NPASS Compound

Natural Product: NPC136172

Natural Product ID	NPC136172
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Theasinensin E
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001712] Complex tannins

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 75 0 0 0 0 0 0 0 0999 V2000 -1.7525 -1.2090 1.2680 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8837 0.1619 1.1706 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0232 0.5469 2.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3343 0.1429 1.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3265 -0.2470 2.4331 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0963 -0.2589 3.7954 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5627 -0.6287 1.9202 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7709 -0.6080 0.5442 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0023 -0.9890 0.0477 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7809 -0.2181 -0.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5528 0.1583 0.2137 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5136 0.5607 -0.5923 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1476 0.5024 -0.2515 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4513 -0.3510 -1.2461 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0057 -1.5931 -1.5496 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4500 -2.4354 -2.4758 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0316 -3.6882 -2.7646 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3068 -2.0366 -3.1250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2810 -2.8775 -4.0763 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2329 -0.8108 -2.8192 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3856 -0.4311 -3.4886 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3027 0.0480 -1.8977 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3633 1.2924 -1.6413 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4448 1.3542 -0.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9789 2.6347 -0.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4513 3.7672 -1.2058 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0123 5.0185 -0.9768 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3587 3.6747 -2.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1672 4.8196 -2.5858 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1855 2.4288 -2.2300 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3084 2.3474 -3.0623 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1508 0.2648 -0.1804 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5228 0.5501 -0.3315 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5486 0.0499 0.4074 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2404 -0.8395 1.4106 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8496 -1.1978 1.6306 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8659 -0.1144 1.1860 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0401 0.9598 2.0549 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2102 -1.4157 2.2306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8773 -2.3134 3.2401 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5264 -1.0453 1.9857 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8582 -0.1572 0.9874 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1723 0.2039 0.7528 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8782 0.3929 0.1966 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5293 -1.4609 2.1850 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0201 0.7469 1.5346 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8789 0.0297 3.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0195 1.6322 2.3424 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6136 0.4579 4.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3580 -0.9391 2.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7004 -1.4815 0.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9106 -0.1913 -1.4076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7745 1.5658 -0.4165 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9053 -1.9298 -1.0527 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0427 -3.7496 -2.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0454 -3.8655 -4.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2426 -0.8952 -3.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8461 2.7748 -0.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4531 5.4953 -1.7610 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1454 4.9681 -3.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8682 1.4960 -3.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9892 -0.6530 -0.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6475 -2.1604 1.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7074 -1.4141 2.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8940 -0.6083 1.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9582 0.6828 3.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4887 -3.2099 2.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3163 -1.4728 2.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7955 0.3917 1.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0893 1.0967 -0.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 5 7 1 0 7 8 2 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 16 18 2 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 2 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 26 28 2 0 28 29 1 0 28 30 1 0 30 31 1 0 24 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 35 39 1 0 39 40 1 0 39 41 2 0 41 42 1 0 42 43 1 0 42 44 2 0 13 2 1 0 22 14 1 0 30 23 2 0 37 32 1 0 11 4 1 0 44 34 1 0 1 45 1 0 2 46 1 1 3 47 1 0 3 48 1 0 6 49 1 0 7 50 1 0 9 51 1 0 10 52 1 0 13 53 1 1 15 54 1 0 17 55 1 0 19 56 1 0 21 57 1 0 25 58 1 0 27 59 1 0 29 60 1 0 31 61 1 0 32 62 1 6 36 63 1 0 36 64 1 0 37 65 1 6 38 66 1 0 40 67 1 0 41 68 1 0 43 69 1 0 44 70 1 0 M END

