NPASS Compound

Structure

NPC472418 OpenBabel07101719142D 45 49 0 0 1 0 0 0 0 0999 V2000 -1.6927 -3.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9165 1.9822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0560 -3.3342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6837 -5.0514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3890 -0.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7717 -1.4966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9748 -1.5727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4025 -1.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9695 -2.5038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2992 1.0583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4473 -4.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 -4.1275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0731 -0.6589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3564 -1.9558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7802 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0731 -0.6589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0731 -3.0731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3660 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0731 -3.0731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7802 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2907 0.9278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8299 -5.0514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9098 -3.3342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4325 -2.3385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.8660 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 -0.6904 0.2650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4558 -3.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6904 -3.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 33 1 0 0 0 0 6 33 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 23 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 34 1 0 0 0 0 17 25 1 0 0 0 0 18 41 1 0 0 0 0 19 25 1 0 0 0 0 19 28 2 0 0 0 0 20 36 2 0 0 0 0 20 42 1 0 0 0 0 21 37 2 0 0 0 0 21 43 1 0 0 0 0 22 38 2 0 0 0 0 22 44 1 0 0 0 0 24 17 1 1 0 0 0 24 29 1 0 0 0 0 24 33 1 0 0 0 0 25 39 2 0 0 0 0 26 35 1 1 0 0 0 26 45 1 0 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 42 1 1 0 0 0 30 32 1 0 0 0 0 30 43 1 6 0 0 0 31 34 1 6 0 0 0 31 35 1 0 0 0 0 32 34 1 1 0 0 0 32 44 1 0 0 0 0 34 7 1 6 0 0 0 35 18 1 6 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.28
Volume:	632.671
LogP:	3.911
LogD:	2.578
LogS:	-4.895
# Rotatable Bonds:	10
TPSA:	134.8
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.189
Synthetic Accessibility Score:	6.172
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203
MDCK Permeability:	3.6576358979800716e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.596
Plasma Protein Binding (PPB):	83.70620727539062%
Volume Distribution (VD):	1.544
Pgp-substrate:	12.01083755493164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.759
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	2.745
Half-life (T1/2):	0.483

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.667
Skin Sensitization:	0.816
Carcinogencity:	0.037
Eye Corrosion:	0.01
Eye Irritation:	0.037
Respiratory Toxicity:	0.851

Download Data

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

Natural Product: NPC472418

Natural Product ID:	NPC472418
*Common Name:**	UJCZSWXREVYNSG-LWXGZBIQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UJCZSWXREVYNSG-LWXGZBIQSA-N
Standard InCHI:	InChI=1S/C35H42O10/c1-19-25(39)17-24-29(42-20(2)36)31-34(7,32(44-22(4)38)30(43-21(3)37)28(19)33(24,5)6)16-15-26(35(31)18-41-35)45-27(40)14-13-23-11-9-8-10-12-23/h8-14,24,26,29-32H,15-18H2,1-7H3/b14-13+/t24-,26-,29+,30+,31-,32-,34+,35-/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H]2[C@]3(CO3)[C@H](CC[C@@]2(C)[C@@H](OC(=O)C)[C@@H](C2=C(C(=O)C[C@@H]1C2(C)C)C)OC(=O)C)OC(=O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL340254
PubChem CID:	15378565
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]
NPO24820	Taxus cuspidata	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]
NPO24820	Taxus cuspidata	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	3

Activity Type	# Activity
NON-MOLECULAR	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Control	=	358.0	%	PMID[459752]
NPT2	Others	Unspecified		Control	=	1027.0	%	PMID[459752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3.0	ug.mL-1	PMID[459752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[459752]
NPT2	Others	Unspecified		Activity	=	139.0	%	PMID[459753]

