NPASS Compound

Natural Product: NPC476878

Natural Product ID	NPC476878
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	23-Acetoxy-3beta-acetylimberbic acid
IUPAC Name	(2R,4aS,6aS,6aS,6bR,8aR,9R,10S,12S,12aR,14bS)-10-acetyloxy-9-(acetyloxymethyl)-12-hydroxy-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	45268131
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 93 97 0 0 0 0 0 0 0 0999 V2000 7.8411 1.3538 2.8283 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3590 1.1349 2.9273 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7255 1.4058 3.9993 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6139 0.6385 1.8859 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2110 0.4241 1.9593 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8378 -0.1340 0.5635 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3830 -0.3883 0.5489 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9442 -1.7128 1.0919 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4554 -1.5786 1.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3606 -1.3659 0.1411 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1941 -0.1867 -0.5516 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6719 -0.0865 -0.7498 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9574 1.4095 -0.9488 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3845 1.7330 -1.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3655 0.8441 -0.4229 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1001 0.1745 -1.4364 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4342 0.3877 -1.6841 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0318 1.2328 -0.9597 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1237 -0.3593 -2.7675 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4930 2.0173 0.2413 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2213 -0.7749 -1.9342 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5802 -0.0240 -1.8412 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9685 0.3282 -1.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5129 -0.1684 -0.3768 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 -1.0967 0.4969 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6181 -2.3948 0.4932 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0420 -2.1367 0.8735 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7049 -1.0435 0.1106 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8897 0.2050 -0.0147 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5464 1.1480 -0.9583 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9257 1.4781 -0.4937 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7162 0.3404 0.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9762 -0.6535 0.8501 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6801 2.0231 -1.7170 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9418 2.5815 0.5229 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5542 3.6659 0.3422 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2679 2.4598 1.7401 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1381 -1.5952 -1.2295 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8294 -0.6599 1.9554 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2880 -2.6576 -0.6195 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6805 -1.4110 0.4772 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2204 1.2263 3.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0965 2.3302 2.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3128 0.5141 2.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7388 1.3938 2.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0381 -0.3201 2.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9295 0.3568 1.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4084 -1.8677 2.0980 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1817 -2.5750 0.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3738 -0.6880 2.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1996 -2.5337 1.9062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0981 0.7099 0.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3883 1.8559 -1.7564 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4969 2.8070 -0.7439 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5973 1.8364 -2.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1419 1.5227 0.0508 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3908 -0.6962 -3.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5981 -1.2913 -2.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9132 0.2678 -3.2300 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4900 3.0027 0.1401 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6828 -0.0875 -2.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9841 -1.5440 -1.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 -1.2964 -2.4974 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1246 0.7456 -2.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5578 -0.9587 -2.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 1.0226 -2.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6223 -2.8885 -0.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2048 -3.0656 1.3040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5973 -3.0865 0.5974 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2060 -2.0785 1.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9029 0.7178 0.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5668 0.8248 -2.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9561 2.1099 -0.9460 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5315 0.7701 0.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2852 -0.2172 -0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5954 -1.5868 0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7712 -0.3423 1.8888 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6837 3.1179 -1.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7552 1.7050 -1.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2661 1.5537 -2.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6092 2.9016 2.5842 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8762 -2.4175 -0.9926 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3292 -2.0730 -1.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6779 -0.8795 -1.8500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3801 0.3112 2.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8952 -0.5621 2.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4264 -1.5094 2.5380 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6040 -3.4615 0.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8961 -2.7163 -1.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7419 -2.9533 -0.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0582 -1.5223 -0.5591 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1633 -2.2849 0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6243 -1.3149 1.0945 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 6 5 1 1 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 1 0 16 17 1 0 17 18 2 0 17 19 1 0 13 20 1 0 12 21 1 6 11 22 1 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 6 31 35 1 0 35 36 2 0 35 37 1 0 28 38 1 6 25 39 1 1 10 40 1 6 6 41 1 0 15 6 1 0 12 7 1 0 25 10 1 0 29 24 1 0 33 28 1 0 1 42 1 0 1 43 1 0 1 44 1 0 5 45 1 0 5 46 1 0 7 47 1 1 8 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 11 52 1 1 13 53 1 6 14 54 1 0 14 55 1 0 15 56 1 1 19 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 26 67 1 0 26 68 1 0 27 69 1 0 27 70 1 0 29 71 1 1 30 72 1 0 30 73 1 0 32 74 1 0 32 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 37 81 1 0 38 82 1 0 38 83 1 0 38 84 1 0 39 85 1 0 39 86 1 0 39 87 1 0 40 88 1 0 40 89 1 0 40 90 1 0 41 91 1 0 41 92 1 0 41 93 1 0 M END

