NPASS Compound

Natural Product: NPC54909

Natural Product ID	NPC54909
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2 Alpha-Acetyl Tomentic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-acetyloxy-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms	2 Alpha-Acetyl Tomentic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL439053
PubChem CID	44436803
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 92 0 0 0 0 0 0 0 0999 V2000 5.5370 2.8581 -1.4589 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1717 1.6829 -0.6180 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0724 0.5008 -0.7526 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4073 -0.8287 -0.7011 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3190 -0.9048 0.3524 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6198 -2.2240 0.1671 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2377 -2.2952 0.7737 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3255 -1.2675 0.1348 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2893 -1.5589 -1.3171 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9834 0.0172 0.5248 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2853 0.9709 1.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1463 0.9172 1.4920 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.0350 0.5115 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2678 0.0269 0.5751 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7930 0.4306 1.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6709 1.2323 -0.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1688 1.3805 -0.3318 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9095 0.1444 -0.7121 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4001 -1.1463 -0.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1157 -1.6529 1.0221 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6787 -2.1898 -1.2881 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9115 -1.1221 -0.0778 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3166 -2.4630 0.3021 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8785 -2.3495 -0.1700 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0994 -1.3423 0.6526 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0112 -1.9036 2.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2446 0.3082 -0.2733 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5643 2.3792 -1.2208 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2797 3.5079 -0.9321 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6005 3.6258 0.2841 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6620 4.5292 -1.9485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4208 0.2954 0.3045 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7206 1.2171 -0.8527 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8502 2.4301 -0.8691 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7030 0.6607 -2.1002 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0541 -1.0232 1.6358 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2925 -1.0498 1.6971 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3178 -1.1063 2.8032 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1167 2.8453 -2.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6424 2.8648 -1.5734 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 3.7861 -0.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1674 2.0160 0.4616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6810 0.5840 -1.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8284 0.5435 0.0865 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0522 -1.1952 -1.6861 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1874 -1.5906 -0.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1901 -3.0445 0.7098 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6588 -2.5955 -0.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8954 -3.3311 0.6025 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3869 -2.0826 1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2255 -1.5691 -1.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9168 -2.6274 -1.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6010 -0.9230 -1.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7864 1.9243 1.4242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6066 1.9228 1.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1751 0.5267 2.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4809 0.3378 -0.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8352 0.2177 2.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1312 0.0007 2.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6892 1.5480 2.0909 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3010 1.1181 -1.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2646 2.1021 0.2407 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5593 1.6908 0.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9864 0.1266 -1.8250 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8340 -0.9015 1.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7953 -2.5061 0.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4239 -2.0721 1.7825 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8518 -2.2206 -2.0151 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5869 -1.9057 -1.8510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7777 -3.2008 -0.8524 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5941 -1.0275 -1.1725 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7952 -3.2264 -0.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4366 -2.7393 1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9939 -1.9975 -1.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4431 -3.3640 -0.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3933 -2.9554 1.9112 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6358 -1.3232 2.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9576 -2.0588 2.5555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8496 -0.2421 -0.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7500 4.1028 -2.9557 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6324 5.0066 -1.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9055 5.3305 -1.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8101 0.9390 1.1728 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1052 3.1867 -0.1001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7925 2.1734 -0.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0864 2.9598 -1.8450 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4797 0.9212 -2.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6697 -0.7280 3.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 17 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 10 32 1 0 32 33 1 0 33 34 1 0 33 35 1 6 5 36 1 1 36 37 2 0 36 38 1 0 33 2 1 0 32 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 1 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 6 47 1 0 6 48 1 0 7 49 1 0 7 50 1 0 9 51 1 0 9 52 1 0 9 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 13 57 1 6 15 58 1 0 15 59 1 0 15 60 1 0 16 61 1 0 16 62 1 0 17 63 1 1 18 64 1 6 20 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 21 70 1 0 22 71 1 6 23 72 1 0 23 73 1 0 24 74 1 0 24 75 1 0 26 76 1 0 26 77 1 0 26 78 1 0 27 79 1 0 31 80 1 0 31 81 1 0 31 82 1 0 32 83 1 1 34 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 38 88 1 0 M END

Standard InCHIKey	HHDNTTOUNUERTJ-BGJCYSRJSA-N
Standard InCHI	InChI=1S/C32H50O6/c1-18-11-14-32(26(35)36)16-15-29(6)20(24(32)31(18,8)37)9-10-23-28(5)17-21(38-19(2)33)25(34)27(3,4)22(28)12-13-30(23,29)7/h9,18,21-25,34,37H,10-17H2,1-8H3,(H,35,36)/t18-,21-,22+,23-,24-,25+,28+,29-,30-,31-,32+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)OC(=O)C)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	530.36	Volume:	564.078 ? Van der Waals volume.
Dense:	0.94	LogP:	2.811 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.779 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.451 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.31	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.101	Fsp³:	0.875
MCE-18:	112.0 ? 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:	0.839	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? 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:	0.274	Promiscuous compounds:	0.212

