NPASS Compound

Natural Product: NPC73506

Natural Product ID	NPC73506
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LPNSAXKZEFPRKW-CJALRUASSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46243634
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 80 83 0 0 0 0 0 0 0 0999 V2000 3.3510 -0.5475 -2.6773 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4568 -0.3407 -1.1805 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1542 -1.4577 -0.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3022 -1.2892 0.9995 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0640 -0.0857 1.3896 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3624 0.0877 1.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1653 -0.9466 0.5392 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0112 1.3202 1.6155 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2397 1.4849 1.4262 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3084 2.3391 2.2352 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8013 -2.4496 1.5946 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2603 0.2447 -0.5518 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0837 1.6116 -1.2581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6381 1.5895 -1.7795 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0369 0.8136 -0.6811 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1166 1.6764 0.5727 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3933 0.4833 -0.8192 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1797 1.1862 -1.6197 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6329 0.7502 -1.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0041 0.6253 -0.2346 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4658 0.6967 -0.0230 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3130 -0.1040 -0.9589 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8820 2.1532 -0.1546 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8280 0.2936 1.3765 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0001 0.2126 1.6456 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8229 0.0015 2.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4455 -0.3037 1.9476 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3280 -0.5213 0.4635 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1472 -1.8094 0.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9350 -0.6716 -0.0564 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9560 -1.2699 0.8877 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4757 -0.9571 0.7798 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9478 -0.3966 -0.5544 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6976 -1.4585 -1.5650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4057 -0.2485 -3.1226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 0.0631 -3.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6804 -1.5914 -2.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2215 0.5111 -1.0909 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1857 -1.5799 -0.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7036 -2.4594 -0.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2833 -1.1809 1.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5632 0.7629 1.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2061 -0.8751 0.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8738 -1.9799 0.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3728 -0.7055 -0.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6924 3.2746 2.2574 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5544 -3.2534 1.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5449 0.4468 0.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2490 2.4357 -0.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7302 1.7343 -2.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2337 2.6409 -1.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5401 1.2078 -2.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2179 2.6964 0.2466 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6655 1.3572 1.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1038 1.7852 0.9964 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 2.0178 -2.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2287 1.5475 -2.1298 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6392 -0.1905 -2.2395 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5801 1.5472 0.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8409 -0.2945 -1.9459 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2374 0.4706 -1.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6841 -1.0475 -0.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0520 2.4295 -1.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8039 2.3698 0.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0702 2.7886 0.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2683 -0.7938 3.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8173 0.9040 3.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7686 0.4878 2.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1944 -1.3041 2.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9484 -1.9477 0.9349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4768 -1.9053 -0.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4237 -2.6606 0.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0735 -1.4345 -0.9034 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2244 -1.0662 1.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0734 -2.3968 0.8431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0600 -1.8662 1.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7790 -0.1832 1.5323 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0595 -2.3075 -1.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6509 -2.0359 -1.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2039 -1.1319 -2.4940 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 4 11 1 0 2 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 6 33 12 1 0 33 15 1 0 30 17 1 0 28 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 6 3 39 1 0 3 40 1 0 4 41 1 1 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 0 12 48 1 1 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 16 53 1 0 16 54 1 0 16 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 20 59 1 1 22 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 23 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 29 70 1 0 29 71 1 0 29 72 1 0 30 73 1 6 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	LPNSAXKZEFPRKW-CJALRUASSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18(16-20(31)17-19(2)26(33)34)21-10-14-30(7)23-8-9-24-27(3,4)25(32)12-13-28(24,5)22(23)11-15-29(21,30)6/h8,17-18,20-22,24,31H,9-16H2,1-7H3,(H,33,34)/b19-17+/t18-,20-,21-,22-,24+,28-,29-,30+/m1/s1
SMILES	C[C@H](C[C@H](/C=C(C)/C(=O)O)O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)[C@@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	517.825 ? Van der Waals volume.
Dense:	0.908	LogP:	3.643 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.199 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.449 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.352	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.849	Fsp³:	0.8
MCE-18:	83.111 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.941	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.409	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.19	MDCK Permeability:	-4.855
Pgp-inhibitor:	0.464	Pgp-substrate:	0.0
PAMPA:	0.906 ? 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%):	0.065	30% Bioavailability (F30%):	0.207
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.922
Plasma Protein Binding (PPB):	91.595%	Volume Distribution (VD):	-0.253
Fu:	9.207% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.016
BSEP inhibitor:	0.992

