NPASS Compound

Structure

NPC256112 OpenBabel07101719122D 26 27 0 0 1 0 0 0 0 0999 V2000 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 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 -1.7321 0.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 15 17 1 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 22 1 6 0 0 0 18 21 1 0 0 0 0 18 22 1 6 0 0 0 19 21 1 0 0 0 0 19 26 1 6 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 22 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.25
Volume:	396.57
LogP:	5.288
LogD:	3.728
LogS:	-4.072
# Rotatable Bonds:	6
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	4.173
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.975
MDCK Permeability:	4.27930208388716e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	90.02896118164062%
Volume Distribution (VD):	0.531
Pgp-substrate:	5.902871608734131%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	2.601
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.75
Skin Sensitization:	0.854
Carcinogencity:	0.045
Eye Corrosion:	0.951
Eye Irritation:	0.98
Respiratory Toxicity:	0.792

Download Data

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

Natural Product: NPC256112

Natural Product ID:	NPC256112
*Common Name:**	JAOSZJFNMXPMLX-BULWIKRESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JAOSZJFNMXPMLX-BULWIKRESA-N
Standard InCHI:	InChI=1S/C22H34O4/c1-14(13-20(24)25)7-9-17-15(2)8-10-18-21(4,5)19(26-16(3)23)11-12-22(17,18)6/h8,13,17-19H,7,9-12H2,1-6H3,(H,24,25)/b14-13+/t17-,18-,19-,22+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC=C([C@@H]2CC/C(=C/C(=O)O)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3315352
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO13331	Solidago canadensis	Species	Asteraceae	Eukaryota	n.a.	Canada	n.a.	PMID[24999828]
NPO13331	Solidago canadensis	Species	Asteraceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3971	Individual Protein	Taste receptor type 2 member 31	Homo sapiens	IC50	>	25000.0	nM	PMID[551080]

☑ 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 NPC256112 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	163
0.1-0.2	1160
0.2-0.3	4583
0.3-0.4	12218
0.4-0.5	11320
0.5-0.6	6805
0.6-0.7	4763
0.7-0.8	1546
0.8-0.85	104
0.85-0.9	32
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.961	High Similarity	NPC170303
0.9367	High Similarity	NPC476927
0.925	High Similarity	NPC306951
0.9	High Similarity	NPC2524
0.8987	High Similarity	NPC281880
0.8902	High Similarity	NPC109528
0.8902	High Similarity	NPC35933
0.8875	High Similarity	NPC159148
0.8861	High Similarity	NPC242767
0.8837	High Similarity	NPC38232
0.8824	High Similarity	NPC78973
0.8795	High Similarity	NPC475069
0.8795	High Similarity	NPC175145
0.8765	High Similarity	NPC471218
0.8721	High Similarity	NPC329842
0.8706	High Similarity	NPC246028
0.8706	High Similarity	NPC170633
0.8706	High Similarity	NPC314727
0.869	High Similarity	NPC166857
0.8675	High Similarity	NPC474013
0.8659	High Similarity	NPC79945
0.8642	High Similarity	NPC25554
0.8608	High Similarity	NPC132542
0.8571	High Similarity	NPC131813
0.8554	High Similarity	NPC102048
0.8554	High Similarity	NPC302360
0.8488	Intermediate Similarity	NPC262858
0.8488	Intermediate Similarity	NPC472240
0.8488	Intermediate Similarity	NPC16265
0.8471	Intermediate Similarity	NPC131329
0.8471	Intermediate Similarity	NPC245004
0.8444	Intermediate Similarity	NPC141401
0.8434	Intermediate Similarity	NPC57370
0.8415	Intermediate Similarity	NPC142163
0.8409	Intermediate Similarity	NPC53555
0.8409	Intermediate Similarity	NPC214697
0.8409	Intermediate Similarity	NPC7349
0.8375	Intermediate Similarity	NPC283619
