NPASS Compound

Natural Product: NPC116274

Natural Product ID	NPC116274
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YZIYZGORSQUAAQ-PJUUHHLVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46216837
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

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 93 96 0 0 0 0 0 0 0 0999 V2000 5.1473 -0.8081 -1.4829 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0367 -1.5958 -0.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5569 -1.0730 0.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0744 0.2550 1.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6703 0.5987 1.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5696 0.3348 0.5415 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9598 1.0340 -0.8001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3403 1.2246 0.9408 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8266 2.5358 1.4512 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3592 3.4261 1.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4480 4.5902 1.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5847 5.5062 1.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5765 5.0245 0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6432 1.3797 -0.1528 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8302 0.2431 -1.0899 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1378 0.7195 -2.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3554 1.5420 -2.5777 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3356 2.7642 -3.0742 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5883 3.5818 -3.1692 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0804 3.3582 -3.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9765 -0.5946 -0.5608 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6731 -1.2542 0.5328 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9246 -1.9691 0.9463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7571 -1.9539 -0.2846 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2396 -1.8434 -0.0339 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9221 -1.8378 -1.3944 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6692 -3.1186 0.6613 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5719 -0.7498 0.7219 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2525 -0.8089 -0.9793 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3262 -1.1951 1.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3072 -1.3520 2.3573 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9377 -0.9618 0.2700 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6595 -2.2169 0.2253 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9069 -2.6402 -0.9871 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1497 -3.1087 1.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2000 -2.8325 2.5860 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6237 -3.7679 3.5391 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0155 -5.0248 3.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9815 -5.3354 1.8300 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5646 -4.4127 0.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2962 -0.7101 -1.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6952 -1.2486 -2.0539 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5015 -3.0183 -0.3073 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5118 0.1965 -1.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2037 -0.8392 -2.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9073 -1.2652 -2.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5848 -1.7687 1.7525 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4718 0.9192 0.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7584 0.6607 1.9845 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7291 1.7641 1.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4172 0.3689 2.5295 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2016 1.7292 -1.1507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8707 1.6630 -0.6259 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2142 0.3245 -1.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1489 0.7183 1.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 2.4471 2.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4650 3.0311 0.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0341 3.0181 2.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5135 5.2000 0.9778 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3860 6.5448 1.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7874 5.5226 2.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5501 5.0567 0.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3436 6.0373 -0.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7271 4.3741 -0.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5455 2.3694 -0.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6579 1.5115 0.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2715 1.2760 -2.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2533 -0.1693 -3.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3045 1.1432 -2.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8778 3.9232 -2.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4105 2.9348 -3.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4324 4.4701 -3.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5606 2.6961 -4.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4150 3.5495 -2.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2570 4.3670 -4.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6997 -2.9782 1.3248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4251 -1.3897 1.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5071 -2.8335 -0.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3566 -1.1729 -2.0830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9729 -1.5117 -1.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9315 -2.8407 -1.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3477 -3.1712 1.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1876 -3.9575 0.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7674 -3.2499 0.5503 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1616 -1.0404 1.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9626 -1.8642 2.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -3.5089 4.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3511 -5.7802 3.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2880 -6.3220 1.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5489 -4.6904 -0.1278 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4506 -3.5188 0.6763 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5263 -3.0370 -0.7321 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8509 -3.5939 -0.9976 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 1 0 24 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 24 29 1 0 22 30 1 0 30 31 2 0 30 32 1 0 32 33 1 6 33 34 2 0 33 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 32 41 1 0 41 42 2 0 2 43 1 0 32 6 1 0 40 35 1 0 41 15 1 0 29 21 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 4 48 1 0 4 49 1 0 5 50 1 0 5 51 1 0 7 52 1 0 7 53 1 0 7 54 1 0 8 55 1 1 9 56 1 0 9 57 1 0 10 58 1 0 12 59 1 0 12 60 1 0 12 61 1 0 13 62 1 0 13 63 1 0 13 64 1 0 14 65 1 0 14 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 19 70 1 0 19 71 1 0 19 72 1 0 20 73 1 0 20 74 1 0 20 75 1 0 23 76 1 0 23 77 1 0 24 78 1 6 26 79 1 0 26 80 1 0 26 81 1 0 27 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 36 86 1 0 37 87 1 0 38 88 1 0 39 89 1 0 40 90 1 0 43 91 1 0 43 92 1 0 43 93 1 0 M END

Standard InCHIKey	YZIYZGORSQUAAQ-PJUUHHLVSA-N
Standard InCHI	InChI=1S/C38H50O5/c1-24(2)14-13-20-36(9)28(18-17-25(3)4)23-37(21-19-26(5)6)33-29(22-30(43-33)35(7,8)42)32(40)38(36,34(37)41)31(39)27-15-11-10-12-16-27/h10-12,14-17,19,28,30,42H,13,18,20-23H2,1-9H3/t28-,30-,36+,37+,38-/m0/s1
SMILES	CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(CC=C(C)C)C3=C(C[C@@H](C(C)(C)O)O3)C(=O)[C@@]1(C(=O)c1ccccc1)C2=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	586.37	Volume:	649.165 ? Van der Waals volume.
Dense:	0.903	LogP:	7.108 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.058 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.998 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	26.0
TPSA:	80.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.169	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.784	Fsp³:	0.553
MCE-18:	113.305 ? 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:	0
Colloidal aggregators:	0.944	Fluc inhibitor:	0.091 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.045 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.628 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.346	Promiscuous compounds:	0.022

