NPASS Compound

Structure

CID77493 OpenBabel06191715412D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.2211 2.2198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4340 0.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4492 -0.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7624 0.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7928 -0.6859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1060 0.4509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1708 0.3574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5031 2.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1369 -0.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1212 -0.3158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1122 0.5761 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5881 -0.2031 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2452 1.6166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4649 -0.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9240 0.1803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3366 1.8189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4697 0.7784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0371 1.9946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4801 -1.4789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2030 1.2604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7933 -0.3421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0530 1.1890 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 1 16 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 11 7 1 6 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 9 1 1 0 0 0 12 15 1 0 0 0 0 13 18 2 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 6 0 0 0 15 23 1 0 0 0 0 16 17 1 1 0 0 0 16 22 1 0 0 0 0 17 20 1 1 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	307.921
LogP:	1.785
LogD:	1.142
LogS:	-3.662
# Rotatable Bonds:	4
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	5.03
Fsp3:	0.529
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	3.0091650842223316e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.303
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.848
Plasma Protein Binding (PPB):	79.98455047607422%
Volume Distribution (VD):	0.831
Pgp-substrate:	26.893308639526367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.558

ADMET: Excretion

Clearance (CL):	14.029
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.361
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.133
Carcinogencity:	0.214
Eye Corrosion:	0.007
Eye Irritation:	0.534
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC77493

Natural Product ID:	NPC77493
*Common Name:**	Paeoniflorigenone
IUPAC Name:	n.a.
Synonyms:	Paeoniflorigenone
Standard InCHIKey:	BANPEMKDTXIFRE-GMKCAIKYSA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-16-8-13(18)11-7-17(16,20)23-15(22-16)12(11)9-21-14(19)10-5-3-2-4-6-10/h2-6,11-12,15,20H,7-9H2,1H3/t11-,12+,15-,16+,17-/m0/s1
SMILES:	O=C(c1ccccc1)OC[C@H]1[C@H]2O[C@]3([C@@](O2)(C[C@@H]1C(=O)C3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077668
PubChem CID:	133475
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
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	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]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
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	Seeds	Yangling, Shaanxi, China	80 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	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 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	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	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30226	Paeonia albiflora	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

☑ 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
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	92.6	%	PMID[573239]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	71.9	%	PMID[573239]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	24.5	%	PMID[573239]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	26.7	%	PMID[573239]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	6870.0	nM	PMID[573241]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[573238]
NPT35	Others	n.a.		IC50	>	500000.0	nM	PMID[573238]

