NPASS Compound

Structure

CID120012 OpenBabel06191715472D 36 41 0 0 1 0 0 0 0 0999 V2000 1.0051 0.2113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9830 0.2924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 0.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7086 -0.8384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0194 0.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6904 -1.0283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2780 -0.8866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8899 1.5414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4114 -2.2939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9286 -1.4038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3822 0.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3458 -0.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8899 0.5138 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0191 -1.8525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7798 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7798 -1.0276 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8899 -1.5414 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5996 0.2968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0276 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4914 -2.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6702 -0.7310 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0532 -1.5937 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0715 -2.8511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3120 -0.6278 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7798 2.0552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6698 0.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6698 -1.5414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8899 -2.5690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9260 1.2420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9712 -3.2876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3276 -0.4629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2550 -0.4585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8899 -1.5414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0720 -1.6333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1379 -3.2095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 31 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 21 1 0 0 0 0 9 23 1 0 0 0 0 10 22 1 0 0 0 0 10 32 1 0 0 0 0 11 18 1 0 0 0 0 12 31 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 13 33 1 0 0 0 0 14 22 1 6 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 1 0 0 0 16 17 1 0 0 0 0 16 27 1 6 0 0 0 17 19 1 0 0 0 0 17 28 1 1 0 0 0 18 29 2 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 19 34 1 6 0 0 0 20 22 1 1 0 0 0 20 35 1 0 0 0 0 20 36 1 0 0 0 0 21 24 1 1 0 0 0 21 35 1 0 0 0 0 22 24 1 6 0 0 0 23 30 1 6 0 0 0 23 36 1 0 0 0 0 24 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.17
Volume:	467.258
LogP:	0.894
LogD:	0.163
LogS:	-3.603
# Rotatable Bonds:	8
TPSA:	173.6
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	6.158
Fsp3:	0.708
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.284
MDCK Permeability:	2.190411032643169e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.854
20% Bioavailability (F20%):	0.372
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	32.382476806640625%
Volume Distribution (VD):	0.537
Pgp-substrate:	32.410179138183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	2.254
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.173
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.454
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.466
Carcinogencity:	0.949
Eye Corrosion:	0.003
Eye Irritation:	0.064
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC120012

Natural Product ID:	NPC120012
*Common Name:**	Mudanpioside D
IUPAC Name:	n.a.
Synonyms:	Mudanpioside D
Standard InCHIKey:	DRTKDQCMAUJQEZ-KTBSYUCQSA-N
Standard InCHI:	InChI=1S/C24H30O12/c1-21-9-23(30)14-7-24(21,34-19-17(28)16(27)15(26)13(8-25)33-19)22(14,20(35-21)36-23)10-32-18(29)11-3-5-12(31-2)6-4-11/h3-6,13-17,19-20,25-28,30H,7-10H2,1-2H3/t13-,14-,15-,16+,17-,19+,20-,21+,22+,23-,24+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@]23C[C@@H]4[C@@]3(COC(=O)c3ccc(cc3)OC)[C@@H]3O[C@@]2(C)C[C@]4(O3)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2205287
