NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	626.15
Volume:	561.108
LogP:	-0.767
LogD:	-0.512
LogS:	-3.622
# Rotatable Bonds:	7
TPSA:	289.66
# H-Bond Aceptor:	17
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	4.775
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.543
MDCK Permeability:	3.313868000986986e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.853
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	80.4518814086914%
Volume Distribution (VD):	0.64
Pgp-substrate:	18.870708465576172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.253
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.402
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.745
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.236
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.007

Download Data

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

Natural Product: NPC60718

Natural Product ID:	NPC60718
*Common Name:**	2-[(3S,4Z,6S)-6-Butyl-6-Ethyl-4-Ethylidenedioxan-3-Yl]Acetic Acid
IUPAC Name:	2-[(3S,4Z,6S)-6-butyl-6-ethyl-4-ethylidenedioxan-3-yl]acetic acid
Synonyms:
Standard InCHIKey:	BJPWYJPXKWNMRI-DRHNYNEPSA-N
Standard InCHI:	InChI=1S/C14H24O4/c1-4-7-8-14(6-3)10-11(5-2)12(17-18-14)9-13(15)16/h5,12H,4,6-10H2,1-3H3,(H,15,16)/b11-5-/t12-,14-/m0/s1
SMILES:	CCCC[C@@]1(CC)C/C(=C/C)/[C@H](CC(=O)O)OO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477543
PubChem CID:	10244142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000368] Dioxanes [CHEMONTID:0001312] 1,2-dioxanes

*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
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	red sea	n.a.	PMID[12762806]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18027906]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22469701]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	collected by hand at a depth of 10 m off the shore of Iriomote Island, Okinawa Prefecture, Japan	2009-JUN	PMID[23855338]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24948562]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27015002]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	New Guinea	n.a.	PMID[8158156]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.5	ug ml-1	PMID[555714]

☑ 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 NPC60718 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	152
0.1-0.2	1003
0.2-0.3	4966
0.3-0.4	12893
0.4-0.5	12188
0.5-0.6	7619
0.6-0.7	3584
0.7-0.8	249
0.8-0.85	26
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC121200
0.9178	High Similarity	NPC281296
0.8904	High Similarity	NPC199445
0.8784	High Similarity	NPC469514
0.8784	High Similarity	NPC474447
0.8684	High Similarity	NPC113363
0.8684	High Similarity	NPC82488
0.8684	High Similarity	NPC308545
0.8625	High Similarity	NPC476982
0.8611	High Similarity	NPC69462
0.8493	Intermediate Similarity	NPC126061
0.8481	Intermediate Similarity	NPC69469
0.8472	Intermediate Similarity	NPC107130
0.8462	Intermediate Similarity	NPC475481
0.8462	Intermediate Similarity	NPC79277
0.8462	Intermediate Similarity	NPC14044
0.8462	Intermediate Similarity	NPC172309
0.8462	Intermediate Similarity	NPC117960
0.8378	Intermediate Similarity	NPC167145
0.8378	Intermediate Similarity	NPC238425
0.8378	Intermediate Similarity	NPC472018
0.8378	Intermediate Similarity	NPC474543
0.8272	Intermediate Similarity	NPC471344
0.8267	Intermediate Similarity	NPC474551
0.8267	Intermediate Similarity	NPC330016
0.825	Intermediate Similarity	NPC476983
0.8182	Intermediate Similarity	NPC476264
0.8182	Intermediate Similarity	NPC476325
0.8171	Intermediate Similarity	NPC476104
0.8158	Intermediate Similarity	NPC255060
0.8052	Intermediate Similarity	NPC239127
0.7952	Intermediate Similarity	NPC262085
