NPASS Compound

Natural Product: NPC246967

Natural Product ID	NPC246967
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Geranylgeranyl-2,4-Dihydroxy-1-Methoxybenzene
IUPAC Name	4-methoxy-5-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]benzene-1,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL484444
PubChem CID	14487957
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 70 70 0 0 0 0 0 0 0 0999 V2000 9.6555 -0.3647 -2.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3121 -0.8251 -0.6721 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1017 -1.2621 -0.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6329 -1.7476 0.8921 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6421 -0.8321 1.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4217 -0.5190 0.7761 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2410 -0.8649 1.2404 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0053 -0.5214 0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2256 0.4186 1.3260 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9639 0.9229 0.7544 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2117 0.7200 1.3450 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4923 1.2244 0.7828 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 0.0861 0.5798 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7528 0.5583 0.0176 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8629 0.3566 0.7194 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1523 0.8251 0.1705 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1459 -0.2171 -0.0965 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8650 -1.5208 -0.3905 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9028 -2.4144 -0.6322 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2172 -1.9912 -0.5768 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5216 -0.6793 -0.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4932 0.1875 -0.0453 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7993 1.4979 0.2524 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9300 2.5410 -0.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8518 -0.2531 -0.2246 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6156 -3.7187 -0.9256 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8753 1.2260 -1.2902 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0388 1.6862 -0.5133 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4934 0.2493 -0.4795 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3950 -0.7579 0.3792 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0973 0.6590 -2.0384 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3835 -1.0636 -2.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7083 -0.2806 -2.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4016 -1.2838 -1.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2524 -2.7906 0.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5422 -1.8510 1.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1073 0.1474 1.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3659 -1.2741 2.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1447 -1.3842 2.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2279 -0.0587 -0.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4480 -1.4457 0.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9289 1.2347 1.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9725 -0.0840 2.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1903 0.1449 2.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2931 1.7741 -0.1562 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9004 1.9738 1.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6620 -0.3558 1.5753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0087 -0.7321 -0.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8823 -0.1401 1.6814 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0649 1.5573 -0.6591 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6009 1.4493 1.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8167 -1.7976 -0.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0662 -2.6588 -0.7608 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5267 2.2551 -1.6774 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3906 3.4462 -0.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9745 2.8371 -0.7971 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0912 0.6687 0.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0681 -4.3570 -0.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9849 1.0837 -1.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6987 0.7013 -1.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0971 2.3017 -1.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4993 2.6738 -0.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6695 1.1720 -1.3983 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0987 1.9881 -0.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8099 1.1414 -0.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2724 -0.2808 -1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5103 0.7349 -0.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4682 -1.7187 0.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0674 0.0701 1.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3659 -0.4682 -0.0594 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 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 21 25 1 0 19 26 1 0 14 27 1 0 10 28 1 0 6 29 1 0 2 30 1 0 22 17 1 0 1 31 1 0 1 32 1 0 1 33 1 0 3 34 1 0 4 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 7 39 1 0 8 40 1 0 8 41 1 0 9 42 1 0 9 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 15 49 1 0 16 50 1 0 16 51 1 0 18 52 1 0 20 53 1 0 24 54 1 0 24 55 1 0 24 56 1 0 25 57 1 0 26 58 1 0 27 59 1 0 27 60 1 0 27 61 1 0 28 62 1 0 28 63 1 0 28 64 1 0 29 65 1 0 29 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 30 70 1 0 M END

Standard InCHIKey	IYYFMQHGUZBMKD-MLAGYPMBSA-N
Standard InCHI	InChI=1S/C27H40O3/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-24-18-25(28)19-26(29)27(24)30-6/h10,12,14,16,18-19,28-29H,7-9,11,13,15,17H2,1-6H3/b21-12+,22-14+,23-16+
SMILES	CC(=CCC/C(=C/CC/C(=C/CC/C(=C/Cc1cc(cc(c1OC)O)O)/C)/C)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.3	Volume:	474.907 ? Van der Waals volume.
Dense:	0.868	LogP:	8.379 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.677 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.929 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	10.0
TPSA:	49.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.344	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.089	Fsp³:	0.481
MCE-18:	11.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.924	Fluc inhibitor:	0.195 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.115 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.677	Promiscuous compounds:	0.281

