NPASS Compound

Natural Product: NPC121798

Natural Product ID	NPC121798
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Alpha,24,29-Trihydroxyolean-12-En-28-Oic Acid
IUPAC Name	(2R,4aR,6aR,6aS,6bR,8aR,9S,10R,12aR,14bS)-10-hydroxy-2,9-bis(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL492675
PubChem CID	44568935
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 83 87 0 0 0 0 0 0 0 0999 V2000 -6.7863 -2.6436 -0.7559 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4217 -2.5077 -0.7788 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9395 -1.4511 0.2260 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3966 -1.9382 1.5865 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6562 -0.1465 -0.0368 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9387 0.6655 -1.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5459 1.0833 -0.6294 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9922 0.1213 0.3542 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4502 -1.3030 0.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 0.1522 0.4420 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9917 -0.1310 1.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4384 -0.1631 1.9777 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2331 0.0037 0.7344 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6594 1.0682 -0.1622 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6189 0.4703 -0.7283 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2663 1.4847 -1.6390 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7234 1.2188 -1.8541 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3964 -0.7947 -1.4909 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2075 2.2871 0.6585 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5383 1.4867 -1.2755 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9818 1.2061 -1.1923 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3085 -0.0837 -0.4356 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7170 0.1269 0.9423 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0613 1.4436 1.5474 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2225 -0.9782 1.8202 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6919 -0.8131 2.0166 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4732 -0.4877 0.8034 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7079 -0.5026 -0.4841 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8110 -1.9436 -1.0216 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5481 0.3074 -1.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8477 -0.2426 -1.3802 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5067 -1.4533 0.6992 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7453 2.4088 0.0388 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1672 3.4006 -0.4492 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5480 2.5206 1.1628 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2150 -2.2615 -1.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9172 -3.4637 -0.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1233 -2.0976 -1.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4857 -3.0599 1.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7174 -1.6003 2.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4106 -1.5603 1.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6786 0.4435 0.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6620 -0.3593 -0.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5794 1.5391 -1.3257 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8987 0.0421 -2.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4285 0.4046 1.3522 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9875 -1.9306 0.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1303 -1.6994 -0.8475 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6794 -0.3640 2.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6578 -1.2072 2.3607 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7309 0.4918 2.8201 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1081 -0.9696 0.1664 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7960 1.3938 -2.6639 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0812 2.5373 -1.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8167 0.3135 -2.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1182 2.0576 -2.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5567 -0.8394 -2.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1955 -0.9006 -2.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4572 -1.7202 -0.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4674 2.1871 1.7330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6005 3.2233 0.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8981 2.3990 0.6724 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4213 2.6056 -1.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1681 1.0883 -2.2665 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4090 1.0269 -2.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5997 2.0629 -0.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6825 -0.8605 -0.9720 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5853 1.4650 2.5629 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7325 2.3282 1.0085 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1377 1.5787 1.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9738 -1.9773 1.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7408 -0.8890 2.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0510 -1.7510 2.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8530 -0.0132 2.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0574 0.4783 0.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6063 -2.6717 -0.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7790 -2.1328 -1.4826 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0252 -2.0923 -1.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2107 0.1464 -2.5249 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6317 1.3570 -1.2146 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1022 -0.7384 -2.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1657 -1.2971 1.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6296 3.4145 1.6163 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 6 14 19 1 1 14 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 28 30 1 0 30 31 1 0 27 32 1 0 7 33 1 1 33 34 2 0 33 35 1 0 9 3 1 0 15 10 1 0 28 22 1 0 17 7 1 0 23 13 1 0 1 36 1 0 2 37 1 0 2 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 8 46 1 1 9 47 1 0 9 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 6 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 6 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 1 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 32 82 1 0 35 83 1 0 M END

Standard InCHIKey	LQETVSULLNKTKF-YSKPPUCTSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-25(17-31)12-14-30(24(34)35)15-13-28(4)19(20(30)16-25)6-7-22-26(2)10-9-23(33)27(3,18-32)21(26)8-11-29(22,28)5/h6,20-23,31-33H,7-18H2,1-5H3,(H,34,35)/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-/m0/s1
SMILES	OC[C@]1(C)CC[C@]2([C@@H](C1)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@H]([C@]1(C)CO)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	2.855 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.662 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.189 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.411	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.959	Fsp³:	0.9
MCE-18:	105.368 ? 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:	0.7	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:	0.379	Promiscuous compounds:	0.175

