NPASS Compound

Natural Product: NPC488870

Natural Product ID	NPC488870
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WLNWTSOEOWZEGI-SVSQYMGHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	20847459
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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 80 83 0 0 0 0 0 0 0 0999 V2000 4.1719 -2.6032 0.7863 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2683 -1.7043 1.7549 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8157 -0.3393 1.5399 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3610 0.2102 0.1813 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8390 0.2462 0.2039 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3571 0.7943 -1.1211 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8353 -0.1045 -2.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9757 1.2361 -1.1573 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6156 1.7686 -2.5379 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8861 2.0777 -2.3451 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2804 1.4042 -1.0822 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6391 0.8172 -1.0280 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6300 1.9422 -1.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9365 1.6686 -0.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1980 0.6099 0.1864 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5200 0.4256 0.7983 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7821 -0.9703 1.2573 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6607 -1.6008 2.0165 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3356 -0.9297 1.8417 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1449 -0.4355 0.4234 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2574 -1.5404 -0.5740 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8201 0.2955 0.3808 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7267 -0.5607 0.8580 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3370 -0.2314 0.4377 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1663 0.3473 -0.9111 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4175 -0.6927 -1.9607 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2423 -1.7898 0.2031 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2989 -0.3442 1.6927 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9663 0.9721 1.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9586 -1.3386 0.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2481 0.5012 2.4925 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6331 1.7350 2.4256 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7710 -3.5801 0.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4862 -2.4042 -0.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9365 -1.9675 2.7523 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7315 1.2238 0.0487 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7448 -0.4285 -0.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5458 0.9474 0.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -0.8043 0.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9835 1.7401 -1.2405 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8384 -1.1756 -1.9393 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9329 0.1265 -2.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3847 0.0786 -3.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8231 2.1395 -0.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6028 0.9442 -3.2864 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1809 2.6491 -2.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4704 1.8233 -3.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9464 3.1873 -2.1847 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1774 2.1058 -0.2192 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8504 0.0646 -1.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2070 2.8659 -0.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7545 2.2068 -2.2849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7296 2.4180 -0.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2898 0.6697 0.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6880 1.1017 1.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6604 -0.9182 1.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8782 -1.6740 3.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5797 -2.6725 1.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5476 -1.6806 2.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2077 -0.0779 2.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3328 -1.7918 -1.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6040 -2.5037 -0.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0321 -1.2456 -1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9136 1.1788 1.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0041 -1.6342 0.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7341 -0.5316 1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1995 -1.2289 0.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1975 0.3618 1.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0966 -0.3067 -2.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9844 -1.5210 -1.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4881 -1.1415 -2.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7076 -1.2544 -0.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5389 -0.6941 2.7243 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0676 0.7458 1.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9588 1.6185 2.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6445 1.5346 0.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6058 -1.1870 -0.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8584 -2.3767 1.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0566 -1.0944 0.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9138 2.2966 2.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 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 2 0 15 16 1 0 16 17 1 0 17 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 6 17 27 1 0 3 28 1 0 28 29 1 0 28 30 1 0 3 31 1 0 31 32 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 33 1 0 1 34 1 0 2 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 6 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 1 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 1 12 50 1 6 13 51 1 0 13 52 1 0 14 53 1 0 16 54 1 0 16 55 1 0 17 56 1 1 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 1 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 29 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 32 80 1 0 M END

Standard InCHIKey	WLNWTSOEOWZEGI-SVSQYMGHSA-N
Standard InCHI	InChI=1S/C29H48O3/c1-7-29(32-31,19(2)3)17-12-20(4)24-10-11-25-23-9-8-21-18-22(30)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-8,19-20,22-26,30-31H,1,9-18H2,2-6H3/t20-,22+,23+,24-,25+,26+,27+,28-,29?/m1/s1
SMILES	C=CC(CC[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)(C(C)C)OO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	444.36	Volume:	497.012 ? Van der Waals volume.
Dense:	0.894	LogP:	6.822 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.062 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.452 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.244	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.834	Fsp³:	0.862
MCE-18:	74.111 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.865	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.542	Promiscuous compounds:	0.091

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.309	MDCK Permeability:	-5.034
Pgp-inhibitor:	0.018	Pgp-substrate:	0.031
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):	0.0
20% Bioavailability (F20%):	0.012	30% Bioavailability (F30%):	0.677
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035	MRP1:	0.05
Plasma Protein Binding (PPB):	90.91%	Volume Distribution (VD):	-0.139
Fu:	7.865% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.806
BSEP inhibitor:	0.052

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.006	CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.977	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.616 ? 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):

