NPASS Compound

Natural Product: NPC252295

Natural Product ID	NPC252295
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Secaubryolide
IUPAC Name	n.a.
Synonyms	Secaubryolide
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2332132
PubChem CID	16099422
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 0 0 0 0 0 0 0 0999 V2000 -5.5629 4.7004 2.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0600 3.3891 2.0735 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7295 2.4219 1.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8803 2.7102 0.9089 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2126 1.0447 1.1638 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0927 1.1665 0.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4761 -0.2109 -0.1729 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9111 -0.8737 0.9671 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0254 -0.3354 -0.2118 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2173 0.8593 0.0444 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1839 0.8552 -0.5989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7762 -0.4512 -0.3183 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0212 -1.3836 -1.2983 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4449 -1.3518 -1.1431 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1331 -1.2840 -2.4679 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5771 -0.9675 -2.4614 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2770 -0.9826 -1.1483 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4780 -2.4066 -0.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7528 -3.1268 0.1625 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3512 -3.0273 -2.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2647 -4.2403 -2.5584 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3450 -1.9656 -3.1663 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5212 -1.2194 -2.7153 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6885 -2.6808 -0.8484 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1409 -2.2474 -0.7980 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1711 -0.7362 -0.7091 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3232 -0.2517 0.0438 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4418 1.2528 0.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6859 1.5120 1.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6380 1.5698 2.2529 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9656 1.6982 0.3500 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0627 1.9128 1.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3345 2.0946 0.2785 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0845 1.9690 2.5018 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7639 -0.8355 1.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6090 -0.9256 1.0947 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8758 5.3591 2.8138 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8651 5.1721 1.3196 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4916 4.5776 2.8934 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0017 0.4456 0.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7978 0.6071 2.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3213 1.7919 0.5994 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4203 1.5838 -0.8177 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7484 -0.2889 1.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6914 -1.9301 1.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 1.0830 1.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6976 1.7715 -0.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6300 1.7678 -0.2414 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0279 1.0209 -1.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7322 -2.3613 -0.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0369 -2.3078 -2.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6456 -0.4928 -3.1118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8283 0.0081 -2.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2735 -0.4879 -1.3055 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8499 -4.1933 0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9080 -2.7432 1.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1410 -1.8170 -3.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6770 -0.2076 -3.0599 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5051 -1.7472 -2.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3093 -3.0921 0.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5538 -3.4722 -1.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5576 -2.7479 0.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7574 -2.6598 -1.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2828 -0.2792 -1.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2101 -0.4683 -0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5864 1.7851 -0.7445 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6317 1.5921 0.8488 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9712 1.6539 -0.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7583 1.1208 0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1236 2.6665 -0.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9985 2.7288 0.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1365 2.0894 2.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4675 2.7811 2.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7599 0.9745 2.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3344 -0.3580 2.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8215 -1.9386 1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8652 -0.5594 1.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6349 -0.0122 1.7507 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2333 -1.5794 1.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4684 -1.5846 1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 7 6 1 1 7 8 1 0 9 8 1 1 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 2 0 18 20 1 0 20 21 2 0 20 22 1 0 13 23 1 6 13 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 29 31 1 0 31 32 2 3 32 33 1 0 32 34 1 0 27 35 1 0 12 36 1 1 17 7 1 0 9 7 1 0 26 12 1 0 14 9 1 0 22 16 1 0 1 37 1 0 1 38 1 0 1 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 8 44 1 0 8 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 14 50 1 1 15 51 1 0 15 52 1 0 16 53 1 6 17 54 1 6 19 55 1 0 19 56 1 0 23 57 1 0 23 58 1 0 23 59 1 0 24 60 1 0 24 61 1 0 25 62 1 0 25 63 1 0 26 64 1 6 27 65 1 6 28 66 1 0 28 67 1 0 31 68 1 0 33 69 1 0 33 70 1 0 33 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 35 75 1 0 35 76 1 0 35 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 M END

Standard InCHIKey	RGFKYIOSMXLVPZ-PDRQEGEBSA-N
Standard InCHI	InChI=1S/C31H44O5/c1-18(2)14-21(32)15-19(3)22-8-10-29(6)24-16-23-26(20(4)27(34)36-23)31(11-9-25(33)35-7)17-30(24,31)13-12-28(22,29)5/h14,19,22-24,26H,4,8-13,15-17H2,1-3,5-7H3/t19-,22-,23-,24+,26-,28-,29+,30+,31-/m1/s1
SMILES	COC(=O)CC[C@@]12C[C@@]32CC[C@]2([C@@]([C@@H]3C[C@@H]3[C@H]1C(=C)C(=O)O3)(C)CC[C@@H]2[C@@H](CC(=O)C=C(C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	496.32	Volume:	532.719 ? Van der Waals volume.
Dense:	0.932	LogP:	4.866 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.067 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.647 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	26.0
TPSA:	69.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.309	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.632	Fsp³:	0.774
MCE-18:	129.836 ? 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:	0.852	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.028 ? 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:	0.427	Promiscuous compounds:	0.338