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.527	MDCK Permeability:	-5.022
Pgp-inhibitor:	0.005	Pgp-substrate:	0.097
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):	0.001
20% Bioavailability (F20%):	0.985	30% Bioavailability (F30%):	0.197
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.632	MRP1:	0.977
Plasma Protein Binding (PPB):	75.406%	Volume Distribution (VD):	-0.418
Fu:	20.923% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.138	BCRP inhibitor:	0.154
BSEP inhibitor:	0.912

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.544	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.025
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):

4.449

Half-life (T1/2):

1.288

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.779	Drug-induced Liver Injury (DILI):	0.062
AMES Toxicity:	0.147	Rat Oral Acute Toxicity:	0.135
Maximum Recommended Daily Dose:	0.341	Skin Sensitization:	0.989
Carcinogencity:	0.978	Eye Corrosion:	0.0
Eye Irritation:	0.615	Respiratory Toxicity:	0.741
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.763
Hematotoxicity:	0.239	Drug-induced Nephrotoxicity:	0.933
Genotoxicity:	0.142	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.127	Hek293 Cytotoxicity:	0.133
BCF:	0.587 ? 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:	3.365 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.951 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.128 ? 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
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]

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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	30000.0	nM	PMID[18341274]

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 NPC121798 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	23763
0.1-0.2	21987
0.2-0.3	3180
0.3-0.4	542
0.4-0.5	239
0.5-0.6	84
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234346
0.8667	High Similarity	NPC270768
0.8667	High Similarity	NPC59263
0.8667	High Similarity	NPC182797
0.8667	High Similarity	NPC210106
0.8667	High Similarity	NPC52169
0.8667	High Similarity	NPC488562
0.7846	Intermediate Similarity	NPC130520
0.7656	Intermediate Similarity	NPC609452
0.75	Intermediate Similarity	NPC229281
0.7385	Intermediate Similarity	NPC61543
0.7385	Intermediate Similarity	NPC293048
0.7385	Intermediate Similarity	NPC225585
0.7344	Intermediate Similarity	NPC480946
0.7344	Intermediate Similarity	NPC130577
0.7344	Intermediate Similarity	NPC142415
0.7344	Intermediate Similarity	NPC102683
0.7273	Intermediate Similarity	NPC298554
0.7164	Intermediate Similarity	NPC191412
0.7164	Intermediate Similarity	NPC114159
0.7164	Intermediate Similarity	NPC6818
0.7121	Intermediate Similarity	NPC472149
0.7059	Intermediate Similarity	NPC127689
0.6957	Remote Similarity	NPC116457
0.6667	Remote Similarity	NPC263393
0.6618	Remote Similarity	NPC231063
0.6618	Remote Similarity	NPC282395
0.6618	Remote Similarity	NPC130278
0.6471	Remote Similarity	NPC282616
0.6377	Remote Similarity	NPC88116
0.6324	Remote Similarity	NPC187722
0.6324	Remote Similarity	NPC198664
0.6286	Remote Similarity	NPC136697
0.625	Remote Similarity	NPC324063
0.6232	Remote Similarity	NPC275809
0.6232	Remote Similarity	NPC51700
0.6232	Remote Similarity	NPC88716
0.6232	Remote Similarity	NPC68160
0.6232	Remote Similarity	NPC606443
0.6143	Remote Similarity	NPC158141
0.6143	Remote Similarity	NPC110308
0.6056	Remote Similarity	NPC202728