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.813	MDCK Permeability:	-4.728
Pgp-inhibitor:	0.999	Pgp-substrate:	0.0
PAMPA:	0.001 ? 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):	0.001
20% Bioavailability (F20%):	0.022	30% Bioavailability (F30%):	0.032
50% Bioavailability (F50%):	0.831

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.977
Plasma Protein Binding (PPB):	96.972%	Volume Distribution (VD):	0.187
Fu:	2.537% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.0
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.954	CYP2C19-substrate:	0.556
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.229
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.189	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

3.734

Half-life (T1/2):

1.336

ADMET: Toxicity

hERG Blockers:	0.183	hERG Blockers (10um):	0.734
Human Hepatotoxicity (H-HT):	0.812	Drug-induced Liver Injury (DILI):	0.073
AMES Toxicity:	0.059	Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.608	Skin Sensitization:	0.99
Carcinogencity:	0.117	Eye Corrosion:	0.0
Eye Irritation:	0.698	Respiratory Toxicity:	0.976
Drug-induced Neurotoxicity:	0.526	Ototoxicity:	0.494
Hematotoxicity:	0.207	Drug-induced Nephrotoxicity:	0.431
Genotoxicity:	0.488	RPMI-8226 Immunitoxicity:	0.126
A549 Cytotoxicity:	0.579	Hek293 Cytotoxicity:	0.63
BCF:	2.059 ? 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:	5.541 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.063 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.308 ? 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
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575963]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1294697]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607355]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2809609]
NPO2678	Synadenium pereskiifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19582	Sarothamnus patens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19221	Echinopsis terscheckii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17795	Corydalis montana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17408	Derris amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18683	Diospyros cornii	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19025	Pemphis acidula	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17408	Derris amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17408	Derris amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17795	Corydalis montana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27847	Suillus granulatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17795	Corydalis montana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19025	Pemphis acidula	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2678	Synadenium pereskiifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18683	Diospyros cornii	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19582	Sarothamnus patens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19221	Echinopsis terscheckii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17408	Derris amazonica	Species	Fabaceae	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
MIC	8
IC50	3

Activity Type	# Activity
Cell line	2
Organism	8
Non-molecular	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[1294697]
NPT168	Cell line	P388	Mus musculus	IC50	=	2.1	ug.mL-1	PMID[1294697]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	100.0	ug.mL-1	PMID[2607355]
NPT4678	Organism	Hafnia alvei	Hafnia alvei	MIC	>	100.0	ug.mL-1	PMID[2607355]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[2607355]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[2607355]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2.2	ug.mL-1	PMID[1294697]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[2607355]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	100.0	ug.mL-1	PMID[2607355]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.56	ug.mL-1	PMID[2607355]
NPT1843	Organism	Aeromonas hydrophila	Aeromonas hydrophila	MIC	=	0.78	ug.mL-1	PMID[2607355]

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 NPC246967 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	15977
0.1-0.2	28661
0.2-0.3	4673
0.3-0.4	434
0.4-0.5	99
0.5-0.6	11
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8163	Intermediate Similarity	NPC147317
0.5614	Remote Similarity	NPC474810
0.5556	Remote Similarity	NPC324362
0.5536	Remote Similarity	NPC474864
0.5333	Remote Similarity	NPC605455
0.5283	Remote Similarity	NPC260775
0.5283	Remote Similarity	NPC130756
0.5283	Remote Similarity	NPC70677
0.5283	Remote Similarity	NPC12931
0.5192	Remote Similarity	NPC12640
0.5167	Remote Similarity	NPC610519
0.5091	Remote Similarity	NPC474612

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4104
0.1-0.2	4964
0.2-0.3	76
0.3-0.4	5
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