NPASS Compound

Natural Product: NPC308843

Natural Product ID	NPC308843
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HCAACQQXSMJKAH-VQKKVCIBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11542224
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 85 91 0 0 0 0 0 0 0 0999 V2000 8.0439 -0.5919 4.3882 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4325 -1.1470 3.1489 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4642 -1.1992 2.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8225 -1.7522 0.9177 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8712 -1.8056 -0.0733 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5733 -1.3226 0.1342 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6223 -1.3717 -0.8557 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9026 -1.8552 -1.9672 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3483 -0.8634 -0.5669 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0402 -0.3288 0.6634 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6963 0.2047 0.9747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4095 0.7115 2.2263 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1526 1.2002 2.5082 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.1756 1.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5848 0.6851 0.2720 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7153 0.1946 0.0274 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 0.6561 -0.7652 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4168 -0.4394 -0.9353 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3491 -0.5476 -1.9277 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4777 0.5079 -2.8201 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6587 1.6330 -2.6748 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7845 2.6851 -3.5568 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6361 2.5951 -4.4669 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9514 3.7679 -3.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0320 3.8210 -2.3530 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1368 4.9778 -2.1385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1540 6.0795 -2.9514 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6675 7.1470 -2.7501 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5579 7.1587 -1.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5991 6.0544 -0.8640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7575 4.9893 -1.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3754 8.2565 -1.5302 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 2.7755 -1.5529 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7250 1.7047 -1.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3959 0.4640 -3.8481 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2717 -1.4802 -0.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9377 -2.6937 -0.0716 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3066 -3.8661 0.5684 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1946 -4.4683 1.6700 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4834 -4.9111 0.9714 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8568 -3.7981 0.0396 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3469 -3.6694 -0.0074 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9758 -4.8434 -0.4078 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2542 -2.5879 0.4423 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2114 -6.1094 0.3629 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4689 -3.4995 2.6524 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1753 -4.8783 -0.3977 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0719 1.6774 1.8551 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4011 2.2003 3.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9858 -0.3056 1.5732 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2061 -0.7741 1.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1662 -0.7255 2.3305 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1743 -2.3476 -1.3235 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8970 -0.5802 5.1079 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7347 0.4555 4.1885 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1808 -1.1192 4.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8265 -2.1117 0.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6182 -0.9039 -1.3443 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2182 0.6987 2.9582 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0893 1.6039 3.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8907 -0.1911 -0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0160 -1.4149 -2.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0412 4.6071 -4.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8265 6.1251 -3.7726 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6171 8.0178 -3.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3016 6.0485 -0.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7707 4.1109 -0.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0891 8.2685 -0.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3045 0.8995 -3.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1386 -2.8993 -1.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3368 -3.6723 1.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6937 -5.3279 2.1476 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2325 -5.1008 1.7604 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4410 -4.0244 -0.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6260 -2.8928 -0.7683 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7941 -3.3913 0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4190 -4.7458 -1.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1597 -6.1041 -0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4523 -3.4445 2.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6673 -5.6489 -0.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3459 1.4536 3.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4579 2.5743 3.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7176 3.0796 3.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8910 -0.3017 3.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7899 -3.2083 -1.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 25 33 1 0 33 34 1 0 20 35 1 0 18 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 39 46 1 0 38 47 1 0 14 48 1 0 48 49 1 0 10 50 1 0 50 51 1 0 51 52 2 0 5 53 1 0 52 3 1 0 51 6 1 0 16 11 1 0 34 17 2 0 44 37 1 0 34 21 1 0 31 26 1 0 1 54 1 0 1 55 1 0 1 56 1 0 4 57 1 0 9 58 1 0 12 59 1 0 13 60 1 0 16 61 1 0 19 62 1 0 24 63 1 0 27 64 1 0 28 65 1 0 30 66 1 0 31 67 1 0 32 68 1 0 35 69 1 0 37 70 1 6 38 71 1 1 39 72 1 1 40 73 1 1 41 74 1 6 42 75 1 0 42 76 1 0 43 77 1 0 45 78 1 0 46 79 1 0 47 80 1 0 49 81 1 0 49 82 1 0 49 83 1 0 52 84 1 0 53 85 1 0 M END

