NPASS Compound

Structure

CID133430 OpenBabel06191715492D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.8987 -0.2068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1221 0.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3078 -0.1287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1190 0.8533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2592 -0.9525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6859 0.0296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3955 -1.1482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5510 -1.0584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8130 -1.4082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3963 -2.6791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2560 -0.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1366 -2.1142 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5980 -1.6861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8130 -1.4082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6260 -0.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6260 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8230 -1.6970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 0.4694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1128 -1.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0310 -0.7039 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1707 -1.8553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4295 -0.8894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8130 -2.3469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5289 -2.0514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -2.3469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4390 -1.4082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4390 0.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8199 -1.6179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1059 -1.0772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3931 -2.5999 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 -0.8130 1.4082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3173 -0.6193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 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 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 23 1 0 0 0 0 8 13 1 0 0 0 0 8 21 1 0 0 0 0 9 24 1 0 0 0 0 10 22 1 0 0 0 0 10 31 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 6 0 0 0 13 25 1 6 0 0 0 14 9 1 6 0 0 0 14 15 1 0 0 0 0 14 32 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 31 1 0 0 0 0 19 32 1 0 0 0 0 19 33 1 6 0 0 0 20 22 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 23 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 6 0 0 0 23 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.16
Volume:	447.092
LogP:	0.37
LogD:	-0.259
LogS:	-3.258
# Rotatable Bonds:	7
TPSA:	172.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	5.83
Fsp3:	0.652
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.261
MDCK Permeability:	9.394149674335495e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.892
Human Intestinal Absorption (HIA):	0.608
20% Bioavailability (F20%):	0.801
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	34.17527389526367%
Volume Distribution (VD):	0.524
Pgp-substrate:	32.75937271118164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.635
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	1.722
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.41
AMES Toxicity:	0.116
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.194
Carcinogencity:	0.22
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC133430

Natural Product ID:	NPC133430
*Common Name:**	Albiflorin
IUPAC Name:	n.a.
Synonyms:	Albiflorin
Standard InCHIKey:	QQUHMASGPODSIW-MBOWWSQSSA-N
Standard InCHI:	InChI=1S/C23H28O11/c1-21-8-13(25)12-7-23(21,33-19-17(28)16(27)15(26)14(9-24)32-19)22(12,20(30)34-21)10-31-18(29)11-5-3-2-4-6-11/h2-6,12-17,19,24-28H,7-10H2,1H3/t12-,13+,14+,15+,16-,17+,19-,21-,22+,23-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@]23C[C@@H]4[C@]3(COC(=O)c3ccccc3)C(=O)O[C@@]2(C)C[C@H]4O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939883
PubChem CID:	15558591
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	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]
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]
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]
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]
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]
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]
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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	78.47	%	PMID[463751]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	87.39	%	PMID[463751]