0.8372	Intermediate Similarity	NPC7280
0.8372	Intermediate Similarity	NPC104560
0.8372	Intermediate Similarity	NPC229612
0.8372	Intermediate Similarity	NPC291665
0.8372	Intermediate Similarity	NPC93411
0.8353	Intermediate Similarity	NPC473226
0.8353	Intermediate Similarity	NPC474970
0.8352	Intermediate Similarity	NPC478056
0.8333	Intermediate Similarity	NPC190713
0.8333	Intermediate Similarity	NPC96055
0.8315	Intermediate Similarity	NPC279410
0.8315	Intermediate Similarity	NPC474922
0.8315	Intermediate Similarity	NPC105490
0.8315	Intermediate Similarity	NPC119562
0.8313	Intermediate Similarity	NPC286786
0.8295	Intermediate Similarity	NPC212948
0.8295	Intermediate Similarity	NPC472811
0.8295	Intermediate Similarity	NPC177641
0.8293	Intermediate Similarity	NPC269791
0.8293	Intermediate Similarity	NPC469802
0.8276	Intermediate Similarity	NPC20946
0.8276	Intermediate Similarity	NPC470734
0.8276	Intermediate Similarity	NPC146554
0.8276	Intermediate Similarity	NPC82876
0.8235	Intermediate Similarity	NPC191965
0.8222	Intermediate Similarity	NPC472441
0.8222	Intermediate Similarity	NPC276110
0.8214	Intermediate Similarity	NPC474789
0.8214	Intermediate Similarity	NPC132386
0.8214	Intermediate Similarity	NPC477124
0.8214	Intermediate Similarity	NPC311070
0.8214	Intermediate Similarity	NPC52108
0.8202	Intermediate Similarity	NPC476304
0.8202	Intermediate Similarity	NPC472812
0.8193	Intermediate Similarity	NPC195334
0.8193	Intermediate Similarity	NPC290495
0.8182	Intermediate Similarity	NPC220216
0.8182	Intermediate Similarity	NPC280149
0.8182	Intermediate Similarity	NPC48732
0.8182	Intermediate Similarity	NPC221111
0.8171	Intermediate Similarity	NPC100906
0.8161	Intermediate Similarity	NPC106332
0.8152	Intermediate Similarity	NPC325229
0.8152	Intermediate Similarity	NPC92275
0.8152	Intermediate Similarity	NPC275086
0.814	Intermediate Similarity	NPC325594
0.814	Intermediate Similarity	NPC84121
0.814	Intermediate Similarity	NPC322159
0.814	Intermediate Similarity	NPC137306
0.814	Intermediate Similarity	NPC73038
0.814	Intermediate Similarity	NPC471219
0.8132	Intermediate Similarity	NPC276103
0.8132	Intermediate Similarity	NPC54248
0.8111	Intermediate Similarity	NPC298973
0.8111	Intermediate Similarity	NPC472416
0.8111	Intermediate Similarity	NPC104925
0.8111	Intermediate Similarity	NPC57117
0.8111	Intermediate Similarity	NPC74751
0.8111	Intermediate Similarity	NPC472360
0.8111	Intermediate Similarity	NPC476186
0.8095	Intermediate Similarity	NPC224455
0.809	Intermediate Similarity	NPC124374
0.809	Intermediate Similarity	NPC477574
0.809	Intermediate Similarity	NPC110923
0.809	Intermediate Similarity	NPC473675
0.809	Intermediate Similarity	NPC74296
0.809	Intermediate Similarity	NPC72845
0.8077	Intermediate Similarity	NPC34834
0.8068	Intermediate Similarity	NPC472983
0.8068	Intermediate Similarity	NPC50488
0.8068	Intermediate Similarity	NPC261320
0.8068	Intermediate Similarity	NPC36668
0.8068	Intermediate Similarity	NPC118011
0.8068	Intermediate Similarity	NPC474396
0.8065	Intermediate Similarity	NPC251680
0.8065	Intermediate Similarity	NPC474190
0.8065	Intermediate Similarity	NPC266955
0.8065	Intermediate Similarity	NPC324841
0.8065	Intermediate Similarity	NPC38855
0.8065	Intermediate Similarity	NPC476274
0.8043	Intermediate Similarity	NPC99726
0.8043	Intermediate Similarity	NPC253826
0.8043	Intermediate Similarity	NPC51499
0.8026	Intermediate Similarity	NPC242945
0.8026	Intermediate Similarity	NPC259156
0.8025	Intermediate Similarity	NPC265588
0.8023	Intermediate Similarity	NPC473251
0.8023	Intermediate Similarity	NPC52628
0.8023	Intermediate Similarity	NPC472442
0.8023	Intermediate Similarity	NPC42586
