NPASS Compound

Natural Product: NPC249570

Natural Product ID	NPC249570
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ROZLRDFWASSJFO-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3394446
PubChem CID	NA
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

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 71 73 0 0 0 0 0 0 0 0999 V2000 -5.3521 -1.9244 -0.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2635 -2.7722 -0.1060 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0232 -2.7379 -0.4815 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5655 -1.7885 -1.5175 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4910 -0.9007 -1.0381 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6504 0.1815 -0.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5408 0.7796 0.2103 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6666 0.3687 -0.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8974 -0.7256 -0.8533 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1990 -1.3737 -1.3533 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -2.3719 -2.0785 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1968 -1.1563 -1.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3830 -2.2753 -1.9492 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2917 -0.5064 -0.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0771 0.5893 0.1650 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7813 1.0335 0.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6063 2.1740 1.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2259 3.4215 0.7195 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0246 3.7471 -0.5049 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1207 2.9230 -1.7122 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6190 5.2336 -0.7005 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1824 1.2519 0.6778 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6654 -0.9810 -0.9500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0169 -2.2006 -0.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0706 -2.2152 0.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9144 -1.0114 0.7249 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4101 -3.4524 1.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9359 0.7199 0.1085 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2462 0.9041 1.4634 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3773 1.4990 1.9138 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6509 1.6645 3.2859 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2967 1.9608 1.0128 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0388 1.8059 -0.3234 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8595 1.1877 -0.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7628 1.1320 -2.1572 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4759 2.5782 1.4293 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6369 -3.7780 0.9651 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2878 -1.6898 -1.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3275 -2.4877 -0.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5227 -1.0213 0.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3044 -3.4015 -0.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1577 -2.4065 -2.3782 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3693 -1.2173 -1.9683 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2108 -3.2192 -1.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8729 1.8702 2.1678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5544 2.3740 1.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0707 4.2997 1.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3120 3.6461 -2.5852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2266 2.3373 -1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0016 2.2884 -1.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1614 5.4789 0.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5269 5.7928 -0.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2232 5.3851 -1.7007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3050 1.2003 1.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6848 -1.2224 -2.0354 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3396 -0.1448 -0.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4141 -3.1155 -0.2760 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2277 -0.6388 -0.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8531 -1.3258 1.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3617 -0.2546 1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9203 -3.4158 2.3295 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0312 -4.3694 0.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4987 -3.5603 1.5218 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5296 0.5443 2.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1523 1.0313 3.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7916 2.1846 -1.0159 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0297 1.5759 -2.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6973 2.6011 2.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6966 -4.7827 0.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6000 -3.5420 1.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7911 -3.7791 1.7026 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 2 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 9 12 1 0 12 13 1 0 12 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 2 3 19 20 1 0 19 21 1 0 15 22 1 0 14 23 1 0 23 24 1 0 24 25 2 3 25 26 1 0 25 27 1 0 6 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 30 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 32 36 1 0 2 37 1 0 10 5 1 0 34 28 1 0 16 8 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 13 44 1 0 17 45 1 0 17 46 1 0 18 47 1 0 20 48 1 0 20 49 1 0 20 50 1 0 21 51 1 0 21 52 1 0 21 53 1 0 22 54 1 0 23 55 1 0 23 56 1 0 24 57 1 0 26 58 1 0 26 59 1 0 26 60 1 0 27 61 1 0 27 62 1 0 27 63 1 0 29 64 1 0 31 65 1 0 33 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	ROZLRDFWASSJFO-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H34O7/c1-15(2)7-10-18-26(34)19(11-8-16(3)4)30-25(27(18)35)28(36)20(12-9-17(5)6)29(37-30)21-13-23(32)24(33)14-22(21)31/h7-9,13-14,31-35H,10-12H2,1-6H3
SMILES	CC(=CCc1c(oc2c(c1=O)c(O)c(c(c2CC=C(C)C)O)CC=C(C)C)c1cc(O)c(cc1O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	506.23	Volume:	534.297 ? Van der Waals volume.
Dense:	0.947	LogP:	6.277 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.247 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.269 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	131.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.509	Fsp³:	0.3
MCE-18:	25.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.995	Fluc inhibitor:	0.358 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.978 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.64 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.559	Promiscuous compounds:	0.199

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.126	MDCK Permeability:	-4.756
Pgp-inhibitor:	0.823	Pgp-substrate:	0.015
PAMPA:	0.667 ? 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):	0.341
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.981
Plasma Protein Binding (PPB):	94.628%	Volume Distribution (VD):	0.212
Fu:	6.144% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.959
BSEP inhibitor:	0.658

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.018	CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.715	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

4.58

Half-life (T1/2):

1.932

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.601
Human Hepatotoxicity (H-HT):	0.493	Drug-induced Liver Injury (DILI):	0.623
AMES Toxicity:	0.617	Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.762	Skin Sensitization:	0.998
Carcinogencity:	0.188	Eye Corrosion:	0.0
Eye Irritation:	0.069	Respiratory Toxicity:	0.98
Drug-induced Neurotoxicity:	0.095	Ototoxicity:	0.688
Hematotoxicity:	0.07	Drug-induced Nephrotoxicity:	0.539
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.74
BCF:	1.845 ? 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:	5.727 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.557 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.194 ? 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
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO12348	Chrysosplenium grayanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955888]
NPO6876	Ixora coccinea	Species	Rubiaceae	Eukaryota	aerial parts	collected on the campus of Kaohsiung Medical University, Taiwan	2007-Oct	PMID[21106454]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO6890	Euphorbia jolkinii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17091	Berberis chilensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12348	Chrysosplenium grayanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15941	Bacillus licheniformis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18019	Dalbergia oliveri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16603	Mundulea sericea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12348	Chrysosplenium grayanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6890	Euphorbia jolkinii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12348	Chrysosplenium grayanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18019	Dalbergia oliveri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6876	Ixora coccinea	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17021	Mahonia aquifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18019	Dalbergia oliveri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17471	Penicillium obscurum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15941	Bacillus licheniformis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17091	Berberis chilensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16603	Mundulea sericea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12348	Chrysosplenium grayanum	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6890	Euphorbia jolkinii	Species	Euphorbiaceae	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	1

Activity Type	# Activity
Cell line	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
NPT196	Cell line	AGS	Homo sapiens	Activity	=	30.0	%	PMID[25537111]

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 NPC249570 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	28914
0.1-0.2	19341
0.2-0.3	1376
0.3-0.4	179
0.4-0.5	33
0.5-0.6	8
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8507	High Similarity	NPC476631
0.7538	Intermediate Similarity	NPC607385
0.6351	Remote Similarity	NPC278427
0.6184	Remote Similarity	NPC218871
0.6026	Remote Similarity	NPC476630
0.6	Remote Similarity	NPC469658
0.5696	Remote Similarity	NPC276444
0.5634	Remote Similarity	NPC96565
0.5405	Remote Similarity	NPC76833
0.527	Remote Similarity	NPC303633
0.5139	Remote Similarity	NPC190637
0.5139	Remote Similarity	NPC482709
0.5135	Remote Similarity	NPC269420
0.5059	Remote Similarity	NPC198829

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC249570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5746
0.1-0.2	3390
0.2-0.3	13
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