NPASS Compound

Structure

NPC110461 OpenBabel07101718192D 22 23 0 0 1 0 0 0 0 0999 V2000 -4.9917 -2.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8748 1.6321 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 0.0000 -3.0000 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 -4.2257 0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5677 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 0.9397 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 -3.3596 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 14 1 0 0 0 0 2 15 2 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 15 18 1 0 0 0 0 16 11 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 9 1 1 0 0 0 17 19 1 0 0 0 0 18 13 1 6 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.2
Volume:	335.892
LogP:	3.407
LogD:	3.227
LogS:	-4.475
# Rotatable Bonds:	4
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	4.681
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:	-4.616
MDCK Permeability:	7.201481639640406e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.83
30% Bioavailability (F30%):	0.516

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.901
Plasma Protein Binding (PPB):	78.0198745727539%
Volume Distribution (VD):	0.439
Pgp-substrate:	13.284518241882324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.308
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.114
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.545
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.631
CYP3A4-inhibitor:	0.587
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	4.932
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.527
Drug-inuced Liver Injury (DILI):	0.138
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.952
Carcinogencity:	0.198
Eye Corrosion:	0.016
Eye Irritation:	0.319
Respiratory Toxicity:	0.765

Download Data

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

Natural Product: NPC110461

Natural Product ID:	NPC110461
*Common Name:**	Acalycixeniolide L
IUPAC Name:	(4S,4aS,7E,11aR)-4-[(E)-5-hydroxypent-3-enyl]-7-methyl-11-methylidene-1,4,4a,5,6,9,10,11a-octahydrocyclonona[c]pyran-3-one
Synonyms:	Acalycixeniolide L
Standard InCHIKey:	XPGKNDIUGKZTKO-HMEATOBQSA-N
Standard InCHI:	InChI=1S/C19H28O3/c1-14-7-6-8-15(2)18-13-22-19(21)17(16(18)11-10-14)9-4-3-5-12-20/h3,5,7,16-18,20H,2,4,6,8-13H2,1H3/b5-3+,14-7+/t16-,17+,18+/m1/s1
SMILES:	C/C/1=CCCC(=C)[C@@H]2COC(=O)[C@@H](CC/C=C/CO)[C@H]2CC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478952
PubChem CID:	11779819
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
NPO32884	acalycigorgia inermis	Species	Acanthogorgiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325246]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	1.5	ug.mL-1	PMID[502076]