PubChem CID:	21631103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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
NPO15265	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.167 + 0.014	n.a.	n.a.	μg/g	PMID[32545196]
NPO15265	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.374 + 0.010	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	3.149 ± 0.013	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.753 ± 0.004	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	2.444 ± 0.018	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.581 ± 0.009	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.746 ± 0.014	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.213 ± 0.004	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.569 ± 0.011	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.181 ± 0.012	n.a.	n.a.	μg/g	PMID[32545196]
NPO9798	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.381 ± 0.025	n.a.	n.a.	μg/g	PMID[32545196]
NPO9798	NPC120012	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.663 + 0.014	n.a.	n.a.	μg/g	PMID[32545196]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[573958]
NPT610	Others	Molecular identity unknown		INH	=	3.67	mM	PMID[573959]
NPT610	Others	Molecular identity unknown		INH	=	2.67	mM	PMID[573959]

☑ 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 NPC120012 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	408
0.1-0.2	1487
0.2-0.3	2995
0.3-0.4	5919
0.4-0.5	9541
0.5-0.6	9497
0.6-0.7	9463
0.7-0.8	3128
0.8-0.85	207
0.85-0.9	27
0.9-0.95	15
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC293568
0.9615	High Similarity	NPC117943
0.9503	High Similarity	NPC148185
0.9434	High Similarity	NPC265600
0.9387	High Similarity	NPC469438
0.9375	High Similarity	NPC469459
0.9277	High Similarity	NPC188217
0.9255	High Similarity	NPC469396
0.9255	High Similarity	NPC469458
0.9255	High Similarity	NPC88176
0.9255	High Similarity	NPC149002
0.9212	High Similarity	NPC469397
0.9146	High Similarity	NPC477617
0.9091	High Similarity	NPC303429
0.9091	High Similarity	NPC222102
0.9032	High Similarity	NPC469415
0.9006	High Similarity	NPC477627
0.8929	High Similarity	NPC80360
0.8876	High Similarity	NPC195114
0.8861	High Similarity	NPC469398
0.8861	High Similarity	NPC469422
0.8817	High Similarity	NPC260300
0.8797	High Similarity	NPC133430
0.8797	High Similarity	NPC469477
0.8788	High Similarity	NPC469419
0.8742	High Similarity	NPC5115
0.8742	High Similarity	NPC34066
0.8698	High Similarity	NPC469354
0.8642	High Similarity	NPC477623
0.8616	High Similarity	NPC267469
0.8616	High Similarity	NPC87630
0.8616	High Similarity	NPC179128
0.8616	High Similarity	NPC116292
0.858	High Similarity	NPC469399
0.8554	High Similarity	NPC100420
0.8538	High Similarity	NPC11062
0.85	High Similarity	NPC35160
0.85	High Similarity	NPC162569
0.8491	Intermediate Similarity	NPC469448
0.8488	Intermediate Similarity	NPC469418
0.8443	Intermediate Similarity	NPC93172
0.8443	Intermediate Similarity	NPC97574
0.8434	Intermediate Similarity	NPC285567
0.8434	Intermediate Similarity	NPC283209
0.8428	Intermediate Similarity	NPC473149
0.8428	Intermediate Similarity	NPC286038
0.8421	Intermediate Similarity	NPC195972
0.8415	Intermediate Similarity	NPC194499
0.8415	Intermediate Similarity	NPC88007
0.8415	Intermediate Similarity	NPC195954
0.8405	Intermediate Similarity	NPC469417
0.8402	Intermediate Similarity	NPC82602
0.8397	Intermediate Similarity	NPC80098
0.8385	Intermediate Similarity	NPC88886
0.8385	Intermediate Similarity	NPC104172
0.8375	Intermediate Similarity	NPC66991
0.8365	Intermediate Similarity	NPC208293
0.8365	Intermediate Similarity	NPC474044
0.8364	Intermediate Similarity	NPC226759
0.8353	Intermediate Similarity	NPC160818
0.8353	Intermediate Similarity	NPC169299
0.8343	Intermediate Similarity	NPC473205
0.8343	Intermediate Similarity	NPC473776
0.8333	Intermediate Similarity	NPC289021
0.8333	Intermediate Similarity	NPC254588
0.8333	Intermediate Similarity	NPC119252
0.8333	Intermediate Similarity	NPC158546
0.8304	Intermediate Similarity	NPC52598
0.8304	Intermediate Similarity	NPC477670
0.8304	Intermediate Similarity	NPC469421
0.8302	Intermediate Similarity	NPC469513
0.8294	Intermediate Similarity	NPC79322
0.8293	Intermediate Similarity	NPC478232
