NPASS Compound

Natural Product: NPC486561

Natural Product ID	NPC486561
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QZJJFBPXTYFVSV-BTHXHEGYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 93 96 0 0 0 0 0 0 0 0999 V2000 9.7611 3.2346 -1.6499 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3648 3.2559 -1.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9035 1.8238 -0.8931 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5125 1.7577 -0.2952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5007 2.4599 -1.1492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1011 2.4240 -0.5877 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6649 0.9984 -0.4561 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2548 0.9349 0.1031 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6315 1.9527 0.3747 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7247 -0.2744 0.2860 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4602 -0.6794 0.7651 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3997 -2.1541 0.8467 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8138 -2.8954 0.5948 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4200 -4.1148 -0.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7931 -4.2672 -0.5010 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3929 -5.0887 -0.7202 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6967 -5.1629 -0.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4159 -4.1864 0.3317 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2283 -2.8069 -0.1887 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3237 -2.0912 0.4579 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3123 -2.9575 0.6241 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6523 -2.6587 1.2541 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9114 -4.2682 0.1093 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6046 -5.1759 -0.3685 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8856 -2.2034 -0.1981 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9950 -0.7520 0.0833 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8013 -0.1033 -1.0211 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6970 0.0218 0.2046 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0747 1.1467 1.0186 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3095 2.4139 0.5131 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1681 2.5371 -0.7521 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 3.5652 1.3333 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8872 4.8144 0.5404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9408 4.7563 -0.5128 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3169 4.4491 0.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2702 4.4254 -1.1655 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4067 -2.2745 -1.5390 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2544 -4.3598 1.6824 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8322 -6.1615 -1.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2582 -5.5144 -2.7099 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4694 -1.2920 2.1167 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 -1.2369 3.0490 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8158 -1.2703 2.8680 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1822 4.2702 -1.6207 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7154 2.9556 -2.7194 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4068 2.5529 -1.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4162 3.8061 -0.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7346 3.7782 -1.8182 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0007 1.3170 -1.8543 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5996 1.3417 -0.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2580 0.6705 -0.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5639 2.1658 0.7204 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5419 2.0767 -2.1832 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8067 3.5368 -1.2199 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0337 2.9204 0.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4352 2.9107 -1.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7361 0.4362 -1.3981 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3041 0.4954 0.2961 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3818 -2.7169 0.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1702 -3.3511 1.5465 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2553 -5.9656 -0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5755 -2.8872 -1.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4206 -1.0647 0.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9423 -1.6321 0.9904 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4295 -3.3383 0.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6144 -2.7208 2.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5860 -0.5267 1.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5372 -0.8025 -1.4732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0782 0.1973 -1.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3078 0.8225 -0.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4995 0.4221 -0.7997 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6413 3.3741 1.8996 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8880 3.7563 2.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 5.7011 1.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9091 4.9950 0.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0248 5.8016 -0.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7300 4.1228 -1.3752 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2829 3.4040 0.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6841 5.1780 0.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2099 3.9063 -0.9178 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4801 5.4537 -1.5149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8181 3.8509 -2.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1664 -2.3535 -2.1671 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7490 -5.2074 1.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0606 -6.7640 -1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6328 -6.8401 -1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7955 -5.7204 -3.5263 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5790 -1.7809 2.7656 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3772 -1.6438 4.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9276 -0.1562 3.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6616 -1.1885 2.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8178 -2.1730 3.5075 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7212 -0.4082 3.5723 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 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 11 10 1 6 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 21 23 1 0 23 24 2 0 19 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 25 37 1 6 18 38 1 1 16 39 1 0 39 40 1 0 12 41 1 0 41 42 1 0 41 43 1 0 28 11 1 0 41 11 1 0 25 13 1 0 23 18 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 6 55 1 0 6 56 1 0 7 57 1 0 7 58 1 0 12 59 1 6 13 60 1 1 17 61 1 0 19 62 1 6 20 63 1 0 22 64 1 0 22 65 1 0 22 66 1 0 26 67 1 1 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 6 32 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 38 84 1 0 39 85 1 0 39 86 1 0 40 87 1 0 42 88 1 0 42 89 1 0 42 90 1 0 43 91 1 0 43 92 1 0 43 93 1 0 M END

