NPASS Compound

Natural Product: NPC603266

Natural Product ID	NPC603266
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RAPHJSKUDKPBNF-IPVOLVKLSA-M
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502431
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 85 88 0 0 0 0 0 0 0 0999 V2000 7.3610 -1.7243 -2.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2655 -0.4938 -2.0374 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4836 0.2659 -1.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0909 -0.0643 -1.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9141 1.1274 -0.8189 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8782 1.8247 -0.4325 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4924 1.4920 -0.4442 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0087 0.4079 0.4634 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9869 0.3746 1.6759 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6836 0.5077 1.0516 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3822 1.6721 1.9560 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9095 1.3809 2.2885 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4309 0.3524 1.2860 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4627 -1.0533 1.7872 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9088 0.6370 0.7097 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9342 0.5386 1.8114 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3400 0.6901 1.2614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5655 -0.4301 0.3035 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9572 -0.3780 -0.3179 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0539 0.7111 -1.3618 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0171 -0.0532 0.7294 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2323 -0.0369 0.0420 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5351 0.3021 1.0393 S 0 0 0 0 0 0 0 0 0 0 0 0 -8.1533 1.2593 2.1335 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6647 0.9178 0.2610 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0899 -1.1334 1.7613 O 0 0 0 0 0 1 0 0 0 0 0 0 -5.2550 -1.7420 -0.8719 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9915 -1.6590 -2.0747 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0284 -2.5925 -1.0563 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8387 -1.8278 -1.5692 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5600 -0.5742 -0.7668 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1272 0.5860 -1.5391 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1951 -0.1397 -0.5139 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0850 -0.9728 -1.0473 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3021 -0.4845 -0.8337 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4755 0.5755 0.1700 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1850 1.9462 -0.3754 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 Na 0 0 0 0 0 15 0 0 0 0 0 0 8.4082 -2.0918 -2.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8143 -2.5135 -2.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8798 -1.6483 -3.8468 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5539 0.2348 -0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4751 1.3092 -2.0491 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3646 -0.2671 -2.0693 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2165 -0.6526 -1.9493 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9834 1.3966 -1.4516 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5185 2.4973 -0.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1405 -0.5643 -0.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1611 1.3992 2.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9265 -0.1186 1.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5285 -0.1869 2.5208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5634 -0.3942 1.7209 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9862 1.6260 2.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4278 2.6548 1.5106 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8969 0.8764 3.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2978 2.2783 2.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6631 -1.0285 2.8765 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5288 -1.5925 1.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1611 -1.7339 1.2577 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9727 1.7283 0.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7856 1.4449 2.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8520 -0.3125 2.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4589 1.6916 0.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0209 0.5122 2.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5555 -1.3849 0.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1175 0.7776 -1.6488 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7554 1.6591 -0.8884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4889 0.4774 -2.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9793 -0.8569 1.4719 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8724 0.9638 1.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9084 -2.2983 -0.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9291 -1.9475 -1.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7190 -3.1405 -0.1303 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2581 -3.3885 -1.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9739 -2.5218 -1.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0176 -1.5681 -2.6562 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3944 1.6253 -1.3198 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7456 0.4728 -2.5951 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1718 -2.0478 -0.7073 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2417 -1.0575 -2.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9757 -1.3510 -0.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7600 -0.1146 -1.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4598 1.8181 -1.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7740 2.6587 0.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0304 2.4704 -0.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 2 0 23 26 1 0 19 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 31 30 1 6 31 32 1 0 33 32 1 6 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 6 36 10 1 0 36 13 1 0 33 15 1 0 31 18 1 0 33 31 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 7 46 1 0 7 47 1 0 8 48 1 6 9 49 1 0 9 50 1 0 9 51 1 0 10 52 1 1 11 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 14 57 1 0 14 58 1 0 14 59 1 0 15 60 1 6 16 61 1 0 16 62 1 0 17 63 1 0 17 64 1 0 18 65 1 1 20 66 1 0 20 67 1 0 20 68 1 0 21 69 1 0 21 70 1 0 27 71 1 1 28 72 1 0 29 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 32 77 1 0 32 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M CHG 2 26 -1 38 1 M END

