NPASS Compound

Natural Product: NPC101579

Natural Product ID	NPC101579
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UIDGLYUNOUKLBM-ZLEZCFKXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12313122
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 76 80 0 0 0 0 0 0 0 0999 V2000 7.1707 -2.7643 0.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4875 -1.4326 0.1859 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4495 -0.3646 -0.2885 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6031 0.6451 -1.0652 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1992 0.7103 -0.5021 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5150 -0.6236 -0.5175 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0042 -1.0317 0.7001 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6926 -1.4639 0.6771 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7829 -0.3663 0.2763 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8138 0.6774 1.4073 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3726 1.9640 0.7465 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1923 1.6105 -0.1435 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4448 0.3333 0.1794 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4494 -0.7566 0.2089 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3568 -0.0539 -0.8814 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5375 -0.6720 -0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4938 -2.0452 -0.4215 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 -2.7050 -0.5327 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6525 -2.7298 -0.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6857 -4.0932 0.0669 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8668 -4.7444 0.3722 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0518 -4.0218 0.4982 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0427 -2.6618 0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8451 -2.0237 0.0117 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7979 -0.7533 -0.1638 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7118 -0.0293 -0.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9724 1.3899 -0.6040 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0721 2.2255 -1.1964 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2873 3.6106 -1.3021 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4744 4.1336 -0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3940 3.3035 -0.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1239 1.9669 -0.1053 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5567 3.8424 0.3347 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5270 3.0031 0.9624 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7093 5.5007 -0.8688 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2211 -4.6766 0.8018 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5288 -4.8350 -0.0514 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5594 1.6728 -1.4986 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0528 2.9400 1.6868 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0290 0.7538 2.0323 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5301 -1.5806 -0.8175 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5333 1.6919 -1.2129 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5972 0.3698 -2.4154 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0811 0.2378 0.7904 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0451 -2.6750 1.0532 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3967 -3.2579 -0.5707 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4346 -3.4217 0.9168 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0396 -1.0875 1.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2048 -0.7462 -0.9969 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0631 1.6395 -0.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3004 1.0440 0.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7622 -0.7152 -1.3175 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5884 -2.3615 0.0167 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4457 -1.8202 1.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0419 0.0653 -0.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0222 0.4082 2.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1951 2.2889 0.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5331 2.4488 0.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0382 0.3519 1.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9332 -5.8090 0.5240 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9239 -2.0373 0.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1535 1.9025 -1.6490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5771 4.2752 -1.7693 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8417 1.3178 0.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7198 2.1200 0.3077 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1119 2.5892 1.9268 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4819 3.5092 1.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4744 5.8542 -1.4377 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1077 -4.1919 0.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4933 -5.7821 -0.3934 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1031 0.9367 -1.9871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3115 3.4569 1.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0485 0.1064 2.7898 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1311 1.3022 -2.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4743 1.2291 -2.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4528 0.9058 1.1671 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 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 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 30 35 1 0 22 36 1 0 20 37 1 0 12 38 1 0 11 39 1 0 10 40 1 0 6 41 1 0 5 42 1 0 4 43 1 0 3 44 1 0 41 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 24 19 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 1 3 49 1 6 4 50 1 6 5 51 1 1 6 52 1 6 8 53 1 0 8 54 1 0 9 55 1 6 10 56 1 1 11 57 1 6 12 58 1 6 13 59 1 1 21 60 1 0 23 61 1 0 28 62 1 0 29 63 1 0 32 64 1 0 34 65 1 0 34 66 1 0 34 67 1 0 35 68 1 0 36 69 1 0 37 70 1 0 38 71 1 0 39 72 1 0 40 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 M END

Standard InCHIKey	UIDGLYUNOUKLBM-ZLEZCFKXSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,24+,27+,28+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)OC)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.572 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.048 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.578 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.749	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.61	Fluc inhibitor:	0.281 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.831 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.626 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.072	Promiscuous compounds:	0.488

