NPASS Compound

Natural Product: NPC112685

Natural Product ID	NPC112685
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Rollicosin
IUPAC Name	(2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R)-5-oxooxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Synonyms	Rollicosin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL461611
PubChem CID	10318589
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

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 64 65 0 0 0 0 0 0 0 0999 V2000 -6.4661 2.4376 2.8817 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5009 2.6317 1.3836 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3133 2.0025 0.7901 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6804 1.0498 -0.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7682 0.1773 -0.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9845 -1.2777 -0.4186 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0826 -2.1767 -1.2067 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6210 -1.8950 -1.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1748 -2.0232 0.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6687 -1.7639 0.5376 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1606 -2.6926 -0.2259 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6112 -2.6342 -0.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4164 -1.4085 -0.2646 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2535 -0.2654 0.6449 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9506 0.9765 0.2684 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4005 0.9916 0.0844 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9598 0.2666 -1.0641 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4901 0.4725 -1.0219 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9081 1.8844 -1.1872 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6990 2.1981 0.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3133 1.1413 1.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3250 1.1884 2.2488 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9201 0.0437 0.2444 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4757 0.7261 -2.3046 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8556 -1.4920 0.9366 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1220 0.9682 -0.0304 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8348 0.1631 -0.6978 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6100 1.9502 0.8400 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4968 2.4128 3.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9217 3.3055 3.3435 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9852 1.4730 3.1406 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5089 3.7020 1.1731 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2922 2.2998 1.0054 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9730 0.2462 -1.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7288 0.4814 -0.6461 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0771 -1.5404 -0.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2720 -3.2189 -0.7951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3862 -2.1573 -2.2905 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0091 -2.5068 -1.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4459 -0.8407 -1.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6363 -1.2100 0.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4443 -2.9764 0.8440 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5133 -0.7251 0.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4230 -1.7248 1.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1278 -3.7839 -0.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0397 -2.4932 -1.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8112 -3.0427 1.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0726 -3.4914 -0.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4927 -1.8100 0.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4811 -1.1032 -1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 0.0097 0.9321 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6717 -0.5526 1.6989 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4078 1.3467 -0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6421 1.7489 1.0793 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7458 2.0816 0.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9277 0.5813 1.0084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8530 -0.8172 -1.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9560 -0.1319 -1.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0773 2.6232 -1.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5321 2.0480 -2.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7899 2.0650 -0.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4925 3.2210 0.4406 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8916 1.5039 -2.1978 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9804 -0.6636 1.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 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 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 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 17 24 1 0 6 25 1 0 4 26 1 0 26 27 2 0 26 28 1 0 28 2 1 0 23 18 1 0 1 29 1 0 1 30 1 0 1 31 1 0 2 32 1 1 3 33 1 0 5 34 1 0 5 35 1 0 6 36 1 6 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 1 18 58 1 6 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 24 63 1 0 25 64 1 0 M END

Standard InCHIKey	QCRUDDMRGHFGNR-MTFMMBMASA-N
Standard InCHI	InChI=1S/C22H36O6/c1-16-14-17(22(26)27-16)15-18(23)10-8-6-4-2-3-5-7-9-11-19(24)20-12-13-21(25)28-20/h14,16,18-20,23-24H,2-13,15H2,1H3/t16-,18+,19+,20+/m0/s1
SMILES	C[C@H]1C=C(C[C@@H](CCCCCCCCCC[C@H]([C@H]2CCC(=O)O2)O)O)C(=O)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	396.25	Volume:	416.787 ? Van der Waals volume.
Dense:	0.951	LogP:	2.752 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.535 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.265 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	12.0
TPSA:	93.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.344	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.032	Fsp³:	0.818
MCE-18:	28.6 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.55	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.165 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.581	Promiscuous compounds:	0.403

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.155	MDCK Permeability:	-4.773
Pgp-inhibitor:	0.341	Pgp-substrate:	0.66
PAMPA:	0.334 ? 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):	0.007
20% Bioavailability (F20%):	0.742	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.87
Plasma Protein Binding (PPB):	88.187%	Volume Distribution (VD):	0.22
Fu:	12.939% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.668
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.034
CYP2C9-inhibitor:	0.045	CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.83
CYP3A4-inhibitor:	0.014	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.984
HLM stability:	0.858 ? 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):

4.987

Half-life (T1/2):

0.987

ADMET: Toxicity

hERG Blockers:	0.087	hERG Blockers (10um):	0.424
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.43
AMES Toxicity:	0.302	Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.656	Skin Sensitization:	0.997
Carcinogencity:	0.58	Eye Corrosion:	0.151
Eye Irritation:	0.943	Respiratory Toxicity:	0.741
Drug-induced Neurotoxicity:	0.324	Ototoxicity:	0.632
Hematotoxicity:	0.242	Drug-induced Nephrotoxicity:	0.958
Genotoxicity:	0.012	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.738	Hek293 Cytotoxicity:	0.157
BCF:	1.086 ? 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:	4.209 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.658 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.443 ? 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
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654411]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608866]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778247]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15739	Rollinia mucosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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	2

