NPASS Compound

Natural Product: NPC155676

Natural Product ID	NPC155676
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(20')-16-Alpha,25-Dihydroxy-3-Oxo-24-Methyllanosta-7,9(11),24(241)-Trien-21-Oic Acid]
IUPAC Name	6-hydroxy-2-[(5R,10S,13R,14R,16R,17R)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	16-alpha,25-dihydroxydehydroeburiconic acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL387874
PubChem CID	16737365
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

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 82 85 0 0 0 0 0 0 0 0999 V2000 7.0904 0.4016 -0.5787 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9661 -0.1559 -0.1488 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9832 0.6780 0.5332 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6187 0.7619 -0.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8217 1.6945 0.7661 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4462 1.9489 0.3548 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2648 2.5679 -1.0098 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1787 2.1985 -1.3977 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7447 1.6570 -0.1028 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0637 2.7811 0.8556 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8997 0.7832 -0.2226 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8741 1.0295 -1.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0693 0.1617 -1.2224 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3431 -0.4362 0.1503 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6917 -1.0343 0.2658 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4332 -0.5025 1.5011 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5906 -0.7209 -0.9152 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5745 -2.5069 0.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2431 -3.2392 -0.2401 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6583 -2.9591 1.5267 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4237 -2.1284 1.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1838 -1.3062 0.4826 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8048 -2.2549 -0.6388 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9888 -0.3999 0.6210 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0312 -0.6957 1.4927 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1822 0.1708 1.6461 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4678 0.8398 0.3357 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7080 -0.1770 -0.7571 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3121 3.9696 -0.9523 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5645 2.9608 0.8538 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9439 3.3840 1.9590 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8425 3.6816 -0.2842 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7907 -1.5972 -0.3953 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6656 -1.9237 -1.3240 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5762 -2.3583 0.9209 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9647 -2.1734 -0.9355 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2575 1.4508 -0.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8452 -0.1713 -1.0867 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 1.7233 0.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8283 0.3518 1.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7393 1.1150 -1.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1893 -0.2814 -0.0294 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8028 1.2233 1.7726 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0324 2.7209 1.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9880 2.2435 -1.7533 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2119 1.4626 -2.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7577 3.0901 -1.6831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6347 3.7522 0.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1811 2.9399 0.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8519 2.5353 1.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8069 1.9040 -1.6970 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9166 -0.5828 -2.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9300 0.8240 -1.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3032 0.4459 0.8577 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5001 -0.3652 1.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3007 -1.1967 2.3637 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9817 0.4806 1.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1251 -0.9204 -1.8797 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8808 0.3495 -0.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4950 -1.3643 -0.8305 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2569 -2.9728 2.4855 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4346 -4.0400 1.3375 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4362 -1.5404 2.6410 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5826 -2.8731 1.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2658 -1.7113 -1.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0578 -2.9584 -0.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6366 -2.8477 -1.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0913 -1.5595 2.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1284 0.8630 2.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0510 -0.5172 1.8479 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9957 -1.1844 -0.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3846 0.1617 -1.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2722 -0.3922 -1.2627 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9631 4.3052 -1.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4302 4.5085 -0.3045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3683 -1.0554 -1.9143 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8360 -2.4166 -0.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9948 -2.6889 -2.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3077 -2.0016 1.6767 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5357 -2.2960 1.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7842 -3.4245 0.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6362 -2.1895 -0.2018 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 6 7 29 1 0 5 30 1 0 30 31 2 0 30 32 1 0 2 33 1 0 33 34 1 0 33 35 1 0 33 36 1 0 27 6 1 0 27 9 1 0 24 11 1 0 22 14 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 6 44 1 1 7 45 1 6 8 46 1 0 8 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 1 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 32 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 36 82 1 0 M END

