NPASS Compound

Natural Product: NPC84113

Natural Product ID	NPC84113
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PWZMNBAVCHYMBK-FMMUPTMQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21594250
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 84 0 0 0 0 0 0 0 0999 V2000 -5.8790 1.9343 0.9939 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1489 1.0953 -0.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3898 1.6705 -1.4122 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6738 1.1975 0.2786 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0349 -0.0557 -0.3392 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5600 0.0611 -0.4013 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0694 0.9730 -1.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3593 1.2583 -1.4563 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1830 0.4292 -0.5604 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6709 0.4389 -0.8002 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1284 -0.3424 -1.9841 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1974 1.8368 -0.9242 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7655 2.3909 0.3571 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9799 1.5832 0.7630 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6827 0.1001 0.7195 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9765 -0.4316 2.1352 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6220 -0.6045 -0.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2338 -0.1224 0.5139 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7404 -1.5011 0.7987 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5719 -1.9710 0.0475 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6033 -0.9518 -0.4602 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0638 -1.4824 -1.7807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6342 -0.7975 0.4299 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3657 -0.0157 1.6834 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2348 -2.1024 0.8068 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6771 -2.0561 1.1648 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5729 -1.2555 0.3181 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8047 -0.9156 1.1935 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6703 -0.3150 0.1022 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3632 -1.1461 -1.0103 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3459 -2.0366 -0.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2073 -3.1632 -1.1717 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1033 1.9161 -0.0038 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9199 1.5752 1.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4379 1.7768 1.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8272 3.0069 0.7744 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5523 1.5370 -2.1097 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3510 1.3462 -1.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4970 2.7880 -1.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2053 2.0502 -0.2951 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4572 1.3143 1.3337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3812 0.0165 -1.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7590 1.5953 -1.8356 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4735 2.3492 -1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6512 1.2224 -2.5265 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0728 0.9038 0.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3487 -0.6311 -2.7039 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6763 -1.2750 -1.7378 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8645 0.2475 -2.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4855 2.5713 -1.3127 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0588 1.8589 -1.6593 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1635 3.4121 0.0916 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0427 2.5470 1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2334 1.9409 1.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0141 -0.2370 2.4299 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6518 -1.4723 2.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3339 0.1810 2.8139 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4286 -1.7012 -0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7394 -0.1854 -1.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6479 -0.5107 0.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7310 0.5400 1.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 -1.6152 1.9067 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6194 -2.1943 0.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9413 -2.6291 -0.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9970 -2.7012 0.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6797 -2.3470 -2.1602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0203 -0.7639 -2.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9655 -1.9345 -1.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 -0.1881 2.1335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1096 -0.3574 2.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6215 1.0802 1.5726 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0727 -2.9306 0.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7005 -2.4344 1.7522 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0542 -3.0983 1.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7579 -1.6626 2.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2411 -1.8909 1.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5678 -0.2485 2.0092 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7344 -0.2985 0.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9730 1.8276 -0.9596 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 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 27 26 1 1 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 14 33 1 0 29 2 1 0 27 5 1 0 23 6 1 0 31 27 1 0 21 9 1 0 18 10 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 6 7 43 1 0 8 44 1 0 8 45 1 0 9 46 1 1 11 47 1 0 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 1 16 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 1 19 62 1 0 19 63 1 0 20 64 1 0 20 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 28 76 1 0 28 77 1 0 29 78 1 1 33 79 1 0 M END

Standard InCHIKey	PWZMNBAVCHYMBK-FMMUPTMQSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-25(2)16-19-18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-29(21,7)28(18,6)14-15-30(19)17-23(25)33-24(30)32/h8,19-23,31H,9-17H2,1-7H3/t19-,20-,21+,22-,23-,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]32C[C@@H]1OC3=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	497.195 ? Van der Waals volume.
Dense:	0.914	LogP:	4.616 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.12 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.699 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.328	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.127	Fsp³:	0.9
MCE-18:	159.175 ? 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:	0.914	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? 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:	0.366	Promiscuous compounds:	0.108

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.224	MDCK Permeability:	-4.984
Pgp-inhibitor:	0.968	Pgp-substrate:	0.129
PAMPA:	0.952 ? 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):	0.003
20% Bioavailability (F20%):	0.733	30% Bioavailability (F30%):	0.197
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09	MRP1:	0.903
Plasma Protein Binding (PPB):	96.701%	Volume Distribution (VD):	-0.068
Fu:	3.972% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.644
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.936	CYP1A2-substrate:	0.028
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.585
CYP2C9-inhibitor:	0.107	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.015	CYP2D6-substrate:	0.286
CYP3A4-inhibitor:	0.081	CYP3A4-substrate:	0.721
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.74
HLM stability:	0.967 ? 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):

