NPASS Compound

Natural Product: NPC471093

Natural Product ID	NPC471093
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lasiokaurin
IUPAC Name	n.a.
Synonyms	Lasiokaurin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2368597
PubChem CID	73348360
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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 2D 59 63 0 0 0 0 0 0 0 0999 V2000 5.2077 -1.1827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 -2.1469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3191 -3.6241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -1.6339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3828 -0.5621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2954 0.6125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7372 3.5163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8940 5.0080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4381 2.7663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9322 3.3764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -3.5623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3567 -0.2186 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1719 -2.3318 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5502 0.1655 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -3.5623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -4.4101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -5.3743 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 -5.3743 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0865 -4.5781 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8482 -0.6575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9856 -0.2832 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4616 -0.3374 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4637 -1.4265 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8991 2.2632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0080 0.4821 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3953 4.0944 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 4.5883 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2643 5.6181 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6804 5.8897 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7981 -4.5264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 -2.5393 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8321 -4.8203 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9071 -0.8170 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7461 -2.6569 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9916 -0.2857 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 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 1 0 20 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 13 27 1 6 8 28 1 0 8 29 1 0 10 5 1 0 16 25 1 6 14 9 1 0 21 16 1 0 17 10 1 0 1 30 1 0 1 31 1 0 1 32 1 0 5 33 1 6 6 34 1 0 6 35 1 0 7 36 1 0 7 37 1 0 9 38 1 6 11 39 1 0 11 40 1 0 14 41 1 1 15 42 1 0 17 43 1 6 18 44 1 0 18 45 1 0 19 46 1 0 19 47 1 0 20 48 1 1 21 49 1 1 22 50 1 0 24 51 1 0 24 52 1 0 27 53 1 0 28 54 1 0 28 55 1 0 28 56 1 0 29 57 1 0 29 58 1 0 29 59 1 0 M END

Standard InCHIKey	DJQLJZNVICMJRV-VPKUEDJQSA-N
Standard InCHI	InChI=1S/C22H30O7/c1-10-12-5-6-13-20-9-28-22(27,21(13,16(10)24)17(12)25)18(26)15(20)19(3,4)8-7-14(20)29-11(2)23/h12-15,17-18,25-27H,1,5-9H2,2-4H3/t12-,13-,14-,15+,17+,18-,20+,21-,22-/m0/s1
SMILES	CC(=O)O[C@H]1CCC([C@@H]2[C@]31CO[C@@]([C@H]2O)([C@@]12[C@H]3CC[C@H]([C@H]2O)C(=C)C1=O)O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	406.2	Volume:	399.908 ? Van der Waals volume.
Dense:	1.016	LogP:	1.132 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.456 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.865 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	25.0
TPSA:	113.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.439	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.812	Fsp³:	0.818
MCE-18:	135.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.245	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.159	Promiscuous compounds:	0.656

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.593	MDCK Permeability:	-4.958
Pgp-inhibitor:	0.619	Pgp-substrate:	0.644
PAMPA:	0.917 ? 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):	0.629
20% Bioavailability (F20%):	0.88	30% Bioavailability (F30%):	0.975
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.651
Plasma Protein Binding (PPB):	50.521%	Volume Distribution (VD):	-0.136
Fu:	57.503% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.051
BSEP inhibitor:	0.591

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.016	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.805
HLM stability:	0.09 ? 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):

3.675

Half-life (T1/2):

2.374

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.201
Human Hepatotoxicity (H-HT):	0.605	Drug-induced Liver Injury (DILI):	0.23
AMES Toxicity:	0.588	Rat Oral Acute Toxicity:	0.612
Maximum Recommended Daily Dose:	0.72	Skin Sensitization:	0.956
Carcinogencity:	0.46	Eye Corrosion:	0.002
Eye Irritation:	0.59	Respiratory Toxicity:	0.8
Drug-induced Neurotoxicity:	0.033	Ototoxicity:	0.713
Hematotoxicity:	0.256	Drug-induced Nephrotoxicity:	0.685
Genotoxicity:	0.789	RPMI-8226 Immunitoxicity:	0.14
A549 Cytotoxicity:	0.024	Hek293 Cytotoxicity:	0.193
BCF:	0.577 ? 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:	3.412 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.195 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.345 ? 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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21534539]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	aerial parts	Shangrila, Yunnan Province, China	2008-AUG	PMID[21534539]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23819871]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17800	Isodon rosthornii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17800	Isodon rosthornii	Species	Lamiaceae	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	18
MIC	3

