NPASS Compound

Natural Product: NPC471720

Natural Product ID	NPC471720
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(17Alpha,21Alpha,23Alpha)-24-Methyl-3Beta-Hydroxy-5Alpha-Lanosta-8,24-Diene-21,23-Lactone
IUPAC Name	(3R,5S)-3-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-(3-methylbut-2-en-2-yl)oxolan-2-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3105554
PubChem CID	76321155
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 86 0 0 0 0 0 0 0 0999 V2000 8.7685 0.6295 0.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5331 -0.0623 0.6912 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5776 -0.2772 -0.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7832 0.2038 -1.5844 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3124 -0.9419 0.0987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1000 -0.0324 -0.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0253 -0.8603 0.4217 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7008 -1.4060 1.6556 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1892 -1.8423 2.7051 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0607 -1.3356 1.4103 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7291 -0.2638 0.7242 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7194 0.9128 1.6691 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2025 1.1738 1.7021 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1192 1.1647 0.2206 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8291 0.1585 -0.3673 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1141 -1.1124 -0.8515 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0496 -1.4691 0.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0279 -0.3256 -0.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5542 0.9022 -0.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5138 2.0248 -0.2512 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9357 1.6886 0.0044 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3829 0.3816 -0.5819 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4188 -0.7404 -0.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8059 -1.5991 0.8393 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1662 -2.1900 0.6915 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1208 -1.3501 -0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7813 0.1123 -0.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0799 0.7704 1.2286 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7425 0.7612 -1.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4319 -1.4567 0.3919 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4034 -1.6897 -1.5546 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4589 0.7479 -1.5860 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1836 2.5987 -0.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3953 -0.5064 2.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4325 -0.0503 -0.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5454 1.4838 -0.4006 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3886 0.9313 1.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4095 1.2488 -1.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8524 0.2218 -1.8513 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2168 -0.4136 -2.3085 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1814 -1.7878 -0.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2217 0.8820 0.4359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0242 0.1739 -1.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8431 -1.7975 -0.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1587 -1.0649 1.3183 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2797 1.7782 1.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0010 0.6114 2.7036 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0083 2.1662 2.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3053 0.4080 2.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8275 -1.9703 -0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2407 -0.9115 -1.8573 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7832 -1.6237 1.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4466 -2.4235 -0.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4420 2.4378 -1.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2731 2.9031 0.4054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5599 2.5117 -0.3996 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0918 1.7331 1.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4685 0.5277 -1.6782 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6336 -1.0548 1.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0800 -2.4394 0.8427 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1146 -3.2406 0.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5924 -2.2895 1.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1052 -1.7051 -1.1562 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1201 0.4610 1.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1201 1.8737 1.1414 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4316 0.5038 2.0553 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5603 0.2690 -2.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7683 0.5498 -0.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5062 1.8343 -1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0951 -1.4392 -0.3282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8226 -2.6877 -1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0815 -1.2893 -2.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4285 -1.8014 -2.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5956 1.1926 -2.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1426 1.5753 -1.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9026 0.0224 -2.2832 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2730 2.8299 -0.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2123 2.8055 -1.2336 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2845 3.2483 0.5599 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2347 -1.6028 2.1676 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3533 -0.3403 2.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5432 -0.0204 2.6150 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 7 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 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 26 30 1 0 23 31 1 0 15 32 1 0 14 33 1 0 2 34 1 0 10 5 1 0 15 11 1 0 19 14 1 0 23 18 1 0 27 22 1 0 1 35 1 0 1 36 1 0 1 37 1 0 4 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 0 13 49 1 0 16 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 20 54 1 0 20 55 1 0 21 56 1 0 21 57 1 0 22 58 1 0 24 59 1 0 24 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 28 64 1 0 28 65 1 0 28 66 1 0 29 67 1 0 29 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 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	QNIOIQFWRJSVOW-HYPRSTRGSA-N
Standard InCHI	InChI=1S/C31H48O3/c1-18(2)19(3)24-17-20(27(33)34-24)21-11-15-31(8)23-9-10-25-28(4,5)26(32)13-14-29(25,6)22(23)12-16-30(21,31)7/h20-21,24-26,32H,9-17H2,1-8H3/t20-,21-,24+,25+,26+,29-,30-,31+/m1/s1
SMILES	CC(=C(C)C1CC(C(=O)O1)C2CCC3(C2(CCC4=C3CCC5C4(CCC(C5(C)C)O)C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.36	Volume:	520.411 ? Van der Waals volume.
Dense:	0.9	LogP:	4.584 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.061 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.653 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.339	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.016	Fsp³:	0.839
MCE-18:	97.368 ? 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:	0.803	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.066 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.075 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.251	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.862	MDCK Permeability:	-4.708
Pgp-inhibitor:	0.27	Pgp-substrate:	0.207
PAMPA:	0.322 ? 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%):	0.016	30% Bioavailability (F30%):	0.028
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859	MRP1:	0.999
Plasma Protein Binding (PPB):	89.035%	Volume Distribution (VD):	0.082
Fu:	10.448% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.442
OATP1B3 inhibitor:	0.975	BCRP inhibitor:	0.012
BSEP inhibitor:	0.805

