NPASS Compound

Natural Product: NPC550169

Natural Product ID	NPC550169
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,4,5-trihydroxy-8-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-1-(3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl)benzo[7]annulen-6-one
IUPAC Name	3,4,5-trihydroxy-8-[(2~{R},3~{S})-3,5,7-trihydroxychroman-2-yl]-1-(3,5,7-trihydroxychroman-2-yl)benzo[7]annulen-6-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 65 70 0 0 0 0 0 0 0 0999 V2000 2.9067 -3.0348 2.9854 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0037 -2.6051 2.2174 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7522 -1.2291 2.2832 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1784 -0.4442 1.2866 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6062 0.9575 1.3062 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9703 1.0619 1.6435 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9120 1.4344 0.7088 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2157 1.7360 1.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1564 2.1071 0.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4629 2.4081 0.5378 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8437 2.1946 -1.1862 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5569 1.8988 -1.5698 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1777 1.9694 -2.9164 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6128 1.5276 -0.6461 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1992 1.2058 -1.0761 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3371 1.7323 0.0558 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8531 3.0390 0.3044 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2824 -0.8677 0.3503 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2922 -2.1235 0.1570 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4475 -2.0589 -0.6030 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9860 -0.7612 -1.0414 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1939 0.0979 0.0798 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0548 1.1565 0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0223 2.1116 1.1332 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8928 3.1782 1.1524 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8751 4.1377 2.1699 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8050 3.2818 0.1204 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8544 2.3553 -0.9027 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7795 2.4683 -1.9413 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9777 1.2972 -0.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0299 0.3137 -1.9897 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4166 -1.0080 -1.5533 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2258 -1.6052 -0.6270 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0417 -3.2912 -0.8668 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -4.4934 -0.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1990 -5.6430 -0.7310 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3704 -4.4975 0.3490 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1539 -5.6786 0.8124 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2491 -3.3074 0.6327 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3737 -3.5261 1.4102 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9428 -4.7862 1.3953 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0390 -0.7281 3.2118 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0396 1.4512 2.1649 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4954 1.6796 2.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0120 1.7472 1.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6022 2.4921 -1.9201 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7235 2.5621 -3.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0893 0.1455 -1.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0169 1.8064 -1.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2638 1.8116 -0.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3131 3.7119 -0.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0394 -0.1412 -0.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4668 -0.2856 -1.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2866 1.9847 1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1176 5.1055 1.9972 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5056 4.1238 0.1191 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7286 2.1191 -1.8548 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0771 0.1168 -2.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4933 0.7325 -2.8750 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3541 -1.6212 -2.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9713 -1.4285 0.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9400 -3.2967 -1.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0521 -5.8331 -0.2090 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0250 -6.0565 1.7344 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6985 -4.9089 0.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 9 11 2 0 11 12 1 0 12 13 1 0 12 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 4 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 25 27 2 0 27 28 1 0 28 29 1 0 28 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 20 34 2 0 34 35 1 0 35 36 1 0 35 37 2 0 37 38 1 0 37 39 1 0 39 40 2 0 40 41 1 0 40 2 1 0 16 5 1 0 39 19 1 0 14 7 1 0 32 21 1 0 30 23 1 0 3 42 1 0 5 43 1 1 8 44 1 0 10 45 1 0 11 46 1 0 13 47 1 0 15 48 1 0 15 49 1 0 16 50 1 6 17 51 1 0 18 52 1 0 21 53 1 0 24 54 1 0 26 55 1 0 27 56 1 0 29 57 1 0 31 58 1 0 31 59 1 0 32 60 1 0 33 61 1 0 34 62 1 0 36 63 1 0 38 64 1 0 41 65 1 0 M END

Standard InCHIKey	IPMYMEWFZKHGAX-NFUGWCFKSA-N
Standard InCHI	InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)/t21-,22?,28+,29?/m0/s1
SMILES	O=C1C=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)C=C2C(C3OC4=CC(O)=CC(O)=C4CC3O)=CC(O)=C(O)C2=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	564.13	Volume:	532.646 ? Van der Waals volume.
Dense:	1.059	LogP:	0.138 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.506 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.738 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	35.0
TPSA:	217.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.16	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.637	Fsp³:	0.207
MCE-18:	127.029 ? 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:	0.758	Fluc inhibitor:	0.043 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.742 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.733 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.471	Promiscuous compounds:	0.287

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.062	MDCK Permeability:	-4.964
Pgp-inhibitor:	0.0	Pgp-substrate:	0.726
PAMPA:	0.987 ? 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%):	0.715	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.993
Plasma Protein Binding (PPB):	94.593%	Volume Distribution (VD):	0.29
Fu:	7.008% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.4
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.032
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.229	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.853	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.308	CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.111	CYP3A4-substrate:	0.056
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.718
HLM stability:	0.087 ? 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):

5.107

Half-life (T1/2):

3.677

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.583
Human Hepatotoxicity (H-HT):	0.783	Drug-induced Liver Injury (DILI):	0.395
AMES Toxicity:	0.75	Rat Oral Acute Toxicity:	0.791
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	0.5
Carcinogencity:	0.369	Eye Corrosion:	0.0
Eye Irritation:	0.434	Respiratory Toxicity:	0.927
Drug-induced Neurotoxicity:	0.112	Ototoxicity:	0.713
Hematotoxicity:	0.076	Drug-induced Nephrotoxicity:	0.51
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.423
A549 Cytotoxicity:	0.978	Hek293 Cytotoxicity:	0.991
BCF:	0.915 ? 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:	3.505 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.753 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.037 ? 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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 16712885]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37255739]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	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 NPC550169 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	28112
0.1-0.2	19992
0.2-0.3	1565
0.3-0.4	147
0.4-0.5	20
0.5-0.6	18
0.6-0.7	4
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	Natural Product ID
0.7031	Intermediate Similarity	NPC607430
0.6207	Remote Similarity	NPC268266
0.6207	Remote Similarity	NPC42760
0.6207	Remote Similarity	NPC220825
0.6207	Remote Similarity	NPC268342
0.5738	Remote Similarity	NPC261619
0.5738	Remote Similarity	NPC61477
0.5738	Remote Similarity	NPC78770
0.5738	Remote Similarity	NPC219876
0.5738	Remote Similarity	NPC126029
0.5738	Remote Similarity	NPC15658
0.5667	Remote Similarity	NPC207179
0.5667	Remote Similarity	NPC167571
0.5667	Remote Similarity	NPC278552
0.5488	Remote Similarity	NPC600812
0.5484	Remote Similarity	NPC47398
0.5484	Remote Similarity	NPC234333
0.5484	Remote Similarity	NPC260898
0.5352	Remote Similarity	NPC9636
0.5303	Remote Similarity	NPC16435
0.5231	Remote Similarity	NPC61946
0.5135	Remote Similarity	NPC308402
0.5075	Remote Similarity	NPC171932

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC550169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6041
0.1-0.2	3092
0.2-0.3	11
0.3-0.4	3
0.4-0.5	0
0.5-0.6	3
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
0.5926	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD1613	Phase 4

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