9.318

Half-life (T1/2):

0.37

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.196
Human Hepatotoxicity (H-HT):	0.657	Drug-induced Liver Injury (DILI):	0.582
AMES Toxicity:	0.806	Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.834	Skin Sensitization:	0.993
Carcinogencity:	0.943	Eye Corrosion:	0.007
Eye Irritation:	0.222	Respiratory Toxicity:	0.721
Drug-induced Neurotoxicity:	0.375	Ototoxicity:	0.5
Hematotoxicity:	0.587	Drug-induced Nephrotoxicity:	0.962
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.795	Hek293 Cytotoxicity:	0.416
BCF:	2.432 ? 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:	4.539 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.682 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.385 ? 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
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12465	Glycyrrhiza yunnanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15413	Glycyrrhiza pallidiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12181	Albizia julibrissin	Species	Fabaceae	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

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

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 NPC84113 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	18183
0.1-0.2	24960
0.2-0.3	5385
0.3-0.4	1023
0.4-0.5	231
0.5-0.6	54
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
0.7538	Intermediate Similarity	NPC164349
0.7302	Intermediate Similarity	NPC246708
0.7273	Intermediate Similarity	NPC49776
0.7273	Intermediate Similarity	NPC63118
0.7273	Intermediate Similarity	NPC474436
0.6308	Remote Similarity	NPC235341
0.6269	Remote Similarity	NPC40552
0.619	Remote Similarity	NPC290598
0.619	Remote Similarity	NPC30590
0.6111	Remote Similarity	NPC294360
0.6104	Remote Similarity	NPC167383
0.6081	Remote Similarity	NPC283343
0.5909	Remote Similarity	NPC101475
0.5789	Remote Similarity	NPC473160
0.5775	Remote Similarity	NPC7260
0.5775	Remote Similarity	NPC210037
0.5775	Remote Similarity	NPC120968
0.5775	Remote Similarity	NPC488519
0.5775	Remote Similarity	NPC227467
0.5775	Remote Similarity	NPC273621
0.5735	Remote Similarity	NPC470588
0.5692	Remote Similarity	NPC27765
0.5692	Remote Similarity	NPC122418
0.5692	Remote Similarity	NPC491014
0.5634	Remote Similarity	NPC136313
0.5556	Remote Similarity	NPC171203
0.5556	Remote Similarity	NPC307426
0.5556	Remote Similarity	NPC98442
0.5556	Remote Similarity	NPC242468
0.5526	Remote Similarity	NPC475263
0.5526	Remote Similarity	NPC488518
0.5507	Remote Similarity	NPC95594
0.5493	Remote Similarity	NPC162107
0.5493	Remote Similarity	NPC46912
0.5455	Remote Similarity	NPC120098
0.5455	Remote Similarity	NPC273668
0.5443	Remote Similarity	NPC191763
0.5441	Remote Similarity	NPC311078
0.5441	Remote Similarity	NPC34177
0.5385	Remote Similarity	NPC258547
0.5366	Remote Similarity	NPC237503
0.5362	Remote Similarity	NPC253807
0.5362	Remote Similarity	NPC158662
0.5333	Remote Similarity	NPC480919
0.5316	Remote Similarity	NPC476132
0.5286	Remote Similarity	NPC159168
0.5278	Remote Similarity	NPC477579
0.5256	Remote Similarity	NPC471433
0.5256	Remote Similarity	NPC88349
0.5256	Remote Similarity	NPC471432
0.5244	Remote Similarity	NPC46388
0.5217	Remote Similarity	NPC196753
0.5205	Remote Similarity	NPC214756
0.5205	Remote Similarity	NPC610937
0.5185	Remote Similarity	NPC603645
0.5143	Remote Similarity	NPC40394
0.5143	Remote Similarity	NPC195334
0.5135	Remote Similarity	NPC474845
0.5135	Remote Similarity	NPC481361
0.5125	Remote Similarity	NPC480921
0.5125	Remote Similarity	NPC480920
0.5122	Remote Similarity	NPC474190
0.5072	Remote Similarity	NPC474989
0.5068	Remote Similarity	NPC477872
0.5067	Remote Similarity	NPC18872
0.5067	Remote Similarity	NPC290614

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC84113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6798
0.1-0.2	2266
0.2-0.3	80
0.3-0.4	4
0.4-0.5	1
0.5-0.6	1
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
0.5775	Remote Similarity	NPD7645	Phase 2

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