NPASS Compound

Structure

CID209851 OpenBabel06191716002D 45 48 0 0 1 0 0 0 0 0999 V2000 -2.7572 -1.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2419 1.7867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3286 -2.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5260 0.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8751 -2.0285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7933 -1.1330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1647 -1.8822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7051 0.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7503 1.6322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7503 2.6102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 1.1432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 3.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0563 1.6322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2093 3.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3623 2.6102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2477 1.2977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2477 0.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7492 0.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8381 -0.6690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0889 1.2977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2477 -2.5550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0370 1.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3641 -1.1815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0563 2.6102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6683 0.2942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6683 1.6322 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5153 3.0992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0889 -1.2977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0889 0.6287 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6683 -0.9632 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4300 0.5125 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8971 -0.3345 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1698 -0.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6683 0.2942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9969 -3.1837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5260 2.2065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3422 -1.1815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1667 1.5515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5153 4.0773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9696 -0.1279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4175 -1.5918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0590 1.3595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8751 -0.3345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6683 2.6102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 33 1 0 0 0 0 7 33 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 24 2 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 34 1 0 0 0 0 18 25 1 0 0 0 0 18 35 1 0 0 0 0 19 25 1 0 0 0 0 19 28 2 0 0 0 0 20 26 1 0 0 0 0 20 29 1 0 0 0 0 21 36 2 0 0 0 0 21 42 1 0 0 0 0 22 37 2 0 0 0 0 22 43 1 0 0 0 0 23 38 2 0 0 0 0 23 44 1 0 0 0 0 25 39 2 0 0 0 0 26 45 1 6 0 0 0 27 40 2 0 0 0 0 27 45 1 0 0 0 0 28 30 1 0 0 0 0 28 33 1 0 0 0 0 29 31 1 0 0 0 0 29 34 1 1 0 0 0 30 32 1 0 0 0 0 30 42 1 1 0 0 0 31 35 1 6 0 0 0 31 43 1 0 0 0 0 32 34 1 6 0 0 0 32 44 1 0 0 0 0 33 35 1 0 0 0 0 34 8 1 1 0 0 0 35 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	255.281
LogP:	3.72
LogD:	3.645
LogS:	-4.772
