NPASS Compound

Natural Product: NPC478312

Natural Product ID	NPC478312
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KNLDCVVYBDMCGK-KDWUTSDDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	71573696
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 83 86 0 0 0 0 0 0 0 0999 V2000 6.8930 -0.1635 1.1446 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7631 1.2314 0.6773 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6901 1.6303 0.0619 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4434 1.0317 -0.3480 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1073 -0.3853 -0.3573 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6122 -0.6004 -0.8343 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6595 -2.1919 -0.8915 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5973 -0.3837 0.2080 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5647 0.9464 0.9337 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2096 0.8864 1.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5875 -0.0941 0.9715 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7715 -1.3738 1.7670 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9613 0.3420 0.6117 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5943 1.3018 1.2387 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9817 1.7417 0.8763 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7547 0.5801 0.2981 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1252 1.0334 -0.0519 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2192 2.3405 -0.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9145 1.1453 1.2614 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7929 -0.0398 -0.8358 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8988 0.2177 -1.2803 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2220 -1.3575 -1.1035 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7413 -1.4820 -0.9635 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0529 -0.1381 -0.7818 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1098 0.5462 -2.1281 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6136 -0.3567 -0.4838 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8896 -1.1836 -1.2147 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4260 -1.4541 -0.9931 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1718 -0.3105 -0.3169 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0322 0.9484 -1.1382 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9176 -1.1847 -1.1776 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5630 -2.3445 -0.9249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4831 -2.8697 0.1991 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3883 -3.0432 -1.9567 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8981 2.1683 0.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8040 3.3293 0.5382 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0161 1.7201 1.5771 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6198 -0.0867 2.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4518 -0.8038 0.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0098 -0.5943 1.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7743 2.7629 -0.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6176 1.7284 0.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3488 1.4033 -1.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0575 -0.8208 0.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5218 -0.2424 -1.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3869 -2.4900 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7059 -2.5971 -1.2152 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8210 -2.5643 0.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -1.1569 0.9859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4562 1.8237 0.3224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 1.0681 1.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4518 0.4704 2.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1731 1.8908 1.8533 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4029 -1.0541 2.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1378 -1.7722 2.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4048 -2.0926 1.2348 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1234 1.8063 2.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4555 2.0793 1.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8902 2.6068 0.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8710 -0.1507 1.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5841 3.1602 -0.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3233 2.7038 -1.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0159 2.2667 -1.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9854 1.0819 1.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6770 2.1450 1.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5625 0.3883 1.9917 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7022 -2.0807 -0.3837 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5910 -1.6981 -2.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3662 -1.9713 -1.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4729 -2.0797 -0.0574 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1359 0.6825 -2.5094 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6161 -0.1659 -2.8513 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4918 1.4562 -2.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3528 -1.7087 -2.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4068 -2.4221 -0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0245 -1.4869 -2.0527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3981 1.7976 -0.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8485 1.2324 -1.7196 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8493 0.7422 -1.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9721 -2.8783 -2.9837 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4527 -2.6884 -1.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3144 -4.1386 -1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8634 2.2638 1.6991 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 6 5 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 2 35 1 0 35 36 2 0 35 37 1 0 29 8 1 0 29 11 1 0 26 13 1 0 24 16 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 1 6 45 1 6 7 46 1 0 7 47 1 0 7 48 1 0 8 49 1 1 9 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 12 54 1 0 12 55 1 0 12 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 1 18 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 19 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 23 70 1 0 25 71 1 0 25 72 1 0 25 73 1 0 27 74 1 0 28 75 1 0 28 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 37 83 1 0 M END

Standard InCHIKey	KNLDCVVYBDMCGK-KDWUTSDDSA-N
Standard InCHI	InChI=1S/C32H46O5/c1-19(28(35)36)9-11-25(37-21(3)33)20(2)22-13-17-32(8)24-10-12-26-29(4,5)27(34)15-16-30(26,6)23(24)14-18-31(22,32)7/h9-10,14,20,22,25-26H,11-13,15-18H2,1-8H3,(H,35,36)/b19-9+/t20-,22+,25-,26-,30+,31+,32-/m0/s1
SMILES	C/C(=CC[C@@H]([C@@H](C)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C)OC(=O)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	510.33	Volume:	555.935 ? Van der Waals volume.
Dense:	0.918	LogP:	3.949 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.313 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	80.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.305	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.015	Fsp³:	0.719
MCE-18:	82.836 ? 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:	0.922	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? 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:	0.53	Promiscuous compounds:	0.267

