NPASS Compound

Natural Product: NPC176808

Natural Product ID	NPC176808
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JUIYKRQGQJORHH-SBUDPTTHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	100998070
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 79 83 0 0 0 0 0 0 0 0999 V2000 5.2482 0.8331 5.0847 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8245 1.8144 4.0946 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1229 1.3060 3.4758 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9167 0.6907 2.1312 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5095 0.3334 1.7818 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4527 1.2271 2.3162 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7361 1.8558 1.3339 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3957 1.7471 1.3175 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8004 0.3679 1.1281 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2556 -0.2580 -0.1594 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8471 -1.7035 -0.1304 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4356 -1.8062 0.3018 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2638 -0.4695 0.4128 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4405 0.4187 1.1735 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7512 0.0645 -0.7863 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9317 -0.2131 -1.4094 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9118 -1.1888 -2.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8258 -1.7308 -2.7304 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0355 -1.5745 -3.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9938 -2.5338 -4.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1727 -2.8480 -4.7670 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3771 -2.2567 -4.4594 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3689 -1.3048 -3.4582 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2088 -0.9440 -2.7770 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2318 -0.0447 -1.8377 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1541 0.3469 -1.1452 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3356 1.3607 -0.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3996 2.0997 0.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6409 2.9945 1.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9560 3.1380 1.9588 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9336 2.4048 1.3895 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6628 1.5352 0.3777 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2733 2.5149 1.8223 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2857 1.7483 1.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1858 4.0384 2.9953 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5756 -2.5781 -5.1142 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4980 -3.5577 -6.1335 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7733 -3.1152 -4.4222 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3374 -2.4723 1.5670 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1291 -2.3797 -1.3081 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6900 0.3512 -1.2640 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9575 2.2432 3.1388 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2348 -1.0215 2.1059 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6579 -0.5241 2.1399 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9702 2.4055 3.3368 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1443 0.8998 5.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6508 0.9992 6.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6203 -0.1696 4.7961 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1051 2.7158 4.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5908 0.5914 4.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3841 1.2795 1.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4702 0.3464 0.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8017 0.6217 3.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8888 2.1789 2.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0051 2.3595 0.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1464 -0.2292 2.0201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3700 -0.1633 -0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4984 -2.1869 0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1304 -2.4545 -0.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2065 -0.7419 0.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1660 -3.5967 -5.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3061 -0.8261 -3.2044 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3615 2.0502 0.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8386 3.5627 1.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4328 0.9537 -0.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1285 0.6518 1.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3872 1.9700 0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2458 2.0015 1.7200 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1881 5.0571 2.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3490 -4.5571 -5.6687 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4933 -3.5664 -6.6298 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7040 -3.3022 -6.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6646 -4.1224 -4.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6403 -2.4943 1.7436 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6164 -3.2239 -1.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2530 0.3037 -2.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7825 -1.5525 1.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4117 -1.0930 2.9249 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2880 2.4221 2.4102 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 36 37 1 0 20 38 1 0 12 39 1 0 11 40 1 0 10 41 1 0 6 42 1 0 5 43 1 0 4 44 1 0 3 45 1 0 42 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 24 19 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 1 3 50 1 1 4 51 1 6 5 52 1 6 6 53 1 1 8 54 1 0 8 55 1 0 9 56 1 1 10 57 1 6 11 58 1 1 12 59 1 6 13 60 1 1 21 61 1 0 23 62 1 0 28 63 1 0 29 64 1 0 32 65 1 0 34 66 1 0 34 67 1 0 34 68 1 0 35 69 1 0 37 70 1 0 37 71 1 0 37 72 1 0 38 73 1 0 39 74 1 0 40 75 1 0 41 76 1 0 43 77 1 0 44 78 1 0 45 79 1 0 M END