☑ 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 NPC77493 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	291
0.1-0.2	1116
0.2-0.3	2283
0.3-0.4	4661
0.4-0.5	9632
0.5-0.6	10959
0.6-0.7	10929
0.7-0.8	2542
0.8-0.85	259
0.85-0.9	21
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9353	High Similarity	NPC469513
0.9214	High Similarity	NPC477737
0.9097	High Similarity	NPC469477
0.9097	High Similarity	NPC133430
0.9041	High Similarity	NPC469417
0.8912	High Similarity	NPC477735
0.8851	High Similarity	NPC469399
0.8851	High Similarity	NPC477736
0.8776	High Similarity	NPC5115
0.8684	High Similarity	NPC477627
0.863	High Similarity	NPC469448
0.8611	High Similarity	NPC127857
0.8571	High Similarity	NPC51602
0.8571	High Similarity	NPC471103
0.8553	High Similarity	NPC477188
0.8553	High Similarity	NPC477190
0.8553	High Similarity	NPC43304
0.854	High Similarity	NPC27712
0.8523	High Similarity	NPC469456
0.8516	High Similarity	NPC469420
0.8516	High Similarity	NPC102465
0.8514	High Similarity	NPC477905
0.8514	High Similarity	NPC472548
0.8503	High Similarity	NPC303429
0.8503	High Similarity	NPC222102
0.8497	Intermediate Similarity	NPC295408
0.8497	Intermediate Similarity	NPC329960
0.8497	Intermediate Similarity	NPC150893
0.8497	Intermediate Similarity	NPC66193
0.8462	Intermediate Similarity	NPC469419
0.8446	Intermediate Similarity	NPC469415
0.8442	Intermediate Similarity	NPC471493
0.8442	Intermediate Similarity	NPC471134
0.844	Intermediate Similarity	NPC472551
0.844	Intermediate Similarity	NPC472545
0.8435	Intermediate Similarity	NPC81698
0.8435	Intermediate Similarity	NPC250046
0.8435	Intermediate Similarity	NPC60509
0.8411	Intermediate Similarity	NPC181924
0.84	Intermediate Similarity	NPC473670
0.84	Intermediate Similarity	NPC21410
0.84	Intermediate Similarity	NPC469422
0.84	Intermediate Similarity	NPC34066
0.84	Intermediate Similarity	NPC282239
0.84	Intermediate Similarity	NPC472549
0.8392	Intermediate Similarity	NPC183270
0.8392	Intermediate Similarity	NPC171207
0.8392	Intermediate Similarity	NPC97667
0.8392	Intermediate Similarity	NPC477904
0.8392	Intermediate Similarity	NPC100913
0.8392	Intermediate Similarity	NPC275592
0.8387	Intermediate Similarity	NPC61891
0.838	Intermediate Similarity	NPC39549
0.8378	Intermediate Similarity	NPC112216
0.8378	Intermediate Similarity	NPC91730
0.8378	Intermediate Similarity	NPC161239
0.8378	Intermediate Similarity	NPC198455
0.8378	Intermediate Similarity	NPC165260
0.8378	Intermediate Similarity	NPC7095
0.8356	Intermediate Similarity	NPC471100
0.8356	Intermediate Similarity	NPC471107
0.8355	Intermediate Similarity	NPC49297
0.8345	Intermediate Similarity	NPC91703
0.8344	Intermediate Similarity	NPC477466
0.8344	Intermediate Similarity	NPC217091
0.8344	Intermediate Similarity	NPC106895
0.8344	Intermediate Similarity	NPC477469
0.8344	Intermediate Similarity	NPC477471
0.8344	Intermediate Similarity	NPC477473
0.8333	Intermediate Similarity	NPC146310
0.8333	Intermediate Similarity	NPC87448
0.8333	Intermediate Similarity	NPC291599
0.8333	Intermediate Similarity	NPC41481
0.8333	Intermediate Similarity	NPC213567
0.8333	Intermediate Similarity	NPC16912
0.8333	Intermediate Similarity	NPC472576
0.8333	Intermediate Similarity	NPC97947
0.8333	Intermediate Similarity	NPC118080
0.8333	Intermediate Similarity	NPC27377
0.8322	Intermediate Similarity	NPC306799
0.8322	Intermediate Similarity	NPC101043
0.8322	Intermediate Similarity	NPC197037
0.8302	Intermediate Similarity	NPC469421
0.8289	Intermediate Similarity	NPC472393
0.828	Intermediate Similarity	NPC40138
0.8278	Intermediate Similarity	NPC469398
0.8276	Intermediate Similarity	NPC182869
0.8273	Intermediate Similarity	NPC262819
0.8269	Intermediate Similarity	NPC477491
0.8264	Intermediate Similarity	NPC472547
0.8264	Intermediate Similarity	NPC90614
0.8258	Intermediate Similarity	NPC322420
0.8255	Intermediate Similarity	NPC476173
0.8243	Intermediate Similarity	NPC217918
0.8239	Intermediate Similarity	NPC477896
0.8239	Intermediate Similarity	NPC473216
0.8239	Intermediate Similarity	NPC473399
0.8239	Intermediate Similarity	NPC477893
0.8235	Intermediate Similarity	NPC471102
