NPASS Compound

Natural Product: NPC471363

Natural Product ID	NPC471363
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Rel-(2S,5R,6R,8S,9S,10R,18S,19R)-19-Acetoxy-18-Ethoxy-18,19-Epoxy-2-(2-Xi-Methylbutanoyloxy)-Cleroda-3,13(16),14-Trien-6-Ol
IUPAC Name	[(1R,3S,5S,6aR,7S,8S,10R,10aR)-1-acetyloxy-3-ethoxy-10-hydroxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] 2-methylbutanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419870
PubChem CID	73352259
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 80 82 0 0 0 0 0 0 0 0999 V2000 -4.5625 1.1915 -3.2819 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6068 2.0617 -4.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4181 2.3439 -3.4010 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6550 1.2639 -3.0852 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4262 1.2313 -3.7108 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3847 0.3806 -2.9356 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1432 0.9726 -1.5571 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2988 1.1898 -1.6176 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0105 1.3587 -0.5248 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3686 1.2039 0.7717 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3488 0.7895 1.7084 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3466 0.8217 3.0287 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2978 1.2936 3.6521 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4138 0.3735 3.9510 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6195 -1.1330 3.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9883 -1.4409 2.4160 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3384 0.8895 5.3366 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5504 -0.1588 0.5371 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5584 0.0964 -0.4411 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9048 0.3572 0.1051 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8501 1.1716 -0.7519 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2380 2.2985 -1.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7611 2.3625 -1.5253 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3025 3.0107 -2.6922 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7679 0.3575 -1.6287 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7681 1.2416 1.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7049 -0.8040 0.5865 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1744 -1.5999 1.7543 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2063 -2.5807 2.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8935 -3.9324 2.0762 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5537 -2.2635 2.5555 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0945 -1.0859 2.7018 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0083 -0.9555 -3.0170 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9032 -1.8622 -3.5777 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0260 -1.3668 -3.9942 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 -3.2870 -3.7059 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1082 0.2637 -2.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1927 1.7305 -2.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3142 0.8372 -4.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3809 1.5768 -5.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1258 3.0464 -4.2060 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1366 0.2739 -3.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4109 0.5725 -3.2721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0726 1.6172 -0.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6585 1.8608 1.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3681 0.7939 3.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4811 -1.3773 4.5059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7262 -1.7009 4.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4621 -0.5494 1.9313 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0285 -1.6035 1.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6838 -2.2774 2.3351 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7994 0.1235 6.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9625 1.8091 5.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3174 1.0504 5.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3437 -0.7994 0.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2978 -0.5535 1.4986 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6635 -0.9326 -0.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5895 1.6566 -0.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7306 3.2527 -1.2491 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5463 2.1405 -2.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3932 2.9653 -0.6922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0760 3.0769 -3.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4959 -0.6769 -1.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7051 0.8232 -2.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8567 0.4932 -1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8220 1.1870 1.8315 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6489 2.2900 1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1417 0.7867 2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7631 -0.5537 0.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5847 -1.5835 -0.2851 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2959 -2.2513 1.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7797 -1.0263 2.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7113 -4.5471 2.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9332 -4.2724 1.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1653 -3.1709 2.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1640 -1.0267 3.0575 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6747 -0.1229 2.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1009 -3.6236 -2.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -3.4718 -4.6104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5757 -3.8977 -3.7417 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 1 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 14 17 1 0 10 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 21 25 1 0 20 26 1 1 20 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 6 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 8 4 1 0 23 7 1 0 19 7 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 2 41 1 0 4 42 1 6 6 43 1 6 9 44 1 0 10 45 1 1 14 46 1 0 15 47 1 0 15 48 1 0 16 49 1 0 16 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 17 54 1 0 18 55 1 0 18 56 1 0 19 57 1 6 21 58 1 1 22 59 1 0 22 60 1 0 23 61 1 1 24 62 1 0 25 63 1 0 25 64 1 0 25 65 1 0 26 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 28 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 M END

Standard InCHIKey	TZUIFFFPPPAOBF-MJSHZTPJSA-N
Standard InCHI	InChI=1S/C29H44O7/c1-9-17(4)12-13-28(8)19(6)14-24(31)29-22(26(33-11-3)36-27(29)34-20(7)30)15-21(16-23(28)29)35-25(32)18(5)10-2/h9,15,18-19,21,23-24,26-27,31H,1,4,10-14,16H2,2-3,5-8H3/t18?,19-,21+,23+,24+,26-,27-,28-,29-/m0/s1
SMILES	CCO[C@H]1O[C@@H]([C@]23C1=C[C@@H](OC(=O)C(CC)C)C[C@@H]3[C@@]([C@H](C[C@H]2O)C)(C)CCC(=C)C=C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.31	Volume:	532.82 ? Van der Waals volume.
Dense:	0.946	LogP:	3.71 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.405 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.449 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	19.0
TPSA:	91.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.252	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.852	Fsp³:	0.724
MCE-18:	88.4 ? 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:	0.751	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.266	Promiscuous compounds:	0.398

