NPASS Compound

Structure

CID58061 OpenBabel06191715392D 45 48 0 0 1 0 0 0 0 0999 V2000 0.8484 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7936 0.0868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9103 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0480 3.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8811 -0.2098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8115 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5518 -0.8094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6352 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7868 -2.9388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6352 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9385 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7868 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0901 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2418 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7659 -1.5904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4290 -2.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1167 -0.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9835 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9385 -1.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6967 -0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2916 -1.5851 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8484 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3934 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1459 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7209 0.3928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7659 0.6108 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7437 -1.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7209 -1.3724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8661 -1.8834 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 2.9388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2021 1.9433 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3934 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3317 1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1963 -2.1170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1742 -2.0102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8484 1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5479 1.5658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5451 -1.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 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 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 29 1 0 0 0 0 16 26 1 0 0 0 0 16 28 1 0 0 0 0 17 25 1 0 0 0 0 17 35 1 0 0 0 0 18 27 1 0 0 0 0 18 35 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 20 30 2 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 34 1 1 0 0 0 26 45 1 6 0 0 0 27 42 1 6 0 0 0 28 34 1 1 0 0 0 28 43 1 0 0 0 0 29 39 2 0 0 0 0 29 45 1 0 0 0 0 30 31 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 0 0 0 0 31 40 1 1 0 0 0 32 34 1 6 0 0 0 32 44 1 0 0 0 0 33 41 1 0 0 0 0 34 8 1 1 0 0 0 35 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.29
Volume:	641.228
LogP:	3.154
LogD:	2.664
LogS:	-4.504
# Rotatable Bonds:	11
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.196
Synthetic Accessibility Score:	5.054
Fsp3:	0.543
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:	-5.338
MDCK Permeability:	0.00011443941184552386
Pgp-inhibitor:	0.953
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.284
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.752
Plasma Protein Binding (PPB):	73.3660659790039%
Volume Distribution (VD):	1.985
Pgp-substrate:	18.830341339111328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.297
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.29
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	3.825
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.867
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.59
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.246
Carcinogencity:	0.204
Eye Corrosion:	0.011
Eye Irritation:	0.026
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC58061

Natural Product ID:	NPC58061
*Common Name:**	[(2S,4R,5R,5As,6S,8S,9Ar,10As)-2,5,6-Triacetyloxy-4-Hydroxy-10A-(2-Hydroxypropan-2-Yl)-3,5A-Dimethyl-9-Methylidene-2,4,5,6,7,8,9A,10-Octahydro-1H-Benzo[F]Azulen-8-Yl] (E)-3-Phenylprop-2-Enoate
