NPASS Compound

Natural Product: NPC472186

Natural Product ID	NPC472186
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HFYZJOCCNNMCMB-OEXXYOJESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3343969
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

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 85 87 0 0 0 0 0 0 0 0999 V2000 -1.0094 7.0038 3.7132 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9299 5.4799 3.8359 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6036 4.9540 2.4734 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4976 3.4658 2.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6747 2.8107 3.5109 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2086 2.7365 1.3378 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0949 1.3528 1.2546 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0407 0.7200 0.2584 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5980 -0.7141 0.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8760 -1.4574 -0.3894 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4299 -0.5889 -1.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4494 -0.1078 -2.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0244 0.0297 -2.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4835 -0.6363 -0.9610 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3591 -1.7934 -1.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5838 -1.1646 -1.6619 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8658 -0.1527 -0.8160 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5436 0.2027 -0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2665 1.0487 0.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7617 -0.6526 0.1644 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9950 -0.0462 0.4345 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2715 0.9797 -0.2460 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9089 -0.6013 1.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1352 0.2734 1.5140 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1342 -0.2173 2.5484 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0688 -2.5143 -2.4435 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2325 -3.8907 -2.5221 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6494 -4.4958 -1.4977 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9129 -4.5686 -3.7890 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6793 -0.5591 -3.2809 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4135 0.3680 -4.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5304 -1.2786 -2.3010 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5933 -2.7985 -1.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6048 -1.5973 0.8863 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8794 -2.2496 1.0876 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0886 -1.8366 0.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7453 -2.7011 -0.3847 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7104 -0.5536 0.5459 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2289 0.4035 1.3043 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1925 7.2951 2.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0221 7.4721 3.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7466 7.4142 4.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1455 5.1813 4.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9210 5.0877 4.1489 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4507 5.2202 1.7872 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3389 5.3813 2.0773 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2689 0.8750 2.2244 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0371 0.8853 0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8779 1.3070 -0.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2181 -1.1643 0.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9854 0.3057 -1.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8407 0.9000 -2.8417 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6117 -0.7299 -3.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2939 1.1138 -2.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6757 -2.4126 -0.4140 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2793 0.7511 -1.3116 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0863 1.6103 1.2086 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2374 -1.6361 1.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4045 -0.6753 2.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5870 0.2493 0.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8437 1.2962 1.8181 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9873 0.4885 2.5499 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6097 -0.2483 3.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5509 -1.2135 2.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0317 -3.8562 -4.6316 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5488 -5.4641 -3.9405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1570 -4.8885 -3.7286 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1678 0.8956 -3.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9715 -0.1683 -4.8099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7708 1.0967 -4.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2931 -1.1540 -3.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5708 -2.3486 -2.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5094 -0.8201 -2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7707 -3.3336 -0.5706 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5983 -2.7552 -2.1420 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5001 -3.4490 -0.8208 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5185 -0.6638 1.5025 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8935 -2.2836 1.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7885 -3.4005 1.0983 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1570 -2.1398 2.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6462 -2.4517 -0.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3203 -3.6752 -0.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6501 -0.3206 -0.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7698 1.3802 1.3475 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3708 0.3931 1.9316 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 2 0 4 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 2 0 17 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 0 15 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 13 30 1 0 30 31 1 0 11 32 1 0 10 33 1 0 10 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 19 7 1 0 14 9 1 0 18 14 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 0 2 44 1 0 3 45 1 0 3 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 15 55 1 0 17 56 1 0 19 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 25 64 1 0 29 65 1 0 29 66 1 0 29 67 1 0 31 68 1 0 31 69 1 0 31 70 1 0 32 71 1 0 32 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 37 81 1 0 37 82 1 0 38 83 1 0 39 84 1 0 39 85 1 0 M END

Standard InCHIKey	HFYZJOCCNNMCMB-OEXXYOJESA-N
Standard InCHI	InChI=1S/C31H46O8/c1-9-12-26(33)37-22-17-23-28(38-27(34)13-10-2)39-29(36-21(6)32)31(23)24(18-22)30(7,15-14-19(4)11-3)20(5)16-25(31)35-8/h11,17,20,22,24-25,28-29H,3-4,9-10,12-16,18H2,1-2,5-8H3/t20-,22+,24+,25+,28+,29-,30-,31-/m1/s1
SMILES	CCCC(=O)OC1CC2C(C(CC(C23C(OC(C3=C1)OC(=O)CCC)OC(=O)C)OC)C)(C)CCC(=C)C=C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	546.32	Volume:	573.566 ? Van der Waals volume.
Dense:	0.952	LogP:	4.523 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.912 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.378 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	20.0
TPSA:	97.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.131	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.745	Fsp³:	0.71
MCE-18:	87.811 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.162	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.333 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.319	Promiscuous compounds:	0.017

