NPASS Compound

Natural Product: NPC147066

Natural Product ID	NPC147066
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Oxotirucalla-7,24-Dien-21-Oic Acid
IUPAC Name	(2S)-6-methyl-2-[(5R,9R,10R,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL481824
PubChem CID	158100
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 79 82 0 0 0 0 0 0 0 0999 V2000 7.2770 2.8231 1.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4669 1.5885 1.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3121 1.7774 0.5071 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2346 0.8846 0.0022 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3911 -0.5482 0.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4226 -1.5152 -0.4564 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0396 -1.6399 -0.0774 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4863 -2.8242 -0.9352 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0137 -2.6714 -1.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2512 -1.6477 0.1008 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9349 -0.6989 -0.2015 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6390 -0.2364 -1.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7898 0.3919 0.7961 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5720 0.6974 1.3306 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 0.4453 0.3343 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5281 -0.9509 -0.1074 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5938 -1.5070 -0.6719 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8960 -0.8576 -0.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9496 0.5142 -0.3499 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0462 0.6487 0.8830 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4766 -0.3332 1.9119 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2269 2.0846 1.3520 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5625 2.1762 2.0730 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5940 1.6697 1.1416 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7644 1.7741 1.5069 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3189 1.0636 -0.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3237 -0.0655 -0.4347 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6591 2.1299 -1.2154 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1110 -2.3772 1.3821 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7304 -1.7689 -1.9294 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0495 -2.8939 -2.3860 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6813 -0.7616 -2.8821 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1512 0.3153 1.2331 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6114 3.6802 1.5645 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9650 2.9940 0.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9003 2.5867 2.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0320 2.8992 0.4295 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3815 1.1690 0.7177 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8606 1.2935 -0.9578 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4473 -0.7934 -0.2370 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4574 -0.8231 1.2189 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8622 -2.5106 -0.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9234 -2.0887 0.9761 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8212 -3.7851 -0.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8690 -2.8046 -1.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5070 -3.6136 -0.6932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4044 -2.3796 -1.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4632 -0.3048 -1.8695 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0673 -1.0116 -2.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 0.7651 -1.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1156 1.3386 0.2574 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4286 0.1668 1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8368 0.1772 2.2691 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6156 1.7918 1.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5558 1.2118 -0.4622 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4776 -2.5632 -0.9955 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -0.7860 -2.0287 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6771 -1.5389 -0.4959 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4452 1.1868 -1.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2214 -0.0028 2.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5865 -0.4292 1.9235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0953 -1.3315 1.6979 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4762 2.4226 2.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3111 2.7102 0.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5749 1.6153 3.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7645 3.2699 2.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3199 0.4647 -0.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1753 -0.5121 -1.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4041 -0.7636 0.3988 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5762 3.1568 -0.7565 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9447 2.1151 -2.0502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7059 2.0469 -1.5511 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4070 -3.3798 1.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1428 -2.6773 1.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3615 -1.8676 2.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3566 -0.6881 -3.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5802 -0.1076 0.2707 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6078 -0.4438 1.8026 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1021 0.4576 1.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 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 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 26 28 1 0 10 29 1 1 6 30 1 0 30 31 2 0 30 32 1 0 2 33 1 0 11 7 1 0 20 15 1 0 16 10 1 0 26 19 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 6 42 1 1 7 43 1 1 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 12 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 6 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 6 21 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 M END

Standard InCHIKey	PYHNHGARAGBCRY-ZYHXIRFQSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,11,20-22,24H,8,10,12-18H2,1-7H3,(H,32,33)/t20-,21-,22-,24-,28+,29-,30+/m0/s1
SMILES	CC(=CCC[C@@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	509.035 ? Van der Waals volume.
Dense:	0.893	LogP:	5.025 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.646 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.412 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.435	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.68	Fsp³:	0.8
MCE-18:	80.593 ? 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:	0.735	Fluc inhibitor:	0.001 ? 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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.611	Promiscuous compounds:	0.089

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.138	Pgp-substrate:	0.0
PAMPA:	0.828 ? 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%):	0.003	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.323

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046	MRP1:	0.97
Plasma Protein Binding (PPB):	94.63%	Volume Distribution (VD):	0.226
Fu:	5.084% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.044
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.994	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.056
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.45
HLM stability:	0.013 ? 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):

5.186

Half-life (T1/2):

0.605

ADMET: Toxicity

hERG Blockers:	0.053	hERG Blockers (10um):	0.131
Human Hepatotoxicity (H-HT):	0.568	Drug-induced Liver Injury (DILI):	0.442
AMES Toxicity:	0.108	Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.415	Skin Sensitization:	0.854
Carcinogencity:	0.636	Eye Corrosion:	0.034
Eye Irritation:	0.45	Respiratory Toxicity:	0.816
Drug-induced Neurotoxicity:	0.3	Ototoxicity:	0.571
Hematotoxicity:	0.653	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.485	RPMI-8226 Immunitoxicity:	0.045
A549 Cytotoxicity:	0.063	Hek293 Cytotoxicity:	0.151
BCF:	1.83 ? 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:	4.567 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.781 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.397 ? 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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11222	Rubus alceifolius	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11222	Rubus alceifolius	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
Inhibition	1

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	IC50	=	20.0	ug.mL-1	PMID[10691716]
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	Inhibition	=	90.0	%	PMID[10691716]

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 NPC147066 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	26879
0.1-0.2	19848
0.2-0.3	2647
0.3-0.4	370
0.4-0.5	69
0.5-0.6	25
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC96496
0.7612	Intermediate Similarity	NPC474570
0.6818	Remote Similarity	NPC142361
0.6818	Remote Similarity	NPC474684
0.6765	Remote Similarity	NPC471896
0.6618	Remote Similarity	NPC475921
0.6618	Remote Similarity	NPC474704
0.6462	Remote Similarity	NPC478800
0.6364	Remote Similarity	NPC201912
0.6364	Remote Similarity	NPC38350
0.6364	Remote Similarity	NPC601139
0.6324	Remote Similarity	NPC478801
0.6269	Remote Similarity	NPC83569
0.6232	Remote Similarity	NPC472239
0.5915	Remote Similarity	NPC6190
0.5909	Remote Similarity	NPC247220
0.5833	Remote Similarity	NPC293081
0.5676	Remote Similarity	NPC73506
0.5522	Remote Similarity	NPC470078
0.5507	Remote Similarity	NPC82902
0.5507	Remote Similarity	NPC474218
0.5362	Remote Similarity	NPC470223
0.5352	Remote Similarity	NPC470047
0.5352	Remote Similarity	NPC470046
0.5211	Remote Similarity	NPC90652
0.5211	Remote Similarity	NPC155255
0.5211	Remote Similarity	NPC470052
0.5211	Remote Similarity	NPC470417
0.5211	Remote Similarity	NPC260992
0.5205	Remote Similarity	NPC28227
0.5135	Remote Similarity	NPC470050
0.5135	Remote Similarity	NPC470375
0.5135	Remote Similarity	NPC67831
0.5135	Remote Similarity	NPC174051
0.5135	Remote Similarity	NPC470376
0.5135	Remote Similarity	NPC470051
0.5067	Remote Similarity	NPC154101
0.5067	Remote Similarity	NPC479667
0.5067	Remote Similarity	NPC605437

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC147066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6662
0.1-0.2	2433
0.2-0.3	54
0.3-0.4	1
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