# Rotatable Bonds:	4
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	3.202
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.843
MDCK Permeability:	1.838559728639666e-05
Pgp-inhibitor:	0.151
Pgp-substrate:	0.204
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92
Plasma Protein Binding (PPB):	87.6731185913086%
Volume Distribution (VD):	1.751
Pgp-substrate:	8.572196006774902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.339
CYP2C19-substrate:	0.479
CYP2C9-inhibitor:	0.202
CYP2C9-substrate:	0.417
CYP2D6-inhibitor:	0.827
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	5.732
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.546
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.463
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.932
Carcinogencity:	0.788
Eye Corrosion:	0.163
Eye Irritation:	0.973
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC209851

Natural Product ID:	NPC209851
*Common Name:**	VBLNERPSGWCFQJ-NINUBRFRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VBLNERPSGWCFQJ-NINUBRFRSA-N
Standard InCHI:	InChI=1S/C35H42O10/c1-19-25(39)18-35(41)31(43-22(4)37)29-20(2)26(45-27(40)15-14-24-12-10-9-11-13-24)16-17-34(29,8)32(44-23(5)38)30(42-21(3)36)28(19)33(35,6)7/h9-15,26,29-32,41H,2,16-18H2,1,3-8H3/b15-14+/t26-,29-,30+,31-,32-,34+,35+/m0/s1
SMILES:	CC1=C2[C@H]([C@@H]([C@]3(C)CC[C@@H](C(=C)[C@H]3[C@@H]([C@](CC1=O)(C2(C)C)O)OC(=O)C)OC(=O)/C=C/c1ccccc1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL128197
PubChem CID:	5315909
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23265441]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561894]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7908950]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5067	Taxus baccata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	4.6	ug.mL-1	PMID[505593]
NPT2	Others	Unspecified		Control	=	167.0	%	PMID[505593]
NPT2	Others	Unspecified		Control	=	436.0	%	PMID[505593]
NPT27	Others	Unspecified		IC50	=	6.9	ug.mL-1	PMID[505593]

☑ 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 NPC209851 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	271
0.1-0.2	940
0.2-0.3	2087
0.3-0.4	4808
0.4-0.5	8309
0.5-0.6	15774
0.6-0.7	9382
0.7-0.8	1050
0.8-0.85	41
0.85-0.9	27
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.968	High Similarity	NPC473443
0.96	High Similarity	NPC225103
0.9524	High Similarity	NPC472388
0.9375	High Similarity	NPC80599
0.9355	High Similarity	NPC469742
0.9213	High Similarity	NPC195224
0.9147	High Similarity	NPC472418
0.9134	High Similarity	NPC473423
0.9044	High Similarity	NPC471912
0.9044	High Similarity	NPC80895
0.9	High Similarity	NPC472361
0.8978	High Similarity	NPC277053
0.8978	High Similarity	NPC301946
0.8968	High Similarity	NPC12016
0.8931	High Similarity	NPC472394
0.8898	High Similarity	NPC472373
0.8897	High Similarity	NPC63737
0.8881	High Similarity	NPC184109
0.8864	High Similarity	NPC472437
0.8849	High Similarity	NPC217918
0.8846	High Similarity	NPC93632
0.8828	High Similarity	NPC471758
0.8806	High Similarity	NPC472372
0.8806	High Similarity	NPC472374
0.8788	High Similarity	NPC475493
0.8788	High Similarity	NPC471880
0.876	High Similarity	NPC45821
0.8759	High Similarity	NPC34012
0.8723	High Similarity	NPC91730
0.872	High Similarity	NPC89324
0.8662	High Similarity	NPC197037
0.8661	High Similarity	NPC473439
0.8661	High Similarity	NPC300827
0.8613	High Similarity	NPC473440
0.8594	High Similarity	NPC473749
0.8571	High Similarity	NPC127857
0.8542	High Similarity	NPC229545
0.8542	High Similarity	NPC248265
0.8542	High Similarity	NPC219419
0.8542	High Similarity	NPC11588