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068	MDCK Permeability:	-4.82
Pgp-inhibitor:	0.04	Pgp-substrate:	0.003
PAMPA:	0.997 ? 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):	0.004
20% Bioavailability (F20%):	0.625	30% Bioavailability (F30%):	0.434
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.849
Plasma Protein Binding (PPB):	78.325%	Volume Distribution (VD):	-0.324
Fu:	18.888% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.521
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.021	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	0.266
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.957
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):

4.554

Half-life (T1/2):

1.184

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.068
Human Hepatotoxicity (H-HT):	0.538	Drug-induced Liver Injury (DILI):	0.372
AMES Toxicity:	0.157	Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.258	Skin Sensitization:	0.673
Carcinogencity:	0.745	Eye Corrosion:	0.005
Eye Irritation:	0.237	Respiratory Toxicity:	0.517
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.642
Hematotoxicity:	0.275	Drug-induced Nephrotoxicity:	0.664
Genotoxicity:	0.171	RPMI-8226 Immunitoxicity:	0.025
A549 Cytotoxicity:	0.053	Hek293 Cytotoxicity:	0.131
BCF:	0.974 ? 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:	3.885 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.646 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.771 ? 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
NPO20072	Verbascum dudleyanum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5696	Premna fulva	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6660	Cecropia lyratiloba	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1029	Vernonia jalcana	Species	Asteraceae	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	10

Activity Type	# Activity
Cell line	7
Non-molecular	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
NPT111	Cell line	K562	Homo sapiens	IC50	=	38350.0	nM	PMID[17889544]
NPT1215	Cell line	8505C	Homo sapiens	IC50	>	30000.0	nM	PMID[22995818]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	24300.0	nM	PMID[22995818]
NPT81	Cell line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[22995818]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	30000.0	nM	PMID[22995818]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	25300.0	nM	PMID[22995818]
NPT886	Cell line	NIH3T3	Mus musculus	IC50	>	30000.0	nM	PMID[22995818]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	41380.0	nM	PMID[17889544]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[22995818]

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 NPC54909 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	17839
0.1-0.2	26223
0.2-0.3	4920
0.3-0.4	618
0.4-0.5	194
0.5-0.6	36
0.6-0.7	18
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
0.7333	Intermediate Similarity	NPC233012
0.7324	Intermediate Similarity	NPC202728
0.7324	Intermediate Similarity	NPC158059
0.7083	Intermediate Similarity	NPC259733
0.7083	Intermediate Similarity	NPC158371
0.7083	Intermediate Similarity	NPC207922
0.7027	Intermediate Similarity	NPC157113
0.6849	Remote Similarity	NPC136697
0.6667	Remote Similarity	NPC327179
0.6667	Remote Similarity	NPC118964
0.6667	Remote Similarity	NPC62516
0.6667	Remote Similarity	NPC148964
0.6579	Remote Similarity	NPC187933
0.6533	Remote Similarity	NPC191412
0.6533	Remote Similarity	NPC114159
0.6533	Remote Similarity	NPC247139
0.6533	Remote Similarity	NPC6818
0.641	Remote Similarity	NPC603658
0.64	Remote Similarity	NPC256247
0.6364	Remote Similarity	NPC284865
0.6316	Remote Similarity	NPC35239
0.6316	Remote Similarity	NPC132824
0.625	Remote Similarity	NPC96693
0.6104	Remote Similarity	NPC118519
0.6053	Remote Similarity	NPC235053
0.5949	Remote Similarity	NPC147232
0.587	Remote Similarity	NPC482052
0.5833	Remote Similarity	NPC600756
0.5823	Remote Similarity	NPC137072
0.5806	Remote Similarity	NPC25491
0.5684	Remote Similarity	NPC482051
0.5638	Remote Similarity	NPC132126
0.56	Remote Similarity	NPC481235
0.5542	Remote Similarity	NPC230151
0.5417	Remote Similarity	NPC482049
0.5417	Remote Similarity	NPC482050
0.54	Remote Similarity	NPC481234
0.54	Remote Similarity	NPC479431
0.5316	Remote Similarity	NPC51700
0.5316	Remote Similarity	NPC88716
0.5316	Remote Similarity	NPC68160
0.525	Remote Similarity	NPC71074
0.525	Remote Similarity	NPC37221
0.525	Remote Similarity	NPC605937
0.5208	Remote Similarity	NPC479744
0.519	Remote Similarity	NPC480946
0.519	Remote Similarity	NPC187722
0.519	Remote Similarity	NPC130577
0.519	Remote Similarity	NPC142415
0.519	Remote Similarity	NPC102683
0.5185	Remote Similarity	NPC293564
0.5181	Remote Similarity	NPC296164
0.5125	Remote Similarity	NPC182797
0.5125	Remote Similarity	NPC84319
0.5125	Remote Similarity	NPC52021
0.5125	Remote Similarity	NPC52169
0.5125	Remote Similarity	NPC488562
0.5125	Remote Similarity	NPC599947
0.5062	Remote Similarity	NPC472149
0.506	Remote Similarity	NPC25299
0.506	Remote Similarity	NPC481322

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC54909 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5714
0.1-0.2	3361
0.2-0.3	64
0.3-0.4	11
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