NPASS Compound

Natural Product: NPC516234

Natural Product ID	NPC516234
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	methyl (2~{R},4~{a}~{R},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},9~{R},10~{S},12~{a}~{R},14~{b}~{S})-10-hydroxy-2,9-bis(hydroxymethyl)-2,6~{a},6~{b},9,12~{a}-pentamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate
IUPAC Name	methyl (2~{R},4~{a}~{R},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},9~{R},10~{S},12~{a}~{R},14~{b}~{S})-10-hydroxy-2,9-bis(hydroxymethyl)-2,6~{a},6~{b},9,12~{a}-pentamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate
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 86 90 0 0 0 0 0 0 0 0999 V2000 -3.7953 -3.9177 -3.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8040 -2.7352 -2.3234 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3735 -2.6574 -0.9909 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9680 -3.6989 -0.4634 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4285 -1.3194 -0.2817 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9085 -0.9949 -0.3407 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1542 -0.1546 -1.5474 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4408 1.1691 -1.5170 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5902 1.7769 -2.9078 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1894 2.0864 -0.5738 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5795 3.3416 -0.4958 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0132 1.0663 -1.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5770 -0.3539 -1.0508 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1703 -0.5782 -0.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3229 -0.7779 -1.6166 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1253 -1.0236 -1.4562 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5036 -0.2246 -0.2188 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9642 0.0318 -0.1462 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8457 -1.1649 -0.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2862 0.9896 -1.2964 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1492 2.1362 -0.9117 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2409 1.8258 0.0474 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2213 1.0010 -0.5084 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6464 1.2708 1.3101 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6107 0.3079 1.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5535 2.4684 2.2733 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7384 3.4463 1.7087 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2699 0.7752 1.1223 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7893 -0.0883 2.2705 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2735 -0.0586 2.1701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7713 -0.7783 0.9298 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9801 -2.2561 1.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7088 -0.5836 0.7329 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1045 0.6005 1.5731 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 -1.7162 1.3720 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9710 -1.6259 1.1074 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3792 -3.6755 -4.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7954 -4.3398 -3.2329 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0963 -4.6656 -2.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5110 -1.9053 -0.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2011 -0.3751 0.5430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9312 -0.7167 -2.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2682 0.0291 -1.5853 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4672 0.9334 -3.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8381 2.5603 -3.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6254 2.1886 -2.9525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3117 1.6575 0.4400 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2066 2.2404 -0.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1697 3.8951 0.0753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8378 1.6924 -0.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4070 1.5537 -1.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7270 -0.6615 -2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6527 -0.7761 -2.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3748 -2.0943 -1.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7144 -0.6574 -2.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0499 0.7998 -0.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4066 -1.4654 0.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2109 -2.0272 -0.6302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5572 -1.0573 -1.2104 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7555 0.4534 -2.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3519 1.4442 -1.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5488 2.9972 -0.5713 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6464 2.5005 -1.8602 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7828 2.8034 0.2285 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1258 1.2393 -0.1540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1665 -0.4507 2.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2850 -0.1052 1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3320 0.8765 2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5594 2.9163 2.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0995 2.1705 3.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2309 4.2263 1.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5884 1.6645 1.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2211 -1.0778 2.3088 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0443 0.4486 3.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0407 1.0165 2.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9448 -0.5149 3.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4765 -2.4881 2.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7024 -2.9055 0.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0617 -2.4911 1.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7101 1.5601 1.2871 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7566 0.3501 2.5946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 0.6302 1.7770 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3804 -1.7308 2.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1944 -2.7171 1.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4469 -2.6178 1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4838 -0.9172 1.7906 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 5 3 1 6 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 1 0 8 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 24 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 1 33 35 1 0 35 36 1 0 13 5 1 0 33 14 1 0 36 5 1 0 31 17 1 0 28 18 1 0 1 37 1 0 1 38 1 0 1 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 9 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 6 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 6 19 57 1 0 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 1 23 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 28 72 1 6 29 73 1 0 29 74 1 0 30 75 1 0 30 76 1 0 32 77 1 0 32 78 1 0 32 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 35 83 1 0 35 84 1 0 36 85 1 0 36 86 1 0 M END

Standard InCHIKey	QCYVRROBMNKQIM-QATYITTFSA-N
Standard InCHI	InChI=1S/C31H50O5/c1-26(18-32)13-15-31(25(35)36-6)16-14-29(4)20(21(31)17-26)7-8-23-27(2)11-10-24(34)28(3,19-33)22(27)9-12-30(23,29)5/h7,21-24,32-34H,8-19H2,1-6H3/t21-,22+,23+,24-,26+,27-,28-,29+,30+,31-/m0/s1
SMILES	COC(=O)[C@]12CC[C@@](C)(CO)C[C@H]1C1=CC[C@@H]3[C@@]4(C)CC[C@H](O)[C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	502.37	Volume:	540.628 ? Van der Waals volume.
Dense:	0.929	LogP:	3.973 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.828 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.045 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	27.0
TPSA:	86.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.362	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.974	Fsp³:	0.903
MCE-18:	104.441 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.803	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.385	Promiscuous compounds:	0.265

