NPASS Compound

Natural Product: NPC35239

Natural Product ID	NPC35239
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Alpha,3Beta,19Alpha-Trihydroxyurs-12-En-23,28-Dioic Acid
IUPAC Name	(2R,3R,4S,4aR,6aR,6bS,8aS,11R,12R,12aS,14aR,14bR)-2,3,12-trihydroxy-4,6a,6b,11,12,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,11,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1079285
PubChem CID	21606530
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 -3.9061 -0.6224 -2.7441 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3344 0.5016 -2.0056 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2153 1.2767 -1.4358 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7598 0.8329 -0.0633 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2021 1.8614 0.9205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2933 -0.5473 0.1969 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7434 -0.7652 0.1004 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3675 0.0584 -0.9975 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1404 1.1199 -0.5287 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4944 -0.6282 1.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9283 -2.2052 -0.3135 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5163 -2.5162 -1.3861 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4707 -3.2695 0.4472 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7734 -1.0392 1.5569 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3192 -1.3802 1.3228 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6038 -0.1369 0.9002 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2663 0.6649 -0.1487 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5073 1.9365 -0.3077 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9482 1.7422 -0.1873 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5706 0.6025 0.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7214 -0.6014 0.2750 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5106 -1.2050 -1.1000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3050 -1.6455 1.1517 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7669 -1.8104 0.9000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5876 -0.5716 0.9590 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0480 0.5792 0.1623 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7269 0.6276 -1.1908 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1168 1.6169 -2.1375 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7155 -0.6096 -1.8324 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1492 1.1046 -0.9100 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9520 1.2587 -2.1712 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8063 0.1832 0.0586 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9906 -0.9737 0.4950 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7278 -0.1907 2.3915 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3478 0.8979 2.8699 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3341 -1.1566 3.2129 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2505 0.6411 2.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9789 -0.4649 -3.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8730 1.1384 -2.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3784 1.2569 -2.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5197 2.3635 -1.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4425 2.8288 0.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5224 2.0275 1.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1885 1.5511 1.3358 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7907 -1.2013 -0.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1025 -0.5608 -1.5999 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9217 1.3106 -1.1151 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2036 0.2509 1.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8318 -0.5464 2.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1620 -1.4958 1.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8887 -4.1901 0.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8189 -0.2186 2.3038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3536 -1.8898 1.9193 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9001 -1.6863 2.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1884 -2.2399 0.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1197 0.1114 -1.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7941 2.7566 0.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7029 2.3283 -1.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5657 2.6469 -0.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4259 -1.7922 -1.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 -0.4672 -1.9153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3203 -1.9742 -1.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1310 -1.5642 2.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -2.6251 0.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1577 -2.4962 1.7096 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9995 -2.3358 -0.0474 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3641 1.5080 0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3802 2.6700 -1.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6413 1.4374 -3.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0563 1.4545 -2.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9391 -0.4513 -2.7672 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0405 2.1002 -0.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7589 0.4961 -2.9238 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0269 1.1796 -1.8847 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8206 2.3075 -2.5454 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7298 -0.2227 -0.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1485 0.7366 0.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4983 -1.4407 1.3766 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9399 -1.8103 -0.2544 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4022 -1.0315 4.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1708 1.7354 1.9894 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6783 0.3391 2.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0462 0.5383 2.9402 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 1 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 1 1 7 11 1 0 11 12 2 0 11 13 1 0 6 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 6 27 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 25 34 1 1 34 35 2 0 34 36 1 0 16 37 1 1 8 2 1 0 21 16 1 0 33 25 1 0 17 4 1 0 26 20 1 0 1 38 1 0 2 39 1 6 3 40 1 0 3 41 1 0 5 42 1 0 5 43 1 0 5 44 1 0 6 45 1 6 8 46 1 6 9 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 17 56 1 6 18 57 1 0 18 58 1 0 19 59 1 0 22 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 26 67 1 1 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 1 31 73 1 0 31 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 33 78 1 0 33 79 1 0 36 80 1 0 37 81 1 0 37 82 1 0 37 83 1 0 M END

Standard InCHIKey	FYGSMJAMPMZYFS-LQXQUUHISA-N
Standard InCHI	InChI=1S/C30H46O7/c1-16-9-12-30(24(35)36)14-13-26(3)17(21(30)29(16,6)37)7-8-19-25(2)15-18(31)22(32)28(5,23(33)34)20(25)10-11-27(19,26)4/h7,16,18-22,31-32,37H,8-15H2,1-6H3,(H,33,34)(H,35,36)/t16-,18-,19-,20-,21-,22+,25-,26-,27-,28+,29-,30+/m1/s1
SMILES	O[C@@H]1C[C@@]2(C)[C@H]([C@]([C@H]1O)(C)C(=O)O)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.32	Volume:	538.276 ? Van der Waals volume.
Dense:	0.963	LogP:	2.285 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.291 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.721 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	135.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.345	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.187	Fsp³:	0.867
MCE-18:	114.0 ? 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:	0.506	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.311 ? 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:	0.298	Promiscuous compounds:	0.076