0.7949	Intermediate Similarity	NPC122847
0.7867	Intermediate Similarity	NPC472017
0.7857	Intermediate Similarity	NPC86005
0.7848	Intermediate Similarity	NPC476986
0.7848	Intermediate Similarity	NPC470905
0.7821	Intermediate Similarity	NPC266119
0.7778	Intermediate Similarity	NPC476988
0.775	Intermediate Similarity	NPC246458
0.7738	Intermediate Similarity	NPC472009
0.7722	Intermediate Similarity	NPC107668
0.7714	Intermediate Similarity	NPC475821
0.7711	Intermediate Similarity	NPC295799
0.7683	Intermediate Similarity	NPC474252
0.7683	Intermediate Similarity	NPC475395
0.7683	Intermediate Similarity	NPC476984
0.7683	Intermediate Similarity	NPC89555
0.7674	Intermediate Similarity	NPC471342
0.7674	Intermediate Similarity	NPC469866
0.7654	Intermediate Similarity	NPC469920
0.7647	Intermediate Similarity	NPC472007
0.7647	Intermediate Similarity	NPC471738
0.7619	Intermediate Similarity	NPC474369
0.7595	Intermediate Similarity	NPC49392
0.7595	Intermediate Similarity	NPC59602
0.7595	Intermediate Similarity	NPC476987
0.7595	Intermediate Similarity	NPC61863
0.7595	Intermediate Similarity	NPC152754
0.7595	Intermediate Similarity	NPC190400
0.759	Intermediate Similarity	NPC476100
0.7561	Intermediate Similarity	NPC52861
0.7561	Intermediate Similarity	NPC470241
0.7561	Intermediate Similarity	NPC88735
0.7558	Intermediate Similarity	NPC472008
0.7534	Intermediate Similarity	NPC234767
0.7532	Intermediate Similarity	NPC320119
0.7531	Intermediate Similarity	NPC475210
0.7529	Intermediate Similarity	NPC469483
0.7529	Intermediate Similarity	NPC116575
0.75	Intermediate Similarity	NPC70424
0.75	Intermediate Similarity	NPC471343
0.75	Intermediate Similarity	NPC114979
0.75	Intermediate Similarity	NPC191476
0.75	Intermediate Similarity	NPC141193
0.75	Intermediate Similarity	NPC469867
0.75	Intermediate Similarity	NPC243618
0.75	Intermediate Similarity	NPC96259
0.75	Intermediate Similarity	NPC158756
0.747	Intermediate Similarity	NPC7414
0.747	Intermediate Similarity	NPC476292
0.747	Intermediate Similarity	NPC474605
0.747	Intermediate Similarity	NPC85772
0.7467	Intermediate Similarity	NPC472875
0.7442	Intermediate Similarity	NPC477959
0.7439	Intermediate Similarity	NPC103634
0.7439	Intermediate Similarity	NPC233377
0.7436	Intermediate Similarity	NPC275098
0.7432	Intermediate Similarity	NPC318420
0.7432	Intermediate Similarity	NPC326268
0.7412	Intermediate Similarity	NPC165162
0.7412	Intermediate Similarity	NPC470755
0.7412	Intermediate Similarity	NPC261380
0.7412	Intermediate Similarity	NPC255307
0.7407	Intermediate Similarity	NPC127526
0.7407	Intermediate Similarity	NPC474341
0.7407	Intermediate Similarity	NPC478122
0.7397	Intermediate Similarity	NPC474552
0.7381	Intermediate Similarity	NPC477784
0.7381	Intermediate Similarity	NPC475989
0.7381	Intermediate Similarity	NPC477786
0.7381	Intermediate Similarity	NPC477785
0.7375	Intermediate Similarity	NPC476985
0.7375	Intermediate Similarity	NPC474316
0.7375	Intermediate Similarity	NPC279537
0.7375	Intermediate Similarity	NPC12740
0.7375	Intermediate Similarity	NPC110461
0.7375	Intermediate Similarity	NPC475744
0.7356	Intermediate Similarity	NPC476805
0.7356	Intermediate Similarity	NPC476803
0.7349	Intermediate Similarity	NPC141810
0.7349	Intermediate Similarity	NPC47031
0.7349	Intermediate Similarity	NPC24417
0.7326	Intermediate Similarity	NPC473226
0.7326	Intermediate Similarity	NPC477993
0.7326	Intermediate Similarity	NPC261721
0.7326	Intermediate Similarity	NPC469910
0.7326	Intermediate Similarity	NPC475461
0.7326	Intermediate Similarity	NPC477994
0.7326	Intermediate Similarity	NPC305475
0.7326	Intermediate Similarity	NPC475181
0.7317	Intermediate Similarity	NPC98557
0.7317	Intermediate Similarity	NPC268502
0.7317	Intermediate Similarity	NPC167881
