NPASS Compound

Natural Product: NPC231310

Natural Product ID	NPC231310
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lanosta-7:9(11),23E-Triene-3Beta,22R,25-Triol
IUPAC Name	(E,5R,6S)-6-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-3-ene-2,5-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL458861
PubChem CID	44581567
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 81 84 0 0 0 0 0 0 0 0999 V2000 2.8057 -2.9776 -1.5655 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1461 -1.5514 -1.1265 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1836 -1.0272 -0.1371 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5182 0.3822 0.2420 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2171 1.1829 0.0965 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2226 0.1065 0.3517 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2505 -0.2616 1.7986 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1498 0.3794 -0.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5966 1.5566 -0.4644 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0460 1.6352 -0.8447 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7726 0.8636 0.2640 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2044 1.2576 0.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9793 1.2180 -0.8907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2074 2.7254 0.8547 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8292 0.4710 1.4940 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5231 -0.9869 1.5035 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0511 -1.2841 1.3772 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5269 -0.6017 0.1480 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1508 -1.2340 -1.0577 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0428 -0.7734 0.0061 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4851 -1.9666 -0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0324 -2.2314 -0.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7560 -0.9929 -0.5529 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5780 -0.5504 -1.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2191 0.6225 1.5446 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5095 -1.7135 -0.4970 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1671 -0.5386 0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9488 0.1976 -0.7908 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6470 1.4198 -0.2984 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9751 1.2142 1.1789 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7118 2.5880 -0.4914 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8595 1.6109 -0.9590 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3223 -2.7099 0.5033 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0432 -3.0172 -2.3332 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7332 -3.3777 -2.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5943 -3.5967 -0.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2542 -0.9196 -2.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2607 -1.6285 0.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2127 0.8507 -0.4745 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8860 0.4767 1.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1411 1.7001 -0.8541 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1964 1.9022 0.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6786 -1.2375 2.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7797 -0.2427 2.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8270 0.4861 2.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9192 2.3702 -0.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2465 1.1808 -1.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4227 2.6603 -0.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2660 1.2003 1.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8527 0.5052 -0.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4770 2.2040 -1.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3520 1.0037 -1.7822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2553 2.9841 1.3495 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0128 2.9105 1.5757 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2903 3.3905 -0.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4477 0.8960 2.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8344 -1.3771 2.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1449 -1.5722 0.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5555 -0.9502 2.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9469 -2.3905 1.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2561 -1.2705 -1.0272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7665 -0.7820 -2.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8175 -2.2926 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1713 -2.8110 -0.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0348 -2.9913 -1.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3055 -2.7318 0.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2831 0.1718 -2.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2945 -1.4047 -2.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4600 0.0004 -2.3633 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4447 1.4241 2.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1667 -2.2611 -1.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0780 -0.2181 1.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0856 -0.0873 -1.8224 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1386 1.4822 1.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8324 1.8723 1.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2825 0.1462 1.2830 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2068 3.5642 -0.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9306 2.5113 0.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2216 2.4464 -1.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5349 1.0715 -0.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1404 -2.2813 1.3803 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 1 6 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 6 15 25 1 0 2 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 26 33 1 0 23 3 1 0 23 6 1 0 20 8 1 0 18 11 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 1 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 1 13 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 1 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 24 67 1 0 24 68 1 0 24 69 1 0 25 70 1 0 26 71 1 6 27 72 1 0 28 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 33 81 1 0 M END

Standard InCHIKey	ODDPCFPKYKNPDA-IBDCHPIJSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-19(23(31)13-15-26(2,3)33)20-11-17-30(8)22-9-10-24-27(4,5)25(32)14-16-28(24,6)21(22)12-18-29(20,30)7/h9,12-13,15,19-20,23-25,31-33H,10-11,14,16-18H2,1-8H3/b15-13+/t19-,20+,23+,24-,25-,28+,29+,30-/m0/s1
SMILES	C[C@@H]([C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)O)[C@@H](/C=C/C(C)(C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	511.671 ? Van der Waals volume.
Dense:	0.892	LogP:	5.09 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.198 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.643 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.442	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.127	Fsp³:	0.8
MCE-18:	84.37 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.878	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.043 ? 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:	0.413	Promiscuous compounds:	0.144

