NPASS Compound

Natural Product: NPC492728

Natural Product ID	NPC492728
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-[3-(3,7-dimethylocta-2,6-dienyl)-4-hydroxy-phenyl]-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
IUPAC Name	2-[3-(3,7-dimethylocta-2,6-dienyl)-4-hydroxy-phenyl]-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 70 72 0 0 0 0 0 0 0 0999 V2000 7.0408 -0.7678 0.5828 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4437 0.5807 0.1176 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6290 1.2133 0.7879 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8370 1.2509 -0.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6507 0.6941 -1.5481 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4521 1.6291 -1.3682 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2562 1.1325 -2.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4038 0.9416 -3.5523 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1223 0.8628 -1.4831 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8065 0.9937 -0.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2836 -0.2857 0.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0684 -0.4481 0.7992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5985 -1.6182 1.3337 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0521 -1.6832 1.5569 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7213 -2.7538 2.0715 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0577 -3.9058 2.4372 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0974 -2.7377 2.2521 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7145 -3.7277 2.7278 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -1.6101 1.8992 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1662 -1.5245 2.0528 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8050 -2.6304 2.5773 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8185 -0.3682 1.6836 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1345 0.7084 1.1647 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8089 1.8849 0.7906 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7710 0.6106 1.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0123 1.7523 0.4958 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1067 1.9769 -0.9389 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7397 1.3428 -1.8711 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5973 0.1534 -1.7960 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5972 1.9020 -3.2987 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0705 -0.5575 1.3855 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7848 -0.6223 1.2366 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2936 -2.6061 1.6025 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6681 -2.4577 1.3567 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1765 -1.2951 0.8281 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5301 -1.1213 0.5755 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8554 -1.4254 -0.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8520 -1.2373 1.1974 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1465 -0.6782 1.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3268 0.3881 1.0345 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1738 1.8756 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2783 1.7850 1.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2208 2.2440 -1.0975 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9020 0.7109 -2.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4397 -0.3103 -1.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7673 2.5796 -1.8995 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3143 1.9143 -0.3268 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2133 0.1972 -3.6975 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6931 1.8797 -4.0565 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4837 0.5062 -3.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3164 0.4952 -2.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9366 1.7149 0.0115 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6130 1.4088 0.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7447 0.3727 0.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2884 -4.3082 3.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6620 -3.0068 2.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9007 -0.3069 1.8061 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3767 2.3712 1.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9434 1.6679 0.8483 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3629 2.6890 1.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5156 2.8701 -1.2915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2129 -0.6728 -1.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6786 0.3886 -1.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6465 -0.3287 -2.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3533 1.0256 -3.9208 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5955 2.2885 -3.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8329 2.6873 -3.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0378 -3.5324 2.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3592 -3.2563 1.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1734 -1.9061 0.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 2 3 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 15 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 2 3 28 29 1 0 28 30 1 0 25 31 2 0 31 32 1 0 13 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 35 11 1 0 32 14 1 0 31 19 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 6 46 1 0 6 47 1 0 8 48 1 0 8 49 1 0 8 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 16 55 1 0 21 56 1 0 22 57 1 0 24 58 1 0 26 59 1 0 26 60 1 0 27 61 1 0 29 62 1 0 29 63 1 0 29 64 1 0 30 65 1 0 30 66 1 0 30 67 1 0 33 68 1 0 34 69 1 0 36 70 1 0 M END

Standard InCHIKey	LAJFCURKIQZXBJ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H34O6/c1-17(2)7-6-8-19(5)10-11-20-15-21(12-14-23(20)31)29-28(35)27(34)26-25(33)16-24(32)22(30(26)36-29)13-9-18(3)4/h7,9-10,12,14-16,31-33,35H,6,8,11,13H2,1-5H3
SMILES	CC(C)=CCCC(C)=CCC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C(CC=C(C)C)=C3O2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	490.24	Volume:	525.507 ? Van der Waals volume.
Dense:	0.933	LogP:	7.714 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.899 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.263 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	21.0
TPSA:	111.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.252	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.277	Fsp³:	0.3
MCE-18:	23.0 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.999	Fluc inhibitor:	0.451 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.953 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.801 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.385	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.984	MDCK Permeability:	-4.7
Pgp-inhibitor:	0.989	Pgp-substrate:	0.004
PAMPA:	0.102 ? 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):	0.013
20% Bioavailability (F20%):	0.862	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.976
Plasma Protein Binding (PPB):	97.063%	Volume Distribution (VD):	0.099
Fu:	2.683% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.995
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.973	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.992	CYP2D6-substrate:	0.566
CYP3A4-inhibitor:	0.0	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):

4.991

Half-life (T1/2):

1.507

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.599
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.642
AMES Toxicity:	0.39	Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.518	Skin Sensitization:	0.986
Carcinogencity:	0.263	Eye Corrosion:	0.0
Eye Irritation:	0.689	Respiratory Toxicity:	0.987
Drug-induced Neurotoxicity:	0.052	Ototoxicity:	0.312
Hematotoxicity:	0.09	Drug-induced Nephrotoxicity:	0.231
Genotoxicity:	0.785	RPMI-8226 Immunitoxicity:	0.079
A549 Cytotoxicity:	0.551	Hek293 Cytotoxicity:	0.555
BCF:	2.127 ? 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:	5.681 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.043 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.661 ? 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
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19338315]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	Fruits	Zhenjiang, Jiangsu Province, China		PMID[23060696]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14875	Morus cathayana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14875	Morus cathayana	Species	Moraceae	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

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

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 NPC492728 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	20468
0.1-0.2	26463
0.2-0.3	2476
0.3-0.4	356
0.4-0.5	66
0.5-0.6	22
0.6-0.7	6
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
0.8438	Intermediate Similarity	NPC293053
0.6974	Remote Similarity	NPC273843
0.6765	Remote Similarity	NPC9117
0.6765	Remote Similarity	NPC63187
0.662	Remote Similarity	NPC59162
0.6528	Remote Similarity	NPC200694
0.6389	Remote Similarity	NPC216978
0.5946	Remote Similarity	NPC273538
0.5867	Remote Similarity	NPC270708
0.5802	Remote Similarity	NPC77856
0.5696	Remote Similarity	NPC37684
0.5696	Remote Similarity	NPC212932
0.557	Remote Similarity	NPC326500
0.5443	Remote Similarity	NPC3980
0.5405	Remote Similarity	NPC482025
0.5309	Remote Similarity	NPC273462
0.5294	Remote Similarity	NPC206153
0.5294	Remote Similarity	NPC271629
0.5256	Remote Similarity	NPC301217
0.5256	Remote Similarity	NPC475799
0.52	Remote Similarity	NPC220062
0.519	Remote Similarity	NPC80962
0.519	Remote Similarity	NPC13779
0.5132	Remote Similarity	NPC88804
0.5128	Remote Similarity	NPC482074
0.5128	Remote Similarity	NPC601414
0.5065	Remote Similarity	NPC190637
0.5063	Remote Similarity	NPC269420
0.5055	Remote Similarity	NPC237418

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC492728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4532
0.1-0.2	4591
0.2-0.3	25
0.3-0.4	1
0.4-0.5	0
0.5-0.6	1
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
0.5946	Remote Similarity	NPD4378	Phase 3

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