NPASS Compound

Natural Product: NPC110906

Natural Product ID	NPC110906
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BCNBWICEIXAVQF-DLVIKRKZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5489470
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 72 76 0 0 0 0 0 0 0 0999 V2000 0.9067 -4.8309 0.6016 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3401 -3.6420 -0.1319 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1646 -3.8673 -0.3424 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5444 -2.7697 -1.3457 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1910 -1.4022 -0.8688 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1352 -1.3582 -0.1387 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4555 -2.4698 0.5591 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2107 -0.9326 -0.9649 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9424 0.2305 -0.6851 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4371 1.4664 -1.1295 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3521 1.4949 -1.7712 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1210 2.6104 -0.8644 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6427 3.8423 -1.2900 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3298 5.0186 -1.0244 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5212 4.9906 -0.3213 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9872 3.7708 0.0955 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3131 2.5885 -0.1617 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7347 1.4301 0.2214 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1239 0.2689 -0.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7921 -0.9048 0.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5417 -2.1969 0.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2182 -3.2433 0.7474 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1428 -3.0419 1.7500 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3931 -1.7506 2.1402 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7338 -0.7223 1.5385 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8029 -4.1142 2.3492 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2253 6.1351 -0.0421 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4588 3.9160 -1.9941 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1957 -0.7947 -0.0942 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7025 0.3600 -0.6866 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1881 0.1817 -0.8831 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8320 0.4049 0.4898 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7541 1.8987 0.7373 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4378 2.3947 0.1791 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9579 3.4777 1.1564 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9045 4.5026 1.2522 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4501 1.4447 0.1557 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8330 2.5608 0.1515 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0031 -0.2106 1.4260 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6957 1.1498 -1.7783 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8620 -2.9656 -1.6573 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4024 -5.0884 -0.9280 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6770 -4.5139 1.3142 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3370 -5.5157 -0.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0862 -5.3977 1.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7674 -3.5927 -1.1585 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6413 -3.7256 0.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8936 -2.9777 -2.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0907 -0.7657 -1.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0366 -0.5195 0.6304 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9384 5.9648 -1.3656 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9102 3.6993 0.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8533 -2.3910 -0.6619 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0188 -4.2758 0.4363 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1099 -1.5303 2.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9452 0.2951 1.8633 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5223 -4.5948 1.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2235 6.1660 0.0714 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4173 4.0940 -1.5499 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2235 0.5707 -1.6779 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4554 -0.7824 -1.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8650 0.0263 0.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8156 2.0338 1.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5670 2.9382 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0128 3.9249 0.8400 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9000 3.0352 2.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2750 4.7129 0.3657 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5684 1.9004 0.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3770 -1.0332 1.7846 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9988 1.2871 -2.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4263 -3.1110 -0.8745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6409 -5.7546 -0.2298 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 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 15 27 1 0 13 28 1 0 5 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 4 41 1 0 3 42 1 0 7 2 1 0 19 9 2 0 25 20 1 0 37 30 1 0 17 12 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 1 4 48 1 6 5 49 1 6 6 50 1 1 14 51 1 0 16 52 1 0 21 53 1 0 22 54 1 0 24 55 1 0 25 56 1 0 26 57 1 0 27 58 1 0 28 59 1 0 30 60 1 6 31 61 1 6 32 62 1 6 33 63 1 1 34 64 1 6 35 65 1 0 35 66 1 0 36 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	BCNBWICEIXAVQF-DLVIKRKZSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-17(32)21(36)25(42-26-22(37)20(35)18(33)15(8-28)40-26)27(38-9)41-24-19(34)16-13(31)6-12(30)7-14(16)39-23(24)10-2-4-11(29)5-3-10/h2-7,9,15,17-18,20-22,25-33,35-37H,8H2,1H3/t9-,15+,17-,18+,20-,21+,22+,25+,26-,27-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	1.019 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.398 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.108 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.159	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.675	Fsp³:	0.444
MCE-18:	119.436 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.6	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.727 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.533 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.286	Promiscuous compounds:	0.558

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.638	MDCK Permeability:	-4.994
Pgp-inhibitor:	0.0	Pgp-substrate:	0.858
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):	0.063
20% Bioavailability (F20%):	0.038	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.043
Plasma Protein Binding (PPB):	83.796%	Volume Distribution (VD):	-0.097
Fu:	13.735% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.853
BSEP inhibitor:	0.007

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:	0.753
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.277 ? 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):

1.691

Half-life (T1/2):