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.861	MDCK Permeability:	-4.685
Pgp-inhibitor:	0.334	Pgp-substrate:	0.878
PAMPA:	0.227 ? 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):	0.043
20% Bioavailability (F20%):	0.918	30% Bioavailability (F30%):	0.956
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.254	MRP1:	0.996
Plasma Protein Binding (PPB):	96.202%	Volume Distribution (VD):	0.17
Fu:	3.487% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.466
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.401
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.069	CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.015	CYP3A4-substrate:	0.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

8.501

Half-life (T1/2):

0.509

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.472
Human Hepatotoxicity (H-HT):	0.459	Drug-induced Liver Injury (DILI):	0.514
AMES Toxicity:	0.675	Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.958	Skin Sensitization:	0.959
Carcinogencity:	0.448	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.12
Drug-induced Neurotoxicity:	0.868	Ototoxicity:	0.803
Hematotoxicity:	0.123	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.857	RPMI-8226 Immunitoxicity:	0.257
A549 Cytotoxicity:	0.181	Hek293 Cytotoxicity:	0.518
BCF:	0.693 ? 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:	3.865 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.822 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.93 ? 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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]
NPO32459	casearia balansae	Species	Salicaceae	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

Activity Type	# Activity
EC50	1

Activity Type	# Activity
Cell line	1

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
NPT681	Cell line	PC-12	Rattus norvegicus	EC50	=	20.2	ug.mL-1	PMID[25286284]

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 NPC472186 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	22856
0.1-0.2	25247
0.2-0.3	1614
0.3-0.4	34
0.4-0.5	44
0.5-0.6	31
0.6-0.7	13
0.7-0.8	0
0.8-0.85	8
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9821	High Similarity	NPC488649
0.9649	High Similarity	NPC481017
0.9464	High Similarity	NPC481019
0.9286	High Similarity	NPC481020
0.9167	High Similarity	NPC472187
0.8772	High Similarity	NPC171598
0.8596	High Similarity	NPC472189
0.8475	Intermediate Similarity	NPC318917
0.8448	Intermediate Similarity	NPC481018
0.8197	Intermediate Similarity	NPC471366
0.8197	Intermediate Similarity	NPC476800
0.8197	Intermediate Similarity	NPC488237
0.8167	Intermediate Similarity	NPC471362
0.8167	Intermediate Similarity	NPC471372
0.8033	Intermediate Similarity	NPC472188
0.7937	Intermediate Similarity	NPC473545
0.75	Intermediate Similarity	NPC471365
0.746	Intermediate Similarity	NPC488236
0.6765	Remote Similarity	NPC488963
0.6765	Remote Similarity	NPC48548
0.6719	Remote Similarity	NPC606965
0.6615	Remote Similarity	NPC132395
0.6615	Remote Similarity	NPC471364
0.6615	Remote Similarity	NPC600724
0.6515	Remote Similarity	NPC479935
0.6364	Remote Similarity	NPC488651
0.6364	Remote Similarity	NPC488648
0.6324	Remote Similarity	NPC473204
0.6232	Remote Similarity	NPC7644
0.6154	Remote Similarity	NPC603601
0.6027	Remote Similarity	NPC127933
0.5972	Remote Similarity	NPC488219
0.5915	Remote Similarity	NPC217921
0.5915	Remote Similarity	NPC88013
0.5915	Remote Similarity	NPC135015
0.589	Remote Similarity	NPC488221
0.589	Remote Similarity	NPC488220
0.589	Remote Similarity	NPC488216
0.5882	Remote Similarity	NPC479934
0.5797	Remote Similarity	NPC479936
0.5797	Remote Similarity	NPC488235
0.5732	Remote Similarity	NPC488962
0.5714	Remote Similarity	NPC479943
0.5676	Remote Similarity	NPC125423
0.56	Remote Similarity	NPC40728
0.5584	Remote Similarity	NPC486752
0.5571	Remote Similarity	NPC479939
0.5556	Remote Similarity	NPC479940
0.5522	Remote Similarity	NPC488650
0.5522	Remote Similarity	NPC481022
0.5493	Remote Similarity	NPC479937
0.5417	Remote Similarity	NPC479938
0.527	Remote Similarity	NPC475889
0.527	Remote Similarity	NPC7613
0.527	Remote Similarity	NPC479942
0.527	Remote Similarity	NPC238397
0.52	Remote Similarity	NPC479941
0.5139	Remote Similarity	NPC88507
0.5135	Remote Similarity	NPC128795
0.5122	Remote Similarity	NPC488217
0.5122	Remote Similarity	NPC488218
0.5067	Remote Similarity	NPC609715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7273
0.1-0.2	1858
0.2-0.3	19
0.3-0.4	0
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