NPASS Compound

Natural Product: NPC125423

Natural Product ID	NPC125423
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Caseamembrin C
IUPAC Name	[(1R,3S,5S,6aR,7R,8R,9R,10S,10aR)-1-acetyloxy-3-butanoyloxy-9,10-dihydroxy-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	caseamembrin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL475879
PubChem CID	11203809
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 86 88 0 0 0 0 0 0 0 0999 V2000 -7.5945 -2.8090 1.9481 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5725 -2.6145 0.8440 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1686 -2.5151 1.3920 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2349 -2.3319 0.2560 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6923 -2.3073 -0.9130 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8669 -2.1829 0.4199 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9864 -2.0107 -0.6787 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0327 -3.0085 -0.6155 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0535 -2.4384 0.0845 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2277 -1.1529 -0.7375 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2070 -0.7135 -0.5131 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6162 0.4805 -0.2542 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6418 1.5637 -0.1441 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1848 2.4929 0.8078 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5324 3.7754 0.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3759 4.1830 -0.7092 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0955 4.6362 1.5653 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4137 6.0192 1.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1580 6.6881 0.5401 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3495 3.9995 2.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7088 1.1178 0.3100 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1851 -0.2154 -0.1592 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5411 -0.0701 -0.9039 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8133 -1.2101 -1.8091 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6730 -1.5084 -2.7727 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3109 -1.3978 -2.2036 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4853 -2.5104 -2.5926 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8602 -2.8465 -3.1980 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2911 -2.4761 -1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3463 1.1475 -1.8277 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5770 0.3115 0.0744 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9686 0.5772 -0.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8299 -0.4339 -0.7969 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2617 -1.4070 0.0299 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3011 -0.4360 -2.1469 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9995 0.4412 -3.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4626 -2.0957 1.3540 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 -2.6090 2.5369 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0073 -3.4118 2.4329 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4772 -2.2662 3.8880 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5490 -3.1188 1.4715 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7773 -1.8726 2.4945 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2764 -3.6524 2.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7858 -1.6524 0.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6308 -3.4054 0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1037 -1.6036 2.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9308 -3.4347 1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5075 -2.0301 -1.6404 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8622 -3.1223 0.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6674 0.6820 -0.1182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6018 2.1100 -1.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3447 4.6967 2.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8106 6.6137 1.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1918 5.9539 0.2633 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2457 6.2821 1.0408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0972 6.5171 -0.5362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1722 7.7859 0.7237 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9930 3.6142 1.2703 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1345 3.1155 2.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9706 4.6835 2.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6848 1.2030 1.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3816 1.9743 -0.0086 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5442 -0.7268 0.8058 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6311 -0.8979 -2.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7838 -0.9171 -3.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1970 -0.5526 -2.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4889 -2.4663 -3.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1778 -3.4446 -2.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3872 -2.4599 -0.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6637 -3.3626 -1.4351 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2908 -2.7353 -1.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9093 0.9652 -2.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7964 2.0574 -1.4417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3020 1.2221 -2.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5733 -0.3886 0.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1756 1.2692 0.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1053 1.4894 -0.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5356 0.8883 0.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9830 -1.4368 1.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9075 -2.1677 -0.3861 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9971 -1.2253 -2.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3743 0.4040 -4.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3323 1.2789 -2.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9952 -3.1109 4.3809 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4152 -2.0447 4.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1947 -1.4318 3.8692 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 6 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 13 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 6 23 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 35 36 2 0 9 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 11 7 1 0 26 10 1 0 22 10 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 7 48 1 6 9 49 1 1 12 50 1 0 13 51 1 6 17 52 1 0 18 53 1 0 18 54 1 0 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 22 63 1 1 24 64 1 6 25 65 1 6 26 66 1 6 27 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 32 77 1 0 32 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 36 82 1 0 36 83 1 0 40 84 1 0 40 85 1 0 40 86 1 0 M END

Standard InCHIKey	BOVQULZBTRBINP-SFNDVPNUSA-N
Standard InCHI	InChI=1S/C31H46O9/c1-9-12-24(33)39-28-22-15-21(38-27(36)18(5)11-3)16-23-30(8,14-13-17(4)10-2)19(6)25(34)26(35)31(22,23)29(40-28)37-20(7)32/h10,15,18-19,21,23,25-26,28-29,34-35H,2,4,9,11-14,16H2,1,3,5-8H3/t18?,19-,21+,23+,25+,26+,28+,29-,30-,31-/m0/s1
SMILES	CCCC(=O)O[C@@H]1O[C@@H]([C@]23C1=C[C@@H](OC(=O)C(CC)C)C[C@@H]3[C@@]([C@H]([C@H]([C@H]2O)O)C)(C)CCC(=C)C=C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.31	Volume:	582.356 ? Van der Waals volume.
Dense:	0.966	LogP:	3.492 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.33 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.366 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	20.0
TPSA:	128.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.163	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.964	Fsp³:	0.71
MCE-18:	94.566 ? 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:	0.897	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.262	Promiscuous compounds:	0.342

