NPASS Compound

Natural Product: NPC544348

Natural Product ID	NPC544348
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gymnestrogenin
IUPAC Name	(3~{S},4~{a}~{S},5~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},9~{R},10~{S},12~{a}~{R},14~{b}~{S})-4~{a},9-bis(hydroxymethyl)-2,2,6~{a},6~{b},9,12~{a}-hexamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-3,5,10-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 -5.4883 0.9157 -2.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5022 1.3309 -1.0580 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5172 2.8474 -1.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1122 0.8811 -1.3872 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7990 -0.5328 -1.0244 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3329 -0.6426 -0.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5810 -0.8026 -1.8763 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8854 -0.9325 -1.8822 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3809 -0.2291 -0.6358 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8537 -0.0025 -0.6530 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6344 -1.1666 -1.2037 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0970 1.1524 -1.6243 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5094 1.6306 -1.6097 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0749 1.8995 -0.2652 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4745 1.9314 -0.3979 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6983 0.9426 0.8168 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7196 -0.1445 1.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7328 1.7976 2.1020 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0321 2.3148 2.2696 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3065 0.4531 0.6900 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9378 -0.6162 1.6894 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4096 -0.5004 1.8074 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7646 -0.9202 0.5119 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8308 -2.4253 0.4626 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7172 -0.5744 0.5061 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8874 0.7143 1.2457 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4946 -1.6089 1.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9517 -1.2174 1.3982 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5451 -2.1886 2.2105 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6085 -1.1683 0.0429 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8292 -2.6448 -0.3438 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5932 -3.2078 0.6665 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9975 -0.6305 0.2351 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9631 0.8572 0.2920 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2350 1.4133 0.4816 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3033 -0.1181 -2.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3711 1.6243 -2.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4954 1.0746 -1.7341 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5046 3.2521 -0.0097 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4120 3.2604 -1.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6383 3.2764 -1.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3802 1.6285 -1.0047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0295 1.0625 -2.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0622 -1.1027 -1.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0722 -0.8477 -2.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1564 -2.0300 -1.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3509 -0.5323 -2.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9100 0.8004 -0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6325 -0.8367 -1.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8756 -1.9489 -0.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0969 -1.5181 -2.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4309 2.0151 -1.3997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8629 0.8547 -2.6677 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4986 2.6098 -2.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2250 1.0101 -2.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7846 2.9571 0.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7316 2.3623 -1.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2347 -0.4705 0.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2724 -0.9643 1.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5441 0.2749 1.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4122 1.2519 2.9842 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0645 2.6718 1.9710 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9603 3.1038 2.8655 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6536 1.3420 0.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2542 -1.6191 1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3202 -0.4028 2.7035 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0751 -1.1150 2.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2826 0.5876 1.9943 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8257 -2.8437 0.3488 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4704 -2.7762 1.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1809 -2.8759 -0.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1952 1.5080 0.9888 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8832 1.1453 1.2577 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6917 0.4578 2.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 -2.6133 0.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1336 -1.6223 2.3857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1195 -0.2709 1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9911 -2.9873 2.3524 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8839 -3.1729 -0.4877 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4645 -2.6370 -1.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2056 -3.9094 0.3390 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6747 -0.9559 -0.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3862 -1.0061 1.2027 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2458 1.2139 1.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6833 0.9058 1.2005 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 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 16 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 6 31 32 1 0 30 33 1 0 33 34 1 0 34 35 1 0 34 2 1 0 30 5 1 0 25 6 1 0 23 9 1 0 20 10 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 6 7 45 1 0 8 46 1 0 8 47 1 0 9 48 1 6 11 49 1 0 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 1 15 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 20 64 1 1 21 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 28 77 1 1 29 78 1 0 31 79 1 0 31 80 1 0 32 81 1 0 33 82 1 0 33 83 1 0 34 84 1 1 35 85 1 0 M END