☑ 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 NPC133430 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	349
0.1-0.2	1213
0.2-0.3	2580
0.3-0.4	5053
0.4-0.5	9543
0.5-0.6	11370
0.6-0.7	10063
0.7-0.8	2074
0.8-0.85	213
0.85-0.9	216
0.9-0.95	18
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469477
0.9728	High Similarity	NPC469399
0.9658	High Similarity	NPC5115
0.9527	High Similarity	NPC469417
0.9444	High Similarity	NPC469513
0.9384	High Similarity	NPC222102
0.9384	High Similarity	NPC303429
0.932	High Similarity	NPC469415
0.9262	High Similarity	NPC34066
0.9262	High Similarity	NPC469422
0.9252	High Similarity	NPC469448
0.9156	High Similarity	NPC477627
0.9133	High Similarity	NPC469398
0.9097	High Similarity	NPC77493
0.906	High Similarity	NPC471103
0.9048	High Similarity	NPC477737
0.9032	High Similarity	NPC471493
0.902	High Similarity	NPC477623
0.9007	High Similarity	NPC469456
0.9	High Similarity	NPC472548
0.9	High Similarity	NPC477905
0.8994	High Similarity	NPC469421
0.8993	High Similarity	NPC91730
0.8981	High Similarity	NPC469420
0.8966	High Similarity	NPC87448
0.8966	High Similarity	NPC97947
0.8966	High Similarity	NPC118080
0.8966	High Similarity	NPC472576
0.8966	High Similarity	NPC27377
0.8966	High Similarity	NPC41481
0.8966	High Similarity	NPC291599
0.8933	High Similarity	NPC51602
0.8933	High Similarity	NPC197037
0.8924	High Similarity	NPC469419
0.891	High Similarity	NPC117943
0.891	High Similarity	NPC293568
0.8897	High Similarity	NPC97667
0.8897	High Similarity	NPC275592
0.8897	High Similarity	NPC90614
0.8897	High Similarity	NPC100913
0.8897	High Similarity	NPC171207
0.8882	High Similarity	NPC472549
0.8867	High Similarity	NPC476173
0.8861	High Similarity	NPC102465
0.8859	High Similarity	NPC217918
0.8851	High Similarity	NPC127857
0.8846	High Similarity	NPC295408
0.8846	High Similarity	NPC329960
0.8846	High Similarity	NPC150893
0.8836	High Similarity	NPC16912
0.8824	High Similarity	NPC106895
0.8816	High Similarity	NPC219419
0.8816	High Similarity	NPC11588
0.8816	High Similarity	NPC229545
0.8816	High Similarity	NPC248265
0.8816	High Similarity	NPC134685
0.8805	High Similarity	NPC469458
0.8805	High Similarity	NPC88176
0.8805	High Similarity	NPC477469
0.8805	High Similarity	NPC469459
0.8805	High Similarity	NPC477473
0.8805	High Similarity	NPC477466
0.8805	High Similarity	NPC469396
0.8805	High Similarity	NPC149002
0.8805	High Similarity	NPC477471
0.88	High Similarity	NPC81698
0.88	High Similarity	NPC250046
0.88	High Similarity	NPC60509
0.8797	High Similarity	NPC120012
0.8784	High Similarity	NPC470152
0.8784	High Similarity	NPC241951
0.8784	High Similarity	NPC475759
0.8782	High Similarity	NPC43304
0.8782	High Similarity	NPC477188
0.8782	High Similarity	NPC477190
0.8767	High Similarity	NPC183270
0.8767	High Similarity	NPC477904
0.8767	High Similarity	NPC472547
0.8766	High Similarity	NPC477735
0.8758	High Similarity	NPC473670
0.8758	High Similarity	NPC473632
0.8758	High Similarity	NPC132599
0.8758	High Similarity	NPC114357
0.8758	High Similarity	NPC21410
0.8758	High Similarity	NPC469730
0.8758	High Similarity	NPC259144
0.8758	High Similarity	NPC155329
0.8758	High Similarity	NPC282239
0.8742	High Similarity	NPC161239
0.8742	High Similarity	NPC265600
0.8742	High Similarity	NPC198455
0.8742	High Similarity	NPC7095
0.8742	High Similarity	NPC165260
0.8734	High Similarity	NPC477491
0.8726	High Similarity	NPC66193
0.8725	High Similarity	NPC471107
0.8725	High Similarity	NPC29704
0.8725	High Similarity	NPC472571
0.8725	High Similarity	NPC177940
0.8725	High Similarity	NPC174982
0.8725	High Similarity	NPC471104
0.8725	High Similarity	NPC472572
0.8725	High Similarity	NPC476973
0.8725	High Similarity	NPC184817
0.8725	High Similarity	NPC472568
0.8725	High Similarity	NPC471100
0.8725	High Similarity	NPC70403
0.8725	High Similarity	NPC96903
0.8725	High Similarity	NPC470157
0.8725	High Similarity	NPC200471
0.8725	High Similarity	NPC473088
0.8725	High Similarity	NPC472575
0.8725	High Similarity	NPC469349
0.8725	High Similarity	NPC158663
0.8725	High Similarity	NPC470159
0.8725	High Similarity	NPC171525
0.8716	High Similarity	NPC163087
0.8716	High Similarity	NPC477894
0.871	High Similarity	NPC477736
0.8684	High Similarity	NPC470153
0.8671	High Similarity	NPC471134
0.8658	High Similarity	NPC125106
0.8658	High Similarity	NPC57628
0.8658	High Similarity	NPC95810
0.8658	High Similarity	NPC472569
0.8658	High Similarity	NPC476974
0.8658	High Similarity	NPC472570
0.8658	High Similarity	NPC188865
0.8658	High Similarity	NPC25768
0.8658	High Similarity	NPC472573
0.8658	High Similarity	NPC163719
0.8658	High Similarity	NPC475122
0.8658	High Similarity	NPC38696
0.8658	High Similarity	NPC95265
0.8658	High Similarity	NPC11685
