NPASS Compound

Natural Product: NPC471372

Natural Product ID	NPC471372
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Rel-(2R,5R,6R,8S,9S,10R,18S,19R)-2,19-Diacetoxy-18-Ethoxy-6-Methoxycleroda-3,13(16),14-Trien-18,19-Oxolane
IUPAC Name	[(1R,3S,5R,6aR,7S,8S,10R,10aR)-1-acetyloxy-3-ethoxy-10-methoxy-7,8-dimethyl-7-(3-methylidenepent-4-enyl)-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2419882
PubChem CID	73346139
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 -5.1659 -2.8462 -0.9212 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5194 -1.8208 -1.8234 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1800 -1.6600 -1.5863 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8926 -1.2537 -0.3264 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1819 -2.1247 0.4946 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2797 -1.3181 1.2567 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7074 -0.4881 0.0453 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1211 0.0104 -0.2530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4467 1.2589 -0.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4678 2.3756 -0.2497 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2231 2.8953 -1.5231 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6027 4.1358 -1.9816 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2259 4.8854 -1.2043 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2402 4.4949 -3.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2793 1.9715 0.5583 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 0.5524 0.5382 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6039 0.6454 -0.0495 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1019 -0.7629 -0.3001 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2119 -1.4047 -1.3378 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2296 -1.5421 -0.8636 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3680 -2.8611 -0.4395 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8532 -3.8190 -1.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2115 -1.6000 0.9439 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5021 1.3043 -1.3844 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4985 1.3131 0.9241 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8921 1.6350 0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8915 0.6269 0.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4355 0.5634 -0.9547 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4511 -0.3507 1.2308 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1279 -0.4889 2.4845 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0668 -0.5096 2.0661 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9638 -0.4105 3.4338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0734 -1.1194 3.9969 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8215 0.4640 4.2698 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9080 -3.4298 -1.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4245 -3.5638 -0.5141 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7047 -2.3440 -0.0981 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6614 -2.1405 -2.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0731 -0.8521 -1.7308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8933 -1.1598 0.1901 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5285 -1.9170 1.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4716 1.5376 -0.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0344 3.2086 0.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2688 3.6454 -4.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8765 5.3468 -3.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1945 4.9201 -3.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4850 2.7193 0.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5256 2.2784 1.6271 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4244 0.2816 1.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1078 -0.6663 -0.7144 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3180 -0.8492 -2.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6105 -2.4080 -1.5131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7702 -1.5170 -1.8154 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3108 -4.0138 -2.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5933 -4.8032 -0.6528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9235 -3.9550 -1.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2109 -2.0775 1.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5467 -2.5081 0.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8170 -1.1624 1.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4677 2.4060 -1.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2989 0.9265 -2.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5617 0.9546 -1.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5543 0.6893 1.8922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9760 2.2338 1.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9664 2.4004 -0.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3595 2.2638 1.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1426 1.2480 -1.7240 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1594 -0.1839 -1.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2280 -1.0492 0.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6044 -1.2543 3.1058 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4161 0.1191 2.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7554 0.6423 3.6633 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3500 1.4063 4.5551 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1737 -0.1245 5.1570 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 1 6 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 10 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 18 23 1 0 17 24 1 6 17 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 6 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 8 4 1 0 20 7 1 0 16 7 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 39 1 0 4 40 1 1 6 41 1 1 9 42 1 0 10 43 1 1 14 44 1 0 14 45 1 0 14 46 1 0 15 47 1 0 15 48 1 0 16 49 1 1 18 50 1 6 19 51 1 0 19 52 1 0 20 53 1 6 22 54 1 0 22 55 1 0 22 56 1 0 23 57 1 0 23 58 1 0 23 59 1 0 24 60 1 0 24 61 1 0 24 62 1 0 25 63 1 0 25 64 1 0 26 65 1 0 26 66 1 0 28 67 1 0 28 68 1 0 29 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	TWFKTSOJWWQSLG-XWOLWVNESA-N
Standard InCHI	InChI=1S/C27H40O7/c1-9-16(3)11-12-26(7)17(4)13-23(30-8)27-21(14-20(15-22(26)27)32-18(5)28)24(31-10-2)34-25(27)33-19(6)29/h9,14,17,20,22-25H,1,3,10-13,15H2,2,4-8H3/t17-,20-,22+,23+,24-,25-,26-,27-/m0/s1
SMILES	CCO[C@H]1O[C@@H]([C@]23C1=C[C@H](OC(=O)C)C[C@@H]3[C@@]([C@H](C[C@H]2OC)C)(C)CCC(=C)C=C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	476.28	Volume:	498.228 ? Van der Waals volume.
Dense:	0.956	LogP:	3.476 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.203 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.14 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	19.0
TPSA:	80.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.271	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.767	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:	0.443	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.371	Promiscuous compounds:	0.63

