NPASS Compound

Natural Product: NPC104585

Natural Product ID	NPC104585
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MZUKFJRNNJXADZ-RZYUKCEPSA-N
IUPAC Name	n.a.
Synonyms	16Alpha-Hydroxycalactin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL556108
PubChem CID	45270717
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 79 85 0 0 0 0 0 0 0 0999 V2000 7.0252 2.1516 -0.5223 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8588 0.8172 0.1390 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2652 -0.3297 -0.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0943 -0.9463 -1.4798 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0055 -1.3400 -0.5025 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3258 -0.7228 0.8174 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5802 0.6559 0.6389 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2689 -0.7910 1.7317 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1689 -0.2178 1.0948 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0545 0.1309 2.0187 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9234 0.6836 1.1748 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0761 1.4181 1.9946 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1726 1.9125 1.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8205 0.6420 0.5200 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8858 -0.1209 -0.3739 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5459 -1.4074 -0.7493 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9625 -1.3059 -1.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8371 -0.4620 -0.2723 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0206 -1.2355 0.9634 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0487 -0.0814 -1.0598 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1953 0.4098 -0.2986 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6969 1.6205 -0.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8382 1.7340 0.5295 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5742 2.7448 0.7282 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0172 0.5544 1.1687 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0284 -0.3359 0.6996 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5138 0.9650 -1.9899 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1182 1.3505 -1.5125 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1545 0.8704 -0.0892 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8716 1.7610 0.6601 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4275 0.4793 -3.3103 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3884 -0.4434 0.3672 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4551 -0.8161 -0.6430 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7777 -1.1137 -0.0367 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7734 -1.0063 -1.0118 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1472 -1.6483 1.2151 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6846 -2.7168 1.0409 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0423 -2.7412 -0.3705 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5819 -2.0623 -2.1576 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0498 2.5353 -0.9074 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4269 2.9169 0.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7310 2.0233 -1.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5476 0.8047 1.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7783 -1.1208 -0.1271 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0067 0.0407 -1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7351 -0.2138 -2.2289 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2036 -1.2407 1.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5414 0.7484 0.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7088 -0.8132 2.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4174 0.8718 2.7455 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3934 1.4167 0.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5077 0.7330 2.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4174 2.2979 2.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9226 2.5159 1.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6535 2.4639 0.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9794 -0.0053 1.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5950 0.4478 -1.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9693 -1.8038 -1.6386 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4097 -2.2159 0.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0828 -1.0610 -2.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3966 -2.3478 -1.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7409 -2.0478 0.8108 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1439 -0.6497 1.8942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0450 -1.7907 1.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3043 -0.9809 -1.6818 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4358 2.4983 -0.9623 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4789 -0.6510 1.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5814 -1.1761 0.2122 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0639 1.8977 -2.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3933 0.8528 -2.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9339 2.4333 -1.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7631 2.6794 0.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2889 0.0465 -3.5321 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5796 0.0490 -1.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1473 -1.6883 -1.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8466 -2.1746 0.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5558 -1.5380 2.0312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1448 -2.9993 0.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9542 -2.8114 -2.1666 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 6 8 1 0 8 9 1 0 9 10 1 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 1 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 20 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 27 31 1 0 15 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 32 36 1 1 36 37 2 0 5 38 1 1 4 39 1 0 7 2 1 0 34 9 1 0 35 5 1 0 32 11 1 0 29 14 1 0 29 18 1 0 26 21 1 0 1 40 1 0 1 41 1 0 1 42 1 0 2 43 1 1 3 44 1 0 3 45 1 0 4 46 1 6 6 47 1 1 9 48 1 6 10 49 1 0 10 50 1 0 11 51 1 6 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 1 15 57 1 6 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 19 62 1 0 19 63 1 0 19 64 1 0 20 65 1 6 22 66 1 0 26 67 1 0 26 68 1 0 27 69 1 6 28 70 1 0 28 71 1 0 30 72 1 0 31 73 1 0 33 74 1 0 33 75 1 0 34 76 1 1 36 77 1 0 38 78 1 0 39 79 1 0 M END