☑ 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 NPC110461 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	148
0.1-0.2	956
0.2-0.3	4926
0.3-0.4	14482
0.4-0.5	10956
0.5-0.6	7321
0.6-0.7	3586
0.7-0.8	306
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12740
0.9718	High Similarity	NPC61863
0.9583	High Similarity	NPC107668
0.9028	High Similarity	NPC135703
0.8734	High Similarity	NPC14575
0.8734	High Similarity	NPC196487
0.8519	High Similarity	NPC234038
0.8519	High Similarity	NPC116575
0.8442	Intermediate Similarity	NPC474341
0.8395	Intermediate Similarity	NPC474369
0.8214	Intermediate Similarity	NPC212598
0.814	Intermediate Similarity	NPC476049
0.8072	Intermediate Similarity	NPC198314
0.8052	Intermediate Similarity	NPC475861
0.8049	Intermediate Similarity	NPC474776
0.8	Intermediate Similarity	NPC106040
0.8	Intermediate Similarity	NPC115179
0.7976	Intermediate Similarity	NPC86005
0.7875	Intermediate Similarity	NPC469617
0.7838	Intermediate Similarity	NPC472875
0.7831	Intermediate Similarity	NPC70424
0.7831	Intermediate Similarity	NPC243618
0.7805	Intermediate Similarity	NPC475936
0.7778	Intermediate Similarity	NPC103634
0.7753	Intermediate Similarity	NPC272050
0.775	Intermediate Similarity	NPC239098
0.7722	Intermediate Similarity	NPC279537
0.7711	Intermediate Similarity	NPC52609
0.7711	Intermediate Similarity	NPC53867
0.7711	Intermediate Similarity	NPC1761
0.7683	Intermediate Similarity	NPC325031
0.7654	Intermediate Similarity	NPC89128
0.7647	Intermediate Similarity	NPC202394
0.7632	Intermediate Similarity	NPC199557
0.7625	Intermediate Similarity	NPC116177
0.7625	Intermediate Similarity	NPC7563
0.7625	Intermediate Similarity	NPC320630
0.7619	Intermediate Similarity	NPC295799
0.7595	Intermediate Similarity	NPC324762
0.7561	Intermediate Similarity	NPC233377
0.7558	Intermediate Similarity	NPC312561
0.7558	Intermediate Similarity	NPC477959
0.7558	Intermediate Similarity	NPC474765
0.7532	Intermediate Similarity	NPC4299
0.7531	Intermediate Similarity	NPC127526
0.7531	Intermediate Similarity	NPC267231
0.7531	Intermediate Similarity	NPC121200
0.7531	Intermediate Similarity	NPC192006
0.7529	Intermediate Similarity	NPC28887
0.75	Intermediate Similarity	NPC69469
0.75	Intermediate Similarity	NPC474447
0.75	Intermediate Similarity	NPC214844
0.747	Intermediate Similarity	NPC470241
0.747	Intermediate Similarity	NPC14203
0.747	Intermediate Similarity	NPC229584
0.747	Intermediate Similarity	NPC88735
0.747	Intermediate Similarity	NPC52861
0.7468	Intermediate Similarity	NPC472966
0.7442	Intermediate Similarity	NPC82979
0.7436	Intermediate Similarity	NPC472254
0.7432	Intermediate Similarity	NPC34883
0.7419	Intermediate Similarity	NPC475053
0.7416	Intermediate Similarity	NPC219874
0.7412	Intermediate Similarity	NPC82297
0.7412	Intermediate Similarity	NPC9868
0.7412	Intermediate Similarity	NPC476804
0.7407	Intermediate Similarity	NPC281296
0.7403	Intermediate Similarity	NPC101622
0.7386	Intermediate Similarity	NPC97577
0.7381	Intermediate Similarity	NPC474252
0.7381	Intermediate Similarity	NPC85772
0.7381	Intermediate Similarity	NPC89555
0.7381	Intermediate Similarity	NPC7414
0.7375	Intermediate Similarity	NPC60718
0.7375	Intermediate Similarity	NPC228978
0.7356	Intermediate Similarity	NPC237540
0.7356	Intermediate Similarity	NPC475678
0.7349	Intermediate Similarity	NPC271104
0.7342	Intermediate Similarity	NPC470237
0.7326	Intermediate Similarity	NPC86316
0.7326	Intermediate Similarity	NPC106416
0.7326	Intermediate Similarity	NPC52628
0.7326	Intermediate Similarity	NPC255307
0.7326	Intermediate Similarity	NPC261380
0.7317	Intermediate Similarity	NPC471465
0.7317	Intermediate Similarity	NPC269543
0.7317	Intermediate Similarity	NPC196653
0.7317	Intermediate Similarity	NPC247783
0.7317	Intermediate Similarity	NPC475994
0.7317	Intermediate Similarity	NPC471220
0.7317	Intermediate Similarity	NPC108816
0.7317	Intermediate Similarity	NPC4436
0.7317	Intermediate Similarity	NPC93763
0.7308	Intermediate Similarity	NPC472955
0.7308	Intermediate Similarity	NPC475310
0.7303	Intermediate Similarity	NPC313670
0.7303	Intermediate Similarity	NPC281942
0.7303	Intermediate Similarity	NPC232426
