NPASS Compound

Natural Product: NPC155332

Natural Product ID	NPC155332
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(E/Z)-3-Epi-29-Hydroxystelliferin E
IUPAC Name	[(3Z,3aS,5aR,6S,7R,9aR,9bS)-3-[(3E,5E,7S)-7-acetyloxy-6,10-dimethylundeca-3,5,9-trien-2-ylidene]-6-(hydroxymethyl)-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-7-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499485
PubChem CID	21668739
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 90 92 0 0 0 0 0 0 0 0999 V2000 -9.2685 0.5806 1.8198 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8653 1.0192 1.7439 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1579 1.0221 0.6356 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7167 0.5807 -0.6490 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9223 -0.5879 -1.2620 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5298 -0.0352 -1.4443 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5033 -0.6365 -0.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1704 -0.0511 -1.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0974 -0.6369 -0.5261 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8034 -0.0311 -0.7558 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2603 -0.5859 -0.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2923 -1.8010 0.6332 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6048 -2.2937 1.3162 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7276 -2.3302 0.4768 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3483 -0.9755 0.6887 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7922 -0.8837 0.8739 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0686 -1.1675 2.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6812 -1.8104 0.1166 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6379 -1.1242 -0.8000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4472 -0.0080 -0.1617 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5795 0.9271 0.6757 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6654 2.3403 0.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1040 1.1132 2.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4072 1.6819 2.0346 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1845 0.5230 0.4871 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1158 1.4328 0.9854 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9248 1.2969 0.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6700 -0.1509 -0.3460 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0445 -0.4750 -1.7623 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9776 0.7163 -1.2566 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3040 0.8427 -1.5828 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1475 0.2734 -0.8625 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6383 1.6613 -2.7884 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7204 1.1921 -1.6161 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3429 1.1648 -2.2738 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9139 -1.6922 -0.3864 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4461 -2.8896 -0.8354 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9130 -2.9452 -2.0027 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4597 -4.0905 0.0630 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1996 1.4916 3.0148 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2786 -0.5329 2.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7533 1.1353 2.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8400 0.8591 0.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1334 1.3621 0.6583 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6291 1.4147 -1.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7538 0.2338 -0.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3645 -0.7899 -2.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6043 -1.5134 -0.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0345 0.8376 -1.6798 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -1.5219 0.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7638 -2.6753 -0.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9762 -3.0535 1.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8502 -0.6234 1.6619 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9414 -1.8262 2.5078 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2016 -1.8205 2.6833 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0160 -0.2774 2.9814 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1343 -2.5640 -0.4989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3169 -2.4754 0.7824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4146 -1.8963 -1.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2104 -0.7946 -1.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2901 -0.4405 0.3922 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4503 3.1213 0.8014 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9267 2.4583 -0.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6636 2.5329 -0.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3140 0.0972 2.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5152 1.7577 2.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7690 1.6882 2.9526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0732 0.5049 -0.6515 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4413 2.5051 0.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7777 1.1567 1.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3414 1.8321 -0.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0815 1.7759 0.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3251 0.5025 -2.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8566 -1.1668 -1.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1952 -0.8485 -2.3860 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4529 1.2096 -3.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7522 1.6934 -3.4740 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8486 2.7274 -2.5315 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2581 1.6017 -1.7599 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3474 1.9735 -1.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2660 1.0117 -2.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2604 1.3338 -2.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0688 2.0815 -1.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5345 1.0156 -3.0206 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8841 -3.6998 1.0350 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1397 -4.8524 -0.3839 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4187 -4.4431 0.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2985 0.8384 3.1521 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8716 2.5436 2.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8689 1.3518 3.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 20 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 10 34 1 0 6 35 1 0 5 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 2 40 1 0 28 11 1 0 28 15 1 0 25 16 1 0 1 41 1 0 1 42 1 0 1 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 6 7 48 1 0 8 49 1 0 9 50 1 0 14 51 1 0 14 52 1 0 15 53 1 1 17 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 1 22 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 25 68 1 6 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 33 76 1 0 33 77 1 0 33 78 1 0 34 79 1 0 34 80 1 0 34 81 1 0 35 82 1 0 35 83 1 0 35 84 1 0 39 85 1 0 39 86 1 0 39 87 1 0 40 88 1 0 40 89 1 0 40 90 1 0 M END

