NPASS Compound

Natural Product: NPC115899

Natural Product ID	NPC115899
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(E/Z)-29-Hydroxystelliferin A
IUPAC Name	[(3Z,3aS,5aR,6S,7S,9aR,9bS)-3-[(3E,5E,7S)-7-hydroxy-6,10-dimethylundeca-3,5,9-trien-2-ylidene]-6-(hydroxymethyl)-3a,6,9a-trimethyl-2-oxo-1,4,5,5a,7,8,9,9b-octahydrocyclopenta[a]naphthalen-7-yl] acetate
Synonyms	(E/Z)-29-Hydroxystelliferin A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL474075
PubChem CID	10720560
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 10.1041 3.3983 4.3987 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0767 2.8052 3.5144 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5688 1.5889 3.7308 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5439 0.9819 2.8594 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2679 0.6679 3.6265 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2690 0.0536 2.6801 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1028 0.6357 2.4548 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1657 0.0237 1.5431 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9717 0.5554 1.2671 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0299 -0.0655 0.3462 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1743 0.4101 0.0799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7156 1.6187 0.6692 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2501 2.3304 1.5650 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0395 1.9295 -0.0076 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4448 0.4864 -0.1830 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7872 0.2087 -0.6929 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7345 0.2083 0.5189 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3900 1.2322 -1.6292 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6953 0.7438 -2.1816 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4830 -0.5674 -2.8691 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0060 -1.6554 -1.8935 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6428 -2.8345 -2.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0748 -2.1167 -0.9878 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6878 -3.0949 -0.0933 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7402 -1.1558 -1.3482 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8793 -2.0261 -0.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 -1.6017 -0.7897 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2461 -0.1085 -0.8262 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8659 0.4125 -2.1841 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5532 -0.9894 -3.6437 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4022 -1.1492 -5.0122 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2706 -0.9035 -5.5412 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4899 -1.5936 -5.9063 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4962 -1.3110 -0.3667 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6523 -1.2186 2.0178 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6239 -0.2529 4.6236 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5776 3.5649 2.3438 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1338 3.2352 4.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9322 3.0539 5.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9070 4.5075 4.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9365 1.0345 4.5900 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9493 0.0806 2.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2985 1.7005 2.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9003 1.5975 4.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9234 1.5597 2.9841 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4206 -0.8996 1.0648 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7691 1.4813 1.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9152 2.4928 -0.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7415 2.4031 0.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 0.0880 0.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2351 0.9011 1.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6931 0.6959 0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7767 -0.7591 1.0163 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7599 1.5393 -2.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6018 2.1496 -1.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9797 1.4691 -3.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5435 0.7484 -1.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5823 -0.4095 -3.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5775 -2.8059 -3.1065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3324 -2.9099 -3.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7711 -3.7482 -2.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8478 -2.6338 -1.6413 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6683 -1.2998 -0.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4864 -3.5968 0.1963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1439 -0.9417 -2.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0968 -1.9972 0.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0194 -3.0775 -0.8534 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1821 -2.1070 -1.7574 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8520 -1.9898 0.0734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2285 0.7078 -2.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9142 -0.4214 -2.9367 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3919 1.3223 -2.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2884 -1.2610 -6.9460 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4675 -1.1530 -5.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5171 -2.7096 -5.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5756 -1.1557 -0.6854 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9825 -1.4375 -1.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5108 -2.1940 0.2749 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6128 -1.1404 0.9128 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6753 -1.5086 2.2980 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9899 -2.0601 2.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1907 -0.9713 4.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1064 4.5391 2.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7570 2.9788 1.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4806 3.6912 2.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 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 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 20 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 10 34 1 0 6 35 1 0 5 36 1 0 2 37 1 0 28 11 1 0 28 15 1 0 25 16 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 1 7 45 1 0 8 46 1 0 9 47 1 0 14 48 1 0 14 49 1 0 15 50 1 1 17 51 1 0 17 52 1 0 17 53 1 0 18 54 1 0 18 55 1 0 19 56 1 0 19 57 1 0 20 58 1 6 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 25 65 1 6 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 29 70 1 0 29 71 1 0 29 72 1 0 33 73 1 0 33 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	QDIPGNADJXRSEJ-BLOHMGETSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-20(2)12-13-24(35)21(3)10-9-11-22(4)29-25(36)18-27-30(6)17-15-28(37-23(5)34)32(8,19-33)26(30)14-16-31(27,29)7/h9-12,24,26-28,33,35H,13-19H2,1-8H3/b11-9+,21-10+,29-22+/t24-,26+,27-,28-,30-,31-,32+/m0/s1
SMILES	CC(=CC[C@@H](/C(=C/C=C/C(=C/1C(=O)C[C@H]2[C@@]3(C)CC[C@@H]([C@](C)(CO)[C@@H]3CC[C@]12C)OC(=O)C)/C)/C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.35	Volume:	564.491 ? Van der Waals volume.
Dense:	0.908	LogP:	3.855 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.76 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.558 ? 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:	4.99	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:	0.727	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.069 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.556	Promiscuous compounds:	0.471

