NPASS Compound

Natural Product: NPC136073

Natural Product ID	NPC136073
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VRBNGKPRTHBEIQ-KKZJBSMNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes

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 72 76 0 0 0 0 0 0 0 0999 V2000 8.0255 0.8465 -0.6732 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7538 0.2512 -0.1272 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6966 1.3593 -0.1623 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4697 0.8407 0.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0667 -0.4973 0.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8964 -1.1935 -0.5594 N 0 0 0 0 0 0 0 0 0 0 0 0 6.2070 -0.8593 -0.9612 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7140 -1.0830 0.4155 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6008 -1.1333 1.9168 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6003 -0.3132 -0.1936 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7332 -0.2171 -1.7027 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3927 0.3394 -2.1078 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5560 -0.4381 -1.2289 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6536 0.4110 -0.6902 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3821 1.2521 -1.6920 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3711 2.0602 -0.8847 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1123 1.4320 0.0217 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1125 2.1962 0.8520 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3313 1.4007 1.1788 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0734 -0.0420 1.4722 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5874 -0.3544 1.5621 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9670 -0.0245 0.2219 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8370 -0.7504 -0.8164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5782 -0.5151 0.0734 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8577 -0.7913 1.3572 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3511 -0.6012 1.2549 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2518 -0.9596 -0.0502 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3420 -2.4729 -0.2373 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2692 1.5770 0.1433 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0389 1.9216 -0.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0388 0.8049 -1.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9312 0.3892 -0.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8812 -0.0177 0.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4949 1.5317 -1.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1064 2.2588 0.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6788 1.6177 0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7345 0.7968 1.6343 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9083 -1.7414 -0.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1854 -0.5202 -2.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6778 -2.1175 0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1819 -2.0748 2.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0904 -0.2555 2.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6553 -1.0503 2.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5311 0.7121 0.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8544 -1.1847 -2.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4766 0.5471 -2.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1819 0.2190 -3.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3096 1.4052 -1.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9960 -1.2520 -1.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1851 1.1285 0.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8507 0.7096 -2.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6717 1.9754 -2.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5104 3.1178 -1.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6188 2.5005 1.7873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4476 3.0927 0.2575 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8056 1.8768 2.0742 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6033 -0.6497 0.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5091 -0.3213 2.4764 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1929 0.3012 2.3757 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4940 -1.4288 1.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5827 -0.0761 -1.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1870 -1.0984 -1.6724 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2642 -1.6845 -0.3967 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5907 -1.5059 -0.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1225 -1.7721 1.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1997 -0.0292 2.0968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0538 0.4154 1.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0466 -1.3082 2.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0611 -2.7271 -1.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6334 -2.8849 -0.5550 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5964 -2.9501 0.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8531 1.9438 -0.6703 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 2 0 6 7 1 0 5 8 1 0 8 9 1 0 8 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 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 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 7 2 1 0 27 10 1 0 27 13 1 0 24 14 1 0 22 17 1 0 1 30 1 0 1 31 1 0 1 32 1 0 2 33 1 1 3 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 7 38 1 0 7 39 1 0 8 40 1 6 9 41 1 0 9 42 1 0 9 43 1 0 10 44 1 1 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 6 14 50 1 1 15 51 1 0 15 52 1 0 16 53 1 0 18 54 1 0 18 55 1 0 19 56 1 1 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 23 61 1 0 23 62 1 0 23 63 1 0 24 64 1 6 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 M END

Standard InCHIKey	VRBNGKPRTHBEIQ-KKZJBSMNSA-N
Standard InCHI	InChI=1S/C27H43NO/c1-17-5-10-25(28-16-17)18(2)22-8-9-23-21-7-6-19-15-20(29)11-13-26(19,3)24(21)12-14-27(22,23)4/h6,17-18,20-24,29H,5,7-16H2,1-4H3/t17-,18-,20-,21+,22+,23+,24+,26-,27+/m0/s1
SMILES	C[C@H]1CCC(=NC1)[C@@H](C)[C@H]1CC[C@@H]2[C@H]3CC=C4C[C@H](CC[C@]4(C)[C@@H]3CC[C@]12C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	397.33	Volume:	447.28 ? Van der Waals volume.
Dense:	0.888	LogP:	5.302 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.369 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.129 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	32.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.535	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.824	Fsp³:	0.889
MCE-18:	82.353 ? 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:	0.922	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.035	Promiscuous compounds:	0.04

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.018	MDCK Permeability:	-4.907
Pgp-inhibitor:	0.404	Pgp-substrate:	0.289
PAMPA:	0.081 ? 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%):	0.051	30% Bioavailability (F30%):	0.044
50% Bioavailability (F50%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026	MRP1:	0.771
Plasma Protein Binding (PPB):	83.205%	Volume Distribution (VD):	0.023
Fu:	14.655% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.56
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.022	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.246
CYP2D6-inhibitor:	0.246	CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.485	CYP3A4-substrate:	0.146
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.634
HLM stability:	0.663 ? 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):

