NPASS Compound

Natural Product: NPC478127

Natural Product ID	NPC478127
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bis(sulfuric acid sodium)23-oxo-5alpha-lanosta-8-ene-3beta,28-diyl ester salt
IUPAC Name	disodium;[(3S,4R,5R,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-4-oxoheptan-2-yl]-3-sulfonatooxy-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-4-yl]methyl sulfate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	25058090
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 91 92 0 0 0 0 0 0 0 0999 V2000 3.8733 -1.4878 2.7770 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0311 -0.9986 1.3564 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8524 0.2315 1.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1392 0.8246 0.0222 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4677 1.7509 -0.3901 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2505 0.2968 -0.8232 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4873 1.1879 -0.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6168 0.6655 -1.5276 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1367 2.6091 -0.9903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8613 -1.1329 0.4962 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5237 -2.6390 0.4201 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0469 -2.6649 0.8484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6046 -1.4365 0.0932 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6034 -0.4156 0.6658 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4253 0.7865 -0.2713 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0239 1.1377 -0.5859 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0101 0.2851 0.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7478 -0.9724 0.3730 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7527 -1.8474 0.9790 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1291 -1.6098 0.4022 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3839 -0.2187 -0.0837 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3733 0.8118 0.2878 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6317 2.0410 -0.6023 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9616 2.0369 -1.2604 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0873 1.5673 -0.4171 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8156 0.1732 0.1347 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2752 0.1855 1.5559 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6840 -0.7961 -0.6400 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5625 -2.1053 -0.2767 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5708 -3.0215 -1.2564 S 0 0 0 0 0 0 0 0 0 0 0 0 -7.0252 -4.2102 -0.4690 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8365 -3.4962 -2.4845 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8387 -2.0430 -1.7424 O 0 0 0 0 0 1 0 0 0 0 0 0 -5.4574 2.4680 0.5810 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9960 3.0942 0.3678 S 0 0 0 0 0 0 0 0 0 0 0 0 -7.3828 2.8730 -1.0861 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0134 2.4281 1.2126 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9698 4.7563 0.6103 O 0 0 0 0 0 1 0 0 0 0 0 0 -2.4277 1.3035 1.6996 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1153 0.0058 1.9840 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 -1.6257 -1.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 Na 0 0 0 0 0 15 0 0 0 0 0 0 0.0000 0.0000 0.0000 Na 0 0 0 0 0 15 0 0 0 0 0 0 3.0515 -2.1473 2.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8534 -0.6266 3.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7926 -2.0663 3.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7779 -1.7779 0.9369 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5036 1.0146 2.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8746 -0.0376 1.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4880 -0.7591 -0.6327 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9397 0.3754 -1.8841 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8446 1.1467 0.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0591 -0.2510 -1.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4069 1.4521 -1.5229 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2483 0.5250 -2.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5724 3.0900 -0.1726 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5037 2.6664 -1.9009 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0818 3.1561 -1.2270 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2024 -0.8893 -0.5604 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1628 -3.2429 1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5494 -3.0251 -0.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5927 -3.5870 0.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9287 -2.5020 1.9192 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0824 0.6147 -1.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8579 1.7068 0.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2286 2.1941 -0.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0671 1.1257 -1.7121 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4791 -2.9262 0.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7550 -1.7956 2.0878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8256 -1.9465 1.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2679 -2.3782 -0.4142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2979 -0.2866 -1.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5031 2.9841 -0.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8823 2.0781 -1.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9884 1.4857 -2.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1837 3.1047 -1.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9862 1.5227 -1.1006 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3834 -0.0198 1.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8383 -0.5423 2.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2078 1.2161 2.0152 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7633 -0.4642 -0.5925 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4493 -0.7303 -1.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3862 1.6395 1.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0274 2.2421 1.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7285 0.5781 2.4422 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6210 -0.3012 2.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0661 1.1392 2.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0327 -0.2722 2.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7519 -2.7450 -1.5533 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6799 -1.2646 -1.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1575 -1.2721 -1.9139 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 4 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 2 10 1 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 2 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 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 2 0 30 33 1 0 25 34 1 0 34 35 1 0 35 36 2 0 35 37 2 0 35 38 1 0 22 39 1 1 14 40 1 1 13 41 1 6 14 10 1 0 18 13 1 0 22 17 1 0 26 21 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 6 3 48 1 0 3 49 1 0 6 50 1 0 6 51 1 0 7 52 1 0 8 53 1 0 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 9 58 1 0 10 59 1 6 11 60 1 0 11 61 1 0 12 62 1 0 12 63 1 0 15 64 1 0 15 65 1 0 16 66 1 0 16 67 1 0 19 68 1 0 19 69 1 0 20 70 1 0 20 71 1 0 21 72 1 6 23 73 1 0 23 74 1 0 24 75 1 0 24 76 1 0 25 77 1 6 27 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 28 82 1 0 39 83 1 0 39 84 1 0 39 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 41 90 1 0 41 91 1 0 M CHG 4 33 -1 38 -1 42 1 43 1 M END

