NPASS Compound

Structure

NPC470686 OpenBabel07101719132D 23 23 0 0 1 0 0 0 0 0999 V2000 0.5307 2.9631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4612 -0.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5115 0.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2464 2.3337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9991 -0.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 1.0751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8672 0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5779 0.4458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0900 1.3461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4215 -0.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4190 -2.5472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -2.9074 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 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 5 22 1 0 0 0 0 7 16 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 4 1 1 0 0 0 14 20 1 0 0 0 0 15 6 1 6 0 0 0 16 17 1 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 8 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.21
Volume:	353.239
LogP:	3.68
LogD:	2.976
LogS:	-3.718
# Rotatable Bonds:	9
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	4.773
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.563
MDCK Permeability:	2.2498881662613712e-05
Pgp-inhibitor:	0.291
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	78.97045135498047%
Volume Distribution (VD):	1.383
Pgp-substrate:	4.049008369445801%

ADMET: Metabolism

CYP1A2-inhibitor:	0.723
CYP1A2-substrate:	0.734
CYP2C19-inhibitor:	0.816
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.629
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	6.024
Half-life (T1/2):	0.434

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.82
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.507
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.577
Carcinogencity:	0.119
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC470686

Natural Product ID:	NPC470686
*Common Name:**	(-)-Gracilioether C
IUPAC Name:	methyl (2Z)-2-[(5R)-3,5-diethyl-5-[(E,2R,5S)-2-ethyl-5-hydroxyhex-3-enyl]furan-2-ylidene]acetate
Synonyms:	(-)-Gracilioether C
Standard InCHIKey:	YNPVSGZQMXBKIO-CEJKPMKJSA-N
Standard InCHI:	InChI=1S/C19H30O4/c1-6-15(10-9-14(4)20)12-19(8-3)13-16(7-2)17(23-19)11-18(21)22-5/h9-11,13-15,20H,6-8,12H2,1-5H3/b10-9+,17-11-/t14-,15-,19+/m0/s1
SMILES:	CC[C@H](C[C@]1(CC)C=C(/C(=C/C(=O)OC)/O1)CC)/C=C/[C@@H](O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2178583
PubChem CID:	66575622
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO33167	plakinastrella mamillaris	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934537]

☑ 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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	10000.0	nM	PMID[572490]

