NPASS Compound

Natural Product: NPC119355

Natural Product ID	NPC119355
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	30-Hydroxy-Betulin
IUPAC Name	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms	30-Hydroxy-Betulin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL141717
PubChem CID	473110
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 -3.6343 2.3000 2.9324 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0802 1.3840 2.0318 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8309 0.2336 2.5970 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2872 -1.0032 2.3605 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8234 1.6008 0.5818 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1693 1.4917 -0.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0372 0.3486 -1.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5593 0.4769 -1.4483 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9876 -0.7224 -2.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4888 -0.5990 -2.1496 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9066 -0.4826 -0.7273 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1624 -1.7970 -0.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5537 0.7142 -0.1210 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9123 1.2529 1.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5542 1.5223 0.7325 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1373 0.1709 0.4213 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6372 0.1466 0.5798 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2909 1.3442 0.0241 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9088 0.1513 2.0959 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3513 0.0787 2.4104 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2300 -0.6230 1.4383 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5592 -1.5065 0.4551 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3822 -1.5297 -0.8447 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6593 -2.9704 0.9389 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1398 -1.1912 0.1489 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7280 -1.5274 -1.2801 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2018 -1.6910 -1.2139 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6049 -0.3325 -0.8663 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8666 0.5544 -2.0502 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1609 0.2605 0.8342 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0277 0.5150 0.0016 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3897 1.7509 -2.1815 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2082 1.6520 -3.3356 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8467 2.1400 3.9717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0817 3.1704 2.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8998 0.3322 3.7214 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8920 0.2025 2.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1535 -1.5583 3.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3915 2.6175 0.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0028 1.2951 0.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4436 2.4505 -0.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6006 0.5651 -2.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2815 -0.6209 -0.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 -0.8505 -3.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3069 -1.6237 -1.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2576 0.2631 -2.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0788 -1.4944 -2.6360 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8622 -2.5808 -0.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2059 -2.0572 0.1249 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5969 -1.9952 0.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4166 1.5433 -0.8832 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0004 0.6299 2.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3263 2.2929 1.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4566 2.1684 -0.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0683 2.0684 1.5199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7551 -0.5210 1.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9521 1.8814 0.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4858 2.1223 -0.1535 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9198 1.2092 -0.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4211 -0.7901 2.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4626 1.0201 2.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7341 1.1380 2.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4442 -0.3156 3.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9214 -1.2722 2.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0978 -0.7540 -1.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1842 -2.5092 -1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4734 -1.5696 -0.6092 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0465 -3.0951 1.8649 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3935 -3.6729 0.1431 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7071 -3.1915 1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5176 -1.9102 0.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0428 -0.7932 -2.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1176 -2.5621 -1.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7864 -2.1319 -2.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0611 -2.3252 -0.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7306 -0.0969 -2.9664 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9146 0.9005 -2.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2376 1.4609 -2.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0330 0.3577 -0.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3302 -0.4287 0.4437 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7016 2.6482 -1.6546 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3824 1.9500 -2.5991 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9155 2.3191 -3.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 2 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 13 31 1 0 8 32 1 6 32 33 1 0 31 5 1 0 31 8 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 5 39 1 1 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 6 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 1 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 1 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 1 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 31 80 1 1 32 81 1 0 32 82 1 0 33 83 1 0 M END

Standard InCHIKey	XTNACZMKNVUNAA-ROUWMTJPSA-N
Standard InCHI	InChI=1S/C30H50O3/c1-19(17-31)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-27(4)12-11-24(33)26(2,3)22(27)10-13-29(23,28)6/h20-25,31-33H,1,7-18H2,2-6H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
SMILES	C=C(CO)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.38	Volume:	508.388 ? Van der Waals volume.
Dense:	0.902	LogP:	4.398 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.13 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.596 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	26.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.457	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.909	Fsp³:	0.933
MCE-18:	100.793 ? 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:	0.639	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.397	Promiscuous compounds:	0.228

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969	MDCK Permeability:	-4.791
Pgp-inhibitor:	0.0	Pgp-substrate:	0.987
PAMPA:	0.946 ? 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):	0.008
20% Bioavailability (F20%):	0.885	30% Bioavailability (F30%):	0.975
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.998	MRP1:	0.848
Plasma Protein Binding (PPB):	88.561%	Volume Distribution (VD):	-0.073
Fu:	12.207% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.592
OATP1B3 inhibitor:	0.257	BCRP inhibitor:	0.445
BSEP inhibitor:	0.026

