136	Remote Similarity	NPC473838
0.5895	Remote Similarity	NPC481745
0.5567	Remote Similarity	NPC486154
0.5543	Remote Similarity	NPC475139
0.5484	Remote Similarity	NPC605479
0.5412	Remote Similarity	NPC475273
0.5412	Remote Similarity	NPC168849
0.5412	Remote Similarity	NPC217901
0.5412	Remote Similarity	NPC611341
0.5152	Remote Similarity	NPC156682
0.5152	Remote Similarity	NPC49297
0.5055	Remote Similarity	NPC181924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6693
0.1-0.2	2436
0.2-0.3	21
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