Standard InCHIKey	QZJJFBPXTYFVSV-BTHXHEGYSA-N
Standard InCHI	InChI=1S/C34H50O9/c1-7-9-11-12-14-16-25(37)43-34-28(31(34,5)6)26-27(38)22(19-35)18-32(40)23(17-20(3)29(32)39)33(26,41)21(4)30(34)42-24(36)15-13-10-8-2/h17-18,21,23,26,28,30,35,40-41H,7-16,19H2,1-6H3/t21-,23-,26+,28-,30-,32-,33+,34-/m1/s1
SMILES	CCCCCCCC(=O)O[C@]12[C@H]([C@@H]3C(=O)C(=C[C@]4([C@@H](C=C(C)C4=O)[C@]3([C@H](C)[C@H]1OC(=O)CCCCC)O)O)CO)C2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.35	Volume:	625.687 ? Van der Waals volume.
Dense:	0.963	LogP:	4.006 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.098 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.272 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	22.0
TPSA:	147.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.209	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.207	Fsp³:	0.765
MCE-18:	80.5 ? 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:	0.255	Fluc inhibitor:	0.005 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.204	Promiscuous compounds:	0.699

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121	MDCK Permeability:	-4.698
Pgp-inhibitor:	0.084	Pgp-substrate:	0.96
PAMPA:	0.991 ? 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):	0.444
20% Bioavailability (F20%):	0.972	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.925
Plasma Protein Binding (PPB):	92.425%	Volume Distribution (VD):	0.222
Fu:	7.573% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.844
OATP1B3 inhibitor:	0.968	BCRP inhibitor:	0.003
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.988
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.666 ? 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):

3.279

Half-life (T1/2):

1.218

ADMET: Toxicity

hERG Blockers:	0.133	hERG Blockers (10um):	0.339
Human Hepatotoxicity (H-HT):	0.722	Drug-induced Liver Injury (DILI):	0.565
AMES Toxicity:	0.192	Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.141	Skin Sensitization:	0.988
Carcinogencity:	0.414	Eye Corrosion:	0.012
Eye Irritation:	0.64	Respiratory Toxicity:	0.749
Drug-induced Neurotoxicity:	0.035	Ototoxicity:	0.738
Hematotoxicity:	0.639	Drug-induced Nephrotoxicity:	0.855
Genotoxicity:	0.02	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.39	Hek293 Cytotoxicity:	0.151
BCF:	1.27 ? 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:	4.375 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.162 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.336 ? 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
NPO40396	Wikstroemia scytophylla	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33172265]

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	1
CC50	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
NPT25	Cell line	MT4	Homo sapiens	CC50	>	164.0	nM	PMID[33172265]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	164.0	nM	PMID[33172265]

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 NPC486561 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	17175
0.1-0.2	30602
0.2-0.3	1906
0.3-0.4	85
0.4-0.5	51
0.5-0.6	20
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC19464
0.8806	High Similarity	NPC607335
0.8806	High Similarity	NPC610849
0.7671	Intermediate Similarity	NPC600879
0.7671	Intermediate Similarity	NPC605007
0.76	Intermediate Similarity	NPC486562
0.7246	Intermediate Similarity	NPC472401
0.7246	Intermediate Similarity	NPC605797
0.7	Intermediate Similarity	NPC609113
0.6974	Remote Similarity	NPC609967
0.6883	Remote Similarity	NPC482200
0.6849	Remote Similarity	NPC472399
0.6267	Remote Similarity	NPC5991
0.6267	Remote Similarity	NPC196500
0.6267	Remote Similarity	NPC471108
0.6267	Remote Similarity	NPC5989
0.6133	Remote Similarity	NPC275696
0.6133	Remote Similarity	NPC255081
0.6053	Remote Similarity	NPC488610
0.5823	Remote Similarity	NPC22628
0.5823	Remote Similarity	NPC600005
0.5811	Remote Similarity	NPC171905
0.5765	Remote Similarity	NPC486559
0.5732	Remote Similarity	NPC484334
0.5698	Remote Similarity	NPC145649
0.5698	Remote Similarity	NPC233581
0.557	Remote Similarity	NPC603912
0.5513	Remote Similarity	NPC485737
0.5432	Remote Similarity	NPC488611
0.5402	Remote Similarity	NPC609007
0.5244	Remote Similarity	NPC10721
0.5181	Remote Similarity	NPC484333
0.5172	Remote Similarity	NPC138641
0.5172	Remote Similarity	NPC611243
0.5125	Remote Similarity	NPC485734
0.5122	Remote Similarity	NPC484252
0.5119	Remote Similarity	NPC609983
0.5114	Remote Similarity	NPC11410
0.5114	Remote Similarity	NPC600144

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6294
0.1-0.2	2802
0.2-0.3	54
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