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.657	CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.072	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.727	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.975
HLM stability:	0.076 ? 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):

8.271

Half-life (T1/2):

1.01

ADMET: Toxicity

hERG Blockers:	0.108	hERG Blockers (10um):	0.195
Human Hepatotoxicity (H-HT):	0.681	Drug-induced Liver Injury (DILI):	0.287
AMES Toxicity:	0.476	Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.452	Skin Sensitization:	0.973
Carcinogencity:	0.936	Eye Corrosion:	0.021
Eye Irritation:	0.729	Respiratory Toxicity:	0.91
Drug-induced Neurotoxicity:	0.097	Ototoxicity:	0.602
Hematotoxicity:	0.603	Drug-induced Nephrotoxicity:	0.795
Genotoxicity:	0.445	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.211	Hek293 Cytotoxicity:	0.404
BCF:	1.666 ? 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:	3.745 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.177 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.524 ? 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
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22423	Microtropis fokienensis	Species	Celastraceae	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	1
EC50	2

Activity Type	# Activity
Cell line	2
Organism	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
NPT759	Cell line	H9	Homo sapiens	IC50	>	140000.0	nM	PMID[26819664]
NPT759	Cell line	H9	Homo sapiens	EC50	=	50800.0	nM	PMID[26819664]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50815.94	nM	PubChem BioAssay data set

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 NPC119355 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	27549
0.1-0.2	19306
0.2-0.3	2479
0.3-0.4	383
0.4-0.5	77
0.5-0.6	36
0.6-0.7	19
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC231256
0.88	High Similarity	NPC178383
0.8077	Intermediate Similarity	NPC248830
0.8077	Intermediate Similarity	NPC212241
0.7547	Intermediate Similarity	NPC78067
0.7547	Intermediate Similarity	NPC278091
0.6964	Remote Similarity	NPC5767
0.6964	Remote Similarity	NPC475742
0.6852	Remote Similarity	NPC192638
0.6852	Remote Similarity	NPC25511
0.6852	Remote Similarity	NPC600137
0.661	Remote Similarity	NPC474484
0.6552	Remote Similarity	NPC86305
0.6552	Remote Similarity	NPC212879
0.6452	Remote Similarity	NPC168231
0.6379	Remote Similarity	NPC93662
0.6271	Remote Similarity	NPC246956
0.6271	Remote Similarity	NPC74595
0.6271	Remote Similarity	NPC264665
0.6271	Remote Similarity	NPC269396
0.6207	Remote Similarity	NPC472742
0.6066	Remote Similarity	NPC12774
0.6034	Remote Similarity	NPC144075
0.6034	Remote Similarity	NPC104387
0.6034	Remote Similarity	NPC301226
0.5893	Remote Similarity	NPC142712
0.5862	Remote Similarity	NPC185536
0.5846	Remote Similarity	NPC16377
0.5789	Remote Similarity	NPC480925
0.5789	Remote Similarity	NPC48079
0.5781	Remote Similarity	NPC607755
0.5763	Remote Similarity	NPC91573
0.5763	Remote Similarity	NPC202540
0.5738	Remote Similarity	NPC201459
0.569	Remote Similarity	NPC606606
0.5667	Remote Similarity	NPC42853
0.5667	Remote Similarity	NPC237460
0.5625	Remote Similarity	NPC5280
0.5593	Remote Similarity	NPC97534
0.5593	Remote Similarity	NPC195155
0.5574	Remote Similarity	NPC296701
0.5574	Remote Similarity	NPC218616
0.5556	Remote Similarity	NPC474233
0.5538	Remote Similarity	NPC483720
0.55	Remote Similarity	NPC245869
0.5469	Remote Similarity	NPC175410
0.5397	Remote Similarity	NPC103754
0.5357	Remote Similarity	NPC232112
0.5323	Remote Similarity	NPC211009
0.5316	Remote Similarity	NPC478270
0.5316	Remote Similarity	NPC478271
0.5303	Remote Similarity	NPC33768
0.5238	Remote Similarity	NPC13554
0.5231	Remote Similarity	NPC477577
0.5156	Remote Similarity	NPC298168
0.5156	Remote Similarity	NPC143133
0.5156	Remote Similarity	NPC126993
0.5152	Remote Similarity	NPC264317
0.5152	Remote Similarity	NPC294438
0.5077	Remote Similarity	NPC49599
0.5077	Remote Similarity	NPC49627

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC119355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7932
0.1-0.2	1166
0.2-0.3	48
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
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
0.5152	Remote Similarity	NPD7520	Phase 1

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