0.8023	Intermediate Similarity	NPC164424
0.8022	Intermediate Similarity	NPC474909
0.8022	Intermediate Similarity	NPC134067
0.8022	Intermediate Similarity	NPC183012
0.8	Intermediate Similarity	NPC71152
0.8	Intermediate Similarity	NPC214756
0.8	Intermediate Similarity	NPC139692
0.8	Intermediate Similarity	NPC95899
0.8	Intermediate Similarity	NPC12283
0.8	Intermediate Similarity	NPC478057
0.8	Intermediate Similarity	NPC23748
0.8	Intermediate Similarity	NPC99653
0.8	Intermediate Similarity	NPC152778
0.8	Intermediate Similarity	NPC205034
0.8	Intermediate Similarity	NPC472440
0.8	Intermediate Similarity	NPC295643
0.8	Intermediate Similarity	NPC476366
0.8	Intermediate Similarity	NPC162615
0.8	Intermediate Similarity	NPC474193
0.8	Intermediate Similarity	NPC201048
0.8	Intermediate Similarity	NPC272075
0.8	Intermediate Similarity	NPC42476
0.8	Intermediate Similarity	NPC49208
0.8	Intermediate Similarity	NPC85742
0.7979	Intermediate Similarity	NPC473160
0.7979	Intermediate Similarity	NPC115862
0.7979	Intermediate Similarity	NPC118174
0.7979	Intermediate Similarity	NPC224720
0.7979	Intermediate Similarity	NPC115899
0.7979	Intermediate Similarity	NPC472554
0.7979	Intermediate Similarity	NPC476240
0.7979	Intermediate Similarity	NPC476223
0.7978	Intermediate Similarity	NPC310479
0.7978	Intermediate Similarity	NPC474728
0.7978	Intermediate Similarity	NPC111585
0.7978	Intermediate Similarity	NPC113989
0.7978	Intermediate Similarity	NPC232202
0.7978	Intermediate Similarity	NPC477147
0.7978	Intermediate Similarity	NPC120840
0.7978	Intermediate Similarity	NPC477149
0.7978	Intermediate Similarity	NPC148414
0.7978	Intermediate Similarity	NPC471896
0.7978	Intermediate Similarity	NPC182136
0.7978	Intermediate Similarity	NPC175628
0.7976	Intermediate Similarity	NPC327002
0.7976	Intermediate Similarity	NPC473420
0.7976	Intermediate Similarity	NPC475944
0.7976	Intermediate Similarity	NPC108476
0.7957	Intermediate Similarity	NPC278673
0.7957	Intermediate Similarity	NPC247233
0.7957	Intermediate Similarity	NPC218107
0.7955	Intermediate Similarity	NPC473879
0.7955	Intermediate Similarity	NPC48107
0.7955	Intermediate Similarity	NPC472809
0.7955	Intermediate Similarity	NPC473229
0.7955	Intermediate Similarity	NPC472810
0.7955	Intermediate Similarity	NPC24816
0.7952	Intermediate Similarity	NPC327674
0.7952	Intermediate Similarity	NPC44083
0.7952	Intermediate Similarity	NPC153987
0.7935	Intermediate Similarity	NPC250757
0.7935	Intermediate Similarity	NPC134072
0.7935	Intermediate Similarity	NPC284194
0.7935	Intermediate Similarity	NPC301534
0.7935	Intermediate Similarity	NPC471765
0.7935	Intermediate Similarity	NPC234993
0.7935	Intermediate Similarity	NPC7124
0.7935	Intermediate Similarity	NPC88009
0.7935	Intermediate Similarity	NPC202833
0.7935	Intermediate Similarity	NPC195366
0.7935	Intermediate Similarity	NPC16967
0.7935	Intermediate Similarity	NPC165632

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 NPC256112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1477
0.2-0.3	3902
0.3-0.4	2412
0.4-0.5	791
0.5-0.6	229
0.6-0.7	181
0.7-0.8	16
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
0.8111	Intermediate Similarity	NPD7748	Approved
0.8065	Intermediate Similarity	NPD7640	Approved
0.8065	Intermediate Similarity	NPD7639	Approved
0.7957	Intermediate Similarity	NPD7638	Approved
0.7889	Intermediate Similarity	NPD7515	Phase 2
0.7849	Intermediate Similarity	NPD7902	Approved
0.7766	Intermediate Similarity	NPD4225	Approved
0.7717	Intermediate Similarity	NPD7900	Approved
0.7717	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7645	Phase 2
0.7528	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD7334	Approved