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.613	MDCK Permeability:	-4.692
Pgp-inhibitor:	0.029	Pgp-substrate:	0.472
PAMPA:	0.439 ? 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%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999	MRP1:	0.988
Plasma Protein Binding (PPB):	82.91%	Volume Distribution (VD):	-0.02
Fu:	17.747% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.679
OATP1B3 inhibitor:	0.02	BCRP inhibitor:	0.004
BSEP inhibitor:	0.942

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.996
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.706 ? 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):

5.029

Half-life (T1/2):

0.786

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.182
Human Hepatotoxicity (H-HT):	0.889	Drug-induced Liver Injury (DILI):	0.294
AMES Toxicity:	0.353	Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.18	Skin Sensitization:	0.998
Carcinogencity:	0.954	Eye Corrosion:	0.0
Eye Irritation:	0.378	Respiratory Toxicity:	0.873
Drug-induced Neurotoxicity:	0.313	Ototoxicity:	0.518
Hematotoxicity:	0.31	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.971	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.025	Hek293 Cytotoxicity:	0.17
BCF:	2.031 ? 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:	5.419 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.341 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.215 ? 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
NPO40864	Hypericum uralum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26583263]
NPO40864	Hypericum uralum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27148858]
NPO40864	Hypericum uralum	Species	Hypericaceae	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
Activity	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
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	57.0	%	PMID[27148858]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	74.4	%	PMID[27148858]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	72.2	%	PMID[27148858]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	77.7	%	PMID[27148858]
NPT681	Cell line	PC-12	Rattus norvegicus	Activity	=	69.9	%	PMID[27148858]

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 NPC116274 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	9148
0.1-0.2	38905
0.2-0.3	1602
0.3-0.4	112
0.4-0.5	37
0.5-0.6	37
0.6-0.7	4
0.7-0.8	0
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC47466
0.8592	High Similarity	NPC483077
0.8382	Intermediate Similarity	NPC328997
0.8382	Intermediate Similarity	NPC294050
0.8382	Intermediate Similarity	NPC610705
0.8286	Intermediate Similarity	NPC482993
0.8194	Intermediate Similarity	NPC146239
0.8194	Intermediate Similarity	NPC483095
0.7407	Intermediate Similarity	NPC144257
0.7297	Intermediate Similarity	NPC482995
0.7162	Intermediate Similarity	NPC61651
0.7105	Intermediate Similarity	NPC483079
0.6329	Remote Similarity	NPC482994
0.6282	Remote Similarity	NPC316553
0.6184	Remote Similarity	NPC483060
0.6	Remote Similarity	NPC325740
0.5976	Remote Similarity	NPC483098
0.5949	Remote Similarity	NPC483061
0.5949	Remote Similarity	NPC483062
0.5946	Remote Similarity	NPC472729
0.5946	Remote Similarity	NPC472730
0.5904	Remote Similarity	NPC483097
0.5904	Remote Similarity	NPC483096
0.5875	Remote Similarity	NPC482999
0.5802	Remote Similarity	NPC482998
0.5802	Remote Similarity	NPC482997
0.5802	Remote Similarity	NPC482996
0.5789	Remote Similarity	NPC472728
0.5789	Remote Similarity	NPC472727
0.5733	Remote Similarity	NPC472733
0.5733	Remote Similarity	NPC472734
0.5714	Remote Similarity	NPC471334
0.5663	Remote Similarity	NPC483065
0.561	Remote Similarity	NPC483000
0.5568	Remote Similarity	NPC273798
0.5529	Remote Similarity	NPC483092
0.5529	Remote Similarity	NPC483093
0.5513	Remote Similarity	NPC471331
0.5513	Remote Similarity	NPC99657
0.5513	Remote Similarity	NPC203388
0.5465	Remote Similarity	NPC483099
0.5455	Remote Similarity	NPC483058
0.5385	Remote Similarity	NPC472732
0.5385	Remote Similarity	NPC472731
0.5375	Remote Similarity	NPC483066
0.5341	Remote Similarity	NPC483094
0.5309	Remote Similarity	NPC260886
0.525	Remote Similarity	NPC483064
0.525	Remote Similarity	NPC483063
0.5185	Remote Similarity	NPC471330
0.5185	Remote Similarity	NPC472687
0.5057	Remote Similarity	NPC471333
0.5057	Remote Similarity	NPC471332

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC116274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3286
0.1-0.2	5818
0.2-0.3	46
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