NPASS Compound

Natural Product: NPC142253

Natural Product ID	NPC142253
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Anwuweizonic Acid
IUPAC Name	(Z,6R)-2-methyl-6-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-2-enoic acid
Synonyms	Anwuweizonic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL457685
PubChem CID	6451093
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 79 82 0 0 0 0 0 0 0 0999 V2000 3.1148 -0.9779 1.5213 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0397 -0.8317 0.0258 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4382 -0.6024 -0.4799 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0441 0.6698 0.1323 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3895 0.8727 -0.3667 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4732 0.9270 0.3508 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8147 1.1482 -0.3415 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4950 0.7904 1.7802 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6577 0.8688 2.3434 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4692 0.5879 2.6552 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0534 0.1814 -0.4083 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9647 0.3560 -1.9001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5014 0.2563 -2.2833 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1480 0.6708 -1.0117 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0272 2.1398 -0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5626 0.2347 -0.8906 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0346 0.2825 0.3567 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1786 0.7400 1.4947 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2606 0.3004 1.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6498 -0.1628 -0.0005 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3255 -1.5996 -0.2541 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4402 -0.1050 0.7172 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3601 -1.2922 1.6013 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0963 1.0373 1.5065 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5846 0.9339 1.5164 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0779 -0.3744 1.0053 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8275 -1.0732 1.6818 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6180 -0.7787 -0.3489 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7606 -2.2629 -0.5812 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5294 -0.0967 -1.3601 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2252 -0.2762 -0.5353 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4698 -1.0869 -1.5950 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3372 -0.1983 -2.0546 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8538 -0.0561 2.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1810 -1.2118 1.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4645 -1.8194 1.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7481 -1.8476 -0.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5313 -0.6168 -1.5759 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0598 -1.4377 -0.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3763 1.5439 -0.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9699 0.5524 1.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5369 0.9963 -1.4620 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1084 2.1909 -0.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6934 0.9355 -1.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5010 0.4070 0.0813 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3958 1.0748 3.5509 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3350 1.1642 0.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2953 1.3741 -2.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 -0.3620 -2.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3078 -0.7694 -2.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2589 0.9189 -3.1429 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7203 2.4090 0.0223 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9172 2.6893 -0.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4828 2.6083 -1.7204 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2752 1.8559 1.5993 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5510 0.3328 2.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5117 -0.4990 2.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8746 1.1831 1.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5051 -2.2719 0.6027 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7593 -1.7006 -0.5452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8837 -2.0059 -1.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4253 -1.8873 1.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1990 -0.9255 2.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2231 -1.9475 1.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7316 1.0238 2.5636 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7700 1.9979 1.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0333 1.1844 2.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9934 1.7087 0.8139 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1742 -2.4782 -1.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5130 -2.7256 0.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7947 -2.8070 -0.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5852 -0.2157 -1.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2306 0.9585 -1.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3431 -0.6185 -2.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3126 0.7547 -0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0363 -2.0075 -1.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1870 -1.2748 -2.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7337 -0.6688 -2.8499 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8257 0.7184 -2.4913 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 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 17 22 1 0 22 23 1 1 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 31 32 1 0 32 33 1 0 20 11 1 0 31 22 1 0 20 14 1 0 33 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 1 12 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 15 52 1 0 15 53 1 0 15 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 6 32 76 1 0 32 77 1 0 33 78 1 0 33 79 1 0 M END

Standard InCHIKey	KDCSSVADTHDYGI-GOEVOFJGSA-N
Standard InCHI	InChI=1S/C30H46O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10,19,21,24H,8-9,11-18H2,1-7H3,(H,32,33)/b20-10-/t19-,21-,24+,28-,29-,30+/m1/s1
SMILES	C[C@H](CC/C=C(/C)C(=O)O)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3

Calculated Properties

Physi-Chem Properties

Molecular Weight:	454.34	Volume:	509.035 ? Van der Waals volume.
Dense:	0.893	LogP:	4.958 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.864 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.71 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.341	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.601	Fsp³:	0.8
MCE-18:	80.593 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.948	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.02 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.676	Promiscuous compounds:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.952	MDCK Permeability:	-4.781
Pgp-inhibitor:	0.103	Pgp-substrate:	0.0
PAMPA:	0.961 ? 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%):	0.045	30% Bioavailability (F30%):	0.079
50% Bioavailability (F50%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.941
Plasma Protein Binding (PPB):	93.859%	Volume Distribution (VD):	-0.223
Fu:	7.15% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.034
BSEP inhibitor:	0.954

