NPASS Compound

Natural Product: NPC531559

Natural Product ID	NPC531559
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-1-(1-formylvinyl)-9-hydroxy-5~{a},5~{b},8,8,11~{a}-pentamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
IUPAC Name	(1~{R},3~{a}~{S},5~{a}~{R},5~{b}~{R},7~{a}~{R},9~{S},11~{a}~{R},11~{b}~{R},13~{a}~{R},13~{b}~{R})-1-(1-formylvinyl)-9-hydroxy-5~{a},5~{b},8,8,11~{a}-pentamethyl-1,2,3,4,5,6,7,7~{a},9,10,11,11~{b},12,13,13~{a},13~{b}-hexadecahydrocyclopenta[a]chrysene-3~{a}-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 80 84 0 0 0 0 0 0 0 0999 V2000 4.4186 0.7715 -2.8505 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4958 1.2176 -1.6082 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7120 2.6442 -1.4207 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8180 3.4010 -2.4140 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3792 0.3274 -0.4938 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4413 -1.1568 -0.8109 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 -1.6897 0.6053 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7516 -0.6274 1.4689 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8821 -0.1023 2.3328 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2381 1.0821 2.3300 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4964 -1.0655 3.1390 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7400 -1.1705 2.3829 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3502 -0.6555 2.2760 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9468 -0.3991 0.8608 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8861 -1.7165 0.1525 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9136 0.5810 0.1929 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5049 0.7322 -1.2540 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0355 1.0982 -1.4092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8643 0.2289 -0.6018 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3131 0.4759 -0.8760 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7266 1.9003 -0.8962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5756 -0.0519 -2.2979 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0396 -0.0908 -2.6242 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8995 -0.7735 -1.6277 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2267 -0.4224 -1.8406 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5697 -0.4619 -0.1870 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0712 -1.6906 0.6000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3493 0.7063 0.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1048 -0.4059 0.0403 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8114 -0.1619 1.5042 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3808 -0.5229 1.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4580 0.2328 0.8413 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4341 1.6458 1.3972 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3081 0.4884 0.5229 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2591 -0.2803 -3.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5068 1.4026 -3.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7896 3.1075 -0.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3580 0.4630 0.0835 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4041 -1.3654 -1.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6405 -1.5205 -1.4382 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9366 -2.6589 0.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4851 -1.8693 0.8724 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3118 -0.8433 3.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7616 -2.2998 2.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0246 -1.0699 3.4784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6730 -1.4838 2.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2132 0.1604 2.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1020 -2.2405 0.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1619 -1.6958 -0.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5742 -2.4816 0.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5126 1.5797 0.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8067 -0.0580 -1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0083 1.6850 -1.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1611 2.1761 -1.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1777 0.8468 -2.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6810 -0.8115 -1.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1472 2.4031 -1.7170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 2.4397 0.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7869 1.9265 -1.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1185 0.6481 -3.0581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1351 -1.0455 -2.3545 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4271 0.9234 -2.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1111 -0.6910 -3.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8460 -1.8849 -1.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8507 -1.1090 -1.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3994 -1.3451 1.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9844 -2.0952 0.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3154 -2.4739 0.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9263 1.1327 -0.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7662 1.4645 0.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1714 0.4111 1.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7190 -1.4559 -0.1523 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1292 0.8076 1.8732 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4306 -0.9248 2.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1486 -0.1798 2.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2866 -1.5992 1.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3341 2.4309 0.6565 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4014 1.8784 1.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3204 1.7969 2.2019 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6199 1.4302 1.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 2 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 9 10 2 0 9 11 1 0 8 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 16 34 1 0 34 5 1 0 34 8 1 0 32 14 1 0 32 19 1 0 29 20 1 0 1 35 1 0 1 36 1 0 3 37 1 0 5 38 1 1 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 11 43 1 0 12 44 1 0 12 45 1 0 13 46 1 0 13 47 1 0 15 48 1 0 15 49 1 0 15 50 1 0 16 51 1 1 17 52 1 0 17 53 1 0 18 54 1 0 18 55 1 0 19 56 1 6 21 57 1 0 21 58 1 0 21 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 24 64 1 1 25 65 1 0 27 66 1 0 27 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 6 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 1 M END

Standard InCHIKey	OTNMMCVDNMEIGO-XNWPAUOFSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-18(17-31)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-27(4)12-11-23(32)26(2,3)21(27)10-13-29(22,28)6/h17,19-24,32H,1,7-16H2,2-6H3,(H,33,34)/t19-,20+,21-,22+,23-,24-,27-,28+,29+,30-/m0/s1
SMILES	C=C(C=O)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	2.99 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.799 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.131 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.377	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.914	Fsp³:	0.867
MCE-18:	104.5 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.721	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.33	Promiscuous compounds:	0.094