☑ 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 NPC472418 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	319
0.1-0.2	1179
0.2-0.3	2338
0.3-0.4	5587
0.4-0.5	9937
0.5-0.6	17220
0.6-0.7	5448
0.7-0.8	588
0.8-0.85	64
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC195224
0.9431	High Similarity	NPC469742
0.9237	High Similarity	NPC184109
0.9213	High Similarity	NPC225103
0.9206	High Similarity	NPC473423
0.9147	High Similarity	NPC209851
0.9147	High Similarity	NPC80599
0.9141	High Similarity	NPC473443
0.9141	High Similarity	NPC472388
0.907	High Similarity	NPC472361
0.9032	High Similarity	NPC300827
0.9032	High Similarity	NPC473439
0.9	High Similarity	NPC472394
0.8943	High Similarity	NPC89324
0.8931	High Similarity	NPC472437
0.8855	High Similarity	NPC471880
0.8855	High Similarity	NPC475493
0.8828	High Similarity	NPC473082
0.881	High Similarity	NPC473749
0.875	High Similarity	NPC473083
0.875	High Similarity	NPC471758
0.874	High Similarity	NPC12016
0.8696	High Similarity	NPC471912
0.8696	High Similarity	NPC80895
0.8686	High Similarity	NPC34012
0.8682	High Similarity	NPC45821
0.8672	High Similarity	NPC472373
0.8633	High Similarity	NPC301946
0.8633	High Similarity	NPC277053
0.8626	High Similarity	NPC93632
0.8603	High Similarity	NPC472395
0.8603	High Similarity	NPC472371
0.8593	High Similarity	NPC472372
0.8593	High Similarity	NPC472374
0.854	High Similarity	NPC183270
0.854	High Similarity	NPC477904
0.8519	High Similarity	NPC291638
0.8519	High Similarity	NPC66761
0.8519	High Similarity	NPC472577
0.8519	High Similarity	NPC195647
0.8519	High Similarity	NPC17877
0.8516	High Similarity	NPC70973
0.8511	High Similarity	NPC217918
0.8489	Intermediate Similarity	NPC477894
0.8444	Intermediate Similarity	NPC474608
0.8444	Intermediate Similarity	NPC4242
0.8444	Intermediate Similarity	NPC471911
0.844	Intermediate Similarity	NPC474935
0.8438	Intermediate Similarity	NPC311175
0.8438	Intermediate Similarity	NPC37641
0.8429	Intermediate Similarity	NPC38696
0.8417	Intermediate Similarity	NPC140021
0.8406	Intermediate Similarity	NPC473109
0.8406	Intermediate Similarity	NPC473613
0.8406	Intermediate Similarity	NPC475400
0.8406	Intermediate Similarity	NPC211137
0.8406	Intermediate Similarity	NPC4341
0.8406	Intermediate Similarity	NPC200592
0.8406	Intermediate Similarity	NPC473081
0.8406	Intermediate Similarity	NPC43241
0.8406	Intermediate Similarity	NPC473758
0.8406	Intermediate Similarity	NPC476094
0.8406	Intermediate Similarity	NPC473060
0.8406	Intermediate Similarity	NPC473112
0.8406	Intermediate Similarity	NPC473085
0.8406	Intermediate Similarity	NPC48017
0.8406	Intermediate Similarity	NPC184747
0.8406	Intermediate Similarity	NPC147880
0.8406	Intermediate Similarity	NPC472547
0.84	Intermediate Similarity	NPC476476
0.8397	Intermediate Similarity	NPC473110
0.8397	Intermediate Similarity	NPC473111
0.8397	Intermediate Similarity	NPC470818
0.8392	Intermediate Similarity	NPC91730
0.8345	Intermediate Similarity	NPC16912
0.8333	Intermediate Similarity	NPC210591
0.8333	Intermediate Similarity	NPC475652
0.8333	Intermediate Similarity	NPC197037
0.8333	Intermediate Similarity	NPC214550
0.8321	Intermediate Similarity	NPC472545
0.8321	Intermediate Similarity	NPC114927
0.8321	Intermediate Similarity	NPC472551
0.8298	Intermediate Similarity	NPC470231
0.8286	Intermediate Similarity	NPC472546
0.8286	Intermediate Similarity	NPC63737
0.8284	Intermediate Similarity	NPC147561
0.8273	Intermediate Similarity	NPC97667
0.8273	Intermediate Similarity	NPC171207
0.8273	Intermediate Similarity	NPC90614
0.8268	Intermediate Similarity	NPC84129
0.8261	Intermediate Similarity	NPC283375
0.8261	Intermediate Similarity	NPC183122
0.8261	Intermediate Similarity	NPC39549
0.8258	Intermediate Similarity	NPC476970
0.8248	Intermediate Similarity	NPC473216
0.8248	Intermediate Similarity	NPC473399
0.8239	Intermediate Similarity	NPC127857
0.8239	Intermediate Similarity	NPC471107
0.8239	Intermediate Similarity	NPC471100
0.8227	Intermediate Similarity	NPC475429
0.8227	Intermediate Similarity	NPC246480
