NPASS Compound

Natural Product: NPC252296

Natural Product ID	NPC252296
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Caseargrewins J
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] hexanoate
Synonyms	caseargrewins J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL231314
PubChem CID	16756889
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 80 82 0 0 0 0 0 0 0 0999 V2000 7.7638 -0.2014 -0.3166 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7854 0.3408 0.6940 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3378 1.7042 0.2279 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3556 2.3367 1.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0950 1.5637 1.3712 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3154 1.3558 0.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6969 1.8340 -0.9902 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1411 0.6227 0.1638 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4276 0.4472 -1.0507 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4175 -0.9774 -1.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3643 -1.7159 -1.5292 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0881 -3.1570 -1.8869 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1394 -3.9770 -1.4799 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6216 -4.7089 -2.5611 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0380 -3.5283 -1.1868 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4903 -2.4126 -0.4454 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0515 -1.2164 -1.2565 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0440 0.0747 -0.5395 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0677 1.0053 -0.9698 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3061 0.8896 -0.6437 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9247 2.3315 -0.2183 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3731 0.5170 0.3764 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9370 0.7136 1.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5272 1.4976 2.6575 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7102 2.2612 2.2972 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2465 3.0321 3.2531 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9413 1.5713 4.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8418 0.9944 -2.0236 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2666 0.0727 -3.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8642 -1.2616 -2.5225 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9716 -2.1375 -2.4070 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3645 0.9039 -2.0153 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8409 -2.4069 0.7930 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5545 -2.6321 1.9567 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7927 -2.8396 1.8671 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9005 -2.6350 3.2975 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5285 -1.2759 -0.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7690 0.4004 -1.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8005 -0.2091 0.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8880 -0.3124 0.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2827 0.3791 1.6749 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2685 2.3455 0.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9873 1.6396 -0.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0648 3.3502 0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8409 2.5361 2.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2698 0.5538 1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4770 2.1443 2.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9698 0.9705 -1.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 -1.4383 -1.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0654 -3.3196 -2.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7789 -5.3403 -2.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4634 -5.3441 -2.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9221 -4.0479 -3.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5833 -2.5709 -0.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8599 -0.1261 0.5333 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1179 1.8077 -0.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1703 1.5435 -1.9038 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9443 2.8283 -0.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5350 2.3647 0.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3791 2.8667 -0.9841 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6242 -0.5836 0.3164 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2309 1.1416 0.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0380 0.1638 2.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1961 2.2671 1.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 3.6371 3.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7802 3.0422 4.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4537 2.5528 4.1804 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7550 1.3734 4.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1835 0.7944 4.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6566 2.0367 -2.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0765 -0.1100 -3.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4352 0.5049 -3.6434 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2343 -1.7227 -3.3094 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7423 -1.7862 -2.9521 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7466 0.7531 -3.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8441 1.8201 -1.6603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6355 -0.0193 -1.4700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.6099 3.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4632 -3.2433 4.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1496 -3.0208 3.2237 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 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 20 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 28 32 1 0 16 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 19 9 1 0 17 11 1 6 30 17 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 0 2 41 1 0 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 5 46 1 0 5 47 1 0 9 48 1 6 10 49 1 0 12 50 1 6 14 51 1 0 14 52 1 0 14 53 1 0 16 54 1 1 18 55 1 1 19 56 1 0 19 57 1 0 21 58 1 0 21 59 1 0 21 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 25 64 1 0 26 65 1 0 26 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 6 29 71 1 0 29 72 1 0 30 73 1 6 31 74 1 0 32 75 1 0 32 76 1 0 32 77 1 0 36 78 1 0 36 79 1 0 36 80 1 0 M END

Standard InCHIKey	LNLATCNMZQLNMH-JHAOYEHPSA-N
Standard InCHI	InChI=1S/C29H44O7/c1-8-10-11-12-25(32)35-21-16-22-26(33-7)36-27(34-20(5)30)29(22)23(17-21)28(6,14-13-18(3)9-2)19(4)15-24(29)31/h9,13,16,19,21,23-24,26-27,31H,2,8,10-12,14-15,17H2,1,3-7H3/b18-13-/t19-,21+,23+,24+,26+,27-,28-,29-/m1/s1
SMILES	CCCCCC(=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:	504.31	Volume:	532.82 ? Van der Waals volume.
Dense:	0.946	LogP:	4.279 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.698 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.291 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	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:	0.188	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.672	Fsp³:	0.724
MCE-18:	85.0 ? 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:	0.591	Fluc inhibitor:	0.001 ? 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:	0.274	Promiscuous compounds:	0.65

