NPASS Compound

Natural Product: NPC470375

Natural Product ID	NPC470375
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Toosendanic Acid B
IUPAC Name	2-[(3R,5R,9R,10R,13S,14S,16S,17S)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2021462
PubChem CID	70696018
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 82 85 0 0 0 0 0 0 0 0999 V2000 4.8984 1.4628 -1.7776 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8897 0.5082 -1.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6122 -0.7412 -1.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3143 -1.4391 -1.2622 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8630 -2.0601 0.0424 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6163 -1.0353 1.1378 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5487 -0.0895 0.8564 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3538 0.9727 1.9474 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3141 1.9909 1.7795 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9619 1.5331 1.7474 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4725 0.8318 0.5263 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1294 -0.5497 0.7251 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5447 -1.0547 2.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7645 -1.3793 -0.4317 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6079 -1.1264 -1.0337 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5703 -0.5621 -0.0596 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9925 0.7212 0.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7454 1.7506 0.7797 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2257 1.7518 0.7270 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7462 0.4382 0.3094 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9253 -0.3194 -0.7057 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8298 0.3440 -2.0462 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5545 -1.6790 -0.9135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7561 -1.9103 -0.0376 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 -0.8736 -0.3480 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2182 0.4886 0.0170 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6705 1.5216 -0.9450 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8803 0.8300 1.3677 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9503 -1.1666 0.3457 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0607 1.5585 -0.6661 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7054 -1.7342 2.4052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7335 -3.0190 2.4327 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7734 -1.1629 3.6670 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2531 1.0867 -0.9421 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4269 2.2828 -2.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3787 1.9964 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2051 1.0229 -2.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4247 -1.3735 -0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4939 -2.2146 -2.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6482 -0.7028 -1.6908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1102 -2.8328 -0.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7852 -2.6146 0.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5883 -0.4138 1.0868 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7921 0.4747 -0.0583 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5135 0.5248 2.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1104 2.6561 2.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0627 2.6322 1.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3257 1.4542 2.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1675 -2.1013 1.8781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2455 -1.0112 2.8863 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3210 -0.4493 2.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4605 -1.2162 -1.2652 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7962 -2.4516 -0.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5363 -0.4165 -1.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9898 -2.0800 -1.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7562 -1.3073 0.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2379 2.6765 1.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5846 1.9423 1.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5019 2.5982 0.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6778 -0.2261 1.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3796 -0.4296 -2.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3025 1.2934 -2.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 0.4111 -2.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8415 -2.5161 -0.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8814 -1.8374 -1.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1874 -2.8945 -0.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5314 -2.0570 1.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0266 -0.9404 -1.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5315 2.1428 -0.5514 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1351 0.9975 -1.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9411 2.2371 -1.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8438 1.9493 1.4652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9314 0.5427 1.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2905 0.4242 2.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7707 -1.4962 1.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2325 2.2497 -1.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8790 2.2515 -0.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4149 0.9235 -1.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8543 -1.6792 4.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0291 0.2948 -1.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3064 1.4854 0.0821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4792 1.9092 -1.6510 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 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 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 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 11 30 1 6 6 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 12 7 1 0 21 16 1 0 17 11 1 0 26 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 7 44 1 6 8 45 1 1 9 46 1 0 10 47 1 0 10 48 1 0 13 49 1 0 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 1 18 57 1 0 19 58 1 0 19 59 1 0 20 60 1 1 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 23 65 1 0 24 66 1 0 24 67 1 0 25 68 1 6 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	IOPZFWUTZDYRHQ-QESNHDJJSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,19-20,22-25,31-32H,8,10,12-17H2,1-7H3,(H,33,34)/t19?,20-,22-,23-,24+,25+,28+,29-,30+/m0/s1
SMILES	CC(=CCCC([C@@H]1[C@@H](O)C[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	4.721 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.611 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.369 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.406	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.913	Fsp³:	0.833
MCE-18:	84.0 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.759	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.062 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.324	Promiscuous compounds:	0.096

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.033	MDCK Permeability:	-4.813
Pgp-inhibitor:	0.002	Pgp-substrate:	0.21
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):	0.001
20% Bioavailability (F20%):	0.106	30% Bioavailability (F30%):	0.018
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.795	MRP1:	0.971
Plasma Protein Binding (PPB):	86.078%	Volume Distribution (VD):	-0.449
Fu:	9.936% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.196
BSEP inhibitor:	0.378

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.897	CYP3A4-substrate:	0.057
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.561
HLM stability:	0.223 ? 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):

6.209

Half-life (T1/2):

1.225

ADMET: Toxicity

hERG Blockers:	0.059	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.576	Drug-induced Liver Injury (DILI):	0.178
AMES Toxicity:	0.109	Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.522	Skin Sensitization:	0.945
Carcinogencity:	0.691	Eye Corrosion:	0.012
Eye Irritation:	0.459	Respiratory Toxicity:	0.828
Drug-induced Neurotoxicity:	0.117	Ototoxicity:	0.71
Hematotoxicity:	0.373	Drug-induced Nephrotoxicity:	0.731
Genotoxicity:	0.124	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.173	Hek293 Cytotoxicity:	0.181
BCF:	1.545 ? 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:	4.232 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.786 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.118 ? 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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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	3

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
NPT116	Cell line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[25127165]
NPT139	Cell line	HT-29	Homo sapiens	IC50	<	10000.0	nM	PMID[16919944]
NPT83	Cell line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[22325897]

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 NPC470375 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	19763
0.1-0.2	24976
0.2-0.3	4263
0.3-0.4	689
0.4-0.5	114
0.5-0.6	27
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470376
0.7656	Intermediate Similarity	NPC142361
0.7656	Intermediate Similarity	NPC474684
0.6471	Remote Similarity	NPC76895
0.6429	Remote Similarity	NPC475921
0.6429	Remote Similarity	NPC474704
0.6308	Remote Similarity	NPC1319
0.6232	Remote Similarity	NPC222845
0.6232	Remote Similarity	NPC296577
0.6056	Remote Similarity	NPC472240
0.6056	Remote Similarity	NPC262858
0.5616	Remote Similarity	NPC480720
0.5541	Remote Similarity	NPC48647
0.5467	Remote Similarity	NPC96496
0.5352	Remote Similarity	NPC470224
0.5342	Remote Similarity	NPC318390
0.5309	Remote Similarity	NPC609156
0.5294	Remote Similarity	NPC100334
0.5278	Remote Similarity	NPC470049
0.5211	Remote Similarity	NPC328052
0.5205	Remote Similarity	NPC486523
0.5135	Remote Similarity	NPC84271
0.5135	Remote Similarity	NPC147066
0.5135	Remote Similarity	NPC102414
0.5135	Remote Similarity	NPC610937
0.5132	Remote Similarity	NPC228784
0.5132	Remote Similarity	NPC324341
0.5132	Remote Similarity	NPC601810
0.507	Remote Similarity	NPC30166
0.5068	Remote Similarity	NPC470077
0.5068	Remote Similarity	NPC125399
0.5068	Remote Similarity	NPC486522
0.5067	Remote Similarity	NPC312215
0.5067	Remote Similarity	NPC112866
0.5065	Remote Similarity	NPC471896
0.5065	Remote Similarity	NPC294480
0.5065	Remote Similarity	NPC484791
0.5065	Remote Similarity	NPC484790

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6042
0.1-0.2	3014
0.2-0.3	87
0.3-0.4	7
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