NPASS Compound

Natural Product: NPC134270

Natural Product ID	NPC134270
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Caseargrewins G
IUPAC Name	[(1S,3S,5R,6aS,7R,8R,10S,10aS)-1-acetyloxy-10-hydroxy-3-methoxy-7,8-dimethyl-7-[(2Z)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] butanoate
Synonyms	caseargrewins G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL231215
PubChem CID	16756886
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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 74 76 0 0 0 0 0 0 0 0999 V2000 7.1235 -3.0064 -0.6045 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8127 -2.3915 -0.1750 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8694 -0.8663 -0.1988 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5274 -0.3843 0.2424 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1756 -0.3282 1.4447 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5830 0.0352 -0.6807 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3432 0.4813 -0.2771 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0615 1.9108 -0.6493 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8105 2.2492 -0.4853 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1154 3.5959 -0.7588 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8603 4.3907 -1.5813 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8978 5.6809 -1.0542 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8939 2.9841 -1.5705 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4288 2.1585 -0.4946 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2900 1.3748 0.0714 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1339 -0.0393 -0.3179 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2118 -0.2184 -1.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3349 -1.1503 0.6391 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8654 -2.1477 0.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4754 -2.0990 0.3779 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8349 -1.6981 0.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6620 -1.9883 -0.6478 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2929 -2.7609 -1.8328 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2291 -2.9918 -2.7658 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0984 -1.5519 -0.4918 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1750 -0.8135 2.0901 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6868 0.5432 2.4446 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1824 1.6255 1.5677 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9661 2.7560 1.8734 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8259 -1.8136 3.0045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5927 1.5914 -0.9284 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7968 2.2070 -0.5287 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6929 3.2130 0.2121 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1435 1.7741 -0.9111 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6397 -2.3004 -1.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7846 -3.2561 0.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9764 -3.9511 -1.2070 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9797 -2.6819 -0.8596 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6226 -2.7108 0.8706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6566 -0.5955 0.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1477 -0.4726 -1.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2568 0.4451 0.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7951 2.5916 -1.0108 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3101 4.0338 0.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5108 6.3348 -1.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2469 5.6637 -0.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1454 6.1153 -1.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6267 3.0209 0.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8910 -0.2160 -1.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1067 0.3478 -2.0007 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4391 -1.2299 -1.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6738 -2.7876 -0.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8190 -1.7291 0.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7117 -2.8792 1.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2234 -2.5922 -0.6286 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4039 -2.9908 1.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2493 -1.1102 1.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3145 -3.1669 -2.0170 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9464 -3.5580 -3.6277 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2399 -2.6390 -2.6877 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4132 -1.0690 -1.4265 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2228 -0.8686 0.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7359 -2.4435 -0.2581 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9186 -0.8074 2.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3351 0.7715 3.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8144 0.5807 2.5223 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 1.9248 1.8583 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1719 2.7791 2.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5634 -1.5939 4.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9504 -1.7277 3.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4993 -2.8542 2.8772 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7501 1.3639 -0.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1538 1.2004 -1.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6861 2.7361 -1.2032 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 22 25 1 0 18 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 26 30 1 0 14 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 17 7 1 0 15 9 1 6 28 15 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 39 1 0 3 40 1 0 3 41 1 0 7 42 1 1 8 43 1 0 10 44 1 1 12 45 1 0 12 46 1 0 12 47 1 0 14 48 1 1 16 49 1 6 17 50 1 0 17 51 1 0 19 52 1 0 19 53 1 0 19 54 1 0 20 55 1 0 20 56 1 0 21 57 1 0 23 58 1 0 24 59 1 0 24 60 1 0 25 61 1 0 25 62 1 0 25 63 1 0 26 64 1 1 27 65 1 0 27 66 1 0 28 67 1 1 29 68 1 0 30 69 1 0 30 70 1 0 30 71 1 0 34 72 1 0 34 73 1 0 34 74 1 0 M END

Standard InCHIKey	HYYVVSPRNZXNBO-MXRYFZCASA-N
Standard InCHI	InChI=1S/C27H40O7/c1-8-10-23(30)33-19-14-20-24(31-7)34-25(32-18(5)28)27(20)21(15-19)26(6,12-11-16(3)9-2)17(4)13-22(27)29/h9,11,14,17,19,21-22,24-25,29H,2,8,10,12-13,15H2,1,3-7H3/b16-11-/t17-,19+,21+,22+,24+,25-,26-,27-/m1/s1
SMILES	CCCC(=O)O[C@H]1C=C2[C@@H](OC)O[C@H]([C@]32[C@@H](C1)[C@](C)(C/C=C(C=C)/C)[C@@H](C[C@@H]3O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.28	Volume:	498.228 ? Van der Waals volume.
Dense:	0.956	LogP:	3.621 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.376 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.995 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	19.0
TPSA:	91.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.314	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.75	Fsp³:	0.704
MCE-18:	85.87 ? 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:	0.58	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.332	Promiscuous compounds:	0.66