IUPAC Name:	[(2S,4R,5R,5aS,6S,8S,9aR,10aS)-2,5,6-triacetyloxy-4-hydroxy-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-9-methylidene-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[f]azulen-8-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	KKUSQQKRXOHDJQ-ZWCBWACKSA-N
Standard InCHI:	InChI=1S/C35H44O10/c1-19-25-17-35(33(6,7)41)18-27(42-21(3)36)20(2)30(35)31(40)32(44-23(5)38)34(25,8)28(43-22(4)37)16-26(19)45-29(39)15-14-24-12-10-9-11-13-24/h9-15,25-28,31-32,40-41H,1,16-18H2,2-8H3/b15-14+/t25-,26+,27+,28+,31-,32+,34+,35+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H](OC(=O)/C=C/c2ccccc2)C(=C)[C@@H]2[C@]1(C)[C@@H](OC(=O)C)[C@H](O)C1=C([C@H](C[C@]1(C2)C(O)(C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL128730
PubChem CID:	5321754
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	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	=	1.2	ug.mL-1	PMID[529946]
NPT2	Others	Unspecified		Control	=	176.0	%	PMID[529946]
NPT2	Others	Unspecified		Control	=	584.0	%	PMID[529946]
NPT27	Others	Unspecified		IC50	=	5.8	ug.mL-1	PMID[529946]

☑ 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 NPC58061 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	233
0.1-0.2	968
0.2-0.3	2132
0.3-0.4	5134
0.4-0.5	9202
0.5-0.6	17221
0.6-0.7	6961
0.7-0.8	768
0.8-0.85	50
0.85-0.9	25
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC284022
0.9023	High Similarity	NPC192658
0.9015	High Similarity	NPC87934
0.9015	High Similarity	NPC162613
0.8939	High Similarity	NPC9905
0.8889	High Similarity	NPC34943
0.8889	High Similarity	NPC45821
0.8828	High Similarity	NPC93632
0.8819	High Similarity	NPC476971
0.8819	High Similarity	NPC476972
0.881	High Similarity	NPC471758
0.8759	High Similarity	NPC20255
0.8759	High Similarity	NPC240115
0.874	High Similarity	NPC470158
0.874	High Similarity	NPC475933
0.874	High Similarity	NPC476970
0.873	High Similarity	NPC472373
0.872	High Similarity	NPC475328
0.8686	High Similarity	NPC311825
0.8686	High Similarity	NPC125882
0.8686	High Similarity	NPC92867
0.8676	High Similarity	NPC95449
0.8667	High Similarity	NPC266374
0.8651	High Similarity	NPC12016
0.8626	High Similarity	NPC476976
0.855	High Similarity	NPC476977
0.8504	High Similarity	NPC473871
0.8504	High Similarity	NPC473870
0.8492	Intermediate Similarity	NPC473439
0.8492	Intermediate Similarity	NPC300827
0.8462	Intermediate Similarity	NPC230331
0.8429	Intermediate Similarity	NPC473760
0.8425	Intermediate Similarity	NPC70973
0.8425	Intermediate Similarity	NPC473889
0.8387	Intermediate Similarity	NPC470820
0.8372	Intermediate Similarity	NPC473083
0.8357	Intermediate Similarity	NPC473602
0.8357	Intermediate Similarity	NPC209592
0.8357	Intermediate Similarity	NPC312393
0.8357	Intermediate Similarity	NPC48599
0.8346	Intermediate Similarity	NPC311175
0.8346	Intermediate Similarity	NPC80599
0.8346	Intermediate Similarity	NPC37641
0.8345	Intermediate Similarity	NPC471139
0.8333	Intermediate Similarity	NPC140021
0.832	Intermediate Similarity	NPC84129
0.8308	Intermediate Similarity	NPC473111
0.8308	Intermediate Similarity	NPC473110
0.8254	Intermediate Similarity	NPC89324
0.8231	Intermediate Similarity	NPC114927
0.8195	Intermediate Similarity	NPC472388
0.8195	Intermediate Similarity	NPC473443
0.8188	Intermediate Similarity	NPC472547
0.8182	Intermediate Similarity	NPC31829
0.8168	Intermediate Similarity	NPC473082
0.816	Intermediate Similarity	NPC476476
0.8156	Intermediate Similarity	NPC472556
0.8154	Intermediate Similarity	NPC470815
0.814	Intermediate Similarity	NPC473749
0.8129	Intermediate Similarity	NPC41481
0.8129	Intermediate Similarity	NPC118080
0.8129	Intermediate Similarity	NPC291599
0.8129	Intermediate Similarity	NPC16912
0.8129	Intermediate Similarity	NPC472576
0.8129	Intermediate Similarity	NPC87448
0.8129	Intermediate Similarity	NPC27377
0.8129	Intermediate Similarity	NPC97947
0.812	Intermediate Similarity	NPC225103
0.8116	Intermediate Similarity	NPC473301
0.8112	Intermediate Similarity	NPC474564
0.811	Intermediate Similarity	NPC473860
0.8088	Intermediate Similarity	NPC28836
0.808	Intermediate Similarity	NPC473869
0.8074	Intermediate Similarity	NPC209851
0.8071	Intermediate Similarity	NPC34012
0.8058	Intermediate Similarity	NPC275592
0.8058	Intermediate Similarity	NPC473440
0.8058	Intermediate Similarity	NPC90614
0.8058	Intermediate Similarity	NPC100913
