NPASS Compound

Natural Product: NPC473613

Natural Product ID	NPC473613
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TXQYRZYWFXMOTA-LNDQYQGUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL447164
PubChem CID	44561297
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 85 89 0 0 0 0 0 0 0 0999 V2000 -1.3129 3.9185 -4.9367 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4646 3.1922 -3.6583 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4594 2.5288 -3.3309 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5433 3.1410 -2.6539 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5595 2.5210 -1.4511 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6862 3.4991 -0.2569 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3940 2.7575 0.8414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3639 1.2550 0.7414 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2100 0.6412 0.0144 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4712 1.6611 -0.9227 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2502 2.3885 0.0328 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7572 3.6392 0.1797 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4878 4.6945 -0.6251 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9041 4.0593 1.6275 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4810 1.0748 -1.8260 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0977 0.6701 -3.1994 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2832 -0.0303 -1.1640 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2145 -0.0208 0.3262 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8458 0.0837 0.9289 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4405 -1.2393 1.2934 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3025 -1.6799 2.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5514 -0.8740 3.5238 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1357 -3.0926 2.9006 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8564 -1.2503 0.7281 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0446 -1.2487 1.4496 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5183 -0.1184 1.7262 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7175 -2.4698 1.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2553 -3.7235 1.6018 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9718 -4.8301 2.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1517 -4.7097 2.7624 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6085 -3.4372 3.0274 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8917 -2.3413 2.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7644 -0.5384 -0.7707 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5405 0.7855 2.0419 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8085 0.2681 2.2392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1632 -0.8804 1.3962 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1949 -0.7992 0.5791 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6356 -1.8714 -0.2987 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0358 -3.1061 -0.3907 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5094 -4.0951 -1.2564 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5919 -3.8714 -2.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2130 -2.6519 -1.9810 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7383 -1.6830 -1.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2379 4.4143 -5.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9717 3.1854 -5.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4727 4.6551 -4.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5465 2.0024 -1.4483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1539 4.4343 -0.5536 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4564 3.1547 0.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0637 3.0734 1.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3141 1.0132 0.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4606 4.2277 -0.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8912 5.0476 -1.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7681 5.5761 -0.0476 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9513 4.4797 1.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9106 3.1946 2.3175 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2361 4.8749 1.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2762 1.8837 -1.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0624 0.7783 -3.5029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4258 -0.3993 -3.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6721 1.2175 -4.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0863 -1.0384 -1.6066 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3970 0.0727 -1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8315 0.8263 0.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9587 0.6170 1.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 -3.4555 3.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1814 -3.6989 1.9985 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0953 -2.9980 3.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3399 -3.8389 1.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6046 -5.8244 1.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6998 -5.5981 3.1038 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5283 -3.3439 3.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3105 -1.3644 2.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8226 -0.3795 -1.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2552 -0.7311 -1.7208 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8161 -1.4626 -0.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5717 1.0810 2.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9719 0.0440 3.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6061 -1.8113 1.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7789 0.1383 0.5432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1820 -3.3153 0.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0175 -5.0544 -1.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9467 -4.6484 -2.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0714 -2.5010 -2.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2594 -0.7454 -1.1083 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 11 12 1 0 12 13 1 0 12 14 1 0 10 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 18 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 9 33 1 6 8 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 10 5 1 0 32 27 1 0 43 38 1 0 12 6 1 0 19 9 1 0 1 44 1 0 1 45 1 0 1 46 1 0 5 47 1 6 6 48 1 6 7 49 1 0 7 50 1 0 8 51 1 6 13 52 1 0 13 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 16 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 1 19 65 1 1 23 66 1 0 23 67 1 0 23 68 1 0 28 69 1 0 29 70 1 0 30 71 1 0 31 72 1 0 32 73 1 0 33 74 1 0 33 75 1 0 33 76 1 0 35 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 39 81 1 0 40 82 1 0 41 83 1 0 42 84 1 0 43 85 1 0 M END

Standard InCHIKey	TXQYRZYWFXMOTA-LNDQYQGUSA-N
Standard InCHI	InChI=1S/C35H42O8/c1-22-20-28(42-32(38)26-17-11-8-12-18-26)31(41-24(3)37)34(6)29(39-19-13-16-25-14-9-7-10-15-25)21-27-30(40-23(2)36)35(22,34)43-33(27,4)5/h7-18,22,27-31H,19-21H2,1-6H3/b16-13+/t22-,27-,28+,29+,30-,31+,34-,35-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]2C[C@@H]([C@]3([C@@]1(OC2(C)C)[C@H](C)C[C@@H]([C@@H]3OC(=O)C)OC(=O)c1ccccc1)C)OC/C=C/c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	590.29	Volume:	615.091 ? Van der Waals volume.
Dense:	0.96	LogP:	4.249 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.685 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.567 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	30.0
TPSA:	97.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.282	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.804	Fsp³:	0.514
MCE-18:	154.528 ? 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:	0.689	Fluc inhibitor:	0.412 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.164 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.245	Promiscuous compounds:	0.209