Standard InCHIKey	JUIYKRQGQJORHH-SBUDPTTHSA-N
Standard InCHI	InChI=1S/C29H34O16/c1-10-19(32)22(35)24(37)28(42-10)41-9-17-20(33)23(36)25(38)29(44-17)45-27-21(34)18-14(31)7-12(39-2)8-16(18)43-26(27)11-4-5-13(30)15(6-11)40-3/h4-8,10,17,19-20,22-25,28-33,35-38H,9H2,1-3H3/t10-,17+,19-,20-,22+,23-,24+,25+,28+,29-/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)OC)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	1.007 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.538 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.299 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	247.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.721	Fsp³:	0.483
MCE-18:	121.279 ? 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:	0.615	Fluc inhibitor:	0.278 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.839 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.642 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.048	Promiscuous compounds:	0.409

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.235	MDCK Permeability:	-5.362
Pgp-inhibitor:	0.003	Pgp-substrate:	0.858
PAMPA:	0.987 ? 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):	0.848
20% Bioavailability (F20%):	0.176	30% Bioavailability (F30%):	0.877
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.231
Plasma Protein Binding (PPB):	83.933%	Volume Distribution (VD):	-0.092
Fu:	15.19% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.851
BSEP inhibitor:	0.1

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	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:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.235
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.961
HLM stability:	0.783 ? 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):

1.18

Half-life (T1/2):

