NPASS Compound

Natural Product: NPC201089

Natural Product ID	NPC201089
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SQCSCAWRXKPACJ-FEYSWINJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5320827
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 71 75 0 0 0 0 0 0 0 0999 V2000 -2.0914 -3.5028 0.8676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8230 -4.6378 1.0804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1079 -4.6170 1.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6423 -3.3999 1.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 -2.2431 1.6726 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6258 -2.2332 1.1665 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7980 -1.0625 0.9893 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1959 0.2211 0.9267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3113 1.2885 0.7596 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7474 2.4636 0.7135 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0328 0.9971 0.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9510 1.9844 0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2895 1.6565 0.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7127 0.3579 0.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7269 -0.6255 0.6060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3919 -0.3319 0.7160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4787 -1.2921 0.8757 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 -0.0108 0.3307 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1189 0.8363 0.1585 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1043 0.7146 1.2935 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1607 -0.3065 1.0760 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7257 -0.3129 -0.3227 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0430 0.7943 -1.1317 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4735 0.6554 -2.5844 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1858 -0.6576 -2.9748 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6906 0.5331 -1.0737 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0984 -0.1946 -0.3600 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7745 -1.5914 1.4681 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6535 1.9457 1.6579 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5271 3.2928 0.4268 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5316 0.5634 1.0115 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3435 0.7811 -0.1191 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0002 2.1706 -0.1006 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4045 2.4491 -1.5243 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8536 1.1606 -2.1443 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2840 0.1152 -1.1749 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5893 0.3339 -0.7315 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3934 -0.1075 -0.1363 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9355 1.4415 -2.9833 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3132 3.4765 -1.6381 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2036 2.1053 0.6393 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9156 -3.2971 2.4002 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7796 -5.8190 1.7753 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0749 -3.5530 0.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3876 -5.6138 0.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3408 -1.2922 1.9502 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9631 2.4933 0.2462 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0882 -1.6429 0.6475 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8385 1.9016 0.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5001 0.3852 2.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0253 -0.0430 1.7537 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3829 -1.2663 -0.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3401 1.7757 -0.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5451 0.9033 -2.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8991 1.3632 -3.2134 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9915 -1.2104 -2.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4656 -0.2554 0.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5695 -1.5738 2.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2263 2.6975 1.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0966 3.7074 -0.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7809 0.6424 -1.0753 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3994 2.9340 0.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4599 2.7551 -2.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0489 0.7027 -2.7898 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -0.8579 -1.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9966 0.9829 -1.3571 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2916 2.3440 -2.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5610 3.7560 -0.7052 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9913 2.1449 1.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6309 -3.8912 1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0621 -6.3847 0.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 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 23 26 1 0 22 27 1 0 21 28 1 0 20 29 1 0 12 30 1 0 8 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 35 39 1 0 34 40 1 0 33 41 1 0 4 42 1 0 3 43 1 0 6 1 1 0 17 7 1 0 26 19 1 0 38 32 1 0 16 11 1 0 1 44 1 0 2 45 1 0 5 46 1 0 13 47 1 0 15 48 1 0 19 49 1 6 20 50 1 1 21 51 1 1 22 52 1 6 23 53 1 1 24 54 1 0 24 55 1 0 25 56 1 0 27 57 1 0 28 58 1 0 29 59 1 0 30 60 1 0 32 61 1 6 33 62 1 1 34 63 1 6 35 64 1 6 36 65 1 6 37 66 1 0 39 67 1 0 40 68 1 0 41 69 1 0 42 70 1 0 43 71 1 0 M END

Standard InCHIKey	SQCSCAWRXKPACJ-FEYSWINJSA-N
Standard InCHI	InChI=1S/C26H28O17/c27-6-13-15(31)17(33)20(36)25(41-13)39-8-4-11(30)14-12(5-8)40-22(7-1-2-9(28)10(29)3-7)23(16(14)32)42-26-21(37)18(34)19(35)24(38)43-26/h1-5,13,15,17-21,24-31,33-38H,6H2/t13-,15-,17+,18-,19+,20-,21-,24-,25-,26+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@@H]1[C@@H]([C@@H]([C@@H]([C@H](O)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	612.13	Volume:	543.812 ? Van der Waals volume.
Dense:	1.126	LogP:	-0.281 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.603 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.617 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	289.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.123	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.804	Fsp³:	0.423
MCE-18:	123.919 ? 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:	0.638	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.907 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.605 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.319	Promiscuous compounds:	0.587

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.566	MDCK Permeability:	-4.933
Pgp-inhibitor:	0.0	Pgp-substrate:	0.734
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):	0.063
20% Bioavailability (F20%):	0.067	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	76.983%	Volume Distribution (VD):	-0.16
Fu:	21.439% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.086
BSEP inhibitor:	0.13

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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.967
HLM stability:	0.028 ? 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):

1.221

Half-life (T1/2):