0.8219	Intermediate Similarity	NPC477894
0.8214	Intermediate Similarity	NPC469519
0.8212	Intermediate Similarity	NPC237549
0.8212	Intermediate Similarity	NPC248265
0.8212	Intermediate Similarity	NPC11588
0.8212	Intermediate Similarity	NPC229545
0.8212	Intermediate Similarity	NPC1173
0.8212	Intermediate Similarity	NPC472030
0.8212	Intermediate Similarity	NPC471135
0.8212	Intermediate Similarity	NPC265395
0.8212	Intermediate Similarity	NPC473414
0.8212	Intermediate Similarity	NPC472658
0.8212	Intermediate Similarity	NPC249471
0.8212	Intermediate Similarity	NPC257213
0.8212	Intermediate Similarity	NPC242262
0.8212	Intermediate Similarity	NPC256142
0.8212	Intermediate Similarity	NPC472022
0.8212	Intermediate Similarity	NPC304876
0.8212	Intermediate Similarity	NPC472005
0.8212	Intermediate Similarity	NPC472657
0.8212	Intermediate Similarity	NPC158333
0.8212	Intermediate Similarity	NPC219419
0.8212	Intermediate Similarity	NPC77719
0.8212	Intermediate Similarity	NPC134685
0.8207	Intermediate Similarity	NPC224491
0.8194	Intermediate Similarity	NPC275477
0.8182	Intermediate Similarity	NPC477623
0.8169	Intermediate Similarity	NPC474608
0.8163	Intermediate Similarity	NPC475122
0.8163	Intermediate Similarity	NPC163719
0.8163	Intermediate Similarity	NPC475759
0.8163	Intermediate Similarity	NPC25768
0.8163	Intermediate Similarity	NPC11685
0.8163	Intermediate Similarity	NPC472569
0.8163	Intermediate Similarity	NPC125106
0.8163	Intermediate Similarity	NPC188865
0.8163	Intermediate Similarity	NPC70716
0.8163	Intermediate Similarity	NPC470152
0.8163	Intermediate Similarity	NPC95810
0.8163	Intermediate Similarity	NPC472573
0.8163	Intermediate Similarity	NPC57628
0.8163	Intermediate Similarity	NPC476974
0.8163	Intermediate Similarity	NPC95265
0.8163	Intermediate Similarity	NPC472570
0.8163	Intermediate Similarity	NPC241951
0.8158	Intermediate Similarity	NPC26033
0.8158	Intermediate Similarity	NPC112523
0.8158	Intermediate Similarity	NPC228204
0.8158	Intermediate Similarity	NPC259144
0.8158	Intermediate Similarity	NPC114357
0.8158	Intermediate Similarity	NPC155329
0.8158	Intermediate Similarity	NPC251139
0.8158	Intermediate Similarity	NPC114410
0.8153	Intermediate Similarity	NPC324769
0.8153	Intermediate Similarity	NPC325732
0.8151	Intermediate Similarity	NPC472546
0.8141	Intermediate Similarity	NPC478073
0.8133	Intermediate Similarity	NPC254558
0.8121	Intermediate Similarity	NPC132652
0.8116	Intermediate Similarity	NPC476033
0.8113	Intermediate Similarity	NPC477488
0.8112	Intermediate Similarity	NPC66761
0.8112	Intermediate Similarity	NPC195647
0.8112	Intermediate Similarity	NPC17877
0.8112	Intermediate Similarity	NPC291638
0.8112	Intermediate Similarity	NPC472577
0.8108	Intermediate Similarity	NPC200471
0.8108	Intermediate Similarity	NPC472572
0.8108	Intermediate Similarity	NPC174982
0.8108	Intermediate Similarity	NPC96903
0.8108	Intermediate Similarity	NPC476973
0.8108	Intermediate Similarity	NPC472571
0.8108	Intermediate Similarity	NPC158663
0.8108	Intermediate Similarity	NPC171525
0.8108	Intermediate Similarity	NPC29704
0.8108	Intermediate Similarity	NPC177940
0.8108	Intermediate Similarity	NPC473088
0.8108	Intermediate Similarity	NPC469349
0.8108	Intermediate Similarity	NPC70403
0.8108	Intermediate Similarity	NPC470159
0.8108	Intermediate Similarity	NPC184817
0.8108	Intermediate Similarity	NPC472575
0.8108	Intermediate Similarity	NPC471104
0.8108	Intermediate Similarity	NPC472568
0.8108	Intermediate Similarity	NPC470157
0.8105	Intermediate Similarity	NPC154675
0.8105	Intermediate Similarity	NPC323001
0.8105	Intermediate Similarity	NPC475548
0.8105	Intermediate Similarity	NPC326235
0.8105	Intermediate Similarity	NPC475638
0.8105	Intermediate Similarity	NPC290683
0.8102	Intermediate Similarity	NPC138798
0.8102	Intermediate Similarity	NPC472704
0.8095	Intermediate Similarity	NPC95449
0.8095	Intermediate Similarity	NPC163087
0.8092	Intermediate Similarity	NPC474620
0.8089	Intermediate Similarity	NPC293568
0.8089	Intermediate Similarity	NPC117943
0.8079	Intermediate Similarity	NPC470153
0.8071	Intermediate Similarity	NPC301857
0.8067	Intermediate Similarity	NPC473215

