NPASS Compound

Natural Product: NPC473665

Natural Product ID	NPC473665
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Vaticanol G
IUPAC Name	n.a.
Synonyms	Vaticanol G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448529
PubChem CID	44566410
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

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 83 91 0 0 0 0 0 0 0 0999 V2000 -2.2900 -0.1644 2.6279 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6643 -0.6854 3.8338 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -1.8604 3.9295 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7158 -2.5318 2.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3277 -1.9873 1.5817 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6173 -0.8121 1.4498 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 -0.2938 0.1066 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9710 -0.7008 -0.4629 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1383 -1.7621 0.0818 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9116 -1.4944 1.0692 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1810 -0.9572 0.9801 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0047 -0.8338 2.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5774 -1.2497 3.3348 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3095 -1.7945 3.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5251 -1.8985 2.3314 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3947 -1.1307 4.4568 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9325 -0.4561 -0.1910 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1572 -0.2753 -1.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6187 -1.6137 -1.7829 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6261 -2.2833 -1.1257 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2420 -3.5207 -1.5527 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8662 -4.1033 -2.6657 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8641 -3.4011 -3.3066 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2534 -2.1523 -2.8773 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4918 -3.9672 -4.4119 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7639 -4.1885 -0.8785 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0626 0.6988 -1.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4907 1.9967 -1.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6650 3.0829 -1.3645 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6053 2.8718 -0.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0884 1.6215 -0.5676 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2178 0.5385 -0.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3921 1.1571 -0.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4443 1.5639 -0.9793 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6729 0.8430 -2.1148 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6838 1.2516 -2.9998 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4515 2.3677 -2.7449 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2198 3.0990 -1.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2289 2.6868 -0.7393 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0068 4.2272 -1.3510 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8857 0.4832 -4.1536 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4540 3.9545 -0.7144 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7859 2.1442 -2.0131 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7798 0.6805 0.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3344 1.7216 1.0310 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1708 2.7392 1.3637 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4724 2.7869 0.9118 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9461 1.7915 0.1081 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0996 0.7597 -0.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2713 3.8740 1.3021 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7392 -2.3653 5.1724 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7165 0.7778 2.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3828 -0.1366 4.7426 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2730 -3.4534 2.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6211 -2.5548 0.6852 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 -0.7571 -0.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2466 -1.0394 -1.5761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7407 -2.6819 0.3841 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0026 -0.4168 2.0521 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9534 -2.1280 4.4265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4441 -2.3416 2.4689 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6012 -0.1888 4.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6655 -1.3141 -0.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8541 0.0914 -2.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5353 -5.0837 -2.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0319 -1.5767 -3.3575 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2220 -4.6436 -4.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5374 -4.7960 -0.1000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0357 4.0882 -1.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5800 1.6672 0.9772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1317 -0.0419 -2.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2390 2.6713 -3.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0370 3.2512 0.1663 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1528 4.5997 -0.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5400 0.8502 -4.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3968 4.7961 -1.2670 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0294 2.0837 -2.9891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3157 1.6952 1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7786 3.5212 2.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9710 1.8500 -0.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4803 -0.0344 -0.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2813 3.7944 1.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5138 -3.0072 5.2994 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 13 16 1 0 11 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 21 26 1 0 18 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 38 40 1 0 36 41 1 0 30 42 1 0 28 43 1 0 17 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 47 50 1 0 3 51 1 0 6 1 1 0 33 7 1 0 32 8 1 0 20 9 1 0 15 10 1 0 24 19 1 0 32 27 1 0 39 34 1 0 49 44 1 0 1 52 1 0 2 53 1 0 4 54 1 0 5 55 1 0 7 56 1 0 8 57 1 0 9 58 1 0 12 59 1 0 14 60 1 0 15 61 1 0 16 62 1 0 17 63 1 0 18 64 1 0 22 65 1 0 24 66 1 0 25 67 1 0 26 68 1 0 29 69 1 0 33 70 1 0 35 71 1 0 37 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 42 76 1 0 43 77 1 0 45 78 1 0 46 79 1 0 48 80 1 0 49 81 1 0 50 82 1 0 51 83 1 0 M END

