NPASS Compound

Natural Product: NPC580585

Natural Product ID	NPC580585
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gymnemanol
IUPAC Name	(3~{S},4~{R},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{S},9~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-4,8~{a}-bis(hydroxymethyl)-4,6~{a},6~{b},11,11,14~{b}-hexamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicene-3,8,9-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 89 0 0 0 0 0 0 0 0999 V2000 -5.2759 -1.2305 2.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7954 -1.4104 0.8859 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1262 -2.8296 0.4655 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4821 -0.4940 -0.1044 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9707 0.8893 -0.0787 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5629 1.6167 -1.0997 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4553 1.0327 -0.1134 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2589 2.5097 0.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8856 3.3550 -0.6249 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9503 0.7032 -1.4534 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0905 1.8843 -2.2335 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6035 0.1782 -1.6596 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7345 -0.1012 -0.4727 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5136 -1.6216 -0.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3824 0.2997 0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7443 0.7886 1.8560 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7273 1.0107 1.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3289 0.3418 0.7260 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8489 0.4635 0.6571 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2361 1.8566 0.3237 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3432 0.0860 2.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8197 0.0642 2.0497 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5291 -0.5784 0.9264 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6713 0.2068 0.6043 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7485 -0.9074 -0.2785 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4167 -0.2187 -1.4742 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9445 -2.4073 -0.5776 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2650 -2.7068 -0.7985 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2992 -0.5764 -0.2953 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7758 -0.2170 -1.6529 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3527 0.1029 -1.7716 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6230 0.5956 -0.5760 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3421 2.0777 -0.7037 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8691 0.1464 0.9277 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2860 -1.2758 0.7823 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1640 -0.5531 2.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5036 -0.7702 2.9333 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5864 -2.2028 2.7430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4680 -3.1251 -0.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9543 -3.5675 1.2687 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1742 -2.9018 0.0984 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4534 -0.9568 -1.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5535 -0.4727 0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2928 1.3555 0.8990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7655 1.0502 -1.8871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2079 2.7359 0.3817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8288 2.6524 1.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0410 4.2147 -0.1492 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7305 0.0254 -1.9293 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5086 1.7594 -3.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7133 -0.7934 -2.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0134 0.7854 -2.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7852 -2.0522 0.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5479 -1.8996 -0.5846 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0228 -2.1202 -1.2906 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2744 1.0668 2.7755 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0808 0.4510 2.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0051 2.0505 2.0712 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1895 -0.7670 0.9321 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2005 2.1750 0.7863 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4941 2.5453 0.7736 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4053 2.0027 -0.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0205 0.9056 2.7368 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8424 -0.8346 2.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1876 1.1264 2.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1066 -0.3945 3.0533 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0280 -1.5075 1.3509 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3879 1.1469 0.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0740 -0.6336 -2.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4147 0.8658 -1.3966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5015 -0.5293 -1.3957 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2792 -2.7231 -1.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5288 -2.9218 0.3381 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6027 -3.2377 -0.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7761 -1.5238 -0.0165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9751 -1.1383 -2.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4360 0.5465 -2.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7660 -0.7471 -2.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2550 0.8915 -2.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1796 2.5643 0.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1781 2.5988 -1.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5706 2.3291 -1.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2065 0.4564 1.9620 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0391 -1.7221 -0.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8898 -1.8405 1.6698 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 5 7 1 0 7 8 1 1 8 9 1 0 7 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 6 25 27 1 0 27 28 1 0 25 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 15 34 1 0 34 35 1 0 35 2 1 0 34 7 1 0 32 13 1 0 32 18 1 0 29 19 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 1 6 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 10 49 1 6 11 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 14 54 1 0 14 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 18 59 1 1 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 23 67 1 1 24 68 1 0 26 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 29 75 1 1 30 76 1 0 30 77 1 0 31 78 1 0 31 79 1 0 33 80 1 0 33 81 1 0 33 82 1 0 34 83 1 1 35 84 1 0 35 85 1 0 M END

Standard InCHIKey	SPCSEMLFKVZFJN-DGNDGBPUSA-N
Standard InCHI	InChI=1S/C30H50O5/c1-25(2)13-19-18-7-8-21-26(3)11-10-22(33)27(4,16-31)20(26)9-12-28(21,5)29(18,6)15-24(35)30(19,17-32)23(34)14-25/h7,19-24,31-35H,8-17H2,1-6H3/t19-,20+,21+,22-,23-,24-,26-,27-,28+,29+,30+/m0/s1
SMILES	CC1(C)C[C@H](O)[C@]2(CO)[C@@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	490.37	Volume:	525.968 ? Van der Waals volume.
Dense:	0.932	LogP:	3.519 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.584 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.524 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	101.15 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.376	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.113	Fsp³:	0.933
MCE-18:	107.586 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.394	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.368	Promiscuous compounds:	0.168

