NPASS Compound

Natural Product: NPC469400

Natural Product ID	NPC469400
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(20Zeta)-3Alpha,16Alpha,25-Trihydroxy-24-Methyllanosta-8,24(241)-Dien-21-Oic Acid
IUPAC Name	(2R)-6-hydroxy-2-[(3R,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms	25-Hydroxy-3-epitumulosic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1077755
PubChem CID	46882675
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 85 88 0 0 0 0 0 0 0 0999 V2000 -2.1926 -1.9385 2.7007 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0408 -1.6908 1.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9370 -2.6155 1.4816 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0022 -0.5341 0.7379 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8849 -0.5030 -0.2234 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9729 0.7538 -1.1092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5581 1.2540 -1.2959 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2460 0.0135 -0.9880 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4930 -0.4555 0.2587 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2901 0.6178 1.3175 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1129 -1.7412 0.7257 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5088 -2.0043 0.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2548 -0.7292 0.0051 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6401 0.3051 -0.5998 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3017 1.6092 -0.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5069 1.7512 0.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3293 0.4838 -0.1737 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6597 -0.6638 0.4759 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6419 -0.6078 1.9807 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4177 -1.9363 0.1019 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6413 -1.6510 -0.7068 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5179 -0.5873 -0.0677 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7745 0.6986 0.1435 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2805 1.7242 -0.8870 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0270 1.3005 1.4950 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5977 -0.3847 -0.9270 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1281 -0.8978 -2.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3470 -0.4034 -0.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4671 -0.2090 0.9516 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7598 -0.1145 0.2417 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6986 -1.0451 0.5183 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1485 0.9037 -0.7502 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5099 0.7925 -1.0710 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3508 0.8210 -2.0081 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9748 2.2952 -0.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8302 -2.8295 2.9665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0116 0.3755 1.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9707 -1.3829 -0.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4278 0.4714 -2.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5093 1.5722 -0.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3623 1.5402 -2.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3292 2.1176 -0.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5029 0.1980 2.3264 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7946 0.8853 1.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9556 1.4745 1.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5938 -2.5690 0.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2374 -1.6474 1.8504 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4530 -2.5917 -0.7087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0649 -2.5994 0.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7047 1.6238 -1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6385 2.4831 -0.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1472 1.7536 1.0880 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1047 2.6514 -0.2039 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2876 0.2978 -1.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1272 -1.5422 2.3259 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0893 0.2200 2.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6847 -0.7243 2.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7386 -2.5683 -0.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7193 -2.5208 0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3935 -1.3820 -1.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2451 -2.5771 -0.7471 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9290 -0.9997 0.8757 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1270 2.7321 -0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3328 1.5496 -1.1328 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6467 1.6953 -1.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1335 1.6020 2.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6739 0.5694 2.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6764 2.2254 1.4420 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3647 -0.6672 -1.8505 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3643 -1.8517 -2.0060 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1502 -1.1198 -2.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 -0.3946 -3.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4344 -1.3087 -0.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2434 0.5451 -0.5812 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2984 0.7622 1.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5412 -0.9796 1.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4910 -1.8237 1.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6742 -1.0645 0.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0406 1.0551 -0.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6311 1.6811 -2.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8758 -0.1613 -2.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0706 0.8916 -2.8877 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9111 2.5329 -0.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5738 2.9922 -0.7159 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3926 2.1960 0.9084 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 1 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 22 26 1 0 8 27 1 6 4 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 9 5 1 0 18 13 1 0 14 8 1 0 23 17 1 0 1 36 1 0 4 37 1 1 5 38 1 6 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 10 43 1 0 10 44 1 0 10 45 1 0 11 46 1 0 11 47 1 0 12 48 1 0 12 49 1 0 15 50 1 0 15 51 1 0 16 52 1 0 16 53 1 0 17 54 1 6 19 55 1 0 19 56 1 0 19 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 22 62 1 1 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 27 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 31 77 1 0 31 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 M END

Standard InCHIKey	DZPUCNLUXQSVQK-SXHVIGTBSA-N
Standard InCHI	InChI=1S/C31H50O4/c1-19(28(4,5)35)9-10-20(26(33)34)21-13-17-31(8)23-11-12-24-27(2,3)25(32)15-16-29(24,6)22(23)14-18-30(21,31)7/h20-21,24-25,32,35H,1,9-18H2,2-8H3,(H,33,34)/t20-,21-,24+,25-,29-,30-,31+/m1/s1
SMILES	OC(=O)[C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)CCC(=C)C(O)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.37	Volume:	537.758 ? Van der Waals volume.
Dense:	0.904	LogP:	3.271 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.926 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.06 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	22.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.357	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.941	Fsp³:	0.839
MCE-18:	88.421 ? 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:	0.903	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.508	Promiscuous compounds:	0.155

