NPASS Compound

Natural Product: NPC154363

Natural Product ID	NPC154363
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KFNWMXLJLRPJCL-WYEIHJKRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2375780
PubChem CID	73347289
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

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 73 0 0 0 0 0 0 0 0999 V2000 5.3702 2.8240 2.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7639 2.1563 0.8536 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5802 1.5635 0.9801 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8921 1.5806 2.2909 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9975 0.9203 -0.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5829 0.9095 -1.3034 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7717 0.2879 -0.0997 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1321 -0.3675 -1.1786 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0644 0.4329 -1.5905 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2006 0.4105 -3.1085 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3756 0.0971 -0.9953 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1403 1.3414 -0.8179 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5436 2.4097 -0.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4944 3.2533 0.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3250 4.5009 1.1502 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7843 2.7779 -0.2166 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8168 3.4156 -0.4933 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5392 1.3086 -0.3560 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7131 0.8202 1.0888 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6446 -0.6605 1.0069 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5845 -1.3461 0.6184 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2381 -0.8159 0.1806 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4305 -2.0140 -0.1449 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8208 -2.2451 0.6285 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1350 -3.7402 0.8803 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2804 -1.4150 1.7619 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8628 -1.7683 -0.7932 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3039 -2.7604 -1.7029 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6497 -2.8582 -1.9819 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5331 -2.1225 -1.4764 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1753 -3.8901 -2.9464 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8584 -1.4274 1.3902 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6376 -2.7863 1.2611 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0845 -0.6696 -1.9599 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7644 3.6928 2.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4707 2.0538 2.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3853 3.1754 1.7905 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3044 2.1655 -0.0988 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1221 0.6637 2.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7895 1.7609 2.1528 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2352 2.4243 2.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8395 -0.3092 -2.0316 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1826 1.5005 -1.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2473 0.2476 -3.4306 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3570 -0.5044 -3.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2830 1.2613 -3.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2099 1.7872 -1.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5254 2.5385 0.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1838 5.1702 0.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1898 4.2703 2.2118 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3977 4.9967 0.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2610 0.8293 -1.0301 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8234 1.1829 1.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6603 1.1918 1.5144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7484 -2.4157 0.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8870 -0.2104 1.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9862 -2.9285 -0.5200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1087 -4.2927 -0.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0933 -3.8481 1.4076 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3235 -4.1148 1.5230 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3940 -1.2687 1.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8623 -0.4335 1.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1022 -1.9694 2.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5723 -4.7103 -2.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3748 -4.2086 -3.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0248 -3.4819 -3.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1142 -1.2290 2.4521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7528 -1.1292 0.7787 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0078 -3.1301 0.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9709 -0.8514 -1.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 24 27 1 0 27 28 1 6 28 29 1 0 29 30 2 0 29 31 1 0 20 32 1 0 32 33 1 0 11 34 1 6 27 8 1 0 22 11 1 0 27 23 1 0 18 12 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 8 42 1 6 9 43 1 1 10 44 1 0 10 45 1 0 10 46 1 0 12 47 1 6 13 48 1 0 15 49 1 0 15 50 1 0 15 51 1 0 18 52 1 6 19 53 1 0 19 54 1 0 21 55 1 0 22 56 1 1 23 57 1 6 25 58 1 0 25 59 1 0 25 60 1 0 26 61 1 0 26 62 1 0 26 63 1 0 31 64 1 0 31 65 1 0 31 66 1 0 32 67 1 0 32 68 1 0 33 69 1 0 34 70 1 0 M END

Standard InCHIKey	KFNWMXLJLRPJCL-WYEIHJKRSA-N
Standard InCHI	InChI=1S/C27H36O7/c1-8-13(2)24(31)33-23-15(4)26(32)19-9-14(3)21(30)18(19)10-17(12-28)11-20(26)22-25(6,7)27(22,23)34-16(5)29/h8-9,11,15,18-20,22-23,28,32H,10,12H2,1-7H3/b13-8+/t15-,18-,19-,20+,22-,23-,26+,27-/m1/s1
SMILES	C/C=C(C)/C(=O)O[C@@H]1[C@@H](C)[C@@]2([C@@H]3C=C(C)C(=O)[C@@H]3CC(=C[C@H]2[C@@H]2C(C)(C)[C@]12OC(=O)C)CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.25	Volume:	487.035 ? Van der Waals volume.
Dense:	0.97	LogP:	1.536 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.822 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.8 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	22.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.368	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.257	Fsp³:	0.667
MCE-18:	80.667 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.088	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.308	Promiscuous compounds:	0.474

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.248	MDCK Permeability:	-4.948
Pgp-inhibitor:	0.765	Pgp-substrate:	0.635
PAMPA:	0.941 ? 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):	0.73
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.913
Plasma Protein Binding (PPB):	76.13%	Volume Distribution (VD):	-0.103
Fu:	22.508% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.52	BCRP inhibitor:	0.0
BSEP inhibitor:	0.946

