NPASS Compound

Natural Product: NPC153843

Natural Product ID	NPC153843
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ATNNLHXCRAAGJS-QZQOTICOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6433893
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002950] Very long-chain fatty acids

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 66 65 0 0 0 0 0 0 0 0999 V2000 -10.1782 -1.3658 -0.5154 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8578 -0.5160 -0.6027 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7137 -0.1507 -2.0178 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6674 0.7167 -2.5279 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2541 0.3605 -2.3507 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7710 0.3713 -0.9553 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2664 -0.0102 -0.9366 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7677 -0.0001 0.4925 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3160 -0.3655 0.5726 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4164 0.5699 -0.1901 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0297 0.2090 -0.1079 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5827 0.2013 1.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0436 -0.1695 1.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8655 0.7970 0.5657 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3316 0.4574 0.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8480 0.4723 2.0144 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3220 0.1331 2.0630 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1529 1.1087 1.2744 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6030 0.6958 1.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8087 -0.6706 0.8372 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6399 -0.8429 -0.1852 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8595 -2.1748 -0.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2844 -3.1915 -0.2801 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7280 -2.3473 -1.8044 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9952 -2.2897 -1.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3508 -1.6471 0.5352 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9841 -0.7364 -0.8940 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1316 -1.2666 -0.2047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8981 0.3384 0.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7195 0.3173 -2.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6852 -1.1154 -2.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8512 1.8020 -2.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8050 0.8686 -3.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0059 -0.6576 -2.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5620 1.0462 -2.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8088 1.4356 -0.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3034 -0.2179 -0.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6923 0.6727 -1.5591 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2324 -1.0410 -1.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9880 1.0086 0.8943 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3262 -0.7171 1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2218 -1.3662 0.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9687 -0.5540 1.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6907 0.5486 -1.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5870 1.6075 0.1609 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2147 -0.7785 -0.5756 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5808 0.9574 -0.7144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5172 1.2501 1.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0442 -0.4324 1.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2465 -1.1957 1.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3339 -0.0421 2.4319 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 0.7612 -0.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6490 1.8130 0.9231 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4459 -0.5832 0.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8575 1.1433 -0.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3376 -0.3664 2.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6978 1.4113 2.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4248 -0.8952 1.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6436 0.2041 3.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9028 1.1040 0.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0713 2.1359 1.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8200 0.6312 2.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2834 1.4316 0.9225 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2988 -1.5123 1.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1306 0.0326 -0.5741 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8288 -3.2490 -2.2560 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 0 7 8 1 0 8 9 1 0 9 10 1 0 10 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 0 5 35 1 0 6 36 1 0 6 37 1 0 7 38 1 0 7 39 1 0 8 40 1 0 8 41 1 0 9 42 1 0 9 43 1 0 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 0 21 65 1 0 24 66 1 0 M END

Standard InCHIKey	ATNNLHXCRAAGJS-QZQOTICOSA-N
Standard InCHI	InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h20-21H,2-19H2,1H3,(H,23,24)/b21-20+
SMILES	CCCCCCCCCCCCCCCCCCC/C=C/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	338.32	Volume:	401.376 ? Van der Waals volume.
Dense:	0.843	LogP:	8.623 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.328 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.526 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	2.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.194	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.052	Fsp³:	0.864
MCE-18:	0.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.596	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.017 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.993	Promiscuous compounds:	0.546

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041	MDCK Permeability:	-4.86
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.004 ? 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):	0.992
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.948
Plasma Protein Binding (PPB):	98.13%	Volume Distribution (VD):	0.183
Fu:	1.323% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.345
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.262
BSEP inhibitor:	0.635

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.088	CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.054 ? 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):

3.592

Half-life (T1/2):

1.693

ADMET: Toxicity

hERG Blockers:	0.31	hERG Blockers (10um):	0.427
Human Hepatotoxicity (H-HT):	0.748	Drug-induced Liver Injury (DILI):	0.36
AMES Toxicity:	0.021	Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.19	Skin Sensitization:	0.998
Carcinogencity:	0.059	Eye Corrosion:	0.971
Eye Irritation:	0.998	Respiratory Toxicity:	0.979
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.227
Hematotoxicity:	0.138	Drug-induced Nephrotoxicity:	0.227
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.029
A549 Cytotoxicity:	0.627	Hek293 Cytotoxicity:	0.048
BCF:	0.414 ? 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:	4.463 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.295 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.696 ? 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
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/10496475.2013.791908]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16394559]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[18181575]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24456525]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24597776]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38202695]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24062	Radix pseudostellariae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24062	Radix pseudostellariae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27018	Cynomorium songaricum	Species	Cynomoriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3846	Melia indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5645	Silybum marianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26770	Pteris multifida	Species	Pteridaceae	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 NPC153843 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	36690
0.1-0.2	11449
0.2-0.3	1391
0.3-0.4	214
0.4-0.5	73
0.5-0.6	35
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC202716
0.75	Intermediate Similarity	NPC221250
0.7143	Intermediate Similarity	NPC34416
0.5806	Remote Similarity	NPC424
0.5806	Remote Similarity	NPC36061
0.5806	Remote Similarity	NPC69510
0.5806	Remote Similarity	NPC77272
0.5806	Remote Similarity	NPC290563
0.5806	Remote Similarity	NPC139029
0.5806	Remote Similarity	NPC281972
0.5806	Remote Similarity	NPC261831
0.5806	Remote Similarity	NPC87564
0.5625	Remote Similarity	NPC95145
0.5625	Remote Similarity	NPC325642
0.5625	Remote Similarity	NPC65174
0.5517	Remote Similarity	NPC118654
0.5484	Remote Similarity	NPC281245
0.5357	Remote Similarity	NPC171736
0.5357	Remote Similarity	NPC301585
0.5357	Remote Similarity	NPC261080
0.5357	Remote Similarity	NPC132565
0.5357	Remote Similarity	NPC209970
0.5357	Remote Similarity	NPC216630
0.5357	Remote Similarity	NPC201844
0.5357	Remote Similarity	NPC301696
0.5357	Remote Similarity	NPC196924
0.5357	Remote Similarity	NPC307783
0.5357	Remote Similarity	NPC154186
0.5357	Remote Similarity	NPC149184
0.5357	Remote Similarity	NPC279026
0.5357	Remote Similarity	NPC113928
0.5357	Remote Similarity	NPC14227
0.5312	Remote Similarity	NPC92114
0.5294	Remote Similarity	NPC154245
0.5294	Remote Similarity	NPC85813
0.5294	Remote Similarity	NPC223697
0.5294	Remote Similarity	NPC6095
0.5278	Remote Similarity	NPC487562

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC153843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6543
0.1-0.2	2329
0.2-0.3	233
0.3-0.4	27
0.4-0.5	12
0.5-0.6	6
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
0.5806	Remote Similarity	NPD3195	Phase 2
0.5806	Remote Similarity	NPD3196	Approved
0.5357	Remote Similarity	NPD2270	Pre-clinical
0.5357	Remote Similarity	NPD633	Phase 3
0.5357	Remote Similarity	NPD9448	Phase 2
0.5294	Remote Similarity	NPD4266	Phase 2

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