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.389	MDCK Permeability:	-4.991
Pgp-inhibitor:	0.069	Pgp-substrate:	0.02
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):	0.004
20% Bioavailability (F20%):	0.992	30% Bioavailability (F30%):	0.142
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.9	MRP1:	0.431
Plasma Protein Binding (PPB):	81.792%	Volume Distribution (VD):	-0.043
Fu:	18.77% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.04	BCRP inhibitor:	0.987
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.06	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.451	CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.006	CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.744	CYP3A4-substrate:	0.932
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.861
HLM stability:	0.252 ? 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):

5.945

Half-life (T1/2):

0.833

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.089
Human Hepatotoxicity (H-HT):	0.82	Drug-induced Liver Injury (DILI):	0.044
AMES Toxicity:	0.193	Rat Oral Acute Toxicity:	0.275
Maximum Recommended Daily Dose:	0.449	Skin Sensitization:	0.984
Carcinogencity:	0.895	Eye Corrosion:	0.0
Eye Irritation:	0.144	Respiratory Toxicity:	0.717
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.795
Hematotoxicity:	0.458	Drug-induced Nephrotoxicity:	0.857
Genotoxicity:	0.033	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.632	Hek293 Cytotoxicity:	0.194
BCF:	1.262 ? 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:	3.762 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.549 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.662 ? 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
NPO55292	Kalidium foliatum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC516234 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	17413
0.1-0.2	26977
0.2-0.3	4359
0.3-0.4	845
0.4-0.5	199
0.5-0.6	56
0.6-0.7	7
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
0.7302	Intermediate Similarity	NPC246708
0.6579	Remote Similarity	NPC237503
0.6406	Remote Similarity	NPC196753
0.6324	Remote Similarity	NPC213412
0.6269	Remote Similarity	NPC40552
0.6212	Remote Similarity	NPC230295
0.6212	Remote Similarity	NPC98386
0.6	Remote Similarity	NPC68419
0.5882	Remote Similarity	NPC29069
0.5857	Remote Similarity	NPC136313
0.5775	Remote Similarity	NPC121798
0.5775	Remote Similarity	NPC234346
0.5753	Remote Similarity	NPC263393
0.5735	Remote Similarity	NPC253402
0.5696	Remote Similarity	NPC167383
0.5672	Remote Similarity	NPC101475
0.5652	Remote Similarity	NPC267517
0.5588	Remote Similarity	NPC235341
0.5584	Remote Similarity	NPC258547
0.5556	Remote Similarity	NPC488519
0.5556	Remote Similarity	NPC481361
0.5507	Remote Similarity	NPC470588
0.5493	Remote Similarity	NPC162107
0.5493	Remote Similarity	NPC46912
0.5488	Remote Similarity	NPC37739
0.5455	Remote Similarity	NPC290598
0.5455	Remote Similarity	NPC30590
0.5422	Remote Similarity	NPC137917
0.5405	Remote Similarity	NPC49776
0.5405	Remote Similarity	NPC63118
0.5405	Remote Similarity	NPC474436
0.5402	Remote Similarity	NPC90856
0.5342	Remote Similarity	NPC270768
0.5342	Remote Similarity	NPC59263
0.5342	Remote Similarity	NPC210106
0.5342	Remote Similarity	NPC229281
0.5319	Remote Similarity	NPC102439
0.5286	Remote Similarity	NPC53744
0.527	Remote Similarity	NPC61543
0.527	Remote Similarity	NPC293048
0.527	Remote Similarity	NPC225585
0.5224	Remote Similarity	NPC27765
0.5224	Remote Similarity	NPC122418
0.5224	Remote Similarity	NPC491014
0.5217	Remote Similarity	NPC311078
0.5205	Remote Similarity	NPC214756
0.5143	Remote Similarity	NPC253807
0.5143	Remote Similarity	NPC40394
0.5143	Remote Similarity	NPC158662
0.5135	Remote Similarity	NPC182797
0.5135	Remote Similarity	NPC307335
0.5135	Remote Similarity	NPC74855
0.5135	Remote Similarity	NPC52169
0.5135	Remote Similarity	NPC480934
0.5135	Remote Similarity	NPC488562
0.5132	Remote Similarity	NPC191412
0.5132	Remote Similarity	NPC114159
0.5132	Remote Similarity	NPC6818
0.5119	Remote Similarity	NPC306746
0.507	Remote Similarity	NPC159168
0.507	Remote Similarity	NPC95594
0.5065	Remote Similarity	NPC127689
0.5065	Remote Similarity	NPC294360
0.5065	Remote Similarity	NPC130520

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC516234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6846
0.1-0.2	2236
0.2-0.3	64
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
0.6471	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