NPASS Compound

Natural Product: NPC226025

Natural Product ID	NPC226025
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Geranyl-5,7-Dihydroxy-3',4'-Dimethoxyflavanone
IUPAC Name	(2S)-2-(3,4-dimethoxyphenyl)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581355
PubChem CID	24854121
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

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 65 67 0 0 0 0 0 0 0 0999 V2000 -8.4005 -1.3157 -0.0310 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4285 -0.9105 0.9971 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1709 -0.6818 0.6673 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7051 -0.8235 -0.7133 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3723 0.4745 -1.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3567 1.2455 -0.6567 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1745 1.4922 -1.2347 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1260 2.2547 -0.5747 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8843 1.5213 -0.2541 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0486 2.0619 0.7378 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1236 1.4574 1.1180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5020 0.2723 0.5054 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7010 -0.2837 -0.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1459 -1.5362 -1.1329 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2661 -2.3116 -1.5121 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6124 -1.7052 -1.2571 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2815 -1.3060 -0.0022 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6964 -0.8431 -0.1737 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1357 -0.1176 -1.2491 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4716 0.2768 -1.3298 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3540 -0.0633 -0.3252 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9008 -0.8013 0.7646 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5860 -1.1788 0.8250 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7934 -1.1458 1.7787 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3122 -1.9010 2.8755 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6983 0.3143 -0.3678 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1275 1.0740 -1.4949 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6476 -0.3921 0.8277 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4705 0.3506 -0.8313 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2566 -0.2240 -1.8115 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4276 3.2492 1.3506 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6118 1.8395 0.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8626 -0.7620 2.4026 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4190 -1.4661 0.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4826 -0.5856 -0.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0656 -2.3020 -0.4417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4223 -0.4119 1.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5082 -1.3300 -1.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8355 -1.5427 -0.7547 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2980 1.1101 -1.4723 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0674 0.3130 -2.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0399 1.1055 -2.2339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 3.1147 -1.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4453 2.7717 0.3546 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7776 1.8684 1.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8598 -2.7825 -1.4747 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9031 -1.1117 -2.1607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3561 -2.2722 0.6196 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4345 0.1487 -2.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8018 0.8402 -2.1670 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2639 -1.7533 1.6860 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0902 -2.0331 3.6505 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1124 -2.9333 2.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4158 -1.4737 3.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8867 0.4643 -2.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5973 2.0263 -1.5736 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2176 1.2053 -1.4877 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9494 -0.6328 -2.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5487 4.0898 0.7784 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4084 2.9495 0.6198 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6844 1.8039 0.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9806 1.4159 1.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8686 -1.1565 2.5651 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1100 -1.3117 3.0194 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8293 0.2904 2.7512 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 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 21 26 1 0 26 27 1 0 17 28 1 0 13 29 2 0 29 30 1 0 10 31 1 0 6 32 1 0 2 33 1 0 29 9 1 0 28 12 1 0 23 18 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 11 45 1 0 16 46 1 0 16 47 1 0 17 48 1 1 19 49 1 0 20 50 1 0 23 51 1 0 25 52 1 0 25 53 1 0 25 54 1 0 27 55 1 0 27 56 1 0 27 57 1 0 30 58 1 0 31 59 1 0 32 60 1 0 32 61 1 0 32 62 1 0 33 63 1 0 33 64 1 0 33 65 1 0 M END

Standard InCHIKey	XMWZSFFOJPSCLZ-VAPFXODJSA-N
Standard InCHI	InChI=1S/C27H32O6/c1-16(2)7-6-8-17(3)9-11-19-20(28)14-25-26(27(19)30)21(29)15-23(33-25)18-10-12-22(31-4)24(13-18)32-5/h7,9-10,12-14,23,28,30H,6,8,11,15H2,1-5H3/b17-9+/t23-/m0/s1
SMILES	CC(=CCC/C(=C/Cc1c(cc2c(C(=O)C[C@@H](c3ccc(c(c3)OC)OC)O2)c1O)O)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	452.22	Volume:	478.892 ? Van der Waals volume.
Dense:	0.944	LogP:	6.263 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.301 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.118 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	20.0
TPSA:	85.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.474	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.352	Fsp³:	0.37
MCE-18:	65.27 ? 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:	0.932	Fluc inhibitor:	0.81 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.506 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.734 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.278	Promiscuous compounds:	0.16

