NPASS Compound

Natural Product: NPC232523

Natural Product ID	NPC232523
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Methyl-5-{8(Z)-Pentadecenyl}Resorcinol
IUPAC Name	2-methyl-5-[(Z)-pentadec-8-enyl]benzene-1,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL470556
PubChem CID	6452209
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

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 60 60 0 0 0 0 0 0 0 0999 V2000 9.1429 1.4259 -1.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3481 0.1486 -1.2941 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1496 0.5529 -0.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2725 -0.6329 -0.1354 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1253 -0.2050 0.7013 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2187 0.8366 0.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1503 1.1018 1.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8906 0.9016 0.7893 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3611 0.3920 -0.4672 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6175 -0.9085 -0.2267 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5495 -0.7578 0.7239 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1792 -2.1263 0.8510 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3656 -2.1354 1.7741 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4729 -1.2256 1.3435 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0261 -1.5686 -0.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1114 -0.5990 -0.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8844 0.5976 -0.9757 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9544 1.4239 -1.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2531 1.1123 -0.8345 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3739 2.0513 -1.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4805 -0.0820 -0.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4117 -0.9132 0.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7830 -0.3812 0.1915 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7262 2.6415 -1.8781 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3833 2.2011 -1.8280 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5670 1.7581 -0.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8750 1.2695 -2.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9454 -0.5599 -0.6836 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9997 -0.3074 -2.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4186 1.0618 0.4774 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5170 1.2799 -1.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8932 -1.4178 0.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8901 -1.1170 -1.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5161 -1.0731 1.0462 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4910 0.2825 1.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9268 0.5238 -0.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8517 1.7755 -0.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4007 1.4941 2.0361 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1367 1.1292 1.5793 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6325 1.1614 -0.8916 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0758 0.2175 -1.2718 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3214 -1.3715 -1.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3683 -1.5961 0.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2456 -0.0023 0.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1605 -0.4169 1.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4036 -2.4977 -0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4113 -2.7907 1.2990 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7580 -3.1718 1.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0624 -1.8657 2.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1933 -0.1594 1.3455 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3023 -1.3469 2.0711 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2464 -1.4629 -0.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3829 -2.6124 -0.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8725 0.8398 -1.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3248 1.4931 -0.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3418 2.8593 -0.3628 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2621 2.4278 -2.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5840 -1.8420 0.5635 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0308 -0.7036 1.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3323 2.8903 -2.6330 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 2 0 8 9 1 0 9 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 2 0 17 18 1 0 18 19 2 0 19 20 1 0 19 21 1 0 21 22 2 0 21 23 1 0 18 24 1 0 22 16 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 0 5 35 1 0 6 36 1 0 6 37 1 0 7 38 1 0 8 39 1 0 9 40 1 0 9 41 1 0 10 42 1 0 10 43 1 0 11 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 17 54 1 0 20 55 1 0 20 56 1 0 20 57 1 0 22 58 1 0 23 59 1 0 24 60 1 0 M END

Standard InCHIKey	LDBPJTXLCRXBIJ-HJWRWDBZSA-N
Standard InCHI	InChI=1S/C22H36O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20-17-21(23)19(2)22(24)18-20/h8-9,17-18,23-24H,3-7,10-16H2,1-2H3/b9-8-
SMILES	CCCCCC/C=CCCCCCCCc1cc(c(C)c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	332.27	Volume:	387.546 ? Van der Waals volume.
Dense:	0.857	LogP:	8.644 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.895 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.802 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	7.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.307	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.374	Fsp³:	0.636
MCE-18:	7.0 ? 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:	0.857	Fluc inhibitor:	0.329 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.138 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.941	Promiscuous compounds:	0.026

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.032	MDCK Permeability:	-4.682
Pgp-inhibitor:	0.948	Pgp-substrate:	0.001
PAMPA:	0.0 ? 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):	0.01
20% Bioavailability (F20%):	0.846	30% Bioavailability (F30%):	0.952
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194	MRP1:	0.891
Plasma Protein Binding (PPB):	99.036%	Volume Distribution (VD):	0.308
Fu:	0.446% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.445
OATP1B3 inhibitor:	0.974	BCRP inhibitor:	0.805
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.996	CYP2C19-substrate:	0.993
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.22	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.052	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.034 ? 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):

