NPASS Compound

Natural Product: NPC247389

Natural Product ID	NPC247389
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GDVPELGSXTWKDA-ZDUSSCGKSA-N
IUPAC Name	n.a.
Synonyms	O-Methylbulbocapnine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL464955
PubChem CID	10246564
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

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 46 50 0 0 0 0 0 0 0 0999 V2000 3.2459 -0.9099 1.3422 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3009 -1.2264 -0.0455 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2640 -0.5134 -0.8059 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7014 0.4696 -1.7631 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3647 0.9820 -1.4042 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0102 2.2755 -1.6158 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7499 2.7250 -1.2870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1895 1.8651 -0.7310 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1793 0.5500 -0.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7099 -0.3913 0.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2331 -1.6500 0.4463 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0718 -2.5627 1.1207 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3231 -2.1928 1.4676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7893 -0.9381 1.1663 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9684 -0.0088 0.4872 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6219 1.1582 0.2469 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5996 1.1955 -0.8466 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0827 -0.6202 1.5495 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8922 -1.5424 2.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1003 -2.1250 0.0966 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9775 -1.2622 -0.6706 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4482 0.1003 -0.8512 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3105 2.5994 -0.5101 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9699 3.9689 -0.5409 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1621 3.9864 -1.4074 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3824 -0.3052 1.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3381 -1.8536 1.9300 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1681 -0.3171 1.6084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8696 -1.2645 -1.3866 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9841 -0.0192 -0.1038 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6546 0.0860 -2.8160 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3849 1.3662 -1.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6997 2.9969 -2.0482 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6720 -3.5599 1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9387 -2.9302 1.9929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1190 1.0302 -1.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9959 2.2237 -0.8173 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4104 0.4961 -0.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9153 -1.0758 2.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9585 -2.4987 1.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4807 -1.8169 3.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9419 -3.1411 -0.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5653 -2.4763 1.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1659 -1.7338 -1.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8012 4.5826 -0.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6053 4.2782 0.4561 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 2 0 7 8 1 0 8 9 2 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 15 16 1 0 16 17 1 0 14 18 1 0 18 19 1 0 11 20 1 0 20 21 1 0 21 22 1 0 8 23 1 0 23 24 1 0 24 25 1 0 21 2 1 0 22 5 2 0 25 7 1 0 22 9 1 0 15 10 1 0 1 26 1 0 1 27 1 0 1 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 6 33 1 0 12 34 1 0 13 35 1 0 17 36 1 0 17 37 1 0 17 38 1 0 19 39 1 0 19 40 1 0 19 41 1 0 20 42 1 0 20 43 1 0 21 44 1 6 24 45 1 0 24 46 1 0 M END

Standard InCHIKey	GDVPELGSXTWKDA-ZDUSSCGKSA-N
Standard InCHI	InChI=1S/C20H21NO4/c1-21-7-6-12-9-15-20(25-10-24-15)18-16(12)13(21)8-11-4-5-14(22-2)19(23-3)17(11)18/h4-5,9,13H,6-8,10H2,1-3H3/t13-/m0/s1
SMILES	CN1CCc2cc3c(c4-c5c(ccc(c5OC)OC)C[C@H]1c24)OCO3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	339.15	Volume:	342.033 ? Van der Waals volume.
Dense:	0.992	LogP:	2.32 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.395 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.303 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	24.0
TPSA:	40.16 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.84	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.171	Fsp³:	0.4
MCE-18:	87.286 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.516	Fluc inhibitor:	0.037 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.77 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.405 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.004	Promiscuous compounds:	0.604

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.741	MDCK Permeability:	-4.732
Pgp-inhibitor:	0.177	Pgp-substrate:	0.362
PAMPA:	0.041 ? 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):	0.012
20% Bioavailability (F20%):	0.226	30% Bioavailability (F30%):	0.122
50% Bioavailability (F50%):	0.874

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.944	MRP1:	0.934
Plasma Protein Binding (PPB):	73.912%	Volume Distribution (VD):	0.35
Fu:	27.726% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.498
OATP1B3 inhibitor:	0.744	BCRP inhibitor:	0.342
BSEP inhibitor:	0.837

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.013
CYP2C9-inhibitor:	0.962	CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.979
CYP3A4-inhibitor:	0.988	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	0.0
HLM stability:	0.052 ? 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):

