NPASS Compound

Natural Product: NPC170597

Natural Product ID	NPC170597
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UKRDIRUVTNZWOU-AHTWRUMCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9830005
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 78 81 0 0 0 0 0 0 0 0999 V2000 2.4652 3.6692 2.8969 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1465 3.7185 2.1580 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9927 5.1509 1.6397 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4965 5.0464 0.2155 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6405 4.0136 0.2447 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0138 2.6735 0.4405 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2307 2.8069 1.1019 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7587 1.7623 1.1137 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0729 0.6262 0.4170 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5839 0.5368 0.3349 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8511 -0.6048 -0.6439 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2260 -0.7443 -0.7283 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6923 -0.3199 -1.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2597 -1.0682 -3.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6523 -2.4868 -3.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9148 -2.7987 -3.6836 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2685 -4.1241 -3.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3914 -5.1121 -3.3502 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1393 -4.8106 -2.8728 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7824 -3.4562 -2.8065 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2715 -1.7586 -0.3183 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4002 -1.8491 0.7016 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1125 -2.4747 1.8950 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5848 -3.7646 1.5608 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6573 -0.6556 1.1308 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7657 -0.8207 1.0295 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6257 -0.7393 2.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1670 -0.5086 3.2219 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0782 -0.9146 1.9460 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6071 -1.1605 0.7657 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0321 -1.3455 0.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4633 -1.5982 -0.7431 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7850 -1.7799 -1.0090 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7527 -1.7233 -0.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3364 -1.4714 1.2615 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9797 -1.2845 1.5374 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2931 -1.4117 2.2540 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0814 -1.9168 -0.3636 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1241 1.6800 -0.2191 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2591 4.1262 -1.0114 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5050 4.5762 -0.5999 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0739 5.8703 2.3849 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5301 2.7986 3.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5611 4.6414 3.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2728 3.6724 2.1242 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3282 3.4686 2.8614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9559 5.6874 1.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0990 6.0227 -0.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2981 4.3168 1.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2258 2.2683 -0.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6786 0.5664 -0.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9571 0.3138 1.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4883 -0.2153 -1.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3966 0.7662 -2.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8292 -0.2217 -1.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1672 -0.9998 -3.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7069 -0.5860 -4.0763 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5894 -2.0169 -3.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2670 -4.3644 -4.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7469 -6.1468 -3.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4607 -5.5818 -2.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7858 -3.2806 -2.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6329 -2.6309 0.4083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9796 -1.9092 2.2362 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4319 -2.6175 2.7569 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8291 -4.4087 1.5042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8400 -0.4619 2.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7242 -0.8441 2.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9148 -1.2250 -0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7484 -1.6568 -1.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0969 -1.9760 -2.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6917 -1.0909 2.5503 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8307 -2.2206 2.5667 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8256 -1.6757 0.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0273 1.8065 0.1978 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6817 5.0223 -1.0165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3990 4.9661 -0.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6585 6.2596 1.8227 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 6 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 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 11 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 34 38 1 0 10 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 7 2 1 0 25 9 1 0 36 31 1 0 20 15 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 6 4 48 1 6 5 49 1 1 6 50 1 6 9 51 1 6 10 52 1 1 11 53 1 6 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 16 58 1 0 17 59 1 0 18 60 1 0 19 61 1 0 20 62 1 0 22 63 1 6 23 64 1 0 23 65 1 0 24 66 1 0 25 67 1 1 29 68 1 0 30 69 1 0 32 70 1 0 33 71 1 0 36 72 1 0 37 73 1 0 38 74 1 0 39 75 1 0 40 76 1 0 41 77 1 0 42 78 1 0 M END

Standard InCHIKey	UKRDIRUVTNZWOU-AHTWRUMCSA-N
Standard InCHI	InChI=1S/C29H36O13/c1-15-22(34)23(35)24(36)29(39-15)42-27-25(37)28(38-12-11-16-5-3-2-4-6-16)40-20(14-30)26(27)41-21(33)10-8-17-7-9-18(31)19(32)13-17/h2-10,13,15,20,22-32,34-37H,11-12,14H2,1H3/b10-8+/t15-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](OCCc2ccccc2)O[C@H](CO)[C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.22	Volume:	569.095 ? Van der Waals volume.
Dense:	1.041	LogP:	1.364 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.828 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.614 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	26.0
TPSA:	204.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	7.0	Rings:	4.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.536	Fsp³:	0.483
MCE-18:	93.558 ? 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:	1
Colloidal aggregators:	0.745	Fluc inhibitor:	0.661 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.181 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.439 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.206	Promiscuous compounds:	0.329