0.8227	Intermediate Similarity	NPC473673
0.8227	Intermediate Similarity	NPC139067
0.8227	Intermediate Similarity	NPC147217
0.8227	Intermediate Similarity	NPC177340
0.8227	Intermediate Similarity	NPC191082
0.8227	Intermediate Similarity	NPC270498
0.8222	Intermediate Similarity	NPC476977
0.8219	Intermediate Similarity	NPC248265
0.8219	Intermediate Similarity	NPC11588
0.8219	Intermediate Similarity	NPC134685
0.8219	Intermediate Similarity	NPC219419
0.8219	Intermediate Similarity	NPC229545
0.8214	Intermediate Similarity	NPC27377
0.8214	Intermediate Similarity	NPC472576
0.8214	Intermediate Similarity	NPC97947
0.8214	Intermediate Similarity	NPC41481
0.8214	Intermediate Similarity	NPC224491
0.8214	Intermediate Similarity	NPC118080
0.8214	Intermediate Similarity	NPC291599
0.8214	Intermediate Similarity	NPC87448
0.8203	Intermediate Similarity	NPC473860
0.8195	Intermediate Similarity	NPC171007
0.8195	Intermediate Similarity	NPC476972
0.8195	Intermediate Similarity	NPC190849
0.8195	Intermediate Similarity	NPC476971
0.8169	Intermediate Similarity	NPC163719
0.8169	Intermediate Similarity	NPC188865
0.8169	Intermediate Similarity	NPC25768
0.8169	Intermediate Similarity	NPC11685
0.8169	Intermediate Similarity	NPC472569
0.8169	Intermediate Similarity	NPC95265
0.8169	Intermediate Similarity	NPC51314
0.8169	Intermediate Similarity	NPC67777
0.8169	Intermediate Similarity	NPC70716
0.8169	Intermediate Similarity	NPC95810
0.8169	Intermediate Similarity	NPC125106
0.8169	Intermediate Similarity	NPC472573
0.8169	Intermediate Similarity	NPC57628
0.8169	Intermediate Similarity	NPC476974
0.8169	Intermediate Similarity	NPC472570
0.8163	Intermediate Similarity	NPC259144
0.8163	Intermediate Similarity	NPC155329
0.8163	Intermediate Similarity	NPC473670
0.8163	Intermediate Similarity	NPC21410
0.8163	Intermediate Similarity	NPC114357
0.8163	Intermediate Similarity	NPC471176
0.8162	Intermediate Similarity	NPC476976
0.8162	Intermediate Similarity	NPC238370
0.8143	Intermediate Similarity	NPC100913
0.8143	Intermediate Similarity	NPC275592
0.8143	Intermediate Similarity	NPC473440
0.8138	Intermediate Similarity	NPC7095
0.8138	Intermediate Similarity	NPC112216
0.8138	Intermediate Similarity	NPC254558
0.8125	Intermediate Similarity	NPC152812
0.812	Intermediate Similarity	NPC475933
0.812	Intermediate Similarity	NPC470158
0.8116	Intermediate Similarity	NPC477893
0.8112	Intermediate Similarity	NPC469349
0.8112	Intermediate Similarity	NPC177940
0.8112	Intermediate Similarity	NPC473088
0.8112	Intermediate Similarity	NPC472556
0.8112	Intermediate Similarity	NPC472575
0.8112	Intermediate Similarity	NPC472568
0.8112	Intermediate Similarity	NPC471104
0.8112	Intermediate Similarity	NPC470157
0.8112	Intermediate Similarity	NPC174982
0.8112	Intermediate Similarity	NPC472572
0.8112	Intermediate Similarity	NPC200471
0.8112	Intermediate Similarity	NPC470159
0.8112	Intermediate Similarity	NPC70403
0.8112	Intermediate Similarity	NPC473541
0.8112	Intermediate Similarity	NPC29704
0.8112	Intermediate Similarity	NPC96903
0.8112	Intermediate Similarity	NPC476973
0.8112	Intermediate Similarity	NPC472571
0.8112	Intermediate Similarity	NPC158663
0.8112	Intermediate Similarity	NPC184817
0.8112	Intermediate Similarity	NPC171525
0.8108	Intermediate Similarity	NPC217091
0.8102	Intermediate Similarity	NPC15850
0.8099	Intermediate Similarity	NPC163087
0.8099	Intermediate Similarity	NPC131966
0.8099	Intermediate Similarity	NPC191387
0.8092	Intermediate Similarity	NPC475328
0.8082	Intermediate Similarity	NPC101043
0.8082	Intermediate Similarity	NPC306799
0.8082	Intermediate Similarity	NPC51602
0.8069	Intermediate Similarity	NPC60509
0.8069	Intermediate Similarity	NPC81698
0.8069	Intermediate Similarity	NPC250046
0.8054	Intermediate Similarity	NPC472393
0.8047	Intermediate Similarity	NPC470820
0.8045	Intermediate Similarity	NPC284022
0.8042	Intermediate Similarity	NPC475122
0.8042	Intermediate Similarity	NPC470152
0.8042	Intermediate Similarity	NPC111466
0.8042	Intermediate Similarity	NPC241951
0.8042	Intermediate Similarity	NPC475759

