NPASS Compound

Structure

NPC4242 OpenBabel07101718312D 44 48 0 0 1 0 0 0 0 0999 V2000 0.7206 0.6978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0401 3.3803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6037 0.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6947 -0.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1670 0.2372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0182 3.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1454 -0.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 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 -1.4067 -2.6456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6874 3.9155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 3.3147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7681 -0.8893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 32 1 0 0 0 0 7 32 1 0 0 0 0 8 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 28 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 33 1 0 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 19 34 1 6 0 0 0 20 27 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 38 2 0 0 0 0 23 43 1 0 0 0 0 25 18 1 6 0 0 0 25 29 1 0 0 0 0 25 32 1 0 0 0 0 26 39 2 0 0 0 0 27 44 1 6 0 0 0 28 40 2 0 0 0 0 28 44 1 0 0 0 0 29 35 1 6 0 0 0 29 41 1 0 0 0 0 30 31 1 0 0 0 0 30 33 1 6 0 0 0 30 42 1 0 0 0 0 31 34 1 1 0 0 0 31 43 1 0 0 0 0 32 34 1 0 0 0 0 33 35 1 1 0 0 0 34 35 1 1 0 0 0 35 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	606.28
Volume:	623.881
LogP:	3.465
LogD:	2.177
LogS:	-5.02
# Rotatable Bonds:	10
TPSA:	122.27
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	6.578
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.288
MDCK Permeability:	3.446477421675809e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.212
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.504

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.711
Plasma Protein Binding (PPB):	56.033485412597656%
Volume Distribution (VD):	1.77
Pgp-substrate:	26.705795288085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.331
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.412
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.508

ADMET: Excretion

Clearance (CL):	3.367
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.739
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.835
Carcinogencity:	0.197
Eye Corrosion:	0.092
Eye Irritation:	0.376
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC4242

Natural Product ID:	NPC4242
*Common Name:**	Taxuspine C
IUPAC Name:	n.a.
Synonyms:	taxuspine C
Standard InCHIKey:	RDKGWOCOLMOGRF-DFVHPHDMSA-N
Standard InCHI:	InChI=1S/C35H42O9/c1-19-26(39)18-25-29(41-21(3)36)35-20(2)27(44-28(40)15-14-24-12-10-9-11-13-24)16-17-33(35,8)30(42-22(4)37)31(43-23(5)38)34(19,35)32(25,6)7/h9-15,19,25,27,29-31H,2,16-18H2,1,3-8H3/b15-14+/t19-,25+,27+,29-,30+,31+,33+,34-,35-/m1/s1
SMILES:	C[C@@H]1C(=O)C[C@H]2[C@H]([C@]34C(=C)[C@H](CC[C@@]3(C)[C@H]([C@@H]([C@@]14C2(C)C)OC(=O)C)OC(=O)C)OC(=O)/C=C/c1ccccc1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453986
PubChem CID:	15385058
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]
NPO33211	japanese yew	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9873389]
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
Cell Line	1
NON-MOLECULAR	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	>	10.0	ug.mL-1	PMID[543583]