0.7294	Intermediate Similarity	NPC475842
0.7294	Intermediate Similarity	NPC215893
0.7294	Intermediate Similarity	NPC250315
0.7284	Intermediate Similarity	NPC471726
0.7284	Intermediate Similarity	NPC474527
0.7284	Intermediate Similarity	NPC271070
0.7283	Intermediate Similarity	NPC165332
0.7283	Intermediate Similarity	NPC195645
0.7283	Intermediate Similarity	NPC180722
0.7262	Intermediate Similarity	NPC475481
0.7262	Intermediate Similarity	NPC47031
0.7262	Intermediate Similarity	NPC79277
0.725	Intermediate Similarity	NPC474551
0.7241	Intermediate Similarity	NPC476982
0.7241	Intermediate Similarity	NPC305475
0.7241	Intermediate Similarity	NPC475461
0.7241	Intermediate Similarity	NPC473226
0.7241	Intermediate Similarity	NPC315395
0.7241	Intermediate Similarity	NPC316426
0.7237	Intermediate Similarity	NPC142423
0.7237	Intermediate Similarity	NPC308294
0.7229	Intermediate Similarity	NPC470239
0.7229	Intermediate Similarity	NPC470244
0.7229	Intermediate Similarity	NPC327674
0.7222	Intermediate Similarity	NPC36491
0.7222	Intermediate Similarity	NPC475972
0.7222	Intermediate Similarity	NPC141831
0.7215	Intermediate Similarity	NPC129665
0.7215	Intermediate Similarity	NPC320119
0.7215	Intermediate Similarity	NPC163003
0.7209	Intermediate Similarity	NPC472957
0.7209	Intermediate Similarity	NPC472326
0.7209	Intermediate Similarity	NPC72464
0.7209	Intermediate Similarity	NPC141193
0.7209	Intermediate Similarity	NPC96259
0.7209	Intermediate Similarity	NPC472958
0.7209	Intermediate Similarity	NPC191476
0.7209	Intermediate Similarity	NPC114979
0.72	Intermediate Similarity	NPC234767
0.72	Intermediate Similarity	NPC470320
0.7195	Intermediate Similarity	NPC41780
0.7195	Intermediate Similarity	NPC40049
0.7195	Intermediate Similarity	NPC187568
0.7195	Intermediate Similarity	NPC61952
0.7195	Intermediate Similarity	NPC316324
0.7191	Intermediate Similarity	NPC251528
0.7191	Intermediate Similarity	NPC256902
0.7191	Intermediate Similarity	NPC118193
0.7191	Intermediate Similarity	NPC474032
0.7191	Intermediate Similarity	NPC295312
0.7179	Intermediate Similarity	NPC296522
0.7179	Intermediate Similarity	NPC144511
0.7176	Intermediate Similarity	NPC474291
0.7176	Intermediate Similarity	NPC145963
0.7174	Intermediate Similarity	NPC472469
0.7174	Intermediate Similarity	NPC134067
0.7174	Intermediate Similarity	NPC107476
0.7162	Intermediate Similarity	NPC174560
0.7162	Intermediate Similarity	NPC201939
0.7162	Intermediate Similarity	NPC125312
0.716	Intermediate Similarity	NPC255060
0.716	Intermediate Similarity	NPC199445
0.716	Intermediate Similarity	NPC472256
0.7159	Intermediate Similarity	NPC179659
0.7159	Intermediate Similarity	NPC471738
0.7159	Intermediate Similarity	NPC231599
0.7159	Intermediate Similarity	NPC128644
0.7143	Intermediate Similarity	NPC26500
0.7143	Intermediate Similarity	NPC99619
0.7143	Intermediate Similarity	NPC200446
0.7143	Intermediate Similarity	NPC304795
0.7143	Intermediate Similarity	NPC195424
0.7143	Intermediate Similarity	NPC306095
0.7143	Intermediate Similarity	NPC115418
0.7126	Intermediate Similarity	NPC165162
0.7126	Intermediate Similarity	NPC283733
0.7126	Intermediate Similarity	NPC21469
0.7126	Intermediate Similarity	NPC147921
0.7126	Intermediate Similarity	NPC125290
0.7126	Intermediate Similarity	NPC65661
0.7126	Intermediate Similarity	NPC137033
0.7125	Intermediate Similarity	NPC474543
0.7125	Intermediate Similarity	NPC275098
0.7125	Intermediate Similarity	NPC35656
0.7125	Intermediate Similarity	NPC167145
0.7125	Intermediate Similarity	NPC238425
0.7125	Intermediate Similarity	NPC472018
0.7125	Intermediate Similarity	NPC477085
0.7111	Intermediate Similarity	NPC166554
0.7111	Intermediate Similarity	NPC265856
0.7111	Intermediate Similarity	NPC77337
0.7111	Intermediate Similarity	NPC474761
0.7111	Intermediate Similarity	NPC476004
0.7111	Intermediate Similarity	NPC232202
0.7111	Intermediate Similarity	NPC469368
0.7111	Intermediate Similarity	NPC477782
0.7111	Intermediate Similarity	NPC473448
0.7108	Intermediate Similarity	NPC39547
0.7108	Intermediate Similarity	NPC218817
0.7108	Intermediate Similarity	NPC169095
0.7108	Intermediate Similarity	NPC469495
0.7108	Intermediate Similarity	NPC11796