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.039	MDCK Permeability:	-4.787
Pgp-inhibitor:	0.982	Pgp-substrate:	0.03
PAMPA:	0.064 ? 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):	0.001
20% Bioavailability (F20%):	0.964	30% Bioavailability (F30%):	0.971
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.675	MRP1:	0.977
Plasma Protein Binding (PPB):	79.111%	Volume Distribution (VD):	0.147
Fu:	20.865% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.349
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.796	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.202	CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.009	CYP3A4-substrate:	0.746
CYP2B6-substrate:	0.037	CYP2C8-inhibitor:	0.989
HLM stability:	0.996 ? 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):

10.492

Half-life (T1/2):

1.214

ADMET: Toxicity

hERG Blockers:	0.101	hERG Blockers (10um):	0.393
Human Hepatotoxicity (H-HT):	0.325	Drug-induced Liver Injury (DILI):	0.856
AMES Toxicity:	0.92	Rat Oral Acute Toxicity:	0.813
Maximum Recommended Daily Dose:	0.842	Skin Sensitization:	0.983
Carcinogencity:	0.595	Eye Corrosion:	0.007
Eye Irritation:	0.202	Respiratory Toxicity:	0.548
Drug-induced Neurotoxicity:	0.608	Ototoxicity:	0.37
Hematotoxicity:	0.499	Drug-induced Nephrotoxicity:	0.669
Genotoxicity:	0.892	RPMI-8226 Immunitoxicity:	0.151
A549 Cytotoxicity:	0.584	Hek293 Cytotoxicity:	0.407
BCF:	0.85 ? 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:	3.73 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.495 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.862 ? 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
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[24033131]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	twigs	n.a.	n.a.	PMID[25286284]
NPO32459	casearia balansae	Species	Salicaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26699618]
NPO32459	casearia balansae	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	5

Activity Type	# Activity
Cell line	5

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
NPT1374	Cell line	WI-38	Homo sapiens	IC50	=	55700.0	nM	Open TG-GATES in vivo data: Hematology
NPT81	Cell line	A549	Homo sapiens	IC50	=	53300.0	nM	PMID[17027268]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	35900.0	nM	PMID[20472446]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	47200.0	nM	PMID[21652215]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	34200.0	nM	PMID[19667291]

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 NPC471372 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	21917
0.1-0.2	25754
0.2-0.3	2046
0.3-0.4	41
0.4-0.5	44
0.5-0.6	29
0.6-0.7	10
0.7-0.8	0
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471362
0.9091	High Similarity	NPC472189
0.8929	High Similarity	NPC171598
0.8596	High Similarity	NPC481018
0.8448	Intermediate Similarity	NPC481020
0.8333	Intermediate Similarity	NPC488649
0.8305	Intermediate Similarity	NPC318917
0.8305	Intermediate Similarity	NPC481019
0.8167	Intermediate Similarity	NPC472186
0.8167	Intermediate Similarity	NPC472188
0.8033	Intermediate Similarity	NPC471366
0.8033	Intermediate Similarity	NPC476800
0.8033	Intermediate Similarity	NPC488237
0.7903	Intermediate Similarity	NPC481017
0.7538	Intermediate Similarity	NPC472187
0.7302	Intermediate Similarity	NPC488236
0.697	Remote Similarity	NPC473545
0.6825	Remote Similarity	NPC606965
0.6462	Remote Similarity	NPC132395
0.6462	Remote Similarity	NPC471364
0.6462	Remote Similarity	NPC488651
0.6462	Remote Similarity	NPC488648
0.6462	Remote Similarity	NPC600724
0.625	Remote Similarity	NPC603601
0.6176	Remote Similarity	NPC473204
0.6087	Remote Similarity	NPC471365
0.5915	Remote Similarity	NPC48548
0.5833	Remote Similarity	NPC471363
0.5735	Remote Similarity	NPC479934
0.5652	Remote Similarity	NPC479935
0.5652	Remote Similarity	NPC479936
0.5652	Remote Similarity	NPC488235
0.561	Remote Similarity	NPC488962
0.5606	Remote Similarity	NPC488650
0.5606	Remote Similarity	NPC481022
0.5571	Remote Similarity	NPC479943
0.5479	Remote Similarity	NPC488963
0.5429	Remote Similarity	NPC479939
0.5417	Remote Similarity	NPC479940
0.5417	Remote Similarity	NPC7644
0.5405	Remote Similarity	NPC488219
0.5352	Remote Similarity	NPC479937
0.5342	Remote Similarity	NPC238397
0.5333	Remote Similarity	NPC488221
0.5333	Remote Similarity	NPC488220
0.5333	Remote Similarity	NPC488216
0.5278	Remote Similarity	NPC479938
0.5135	Remote Similarity	NPC217921
0.5135	Remote Similarity	NPC88013
0.5135	Remote Similarity	NPC475889
0.5135	Remote Similarity	NPC7613
0.5135	Remote Similarity	NPC479942
0.5135	Remote Similarity	NPC135015
0.5067	Remote Similarity	NPC479941
0.5063	Remote Similarity	NPC486752

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471372 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6964
0.1-0.2	2169
0.2-0.3	17
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