NPASS Compound

Natural Product: NPC76895

Natural Product ID	NPC76895
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LPHOGVFYEBRXSC-WIUKAADNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9890992
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 82 85 0 0 0 0 0 0 0 0999 V2000 6.1794 0.9788 3.6229 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4666 0.4744 2.4235 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5812 1.1465 1.2873 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8775 0.6901 0.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9466 1.7713 -0.4587 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2021 1.5760 -1.6931 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2421 0.5140 -1.9471 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5681 -0.9043 -1.9221 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3426 -1.6582 -1.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2450 -0.6772 -1.5849 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1761 -0.7375 -3.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9519 -0.8039 -0.7400 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 0.3050 -0.4912 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2748 1.6478 -1.0174 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0589 1.7136 -1.6780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9287 0.6131 -1.1840 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1659 0.5869 0.2781 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8659 0.2264 0.3560 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4460 0.3915 1.7749 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8168 1.3884 0.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9697 1.3446 1.0016 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 0.0511 1.2004 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8094 -1.1855 1.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4074 -1.8185 2.3221 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7395 -2.2099 0.3245 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6701 -0.9997 0.0604 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8880 -2.2515 -0.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4044 -2.0966 -0.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1222 0.0069 2.5199 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7789 -1.3891 -3.2521 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2474 1.6537 -2.8127 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4414 0.7241 -3.5989 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9467 2.8501 -2.8595 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6528 -0.7650 2.5401 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1055 1.4992 3.2668 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4534 0.1652 4.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5527 1.6908 4.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1813 2.0445 1.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6745 0.4605 -0.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4112 -0.2481 0.3135 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6460 2.6634 -0.6556 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 2.1821 0.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6298 2.5572 -1.9143 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8755 0.7242 -3.0353 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4063 -1.2864 -1.3702 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4984 -1.9656 -0.3291 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1725 -2.5432 -1.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0655 -0.0847 -3.2509 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6043 -1.7794 -3.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6235 -0.6721 -3.7604 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2381 2.4058 -0.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0365 2.0095 -1.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4978 2.7272 -1.4894 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0787 1.6040 -2.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1094 0.1589 0.6096 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3754 -0.0676 0.7580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0438 1.5670 0.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9816 1.4223 1.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6239 -0.3043 2.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2532 0.4253 2.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3024 2.3673 0.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1414 1.3225 -1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6182 1.8269 1.9633 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7107 2.1117 0.6153 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5723 0.0387 0.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8251 -1.2464 3.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3157 -1.9679 2.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8444 -2.8474 2.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8064 -1.9688 0.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6133 -2.1980 -0.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5645 -3.2209 0.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1660 -0.7905 -0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1847 -2.8098 -1.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0996 -3.0166 0.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9786 -2.2699 0.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9544 -2.9278 -0.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0692 -0.1928 2.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8814 -2.3745 -3.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7451 2.9684 -3.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7411 -1.1844 3.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5831 -0.6112 2.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0515 -1.5217 1.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 0 10 11 1 6 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 13 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 22 29 1 0 8 30 1 0 6 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 16 7 1 0 26 18 1 0 16 10 1 0 28 12 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 7 44 1 6 8 45 1 1 9 46 1 0 9 47 1 0 11 48 1 0 11 49 1 0 11 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 17 55 1 0 17 56 1 0 17 57 1 0 19 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 6 24 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 26 72 1 6 27 73 1 0 27 74 1 0 28 75 1 0 28 76 1 0 29 77 1 0 30 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	LPHOGVFYEBRXSC-WIUKAADNSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,19,22-25,31-32H,8,10-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24+,25+,28-,29-,30+/m1/s1
SMILES	CC(=CCC[C@H]([C@H]1[C@@H](C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)O)O)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	3.514 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.071 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.995 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.398	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.918	Fsp³:	0.833
MCE-18:	84.0 ? 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:	0.912	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.064 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.009 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.366	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.491	MDCK Permeability:	-5.133
Pgp-inhibitor:	0.001	Pgp-substrate:	0.179
PAMPA:	1.0 ? 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%):	0.16	30% Bioavailability (F30%):	0.011
50% Bioavailability (F50%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272	MRP1:	0.997
Plasma Protein Binding (PPB):	92.002%	Volume Distribution (VD):	-0.394
Fu:	5.957% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.954	BCRP inhibitor:	0.004
BSEP inhibitor:	0.671

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.173	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.012 ? 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):

6.449

Half-life (T1/2):

0.95

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.572	Drug-induced Liver Injury (DILI):	0.166
AMES Toxicity:	0.307	Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.117	Skin Sensitization:	0.998
Carcinogencity:	0.769	Eye Corrosion:	0.118
Eye Irritation:	0.798	Respiratory Toxicity:	0.804
Drug-induced Neurotoxicity:	0.023	Ototoxicity:	0.623
Hematotoxicity:	0.485	Drug-induced Nephrotoxicity:	0.936
Genotoxicity:	0.103	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.179	Hek293 Cytotoxicity:	0.066
BCF:	1.263 ? 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:	4.055 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.598 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.903 ? 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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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	4

Activity Type	# Activity
Cell line	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
NPT111	Cell line	K562	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	>	40000.0	nM	PMID[27808511]

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 NPC76895 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	18619
0.1-0.2	26682
0.2-0.3	4050
0.3-0.4	387
0.4-0.5	70
0.5-0.6	31
0.6-0.7	7
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
0.7869	Intermediate Similarity	NPC484974
0.7869	Intermediate Similarity	NPC23434
0.7581	Intermediate Similarity	NPC233836
0.7581	Intermediate Similarity	NPC159046
0.7581	Intermediate Similarity	NPC187376
0.75	Intermediate Similarity	NPC484976
0.6923	Remote Similarity	NPC173272
0.6667	Remote Similarity	NPC222845
0.6667	Remote Similarity	NPC296577
0.6567	Remote Similarity	NPC312215
0.6522	Remote Similarity	NPC294480
0.6471	Remote Similarity	NPC470375
0.6471	Remote Similarity	NPC470376
0.5938	Remote Similarity	NPC46160
0.5938	Remote Similarity	NPC202642
0.5915	Remote Similarity	NPC48647
0.5915	Remote Similarity	NPC482518
0.5882	Remote Similarity	NPC55309
0.5882	Remote Similarity	NPC28252
0.5833	Remote Similarity	NPC484973
0.5821	Remote Similarity	NPC94755
0.5797	Remote Similarity	NPC469400
0.5775	Remote Similarity	NPC484971
0.5775	Remote Similarity	NPC484970
0.5758	Remote Similarity	NPC214570
0.5753	Remote Similarity	NPC184848
0.5753	Remote Similarity	NPC69548
0.5634	Remote Similarity	NPC54689
0.5556	Remote Similarity	NPC243866
0.5556	Remote Similarity	NPC45324
0.5556	Remote Similarity	NPC162001
0.5493	Remote Similarity	NPC84271
0.5493	Remote Similarity	NPC102414
0.5479	Remote Similarity	NPC186810
0.5455	Remote Similarity	NPC275910
0.5352	Remote Similarity	NPC48330
0.527	Remote Similarity	NPC484975
0.527	Remote Similarity	NPC321301
0.5147	Remote Similarity	NPC87489
0.5135	Remote Similarity	NPC148414
0.5135	Remote Similarity	NPC111585
0.5135	Remote Similarity	NPC175628
0.5135	Remote Similarity	NPC183546
0.5068	Remote Similarity	NPC155479

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC76895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5976
0.1-0.2	3067
0.2-0.3	101
0.3-0.4	6
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