NPASS Compound

Structure

NPC289407 OpenBabel06302215172D 32 36 0 0 1 0 0 0 0 0999 V2000 0.7071 0.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 -0.5000 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 28 1 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 6 0 0 0 5 7 1 0 0 0 0 5 30 1 0 0 0 0 8 7 1 1 0 0 0 8 9 1 0 0 0 0 9 25 1 0 0 0 0 9 10 1 1 0 0 0 9 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 24 1 0 0 0 0 13 14 1 6 0 0 0 13 15 1 0 0 0 0 15 21 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 19 20 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 25 26 1 6 0 0 0 25 27 1 0 0 0 0 27 28 1 0 0 0 0 30 31 2 0 0 0 0 30 32 1 0 0 0 0 M CHG 1 29 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.26
Volume:	469.404
LogP:	4.489
LogD:	3.145
LogS:	-4.693
# Rotatable Bonds:	1
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	4.944
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.441
MDCK Permeability:	2.0398487322381698e-05
Pgp-inhibitor:	0.529
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.104
Plasma Protein Binding (PPB):	92.98043823242188%
Volume Distribution (VD):	0.676
Pgp-substrate:	6.339766025543213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.706
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.556
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	0.762
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.811
Drug-inuced Liver Injury (DILI):	0.185
AMES Toxicity:	0.74
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.651
Skin Sensitization:	0.932
Carcinogencity:	0.786
Eye Corrosion:	0.067
Eye Irritation:	0.031
Respiratory Toxicity:	0.971

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC289407

Natural Product ID:	NPC289407
*Common Name:**	FXLVCCDIUNLGKU-BRUCSKOJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FXLVCCDIUNLGKU-BRUCSKOJSA-N
Standard InCHI:	InChI=1S/C28H36O4/c1-24-8-9-25(2,23(31)32)16-22(24)28(5)13-11-26(3)18-15-20(30)19(29)14-17(18)6-7-21(26)27(28,4)12-10-24/h6-7,14-15,22,29H,8-13,16H2,1-5H3,(H,31,32)/p-1/t22-,24-,25-,26+,27-,28+/m1/s1
SMILES:	C[C@@]12CC[C@](C)(C[C@H]2[C@]2(C)CC[C@@]3(C)C4=CC(=O)C(=CC4=CC=C3[C@@]2(C)CC1)[O-])C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5701992
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/S0040-4039(99)00339-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10746886]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10757718]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[20167482]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22256754]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[23252270]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	Roots	Yucatan Peninsula	n.a.	PMID[24709561]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[27113553]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2801129]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[535601]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8328267]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Phytochemistry, 2000, 53, 715-722.]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	root bark	Kunming, Yunnan, China	n.a.	Database[Title]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO18477	Celastrus scandens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17762	Crossopetalum gaumeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1152	Tripterygium hypoglaucum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	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	NP ID	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC289407 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1190
0.2-0.3	4671
0.3-0.4	12893
0.4-0.5	11484
0.5-0.6	6859
0.6-0.7	4257
0.7-0.8	1017
0.8-0.85	86
0.85-0.9	25
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC289407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1399
0.2-0.3	3655
0.3-0.4	2573
0.4-0.5	865
0.5-0.6	222
0.6-0.7	164
0.7-0.8	62
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage

Bioactivity similarity: Similar Natural Products in NPASS

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