NPASS Compound

Natural Product: NPC471128

Natural Product ID	NPC471128
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DLQKPYHIZBVQDA-RSGVYCAMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2375795
PubChem CID	73356431
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 80 83 0 0 0 0 0 0 0 0999 V2000 -5.3451 2.6631 -1.8136 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6981 1.5217 -2.2700 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8120 0.9196 -1.2405 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5359 0.8331 -1.5459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3473 0.3211 -0.8408 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3226 1.4508 -0.9267 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9205 1.3867 -1.6973 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9536 1.1049 -0.2517 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4367 2.1287 0.5810 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5534 2.2190 1.3172 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3714 1.2694 1.3140 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7906 3.4294 2.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8818 3.5320 2.8406 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1856 4.7423 3.6757 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8247 4.5493 2.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9979 -0.2598 0.3299 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2262 -0.8469 0.9348 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4687 -0.0634 0.5752 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6221 -0.7839 1.0921 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8542 -0.9127 0.2704 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4340 0.4513 0.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6480 -1.5422 -0.9467 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6648 -1.7522 1.1895 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8653 -1.6946 1.5124 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6485 -2.7194 1.6485 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4497 -2.1576 1.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9581 -4.1226 2.1069 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3202 1.1569 1.3127 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0401 -0.9123 2.4424 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5942 -1.1359 -0.6205 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7264 -1.8303 -0.3885 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2593 -1.6883 0.7205 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4023 -2.7562 -1.3365 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4030 -3.8380 -1.7015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0125 -4.8353 -2.6727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8254 -2.0514 -2.6017 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1491 0.3849 -2.7824 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5346 2.7385 -2.1322 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9704 2.8902 -0.9045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0833 1.7164 -3.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4247 0.7167 -2.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2910 1.2315 -2.5556 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9966 -0.5706 -1.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7326 2.4580 -0.7326 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5716 2.6896 2.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5720 4.7778 4.5959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2401 4.6870 4.0042 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9750 5.6576 3.0897 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 5.0045 3.1165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2087 5.3116 1.3905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8338 4.2159 1.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7244 -0.2689 1.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4403 -1.8792 0.5966 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9843 -0.2106 2.0233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5347 0.4734 -0.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0844 1.1330 0.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4685 -1.3726 -1.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5826 -2.7344 1.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1901 -4.4725 2.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9440 -4.1272 2.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9653 -4.8379 1.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8166 1.8843 0.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9790 -0.6986 3.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4638 -1.8471 2.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6628 -0.0913 2.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2630 -3.2778 -0.8710 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0661 -4.3725 -0.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4845 -3.4104 -2.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6546 -4.6768 -3.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7295 -5.8735 -2.4063 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1272 -4.7883 -2.6488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7422 -2.5730 -2.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0764 -1.0174 -2.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0667 -2.1431 -3.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7077 -0.5897 -2.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 0.3153 -3.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6825 0.8047 -3.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3322 3.5292 -1.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2009 2.9292 -3.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6375 2.5076 -2.2271 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 1 9 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 12 15 1 0 8 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 6 20 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 25 27 1 0 18 28 1 1 17 29 1 0 16 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 7 37 1 0 7 38 1 0 21 3 1 0 18 5 1 0 26 19 1 0 8 6 1 0 1 39 1 0 2 40 1 0 2 41 1 0 4 42 1 0 5 43 1 6 6 44 1 1 13 45 1 0 14 46 1 0 14 47 1 0 14 48 1 0 15 49 1 0 15 50 1 0 15 51 1 0 16 52 1 1 17 53 1 6 19 54 1 1 21 55 1 0 21 56 1 0 22 57 1 0 26 58 1 0 27 59 1 0 27 60 1 0 27 61 1 0 28 62 1 0 29 63 1 0 29 64 1 0 29 65 1 0 33 66 1 0 34 67 1 0 34 68 1 0 35 69 1 0 35 70 1 0 35 71 1 0 36 72 1 0 36 73 1 0 36 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 38 78 1 0 38 79 1 0 38 80 1 0 M END

Standard InCHIKey	DLQKPYHIZBVQDA-RSGVYCAMSA-N
Standard InCHI	InChI=1S/C30H42O8/c1-9-15(3)25(33)37-24-18(6)29(36)20(22-27(7,8)30(22,24)38-26(34)16(4)10-2)12-19(14-31)13-28(35)21(29)11-17(5)23(28)32/h10-12,15,18,20-22,24,31,35-36H,9,13-14H2,1-8H3/b16-10+/t15?,18-,20+,21-,22-,24-,28-,29-,30-/m1/s1
SMILES	OCC1=C[C@H]2[C@@H]3C([C@]3(OC(=O)/C(=C/C)/C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)OC(=O)C(CC)C)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	530.29	Volume:	547.713 ? Van der Waals volume.
Dense:	0.968	LogP:	2.523 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.896 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.445 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	22.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.359	Fsp³:	0.7
MCE-18:	86.118 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.232	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.313	Promiscuous compounds:	0.315

