NPASS Compound

Natural Product: NPC148964

Natural Product ID	NPC148964
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	19Alpha,24-Dihydroxyurs-12-En-3-On-28-Oic Acid
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,9S,12aR,14bS)-1-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-2H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL494111
PubChem CID	10600994
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 81 85 0 0 0 0 0 0 0 0999 V2000 -5.5039 0.4804 -2.5103 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7362 -0.0248 -1.2421 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0198 0.6695 -0.1449 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5119 2.1372 -0.1992 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5387 0.1850 1.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6024 -0.3900 1.1926 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7393 0.4235 2.3532 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2961 0.1476 2.2225 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8446 -0.2488 0.8014 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5609 0.6863 -0.1443 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9237 0.7307 -1.5141 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4853 1.1266 -1.4663 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7460 0.1832 -0.5513 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3659 0.0597 0.7892 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5626 -0.7898 1.7041 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8272 -1.0120 1.2193 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 -0.3240 0.2873 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6563 0.7809 -0.3217 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5720 1.9304 0.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2614 1.3049 -1.5613 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7029 1.5932 -1.3541 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5438 0.4553 -0.8670 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8513 -0.6426 -0.1521 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6136 -1.3757 0.8865 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3382 -2.8739 0.7682 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4090 -0.9071 2.1788 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1014 -1.2333 0.6420 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4287 0.2319 0.8154 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6727 1.1212 -0.0833 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9023 -1.9368 1.7322 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2217 -0.0756 -2.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0171 -1.2169 -2.5699 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0993 0.7632 -2.7731 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5531 -1.1110 -1.2788 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1793 -1.6872 0.6790 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2788 -0.1868 -3.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8346 0.0318 -1.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5066 -1.1081 -1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6296 2.3939 -1.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5112 2.2044 0.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7691 2.8140 0.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9218 1.5004 2.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1352 -0.1636 3.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7336 1.0546 2.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9596 -0.6503 2.9479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 1.6994 0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4640 1.5605 -2.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0503 -0.1575 -2.1083 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4087 2.1787 -1.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0613 0.9816 -2.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3144 1.1109 1.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9919 -1.8025 1.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4683 -0.3095 2.7197 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3623 -1.8257 1.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5684 1.5946 1.7281 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2818 2.6274 0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4515 2.6046 0.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7740 2.3005 -1.7740 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1355 0.7276 -2.4773 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0900 1.9352 -2.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8982 2.4872 -0.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6665 -1.4263 -0.9714 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2127 -3.4183 0.3000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5122 -3.0964 0.0513 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2214 -3.3148 1.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0209 -0.0196 2.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4360 -1.6096 -0.3298 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5336 0.3729 0.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1387 0.4823 1.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3645 1.5514 -0.8368 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2677 2.0429 0.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9008 -2.1503 1.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0620 -1.2774 2.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4516 -2.8659 2.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3826 0.6481 -3.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3585 -1.9879 -0.6628 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2889 -1.0496 -2.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4341 -1.3783 -1.9236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9529 -2.1733 1.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6340 -2.2752 -0.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2797 -1.8196 0.6045 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 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 1 24 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 22 31 1 6 31 32 2 0 31 33 1 0 13 34 1 6 9 35 1 6 10 3 1 0 18 13 1 0 29 22 1 0 14 9 1 0 23 17 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 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 10 46 1 1 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 14 51 1 1 15 52 1 0 15 53 1 0 16 54 1 0 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 23 62 1 6 25 63 1 0 25 64 1 0 25 65 1 0 26 66 1 0 27 67 1 6 28 68 1 0 28 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 35 79 1 0 35 80 1 0 35 81 1 0 M END

Standard InCHIKey	DICFMPCEXYENLE-OGHVSZAPSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-18-9-14-30(24(33)34)16-15-27(4)19(23(30)29(18,6)35)7-8-21-25(2)12-11-22(32)26(3,17-31)20(25)10-13-28(21,27)5/h7,18,20-21,23,31,35H,8-17H2,1-6H3,(H,33,34)/t18-,20-,21-,23-,25+,26-,27-,28-,29-,30+/m1/s1
SMILES	OC[C@@]1(C)C(=O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@@H](CC1)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	2.872 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.63 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.159 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	94.83 ? 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:	0.455	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.029	Fsp³:	0.867
MCE-18:	107.143 ? 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:	0.575	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.107 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.322	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.447	MDCK Permeability:	-5.085
Pgp-inhibitor:	0.001	Pgp-substrate:	0.004
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):	0.0
20% Bioavailability (F20%):	0.062	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223	MRP1:	0.997
Plasma Protein Binding (PPB):	87.996%	Volume Distribution (VD):	-0.412
Fu:	10.994% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.956	BCRP inhibitor:	0.006
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.126	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.657	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.016
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.034
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):

3.332

Half-life (T1/2):