ADMET: Metabolism

CYP1A2-inhibitor:	0.106	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.067	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.721
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.997
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
HLM stability:	0.988 ? 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):

2.955

Half-life (T1/2):

1.09

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.091
Human Hepatotoxicity (H-HT):	0.733	Drug-induced Liver Injury (DILI):	0.8
AMES Toxicity:	0.149	Rat Oral Acute Toxicity:	0.56
Maximum Recommended Daily Dose:	0.735	Skin Sensitization:	0.969
Carcinogencity:	0.642	Eye Corrosion:	0.029
Eye Irritation:	0.466	Respiratory Toxicity:	0.872
Drug-induced Neurotoxicity:	0.395	Ototoxicity:	0.664
Hematotoxicity:	0.712	Drug-induced Nephrotoxicity:	0.887
Genotoxicity:	0.917	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.394	Hek293 Cytotoxicity:	0.243
BCF:	0.667 ? 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:	3.682 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.371 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.529 ? 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
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	trunk	n.a.	n.a.	PMID[24224862]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	Trunk	n.a.	n.a.	PMID[26812172]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30063340]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29383	Abies holophylla	Species	Pinaceae	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	5
Activity	3

Activity Type	# Activity
Cell line	8

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
NPT34	Cell line	BV-2	Mus musculus	IC50	=	29800.0	nM	PMID[30063340]
NPT148	Cell line	HCT-15	Homo sapiens	IC50	>	10000.0	nM	PMID[30063340]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	=	8800.0	nM	PMID[30063340]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[30063340]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[30063340]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	110.8	%	PMID[30063340]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	140.9	%	PMID[30063340]
NPT34	Cell line	BV-2	Mus musculus	Activity	=	125.2	%	PMID[30063340]

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 NPC73506 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	18584
0.1-0.2	26300
0.2-0.3	4133
0.3-0.4	679
0.4-0.5	115
0.5-0.6	33
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
0.7353	Intermediate Similarity	NPC472239
0.7273	Intermediate Similarity	NPC90652
0.7273	Intermediate Similarity	NPC155255
0.7246	Intermediate Similarity	NPC6190
0.7206	Intermediate Similarity	NPC471224
0.6901	Remote Similarity	NPC293081
0.6714	Remote Similarity	NPC486521
0.6714	Remote Similarity	NPC262870
0.6528	Remote Similarity	NPC479661
0.6522	Remote Similarity	NPC260992
0.6176	Remote Similarity	NPC470078
0.6056	Remote Similarity	NPC470417
0.5972	Remote Similarity	NPC470047
0.5972	Remote Similarity	NPC470046
0.589	Remote Similarity	NPC476174
0.5867	Remote Similarity	NPC479667
0.5833	Remote Similarity	NPC470052
0.5733	Remote Similarity	NPC472240
0.5733	Remote Similarity	NPC67831
0.5733	Remote Similarity	NPC174051
0.5733	Remote Similarity	NPC262858
0.5714	Remote Similarity	NPC273669
0.5714	Remote Similarity	NPC484802
0.5714	Remote Similarity	NPC118647
0.5676	Remote Similarity	NPC147066
0.5556	Remote Similarity	NPC470223
0.5556	Remote Similarity	NPC484792
0.5455	Remote Similarity	NPC605437
0.5309	Remote Similarity	NPC63023
0.5309	Remote Similarity	NPC121566
0.5309	Remote Similarity	NPC100955
0.5309	Remote Similarity	NPC95243
0.527	Remote Similarity	NPC82902
0.5263	Remote Similarity	NPC480960
0.5205	Remote Similarity	NPC247220
0.519	Remote Similarity	NPC193750
0.5181	Remote Similarity	NPC189282
0.5181	Remote Similarity	NPC237402
0.5132	Remote Similarity	NPC2983
0.5132	Remote Similarity	NPC469994
0.5128	Remote Similarity	NPC470050
0.5128	Remote Similarity	NPC470051
0.5128	Remote Similarity	NPC607625
0.5067	Remote Similarity	NPC474218
0.5063	Remote Similarity	NPC214697

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5629
0.1-0.2	3388
0.2-0.3	128
0.3-0.4	5
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