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.006	MDCK Permeability:	-4.678
Pgp-inhibitor:	0.556	Pgp-substrate:	0.994
PAMPA:	0.962 ? 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):	0.297
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.963
Plasma Protein Binding (PPB):	75.964%	Volume Distribution (VD):	0.008
Fu:	26.163% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.807
OATP1B3 inhibitor:	0.3	BCRP inhibitor:	0.007
BSEP inhibitor:	0.938

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.046	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.603	CYP3A4-substrate:	0.599
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.991
HLM stability:	0.954 ? 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):

7.731

Half-life (T1/2):

1.28

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.253
Human Hepatotoxicity (H-HT):	0.675	Drug-induced Liver Injury (DILI):	0.478
AMES Toxicity:	0.332	Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.262	Skin Sensitization:	0.908
Carcinogencity:	0.529	Eye Corrosion:	0.017
Eye Irritation:	0.496	Respiratory Toxicity:	0.746
Drug-induced Neurotoxicity:	0.153	Ototoxicity:	0.647
Hematotoxicity:	0.707	Drug-induced Nephrotoxicity:	0.646
Genotoxicity:	0.55	RPMI-8226 Immunitoxicity:	0.104
A549 Cytotoxicity:	0.055	Hek293 Cytotoxicity:	0.148
BCF:	0.586 ? 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:	3.419 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.407 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.552 ? 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
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049973]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701597]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25819096]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2978	Croton tiglium	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2978	Croton tiglium	Species	Euphorbiaceae	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
NPT890	Cell line	SNU-387	Homo sapiens	IC50	>	10000.0	nM	PMID[23819871]

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 NPC471128 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	16265
0.1-0.2	31718
0.2-0.3	1699
0.3-0.4	56
0.4-0.5	53
0.5-0.6	39
0.6-0.7	17
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8788	High Similarity	NPC471126
0.8615	High Similarity	NPC471125
0.8209	Intermediate Similarity	NPC145182
0.8182	Intermediate Similarity	NPC157252
0.8182	Intermediate Similarity	NPC472758
0.8	Intermediate Similarity	NPC22628
0.7612	Intermediate Similarity	NPC472397
0.75	Intermediate Similarity	NPC600005
0.7353	Intermediate Similarity	NPC171905
0.6944	Remote Similarity	NPC275696
0.6944	Remote Similarity	NPC255081
0.6849	Remote Similarity	NPC5991
0.6849	Remote Similarity	NPC196500
0.6849	Remote Similarity	NPC471108
0.6849	Remote Similarity	NPC5989
0.675	Remote Similarity	NPC482198
0.6667	Remote Similarity	NPC243902
0.6582	Remote Similarity	NPC472398
0.6582	Remote Similarity	NPC600915
0.6579	Remote Similarity	NPC478999
0.6494	Remote Similarity	NPC484333
0.641	Remote Similarity	NPC145238
0.6338	Remote Similarity	NPC71889
0.6296	Remote Similarity	NPC482199
0.6296	Remote Similarity	NPC482197
0.6111	Remote Similarity	NPC475937
0.5974	Remote Similarity	NPC471127
0.5974	Remote Similarity	NPC481531
0.5882	Remote Similarity	NPC479001
0.5882	Remote Similarity	NPC479002
0.5867	Remote Similarity	NPC481522
0.5867	Remote Similarity	NPC606275
0.5833	Remote Similarity	NPC138641
0.5833	Remote Similarity	NPC611243
0.5789	Remote Similarity	NPC481520
0.5769	Remote Similarity	NPC474872
0.5696	Remote Similarity	NPC472399
0.5632	Remote Similarity	NPC601392
0.5632	Remote Similarity	NPC601964
0.5616	Remote Similarity	NPC158523
0.5584	Remote Similarity	NPC605797
0.5568	Remote Similarity	NPC601559
0.5556	Remote Similarity	NPC153036
0.5556	Remote Similarity	NPC611949
0.5513	Remote Similarity	NPC234858
0.5513	Remote Similarity	NPC179207
0.5506	Remote Similarity	NPC283875
0.5506	Remote Similarity	NPC22571
0.5455	Remote Similarity	NPC472757
0.5455	Remote Similarity	NPC154363
0.5375	Remote Similarity	NPC481525
0.5301	Remote Similarity	NPC607335
0.5301	Remote Similarity	NPC610849
0.527	Remote Similarity	NPC156252
0.5238	Remote Similarity	NPC609983
0.519	Remote Similarity	NPC472401
0.5185	Remote Similarity	NPC481528
0.5185	Remote Similarity	NPC488610
0.5181	Remote Similarity	NPC10721
0.5116	Remote Similarity	NPC600879
0.5116	Remote Similarity	NPC609967
0.5063	Remote Similarity	NPC485736
0.5063	Remote Similarity	NPC277477
0.5063	Remote Similarity	NPC479003
0.5063	Remote Similarity	NPC485735

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6707
0.1-0.2	2424
0.2-0.3	19
0.3-0.4	0
0.4-0.5	0
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