NPASS Compound

Natural Product: NPC567776

Natural Product ID	NPC567776
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(4~{a}~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},12~{a}~{R},14~{b}~{S})-10-acetoxy-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-4~{a}-carboxylic acid
IUPAC Name	(4~{a}~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},12~{a}~{R},14~{b}~{S})-10-acetoxy-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-4~{a}-carboxylic acid
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 8.7435 1.2443 0.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3432 1.1431 -0.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1975 1.4496 -1.6079 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2874 0.7441 0.4202 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0055 0.6801 -0.1634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1152 1.5700 0.6667 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8039 1.7423 -0.0159 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1866 0.4191 -0.4925 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2753 0.4233 -1.9768 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7987 0.3802 0.0698 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0622 1.6027 -0.3603 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 1.3816 -0.4775 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0255 0.3290 0.0436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4914 0.2696 -0.1693 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0743 1.4278 0.6215 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5629 1.4483 0.6734 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9443 2.3442 1.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1099 2.1465 -0.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1399 0.0616 0.8663 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0381 -0.9152 1.3040 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1314 -1.0370 0.0888 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0459 -1.3828 -1.0404 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1421 -0.5848 -2.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7897 -2.5371 -1.0764 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1756 -2.1812 0.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9848 -1.9292 1.0734 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2312 -0.6953 0.7928 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8935 -0.0217 2.1316 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0556 -0.8940 -0.0207 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3538 -1.3880 -1.3559 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9131 -1.9858 0.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2578 -1.9762 -0.1070 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9723 -0.6863 0.1696 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4197 -0.7122 -0.1170 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8258 -1.4281 -1.3607 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1106 -1.4151 1.0617 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9847 2.3451 0.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3963 0.7712 -0.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8499 0.8217 1.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0770 0.9738 -1.2045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5479 2.5809 0.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0167 1.1095 1.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9513 2.4523 -0.8604 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1431 2.2767 0.7021 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6423 -0.5269 -2.4110 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3309 0.6945 -2.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0008 1.2026 -2.3634 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9618 0.5260 1.1882 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1521 2.4596 0.3777 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4407 2.0550 -1.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9840 2.1199 -1.0164 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6515 0.5574 -1.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7223 2.3532 0.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6803 1.4661 1.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5753 1.8804 2.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0023 2.5998 1.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3598 3.2806 1.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9408 1.5206 -0.9470 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5196 3.1370 -0.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3514 2.2057 -1.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6311 -0.2983 -0.0478 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8689 0.1038 1.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5425 -1.8920 1.4507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5304 -0.5279 2.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6851 -2.5029 -1.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9760 -2.5714 -0.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7569 -3.0083 0.7218 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3874 -2.8747 1.0617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3872 -1.9101 2.1338 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7963 -0.2283 2.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0512 -0.4863 2.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8333 1.0614 2.0525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4700 -1.4826 -2.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6359 -2.4780 -1.2009 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2329 -0.9210 -1.7976 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5101 -3.0132 0.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0700 -1.8818 1.6720 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1657 -2.2252 -1.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8579 -2.7909 0.3649 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8474 -0.5040 1.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1559 -2.2367 -1.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0251 -0.7061 -2.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8285 -1.9110 -1.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1550 -1.0653 1.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6438 -1.0490 2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0389 -2.5003 0.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 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 6 22 23 2 0 22 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 34 5 1 0 33 8 1 0 29 10 1 0 27 13 1 0 21 14 1 0 1 37 1 0 1 38 1 0 1 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 1 11 49 1 0 11 50 1 0 12 51 1 0 14 52 1 6 15 53 1 0 15 54 1 0 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 30 73 1 0 30 74 1 0 30 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 33 80 1 1 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 36 86 1 0 M END

Standard InCHIKey	RIXNFYQZWDGQAE-SHHPMBJQSA-N
Standard InCHI	InChI=1S/C32H50O4/c1-20(33)36-25-12-13-29(6)23(28(25,4)5)11-14-31(8)24(29)10-9-21-22-19-27(2,3)15-17-32(22,26(34)35)18-16-30(21,31)7/h9,22-25H,10-19H2,1-8H3,(H,34,35)/t22-,23-,24+,25?,29-,30+,31+,32-/m0/s1
SMILES	CC(=O)OC1CC[C@]2(C)[C@H]3CC=C4[C@@H]5CC(C)(C)CC[C@]5(C(=O)O)CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	498.37	Volume:	546.497 ? Van der Waals volume.
Dense:	0.912	LogP:	3.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.728 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.311	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.624	Fsp³:	0.875
MCE-18:	106.667 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.872	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.467	Promiscuous compounds:	0.048

