NPASS Compound

Natural Product: NPC127855

Natural Product ID	NPC127855
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HLBZSQOUBVLLLL-CWCCKSQSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11443665
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 89 93 0 0 0 0 0 0 0 0999 V2000 -5.0403 -2.3257 -1.9464 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0270 -1.0322 -1.1431 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3887 0.0287 -2.0096 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1417 1.3270 -1.3093 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8950 1.1949 0.1741 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9825 2.2634 0.7161 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 1.7531 1.2872 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9855 0.8791 0.3295 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5395 1.7115 -0.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9343 -0.2196 -0.0361 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3831 -1.2058 -0.7357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0456 -1.2791 -1.1471 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9128 -0.4454 -0.3006 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3028 -0.9663 -0.0135 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3722 -2.2516 0.7165 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9706 -1.1823 -1.3726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7859 -0.0221 -1.8121 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9010 0.3585 -0.8796 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5084 0.1482 0.5748 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9824 1.3587 1.4024 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1790 -1.0282 1.1597 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0206 0.1902 0.6220 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4459 0.5318 1.9560 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0374 1.0625 1.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2068 0.1026 0.8989 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2515 -0.9686 1.8559 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1252 -0.2574 -1.2009 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2486 0.4549 -1.5907 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1566 1.7058 -1.6559 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5552 -0.1553 -1.9374 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3097 -0.1464 0.4442 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2018 -1.3015 0.0955 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2102 -1.5638 1.2260 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2103 1.3949 0.9003 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2852 1.6158 0.3126 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1830 1.3252 2.2721 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3291 1.4929 3.0811 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3980 -3.1179 -1.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0290 -2.6205 -2.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7710 -2.2830 -2.7780 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0920 -0.8274 -0.9102 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1404 0.2439 -2.8235 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5200 -0.3981 -2.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9731 2.0604 -1.4900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2569 1.7880 -1.7729 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4686 2.8132 1.5853 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8848 3.0531 -0.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0575 2.6466 1.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9143 1.3109 2.2717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5458 1.2093 -1.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4431 2.2326 -0.6058 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2158 2.6045 -0.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0727 -2.0022 -1.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2807 -2.3697 -1.1267 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0555 -1.0335 -2.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1580 0.4555 -0.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1932 -2.9290 0.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -2.1992 1.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4573 -2.8991 0.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2184 -1.3791 -2.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6211 -2.0974 -1.3543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0980 0.8383 -2.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2475 -0.2840 -2.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 1.4521 -1.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0686 1.5532 1.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3719 2.2418 1.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9857 1.0099 2.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3356 -1.8754 0.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2348 -0.7052 1.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7296 -1.3029 2.1214 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7519 1.0748 -0.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9803 1.3801 2.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4230 -0.2838 2.6723 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1440 2.0632 1.2842 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4967 1.1950 2.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0670 -0.5278 2.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5780 -1.0963 2.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5474 -1.9118 1.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0306 0.4082 -2.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2671 -0.0138 -1.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4701 -1.2063 -2.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2437 -0.1912 1.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6566 -2.2786 0.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7421 -1.3582 2.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4834 -2.6451 1.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1138 -0.9698 1.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1967 2.4058 3.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2300 1.5926 2.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3737 0.6248 3.7711 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 18 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 10 31 1 0 31 32 1 0 32 33 1 0 5 34 1 1 34 35 2 0 34 36 1 0 36 37 1 0 32 2 1 0 31 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 1 3 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 9 50 1 0 9 51 1 0 9 52 1 0 11 53 1 0 12 54 1 0 12 55 1 0 13 56 1 6 15 57 1 0 15 58 1 0 15 59 1 0 16 60 1 0 16 61 1 0 17 62 1 0 17 63 1 0 18 64 1 1 20 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 21 70 1 0 22 71 1 6 23 72 1 0 23 73 1 0 24 74 1 0 24 75 1 0 26 76 1 0 26 77 1 0 26 78 1 0 30 79 1 0 30 80 1 0 30 81 1 0 31 82 1 1 32 83 1 6 33 84 1 0 33 85 1 0 33 86 1 0 37 87 1 0 37 88 1 0 37 89 1 0 M END