ADMET: Metabolism

CYP1A2-inhibitor:	0.588	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.056	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.998
HLM stability:	0.689 ? 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):

4.776

Half-life (T1/2):

0.638

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.03
Human Hepatotoxicity (H-HT):	0.771	Drug-induced Liver Injury (DILI):	0.792
AMES Toxicity:	0.141	Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.305	Skin Sensitization:	0.962
Carcinogencity:	0.664	Eye Corrosion:	0.352
Eye Irritation:	0.802	Respiratory Toxicity:	0.737
Drug-induced Neurotoxicity:	0.093	Ototoxicity:	0.601
Hematotoxicity:	0.816	Drug-induced Nephrotoxicity:	0.956
Genotoxicity:	0.633	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.067
BCF:	1.221 ? 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:	4.265 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.644 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.982 ? 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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO8974	Chlamys hastata	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3651433]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11529	Alcyonium palmatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8974	Chlamys hastata	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11529	Alcyonium palmatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26128	Clonostachys rosea	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7374	Seseli montanum	Species	Apiaceae	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	1

Activity Type	# Activity
Cell line	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
NPT759	Cell line	H9	Homo sapiens	IC50	=	2.14	ug.mL-1	PMID[11678650]

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 NPC142253 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	26159
0.1-0.2	20904
0.2-0.3	2308
0.3-0.4	334
0.4-0.5	101
0.5-0.6	36
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC3511
0.7742	Intermediate Similarity	NPC8571
0.7619	Intermediate Similarity	NPC489792
0.7273	Intermediate Similarity	NPC489798
0.7231	Intermediate Similarity	NPC479661
0.7164	Intermediate Similarity	NPC489789
0.7015	Intermediate Similarity	NPC69982
0.6812	Remote Similarity	NPC489802
0.6769	Remote Similarity	NPC162703
0.6667	Remote Similarity	NPC87552
0.6406	Remote Similarity	NPC474083
0.6324	Remote Similarity	NPC472239
0.6111	Remote Similarity	NPC604630
0.597	Remote Similarity	NPC201912
0.597	Remote Similarity	NPC38350
0.597	Remote Similarity	NPC601139
0.5915	Remote Similarity	NPC456
0.5915	Remote Similarity	NPC472941
0.5915	Remote Similarity	NPC202814
0.5909	Remote Similarity	NPC606148
0.5775	Remote Similarity	NPC601194
0.5714	Remote Similarity	NPC479662
0.5672	Remote Similarity	NPC16287
0.5672	Remote Similarity	NPC90965
0.5507	Remote Similarity	NPC260956
0.5507	Remote Similarity	NPC482576
0.5493	Remote Similarity	NPC289213
0.5479	Remote Similarity	NPC483394
0.5467	Remote Similarity	NPC478297
0.5443	Remote Similarity	NPC489806
0.5443	Remote Similarity	NPC198442
0.5429	Remote Similarity	NPC41539
0.5362	Remote Similarity	NPC109512
0.5362	Remote Similarity	NPC605549
0.5352	Remote Similarity	NPC604148
0.5333	Remote Similarity	NPC285702
0.5333	Remote Similarity	NPC166745
0.5333	Remote Similarity	NPC235464
0.5325	Remote Similarity	NPC478299
0.5256	Remote Similarity	NPC478311
0.5211	Remote Similarity	NPC472940
0.5211	Remote Similarity	NPC219495
0.5195	Remote Similarity	NPC472924
0.519	Remote Similarity	NPC478309
0.5128	Remote Similarity	NPC478302
0.5128	Remote Similarity	NPC137552
0.5128	Remote Similarity	NPC99411
0.5068	Remote Similarity	NPC54689
0.5067	Remote Similarity	NPC478308

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC142253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6651
0.1-0.2	2366
0.2-0.3	133
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