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 NPC472418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	805
0.2-0.3	1612
0.3-0.4	3139
0.4-0.5	2054
0.5-0.6	1119
0.6-0.7	144
0.7-0.8	4
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
0.7462	Intermediate Similarity	NPD7094	Approved
0.7462	Intermediate Similarity	NPD6858	Approved
0.7423	Intermediate Similarity	NPD8368	Discontinued
0.7383	Intermediate Similarity	NPD7236	Approved
0.7346	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD8407	Phase 2
0.7255	Intermediate Similarity	NPD7239	Suspended
0.7248	Intermediate Similarity	NPD8166	Discontinued
0.7226	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8434	Phase 2
0.7178	Intermediate Similarity	NPD7799	Discontinued
0.7153	Intermediate Similarity	NPD7961	Discontinued
0.7118	Intermediate Similarity	NPD8361	Approved
0.7118	Intermediate Similarity	NPD8360	Approved
0.7118	Intermediate Similarity	NPD8435	Approved
0.7099	Intermediate Similarity	NPD2067	Discontinued
0.7063	Intermediate Similarity	NPD7798	Approved
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD8127	Discontinued
0.6963	Remote Similarity	NPD2629	Approved
0.6917	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4198	Discontinued
0.6894	Remote Similarity	NPD2182	Approved
0.6879	Remote Similarity	NPD6637	Approved
0.6875	Remote Similarity	NPD8485	Approved
0.6863	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5909	Discontinued
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7057	Phase 3
0.6832	Remote Similarity	NPD7058	Phase 2
0.6797	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7115	Discovery
0.6788	Remote Similarity	NPD3317	Approved
0.6769	Remote Similarity	NPD6647	Phase 2
0.6765	Remote Similarity	NPD6010	Discontinued
0.6763	Remote Similarity	NPD7741	Discontinued
0.676	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6190	Approved
0.6744	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7055	Discontinued
0.6705	Remote Similarity	NPD8150	Discontinued
0.669	Remote Similarity	NPD6287	Discontinued
0.669	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7305	Phase 1
0.6689	Remote Similarity	NPD8032	Phase 2
0.6688	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD2066	Phase 3
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD2438	Suspended
0.6642	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4966	Approved
0.6626	Remote Similarity	NPD4967	Phase 2
0.6626	Remote Similarity	NPD4965	Approved
0.6618	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6685	Approved
0.6605	Remote Similarity	NPD7819	Suspended
0.6594	Remote Similarity	NPD5951	Approved
0.6591	Remote Similarity	NPD164	Approved
0.6577	Remote Similarity	NPD6663	Approved
0.6571	Remote Similarity	NPD7610	Discontinued
0.6562	Remote Similarity	NPD1989	Approved
0.6549	Remote Similarity	NPD5126	Approved
0.6549	Remote Similarity	NPD5125	Phase 3
0.6545	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6234	Discontinued
0.6541	Remote Similarity	NPD5048	Discontinued
0.6541	Remote Similarity	NPD6008	Approved
0.6538	Remote Similarity	NPD6648	Approved
0.6531	Remote Similarity	NPD5736	Approved
0.6531	Remote Similarity	NPD7084	Phase 3
0.6515	Remote Similarity	NPD1930	Approved
0.6515	Remote Similarity	NPD1929	Approved
0.6515	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3495	Discontinued
0.651	Remote Similarity	NPD3764	Approved
0.6509	Remote Similarity	NPD7473	Discontinued
0.6494	Remote Similarity	NPD7266	Discontinued
0.6494	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3748	Approved
0.646	Remote Similarity	NPD7458	Discontinued
0.6454	Remote Similarity	NPD6065	Approved
0.6441	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD8313	Approved
0.6437	Remote Similarity	NPD8312	Approved
0.6434	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3672	Approved
0.6429	Remote Similarity	NPD3673	Approved
0.6424	Remote Similarity	NPD2979	Phase 3
0.642	Remote Similarity	NPD6599	Discontinued
0.6416	Remote Similarity	NPD7685	Pre-registration