NPT2	Others	Unspecified		VCR accumulation	=	213.0	n.a.	PMID[543583]
NPT2	Others	Unspecified		VCR accumulation	=	219.0	n.a.	PMID[543583]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[543583]
NPT2	Others	Unspecified		Activity	=	104.0	%	PMID[543584]

☑ 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 NPC4242 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	333
0.1-0.2	1146
0.2-0.3	2172
0.3-0.4	5030
0.4-0.5	9380
0.5-0.6	18308
0.6-0.7	5207
0.7-0.8	1025
0.8-0.85	89
0.85-0.9	2
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471911
0.9618	High Similarity	NPC473440
0.9474	High Similarity	NPC475135
0.9185	High Similarity	NPC63737
0.9141	High Similarity	NPC473423
0.876	High Similarity	NPC469742
0.8636	High Similarity	NPC195224
0.8582	High Similarity	NPC472361
0.8571	High Similarity	NPC225103
0.8519	High Similarity	NPC475493
0.8507	High Similarity	NPC473443
0.8507	High Similarity	NPC472388
0.8478	Intermediate Similarity	NPC184109
0.8456	Intermediate Similarity	NPC472437
0.8444	Intermediate Similarity	NPC472418
0.8382	Intermediate Similarity	NPC472394
0.8382	Intermediate Similarity	NPC209851
0.8357	Intermediate Similarity	NPC475660
0.8346	Intermediate Similarity	NPC473082
0.831	Intermediate Similarity	NPC131966
0.831	Intermediate Similarity	NPC191387
0.8273	Intermediate Similarity	NPC194769
0.8273	Intermediate Similarity	NPC285221
0.8271	Intermediate Similarity	NPC473083
0.8252	Intermediate Similarity	NPC80895
0.8252	Intermediate Similarity	NPC471912
0.8248	Intermediate Similarity	NPC80599
0.8248	Intermediate Similarity	NPC471880
0.8235	Intermediate Similarity	NPC475452
0.8235	Intermediate Similarity	NPC475671
0.8214	Intermediate Similarity	NPC475373
0.8209	Intermediate Similarity	NPC470818
0.8201	Intermediate Similarity	NPC265459
0.8201	Intermediate Similarity	NPC475262
0.8201	Intermediate Similarity	NPC290833
0.8194	Intermediate Similarity	NPC277053
0.8194	Intermediate Similarity	NPC301946
0.8188	Intermediate Similarity	NPC70344
0.8188	Intermediate Similarity	NPC472656
0.8182	Intermediate Similarity	NPC473749
0.8175	Intermediate Similarity	NPC470278
0.8169	Intermediate Similarity	NPC187566
0.8158	Intermediate Similarity	NPC55744
0.8156	Intermediate Similarity	NPC472395
0.8156	Intermediate Similarity	NPC53361
0.8156	Intermediate Similarity	NPC121268
0.8156	Intermediate Similarity	NPC325805
0.8156	Intermediate Similarity	NPC272523
0.8156	Intermediate Similarity	NPC472371
0.8154	Intermediate Similarity	NPC89324
0.8129	Intermediate Similarity	NPC329913
0.8129	Intermediate Similarity	NPC153617
0.8129	Intermediate Similarity	NPC472250
0.8121	Intermediate Similarity	NPC471176
0.8112	Intermediate Similarity	NPC472236
0.8112	Intermediate Similarity	NPC472235
0.8106	Intermediate Similarity	NPC300827
0.8106	Intermediate Similarity	NPC473439
0.8102	Intermediate Similarity	NPC475138
0.8102	Intermediate Similarity	NPC475508
0.8099	Intermediate Similarity	NPC475400
0.8095	Intermediate Similarity	NPC125033
0.8085	Intermediate Similarity	NPC86772
0.8085	Intermediate Similarity	NPC205305
0.8085	Intermediate Similarity	NPC327511
0.8071	Intermediate Similarity	NPC66761
0.8071	Intermediate Similarity	NPC17877
0.8071	Intermediate Similarity	NPC472577
0.8071	Intermediate Similarity	NPC291638
0.8071	Intermediate Similarity	NPC149401
0.8071	Intermediate Similarity	NPC279637
0.8071	Intermediate Similarity	NPC195647