0.7317	Intermediate Similarity	NPC19841
0.7317	Intermediate Similarity	NPC254996
0.7303	Intermediate Similarity	NPC300312
0.7303	Intermediate Similarity	NPC111114
0.7303	Intermediate Similarity	NPC261607
0.7303	Intermediate Similarity	NPC472199
0.7303	Intermediate Similarity	NPC470373
0.7303	Intermediate Similarity	NPC470379
0.7294	Intermediate Similarity	NPC476804
0.7294	Intermediate Similarity	NPC9868
0.7294	Intermediate Similarity	NPC472326
0.7294	Intermediate Similarity	NPC474776
0.7294	Intermediate Similarity	NPC72464
0.7284	Intermediate Similarity	NPC474278
0.7284	Intermediate Similarity	NPC474760
0.7284	Intermediate Similarity	NPC120776
0.7284	Intermediate Similarity	NPC240170
0.7273	Intermediate Similarity	NPC212598
0.7273	Intermediate Similarity	NPC101622
0.7273	Intermediate Similarity	NPC97577
0.7262	Intermediate Similarity	NPC229825
0.7262	Intermediate Similarity	NPC475936
0.7253	Intermediate Similarity	NPC475659
0.725	Intermediate Similarity	NPC475861
0.7241	Intermediate Similarity	NPC72513
0.7237	Intermediate Similarity	NPC26500
0.7237	Intermediate Similarity	NPC99619
0.7229	Intermediate Similarity	NPC271104
0.7229	Intermediate Similarity	NPC470947
0.7229	Intermediate Similarity	NPC115418
0.7229	Intermediate Similarity	NPC470945
0.7229	Intermediate Similarity	NPC470946
0.7222	Intermediate Similarity	NPC320089
0.7222	Intermediate Similarity	NPC475302
0.7215	Intermediate Similarity	NPC326024
0.7215	Intermediate Similarity	NPC135703
0.7209	Intermediate Similarity	NPC125290
0.7209	Intermediate Similarity	NPC187529
0.7195	Intermediate Similarity	NPC108816
0.7195	Intermediate Similarity	NPC476627
0.7195	Intermediate Similarity	NPC93763
0.7195	Intermediate Similarity	NPC27949
0.7195	Intermediate Similarity	NPC39547
0.7195	Intermediate Similarity	NPC323249
0.7195	Intermediate Similarity	NPC260814
0.7195	Intermediate Similarity	NPC267231
0.7195	Intermediate Similarity	NPC192006
0.7195	Intermediate Similarity	NPC231739
0.7195	Intermediate Similarity	NPC218817
0.7195	Intermediate Similarity	NPC11796
0.7191	Intermediate Similarity	NPC316228
0.7191	Intermediate Similarity	NPC77337
0.7191	Intermediate Similarity	NPC313670
0.7179	Intermediate Similarity	NPC4299
0.7179	Intermediate Similarity	NPC472955
0.7179	Intermediate Similarity	NPC475310
0.7176	Intermediate Similarity	NPC59097
0.7176	Intermediate Similarity	NPC169575
0.7176	Intermediate Similarity	NPC40746
0.7176	Intermediate Similarity	NPC16488
0.7176	Intermediate Similarity	NPC170286
0.7176	Intermediate Similarity	NPC473390
0.7176	Intermediate Similarity	NPC53867
0.7176	Intermediate Similarity	NPC131669
0.7174	Intermediate Similarity	NPC180722
0.7174	Intermediate Similarity	NPC230800
0.7174	Intermediate Similarity	NPC473859
0.7174	Intermediate Similarity	NPC195645
0.7174	Intermediate Similarity	NPC165332
0.716	Intermediate Similarity	NPC271070
0.7159	Intermediate Similarity	NPC475819
0.7159	Intermediate Similarity	NPC473658
0.7159	Intermediate Similarity	NPC136879
0.7159	Intermediate Similarity	NPC477302
0.7143	Intermediate Similarity	NPC25684
0.7143	Intermediate Similarity	NPC301477

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 NPC60718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1447
0.2-0.3	3781
0.3-0.4	2469
0.4-0.5	850
0.5-0.6	400
0.6-0.7	58
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
0.747	Intermediate Similarity	NPD4269	Approved
0.747	Intermediate Similarity	NPD4270	Approved
0.7439	Intermediate Similarity	NPD4822	Approved
0.7439	Intermediate Similarity	NPD4820	Approved
0.7439	Intermediate Similarity	NPD4821	Approved
0.7439	Intermediate Similarity	NPD4819	Approved
0.7386	Intermediate Similarity	NPD46	Approved
0.7386	Intermediate Similarity	NPD6698	Approved
0.7381	Intermediate Similarity	NPD7154	Phase 3