0.8542	High Similarity	NPC134685
0.854	High Similarity	NPC472395
0.854	High Similarity	NPC472371
0.8511	High Similarity	NPC474935
0.85	High Similarity	NPC38696
0.8483	Intermediate Similarity	NPC114357
0.8483	Intermediate Similarity	NPC155329
0.8483	Intermediate Similarity	NPC259144
0.8483	Intermediate Similarity	NPC21410
0.8483	Intermediate Similarity	NPC473670
0.8478	Intermediate Similarity	NPC472547
0.8462	Intermediate Similarity	NPC7095
0.8462	Intermediate Similarity	NPC112216
0.8444	Intermediate Similarity	NPC15850
0.8425	Intermediate Similarity	NPC217091
0.8417	Intermediate Similarity	NPC16912
0.8409	Intermediate Similarity	NPC171007
0.8409	Intermediate Similarity	NPC190849
0.8403	Intermediate Similarity	NPC51602
0.8403	Intermediate Similarity	NPC101043
0.8403	Intermediate Similarity	NPC306799
0.8394	Intermediate Similarity	NPC472545
0.8394	Intermediate Similarity	NPC472551
0.8392	Intermediate Similarity	NPC60509
0.8392	Intermediate Similarity	NPC81698
0.8392	Intermediate Similarity	NPC250046
0.8382	Intermediate Similarity	NPC4242
0.8382	Intermediate Similarity	NPC471911
0.8367	Intermediate Similarity	NPC472393
0.8357	Intermediate Similarity	NPC472546
0.8345	Intermediate Similarity	NPC97667
0.8345	Intermediate Similarity	NPC475400
0.8345	Intermediate Similarity	NPC183270
0.8345	Intermediate Similarity	NPC472548
0.8345	Intermediate Similarity	NPC477904
0.8345	Intermediate Similarity	NPC171207
0.8333	Intermediate Similarity	NPC198455
0.8333	Intermediate Similarity	NPC161239
0.8333	Intermediate Similarity	NPC39549
0.8333	Intermediate Similarity	NPC476970
0.8333	Intermediate Similarity	NPC165260
0.8333	Intermediate Similarity	NPC473082
0.8308	Intermediate Similarity	NPC475328
0.8296	Intermediate Similarity	NPC476977
0.8288	Intermediate Similarity	NPC257213
0.8288	Intermediate Similarity	NPC1173
0.8288	Intermediate Similarity	NPC242262
0.8288	Intermediate Similarity	NPC265395
0.8288	Intermediate Similarity	NPC237549
0.8288	Intermediate Similarity	NPC472022
0.8288	Intermediate Similarity	NPC256142
0.8288	Intermediate Similarity	NPC304876
0.8288	Intermediate Similarity	NPC158333
0.8288	Intermediate Similarity	NPC472005
0.8288	Intermediate Similarity	NPC472030
0.8288	Intermediate Similarity	NPC77719
0.8288	Intermediate Similarity	NPC473414
0.8288	Intermediate Similarity	NPC249471
0.8286	Intermediate Similarity	NPC41481
0.8286	Intermediate Similarity	NPC291599
0.8286	Intermediate Similarity	NPC87448
0.8286	Intermediate Similarity	NPC224491
0.8286	Intermediate Similarity	NPC118080
0.8286	Intermediate Similarity	NPC27377
0.8286	Intermediate Similarity	NPC472576
0.8286	Intermediate Similarity	NPC97947
0.8276	Intermediate Similarity	NPC471103
0.8271	Intermediate Similarity	NPC476972
0.8271	Intermediate Similarity	NPC476971
0.8268	Intermediate Similarity	NPC470820
0.8258	Intermediate Similarity	NPC473083
0.8239	Intermediate Similarity	NPC472569
0.8239	Intermediate Similarity	NPC95265
0.8239	Intermediate Similarity	NPC11685
0.8239	Intermediate Similarity	NPC95810
0.8239	Intermediate Similarity	NPC111466
0.8239	Intermediate Similarity	NPC57628
0.8239	Intermediate Similarity	NPC188865
0.8239	Intermediate Similarity	NPC163719
0.8239	Intermediate Similarity	NPC472573
0.8239	Intermediate Similarity	NPC25768
0.8239	Intermediate Similarity	NPC70716
0.8239	Intermediate Similarity	NPC125106
0.8239	Intermediate Similarity	NPC472570
0.8239	Intermediate Similarity	NPC476974
0.8235	Intermediate Similarity	NPC476976
0.8231	Intermediate Similarity	NPC228204
0.8231	Intermediate Similarity	NPC282239
0.8231	Intermediate Similarity	NPC114410
0.8231	Intermediate Similarity	NPC472549
