NPASS Compound

Natural Product: NPC48949

Natural Product ID	NPC48949
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Guttiferone L
IUPAC Name	n.a.
Synonyms	16-Hydroxyguttiferone K
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL387644
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

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 95 97 0 0 0 0 0 0 0 0999 V2000 -3.9661 -3.9567 -1.2573 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0038 -2.6029 -0.6404 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4182 -2.3936 0.5069 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3342 -1.1806 1.2679 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1181 -0.4111 1.5524 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2857 0.2001 0.5344 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3132 1.0260 -0.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4717 1.3818 1.1680 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1715 2.1888 2.1957 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3714 2.9180 1.8792 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4623 2.9770 2.5745 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6653 2.2829 3.8609 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6200 3.8011 2.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0492 2.3333 0.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4996 1.7589 -1.1652 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3025 2.7347 -2.3226 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0620 3.9902 -2.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8685 4.4256 -3.1021 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6268 5.7037 -2.8943 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9851 3.6572 -4.3675 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9369 1.4055 -1.0316 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2214 0.3106 -0.2817 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6241 0.0887 -0.0129 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3991 1.0858 -0.3888 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3541 -0.9955 0.5857 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5634 -0.6463 1.2541 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2660 -1.5672 1.9914 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8403 -2.8661 2.1213 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6829 -3.2309 1.4875 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9872 -2.2834 0.7432 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8510 -2.7272 0.1172 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5522 -3.7898 2.8689 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4535 -1.2069 2.6425 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0944 -0.3973 0.3067 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2679 -0.9877 1.3918 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3150 -0.4485 -0.3447 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4414 -1.8318 -0.8196 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3655 -2.9469 0.1233 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0810 -4.1276 -0.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5342 -4.4054 -1.5944 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1433 -5.2271 0.7717 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1724 0.4793 -1.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5432 0.2576 -2.6107 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9166 2.1303 -1.6227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7142 -1.5405 -1.3649 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2578 -3.8710 -2.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9683 -4.2241 -1.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6045 -4.6852 -0.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9603 -3.3094 0.9593 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1770 -0.5002 0.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8406 -1.4709 2.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4568 0.4300 2.2391 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5216 -1.0285 2.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8759 1.9425 -0.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5305 0.4016 -1.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2001 1.2666 0.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3863 0.9211 1.6688 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 2.9998 2.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2234 1.6508 3.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3650 3.5110 0.9400 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1014 1.2621 3.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3606 2.8813 4.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7123 2.2412 4.4345 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3381 4.8733 2.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8743 3.4617 1.0231 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5083 3.7155 2.6882 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9808 2.7826 0.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6045 3.2373 0.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7556 3.0247 -2.4386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5618 2.2128 -3.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9668 4.5716 -1.2483 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1815 5.9990 -3.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8500 6.4590 -2.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2546 5.5506 -1.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6628 4.1660 -5.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2976 2.6170 -4.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9850 3.6439 -4.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9197 0.3559 1.1743 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2946 -4.2432 1.5520 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6764 -2.4873 -0.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7303 -4.6954 2.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1062 -1.8955 2.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4398 -1.9819 -1.5338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3097 -2.0303 -1.4826 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6651 -2.8516 1.1803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 -4.4283 -1.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1942 -5.4685 -1.8560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0456 -3.7437 -2.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8375 -5.0336 1.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3109 -6.2181 0.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8813 -5.3016 1.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5375 1.8693 -2.3664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0559 -1.1480 -2.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5448 -2.0481 -1.9539 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1608 -0.7498 -0.7689 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 6 5 1 1 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 3 11 12 1 0 11 13 1 0 8 14 1 0 14 15 1 0 15 16 1 6 16 17 1 0 17 18 2 3 18 19 1 0 18 20 1 0 15 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 28 32 1 0 27 33 1 0 22 34 1 0 34 35 2 0 34 36 1 0 36 37 1 6 37 38 1 0 38 39 2 3 39 40 1 0 39 41 1 0 36 42 1 0 42 43 2 0 21 44 1 0 2 45 1 0 36 6 1 0 42 15 1 0 30 25 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 7 54 1 0 7 55 1 0 7 56 1 0 8 57 1 1 9 58 1 0 9 59 1 0 10 60 1 0 12 61 1 0 12 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 13 66 1 0 14 67 1 0 14 68 1 0 16 69 1 0 16 70 1 0 17 71 1 0 19 72 1 0 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 20 77 1 0 26 78 1 0 29 79 1 0 31 80 1 0 32 81 1 0 33 82 1 0 37 83 1 0 37 84 1 0 38 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 41 90 1 0 41 91 1 0 44 92 1 0 45 93 1 0 45 94 1 0 45 95 1 0 M END