☑ 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 NPC470686 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	164
0.1-0.2	1151
0.2-0.3	6251
0.3-0.4	16948
0.4-0.5	11342
0.5-0.6	4920
0.6-0.7	1662
0.7-0.8	242
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC191233
0.8857	High Similarity	NPC470693
0.8824	High Similarity	NPC220766
0.8356	Intermediate Similarity	NPC316185
0.8333	Intermediate Similarity	NPC232812
0.8289	Intermediate Similarity	NPC315394
0.8219	Intermediate Similarity	NPC64234
0.8219	Intermediate Similarity	NPC37929
0.8219	Intermediate Similarity	NPC59558
0.8133	Intermediate Similarity	NPC315843
0.8082	Intermediate Similarity	NPC151481
0.7973	Intermediate Similarity	NPC329904
0.7973	Intermediate Similarity	NPC473361
0.7945	Intermediate Similarity	NPC474823
0.7907	Intermediate Similarity	NPC29798
0.7907	Intermediate Similarity	NPC282644
0.7895	Intermediate Similarity	NPC107654
0.7857	Intermediate Similarity	NPC55376
0.7857	Intermediate Similarity	NPC260343
0.7838	Intermediate Similarity	NPC475004
0.7821	Intermediate Similarity	NPC473825
0.7808	Intermediate Similarity	NPC472266
0.7805	Intermediate Similarity	NPC475706
0.7792	Intermediate Similarity	NPC329852
0.7778	Intermediate Similarity	NPC474028
0.7778	Intermediate Similarity	NPC282760
0.7778	Intermediate Similarity	NPC470688
0.7778	Intermediate Similarity	NPC474439
0.7746	Intermediate Similarity	NPC473737
0.7733	Intermediate Similarity	NPC316029
0.7733	Intermediate Similarity	NPC4299
0.7733	Intermediate Similarity	NPC315285
0.7733	Intermediate Similarity	NPC315597
0.7722	Intermediate Similarity	NPC209135
0.7722	Intermediate Similarity	NPC474816
0.7711	Intermediate Similarity	NPC474424
0.7711	Intermediate Similarity	NPC67081
0.7711	Intermediate Similarity	NPC471223
0.7703	Intermediate Similarity	NPC313444
0.7703	Intermediate Similarity	NPC276290
0.7703	Intermediate Similarity	NPC238223
0.7701	Intermediate Similarity	NPC59646
0.7683	Intermediate Similarity	NPC474809
0.7683	Intermediate Similarity	NPC475714
0.7674	Intermediate Similarity	NPC3436
0.7671	Intermediate Similarity	NPC37382
0.7671	Intermediate Similarity	NPC315115
0.7671	Intermediate Similarity	NPC146811
0.7662	Intermediate Similarity	NPC474758
0.7654	Intermediate Similarity	NPC325031
0.7654	Intermediate Similarity	NPC315731
0.7654	Intermediate Similarity	NPC112868
0.7632	Intermediate Similarity	NPC477087
0.7632	Intermediate Similarity	NPC477086
0.7625	Intermediate Similarity	NPC471537
0.7625	Intermediate Similarity	NPC55304
0.7625	Intermediate Similarity	NPC226226
0.7614	Intermediate Similarity	NPC470521
0.7606	Intermediate Similarity	NPC26810
0.76	Intermediate Similarity	NPC101622
0.7595	Intermediate Similarity	NPC471225
0.7595	Intermediate Similarity	NPC262747
0.7595	Intermediate Similarity	NPC68156
0.7586	Intermediate Similarity	NPC470520
0.7568	Intermediate Similarity	NPC132286
0.7564	Intermediate Similarity	NPC478194
0.7564	Intermediate Similarity	NPC478191
0.7564	Intermediate Similarity	NPC478195
0.7564	Intermediate Similarity	NPC478192
0.7564	Intermediate Similarity	NPC478196
0.7564	Intermediate Similarity	NPC478193
0.7561	Intermediate Similarity	NPC324170
0.7558	Intermediate Similarity	NPC225283
0.7534	Intermediate Similarity	NPC182794
0.7534	Intermediate Similarity	NPC471566
0.7534	Intermediate Similarity	NPC471556
0.7532	Intermediate Similarity	NPC477085
0.7529	Intermediate Similarity	NPC45409
0.75	Intermediate Similarity	NPC476037
0.75	Intermediate Similarity	NPC108816
0.75	Intermediate Similarity	NPC179087
0.75	Intermediate Similarity	NPC217940
0.75	Intermediate Similarity	NPC93763
0.75	Intermediate Similarity	NPC267231
0.75	Intermediate Similarity	NPC44343
0.75	Intermediate Similarity	NPC210303
0.747	Intermediate Similarity	NPC16488
0.747	Intermediate Similarity	NPC44261
0.7468	Intermediate Similarity	NPC469880
0.7465	Intermediate Similarity	NPC98519
0.7465	Intermediate Similarity	NPC130953
0.7442	Intermediate Similarity	NPC475739
0.7439	Intermediate Similarity	NPC8538
0.7439	Intermediate Similarity	NPC184208
0.7439	Intermediate Similarity	NPC42470
0.7439	Intermediate Similarity	NPC475944
0.7436	Intermediate Similarity	NPC294434
