NPASS Compound

Natural Product: NPC488976

Natural Product ID	NPC488976
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DOSVOFXLQSKXJN-ULLQBVCOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	71718796
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 79 82 0 0 0 0 0 0 0 0999 V2000 -8.4729 -2.8858 2.0631 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0512 -2.4505 1.7376 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8768 -1.3866 1.0166 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6843 -0.7441 0.5567 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7821 0.3247 -0.1586 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3164 -1.1965 0.8273 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2767 -0.1950 0.2485 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6124 1.1061 1.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9106 -0.6892 0.6766 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6359 -2.1110 0.2052 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 -2.2340 0.0877 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3967 -0.8864 0.4888 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6498 -0.9111 1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6430 -0.5041 -0.2232 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8395 -0.8327 0.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0066 -0.8981 -0.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2839 0.4926 -0.8143 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1515 0.3517 -2.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9414 0.8085 -3.2013 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4318 -0.3752 -1.8227 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7510 -0.8529 -0.7313 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3202 -0.5360 -2.8908 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0909 1.3612 -1.0491 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4477 2.8426 -1.0577 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0690 3.3520 0.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3239 4.8255 -0.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0708 5.3823 -1.1426 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8647 5.6356 0.9565 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1516 1.0387 -2.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7645 0.9102 -0.6782 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8360 1.8790 -0.0788 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4451 1.3802 0.5050 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7555 0.0083 0.0531 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8646 -0.1173 -1.4463 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9935 -3.3092 2.2922 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8140 -2.2982 2.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1369 -2.6352 1.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5014 -3.9725 2.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8315 -0.8914 0.6949 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1677 -2.1769 0.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1341 -1.2181 1.9010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4234 0.0019 -0.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6320 1.9778 0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5395 1.0235 1.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8053 1.2696 1.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9486 -0.6281 1.7988 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0894 -2.2764 -0.7638 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0336 -2.8462 0.9641 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2529 -3.0470 0.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 -2.4907 -0.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3250 -0.0847 2.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1300 -1.9177 2.1716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2140 -0.8897 2.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7348 -1.2092 -1.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0939 -0.0224 1.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8126 -1.8423 1.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8653 -1.3036 0.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7474 -1.5938 -1.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9105 0.9664 -0.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6737 0.6255 -4.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0934 1.3894 -3.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1455 -1.0752 -2.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1523 3.1038 -1.8980 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5250 3.4522 -1.3067 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4910 3.2851 1.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1046 2.9316 0.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5637 6.3342 0.7393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2178 0.1185 -2.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5830 1.8476 -2.6925 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3544 2.4958 0.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5622 2.6179 -0.8944 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.3844 1.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2511 2.1375 0.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0819 -0.7514 -1.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8142 -0.5729 -1.7608 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7322 0.9098 -1.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4092 -2.7770 3.0613 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3551 -3.7762 1.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4739 -4.1596 2.8800 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 20 22 1 0 17 23 1 0 23 24 1 6 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 23 29 1 0 30 29 1 6 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 6 2 35 1 0 33 9 1 0 33 12 1 0 30 14 1 0 30 23 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 6 40 1 0 6 41 1 0 7 42 1 6 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 1 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 13 51 1 0 13 52 1 0 13 53 1 0 14 54 1 6 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 1 19 60 1 0 19 61 1 0 22 62 1 0 24 63 1 0 24 64 1 0 25 65 1 0 25 66 1 0 28 67 1 0 29 68 1 0 29 69 1 0 31 70 1 0 31 71 1 0 32 72 1 0 32 73 1 0 34 74 1 0 34 75 1 0 34 76 1 0 35 77 1 0 35 78 1 0 35 79 1 0 M END

Standard InCHIKey	DOSVOFXLQSKXJN-ULLQBVCOSA-N
Standard InCHI	InChI=1S/C30H44O5/c1-18(2)15-21(31)16-19(3)22-9-11-28(6)24-8-7-23(20(4)26(34)35)29(12-10-25(32)33)17-30(24,29)14-13-27(22,28)5/h15,19,22-24H,4,7-14,16-17H2,1-3,5-6H3,(H,32,33)(H,34,35)/t19-,22-,23+,24+,27-,28+,29-,30+/m1/s1
SMILES	CC(=CC(=O)C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(=C)C(=O)O)[C@@]4(CCC(=O)O)C[C@@]34CC[C@]12C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.32	Volume:	523.979 ? Van der Waals volume.
Dense:	0.924	LogP:	4.719 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.393 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.53 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	22.0
TPSA:	91.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.357	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.482	Fsp³:	0.767
MCE-18:	116.434 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.724	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.588	Promiscuous compounds:	0.308