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.159	MDCK Permeability:	-4.86
Pgp-inhibitor:	0.424	Pgp-substrate:	0.0
PAMPA:	0.951 ? 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):	0.001
20% Bioavailability (F20%):	0.609	30% Bioavailability (F30%):	0.241
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306	MRP1:	0.952
Plasma Protein Binding (PPB):	93.914%	Volume Distribution (VD):	-0.325
Fu:	6.004% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.881	BCRP inhibitor:	0.016
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.016	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.989	CYP3A4-substrate:	0.947
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.033 ? 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):

2.495

Half-life (T1/2):

0.948

ADMET: Toxicity

hERG Blockers:	0.086	hERG Blockers (10um):	0.179
Human Hepatotoxicity (H-HT):	0.726	Drug-induced Liver Injury (DILI):	0.691
AMES Toxicity:	0.102	Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.597	Skin Sensitization:	0.815
Carcinogencity:	0.859	Eye Corrosion:	0.062
Eye Irritation:	0.647	Respiratory Toxicity:	0.781
Drug-induced Neurotoxicity:	0.113	Ototoxicity:	0.467
Hematotoxicity:	0.309	Drug-induced Nephrotoxicity:	0.652
Genotoxicity:	0.284	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.059	Hek293 Cytotoxicity:	0.21
BCF:	1.909 ? 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:	4.737 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.227 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.732 ? 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
NPO57230	Myrcia lingua	Genus	Myrtaceae	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 NPC567776 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	22586
0.1-0.2	23016
0.2-0.3	3113
0.3-0.4	748
0.4-0.5	223
0.5-0.6	117
0.6-0.7	49
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120840
0.7761	Intermediate Similarity	NPC296164
0.7761	Intermediate Similarity	NPC488521
0.7612	Intermediate Similarity	NPC608622
0.6974	Remote Similarity	NPC283849
0.6957	Remote Similarity	NPC485589
0.6901	Remote Similarity	NPC96580
0.6812	Remote Similarity	NPC200752
0.6806	Remote Similarity	NPC485588
0.6769	Remote Similarity	NPC604575
0.6753	Remote Similarity	NPC606107
0.6667	Remote Similarity	NPC158141
0.6618	Remote Similarity	NPC480946
0.6618	Remote Similarity	NPC130577
0.6618	Remote Similarity	NPC142415
0.6618	Remote Similarity	NPC102683
0.6582	Remote Similarity	NPC286347
0.6575	Remote Similarity	NPC485586
0.6571	Remote Similarity	NPC298554
0.6543	Remote Similarity	NPC284807
0.6543	Remote Similarity	NPC473538
0.6522	Remote Similarity	NPC156981
0.6512	Remote Similarity	NPC610795
0.6463	Remote Similarity	NPC191410
0.64	Remote Similarity	NPC23241
0.64	Remote Similarity	NPC481362
0.6386	Remote Similarity	NPC475472
0.6386	Remote Similarity	NPC475611
0.6364	Remote Similarity	NPC195334
0.6329	Remote Similarity	NPC28198
0.6329	Remote Similarity	NPC476123
0.6296	Remote Similarity	NPC100383
0.6286	Remote Similarity	NPC270768
0.6286	Remote Similarity	NPC59263
0.6286	Remote Similarity	NPC210106
0.6269	Remote Similarity	NPC224145
0.6203	Remote Similarity	NPC204407
0.6143	Remote Similarity	NPC191965
0.6118	Remote Similarity	NPC22676
0.6118	Remote Similarity	NPC164194
0.6092	Remote Similarity	NPC56713
0.6087	Remote Similarity	NPC280654
0.6056	Remote Similarity	NPC275809
0.6056	Remote Similarity	NPC84319
0.6056	Remote Similarity	NPC52021
0.6056	Remote Similarity	NPC599947
0.6027	Remote Similarity	NPC113989
0.6023	Remote Similarity	NPC127056
0.6	Remote Similarity	NPC162107
0.6	Remote Similarity	NPC171007
0.6	Remote Similarity	NPC46912
0.6	Remote Similarity	NPC469945
0.6	Remote Similarity	NPC190849
0.5972	Remote Similarity	NPC231063
0.5972	Remote Similarity	NPC282395
0.5972	Remote Similarity	NPC481360
0.5972	Remote Similarity	NPC110308
0.5955	Remote Similarity	NPC6377
0.5955	Remote Similarity	NPC488561
0.5955	Remote Similarity	NPC208381
0.5952	Remote Similarity	NPC294112
0.5921	Remote Similarity	NPC474727
0.5915	Remote Similarity	NPC30522