ADMET: Metabolism

CYP1A2-inhibitor:	0.031	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.007	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.526	CYP3A4-substrate:	0.635
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.929
HLM stability:	0.5 ? 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):

7.432

Half-life (T1/2):

1.16

ADMET: Toxicity

hERG Blockers:	0.043	hERG Blockers (10um):	0.245
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.745
AMES Toxicity:	0.82	Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.484	Skin Sensitization:	0.988
Carcinogencity:	0.912	Eye Corrosion:	0.012
Eye Irritation:	0.55	Respiratory Toxicity:	0.576
Drug-induced Neurotoxicity:	0.554	Ototoxicity:	0.517
Hematotoxicity:	0.803	Drug-induced Nephrotoxicity:	0.83
Genotoxicity:	0.913	RPMI-8226 Immunitoxicity:	0.211
A549 Cytotoxicity:	0.522	Hek293 Cytotoxicity:	0.551
BCF:	0.584 ? 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:	3.31 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.947 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.33 ? 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]
NPO40822	Croton damayeshu	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117522]
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	5
Inhibition	2

Activity Type	# Activity
Cell line	6
Organism	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	DOI[10.6019/CHEMBL1201861]
NPT81	Cell line	A549	Homo sapiens	Inhibition	<	50.0	%	PMID[31117522]
NPT116	Cell line	HL-60	Homo sapiens	Inhibition	<	50.0	%	PMID[31117522]
NPT1229	Cell line	Huh-7	Homo sapiens	IC50	=	3360.0	nM	PMID[27623549]
NPT81	Cell line	A549	Homo sapiens	IC50	=	8500.0	nM	PMID[27623549]
NPT111	Cell line	K562	Homo sapiens	IC50	=	70.0	nM	PMID[27623549]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	IC50	=	20500.0	nM	PMID[27623549]

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 NPC154363 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	18403
0.1-0.2	28660
0.2-0.3	2635
0.3-0.4	67
0.4-0.5	36
0.5-0.6	20
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9016	High Similarity	NPC234858
0.9016	High Similarity	NPC179207
0.873	High Similarity	NPC471127
0.873	High Similarity	NPC481525
0.873	High Similarity	NPC481531
0.8333	Intermediate Similarity	NPC10721
0.8065	Intermediate Similarity	NPC482406
0.7812	Intermediate Similarity	NPC472757
0.7727	Intermediate Similarity	NPC485737
0.7612	Intermediate Similarity	NPC476111
0.7538	Intermediate Similarity	NPC481522
0.7534	Intermediate Similarity	NPC140021
0.75	Intermediate Similarity	NPC90814
0.75	Intermediate Similarity	NPC189393
0.75	Intermediate Similarity	NPC608501
0.7424	Intermediate Similarity	NPC481520
0.7313	Intermediate Similarity	NPC482405
0.7286	Intermediate Similarity	NPC236918
0.7286	Intermediate Similarity	NPC156745
0.726	Intermediate Similarity	NPC611138
0.7101	Intermediate Similarity	NPC481528
0.6849	Remote Similarity	NPC472759
0.6622	Remote Similarity	NPC482221
0.6533	Remote Similarity	NPC482220
0.6447	Remote Similarity	NPC482222
0.6364	Remote Similarity	NPC482219
0.625	Remote Similarity	NPC485734
0.6197	Remote Similarity	NPC157252
0.6104	Remote Similarity	NPC481523
0.6049	Remote Similarity	NPC112752
0.6049	Remote Similarity	NPC311054
0.6027	Remote Similarity	NPC145182
0.6026	Remote Similarity	NPC329080
0.5867	Remote Similarity	NPC471126
0.5775	Remote Similarity	NPC600179
0.5775	Remote Similarity	NPC602150
0.5714	Remote Similarity	NPC600005
0.5455	Remote Similarity	NPC471128
0.5417	Remote Similarity	NPC481526
0.5405	Remote Similarity	NPC606275
0.5352	Remote Similarity	NPC481521
0.527	Remote Similarity	NPC472397
0.5205	Remote Similarity	NPC481530
0.5205	Remote Similarity	NPC472400
0.5132	Remote Similarity	NPC472758
0.5128	Remote Similarity	NPC5991
0.5128	Remote Similarity	NPC196500
0.5128	Remote Similarity	NPC471108
0.5128	Remote Similarity	NPC5989
0.5067	Remote Similarity	NPC171905
0.5063	Remote Similarity	NPC472399
0.5059	Remote Similarity	NPC21483
0.5059	Remote Similarity	NPC198205

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC154363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6712
0.1-0.2	2387
0.2-0.3	49
0.3-0.4	2
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