NPASS Compound

Natural Product: NPC477579

Natural Product ID	NPC477579
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-[(1S,2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picen-4a-yl]acetaldehyde
IUPAC Name	2-[(1S,2R,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picen-4a-yl]acetaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44583866
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 -5.9035 -1.4514 1.8086 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1382 -0.2926 1.2058 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7614 0.0170 -0.1408 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7701 0.0418 -1.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5601 0.8422 -0.8740 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4893 0.8982 -1.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5609 -0.2933 -1.9301 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7371 -0.4653 -0.6994 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4690 0.2917 0.3657 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8021 0.9723 1.2807 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6636 1.1131 1.4219 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3085 0.1667 0.4957 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7142 -0.1108 -0.8056 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4886 -1.3433 -1.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9776 -1.0198 -1.4683 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5258 -0.6020 -0.1266 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7886 0.4892 0.5402 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1502 0.3136 2.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5223 -0.1510 2.2747 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5262 -0.0095 1.1987 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0068 -0.5268 -0.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5179 -1.9786 -0.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6562 0.2277 -1.2194 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0595 1.2936 1.0876 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1531 1.8815 0.2144 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9658 0.8791 -1.9194 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9448 0.3517 0.4216 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7104 -0.8194 0.8849 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2289 -1.4251 2.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8318 -1.9447 -0.3057 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0713 2.2911 -0.7293 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6405 2.7938 -1.9740 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9254 3.0826 -2.9089 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5021 -2.4404 1.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9810 -1.4501 1.4950 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8755 -1.4479 2.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0861 0.5747 1.8810 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2978 0.9874 -0.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5482 -0.7425 -0.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5368 -0.9225 -1.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2635 0.6348 -2.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9362 0.9740 -2.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9490 1.8585 -1.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0212 -0.2370 -2.8877 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2397 -1.1920 -2.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4511 1.4988 2.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9725 2.1788 1.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8947 0.8344 2.4836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2955 -0.8420 1.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4427 -2.1881 -0.6501 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2125 -1.5579 -2.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2447 -0.4104 -2.3157 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4436 -2.0337 -1.6720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2888 -1.5207 0.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4586 -0.4394 2.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9660 1.2644 2.5782 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5473 -1.2356 2.5969 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9407 0.3781 3.1834 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4271 -0.6130 1.5320 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4231 -2.2944 -1.2699 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8930 -2.5926 0.4654 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5870 -1.9490 0.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1637 1.1572 -0.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5284 -0.3417 -1.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0422 0.5047 -2.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7747 1.8169 1.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5884 2.4678 1.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9342 1.9910 -0.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3270 2.5574 -0.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8797 0.3699 -2.9290 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0525 1.1695 -1.9649 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4250 1.8103 -1.8477 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2717 1.1553 1.1594 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9980 -1.5763 0.1183 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0839 -2.5135 1.9836 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8537 -1.2301 3.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2168 -0.9986 2.3844 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8480 -2.3110 -0.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4430 -2.5994 -1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1829 -2.1269 0.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7673 2.3047 0.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1735 2.8884 -0.3909 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7064 2.9163 -2.0833 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 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 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 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 17 25 1 6 13 26 1 6 9 27 1 0 27 28 1 0 28 29 1 0 8 30 1 1 5 31 1 1 31 32 1 0 32 33 2 0 28 2 1 0 27 5 1 0 13 8 1 0 17 12 1 0 21 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 1 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 1 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 20 59 1 1 22 60 1 0 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 23 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 27 73 1 1 28 74 1 6 29 75 1 0 29 76 1 0 29 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 31 82 1 0 32 83 1 0 M END

Standard InCHIKey	XVYNHNJCVHARPC-JFEQRZBLSA-N
Standard InCHI	InChI=1S/C31H50O2/c1-20-10-15-31(18-19-32)17-16-29(6)22(26(31)21(20)2)8-9-24-28(5)13-12-25(33)27(3,4)23(28)11-14-30(24,29)7/h8,19-21,23-26,33H,9-18H2,1-7H3/t20-,21+,23+,24-,25+,26+,28+,29-,30-,31-/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)CC=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.38	Volume:	514.257 ? Van der Waals volume.
Dense:	0.884	LogP:	5.273 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.115 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.795 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.344	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.95	Fsp³:	0.903
MCE-18:	99.085 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.945	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? 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:	0.482	Promiscuous compounds:	0.05

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.521	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.667	Pgp-substrate:	0.091
PAMPA:	0.921 ? 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%):	0.943	30% Bioavailability (F30%):	0.566
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977	MRP1:	0.889
Plasma Protein Binding (PPB):	97.544%	Volume Distribution (VD):	-0.255
Fu:	3.475% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.877	BCRP inhibitor:	0.581
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.522	CYP1A2-substrate:	0.71
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.291	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.067	CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.978 ? 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):