14.509

Half-life (T1/2):

0.932

ADMET: Toxicity

hERG Blockers:	0.183	hERG Blockers (10um):	0.304
Human Hepatotoxicity (H-HT):	0.598	Drug-induced Liver Injury (DILI):	0.679
AMES Toxicity:	0.583	Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.651	Skin Sensitization:	0.993
Carcinogencity:	0.886	Eye Corrosion:	0.204
Eye Irritation:	0.7	Respiratory Toxicity:	0.625
Drug-induced Neurotoxicity:	0.11	Ototoxicity:	0.489
Hematotoxicity:	0.333	Drug-induced Nephrotoxicity:	0.372
Genotoxicity:	0.202	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.158	Hek293 Cytotoxicity:	0.73
BCF:	2.466 ? 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:	4.478 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.586 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.226 ? 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
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17637068]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13278	Strychnos spinosa	Species	Loganiaceae	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

Activity Type	# Activity
IC50	6
Ratio IC50	1

Activity Type	# Activity
Cell line	1
Organism	1
Others	1
Non-molecular	4

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
NPT1886	Cell line	J774	Mus musculus	IC50	=	16400.0	nM	PMID[17637068]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	700.0	nM	PMID[17637068]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	3200.0	nM	PMID[17637068]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	5.2	n.a.	PMID[17637068]

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 NPC488870 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	21936
0.1-0.2	24218
0.2-0.3	3358
0.3-0.4	218
0.4-0.5	72
0.5-0.6	21
0.6-0.7	19
0.7-0.8	1
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
0.7895	Intermediate Similarity	NPC603646
0.7333	Intermediate Similarity	NPC47761
0.7273	Intermediate Similarity	NPC162742
0.7273	Intermediate Similarity	NPC304309
0.7273	Intermediate Similarity	NPC470228
0.7167	Intermediate Similarity	NPC473943
0.7143	Intermediate Similarity	NPC22105
0.7143	Intermediate Similarity	NPC34019
0.7143	Intermediate Similarity	NPC107059
0.7018	Intermediate Similarity	NPC136188
0.7018	Intermediate Similarity	NPC28657
0.7018	Intermediate Similarity	NPC474216
0.6897	Remote Similarity	NPC230301
0.6897	Remote Similarity	NPC198968
0.6897	Remote Similarity	NPC285893
0.6897	Remote Similarity	NPC134847
0.6833	Remote Similarity	NPC59453
0.678	Remote Similarity	NPC241290
0.678	Remote Similarity	NPC164840
0.678	Remote Similarity	NPC484739
0.678	Remote Similarity	NPC209944
0.678	Remote Similarity	NPC155986
0.6667	Remote Similarity	NPC321381
0.6557	Remote Similarity	NPC472265
0.65	Remote Similarity	NPC264245
0.6349	Remote Similarity	NPC155011
0.6333	Remote Similarity	NPC113733
0.6271	Remote Similarity	NPC221758
0.6271	Remote Similarity	NPC600590
0.6167	Remote Similarity	NPC154330
0.6032	Remote Similarity	NPC33913
0.5968	Remote Similarity	NPC51014
0.5846	Remote Similarity	NPC243985
0.5846	Remote Similarity	NPC280710
0.5846	Remote Similarity	NPC240650
0.5645	Remote Similarity	NPC328313
0.5625	Remote Similarity	NPC328714
0.5606	Remote Similarity	NPC475789
0.5538	Remote Similarity	NPC318495
0.5522	Remote Similarity	NPC474164
0.5507	Remote Similarity	NPC601043
0.5507	Remote Similarity	NPC605412
0.5455	Remote Similarity	NPC477522
0.5424	Remote Similarity	NPC96319
0.5385	Remote Similarity	NPC87604
0.5362	Remote Similarity	NPC489873
0.5238	Remote Similarity	NPC151519
0.5156	Remote Similarity	NPC20688
0.5147	Remote Similarity	NPC489872
0.5077	Remote Similarity	NPC76879
0.5075	Remote Similarity	NPC1272
0.5075	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 NPC488870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7397
0.1-0.2	1579
0.2-0.3	144
0.3-0.4	23
0.4-0.5	2
0.5-0.6	2
0.6-0.7	2
0.7-0.8	1
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
0.7018	Intermediate Similarity	NPD6942	Phase 4
0.6897	Remote Similarity	NPD7339	Approved
0.6271	Remote Similarity	NPD4786	Phase 1
0.5424	Remote Similarity	NPD3701	Pre-clinical
0.5238	Remote Similarity	NPD3667	Phase 4

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