0.7528	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD6409	Approved
0.7528	Intermediate Similarity	NPD7146	Approved
0.7528	Intermediate Similarity	NPD7521	Approved
0.7473	Intermediate Similarity	NPD6051	Approved
0.7471	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6399	Phase 3
0.7416	Intermediate Similarity	NPD1694	Approved
0.7363	Intermediate Similarity	NPD6903	Approved
0.7363	Intermediate Similarity	NPD6672	Approved
0.7363	Intermediate Similarity	NPD5737	Approved
0.7363	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7632	Discontinued
0.7333	Intermediate Similarity	NPD3618	Phase 1
0.7303	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5739	Approved
0.73	Intermediate Similarity	NPD7128	Approved
0.73	Intermediate Similarity	NPD6675	Approved
0.73	Intermediate Similarity	NPD6402	Approved
0.7283	Intermediate Similarity	NPD5328	Approved
0.7262	Intermediate Similarity	NPD8264	Approved
0.7253	Intermediate Similarity	NPD3573	Approved
0.7241	Intermediate Similarity	NPD7525	Registered
0.7157	Intermediate Similarity	NPD6881	Approved
0.7157	Intermediate Similarity	NPD6899	Approved
0.7157	Intermediate Similarity	NPD7320	Approved
0.7143	Intermediate Similarity	NPD6648	Approved
0.7128	Intermediate Similarity	NPD6079	Approved
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD7115	Discovery
0.7087	Intermediate Similarity	NPD6372	Approved
0.7087	Intermediate Similarity	NPD6373	Approved
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7083	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5344	Discontinued
0.7059	Intermediate Similarity	NPD7339	Approved
0.7059	Intermediate Similarity	NPD5701	Approved
0.7059	Intermediate Similarity	NPD6942	Approved
0.7059	Intermediate Similarity	NPD5697	Approved
0.7053	Intermediate Similarity	NPD5779	Approved
0.7053	Intermediate Similarity	NPD5778	Approved
0.7019	Intermediate Similarity	NPD7290	Approved
0.7019	Intermediate Similarity	NPD7102	Approved
0.7019	Intermediate Similarity	NPD6883	Approved
0.699	Remote Similarity	NPD6011	Approved
0.6977	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6650	Approved
0.6952	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD8130	Phase 1
0.6952	Remote Similarity	NPD6649	Approved
0.6952	Remote Similarity	NPD6617	Approved
0.6952	Remote Similarity	NPD6869	Approved
0.6952	Remote Similarity	NPD6847	Approved
0.6947	Remote Similarity	NPD6411	Approved
0.6947	Remote Similarity	NPD8035	Phase 2
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD7637	Suspended
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD6013	Approved
0.6923	Remote Similarity	NPD4786	Approved
0.6923	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD3133	Approved
0.6915	Remote Similarity	NPD6673	Approved
0.6915	Remote Similarity	NPD6904	Approved
0.6915	Remote Similarity	NPD6080	Approved
0.6889	Remote Similarity	NPD3667	Approved
0.6887	Remote Similarity	NPD8297	Approved
0.6887	Remote Similarity	NPD6882	Approved
0.6875	Remote Similarity	NPD4202	Approved
0.6869	Remote Similarity	NPD5696	Approved
0.6848	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5222	Approved
0.6837	Remote Similarity	NPD4697	Phase 3
0.6837	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5221	Approved
0.6835	Remote Similarity	NPD4191	Approved
0.6835	Remote Similarity	NPD4192	Approved
0.6835	Remote Similarity	NPD4193	Approved
0.6835	Remote Similarity	NPD4194	Approved
0.6832	Remote Similarity	NPD5211	Phase 2
0.6813	Remote Similarity	NPD6695	Phase 3
0.6796	Remote Similarity	NPD6008	Approved
0.679	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD4519	Discontinued
0.6771	Remote Similarity	NPD6050	Approved
0.6771	Remote Similarity	NPD5693	Phase 1
