NPASS Compound

Natural Product: NPC147284

Natural Product ID	NPC147284
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Heptadec-10'(Z)-Enylphenol
IUPAC Name	3-[(Z)-heptadec-10-enyl]phenol
Synonyms	3-[10'(Z)-Heptadecenyl]Phenol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL470127
PubChem CID	44575468
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

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 62 62 0 0 0 0 0 0 0 0999 V2000 -6.0949 3.1073 0.3610 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3714 1.8478 -0.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3561 0.8266 -0.5864 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0420 -0.4326 -1.2267 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1808 -1.4843 -0.7586 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7243 -1.4623 -0.6412 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9896 -0.5300 0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 -0.8595 1.2054 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0979 -2.2315 1.6834 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6023 -2.5916 1.6102 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1136 -2.4827 0.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3319 -2.8193 0.0391 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2447 -1.9451 0.8322 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1285 -0.4807 0.4363 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0604 0.3769 1.2520 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9842 1.8231 0.8860 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4093 2.0522 -0.5264 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8410 1.6286 -0.6673 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1840 0.3615 -1.0524 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5520 0.0768 -1.1437 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5076 1.0049 -0.8662 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1159 2.2652 -0.4832 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7884 2.6001 -0.3767 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0780 3.2517 -0.1882 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2799 3.7643 0.7092 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7507 3.5456 -0.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6745 2.7109 1.2280 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6961 2.2155 -0.9774 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8360 1.4991 0.7371 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1158 1.3567 -1.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0342 0.6227 0.3243 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8189 -0.1996 -2.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0881 -0.9385 -1.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5885 -1.8170 0.2715 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4291 -2.4264 -1.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3273 -2.5208 -0.4455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2949 -1.3543 -1.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9629 0.5544 -0.0968 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7257 -0.0749 1.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6356 -3.0228 1.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3450 -2.2028 2.7975 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0601 -1.8230 2.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4072 -3.5656 2.0553 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6965 -3.2054 -0.4232 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2845 -1.4701 -0.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.7237 -1.0276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5423 -3.8714 0.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0771 -2.0889 1.8975 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2902 -2.2429 0.5997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2105 -0.3110 -0.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0777 -0.1742 0.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0813 -0.0490 1.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8428 0.2572 2.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6696 2.4315 1.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9517 2.2174 1.0826 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8159 1.4788 -1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3434 3.1455 -0.7953 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4515 -0.4002 -1.2844 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8246 -0.9181 -1.4459 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5654 0.7623 -0.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4736 3.6090 -0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8314 3.3268 -0.8803 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 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 23 18 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 0 5 35 1 0 6 36 1 0 6 37 1 0 7 38 1 0 8 39 1 0 9 40 1 0 9 41 1 0 10 42 1 0 10 43 1 0 11 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 19 58 1 0 20 59 1 0 21 60 1 0 23 61 1 0 24 62 1 0 M END

Standard InCHIKey	BIEZSEGUHJMPKG-FPLPWBNLSA-N
Standard InCHI	InChI=1S/C23H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-22-19-17-20-23(24)21-22/h7-8,17,19-21,24H,2-6,9-16,18H2,1H3/b8-7-
SMILES	CCCCCC/C=CCCCCCCCCCc1cccc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	330.29	Volume:	396.052 ? Van der Waals volume.
Dense:	0.834	LogP:	9.223 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.984 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.848 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	7.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.259	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.109	Fsp³:	0.652
MCE-18:	5.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.687	Fluc inhibitor:	0.434 ? 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:	0.163 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.98	Promiscuous compounds:	0.134

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.044	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.934	Pgp-substrate:	0.001
PAMPA:	0.0 ? 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):	0.08
20% Bioavailability (F20%):	0.814	30% Bioavailability (F30%):	0.985
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043	MRP1:	0.822
Plasma Protein Binding (PPB):	98.909%	Volume Distribution (VD):	0.383
Fu:	0.272% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.147
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.896
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.529
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.987
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.039	CYP2C8-inhibitor:	1.0
HLM stability:	0.299 ? 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):

4.994

Half-life (T1/2):

0.394

ADMET: Toxicity

hERG Blockers:	0.737	hERG Blockers (10um):	0.915
Human Hepatotoxicity (H-HT):	0.293	Drug-induced Liver Injury (DILI):	0.004
AMES Toxicity:	0.128	Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.383	Skin Sensitization:	1.0
Carcinogencity:	0.077	Eye Corrosion:	0.99
Eye Irritation:	0.995	Respiratory Toxicity:	0.81
Drug-induced Neurotoxicity:	0.025	Ototoxicity:	0.14
Hematotoxicity:	0.019	Drug-induced Nephrotoxicity:	0.313
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.954	Hek293 Cytotoxicity:	0.756
BCF:	1.419 ? 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:	5.472 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.316 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.409 ? 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
NPO28164	Knema laurina	Species	Myristicaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[21641207]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[27140807]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	n.a.	n.a.	PMID[33127538]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	fresh sarcotestas	Kwanak Campus of Seoul National University, Seoul, Korea	1996-Sep	PMID[9677265]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	St. Louis	1996-SEP	PMID[9834151]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834158]
NPO28164	Knema laurina	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Wood	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28164	Knema laurina	Species	Myristicaceae	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	7