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.329	MDCK Permeability:	-5.061
Pgp-inhibitor:	0.968	Pgp-substrate:	0.0
PAMPA:	0.473 ? 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):	0.002
20% Bioavailability (F20%):	0.198	30% Bioavailability (F30%):	0.554
50% Bioavailability (F50%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.951
Plasma Protein Binding (PPB):	88.351%	Volume Distribution (VD):	-0.046
Fu:	12.361% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.046
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.019	CYP2C19-substrate:	0.013
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.9 ? 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):

4.988

Half-life (T1/2):

0.558

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.044
Human Hepatotoxicity (H-HT):	0.732	Drug-induced Liver Injury (DILI):	0.716
AMES Toxicity:	0.074	Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.3	Skin Sensitization:	0.943
Carcinogencity:	0.443	Eye Corrosion:	0.013
Eye Irritation:	0.223	Respiratory Toxicity:	0.374
Drug-induced Neurotoxicity:	0.089	Ototoxicity:	0.706
Hematotoxicity:	0.465	Drug-induced Nephrotoxicity:	0.747
Genotoxicity:	0.936	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.08	Hek293 Cytotoxicity:	0.15
BCF:	0.603 ? 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:	3.713 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.549 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.711 ? 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
NPO40141	Ganoderma sp. BCC 16642	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26716912]
NPO40141	Ganoderma sp. BCC 16642	Strain	Polyporaceae	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
MIC	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	35000.0	nM	PMID[26716912]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	>	50.0	ug.mL-1	PMID[26716912]

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 NPC478312 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	21746
0.1-0.2	24035
0.2-0.3	3673
0.3-0.4	268
0.4-0.5	82
0.5-0.6	36
0.6-0.7	8
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	Natural Product ID
0.7606	Intermediate Similarity	NPC92022
0.7536	Intermediate Similarity	NPC276127
0.7536	Intermediate Similarity	NPC141401
0.7536	Intermediate Similarity	NPC478307
0.7397	Intermediate Similarity	NPC166120
0.7206	Intermediate Similarity	NPC87552
0.7042	Intermediate Similarity	NPC69982
0.6849	Remote Similarity	NPC478297
0.6579	Remote Similarity	NPC478311
0.6494	Remote Similarity	NPC478309
0.6234	Remote Similarity	NPC482568
0.6234	Remote Similarity	NPC137552
0.6234	Remote Similarity	NPC99411
0.6076	Remote Similarity	NPC482567
0.6026	Remote Similarity	NPC478299
0.5921	Remote Similarity	NPC478313
0.5921	Remote Similarity	NPC489790
0.5854	Remote Similarity	NPC482569
0.5854	Remote Similarity	NPC146822
0.5844	Remote Similarity	NPC85742
0.5844	Remote Similarity	NPC489791
0.5844	Remote Similarity	NPC22421
0.5769	Remote Similarity	NPC58410
0.5753	Remote Similarity	NPC470048
0.5616	Remote Similarity	NPC89077
0.5616	Remote Similarity	NPC4166
0.561	Remote Similarity	NPC76162
0.561	Remote Similarity	NPC489805
0.5556	Remote Similarity	NPC484794
0.5556	Remote Similarity	NPC170793
0.5541	Remote Similarity	NPC83569
0.5476	Remote Similarity	NPC478310
0.5443	Remote Similarity	NPC285702
0.5443	Remote Similarity	NPC166745
0.5443	Remote Similarity	NPC235464
0.5405	Remote Similarity	NPC311092
0.5395	Remote Similarity	NPC212948
0.5395	Remote Similarity	NPC69279
0.5395	Remote Similarity	NPC44181
0.5395	Remote Similarity	NPC606857
0.5375	Remote Similarity	NPC489807
0.5375	Remote Similarity	NPC489808
0.5375	Remote Similarity	NPC478298
0.5375	Remote Similarity	NPC489800
0.5325	Remote Similarity	NPC66429
0.5256	Remote Similarity	NPC214697
0.519	Remote Similarity	NPC152897
0.5125	Remote Similarity	NPC155676
0.506	Remote Similarity	NPC489788
0.506	Remote Similarity	NPC484796
0.506	Remote Similarity	NPC299325

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6317
0.1-0.2	2722
0.2-0.3	110
0.3-0.4	1
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