5.767

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.201
Human Hepatotoxicity (H-HT):	0.377	Drug-induced Liver Injury (DILI):	0.836
AMES Toxicity:	0.844	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	0.996
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.027	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.042	Drug-induced Nephrotoxicity:	0.385
Genotoxicity:	0.287	RPMI-8226 Immunitoxicity:	0.039
A549 Cytotoxicity:	0.118	Hek293 Cytotoxicity:	0.098
BCF:	0.411 ? 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:	3.01 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.738 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.728 ? 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
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	roots	n.a.	n.a.	PMID[18177012]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26595875]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17551	Phytolacca americana	Species	Phytolaccaceae	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 NPC201089 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	27753
0.1-0.2	19154
0.2-0.3	1962
0.3-0.4	531
0.4-0.5	269
0.5-0.6	131
0.6-0.7	44
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8784	High Similarity	NPC136042
0.8228	Intermediate Similarity	NPC605784
0.8182	Intermediate Similarity	NPC84362
0.7821	Intermediate Similarity	NPC297987
0.7468	Intermediate Similarity	NPC289667
0.7349	Intermediate Similarity	NPC116458
0.7349	Intermediate Similarity	NPC246943
0.716	Intermediate Similarity	NPC277205
0.716	Intermediate Similarity	NPC37919
0.7073	Intermediate Similarity	NPC271692
0.6951	Remote Similarity	NPC145038
0.6951	Remote Similarity	NPC56077
0.6951	Remote Similarity	NPC281131
0.6951	Remote Similarity	NPC253662
0.6951	Remote Similarity	NPC179950
0.6951	Remote Similarity	NPC88789
0.6951	Remote Similarity	NPC189142
0.6951	Remote Similarity	NPC77660
0.6951	Remote Similarity	NPC491374
0.6905	Remote Similarity	NPC488071
0.6897	Remote Similarity	NPC251417
0.6737	Remote Similarity	NPC14187
0.6627	Remote Similarity	NPC249281
0.6588	Remote Similarity	NPC42773
0.6588	Remote Similarity	NPC45522
0.6522	Remote Similarity	NPC64425
0.6465	Remote Similarity	NPC480441
0.6395	Remote Similarity	NPC599850
0.6353	Remote Similarity	NPC323593
0.6353	Remote Similarity	NPC203500
0.6279	Remote Similarity	NPC46420
0.6264	Remote Similarity	NPC480466
0.6235	Remote Similarity	NPC39360
0.6235	Remote Similarity	NPC77672
0.6235	Remote Similarity	NPC133671
0.6235	Remote Similarity	NPC135391
0.6235	Remote Similarity	NPC29763
0.6235	Remote Similarity	NPC78263
0.6235	Remote Similarity	NPC210003
0.6235	Remote Similarity	NPC250069
0.6211	Remote Similarity	NPC35119
0.619	Remote Similarity	NPC67037
0.619	Remote Similarity	NPC255615
0.6163	Remote Similarity	NPC158674
0.6136	Remote Similarity	NPC611303
0.6111	Remote Similarity	NPC276377
0.6092	Remote Similarity	NPC24043
0.6047	Remote Similarity	NPC19388
0.6047	Remote Similarity	NPC240431
0.6047	Remote Similarity	NPC55786
0.6047	Remote Similarity	NPC238376
0.6042	Remote Similarity	NPC32641
0.6042	Remote Similarity	NPC256188
0.6022	Remote Similarity	NPC471748
0.5979	Remote Similarity	NPC486577
0.5977	Remote Similarity	NPC64305
0.5957	Remote Similarity	NPC150164
0.5957	Remote Similarity	NPC156869
0.5955	Remote Similarity	NPC285197
0.5914	Remote Similarity	NPC29958
0.5909	Remote Similarity	NPC27640
0.5889	Remote Similarity	NPC601144
0.5865	Remote Similarity	NPC470716
0.5862	Remote Similarity	NPC127546
0.5862	Remote Similarity	NPC261866
0.5862	Remote Similarity	NPC57625
0.5862	Remote Similarity	NPC19709
0.5862	Remote Similarity	NPC173637
0.5862	Remote Similarity	NPC317489
0.5862	Remote Similarity	NPC223424
0.5862	Remote Similarity	NPC600591
0.5843	Remote Similarity	NPC472459
0.5825	Remote Similarity	NPC25523
0.5825	Remote Similarity	NPC164704
0.5824	Remote Similarity	NPC311830
0.5795	Remote Similarity	NPC95090
0.5795	Remote Similarity	NPC27408
0.5778	Remote Similarity	NPC60735
0.5778	Remote Similarity	NPC307938
0.5778	Remote Similarity	NPC26230