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.075	MDCK Permeability:	-4.848
Pgp-inhibitor:	0.027	Pgp-substrate:	0.747
PAMPA:	0.956 ? 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%):	0.013	30% Bioavailability (F30%):	0.083
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.966
Plasma Protein Binding (PPB):	83.293%	Volume Distribution (VD):	0.079
Fu:	14.567% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.955
OATP1B3 inhibitor:	0.715	BCRP inhibitor:	0.018
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.431	CYP2C19-substrate:	0.103
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.119
CYP2D6-inhibitor:	0.014	CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.641
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.27 ? 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):

8.74

Half-life (T1/2):

0.622

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.223
Human Hepatotoxicity (H-HT):	0.489	Drug-induced Liver Injury (DILI):	0.29
AMES Toxicity:	0.433	Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.291	Skin Sensitization:	0.932
Carcinogencity:	0.792	Eye Corrosion:	0.007
Eye Irritation:	0.317	Respiratory Toxicity:	0.255
Drug-induced Neurotoxicity:	0.025	Ototoxicity:	0.651
Hematotoxicity:	0.542	Drug-induced Nephrotoxicity:	0.525
Genotoxicity:	0.328	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.115	Hek293 Cytotoxicity:	0.117
BCF:	1.142 ? 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:	4.196 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.995 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.229 ? 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
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]
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]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	2

Activity Type	# Activity
Cell line	2

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
NPT375	Cell line	Malme-3M	Homo sapiens	IC50	=	0.11	ug.mL-1	PMID[15787444]
NPT112	Cell line	MOLT-4	Homo sapiens	IC50	=	1.62	ug.mL-1	PMID[16643030]

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 NPC115899 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	17091
0.1-0.2	25716
0.2-0.3	6823
0.3-0.4	169
0.4-0.5	30
0.5-0.6	25
0.6-0.7	1
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
0.8438	Intermediate Similarity	NPC266955
0.75	Intermediate Similarity	NPC155332
0.75	Intermediate Similarity	NPC114540
0.6912	Remote Similarity	NPC474690
0.5972	Remote Similarity	NPC473435
0.5972	Remote Similarity	NPC473280
0.5972	Remote Similarity	NPC471078
0.5915	Remote Similarity	NPC151725
0.5789	Remote Similarity	NPC473284
0.5789	Remote Similarity	NPC32577
0.5733	Remote Similarity	NPC110937
0.5694	Remote Similarity	NPC474842
0.5694	Remote Similarity	NPC475965
0.5694	Remote Similarity	NPC604299
0.56	Remote Similarity	NPC106425
0.56	Remote Similarity	NPC122324
0.56	Remote Similarity	NPC605871
0.5584	Remote Similarity	NPC473482
0.5513	Remote Similarity	NPC473283
0.5513	Remote Similarity	NPC475526
0.5476	Remote Similarity	NPC473617
0.5476	Remote Similarity	NPC473828
0.5278	Remote Similarity	NPC2049
0.5205	Remote Similarity	NPC310752
0.5195	Remote Similarity	NPC6206
0.5132	Remote Similarity	NPC292491
0.5128	Remote Similarity	NPC10064
0.5128	Remote Similarity	NPC170221
0.5067	Remote Similarity	NPC141292

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC115899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6495
0.1-0.2	2559
0.2-0.3	96
0.3-0.4	0
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