0.7349	Intermediate Similarity	NPD5369	Approved
0.7303	Intermediate Similarity	NPD7983	Approved
0.7273	Intermediate Similarity	NPD6101	Approved
0.7273	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4252	Approved
0.7222	Intermediate Similarity	NPD5778	Approved
0.7222	Intermediate Similarity	NPD5779	Approved
0.7209	Intermediate Similarity	NPD5363	Approved
0.7195	Intermediate Similarity	NPD4268	Approved
0.7195	Intermediate Similarity	NPD4271	Approved
0.7176	Intermediate Similarity	NPD5362	Discontinued
0.7174	Intermediate Similarity	NPD7839	Suspended
0.7126	Intermediate Similarity	NPD5786	Approved
0.7111	Intermediate Similarity	NPD6411	Approved
0.7024	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5368	Approved
0.6988	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7331	Phase 2
0.6882	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6435	Approved
0.6813	Remote Similarity	NPD5785	Approved
0.6782	Remote Similarity	NPD5331	Approved
0.6782	Remote Similarity	NPD5332	Approved
0.6774	Remote Similarity	NPD5282	Discontinued
0.6744	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD4756	Discovery
0.6627	Remote Similarity	NPD8039	Approved
0.6623	Remote Similarity	NPD3197	Phase 1
0.662	Remote Similarity	NPD3172	Approved
0.6588	Remote Similarity	NPD3732	Approved
0.6579	Remote Similarity	NPD368	Approved
0.6559	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7637	Suspended
0.6556	Remote Similarity	NPD6422	Discontinued
0.6556	Remote Similarity	NPD4249	Approved
0.6538	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4266	Approved
0.6528	Remote Similarity	NPD3195	Phase 2
0.6528	Remote Similarity	NPD3194	Approved
0.6528	Remote Similarity	NPD3196	Approved
0.6522	Remote Similarity	NPD5370	Suspended
0.6489	Remote Similarity	NPD6399	Phase 3
0.6484	Remote Similarity	NPD4250	Approved
0.6484	Remote Similarity	NPD4251	Approved
0.6447	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6371	Approved
0.6344	Remote Similarity	NPD1695	Approved
0.6329	Remote Similarity	NPD7341	Phase 2
0.6327	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4225	Approved
0.6292	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3667	Approved
0.6286	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7838	Discovery
0.6211	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD622	Approved
0.6111	Remote Similarity	NPD28	Approved
0.6111	Remote Similarity	NPD29	Approved
0.6111	Remote Similarity	NPD5209	Approved
0.6087	Remote Similarity	NPD1694	Approved
0.6082	Remote Similarity	NPD7748	Approved
0.6081	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6053	Discontinued
0.6071	Remote Similarity	NPD8513	Phase 3
0.6071	Remote Similarity	NPD8516	Approved
0.6071	Remote Similarity	NPD8517	Approved
0.6071	Remote Similarity	NPD8515	Approved
0.6067	Remote Similarity	NPD4695	Discontinued
0.6067	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6083	Phase 2
0.6061	Remote Similarity	NPD6084	Phase 2
0.6061	Remote Similarity	NPD7902	Approved
0.6056	Remote Similarity	NPD3173	Approved
0.6049	Remote Similarity	NPD3704	Approved
0.6042	Remote Similarity	NPD5281	Approved
0.6042	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD342	Phase 1
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD7115	Discovery
0.5978	Remote Similarity	NPD3668	Phase 3
0.5978	Remote Similarity	NPD3666	Approved
0.5978	Remote Similarity	NPD3665	Phase 1
0.5978	Remote Similarity	NPD3133	Approved
0.5962	Remote Similarity	NPD7128	Approved
0.5962	Remote Similarity	NPD6675	Approved
0.5962	Remote Similarity	NPD5048	Discontinued
0.5962	Remote Similarity	NPD6402	Approved
0.5962	Remote Similarity	NPD5739	Approved
0.5934	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD1696	Phase 3
0.5905	Remote Similarity	NPD5697	Approved
