NPASS Compound

Natural Product: NPC32577

Natural Product ID	NPC32577
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(E/Z)-Stelliferin G
IUPAC Name	[(5S,6E,8E,10Z)-10-[(3aS,5aR,6S,7R,9aR,9bS)-7-hydroxy-6-(hydroxymethyl)-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,6,8-trien-5-yl] acetate
Synonyms	(E/Z)-Stelliferin G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL473452
PubChem CID	10768096
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 85 87 0 0 0 0 0 0 0 0999 V2000 -6.9699 -1.8710 1.0515 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1446 -0.5340 1.2967 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4734 0.3894 0.3057 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1402 -0.0161 -1.0293 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9816 1.7708 0.6205 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2254 1.9265 -0.0278 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1258 2.8986 0.2008 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6670 2.6698 0.1077 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2067 1.4080 0.8254 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9967 0.2833 0.2081 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4382 -1.0554 0.5143 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9547 -1.2322 0.3805 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2960 -0.0193 -0.1121 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7815 1.1340 0.6623 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9327 2.2581 0.1244 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6149 1.5234 0.3761 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4293 2.1071 0.7765 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8378 0.1162 0.0715 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1130 -0.8076 -0.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5034 -0.4674 0.1896 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5291 -1.2858 0.1569 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9215 -0.8447 0.3996 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9046 -1.7046 0.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2857 -1.2776 0.5905 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2214 -2.0033 -0.1888 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1360 -2.8790 0.2972 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2094 -3.1070 1.5201 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0611 -3.5771 -0.6198 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5459 0.1848 0.5974 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2692 0.9098 -0.6442 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2921 1.5712 -1.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6514 1.5816 -0.6150 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0502 2.3162 -2.4645 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5680 -3.1268 0.1215 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3317 -2.1667 -0.4197 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4815 0.0509 -1.6146 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5547 1.6083 2.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9219 -2.4069 1.8609 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0111 -0.2453 2.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2543 -0.3506 1.1232 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1459 0.3675 -1.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5007 0.4306 -1.8184 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0612 -1.1215 -1.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2928 1.8234 1.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3921 2.8910 -0.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3582 3.7668 0.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4529 3.2946 -0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2929 2.6050 -0.9433 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1384 3.5128 0.6376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8027 0.4506 -0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7539 -1.4241 1.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0144 -1.7735 -0.1560 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5712 -1.5923 1.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8597 -2.0383 -0.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3473 0.9792 1.7047 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9212 3.1320 0.8036 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0752 2.5474 -0.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7505 0.5567 0.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3812 -2.3171 -0.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0305 0.2133 0.6276 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5074 -1.6164 1.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1164 -3.5621 -0.2317 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7418 -4.6488 -0.6518 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0093 -3.1886 -1.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8668 0.6299 1.3861 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5910 0.3272 0.9487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3148 0.9314 -1.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6002 2.0128 0.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3511 2.1078 -1.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9958 0.5107 -0.5151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2682 3.0848 -2.2301 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7055 1.6385 -3.2799 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9338 2.8601 -2.8171 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9783 -3.5234 0.9929 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4738 -3.7788 0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0380 -3.2876 -0.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7754 -2.7582 0.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6321 -2.7380 -0.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8296 -2.2332 -1.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8121 1.0314 -1.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1023 -0.8100 -1.9987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5134 -0.1039 -2.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8857 0.7024 2.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1585 2.5173 2.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5778 1.8611 2.8165 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 3 5 1 0 5 6 1 0 5 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 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 24 29 1 0 29 30 1 0 30 31 2 3 31 32 1 0 31 33 1 0 23 34 1 0 19 35 1 0 13 36 1 6 9 37 1 1 10 3 1 0 18 13 1 0 14 9 1 0 1 38 1 0 2 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 4 43 1 0 5 44 1 1 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 6 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 14 55 1 1 15 56 1 0 15 57 1 0 20 58 1 0 21 59 1 0 22 60 1 0 24 61 1 1 28 62 1 0 28 63 1 0 28 64 1 0 29 65 1 0 29 66 1 0 30 67 1 0 32 68 1 0 32 69 1 0 32 70 1 0 33 71 1 0 33 72 1 0 33 73 1 0 34 74 1 0 34 75 1 0 34 76 1 0 35 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 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	LRKJRNYRZIABOX-SVOIAGRFSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-20(2)12-13-25(37-23(5)34)21(3)10-9-11-22(4)29-24(35)18-27-30(6)17-15-28(36)32(8,19-33)26(30)14-16-31(27,29)7/h9-12,25-28,33,36H,13-19H2,1-8H3/b11-9+,21-10+,29-22+/t25-,26+,27-,28+,30-,31-,32+/m0/s1
SMILES	OC[C@@]1(C)[C@H](O)CC[C@]2([C@H]1CC[C@]1([C@H]2CC(=O)/C/1=C(C=CC=C([C@@H](OC(=O)C)CC=C(C)C)/C)/C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.35	Volume:	564.491 ? Van der Waals volume.
Dense:	0.908	LogP:	3.884 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.674 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.998 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	21.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.182	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.004	Fsp³:	0.688
MCE-18:	67.407 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.68	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.074 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.553	Promiscuous compounds:	0.519