Standard InCHIKey	SQDBINMAYPNYDY-BBQKHDEISA-N
Standard InCHI	InChI=1S/C31H46O5/c1-18(28(4,5)36)9-10-19(26(34)35)25-22(32)17-31(8)21-11-12-23-27(2,3)24(33)14-15-29(23,6)20(21)13-16-30(25,31)7/h11,13,19,22-23,25,32,36H,1,9-10,12,14-17H2,2-8H3,(H,34,35)/t19?,22-,23+,25+,29-,30-,31+/m1/s1
SMILES	C=C(CCC([C@H]1[C@@H](C[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C)O)C(=O)O)C(C)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.33	Volume:	541.275 ? Van der Waals volume.
Dense:	0.921	LogP:	2.892 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.71 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.02 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	23.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.399	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.234	Fsp³:	0.742
MCE-18:	88.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.733	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.307	Promiscuous compounds:	0.046

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097	MDCK Permeability:	-4.799
Pgp-inhibitor:	0.001	Pgp-substrate:	0.0
PAMPA:	0.992 ? 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):	0.0
20% Bioavailability (F20%):	0.014	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.991
Plasma Protein Binding (PPB):	81.535%	Volume Distribution (VD):	-0.183
Fu:	19.86% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.1
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.941
HLM stability:	0.197 ? 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):

5.422

Half-life (T1/2):

0.781

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.071
Human Hepatotoxicity (H-HT):	0.603	Drug-induced Liver Injury (DILI):	0.15
AMES Toxicity:	0.237	Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.397	Skin Sensitization:	0.731
Carcinogencity:	0.654	Eye Corrosion:	0.006
Eye Irritation:	0.314	Respiratory Toxicity:	0.52
Drug-induced Neurotoxicity:	0.089	Ototoxicity:	0.606
Hematotoxicity:	0.505	Drug-induced Nephrotoxicity:	0.699
Genotoxicity:	0.94	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.064	Hek293 Cytotoxicity:	0.299
BCF:	0.495 ? 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:	3.373 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.013 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.057 ? 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
NPO33546	Poria coco	Species	n.a.	Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO10608	Exodermis poria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

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
Inhibition	4
Activity	1

Activity Type	# Activity
Cell line	1
Organism	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	39.5	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	65.3	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	91.7	%	PMID[17488130]

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 NPC155676 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	18414
0.1-0.2	27627
0.2-0.3	3467
0.3-0.4	271
0.4-0.5	46
0.5-0.6	17
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8594	High Similarity	NPC152897
0.8	Intermediate Similarity	NPC66429
0.7353	Intermediate Similarity	NPC186810
0.7286	Intermediate Similarity	NPC263347
0.6714	Remote Similarity	NPC243866
0.6667	Remote Similarity	NPC7165
0.6479	Remote Similarity	NPC45269
0.625	Remote Similarity	NPC45324
0.625	Remote Similarity	NPC162001
0.6164	Remote Similarity	NPC484975
0.6164	Remote Similarity	NPC321301
0.6111	Remote Similarity	NPC69279
0.6081	Remote Similarity	NPC484967
0.6053	Remote Similarity	NPC288464
0.6053	Remote Similarity	NPC477813
0.6053	Remote Similarity	NPC607198
0.5974	Remote Similarity	NPC469432
0.5753	Remote Similarity	NPC222845
0.5753	Remote Similarity	NPC296577
0.5733	Remote Similarity	NPC484966
0.5676	Remote Similarity	NPC54689
0.5658	Remote Similarity	NPC123854
0.5641	Remote Similarity	NPC484969
0.5616	Remote Similarity	NPC83569
0.5526	Remote Similarity	NPC48647
0.5467	Remote Similarity	NPC48866
0.527	Remote Similarity	NPC89077
0.5132	Remote Similarity	NPC247406
0.5125	Remote Similarity	NPC478312
0.5065	Remote Similarity	NPC44181
0.5065	Remote Similarity	NPC87552
0.5065	Remote Similarity	NPC606857
0.5063	Remote Similarity	NPC484968

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC155676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5768
0.1-0.2	3273
0.2-0.3	109
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