0.8058	Intermediate Similarity	NPC171207
0.8058	Intermediate Similarity	NPC97667
0.8056	Intermediate Similarity	NPC475218
0.8056	Intermediate Similarity	NPC70236
0.8056	Intermediate Similarity	NPC476092
0.8056	Intermediate Similarity	NPC475447
0.8045	Intermediate Similarity	NPC195224
0.8043	Intermediate Similarity	NPC39549
0.8042	Intermediate Similarity	NPC327031
0.8028	Intermediate Similarity	NPC301946
0.8028	Intermediate Similarity	NPC472568
0.8028	Intermediate Similarity	NPC96903
0.8028	Intermediate Similarity	NPC158663
0.8028	Intermediate Similarity	NPC171525
0.8028	Intermediate Similarity	NPC470157
0.8028	Intermediate Similarity	NPC277053
0.8028	Intermediate Similarity	NPC200471
0.8028	Intermediate Similarity	NPC70403
0.8028	Intermediate Similarity	NPC473088
0.8028	Intermediate Similarity	NPC471104
0.8028	Intermediate Similarity	NPC469349
0.8028	Intermediate Similarity	NPC184817
0.8028	Intermediate Similarity	NPC472571
0.8028	Intermediate Similarity	NPC476973
0.8028	Intermediate Similarity	NPC177940
0.8028	Intermediate Similarity	NPC174982
0.8028	Intermediate Similarity	NPC29704
0.8028	Intermediate Similarity	NPC470159
0.8028	Intermediate Similarity	NPC472572
0.8028	Intermediate Similarity	NPC472575
0.8015	Intermediate Similarity	NPC472248
0.8	Intermediate Similarity	NPC478123
0.8	Intermediate Similarity	NPC62792
0.8	Intermediate Similarity	NPC325078
0.7972	Intermediate Similarity	NPC478263
0.7971	Intermediate Similarity	NPC472551
0.7971	Intermediate Similarity	NPC472372
0.7971	Intermediate Similarity	NPC472545
0.7971	Intermediate Similarity	NPC472374
0.7959	Intermediate Similarity	NPC469730
0.7959	Intermediate Similarity	NPC473632
0.7959	Intermediate Similarity	NPC132599
0.7959	Intermediate Similarity	NPC473611
0.7958	Intermediate Similarity	NPC475122
0.7958	Intermediate Similarity	NPC472570
0.7958	Intermediate Similarity	NPC80895
0.7958	Intermediate Similarity	NPC188865
0.7958	Intermediate Similarity	NPC57628
0.7958	Intermediate Similarity	NPC95810
0.7958	Intermediate Similarity	NPC472573
0.7958	Intermediate Similarity	NPC475759
0.7958	Intermediate Similarity	NPC70716
0.7958	Intermediate Similarity	NPC95265
0.7958	Intermediate Similarity	NPC163719
0.7958	Intermediate Similarity	NPC125106
0.7958	Intermediate Similarity	NPC11685
0.7958	Intermediate Similarity	NPC470152
0.7958	Intermediate Similarity	NPC25768
0.7958	Intermediate Similarity	NPC241951
0.7958	Intermediate Similarity	NPC38696
0.7958	Intermediate Similarity	NPC471912
0.7958	Intermediate Similarity	NPC472569
0.7958	Intermediate Similarity	NPC476974
0.7956	Intermediate Similarity	NPC311492
0.7945	Intermediate Similarity	NPC138641
0.7945	Intermediate Similarity	NPC22571
0.7945	Intermediate Similarity	NPC233581
0.7945	Intermediate Similarity	NPC145649
0.7945	Intermediate Similarity	NPC469648
0.7945	Intermediate Similarity	NPC469647
0.7945	Intermediate Similarity	NPC283875
0.7943	Intermediate Similarity	NPC475513
0.7943	Intermediate Similarity	NPC473755
0.7943	Intermediate Similarity	NPC63737
0.7943	Intermediate Similarity	NPC472546
0.7941	Intermediate Similarity	NPC233860
0.7941	Intermediate Similarity	NPC239358
0.7941	Intermediate Similarity	NPC233692
0.7939	Intermediate Similarity	NPC108286
0.7931	Intermediate Similarity	NPC476173
0.7917	Intermediate Similarity	NPC132652
0.7914	Intermediate Similarity	NPC27721
0.7905	Intermediate Similarity	NPC11410
0.7902	Intermediate Similarity	NPC471162
0.7902	Intermediate Similarity	NPC134131
0.7902	Intermediate Similarity	NPC478264
0.7902	Intermediate Similarity	NPC25043
0.7899	Intermediate Similarity	NPC200154
0.7891	Intermediate Similarity	NPC471135
0.7887	Intermediate Similarity	NPC131966
0.7887	Intermediate Similarity	NPC163087
0.7887	Intermediate Similarity	NPC191387
0.7887	Intermediate Similarity	NPC91703
0.7887	Intermediate Similarity	NPC477894
0.7877	Intermediate Similarity	NPC298072
0.7877	Intermediate Similarity	NPC470153
0.7872	Intermediate Similarity	NPC242355
0.7872	Intermediate Similarity	NPC224491
0.7868	Intermediate Similarity	NPC472418
0.7862	Intermediate Similarity	NPC92293
0.7862	Intermediate Similarity	NPC476975
0.7862	Intermediate Similarity	NPC266265
0.7862	Intermediate Similarity	NPC270590
0.7862	Intermediate Similarity	NPC301556
0.7862	Intermediate Similarity	NPC471101
0.7847	Intermediate Similarity	NPC474935
