NPASS Compound

Natural Product: NPC206615

Natural Product ID	NPC206615
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3R,5S)-1-(4-Hydroxy-3,5-Dimethoxyphenyl)-7-(4-Hydroxy-3-Methoxyphenyl)Heptane-3,5-Diol
IUPAC Name	(3R,5S)-1-(4-hydroxy-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2426108
PubChem CID	21577371
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

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 59 60 0 0 0 0 0 0 0 0999 V2000 -5.9844 2.3545 -3.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4432 2.5032 -1.7202 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1272 1.7066 -0.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2767 0.6336 -0.8111 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 -0.1409 0.3005 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0593 -1.3030 0.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6663 -0.7842 0.3370 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6635 -1.9291 0.1427 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2921 -1.3130 0.4054 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7890 -2.3280 0.2491 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1257 -1.7045 0.5230 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3784 -0.5884 -0.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7394 -0.0108 -0.1304 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8420 1.0170 0.7729 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0861 1.5237 1.0308 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2234 2.5583 1.9348 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1247 3.1157 2.6061 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1884 1.0226 0.4094 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0680 -0.0096 -0.4952 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8405 -0.5365 -0.7737 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1899 -0.5119 -1.1208 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1353 -1.5603 -2.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4427 1.5292 0.6655 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5684 -3.4488 1.0539 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9590 -2.9462 1.0189 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5189 0.1233 1.5504 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3624 1.2022 1.6681 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6679 1.9927 0.5761 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5191 3.0537 0.7734 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7207 1.7832 -3.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9875 1.8965 -3.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9048 3.3612 -3.5128 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8328 0.3801 -1.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2871 -2.0771 0.8440 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1420 -1.6838 -0.9329 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6039 -0.4256 1.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3988 0.0426 -0.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6956 -2.2968 -0.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1633 -0.5054 -0.3622 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2736 -0.8950 1.4261 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7534 -2.6757 -0.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9573 -2.4408 0.4824 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0764 -1.3180 1.5742 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3951 -0.8870 -1.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6540 0.2635 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9489 1.4002 1.2561 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7921 2.4102 3.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4439 4.0960 3.0236 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3040 3.3105 1.8785 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7213 -1.3580 -1.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3119 -1.4580 -2.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0260 -2.5225 -1.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1098 -1.5902 -2.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2924 1.0467 0.4431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7856 -4.2698 0.5804 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2901 -2.6230 1.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2694 -0.5003 2.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7760 1.4049 2.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4399 2.9106 1.1445 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 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 18 23 1 0 10 24 1 0 8 25 1 0 5 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 28 3 1 0 20 13 1 0 1 30 1 0 1 31 1 0 1 32 1 0 4 33 1 0 6 34 1 0 6 35 1 0 7 36 1 0 7 37 1 0 8 38 1 6 9 39 1 0 9 40 1 0 10 41 1 6 11 42 1 0 11 43 1 0 12 44 1 0 12 45 1 0 14 46 1 0 17 47 1 0 17 48 1 0 17 49 1 0 20 50 1 0 22 51 1 0 22 52 1 0 22 53 1 0 23 54 1 0 24 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 29 59 1 0 M END

Standard InCHIKey	UEKHBUNMFZUBFK-DLBZAZTESA-N
Standard InCHI	InChI=1S/C22H30O7/c1-27-19-10-14(6-9-18(19)25)4-7-16(23)13-17(24)8-5-15-11-20(28-2)22(26)21(12-15)29-3/h6,9-12,16-17,23-26H,4-5,7-8,13H2,1-3H3/t16-,17+/m0/s1
SMILES	COc1cc(CC[C@@H](C[C@@H](CCc2cc(OC)c(c(c2)OC)O)O)O)ccc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	406.2	Volume:	417.668 ? Van der Waals volume.
Dense:	0.973	LogP:	1.638 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.862 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.646 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	12.0
TPSA:	108.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.454	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.077	Fsp³:	0.455
MCE-18:	30.0 ? 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:	0.289	Fluc inhibitor:	0.016 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.235 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.434	Promiscuous compounds:	0.574

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.037	MDCK Permeability:	-4.786
Pgp-inhibitor:	0.452	Pgp-substrate:	0.869
PAMPA:	0.002 ? 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):	0.002
20% Bioavailability (F20%):	0.139	30% Bioavailability (F30%):	0.581
50% Bioavailability (F50%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.855
Plasma Protein Binding (PPB):	90.91%	Volume Distribution (VD):	-0.26
Fu:	11.645% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.958	BCRP inhibitor:	0.64
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.564
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	0.993	CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.637	CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.991 ? 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):

8.662

Half-life (T1/2):