Activity Type	# Activity
Cell line	1
Non-molecular	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
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[12608866]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	0.021	ug.mL-1	PMID[12608866]

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 NPC112685 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	15988
0.1-0.2	29879
0.2-0.3	3620
0.3-0.4	148
0.4-0.5	34
0.5-0.6	77
0.6-0.7	59
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
0.7907	Intermediate Similarity	NPC606043
0.775	Intermediate Similarity	NPC608138
0.7727	Intermediate Similarity	NPC107986
0.7727	Intermediate Similarity	NPC223871
0.7727	Intermediate Similarity	NPC231009
0.7727	Intermediate Similarity	NPC103284
0.7727	Intermediate Similarity	NPC110710
0.7727	Intermediate Similarity	NPC1083
0.7727	Intermediate Similarity	NPC82795
0.7727	Intermediate Similarity	NPC286338
0.7727	Intermediate Similarity	NPC603931
0.7727	Intermediate Similarity	NPC604237
0.7556	Intermediate Similarity	NPC488253
0.7556	Intermediate Similarity	NPC473669
0.7556	Intermediate Similarity	NPC488251
0.7391	Intermediate Similarity	NPC81045
0.7391	Intermediate Similarity	NPC232555
0.7391	Intermediate Similarity	NPC39754
0.7391	Intermediate Similarity	NPC171135
0.7391	Intermediate Similarity	NPC171174
0.7391	Intermediate Similarity	NPC182383
0.7391	Intermediate Similarity	NPC114694
0.7391	Intermediate Similarity	NPC61257
0.7391	Intermediate Similarity	NPC320569
0.7391	Intermediate Similarity	NPC485248
0.7391	Intermediate Similarity	NPC133730
0.7391	Intermediate Similarity	NPC191929
0.7391	Intermediate Similarity	NPC142117
0.7391	Intermediate Similarity	NPC100454
0.7391	Intermediate Similarity	NPC242364
0.7391	Intermediate Similarity	NPC480249
0.7391	Intermediate Similarity	NPC172821
0.7391	Intermediate Similarity	NPC485249
0.7391	Intermediate Similarity	NPC274446
0.7391	Intermediate Similarity	NPC485251
0.7391	Intermediate Similarity	NPC151403
0.7391	Intermediate Similarity	NPC240695
0.7391	Intermediate Similarity	NPC261952
0.7391	Intermediate Similarity	NPC605171
0.7234	Intermediate Similarity	NPC93794
0.7234	Intermediate Similarity	NPC488632
0.7234	Intermediate Similarity	NPC134865
0.7234	Intermediate Similarity	NPC473504
0.7234	Intermediate Similarity	NPC103523
0.7234	Intermediate Similarity	NPC81778
0.7234	Intermediate Similarity	NPC40066
0.7234	Intermediate Similarity	NPC488627
0.7234	Intermediate Similarity	NPC488631
0.7083	Intermediate Similarity	NPC280621
0.7083	Intermediate Similarity	NPC48338
0.7083	Intermediate Similarity	NPC488628
0.6939	Remote Similarity	NPC178215
0.6939	Remote Similarity	NPC42598
0.6939	Remote Similarity	NPC473687
0.6939	Remote Similarity	NPC204686
0.6939	Remote Similarity	NPC219498
0.6939	Remote Similarity	NPC308412
0.6939	Remote Similarity	NPC134885
0.6939	Remote Similarity	NPC488247
0.6939	Remote Similarity	NPC210218
0.6939	Remote Similarity	NPC488248
0.6875	Remote Similarity	NPC47937
0.68	Remote Similarity	NPC20621
0.68	Remote Similarity	NPC318963
0.68	Remote Similarity	NPC488250
0.68	Remote Similarity	NPC602738
0.68	Remote Similarity	NPC605101
0.6667	Remote Similarity	NPC473478
0.6667	Remote Similarity	NPC69082
0.6667	Remote Similarity	NPC473651
0.6667	Remote Similarity	NPC488249
0.6667	Remote Similarity	NPC20339
0.6667	Remote Similarity	NPC66346
0.6538	Remote Similarity	NPC283085
0.6538	Remote Similarity	NPC169511
0.6538	Remote Similarity	NPC287164
0.6538	Remote Similarity	NPC234077
0.6538	Remote Similarity	NPC130359
0.6538	Remote Similarity	NPC14901
0.6531	Remote Similarity	NPC477011
0.6471	Remote Similarity	NPC134807
0.6415	Remote Similarity	NPC488623
0.6415	Remote Similarity	NPC488624
0.6415	Remote Similarity	NPC488629
