NPASS Compound

Natural Product: NPC603079

Natural Product ID	NPC603079
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GAWOMYRLBFCSGL-LYCJLDPISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3355092
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 87 0 0 0 0 0 0 0 0999 V2000 4.2937 0.5519 -1.9273 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7340 0.5688 -0.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9444 -0.0210 0.2227 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7183 -0.6229 0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6412 0.2834 -0.5584 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5033 -0.3781 -0.7070 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5751 -0.3704 0.0571 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6993 -1.5658 0.8283 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7457 -2.4318 0.7374 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7624 -3.5189 -0.0671 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6907 -3.9223 -0.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5919 -3.5268 -0.8043 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5807 -3.9352 -1.6903 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2842 -4.7719 -2.7251 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2427 -5.2135 -3.6454 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0148 -5.2054 -2.8757 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9693 -4.7807 -1.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8627 -4.3134 -0.1031 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9247 -4.1103 0.5933 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0399 -4.9450 0.5343 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1447 -4.6654 1.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2491 -5.4818 1.2603 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1785 -3.5840 2.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0728 -2.7364 2.2178 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0635 -1.6420 3.0389 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9949 -3.0433 1.4342 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8792 -2.1887 1.5052 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9346 -1.2085 2.2779 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7105 0.8162 0.9358 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5327 1.8260 0.3472 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6775 2.3298 0.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0521 1.8699 2.0078 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4470 3.3556 0.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5957 3.8644 0.7411 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3514 4.8441 0.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5165 5.3385 0.6817 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8922 5.2823 -1.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6093 6.2542 -1.7896 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7469 4.7970 -1.6883 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3382 5.2747 -2.9040 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0161 3.8186 -1.0186 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5992 1.3671 1.3932 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1381 0.5672 2.3940 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5572 1.5704 0.2370 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1692 2.6277 -0.5495 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0250 1.1872 -0.4254 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7611 1.7422 -1.4444 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0024 2.3456 -1.1907 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7089 2.8891 -2.2369 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4939 2.3872 0.0808 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7051 2.9722 0.3490 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7702 1.8371 1.1103 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2415 1.8641 2.4069 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5491 1.2467 0.8425 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3269 -0.9881 0.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7504 -1.4990 -0.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0053 0.6034 -1.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5344 -0.3234 -0.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -2.8910 -0.0028 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6098 -3.6224 -1.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5792 -4.6262 -4.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2391 -5.8670 -3.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9829 -5.1476 -2.1375 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9749 -5.7890 -0.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2242 -6.3392 0.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0396 -3.3472 2.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2054 -1.6897 4.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2539 0.5728 1.8955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9500 3.5179 1.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5488 5.3856 1.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5737 7.2333 -1.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8625 6.1419 -3.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1044 3.4012 -1.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4102 2.3794 1.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7630 1.1500 2.9286 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5571 1.7731 0.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6042 2.6549 -1.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4302 1.7429 -2.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3935 2.3862 -2.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5076 2.6653 -0.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6655 2.2042 3.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0001 0.8219 1.6685 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 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 10 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 21 23 2 0 23 24 1 0 24 25 1 0 24 26 2 0 26 27 1 0 27 28 2 0 7 29 1 0 29 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 35 37 2 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 2 0 29 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 2 46 1 0 46 47 2 0 47 48 1 0 48 49 1 0 48 50 2 0 50 51 1 0 50 52 1 0 52 53 1 0 52 54 2 0 44 5 1 0 54 46 1 0 27 9 1 0 41 33 1 0 17 11 1 0 26 19 1 0 4 55 1 0 4 56 1 0 5 57 1 6 7 58 1 6 12 59 1 0 13 60 1 0 15 61 1 0 16 62 1 0 17 63 1 0 20 64 1 0 22 65 1 0 23 66 1 0 25 67 1 0 29 68 1 1 34 69 1 0 36 70 1 0 38 71 1 0 40 72 1 0 41 73 1 0 42 74 1 1 43 75 1 0 44 76 1 1 45 77 1 0 47 78 1 0 49 79 1 0 51 80 1 0 53 81 1 0 54 82 1 0 M END