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.867	MDCK Permeability:	-4.75
Pgp-inhibitor:	0.128	Pgp-substrate:	0.27
PAMPA:	0.819 ? 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):	0.016
20% Bioavailability (F20%):	0.986	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.043
Plasma Protein Binding (PPB):	87.25%	Volume Distribution (VD):	-0.102
Fu:	11.838% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.96
BSEP inhibitor:	0.617

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.734	CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.916	CYP3A4-substrate:	0.99
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.633 ? 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):

15.68

Half-life (T1/2):

0.929

ADMET: Toxicity

hERG Blockers:	0.081	hERG Blockers (10um):	0.217
Human Hepatotoxicity (H-HT):	0.588	Drug-induced Liver Injury (DILI):	0.045
AMES Toxicity:	0.37	Rat Oral Acute Toxicity:	0.46
Maximum Recommended Daily Dose:	0.765	Skin Sensitization:	0.867
Carcinogencity:	0.862	Eye Corrosion:	0.001
Eye Irritation:	0.289	Respiratory Toxicity:	0.705
Drug-induced Neurotoxicity:	0.07	Ototoxicity:	0.711
Hematotoxicity:	0.356	Drug-induced Nephrotoxicity:	0.531
Genotoxicity:	0.749	RPMI-8226 Immunitoxicity:	0.178
A549 Cytotoxicity:	0.562	Hek293 Cytotoxicity:	0.713
BCF:	1.578 ? 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:	3.87 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.458 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.677 ? 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
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[17049251]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[18387711]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24359303]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	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
Activity	5
IC50	1

Activity Type	# Activity
Cell line	1
Others	5

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	=	70.0	%	PMID[9868159]
NPT2	Others	Unspecified	n.a.	Activity	=	0.0	%	PMID[15787442]
NPT2	Others	Unspecified	n.a.	Activity	=	67.3	%	PMID[20438092]
NPT2	Others	Unspecified	n.a.	Activity	=	88.2	%	PMID[9392888]
NPT2	Others	Unspecified	n.a.	IC50	=	228.0	molar ratio	PMID[25136754]
NPT2	Others	Unspecified	n.a.	Activity	=	25.1	%	DOI[10.6019/CHEMBL1201861]

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 NPC231310 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	26121
0.1-0.2	20919
0.2-0.3	2486
0.3-0.4	261
0.4-0.5	44
0.5-0.6	18
0.6-0.7	6
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
0.6949	Remote Similarity	NPC6707
0.678	Remote Similarity	NPC205455
0.65	Remote Similarity	NPC87489
0.6452	Remote Similarity	NPC202389
0.625	Remote Similarity	NPC475772
0.6	Remote Similarity	NPC484797
0.597	Remote Similarity	NPC212948
0.5857	Remote Similarity	NPC141401
0.5806	Remote Similarity	NPC20853
0.5797	Remote Similarity	NPC214697
0.5556	Remote Similarity	NPC72507
0.5362	Remote Similarity	NPC84271
0.5362	Remote Similarity	NPC222845
0.5362	Remote Similarity	NPC102414
0.5362	Remote Similarity	NPC296577
0.5352	Remote Similarity	NPC186810
0.5211	Remote Similarity	NPC45324
0.5211	Remote Similarity	NPC162001
0.5211	Remote Similarity	NPC77168
0.5152	Remote Similarity	NPC147568
0.5139	Remote Similarity	NPC469406
0.5139	Remote Similarity	NPC484975
0.5139	Remote Similarity	NPC48647
0.5139	Remote Similarity	NPC321301

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC231310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8124
0.1-0.2	977
0.2-0.3	49
0.3-0.4	0
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