1.745

ADMET: Toxicity

hERG Blockers:	0.621	hERG Blockers (10um):	0.82
Human Hepatotoxicity (H-HT):	0.745	Drug-induced Liver Injury (DILI):	0.203
AMES Toxicity:	0.298	Rat Oral Acute Toxicity:	0.336
Maximum Recommended Daily Dose:	0.929	Skin Sensitization:	0.988
Carcinogencity:	0.249	Eye Corrosion:	0.001
Eye Irritation:	0.162	Respiratory Toxicity:	0.979
Drug-induced Neurotoxicity:	0.657	Ototoxicity:	0.916
Hematotoxicity:	0.882	Drug-induced Nephrotoxicity:	0.982
Genotoxicity:	0.03	RPMI-8226 Immunitoxicity:	0.233
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	0.931
BCF:	0.74 ? 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:	3.47 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.664 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.036 ? 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
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np100392m]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	Kampaengsaen district, Nakhon Pathom province, Thailand	n.a.	PMID[18554915]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20196571]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23910596]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176399]
NPO22901	Curcuma comosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22901	Curcuma comosa	Species	Zingiberaceae	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
Inhibition	7
IC50	2

Activity Type	# Activity
Individual protein	1
Unchecked	2
Non-molecular	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	<	17.0	%	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	27.3	%	PMID[38516598]
NPT28438	Unchecked	Unchecked	n.a.	IC50	>	250000.0	nM	PMID[38516598]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[23910596]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	34.4	%	PMID[23910596]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	50.3	%	PMID[23910596]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	38.4	%	PMID[23910596]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	43.2	%	PMID[23910596]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	35.4	%	PMID[23910596]

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 NPC206615 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	22048
0.1-0.2	22326
0.2-0.3	4720
0.3-0.4	556
0.4-0.5	135
0.5-0.6	40
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98631
0.9	High Similarity	NPC312675
0.9	High Similarity	NPC262156
0.9	High Similarity	NPC184651
0.9	High Similarity	NPC113865
0.8182	Intermediate Similarity	NPC473853
0.8182	Intermediate Similarity	NPC470212
0.8	Intermediate Similarity	NPC324571
0.7955	Intermediate Similarity	NPC186843
0.7826	Intermediate Similarity	NPC343720
0.7826	Intermediate Similarity	NPC54872
0.75	Intermediate Similarity	NPC311595
0.75	Intermediate Similarity	NPC24474
0.7209	Intermediate Similarity	NPC17943
0.6863	Remote Similarity	NPC310718
0.6735	Remote Similarity	NPC164386
0.66	Remote Similarity	NPC137427
0.6279	Remote Similarity	NPC8547
0.6136	Remote Similarity	NPC193544
0.6111	Remote Similarity	NPC215941
0.6111	Remote Similarity	NPC123196
0.6111	Remote Similarity	NPC311419
0.6	Remote Similarity	NPC275724
0.6	Remote Similarity	NPC481914
0.6	Remote Similarity	NPC244246
0.6	Remote Similarity	NPC611247
0.5962	Remote Similarity	NPC470213
0.5893	Remote Similarity	NPC65935
0.5893	Remote Similarity	NPC319282
0.5789	Remote Similarity	NPC207613
0.5778	Remote Similarity	NPC471693
0.5769	Remote Similarity	NPC485986
0.5745	Remote Similarity	NPC299406
0.5714	Remote Similarity	NPC476968
0.5652	Remote Similarity	NPC255675
0.5581	Remote Similarity	NPC156840
0.5556	Remote Similarity	NPC481913
0.5556	Remote Similarity	NPC221049
0.5532	Remote Similarity	NPC474320
0.551	Remote Similarity	NPC177291
0.551	Remote Similarity	NPC127937
0.5333	Remote Similarity	NPC49341
0.5333	Remote Similarity	NPC257124
0.5294	Remote Similarity	NPC51840
0.5294	Remote Similarity	NPC82679
0.5283	Remote Similarity	NPC212015
0.5283	Remote Similarity	NPC159968
0.5263	Remote Similarity	NPC20287
0.5263	Remote Similarity	NPC20404
0.5227	Remote Similarity	NPC91461
0.5227	Remote Similarity	NPC7686
0.5227	Remote Similarity	NPC40258
0.5217	Remote Similarity	NPC140359
0.5217	Remote Similarity	NPC474272
0.5208	Remote Similarity	NPC85488
0.52	Remote Similarity	NPC474214
0.5185	Remote Similarity	NPC303680
0.5172	Remote Similarity	NPC12022
0.5172	Remote Similarity	NPC278308
0.5106	Remote Similarity	NPC165133
0.5106	Remote Similarity	NPC242885
0.5106	Remote Similarity	NPC95614
0.5106	Remote Similarity	NPC232316
0.5094	Remote Similarity	NPC5018
0.5094	Remote Similarity	NPC74817
0.5077	Remote Similarity	NPC52277

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC206615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4046
0.1-0.2	4833
0.2-0.3	263
0.3-0.4	6
0.4-0.5	1
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
0.5333	Remote Similarity	NPD228	Phase 0

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