NPASS Compound

Natural Product: NPC477813

Natural Product ID	NPC477813
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
IUPAC Name	2-[(3S,5R,10S,13R,14R,16R,17R)-3-acetyloxy-16-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	Dehydropachymic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12133289
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 88 91 0 0 0 0 0 0 0 0999 V2000 -5.2535 2.4624 1.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3254 1.4753 1.6369 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6212 1.9592 1.0903 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0405 0.0834 1.1441 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9175 -0.4666 0.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7885 -0.5723 1.5539 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2419 -1.7348 0.8869 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7173 -1.7850 -0.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6017 -0.9116 -0.9068 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7967 0.5543 -0.8737 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5861 1.1294 -0.1103 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5452 0.1608 -0.5998 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2628 -1.1667 -0.2986 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4486 -2.2118 -1.0083 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0002 -2.0960 -0.6989 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5763 -1.0306 -0.1665 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7060 0.1230 0.1376 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0892 1.0227 1.0308 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4157 0.8132 1.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3490 0.4121 0.5703 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0291 -0.9744 0.1413 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8213 -1.3104 -1.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3017 -1.1207 -0.8308 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5187 0.3132 -0.4783 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7889 0.6977 0.8041 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3983 0.0922 2.0157 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9377 2.2150 0.9200 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8577 0.7147 -0.4604 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3772 1.6911 -1.3139 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5804 2.2239 -2.1341 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7861 2.1199 -1.3015 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2695 -2.0173 1.2017 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2147 -1.4058 1.1624 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2621 0.3595 -2.0464 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7577 1.1099 -2.1908 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7262 -1.9784 -1.5382 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9715 -1.1112 -2.4262 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4916 -3.1583 -1.6427 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2809 2.2761 1.8428 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1496 2.7126 0.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5999 3.4414 1.8121 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4527 1.4480 2.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6682 2.0492 -0.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4587 1.3459 1.4637 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8549 2.9963 1.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7900 -1.4501 -0.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8299 0.0887 0.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0505 0.2662 1.7245 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0525 -0.9494 2.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1628 -2.4831 0.8447 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6131 -2.3814 1.6200 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1752 -2.8593 -0.5306 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4545 -1.1725 -2.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6848 0.9586 -0.4334 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7409 1.1317 0.9649 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3369 2.1349 -0.5057 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6489 -2.2711 -2.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7762 -3.2052 -0.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -2.9399 -0.9258 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4397 1.8462 1.2391 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2900 0.0369 2.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7614 1.7304 2.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0610 1.0717 -0.3075 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5521 -0.5430 -1.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5889 -2.2952 -1.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8487 -1.2945 -1.7994 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6904 -1.8053 -0.0600 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0151 0.9238 -1.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7604 0.2655 2.8807 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3542 0.6599 2.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7336 -0.9620 1.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2702 2.7483 0.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6593 2.5208 1.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9781 2.5334 0.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3777 1.4721 -0.6363 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7942 3.1854 -0.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2539 2.1288 -2.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3985 -2.7291 1.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1048 -2.6672 0.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4502 -1.6222 2.1982 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2680 -2.4481 1.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9047 -0.7843 1.7670 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1841 -1.0679 1.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7796 -0.2914 -2.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4516 1.4164 -2.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 0.2171 -2.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6526 1.2999 -2.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0504 -3.3651 -2.4592 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 2 0 4 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 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 21 32 1 1 13 33 1 1 12 34 1 6 10 35 1 0 8 36 1 0 36 37 2 0 36 38 1 0 13 9 1 0 17 12 1 0 21 16 1 0 25 20 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 0 3 43 1 0 3 44 1 0 3 45 1 0 5 46 1 0 5 47 1 0 6 48 1 0 6 49 1 0 7 50 1 0 7 51 1 0 8 52 1 0 9 53 1 6 10 54 1 1 11 55 1 0 11 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 6 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 24 68 1 6 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 27 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 38 88 1 0 M END