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.1	MDCK Permeability:	-4.74
Pgp-inhibitor:	1.0	Pgp-substrate:	0.072
PAMPA:	0.067 ? 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%):	0.175	30% Bioavailability (F30%):	0.707
50% Bioavailability (F50%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.335	MRP1:	0.993
Plasma Protein Binding (PPB):	96.513%	Volume Distribution (VD):	-0.398
Fu:	3.566% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.045
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.289
CYP2C9-inhibitor:	0.041	CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.47	CYP2D6-substrate:	0.326
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.998 ? 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):

7.375

Half-life (T1/2):

0.492

ADMET: Toxicity

hERG Blockers:	0.19	hERG Blockers (10um):	0.707
Human Hepatotoxicity (H-HT):	0.226	Drug-induced Liver Injury (DILI):	0.618
AMES Toxicity:	0.431	Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.416	Skin Sensitization:	0.988
Carcinogencity:	0.159	Eye Corrosion:	0.001
Eye Irritation:	0.158	Respiratory Toxicity:	0.182
Drug-induced Neurotoxicity:	0.481	Ototoxicity:	0.402
Hematotoxicity:	0.09	Drug-induced Nephrotoxicity:	0.484
Genotoxicity:	0.096	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.19	Hek293 Cytotoxicity:	0.315
BCF:	1.099 ? 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:	4.069 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.847 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.356 ? 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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	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
Activity	1

Activity Type	# Activity
Cell line	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
NPT116	Cell line	HL-60	Homo sapiens	Activity	<	50.0	%	PMID[20022253]

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 NPC473613 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	14102
0.1-0.2	33367
0.2-0.3	1852
0.3-0.4	383
0.4-0.5	97
0.5-0.6	33
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8028	Intermediate Similarity	NPC473085
0.7727	Intermediate Similarity	NPC473081
0.7534	Intermediate Similarity	NPC473112
0.7297	Intermediate Similarity	NPC607428
0.7206	Intermediate Similarity	NPC195647
0.7206	Intermediate Similarity	NPC270498
0.6842	Remote Similarity	NPC475652
0.6714	Remote Similarity	NPC200592
0.6714	Remote Similarity	NPC610542
0.6622	Remote Similarity	NPC139067
0.6575	Remote Similarity	NPC70973
0.6575	Remote Similarity	NPC473111
0.6486	Remote Similarity	NPC4341
0.6447	Remote Similarity	NPC472574
0.64	Remote Similarity	NPC473871
0.6282	Remote Similarity	NPC184747
0.6184	Remote Similarity	NPC67777
0.6184	Remote Similarity	NPC43241
0.6053	Remote Similarity	NPC479047
0.6053	Remote Similarity	NPC191082
0.6053	Remote Similarity	NPC291638
0.5926	Remote Similarity	NPC481050
0.5875	Remote Similarity	NPC210591
0.5833	Remote Similarity	NPC483865
0.5823	Remote Similarity	NPC479044
0.5783	Remote Similarity	NPC475122
0.5783	Remote Similarity	NPC88593
0.5769	Remote Similarity	NPC177340
0.5732	Remote Similarity	NPC609221
0.5696	Remote Similarity	NPC473673
0.5676	Remote Similarity	NPC474608
0.5595	Remote Similarity	NPC14499
0.5529	Remote Similarity	NPC605086
0.5526	Remote Similarity	NPC481047
0.5526	Remote Similarity	NPC481045
0.5488	Remote Similarity	NPC214550
0.5443	Remote Similarity	NPC483883
0.5443	Remote Similarity	NPC151585
0.5263	Remote Similarity	NPC283375
0.5263	Remote Similarity	NPC183122
0.525	Remote Similarity	NPC48017
0.519	Remote Similarity	NPC311175
0.5185	Remote Similarity	NPC27377
0.5185	Remote Similarity	NPC137718
0.5181	Remote Similarity	NPC479043
0.5181	Remote Similarity	NPC609924
0.5169	Remote Similarity	NPC75600
0.5169	Remote Similarity	NPC483884
0.5125	Remote Similarity	NPC17877
0.5125	Remote Similarity	NPC51314
0.5122	Remote Similarity	NPC473889
0.506	Remote Similarity	NPC41481
0.5056	Remote Similarity	NPC188865
0.5056	Remote Similarity	NPC184817

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4101
0.1-0.2	4939
0.2-0.3	109
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