0.5905	Remote Similarity	NPD5701	Approved
0.59	Remote Similarity	NPD4755	Approved
0.5882	Remote Similarity	NPD5344	Discontinued
0.5862	Remote Similarity	NPD8273	Phase 1
0.5857	Remote Similarity	NPD634	Phase 3
0.5851	Remote Similarity	NPD5330	Approved
0.5851	Remote Similarity	NPD7146	Approved
0.5851	Remote Similarity	NPD6684	Approved
0.5851	Remote Similarity	NPD3618	Phase 1
0.5851	Remote Similarity	NPD7521	Approved
0.5851	Remote Similarity	NPD5279	Phase 3
0.5851	Remote Similarity	NPD6409	Approved
0.5851	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7334	Approved
0.5851	Remote Similarity	NPD4519	Discontinued
0.5851	Remote Similarity	NPD4623	Approved
0.5849	Remote Similarity	NPD6881	Approved
0.5849	Remote Similarity	NPD6899	Approved
0.5849	Remote Similarity	NPD7320	Approved
0.5842	Remote Similarity	NPD7638	Approved
0.5833	Remote Similarity	NPD1719	Phase 1
0.5833	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5211	Phase 2
0.5824	Remote Similarity	NPD857	Phase 3
0.5816	Remote Similarity	NPD4202	Approved
0.5814	Remote Similarity	NPD4732	Discontinued
0.5812	Remote Similarity	NPD8074	Phase 3
0.5806	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6013	Approved
0.5794	Remote Similarity	NPD6014	Approved
0.5794	Remote Similarity	NPD6373	Approved
0.5794	Remote Similarity	NPD6012	Approved
0.5794	Remote Similarity	NPD6372	Approved
0.5789	Remote Similarity	NPD8444	Approved
0.5784	Remote Similarity	NPD5285	Approved
0.5784	Remote Similarity	NPD7639	Approved
0.5784	Remote Similarity	NPD4700	Approved
0.5784	Remote Similarity	NPD7640	Approved
0.5784	Remote Similarity	NPD4696	Approved
0.5784	Remote Similarity	NPD5286	Approved
0.5784	Remote Similarity	NPD6648	Approved
0.5776	Remote Similarity	NPD8340	Approved
0.5776	Remote Similarity	NPD8342	Approved
0.5776	Remote Similarity	NPD8341	Approved
0.5776	Remote Similarity	NPD8299	Approved
0.5769	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4223	Phase 3
0.5761	Remote Similarity	NPD4221	Approved
0.5758	Remote Similarity	NPD7900	Approved
0.5758	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.575	Remote Similarity	NPD4191	Approved
0.575	Remote Similarity	NPD4194	Approved
0.575	Remote Similarity	NPD4192	Approved
0.575	Remote Similarity	NPD4193	Approved
0.5747	Remote Similarity	NPD6924	Approved
0.5747	Remote Similarity	NPD6926	Approved
0.5745	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7290	Approved
0.5741	Remote Similarity	NPD7102	Approved
0.5741	Remote Similarity	NPD6883	Approved
0.5729	Remote Similarity	NPD5737	Approved
0.5729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6903	Approved
0.5729	Remote Similarity	NPD6672	Approved
0.5726	Remote Similarity	NPD8451	Approved
0.5714	Remote Similarity	NPD7514	Phase 3
0.5714	Remote Similarity	NPD6930	Phase 2
0.5714	Remote Similarity	NPD8034	Phase 2
0.5714	Remote Similarity	NPD8035	Phase 2
0.5714	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD7332	Phase 2
0.5714	Remote Similarity	NPD6931	Approved
0.5701	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6011	Approved
0.57	Remote Similarity	NPD5210	Approved
0.57	Remote Similarity	NPD4629	Approved
0.5699	Remote Similarity	NPD6695	Phase 3
0.5696	Remote Similarity	NPD3198	Approved
0.569	Remote Similarity	NPD7829	Approved
0.569	Remote Similarity	NPD7642	Approved
0.569	Remote Similarity	NPD7830	Approved
0.5688	Remote Similarity	NPD6847	Approved
0.5688	Remote Similarity	NPD6650	Approved
0.5688	Remote Similarity	NPD6869	Approved
0.5688	Remote Similarity	NPD6649	Approved
0.5688	Remote Similarity	NPD6617	Approved
0.5688	Remote Similarity	NPD8130	Phase 1
0.5686	Remote Similarity	NPD9495	Approved
0.5682	Remote Similarity	NPD8264	Approved
0.5678	Remote Similarity	NPD8448	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