NPASS Compound

Natural Product: NPC475393

Natural Product ID	NPC475393
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Pampulhamine
IUPAC Name	(1R)-1-[[3-[4-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]phenoxy]-4-methoxyphenyl]methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Synonyms	Pampulhamine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL504801
PubChem CID	13992155
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

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 90 95 0 0 0 0 0 0 0 0999 V2000 -0.1388 -1.1742 3.3451 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0110 -0.7355 2.0146 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0601 -0.9095 1.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2148 -1.5164 1.5954 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3015 -1.7216 0.7714 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2838 -1.3264 -0.5626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1189 -0.7269 -0.9822 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0135 -0.5085 -0.1771 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1304 0.1008 -0.6613 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3886 -0.4053 -0.7263 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7616 -1.2450 -1.7837 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0313 -1.7739 -1.8786 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9910 -1.4948 -0.9295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6445 -0.6686 0.1212 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3491 -0.1318 0.2136 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3515 -2.0755 -1.0654 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2629 -1.1212 -1.8447 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7481 -0.8800 -3.1536 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9077 0.4485 -3.6491 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2147 1.3711 -2.6379 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0589 1.3073 -1.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5636 0.0830 -1.0499 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3678 -0.0401 0.0894 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6759 1.0472 0.8731 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4666 0.9702 2.0078 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0098 -0.2732 2.4240 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1591 2.2746 0.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3590 2.4010 -0.6411 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4522 3.3866 1.2625 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9916 4.6756 0.9818 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4229 -1.5550 -1.4381 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4670 -0.4762 -1.5122 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4752 -0.9184 -2.4103 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.4657 -2.2898 -2.7854 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7925 -0.5193 -2.1035 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1166 -0.9240 -0.6656 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1669 -0.1650 0.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8757 0.0651 -0.2322 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0308 0.7873 0.5615 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4370 1.2879 1.8091 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5722 2.0208 2.6070 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2443 2.2650 2.1382 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7197 1.0549 2.2632 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5759 0.3143 1.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1092 1.5516 3.4951 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3750 1.3868 4.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0506 -0.6740 3.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3407 -2.2722 3.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7391 -0.9070 3.9685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2607 -1.8388 2.6334 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1630 -2.1954 1.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0127 -0.3809 -2.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0130 -1.4596 -2.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3049 -2.4246 -2.7063 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4013 -0.4530 0.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1454 0.5174 1.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8485 -2.2771 -0.1024 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3418 -3.0254 -1.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2285 -1.6821 -1.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9837 -1.6084 -3.8373 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4581 0.5243 -4.6380 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9938 0.7167 -3.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1301 2.3841 -3.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1970 0.9942 -2.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7611 -1.0031 0.3700 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2770 -1.1011 2.3396 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9481 -0.5356 1.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2430 -0.1888 3.5168 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9639 3.3510 -0.9285 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3442 5.0290 -0.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8847 4.7000 0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3519 5.3694 1.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8552 -2.5520 -1.1843 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0009 -1.6952 -2.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9672 0.3941 -2.0536 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2943 -2.4244 -3.5197 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6886 -3.0013 -1.9361 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5697 -2.6683 -3.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4983 -1.0728 -2.7583 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0118 0.5457 -2.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0637 -2.0123 -0.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1539 -0.6026 -0.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0111 1.0277 0.2918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3839 2.7980 1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6978 1.3279 1.9703 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7049 2.9564 2.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5810 0.1143 1.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5658 2.2855 4.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4237 0.4536 4.7086 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1567 1.3434 3.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 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 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 24 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 6 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 40 43 1 0 43 44 2 0 43 45 1 0 45 46 1 0 8 3 1 0 15 10 1 0 22 17 1 0 38 32 1 0 28 21 1 0 44 37 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 5 51 1 0 7 52 1 0 11 53 1 0 12 54 1 0 14 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 6 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 23 65 1 0 26 66 1 0 26 67 1 0 26 68 1 0 28 69 1 0 30 70 1 0 30 71 1 0 30 72 1 0 31 73 1 0 31 74 1 0 32 75 1 6 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 36 81 1 0 36 82 1 0 39 83 1 0 42 84 1 0 42 85 1 0 42 86 1 0 44 87 1 0 46 88 1 0 46 89 1 0 46 90 1 0 M END

Standard InCHIKey	IUALMDJBFWMRDF-ROJLCIKYSA-N
Standard InCHI	InChI=1S/C38H44N2O6/c1-40-16-14-27-21-35(43-4)37(45-6)23-30(27)32(40)18-25-9-12-33(41-2)38(19-25)46-28-10-7-24(8-11-28)17-31-29-22-36(44-5)34(42-3)20-26(29)13-15-39-31/h7-12,19-23,31-32,39H,13-18H2,1-6H3/t31-,32-/m1/s1
SMILES	COc1ccc(cc1Oc1ccc(cc1)C[C@H]1NCCc2c1cc(OC)c(c2)OC)C[C@H]1N(C)CCc2c1cc(OC)c(c2)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.32	Volume:	657.563 ? Van der Waals volume.
Dense:	0.949	LogP:	3.078 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.067 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.38 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	34.0
TPSA:	70.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.197	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.56	Fsp³:	0.368
MCE-18:	109.846 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.989	Fluc inhibitor:	0.088 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.428 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.882 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.582