0.8231	Intermediate Similarity	NPC26033
0.8231	Intermediate Similarity	NPC112523
0.8227	Intermediate Similarity	NPC140021
0.8219	Intermediate Similarity	NPC477905
0.8214	Intermediate Similarity	NPC275592
0.8214	Intermediate Similarity	NPC90614
0.8214	Intermediate Similarity	NPC100913
0.8195	Intermediate Similarity	NPC470158
0.8195	Intermediate Similarity	NPC470818
0.8195	Intermediate Similarity	NPC475933
0.8188	Intermediate Similarity	NPC477893
0.8188	Intermediate Similarity	NPC477896
0.8182	Intermediate Similarity	NPC472568
0.8182	Intermediate Similarity	NPC70403
0.8182	Intermediate Similarity	NPC140118
0.8182	Intermediate Similarity	NPC470157
0.8182	Intermediate Similarity	NPC174982
0.8182	Intermediate Similarity	NPC184817
0.8182	Intermediate Similarity	NPC158663
0.8182	Intermediate Similarity	NPC171525
0.8182	Intermediate Similarity	NPC476973
0.8182	Intermediate Similarity	NPC472571
0.8182	Intermediate Similarity	NPC473088
0.8182	Intermediate Similarity	NPC469349
0.8182	Intermediate Similarity	NPC29704
0.8182	Intermediate Similarity	NPC471104
0.8182	Intermediate Similarity	NPC472556
0.8182	Intermediate Similarity	NPC177940
0.8182	Intermediate Similarity	NPC200471
0.8182	Intermediate Similarity	NPC40085
0.8182	Intermediate Similarity	NPC472575
0.8182	Intermediate Similarity	NPC472572
0.8182	Intermediate Similarity	NPC12881
0.8182	Intermediate Similarity	NPC264270
0.8182	Intermediate Similarity	NPC470159
0.8182	Intermediate Similarity	NPC96903
0.8176	Intermediate Similarity	NPC106895
0.8169	Intermediate Similarity	NPC477894
0.8158	Intermediate Similarity	NPC471493
0.8156	Intermediate Similarity	NPC213567
0.8151	Intermediate Similarity	NPC329657
0.8151	Intermediate Similarity	NPC470153
0.8134	Intermediate Similarity	NPC146239
0.8125	Intermediate Similarity	NPC473602
0.8121	Intermediate Similarity	NPC469771
0.812	Intermediate Similarity	NPC284022
0.8112	Intermediate Similarity	NPC241951
0.8112	Intermediate Similarity	NPC470152
0.8112	Intermediate Similarity	NPC475759
0.8112	Intermediate Similarity	NPC475122
0.8099	Intermediate Similarity	NPC192658
0.8099	Intermediate Similarity	NPC182869
0.8088	Intermediate Similarity	NPC475138
0.8082	Intermediate Similarity	NPC473214
0.8082	Intermediate Similarity	NPC470245
0.8074	Intermediate Similarity	NPC58061
0.8074	Intermediate Similarity	NPC230331
0.8069	Intermediate Similarity	NPC281717
0.8069	Intermediate Similarity	NPC132652
0.8067	Intermediate Similarity	NPC471102
0.806	Intermediate Similarity	NPC328997
0.806	Intermediate Similarity	NPC470816
0.806	Intermediate Similarity	NPC294050
0.8058	Intermediate Similarity	NPC472577
0.8058	Intermediate Similarity	NPC291638
0.8058	Intermediate Similarity	NPC66761
0.8058	Intermediate Similarity	NPC17877
0.8058	Intermediate Similarity	NPC195647
0.8056	Intermediate Similarity	NPC471100
0.8056	Intermediate Similarity	NPC473541

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 NPC209851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	236
0.1-0.2	695
0.2-0.3	1481
0.3-0.4	2898
0.4-0.5	2225
0.5-0.6	1311
0.6-0.7	293
0.7-0.8	11
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
0.7914	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD8368	Discontinued
0.7561	Intermediate Similarity	NPD8407	Phase 2
0.7551	Intermediate Similarity	NPD8166	Discontinued
0.747	Intermediate Similarity	NPD8434	Phase 2
0.7465	Intermediate Similarity	NPD7961	Discontinued
0.7453	Intermediate Similarity	NPD7799	Discontinued
0.745	Intermediate Similarity	NPD7236	Approved
0.7424	Intermediate Similarity	NPD2629	Approved
