NPASS Compound

Natural Product: NPC214570

Natural Product ID	NPC214570
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lanosta-8,24-Dien-3Beta,21-Diol
IUPAC Name	(3S,5R,10S,13R,14R,17R)-17-[(2R)-1-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL456903
PubChem CID	13990809
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 3.9637 1.5858 1.2049 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4814 0.6691 2.0812 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2851 -0.7276 1.5835 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3453 -0.8078 0.3764 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2030 -2.2565 -0.0556 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7246 -2.4718 -0.3739 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2261 -1.0916 -0.5418 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9562 -0.3857 0.6163 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4540 -0.9634 1.8989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6331 1.0644 0.4069 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8223 1.2828 0.6168 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6827 0.1856 0.1268 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2447 -0.9405 -0.4205 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1003 -2.0406 -0.9123 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4955 -1.6156 -1.2559 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7456 -0.1407 -1.0373 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1624 0.3350 0.2478 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5846 -0.4902 1.4397 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5026 1.7857 0.4410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9817 1.9422 0.4943 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7060 1.4019 -0.6840 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1859 0.1344 -1.2473 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4109 0.2111 -2.7697 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0718 -1.0423 -0.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0471 1.1833 -0.2878 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6152 -0.5617 -1.8795 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5176 -1.4984 1.4724 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6360 -1.1461 0.5981 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3265 0.1336 0.8000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5706 0.9924 -0.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1504 0.6833 -1.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2791 2.2481 0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5553 2.4900 1.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6076 1.0479 2.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2818 0.5781 2.9057 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7167 -1.2235 2.4690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8870 -0.2080 -0.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7557 -2.4207 -0.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4163 -2.9774 0.7596 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1898 -3.0045 0.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6149 -3.0727 -1.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6415 -1.1414 1.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8960 -1.9799 2.0275 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6423 -0.2868 2.7547 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2197 1.7839 0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8313 1.2632 -0.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1904 2.2446 0.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0236 1.3891 1.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6141 -2.4841 -1.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0705 -2.8472 -0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1903 -2.2608 -0.6772 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7098 -1.8217 -2.3258 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1761 0.3833 -1.8624 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8426 -0.2553 2.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5624 -0.2383 1.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5554 -1.5555 1.2210 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0760 2.1995 1.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1317 2.3429 -0.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4240 1.5661 1.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1884 3.0540 0.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7864 2.2129 -1.4668 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1397 -0.7156 -3.2709 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4547 0.5488 -2.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7488 1.0205 -3.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9820 -1.8438 -1.5969 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1307 -0.7052 -0.8425 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8331 -1.4070 0.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0859 0.7737 0.6089 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5951 -0.1146 -1.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5771 -1.4241 -2.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1296 0.1749 -2.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2921 -2.6308 1.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9648 -1.5061 2.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3168 -1.1543 -0.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4800 -1.9214 0.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 0.3614 1.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0651 0.7002 -1.7359 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5186 -0.3300 -1.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6263 1.3962 -2.3021 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0867 1.9520 0.8728 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7277 2.7553 -0.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5624 2.8828 0.6987 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 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 21 25 1 0 7 26 1 6 3 27 1 0 27 28 1 0 28 29 1 0 29 30 2 3 30 31 1 0 30 32 1 0 8 4 1 0 17 12 1 0 13 7 1 0 22 16 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 4 37 1 6 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 9 42 1 0 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 6 18 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 21 61 1 6 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	NOXQLVJQLGRLCH-ILLHTMCHSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-20(2)9-8-10-21(19-31)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,21-22,25-26,31-32H,8,10-19H2,1-7H3/t21-,22+,25-,26-,28+,29+,30-/m0/s1
SMILES	OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)CCC=C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	505.518 ? Van der Waals volume.
Dense:	0.875	LogP:	5.195 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.263 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.666 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.434	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.751	Fsp³:	0.867
MCE-18:	78.607 ? 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:	0.955	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.654	Promiscuous compounds:	0.282