5.26

Half-life (T1/2):

0.502

ADMET: Toxicity

hERG Blockers:	0.409	hERG Blockers (10um):	0.853
Human Hepatotoxicity (H-HT):	0.332	Drug-induced Liver Injury (DILI):	0.005
AMES Toxicity:	0.171	Rat Oral Acute Toxicity:	0.279
Maximum Recommended Daily Dose:	0.294	Skin Sensitization:	1.0
Carcinogencity:	0.049	Eye Corrosion:	0.984
Eye Irritation:	0.998	Respiratory Toxicity:	0.98
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.241
Hematotoxicity:	0.026	Drug-induced Nephrotoxicity:	0.182
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.954	Hek293 Cytotoxicity:	0.784
BCF:	1.453 ? 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:	5.0 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.111 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.717 ? 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
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12510	Aronia arbutifolia	Species	Rosaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	24.0	%	PMID[8021657]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC232523 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	27382
0.1-0.2	20298
0.2-0.3	1894
0.3-0.4	164
0.4-0.5	60
0.5-0.6	31
0.6-0.7	20
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
0.8684	High Similarity	NPC158253
0.775	Intermediate Similarity	NPC204901
0.7179	Intermediate Similarity	NPC146798
0.7179	Intermediate Similarity	NPC222522
0.7179	Intermediate Similarity	NPC106396
0.7179	Intermediate Similarity	NPC94351
0.7179	Intermediate Similarity	NPC168303
0.6923	Remote Similarity	NPC53051
0.6923	Remote Similarity	NPC24404
0.6923	Remote Similarity	NPC313030
0.6829	Remote Similarity	NPC488413
0.6829	Remote Similarity	NPC488412
0.6667	Remote Similarity	NPC71002
0.6667	Remote Similarity	NPC249828
0.641	Remote Similarity	NPC470700
0.641	Remote Similarity	NPC54844
0.641	Remote Similarity	NPC39097
0.641	Remote Similarity	NPC302681
0.641	Remote Similarity	NPC118286
0.641	Remote Similarity	NPC109691
0.6316	Remote Similarity	NPC59506
0.6279	Remote Similarity	NPC94139
0.6279	Remote Similarity	NPC302219
0.6279	Remote Similarity	NPC147284
0.6098	Remote Similarity	NPC39664
0.6047	Remote Similarity	NPC483454
0.6047	Remote Similarity	NPC162314
0.5909	Remote Similarity	NPC129373
0.5909	Remote Similarity	NPC242342
0.5909	Remote Similarity	NPC85479
0.5909	Remote Similarity	NPC488416
0.5897	Remote Similarity	NPC37802
0.5814	Remote Similarity	NPC196479
0.5714	Remote Similarity	NPC305603
0.5682	Remote Similarity	NPC166761
0.5641	Remote Similarity	NPC294186
0.5641	Remote Similarity	NPC147310
0.5641	Remote Similarity	NPC137415
0.5641	Remote Similarity	NPC166313
0.5641	Remote Similarity	NPC192032
0.5641	Remote Similarity	NPC24407
0.5641	Remote Similarity	NPC11280
0.5581	Remote Similarity	NPC55561
0.5556	Remote Similarity	NPC10588
0.5532	Remote Similarity	NPC210497
0.55	Remote Similarity	NPC244513
0.5435	Remote Similarity	NPC72947
0.5366	Remote Similarity	NPC488411
0.5366	Remote Similarity	NPC488410
0.5366	Remote Similarity	NPC488409
0.5349	Remote Similarity	NPC177420
0.525	Remote Similarity	NPC227458
0.5217	Remote Similarity	NPC284011
0.5208	Remote Similarity	NPC48730
0.5111	Remote Similarity	NPC487734
0.5106	Remote Similarity	NPC252105
0.5102	Remote Similarity	NPC483450
0.5098	Remote Similarity	NPC61033

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC232523 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6169
0.1-0.2	2853
0.2-0.3	119
0.3-0.4	5
0.4-0.5	4
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