0.8658	High Similarity	NPC70716
0.8649	High Similarity	NPC34012
0.8645	High Similarity	NPC472393
0.8645	High Similarity	NPC181924
0.8636	High Similarity	NPC473611
0.8636	High Similarity	NPC228204
0.8636	High Similarity	NPC26033
0.863	High Similarity	NPC39549
0.8621	High Similarity	NPC17877
0.8621	High Similarity	NPC195647
0.8621	High Similarity	NPC66761
0.8621	High Similarity	NPC291638
0.8621	High Similarity	NPC472577
0.8618	High Similarity	NPC112216
0.8616	High Similarity	NPC61891
0.8608	High Similarity	NPC478073
0.8606	High Similarity	NPC469418
0.8598	High Similarity	NPC469438
0.8591	High Similarity	NPC91703
0.859	High Similarity	NPC49297
0.859	High Similarity	NPC471102
0.8589	High Similarity	NPC477617
0.8589	High Similarity	NPC148185
0.8581	High Similarity	NPC217091
0.8571	High Similarity	NPC473414
0.8571	High Similarity	NPC472657
0.8571	High Similarity	NPC265395
0.8571	High Similarity	NPC471135
0.8571	High Similarity	NPC237549
0.8571	High Similarity	NPC146310
0.8571	High Similarity	NPC304876
0.8571	High Similarity	NPC477488
0.8571	High Similarity	NPC249471
0.8571	High Similarity	NPC256142
0.8571	High Similarity	NPC472030
0.8571	High Similarity	NPC472022
0.8571	High Similarity	NPC1173
0.8571	High Similarity	NPC472658
0.8571	High Similarity	NPC257213
0.8571	High Similarity	NPC472005
0.8571	High Similarity	NPC242262
0.8571	High Similarity	NPC158333
0.8562	High Similarity	NPC472551
0.8562	High Similarity	NPC101043
0.8562	High Similarity	NPC306799
0.8562	High Similarity	NPC472545
0.8553	High Similarity	NPC471101
0.8553	High Similarity	NPC476975
0.8553	High Similarity	NPC266265
0.8553	High Similarity	NPC92293
0.8553	High Similarity	NPC301556
0.8553	High Similarity	NPC270590
0.8552	High Similarity	NPC474608
0.8543	High Similarity	NPC478263
0.8543	High Similarity	NPC474935
0.8523	High Similarity	NPC182869
0.8516	High Similarity	NPC112523
0.8516	High Similarity	NPC114410
0.8509	High Similarity	NPC40138
0.8497	Intermediate Similarity	NPC473214
0.8497	Intermediate Similarity	NPC470245
0.8497	Intermediate Similarity	NPC254558
0.8494	Intermediate Similarity	NPC80360
0.8494	Intermediate Similarity	NPC260300
0.8493	Intermediate Similarity	NPC473216

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 NPC133430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	758
0.2-0.3	1677
0.3-0.4	3013
0.4-0.5	2214
0.5-0.6	936
0.6-0.7	226
0.7-0.8	36
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8274	Intermediate Similarity	NPD8407	Phase 2
0.8204	Intermediate Similarity	NPD8368	Discontinued
0.8182	Intermediate Similarity	NPD7799	Discontinued
0.8133	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD8434	Phase 2
0.7785	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8435	Approved
0.7771	Intermediate Similarity	NPD8361	Approved
0.7771	Intermediate Similarity	NPD8360	Approved
0.7658	Intermediate Similarity	NPD7236	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7239	Suspended
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3818	Discontinued
0.7381	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6559	Discontinued
0.7349	Intermediate Similarity	NPD37	Approved
0.7347	Intermediate Similarity	NPD5125	Phase 3
0.7347	Intermediate Similarity	NPD5126	Approved
0.7346	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD8485	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.7321	Intermediate Similarity	NPD4966	Approved
0.7312	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD6535	Approved
0.7308	Intermediate Similarity	NPD6534	Approved
0.7288	Intermediate Similarity	NPD8312	Approved
0.7288	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD7228	Approved
0.7235	Intermediate Similarity	NPD6234	Discontinued
0.7232	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7058	Phase 2
0.7219	Intermediate Similarity	NPD7057	Phase 3
0.7189	Intermediate Similarity	NPD7700	Phase 2
0.7189	Intermediate Similarity	NPD7699	Phase 2
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.716	Intermediate Similarity	NPD6190	Approved
0.7159	Intermediate Similarity	NPD7074	Phase 3
0.715	Intermediate Similarity	NPD8462	Phase 1
0.7143	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD8319	Approved
0.7126	Intermediate Similarity	NPD4380	Phase 2
0.7124	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.7102	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5844	Phase 1
0.7102	Intermediate Similarity	NPD7054	Approved
0.7101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7819	Suspended
0.7093	Intermediate Similarity	NPD5494	Approved
0.7079	Intermediate Similarity	NPD7240	Approved
0.7076	Intermediate Similarity	NPD7075	Discontinued
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7062	Intermediate Similarity	NPD7472	Approved
0.7055	Intermediate Similarity	NPD2629	Approved