3.329

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.2
Human Hepatotoxicity (H-HT):	0.405	Drug-induced Liver Injury (DILI):	0.909
AMES Toxicity:	0.917	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.039	Skin Sensitization:	0.994
Carcinogencity:	0.072	Eye Corrosion:	0.0
Eye Irritation:	0.263	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.876
Hematotoxicity:	0.232	Drug-induced Nephrotoxicity:	0.495
Genotoxicity:	0.437	RPMI-8226 Immunitoxicity:	0.226
A549 Cytotoxicity:	0.68	Hek293 Cytotoxicity:	0.553
BCF:	0.477 ? 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:	3.183 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.653 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.847 ? 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
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO376	Suillus tridentinus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29658	Spinulum annotinum	Species	Lycopodiaceae	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 NPC176808 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	20573
0.1-0.2	25489
0.2-0.3	2792
0.3-0.4	520
0.4-0.5	277
0.5-0.6	125
0.6-0.7	55
0.7-0.8	2
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8315	Intermediate Similarity	NPC476472
0.8315	Intermediate Similarity	NPC294815
0.8315	Intermediate Similarity	NPC16194
0.8161	Intermediate Similarity	NPC186816
0.7391	Intermediate Similarity	NPC470443
0.7097	Intermediate Similarity	NPC126784
0.7097	Intermediate Similarity	NPC241423
0.7093	Intermediate Similarity	NPC46420
0.7093	Intermediate Similarity	NPC271692
0.7053	Intermediate Similarity	NPC142142
0.6989	Remote Similarity	NPC473571
0.6989	Remote Similarity	NPC110941
0.6957	Remote Similarity	NPC173582
0.6957	Remote Similarity	NPC265885
0.6957	Remote Similarity	NPC181465
0.6957	Remote Similarity	NPC215710
0.6957	Remote Similarity	NPC67105
0.6957	Remote Similarity	NPC473438
0.6957	Remote Similarity	NPC253788
0.6947	Remote Similarity	NPC209296
0.6947	Remote Similarity	NPC473327
0.6915	Remote Similarity	NPC153755
0.6882	Remote Similarity	NPC203259
0.6882	Remote Similarity	NPC33054
0.6882	Remote Similarity	NPC210073
0.6882	Remote Similarity	NPC176740
0.6882	Remote Similarity	NPC471725
0.6882	Remote Similarity	NPC134532
0.6882	Remote Similarity	NPC602582
0.6869	Remote Similarity	NPC89052
0.6778	Remote Similarity	NPC223747
0.6774	Remote Similarity	NPC44931
0.6742	Remote Similarity	NPC611303
0.6733	Remote Similarity	NPC173837
0.6702	Remote Similarity	NPC22062
0.6702	Remote Similarity	NPC473634
0.6702	Remote Similarity	NPC138811
0.6667	Remote Similarity	NPC249281
0.6667	Remote Similarity	NPC480441
0.6667	Remote Similarity	NPC25523
0.6633	Remote Similarity	NPC473073
0.6591	Remote Similarity	NPC158674
0.6535	Remote Similarity	NPC121703
0.6526	Remote Similarity	NPC65563
0.6526	Remote Similarity	NPC470949
0.6522	Remote Similarity	NPC276377
0.6421	Remote Similarity	NPC39834
0.6421	Remote Similarity	NPC227508
0.6237	Remote Similarity	NPC116458
0.6237	Remote Similarity	NPC246943
0.6237	Remote Similarity	NPC605784
0.6224	Remote Similarity	NPC488073
0.62	Remote Similarity	NPC486577
0.6186	Remote Similarity	NPC150164
0.6126	Remote Similarity	NPC192539
0.61	Remote Similarity	NPC606657
0.6061	Remote Similarity	NPC240306
0.6061	Remote Similarity	NPC488074
0.6042	Remote Similarity	NPC251417
0.6038	Remote Similarity	NPC217520
0.6036	Remote Similarity	NPC209550
0.602	Remote Similarity	NPC156869
0.6	Remote Similarity	NPC203050
0.6	Remote Similarity	NPC488072
0.6	Remote Similarity	NPC225434
0.5981	Remote Similarity	NPC277532
0.5979	Remote Similarity	NPC471079
0.5976	Remote Similarity	NPC78326
0.5962	Remote Similarity	NPC14187
0.5941	Remote Similarity	NPC32641
0.5941	Remote Similarity	NPC256188
0.5941	Remote Similarity	NPC72016
0.5926	Remote Similarity	NPC139571
0.5918	Remote Similarity	NPC67326
0.587	Remote Similarity	NPC297987
0.587	Remote Similarity	NPC136042
0.5865	Remote Similarity	NPC470446
0.5859	Remote Similarity	NPC303913
0.5825	Remote Similarity	NPC220173
0.5816	Remote Similarity	NPC609888
0.5806	Remote Similarity	NPC84362
0.5806	Remote Similarity	NPC27640
0.58	Remote Similarity	NPC204693
0.5789	Remote Similarity	NPC101026