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.313	MDCK Permeability:	-5.005
Pgp-inhibitor:	0.855	Pgp-substrate:	0.961
PAMPA:	0.48 ? 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):	0.037
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.989
Plasma Protein Binding (PPB):	80.367%	Volume Distribution (VD):	-0.22
Fu:	15.035% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.802	BCRP inhibitor:	0.317
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.229	CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.603	CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.113	CYP3A4-substrate:	0.108
CYP2B6-substrate:	0.057	CYP2C8-inhibitor:	0.986
HLM stability:	0.999 ? 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):

9.192

Half-life (T1/2):

1.085

ADMET: Toxicity

hERG Blockers:	0.11	hERG Blockers (10um):	0.56
Human Hepatotoxicity (H-HT):	0.418	Drug-induced Liver Injury (DILI):	0.754
AMES Toxicity:	0.838	Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.994	Skin Sensitization:	0.985
Carcinogencity:	0.522	Eye Corrosion:	0.0
Eye Irritation:	0.129	Respiratory Toxicity:	0.988
Drug-induced Neurotoxicity:	0.907	Ototoxicity:	0.623
Hematotoxicity:	0.626	Drug-induced Nephrotoxicity:	0.823
Genotoxicity:	0.917	RPMI-8226 Immunitoxicity:	0.336
A549 Cytotoxicity:	0.655	Hek293 Cytotoxicity:	0.461
BCF:	0.871 ? 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:	3.671 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.522 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.827 ? 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
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	bark	n.a.	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	bark	in the campus of Khon Kaen University, Khon Kaen, Thailand	2001-SEP	PMID[15730240]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17567069]
NPO31460	Casearia grewiifolia	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26516994]
NPO31460	Casearia grewiifolia	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	3

Activity Type	# Activity
Cell line	2
Non-molecular	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
NPT91	Cell line	KB	Homo sapiens	IC50	=	0.67	ug.mL-1	PMID[8277309]
NPT639	Cell line	NCI-H187	Homo sapiens	IC50	=	5.57	ug.mL-1	PMID[12398531]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3.97	ug.mL-1	PMID[17567069]

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 NPC134270 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	17731
0.1-0.2	28014
0.2-0.3	3965
0.3-0.4	38
0.4-0.5	47
0.5-0.6	21
0.6-0.7	14
0.7-0.8	0
0.8-0.85	6
0.85-0.9	8
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9322	High Similarity	NPC201880
0.918	High Similarity	NPC252296
0.9167	High Similarity	NPC609715
0.9138	High Similarity	NPC488659
0.9138	High Similarity	NPC604149
0.9	High Similarity	NPC488654
0.8689	High Similarity	NPC488660
0.8689	High Similarity	NPC488657
0.8689	High Similarity	NPC609880
0.8571	High Similarity	NPC488964
0.8571	High Similarity	NPC184512
0.8548	High Similarity	NPC488658
0.8548	High Similarity	NPC488655
0.85	High Similarity	NPC602188
0.8387	Intermediate Similarity	NPC81567
0.8387	Intermediate Similarity	NPC488652
0.8361	Intermediate Similarity	NPC488653
0.8095	Intermediate Similarity	NPC329623
0.8095	Intermediate Similarity	NPC609711
0.8065	Intermediate Similarity	NPC488656
0.7969	Intermediate Similarity	NPC330003
0.7969	Intermediate Similarity	NPC470321
0.7969	Intermediate Similarity	NPC264867
0.7969	Intermediate Similarity	NPC473207
0.7273	Intermediate Similarity	NPC7644
0.7101	Intermediate Similarity	NPC119550
0.7027	Intermediate Similarity	NPC109376
0.7015	Intermediate Similarity	NPC479491
0.6716	Remote Similarity	NPC479943
0.6667	Remote Similarity	NPC238397
0.6533	Remote Similarity	NPC116292
0.6528	Remote Similarity	NPC127933
0.6522	Remote Similarity	NPC479940
0.6522	Remote Similarity	NPC316974
0.6522	Remote Similarity	NPC479497
0.6286	Remote Similarity	NPC311223
0.6197	Remote Similarity	NPC475889
0.6197	Remote Similarity	NPC7613
0.6197	Remote Similarity	NPC479942
0.6111	Remote Similarity	NPC479941
0.6087	Remote Similarity	NPC88507
0.6027	Remote Similarity	NPC471363
0.5972	Remote Similarity	NPC217921
0.5972	Remote Similarity	NPC135015
0.5952	Remote Similarity	NPC320734
0.5942	Remote Similarity	NPC600724
0.5797	Remote Similarity	NPC606965
0.5758	Remote Similarity	NPC604446
0.5753	Remote Similarity	NPC88013
0.5735	Remote Similarity	NPC603601
0.5616	Remote Similarity	NPC311166
0.5542	Remote Similarity	NPC224660
0.55	Remote Similarity	NPC179128
0.5479	Remote Similarity	NPC473204
0.5417	Remote Similarity	NPC488235
0.5366	Remote Similarity	NPC316708
0.5366	Remote Similarity	NPC486751
0.5256	Remote Similarity	NPC40728
0.52	Remote Similarity	NPC128795
0.5132	Remote Similarity	NPC218158
0.5128	Remote Similarity	NPC125423
0.5122	Remote Similarity	NPC87630
0.5068	Remote Similarity	NPC481020

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC134270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6956
0.1-0.2	2157
0.2-0.3	37
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