4.194

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.072
Human Hepatotoxicity (H-HT):	0.463	Drug-induced Liver Injury (DILI):	0.918
AMES Toxicity:	0.889	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.062	Skin Sensitization:	0.999
Carcinogencity:	0.141	Eye Corrosion:	0.0
Eye Irritation:	0.584	Respiratory Toxicity:	0.014
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.938
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.209
Genotoxicity:	0.931	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	0.747	Hek293 Cytotoxicity:	0.816
BCF:	0.424 ? 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:	3.053 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.479 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.599 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	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 NPC110906 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	21178
0.1-0.2	23918
0.2-0.3	3803
0.3-0.4	494
0.4-0.5	198
0.5-0.6	81
0.6-0.7	76
0.7-0.8	0
0.8-0.85	6
0.85-0.9	0
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC163242
0.9103	High Similarity	NPC272068
0.9079	High Similarity	NPC170052
0.9079	High Similarity	NPC476215
0.9079	High Similarity	NPC135846
0.8372	Intermediate Similarity	NPC602448
0.8293	Intermediate Similarity	NPC155877
0.825	Intermediate Similarity	NPC254855
0.825	Intermediate Similarity	NPC94610
0.825	Intermediate Similarity	NPC95866
0.8171	Intermediate Similarity	NPC470405
0.7857	Intermediate Similarity	NPC304741
0.7791	Intermediate Similarity	NPC12013
0.7791	Intermediate Similarity	NPC11432
0.7791	Intermediate Similarity	NPC477613
0.7727	Intermediate Similarity	NPC220173
0.764	Intermediate Similarity	NPC292929
0.7625	Intermediate Similarity	NPC216496
0.7468	Intermediate Similarity	NPC77672
0.7468	Intermediate Similarity	NPC133671
0.7468	Intermediate Similarity	NPC135391
0.7468	Intermediate Similarity	NPC78263
0.7468	Intermediate Similarity	NPC250069
0.7439	Intermediate Similarity	NPC224530
0.7412	Intermediate Similarity	NPC139320
0.7356	Intermediate Similarity	NPC470444
0.7303	Intermediate Similarity	NPC35119
0.7273	Intermediate Similarity	NPC240306
0.7253	Intermediate Similarity	NPC221342
0.7253	Intermediate Similarity	NPC476470
0.7159	Intermediate Similarity	NPC255157
0.7159	Intermediate Similarity	NPC259896
0.7125	Intermediate Similarity	NPC111929
0.7125	Intermediate Similarity	NPC320283
0.7125	Intermediate Similarity	NPC41121
0.7111	Intermediate Similarity	NPC122467
0.7111	Intermediate Similarity	NPC32641
0.7111	Intermediate Similarity	NPC256188
0.7041	Intermediate Similarity	NPC488734
0.7041	Intermediate Similarity	NPC488735
0.7041	Intermediate Similarity	NPC488739
0.7041	Intermediate Similarity	NPC488732
0.7041	Intermediate Similarity	NPC488738
0.6957	Remote Similarity	NPC76831
0.6897	Remote Similarity	NPC473682
0.6875	Remote Similarity	NPC288084
0.6842	Remote Similarity	NPC203145
0.68	Remote Similarity	NPC480445
0.6765	Remote Similarity	NPC488737
0.6747	Remote Similarity	NPC145038
0.6747	Remote Similarity	NPC56077
0.6747	Remote Similarity	NPC281131
0.6747	Remote Similarity	NPC64305
0.6747	Remote Similarity	NPC253662
0.6747	Remote Similarity	NPC179950
0.6747	Remote Similarity	NPC88789
0.6747	Remote Similarity	NPC491374
0.6742	Remote Similarity	NPC471748
0.6701	Remote Similarity	NPC219043
0.6667	Remote Similarity	NPC89052
0.6633	Remote Similarity	NPC25523
0.6629	Remote Similarity	NPC29958
0.6598	Remote Similarity	NPC189564
0.6588	Remote Similarity	NPC472459
0.6569	Remote Similarity	NPC488740
0.6569	Remote Similarity	NPC488736
0.6569	Remote Similarity	NPC488733
0.6556	Remote Similarity	NPC173582
0.6556	Remote Similarity	NPC265885
0.6556	Remote Similarity	NPC181465
0.6556	Remote Similarity	NPC215710
0.6556	Remote Similarity	NPC473438
0.6556	Remote Similarity	NPC253788
0.6538	Remote Similarity	NPC192539
0.6522	Remote Similarity	NPC61904
0.6484	Remote Similarity	NPC605592
0.6465	Remote Similarity	NPC303694
0.6429	Remote Similarity	NPC127546
0.6429	Remote Similarity	NPC57625
0.6429	Remote Similarity	NPC173637
0.6429	Remote Similarity	NPC317489
0.6429	Remote Similarity	NPC223424
0.6429	Remote Similarity	NPC600591
0.6421	Remote Similarity	NPC89127
0.6415	Remote Similarity	NPC25946