0.7052	Intermediate Similarity	NPD7199	Phase 2
0.7048	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2534	Approved
0.703	Intermediate Similarity	NPD2532	Approved
0.703	Intermediate Similarity	NPD2533	Approved
0.7024	Intermediate Similarity	NPD6599	Discontinued
0.7022	Intermediate Similarity	NPD6797	Phase 2
0.7019	Intermediate Similarity	NPD7266	Discontinued
0.7018	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6232	Discontinued
0.7005	Intermediate Similarity	NPD8404	Phase 2
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7473	Discontinued
0.6983	Remote Similarity	NPD7251	Discontinued
0.6973	Remote Similarity	NPD6213	Phase 3
0.6973	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6212	Phase 3
0.697	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7874	Approved
0.6959	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3751	Discontinued
0.6944	Remote Similarity	NPD7808	Phase 3
0.6943	Remote Similarity	NPD3764	Approved
0.6941	Remote Similarity	NPD6801	Discontinued
0.6936	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3787	Discontinued
0.6911	Remote Similarity	NPD7696	Phase 3
0.6911	Remote Similarity	NPD7698	Approved
0.6911	Remote Similarity	NPD7697	Approved
0.6901	Remote Similarity	NPD8455	Phase 2
0.6901	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4198	Discontinued
0.6887	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7008	Discontinued
0.6875	Remote Similarity	NPD7871	Phase 2
0.6875	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7870	Phase 2
0.6864	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5402	Approved
0.686	Remote Similarity	NPD3817	Phase 2
0.6859	Remote Similarity	NPD6823	Phase 2
0.6857	Remote Similarity	NPD8127	Discontinued
0.6856	Remote Similarity	NPD7701	Phase 2
0.6842	Remote Similarity	NPD1934	Approved
0.6839	Remote Similarity	NPD7319	Approved
0.6837	Remote Similarity	NPD7801	Approved
0.6826	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8151	Discontinued
0.6813	Remote Similarity	NPD230	Phase 1
0.681	Remote Similarity	NPD2346	Discontinued
0.6796	Remote Similarity	NPD6764	Approved
0.6796	Remote Similarity	NPD6765	Approved
0.6786	Remote Similarity	NPD6273	Approved
0.6784	Remote Similarity	NPD7411	Suspended
0.6766	Remote Similarity	NPD6799	Approved
0.6765	Remote Similarity	NPD3226	Approved
0.6759	Remote Similarity	NPD2182	Approved
0.6757	Remote Similarity	NPD6010	Discontinued
0.6755	Remote Similarity	NPD7741	Discontinued
0.6753	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7783	Phase 2
0.6742	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6166	Phase 2
0.6742	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7497	Discontinued
0.6724	Remote Similarity	NPD3882	Suspended
0.6711	Remote Similarity	NPD8513	Phase 3
0.6711	Remote Similarity	NPD8516	Approved
0.6711	Remote Similarity	NPD8517	Approved
0.6711	Remote Similarity	NPD5951	Approved
0.6711	Remote Similarity	NPD8515	Approved
0.6705	Remote Similarity	NPD2801	Approved
0.669	Remote Similarity	NPD6686	Approved
0.6687	Remote Similarity	NPD8166	Discontinued
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7961	Discontinued
0.6686	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD7999	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7930	Approved
0.6649	Remote Similarity	NPD6784	Approved
0.6649	Remote Similarity	NPD6785	Approved
0.6648	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5403	Approved
0.6646	Remote Similarity	NPD2935	Discontinued
0.6645	Remote Similarity	NPD7507	Approved
0.6629	Remote Similarity	NPD5710	Approved
0.6629	Remote Similarity	NPD5711	Approved
0.6628	Remote Similarity	NPD7028	Phase 2
0.6627	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5401	Approved
0.6622	Remote Similarity	NPD969	Suspended
0.6618	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1465	Phase 2
0.6608	Remote Similarity	NPD1653	Approved
0.6585	Remote Similarity	NPD7033	Discontinued
0.6585	Remote Similarity	NPD2799	Discontinued
0.6573	Remote Similarity	NPD6959	Discontinued
0.657	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1549	Phase 2
0.6556	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5048	Discontinued
0.6545	Remote Similarity	NPD2796	Approved
0.6536	Remote Similarity	NPD9545	Approved
0.6531	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD6674	Discontinued
0.6527	Remote Similarity	NPD2800	Approved
0.6524	Remote Similarity	NPD7097	Phase 1
0.6522	Remote Similarity	NPD2313	Discontinued
0.6516	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1933	Approved
0.649	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7003	Approved
0.6488	Remote Similarity	NPD2575	Approved
0.6485	Remote Similarity	NPD1510	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