NPASS Compound

Natural Product: NPC273669

Natural Product ID	NPC273669
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RNETYSXHFSDFMM-GPWRYVIMSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	91895451
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 86 0 0 0 0 0 0 0 0999 V2000 6.4158 0.0436 2.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8862 0.0321 0.6706 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6558 -1.0605 -0.0280 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3998 -0.1773 0.6427 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0769 -1.5960 0.3726 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6819 -1.7475 -0.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7987 -0.7824 -0.2638 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1725 0.6336 0.0149 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3918 1.6219 -0.7594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0951 1.3690 -0.7752 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4975 0.0311 -0.2493 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4883 -0.0071 1.2434 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7535 -0.5311 -0.8532 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7261 -1.9299 -0.3017 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2275 -2.2784 -0.2115 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4568 -1.0691 -0.7495 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4480 -1.1474 -2.2671 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9854 0.2282 -0.7271 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5285 0.5382 0.6123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9117 1.1730 0.3689 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7922 0.0547 -0.1809 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7636 -0.4145 0.8837 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5668 -1.5620 0.2856 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6592 0.7105 1.3267 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0369 -0.9214 1.9472 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0037 -1.0066 -0.6199 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0736 -0.5020 -1.5201 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8365 2.1575 -0.6041 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6683 0.8388 -0.2134 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9796 0.7593 -1.6624 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9974 2.2058 0.3486 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4751 2.5064 0.3488 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3111 1.3315 0.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3258 1.4150 -0.6097 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6170 -0.9940 2.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3796 0.5882 2.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6677 0.4701 2.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7370 -0.7669 0.0392 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5840 -2.0394 0.4743 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4284 -1.1808 -1.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0386 0.0502 1.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7343 -2.0767 -0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1267 -2.1609 1.3504 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3546 -2.7787 -0.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0280 0.8090 1.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5287 2.6264 -0.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7199 1.7699 -1.7972 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5056 1.4432 -1.8230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6592 2.1352 -0.2025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2870 1.0015 1.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4210 -0.4102 1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3077 -0.7044 1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5439 -0.6404 -1.9600 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2671 -2.6152 -0.9730 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1367 -2.0379 0.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0946 -3.1788 -0.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0752 -2.5330 0.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1845 -1.9618 -2.6590 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5045 -1.4302 -2.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2641 -0.1936 -2.7642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8532 1.1983 -1.2631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7555 -0.3420 1.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9467 1.3304 1.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3299 1.5925 1.2824 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3912 0.3965 -1.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8599 -2.4391 0.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4273 -1.8256 0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8850 -1.3747 -0.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6061 0.2685 1.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8775 1.3885 0.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1586 1.2703 2.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0623 -0.3302 2.7236 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6572 -1.3905 -2.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5297 0.1292 -2.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7087 2.2454 -1.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4197 -0.0451 -2.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0412 0.5954 -1.8998 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7348 1.7683 -2.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5175 3.0292 -0.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6201 2.2325 1.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7492 3.2990 -0.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7746 2.8957 1.3629 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 21 26 1 0 26 27 1 0 20 28 1 0 8 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 33 2 1 0 29 4 1 0 16 7 1 0 27 18 1 0 16 11 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 1 5 42 1 0 5 43 1 0 6 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 6 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 6 19 62 1 0 19 63 1 0 20 64 1 1 21 65 1 6 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	RNETYSXHFSDFMM-GPWRYVIMSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-26(2)23-9-8-21-20(28(23,5)13-12-24(26)32)11-15-29(6)19(10-14-30(21,29)7)18-16-22(31)25(34-17-18)27(3,4)33/h8,18-20,22-23,25,31,33H,9-17H2,1-7H3/t18-,19+,20+,22-,23+,25-,28-,29+,30-/m1/s1
SMILES	CC1(C)[C@@H]2CC=C3[C@H](CC[C@@]4(C)[C@@H](CC[C@]34C)[C@@H]3C[C@H]([C@H](C(C)(C)O)OC3)O)[C@@]2(C)CCC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	4.152 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.707 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.089 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.506	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.041	Fsp³:	0.9
MCE-18:	101.333 ? 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:	0.868	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.277	Promiscuous compounds:	0.363