0.6056	Remote Similarity	NPC158059
0.6056	Remote Similarity	NPC293564
0.6027	Remote Similarity	NPC187933
0.6	Remote Similarity	NPC64872
0.6	Remote Similarity	NPC84319
0.6	Remote Similarity	NPC25906
0.6	Remote Similarity	NPC52021
0.6	Remote Similarity	NPC599947
0.597	Remote Similarity	NPC604575
0.5915	Remote Similarity	NPC106112
0.5915	Remote Similarity	NPC261935
0.5733	Remote Similarity	NPC6255
0.5694	Remote Similarity	NPC73489
0.5694	Remote Similarity	NPC173744
0.5694	Remote Similarity	NPC204961
0.5694	Remote Similarity	NPC73004
0.5694	Remote Similarity	NPC481360
0.5676	Remote Similarity	NPC137072
0.5672	Remote Similarity	NPC196753
0.5658	Remote Similarity	NPC474727
0.5634	Remote Similarity	NPC274330
0.5616	Remote Similarity	NPC228784
0.5616	Remote Similarity	NPC324341
0.5616	Remote Similarity	NPC32407
0.5616	Remote Similarity	NPC263548
0.5616	Remote Similarity	NPC601810
0.5616	Remote Similarity	NPC606320
0.56	Remote Similarity	NPC222047
0.5556	Remote Similarity	NPC204407
0.5556	Remote Similarity	NPC307282
0.5556	Remote Similarity	NPC37038
0.5556	Remote Similarity	NPC171203
0.5556	Remote Similarity	NPC307426
0.5556	Remote Similarity	NPC98442
0.5556	Remote Similarity	NPC242468
0.5541	Remote Similarity	NPC247139
0.5507	Remote Similarity	NPC230295
0.5507	Remote Similarity	NPC253402
0.5507	Remote Similarity	NPC98386
0.5493	Remote Similarity	NPC477872
0.5488	Remote Similarity	NPC28198
0.5488	Remote Similarity	NPC476123
0.5488	Remote Similarity	NPC606107
0.5417	Remote Similarity	NPC213412
0.5405	Remote Similarity	NPC200752
0.5405	Remote Similarity	NPC120840
0.5395	Remote Similarity	NPC20235
0.5395	Remote Similarity	NPC299996
0.5375	Remote Similarity	NPC603645
0.5352	Remote Similarity	NPC280654
0.5349	Remote Similarity	NPC284807
0.5342	Remote Similarity	NPC7260
0.5342	Remote Similarity	NPC210037
0.5342	Remote Similarity	NPC120968
0.5342	Remote Similarity	NPC227467
0.5342	Remote Similarity	NPC273621
0.5342	Remote Similarity	NPC112866
0.5333	Remote Similarity	NPC201657
0.5333	Remote Similarity	NPC132824
0.5333	Remote Similarity	NPC474963
0.5316	Remote Similarity	NPC188833
0.5301	Remote Similarity	NPC283849
0.5281	Remote Similarity	NPC198621
0.5281	Remote Similarity	NPC216940
0.527	Remote Similarity	NPC38754
0.527	Remote Similarity	NPC37221
0.52	Remote Similarity	NPC173089
0.52	Remote Similarity	NPC145667
0.5195	Remote Similarity	NPC174663
0.5176	Remote Similarity	NPC286347
0.5169	Remote Similarity	NPC488215
0.5139	Remote Similarity	NPC488164
0.5139	Remote Similarity	NPC264005
0.5135	Remote Similarity	NPC156981
0.5132	Remote Similarity	NPC118519
0.5132	Remote Similarity	NPC91010
0.5128	Remote Similarity	NPC479743
0.5128	Remote Similarity	NPC96580
0.5116	Remote Similarity	NPC100383
0.5114	Remote Similarity	NPC191410
0.5067	Remote Similarity	NPC126369
0.5067	Remote Similarity	NPC470589
0.5067	Remote Similarity	NPC271614
0.5067	Remote Similarity	NPC111110
0.5067	Remote Similarity	NPC71074
0.5067	Remote Similarity	NPC111214
0.5067	Remote Similarity	NPC481314
0.5067	Remote Similarity	NPC605937
0.5065	Remote Similarity	NPC148964
0.5065	Remote Similarity	NPC481316
0.5056	Remote Similarity	NPC475472
0.5055	Remote Similarity	NPC136877

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121798 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6570
0.1-0.2	2529
0.2-0.3	46
0.3-0.4	2
0.4-0.5	2
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
0.5342	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