NPASS Compound

Natural Product: NPC547258

Natural Product ID	NPC547258
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{R})-2,5,7,8-tetramethyl-2-[(3~{Z},7~{E})-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol
IUPAC Name	(2~{R})-2,5,7,8-tetramethyl-2-[(3~{Z},7~{E})-4,8,12-trimethyltrideca-3,7,11-trienyl]chroman-6-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 75 76 0 0 0 0 0 0 0 0999 V2000 5.7022 2.9105 -1.0223 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1505 1.5672 -1.4667 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3751 0.9786 -0.8886 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4448 0.9279 -2.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7864 -0.4218 -2.9052 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6289 -1.3555 -2.6444 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2849 -1.5178 -1.2213 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2504 -2.0580 -0.2202 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0394 -1.1587 -0.8401 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6826 -1.3124 0.5594 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5656 -2.2725 0.8810 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2698 -1.9766 0.3000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1115 -1.9787 -1.1934 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8154 -1.7280 0.9864 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8483 -1.7205 2.4508 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1071 -0.3484 3.0008 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3962 0.2346 2.5502 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4901 1.6213 3.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5644 -0.6109 2.9645 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8668 -0.0362 2.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7506 0.5230 1.0849 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8962 0.8239 0.3686 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2050 0.5486 1.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8124 1.3488 -0.8932 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9835 1.6506 -1.6112 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5892 1.5971 -1.4970 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5021 2.1667 -2.8653 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4550 1.3022 -0.7955 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0992 1.5479 -1.3934 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5440 0.7645 0.4968 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3710 0.4809 1.1701 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5549 3.4414 -0.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3219 3.4763 -1.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8563 2.7933 -0.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9446 1.7636 -0.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0480 0.5617 -1.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1406 0.1370 -0.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5386 1.3828 -2.8004 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7392 -0.7976 -2.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8656 -0.3178 -4.0065 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7406 -1.0446 -3.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8767 -2.3929 -3.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9369 -3.0697 0.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2087 -2.2366 -0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4728 -1.3705 0.5941 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3722 -0.7608 -1.5901 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3081 -0.3037 0.9142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5471 -1.5163 1.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8357 -3.3108 0.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6069 -2.4108 1.9787 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 -2.5921 -1.6512 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0362 -0.9475 -1.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4935 -1.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7824 -1.5305 0.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0340 -2.1958 2.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 -2.4318 2.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0429 -0.3528 4.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3015 0.3707 2.6478 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5447 1.8706 3.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9834 1.5529 4.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9189 2.3441 2.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4948 -1.6527 2.6466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6240 -0.5771 4.0715 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6633 -0.8206 2.3996 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2265 0.7165 3.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2002 1.0922 2.0062 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0456 0.9045 0.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3009 -0.5436 1.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4403 0.9072 -2.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6034 1.7757 -3.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4289 1.8919 -3.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4116 3.2665 -2.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1807 2.4285 -2.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8149 0.6625 -1.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3514 1.7313 -0.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 2 0 14 15 1 0 15 16 1 0 17 16 1 1 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 2 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 2 0 30 31 1 0 31 17 1 0 30 21 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 13 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 18 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 25 69 1 0 27 70 1 0 27 71 1 0 27 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 M END

Standard InCHIKey	RZFHLOLGZPDCHJ-MXTWWLCESA-N
Standard InCHI	InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16-/t29-/m1/s1
SMILES	CC(C)=CCC/C(C)=C/CC/C(C)=CCC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	424.33	Volume:	494.789 ? Van der Waals volume.
Dense:	0.858	LogP:	9.269 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.087 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.319 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	14.0
TPSA:	29.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.402	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.606	Fsp³:	0.586
MCE-18:	56.348 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.995	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.049 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.236 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.651	Promiscuous compounds:	0.18

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.906	MDCK Permeability:	-4.773
Pgp-inhibitor:	1.0	Pgp-substrate:	0.0
PAMPA:	0.001 ? 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%):	0.012	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.681

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.957	MRP1:	1.0
Plasma Protein Binding (PPB):	97.117%	Volume Distribution (VD):	0.18
Fu:	3.104% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.002
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.107	CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.317
CYP2C9-inhibitor:	0.883	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.949	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

7.548

Half-life (T1/2):

0.514

ADMET: Toxicity

hERG Blockers:	0.242	hERG Blockers (10um):	0.728
Human Hepatotoxicity (H-HT):	0.696	Drug-induced Liver Injury (DILI):	0.008
AMES Toxicity:	0.107	Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.186	Skin Sensitization:	0.999
Carcinogencity:	0.155	Eye Corrosion:	0.034
Eye Irritation:	0.802	Respiratory Toxicity:	0.944
Drug-induced Neurotoxicity:	0.447	Ototoxicity:	0.503
Hematotoxicity:	0.257	Drug-induced Nephrotoxicity:	0.318
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.081
A549 Cytotoxicity:	0.178	Hek293 Cytotoxicity:	0.286
BCF:	2.168 ? 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:	5.922 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.417 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.699 ? 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
NPO51793	Avena sativa L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO51497	Vitis vinifera L.	Genus	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61721	Vaccinium macrocarpon Aiton	Genus	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54065	Secale cereale L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56122	Hordeum vulgare L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47968	Hevea brasiliensis Mull.Arg.	Genus	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53457	Gevuina avellana Mol.	Genus	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63328	Foeniculum vulgare L.	Genus	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50284	Elaeis guineensis Jacq.	Genus	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47500	Delphinium ajacis L.	Genus	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO60041	Cocos nucifera L.	Genus	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO43780	Coriandrum sativum L.	Genus	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO46802	Amaranthus hypochondriacus L.	Genus	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56140	Aesculus hippocastanum Hort.	Genus	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO57885	Zea mays L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45500	Rosmarinus officinalis L.	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO46843	Calophyllum inophyllum L.	Genus	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO43508	Carum carvi L.	Genus	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO44442	Oryza sativa L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50353	Bixa orellana L.	Genus	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54537	Nicotiana tabacum L.	Genus	Solanaceae	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

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 NPC547258 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	21665
0.1-0.2	26207
0.2-0.3	1752
0.3-0.4	181
0.4-0.5	30
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC139047
0.7018	Intermediate Similarity	NPC45663
0.6271	Remote Similarity	NPC69539
0.6167	Remote Similarity	NPC469907
0.5735	Remote Similarity	NPC609806
0.569	Remote Similarity	NPC126759
0.569	Remote Similarity	NPC242580
0.569	Remote Similarity	NPC236070
0.5606	Remote Similarity	NPC610467
0.5441	Remote Similarity	NPC232295
0.5385	Remote Similarity	NPC32152
0.5385	Remote Similarity	NPC147896
0.5323	Remote Similarity	NPC489686
0.5254	Remote Similarity	NPC320847
0.5217	Remote Similarity	NPC479050
0.5217	Remote Similarity	NPC610441
0.5217	Remote Similarity	NPC611336
0.5143	Remote Similarity	NPC204535
0.5143	Remote Similarity	NPC474131
0.5143	Remote Similarity	NPC46586
0.5139	Remote Similarity	NPC474237
0.507	Remote Similarity	NPC271832
0.507	Remote Similarity	NPC59654
0.507	Remote Similarity	NPC601388

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC547258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5824
0.1-0.2	3292
0.2-0.3	26
0.3-0.4	5
0.4-0.5	0
0.5-0.6	3
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
0.5738	Remote Similarity	NPD6671	Approved
0.569	Remote Similarity	NPD7340	Approved
0.549	Remote Similarity	NPD1398	Phase 1

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