Standard InCHIKey	QXPAJOLIJPTFGE-FKWVCUGYSA-L
Standard InCHI	InChI=1S/C30H50O9S2.2Na/c1-19(2)16-21(31)17-20(3)22-10-14-30(7)24-8-9-25-27(4,23(24)11-15-29(22,30)6)13-12-26(39-41(35,36)37)28(25,5)18-38-40(32,33)34;;/h19-20,22,25-26H,8-18H2,1-7H3,(H,32,33,34)(H,35,36,37);;/q;2*+1/p-2/t20-,22-,25-,26+,27-,28+,29-,30+;;/m1../s1
SMILES	C[C@H](CC(=O)CC(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H]([C@@]4(C)COS(=O)(=O)[O-])OS(=O)(=O)[O-])C)C)C.[Na+].[Na+]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	616.28	Volume:	601.431 ? Van der Waals volume.
Dense:	1.025	LogP:	2.695 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.439 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.821 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	25.0
TPSA:	149.93 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.172	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.463	Fsp³:	0.9
MCE-18:	96.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.979	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? 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:	0.423	Promiscuous compounds:	0.062

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.315	MDCK Permeability:	-4.794
Pgp-inhibitor:	0.112	Pgp-substrate:	0.0
PAMPA:	0.983 ? 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):	0.003
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.063
50% Bioavailability (F50%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.601
Plasma Protein Binding (PPB):	90.92%	Volume Distribution (VD):	0.066
Fu:	6.607% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	0.923

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.049	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.072	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.018	CYP2C8-inhibitor:	0.006
HLM stability:	0.039 ? 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):

5.752

Half-life (T1/2):

0.44

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.073
Human Hepatotoxicity (H-HT):	0.974	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.601	Rat Oral Acute Toxicity:	0.317
Maximum Recommended Daily Dose:	0.547	Skin Sensitization:	1.0
Carcinogencity:	0.772	Eye Corrosion:	0.39
Eye Irritation:	0.423	Respiratory Toxicity:	0.499
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.604
Hematotoxicity:	0.75	Drug-induced Nephrotoxicity:	0.251
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.043
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.038
BCF:	0.715 ? 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:	3.05 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.804 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.489 ? 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
NPO33593	Tydemania expeditionis	Species	n.a.	Eukaryota	n.a.	depths of 720 m at Herald Pass, Kadavu Province, Fiji (1846.370' S, 17827.746' E)	n.a.	PMID[18763828]

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	12
Activity	1

Activity Type	# Activity
Cell line	10
Others	2
Organism	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
NPT1900	Cell line	DU-4475	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT457	Cell line	BT-549	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT784	Cell line	MDA-MB-468	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT937	Cell line	NCI-H446	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT2155	Cell line	SHP77	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT404	Cell line	CCRF-CEM	Homo sapiens	IC50	=	31000	nM	PMID[18763828]
NPT3927	Organism	Rotifers	Rotifera	Activity	=	9	%	PMID[18763828]
NPT2	Others	Unspecified	n.a.	IC50	=	31000	nM	PMID[18763828]

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 NPC478127 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	27731
0.1-0.2	21085
0.2-0.3	920
0.3-0.4	108
0.4-0.5	13
0.5-0.6	0
0.6-0.7	1
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
0.6	Remote Similarity	NPC478128

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7333
0.1-0.2	1799
0.2-0.3	18
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