0.6364	Remote Similarity	NPC48984
0.6364	Remote Similarity	NPC136761
0.6346	Remote Similarity	NPC480444
0.6322	Remote Similarity	NPC60735
0.6322	Remote Similarity	NPC26230
0.6322	Remote Similarity	NPC48093
0.6316	Remote Similarity	NPC142142
0.6304	Remote Similarity	NPC156869
0.6292	Remote Similarity	NPC203050
0.6292	Remote Similarity	NPC225434
0.625	Remote Similarity	NPC120099
0.625	Remote Similarity	NPC259957
0.6237	Remote Similarity	NPC35167
0.6235	Remote Similarity	NPC19388
0.6235	Remote Similarity	NPC240431
0.6235	Remote Similarity	NPC55786
0.619	Remote Similarity	NPC67037
0.619	Remote Similarity	NPC255615
0.618	Remote Similarity	NPC116458
0.618	Remote Similarity	NPC246943
0.617	Remote Similarity	NPC64425
0.6139	Remote Similarity	NPC470712
0.6091	Remote Similarity	NPC473554
0.6087	Remote Similarity	NPC471079
0.6082	Remote Similarity	NPC473071
0.6067	Remote Similarity	NPC609478
0.604	Remote Similarity	NPC292019
0.604	Remote Similarity	NPC202908
0.604	Remote Similarity	NPC173837
0.6023	Remote Similarity	NPC325555
0.6023	Remote Similarity	NPC226304
0.6	Remote Similarity	NPC253521
0.6	Remote Similarity	NPC223747
0.6	Remote Similarity	NPC113836
0.598	Remote Similarity	NPC480441
0.5977	Remote Similarity	NPC297987
0.5957	Remote Similarity	NPC203259
0.5957	Remote Similarity	NPC65003
0.5957	Remote Similarity	NPC33054
0.5957	Remote Similarity	NPC176740
0.5957	Remote Similarity	NPC471725
0.5957	Remote Similarity	NPC134532
0.5957	Remote Similarity	NPC602582
0.5955	Remote Similarity	NPC159579
0.5955	Remote Similarity	NPC219904
0.5952	Remote Similarity	NPC54802
0.5952	Remote Similarity	NPC197304
0.593	Remote Similarity	NPC135599
0.593	Remote Similarity	NPC73855
0.593	Remote Similarity	NPC113968
0.593	Remote Similarity	NPC328940
0.593	Remote Similarity	NPC277174
0.593	Remote Similarity	NPC606877
0.5914	Remote Similarity	NPC258044
0.5914	Remote Similarity	NPC217387
0.5909	Remote Similarity	NPC21359
0.5909	Remote Similarity	NPC460984
0.5909	Remote Similarity	NPC488080
0.5909	Remote Similarity	NPC169977
0.59	Remote Similarity	NPC14187
0.5877	Remote Similarity	NPC249560
0.5865	Remote Similarity	NPC470718
0.5862	Remote Similarity	NPC104677
0.5804	Remote Similarity	NPC231787
0.5795	Remote Similarity	NPC8573
0.5795	Remote Similarity	NPC265530
0.5794	Remote Similarity	NPC162394
0.5778	Remote Similarity	NPC129217
0.5714	Remote Similarity	NPC482026
0.5701	Remote Similarity	NPC470713
0.57	Remote Similarity	NPC287889
0.5698	Remote Similarity	NPC34531
0.5688	Remote Similarity	NPC209550
0.5682	Remote Similarity	NPC249281
0.5657	Remote Similarity	NPC603079
0.5631	Remote Similarity	NPC473072
0.5612	Remote Similarity	NPC297503
0.5604	Remote Similarity	NPC175107
0.56	Remote Similarity	NPC476472
0.56	Remote Similarity	NPC294815
0.56	Remote Similarity	NPC16194
0.5575	Remote Similarity	NPC487499
0.5567	Remote Similarity	NPC129264
0.5567	Remote Similarity	NPC115674
0.5556	Remote Similarity	NPC46420
0.5556	Remote Similarity	NPC24043
0.5556	Remote Similarity	NPC473327
0.5543	Remote Similarity	NPC85707
0.5532	Remote Similarity	NPC116864
0.5532	Remote Similarity	NPC244776
0.5521	Remote Similarity	NPC67326
0.5521	Remote Similarity	NPC39834
0.5517	Remote Similarity	NPC487502
0.551	Remote Similarity	NPC470125
0.55	Remote Similarity	NPC101399
0.55	Remote Similarity	NPC221288
0.55	Remote Similarity	NPC217822
0.55	Remote Similarity	NPC11847
0.55	Remote Similarity	NPC198938
0.55	Remote Similarity	NPC194836
0.55	Remote Similarity	NPC91493
0.55	Remote Similarity	NPC605081
0.549	Remote Similarity	NPC218161
0.5484	Remote Similarity	NPC605784
0.5481	Remote Similarity	NPC488075
0.5474	Remote Similarity	NPC8856
0.5455	Remote Similarity	NPC103342
0.5446	Remote Similarity	NPC471669
0.5431	Remote Similarity	NPC30011
0.54	Remote Similarity	NPC270448
0.5385	Remote Similarity	NPC52550
0.5377	Remote Similarity	NPC164704
0.5364	Remote Similarity	NPC474522
0.5357	Remote Similarity	NPC480443
0.5357	Remote Similarity	NPC175429

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5812
0.1-0.2	3248
0.2-0.3	78
0.3-0.4	8
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
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
0.5957	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