0.7436	Intermediate Similarity	NPC15499
0.7436	Intermediate Similarity	NPC259599
0.7436	Intermediate Similarity	NPC117746
0.7412	Intermediate Similarity	NPC315395
0.7412	Intermediate Similarity	NPC61527
0.7412	Intermediate Similarity	NPC291712
0.7412	Intermediate Similarity	NPC316426
0.7407	Intermediate Similarity	NPC271632
0.7403	Intermediate Similarity	NPC319163
0.7403	Intermediate Similarity	NPC67076
0.7403	Intermediate Similarity	NPC472254
0.7386	Intermediate Similarity	NPC32494
0.7386	Intermediate Similarity	NPC175842
0.7381	Intermediate Similarity	NPC471301
0.7375	Intermediate Similarity	NPC476439
0.7375	Intermediate Similarity	NPC84360
0.7375	Intermediate Similarity	NPC7563
0.7375	Intermediate Similarity	NPC316324
0.7375	Intermediate Similarity	NPC320630
0.7375	Intermediate Similarity	NPC116177
0.7368	Intermediate Similarity	NPC236208
0.7368	Intermediate Similarity	NPC265574
0.7356	Intermediate Similarity	NPC51358
0.7356	Intermediate Similarity	NPC307092
0.7356	Intermediate Similarity	NPC212598
0.7349	Intermediate Similarity	NPC85772
0.7349	Intermediate Similarity	NPC471298
0.7349	Intermediate Similarity	NPC323251
0.7342	Intermediate Similarity	NPC315552
0.7333	Intermediate Similarity	NPC194871
0.7326	Intermediate Similarity	NPC313658
0.7326	Intermediate Similarity	NPC316138
0.7326	Intermediate Similarity	NPC160138
0.7324	Intermediate Similarity	NPC222852
0.7308	Intermediate Similarity	NPC316851
0.7308	Intermediate Similarity	NPC16349
0.7308	Intermediate Similarity	NPC215745
0.7308	Intermediate Similarity	NPC12815
0.7308	Intermediate Similarity	NPC222244
0.7308	Intermediate Similarity	NPC329890
0.7308	Intermediate Similarity	NPC287878
0.7308	Intermediate Similarity	NPC238948
0.7297	Intermediate Similarity	NPC470123
0.7297	Intermediate Similarity	NPC471565
0.7294	Intermediate Similarity	NPC261380
0.7294	Intermediate Similarity	NPC471494
0.7286	Intermediate Similarity	NPC44542
0.7286	Intermediate Similarity	NPC129150
0.7284	Intermediate Similarity	NPC279532
0.7284	Intermediate Similarity	NPC474005
0.7273	Intermediate Similarity	NPC67183
0.7273	Intermediate Similarity	NPC473448
0.7273	Intermediate Similarity	NPC475879
0.7273	Intermediate Similarity	NPC476012
0.7273	Intermediate Similarity	NPC182136
0.7262	Intermediate Similarity	NPC169575
0.7262	Intermediate Similarity	NPC40746
0.7262	Intermediate Similarity	NPC42476
0.7262	Intermediate Similarity	NPC311070
0.7262	Intermediate Similarity	NPC161045
0.7262	Intermediate Similarity	NPC471297
0.726	Intermediate Similarity	NPC68110
0.726	Intermediate Similarity	NPC2328
0.7253	Intermediate Similarity	NPC16967
0.725	Intermediate Similarity	NPC68819
0.725	Intermediate Similarity	NPC123360
0.7241	Intermediate Similarity	NPC60765
0.7241	Intermediate Similarity	NPC26078
0.7241	Intermediate Similarity	NPC473658
0.7237	Intermediate Similarity	NPC287705
0.7237	Intermediate Similarity	NPC310210
0.7237	Intermediate Similarity	NPC470256
0.7229	Intermediate Similarity	NPC474894
0.7222	Intermediate Similarity	NPC191521
0.7222	Intermediate Similarity	NPC19241
0.7222	Intermediate Similarity	NPC470255
0.7215	Intermediate Similarity	NPC114727
0.7215	Intermediate Similarity	NPC474280
0.7215	Intermediate Similarity	NPC476355
0.7215	Intermediate Similarity	NPC476590
0.7209	Intermediate Similarity	NPC116575
0.7209	Intermediate Similarity	NPC311163
0.7209	Intermediate Similarity	NPC122502
0.7209	Intermediate Similarity	NPC234038
0.72	Intermediate Similarity	NPC248125
0.7195	Intermediate Similarity	NPC99651
0.7195	Intermediate Similarity	NPC139712
0.7191	Intermediate Similarity	NPC32552
0.7183	Intermediate Similarity	NPC189700
0.7183	Intermediate Similarity	NPC223679
0.7179	Intermediate Similarity	NPC293114
0.7176	Intermediate Similarity	NPC78673
0.7176	Intermediate Similarity	NPC161670
0.7176	Intermediate Similarity	NPC14575
0.7176	Intermediate Similarity	NPC160517
0.7176	Intermediate Similarity	NPC471302
0.7176	Intermediate Similarity	NPC31086
0.7176	Intermediate Similarity	NPC186155
0.7176	Intermediate Similarity	NPC126518
0.7176	Intermediate Similarity	NPC196487
0.7176	Intermediate Similarity	NPC474865
0.716	Intermediate Similarity	NPC57744
0.716	Intermediate Similarity	NPC474278