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.099	MDCK Permeability:	-4.784
Pgp-inhibitor:	0.145	Pgp-substrate:	0.704
PAMPA:	0.428 ? 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):	0.008
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98	MRP1:	0.997
Plasma Protein Binding (PPB):	77.101%	Volume Distribution (VD):	-0.025
Fu:	15.192% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.773
OATP1B3 inhibitor:	0.773	BCRP inhibitor:	0.157
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.015	CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.244	CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.022	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.784
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.233
CYP2B6-substrate:	0.022	CYP2C8-inhibitor:	0.999
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):

6.49

Half-life (T1/2):

1.053

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.301
Human Hepatotoxicity (H-HT):	0.653	Drug-induced Liver Injury (DILI):	0.966
AMES Toxicity:	0.991	Rat Oral Acute Toxicity:	0.814
Maximum Recommended Daily Dose:	0.963	Skin Sensitization:	1.0
Carcinogencity:	0.751	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.482
Drug-induced Neurotoxicity:	0.975	Ototoxicity:	0.741
Hematotoxicity:	0.897	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.992	RPMI-8226 Immunitoxicity:	0.524
A549 Cytotoxicity:	0.977	Hek293 Cytotoxicity:	0.713
BCF:	0.55 ? 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:	3.532 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.297 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.658 ? 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
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14709876]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	twig	n.a.	PMID[14709876]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[15043402]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309320]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24498	Casearia membranacea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24498	Casearia membranacea	Species	Salicaceae	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	2

Activity Type	# Activity
Cell line	1
Non-molecular	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
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	600.0	nM	PMID[15043402]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	800.0	nM	PMID[15043402]

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 NPC125423 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	18869
0.1-0.2	27572
0.2-0.3	3274
0.3-0.4	40
0.4-0.5	55
0.5-0.6	30
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8594	High Similarity	NPC88013
0.7826	Intermediate Similarity	NPC127933
0.7826	Intermediate Similarity	NPC40728
0.7	Intermediate Similarity	NPC475889
0.7	Intermediate Similarity	NPC7613
0.7	Intermediate Similarity	NPC479942
0.6761	Remote Similarity	NPC238397
0.662	Remote Similarity	NPC7644
0.6575	Remote Similarity	NPC471363
0.6528	Remote Similarity	NPC217921
0.6528	Remote Similarity	NPC135015
0.6438	Remote Similarity	NPC488963
0.6351	Remote Similarity	NPC472187
0.6164	Remote Similarity	NPC311223
0.6111	Remote Similarity	NPC479943
0.6081	Remote Similarity	NPC473545
0.6053	Remote Similarity	NPC119550
0.6	Remote Similarity	NPC48548
0.5946	Remote Similarity	NPC479940
0.5946	Remote Similarity	NPC128795
0.5789	Remote Similarity	NPC479941
0.5676	Remote Similarity	NPC472186
0.5676	Remote Similarity	NPC488236
0.5676	Remote Similarity	NPC479937
0.5658	Remote Similarity	NPC330003
0.5658	Remote Similarity	NPC470321
0.5658	Remote Similarity	NPC264867
0.5658	Remote Similarity	NPC473207
0.5658	Remote Similarity	NPC609715
0.56	Remote Similarity	NPC471366
0.56	Remote Similarity	NPC476800
0.56	Remote Similarity	NPC488649
0.56	Remote Similarity	NPC488237
0.5526	Remote Similarity	NPC481017
0.5476	Remote Similarity	NPC316708
0.5467	Remote Similarity	NPC472188
0.5465	Remote Similarity	NPC470026
0.5455	Remote Similarity	NPC488658
0.5455	Remote Similarity	NPC488655
0.5333	Remote Similarity	NPC479935
0.5333	Remote Similarity	NPC481019
0.5325	Remote Similarity	NPC201880
0.5294	Remote Similarity	NPC486751
0.52	Remote Similarity	NPC481020
0.5132	Remote Similarity	NPC479939
0.5128	Remote Similarity	NPC134270
0.5128	Remote Similarity	NPC329623
0.5059	Remote Similarity	NPC87630

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7148
0.1-0.2	1958
0.2-0.3	44
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