Standard InCHIKey	ZFNWQRALNVEBDQ-AEJDOHNSSA-N
Standard InCHI	InChI=1S/C34H50O6/c1-21(2)13-14-27(39-24(5)36)22(3)11-10-12-23(4)31-26(38)19-29-32(7)18-16-30(40-25(6)37)34(9,20-35)28(32)15-17-33(29,31)8/h10-13,27-30,35H,14-20H2,1-9H3/b12-10+,22-11+,31-23+/t27-,28+,29-,30+,32-,33-,34+/m0/s1
SMILES	CC(=CC[C@@H](/C(=C/C=C/C(=C/1C(=O)C[C@H]2[C@@]3(C)CC[C@H]([C@](C)(CO)[C@@H]3CC[C@]12C)OC(=O)C)/C)/C)OC(=O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	554.36	Volume:	605.237 ? Van der Waals volume.
Dense:	0.916	LogP:	4.001 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.625 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.287 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	22.0
TPSA:	89.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.153	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.029	Fsp³:	0.676
MCE-18:	69.193 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.693	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.051 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.59	Promiscuous compounds:	0.674

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.944	MDCK Permeability:	-4.776
Pgp-inhibitor:	0.996	Pgp-substrate:	0.192
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%):	0.015	30% Bioavailability (F30%):	0.057
50% Bioavailability (F50%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.995
Plasma Protein Binding (PPB):	89.69%	Volume Distribution (VD):	-0.089
Fu:	8.671% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.026
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.954	CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.83
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	1.0
HLM stability:	0.975 ? 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):

8.215

Half-life (T1/2):

0.427

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.16
Human Hepatotoxicity (H-HT):	0.541	Drug-induced Liver Injury (DILI):	0.523
AMES Toxicity:	0.445	Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.3	Skin Sensitization:	0.98
Carcinogencity:	0.819	Eye Corrosion:	0.015
Eye Irritation:	0.242	Respiratory Toxicity:	0.267
Drug-induced Neurotoxicity:	0.05	Ototoxicity:	0.362
Hematotoxicity:	0.621	Drug-induced Nephrotoxicity:	0.587
Genotoxicity:	0.723	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.227	Hek293 Cytotoxicity:	0.216
BCF:	1.153 ? 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:	4.225 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.983 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.337 ? 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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO33335	Jaspis sp.	Species	Ancorinidae	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	2

Activity Type	# Activity
Cell line	2

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
NPT375	Cell line	Malme-3M	Homo sapiens	IC50	=	1.2	ug.mL-1	PMID[15787444]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	16.62	ug.mL-1	PMID[15787444]

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 NPC155332 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	17683
0.1-0.2	25867
0.2-0.3	6110
0.3-0.4	137
0.4-0.5	30
0.5-0.6	14
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114540
0.7727	Intermediate Similarity	NPC110937
0.75	Intermediate Similarity	NPC115899
0.75	Intermediate Similarity	NPC32577
0.7059	Intermediate Similarity	NPC605871
0.6538	Remote Similarity	NPC473617
0.6538	Remote Similarity	NPC473828
0.625	Remote Similarity	NPC266955
0.6056	Remote Similarity	NPC473435
0.6056	Remote Similarity	NPC473879
0.6056	Remote Similarity	NPC473280
0.6056	Remote Similarity	NPC471078
0.6	Remote Similarity	NPC151725
0.5972	Remote Similarity	NPC474844
0.5789	Remote Similarity	NPC473283
0.5789	Remote Similarity	NPC475526
0.5775	Remote Similarity	NPC474842
0.5775	Remote Similarity	NPC475965
0.5775	Remote Similarity	NPC604299
0.5676	Remote Similarity	NPC106425
0.5676	Remote Similarity	NPC122324
0.5658	Remote Similarity	NPC473482
0.5658	Remote Similarity	NPC473284
0.5625	Remote Similarity	NPC475163
0.5352	Remote Similarity	NPC2049
0.5068	Remote Similarity	NPC310752
0.5065	Remote Similarity	NPC6206

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC155332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6601
0.1-0.2	2470
0.2-0.3	79
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