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 NPC77493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	722
0.2-0.3	1380
0.3-0.4	2747
0.4-0.5	2441
0.5-0.6	1171
0.6-0.7	416
0.7-0.8	29
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
0.7972	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7799	Discontinued
0.7887	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8407	Phase 2
0.7651	Intermediate Similarity	NPD8368	Discontinued
0.7516	Intermediate Similarity	NPD7236	Approved
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.747	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4628	Phase 3
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3764	Approved
0.7342	Intermediate Similarity	NPD7458	Discontinued
0.7337	Intermediate Similarity	NPD7685	Pre-registration
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7305	Intermediate Similarity	NPD5126	Approved
0.7305	Intermediate Similarity	NPD5125	Phase 3
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.7278	Intermediate Similarity	NPD7239	Suspended
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7251	Intermediate Similarity	NPD8312	Approved
0.7251	Intermediate Similarity	NPD8313	Approved
0.7244	Intermediate Similarity	NPD6799	Approved
0.7241	Intermediate Similarity	NPD8435	Approved
0.7241	Intermediate Similarity	NPD8361	Approved
0.7241	Intermediate Similarity	NPD8360	Approved
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7219	Intermediate Similarity	NPD7074	Phase 3
0.7194	Intermediate Similarity	NPD4198	Discontinued
0.7193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3882	Suspended
0.716	Intermediate Similarity	NPD7054	Approved
0.7152	Intermediate Similarity	NPD5494	Approved
0.7126	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8150	Discontinued
0.7122	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7472	Approved
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD1934	Approved
0.7099	Intermediate Similarity	NPD37	Approved
0.7097	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6234	Discontinued
0.7089	Intermediate Similarity	NPD2532	Approved
0.7089	Intermediate Similarity	NPD2534	Approved
0.7089	Intermediate Similarity	NPD2533	Approved
0.7086	Intermediate Similarity	NPD230	Phase 1
0.7081	Intermediate Similarity	NPD4380	Phase 2
0.7079	Intermediate Similarity	NPD6534	Approved
0.7079	Intermediate Similarity	NPD6535	Approved
0.7078	Intermediate Similarity	NPD7266	Discontinued
0.7078	Intermediate Similarity	NPD2346	Discontinued
0.7076	Intermediate Similarity	NPD6797	Phase 2
0.7075	Intermediate Similarity	NPD2798	Approved
0.7073	Intermediate Similarity	NPD4967	Phase 2
0.7073	Intermediate Similarity	NPD4966	Approved
0.7073	Intermediate Similarity	NPD4965	Approved
0.7073	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2182	Approved
0.7055	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD9545	Approved
0.7041	Intermediate Similarity	NPD7473	Discontinued
0.7037	Intermediate Similarity	NPD7411	Suspended
0.7035	Intermediate Similarity	NPD7251	Discontinued
0.703	Intermediate Similarity	NPD3749	Approved
0.7029	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8320	Phase 1
0.7011	Intermediate Similarity	NPD8319	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD2629	Approved
0.6994	Remote Similarity	NPD7808	Phase 3
0.6994	Remote Similarity	NPD6801	Discontinued
0.6978	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1933	Approved
0.697	Remote Similarity	NPD7058	Phase 2
0.697	Remote Similarity	NPD7057	Phase 3
0.6964	Remote Similarity	NPD6232	Discontinued
0.6961	Remote Similarity	NPD7699	Phase 2
0.6961	Remote Similarity	NPD7700	Phase 2
0.6957	Remote Similarity	NPD7435	Discontinued