Standard InCHIKey	HCAACQQXSMJKAH-VQKKVCIBSA-N
Standard InCHI	InChI=1S/C38H32O15/c1-48-19-10-21(41)32-22(42)12-27(50-28(32)11-19)17-5-8-25(49-2)20(9-17)31-29(52-38-36(47)35(46)34(45)30(15-39)53-38)14-24(44)33-23(43)13-26(51-37(31)33)16-3-6-18(40)7-4-16/h3-14,30,34-36,38-41,44-47H,15H2,1-2H3/t30-,34-,35+,36-,38-/m1/s1
SMILES	COc1cc(c2c(=O)cc(c3ccc(c(c3)c3c(cc(c4c(=O)cc(c5ccc(cc5)O)oc34)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC)oc2c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	728.17	Volume:	695.579 ? Van der Waals volume.
Dense:	1.047	LogP:	3.082 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.09 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.99 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	42.0
TPSA:	238.95 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.523	Fsp³:	0.211
MCE-18:	141.565 ? 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:	0.714	Fluc inhibitor:	0.23 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.978 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.999 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.081	Promiscuous compounds:	0.724

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.056	MDCK Permeability:	-5.24
Pgp-inhibitor:	0.001	Pgp-substrate:	0.277
PAMPA:	0.844 ? 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):	0.072
20% Bioavailability (F20%):	0.105	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.442
Plasma Protein Binding (PPB):	94.665%	Volume Distribution (VD):	-0.059
Fu:	5.593% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.854
BSEP inhibitor:	0.317

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
HLM stability:	0.034 ? 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):

1.878

Half-life (T1/2):