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.495	MDCK Permeability:	-5.013
Pgp-inhibitor:	0.128	Pgp-substrate:	0.15
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):	0.015
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	0.368
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988	MRP1:	0.088
Plasma Protein Binding (PPB):	79.347%	Volume Distribution (VD):	-0.033
Fu:	22.057% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.002	BCRP inhibitor:	0.958
BSEP inhibitor:	0.963

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.424	CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.095
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.243
HLM stability:	0.051 ? 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):

7.477

Half-life (T1/2):

1.491

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.104
Human Hepatotoxicity (H-HT):	0.475	Drug-induced Liver Injury (DILI):	0.083
AMES Toxicity:	0.466	Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.847	Skin Sensitization:	0.995
Carcinogencity:	0.981	Eye Corrosion:	0.001
Eye Irritation:	0.374	Respiratory Toxicity:	0.965
Drug-induced Neurotoxicity:	0.127	Ototoxicity:	0.648
Hematotoxicity:	0.526	Drug-induced Nephrotoxicity:	0.925
Genotoxicity:	0.465	RPMI-8226 Immunitoxicity:	0.093
A549 Cytotoxicity:	0.913	Hek293 Cytotoxicity:	0.643
BCF:	1.198 ? 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:	3.578 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.241 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.305 ? 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
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11274-011-0870-8]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-014-9655-8]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29166	Gymnema sylvestre	Species	Apocynaceae	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 NPC580585 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	27878
0.1-0.2	18528
0.2-0.3	2598
0.3-0.4	660
0.4-0.5	147
0.5-0.6	34
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8491	Intermediate Similarity	NPC311078
0.7857	Intermediate Similarity	NPC230295
0.7857	Intermediate Similarity	NPC253402
0.7857	Intermediate Similarity	NPC98386
0.7193	Intermediate Similarity	NPC196753
0.678	Remote Similarity	NPC253807
0.678	Remote Similarity	NPC158662
0.6667	Remote Similarity	NPC159168
0.6508	Remote Similarity	NPC213412
0.6393	Remote Similarity	NPC53744
0.6393	Remote Similarity	NPC238992
0.6377	Remote Similarity	NPC258547
0.6333	Remote Similarity	NPC101475
0.6333	Remote Similarity	NPC34177
0.5833	Remote Similarity	NPC290598
0.5833	Remote Similarity	NPC30590
0.5797	Remote Similarity	NPC294360
0.5672	Remote Similarity	NPC270768
0.5672	Remote Similarity	NPC59263
0.5672	Remote Similarity	NPC210106
0.5672	Remote Similarity	NPC488519
0.5652	Remote Similarity	NPC263393
0.5556	Remote Similarity	NPC283343
0.5469	Remote Similarity	NPC235341
0.5469	Remote Similarity	NPC478657
0.5441	Remote Similarity	NPC229281
0.5441	Remote Similarity	NPC121798
0.5441	Remote Similarity	NPC234346
0.5429	Remote Similarity	NPC191412
0.5429	Remote Similarity	NPC114159
0.5429	Remote Similarity	NPC6818
0.5362	Remote Similarity	NPC61543
0.5362	Remote Similarity	NPC293048
0.5362	Remote Similarity	NPC225585
0.5294	Remote Similarity	NPC99254
0.5278	Remote Similarity	NPC116457
0.5256	Remote Similarity	NPC237503
0.5231	Remote Similarity	NPC480924
0.5224	Remote Similarity	NPC246708
0.5211	Remote Similarity	NPC480919
0.5156	Remote Similarity	NPC474989
0.5139	Remote Similarity	NPC127689
0.5139	Remote Similarity	NPC130520
0.5077	Remote Similarity	NPC132478
0.5077	Remote Similarity	NPC237344
0.5075	Remote Similarity	NPC480950
0.507	Remote Similarity	NPC164349
0.5067	Remote Similarity	NPC473160

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC580585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8146
0.1-0.2	970
0.2-0.3	30
0.3-0.4	2
0.4-0.5	1
0.5-0.6	0
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
0.6406	Remote Similarity	NPD7645	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