NPASS Compound

Natural Product: NPC60445

Natural Product ID	NPC60445
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BEPYKTSNKZMROV-LRZMEQEMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10483251
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 66 72 0 0 0 0 0 0 0 0999 V2000 6.5627 0.4887 -1.4972 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7589 -0.2125 -1.5001 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8010 -1.4170 -0.8445 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7045 -1.9236 -0.2031 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5208 -1.2034 -0.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4382 0.0099 -0.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1796 0.8063 -0.8921 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0066 1.6157 0.3711 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7211 2.4291 0.1611 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6315 1.4051 0.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8548 0.2354 -0.5656 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8749 -0.7438 -0.6518 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3588 -0.4833 -0.0323 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6128 0.6826 0.6368 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9012 0.9845 1.2981 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8203 1.8321 0.5050 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0972 3.1197 0.8478 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9800 3.8269 0.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5541 3.2658 -1.0995 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2519 1.9450 -1.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 1.2277 -0.6296 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0330 -0.0712 -0.8539 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6848 -1.0093 0.1409 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5486 -2.2111 0.1369 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0893 -3.4910 0.4572 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9219 -4.5825 0.4422 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2474 -4.4604 0.1098 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7253 -3.2091 -0.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8834 -2.1215 -0.1923 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0746 -3.1195 -0.5427 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0912 -5.5869 0.0980 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6768 -0.3214 1.5126 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9673 -0.0950 1.9141 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3469 -1.4642 -0.1139 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4274 3.9671 -1.9214 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5543 3.7242 1.9530 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4295 1.6359 0.6862 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2186 2.8178 1.3487 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0753 -0.0189 -1.1773 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0466 2.5645 0.3856 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7685 -3.1357 0.4495 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9774 -2.1512 -0.8226 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5188 1.4410 -2.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5863 0.2192 -2.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6606 -1.6266 0.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2487 1.5721 -1.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9679 1.0158 1.2799 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8224 2.8763 -0.8513 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5653 3.1651 0.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0047 -1.6701 -1.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7264 1.4099 2.3195 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1923 4.8438 0.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6708 1.4503 -2.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0372 -3.5524 0.7151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5412 -5.5534 0.6929 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3061 -1.1520 -0.4526 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8116 -3.0024 0.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2256 -6.0316 -0.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0807 -0.9405 2.1938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0160 -0.1676 2.9143 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5900 4.9419 -1.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5859 3.3839 2.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2977 3.7454 0.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9960 3.0233 -0.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8940 -3.2236 1.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8911 -1.7190 -0.7851 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 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 1 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 27 31 1 0 23 32 1 0 32 33 1 0 23 34 1 0 19 35 1 0 17 36 1 0 14 37 2 0 37 38 1 0 11 39 1 0 8 40 1 0 4 41 1 0 3 42 1 0 6 1 1 0 39 7 1 0 37 10 1 0 34 13 1 0 32 15 1 0 21 16 1 0 29 24 1 0 1 43 1 0 2 44 1 0 5 45 1 0 7 46 1 6 8 47 1 1 9 48 1 0 9 49 1 0 12 50 1 0 15 51 1 1 18 52 1 0 20 53 1 0 25 54 1 0 26 55 1 0 29 56 1 0 30 57 1 0 31 58 1 0 32 59 1 1 33 60 1 0 35 61 1 0 36 62 1 0 38 63 1 0 40 64 1 0 41 65 1 0 42 66 1 0 M END

Standard InCHIKey	BEPYKTSNKZMROV-LRZMEQEMSA-N
Standard InCHI	InChI=1S/C30H24O12/c31-13-7-19(36)24-22(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-23(42-30)10-21-14(27(25)38)9-20(37)28(40-21)11-1-3-15(32)17(34)5-11/h1-8,10,20,26,28-29,31-39H,9H2/t20-,26+,28+,29+,30-/m0/s1
SMILES	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc3c([C@H]4c5c(cc(cc5O[C@](c5ccc(c(c5)O)O)([C@@H]4O)O3)O)O)c2O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.13	Volume:	541.386 ? Van der Waals volume.
Dense:	1.064	LogP:	1.488 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.643 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.431 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	37.0
TPSA:	209.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.158	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.378	Fsp³:	0.2
MCE-18:	143.333 ? 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:	0.801	Fluc inhibitor:	0.067 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.615 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.622 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.499	Promiscuous compounds:	0.109