0.8291	Intermediate Similarity	NPC242756
0.8284	Intermediate Similarity	NPC180586
0.8284	Intermediate Similarity	NPC469420
0.8284	Intermediate Similarity	NPC475979
0.8284	Intermediate Similarity	NPC100333
0.828	Intermediate Similarity	NPC79908
0.8274	Intermediate Similarity	NPC41009
0.8263	Intermediate Similarity	NPC79571
0.8263	Intermediate Similarity	NPC68848
0.8263	Intermediate Similarity	NPC211777
0.8263	Intermediate Similarity	NPC474936
0.8256	Intermediate Similarity	NPC471922
0.8256	Intermediate Similarity	NPC471921
0.8256	Intermediate Similarity	NPC312006
0.8256	Intermediate Similarity	NPC20114
0.8256	Intermediate Similarity	NPC471920
0.8256	Intermediate Similarity	NPC292712
0.8256	Intermediate Similarity	NPC474075
0.8256	Intermediate Similarity	NPC129930
0.8256	Intermediate Similarity	NPC114550
0.8253	Intermediate Similarity	NPC475663
0.8253	Intermediate Similarity	NPC286919
0.8253	Intermediate Similarity	NPC4747
0.8253	Intermediate Similarity	NPC104275
0.825	Intermediate Similarity	NPC320734
0.8249	Intermediate Similarity	NPC299855
0.8249	Intermediate Similarity	NPC96194
0.8239	Intermediate Similarity	NPC186746
0.8232	Intermediate Similarity	NPC137813
0.8225	Intermediate Similarity	NPC471286
0.8225	Intermediate Similarity	NPC307781
0.8225	Intermediate Similarity	NPC91288
0.8225	Intermediate Similarity	NPC472670
0.8225	Intermediate Similarity	NPC121995
0.8221	Intermediate Similarity	NPC475379
0.8221	Intermediate Similarity	NPC474620
0.8217	Intermediate Similarity	NPC291599
0.8217	Intermediate Similarity	NPC27377
0.8217	Intermediate Similarity	NPC472576
0.8217	Intermediate Similarity	NPC97947
0.8217	Intermediate Similarity	NPC41481
0.8217	Intermediate Similarity	NPC87448
0.8217	Intermediate Similarity	NPC118080
0.8214	Intermediate Similarity	NPC152424
0.8214	Intermediate Similarity	NPC198047
0.8214	Intermediate Similarity	NPC472139
0.8214	Intermediate Similarity	NPC100465
0.821	Intermediate Similarity	NPC161955
0.821	Intermediate Similarity	NPC125182
0.821	Intermediate Similarity	NPC69647
0.8208	Intermediate Similarity	NPC475197
0.8208	Intermediate Similarity	NPC262386
0.8208	Intermediate Similarity	NPC473467
0.8208	Intermediate Similarity	NPC316539
0.8208	Intermediate Similarity	NPC184624
0.8204	Intermediate Similarity	NPC8389
0.8204	Intermediate Similarity	NPC50430
0.8204	Intermediate Similarity	NPC76211
0.8204	Intermediate Similarity	NPC279732
0.8204	Intermediate Similarity	NPC68619
0.8204	Intermediate Similarity	NPC469384
0.8202	Intermediate Similarity	NPC189704
0.8199	Intermediate Similarity	NPC469700
0.8199	Intermediate Similarity	NPC470330
0.8193	Intermediate Similarity	NPC17521
0.8193	Intermediate Similarity	NPC304692
0.8187	Intermediate Similarity	NPC118086
0.8176	Intermediate Similarity	NPC294722
0.8176	Intermediate Similarity	NPC478250
0.8176	Intermediate Similarity	NPC102465
0.8171	Intermediate Similarity	NPC294511
0.8171	Intermediate Similarity	NPC228662
0.8171	Intermediate Similarity	NPC134905
0.8171	Intermediate Similarity	NPC469456
0.8171	Intermediate Similarity	NPC121615
0.8171	Intermediate Similarity	NPC48671
0.8171	Intermediate Similarity	NPC36130
0.8171	Intermediate Similarity	NPC23253
0.8171	Intermediate Similarity	NPC478235
0.8171	Intermediate Similarity	NPC268905
0.8171	Intermediate Similarity	NPC35266
0.8166	Intermediate Similarity	NPC476011
0.8166	Intermediate Similarity	NPC206815
0.8161	Intermediate Similarity	NPC193377
0.8161	Intermediate Similarity	NPC472665
0.816	Intermediate Similarity	NPC182350
0.816	Intermediate Similarity	NPC227980
0.816	Intermediate Similarity	NPC228842
0.8156	Intermediate Similarity	NPC476067
0.8156	Intermediate Similarity	NPC475121
0.8155	Intermediate Similarity	NPC218471
0.8155	Intermediate Similarity	NPC43971
0.8155	Intermediate Similarity	NPC188649
0.8155	Intermediate Similarity	NPC239818
0.8155	Intermediate Similarity	NPC19554
0.8155	Intermediate Similarity	NPC470358
0.8155	Intermediate Similarity	NPC18986
0.8155	Intermediate Similarity	NPC207978
0.8155	Intermediate Similarity	NPC200782
0.8155	Intermediate Similarity	NPC328093
0.8155	Intermediate Similarity	NPC74749
0.8155	Intermediate Similarity	NPC474770
0.8153	Intermediate Similarity	NPC97667
0.8153	Intermediate Similarity	NPC90614
0.8153	Intermediate Similarity	NPC100913
0.8153	Intermediate Similarity	NPC171207
