NPASS Compound

Natural Product: NPC48079

Natural Product ID	NPC48079
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Alpha,20-Lupandiol
IUPAC Name	(1R,3aR,5aR,5bR,7aR,9R,11aR,11bR,13aR,13bS)-1-(2-hydroxypropan-2-yl)-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms	3Alpha,20-Lupandiol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL481837
PubChem CID	11647965
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 84 88 0 0 0 0 0 0 0 0999 V2000 6.5949 0.3225 1.3635 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6015 0.7264 0.4325 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7368 1.7081 1.1085 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3203 1.3055 1.3541 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7334 0.7553 0.0380 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4900 -0.5440 -0.1262 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9598 -0.4136 -0.2636 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5655 -1.6901 0.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4157 -0.5018 -1.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9026 -1.4332 -1.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4905 -1.8186 -0.7680 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6587 -0.5638 -0.5899 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3061 0.4422 0.3180 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4457 1.6408 0.3705 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0107 1.4328 0.5602 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6211 0.2455 -0.0907 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6632 -0.9144 0.0840 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4688 -1.1782 1.5813 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1048 -2.2116 -0.4852 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5062 -2.5540 -0.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3595 -1.3765 -0.4300 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0052 -0.1267 0.3689 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1338 0.7144 0.0671 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3203 -0.2214 -0.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7892 -1.6185 0.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6789 1.7189 1.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7413 2.6696 1.3419 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3740 1.1298 2.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7717 2.5183 0.2749 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4732 -1.1602 -1.8927 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3673 -0.0371 -1.9611 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9766 1.7784 -0.9925 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4574 0.1806 0.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2111 1.2976 -0.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1437 2.0174 2.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6928 2.6980 0.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7691 2.1660 1.7244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3218 0.4541 2.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2935 -1.0855 0.8525 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2833 -2.5868 -0.1858 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6753 -1.5586 0.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4068 -1.7167 1.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6058 -1.5346 -2.0448 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7274 -0.0500 -2.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3933 0.0385 -1.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9863 -1.0800 -2.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4890 -2.3978 -1.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5619 -2.4252 0.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0662 -2.4208 -1.5794 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2963 -0.0177 1.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6990 2.2837 -0.5237 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7965 2.2776 1.2373 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3035 1.5628 1.6293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4512 2.3409 0.0467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6987 0.4670 -1.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4262 -1.8045 1.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5384 -0.2762 2.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3298 -1.8288 1.9221 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9646 -2.3436 -1.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4515 -3.0017 -0.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8400 -3.3625 -0.8378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6432 -2.9854 0.8793 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9154 -0.4886 1.4194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9564 1.2416 -0.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6300 -0.2165 -1.2558 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1517 -0.0739 0.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3003 -2.3884 -0.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7533 -1.8785 1.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6421 3.3467 0.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1188 1.8100 3.0799 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4744 1.1519 2.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0760 0.1051 2.4435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7584 2.0257 0.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8795 3.5298 0.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4959 2.6749 -0.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7264 -1.8026 -2.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3088 -0.1399 -2.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4635 -1.5187 -2.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5006 -0.5711 -2.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 1.0227 -2.0197 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2097 -0.2185 -2.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6756 2.7757 -0.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0496 1.8790 -1.1914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4570 1.6809 -1.9381 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 0 7 9 1 0 6 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 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 21 30 1 6 12 31 1 6 5 32 1 6 7 2 1 0 17 12 1 0 25 21 1 0 13 5 1 0 22 16 1 0 1 33 1 0 2 34 1 6 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 6 39 1 1 8 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 13 50 1 1 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 6 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 22 63 1 1 23 64 1 6 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 32 83 1 0 32 84 1 0 M END

Standard InCHIKey	YDNYDUBBAZTLTQ-FSEYCXJLSA-N
Standard InCHI	InChI=1S/C30H52O2/c1-25(2)21-12-16-30(8)22(28(21,6)15-13-23(25)31)10-9-20-24-19(26(3,4)32)11-14-27(24,5)17-18-29(20,30)7/h19-24,31-32H,9-18H2,1-8H3/t19-,20-,21+,22-,23-,24-,27-,28+,29-,30-/m1/s1
SMILES	O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(O)(C)C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	444.4	Volume:	502.234 ? Van der Waals volume.
Dense:	0.885	LogP:	5.966 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.938 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.292 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	25.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.448	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.747	Fsp³:	1.0
MCE-18:	105.3 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.845	Fluc inhibitor:	0.003 ? 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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.558	Promiscuous compounds:	0.386

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.277	MDCK Permeability:	-4.945
Pgp-inhibitor:	0.909	Pgp-substrate:	0.07
PAMPA:	0.367 ? 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%):	0.013
50% Bioavailability (F50%):	0.717