0.8071	Intermediate Similarity	NPC477893
0.8069	Intermediate Similarity	NPC471162
0.8069	Intermediate Similarity	NPC471100
0.8069	Intermediate Similarity	NPC471107
0.806	Intermediate Similarity	NPC8990
0.8056	Intermediate Similarity	NPC82467
0.8045	Intermediate Similarity	NPC70973
0.8043	Intermediate Similarity	NPC72915
0.8039	Intermediate Similarity	NPC165234
0.8039	Intermediate Similarity	NPC475536
0.8028	Intermediate Similarity	NPC276652
0.8027	Intermediate Similarity	NPC76103
0.8014	Intermediate Similarity	NPC477095
0.8014	Intermediate Similarity	NPC478263
0.8	Intermediate Similarity	NPC469456
0.8	Intermediate Similarity	NPC298547
0.8	Intermediate Similarity	NPC474608
0.8	Intermediate Similarity	NPC126516
0.8	Intermediate Similarity	NPC324898
0.8	Intermediate Similarity	NPC477369
0.8	Intermediate Similarity	NPC203486
0.8	Intermediate Similarity	NPC134937
0.8	Intermediate Similarity	NPC48929
0.7987	Intermediate Similarity	NPC475505
0.7987	Intermediate Similarity	NPC475464
0.7987	Intermediate Similarity	NPC475437
0.7987	Intermediate Similarity	NPC475300
0.7987	Intermediate Similarity	NPC473641
0.7987	Intermediate Similarity	NPC473797
0.7986	Intermediate Similarity	NPC140021
0.7985	Intermediate Similarity	NPC12016
0.7973	Intermediate Similarity	NPC254558
0.7972	Intermediate Similarity	NPC184747
0.7972	Intermediate Similarity	NPC79921
0.7972	Intermediate Similarity	NPC48017
0.7972	Intermediate Similarity	NPC473758
0.7972	Intermediate Similarity	NPC211137
0.7972	Intermediate Similarity	NPC147880
0.7972	Intermediate Similarity	NPC4341
0.7972	Intermediate Similarity	NPC473112
0.7972	Intermediate Similarity	NPC473060
0.7972	Intermediate Similarity	NPC473109
0.7972	Intermediate Similarity	NPC473081
0.7972	Intermediate Similarity	NPC200592
0.7972	Intermediate Similarity	NPC43241
0.7972	Intermediate Similarity	NPC251294
0.7972	Intermediate Similarity	NPC473613
0.7972	Intermediate Similarity	NPC476094
0.7972	Intermediate Similarity	NPC473085
0.7971	Intermediate Similarity	NPC3450
0.7971	Intermediate Similarity	NPC147561
0.7971	Intermediate Similarity	NPC122504
0.797	Intermediate Similarity	NPC311175
0.797	Intermediate Similarity	NPC37641
0.7959	Intermediate Similarity	NPC205389
0.7945	Intermediate Similarity	NPC127857
0.7945	Intermediate Similarity	NPC478264
0.7943	Intermediate Similarity	NPC79699
0.7943	Intermediate Similarity	NPC477896
0.7943	Intermediate Similarity	NPC270364
0.7941	Intermediate Similarity	NPC473111
0.7941	Intermediate Similarity	NPC473110
0.7939	Intermediate Similarity	NPC152812
0.7939	Intermediate Similarity	NPC84129
0.7931	Intermediate Similarity	NPC477094
0.7931	Intermediate Similarity	NPC95449
0.7931	Intermediate Similarity	NPC477894
0.7931	Intermediate Similarity	NPC45307
0.7931	Intermediate Similarity	NPC477096
0.7926	Intermediate Similarity	NPC472373
0.7919	Intermediate Similarity	NPC96308
0.7919	Intermediate Similarity	NPC51602
0.7917	Intermediate Similarity	NPC473497
0.7917	Intermediate Similarity	NPC242355
0.7917	Intermediate Similarity	NPC16912
0.7917	Intermediate Similarity	NPC325078
0.7917	Intermediate Similarity	NPC266374
0.7917	Intermediate Similarity	NPC473654
0.7902	Intermediate Similarity	NPC214550
0.7902	Intermediate Similarity	NPC210591
0.7902	Intermediate Similarity	NPC473301
0.7902	Intermediate Similarity	NPC475652
0.7891	Intermediate Similarity	NPC475552