0.5909	Remote Similarity	NPC25605
0.5882	Remote Similarity	NPC290495
0.587	Remote Similarity	NPC180550
0.587	Remote Similarity	NPC35405
0.5857	Remote Similarity	NPC31031
0.5843	Remote Similarity	NPC114441
0.5843	Remote Similarity	NPC109079
0.5833	Remote Similarity	NPC282616
0.5833	Remote Similarity	NPC37038
0.5833	Remote Similarity	NPC286786
0.5795	Remote Similarity	NPC605663
0.5778	Remote Similarity	NPC472949
0.5753	Remote Similarity	NPC106112
0.5753	Remote Similarity	NPC261935
0.5745	Remote Similarity	NPC481082
0.5745	Remote Similarity	NPC73829
0.5745	Remote Similarity	NPC164419
0.5714	Remote Similarity	NPC22956
0.5714	Remote Similarity	NPC485587
0.5699	Remote Similarity	NPC104400
0.5699	Remote Similarity	NPC10320
0.5684	Remote Similarity	NPC119794
0.5647	Remote Similarity	NPC173569
0.5641	Remote Similarity	NPC230151
0.5641	Remote Similarity	NPC600880
0.5618	Remote Similarity	NPC136877
0.5616	Remote Similarity	NPC182797
0.5616	Remote Similarity	NPC52169
0.5616	Remote Similarity	NPC488562
0.56	Remote Similarity	NPC474963
0.5591	Remote Similarity	NPC114304
0.5579	Remote Similarity	NPC257468
0.557	Remote Similarity	NPC327179
0.557	Remote Similarity	NPC233012
0.5568	Remote Similarity	NPC270667
0.5567	Remote Similarity	NPC324875
0.5567	Remote Similarity	NPC292677
0.5556	Remote Similarity	NPC174679
0.5556	Remote Similarity	NPC279554
0.5556	Remote Similarity	NPC59804
0.5556	Remote Similarity	NPC485585
0.5542	Remote Similarity	NPC485882
0.5541	Remote Similarity	NPC470590
0.5541	Remote Similarity	NPC285184
0.5529	Remote Similarity	NPC242611
0.5521	Remote Similarity	NPC79718
0.55	Remote Similarity	NPC478836
0.5479	Remote Similarity	NPC10005
0.5479	Remote Similarity	NPC91525
0.5479	Remote Similarity	NPC198664
0.5444	Remote Similarity	NPC12288
0.5443	Remote Similarity	NPC601365
0.5412	Remote Similarity	NPC31839
0.5405	Remote Similarity	NPC121798
0.5405	Remote Similarity	NPC234346
0.54	Remote Similarity	NPC280941
0.54	Remote Similarity	NPC62725
0.54	Remote Similarity	NPC235772
0.5395	Remote Similarity	NPC480949
0.5375	Remote Similarity	NPC188833
0.5368	Remote Similarity	NPC601567
0.5368	Remote Similarity	NPC606631
0.5354	Remote Similarity	NPC488564
0.5342	Remote Similarity	NPC127855
0.5333	Remote Similarity	NPC23621
0.5309	Remote Similarity	NPC93744
0.5309	Remote Similarity	NPC476888
0.5301	Remote Similarity	NPC476890
0.5301	Remote Similarity	NPC476889
0.5281	Remote Similarity	NPC480938
0.5275	Remote Similarity	NPC172311
0.527	Remote Similarity	NPC4309
0.5263	Remote Similarity	NPC291028
0.5256	Remote Similarity	NPC488520
0.5256	Remote Similarity	NPC324063
0.5244	Remote Similarity	NPC603645
0.5222	Remote Similarity	NPC76999
0.5217	Remote Similarity	NPC132126
0.5204	Remote Similarity	NPC53520
0.52	Remote Similarity	NPC307282
0.52	Remote Similarity	NPC64872
0.52	Remote Similarity	NPC25906
0.5165	Remote Similarity	NPC198621
0.5165	Remote Similarity	NPC216940
0.5155	Remote Similarity	NPC139044
0.5155	Remote Similarity	NPC471383
0.5152	Remote Similarity	NPC276093
0.5143	Remote Similarity	NPC166422
0.5143	Remote Similarity	NPC219180
0.5143	Remote Similarity	NPC251263
0.5135	Remote Similarity	NPC267691
0.5132	Remote Similarity	NPC60755
0.5132	Remote Similarity	NPC77099
0.5132	Remote Similarity	NPC130278
0.5132	Remote Similarity	NPC472149
0.5132	Remote Similarity	NPC609452
0.5114	Remote Similarity	NPC43353
0.51	Remote Similarity	NPC323359
0.5067	Remote Similarity	NPC187722
0.5067	Remote Similarity	NPC329943
0.5065	Remote Similarity	NPC488523
0.5065	Remote Similarity	NPC228784
0.5065	Remote Similarity	NPC324341
0.5065	Remote Similarity	NPC601810
0.5063	Remote Similarity	NPC74751
0.5063	Remote Similarity	NPC222047
0.5047	Remote Similarity	NPC54636

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC567776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6231
0.1-0.2	2872
0.2-0.3	33
0.3-0.4	10
0.4-0.5	3
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
0.5063	Remote Similarity	NPD7748	Pre-clinical

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