0.6951	Remote Similarity	NPD2801	Approved
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1510	Phase 2
0.6923	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1549	Phase 2
0.6914	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD969	Suspended
0.6903	Remote Similarity	NPD2796	Approved
0.6901	Remote Similarity	NPD3751	Discontinued
0.6887	Remote Similarity	NPD2313	Discontinued
0.6885	Remote Similarity	NPD6778	Approved
0.6885	Remote Similarity	NPD6780	Approved
0.6885	Remote Similarity	NPD6776	Approved
0.6885	Remote Similarity	NPD6781	Approved
0.6885	Remote Similarity	NPD6777	Approved
0.6885	Remote Similarity	NPD6779	Approved
0.6885	Remote Similarity	NPD6782	Approved
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3787	Discontinued
0.686	Remote Similarity	NPD5844	Phase 1
0.6859	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6287	Discontinued
0.6848	Remote Similarity	NPD8455	Phase 2
0.6842	Remote Similarity	NPD2066	Phase 3
0.6842	Remote Similarity	NPD1238	Approved
0.6839	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD7240	Approved
0.6838	Remote Similarity	NPD5048	Discontinued
0.6835	Remote Similarity	NPD8166	Discontinued
0.6833	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6212	Phase 3
0.6833	Remote Similarity	NPD6213	Phase 3
0.6821	Remote Similarity	NPD7008	Discontinued
0.6818	Remote Similarity	NPD1607	Approved
0.6815	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1930	Approved
0.6815	Remote Similarity	NPD1929	Approved
0.6813	Remote Similarity	NPD8485	Approved
0.6807	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5402	Approved
0.6803	Remote Similarity	NPD1608	Approved
0.6797	Remote Similarity	NPD1240	Approved
0.6797	Remote Similarity	NPD943	Approved
0.6795	Remote Similarity	NPD2935	Discontinued
0.679	Remote Similarity	NPD5403	Approved
0.6786	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5401	Approved
0.677	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7028	Phase 2
0.6765	Remote Similarity	NPD164	Approved
0.6761	Remote Similarity	NPD5951	Approved
0.6759	Remote Similarity	NPD8516	Approved
0.6759	Remote Similarity	NPD8515	Approved
0.6759	Remote Similarity	NPD8517	Approved
0.6759	Remote Similarity	NPD8513	Phase 3
0.6753	Remote Similarity	NPD6355	Discontinued
0.6752	Remote Similarity	NPD2344	Approved
0.6752	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5761	Phase 2
0.6747	Remote Similarity	NPD5760	Phase 2
0.6737	Remote Similarity	NPD7874	Approved
0.6737	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7961	Discontinued
0.673	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3750	Approved
0.6714	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5306	Approved
0.6712	Remote Similarity	NPD5305	Approved
0.6708	Remote Similarity	NPD1511	Approved
0.6688	Remote Similarity	NPD5406	Approved
0.6688	Remote Similarity	NPD5408	Approved
0.6688	Remote Similarity	NPD5404	Approved
0.6688	Remote Similarity	NPD1551	Phase 2
0.6688	Remote Similarity	NPD5405	Approved
0.6687	Remote Similarity	NPD920	Approved
0.6686	Remote Similarity	NPD919	Approved
0.6686	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8151	Discontinued
0.6684	Remote Similarity	NPD7696	Phase 3
0.6684	Remote Similarity	NPD7698	Approved
0.6684	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD2567	Approved
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD8462	Phase 1
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5710	Approved
0.6649	Remote Similarity	NPD7871	Phase 2
0.6649	Remote Similarity	NPD7870	Phase 2
0.6648	Remote Similarity	NPD6765	Approved
0.6648	Remote Similarity	NPD6764	Approved
0.6647	Remote Similarity	NPD1465	Phase 2

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