NPASS Compound

Natural Product: NPC293803

Natural Product ID	NPC293803
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Glochidone
IUPAC Name	(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aS,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysen-9-one
Synonyms	Glochidone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL469628
PubChem CID	44559199
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 77 81 0 0 0 0 0 0 0 0999 V2000 -5.0140 -1.2284 -2.8954 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0361 -0.2067 -2.3620 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4425 0.5696 -3.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8508 -0.2097 -0.9085 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1822 0.3235 -0.3306 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8156 1.3943 0.6781 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4363 0.8758 1.0421 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8721 0.7240 -0.3293 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4239 0.3906 -0.4080 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2044 -1.0265 -0.8508 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2411 -1.4451 -0.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1743 -0.3654 -0.3729 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6832 0.0671 0.9629 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5725 0.8837 0.7024 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1114 2.3259 0.3756 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2962 1.0617 2.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6034 1.8249 1.8182 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3370 -1.1147 1.8665 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6824 0.8648 1.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9673 0.0706 1.8003 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4891 0.0922 0.3823 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6028 -0.7177 -0.5305 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9064 -2.1975 -0.4703 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0521 -0.3290 -1.9131 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3484 -0.1649 -2.1351 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3514 -0.3416 -1.1105 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5466 -0.5965 -1.3636 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9385 -0.2131 0.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6691 1.0461 0.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4229 -1.3414 1.1593 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6764 -0.3676 1.8226 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8021 -1.4207 -2.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4680 -2.1921 -3.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4040 -0.9179 -3.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6225 0.5099 -4.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7419 1.3241 -2.8961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7866 -1.2501 -0.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8171 0.7394 -1.1452 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7786 -0.5020 0.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4889 1.3861 1.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7747 2.3507 0.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0858 1.7279 -0.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0565 0.9685 -1.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8552 -1.7809 -0.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5371 -1.1324 -1.9343 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3111 -2.3906 -0.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6099 -1.6951 -1.9070 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9812 0.5023 -1.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9188 2.8364 -0.1967 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0562 2.9199 1.2851 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7958 2.3417 -0.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6940 1.7007 2.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4753 0.1195 2.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9920 2.0840 2.8225 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3828 2.7141 1.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3016 -0.8028 2.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0956 -1.9168 1.8278 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6853 -1.4970 1.6721 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9055 1.8506 1.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3051 0.8861 2.8185 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8510 -0.9657 2.1004 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7247 0.5376 2.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3671 1.1638 0.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8970 -2.3568 -0.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9566 -2.6294 0.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1812 -2.7084 -1.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3671 -0.1793 -2.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6815 0.1159 -3.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0846 1.9300 0.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7683 1.0289 1.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6628 1.0529 0.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7118 -1.7413 1.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7812 -2.2130 0.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3425 -1.0730 1.7616 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0482 -1.2251 1.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4663 -0.1322 2.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7322 -0.7170 1.8350 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 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 13 18 1 1 13 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 1 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 7 31 1 1 8 4 1 0 14 9 1 0 28 21 1 0 17 7 1 0 22 12 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 4 37 1 1 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 8 42 1 6 9 43 1 6 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 6 15 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 17 54 1 0 17 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 25 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 M END

Standard InCHIKey	FWBYBHVDDGVPDF-IAFKSKRFSA-N
Standard InCHI	InChI=1S/C30H46O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h13,15,20-23,25H,1,9-12,14,16-18H2,2-8H3/t20-,21-,22-,23+,25+,27+,28-,29+,30+/m0/s1
SMILES	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)C=CC(=O)C1(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	422.35	Volume:	485.535 ? Van der Waals volume.
Dense:	0.87	LogP:	6.502 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.81 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.57 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.391	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.814	Fsp³:	0.833
MCE-18:	98.218 ? 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:	0.959	Fluc inhibitor:	0.015 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.682	Promiscuous compounds:	0.291

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.143	MDCK Permeability:	-4.872
Pgp-inhibitor:	0.939	Pgp-substrate:	0.001
PAMPA:	0.205 ? 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%):	0.083	30% Bioavailability (F30%):	0.126
50% Bioavailability (F50%):	0.788

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.937	MRP1:	0.88
Plasma Protein Binding (PPB):	97.086%	Volume Distribution (VD):	0.319
Fu:	3.104% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.46
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.017	CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.279	CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.981	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.116
HLM stability:	0.577 ? 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):

11.983

Half-life (T1/2):

0.198

ADMET: Toxicity

hERG Blockers:	0.177	hERG Blockers (10um):	0.366
Human Hepatotoxicity (H-HT):	0.641	Drug-induced Liver Injury (DILI):	0.384
AMES Toxicity:	0.208	Rat Oral Acute Toxicity:	0.675
Maximum Recommended Daily Dose:	0.851	Skin Sensitization:	0.84
Carcinogencity:	0.918	Eye Corrosion:	0.329
Eye Irritation:	0.936	Respiratory Toxicity:	0.966
Drug-induced Neurotoxicity:	0.21	Ototoxicity:	0.403
Hematotoxicity:	0.514	Drug-induced Nephrotoxicity:	0.797
Genotoxicity:	0.741	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.094	Hek293 Cytotoxicity:	0.451
BCF:	3.156 ? 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:	5.043 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.741 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.92 ? 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
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713421]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738378]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[14738378]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	root bark;leaves	Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador	n.a.	PMID[16038541]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19122328]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	root bark	Urubamba, Cusco, Peru	n.a.	PMID[25927586]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106289]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15526	Glochidion zeylanicum	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22471	Maytenus cuzcoina	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1333	Maytenus chiapensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2706	Glochidion eriocarpum	Species	Phyllanthaceae	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	3
Inhibition	1

Activity Type	# Activity
Cell line	3
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
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[16038541]
NPT1171	Cell line	HEp-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[16038541]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	>	10.0	ug.mL-1	PMID[16038541]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[25927586]

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 NPC293803 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	27184
0.1-0.2	20912
0.2-0.3	1558
0.3-0.4	156
0.4-0.5	32
0.5-0.6	11
0.6-0.7	1
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
0.7736	Intermediate Similarity	NPC474509
0.7455	Intermediate Similarity	NPC93778
0.7018	Intermediate Similarity	NPC272746
0.6071	Remote Similarity	NPC43300
0.5667	Remote Similarity	NPC57469
0.541	Remote Similarity	NPC305835
0.5246	Remote Similarity	NPC159497
0.5085	Remote Similarity	NPC192638
0.5085	Remote Similarity	NPC80297
0.5085	Remote Similarity	NPC475727
0.5085	Remote Similarity	NPC25511
0.5085	Remote Similarity	NPC116119
0.5085	Remote Similarity	NPC600137
0.5079	Remote Similarity	NPC103754
0.5077	Remote Similarity	NPC611062

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC293803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7246
0.1-0.2	1865
0.2-0.3	37
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