Standard InCHIKey	SIBYGGBNBRCVQI-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)14-24(35)30(19,17-32)15-23(25)34/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]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@H](O)[C@@]2(CO)C[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	490.37	Volume:	525.968 ? Van der Waals volume.
Dense:	0.932	LogP:	2.923 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.112 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.461 ? 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:	5.237	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:	0.422	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:	0.391	Promiscuous compounds:	0.133

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091	MDCK Permeability:	-4.75
Pgp-inhibitor:	0.004	Pgp-substrate:	0.392
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):	0.027
20% Bioavailability (F20%):	0.986	30% Bioavailability (F30%):	0.148
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.893	MRP1:	0.145
Plasma Protein Binding (PPB):	82.226%	Volume Distribution (VD):	-0.142
Fu:	16.813% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.025	BCRP inhibitor:	0.97
BSEP inhibitor:	0.71

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.975	CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.079
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.751
HLM stability:	0.08 ? 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):

8.568

Half-life (T1/2):

1.049

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.078
Human Hepatotoxicity (H-HT):	0.586	Drug-induced Liver Injury (DILI):	0.139
AMES Toxicity:	0.689	Rat Oral Acute Toxicity:	0.688
Maximum Recommended Daily Dose:	0.594	Skin Sensitization:	0.985
Carcinogencity:	0.943	Eye Corrosion:	0.0
Eye Irritation:	0.258	Respiratory Toxicity:	0.817
Drug-induced Neurotoxicity:	0.053	Ototoxicity:	0.729
Hematotoxicity:	0.6	Drug-induced Nephrotoxicity:	0.705
Genotoxicity:	0.405	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.96	Hek293 Cytotoxicity:	0.53
BCF:	1.171 ? 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:	3.544 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.139 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.262 ? 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 NPC544348 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	25695
0.1-0.2	20279
0.2-0.3	3022
0.3-0.4	681
0.4-0.5	138
0.5-0.6	32
0.6-0.7	8
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
0.7586	Intermediate Similarity	NPC253402
0.6833	Remote Similarity	NPC253807
0.6833	Remote Similarity	NPC158662
0.6452	Remote Similarity	NPC230295
0.6452	Remote Similarity	NPC159168
0.6452	Remote Similarity	NPC98386
0.6393	Remote Similarity	NPC196753
0.6129	Remote Similarity	NPC311078
0.6061	Remote Similarity	NPC213412
0.5972	Remote Similarity	NPC258547
0.5735	Remote Similarity	NPC229281
0.5714	Remote Similarity	NPC263393
0.5692	Remote Similarity	NPC53744
0.5625	Remote Similarity	NPC34177
0.5507	Remote Similarity	NPC270768
0.5507	Remote Similarity	NPC59263
0.5507	Remote Similarity	NPC210106
0.5507	Remote Similarity	NPC121798
0.5507	Remote Similarity	NPC234346
0.5493	Remote Similarity	NPC191412
0.5493	Remote Similarity	NPC114159
0.5493	Remote Similarity	NPC6818
0.5429	Remote Similarity	NPC61543
0.5429	Remote Similarity	NPC293048
0.5429	Remote Similarity	NPC225585
0.5385	Remote Similarity	NPC101475
0.5342	Remote Similarity	NPC116457
0.5303	Remote Similarity	NPC235341
0.5286	Remote Similarity	NPC488519
0.5205	Remote Similarity	NPC127689
0.5205	Remote Similarity	NPC130520
0.52	Remote Similarity	NPC86368
0.52	Remote Similarity	NPC283343
0.5156	Remote Similarity	NPC290598
0.5156	Remote Similarity	NPC30590
0.5152	Remote Similarity	NPC237344
0.5147	Remote Similarity	NPC133954
0.5139	Remote Similarity	NPC164349
0.5132	Remote Similarity	NPC473160
0.5125	Remote Similarity	NPC237503
0.5075	Remote Similarity	NPC480924

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC544348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7918
0.1-0.2	1204
0.2-0.3	24
0.3-0.4	2
0.4-0.5	1
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
0.597	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