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.531	MDCK Permeability:	-5.088
Pgp-inhibitor:	0.0	Pgp-substrate:	0.047
PAMPA:	0.996 ? 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):	0.0
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	0.481
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.906	MRP1:	0.96
Plasma Protein Binding (PPB):	97.3%	Volume Distribution (VD):	-0.301
Fu:	3.081% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.49	BCRP inhibitor:	0.029
BSEP inhibitor:	0.529

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.194	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

4.411

Half-life (T1/2):

0.822

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.044
Human Hepatotoxicity (H-HT):	0.572	Drug-induced Liver Injury (DILI):	0.592
AMES Toxicity:	0.457	Rat Oral Acute Toxicity:	0.513
Maximum Recommended Daily Dose:	0.524	Skin Sensitization:	0.987
Carcinogencity:	0.913	Eye Corrosion:	0.261
Eye Irritation:	0.809	Respiratory Toxicity:	0.922
Drug-induced Neurotoxicity:	0.083	Ototoxicity:	0.472
Hematotoxicity:	0.53	Drug-induced Nephrotoxicity:	0.858
Genotoxicity:	0.969	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.256	Hek293 Cytotoxicity:	0.293
BCF:	0.637 ? 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:	3.584 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.209 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.609 ? 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
NPO18975	Melilotus messanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18975	Melilotus messanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18975	Melilotus messanensis	Species	Fabaceae	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 NPC531559 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	20183
0.1-0.2	24664
0.2-0.3	4108
0.3-0.4	653
0.4-0.5	172
0.5-0.6	47
0.6-0.7	14
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8621	High Similarity	NPC264317
0.8621	High Similarity	NPC294438
0.8525	High Similarity	NPC488165
0.8197	Intermediate Similarity	NPC16377
0.7419	Intermediate Similarity	NPC30583
0.7344	Intermediate Similarity	NPC151191
0.7302	Intermediate Similarity	NPC488164
0.7302	Intermediate Similarity	NPC264005
0.6818	Remote Similarity	NPC2783
0.6769	Remote Similarity	NPC476071
0.6567	Remote Similarity	NPC18064
0.6562	Remote Similarity	NPC472608
0.6515	Remote Similarity	NPC488506
0.6515	Remote Similarity	NPC220498
0.6418	Remote Similarity	NPC201655
0.6269	Remote Similarity	NPC24772
0.6269	Remote Similarity	NPC213832
0.625	Remote Similarity	NPC269396
0.6111	Remote Similarity	NPC481311
0.6056	Remote Similarity	NPC169933
0.6	Remote Similarity	NPC68828
0.6	Remote Similarity	NPC601275
0.597	Remote Similarity	NPC192744
0.5915	Remote Similarity	NPC486704
0.5882	Remote Similarity	NPC80590
0.5857	Remote Similarity	NPC4309
0.5797	Remote Similarity	NPC211162
0.5797	Remote Similarity	NPC183374
0.5797	Remote Similarity	NPC291373
0.5797	Remote Similarity	NPC30322
0.5775	Remote Similarity	NPC269360
0.5775	Remote Similarity	NPC475061
0.5735	Remote Similarity	NPC119743
0.5714	Remote Similarity	NPC271974
0.5714	Remote Similarity	NPC247312
0.5696	Remote Similarity	NPC486709
0.5694	Remote Similarity	NPC160506
0.5616	Remote Similarity	NPC608379
0.5571	Remote Similarity	NPC474686
0.5556	Remote Similarity	NPC488213
0.5522	Remote Similarity	NPC246445
0.5493	Remote Similarity	NPC195395
0.5488	Remote Similarity	NPC486699
0.5405	Remote Similarity	NPC478841
0.5405	Remote Similarity	NPC488166
0.5405	Remote Similarity	NPC600004
0.5357	Remote Similarity	NPC290349
0.5352	Remote Similarity	NPC181225
0.5342	Remote Similarity	NPC474719
0.5294	Remote Similarity	NPC74595
0.5294	Remote Similarity	NPC264665
0.5278	Remote Similarity	NPC277399
0.5278	Remote Similarity	NPC474512
0.527	Remote Similarity	NPC611139
0.525	Remote Similarity	NPC605397
0.5231	Remote Similarity	NPC192638
0.5231	Remote Similarity	NPC25511
0.5231	Remote Similarity	NPC600137
0.5217	Remote Similarity	NPC298168
0.5217	Remote Similarity	NPC143133
0.52	Remote Similarity	NPC601176
0.5161	Remote Similarity	NPC232112
0.5143	Remote Similarity	NPC12774
0.5125	Remote Similarity	NPC606354
0.5067	Remote Similarity	NPC252714
0.5065	Remote Similarity	NPC603461
0.5062	Remote Similarity	NPC611262
0.5056	Remote Similarity	NPC486700
0.5056	Remote Similarity	NPC275312

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC531559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5466
0.1-0.2	3585
0.2-0.3	89
0.3-0.4	6
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	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD7520	Phase 1
0.5694	Remote Similarity	NPD8035	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