NPASS Compound

Natural Product: NPC471293

Natural Product ID	NPC471293
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cochinchinoid K
IUPAC Name	(3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-3-[(3S,5R,9R,10R,13S,14S,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]oxolan-2-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2409065
PubChem CID	71745149
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 83 87 0 0 0 0 0 0 0 0999 V2000 -5.9528 -2.0513 0.7293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3983 -0.6450 1.0271 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0263 0.3704 0.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1668 0.8995 -0.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7634 1.2356 -0.6058 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2285 0.5799 0.6205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9032 -0.7700 0.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5737 -1.7309 -0.2677 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3636 -1.4097 -1.0227 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4851 -0.4912 -0.6698 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7536 0.2584 0.5741 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8644 1.4436 0.7438 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5646 0.9260 0.4767 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6692 0.7398 -0.9956 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2981 -0.2928 -1.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4822 -1.6040 -1.5256 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8186 -1.1151 -2.0410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9769 0.3093 -1.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1673 0.4348 -0.6627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1695 -0.4010 0.5811 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6239 -0.8680 0.6950 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9350 -1.0605 -0.6665 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3638 -0.0433 -1.3895 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7647 0.4338 -2.4975 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4839 0.2501 1.2231 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9457 -0.1234 1.1454 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4569 -0.3123 -0.2512 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7502 1.0439 1.7360 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1995 -1.2460 1.9051 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2183 0.5043 2.5740 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5926 0.0156 -2.9608 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2913 2.0949 -1.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5436 1.4877 1.7918 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1286 -0.2567 -0.5043 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7517 -0.4031 2.5004 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8689 -2.2273 1.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2983 -2.1442 -0.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2392 -2.8367 1.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5007 1.1776 0.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6676 1.8443 -1.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2462 0.2174 -1.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6621 2.3564 -0.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1403 1.0227 -1.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -1.1751 1.7772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 -2.7739 0.1430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4056 -1.8563 -0.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1897 -1.9793 -1.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5123 -0.4536 1.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8052 1.7297 1.8367 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0932 2.2875 0.1030 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6065 -0.0050 1.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2251 1.7259 0.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5305 -2.0759 -0.5450 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0089 -2.2724 -2.2374 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6065 -1.7872 -1.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7717 -1.1839 -3.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2129 0.9119 -2.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3721 1.5127 -0.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9579 0.2127 1.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5085 -1.2694 0.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6861 -1.7820 1.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2795 1.1724 0.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2468 -1.3336 -0.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1658 0.4986 -0.9351 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5767 -0.2649 -0.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7509 0.6490 2.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2860 1.4157 2.6652 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8943 1.8511 1.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9180 -2.0681 1.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2308 -0.3516 3.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4537 0.6874 -3.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2707 0.5032 -3.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7487 -0.9384 -3.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7614 2.1499 -1.8883 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5300 2.9331 -0.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9637 2.2715 -2.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4484 2.0798 1.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5754 0.9768 2.7525 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7472 2.2841 1.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7075 -0.7081 0.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7254 -0.9359 2.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0148 -0.8954 3.1658 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9497 0.6435 2.7251 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 0 9 10 2 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 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 21 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 25 30 1 0 15 31 1 0 14 32 1 0 6 33 1 0 3 34 1 0 2 35 1 0 7 2 1 0 11 6 1 0 15 10 1 0 18 14 1 0 23 19 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 25 62 1 0 27 63 1 0 27 64 1 0 27 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	QDVOKJAQMSSOJK-FQARURFKSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-26(2)22-9-8-20-19(28(22,5)13-12-23(26)31)11-15-29(6)18(10-14-30(20,29)7)17-16-21(35-25(17)33)24(32)27(3,4)34/h8,17-19,21-24,31-32,34H,9-16H2,1-7H3/t17-,18-,19-,21+,22-,23-,24-,28+,29-,30+/m0/s1
SMILES	CC1(C(CCC2(C1CC=C3C2CCC4(C3(CCC4C5CC(OC5=O)C(C(C)(C)O)O)C)C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	3.169 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.55 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.89 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	26.0
TPSA:	86.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.384	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.035	Fsp³:	0.9
MCE-18:	102.632 ? 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:	0.05	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.046 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.227	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89	MDCK Permeability:	-4.814
Pgp-inhibitor:	0.001	Pgp-substrate:	0.211
PAMPA:	0.445 ? 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%):	0.001	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.912	MRP1:	0.999
Plasma Protein Binding (PPB):	76.819%	Volume Distribution (VD):	-0.158
Fu:	22.381% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.01
OATP1B3 inhibitor:	0.922	BCRP inhibitor:	0.009
BSEP inhibitor:	0.521

