NPASS Compound

Natural Product: NPC479491

Natural Product ID	NPC479491
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SYKRCLPYCLOJHX-BCLGWYQUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 77 79 0 0 0 0 0 0 0 0999 V2000 6.5795 -1.5864 0.6277 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0317 -2.1510 -0.6580 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4988 -3.5320 -0.4225 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9679 -1.2535 -1.2248 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8244 -1.0800 -0.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7429 -1.6145 0.8306 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7833 -0.2734 -0.7098 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6240 -0.0334 0.1068 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5498 1.4522 0.2703 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4093 2.0476 0.3990 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0217 3.4625 0.5701 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0818 4.3478 0.2581 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6438 5.2550 1.1114 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1815 5.3166 2.2890 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7524 6.1154 0.6334 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0399 3.5871 -0.2801 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 2.3607 -0.5545 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9450 1.3581 0.4011 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9022 0.0182 -0.1805 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4534 -0.4044 -0.7481 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5160 -1.0690 0.6566 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6375 -1.4469 1.8626 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7119 -2.3591 -0.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5684 -2.3170 -1.2360 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6774 -3.0237 -1.3669 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0977 -3.9258 -0.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5169 -2.9618 -2.5494 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5663 -3.6277 -2.6781 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7860 -0.5956 1.2498 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8757 -0.1765 0.3665 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4578 0.4915 2.2454 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5542 1.5546 1.7267 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3129 2.7573 1.7742 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4499 1.9725 -1.8965 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5129 1.8140 -2.7368 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6700 2.0242 -2.2925 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3651 1.3980 -4.1746 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6393 -1.2667 0.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9915 -0.7024 0.9159 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5325 -2.3088 1.4581 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8526 -2.1970 -1.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3839 -4.2212 -0.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9770 -3.5829 0.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8353 -3.7988 -1.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6282 -1.6609 -2.2031 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4643 -0.2764 -1.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7749 -0.5891 1.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4630 2.0277 0.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2122 3.7007 1.6476 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4090 6.8870 -0.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2129 6.6767 1.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5529 5.5482 0.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6977 2.4794 -0.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5521 0.0186 -1.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5832 0.2130 -1.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4295 -1.4375 -1.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1202 -2.1920 1.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1923 -0.5948 2.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2888 -1.9386 2.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2082 -3.0523 0.6794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7498 -2.8966 -0.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3042 -1.6715 -2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2500 -4.6254 -0.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9616 -4.5479 -0.5478 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3641 -3.3768 0.6554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2199 -2.3112 -3.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1720 -1.4604 1.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8290 -0.7681 0.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7075 -0.2017 -0.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2068 0.8799 0.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0220 -0.0063 3.1593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4382 0.8780 2.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7680 1.7432 2.4918 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8843 2.7773 2.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3244 1.3959 -4.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8690 0.4223 -4.3104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9928 2.1357 -4.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 11 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 25 27 1 0 27 28 2 0 21 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 32 33 1 0 17 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 20 8 1 0 18 10 1 1 32 18 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 3 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 8 47 1 1 9 48 1 0 11 49 1 1 15 50 1 0 15 51 1 0 15 52 1 0 17 53 1 1 19 54 1 6 20 55 1 0 20 56 1 0 22 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 26 63 1 0 26 64 1 0 26 65 1 0 27 66 1 0 29 67 1 1 30 68 1 0 30 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 32 73 1 1 33 74 1 0 37 75 1 0 37 76 1 0 37 77 1 0 M END

Standard InCHIKey	SYKRCLPYCLOJHX-BCLGWYQUSA-N
Standard InCHI	InChI=1S/C28H40O9/c1-15(2)10-24(33)36-20-12-21-25(34-18(5)30)37-26(35-19(6)31)28(21)22(13-20)27(7,9-8-16(3)14-29)17(4)11-23(28)32/h8,12,14-15,17,20,22-23,25-26,32H,9-11,13H2,1-7H3/b16-8+/t17-,20+,22+,23+,25+,26-,27-,28-/m1/s1
SMILES	CC(C)CC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@]32[C@@H](C1)[C@](C)(C/C=C(C)/C=O)[C@H](C)C[C@@H]3O)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	520.27	Volume:	530.468 ? Van der Waals volume.
Dense:	0.981	LogP:	3.129 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.199 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.129 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	20.0
TPSA:	125.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.738	Fsp³:	0.714
MCE-18:	92.25 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.731	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.294	Promiscuous compounds:	0.68