0.6768	Remote Similarity	NPD5173	Approved
0.6768	Remote Similarity	NPD4755	Approved
0.6762	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4195	Approved
0.6739	Remote Similarity	NPD3668	Phase 3
0.6739	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6101	Approved
0.6737	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7328	Approved
0.6727	Remote Similarity	NPD7327	Approved
0.6702	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5141	Approved
0.6698	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6634	Remote Similarity	NPD4696	Approved
0.6634	Remote Similarity	NPD5285	Approved
0.6634	Remote Similarity	NPD5286	Approved
0.6634	Remote Similarity	NPD4700	Approved
0.6633	Remote Similarity	NPD6001	Approved
0.6632	Remote Similarity	NPD5208	Approved
0.6629	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD368	Approved
0.6607	Remote Similarity	NPD8377	Approved
0.6607	Remote Similarity	NPD8294	Approved
0.6598	Remote Similarity	NPD5694	Approved
0.6598	Remote Similarity	NPD5284	Approved
0.6598	Remote Similarity	NPD5281	Approved
0.6596	Remote Similarity	NPD5279	Phase 3
0.6596	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6098	Approved
0.6577	Remote Similarity	NPD6335	Approved
0.6571	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5223	Approved
0.6562	Remote Similarity	NPD4753	Phase 2
0.6556	Remote Similarity	NPD6929	Approved
0.6552	Remote Similarity	NPD6926	Approved
0.6552	Remote Similarity	NPD6924	Approved
0.6549	Remote Similarity	NPD8296	Approved
0.6549	Remote Similarity	NPD8033	Approved
0.6549	Remote Similarity	NPD8378	Approved
0.6549	Remote Similarity	NPD8380	Approved
0.6549	Remote Similarity	NPD8335	Approved
0.6549	Remote Similarity	NPD7503	Approved
0.6549	Remote Similarity	NPD8379	Approved
0.6545	Remote Similarity	NPD6274	Approved
0.6535	Remote Similarity	NPD5290	Discontinued
0.6526	Remote Similarity	NPD7524	Approved
0.6526	Remote Similarity	NPD7750	Discontinued
0.6522	Remote Similarity	NPD4221	Approved
0.6522	Remote Similarity	NPD4223	Phase 3
0.6518	Remote Similarity	NPD7101	Approved
0.6518	Remote Similarity	NPD7100	Approved
0.6514	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD4243	Approved
0.6505	Remote Similarity	NPD5226	Approved
0.6505	Remote Similarity	NPD5225	Approved
0.6505	Remote Similarity	NPD4633	Approved
0.6505	Remote Similarity	NPD5224	Approved
0.6495	Remote Similarity	NPD5207	Approved
0.6495	Remote Similarity	NPD5785	Approved
0.6489	Remote Similarity	NPD1696	Phase 3
0.6489	Remote Similarity	NPD5329	Approved
0.6486	Remote Similarity	NPD6317	Approved
0.6484	Remote Similarity	NPD6931	Approved
0.6484	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6404	Discontinued
0.6452	Remote Similarity	NPD5362	Discontinued
0.6452	Remote Similarity	NPD7154	Phase 3
0.6444	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5174	Approved
0.6442	Remote Similarity	NPD4754	Approved
0.6442	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD6313	Approved
0.6429	Remote Similarity	NPD6314	Approved
0.6415	Remote Similarity	NPD6412	Phase 2
0.6404	Remote Similarity	NPD6909	Approved
0.6404	Remote Similarity	NPD6908	Approved
0.6404	Remote Similarity	NPD6933	Approved
0.6383	Remote Similarity	NPD4197	Approved
0.6364	Remote Similarity	NPD4785	Approved
0.6364	Remote Similarity	NPD4784	Approved
0.6344	Remote Similarity	NPD5209	Approved
0.6339	Remote Similarity	NPD6009	Approved
0.6337	Remote Similarity	NPD7614	Phase 1
0.6337	Remote Similarity	NPD7732	Phase 3
0.6333	Remote Similarity	NPD6925	Approved
0.6333	Remote Similarity	NPD5776	Phase 2
0.6327	Remote Similarity	NPD6698	Approved
0.6327	Remote Similarity	NPD46	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