0.7407	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7094	Approved
0.7405	Intermediate Similarity	NPD6858	Approved
0.7381	Intermediate Similarity	NPD8361	Approved
0.7381	Intermediate Similarity	NPD8360	Approved
0.7381	Intermediate Similarity	NPD8435	Approved
0.7368	Intermediate Similarity	NPD4198	Discontinued
0.7324	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7239	Suspended
0.7262	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6010	Discontinued
0.7174	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8485	Approved
0.7109	Intermediate Similarity	NPD6647	Phase 2
0.7086	Intermediate Similarity	NPD4628	Phase 3
0.7054	Intermediate Similarity	NPD5909	Discontinued
0.7045	Intermediate Similarity	NPD2067	Discontinued
0.7039	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8127	Discontinued
0.7016	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD2066	Phase 3
0.7006	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5048	Discontinued
0.6985	Remote Similarity	NPD7115	Discovery
0.698	Remote Similarity	NPD7305	Phase 1
0.6978	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7008	Discontinued
0.6959	Remote Similarity	NPD8150	Discontinued
0.6957	Remote Similarity	NPD7741	Discontinued
0.6928	Remote Similarity	NPD6190	Approved
0.6912	Remote Similarity	NPD5951	Approved
0.6903	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7058	Phase 2
0.6894	Remote Similarity	NPD7057	Phase 3
0.6884	Remote Similarity	NPD7610	Discontinued
0.6875	Remote Similarity	NPD7819	Suspended
0.6875	Remote Similarity	NPD7798	Approved
0.6875	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6663	Approved
0.6866	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3317	Approved
0.6857	Remote Similarity	NPD5125	Phase 3
0.6857	Remote Similarity	NPD5126	Approved
0.6846	Remote Similarity	NPD1930	Approved
0.6846	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1929	Approved
0.6842	Remote Similarity	NPD2182	Approved
0.6831	Remote Similarity	NPD6637	Approved
0.6828	Remote Similarity	NPD5736	Approved
0.6818	Remote Similarity	NPD6685	Approved
0.6803	Remote Similarity	NPD3764	Approved
0.6802	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8313	Approved
0.6784	Remote Similarity	NPD8312	Approved
0.6782	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2346	Discontinued
0.677	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6085	Phase 2
0.6748	Remote Similarity	NPD7075	Discontinued
0.6738	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3226	Approved
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD7473	Discontinued
0.6646	Remote Similarity	NPD6273	Approved
0.6645	Remote Similarity	NPD2799	Discontinued
0.6644	Remote Similarity	NPD8032	Phase 2
0.6643	Remote Similarity	NPD6287	Discontinued
0.6643	Remote Similarity	NPD4807	Approved
0.6643	Remote Similarity	NPD4806	Approved
0.6642	Remote Similarity	NPD6686	Approved
0.6641	Remote Similarity	NPD1932	Approved
0.6625	Remote Similarity	NPD7458	Discontinued
0.6622	Remote Similarity	NPD7095	Approved
0.662	Remote Similarity	NPD5306	Approved
0.662	Remote Similarity	NPD5305	Approved
0.662	Remote Similarity	NPD2932	Approved
0.6606	Remote Similarity	NPD6234	Discontinued
0.6605	Remote Similarity	NPD37	Approved
0.6599	Remote Similarity	NPD7084	Phase 3
0.6596	Remote Similarity	NPD8462	Phase 1
0.6596	Remote Similarity	NPD6319	Approved
0.6596	Remote Similarity	NPD7009	Phase 2
0.6593	Remote Similarity	NPD2329	Discontinued
0.6591	Remote Similarity	NPD5765	Approved
0.6585	Remote Similarity	NPD4967	Phase 2
0.6585	Remote Similarity	NPD4966	Approved
0.6585	Remote Similarity	NPD4965	Approved
0.6584	Remote Similarity	NPD4380	Phase 2