0.7842	Intermediate Similarity	NPC202729
0.7838	Intermediate Similarity	NPC251139
0.7838	Intermediate Similarity	NPC471176
0.7808	Intermediate Similarity	NPC473214
0.7808	Intermediate Similarity	NPC470245
0.78	Intermediate Similarity	NPC319404
0.7794	Intermediate Similarity	NPC475138
0.7793	Intermediate Similarity	NPC281717
0.7793	Intermediate Similarity	NPC320734
0.7785	Intermediate Similarity	NPC475548
0.7785	Intermediate Similarity	NPC475638
0.7785	Intermediate Similarity	NPC290683
0.777	Intermediate Similarity	NPC66761
0.777	Intermediate Similarity	NPC477896
0.777	Intermediate Similarity	NPC17877

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 NPC58061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	687
0.2-0.3	1532
0.3-0.4	3096
0.4-0.5	2143
0.5-0.6	1313
0.6-0.7	169
0.7-0.8	7
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
0.7708	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7741	Discontinued
0.75	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6647	Phase 2
0.7302	Intermediate Similarity	NPD6685	Approved
0.7197	Intermediate Similarity	NPD4198	Discontinued
0.7181	Intermediate Similarity	NPD7236	Approved
0.7121	Intermediate Similarity	NPD2629	Approved
0.7075	Intermediate Similarity	NPD7266	Discontinued
0.7071	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5765	Approved
0.7059	Intermediate Similarity	NPD5125	Phase 3
0.7059	Intermediate Similarity	NPD5126	Approved
0.7059	Intermediate Similarity	NPD7239	Suspended
0.7023	Intermediate Similarity	NPD6912	Phase 3
0.6994	Remote Similarity	NPD7799	Discontinued
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD5762	Approved
0.6905	Remote Similarity	NPD5344	Discontinued
0.6848	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6648	Approved
0.6822	Remote Similarity	NPD5048	Discontinued
0.6821	Remote Similarity	NPD4628	Phase 3
0.6806	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8127	Discontinued
0.6783	Remote Similarity	NPD5736	Approved
0.6776	Remote Similarity	NPD6190	Approved
0.6761	Remote Similarity	NPD3094	Phase 2
0.6739	Remote Similarity	NPD7503	Approved
0.6726	Remote Similarity	NPD8368	Discontinued
0.6725	Remote Similarity	NPD8434	Phase 2
0.6716	Remote Similarity	NPD7094	Approved
0.6716	Remote Similarity	NPD6858	Approved
0.6712	Remote Similarity	NPD7961	Discontinued
0.6711	Remote Similarity	NPD8166	Discontinued
0.671	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8407	Phase 2
0.6689	Remote Similarity	NPD6653	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7057	Phase 3
0.6646	Remote Similarity	NPD7058	Phase 2
0.6642	Remote Similarity	NPD7328	Approved
0.6642	Remote Similarity	NPD7327	Approved
0.6642	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD8033	Approved
0.6619	Remote Similarity	NPD8296	Approved
0.6619	Remote Similarity	NPD8379	Approved
0.6619	Remote Similarity	NPD8378	Approved
0.6619	Remote Similarity	NPD8380	Approved
0.6619	Remote Similarity	NPD8335	Approved
0.6617	Remote Similarity	NPD2067	Discontinued
0.6615	Remote Similarity	NPD5909	Discontinued
0.6614	Remote Similarity	NPD4225	Approved
0.6599	Remote Similarity	NPD6663	Approved
0.6596	Remote Similarity	NPD3092	Approved
0.6594	Remote Similarity	NPD7516	Approved
0.6585	Remote Similarity	NPD7838	Discovery
0.6554	Remote Similarity	NPD4060	Phase 1
0.6552	Remote Similarity	NPD8361	Approved
0.6552	Remote Similarity	NPD8360	Approved
0.6547	Remote Similarity	NPD8294	Approved
0.6547	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD969	Suspended
0.6513	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6004	Phase 3
0.6513	Remote Similarity	NPD6002	Phase 3
0.6513	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6005	Phase 3
0.651	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6355	Discontinued
0.651	Remote Similarity	NPD5124	Phase 1
0.651	Remote Similarity	NPD5735	Approved
0.6496	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3027	Phase 3
0.6463	Remote Similarity	NPD7095	Approved
0.646	Remote Similarity	NPD37	Approved
0.6457	Remote Similarity	NPD8435	Approved
0.6449	Remote Similarity	NPD7157	Approved
0.6444	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4967	Phase 2
0.6442	Remote Similarity	NPD4966	Approved
0.6442	Remote Similarity	NPD4965	Approved
0.6437	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7798	Approved