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 NPC110461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1348
0.2-0.3	3788
0.3-0.4	2580
0.4-0.5	808
0.5-0.6	392
0.6-0.7	81
0.7-0.8	14
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
0.7711	Intermediate Similarity	NPD7154	Phase 3
0.7711	Intermediate Similarity	NPD5362	Discontinued
0.7528	Intermediate Similarity	NPD5778	Approved
0.7528	Intermediate Similarity	NPD5779	Approved
0.7442	Intermediate Similarity	NPD5786	Approved
0.7386	Intermediate Similarity	NPD6101	Approved
0.7386	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4270	Approved
0.7381	Intermediate Similarity	NPD4269	Approved
0.7375	Intermediate Similarity	NPD8039	Approved
0.7349	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7839	Suspended
0.7222	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD7983	Approved
0.7176	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD4252	Approved
0.7143	Intermediate Similarity	NPD4820	Approved
0.7143	Intermediate Similarity	NPD4822	Approved
0.7143	Intermediate Similarity	NPD4819	Approved
0.7143	Intermediate Similarity	NPD4821	Approved
0.7126	Intermediate Similarity	NPD5363	Approved
0.7111	Intermediate Similarity	NPD46	Approved
0.7111	Intermediate Similarity	NPD6698	Approved
0.7108	Intermediate Similarity	NPD4268	Approved
0.7108	Intermediate Similarity	NPD4271	Approved
0.7093	Intermediate Similarity	NPD5331	Approved
0.7093	Intermediate Similarity	NPD5332	Approved
0.7059	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD4790	Discontinued
0.6977	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5368	Approved
0.6923	Remote Similarity	NPD5785	Approved
0.6854	Remote Similarity	NPD6422	Discontinued
0.6854	Remote Similarity	NPD4249	Approved
0.6778	Remote Similarity	NPD4250	Approved
0.6778	Remote Similarity	NPD4251	Approved
0.6761	Remote Similarity	NPD3172	Approved
0.6667	Remote Similarity	NPD3196	Approved
0.6667	Remote Similarity	NPD3195	Phase 2
0.6667	Remote Similarity	NPD4266	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD3194	Approved
0.6632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4756	Discovery
0.6582	Remote Similarity	NPD7331	Phase 2
0.6579	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD3197	Phase 1
0.65	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD28	Approved
0.6479	Remote Similarity	NPD29	Approved
0.6456	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5370	Suspended
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6399	Phase 3
0.6413	Remote Similarity	NPD3573	Approved
0.6404	Remote Similarity	NPD3667	Approved
0.6374	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD342	Phase 1
0.6329	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3732	Approved
0.6304	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD7521	Approved
0.6304	Remote Similarity	NPD7334	Approved
0.6304	Remote Similarity	NPD7146	Approved
0.6304	Remote Similarity	NPD5330	Approved
0.6304	Remote Similarity	NPD6409	Approved
0.6282	Remote Similarity	NPD4193	Approved
0.6282	Remote Similarity	NPD4192	Approved
0.6282	Remote Similarity	NPD368	Approved
0.6282	Remote Similarity	NPD4194	Approved
0.6282	Remote Similarity	NPD4191	Approved
0.6264	Remote Similarity	NPD4786	Approved
0.6263	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.6226	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5209	Approved
0.6211	Remote Similarity	NPD3673	Approved
0.6211	Remote Similarity	NPD7838	Discovery
0.6211	Remote Similarity	NPD3672	Approved
0.62	Remote Similarity	NPD7640	Approved
0.62	Remote Similarity	NPD7639	Approved
0.6197	Remote Similarity	NPD3173	Approved
0.6186	Remote Similarity	NPD7748	Approved