Standard InCHIKey	JHPUYVYFNUDTGJ-QJPZVTGISA-N
Standard InCHI	InChI=1S/C34H52O7/c1-20(35)40-19-31(5)24-11-12-33(7)25(34(24,8)26(37)17-27(31)41-21(2)36)10-9-22-23-18-30(4,28(38)39)14-13-29(23,3)15-16-32(22,33)6/h9,23-27,37H,10-19H2,1-8H3,(H,38,39)/t23-,24+,25+,26+,27+,29-,30-,31+,32-,33-,34+/m1/s1
SMILES	CC(=O)OC[C@]1([C@@H]2CC[C@@]3([C@@H]([C@]2([C@H](C[C@@H]1OC(=O)C)O)C)CC=C4[C@]3(CC[C@@]5([C@@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	572.37	Volume:	604.823 ? Van der Waals volume.
Dense:	0.946	LogP:	2.957 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.05 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.579 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	29.0
TPSA:	110.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.179	Fsp³:	0.853
MCE-18:	110.667 ? 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:	0.895	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.174 ? 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:	0.266	Promiscuous compounds:	0.26

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.179	MDCK Permeability:	-4.92
Pgp-inhibitor:	0.004	Pgp-substrate:	0.005
PAMPA:	1.0 ? 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%):	0.283	30% Bioavailability (F30%):	0.041
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.473	MRP1:	0.976
Plasma Protein Binding (PPB):	83.626%	Volume Distribution (VD):	-0.61
Fu:	12.709% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.741	BCRP inhibitor:	0.335
BSEP inhibitor:	0.975

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.871	CYP3A4-substrate:	0.982
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.001 ? 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):

0.658

Half-life (T1/2):

1.783

ADMET: Toxicity

hERG Blockers:	0.102	hERG Blockers (10um):	0.137
Human Hepatotoxicity (H-HT):	0.599	Drug-induced Liver Injury (DILI):	0.714
AMES Toxicity:	0.203	Rat Oral Acute Toxicity:	0.536
Maximum Recommended Daily Dose:	0.673	Skin Sensitization:	0.96
Carcinogencity:	0.91	Eye Corrosion:	0.001
Eye Irritation:	0.014	Respiratory Toxicity:	0.86
Drug-induced Neurotoxicity:	0.063	Ototoxicity:	0.361
Hematotoxicity:	0.322	Drug-induced Nephrotoxicity:	0.497
Genotoxicity:	0.723	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.191	Hek293 Cytotoxicity:	0.351
BCF:	0.541 ? 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:	3.868 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.905 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.175 ? 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
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	leaves, flowers	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	leaves	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	flowers	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]

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
Ki	1
IC50	3

Activity Type	# Activity
Individual protein	1
Cell line	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2796	Individual protein	Apoptosis regulator Bcl-X	Homo sapiens	Ki	=	17800	nM	PMID[19572612]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	4700	nM	PMID[19572612]
NPT91	Cell line	KB	Homo sapiens	IC50	=	5400	nM	PMID[19572612]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	6000	nM	PMID[19572612]

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 NPC476878 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	17967
0.1-0.2	26157
0.2-0.3	4798
0.3-0.4	814
0.4-0.5	91
0.5-0.6	22
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
0.6667	Remote Similarity	NPC476882
0.6538	Remote Similarity	NPC474529
0.6234	Remote Similarity	NPC171203
0.6234	Remote Similarity	NPC307426
0.6234	Remote Similarity	NPC98442
0.6234	Remote Similarity	NPC242468
0.617	Remote Similarity	NPC476881
0.6105	Remote Similarity	NPC476880
0.5926	Remote Similarity	NPC46441
0.5926	Remote Similarity	NPC78580
0.5895	Remote Similarity	NPC476886
0.5802	Remote Similarity	NPC263393
0.5802	Remote Similarity	NPC474525
0.5761	Remote Similarity	NPC476887
0.5488	Remote Similarity	NPC155120
0.5488	Remote Similarity	NPC288833
0.5488	Remote Similarity	NPC104545
0.5432	Remote Similarity	NPC263272
0.5366	Remote Similarity	NPC474537
0.5357	Remote Similarity	NPC476879
0.5294	Remote Similarity	NPC74751
0.5238	Remote Similarity	NPC474964
0.5195	Remote Similarity	NPC221647
0.5122	Remote Similarity	NPC260385
0.5122	Remote Similarity	NPC110094
0.5059	Remote Similarity	NPC4036
0.5059	Remote Similarity	NPC65120
0.5059	Remote Similarity	NPC145067
0.5059	Remote Similarity	NPC233455
0.5059	Remote Similarity	NPC158030

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5576
0.1-0.2	3499
0.2-0.3	67
0.3-0.4	4
0.4-0.5	2
0.5-0.6	2
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
0.5294	Remote Similarity	NPD7748	Pre-clinical
0.5059	Remote Similarity	NPD7515	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