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.995	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.958	Pgp-substrate:	0.615
PAMPA:	0.168 ? 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%):	0.069	30% Bioavailability (F30%):	0.048
50% Bioavailability (F50%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.991
Plasma Protein Binding (PPB):	84.107%	Volume Distribution (VD):	0.022
Fu:	16.214% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.035
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.024	CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.948	CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.014	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.637
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.999
HLM stability:	0.73 ? 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):

10.078

Half-life (T1/2):

0.832

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.182
Human Hepatotoxicity (H-HT):	0.553	Drug-induced Liver Injury (DILI):	0.149
AMES Toxicity:	0.398	Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.601	Skin Sensitization:	0.98
Carcinogencity:	0.901	Eye Corrosion:	0.006
Eye Irritation:	0.473	Respiratory Toxicity:	0.591
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.512
Hematotoxicity:	0.293	Drug-induced Nephrotoxicity:	0.65
Genotoxicity:	0.47	RPMI-8226 Immunitoxicity:	0.112
A549 Cytotoxicity:	0.153	Hek293 Cytotoxicity:	0.255
BCF:	1.224 ? 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:	4.092 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.758 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.054 ? 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
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10924	Stelletta globostellata	Species	Ancorinidae	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
GI50	1
IC50	2

Activity Type	# Activity
Cell line	3

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
NPT168	Cell line	P388	Mus musculus	GI50	=	160.0	nM	PMID[14643329]
NPT375	Cell line	Malme-3M	Homo sapiens	IC50	=	0.23	ug.mL-1	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	4.11	ug.mL-1	PubChem BioAssay data set

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 NPC32577 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	16545
0.1-0.2	26163
0.2-0.3	6831
0.3-0.4	261
0.4-0.5	30
0.5-0.6	16
0.6-0.7	8
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
0.75	Intermediate Similarity	NPC155332
0.75	Intermediate Similarity	NPC114540
0.7077	Intermediate Similarity	NPC310752
0.6912	Remote Similarity	NPC474690
0.6912	Remote Similarity	NPC292491
0.6667	Remote Similarity	NPC474785
0.662	Remote Similarity	NPC110937
0.6579	Remote Similarity	NPC475163
0.6049	Remote Similarity	NPC473617
0.6049	Remote Similarity	NPC473828
0.6027	Remote Similarity	NPC605871
0.5915	Remote Similarity	NPC141292
0.589	Remote Similarity	NPC474844
0.5789	Remote Similarity	NPC115899
0.5753	Remote Similarity	NPC471153
0.5541	Remote Similarity	NPC57079
0.5541	Remote Similarity	NPC108368
0.5526	Remote Similarity	NPC266955
0.5263	Remote Similarity	NPC180950
0.5132	Remote Similarity	NPC473435
0.5132	Remote Similarity	NPC473879
0.5132	Remote Similarity	NPC473280
0.5132	Remote Similarity	NPC471078
0.5128	Remote Similarity	NPC250757
0.5128	Remote Similarity	NPC301534
0.5067	Remote Similarity	NPC151725
0.5059	Remote Similarity	NPC266570

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC32577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6586
0.1-0.2	2473
0.2-0.3	89
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