0.7891	Intermediate Similarity	NPC473602
0.7891	Intermediate Similarity	NPC312393
0.7887	Intermediate Similarity	NPC472372
0.7887	Intermediate Similarity	NPC472374
0.7885	Intermediate Similarity	NPC477491
0.7881	Intermediate Similarity	NPC473611
0.7877	Intermediate Similarity	NPC470231
0.7868	Intermediate Similarity	NPC471758
0.7868	Intermediate Similarity	NPC284022
0.7868	Intermediate Similarity	NPC114927
0.7862	Intermediate Similarity	NPC182869
0.7857	Intermediate Similarity	NPC233860
0.7852	Intermediate Similarity	NPC475561
0.7852	Intermediate Similarity	NPC232583
0.7852	Intermediate Similarity	NPC475417
0.7852	Intermediate Similarity	NPC112216
0.7852	Intermediate Similarity	NPC7095
0.7852	Intermediate Similarity	NPC25484
0.7847	Intermediate Similarity	NPC90614
0.7847	Intermediate Similarity	NPC477904
0.7847	Intermediate Similarity	NPC97667
0.7847	Intermediate Similarity	NPC171207
0.7847	Intermediate Similarity	NPC183270
0.7838	Intermediate Similarity	NPC327031
0.7832	Intermediate Similarity	NPC283375
0.7832	Intermediate Similarity	NPC262324
0.7832	Intermediate Similarity	NPC183122
0.7829	Intermediate Similarity	NPC326235
0.7829	Intermediate Similarity	NPC323001
0.7817	Intermediate Similarity	NPC473216
0.7817	Intermediate Similarity	NPC471864
0.7817	Intermediate Similarity	NPC473399
0.7817	Intermediate Similarity	NPC200154
0.7815	Intermediate Similarity	NPC472658
0.7815	Intermediate Similarity	NPC471135
0.7815	Intermediate Similarity	NPC472657
0.781	Intermediate Similarity	NPC476970
0.781	Intermediate Similarity	NPC45821
0.781	Intermediate Similarity	NPC477366
0.7808	Intermediate Similarity	NPC473673
0.7808	Intermediate Similarity	NPC139067
0.7808	Intermediate Similarity	NPC177340
0.7808	Intermediate Similarity	NPC246480
0.7808	Intermediate Similarity	NPC153214
0.7808	Intermediate Similarity	NPC270498

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 NPC4242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	735
0.2-0.3	1468
0.3-0.4	3254
0.4-0.5	2180
0.5-0.6	999
0.6-0.7	227
0.7-0.8	13
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
0.7969	Intermediate Similarity	NPD7094	Approved
0.7969	Intermediate Similarity	NPD6858	Approved
0.7823	Intermediate Similarity	NPD7236	Approved
0.7799	Intermediate Similarity	NPD7799	Discontinued
0.7704	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7239	Suspended
0.7483	Intermediate Similarity	NPD7961	Discontinued
0.7361	Intermediate Similarity	NPD6663	Approved
0.731	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7058	Phase 2
0.7233	Intermediate Similarity	NPD7057	Phase 3
0.716	Intermediate Similarity	NPD8127	Discontinued
0.7153	Intermediate Similarity	NPD7055	Discontinued
0.7133	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5736	Approved
0.7068	Intermediate Similarity	NPD2067	Discontinued
0.7007	Intermediate Similarity	NPD8032	Phase 2
0.7	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD8166	Discontinued
0.6978	Remote Similarity	NPD7741	Discontinued
0.697	Remote Similarity	NPD6685	Approved
0.6919	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7610	Discontinued
0.6899	Remote Similarity	NPD7798	Approved
0.6894	Remote Similarity	NPD6008	Approved
0.6889	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7305	Phase 1
0.6879	Remote Similarity	NPD6273	Approved
0.6849	Remote Similarity	NPD7084	Phase 3
0.6812	Remote Similarity	NPD2629	Approved