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.19	MDCK Permeability:	-4.87
Pgp-inhibitor:	0.03	Pgp-substrate:	0.001
PAMPA:	0.047 ? 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%):	0.749	30% Bioavailability (F30%):	0.124
50% Bioavailability (F50%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.461	MRP1:	0.987
Plasma Protein Binding (PPB):	95.846%	Volume Distribution (VD):	0.032
Fu:	3.541% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.001
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.328	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.013
HLM stability:	0.02 ? 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):

8.474

Half-life (T1/2):

0.471

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.211
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.472
AMES Toxicity:	0.761	Rat Oral Acute Toxicity:	0.426
Maximum Recommended Daily Dose:	0.61	Skin Sensitization:	0.998
Carcinogencity:	0.889	Eye Corrosion:	0.035
Eye Irritation:	0.606	Respiratory Toxicity:	0.709
Drug-induced Neurotoxicity:	0.679	Ototoxicity:	0.513
Hematotoxicity:	0.977	Drug-induced Nephrotoxicity:	0.971
Genotoxicity:	0.947	RPMI-8226 Immunitoxicity:	0.225
A549 Cytotoxicity:	0.343	Hek293 Cytotoxicity:	0.407
BCF:	1.496 ? 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:	4.27 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.704 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.181 ? 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
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190447]
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[23550966]
NPO4042	Gardenia aubryi	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4042	Gardenia aubryi	Species	Rubiaceae	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
Inhibition	1
IC50	4
ED50	7

Activity Type	# Activity
Individual protein	1
Cell line	10
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	0.4	%	PMID[23550966]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	52000.0	nM	PMID[20421396]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	21000.0	nM	PMID[20421396]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	35000.0	nM	PMID[20655237]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	40000.0	nM	PMID[25611215]
NPT71	Cell line	HEK293	Homo sapiens	ED50	=	3.2	uM	PMID[27317644]
NPT1034	Cell line	Lu1	Homo sapiens	ED50	=	5.0	uM	PMID[25211145]
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	4.2	uM	DrugMatrix in vivo data: Pathology
NPT1851	Cell line	Col2	Homo sapiens	ED50	=	5.8	uM	PMID[19743809]
NPT91	Cell line	KB	Homo sapiens	ED50	=	2.0	uM	PMID[19674905]
NPT168	Cell line	P388	Mus musculus	ED50	=	1.0	uM	Open TG-GATES in vivo data: Biochemistry
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	4.6	uM	PMID[23550966]

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 NPC252295 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	21224
0.1-0.2	25406
0.2-0.3	3028
0.3-0.4	153
0.4-0.5	22
0.5-0.6	16
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	Natural Product ID
0.7969	Intermediate Similarity	NPC307164
0.7612	Intermediate Similarity	NPC470906
0.7612	Intermediate Similarity	NPC147473
0.7612	Intermediate Similarity	NPC603020
0.7391	Intermediate Similarity	NPC245284
0.7143	Intermediate Similarity	NPC476237
0.6133	Remote Similarity	NPC470277
0.6076	Remote Similarity	NPC470273
0.6027	Remote Similarity	NPC81256
0.5952	Remote Similarity	NPC470278
0.5875	Remote Similarity	NPC56731
0.5867	Remote Similarity	NPC476303
0.5696	Remote Similarity	NPC470275
0.5694	Remote Similarity	NPC37153
0.5682	Remote Similarity	NPC470279
0.5641	Remote Similarity	NPC176883
0.5422	Remote Similarity	NPC470276
0.5325	Remote Similarity	NPC486370
0.5325	Remote Similarity	NPC486371
0.5325	Remote Similarity	NPC486372
0.5312	Remote Similarity	NPC470280
0.5278	Remote Similarity	NPC33473
0.5256	Remote Similarity	NPC486361
0.5161	Remote Similarity	NPC470274
0.5125	Remote Similarity	NPC486367

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7081
0.1-0.2	2005
0.2-0.3	63
0.3-0.4	1
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