4.127

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.135
Human Hepatotoxicity (H-HT):	0.727	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.94	Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.7	Skin Sensitization:	0.963
Carcinogencity:	0.675	Eye Corrosion:	0.0
Eye Irritation:	0.334	Respiratory Toxicity:	0.132
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.679
Hematotoxicity:	0.104	Drug-induced Nephrotoxicity:	0.154
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.722	Hek293 Cytotoxicity:	0.914
BCF:	1.007 ? 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:	3.949 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.976 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.529 ? 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 NPC308843 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	23895
0.1-0.2	22516
0.2-0.3	2337
0.3-0.4	739
0.4-0.5	240
0.5-0.6	98
0.6-0.7	23
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	Natural Product ID
0.75	Intermediate Similarity	NPC39360
0.75	Intermediate Similarity	NPC29763
0.75	Intermediate Similarity	NPC210003
0.7381	Intermediate Similarity	NPC159707
0.7209	Intermediate Similarity	NPC95090
0.7209	Intermediate Similarity	NPC27408
0.6813	Remote Similarity	NPC607707
0.6703	Remote Similarity	NPC22832
0.6703	Remote Similarity	NPC243930
0.663	Remote Similarity	NPC311830
0.6629	Remote Similarity	NPC189142
0.6629	Remote Similarity	NPC77660
0.6628	Remote Similarity	NPC248739
0.6484	Remote Similarity	NPC27942
0.6444	Remote Similarity	NPC93337
0.6404	Remote Similarity	NPC331652
0.6374	Remote Similarity	NPC105025
0.6344	Remote Similarity	NPC601144
0.6333	Remote Similarity	NPC261866
0.6264	Remote Similarity	NPC323593
0.6264	Remote Similarity	NPC203500
0.6196	Remote Similarity	NPC265624
0.6196	Remote Similarity	NPC610763
0.6154	Remote Similarity	NPC58053
0.6154	Remote Similarity	NPC215203
0.6087	Remote Similarity	NPC146792
0.6022	Remote Similarity	NPC186807
0.6022	Remote Similarity	NPC181712
0.6	Remote Similarity	NPC603508
0.5978	Remote Similarity	NPC143851
0.596	Remote Similarity	NPC44931
0.5914	Remote Similarity	NPC297987
0.59	Remote Similarity	NPC65003
0.5784	Remote Similarity	NPC64051
0.5761	Remote Similarity	NPC158027
0.5745	Remote Similarity	NPC205026
0.5743	Remote Similarity	NPC22062
0.5743	Remote Similarity	NPC473634
0.5743	Remote Similarity	NPC138811
0.5699	Remote Similarity	NPC186227
0.5684	Remote Similarity	NPC84362
0.5684	Remote Similarity	NPC45638
0.567	Remote Similarity	NPC486578
0.5638	Remote Similarity	NPC19709
0.5638	Remote Similarity	NPC83283
0.5625	Remote Similarity	NPC201292
0.5619	Remote Similarity	NPC270675
0.5619	Remote Similarity	NPC195685
0.5612	Remote Similarity	NPC88023
0.5612	Remote Similarity	NPC116458
0.5612	Remote Similarity	NPC246943
0.5612	Remote Similarity	NPC309025
0.56	Remote Similarity	NPC8856
0.5579	Remote Similarity	NPC277205
0.5579	Remote Similarity	NPC37919
0.5579	Remote Similarity	NPC259152
0.5567	Remote Similarity	NPC609451
0.5566	Remote Similarity	NPC475382
0.5556	Remote Similarity	NPC601586
0.5545	Remote Similarity	NPC472993
0.5542	Remote Similarity	NPC234133
0.5532	Remote Similarity	NPC14606
0.5526	Remote Similarity	NPC298666
0.5524	Remote Similarity	NPC473623
0.5514	Remote Similarity	NPC101636
0.5514	Remote Similarity	NPC298171
0.551	Remote Similarity	NPC80188
0.551	Remote Similarity	NPC605067
0.5481	Remote Similarity	NPC46202
0.5481	Remote Similarity	NPC64425
0.5474	Remote Similarity	NPC289667
0.5472	Remote Similarity	NPC488089
0.5463	Remote Similarity	NPC472994
0.5455	Remote Similarity	NPC220169
0.5455	Remote Similarity	NPC602805
0.5417	Remote Similarity	NPC168822
0.5417	Remote Similarity	NPC136042
0.5408	Remote Similarity	NPC191306
0.5408	Remote Similarity	NPC307938
0.5408	Remote Similarity	NPC285197
0.54	Remote Similarity	NPC190003
0.5385	Remote Similarity	NPC122809
0.5377	Remote Similarity	NPC209296
0.5368	Remote Similarity	NPC194593
0.5361	Remote Similarity	NPC58716
0.5361	Remote Similarity	NPC46420
0.5354	Remote Similarity	NPC601710
0.5347	Remote Similarity	NPC172807
0.5319	Remote Similarity	NPC601984
0.5312	Remote Similarity	NPC45618
0.5312	Remote Similarity	NPC108831
0.5312	Remote Similarity	NPC182634
0.531	Remote Similarity	NPC311850
0.5294	Remote Similarity	NPC472607
0.5288	Remote Similarity	NPC210073
0.5287	Remote Similarity	NPC610914
0.5278	Remote Similarity	NPC195257
0.5263	Remote Similarity	NPC488083
0.5258	Remote Similarity	NPC197896
0.5258	Remote Similarity	NPC313163
0.5253	Remote Similarity	NPC282169
0.5238	Remote Similarity	NPC115674
0.5234	Remote Similarity	NPC210961
0.5234	Remote Similarity	NPC229409
0.5208	Remote Similarity	NPC473043
0.5204	Remote Similarity	NPC84265
0.5204	Remote Similarity	NPC24043
0.5204	Remote Similarity	NPC73511
0.5182	Remote Similarity	NPC179862
0.5172	Remote Similarity	NPC68592
0.5155	Remote Similarity	NPC121649
0.5152	Remote Similarity	NPC182045
0.5149	Remote Similarity	NPC605784
0.514	Remote Similarity	NPC65711
0.5104	Remote Similarity	NPC71061
0.5104	Remote Similarity	NPC600396
0.51	Remote Similarity	NPC168584
0.5093	Remote Similarity	NPC124155
0.5093	Remote Similarity	NPC35119
0.5088	Remote Similarity	NPC25523
0.5088	Remote Similarity	NPC164704
0.5059	Remote Similarity	NPC29353
0.5054	Remote Similarity	NPC191154
0.5051	Remote Similarity	NPC22195
0.5051	Remote Similarity	NPC21190
0.505	Remote Similarity	NPC608742
0.5047	Remote Similarity	NPC240306

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC308843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5873
0.1-0.2	3215
0.2-0.3	49
0.3-0.4	7
0.4-0.5	5
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
0.5377	Remote Similarity	NPD7054	Phase 4

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