Standard InCHIKey	JPBGHWKYWUEIOT-XYTTVBAYSA-N
Standard InCHI	InChI=1S/C30H26O14/c31-9-1-15(33)11-5-19(37)29(43-21(11)3-9)13-7-17(35)25(39)27(41)23(13)24-14(8-18(36)26(40)28(24)42)30-20(38)6-12-16(34)2-10(32)4-22(12)44-30/h1-4,7-8,19-20,29-42H,5-6H2/t19-,20-,29-,30-/m1/s1
SMILES	O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C(O)=C1C1=C(C=C(O)C(O)=C1O)[C@H]1OC2=C(C[C@H]1O)C(O)=CC(O)=C2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.13	Volume:	567.523 ? Van der Waals volume.
Dense:	1.075	LogP:	0.161 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.729 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.092 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	34.0
TPSA:	261.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.537	Fsp³:	0.2
MCE-18:	133.333 ? 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:	0.844	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.609 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.478 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.623	Promiscuous compounds:	0.415

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.656	MDCK Permeability:	-4.777
Pgp-inhibitor:	0.0	Pgp-substrate:	0.315
PAMPA:	0.999 ? 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):	0.0
20% Bioavailability (F20%):	0.883	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	88.365%	Volume Distribution (VD):	-0.001
Fu:	14.642% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.413
OATP1B3 inhibitor:	0.152	BCRP inhibitor:	0.027
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.246	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.989	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.25	CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.174
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.539
HLM stability:	0.003 ? 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):

7.779

Half-life (T1/2):

4.317

ADMET: Toxicity

hERG Blockers:	0.061	hERG Blockers (10um):	0.859
Human Hepatotoxicity (H-HT):	0.727	Drug-induced Liver Injury (DILI):	0.471
AMES Toxicity:	0.837	Rat Oral Acute Toxicity:	0.541
Maximum Recommended Daily Dose:	0.975	Skin Sensitization:	1.0
Carcinogencity:	0.082	Eye Corrosion:	0.0
Eye Irritation:	0.975	Respiratory Toxicity:	0.873
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.986
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.017
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.011
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.959
BCF:	0.784 ? 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:	3.266 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.479 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.915 ? 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
NPO8258	Camellia sinensis	Tea Or Coffee	Leaf	1.4	1.4	1.4	mg/100g	Database [DUKE]

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 NPC136172 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	25055
0.1-0.2	22042
0.2-0.3	2500
0.3-0.4	156
0.4-0.5	67
0.5-0.6	15
0.6-0.7	12
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
0.72	Intermediate Similarity	NPC268266
0.72	Intermediate Similarity	NPC42760
0.72	Intermediate Similarity	NPC220825
0.72	Intermediate Similarity	NPC268342
0.6604	Remote Similarity	NPC261619
0.6604	Remote Similarity	NPC61477
0.6604	Remote Similarity	NPC78770
0.6604	Remote Similarity	NPC219876
0.6604	Remote Similarity	NPC126029
0.6604	Remote Similarity	NPC15658
0.6226	Remote Similarity	NPC207179
0.6226	Remote Similarity	NPC167571
0.6226	Remote Similarity	NPC278552
0.6	Remote Similarity	NPC47398
0.6	Remote Similarity	NPC234333
0.6	Remote Similarity	NPC260898
0.569	Remote Similarity	NPC61946
0.5538	Remote Similarity	NPC9636
0.55	Remote Similarity	NPC16435
0.55	Remote Similarity	NPC171932
0.5469	Remote Similarity	NPC96576
0.5303	Remote Similarity	NPC607430
0.5294	Remote Similarity	NPC308402
0.5143	Remote Similarity	NPC470802
0.5075	Remote Similarity	NPC58190
0.5075	Remote Similarity	NPC108811
0.5075	Remote Similarity	NPC170103
0.5075	Remote Similarity	NPC236202
0.5075	Remote Similarity	NPC262911
0.5075	Remote Similarity	NPC202742
0.5072	Remote Similarity	NPC28440

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5558
0.1-0.2	3553
0.2-0.3	32
0.3-0.4	3
0.4-0.5	2
0.5-0.6	0
0.6-0.7	2
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
0.6604	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6604	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