0.6415	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1238	Approved
0.6407	Remote Similarity	NPD5494	Approved
0.6406	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7900	Approved
0.6405	Remote Similarity	NPD7097	Phase 1
0.6402	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5765	Approved
0.6387	Remote Similarity	NPD2346	Discontinued
0.6386	Remote Similarity	NPD7075	Discontinued
0.6382	Remote Similarity	NPD6355	Discontinued
0.6377	Remote Similarity	NPD6912	Phase 3
0.6377	Remote Similarity	NPD8297	Approved
0.6375	Remote Similarity	NPD6273	Approved
0.6374	Remote Similarity	NPD7228	Approved
0.6369	Remote Similarity	NPD4110	Phase 3
0.6369	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD8462	Phase 1
0.6364	Remote Similarity	NPD5585	Approved
0.6364	Remote Similarity	NPD3024	Approved
0.6364	Remote Similarity	NPD3025	Approved
0.6358	Remote Similarity	NPD3226	Approved
0.6358	Remote Similarity	NPD7713	Phase 3
0.6337	Remote Similarity	NPD5844	Phase 1
0.6336	Remote Similarity	NPD5926	Approved
0.6335	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD6232	Discontinued
0.6328	Remote Similarity	NPD7631	Approved
0.6327	Remote Similarity	NPD5667	Approved
0.6325	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6686	Approved
0.6323	Remote Similarity	NPD6099	Approved
0.6323	Remote Similarity	NPD6100	Approved
0.6322	Remote Similarity	NPD6765	Approved
0.6322	Remote Similarity	NPD6764	Approved
0.6319	Remote Similarity	NPD2932	Approved
0.6319	Remote Similarity	NPD7028	Phase 2
0.6316	Remote Similarity	NPD1932	Approved
0.6312	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8455	Phase 2
0.6294	Remote Similarity	NPD7009	Phase 2
0.6284	Remote Similarity	NPD3267	Approved
0.6284	Remote Similarity	NPD3266	Approved
0.6279	Remote Similarity	NPD3751	Discontinued
0.6277	Remote Similarity	NPD2329	Discontinued
0.6276	Remote Similarity	NPD3026	Approved
0.6276	Remote Similarity	NPD3023	Approved
0.6269	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD6832	Phase 2
0.6266	Remote Similarity	NPD3750	Approved
0.6266	Remote Similarity	NPD7003	Approved
0.6265	Remote Similarity	NPD3817	Phase 2
0.6265	Remote Similarity	NPD5402	Approved
0.626	Remote Similarity	NPD7902	Approved
0.6258	Remote Similarity	NPD2799	Discontinued
0.6258	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8285	Discontinued
0.625	Remote Similarity	NPD7715	Approved
0.625	Remote Similarity	NPD7609	Phase 3
0.625	Remote Similarity	NPD7714	Approved
0.625	Remote Similarity	NPD5691	Approved
0.6242	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6801	Discontinued
0.6242	Remote Similarity	NPD6085	Phase 2
0.6241	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD8404	Phase 2
0.6233	Remote Similarity	NPD1281	Approved
0.6233	Remote Similarity	NPD4806	Approved
0.6233	Remote Similarity	NPD4807	Approved
0.6231	Remote Similarity	NPD6049	Phase 2
0.6231	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD7240	Approved
0.6225	Remote Similarity	NPD7095	Approved
0.622	Remote Similarity	NPD4380	Phase 2
0.6218	Remote Similarity	NPD2796	Approved
0.6212	Remote Similarity	NPD7638	Approved
0.6207	Remote Similarity	NPD17	Approved
0.6207	Remote Similarity	NPD5306	Approved
0.6207	Remote Similarity	NPD3019	Approved
0.6207	Remote Similarity	NPD5305	Approved
0.6205	Remote Similarity	NPD5760	Phase 2
0.6205	Remote Similarity	NPD5761	Phase 2
0.6204	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD1088	Approved
0.619	Remote Similarity	NPD1282	Approved
0.619	Remote Similarity	NPD3972	Approved
0.619	Remote Similarity	NPD1087	Approved
0.6187	Remote Similarity	NPD6650	Approved
0.6187	Remote Similarity	NPD6649	Approved
0.6184	Remote Similarity	NPD6798	Discontinued
0.6184	Remote Similarity	NPD3268	Approved
0.6184	Remote Similarity	NPD2313	Discontinued
0.6184	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6386	Approved
0.6182	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6385	Approved
0.6181	Remote Similarity	NPD6319	Approved
0.618	Remote Similarity	NPD6785	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