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.387	MDCK Permeability:	-5.28
Pgp-inhibitor:	0.0	Pgp-substrate:	0.964
PAMPA:	0.998 ? 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):	0.017
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.816
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.025
Plasma Protein Binding (PPB):	84.727%	Volume Distribution (VD):	-0.096
Fu:	13.976% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.933
BSEP inhibitor:	0.637

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.095
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.889 ? 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):

1.373

Half-life (T1/2):

4.583

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.3
Human Hepatotoxicity (H-HT):	0.217	Drug-induced Liver Injury (DILI):	0.491
AMES Toxicity:	0.692	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.103	Skin Sensitization:	0.861
Carcinogencity:	0.019	Eye Corrosion:	0.0
Eye Irritation:	0.316	Respiratory Toxicity:	0.015
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.938
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.195
Genotoxicity:	0.227	RPMI-8226 Immunitoxicity:	0.166
A549 Cytotoxicity:	0.256	Hek293 Cytotoxicity:	0.437
BCF:	0.465 ? 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:	3.127 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.568 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.689 ? 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
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9233	Plexaura homomalla	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9233	Plexaura homomalla	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5859	Bacterium sa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO199	Dryopteris aitoniana	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4351	Hedyosmum arborescens	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9869	Crassostrea gigas	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9598	Psorospermum adamauense	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8941	Salacia longipes	Species	Sertulariidae	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 NPC101579 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	18774
0.1-0.2	27186
0.2-0.3	2853
0.3-0.4	550
0.4-0.5	239
0.5-0.6	88
0.6-0.7	77
0.7-0.8	0
0.8-0.85	17
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476472
1.0	High Similarity	NPC294815
1.0	High Similarity	NPC16194
0.8471	Intermediate Similarity	NPC173582
0.8471	Intermediate Similarity	NPC265885
0.8471	Intermediate Similarity	NPC181465
0.8471	Intermediate Similarity	NPC215710
0.8471	Intermediate Similarity	NPC473438
0.8471	Intermediate Similarity	NPC253788
0.8409	Intermediate Similarity	NPC473327
0.8391	Intermediate Similarity	NPC153755
0.8372	Intermediate Similarity	NPC203259
0.8372	Intermediate Similarity	NPC33054
0.8372	Intermediate Similarity	NPC176740
0.8372	Intermediate Similarity	NPC471725
0.8372	Intermediate Similarity	NPC134532
0.8372	Intermediate Similarity	NPC602582
0.8313	Intermediate Similarity	NPC223747
0.8261	Intermediate Similarity	NPC89052
0.8085	Intermediate Similarity	NPC173837
0.7841	Intermediate Similarity	NPC39834
0.7473	Intermediate Similarity	NPC473571
0.7473	Intermediate Similarity	NPC110941
0.7391	Intermediate Similarity	NPC126784