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.277	MDCK Permeability:	-5.011
Pgp-inhibitor:	0.697	Pgp-substrate:	0.953
PAMPA:	0.417 ? 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):	0.019
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011	MRP1:	0.99
Plasma Protein Binding (PPB):	92.658%	Volume Distribution (VD):	-0.266
Fu:	6.469% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.976
OATP1B3 inhibitor:	0.652	BCRP inhibitor:	0.383
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.825	CYP2C19-substrate:	0.129
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.016	CYP2D6-substrate:	0.347
CYP3A4-inhibitor:	0.018	CYP3A4-substrate:	0.945
CYP2B6-substrate:	0.326	CYP2C8-inhibitor:	0.999
HLM stability:	0.998 ? 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):

7.707

Half-life (T1/2):

0.803

ADMET: Toxicity

hERG Blockers:	0.175	hERG Blockers (10um):	0.665
Human Hepatotoxicity (H-HT):	0.439	Drug-induced Liver Injury (DILI):	0.793
AMES Toxicity:	0.849	Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	0.995
Carcinogencity:	0.466	Eye Corrosion:	0.0
Eye Irritation:	0.169	Respiratory Toxicity:	0.992
Drug-induced Neurotoxicity:	0.889	Ototoxicity:	0.592
Hematotoxicity:	0.582	Drug-induced Nephrotoxicity:	0.827
Genotoxicity:	0.68	RPMI-8226 Immunitoxicity:	0.34
A549 Cytotoxicity:	0.837	Hek293 Cytotoxicity:	0.517
BCF:	1.192 ? 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:	4.041 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.736 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.135 ? 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	2

Activity Type	# Activity
Cell line	1
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
NPT639	Cell line	NCI-H187	Homo sapiens	IC50	=	1.22	ug.mL-1	PMID[25479041]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	0.99	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 NPC252296 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	17480
0.1-0.2	28028
0.2-0.3	4194
0.3-0.4	47
0.4-0.5	50
0.5-0.6	22
0.6-0.7	11
0.7-0.8	0
0.8-0.85	9
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC488964
0.9355	High Similarity	NPC184512
0.918	High Similarity	NPC134270
0.8689	High Similarity	NPC488659
0.8689	High Similarity	NPC604149
0.8571	High Similarity	NPC201880
0.8571	High Similarity	NPC488654
0.8438	Intermediate Similarity	NPC609715
0.8281	Intermediate Similarity	NPC488660
0.8281	Intermediate Similarity	NPC488657
0.8281	Intermediate Similarity	NPC609880
0.8154	Intermediate Similarity	NPC488658
0.8154	Intermediate Similarity	NPC488655
0.8095	Intermediate Similarity	NPC602188
0.8	Intermediate Similarity	NPC81567
0.8	Intermediate Similarity	NPC488652
0.7969	Intermediate Similarity	NPC488653
0.7794	Intermediate Similarity	NPC119550
0.7727	Intermediate Similarity	NPC329623
0.7727	Intermediate Similarity	NPC609711
0.7692	Intermediate Similarity	NPC488656
0.7612	Intermediate Similarity	NPC330003
0.7612	Intermediate Similarity	NPC470321
0.7612	Intermediate Similarity	NPC264867
0.7612	Intermediate Similarity	NPC473207
0.72	Intermediate Similarity	NPC109376
0.6714	Remote Similarity	NPC7644
0.6714	Remote Similarity	NPC479491
0.6479	Remote Similarity	NPC316974
0.6429	Remote Similarity	NPC479943
0.6389	Remote Similarity	NPC238397
0.6282	Remote Similarity	NPC116292
0.625	Remote Similarity	NPC479940
0.625	Remote Similarity	NPC311166
0.625	Remote Similarity	NPC479497
0.6053	Remote Similarity	NPC127933
0.6027	Remote Similarity	NPC311223
0.5946	Remote Similarity	NPC475889
0.5946	Remote Similarity	NPC7613
0.5946	Remote Similarity	NPC479942
0.5867	Remote Similarity	NPC479941
0.5789	Remote Similarity	NPC471363
0.5747	Remote Similarity	NPC320734
0.5733	Remote Similarity	NPC217921
0.5733	Remote Similarity	NPC135015
0.5714	Remote Similarity	NPC224660
0.5694	Remote Similarity	NPC600724
0.5616	Remote Similarity	NPC88507
0.5556	Remote Similarity	NPC606965
0.5542	Remote Similarity	NPC316708
0.5507	Remote Similarity	NPC604446
0.5493	Remote Similarity	NPC603601
0.5325	Remote Similarity	NPC88013
0.5301	Remote Similarity	NPC179128
0.5263	Remote Similarity	NPC473204
0.52	Remote Similarity	NPC488235
0.5195	Remote Similarity	NPC128795
0.5176	Remote Similarity	NPC486751
0.5062	Remote Similarity	NPC40728

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6831
0.1-0.2	2257
0.2-0.3	62
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