Standard InCHIKey	HLBZSQOUBVLLLL-CWCCKSQSSA-N
Standard InCHI	InChI=1S/C33H52O4/c1-20-12-17-33(28(35)36-9)19-18-31(7)23(27(33)21(20)2)10-11-25-30(6)15-14-26(37-22(3)34)29(4,5)24(30)13-16-32(25,31)8/h10,20-21,24-27H,11-19H2,1-9H3/t20-,21+,24+,25-,26+,27+,30+,31-,32-,33+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)C)[C@@H]2[C@H]1C)C(=O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.39	Volume:	563.793 ? Van der Waals volume.
Dense:	0.909	LogP:	5.771 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.469 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.151 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	52.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.28	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.782	Fsp³:	0.879
MCE-18:	103.161 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.955	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.065 ? 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:	0.396	Promiscuous compounds:	0.266

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.349	MDCK Permeability:	-4.974
Pgp-inhibitor:	0.995	Pgp-substrate:	0.01
PAMPA:	0.416 ? 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%):	0.381	30% Bioavailability (F30%):	0.562
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15	MRP1:	0.729
Plasma Protein Binding (PPB):	96.209%	Volume Distribution (VD):	-0.082
Fu:	4.348% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.584
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.042	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.684	CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.012	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.992	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.944 ? 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):

6.998

Half-life (T1/2):

0.352

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.16
Human Hepatotoxicity (H-HT):	0.506	Drug-induced Liver Injury (DILI):	0.634
AMES Toxicity:	0.383	Rat Oral Acute Toxicity:	0.352
Maximum Recommended Daily Dose:	0.489	Skin Sensitization:	0.874
Carcinogencity:	0.892	Eye Corrosion:	0.151
Eye Irritation:	0.604	Respiratory Toxicity:	0.833
Drug-induced Neurotoxicity:	0.044	Ototoxicity:	0.31
Hematotoxicity:	0.633	Drug-induced Nephrotoxicity:	0.727
Genotoxicity:	0.69	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.451	Hek293 Cytotoxicity:	0.368
BCF:	2.228 ? 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:	4.527 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.631 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.347 ? 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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22067	Pogostemon stellatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	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
Inhibition	1
IC50	1

Activity Type	# Activity
Individual protein	1
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	3.7	%	PMID[34688014]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	20000.0	nM	PMID[34688014]

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 NPC127855 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	23772
0.1-0.2	22129
0.2-0.3	3152
0.3-0.4	683
0.4-0.5	81
0.5-0.6	28
0.6-0.7	8
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
0.7931	Intermediate Similarity	NPC290495
0.7143	Intermediate Similarity	NPC162107
0.7143	Intermediate Similarity	NPC46912
0.6984	Remote Similarity	NPC40552
0.6984	Remote Similarity	NPC606009
0.6769	Remote Similarity	NPC329943
0.6418	Remote Similarity	NPC307335
0.6418	Remote Similarity	NPC74855
0.6389	Remote Similarity	NPC171208
0.625	Remote Similarity	NPC195334
0.6154	Remote Similarity	NPC224145
0.5972	Remote Similarity	NPC488520
0.5915	Remote Similarity	NPC113989
0.5797	Remote Similarity	NPC191965
0.5735	Remote Similarity	NPC610552
0.5714	Remote Similarity	NPC286786
0.5694	Remote Similarity	NPC485589
0.5595	Remote Similarity	NPC477291
0.5417	Remote Similarity	NPC184006
0.5395	Remote Similarity	NPC488522
0.5352	Remote Similarity	NPC9892
0.5352	Remote Similarity	NPC10005
0.5352	Remote Similarity	NPC91525
0.5342	Remote Similarity	NPC488523
0.5342	Remote Similarity	NPC120840
0.5256	Remote Similarity	NPC488524
0.5217	Remote Similarity	NPC95594
0.5211	Remote Similarity	NPC73013
0.5211	Remote Similarity	NPC477579
0.52	Remote Similarity	NPC488525
0.52	Remote Similarity	NPC477875
0.5195	Remote Similarity	NPC485586
0.5195	Remote Similarity	NPC485588
0.5195	Remote Similarity	NPC477876
0.5176	Remote Similarity	NPC182249
0.5152	Remote Similarity	NPC27765
0.5152	Remote Similarity	NPC122418
0.5152	Remote Similarity	NPC491014
0.5075	Remote Similarity	NPC82477

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC127855 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7488
0.1-0.2	1622
0.2-0.3	34
0.3-0.4	4
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