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.86	MDCK Permeability:	-4.644
Pgp-inhibitor:	1.0	Pgp-substrate:	0.001
PAMPA:	0.001 ? 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):	0.005
20% Bioavailability (F20%):	0.016	30% Bioavailability (F30%):	0.239
50% Bioavailability (F50%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.694
Plasma Protein Binding (PPB):	97.266%	Volume Distribution (VD):	0.19
Fu:	2.211% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.932
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.641	CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.76	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.885	CYP2D6-substrate:	0.638
CYP3A4-inhibitor:	0.772	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	1.0
HLM stability:	0.993 ? 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):

5.984

Half-life (T1/2):

1.146

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.539
Human Hepatotoxicity (H-HT):	0.869	Drug-induced Liver Injury (DILI):	0.939
AMES Toxicity:	0.44	Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.658	Skin Sensitization:	0.975
Carcinogencity:	0.471	Eye Corrosion:	0.001
Eye Irritation:	0.847	Respiratory Toxicity:	0.99
Drug-induced Neurotoxicity:	0.698	Ototoxicity:	0.56
Hematotoxicity:	0.429	Drug-induced Nephrotoxicity:	0.877
Genotoxicity:	0.956	RPMI-8226 Immunitoxicity:	0.35
A549 Cytotoxicity:	0.847	Hek293 Cytotoxicity:	0.583
BCF:	2.189 ? 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:	5.094 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.697 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.17 ? 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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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	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
NPT1970	Cell line	THP-1	Homo sapiens	IC50	<	10000.0	nM	PMID[22194678]

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 NPC226025 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	18241
0.1-0.2	26824
0.2-0.3	4074
0.3-0.4	554
0.4-0.5	107
0.5-0.6	19
0.6-0.7	22
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8636	High Similarity	NPC64915
0.8028	Intermediate Similarity	NPC472626
0.8028	Intermediate Similarity	NPC195796
0.8	Intermediate Similarity	NPC278778
0.7971	Intermediate Similarity	NPC470328
0.7971	Intermediate Similarity	NPC209614
0.7714	Intermediate Similarity	NPC164272
0.7714	Intermediate Similarity	NPC470327
0.7681	Intermediate Similarity	NPC228504
0.7571	Intermediate Similarity	NPC213896
0.7534	Intermediate Similarity	NPC45849
0.7429	Intermediate Similarity	NPC290133
0.7361	Intermediate Similarity	NPC185276
0.7027	Intermediate Similarity	NPC298692
0.6667	Remote Similarity	NPC35038
0.6623	Remote Similarity	NPC210459
0.641	Remote Similarity	NPC488557
0.6377	Remote Similarity	NPC1089
0.6375	Remote Similarity	NPC474055
0.6364	Remote Similarity	NPC488558
0.6296	Remote Similarity	NPC472634
0.6282	Remote Similarity	NPC472630
0.6203	Remote Similarity	NPC472631
0.6125	Remote Similarity	NPC27337
0.6125	Remote Similarity	NPC472598
0.6111	Remote Similarity	NPC125855
0.6104	Remote Similarity	NPC488556
0.6076	Remote Similarity	NPC472628
0.6076	Remote Similarity	NPC488554
0.6049	Remote Similarity	NPC287328
0.6049	Remote Similarity	NPC488555
0.6049	Remote Similarity	NPC484418
0.6026	Remote Similarity	NPC472627
0.6026	Remote Similarity	NPC58805
0.6026	Remote Similarity	NPC261063
0.6	Remote Similarity	NPC282009
0.5949	Remote Similarity	NPC321779
0.5867	Remote Similarity	NPC223787
0.5833	Remote Similarity	NPC321399
0.5823	Remote Similarity	NPC299436
0.5769	Remote Similarity	NPC472629
0.5769	Remote Similarity	NPC279650
0.575	Remote Similarity	NPC470326
0.5696	Remote Similarity	NPC262039
0.5676	Remote Similarity	NPC223500
0.5625	Remote Similarity	NPC22192
0.5584	Remote Similarity	NPC477242
0.5467	Remote Similarity	NPC166689
0.5366	Remote Similarity	NPC201800
0.525	Remote Similarity	NPC96408
0.525	Remote Similarity	NPC610511
0.5211	Remote Similarity	NPC601395
0.5181	Remote Similarity	NPC67396
0.5172	Remote Similarity	NPC293319
0.5125	Remote Similarity	NPC166934

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC226025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3770
0.1-0.2	5237
0.2-0.3	137
0.3-0.4	5
0.4-0.5	1
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