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.098	MDCK Permeability:	-4.904
Pgp-inhibitor:	0.0	Pgp-substrate:	0.157
PAMPA:	0.279 ? 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%):	0.976	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.965
Plasma Protein Binding (PPB):	93.586%	Volume Distribution (VD):	0.203
Fu:	9.239% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.004
BSEP inhibitor:	0.1

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

8.805

Half-life (T1/2):

3.876

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.899
Human Hepatotoxicity (H-HT):	0.937	Drug-induced Liver Injury (DILI):	0.743
AMES Toxicity:	0.683	Rat Oral Acute Toxicity:	0.755
Maximum Recommended Daily Dose:	0.992	Skin Sensitization:	1.0
Carcinogencity:	0.024	Eye Corrosion:	0.0
Eye Irritation:	0.498	Respiratory Toxicity:	0.74
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.987
Hematotoxicity:	0.018	Drug-induced Nephrotoxicity:	0.414
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.964
BCF:	1.273 ? 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:	3.753 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.269 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.546 ? 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
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	2007; 2008	DOI[10.1007/s11746-010-1589-7]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	cotyledon	n.a.	PMID[11283027]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[12670184]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[21348467]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22537213]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Peanut Skins	n.a.	n.a.	PMID[28231711]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36431807]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oil	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oils	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seeds	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	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 NPC60445 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	27272
0.1-0.2	20279
0.2-0.3	2016
0.3-0.4	170
0.4-0.5	54
0.5-0.6	23
0.6-0.7	33
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
0.7465	Intermediate Similarity	NPC272552
0.7465	Intermediate Similarity	NPC226108
0.7465	Intermediate Similarity	NPC322899
0.7089	Intermediate Similarity	NPC78074
0.7089	Intermediate Similarity	NPC478340
0.7067	Intermediate Similarity	NPC478616
0.7067	Intermediate Similarity	NPC478339
0.6892	Remote Similarity	NPC46283
0.6892	Remote Similarity	NPC469944
0.6892	Remote Similarity	NPC134911
0.6875	Remote Similarity	NPC106601
0.6875	Remote Similarity	NPC151474
0.68	Remote Similarity	NPC44192
0.679	Remote Similarity	NPC212614
0.679	Remote Similarity	NPC478337
0.679	Remote Similarity	NPC478338
0.679	Remote Similarity	NPC205613
0.6747	Remote Similarity	NPC159526
0.6709	Remote Similarity	NPC147743
0.6709	Remote Similarity	NPC4809
0.6709	Remote Similarity	NPC73517
0.6543	Remote Similarity	NPC86630
0.6456	Remote Similarity	NPC471404
0.6389	Remote Similarity	NPC294558
0.6389	Remote Similarity	NPC18185
0.6389	Remote Similarity	NPC263940
0.6133	Remote Similarity	NPC155564
0.6027	Remote Similarity	NPC58190
0.6027	Remote Similarity	NPC108811
0.6027	Remote Similarity	NPC170103
0.6027	Remote Similarity	NPC236202
0.6027	Remote Similarity	NPC262911
0.6027	Remote Similarity	NPC202742
0.6023	Remote Similarity	NPC478617
0.6	Remote Similarity	NPC261619
0.6	Remote Similarity	NPC61477
0.6	Remote Similarity	NPC78770
0.6	Remote Similarity	NPC219876
0.6	Remote Similarity	NPC126029
0.6	Remote Similarity	NPC15658
0.5974	Remote Similarity	NPC226809
0.5946	Remote Similarity	NPC246202
0.5946	Remote Similarity	NPC224161
0.5946	Remote Similarity	NPC46335
0.5946	Remote Similarity	NPC279406
0.5946	Remote Similarity	NPC486519
0.5875	Remote Similarity	NPC20050
0.561	Remote Similarity	NPC306267
0.5571	Remote Similarity	NPC178054
0.5444	Remote Similarity	NPC484331
0.5432	Remote Similarity	NPC278548
0.5385	Remote Similarity	NPC12326
0.5195	Remote Similarity	NPC82917
0.519	Remote Similarity	NPC313116
0.519	Remote Similarity	NPC28440
0.519	Remote Similarity	NPC603340
0.5062	Remote Similarity	NPC70409
0.5062	Remote Similarity	NPC204770
0.5062	Remote Similarity	NPC600551
0.5062	Remote Similarity	NPC601980
0.5062	Remote Similarity	NPC602065
0.5062	Remote Similarity	NPC611024
0.506	Remote Similarity	NPC302549

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC60445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5758
0.1-0.2	3362
0.2-0.3	20
0.3-0.4	8
0.4-0.5	0
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
0.6	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6	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