7.201

Half-life (T1/2):

2.224

ADMET: Toxicity

hERG Blockers:	0.499	hERG Blockers (10um):	0.68
Human Hepatotoxicity (H-HT):	0.562	Drug-induced Liver Injury (DILI):	0.086
AMES Toxicity:	0.712	Rat Oral Acute Toxicity:	0.698
Maximum Recommended Daily Dose:	0.913	Skin Sensitization:	0.436
Carcinogencity:	0.868	Eye Corrosion:	0.001
Eye Irritation:	0.131	Respiratory Toxicity:	0.918
Drug-induced Neurotoxicity:	0.892	Ototoxicity:	0.313
Hematotoxicity:	0.21	Drug-induced Nephrotoxicity:	0.414
Genotoxicity:	0.866	RPMI-8226 Immunitoxicity:	0.082
A549 Cytotoxicity:	0.183	Hek293 Cytotoxicity:	0.354
BCF:	2.087 ? 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:	4.215 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.12 ? 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
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO23076	Illigera luzonensis	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214740]
NPO23076	Illigera luzonensis	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22727	Avena fatua	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21569	Helichrysum fulvum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16798	Piper sylvaticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2204	Lindera megaphylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16798	Piper sylvaticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23076	Illigera luzonensis	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22727	Avena fatua	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21569	Helichrysum fulvum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	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
Activity	14

Activity Type	# Activity
Cell line	2
Non-molecular	8
Tissue	4

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	47.9	%	PMID[9214740]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[9214740]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	75.1	%	PMID[9214740]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	50.4	%	PMID[9214740]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	72.5	%	PMID[9214740]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	83.4	%	PMID[9214740]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	22.9	%	DOI[10.1021/np50123a013]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	68.1	%	DOI[10.1021/np50123a013]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	55.2	%	DOI[10.1021/np50123a013]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	88.5	%	DOI[10.1021/np50123a013]
NPT20967	Cell line	Platelet	n.a.	Activity	=	73.0	%	DOI[10.1021/np50123a013]
NPT20967	Cell line	Platelet	n.a.	Activity	=	60.8	%	DOI[10.1021/np50123a013]

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 NPC247389 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	33861
0.1-0.2	14520
0.2-0.3	1156
0.3-0.4	234
0.4-0.5	48
0.5-0.6	13
0.6-0.7	15
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
0.8	Intermediate Similarity	NPC219341
0.746	Intermediate Similarity	NPC320223
0.7231	Intermediate Similarity	NPC114364
0.7143	Intermediate Similarity	NPC266753
0.7143	Intermediate Similarity	NPC160298
0.7097	Intermediate Similarity	NPC63997
0.7097	Intermediate Similarity	NPC16805
0.7097	Intermediate Similarity	NPC167546
0.6923	Remote Similarity	NPC600118
0.6825	Remote Similarity	NPC306902
0.6825	Remote Similarity	NPC232924
0.6667	Remote Similarity	NPC610764
0.6615	Remote Similarity	NPC476432
0.6615	Remote Similarity	NPC24264
0.6567	Remote Similarity	NPC128560
0.6567	Remote Similarity	NPC229166
0.6406	Remote Similarity	NPC117188
0.6406	Remote Similarity	NPC145832
0.6406	Remote Similarity	NPC600388
0.6364	Remote Similarity	NPC19520
0.6176	Remote Similarity	NPC298979
0.6061	Remote Similarity	NPC205421
0.6061	Remote Similarity	NPC607722
0.5938	Remote Similarity	NPC326316
0.5938	Remote Similarity	NPC81733
0.5882	Remote Similarity	NPC605845
0.5873	Remote Similarity	NPC99659
0.5873	Remote Similarity	NPC325871
0.5588	Remote Similarity	NPC474931
0.5441	Remote Similarity	NPC136508
0.5352	Remote Similarity	NPC199465
0.5294	Remote Similarity	NPC27887
0.5278	Remote Similarity	NPC248642
0.5224	Remote Similarity	NPC158376
0.5211	Remote Similarity	NPC226102
0.5205	Remote Similarity	NPC602113

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC247389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4913
0.1-0.2	4055
0.2-0.3	168
0.3-0.4	10
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