Standard InCHIKey	MZUKFJRNNJXADZ-RZYUKCEPSA-N
Standard InCHI	InChI=1S/C29H40O10/c1-14-7-22(32)29(35)25(37-14)38-20-9-16-3-4-18-17(27(16,13-30)11-21(20)39-29)5-6-26(2)24(15-8-23(33)36-12-15)19(31)10-28(18,26)34/h8,13-14,16-22,24-25,31-32,34-35H,3-7,9-12H2,1-2H3/t14-,16+,17+,18-,19-,20-,21-,22-,24+,25+,26-,27-,28+,29+/m1/s1
SMILES	C[C@@H]1C[C@H]([C@]2([C@@H](O1)O[C@@H]1C[C@@H]3CC[C@@H]4[C@H](CC[C@]5(C)[C@@H](C6=CC(=O)OC6)[C@@H](C[C@]45O)O)[C@]3(C[C@H]1O2)C=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	548.26	Volume:	530.238 ? Van der Waals volume.
Dense:	1.034	LogP:	0.589 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.113 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.301 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	37.0
TPSA:	151.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	7.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.223	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.774	Fsp³:	0.862
MCE-18:	128.333 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.652	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.148	Promiscuous compounds:	0.722

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.225	MDCK Permeability:	-4.97
Pgp-inhibitor:	0.001	Pgp-substrate:	0.86
PAMPA:	0.993 ? 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):	0.01
20% Bioavailability (F20%):	0.473	30% Bioavailability (F30%):	0.679
50% Bioavailability (F50%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.432
Plasma Protein Binding (PPB):	83.417%	Volume Distribution (VD):	0.059
Fu:	15.445% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.034
BSEP inhibitor:	0.753

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.022	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.074	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.671
HLM stability:	0.033 ? 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):

1.954

Half-life (T1/2):

3.569

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.264
Human Hepatotoxicity (H-HT):	0.7	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.975	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.989
Drug-induced Neurotoxicity:	0.512	Ototoxicity:	0.727
Hematotoxicity:	0.978	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.973
A549 Cytotoxicity:	0.767	Hek293 Cytotoxicity:	0.983
BCF:	0.532 ? 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:	3.336 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.08 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.229 ? 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
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	roots	Wadi Um Hebal, Egypt	2001-JAN	PMID[16989527]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555122]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30629433]
NPO33139	Pergularia tomentosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	7

Activity Type	# Activity
Cell line	5
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
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	1000.0	nM	PMID[19133778]
NPT1081	Cell line	BXPC-3	Homo sapiens	IC50	=	2300.0	nM	PMID[21506603]
NPT114	Cell line	LoVo	Homo sapiens	IC50	=	4400.0	nM	PMID[21506603]
NPT81	Cell line	A549	Homo sapiens	IC50	=	400.0	nM	PMID[25650896]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	3800.0	nM	PMID[21090801]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2600.0	nM	PMID[19555122]
NPT2	Others	Unspecified	n.a.	IC50	=	1700.0	nM	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 NPC104585 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	15958
0.1-0.2	31833
0.2-0.3	1842
0.3-0.4	158
0.4-0.5	33
0.5-0.6	9
0.6-0.7	12
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8312	Intermediate Similarity	NPC253456
0.8312	Intermediate Similarity	NPC159338
0.8205	Intermediate Similarity	NPC488160
0.7901	Intermediate Similarity	NPC157817
0.7654	Intermediate Similarity	NPC42670
0.7654	Intermediate Similarity	NPC19124
0.7561	Intermediate Similarity	NPC298783
0.7381	Intermediate Similarity	NPC33934
0.7349	Intermediate Similarity	NPC488162
0.7349	Intermediate Similarity	NPC93416
0.7349	Intermediate Similarity	NPC488161
0.7349	Intermediate Similarity	NPC16569
0.7011	Intermediate Similarity	NPC225385
0.6818	Remote Similarity	NPC488163
0.6706	Remote Similarity	NPC277374
0.6404	Remote Similarity	NPC488158
0.6404	Remote Similarity	NPC488159
0.6395	Remote Similarity	NPC171619
0.6364	Remote Similarity	NPC79193
0.6292	Remote Similarity	NPC474466
0.618	Remote Similarity	NPC91
0.618	Remote Similarity	NPC329905
0.618	Remote Similarity	NPC609258
0.6154	Remote Similarity	NPC142756
0.6044	Remote Similarity	NPC163365
0.5957	Remote Similarity	NPC470094
0.5789	Remote Similarity	NPC480905
0.5789	Remote Similarity	NPC85369
0.5729	Remote Similarity	NPC473040
0.5714	Remote Similarity	NPC476221
0.5714	Remote Similarity	NPC477709
0.5556	Remote Similarity	NPC24839
0.5532	Remote Similarity	NPC475136
0.525	Remote Similarity	NPC220217

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC104585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6500
0.1-0.2	2577
0.2-0.3	61
0.3-0.4	9
0.4-0.5	3
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