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.671	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.163	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.005	CYP2C8-inhibitor:	0.72
HLM stability:	0.978 ? 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):

10.552

Half-life (T1/2):

1.401

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.432
Human Hepatotoxicity (H-HT):	0.407	Drug-induced Liver Injury (DILI):	0.055
AMES Toxicity:	0.026	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.814	Skin Sensitization:	0.187
Carcinogencity:	0.151	Eye Corrosion:	0.0
Eye Irritation:	0.014	Respiratory Toxicity:	0.125
Drug-induced Neurotoxicity:	0.128	Ototoxicity:	0.973
Hematotoxicity:	0.033	Drug-induced Nephrotoxicity:	0.104
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.018
A549 Cytotoxicity:	0.18	Hek293 Cytotoxicity:	0.384
BCF:	1.867 ? 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:	4.611 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.007 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.4 ? 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
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	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	2
Inhibition	2

Activity Type	# Activity
Individual protein	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	3200.0	nM	PMID[21800409]
NPT1137	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	>	60.0	%	DOI[10.1016/j.cropro.2012.12.021]
NPT4862	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	820.0	nM	PMID[21800409]
NPT4862	Individual protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	>	60.0	%	PMID[21800409]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC471293 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	18896
0.1-0.2	23702
0.2-0.3	6530
0.3-0.4	584
0.4-0.5	107
0.5-0.6	23
0.6-0.7	11
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
0.6957	Remote Similarity	NPC5358
0.6957	Remote Similarity	NPC216260
0.6716	Remote Similarity	NPC486523
0.6418	Remote Similarity	NPC470224
0.6364	Remote Similarity	NPC30166
0.6324	Remote Similarity	NPC470049
0.6111	Remote Similarity	NPC324598
0.6087	Remote Similarity	NPC125399
0.6087	Remote Similarity	NPC486522
0.6027	Remote Similarity	NPC484791
0.6027	Remote Similarity	NPC484790
0.5972	Remote Similarity	NPC484789
0.5972	Remote Similarity	NPC484801
0.5972	Remote Similarity	NPC484786
0.5972	Remote Similarity	NPC484787
0.5972	Remote Similarity	NPC484788
0.5857	Remote Similarity	NPC470077
0.5769	Remote Similarity	NPC85593
0.5769	Remote Similarity	NPC31430
0.5616	Remote Similarity	NPC210268
0.5616	Remote Similarity	NPC190604
0.5571	Remote Similarity	NPC328052
0.557	Remote Similarity	NPC189282
0.557	Remote Similarity	NPC237402
0.5541	Remote Similarity	NPC472240
0.5541	Remote Similarity	NPC262858
0.5513	Remote Similarity	NPC121566
0.5513	Remote Similarity	NPC100955
0.5422	Remote Similarity	NPC101450
0.5395	Remote Similarity	NPC480955
0.52	Remote Similarity	NPC142361
0.52	Remote Similarity	NPC474684
0.5132	Remote Similarity	NPC67831
0.5132	Remote Similarity	NPC174051

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6978
0.1-0.2	2045
0.2-0.3	123
0.3-0.4	4
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