NPASS Compound

Natural Product: NPC145238

Natural Product ID	NPC145238
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UUDRJPRIBMGADE-YNOQIDMFSA-N
IUPAC Name	n.a.
Synonyms	NSC-336793
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446957
PubChem CID	6450291
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

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 82 85 0 0 0 0 0 0 0 0999 V2000 9.4518 1.6034 -7.6380 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8101 1.1146 -6.3722 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3789 0.7061 -6.6842 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6621 0.2037 -5.4857 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5721 0.7505 -4.9998 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9053 0.2344 -3.8366 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8110 0.7586 -3.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2195 0.1582 -2.1456 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1303 0.6089 -1.5709 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5018 0.0356 -0.3831 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9653 -0.9717 0.2128 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3412 0.5817 0.1585 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3069 0.0520 1.3274 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5606 -0.7162 0.8354 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0717 -2.0693 0.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5263 -0.6941 1.9288 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8742 -0.9326 3.1502 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 0.7647 1.9945 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9126 1.4761 2.7050 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5459 1.0286 2.3969 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3620 0.9828 3.4839 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 1.2443 3.3273 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2333 1.5544 2.2392 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6617 1.1792 4.4943 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9724 2.4369 2.0829 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5423 3.5654 3.0298 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0828 2.8990 0.6709 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2955 0.7872 2.6898 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4380 0.2640 2.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7449 -0.4761 0.9965 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6157 -1.4741 0.7274 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7092 -1.5790 1.8917 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4159 -2.9958 2.0953 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2480 -3.7336 1.3995 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1637 -2.8681 0.6735 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2371 -3.2532 0.1005 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2658 -5.2508 1.3478 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0296 -1.1961 -0.4806 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6134 0.4241 3.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0931 -0.8353 3.5273 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3122 0.9753 -7.9614 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8358 2.6556 -7.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6971 1.6308 -8.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4205 0.3012 -5.9677 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7949 1.9743 -5.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4469 -0.1037 -7.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8623 1.5961 -7.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0323 -0.6799 -4.9371 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1697 1.6184 -5.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3400 -0.6514 -3.3485 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3819 1.6211 -3.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6739 -0.7120 -1.6812 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6715 1.4848 -2.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3317 -0.7710 1.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8884 -0.1983 -0.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5021 -1.8884 -0.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8625 -2.7723 0.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3544 -2.4982 1.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 -0.6316 3.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1780 1.0711 0.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1375 1.5627 3.8102 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3418 2.0598 4.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1527 1.0253 5.4460 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2951 0.2871 4.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1118 3.1655 3.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4837 3.8688 3.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1209 4.4177 2.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 3.9975 0.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9040 2.4125 0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1086 2.8537 0.1116 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3786 1.2731 3.6643 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6641 -1.0564 1.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8197 0.2146 0.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3164 -1.2879 2.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6216 -3.3718 2.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3311 -5.6290 0.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3242 -5.6474 2.4017 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1884 -5.5640 0.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8719 -2.0343 -0.9882 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3055 0.9760 4.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3925 0.9551 2.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7673 -1.1860 2.8790 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 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 21 22 1 0 22 23 2 0 22 24 1 0 20 25 1 0 25 26 1 0 25 27 1 0 18 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 31 38 1 6 29 39 1 0 39 40 1 0 20 13 1 0 35 31 1 0 32 16 1 0 25 19 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 2 45 1 0 3 46 1 0 3 47 1 0 4 48 1 0 5 49 1 0 6 50 1 0 7 51 1 0 8 52 1 0 9 53 1 0 13 54 1 1 14 55 1 6 15 56 1 0 15 57 1 0 15 58 1 0 17 59 1 0 18 60 1 6 19 61 1 1 24 62 1 0 24 63 1 0 24 64 1 0 26 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 30 72 1 0 30 73 1 0 32 74 1 1 33 75 1 0 37 76 1 0 37 77 1 0 37 78 1 0 38 79 1 0 39 80 1 0 39 81 1 0 40 82 1 0 M END

Standard InCHIKey	UUDRJPRIBMGADE-YNOQIDMFSA-N
Standard InCHI	InChI=1S/C32H42O8/c1-7-8-9-10-11-12-13-14-25(35)39-28-20(3)31(38)23(26-29(5,6)32(26,28)40-21(4)34)16-22(18-33)17-30(37)24(31)15-19(2)27(30)36/h9-16,20,23-24,26,28,33,37-38H,7-8,17-18H2,1-6H3/b10-9+,12-11+,14-13+/t20-,23+,24-,26-,28-,30-,31-,32-/m1/s1
SMILES	CCC/C=C/C=C/C=C/C(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	554.29	Volume:	577.032 ? Van der Waals volume.
Dense:	0.961	LogP:	2.573 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.734 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.328 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	24.0
TPSA:	130.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.18	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.367	Fsp³:	0.594
MCE-18:	81.333 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.526	Fluc inhibitor:	0.026 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.092 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.412	Promiscuous compounds:	0.398