10.43

Half-life (T1/2):

0.31

ADMET: Toxicity

hERG Blockers:	0.07	hERG Blockers (10um):	0.154
Human Hepatotoxicity (H-HT):	0.593	Drug-induced Liver Injury (DILI):	0.43
AMES Toxicity:	0.57	Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.486	Skin Sensitization:	0.965
Carcinogencity:	0.874	Eye Corrosion:	0.066
Eye Irritation:	0.59	Respiratory Toxicity:	0.813
Drug-induced Neurotoxicity:	0.221	Ototoxicity:	0.488
Hematotoxicity:	0.724	Drug-induced Nephrotoxicity:	0.888
Genotoxicity:	0.977	RPMI-8226 Immunitoxicity:	0.073
A549 Cytotoxicity:	0.604	Hek293 Cytotoxicity:	0.574
BCF:	1.945 ? 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:	4.375 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.441 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.068 ? 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
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	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	5

Activity Type	# Activity
Cell line	3
Others	2

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
NPT1475	Cell line	WI-38 VA13	Homo sapiens	IC50	=	85400	nM	PMID[16933868]
NPT81	Cell line	A549	Homo sapiens	IC50	=	158000	nM	PMID[16933868]
NPT81	Cell line	A549	Homo sapiens	IC50	=	205000	nM	PMID[16933868]
NPT27	Others	Unspecified	n.a.	IC50	=	94700	nM	PMID[16933868]
NPT2	Others	Unspecified	n.a.	IC50	=	99000	nM	PMID[16933868]

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 NPC477579 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	20976
0.1-0.2	24404
0.2-0.3	3517
0.3-0.4	760
0.4-0.5	141
0.5-0.6	51
0.6-0.7	3
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
0.7797	Intermediate Similarity	NPC95594
0.7544	Intermediate Similarity	NPC27765
0.7544	Intermediate Similarity	NPC122418
0.7544	Intermediate Similarity	NPC491014
0.7541	Intermediate Similarity	NPC40552
0.7049	Intermediate Similarity	NPC40394
0.6613	Remote Similarity	NPC132478
0.6129	Remote Similarity	NPC120098
0.6	Remote Similarity	NPC235341
0.5942	Remote Similarity	NPC307335
0.5942	Remote Similarity	NPC74855
0.5873	Remote Similarity	NPC290598
0.5873	Remote Similarity	NPC30590
0.5797	Remote Similarity	NPC610937
0.5758	Remote Similarity	NPC291379
0.5714	Remote Similarity	NPC51700
0.5714	Remote Similarity	NPC88716
0.5714	Remote Similarity	NPC68160
0.5672	Remote Similarity	NPC602872
0.5634	Remote Similarity	NPC18872
0.5634	Remote Similarity	NPC290614
0.5507	Remote Similarity	NPC246708
0.5493	Remote Similarity	NPC171203
0.5493	Remote Similarity	NPC307426
0.5493	Remote Similarity	NPC98442
0.5493	Remote Similarity	NPC242468
0.5493	Remote Similarity	NPC195019
0.5373	Remote Similarity	NPC101475
0.5352	Remote Similarity	NPC272075
0.5352	Remote Similarity	NPC86372
0.5342	Remote Similarity	NPC49776
0.5342	Remote Similarity	NPC63118
0.5342	Remote Similarity	NPC474436
0.5303	Remote Similarity	NPC82477
0.5294	Remote Similarity	NPC290495
0.5294	Remote Similarity	NPC477292
0.5286	Remote Similarity	NPC606009
0.5278	Remote Similarity	NPC7260
0.5278	Remote Similarity	NPC210037
0.5278	Remote Similarity	NPC120968
0.5278	Remote Similarity	NPC227467
0.5278	Remote Similarity	NPC273621
0.5278	Remote Similarity	NPC112866
0.5217	Remote Similarity	NPC470588
0.5211	Remote Similarity	NPC127855
0.5211	Remote Similarity	NPC479748
0.5211	Remote Similarity	NPC477872
0.5139	Remote Similarity	NPC480946
0.5139	Remote Similarity	NPC187722
0.5139	Remote Similarity	NPC274330
0.5139	Remote Similarity	NPC130577
0.5139	Remote Similarity	NPC142415
0.5139	Remote Similarity	NPC102683
0.5128	Remote Similarity	NPC171208
0.507	Remote Similarity	NPC610552
0.5068	Remote Similarity	NPC182797
0.5068	Remote Similarity	NPC488519
0.5068	Remote Similarity	NPC52169
0.5068	Remote Similarity	NPC488562
0.5068	Remote Similarity	NPC606443

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7163
0.1-0.2	1930
0.2-0.3	54
0.3-0.4	1
0.4-0.5	2
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