0.5789	Remote Similarity	NPC488077
0.5784	Remote Similarity	NPC35119
0.5769	Remote Similarity	NPC470449
0.5769	Remote Similarity	NPC470445
0.5745	Remote Similarity	NPC59534
0.5729	Remote Similarity	NPC311830
0.5702	Remote Similarity	NPC175429
0.5701	Remote Similarity	NPC189564
0.5686	Remote Similarity	NPC12013
0.5686	Remote Similarity	NPC11432
0.5686	Remote Similarity	NPC477613
0.5673	Remote Similarity	NPC195257
0.5673	Remote Similarity	NPC470447
0.567	Remote Similarity	NPC601586
0.5664	Remote Similarity	NPC488079
0.5648	Remote Similarity	NPC292019
0.5648	Remote Similarity	NPC202908
0.5638	Remote Similarity	NPC305811
0.5631	Remote Similarity	NPC122467
0.5631	Remote Similarity	NPC473623
0.5619	Remote Similarity	NPC101636
0.5614	Remote Similarity	NPC138990
0.5612	Remote Similarity	NPC116864
0.5612	Remote Similarity	NPC244776
0.5607	Remote Similarity	NPC203145
0.56	Remote Similarity	NPC275454
0.5591	Remote Similarity	NPC289667
0.5591	Remote Similarity	NPC238376
0.5577	Remote Similarity	NPC488089
0.5566	Remote Similarity	NPC135358
0.5556	Remote Similarity	NPC473072
0.5534	Remote Similarity	NPC65711
0.5524	Remote Similarity	NPC89127
0.5521	Remote Similarity	NPC219904
0.55	Remote Similarity	NPC187379
0.5484	Remote Similarity	NPC111929
0.5484	Remote Similarity	NPC320283
0.5484	Remote Similarity	NPC41121
0.5472	Remote Similarity	NPC221342
0.5472	Remote Similarity	NPC476470
0.5463	Remote Similarity	NPC11468
0.5455	Remote Similarity	NPC265115
0.5437	Remote Similarity	NPC475366
0.5426	Remote Similarity	NPC127546
0.5426	Remote Similarity	NPC57625
0.5426	Remote Similarity	NPC108831
0.5426	Remote Similarity	NPC19709
0.5426	Remote Similarity	NPC173637
0.5426	Remote Similarity	NPC317489
0.5426	Remote Similarity	NPC223424
0.5426	Remote Similarity	NPC182634
0.5426	Remote Similarity	NPC600591
0.5421	Remote Similarity	NPC602448
0.5408	Remote Similarity	NPC206123
0.537	Remote Similarity	NPC470455
0.5368	Remote Similarity	NPC265530
0.5351	Remote Similarity	NPC198199
0.5333	Remote Similarity	NPC229409
0.5319	Remote Similarity	NPC331652
0.5312	Remote Similarity	NPC349108
0.5306	Remote Similarity	NPC601144
0.5288	Remote Similarity	NPC46202
0.5288	Remote Similarity	NPC64425
0.5288	Remote Similarity	NPC64051
0.5273	Remote Similarity	NPC470451
0.5253	Remote Similarity	NPC99957
0.5238	Remote Similarity	NPC483414
0.5238	Remote Similarity	NPC483415
0.5225	Remote Similarity	NPC219043
0.5225	Remote Similarity	NPC480796
0.5225	Remote Similarity	NPC472993
0.5225	Remote Similarity	NPC477895
0.5214	Remote Similarity	NPC120952
0.5214	Remote Similarity	NPC241781
0.5207	Remote Similarity	NPC473554
0.5196	Remote Similarity	NPC480466
0.5189	Remote Similarity	NPC483416
0.5185	Remote Similarity	NPC298171
0.5179	Remote Similarity	NPC473644
0.5179	Remote Similarity	NPC303694
0.5152	Remote Similarity	NPC181616
0.5138	Remote Similarity	NPC470450
0.5135	Remote Similarity	NPC470416
0.5133	Remote Similarity	NPC311850
0.5128	Remote Similarity	NPC470720
0.5128	Remote Similarity	NPC488078
0.5096	Remote Similarity	NPC473512
0.5096	Remote Similarity	NPC479405
0.5096	Remote Similarity	NPC129827
0.5096	Remote Similarity	NPC605592
0.5093	Remote Similarity	NPC231194
0.5093	Remote Similarity	NPC85751
0.5093	Remote Similarity	NPC471669
0.5093	Remote Similarity	NPC19240
0.5082	Remote Similarity	NPC483159
0.5082	Remote Similarity	NPC483160
0.5056	Remote Similarity	NPC469622
0.5051	Remote Similarity	NPC488071
0.505	Remote Similarity	NPC355481
0.5048	Remote Similarity	NPC129264
0.5048	Remote Similarity	NPC479404
0.5046	Remote Similarity	NPC36138
0.5043	Remote Similarity	NPC156785
0.5043	Remote Similarity	NPC162394
0.5043	Remote Similarity	NPC474522
0.5043	Remote Similarity	NPC470717

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC176808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5405
0.1-0.2	3694
0.2-0.3	42
0.3-0.4	2
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	2
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
0.7717	Intermediate Similarity	NPD7251	Phase 2
0.7396	Intermediate Similarity	NPD7808	Phase 3
0.6947	Remote Similarity	NPD7054	Phase 4
0.6882	Remote Similarity	NPD6797	Phase 2
0.5607	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