NPASS Compound

Natural Product: NPC321355

Natural Product ID	NPC321355
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PFCVZKFJHRCLCC-OCZSFEIKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5317733
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 82 86 0 0 0 0 0 0 0 0999 V2000 5.6227 2.2000 -1.5707 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8100 1.6854 -0.3881 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9849 2.2741 0.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8808 0.5682 -0.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5953 -0.6406 -1.1738 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6793 -1.6365 -0.0786 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5338 -1.3220 0.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0882 0.0541 0.5628 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6052 0.2208 0.3372 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0205 0.4825 1.7319 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4449 0.5075 1.8026 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9568 0.4955 0.3921 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6070 -0.6766 -0.3980 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8967 -0.9319 -0.2637 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1138 -2.0884 0.7274 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5454 -2.4088 0.9241 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3865 -1.4354 -1.5657 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0296 -0.3491 -1.8183 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0213 0.7013 -2.0057 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0136 1.0148 -0.9217 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3937 0.9638 0.4304 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0889 0.2200 1.5011 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5854 0.4410 1.3708 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9382 -0.2692 0.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3647 0.4125 -1.1192 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4341 1.4611 -1.5063 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4640 -0.5786 -2.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3372 -0.3337 0.0432 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9320 1.7645 1.3469 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2830 2.4150 0.9858 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2675 -1.9845 -0.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -1.3365 2.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2001 -0.3319 3.0004 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8569 -2.4762 2.7041 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4900 3.2961 -1.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6875 1.9893 -1.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2070 1.8195 -2.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7050 3.1174 0.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5020 2.0470 1.7001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1621 0.9873 -1.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1879 -0.9915 -2.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6386 -0.2875 -1.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4866 -2.6521 -0.5293 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6628 -1.6377 0.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3223 0.6891 1.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5504 1.1468 -0.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4654 1.4855 2.0134 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5021 -0.2192 2.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9261 -0.2541 2.4493 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7685 1.4903 2.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4329 1.3672 -0.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6412 -1.8976 1.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6447 -3.0396 0.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8742 -3.1997 0.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5771 -3.0271 1.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8153 -0.7321 -2.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5526 -1.9844 -2.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1703 -2.2458 -1.4622 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3324 -1.2764 -2.3901 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0727 -0.0616 -2.3477 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4840 1.6465 -2.3294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6421 0.4710 -2.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2299 2.1260 -1.1152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8742 -0.8362 1.6321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8407 0.6757 2.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0541 -0.1310 2.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5961 -1.3193 0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2880 1.7717 -2.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4119 1.0334 -1.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2003 2.3519 -0.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7066 -1.3497 -2.1948 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5687 -0.0865 -3.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4513 -1.1100 -2.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6807 -1.1971 0.3914 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2698 2.1397 2.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2860 2.8397 0.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5235 2.4844 2.0394 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9774 3.0569 0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1797 -2.3590 0.9185 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8951 -2.7063 -0.8844 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3698 -2.0050 -0.3461 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3522 -2.5081 3.5866 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 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 14 17 1 0 13 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 24 28 1 0 23 29 1 0 21 30 1 0 13 31 1 0 7 32 1 0 32 33 2 0 32 34 1 0 8 4 1 0 16 7 1 0 14 9 1 0 21 12 1 0 25 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 31 80 1 0 31 81 1 0 34 82 1 0 M END

Standard InCHIKey	PFCVZKFJHRCLCC-OCZSFEIKSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-17(2)18-10-13-30(25(33)34)15-14-28(6)19(23(18)30)8-9-22-27(5)16-20(31)24(32)26(3,4)21(27)11-12-29(22,28)7/h18-24,31-32H,1,8-16H2,2-7H3,(H,33,34)/t18?,19?,20?,21?,22?,23?,24-,27-,28?,29?,30?/m0/s1
SMILES	CC(=C)C1CCC2(C1C3CCC4C(C3(CC2)C)(CCC5C4(CC(C(C5(C)C)O)O)C)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.764 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.357 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.939 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.427	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.874	Fsp³:	0.9
MCE-18:	106.737 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.124	Fluc inhibitor:	0.0 ? 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:	0.032 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.235	Promiscuous compounds:	0.032

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.333	MDCK Permeability:	-4.941
Pgp-inhibitor:	0.001	Pgp-substrate:	0.0
PAMPA:	0.037 ? 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%):	0.001	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.838

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98	MRP1:	1.0
Plasma Protein Binding (PPB):	87.405%	Volume Distribution (VD):	-0.154
Fu:	9.149% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.034
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.001
BSEP inhibitor:	0.81

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.015	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.053	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

5.915

Half-life (T1/2):