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.425	MDCK Permeability:	-5.073
Pgp-inhibitor:	0.539	Pgp-substrate:	0.055
PAMPA:	0.97 ? 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%):	0.375	30% Bioavailability (F30%):	0.064
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.892	MRP1:	0.873
Plasma Protein Binding (PPB):	90.837%	Volume Distribution (VD):	-0.133
Fu:	6.85% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.633
BSEP inhibitor:	0.833

ADMET: Metabolism

CYP1A2-inhibitor:	0.135	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.211	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.743	CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.078	CYP3A4-substrate:	0.961
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.009
HLM stability:	0.054 ? 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):

12.009

Half-life (T1/2):

0.5

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.19
Human Hepatotoxicity (H-HT):	0.682	Drug-induced Liver Injury (DILI):	0.089
AMES Toxicity:	0.239	Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.107	Skin Sensitization:	0.998
Carcinogencity:	0.82	Eye Corrosion:	0.444
Eye Irritation:	0.938	Respiratory Toxicity:	0.759
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.631
Hematotoxicity:	0.502	Drug-induced Nephrotoxicity:	0.814
Genotoxicity:	0.019	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.378	Hek293 Cytotoxicity:	0.157
BCF:	2.34 ? 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:	4.828 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.935 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.53 ? 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[11473410]
NPT2	Others	Unspecified	n.a.	Activity	=	10.9	%	PMID[8988597]
NPT2	Others	Unspecified	n.a.	Activity	=	77.5	%	PMID[16252909]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[9599262]
NPT2	Others	Unspecified	n.a.	IC50	=	392.0	molar ratio	PMID[20591538]
NPT2	Others	Unspecified	n.a.	Activity	=	47.1	%	Open TG-GATES in vivo data: Organ Weight

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 NPC214570 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	23394
0.1-0.2	22633
0.2-0.3	3435
0.3-0.4	297
0.4-0.5	58
0.5-0.6	22
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8113	Intermediate Similarity	NPC46160
0.8113	Intermediate Similarity	NPC202642
0.7636	Intermediate Similarity	NPC73875
0.7544	Intermediate Similarity	NPC94755
0.7143	Intermediate Similarity	NPC275910
0.6724	Remote Similarity	NPC231477
0.6724	Remote Similarity	NPC123724
0.6441	Remote Similarity	NPC87489
0.6379	Remote Similarity	NPC118508
0.6379	Remote Similarity	NPC484086
0.6094	Remote Similarity	NPC486193
0.6094	Remote Similarity	NPC233836
0.6094	Remote Similarity	NPC159046
0.6094	Remote Similarity	NPC187376
0.6066	Remote Similarity	NPC132635
0.6066	Remote Similarity	NPC601223
0.5968	Remote Similarity	NPC471724
0.5781	Remote Similarity	NPC275740
0.5781	Remote Similarity	NPC308041
0.5781	Remote Similarity	NPC16350
0.5781	Remote Similarity	NPC86319
0.5758	Remote Similarity	NPC486187
0.5758	Remote Similarity	NPC76895
0.5692	Remote Similarity	NPC20388
0.5672	Remote Similarity	NPC482597
0.5667	Remote Similarity	NPC73428
0.5667	Remote Similarity	NPC606082
0.5606	Remote Similarity	NPC471720
0.5522	Remote Similarity	NPC191684
0.5455	Remote Similarity	NPC471722
0.5455	Remote Similarity	NPC605915
0.5294	Remote Similarity	NPC69454
0.5238	Remote Similarity	NPC318136
0.5156	Remote Similarity	NPC205455
0.5147	Remote Similarity	NPC484084
0.5072	Remote Similarity	NPC173272
0.5072	Remote Similarity	NPC486197
0.507	Remote Similarity	NPC474922

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC214570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7796
0.1-0.2	1274
0.2-0.3	78
0.3-0.4	2
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