Standard InCHIKey	GAWOMYRLBFCSGL-LYCJLDPISA-N
Standard InCHI	InChI=1S/C35H28O19/c36-15-3-1-12(2-4-15)30-31(28(46)24-17(38)9-16(37)10-22(24)51-30)54-35-32(53-34(49)14-7-20(41)26(44)21(42)8-14)29(47)27(45)23(52-35)11-50-33(48)13-5-18(39)25(43)19(40)6-13/h1-10,23,27,29,32,35-45,47H,11H2/t23-,27-,29+,32-,35+/m1/s1
SMILES	O=C(OC[C@H]1O[C@@H](Oc2c(-c3ccc(O)cc3)oc3cc(O)cc(O)c3c2=O)[C@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H](O)[C@@H]1O)c1cc(O)c(O)c(O)c1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	752.12	Volume:	687.408 ? Van der Waals volume.
Dense:	1.094	LogP:	1.126 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.077 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.572 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	38.0
TPSA:	323.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.079	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.634	Fsp³:	0.171
MCE-18:	136.244 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.89	Fluc inhibitor:	0.298 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.781 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.663 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.3	Promiscuous compounds:	0.976

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.935	MDCK Permeability:	-4.802
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	1.0 ? 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%):	0.665	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	87.879%	Volume Distribution (VD):	-0.142
Fu:	10.617% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.997
BSEP inhibitor:	0.777

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.992
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.214 ? 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):

3.754

Half-life (T1/2):

3.554

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.921
Human Hepatotoxicity (H-HT):	0.077	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.51	Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.89	Skin Sensitization:	1.0
Carcinogencity:	0.158	Eye Corrosion:	0.0
Eye Irritation:	0.985	Respiratory Toxicity:	0.06
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.972
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.001
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.807
BCF:	0.691 ? 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:	3.714 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.523 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.203 ? 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
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	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	6
Retention_time	1
Survival	1

Activity Type	# Activity
Cell line	6
No target	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
NPT116	Cell line	HL-60	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[25074815]
NPT28833	No target	No relevant target	n.a.	Retention_time	=	23.37	min	PMID[25074815]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Survival	=	24.6	%	PMID[25074815]