0.679	Remote Similarity	NPD5760	Phase 2
0.679	Remote Similarity	NPD5761	Phase 2
0.6784	Remote Similarity	NPD6765	Approved
0.6784	Remote Similarity	NPD8368	Discontinued
0.6784	Remote Similarity	NPD6764	Approved
0.6774	Remote Similarity	NPD4628	Phase 3
0.6763	Remote Similarity	NPD4198	Discontinued
0.6763	Remote Similarity	NPD8407	Phase 2
0.6742	Remote Similarity	NPD6647	Phase 2
0.6742	Remote Similarity	NPD5765	Approved
0.6741	Remote Similarity	NPD2182	Approved
0.6736	Remote Similarity	NPD7507	Approved
0.6736	Remote Similarity	NPD6637	Approved
0.6727	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD8297	Approved
0.6715	Remote Similarity	NPD6912	Phase 3
0.6692	Remote Similarity	NPD5909	Discontinued
0.6691	Remote Similarity	NPD4766	Approved
0.669	Remote Similarity	NPD3025	Approved
0.669	Remote Similarity	NPD3024	Approved
0.6689	Remote Similarity	NPD5735	Approved
0.6686	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8434	Phase 2
0.6686	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6085	Phase 2
0.6644	Remote Similarity	NPD7736	Approved
0.6644	Remote Similarity	NPD7008	Discontinued
0.6643	Remote Similarity	NPD3317	Approved
0.663	Remote Similarity	NPD7497	Discontinued
0.6629	Remote Similarity	NPD6785	Approved
0.6629	Remote Similarity	NPD6784	Approved
0.6624	Remote Similarity	NPD6190	Approved
0.6623	Remote Similarity	NPD4140	Approved
0.662	Remote Similarity	NPD6319	Approved
0.662	Remote Similarity	NPD7009	Phase 2
0.6619	Remote Similarity	NPD6010	Discontinued
0.6617	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8360	Approved
0.661	Remote Similarity	NPD8361	Approved
0.661	Remote Similarity	NPD8435	Approved
0.6605	Remote Similarity	NPD7028	Phase 2
0.6599	Remote Similarity	NPD7319	Approved
0.6597	Remote Similarity	NPD3026	Approved
0.6597	Remote Similarity	NPD3023	Approved
0.6581	Remote Similarity	NPD5763	Approved
0.6581	Remote Similarity	NPD5762	Approved
0.6575	Remote Similarity	NPD5327	Phase 3
0.6575	Remote Similarity	NPD7078	Approved
0.6571	Remote Similarity	NPD5951	Approved
0.6565	Remote Similarity	NPD7638	Approved
0.6552	Remote Similarity	NPD6287	Discontinued
0.6552	Remote Similarity	NPD7492	Approved
0.6547	Remote Similarity	NPD4632	Approved
0.6543	Remote Similarity	NPD7458	Discontinued
0.6528	Remote Similarity	NPD3019	Approved
0.6522	Remote Similarity	NPD6649	Approved
0.6522	Remote Similarity	NPD6650	Approved
0.6519	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5048	Discontinued
0.6515	Remote Similarity	NPD7640	Approved
0.6515	Remote Similarity	NPD2066	Phase 3
0.6515	Remote Similarity	NPD7639	Approved
0.6512	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6616	Approved
0.6506	Remote Similarity	NPD4965	Approved
0.6506	Remote Similarity	NPD4966	Approved
0.6506	Remote Similarity	NPD4967	Phase 2
0.6503	Remote Similarity	NPD6054	Approved
0.65	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3764	Approved
0.6486	Remote Similarity	NPD3094	Phase 2
0.6485	Remote Similarity	NPD7819	Suspended
0.6475	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6004	Phase 3
0.6474	Remote Similarity	NPD6005	Phase 3
0.6474	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6002	Phase 3
0.6474	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7199	Phase 2
0.6444	Remote Similarity	NPD164	Approved
0.6438	Remote Similarity	NPD3092	Approved
0.6438	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6065	Approved