0.8153	Intermediate Similarity	NPC275592
0.815	Intermediate Similarity	NPC38438
0.8148	Intermediate Similarity	NPC476173
0.8144	Intermediate Similarity	NPC472860
0.8144	Intermediate Similarity	NPC475967
0.814	Intermediate Similarity	NPC473202
0.814	Intermediate Similarity	NPC191653
0.814	Intermediate Similarity	NPC21956
0.814	Intermediate Similarity	NPC475641
0.814	Intermediate Similarity	NPC294512
0.814	Intermediate Similarity	NPC475237
0.8137	Intermediate Similarity	NPC291153
0.8137	Intermediate Similarity	NPC473867
0.8137	Intermediate Similarity	NPC474268
0.8137	Intermediate Similarity	NPC475539
0.8137	Intermediate Similarity	NPC143246
0.8137	Intermediate Similarity	NPC119773
0.8136	Intermediate Similarity	NPC473883
0.8133	Intermediate Similarity	NPC172920
0.8133	Intermediate Similarity	NPC104736
0.8133	Intermediate Similarity	NPC10205

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 NPC120012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	823
0.2-0.3	1840
0.3-0.4	2754
0.4-0.5	2100
0.5-0.6	953
0.6-0.7	278
0.7-0.8	56
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4966	Approved
0.8084	Intermediate Similarity	NPD4967	Phase 2
0.8084	Intermediate Similarity	NPD4965	Approved
0.8081	Intermediate Similarity	NPD7228	Approved
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7988	Intermediate Similarity	NPD6234	Discontinued
0.7978	Intermediate Similarity	NPD8434	Phase 2
0.7904	Intermediate Similarity	NPD37	Approved
0.7898	Intermediate Similarity	NPD7240	Approved
0.7824	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7685	Pre-registration
0.7797	Intermediate Similarity	NPD6559	Discontinued
0.7791	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD3818	Discontinued
0.7744	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5844	Phase 1
0.7725	Intermediate Similarity	NPD7458	Discontinued
0.7711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7074	Phase 3
0.7647	Intermediate Similarity	NPD8455	Phase 2
0.7627	Intermediate Similarity	NPD7054	Approved
0.7627	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8312	Approved
0.7611	Intermediate Similarity	NPD8313	Approved
0.76	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7472	Approved
0.7574	Intermediate Similarity	NPD4380	Phase 2
0.7558	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7819	Suspended
0.7544	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6797	Phase 2
0.7529	Intermediate Similarity	NPD5494	Approved
0.7528	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD7251	Discontinued
0.7486	Intermediate Similarity	NPD8127	Discontinued
0.7472	Intermediate Similarity	NPD7799	Discontinued
0.7471	Intermediate Similarity	NPD6599	Discontinued
0.7459	Intermediate Similarity	NPD7808	Phase 3
0.744	Intermediate Similarity	NPD6273	Approved
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7396	Intermediate Similarity	NPD7497	Discontinued
0.7384	Intermediate Similarity	NPD6801	Discontinued
0.7381	Intermediate Similarity	NPD2534	Approved
0.7381	Intermediate Similarity	NPD2533	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2532	Approved
0.7378	Intermediate Similarity	NPD7266	Discontinued
0.7377	Intermediate Similarity	NPD8407	Phase 2
0.7368	Intermediate Similarity	NPD7028	Phase 2
0.7353	Intermediate Similarity	NPD1653	Approved
0.7349	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6232	Discontinued
0.7341	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6776	Approved
0.733	Intermediate Similarity	NPD6780	Approved
0.733	Intermediate Similarity	NPD6779	Approved
0.733	Intermediate Similarity	NPD6781	Approved
0.733	Intermediate Similarity	NPD6778	Approved
0.733	Intermediate Similarity	NPD6777	Approved
0.733	Intermediate Similarity	NPD6782	Approved
0.732	Intermediate Similarity	NPD7999	Approved
0.7318	Intermediate Similarity	NPD7473	Discontinued
0.7312	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6764	Approved
0.7308	Intermediate Similarity	NPD6765	Approved
0.7308	Intermediate Similarity	NPD8368	Discontinued
0.7305	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD3817	Phase 2
0.7289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1934	Approved
0.7277	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6166	Phase 2
0.7253	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD5761	Phase 2