0.7391	Intermediate Similarity	NPC241423
0.7386	Intermediate Similarity	NPC203050
0.7386	Intermediate Similarity	NPC225434
0.7363	Intermediate Similarity	NPC156869
0.7333	Intermediate Similarity	NPC471079
0.7308	Intermediate Similarity	NPC192539
0.7273	Intermediate Similarity	NPC217520
0.7253	Intermediate Similarity	NPC67326
0.7143	Intermediate Similarity	NPC609888
0.7129	Intermediate Similarity	NPC139571
0.7083	Intermediate Similarity	NPC220173
0.6989	Remote Similarity	NPC65563
0.6989	Remote Similarity	NPC470949
0.6947	Remote Similarity	NPC12013
0.6947	Remote Similarity	NPC470443
0.6947	Remote Similarity	NPC11432
0.6947	Remote Similarity	NPC477613
0.6923	Remote Similarity	NPC116864
0.6923	Remote Similarity	NPC244776
0.6915	Remote Similarity	NPC186816
0.69	Remote Similarity	NPC189564
0.6875	Remote Similarity	NPC122467
0.686	Remote Similarity	NPC111929
0.686	Remote Similarity	NPC320283
0.686	Remote Similarity	NPC41121
0.6854	Remote Similarity	NPC219904
0.6832	Remote Similarity	NPC292019
0.6832	Remote Similarity	NPC202908
0.68	Remote Similarity	NPC203145
0.6782	Remote Similarity	NPC127546
0.6782	Remote Similarity	NPC57625
0.6782	Remote Similarity	NPC173637
0.6782	Remote Similarity	NPC317489
0.6782	Remote Similarity	NPC223424
0.6782	Remote Similarity	NPC600591
0.6735	Remote Similarity	NPC89127
0.6705	Remote Similarity	NPC265530
0.6667	Remote Similarity	NPC221342
0.6667	Remote Similarity	NPC476470
0.66	Remote Similarity	NPC602448
0.6596	Remote Similarity	NPC187379
0.6495	Remote Similarity	NPC488073
0.6495	Remote Similarity	NPC488074
0.6346	Remote Similarity	NPC219043
0.6346	Remote Similarity	NPC477895
0.6292	Remote Similarity	NPC135599
0.6292	Remote Similarity	NPC73855
0.6292	Remote Similarity	NPC113968
0.6292	Remote Similarity	NPC328940
0.6292	Remote Similarity	NPC277174
0.6292	Remote Similarity	NPC606877
0.6289	Remote Similarity	NPC605592
0.6286	Remote Similarity	NPC303694
0.6273	Remote Similarity	NPC241781
0.6238	Remote Similarity	NPC85751
0.6238	Remote Similarity	NPC473073
0.6238	Remote Similarity	NPC471669
0.6238	Remote Similarity	NPC19240
0.6228	Remote Similarity	NPC473554
0.6224	Remote Similarity	NPC129264
0.6196	Remote Similarity	NPC325555
0.6196	Remote Similarity	NPC226304
0.6176	Remote Similarity	NPC470449
0.6162	Remote Similarity	NPC470125
0.6129	Remote Similarity	NPC175107
0.6117	Remote Similarity	NPC470446
0.6117	Remote Similarity	NPC223426
0.6105	Remote Similarity	NPC476215
0.6091	Remote Similarity	NPC156785
0.6091	Remote Similarity	NPC162394
0.6091	Remote Similarity	NPC474522
0.6078	Remote Similarity	NPC470447
0.6064	Remote Similarity	NPC101026
0.6064	Remote Similarity	NPC120099
0.6064	Remote Similarity	NPC488077
0.6058	Remote Similarity	NPC214621
0.6058	Remote Similarity	NPC34267
0.6058	Remote Similarity	NPC81042
0.6044	Remote Similarity	NPC77672
0.6044	Remote Similarity	NPC133671
0.6044	Remote Similarity	NPC135391
0.6044	Remote Similarity	NPC78263
0.6044	Remote Similarity	NPC250069
0.6042	Remote Similarity	NPC95866
0.604	Remote Similarity	NPC37668
0.604	Remote Similarity	NPC270448
0.6019	Remote Similarity	NPC470445
0.6	Remote Similarity	NPC480445
0.598	Remote Similarity	NPC142142
0.5978	Remote Similarity	NPC145038
0.5978	Remote Similarity	NPC56077
0.5978	Remote Similarity	NPC281131
0.5978	Remote Similarity	NPC253662
0.5978	Remote Similarity	NPC179950