0.6579	Remote Similarity	NPD7097	Phase 1
0.6577	Remote Similarity	NPD2313	Discontinued
0.6569	Remote Similarity	NPD6912	Phase 3
0.6569	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD164	Approved
0.6538	Remote Similarity	NPD4110	Phase 3
0.6538	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD1088	Approved
0.6533	Remote Similarity	NPD7714	Approved
0.6533	Remote Similarity	NPD7715	Approved
0.6524	Remote Similarity	NPD5402	Approved
0.6522	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1989	Approved
0.6506	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6801	Discontinued
0.6503	Remote Similarity	NPD3019	Approved
0.6494	Remote Similarity	NPD2438	Suspended
0.6488	Remote Similarity	NPD6232	Discontinued
0.6481	Remote Similarity	NPD7028	Phase 2
0.6478	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6765	Approved
0.6474	Remote Similarity	NPD6764	Approved
0.6474	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6798	Discontinued
0.6466	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5761	Phase 2
0.6463	Remote Similarity	NPD5760	Phase 2
0.6463	Remote Similarity	NPD1470	Approved
0.6463	Remote Similarity	NPD8455	Phase 2
0.6462	Remote Similarity	NPD7902	Approved
0.6462	Remote Similarity	NPD3495	Discontinued
0.6458	Remote Similarity	NPD8328	Phase 3
0.6458	Remote Similarity	NPD8404	Phase 2
0.6458	Remote Similarity	NPD4106	Approved
0.6458	Remote Similarity	NPD4136	Approved
0.6458	Remote Similarity	NPD4135	Approved
0.6452	Remote Similarity	NPD5762	Approved
0.6452	Remote Similarity	NPD5763	Approved
0.6449	Remote Similarity	NPD8297	Approved
0.6434	Remote Similarity	NPD1693	Approved
0.6434	Remote Similarity	NPD8513	Phase 3
0.6434	Remote Similarity	NPD8516	Approved
0.6434	Remote Similarity	NPD8517	Approved
0.6434	Remote Similarity	NPD8515	Approved
0.6433	Remote Similarity	NPD7228	Approved
0.6433	Remote Similarity	NPD7003	Approved
0.6424	Remote Similarity	NPD6233	Phase 2
0.6424	Remote Similarity	NPD3817	Phase 2
0.6424	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5647	Approved
0.6415	Remote Similarity	NPD6799	Approved
0.6412	Remote Similarity	NPD7638	Approved
0.6408	Remote Similarity	NPD6065	Approved
0.6403	Remote Similarity	NPD4632	Approved
0.6398	Remote Similarity	NPD5403	Approved
0.6398	Remote Similarity	NPD8320	Phase 1
0.6398	Remote Similarity	NPD8319	Approved
0.6395	Remote Similarity	NPD1283	Approved
0.6387	Remote Similarity	NPD6099	Approved
0.6387	Remote Similarity	NPD5406	Approved
0.6387	Remote Similarity	NPD5405	Approved
0.6387	Remote Similarity	NPD5404	Approved
0.6387	Remote Similarity	NPD6100	Approved
0.6387	Remote Similarity	NPD2935	Discontinued
0.6387	Remote Similarity	NPD5408	Approved
0.6386	Remote Similarity	NPD7768	Phase 2
0.6386	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2979	Phase 3
0.6382	Remote Similarity	NPD4140	Approved
0.6379	Remote Similarity	NPD7685	Pre-registration
0.6379	Remote Similarity	NPD6559	Discontinued
0.6378	Remote Similarity	NPD3673	Approved
0.6378	Remote Similarity	NPD1090	Approved
0.6378	Remote Similarity	NPD1089	Approved
0.6378	Remote Similarity	NPD1086	Approved
0.6378	Remote Similarity	NPD3672	Approved
0.6375	Remote Similarity	NPD2534	Approved
0.6375	Remote Similarity	NPD5401	Approved
0.6375	Remote Similarity	NPD2532	Approved
0.6375	Remote Similarity	NPD2533	Approved
0.6375	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1608	Approved
0.6364	Remote Similarity	NPD9545	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1238	Approved
0.6357	Remote Similarity	NPD2652	Approved
0.6357	Remote Similarity	NPD2650	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