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.439	MDCK Permeability:	-5.031
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.978 ? 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%):	0.699	30% Bioavailability (F30%):	0.073
50% Bioavailability (F50%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016	MRP1:	0.999
Plasma Protein Binding (PPB):	96.58%	Volume Distribution (VD):	-0.45
Fu:	4.428% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.927	BCRP inhibitor:	0.0
BSEP inhibitor:	0.854

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:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.845
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

0.71

Half-life (T1/2):

1.375

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.015
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.534
AMES Toxicity:	0.061	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.209	Skin Sensitization:	0.787
Carcinogencity:	0.243	Eye Corrosion:	0.051
Eye Irritation:	0.696	Respiratory Toxicity:	0.787
Drug-induced Neurotoxicity:	0.077	Ototoxicity:	0.801
Hematotoxicity:	0.837	Drug-induced Nephrotoxicity:	0.851
Genotoxicity:	0.773	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.006	Hek293 Cytotoxicity:	0.021
BCF:	0.776 ? 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:	3.763 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.184 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.321 ? 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
NPO16360	Gardenia carinata	Species	Rubiaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[23550966]
NPO16360	Gardenia carinata	Species	Rubiaceae	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	2
Inhibition	1
Ratio IC50/EC50	1
EC50	1
ED50	7

Activity Type	# Activity
Individual protein	2
Cell line	6
Organism	1
Others	2
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	68700.0	nM	PMID[23550966]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	88.1	%	PMID[23550966]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell line	HEK293	Homo sapiens	ED50	>	10.0	uM	PMID[23550966]
NPT1034	Cell line	Lu1	Homo sapiens	ED50	>	10.0	uM	PMID[23550966]
NPT83	Cell line	MCF7	Homo sapiens	ED50	>	10.0	uM	PMID[23550966]
NPT1851	Cell line	Col2	Homo sapiens	ED50	>	10.0	uM	PMID[23550966]
NPT91	Cell line	KB	Homo sapiens	ED50	>	10.0	uM	PMID[23550966]
NPT168	Cell line	P388	Mus musculus	ED50	>	10.0	uM	PMID[23550966]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	uM	PMID[23550966]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	<	8300.0	nM	PMID[23550966]
NPT2	Others	Unspecified	n.a.	Ratio IC50/EC50	>	7.0	n.a.	PMID[23550966]
NPT27	Others	Unspecified	n.a.	IC50	=	57700.0	nM	PMID[23550966]

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 NPC488976 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	26242
0.1-0.2	21294
0.2-0.3	2052
0.3-0.4	176
0.4-0.5	58
0.5-0.6	28
0.6-0.7	4
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
0.7812	Intermediate Similarity	NPC81256
0.6479	Remote Similarity	NPC245284
0.6269	Remote Similarity	NPC486365
0.6056	Remote Similarity	NPC124207
0.6056	Remote Similarity	NPC486363
0.597	Remote Similarity	NPC60350
0.5909	Remote Similarity	NPC158846
0.5882	Remote Similarity	NPC186975
0.5821	Remote Similarity	NPC236618
0.5676	Remote Similarity	NPC486361
0.5616	Remote Similarity	NPC312900
0.5606	Remote Similarity	NPC606508
0.5526	Remote Similarity	NPC486367
0.5493	Remote Similarity	NPC194937
0.5493	Remote Similarity	NPC37153
0.5493	Remote Similarity	NPC476038
0.5479	Remote Similarity	NPC603267
0.5429	Remote Similarity	NPC162481
0.5352	Remote Similarity	NPC117122
0.5342	Remote Similarity	NPC603266
0.5303	Remote Similarity	NPC483442
0.5303	Remote Similarity	NPC69408
0.5286	Remote Similarity	NPC321690
0.527	Remote Similarity	NPC478129
0.5211	Remote Similarity	NPC488282
0.5211	Remote Similarity	NPC477372
0.5143	Remote Similarity	NPC16287
0.5139	Remote Similarity	NPC128496
0.5132	Remote Similarity	NPC486370
0.5132	Remote Similarity	NPC486371
0.5132	Remote Similarity	NPC486372
0.5068	Remote Similarity	NPC488278
0.5065	Remote Similarity	NPC476303

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6370
0.1-0.2	2685
0.2-0.3	93
0.3-0.4	2
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