Standard InCHIKey	FERVNTMHOSAJOS-HYOCDBLYSA-N
Standard InCHI	InChI=1S/C38H50O7/c1-22(2)11-10-16-36(9)26(13-12-23(3)4)21-37(17-14-24(5)6)33(43)31(32(42)27-19-29(40)30(41)20-28(27)39)34(44)38(36,35(37)45)18-15-25(7)8/h11-12,14-15,19-20,26,39-41,43H,10,13,16-18,21H2,1-9H3/t26-,36+,37+,38-/m1/s1
SMILES	CC(=CCC[C@@]1(C)[C@H](CC=C(C)C)C[C@@]2(CC=C(C)C)C(=C(C(=O)c3cc(c(cc3O)O)O)C(=O)[C@]1(CC=C(C)C)C2=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.36	Volume:	672.665 ? Van der Waals volume.
Dense:	0.919	LogP:	6.934 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.738 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.9 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	23.0
TPSA:	132.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.683	Fsp³:	0.5
MCE-18:	101.614 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.994	Fluc inhibitor:	0.215 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.179 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.66 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.622	Promiscuous compounds:	0.228

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864	MDCK Permeability:	-4.671
Pgp-inhibitor:	0.0	Pgp-substrate:	0.001
PAMPA:	0.997 ? 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%):	0.002	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.977
Plasma Protein Binding (PPB):	88.087%	Volume Distribution (VD):	0.114
Fu:	13.314% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.88	BCRP inhibitor:	0.015
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	0.991	CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.544	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.947
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):

5.538

Half-life (T1/2):

1.358

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.215
Human Hepatotoxicity (H-HT):	0.742	Drug-induced Liver Injury (DILI):	0.611
AMES Toxicity:	0.377	Rat Oral Acute Toxicity:	0.684
Maximum Recommended Daily Dose:	0.181	Skin Sensitization:	0.998
Carcinogencity:	0.373	Eye Corrosion:	0.0
Eye Irritation:	0.141	Respiratory Toxicity:	0.891
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.905
Hematotoxicity:	0.435	Drug-induced Nephrotoxicity:	0.942
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.826	Hek293 Cytotoxicity:	0.175
BCF:	1.782 ? 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:	5.859 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.905 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.733 ? 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
NPO17459	Rheedia calcicola	Species	Clusiaceae	Eukaryota	n.a.	Madagascar rain forest	n.a.	PMID[17348706]
NPO17459	Rheedia calcicola	Species	Clusiaceae	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	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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[21067210]

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 NPC48949 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	9364
0.1-0.2	38874
0.2-0.3	1481
0.3-0.4	86
0.4-0.5	19
0.5-0.6	21
0.6-0.7	9
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	Natural Product ID
0.7681	Intermediate Similarity	NPC289358
0.7681	Intermediate Similarity	NPC4289
0.7681	Intermediate Similarity	NPC42384
0.7067	Intermediate Similarity	NPC5014
0.6986	Remote Similarity	NPC198803
0.6933	Remote Similarity	NPC23667
0.6933	Remote Similarity	NPC157284
0.65	Remote Similarity	NPC482618
0.6494	Remote Similarity	NPC482621
0.642	Remote Similarity	NPC482617
0.642	Remote Similarity	NPC482616
0.6329	Remote Similarity	NPC25736
0.6164	Remote Similarity	NPC149773
0.5949	Remote Similarity	NPC165191
0.5949	Remote Similarity	NPC177501
0.5823	Remote Similarity	NPC114333
0.5823	Remote Similarity	NPC28592
0.5823	Remote Similarity	NPC51531
0.575	Remote Similarity	NPC473479
0.575	Remote Similarity	NPC50615
0.575	Remote Similarity	NPC141650
0.5556	Remote Similarity	NPC30846
0.5405	Remote Similarity	NPC259400
0.5405	Remote Similarity	NPC130591
0.5405	Remote Similarity	NPC234637
0.5375	Remote Similarity	NPC46242
0.5375	Remote Similarity	NPC91887
0.5375	Remote Similarity	NPC93556
0.5309	Remote Similarity	NPC297797
0.5181	Remote Similarity	NPC469857
0.5181	Remote Similarity	NPC245760
0.5059	Remote Similarity	NPC471971
0.5059	Remote Similarity	NPC471972
0.5059	Remote Similarity	NPC469855

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC48949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5014
0.1-0.2	4121
0.2-0.3	15
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