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.219	MDCK Permeability:	-4.823
Pgp-inhibitor:	0.817	Pgp-substrate:	0.052
PAMPA:	0.038 ? 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):	0.001
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.984
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956	MRP1:	0.997
Plasma Protein Binding (PPB):	77.06%	Volume Distribution (VD):	-0.094
Fu:	16.507% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.912
OATP1B3 inhibitor:	0.753	BCRP inhibitor:	0.579
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.74
CYP2C19-inhibitor:	0.538	CYP2C19-substrate:	0.701
CYP2C9-inhibitor:	0.117	CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	0.708
CYP2B6-substrate:	0.005	CYP2C8-inhibitor:	0.999
HLM stability:	0.999 ? 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):

9.862

Half-life (T1/2):

1.163

ADMET: Toxicity

hERG Blockers:	0.158	hERG Blockers (10um):	0.572
Human Hepatotoxicity (H-HT):	0.409	Drug-induced Liver Injury (DILI):	0.828
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.963	Skin Sensitization:	0.996
Carcinogencity:	0.686	Eye Corrosion:	0.001
Eye Irritation:	0.082	Respiratory Toxicity:	0.892
Drug-induced Neurotoxicity:	0.9	Ototoxicity:	0.482
Hematotoxicity:	0.619	Drug-induced Nephrotoxicity:	0.811
Genotoxicity:	0.849	RPMI-8226 Immunitoxicity:	0.283
A549 Cytotoxicity:	0.895	Hek293 Cytotoxicity:	0.684
BCF:	0.941 ? 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:	3.789 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.47 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.839 ? 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
IC50	5

Activity Type	# Activity
Cell line	5

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
NPT1374	Cell line	WI-38	Homo sapiens	IC50	=	60200.0	nM	PMID[12444684]
NPT81	Cell line	A549	Homo sapiens	IC50	=	49800.0	nM	PMID[25237727]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	15300.0	nM	DrugMatrix in vivo data: Biochemistry
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	14800.0	nM	PMID[15920768]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	46900.0	nM	PMID[11858756]

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 NPC471363 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	17691
0.1-0.2	27485
0.2-0.3	4518
0.3-0.4	57
0.4-0.5	34
0.5-0.6	32
0.6-0.7	21
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC475889
0.9032	High Similarity	NPC7613
0.9032	High Similarity	NPC479942
0.9032	High Similarity	NPC238397
0.8485	Intermediate Similarity	NPC127933
0.7969	Intermediate Similarity	NPC479943
0.7727	Intermediate Similarity	NPC479940
0.7727	Intermediate Similarity	NPC7644
0.75	Intermediate Similarity	NPC479941
0.7101	Intermediate Similarity	NPC330003
0.7101	Intermediate Similarity	NPC470321
0.7101	Intermediate Similarity	NPC264867
0.7101	Intermediate Similarity	NPC488658
0.7101	Intermediate Similarity	NPC473207
0.7101	Intermediate Similarity	NPC488655
0.6753	Remote Similarity	NPC486751
0.6575	Remote Similarity	NPC125423
0.6494	Remote Similarity	NPC87630
0.6494	Remote Similarity	NPC179128
0.6486	Remote Similarity	NPC40728
0.6479	Remote Similarity	NPC488660
0.6479	Remote Similarity	NPC488657
0.6479	Remote Similarity	NPC329623
0.6286	Remote Similarity	NPC488659
0.6286	Remote Similarity	NPC602188
0.6286	Remote Similarity	NPC604149
0.6176	Remote Similarity	NPC89171
0.6164	Remote Similarity	NPC88013
0.6027	Remote Similarity	NPC201880
0.6027	Remote Similarity	NPC134270
0.6027	Remote Similarity	NPC479497
0.6027	Remote Similarity	NPC81567
0.6027	Remote Similarity	NPC488652
0.6027	Remote Similarity	NPC488654
0.6027	Remote Similarity	NPC609711
0.6027	Remote Similarity	NPC609880
0.5972	Remote Similarity	NPC472188
0.5972	Remote Similarity	NPC488656
0.5972	Remote Similarity	NPC488236
0.5972	Remote Similarity	NPC479937
0.5946	Remote Similarity	NPC217921
0.5946	Remote Similarity	NPC135015
0.5946	Remote Similarity	NPC609715
0.589	Remote Similarity	NPC471366
0.589	Remote Similarity	NPC476800
0.589	Remote Similarity	NPC488237
0.5833	Remote Similarity	NPC471362
0.5833	Remote Similarity	NPC471372
0.5811	Remote Similarity	NPC128795
0.5789	Remote Similarity	NPC488964
0.5789	Remote Similarity	NPC184512
0.5789	Remote Similarity	NPC252296
0.5733	Remote Similarity	NPC473545
0.56	Remote Similarity	NPC479491
0.5584	Remote Similarity	NPC472187
0.5541	Remote Similarity	NPC488653
0.5405	Remote Similarity	NPC479939
0.5342	Remote Similarity	NPC481018
0.527	Remote Similarity	NPC479934
0.5256	Remote Similarity	NPC488963
0.5205	Remote Similarity	NPC472189
0.5176	Remote Similarity	NPC109376
0.5172	Remote Similarity	NPC224660
0.5139	Remote Similarity	NPC476802
0.5135	Remote Similarity	NPC171598
0.5119	Remote Similarity	NPC116292
0.5067	Remote Similarity	NPC481020
0.5063	Remote Similarity	NPC48548

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6798
0.1-0.2	2302
0.2-0.3	50
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