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008	MDCK Permeability:	-4.868
Pgp-inhibitor:	0.767	Pgp-substrate:	0.002
PAMPA:	0.059 ? 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%):	0.003	30% Bioavailability (F30%):	0.003
50% Bioavailability (F50%):	0.401

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.376	MRP1:	0.87
Plasma Protein Binding (PPB):	88.477%	Volume Distribution (VD):	0.264
Fu:	14.622% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.666
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.765	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.184	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.982
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.992 ? 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):

9.362

Half-life (T1/2):

0.598

ADMET: Toxicity

hERG Blockers:	0.077	hERG Blockers (10um):	0.191
Human Hepatotoxicity (H-HT):	0.6	Drug-induced Liver Injury (DILI):	0.344
AMES Toxicity:	0.409	Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.712	Skin Sensitization:	0.745
Carcinogencity:	0.84	Eye Corrosion:	0.001
Eye Irritation:	0.167	Respiratory Toxicity:	0.547
Drug-induced Neurotoxicity:	0.227	Ototoxicity:	0.658
Hematotoxicity:	0.663	Drug-induced Nephrotoxicity:	0.588
Genotoxicity:	0.918	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.248	Hek293 Cytotoxicity:	0.595
BCF:	1.534 ? 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:	3.904 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.441 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.736 ? 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
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30106297]
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36671701]
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38672940]
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619885]
NPO40427	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20997	Eurycoma sp.	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20997	Eurycoma sp.	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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
NPT81	Cell line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[30106297]
NPT401	Cell line	786-0	Homo sapiens	IC50	>	40000.0	nM	PMID[30106297]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[30106297]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	40000.0	nM	PMID[30106297]

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 NPC273669 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	18712
0.1-0.2	25166
0.2-0.3	5475
0.3-0.4	402
0.4-0.5	52
0.5-0.6	30
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC484802
1.0	High Similarity	NPC118647
0.7612	Intermediate Similarity	NPC478557
0.7123	Intermediate Similarity	NPC484792
0.6957	Remote Similarity	NPC470050
0.6957	Remote Similarity	NPC470051
0.6818	Remote Similarity	NPC470223
0.6812	Remote Similarity	NPC486521
0.6812	Remote Similarity	NPC262870
0.6618	Remote Similarity	NPC90652
0.6618	Remote Similarity	NPC155255
0.6479	Remote Similarity	NPC67831
0.6479	Remote Similarity	NPC174051
0.6377	Remote Similarity	NPC470417
0.6377	Remote Similarity	NPC260992
0.6111	Remote Similarity	NPC471224
0.6026	Remote Similarity	NPC189282
0.6026	Remote Similarity	NPC237402
0.5974	Remote Similarity	NPC121566
0.5974	Remote Similarity	NPC100955
0.5946	Remote Similarity	NPC605437
0.5833	Remote Similarity	NPC470047
0.5833	Remote Similarity	NPC470046
0.5797	Remote Similarity	NPC470078
0.5775	Remote Similarity	NPC472744
0.5769	Remote Similarity	NPC63023
0.5769	Remote Similarity	NPC95243
0.5733	Remote Similarity	NPC479667
0.5714	Remote Similarity	NPC73506
0.5694	Remote Similarity	NPC470052
0.557	Remote Similarity	NPC484793
0.5405	Remote Similarity	NPC171441
0.5405	Remote Similarity	NPC2983
0.5395	Remote Similarity	NPC317590
0.5385	Remote Similarity	NPC474327
0.5342	Remote Similarity	NPC82902
0.5342	Remote Similarity	NPC470224
0.5342	Remote Similarity	NPC474218
0.5263	Remote Similarity	NPC210268
0.5263	Remote Similarity	NPC190604
0.5256	Remote Similarity	NPC107243
0.5256	Remote Similarity	NPC293081
0.52	Remote Similarity	NPC469994
0.5195	Remote Similarity	NPC472239
0.5128	Remote Similarity	NPC154101
0.5128	Remote Similarity	NPC6190
0.5068	Remote Similarity	NPC247220
0.5063	Remote Similarity	NPC488538

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6584
0.1-0.2	2380
0.2-0.3	185
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