0.5761	Remote Similarity	NPC203050
0.5761	Remote Similarity	NPC488072
0.5761	Remote Similarity	NPC225434
0.5761	Remote Similarity	NPC601586
0.573	Remote Similarity	NPC488080
0.573	Remote Similarity	NPC169977
0.5729	Remote Similarity	NPC186816
0.5714	Remote Similarity	NPC22832
0.5714	Remote Similarity	NPC120099
0.5714	Remote Similarity	NPC486578
0.5702	Remote Similarity	NPC223860
0.5673	Remote Similarity	NPC470715
0.567	Remote Similarity	NPC488073
0.5667	Remote Similarity	NPC59534
0.5638	Remote Similarity	NPC8856
0.5618	Remote Similarity	NPC8573
0.5618	Remote Similarity	NPC168822
0.5604	Remote Similarity	NPC175107
0.5596	Remote Similarity	NPC470720
0.5595	Remote Similarity	NPC191154
0.5556	Remote Similarity	NPC245014
0.5556	Remote Similarity	NPC58716
0.5556	Remote Similarity	NPC305811
0.5556	Remote Similarity	NPC72016
0.5556	Remote Similarity	NPC45638
0.5556	Remote Similarity	NPC606657
0.5543	Remote Similarity	NPC101026
0.5543	Remote Similarity	NPC243930
0.5543	Remote Similarity	NPC21666
0.5543	Remote Similarity	NPC488077
0.5532	Remote Similarity	NPC254855
0.5532	Remote Similarity	NPC94610
0.5521	Remote Similarity	NPC275454
0.5517	Remote Similarity	NPC288084
0.551	Remote Similarity	NPC240306
0.5505	Remote Similarity	NPC470719
0.5505	Remote Similarity	NPC470717
0.5495	Remote Similarity	NPC325555
0.5495	Remote Similarity	NPC226304
0.5495	Remote Similarity	NPC117260
0.5495	Remote Similarity	NPC201292
0.5474	Remote Similarity	NPC480463
0.5472	Remote Similarity	NPC277532
0.5463	Remote Similarity	NPC295625
0.5429	Remote Similarity	NPC292019
0.5429	Remote Similarity	NPC202908
0.5426	Remote Similarity	NPC190003
0.5417	Remote Similarity	NPC139320
0.5385	Remote Similarity	NPC188871
0.5376	Remote Similarity	NPC609478
0.5368	Remote Similarity	NPC116864
0.5368	Remote Similarity	NPC244776
0.5368	Remote Similarity	NPC265115
0.5361	Remote Similarity	NPC67105
0.5341	Remote Similarity	NPC34531
0.5333	Remote Similarity	NPC108831
0.5333	Remote Similarity	NPC182634
0.5319	Remote Similarity	NPC607707
0.5306	Remote Similarity	NPC605592
0.53	Remote Similarity	NPC483415
0.5275	Remote Similarity	NPC282987
0.5275	Remote Similarity	NPC197896
0.5275	Remote Similarity	NPC313163
0.5275	Remote Similarity	NPC609879
0.5253	Remote Similarity	NPC115674
0.5248	Remote Similarity	NPC483416
0.5238	Remote Similarity	NPC121703
0.5222	Remote Similarity	NPC111929
0.5222	Remote Similarity	NPC320283
0.5222	Remote Similarity	NPC473043
0.5222	Remote Similarity	NPC331652
0.5222	Remote Similarity	NPC41121
0.5217	Remote Similarity	NPC603655
0.5204	Remote Similarity	NPC67326
0.5179	Remote Similarity	NPC488078
0.5172	Remote Similarity	NPC134819
0.5169	Remote Similarity	NPC276222
0.5169	Remote Similarity	NPC274618
0.5169	Remote Similarity	NPC118284
0.5169	Remote Similarity	NPC608147
0.5158	Remote Similarity	NPC206123
0.5152	Remote Similarity	NPC203259
0.5152	Remote Similarity	NPC33054
0.5152	Remote Similarity	NPC210073
0.5152	Remote Similarity	NPC155877
0.5152	Remote Similarity	NPC176740
0.5152	Remote Similarity	NPC471725
0.5152	Remote Similarity	NPC134532
0.5152	Remote Similarity	NPC602582
0.5149	Remote Similarity	NPC470443
0.5149	Remote Similarity	NPC483414
0.5149	Remote Similarity	NPC65711
0.5109	Remote Similarity	NPC234739
0.5106	Remote Similarity	NPC168584
0.5106	Remote Similarity	NPC80140
0.5102	Remote Similarity	NPC476773
0.5098	Remote Similarity	NPC229409
0.5055	Remote Similarity	NPC135599
0.5055	Remote Similarity	NPC73855
0.5055	Remote Similarity	NPC113968
0.5055	Remote Similarity	NPC328940
0.5055	Remote Similarity	NPC277174
0.5055	Remote Similarity	NPC606877
0.5054	Remote Similarity	NPC610763
0.5053	Remote Similarity	NPC148710

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC201089 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6447
0.1-0.2	2642
0.2-0.3	49
0.3-0.4	6
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
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
0.6082	Remote Similarity	NPD7251	Phase 2
0.5152	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