NPASS Compound

Natural Product: NPC196136

Natural Product ID	NPC196136
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(24S)-Ergostane-3Beta,5Alpha,6Beta,25-Tetraol
IUPAC Name	(3S,5R,6R,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-6-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,5,6-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1762127
PubChem CID	14034726
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

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 7.7426 -0.7393 -0.8075 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7047 -0.0438 -1.4556 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8006 -0.9757 -2.1690 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5538 -1.3537 -1.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0069 -0.3816 -0.4986 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5409 0.9959 -0.7882 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0502 0.9057 -0.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4454 1.1586 -2.1923 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8983 2.0992 -0.0587 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9153 2.7848 0.6539 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8142 1.7902 0.8825 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1443 0.4849 0.7713 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5152 -0.2957 -0.4954 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8563 -1.6335 -0.4350 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3519 -1.4948 -0.3445 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0235 -0.7710 0.8984 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6651 0.6013 0.7658 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0440 1.4017 1.8280 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4027 0.9534 1.8053 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4438 -0.2890 0.9376 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4680 -1.1999 1.4751 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8097 -0.4815 1.4196 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2474 -0.0713 0.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6095 0.6230 0.2095 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1183 1.0702 -1.1451 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2701 1.9555 -1.7633 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3607 -0.1220 -2.0536 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4525 1.7598 -0.9558 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6226 -0.2985 0.8539 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6348 -2.4970 0.7339 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3395 -1.4437 2.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4926 -0.7978 0.8908 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4731 -0.1659 -0.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2358 0.5773 -2.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5864 -0.6046 -3.2154 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3851 -1.9273 -2.3553 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7624 -1.5252 -2.2631 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6404 -2.3532 -0.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2518 0.6716 0.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4160 1.9647 -0.6611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6626 0.7070 -2.5584 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5629 2.8657 -0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3221 3.4933 0.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1537 1.9098 1.9562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0235 2.5961 0.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4291 -0.1948 1.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0923 0.2674 -1.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2324 -2.3019 0.3534 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0401 -2.1907 -1.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0549 -2.5172 -0.4282 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0144 -0.9171 -1.2101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3495 0.9974 -0.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0607 2.4962 1.5640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5099 1.3356 2.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0576 1.7463 1.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6504 0.7057 2.8780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7215 -0.0030 -0.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3113 -1.4420 2.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6183 -1.1349 1.8617 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8095 0.4336 2.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5814 0.7436 -0.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3811 -0.8658 -0.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5337 1.5257 0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7714 2.5061 -1.0820 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0252 -0.8505 -1.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9488 0.2428 -2.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4374 -0.5720 -2.4207 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3117 1.0676 -1.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5338 2.2387 0.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5898 2.5388 -1.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6265 -0.0641 0.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5166 -0.1720 1.9595 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3114 -1.3450 0.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6494 -2.3386 -0.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8976 -3.2660 0.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6206 -2.9288 1.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4448 -0.6863 2.9746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3083 -1.9816 2.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4207 -2.1727 2.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6100 0.0448 1.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5270 -1.2266 0.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8970 -1.6224 1.3114 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 6 8 1 6 6 9 1 0 9 10 1 0 9 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 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 24 29 1 0 21 30 1 0 16 31 1 1 5 32 1 1 7 2 1 0 17 12 1 0 13 5 1 0 20 16 1 0 1 33 1 0 2 34 1 6 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 7 39 1 0 7 40 1 0 8 41 1 0 9 42 1 6 10 43 1 0 11 44 1 0 11 45 1 0 12 46 1 1 13 47 1 6 14 48 1 0 14 49 1 0 15 50 1 0 15 51 1 0 17 52 1 6 18 53 1 0 18 54 1 0 19 55 1 0 19 56 1 0 20 57 1 6 21 58 1 1 22 59 1 0 22 60 1 0 23 61 1 0 23 62 1 0 24 63 1 1 26 64 1 0 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	DDUGSCXKUOFBQJ-UXTULTQLSA-N
Standard InCHI	InChI=1S/C28H50O4/c1-17(7-8-18(2)25(3,4)31)21-9-10-22-20-15-24(30)28(32)16-19(29)11-14-27(28,6)23(20)12-13-26(21,22)5/h17-24,29-32H,7-16H2,1-6H3/t17-,18+,19+,20+,21-,22+,23+,24-,26-,27-,28+/m1/s1
SMILES	O[C@H]1CC[C@]2([C@@](C1)(O)[C@H](O)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CC[C@@H](C(O)(C)C)C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	450.37	Volume:	493.779 ? Van der Waals volume.
Dense:	0.912	LogP:	5.664 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.636 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.38 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.479	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.826	Fsp³:	1.0
MCE-18:	83.429 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.551	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? 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:	0.39	Promiscuous compounds:	0.421

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9	MDCK Permeability:	-4.755
Pgp-inhibitor:	0.001	Pgp-substrate:	0.869
PAMPA:	0.654 ? 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%):	0.024	30% Bioavailability (F30%):	0.087
50% Bioavailability (F50%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199	MRP1:	0.323
Plasma Protein Binding (PPB):	94.191%	Volume Distribution (VD):	-0.196
Fu:	5.673% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.836
BSEP inhibitor:	0.855

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.015	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.933
HLM stability:	0.051 ? 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):

6.072

Half-life (T1/2):

2.527

ADMET: Toxicity

hERG Blockers:	0.066	hERG Blockers (10um):	0.15
Human Hepatotoxicity (H-HT):	0.502	Drug-induced Liver Injury (DILI):	0.048
AMES Toxicity:	0.149	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.735	Skin Sensitization:	0.957
Carcinogencity:	0.75	Eye Corrosion:	0.024
Eye Irritation:	0.788	Respiratory Toxicity:	0.725
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.824
Hematotoxicity:	0.237	Drug-induced Nephrotoxicity:	0.682
Genotoxicity:	0.029	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.088	Hek293 Cytotoxicity:	0.496
BCF:	1.594 ? 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:	3.798 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.256 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.52 ? 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
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217734]
NPO4141	Gaillardia arizonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3043	Plocamium hamatum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14478	Helenium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13946	Dolichospermum spiroides	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12200	Eucalyptus carnea	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13780	Mesua racemosa	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4141	Gaillardia arizonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14070	Spongosorites genitrix	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3043	Plocamium hamatum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14478	Helenium laciniatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5349	Citrus hybrid	Species	Rutaceae	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	2

Activity Type	# Activity
Cell line	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
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[21354791]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	59060.0	nM	PMID[21354791]

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 NPC196136 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	27583
0.1-0.2	20416
0.2-0.3	1621
0.3-0.4	197
0.4-0.5	23
0.5-0.6	10
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8696	High Similarity	NPC192501
0.8163	Intermediate Similarity	NPC10476
0.7959	Intermediate Similarity	NPC228994
0.75	Intermediate Similarity	NPC486085
0.7407	Intermediate Similarity	NPC60018
0.7407	Intermediate Similarity	NPC202688
0.661	Remote Similarity	NPC486086
0.5862	Remote Similarity	NPC85095
0.569	Remote Similarity	NPC67657
0.5469	Remote Similarity	NPC486638
0.5323	Remote Similarity	NPC154043
0.5263	Remote Similarity	NPC158208
0.5254	Remote Similarity	NPC198968
0.5231	Remote Similarity	NPC219516
0.5167	Remote Similarity	NPC211135
0.5143	Remote Similarity	NPC293609
0.5085	Remote Similarity	NPC216420

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC196136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7698
0.1-0.2	1301
0.2-0.3	137
0.3-0.4	12
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