1.519

ADMET: Toxicity

hERG Blockers:	0.071	hERG Blockers (10um):	0.354
Human Hepatotoxicity (H-HT):	0.45	Drug-induced Liver Injury (DILI):	0.137
AMES Toxicity:	0.051	Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.636	Skin Sensitization:	0.021
Carcinogencity:	0.168	Eye Corrosion:	0.008
Eye Irritation:	0.486	Respiratory Toxicity:	0.533
Drug-induced Neurotoxicity:	0.215	Ototoxicity:	0.942
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.159
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.016
A549 Cytotoxicity:	0.039	Hek293 Cytotoxicity:	0.133
BCF:	1.763 ? 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:	4.845 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.148 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.323 ? 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
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	barks	n.a.	n.a.	PMID[23066712]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5986.3	Ziziphus jujuba mill. var. inermis (bge.) rehd.	Varieties	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17191	Dryobalanops aromatica	Species	Dipterocarpaceae	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

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

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 NPC321355 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	25173
0.1-0.2	21382
0.2-0.3	2748
0.3-0.4	394
0.4-0.5	90
0.5-0.6	46
0.6-0.7	17
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488506
1.0	High Similarity	NPC220498
0.8475	Intermediate Similarity	NPC488213
0.7966	Intermediate Similarity	NPC291373
0.75	Intermediate Similarity	NPC264317
0.75	Intermediate Similarity	NPC294438
0.7258	Intermediate Similarity	NPC277399
0.6825	Remote Similarity	NPC24772
0.6825	Remote Similarity	NPC488164
0.6825	Remote Similarity	NPC213832
0.6825	Remote Similarity	NPC264005
0.6667	Remote Similarity	NPC80590
0.6615	Remote Similarity	NPC16377
0.6562	Remote Similarity	NPC211162
0.6562	Remote Similarity	NPC183374
0.6557	Remote Similarity	NPC68828
0.6462	Remote Similarity	NPC201655
0.6418	Remote Similarity	NPC486704
0.6364	Remote Similarity	NPC151191
0.629	Remote Similarity	NPC246445
0.625	Remote Similarity	NPC192744
0.6212	Remote Similarity	NPC195395
0.6119	Remote Similarity	NPC2783
0.6029	Remote Similarity	NPC474719
0.597	Remote Similarity	NPC271974
0.597	Remote Similarity	NPC247312
0.5942	Remote Similarity	NPC488165
0.5921	Remote Similarity	NPC486709
0.5909	Remote Similarity	NPC30583
0.5902	Remote Similarity	NPC102708
0.5882	Remote Similarity	NPC4309
0.5797	Remote Similarity	NPC475061
0.5797	Remote Similarity	NPC601275
0.5758	Remote Similarity	NPC119743
0.5714	Remote Similarity	NPC160506
0.5696	Remote Similarity	NPC486699
0.5634	Remote Similarity	NPC478841
0.5634	Remote Similarity	NPC488166
0.5634	Remote Similarity	NPC607677
0.5571	Remote Similarity	NPC269360
0.5556	Remote Similarity	NPC290349
0.5429	Remote Similarity	NPC57954
0.5417	Remote Similarity	NPC169933
0.5417	Remote Similarity	NPC601176
0.5417	Remote Similarity	NPC608379
0.5362	Remote Similarity	NPC476071
0.5357	Remote Similarity	NPC475138
0.5286	Remote Similarity	NPC609710
0.5278	Remote Similarity	NPC71074
0.5278	Remote Similarity	NPC37221
0.5278	Remote Similarity	NPC605937
0.5278	Remote Similarity	NPC611139
0.5233	Remote Similarity	NPC486700
0.5233	Remote Similarity	NPC275312
0.5211	Remote Similarity	NPC18064
0.5205	Remote Similarity	NPC259733
0.5205	Remote Similarity	NPC158371
0.5205	Remote Similarity	NPC207922
0.5205	Remote Similarity	NPC600004
0.52	Remote Similarity	NPC198245
0.5172	Remote Similarity	NPC101863
0.5147	Remote Similarity	NPC472608
0.5139	Remote Similarity	NPC84319
0.5139	Remote Similarity	NPC52021
0.5139	Remote Similarity	NPC599947
0.5128	Remote Similarity	NPC606354
0.5114	Remote Similarity	NPC487491
0.5068	Remote Similarity	NPC472149
0.5067	Remote Similarity	NPC25299
0.5067	Remote Similarity	NPC481322

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC321355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6205
0.1-0.2	2875
0.2-0.3	65
0.3-0.4	2
0.4-0.5	0
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.75	Intermediate Similarity	NPD7520	Phase 1
0.5714	Remote Similarity	NPD8035	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