14.949

Half-life (T1/2):

1.069

ADMET: Toxicity

hERG Blockers:	0.079	hERG Blockers (10um):	0.239
Human Hepatotoxicity (H-HT):	0.695	Drug-induced Liver Injury (DILI):	0.407
AMES Toxicity:	0.405	Rat Oral Acute Toxicity:	0.238
Maximum Recommended Daily Dose:	0.85	Skin Sensitization:	0.991
Carcinogencity:	0.977	Eye Corrosion:	0.059
Eye Irritation:	0.895	Respiratory Toxicity:	0.899
Drug-induced Neurotoxicity:	0.087	Ototoxicity:	0.542
Hematotoxicity:	0.324	Drug-induced Nephrotoxicity:	0.711
Genotoxicity:	0.012	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.176	Hek293 Cytotoxicity:	0.463
BCF:	2.303 ? 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:	3.908 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.867 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.598 ? 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
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24689280]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[24689280]
NPO11185	Hohenbuehelia grisea	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29356520]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446568]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38731460]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39596244]
NPO4897	Veratrum grandiflorum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4179	Uta tuberculata	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15380	Melicope ternata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11185	Hohenbuehelia grisea	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4897	Veratrum grandiflorum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4897	Veratrum grandiflorum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4179	Uta tuberculata	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15380	Melicope ternata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11185	Hohenbuehelia grisea	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4897	Veratrum grandiflorum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9996	Garcinia quaesita	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2906	Leptactina senegambica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4347	Artemisia chinensis	Species	Asteraceae	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 NPC136073 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	19764
0.1-0.2	25668
0.2-0.3	4042
0.3-0.4	256
0.4-0.5	71
0.5-0.6	18
0.6-0.7	33
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC243985
1.0	High Similarity	NPC280710
0.8214	Intermediate Similarity	NPC240650
0.7	Intermediate Similarity	NPC45365
0.7	Intermediate Similarity	NPC293299
0.6842	Remote Similarity	NPC136188
0.6842	Remote Similarity	NPC28657
0.6825	Remote Similarity	NPC601043
0.6825	Remote Similarity	NPC605412
0.6667	Remote Similarity	NPC221758
0.6667	Remote Similarity	NPC33913
0.6667	Remote Similarity	NPC59453
0.6667	Remote Similarity	NPC600590
0.6491	Remote Similarity	NPC162742
0.6491	Remote Similarity	NPC304309
0.6491	Remote Similarity	NPC470228
0.6393	Remote Similarity	NPC472265
0.6393	Remote Similarity	NPC318495
0.6379	Remote Similarity	NPC22105
0.6379	Remote Similarity	NPC34019
0.6379	Remote Similarity	NPC107059
0.6333	Remote Similarity	NPC51014
0.629	Remote Similarity	NPC603646
0.6271	Remote Similarity	NPC474216
0.6271	Remote Similarity	NPC154330
0.6167	Remote Similarity	NPC230301
0.6167	Remote Similarity	NPC113733
0.6167	Remote Similarity	NPC198968
0.6167	Remote Similarity	NPC285893
0.6167	Remote Similarity	NPC134847
0.6066	Remote Similarity	NPC241290
0.6066	Remote Similarity	NPC164840
0.6066	Remote Similarity	NPC484739
0.6066	Remote Similarity	NPC209944
0.6066	Remote Similarity	NPC264245
0.6066	Remote Similarity	NPC155986
0.6	Remote Similarity	NPC328313
0.6	Remote Similarity	NPC192456
0.5968	Remote Similarity	NPC328714
0.5968	Remote Similarity	NPC321381
0.5938	Remote Similarity	NPC473943
0.5938	Remote Similarity	NPC155011
0.5846	Remote Similarity	NPC47761
0.5846	Remote Similarity	NPC488870
0.5833	Remote Similarity	NPC151519
0.5645	Remote Similarity	NPC249312
0.5606	Remote Similarity	NPC474164
0.5517	Remote Similarity	NPC96319
0.5484	Remote Similarity	NPC20688
0.5397	Remote Similarity	NPC76879
0.5303	Remote Similarity	NPC477522
0.5286	Remote Similarity	NPC5985
0.5278	Remote Similarity	NPC235126
0.5278	Remote Similarity	NPC242419
0.5152	Remote Similarity	NPC1272
0.5152	Remote Similarity	NPC470614

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136073 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6787
0.1-0.2	2144
0.2-0.3	191
0.3-0.4	20
0.4-0.5	3
0.5-0.6	2
0.6-0.7	3
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
0.6842	Remote Similarity	NPD6942	Phase 4
0.6667	Remote Similarity	NPD4786	Phase 1
0.6167	Remote Similarity	NPD7339	Approved
0.5833	Remote Similarity	NPD3667	Phase 4
0.5517	Remote Similarity	NPD3701	Pre-clinical

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