0.6429	Remote Similarity	NPD6234	Discontinued
0.6429	Remote Similarity	NPD6353	Approved
0.6424	Remote Similarity	NPD37	Approved
0.6423	Remote Similarity	NPD7320	Approved
0.6423	Remote Similarity	NPD6881	Approved
0.6423	Remote Similarity	NPD6899	Approved
0.642	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5125	Phase 3
0.6414	Remote Similarity	NPD2932	Approved
0.6414	Remote Similarity	NPD5126	Approved
0.6414	Remote Similarity	NPD6370	Approved
0.6412	Remote Similarity	NPD1989	Approved
0.641	Remote Similarity	NPD2438	Suspended
0.6408	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD7115	Discovery
0.6404	Remote Similarity	NPD8150	Discontinued
0.6403	Remote Similarity	NPD8130	Phase 1
0.6403	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7473	Discontinued
0.6393	Remote Similarity	NPD8485	Approved
0.6392	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6903	Approved
0.6377	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6373	Approved
0.6377	Remote Similarity	NPD6372	Approved
0.6374	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1930	Approved
0.637	Remote Similarity	NPD7604	Phase 2
0.637	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1929	Approved
0.6364	Remote Similarity	NPD6355	Discontinued
0.6364	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6882	Approved
0.6357	Remote Similarity	NPD6053	Discontinued
0.6352	Remote Similarity	NPD4110	Phase 3
0.6352	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD8293	Discontinued
0.635	Remote Similarity	NPD5697	Approved
0.6345	Remote Similarity	NPD6015	Approved
0.6345	Remote Similarity	NPD8033	Approved
0.6345	Remote Similarity	NPD5983	Phase 2
0.6345	Remote Similarity	NPD6016	Approved
0.6341	Remote Similarity	NPD3226	Approved
0.6341	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7713	Phase 3
0.6338	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7290	Approved
0.6331	Remote Similarity	NPD6883	Approved
0.6331	Remote Similarity	NPD7102	Approved
0.6309	Remote Similarity	NPD1876	Approved
0.6306	Remote Similarity	NPD7137	Phase 2
0.6304	Remote Similarity	NPD6011	Approved
0.6303	Remote Similarity	NPD6599	Discontinued
0.6301	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5988	Approved
0.6301	Remote Similarity	NPD17	Approved
0.6301	Remote Similarity	NPD3095	Discontinued
0.6299	Remote Similarity	NPD2979	Phase 3
0.6296	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5494	Approved
0.6291	Remote Similarity	NPD7260	Phase 2
0.629	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6847	Approved
0.6286	Remote Similarity	NPD6869	Approved
0.6286	Remote Similarity	NPD6617	Approved
0.6284	Remote Similarity	NPD6336	Discontinued
0.6284	Remote Similarity	NPD3972	Approved
0.6279	Remote Similarity	NPD3673	Approved
0.6279	Remote Similarity	NPD3672	Approved
0.6277	Remote Similarity	NPD6402	Approved
0.6277	Remote Similarity	NPD7128	Approved
0.6277	Remote Similarity	NPD5739	Approved
0.6277	Remote Similarity	NPD6675	Approved
0.6276	Remote Similarity	NPD6059	Approved
0.6276	Remote Similarity	NPD8294	Approved
0.6276	Remote Similarity	NPD3091	Approved
0.6276	Remote Similarity	NPD8377	Approved
0.6272	Remote Similarity	NPD7075	Discontinued
0.6271	Remote Similarity	NPD7962	Phase 2
0.6269	Remote Similarity	NPD1238	Approved
0.6264	Remote Similarity	NPD7879	Clinical (unspecified phase)

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