0.641	Remote Similarity	NPC609089
0.6296	Remote Similarity	NPC239517
0.625	Remote Similarity	NPC100921
0.625	Remote Similarity	NPC475159
0.625	Remote Similarity	NPC131002
0.625	Remote Similarity	NPC473780
0.625	Remote Similarity	NPC477018
0.625	Remote Similarity	NPC604521
0.625	Remote Similarity	NPC606903
0.6226	Remote Similarity	NPC231096
0.6226	Remote Similarity	NPC475581
0.6226	Remote Similarity	NPC62118
0.6226	Remote Similarity	NPC132496
0.6226	Remote Similarity	NPC107717
0.6226	Remote Similarity	NPC488252
0.62	Remote Similarity	NPC488246
0.62	Remote Similarity	NPC480080
0.6182	Remote Similarity	NPC488630
0.6182	Remote Similarity	NPC488625
0.6182	Remote Similarity	NPC91067
0.6182	Remote Similarity	NPC488626
0.6111	Remote Similarity	NPC233551
0.6111	Remote Similarity	NPC40376
0.6111	Remote Similarity	NPC21208
0.6078	Remote Similarity	NPC480079
0.6	Remote Similarity	NPC156804
0.5965	Remote Similarity	NPC473663
0.5965	Remote Similarity	NPC473723
0.5965	Remote Similarity	NPC475173
0.5957	Remote Similarity	NPC73310
0.5957	Remote Similarity	NPC473529
0.5957	Remote Similarity	NPC180363
0.5957	Remote Similarity	NPC94875
0.5957	Remote Similarity	NPC11332
0.5957	Remote Similarity	NPC145914
0.5957	Remote Similarity	NPC601174
0.5957	Remote Similarity	NPC601403
0.5957	Remote Similarity	NPC603568
0.5957	Remote Similarity	NPC604330
0.5957	Remote Similarity	NPC608300
0.5957	Remote Similarity	NPC611200
0.5957	Remote Similarity	NPC611571
0.5926	Remote Similarity	NPC606740
0.5926	Remote Similarity	NPC608614
0.5893	Remote Similarity	NPC480081
0.5882	Remote Similarity	NPC473649
0.5882	Remote Similarity	NPC473156
0.5882	Remote Similarity	NPC154097
0.5882	Remote Similarity	NPC163093
0.5882	Remote Similarity	NPC159750
0.5882	Remote Similarity	NPC73248
0.5882	Remote Similarity	NPC282815
0.5882	Remote Similarity	NPC470401
0.5882	Remote Similarity	NPC600956
0.5882	Remote Similarity	NPC610454
0.5769	Remote Similarity	NPC473671
0.5769	Remote Similarity	NPC475268
0.5769	Remote Similarity	NPC470400
0.5769	Remote Similarity	NPC77871
0.5769	Remote Similarity	NPC9678
0.5769	Remote Similarity	NPC319036
0.5769	Remote Similarity	NPC604764
0.5769	Remote Similarity	NPC605867
0.5741	Remote Similarity	NPC473707
0.566	Remote Similarity	NPC132940
0.5636	Remote Similarity	NPC488244
0.56	Remote Similarity	NPC25764
0.56	Remote Similarity	NPC235809
0.56	Remote Similarity	NPC329829
0.56	Remote Similarity	NPC39279
0.56	Remote Similarity	NPC39167
0.56	Remote Similarity	NPC292809
0.56	Remote Similarity	NPC202055
0.56	Remote Similarity	NPC606804
0.56	Remote Similarity	NPC607425
0.56	Remote Similarity	NPC608574
0.5556	Remote Similarity	NPC309211
0.5556	Remote Similarity	NPC329838
0.5556	Remote Similarity	NPC20533
0.5556	Remote Similarity	NPC477010
0.55	Remote Similarity	NPC482766
0.55	Remote Similarity	NPC279267
0.5435	Remote Similarity	NPC609415
0.5357	Remote Similarity	NPC120398
0.5357	Remote Similarity	NPC258068
0.5357	Remote Similarity	NPC471567
0.5357	Remote Similarity	NPC476583
0.5283	Remote Similarity	NPC144415
0.5283	Remote Similarity	NPC600524
0.5283	Remote Similarity	NPC607439
0.5283	Remote Similarity	NPC608157
0.5283	Remote Similarity	NPC608355
0.5263	Remote Similarity	NPC89001
0.5263	Remote Similarity	NPC477014
0.5263	Remote Similarity	NPC477013
0.5185	Remote Similarity	NPC219652
0.5185	Remote Similarity	NPC473840
0.5185	Remote Similarity	NPC25703
0.5185	Remote Similarity	NPC241360
0.5185	Remote Similarity	NPC293136
0.5091	Remote Similarity	NPC473904
0.5091	Remote Similarity	NPC65930
0.5082	Remote Similarity	NPC488245

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC112685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6182
0.1-0.2	2881
0.2-0.3	83
0.3-0.4	4
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