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.681	MDCK Permeability:	-5.176
Pgp-inhibitor:	0.0	Pgp-substrate:	0.013
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):	0.003
20% Bioavailability (F20%):	0.057	30% Bioavailability (F30%):	0.012
50% Bioavailability (F50%):	0.459

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.998
Plasma Protein Binding (PPB):	81.214%	Volume Distribution (VD):	-0.389
Fu:	14.682% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.786	BCRP inhibitor:	0.0
BSEP inhibitor:	0.784

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.028	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.028	CYP3A4-substrate:	0.034
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.011
HLM stability:	0.001 ? 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):

0.934

Half-life (T1/2):

1.81

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.614	Drug-induced Liver Injury (DILI):	0.707
AMES Toxicity:	0.138	Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.119	Skin Sensitization:	0.961
Carcinogencity:	0.727	Eye Corrosion:	0.012
Eye Irritation:	0.274	Respiratory Toxicity:	0.759
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.857
Hematotoxicity:	0.515	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.933	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.023	Hek293 Cytotoxicity:	0.017
BCF:	0.534 ? 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:	5.014 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.092 ? 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
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19795885]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[38455614]
NPO23655.1	Rubus ellipticus	Under-species	n.a.	n.a.	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	IC50	=	1680000.0	nM	PMID[19928902]

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 NPC35239 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	24931
0.1-0.2	21876
0.2-0.3	2512
0.3-0.4	356
0.4-0.5	115
0.5-0.6	32
0.6-0.7	23
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
0.7879	Intermediate Similarity	NPC132824
0.7463	Intermediate Similarity	NPC259733
0.7463	Intermediate Similarity	NPC158371
0.7463	Intermediate Similarity	NPC207922
0.7353	Intermediate Similarity	NPC247139
0.7313	Intermediate Similarity	NPC106112
0.7313	Intermediate Similarity	NPC261935
0.7313	Intermediate Similarity	NPC111214
0.6957	Remote Similarity	NPC202728
0.6957	Remote Similarity	NPC158059
0.6957	Remote Similarity	NPC136697
0.6857	Remote Similarity	NPC191412
0.6857	Remote Similarity	NPC114159
0.6857	Remote Similarity	NPC6818
0.6761	Remote Similarity	NPC62516
0.6757	Remote Similarity	NPC96693
0.6667	Remote Similarity	NPC187933
0.6667	Remote Similarity	NPC157113
0.6528	Remote Similarity	NPC148964
0.6479	Remote Similarity	NPC256247
0.6389	Remote Similarity	NPC118519
0.6338	Remote Similarity	NPC271614
0.6338	Remote Similarity	NPC235053
0.6316	Remote Similarity	NPC54909
0.6316	Remote Similarity	NPC233012
0.6301	Remote Similarity	NPC137072
0.6301	Remote Similarity	NPC118964
0.6267	Remote Similarity	NPC603658
0.6216	Remote Similarity	NPC284865
0.6	Remote Similarity	NPC147232
0.6	Remote Similarity	NPC174663
0.5897	Remote Similarity	NPC327179
0.5541	Remote Similarity	NPC282616
0.5526	Remote Similarity	NPC9613
0.5488	Remote Similarity	NPC600756
0.5467	Remote Similarity	NPC88116
0.5467	Remote Similarity	NPC472149
0.5467	Remote Similarity	NPC71074
0.5467	Remote Similarity	NPC37221
0.5467	Remote Similarity	NPC481360
0.5467	Remote Similarity	NPC605937
0.5467	Remote Similarity	NPC609452
0.5435	Remote Similarity	NPC482049
0.5435	Remote Similarity	NPC482050
0.5395	Remote Similarity	NPC87095
0.5395	Remote Similarity	NPC32407
0.5395	Remote Similarity	NPC263548
0.5395	Remote Similarity	NPC606320
0.5333	Remote Similarity	NPC84319
0.5333	Remote Similarity	NPC52021
0.5333	Remote Similarity	NPC599947
0.5263	Remote Similarity	NPC231063
0.5263	Remote Similarity	NPC282395
0.5263	Remote Similarity	NPC173744
0.5263	Remote Similarity	NPC204961
0.5263	Remote Similarity	NPC73004
0.5263	Remote Similarity	NPC110308
0.519	Remote Similarity	NPC116457
0.5161	Remote Similarity	NPC25491
0.5063	Remote Similarity	NPC25299
0.5063	Remote Similarity	NPC481322
0.5054	Remote Similarity	NPC482052
0.5053	Remote Similarity	NPC482051

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC35239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6608
0.1-0.2	2498
0.2-0.3	40
0.3-0.4	4
0.4-0.5	0
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