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.38	MDCK Permeability:	-5.267
Pgp-inhibitor:	0.0	Pgp-substrate:	0.144
PAMPA:	0.992 ? 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):	0.697
20% Bioavailability (F20%):	0.961	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049	MRP1:	0.021
Plasma Protein Binding (PPB):	72.963%	Volume Distribution (VD):	-0.524
Fu:	23.801% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.01
BSEP inhibitor:	0.004

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:	0.002
CYP3A4-inhibitor:	0.025	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.933 ? 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):

2.501

Half-life (T1/2):

3.651

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.38
Human Hepatotoxicity (H-HT):	0.518	Drug-induced Liver Injury (DILI):	0.845
AMES Toxicity:	0.944	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.035	Skin Sensitization:	1.0
Carcinogencity:	0.057	Eye Corrosion:	0.0
Eye Irritation:	0.112	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.987
Hematotoxicity:	0.232	Drug-induced Nephrotoxicity:	0.672
Genotoxicity:	0.389	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.956	Hek293 Cytotoxicity:	0.656
BCF:	0.638 ? 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:	3.329 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.009 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.355 ? 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
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	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 NPC170597 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	12906
0.1-0.2	31797
0.2-0.3	4530
0.3-0.4	496
0.4-0.5	61
0.5-0.6	27
0.6-0.7	20
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC472350
0.8947	High Similarity	NPC197316
0.8947	High Similarity	NPC89105
0.8313	Intermediate Similarity	NPC112
0.8293	Intermediate Similarity	NPC269141
0.8205	Intermediate Similarity	NPC46137
0.8193	Intermediate Similarity	NPC252292
0.7619	Intermediate Similarity	NPC263829
0.7586	Intermediate Similarity	NPC100998
0.7381	Intermediate Similarity	NPC76406
0.7356	Intermediate Similarity	NPC298257
0.7356	Intermediate Similarity	NPC175214
0.7349	Intermediate Similarity	NPC483705
0.7294	Intermediate Similarity	NPC611289
0.7262	Intermediate Similarity	NPC134405
0.7241	Intermediate Similarity	NPC34587
0.7229	Intermediate Similarity	NPC483706
0.7191	Intermediate Similarity	NPC34927
0.6966	Remote Similarity	NPC205864
0.6966	Remote Similarity	NPC247032
0.6923	Remote Similarity	NPC96795
0.6923	Remote Similarity	NPC264632
0.6848	Remote Similarity	NPC300894
0.6848	Remote Similarity	NPC23845
0.6703	Remote Similarity	NPC296954
0.6702	Remote Similarity	NPC106818
0.6667	Remote Similarity	NPC473285
0.6477	Remote Similarity	NPC68092
0.6429	Remote Similarity	NPC87403
0.6264	Remote Similarity	NPC106677
0.6211	Remote Similarity	NPC610636
0.6207	Remote Similarity	NPC81515
0.6098	Remote Similarity	NPC886
0.6067	Remote Similarity	NPC64141
0.6061	Remote Similarity	NPC476381
0.604	Remote Similarity	NPC306890
0.602	Remote Similarity	NPC476384
0.6	Remote Similarity	NPC470933
0.598	Remote Similarity	NPC94871
0.5979	Remote Similarity	NPC259347
0.5941	Remote Similarity	NPC64195
0.5833	Remote Similarity	NPC119537
0.5761	Remote Similarity	NPC222433
0.5686	Remote Similarity	NPC471062
0.5673	Remote Similarity	NPC473427
0.5644	Remote Similarity	NPC196063
0.5644	Remote Similarity	NPC604195
0.5631	Remote Similarity	NPC470934
0.56	Remote Similarity	NPC476382
0.5588	Remote Similarity	NPC476380
0.5543	Remote Similarity	NPC205195
0.5521	Remote Similarity	NPC476385
0.5495	Remote Similarity	NPC235294
0.5474	Remote Similarity	NPC476377
0.5472	Remote Similarity	NPC229505
0.5392	Remote Similarity	NPC476375
0.5349	Remote Similarity	NPC287597
0.5294	Remote Similarity	NPC141455
0.5229	Remote Similarity	NPC476386
0.5179	Remote Similarity	NPC257970
0.5161	Remote Similarity	NPC260425
0.51	Remote Similarity	NPC105005
0.5063	Remote Similarity	NPC232880
0.5057	Remote Similarity	NPC477294
0.5053	Remote Similarity	NPC40305

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC170597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4129
0.1-0.2	4886
0.2-0.3	132
0.3-0.4	2
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	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD7266	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