0.5978	Remote Similarity	NPC88789
0.5978	Remote Similarity	NPC491374
0.5914	Remote Similarity	NPC305811
0.5914	Remote Similarity	NPC46420
0.5904	Remote Similarity	NPC279989
0.5893	Remote Similarity	NPC480444
0.5865	Remote Similarity	NPC292929
0.5859	Remote Similarity	NPC163242
0.5859	Remote Similarity	NPC272068
0.5859	Remote Similarity	NPC67105
0.5851	Remote Similarity	NPC472459
0.5833	Remote Similarity	NPC206123
0.582	Remote Similarity	NPC487501
0.58	Remote Similarity	NPC155877
0.5789	Remote Similarity	NPC60735
0.5789	Remote Similarity	NPC26230
0.5778	Remote Similarity	NPC54802
0.5778	Remote Similarity	NPC197304
0.5758	Remote Similarity	NPC139320
0.5755	Remote Similarity	NPC470455
0.5745	Remote Similarity	NPC271692
0.5738	Remote Similarity	NPC487500
0.5729	Remote Similarity	NPC609478
0.5728	Remote Similarity	NPC209296
0.5714	Remote Similarity	NPC288084
0.5714	Remote Similarity	NPC276222
0.5714	Remote Similarity	NPC274618
0.5714	Remote Similarity	NPC118284
0.5714	Remote Similarity	NPC608147
0.5701	Remote Similarity	NPC121703
0.57	Remote Similarity	NPC44931
0.57	Remote Similarity	NPC471748
0.5688	Remote Similarity	NPC25523
0.5652	Remote Similarity	NPC67037
0.5652	Remote Similarity	NPC255615
0.5644	Remote Similarity	NPC210073
0.5638	Remote Similarity	NPC64305
0.5625	Remote Similarity	NPC159579
0.5612	Remote Similarity	NPC488072
0.56	Remote Similarity	NPC29958
0.5596	Remote Similarity	NPC48984
0.5593	Remote Similarity	NPC487499
0.5567	Remote Similarity	NPC197285
0.5556	Remote Similarity	NPC4390
0.5546	Remote Similarity	NPC275977
0.5545	Remote Similarity	NPC480441
0.5537	Remote Similarity	NPC487502
0.5534	Remote Similarity	NPC296018
0.5534	Remote Similarity	NPC154741
0.5532	Remote Similarity	NPC19388
0.5532	Remote Similarity	NPC240431
0.5532	Remote Similarity	NPC249281
0.5532	Remote Similarity	NPC55786
0.551	Remote Similarity	NPC209023
0.5505	Remote Similarity	NPC470451
0.5505	Remote Similarity	NPC470416
0.549	Remote Similarity	NPC22062
0.549	Remote Similarity	NPC473634
0.549	Remote Similarity	NPC138811
0.5487	Remote Similarity	NPC488734
0.5487	Remote Similarity	NPC488735
0.5487	Remote Similarity	NPC488739
0.5487	Remote Similarity	NPC488732
0.5487	Remote Similarity	NPC488738
0.5464	Remote Similarity	NPC611303
0.5455	Remote Similarity	NPC72554
0.5455	Remote Similarity	NPC276377
0.5424	Remote Similarity	NPC25946
0.5421	Remote Similarity	NPC287889
0.5421	Remote Similarity	NPC36138
0.5417	Remote Similarity	NPC52550
0.5417	Remote Similarity	NPC27640
0.5408	Remote Similarity	NPC601710
0.5392	Remote Similarity	NPC470405
0.5392	Remote Similarity	NPC227508
0.5391	Remote Similarity	NPC488740
0.5391	Remote Similarity	NPC488736
0.5391	Remote Similarity	NPC488733
0.5378	Remote Similarity	NPC21359
0.5378	Remote Similarity	NPC460984
0.537	Remote Similarity	NPC470450
0.5361	Remote Similarity	NPC216496

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC101579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5416
0.1-0.2	3680
0.2-0.3	43
0.3-0.4	4
0.4-0.5	2
0.5-0.6	2
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD6797	Phase 2
0.64	Remote Similarity	NPD7251	Phase 2
0.6154	Remote Similarity	NPD7808	Phase 3
0.5728	Remote Similarity	NPD7054	Phase 4
0.5135	Remote Similarity	NPD7472	Pre-clinical

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