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.494	MDCK Permeability:	-5.105
Pgp-inhibitor:	0.895	Pgp-substrate:	0.984
PAMPA:	0.961 ? 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):	0.273
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.095
Plasma Protein Binding (PPB):	68.348%	Volume Distribution (VD):	-0.115
Fu:	32.132% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.819
CYP3A4-inhibitor:	0.021	CYP3A4-substrate:	0.77
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

5.386

Half-life (T1/2):

1.298

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.287
Human Hepatotoxicity (H-HT):	0.733	Drug-induced Liver Injury (DILI):	0.53
AMES Toxicity:	0.873	Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.724	Skin Sensitization:	0.996
Carcinogencity:	0.649	Eye Corrosion:	0.003
Eye Irritation:	0.583	Respiratory Toxicity:	0.81
Drug-induced Neurotoxicity:	0.254	Ototoxicity:	0.673
Hematotoxicity:	0.669	Drug-induced Nephrotoxicity:	0.859
Genotoxicity:	0.793	RPMI-8226 Immunitoxicity:	0.132
A549 Cytotoxicity:	0.086	Hek293 Cytotoxicity:	0.33
BCF:	0.654 ? 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:	3.499 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.376 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.597 ? 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
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	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
ED50	1

Activity Type	# Activity
Cell line	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
NPT168	Cell line	P388	Mus musculus	ED50	=	0.0022	ug ml-1	PMID[19072214]

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 NPC145238 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	17370
0.1-0.2	31213
0.2-0.3	1076
0.3-0.4	82
0.4-0.5	55
0.5-0.6	24
0.6-0.7	16
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8378	Intermediate Similarity	NPC482199
0.8378	Intermediate Similarity	NPC482197
0.831	Intermediate Similarity	NPC478999
0.8194	Intermediate Similarity	NPC484333
0.8158	Intermediate Similarity	NPC482198
0.7595	Intermediate Similarity	NPC479001
0.7595	Intermediate Similarity	NPC479002
0.7183	Intermediate Similarity	NPC171905
0.7183	Intermediate Similarity	NPC472397
0.7162	Intermediate Similarity	NPC5991
0.7162	Intermediate Similarity	NPC196500
0.7162	Intermediate Similarity	NPC471108
0.7162	Intermediate Similarity	NPC5989
0.7027	Intermediate Similarity	NPC275696
0.7027	Intermediate Similarity	NPC255081
0.6986	Remote Similarity	NPC472758
0.6883	Remote Similarity	NPC236918
0.6883	Remote Similarity	NPC156745
0.6757	Remote Similarity	NPC157252
0.6753	Remote Similarity	NPC243902
0.6667	Remote Similarity	NPC471125
0.6579	Remote Similarity	NPC145182
0.6456	Remote Similarity	NPC22628
0.6456	Remote Similarity	NPC600005
0.642	Remote Similarity	NPC482220
0.641	Remote Similarity	NPC471128
0.641	Remote Similarity	NPC471126
0.641	Remote Similarity	NPC608501
0.6296	Remote Similarity	NPC472759
0.6296	Remote Similarity	NPC482221
0.6279	Remote Similarity	NPC601392
0.5882	Remote Similarity	NPC482219
0.5823	Remote Similarity	NPC482454
0.5698	Remote Similarity	NPC482200
0.5667	Remote Similarity	NPC601559
0.5604	Remote Similarity	NPC283875
0.5568	Remote Similarity	NPC138641
0.5568	Remote Similarity	NPC611243
0.5556	Remote Similarity	NPC601964
0.5517	Remote Similarity	NPC472398
0.5517	Remote Similarity	NPC600915
0.5467	Remote Similarity	NPC153036
0.5435	Remote Similarity	NPC22571
0.5402	Remote Similarity	NPC472760
0.5402	Remote Similarity	NPC153651
0.5402	Remote Similarity	NPC482222
0.5301	Remote Similarity	NPC488610
0.5227	Remote Similarity	NPC484334
0.5195	Remote Similarity	NPC156252
0.5172	Remote Similarity	NPC609983
0.5128	Remote Similarity	NPC158523
0.5116	Remote Similarity	NPC488611
0.5109	Remote Similarity	NPC185876
0.5109	Remote Similarity	NPC19336
0.5059	Remote Similarity	NPC485732

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC145238 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6676
0.1-0.2	2464
0.2-0.3	10
0.3-0.4	0
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