NPASS Compound

Natural Product: NPC576406

Natural Product ID	NPC576406
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sitakisogenin
IUPAC Name	(3~{S},4~{a}~{S},5~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},10~{S},12~{a}~{R},14~{b}~{S})-4~{a}-(hydroxymethyl)-2,2,6~{a},6~{b},9,9,12~{a}-heptamethyl-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 84 88 0 0 0 0 0 0 0 0999 V2000 -5.0296 -2.4741 2.1431 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4319 -1.6676 0.9714 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4498 -2.6264 -0.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0830 -1.1348 1.2925 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7756 0.2591 0.8368 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3275 0.4910 0.5877 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6008 0.9100 1.6000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8290 1.2121 1.6242 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4404 0.3849 0.4819 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9334 0.4328 0.5618 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5033 1.7922 0.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -0.3301 1.8572 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5189 -1.1246 1.7876 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5418 -0.6828 0.8001 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2085 0.4952 1.2088 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9855 -0.5468 -0.5845 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2648 -1.8933 -1.2839 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7738 0.4857 -1.3136 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5229 -0.3802 -0.5473 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9292 -0.0151 -1.9015 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4313 -0.2798 -1.8492 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7715 0.5959 -0.8028 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8556 2.0002 -1.3601 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7030 0.2672 -0.7133 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8450 -1.1511 -1.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5153 1.1042 -1.7079 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9615 0.7367 -1.6358 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6289 1.6746 -2.4712 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5869 0.8174 -0.2856 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7707 2.3185 -0.0173 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5117 2.9412 -0.9905 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9674 0.2452 -0.3983 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4006 -0.5204 0.8009 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3361 0.2711 1.9410 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5407 -3.4403 2.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0887 -2.6802 1.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0836 -1.8570 3.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4558 -3.1292 -0.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1779 -2.1953 -1.1558 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7331 -3.4450 0.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2783 -1.8822 1.0084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0114 -1.2205 2.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0951 0.8877 1.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1170 1.0617 2.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0061 2.2776 1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3369 0.8239 2.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1685 -0.6785 0.7865 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9610 1.9760 1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2999 2.0609 0.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7464 2.5924 0.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4494 -0.9970 2.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3891 0.4004 2.7123 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2874 -2.2052 1.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0225 -1.1485 2.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3622 -1.4609 0.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3019 0.5277 2.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4634 -2.5843 -0.9684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2834 -2.2310 -0.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2764 -1.7513 -2.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5673 0.0020 -1.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2159 1.1354 -1.9824 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3977 1.1138 -0.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0983 -1.4070 -0.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2072 0.9674 -2.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3389 -0.7577 -2.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3399 -1.3452 -1.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0792 -0.0574 -2.8761 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4315 1.9515 -2.3896 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8925 2.3481 -1.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3638 2.7534 -0.7254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9026 -1.4874 -1.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3338 -1.9022 -0.6042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5213 -1.1303 -2.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4097 2.1757 -1.5515 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2122 0.8613 -2.7564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2095 -0.2325 -2.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0742 1.9028 -3.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2784 2.3672 0.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7713 2.7777 0.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2877 3.3911 -0.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1076 -0.4046 -1.2937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7471 1.0517 -0.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4385 -0.8793 0.6188 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2803 0.4940 2.1960 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 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 1 30 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 33 2 1 0 29 5 1 0 24 6 1 0 22 9 1 0 19 10 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 1 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 1 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 6 15 56 1 0 17 57 1 0 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 18 62 1 0 19 63 1 1 20 64 1 0 20 65 1 0 21 66 1 0 21 67 1 0 23 68 1 0 23 69 1 0 23 70 1 0 25 71 1 0 25 72 1 0 25 73 1 0 26 74 1 0 26 75 1 0 27 76 1 6 28 77 1 0 30 78 1 0 30 79 1 0 31 80 1 0 32 81 1 0 32 82 1 0 33 83 1 6 34 84 1 0 M END

Standard InCHIKey	XRTLKHZNPLDRSH-XRWCDFGBSA-N
Standard InCHI	InChI=1S/C30H50O4/c1-25(2)14-19-18-8-9-21-27(5)12-11-22(32)26(3,4)20(27)10-13-28(21,6)29(18,7)15-24(34)30(19,17-31)16-23(25)33/h8,19-24,31-34H,9-17H2,1-7H3/t19-,20-,21+,22-,23-,24-,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)(C)[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:	474.37	Volume:	517.178 ? Van der Waals volume.
Dense:	0.917	LogP:	3.746 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.739 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.123 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.399	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.101	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:	0.501	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.389	Promiscuous compounds:	0.08

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.127	MDCK Permeability:	-4.774
Pgp-inhibitor:	0.002	Pgp-substrate:	0.863
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):	0.013
20% Bioavailability (F20%):	0.962	30% Bioavailability (F30%):	0.326
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956	MRP1:	0.588
Plasma Protein Binding (PPB):	91.074%	Volume Distribution (VD):	-0.138
Fu:	8.162% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.931	BCRP inhibitor:	0.833
BSEP inhibitor:	0.212