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.156	MDCK Permeability:	-4.783
Pgp-inhibitor:	0.001	Pgp-substrate:	0.029
PAMPA:	0.999 ? 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%):	0.042	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.981
Plasma Protein Binding (PPB):	89.259%	Volume Distribution (VD):	-0.238
Fu:	7.086% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.037
BSEP inhibitor:	0.919

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.681	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.148	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.014
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.009
HLM stability:	0.002 ? 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):

8.843

Half-life (T1/2):

0.831

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.019
Human Hepatotoxicity (H-HT):	0.556	Drug-induced Liver Injury (DILI):	0.08
AMES Toxicity:	0.238	Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.192	Skin Sensitization:	0.964
Carcinogencity:	0.767	Eye Corrosion:	0.158
Eye Irritation:	0.865	Respiratory Toxicity:	0.585
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.61
Hematotoxicity:	0.494	Drug-induced Nephrotoxicity:	0.926
Genotoxicity:	0.105	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.104
BCF:	1.001 ? 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:	3.902 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.575 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.678 ? 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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	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	3
Inhibition	5

Activity Type	# Activity
Cell line	2
Others	5
Non-molecular	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	18600.0	nM	PMID[18024584]
NPT80	Cell line	Raji	Homo sapiens	Inhibition	=	70.0	%	PMID[26317881]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	99900.0	nM	PMID[19746919]
NPT2	Others	Unspecified	n.a.	IC50	=	238.0	molar ratio	PMID[19445517]
NPT2	Others	Unspecified	n.a.	Inhibition	=	93.1	%	PMID[3681893]
NPT2	Others	Unspecified	n.a.	Inhibition	=	69.4	%	PMID[26907951]
NPT2	Others	Unspecified	n.a.	Inhibition	=	20.5	%	PMID[10978218]
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PubChem BioAssay data set

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 NPC469400 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	22431
0.1-0.2	24118
0.2-0.3	2942
0.3-0.4	278
0.4-0.5	47
0.5-0.6	31
0.6-0.7	4
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8448	Intermediate Similarity	NPC55309
0.8448	Intermediate Similarity	NPC28252
0.7705	Intermediate Similarity	NPC233836
0.7705	Intermediate Similarity	NPC159046
0.7705	Intermediate Similarity	NPC187376
0.6364	Remote Similarity	NPC482908
0.6364	Remote Similarity	NPC48330
0.6364	Remote Similarity	NPC484974
0.6364	Remote Similarity	NPC23434
0.5942	Remote Similarity	NPC289213
0.5857	Remote Similarity	NPC484976
0.5797	Remote Similarity	NPC76895
0.5797	Remote Similarity	NPC173272
0.5775	Remote Similarity	NPC482518
0.5714	Remote Similarity	NPC474889
0.5634	Remote Similarity	NPC77168
0.5417	Remote Similarity	NPC243866
0.5385	Remote Similarity	NPC118508
0.5385	Remote Similarity	NPC484086
0.5342	Remote Similarity	NPC186810
0.5294	Remote Similarity	NPC471724
0.5231	Remote Similarity	NPC606082
0.5224	Remote Similarity	NPC231477
0.5224	Remote Similarity	NPC87489
0.5224	Remote Similarity	NPC123724
0.5224	Remote Similarity	NPC73875
0.5211	Remote Similarity	NPC242864
0.5205	Remote Similarity	NPC148414
0.5205	Remote Similarity	NPC111585
0.5205	Remote Similarity	NPC175628
0.5147	Remote Similarity	NPC132635
0.5147	Remote Similarity	NPC601223
0.5139	Remote Similarity	NPC84271
0.5139	Remote Similarity	NPC102414
0.5075	Remote Similarity	NPC275910
0.5075	Remote Similarity	NPC46160
0.5075	Remote Similarity	NPC202642
0.507	Remote Similarity	NPC201912
0.507	Remote Similarity	NPC38350
0.507	Remote Similarity	NPC601139

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC469400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6391
0.1-0.2	2699
0.2-0.3	58
0.3-0.4	2
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