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.848	MDCK Permeability:	-4.643
Pgp-inhibitor:	0.022	Pgp-substrate:	0.819
PAMPA:	0.908 ? 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):	0.031
20% Bioavailability (F20%):	0.853	30% Bioavailability (F30%):	0.855
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.829	MRP1:	0.968
Plasma Protein Binding (PPB):	64.915%	Volume Distribution (VD):	-0.394
Fu:	29.771% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.023
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.765	CYP2C19-substrate:	0.459
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.589	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.83
HLM stability:	0.969 ? 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):

6.42

Half-life (T1/2):

1.014

ADMET: Toxicity

hERG Blockers:	0.078	hERG Blockers (10um):	0.288
Human Hepatotoxicity (H-HT):	0.679	Drug-induced Liver Injury (DILI):	0.876
AMES Toxicity:	0.972	Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.991	Skin Sensitization:	0.988
Carcinogencity:	0.784	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.732
Drug-induced Neurotoxicity:	0.918	Ototoxicity:	0.56
Hematotoxicity:	0.768	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.998	RPMI-8226 Immunitoxicity:	0.447
A549 Cytotoxicity:	0.852	Hek293 Cytotoxicity:	0.505
BCF:	0.799 ? 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:	3.758 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.6 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.097 ? 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
NPO40811	Casearia kurzii	Species	Salicaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[33001650]
NPO40811	Casearia kurzii	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	13

Activity Type	# Activity
Cell line	14

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
NPT81	Cell line	A549	Homo sapiens	IC50	=	4400.0	nM	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	6.14	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	27.45	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	11.09	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	56.99	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	23.87	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	19.14	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	44.84	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	34.59	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	20.56	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	6.04	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	9.94	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	13.7	%	PMID[33001650]
NPT81	Cell line	A549	Homo sapiens	Activity	=	25.27	%	PMID[33001650]

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 NPC479491 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	18536
0.1-0.2	27719
0.2-0.3	3467
0.3-0.4	52
0.4-0.5	33
0.5-0.6	15
0.6-0.7	16
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8387	Intermediate Similarity	NPC81567
0.8387	Intermediate Similarity	NPC488652
0.7812	Intermediate Similarity	NPC488654
0.7619	Intermediate Similarity	NPC602188
0.7538	Intermediate Similarity	NPC201880
0.7273	Intermediate Similarity	NPC479940
0.7273	Intermediate Similarity	NPC479497
0.7273	Intermediate Similarity	NPC329623
0.7273	Intermediate Similarity	NPC609711
0.7231	Intermediate Similarity	NPC488653
0.7206	Intermediate Similarity	NPC488964
0.7206	Intermediate Similarity	NPC184512
0.7164	Intermediate Similarity	NPC330003
0.7164	Intermediate Similarity	NPC470321
0.7164	Intermediate Similarity	NPC264867
0.7164	Intermediate Similarity	NPC473207
0.7164	Intermediate Similarity	NPC609715
0.7077	Intermediate Similarity	NPC488659
0.7077	Intermediate Similarity	NPC604149
0.7015	Intermediate Similarity	NPC134270
0.6765	Remote Similarity	NPC488660
0.6765	Remote Similarity	NPC488657
0.6765	Remote Similarity	NPC609880
0.6716	Remote Similarity	NPC479943
0.6714	Remote Similarity	NPC252296
0.6667	Remote Similarity	NPC488658
0.6667	Remote Similarity	NPC488655
0.6522	Remote Similarity	NPC7644
0.6522	Remote Similarity	NPC316974
0.6286	Remote Similarity	NPC311223
0.6232	Remote Similarity	NPC488656
0.6197	Remote Similarity	NPC475889
0.6197	Remote Similarity	NPC7613
0.6197	Remote Similarity	NPC479942
0.6154	Remote Similarity	NPC109376
0.6111	Remote Similarity	NPC479941
0.5897	Remote Similarity	NPC116292
0.5833	Remote Similarity	NPC128795
0.5753	Remote Similarity	NPC238397
0.5658	Remote Similarity	NPC127933
0.56	Remote Similarity	NPC471363
0.5366	Remote Similarity	NPC486751
0.5357	Remote Similarity	NPC224660
0.5333	Remote Similarity	NPC217921
0.5333	Remote Similarity	NPC135015
0.5132	Remote Similarity	NPC88013
0.5128	Remote Similarity	NPC119550
0.5122	Remote Similarity	NPC87630
0.5072	Remote Similarity	NPC604446
0.507	Remote Similarity	NPC603601
0.5068	Remote Similarity	NPC600724

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6732
0.1-0.2	2393
0.2-0.3	25
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