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.983	MDCK Permeability:	-4.764
Pgp-inhibitor:	1.0	Pgp-substrate:	0.455
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):	0.003
20% Bioavailability (F20%):	0.259	30% Bioavailability (F30%):	0.019
50% Bioavailability (F50%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.892
Plasma Protein Binding (PPB):	67.612%	Volume Distribution (VD):	0.181
Fu:	28.28% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.971
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.903	CYP2C8-inhibitor:	0.203
HLM stability:	0.977 ? 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):

10.265

Half-life (T1/2):

2.334

ADMET: Toxicity

hERG Blockers:	0.926	hERG Blockers (10um):	0.744
Human Hepatotoxicity (H-HT):	0.964	Drug-induced Liver Injury (DILI):	0.723
AMES Toxicity:	0.751	Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.986	Skin Sensitization:	0.316
Carcinogencity:	0.307	Eye Corrosion:	0.0
Eye Irritation:	0.026	Respiratory Toxicity:	0.533
Drug-induced Neurotoxicity:	0.982	Ototoxicity:	0.935
Hematotoxicity:	0.176	Drug-induced Nephrotoxicity:	0.667
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.086
A549 Cytotoxicity:	0.15	Hek293 Cytotoxicity:	0.871
BCF:	2.275 ? 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:	4.594 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.218 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.474 ? 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
NPO31148	Aristolochia gigantea	Species	Aristolochiaceae	Eukaryota	n.a.	stem	n.a.	PMID[21178901]
NPO31148	Aristolochia gigantea	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8676127]

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
Ratio IC50	2

Activity Type	# Activity
Individual protein	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1073	Individual protein	Dopamine transporter	Rattus norvegicus	IC50	=	84200.0	nM	PMID[18177008]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Ratio IC50	>	1.2	n.a.	PMID[23398362]

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 NPC475393 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	34687
0.1-0.2	14460
0.2-0.3	459
0.3-0.4	125
0.4-0.5	64
0.5-0.6	36
0.6-0.7	15
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
0.7821	Intermediate Similarity	NPC323537
0.7531	Intermediate Similarity	NPC239584
0.7375	Intermediate Similarity	NPC475479
0.7375	Intermediate Similarity	NPC243454
0.7353	Intermediate Similarity	NPC247639
0.7353	Intermediate Similarity	NPC25084
0.6941	Remote Similarity	NPC11296
0.6941	Remote Similarity	NPC281581
0.6941	Remote Similarity	NPC274661
0.6941	Remote Similarity	NPC82457
0.6329	Remote Similarity	NPC603603
0.6264	Remote Similarity	NPC48490
0.6203	Remote Similarity	NPC276890
0.6087	Remote Similarity	NPC60295
0.6076	Remote Similarity	NPC76682
0.6076	Remote Similarity	NPC10908
0.6076	Remote Similarity	NPC63646
0.6076	Remote Similarity	NPC317145
0.6076	Remote Similarity	NPC198498
0.6076	Remote Similarity	NPC115284
0.6022	Remote Similarity	NPC175890
0.5854	Remote Similarity	NPC12424
0.5854	Remote Similarity	NPC129518
0.5854	Remote Similarity	NPC251580
0.5797	Remote Similarity	NPC213206
0.5797	Remote Similarity	NPC188163
0.5797	Remote Similarity	NPC328750
0.5783	Remote Similarity	NPC603853
0.5745	Remote Similarity	NPC191132
0.5732	Remote Similarity	NPC227060
0.5714	Remote Similarity	NPC290582
0.5714	Remote Similarity	NPC217748
0.5714	Remote Similarity	NPC73492
0.5714	Remote Similarity	NPC182052
0.5714	Remote Similarity	NPC271013
0.5714	Remote Similarity	NPC299990
0.5714	Remote Similarity	NPC42663
0.5714	Remote Similarity	NPC15414
0.5696	Remote Similarity	NPC475215
0.5647	Remote Similarity	NPC279228
0.5581	Remote Similarity	NPC311973
0.557	Remote Similarity	NPC317272
0.557	Remote Similarity	NPC268503
0.5529	Remote Similarity	NPC480587
0.5517	Remote Similarity	NPC116465
0.55	Remote Similarity	NPC30779
0.5429	Remote Similarity	NPC314682
0.5402	Remote Similarity	NPC286119
0.5402	Remote Similarity	NPC239824
0.5341	Remote Similarity	NPC254441
0.5333	Remote Similarity	NPC195538
0.5238	Remote Similarity	NPC41376
0.5181	Remote Similarity	NPC256012
0.5181	Remote Similarity	NPC610965
0.5149	Remote Similarity	NPC256124
0.5116	Remote Similarity	NPC240841
0.5111	Remote Similarity	NPC229373

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4790
0.1-0.2	4246
0.2-0.3	101
0.3-0.4	7
0.4-0.5	2
0.5-0.6	3
0.6-0.7	1
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
0.6076	Remote Similarity	NPD8099	Discontinued
0.5797	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD8156	Discontinued
0.5714	Remote Similarity	NPD8095	Phase 1

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