ADMET: Metabolism

CYP1A2-inhibitor:	0.675	CYP1A2-substrate:	0.012
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.96	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.31	CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.988	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.999	CYP2C8-inhibitor:	0.877
HLM stability:	0.998 ? 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):

12.73

Half-life (T1/2):

1.047

ADMET: Toxicity

hERG Blockers:	0.102	hERG Blockers (10um):	0.531
Human Hepatotoxicity (H-HT):	0.588	Drug-induced Liver Injury (DILI):	0.255
AMES Toxicity:	0.062	Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.77	Skin Sensitization:	0.53
Carcinogencity:	0.279	Eye Corrosion:	0.0
Eye Irritation:	0.087	Respiratory Toxicity:	0.225
Drug-induced Neurotoxicity:	0.442	Ototoxicity:	0.888
Hematotoxicity:	0.109	Drug-induced Nephrotoxicity:	0.256
Genotoxicity:	0.025	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.154	Hek293 Cytotoxicity:	0.273
BCF:	2.144 ? 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:	4.959 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.27 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.067 ? 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
Inhibition	1
Survival	1

Activity Type	# Activity
Non-molecular	1
Others	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	71.9	%	PMID[24359303]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Survival	=	91.0	%	DrugMatrix in vivo data: Biochemistry

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 NPC471720 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	19306
0.1-0.2	24975
0.2-0.3	5203
0.3-0.4	287
0.4-0.5	58
0.5-0.6	21
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
0.6719	Remote Similarity	NPC20388
0.6515	Remote Similarity	NPC486187
0.6364	Remote Similarity	NPC486193
0.6094	Remote Similarity	NPC132635
0.6094	Remote Similarity	NPC601223
0.6	Remote Similarity	NPC471724
0.5909	Remote Similarity	NPC94755
0.5873	Remote Similarity	NPC118508
0.5873	Remote Similarity	NPC484086
0.5821	Remote Similarity	NPC308041
0.5821	Remote Similarity	NPC16350
0.5781	Remote Similarity	NPC275910
0.5781	Remote Similarity	NPC46160
0.5781	Remote Similarity	NPC202642
0.5692	Remote Similarity	NPC231477
0.5692	Remote Similarity	NPC87489
0.5692	Remote Similarity	NPC123724
0.5692	Remote Similarity	NPC73875
0.5606	Remote Similarity	NPC214570
0.525	Remote Similarity	NPC195708
0.52	Remote Similarity	NPC486185
0.5185	Remote Similarity	NPC265655
0.5139	Remote Similarity	NPC486197
0.5067	Remote Similarity	NPC11903
0.506	Remote Similarity	NPC292196
0.506	Remote Similarity	NPC129340
0.506	Remote Similarity	NPC220293

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6702
0.1-0.2	2329
0.2-0.3	118
0.3-0.4	1
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