0.7241	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7411	Suspended
0.7219	Intermediate Similarity	NPD6799	Approved
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7680	Approved
0.7216	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD8151	Discontinued
0.7182	Intermediate Similarity	NPD3751	Discontinued
0.7175	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7151	Intermediate Similarity	NPD6784	Approved
0.7151	Intermediate Similarity	NPD6785	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7129	Intermediate Similarity	NPD8404	Phase 2
0.7114	Intermediate Similarity	NPD7930	Approved
0.7112	Intermediate Similarity	NPD8150	Discontinued
0.711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2935	Discontinued
0.7102	Intermediate Similarity	NPD5402	Approved
0.7102	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3764	Approved
0.7095	Intermediate Similarity	NPD6959	Discontinued
0.7092	Intermediate Similarity	NPD8319	Approved
0.7092	Intermediate Similarity	NPD8320	Phase 1
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7091	Intermediate Similarity	NPD7097	Phase 1
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7077	Intermediate Similarity	NPD6823	Phase 2
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7073	Intermediate Similarity	NPD230	Phase 1
0.7068	Intermediate Similarity	NPD6535	Approved
0.7068	Intermediate Similarity	NPD6534	Approved
0.7066	Intermediate Similarity	NPD6004	Phase 3
0.7066	Intermediate Similarity	NPD6005	Phase 3
0.7066	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6002	Phase 3
0.7062	Intermediate Similarity	NPD3882	Suspended
0.7059	Intermediate Similarity	NPD7236	Approved
0.705	Intermediate Similarity	NPD7801	Approved
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7045	Intermediate Similarity	NPD2801	Approved
0.7041	Intermediate Similarity	NPD3750	Approved
0.7041	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4110	Phase 3
0.7024	Intermediate Similarity	NPD1549	Phase 2
0.7022	Intermediate Similarity	NPD3749	Approved
0.7012	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD2438	Suspended
0.7006	Intermediate Similarity	NPD2796	Approved
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7005	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5403	Approved
0.6994	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5401	Approved
0.6964	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2346	Discontinued
0.6964	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5710	Approved
0.6961	Remote Similarity	NPD5711	Approved
0.6954	Remote Similarity	NPD7239	Suspended
0.6951	Remote Similarity	NPD6233	Phase 2
0.6947	Remote Similarity	NPD8435	Approved
0.6947	Remote Similarity	NPD8360	Approved
0.6947	Remote Similarity	NPD8361	Approved
0.6946	Remote Similarity	NPD1510	Phase 2
0.6946	Remote Similarity	NPD2799	Discontinued
0.6946	Remote Similarity	NPD3748	Approved
0.6946	Remote Similarity	NPD7033	Discontinued
0.6941	Remote Similarity	NPD8166	Discontinued
0.6936	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7583	Approved
0.6923	Remote Similarity	NPD9545	Approved
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD3972	Approved
0.691	Remote Similarity	NPD5353	Approved
0.6909	Remote Similarity	NPD4140	Approved
0.69	Remote Similarity	NPD7585	Approved
0.6897	Remote Similarity	NPD920	Approved
0.689	Remote Similarity	NPD6798	Discontinued
0.6889	Remote Similarity	NPD919	Approved
0.6882	Remote Similarity	NPD2800	Approved
0.6879	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7768	Phase 2
0.6868	Remote Similarity	NPD7229	Phase 3
0.6867	Remote Similarity	NPD5124	Phase 1
0.6867	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1933	Approved
0.6864	Remote Similarity	NPD5763	Approved
0.6864	Remote Similarity	NPD5762	Approved
0.6864	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5058	Phase 3
0.6855	Remote Similarity	NPD3705	Approved
0.6855	Remote Similarity	NPD1091	Approved
0.6852	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2798	Approved
0.6842	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1283	Approved
0.6829	Remote Similarity	NPD7095	Approved
0.6827	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1607	Approved
0.6824	Remote Similarity	NPD2424	Discontinued
0.6821	Remote Similarity	NPD1511	Approved

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