1.015

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.044
Human Hepatotoxicity (H-HT):	0.766	Drug-induced Liver Injury (DILI):	0.684
AMES Toxicity:	0.347	Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.418	Skin Sensitization:	0.965
Carcinogencity:	0.96	Eye Corrosion:	0.006
Eye Irritation:	0.486	Respiratory Toxicity:	0.895
Drug-induced Neurotoxicity:	0.312	Ototoxicity:	0.624
Hematotoxicity:	0.572	Drug-induced Nephrotoxicity:	0.971
Genotoxicity:	0.982	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.158	Hek293 Cytotoxicity:	0.235
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:	3.413 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.007 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.28 ? 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]
NPO27309	Rubus chroosepalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27309	Rubus chroosepalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27309	Rubus chroosepalus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27309	Rubus chroosepalus	Species	Rosaceae	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

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	=	8100.0	nM	PMID[18798681]

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 NPC148964 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	18656
0.1-0.2	26395
0.2-0.3	3944
0.3-0.4	603
0.4-0.5	171
0.5-0.6	43
0.6-0.7	22
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
0.7353	Intermediate Similarity	NPC202728
0.7353	Intermediate Similarity	NPC173089
0.7353	Intermediate Similarity	NPC158059
0.7353	Intermediate Similarity	NPC136697
0.7246	Intermediate Similarity	NPC191412
0.7246	Intermediate Similarity	NPC114159
0.7246	Intermediate Similarity	NPC6818
0.7206	Intermediate Similarity	NPC158141
0.7143	Intermediate Similarity	NPC62516
0.7042	Intermediate Similarity	NPC187933
0.7042	Intermediate Similarity	NPC157113
0.7	Intermediate Similarity	NPC247139
0.6857	Remote Similarity	NPC259733
0.6857	Remote Similarity	NPC158371
0.6857	Remote Similarity	NPC207922
0.6714	Remote Similarity	NPC235053
0.6667	Remote Similarity	NPC54909
0.6667	Remote Similarity	NPC118964
0.6667	Remote Similarity	NPC233012
0.6622	Remote Similarity	NPC603658
0.6575	Remote Similarity	NPC147232
0.6575	Remote Similarity	NPC284865
0.6528	Remote Similarity	NPC35239
0.6528	Remote Similarity	NPC132824
0.6389	Remote Similarity	NPC256247
0.6267	Remote Similarity	NPC6255
0.6234	Remote Similarity	NPC96693
0.6216	Remote Similarity	NPC137072
0.6203	Remote Similarity	NPC600756
0.6081	Remote Similarity	NPC118519
0.6056	Remote Similarity	NPC274050
0.6056	Remote Similarity	NPC162632
0.6027	Remote Similarity	NPC38754
0.6026	Remote Similarity	NPC327179
0.5926	Remote Similarity	NPC476890
0.5926	Remote Similarity	NPC476889
0.5843	Remote Similarity	NPC482052
0.5526	Remote Similarity	NPC477288
0.5513	Remote Similarity	NPC116457
0.5435	Remote Similarity	NPC25491
0.5376	Remote Similarity	NPC482049
0.5376	Remote Similarity	NPC482050
0.5319	Remote Similarity	NPC482051
0.5263	Remote Similarity	NPC182797
0.5263	Remote Similarity	NPC51700
0.5263	Remote Similarity	NPC88716
0.5263	Remote Similarity	NPC68160
0.5263	Remote Similarity	NPC52169
0.5263	Remote Similarity	NPC488562
0.5256	Remote Similarity	NPC9613
0.52	Remote Similarity	NPC201655
0.5195	Remote Similarity	NPC61543
0.5195	Remote Similarity	NPC293048
0.5195	Remote Similarity	NPC225585
0.5195	Remote Similarity	NPC88116
0.5195	Remote Similarity	NPC37221
0.5132	Remote Similarity	NPC480946
0.5132	Remote Similarity	NPC187722
0.5132	Remote Similarity	NPC130577
0.5132	Remote Similarity	NPC142415
0.5132	Remote Similarity	NPC102683
0.5128	Remote Similarity	NPC291028
0.5128	Remote Similarity	NPC32407
0.5128	Remote Similarity	NPC293564
0.5128	Remote Similarity	NPC263548
0.5128	Remote Similarity	NPC606320
0.5125	Remote Similarity	NPC324063
0.5065	Remote Similarity	NPC270768
0.5065	Remote Similarity	NPC59263
0.5065	Remote Similarity	NPC263272
0.5065	Remote Similarity	NPC210106
0.5065	Remote Similarity	NPC229281
0.5065	Remote Similarity	NPC121798
0.5065	Remote Similarity	NPC234346
0.5063	Remote Similarity	NPC193750
0.5051	Remote Similarity	NPC481234
0.5051	Remote Similarity	NPC479431

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC148964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5456
0.1-0.2	3607
0.2-0.3	80
0.3-0.4	6
0.4-0.5	1
0.5-0.6	0
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
		NPD

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