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 NPC470686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1480
0.2-0.3	4226
0.3-0.4	2500
0.4-0.5	630
0.5-0.6	139
0.6-0.7	37
0.7-0.8	3
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
0.7534	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5209	Approved
0.7059	Intermediate Similarity	NPD7154	Phase 3
0.6889	Remote Similarity	NPD7838	Discovery
0.6757	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6629	Remote Similarity	NPD4249	Approved
0.6618	Remote Similarity	NPD4220	Pre-registration
0.6556	Remote Similarity	NPD4250	Approved
0.6556	Remote Similarity	NPD4251	Approved
0.6522	Remote Similarity	NPD5785	Approved
0.6517	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4819	Approved
0.6512	Remote Similarity	NPD4821	Approved
0.6512	Remote Similarity	NPD4822	Approved
0.6512	Remote Similarity	NPD4820	Approved
0.6495	Remote Similarity	NPD6648	Approved
0.6477	Remote Similarity	NPD5362	Discontinued
0.6471	Remote Similarity	NPD4271	Approved
0.6471	Remote Similarity	NPD4268	Approved
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4756	Discovery
0.6344	Remote Similarity	NPD6698	Approved
0.6344	Remote Similarity	NPD46	Approved
0.6333	Remote Similarity	NPD5363	Approved
0.6322	Remote Similarity	NPD4252	Approved
0.631	Remote Similarity	NPD8039	Approved
0.6292	Remote Similarity	NPD5332	Approved
0.6292	Remote Similarity	NPD5331	Approved
0.6277	Remote Similarity	NPD7983	Approved
0.6263	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4790	Discontinued
0.6234	Remote Similarity	NPD368	Approved
0.6224	Remote Similarity	NPD4225	Approved
0.6211	Remote Similarity	NPD5778	Approved
0.6211	Remote Similarity	NPD5779	Approved
0.6197	Remote Similarity	NPD6927	Phase 3
0.618	Remote Similarity	NPD4270	Approved
0.618	Remote Similarity	NPD4269	Approved
0.6162	Remote Similarity	NPD7640	Approved
0.6162	Remote Similarity	NPD7639	Approved
0.6139	Remote Similarity	NPD6647	Phase 2
0.6111	Remote Similarity	NPD6110	Phase 1
0.6092	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5786	Approved
0.6082	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4732	Discontinued
0.6067	Remote Similarity	NPD5369	Approved
0.6061	Remote Similarity	NPD7638	Approved
0.6022	Remote Similarity	NPD1282	Approved
0.602	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7839	Suspended
0.6	Remote Similarity	NPD4219	Approved
0.6	Remote Similarity	NPD6435	Approved
0.5978	Remote Similarity	NPD1694	Approved
0.5955	Remote Similarity	NPD7514	Phase 3
0.5955	Remote Similarity	NPD7332	Phase 2
0.5934	Remote Similarity	NPD6695	Phase 3
0.593	Remote Similarity	NPD8264	Approved
0.5909	Remote Similarity	NPD7505	Discontinued
0.5895	Remote Similarity	NPD6051	Approved
0.5895	Remote Similarity	NPD689	Discontinued
0.5895	Remote Similarity	NPD6101	Approved
0.5895	Remote Similarity	NPD5370	Suspended
0.5895	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD342	Phase 1
0.5844	Remote Similarity	NPD9119	Approved
0.5844	Remote Similarity	NPD69	Approved
0.5841	Remote Similarity	NPD7503	Approved
0.5833	Remote Similarity	NPD6053	Discontinued
0.5806	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD2067	Discontinued
0.5794	Remote Similarity	NPD6371	Approved
0.5778	Remote Similarity	NPD5368	Approved
0.5778	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD6411	Approved
0.5769	Remote Similarity	NPD5909	Discontinued
0.5755	Remote Similarity	NPD6686	Approved
0.573	Remote Similarity	NPD7145	Approved
0.5714	Remote Similarity	NPD4265	Approved
0.5714	Remote Similarity	NPD694	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6902	Approved
0.5714	Remote Similarity	NPD9118	Approved
0.5714	Remote Similarity	NPD4211	Phase 1
0.5684	Remote Similarity	NPD7524	Approved
0.5684	Remote Similarity	NPD7750	Discontinued
0.566	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD5282	Discontinued
0.5647	Remote Similarity	NPD7144	Approved
0.5647	Remote Similarity	NPD7143	Approved
0.5641	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6109	Phase 1
0.5632	Remote Similarity	NPD6926	Approved
0.5632	Remote Similarity	NPD6924	Approved
0.5625	Remote Similarity	NPD7115	Discovery
0.5618	Remote Similarity	NPD6932	Approved
0.5618	Remote Similarity	NPD6925	Approved
0.5618	Remote Similarity	NPD5776	Phase 2
0.5604	Remote Similarity	NPD6931	Approved
0.5604	Remote Similarity	NPD6930	Phase 2

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