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 NPC603079 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	18289
0.1-0.2	28317
0.2-0.3	2455
0.3-0.4	486
0.4-0.5	152
0.5-0.6	119
0.6-0.7	13
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC97119
0.8276	Intermediate Similarity	NPC61904
0.8068	Intermediate Similarity	NPC296018
0.7889	Intermediate Similarity	NPC270448
0.7753	Intermediate Similarity	NPC35167
0.7667	Intermediate Similarity	NPC253521
0.7667	Intermediate Similarity	NPC113836
0.7473	Intermediate Similarity	NPC154741
0.7416	Intermediate Similarity	NPC258044
0.7416	Intermediate Similarity	NPC217387
0.7363	Intermediate Similarity	NPC144097
0.7312	Intermediate Similarity	NPC37668
0.7021	Intermediate Similarity	NPC297503
0.6809	Remote Similarity	NPC129264
0.6804	Remote Similarity	NPC135831
0.65	Remote Similarity	NPC218161
0.6327	Remote Similarity	NPC12013
0.6327	Remote Similarity	NPC11432
0.6327	Remote Similarity	NPC477613
0.6264	Remote Similarity	NPC216496
0.6129	Remote Similarity	NPC224530
0.6078	Remote Similarity	NPC292929
0.6078	Remote Similarity	NPC221342
0.6078	Remote Similarity	NPC476470
0.6071	Remote Similarity	NPC4013
0.6019	Remote Similarity	NPC602448
0.598	Remote Similarity	NPC89127
0.5941	Remote Similarity	NPC122467
0.5918	Remote Similarity	NPC196127
0.5918	Remote Similarity	NPC267680
0.5909	Remote Similarity	NPC480445
0.5882	Remote Similarity	NPC486577
0.5833	Remote Similarity	NPC170052
0.5833	Remote Similarity	NPC476215
0.5833	Remote Similarity	NPC135846
0.5795	Remote Similarity	NPC90905
0.5789	Remote Similarity	NPC259957
0.5776	Remote Similarity	NPC487499
0.5714	Remote Similarity	NPC162394
0.57	Remote Similarity	NPC304741
0.5664	Remote Similarity	NPC480444
0.566	Remote Similarity	NPC214621
0.566	Remote Similarity	NPC34267
0.5604	Remote Similarity	NPC288084
0.56	Remote Similarity	NPC163242
0.56	Remote Similarity	NPC272068
0.5596	Remote Similarity	NPC303694
0.5593	Remote Similarity	NPC473554
0.5536	Remote Similarity	NPC488734
0.5536	Remote Similarity	NPC488735
0.5536	Remote Similarity	NPC488739
0.5536	Remote Similarity	NPC488732
0.5536	Remote Similarity	NPC488738
0.5524	Remote Similarity	NPC85751
0.5524	Remote Similarity	NPC19240
0.5521	Remote Similarity	NPC48093
0.5505	Remote Similarity	NPC173837
0.55	Remote Similarity	NPC471079
0.5484	Remote Similarity	NPC111929
0.5484	Remote Similarity	NPC320283
0.5484	Remote Similarity	NPC41121
0.5478	Remote Similarity	NPC488737
0.5463	Remote Similarity	NPC89052
0.5455	Remote Similarity	NPC254855
0.5455	Remote Similarity	NPC116864
0.5455	Remote Similarity	NPC244776
0.5455	Remote Similarity	NPC94610
0.5455	Remote Similarity	NPC95866
0.5446	Remote Similarity	NPC173582
0.5446	Remote Similarity	NPC470405
0.5446	Remote Similarity	NPC265885
0.5446	Remote Similarity	NPC181465
0.5446	Remote Similarity	NPC215710
0.5446	Remote Similarity	NPC473438
0.5446	Remote Similarity	NPC253788
0.5437	Remote Similarity	NPC470125
0.5429	Remote Similarity	NPC221288
0.5429	Remote Similarity	NPC194836
0.5429	Remote Similarity	NPC91493
0.5429	Remote Similarity	NPC605081
0.5426	Remote Similarity	NPC104677
0.5426	Remote Similarity	NPC77672
0.5426	Remote Similarity	NPC133671
0.5426	Remote Similarity	NPC135391
0.5426	Remote Similarity	NPC78263
0.5426	Remote Similarity	NPC250069
0.5361	Remote Similarity	NPC159579
0.534	Remote Similarity	NPC255157
0.534	Remote Similarity	NPC259896
0.5339	Remote Similarity	NPC25946
0.5328	Remote Similarity	NPC487502
0.5326	Remote Similarity	NPC54802
0.5326	Remote Similarity	NPC197304
0.5306	Remote Similarity	NPC484158
0.5304	Remote Similarity	NPC488740
0.5304	Remote Similarity	NPC488736
0.5304	Remote Similarity	NPC488733
0.5278	Remote Similarity	NPC223426
0.5243	Remote Similarity	NPC155877
0.5229	Remote Similarity	NPC81042
0.5213	Remote Similarity	NPC67037
0.5213	Remote Similarity	NPC255615
0.5204	Remote Similarity	NPC129217
0.5161	Remote Similarity	NPC249560
0.5159	Remote Similarity	NPC487500
0.5158	Remote Similarity	NPC476771
0.5152	Remote Similarity	NPC85707
0.5146	Remote Similarity	NPC67326
0.514	Remote Similarity	NPC101399
0.514	Remote Similarity	NPC142142
0.514	Remote Similarity	NPC217822
0.514	Remote Similarity	NPC11847
0.514	Remote Similarity	NPC198938
0.5106	Remote Similarity	NPC34531
0.5104	Remote Similarity	NPC127546
0.5104	Remote Similarity	NPC57625
0.5104	Remote Similarity	NPC173637
0.5104	Remote Similarity	NPC317489
0.5104	Remote Similarity	NPC223424
0.5104	Remote Similarity	NPC476772
0.5104	Remote Similarity	NPC600591
0.5096	Remote Similarity	NPC203259
0.5096	Remote Similarity	NPC473862
0.5096	Remote Similarity	NPC33054
0.5096	Remote Similarity	NPC176740
0.5096	Remote Similarity	NPC471725
0.5096	Remote Similarity	NPC134532
0.5096	Remote Similarity	NPC156869
0.5096	Remote Similarity	NPC602582
0.5091	Remote Similarity	NPC96605
0.5091	Remote Similarity	NPC280642
0.5052	Remote Similarity	NPC145038
0.5052	Remote Similarity	NPC56077
0.5052	Remote Similarity	NPC281131
0.5052	Remote Similarity	NPC64305
0.5052	Remote Similarity	NPC253662
0.5052	Remote Similarity	NPC179950
0.5052	Remote Similarity	NPC88789
0.5052	Remote Similarity	NPC491374
0.5051	Remote Similarity	NPC175107
0.5047	Remote Similarity	NPC104883
0.5047	Remote Similarity	NPC488679
0.5044	Remote Similarity	NPC470712
0.5041	Remote Similarity	NPC21359
0.5041	Remote Similarity	NPC460984

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC603079 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4512
0.1-0.2	4581
0.2-0.3	49
0.3-0.4	7
0.4-0.5	0
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
0.5096	Remote Similarity	NPD6797	Phase 2

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