Activity Type	# Activity
Cell line	18
Organism	3

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	1600.0	nM	PMID[10757713]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	3200.0	nM	PMID[23229055]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	2000.0	nM	DOI[10.1007/s00044-012-9973-5]
NPT81	Cell line	A549	Homo sapiens	IC50	=	7600.0	nM	DOI[10.1007/s00044-011-9964-y]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	5300.0	nM	DOI[10.1007/s00044-011-9964-y]
NPT660	Cell line	SW480	Homo sapiens	IC50	=	2300.0	nM	PMID[9873651]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	1900.0	nM	PubChem BioAssay data set
NPT660	Cell line	SW480	Homo sapiens	IC50	=	2400.0	nM	PMID[19555123]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	2500.0	nM	DrugMatrix in vivo data: Hematology
NPT81	Cell line	A549	Homo sapiens	IC50	=	6700.0	nM	PMID[12444688]
NPT659	Cell line	SMMC-7721	Homo sapiens	IC50	=	2700.0	nM	PMID[18341274]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	1800.0	nM	PMID[22901896]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	11940.0	nM	PMID[31877536]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	19820.0	nM	PMID[31877536]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	13480.0	nM	PMID[31877536]
NPT319	Cell line	B16	Mus musculus	IC50	=	32570.0	nM	PMID[31877536]
NPT111	Cell line	K562	Homo sapiens	IC50	=	521000.0	nM	PMID[31877536]
NPT1830	Organism	Mycobacterium marinum	Mycobacterium marinum	MIC	=	32.0	ug.mL-1	DOI[10.1007/s00044-012-0320-7]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	16.0	ug.mL-1	PMID[19654408]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	1.0	ug.mL-1	PMID[20718449]
NPT21742	Cell line	L02	Homo sapiens	IC50	=	25390.0	nM	PMID[31877536]

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 NPC471093 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	17898
0.1-0.2	25562
0.2-0.3	6111
0.3-0.4	209
0.4-0.5	38
0.5-0.6	22
0.6-0.7	11
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
0.8136	Intermediate Similarity	NPC474927
0.7097	Intermediate Similarity	NPC63841
0.7049	Intermediate Similarity	NPC202793
0.6984	Remote Similarity	NPC488148
0.6774	Remote Similarity	NPC144486
0.6667	Remote Similarity	NPC132668
0.6667	Remote Similarity	NPC483265
0.6462	Remote Similarity	NPC88945
0.6393	Remote Similarity	NPC55973
0.6393	Remote Similarity	NPC89860
0.6393	Remote Similarity	NPC189663
0.6393	Remote Similarity	NPC153234
0.6308	Remote Similarity	NPC470172
0.6	Remote Similarity	NPC488143
0.5909	Remote Similarity	NPC483206
0.5909	Remote Similarity	NPC488142
0.5909	Remote Similarity	NPC102741
0.5909	Remote Similarity	NPC213320
0.5873	Remote Similarity	NPC471461
0.5797	Remote Similarity	NPC137104
0.5797	Remote Similarity	NPC325618
0.5781	Remote Similarity	NPC488144
0.5781	Remote Similarity	NPC483202
0.5735	Remote Similarity	NPC243354
0.5714	Remote Similarity	NPC473352
0.5692	Remote Similarity	NPC488145
0.5362	Remote Similarity	NPC29505
0.5294	Remote Similarity	NPC488149
0.5294	Remote Similarity	NPC471244
0.5286	Remote Similarity	NPC471245
0.5231	Remote Similarity	NPC252679
0.5231	Remote Similarity	NPC118721
0.5211	Remote Similarity	NPC194273
0.5077	Remote Similarity	NPC289148
0.5075	Remote Similarity	NPC471476
0.5075	Remote Similarity	NPC473324

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6397
0.1-0.2	2646
0.2-0.3	107
0.3-0.4	0
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