Activity Type	# Activity
Cell line	4
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT657	Individual protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Bos taurus	IC50	=	9730.0	nM	PMID[16420055]
NPT657	Individual protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Bos taurus	IC50	=	95020.0	nM	Open TG-GATES in vivo data: Hematology
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	13114.0	nM	PMID[17850214]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	7.19	ug.mL-1	PMID[17125239]
NPT81	Cell line	A549	Homo sapiens	IC50	=	11.8	ug.mL-1	PMID[19285413]
NPT658	Cell line	HT1197	Homo sapiens	IC50	=	20.84	ug.mL-1	PMID[16919944]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	32.9	ug.mL-1	PMID[17950599]

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 NPC147284 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	24174
0.1-0.2	22582
0.2-0.3	2736
0.3-0.4	221
0.4-0.5	65
0.5-0.6	32
0.6-0.7	22
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC94139
0.9722	High Similarity	NPC483454
0.9722	High Similarity	NPC162314
0.875	High Similarity	NPC210497
0.8421	Intermediate Similarity	NPC487734
0.8333	Intermediate Similarity	NPC3358
0.8333	Intermediate Similarity	NPC306884
0.8333	Intermediate Similarity	NPC603092
0.7857	Intermediate Similarity	NPC192
0.7317	Intermediate Similarity	NPC487735
0.725	Intermediate Similarity	NPC146798
0.725	Intermediate Similarity	NPC222522
0.725	Intermediate Similarity	NPC106396
0.725	Intermediate Similarity	NPC94351
0.725	Intermediate Similarity	NPC168303
0.7	Intermediate Similarity	NPC53051
0.7	Intermediate Similarity	NPC24404
0.7	Intermediate Similarity	NPC313030
0.6923	Remote Similarity	NPC76938
0.6923	Remote Similarity	NPC32714
0.6757	Remote Similarity	NPC610566
0.6744	Remote Similarity	NPC71002
0.6744	Remote Similarity	NPC249828
0.6667	Remote Similarity	NPC196479
0.65	Remote Similarity	NPC470700
0.65	Remote Similarity	NPC54844
0.65	Remote Similarity	NPC39097
0.65	Remote Similarity	NPC302681
0.65	Remote Similarity	NPC118286
0.65	Remote Similarity	NPC109691
0.6429	Remote Similarity	NPC55561
0.6364	Remote Similarity	NPC302219
0.6364	Remote Similarity	NPC129373
0.6279	Remote Similarity	NPC232523
0.619	Remote Similarity	NPC39664
0.619	Remote Similarity	NPC177420
0.6136	Remote Similarity	NPC488413
0.6136	Remote Similarity	NPC488412
0.6	Remote Similarity	NPC242342
0.6	Remote Similarity	NPC85479
0.5909	Remote Similarity	NPC487736
0.58	Remote Similarity	NPC305603
0.5789	Remote Similarity	NPC606762
0.5778	Remote Similarity	NPC166761
0.575	Remote Similarity	NPC294186
0.575	Remote Similarity	NPC147310
0.575	Remote Similarity	NPC137415
0.575	Remote Similarity	NPC166313
0.575	Remote Similarity	NPC123273
0.575	Remote Similarity	NPC192032
0.575	Remote Similarity	NPC318325
0.575	Remote Similarity	NPC24407
0.575	Remote Similarity	NPC11280
0.5682	Remote Similarity	NPC280347
0.5652	Remote Similarity	NPC10588
0.5625	Remote Similarity	NPC48730
0.5625	Remote Similarity	NPC294741
0.5532	Remote Similarity	NPC158253
0.5532	Remote Similarity	NPC72947
0.5349	Remote Similarity	NPC241891
0.5349	Remote Similarity	NPC134829
0.5319	Remote Similarity	NPC284011
0.5319	Remote Similarity	NPC488416
0.5306	Remote Similarity	NPC219070
0.52	Remote Similarity	NPC483450
0.5192	Remote Similarity	NPC61033
0.5192	Remote Similarity	NPC249836
0.5135	Remote Similarity	NPC27974
0.5128	Remote Similarity	NPC210849
0.5116	Remote Similarity	NPC25493
0.5102	Remote Similarity	NPC470161
0.5091	Remote Similarity	NPC123559

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC147284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4814
0.1-0.2	4063
0.2-0.3	256
0.3-0.4	14
0.4-0.5	3
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