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.804	MRP1:	0.914
Plasma Protein Binding (PPB):	96.94%	Volume Distribution (VD):	-0.203
Fu:	3.542% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.68
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.343	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.198	CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.722
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.745
HLM stability:	0.976 ? 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):

13.283

Half-life (T1/2):

0.57

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.128
Human Hepatotoxicity (H-HT):	0.572	Drug-induced Liver Injury (DILI):	0.129
AMES Toxicity:	0.324	Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.481	Skin Sensitization:	0.968
Carcinogencity:	0.947	Eye Corrosion:	0.265
Eye Irritation:	0.904	Respiratory Toxicity:	0.848
Drug-induced Neurotoxicity:	0.008	Ototoxicity:	0.517
Hematotoxicity:	0.57	Drug-induced Nephrotoxicity:	0.712
Genotoxicity:	0.256	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.068	Hek293 Cytotoxicity:	0.351
BCF:	2.208 ? 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:	4.245 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.338 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.947 ? 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
NPO4645	Grewia bilamellata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16562832]
NPO4645	Grewia bilamellata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7348	Streptomyces gannmycicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7348	Streptomyces gannmycicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4645	Grewia bilamellata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4154	Cortinarius violaceus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10592	Phascolosoma elongatum	Species	Phascolosomatidae	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
ED50	1
IC50	2

Activity Type	# Activity
Cell line	1
Organism	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
NPT91	Cell line	KB	Homo sapiens	ED50	>	90.0	uM	PMID[16562832]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	19800.0	nM	PMID[16562832]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	19100.0	nM	PMID[16562832]

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 NPC48079 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	29077
0.1-0.2	17907
0.2-0.3	2308
0.3-0.4	410
0.4-0.5	89
0.5-0.6	43
0.6-0.7	14
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	NPC480925
0.766	Intermediate Similarity	NPC142712
0.7347	Intermediate Similarity	NPC192638
0.7347	Intermediate Similarity	NPC25511
0.7347	Intermediate Similarity	NPC600137
0.72	Intermediate Similarity	NPC97534
0.72	Intermediate Similarity	NPC472741
0.72	Intermediate Similarity	NPC195155
0.6923	Remote Similarity	NPC248830
0.6923	Remote Similarity	NPC212241
0.6731	Remote Similarity	NPC301226
0.6667	Remote Similarity	NPC269396
0.6545	Remote Similarity	NPC298168
0.6545	Remote Similarity	NPC143133
0.6415	Remote Similarity	NPC144075
0.6154	Remote Similarity	NPC129829
0.6111	Remote Similarity	NPC245869
0.6	Remote Similarity	NPC285761
0.6	Remote Similarity	NPC34930
0.6	Remote Similarity	NPC231256
0.6	Remote Similarity	NPC232112
0.6	Remote Similarity	NPC178383
0.5893	Remote Similarity	NPC5767
0.5893	Remote Similarity	NPC475742
0.5789	Remote Similarity	NPC246956
0.5789	Remote Similarity	NPC13554
0.5789	Remote Similarity	NPC74595
0.5789	Remote Similarity	NPC119355
0.5789	Remote Similarity	NPC264665
0.5614	Remote Similarity	NPC93662
0.5593	Remote Similarity	NPC12774
0.5574	Remote Similarity	NPC483720
0.5536	Remote Similarity	NPC91573
0.5536	Remote Similarity	NPC104387
0.5536	Remote Similarity	NPC202540
0.5517	Remote Similarity	NPC91387
0.5517	Remote Similarity	NPC231680
0.5517	Remote Similarity	NPC270306
0.5517	Remote Similarity	NPC66105
0.55	Remote Similarity	NPC477578
0.55	Remote Similarity	NPC477577
0.5455	Remote Similarity	NPC606606
0.5439	Remote Similarity	NPC42853
0.541	Remote Similarity	NPC289486
0.5357	Remote Similarity	NPC185536
0.5345	Remote Similarity	NPC211009
0.5345	Remote Similarity	NPC296701
0.5345	Remote Similarity	NPC201725
0.5345	Remote Similarity	NPC218616
0.5345	Remote Similarity	NPC602784
0.5323	Remote Similarity	NPC131665
0.5323	Remote Similarity	NPC476071
0.5323	Remote Similarity	NPC255387
0.5323	Remote Similarity	NPC481321
0.5323	Remote Similarity	NPC607755
0.5263	Remote Similarity	NPC240235
0.5263	Remote Similarity	NPC14112
0.5254	Remote Similarity	NPC23884
0.5172	Remote Similarity	NPC58631
0.5172	Remote Similarity	NPC237460
0.5094	Remote Similarity	NPC127094
0.5094	Remote Similarity	NPC11908
0.5088	Remote Similarity	NPC102708
0.5082	Remote Similarity	NPC472608
0.5082	Remote Similarity	NPC603388

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC48079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7803
0.1-0.2	1289
0.2-0.3	54
0.3-0.4	3
0.4-0.5	1
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