Standard InCHIKey	RWIALJIVPUCERT-MTHWCOGXSA-N
Standard InCHI	InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h12,14,19,22,25-28,35H,3,10-11,13,15-18H2,1-2,4-9H3,(H,36,37)/t22?,25-,26+,27+,28+,31-,32-,33+/m1/s1
SMILES	CC(C)C(=C)CCC([C@H]1[C@@H](C[C@@]2([C@@]1(CC=C3C2=CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)OC(=O)C)C)C)C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	526.37	Volume:	575.867 ? Van der Waals volume.
Dense:	0.914	LogP:	4.269 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.51 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.766 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	23.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.273	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.14	Fsp³:	0.758
MCE-18:	85.69 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.893	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.123 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.257	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.955	Pgp-substrate:	0.0
PAMPA:	0.171 ? 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%):	0.886	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.997
Plasma Protein Binding (PPB):	89.084%	Volume Distribution (VD):	-0.384
Fu:	9.821% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.059
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.259 ? 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):

4.03

Half-life (T1/2):

0.759

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.526	Drug-induced Liver Injury (DILI):	0.246
AMES Toxicity:	0.149	Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.231	Skin Sensitization:	0.909
Carcinogencity:	0.561	Eye Corrosion:	0.031
Eye Irritation:	0.598	Respiratory Toxicity:	0.372
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.59
Hematotoxicity:	0.439	Drug-induced Nephrotoxicity:	0.522
Genotoxicity:	0.577	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.07	Hek293 Cytotoxicity:	0.113
BCF:	0.983 ? 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:	3.934 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.907 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.088 ? 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
NPO33546	Poria coco	Species	n.a.	Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]

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
Inhibition	4
Activity	1

Activity Type	# Activity
Cell line	1
Organism	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	28.1	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	72.4	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	95.1	%	PMID[17488130]

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 NPC477813 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	15626
0.1-0.2	28280
0.2-0.3	5617
0.3-0.4	249
0.4-0.5	45
0.5-0.6	18
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
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	NPC288464
1.0	High Similarity	NPC607198
0.8235	Intermediate Similarity	NPC484969
0.75	Intermediate Similarity	NPC45324
0.75	Intermediate Similarity	NPC162001
0.7083	Intermediate Similarity	NPC263347
0.7042	Intermediate Similarity	NPC152897
0.7042	Intermediate Similarity	NPC484967
0.6944	Remote Similarity	NPC184848
0.6575	Remote Similarity	NPC123854
0.6438	Remote Similarity	NPC186810
0.6164	Remote Similarity	NPC48866
0.6133	Remote Similarity	NPC484973
0.6133	Remote Similarity	NPC484968
0.6053	Remote Similarity	NPC155676
0.6027	Remote Similarity	NPC222845
0.6027	Remote Similarity	NPC296577
0.6	Remote Similarity	NPC484975
0.6	Remote Similarity	NPC321301
0.6	Remote Similarity	NPC608955
0.5844	Remote Similarity	NPC69548
0.5789	Remote Similarity	NPC48647
0.5658	Remote Similarity	NPC66429
0.5658	Remote Similarity	NPC77168
0.5641	Remote Similarity	NPC276127
0.5641	Remote Similarity	NPC7165
0.5641	Remote Similarity	NPC478307
0.5584	Remote Similarity	NPC484966
0.5584	Remote Similarity	NPC477812
0.5443	Remote Similarity	NPC478313
0.5443	Remote Similarity	NPC489790
0.5432	Remote Similarity	NPC469432
0.5325	Remote Similarity	NPC474889
0.5256	Remote Similarity	NPC45269
0.5256	Remote Similarity	NPC203035
0.5176	Remote Similarity	NPC484972
0.5119	Remote Similarity	NPC94393
0.5065	Remote Similarity	NPC23434

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5418
0.1-0.2	3616
0.2-0.3	114
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