0.6434	Remote Similarity	NPD7640	Approved
0.6434	Remote Similarity	NPD7639	Approved
0.6434	Remote Similarity	NPD6637	Approved
0.6433	Remote Similarity	NPD7685	Pre-registration
0.6433	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3091	Approved
0.6423	Remote Similarity	NPD6010	Discontinued
0.6419	Remote Similarity	NPD3764	Approved
0.6418	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3496	Discontinued
0.6392	Remote Similarity	NPD6273	Approved
0.6391	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7305	Phase 1
0.6378	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6049	Phase 2
0.637	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6085	Phase 2
0.637	Remote Similarity	NPD6371	Approved
0.6364	Remote Similarity	NPD6234	Discontinued
0.6364	Remote Similarity	NPD4807	Approved
0.6364	Remote Similarity	NPD4806	Approved
0.6357	Remote Similarity	NPD7638	Approved
0.6357	Remote Similarity	NPD5926	Approved
0.6357	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7008	Discontinued
0.6345	Remote Similarity	NPD8651	Approved
0.6343	Remote Similarity	NPD6406	Approved
0.6343	Remote Similarity	NPD6686	Approved
0.6341	Remote Similarity	NPD7524	Approved
0.6341	Remote Similarity	NPD1282	Approved
0.634	Remote Similarity	NPD7137	Phase 2
0.6338	Remote Similarity	NPD5306	Approved
0.6338	Remote Similarity	NPD5305	Approved
0.6338	Remote Similarity	NPD3095	Discontinued
0.6333	Remote Similarity	NPD8485	Approved
0.6333	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD2238	Phase 2
0.6333	Remote Similarity	NPD3620	Phase 2
0.6331	Remote Similarity	NPD7115	Discovery
0.6329	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2861	Phase 2
0.6323	Remote Similarity	NPD1652	Phase 2
0.6319	Remote Similarity	NPD7819	Suspended
0.6316	Remote Similarity	NPD7097	Phase 1
0.6312	Remote Similarity	NPD1653	Approved
0.6311	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD2066	Phase 3
0.6304	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7075	Discontinued
0.6299	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2182	Approved
0.6294	Remote Similarity	NPD7228	Approved
0.6287	Remote Similarity	NPD7199	Phase 2
0.6281	Remote Similarity	NPD3971	Phase 1
0.6276	Remote Similarity	NPD7876	Discontinued
0.6275	Remote Similarity	NPD7033	Discontinued
0.627	Remote Similarity	NPD7637	Suspended
0.6259	Remote Similarity	NPD5951	Approved
0.6258	Remote Similarity	NPD2424	Discontinued
0.625	Remote Similarity	NPD8150	Discontinued
0.6242	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD7610	Discontinued
0.624	Remote Similarity	NPD689	Discontinued
0.6235	Remote Similarity	NPD4380	Phase 2
0.6235	Remote Similarity	NPD6599	Discontinued
0.6232	Remote Similarity	NPD7843	Approved
0.623	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1613	Approved
0.6225	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4626	Approved
0.622	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5760	Phase 2
0.622	Remote Similarity	NPD5761	Phase 2
0.622	Remote Similarity	NPD8455	Phase 2
0.6207	Remote Similarity	NPD7507	Approved
0.6201	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6362	Approved
0.619	Remote Similarity	NPD7319	Approved
0.6184	Remote Similarity	NPD230	Phase 1
0.6182	Remote Similarity	NPD5402	Approved
0.6181	Remote Similarity	NPD4106	Approved
0.6181	Remote Similarity	NPD4135	Approved
0.6181	Remote Similarity	NPD4136	Approved
0.6178	Remote Similarity	NPD4110	Phase 3
0.6178	Remote Similarity	NPD2575	Approved
0.6178	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4908	Phase 1
0.6171	Remote Similarity	NPD8312	Approved
0.6171	Remote Similarity	NPD8313	Approved
0.6165	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD1929	Approved
0.6165	Remote Similarity	NPD1930	Approved
0.6165	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5327	Phase 3
0.6163	Remote Similarity	NPD5844	Phase 1
0.6159	Remote Similarity	NPD7715	Approved
0.6159	Remote Similarity	NPD6801	Discontinued
0.6159	Remote Similarity	NPD8297	Approved
0.6159	Remote Similarity	NPD7714	Approved
0.6154	Remote Similarity	NPD5691	Approved
0.6149	Remote Similarity	NPD5403	Approved
0.6149	Remote Similarity	NPD6764	Approved
0.6149	Remote Similarity	NPD5647	Approved
0.6149	Remote Similarity	NPD6765	Approved
0.6148	Remote Similarity	NPD6695	Phase 3

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