Standard InCHIKey	RAPHJSKUDKPBNF-IPVOLVKLSA-M
Standard InCHI	InChI=1S/C30H48O6S.Na/c1-19(2)15-21(31)16-20(3)22-9-11-28(6)24-8-7-23-26(4,18-36-37(33,34)35)25(32)10-12-29(23)17-30(24,29)14-13-27(22,28)5;/h15,20,22-25,32H,7-14,16-18H2,1-6H3,(H,33,34,35);/q;+1/p-1/t20-,22-,23+,24+,25+,26+,27-,28+,29-,30+;/m1./s1
SMILES	CC(C)=CC(=O)C[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@](C)(COS(=O)(=O)[O-])[C@@H](O)CC[C@@]45C[C@@]35CC[C@]12C.[Na+]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	535.31	Volume:	549.313 ? Van der Waals volume.
Dense:	0.975	LogP:	2.422 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.505 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.697 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	26.0
TPSA:	103.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.251	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.022	Fsp³:	0.9
MCE-18:	145.263 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.734	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.21	Promiscuous compounds:	0.179

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.302	MDCK Permeability:	-5.067
Pgp-inhibitor:	0.016	Pgp-substrate:	0.0
PAMPA:	0.968 ? 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%):	0.003	30% Bioavailability (F30%):	0.063
50% Bioavailability (F50%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.242
Plasma Protein Binding (PPB):	93.294%	Volume Distribution (VD):	-0.032
Fu:	5.562% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.018
BSEP inhibitor:	0.962

ADMET: Metabolism

CYP1A2-inhibitor:	0.191	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.997	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.404
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.758 ? 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):

7.189

Half-life (T1/2):

1.018

ADMET: Toxicity

hERG Blockers:	0.163	hERG Blockers (10um):	0.297
Human Hepatotoxicity (H-HT):	0.887	Drug-induced Liver Injury (DILI):	0.487
AMES Toxicity:	0.546	Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.683	Skin Sensitization:	0.947
Carcinogencity:	0.835	Eye Corrosion:	0.001
Eye Irritation:	0.084	Respiratory Toxicity:	0.702
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.603
Hematotoxicity:	0.608	Drug-induced Nephrotoxicity:	0.14
Genotoxicity:	0.958	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.09	Hek293 Cytotoxicity:	0.19
BCF:	0.737 ? 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:	3.813 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.619 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.655 ? 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
NPO52	Tydemania expeditionis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8158167]
NPO52	Tydemania expeditionis	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO52	Tydemania expeditionis	Species	Udoteaceae	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	12
Activity	1

Activity Type	# Activity
Cell line	10
Non-molecular	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
NPT2155	Cell line	SHP77	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT1900	Cell line	DU-4475	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT937	Cell line	NCI-H446	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT457	Cell line	BT-549	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT784	Cell line	MDA-MB-468	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	6000.0	nM	PMID[18763828]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	6000.0	nM	PMID[18763828]
NPT3927	Organism	Rotifers	Rotifera	Activity	=	9.0	%	PMID[18763828]

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 NPC603266 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	20301
0.1-0.2	26299
0.2-0.3	2977
0.3-0.4	179
0.4-0.5	70
0.5-0.6	26
0.6-0.7	5
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
0.7213	Intermediate Similarity	NPC606508
0.6912	Remote Similarity	NPC478129
0.6429	Remote Similarity	NPC603267
0.6027	Remote Similarity	NPC486370
0.6027	Remote Similarity	NPC486371
0.6027	Remote Similarity	NPC486372
0.589	Remote Similarity	NPC486363
0.5857	Remote Similarity	NPC486365
0.5616	Remote Similarity	NPC601543
0.557	Remote Similarity	NPC239293
0.5526	Remote Similarity	NPC486361
0.5467	Remote Similarity	NPC312900
0.5342	Remote Similarity	NPC488976
0.5342	Remote Similarity	NPC478128
0.5294	Remote Similarity	NPC12722
0.5263	Remote Similarity	NPC124207
0.5224	Remote Similarity	NPC22133
0.5217	Remote Similarity	NPC89747
0.5195	Remote Similarity	NPC609052
0.519	Remote Similarity	NPC486367
0.5152	Remote Similarity	NPC85346
0.5152	Remote Similarity	NPC65897
0.5152	Remote Similarity	NPC80237
0.5147	Remote Similarity	NPC76518
0.5147	Remote Similarity	NPC483442
0.5147	Remote Similarity	NPC69408
0.5135	Remote Similarity	NPC486417
0.5135	Remote Similarity	NPC37153
0.5135	Remote Similarity	NPC478130
0.5077	Remote Similarity	NPC607543
0.5075	Remote Similarity	NPC273366
0.5065	Remote Similarity	NPC81256

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC603266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6663
0.1-0.2	2376
0.2-0.3	111
0.3-0.4	0
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