ADMET: Metabolism

CYP1A2-inhibitor:	0.029	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.99
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.028	CYP3A4-substrate:	0.189
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.94
HLM stability:	0.622 ? 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):

10.007

Half-life (T1/2):

0.738

ADMET: Toxicity

hERG Blockers:	0.032	hERG Blockers (10um):	0.135
Human Hepatotoxicity (H-HT):	0.569	Drug-induced Liver Injury (DILI):	0.184
AMES Toxicity:	0.767	Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.741	Skin Sensitization:	0.968
Carcinogencity:	0.937	Eye Corrosion:	0.001
Eye Irritation:	0.353	Respiratory Toxicity:	0.89
Drug-induced Neurotoxicity:	0.083	Ototoxicity:	0.637
Hematotoxicity:	0.541	Drug-induced Nephrotoxicity:	0.729
Genotoxicity:	0.7	RPMI-8226 Immunitoxicity:	0.085
A549 Cytotoxicity:	0.926	Hek293 Cytotoxicity:	0.589
BCF:	1.508 ? 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:	3.693 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.26 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.513 ? 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 NPC576406 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	23128
0.1-0.2	22103
0.2-0.3	3442
0.3-0.4	956
0.4-0.5	146
0.5-0.6	65
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8036	Intermediate Similarity	NPC253807
0.8036	Intermediate Similarity	NPC158662
0.7586	Intermediate Similarity	NPC159168
0.7241	Intermediate Similarity	NPC311078
0.6667	Remote Similarity	NPC34177
0.6452	Remote Similarity	NPC253402
0.6393	Remote Similarity	NPC101475
0.629	Remote Similarity	NPC235341
0.6212	Remote Similarity	NPC488519
0.6167	Remote Similarity	NPC290598
0.6167	Remote Similarity	NPC30590
0.6129	Remote Similarity	NPC237344
0.6056	Remote Similarity	NPC283343
0.6032	Remote Similarity	NPC480924
0.6029	Remote Similarity	NPC164349
0.5972	Remote Similarity	NPC473160
0.5873	Remote Similarity	NPC132478
0.5857	Remote Similarity	NPC294360
0.5758	Remote Similarity	NPC246708
0.5692	Remote Similarity	NPC238992
0.5645	Remote Similarity	NPC27765
0.5645	Remote Similarity	NPC122418
0.5645	Remote Similarity	NPC491014
0.5625	Remote Similarity	NPC196753
0.5616	Remote Similarity	NPC471433
0.5616	Remote Similarity	NPC471432
0.5606	Remote Similarity	NPC480950
0.5588	Remote Similarity	NPC187722
0.5538	Remote Similarity	NPC40394
0.5507	Remote Similarity	NPC7260
0.5507	Remote Similarity	NPC182797
0.5507	Remote Similarity	NPC210037
0.5507	Remote Similarity	NPC120968
0.5507	Remote Similarity	NPC171203
0.5507	Remote Similarity	NPC307426
0.5507	Remote Similarity	NPC98442
0.5507	Remote Similarity	NPC242468
0.5507	Remote Similarity	NPC227467
0.5507	Remote Similarity	NPC273621
0.5507	Remote Similarity	NPC52169
0.5507	Remote Similarity	NPC488562
0.5469	Remote Similarity	NPC474989
0.5455	Remote Similarity	NPC230295
0.5455	Remote Similarity	NPC95594
0.5455	Remote Similarity	NPC98386
0.5405	Remote Similarity	NPC86368
0.5397	Remote Similarity	NPC120098
0.5373	Remote Similarity	NPC133954
0.5362	Remote Similarity	NPC480946
0.5362	Remote Similarity	NPC130577
0.5362	Remote Similarity	NPC142415
0.5362	Remote Similarity	NPC102683
0.5352	Remote Similarity	NPC202728
0.5352	Remote Similarity	NPC158059
0.5352	Remote Similarity	NPC228784
0.5352	Remote Similarity	NPC49776
0.5352	Remote Similarity	NPC324341
0.5352	Remote Similarity	NPC63118
0.5352	Remote Similarity	NPC474436
0.5352	Remote Similarity	NPC601810
0.5333	Remote Similarity	NPC258547
0.5286	Remote Similarity	NPC51700
0.5286	Remote Similarity	NPC88716
0.5286	Remote Similarity	NPC68160
0.5278	Remote Similarity	NPC480919
0.5224	Remote Similarity	NPC470588
0.5217	Remote Similarity	NPC477872
0.52	Remote Similarity	NPC88349
0.5143	Remote Similarity	NPC274330
0.5143	Remote Similarity	NPC213412
0.5143	Remote Similarity	NPC198664
0.5143	Remote Similarity	NPC2539
0.5143	Remote Similarity	NPC610937
0.5139	Remote Similarity	NPC293564
0.5075	Remote Similarity	NPC291379
0.5072	Remote Similarity	NPC40552
0.507	Remote Similarity	NPC112866
0.507	Remote Similarity	NPC606443
0.5068	Remote Similarity	NPC263393
0.5063	Remote Similarity	NPC167383

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC576406 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7607
0.1-0.2	1495
0.2-0.3	43
0.3-0.4	4
0.4-0.5	0
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
0.5286	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