Standard InCHIKey	FWPQMKZSFDFHKZ-NDCCRSDUSA-N
Standard InCHI	InChI=1S/C42H32O9/c43-21-5-1-18(2-6-21)33-28-14-23(45)9-10-27(28)37-36-29(15-26(48)16-30(36)49)38(33)40-32(51)17-31(50)39-35(20-11-24(46)13-25(47)12-20)34(41(37)42(39)40)19-3-7-22(44)8-4-19/h1-17,33-35,37-38,41,43-51H/t33-,34+,35+,37-,38+,41-/m1/s1
SMILES	C1=CC(=CC=C1C2C3C4C5=C(C=C(C=C5)O)C(C(C6=C4C(=CC(=C6)O)O)C7=C(C=C(C(=C37)C2C8=CC(=CC(=C8)O)O)O)O)C9=CC=C(C=C9)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	680.2	Volume:	689.635 ? Van der Waals volume.
Dense:	0.986	LogP:	3.355 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.929 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.719 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	47.0
TPSA:	182.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	9.0	Rings:	9.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.329	Fsp³:	0.143
MCE-18:	169.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.124 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.173 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.25 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.695	Promiscuous compounds:	0.194

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.795	MDCK Permeability:	-4.836
Pgp-inhibitor:	0.0	Pgp-substrate:	0.249
PAMPA:	0.101 ? 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%):	0.974	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.937
Plasma Protein Binding (PPB):	91.271%	Volume Distribution (VD):	-0.119
Fu:	12.793% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.149
BSEP inhibitor:	0.061

ADMET: Metabolism

CYP1A2-inhibitor:	0.961	CYP1A2-substrate:	0.02
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.978	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.234	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.83 ? 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):

1.405

Half-life (T1/2):

3.953

ADMET: Toxicity

hERG Blockers:	0.14	hERG Blockers (10um):	0.878
Human Hepatotoxicity (H-HT):	0.674	Drug-induced Liver Injury (DILI):	0.033
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	0.009
Carcinogencity:	0.913	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.923
Drug-induced Neurotoxicity:	0.316	Ototoxicity:	0.98
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.033
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.965	Hek293 Cytotoxicity:	0.999
BCF:	1.431 ? 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:	5.259 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.614 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.506 ? 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
NPO14000	Hopea exalata	Species	Dipterocarpaceae	Eukaryota	stem bark	Botanical Garden at Jianfeng Town, Ledong County, Hainan Province, China	2004-JUL	PMID[17190464]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	Barks	n.a.	n.a.	PMID[22209731]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26194	Shorea roxburghii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14000	Hopea exalata	Species	Dipterocarpaceae	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	3
Inhibition	3
MIC	6

Activity Type	# Activity
Individual protein	6
Organism	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual protein	Sucrase-isomaltase	Rattus norvegicus	IC50	>	400000.0	nM	PMID[26341134]
NPT462	Individual protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	=	37.8	%	Open TG-GATES in vivo data: Biochemistry
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	IC50	>	100000.0	nM	PMID[19813743]
NPT68	Individual protein	Aldose reductase	Rattus norvegicus	Inhibition	=	46.7	%	PMID[12880317]
NPT671	Individual protein	Acidic alpha-glucosidase	Rattus norvegicus	IC50	>	400000.0	nM	PMID[8277312]
NPT671	Individual protein	Acidic alpha-glucosidase	Rattus norvegicus	Inhibition	=	32.2	%	PMID[199729]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	MIC	=	0.78	ug.mL-1	PMID[23642481]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	>	50.0	ug.mL-1	PMID[12617583]
NPT2648	Organism	Fusarium oxysporum f. sp. vasinfectum	Fusarium oxysporum f. sp. vasinfectum	MIC	>	50.0	ug.mL-1	PMID[1517739]
NPT1199	Organism	Valsa mali	Valsa mali	MIC	>	50.0	ug.mL-1	PMID[25739048]
NPT2705	Organism	Alternaria solani	Alternaria solani	MIC	=	24.6	ug.mL-1	PMID[25739048]
NPT2637	Organism	Colletotrichum lagenarium	Colletotrichum lagenarium	MIC	>	50.0	ug.mL-1	PMID[12617583]

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 NPC473665 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	38215
0.1-0.2	11207
0.2-0.3	401
0.3-0.4	18
0.4-0.5	9
0.5-0.6	8
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	Natural Product ID
0.5862	Remote Similarity	NPC9292
0.5862	Remote Similarity	NPC145659
0.5342	Remote Similarity	NPC122980
0.5342	Remote Similarity	NPC148516
0.5342	Remote Similarity	NPC107862
0.5342	Remote Similarity	NPC177172
0.5128	Remote Similarity	NPC105073
0.5128	Remote Similarity	NPC224528

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7996
0.1-0.2	1121
0.2-0.3	32
0.3-0.4	1
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