0.6186	Remote Similarity	NPD5282	Discontinued
0.617	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD5737	Approved
0.617	Remote Similarity	NPD6672	Approved
0.617	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD8264	Approved
0.6162	Remote Similarity	NPD6084	Phase 2
0.6162	Remote Similarity	NPD6083	Phase 2
0.6146	Remote Similarity	NPD7515	Phase 2
0.6129	Remote Similarity	NPD4623	Approved
0.6129	Remote Similarity	NPD4519	Discontinued
0.6122	Remote Similarity	NPD5695	Phase 3
0.6105	Remote Similarity	NPD1695	Approved
0.61	Remote Similarity	NPD7638	Approved
0.6095	Remote Similarity	NPD6686	Approved
0.6087	Remote Similarity	NPD3133	Approved
0.6087	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3666	Approved
0.6087	Remote Similarity	NPD3665	Phase 1
0.6056	Remote Similarity	NPD5343	Approved
0.6056	Remote Similarity	NPD622	Approved
0.6053	Remote Similarity	NPD4219	Approved
0.6027	Remote Similarity	NPD6927	Phase 3
0.6022	Remote Similarity	NPD1696	Phase 3
0.6019	Remote Similarity	NPD6053	Discontinued
0.6019	Remote Similarity	NPD6647	Phase 2
0.6018	Remote Similarity	NPD8517	Approved
0.6018	Remote Similarity	NPD8513	Phase 3
0.6018	Remote Similarity	NPD8515	Approved
0.6018	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD3174	Discontinued
0.6	Remote Similarity	NPD5697	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.5981	Remote Similarity	NPD6371	Approved
0.5981	Remote Similarity	NPD6420	Discontinued
0.598	Remote Similarity	NPD5344	Discontinued
0.5979	Remote Similarity	NPD6079	Approved
0.5978	Remote Similarity	NPD6110	Phase 1
0.5976	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3704	Approved
0.5962	Remote Similarity	NPD5909	Discontinued
0.5957	Remote Similarity	NPD6098	Approved
0.5957	Remote Similarity	NPD3618	Phase 1
0.5957	Remote Similarity	NPD5279	Phase 3
0.5955	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7115	Discovery
0.5943	Remote Similarity	NPD6011	Approved
0.5943	Remote Similarity	NPD6881	Approved
0.5943	Remote Similarity	NPD6899	Approved
0.5941	Remote Similarity	NPD5696	Approved
0.5938	Remote Similarity	NPD5328	Approved
0.5934	Remote Similarity	NPD857	Phase 3
0.5914	Remote Similarity	NPD3668	Phase 3
0.5905	Remote Similarity	NPD5739	Approved
0.5905	Remote Similarity	NPD7128	Approved
0.5905	Remote Similarity	NPD6402	Approved
0.5905	Remote Similarity	NPD6675	Approved
0.59	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.59	Remote Similarity	NPD1989	Approved
0.59	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6012	Approved
0.5888	Remote Similarity	NPD6013	Approved
0.5888	Remote Similarity	NPD6014	Approved
0.5882	Remote Similarity	NPD6648	Approved
0.5876	Remote Similarity	NPD1086	Approved
0.5876	Remote Similarity	NPD1090	Approved
0.5876	Remote Similarity	NPD1089	Approved
0.5876	Remote Similarity	NPD5207	Approved
0.5859	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7900	Approved
0.5856	Remote Similarity	NPD2629	Approved
0.5851	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD7290	Approved
0.5833	Remote Similarity	NPD7102	Approved
0.5833	Remote Similarity	NPD6883	Approved
0.5833	Remote Similarity	NPD5208	Approved
0.5824	Remote Similarity	NPD7514	Phase 3
0.5824	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7332	Phase 2
0.5823	Remote Similarity	NPD3198	Approved
0.5816	Remote Similarity	NPD5281	Approved
0.5816	Remote Similarity	NPD5693	Phase 1
0.5816	Remote Similarity	NPD5694	Approved
0.5816	Remote Similarity	NPD5284	Approved
0.5806	Remote Similarity	NPD6695	Phase 3
0.5802	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7320	Approved
0.578	Remote Similarity	NPD6617	Approved
0.578	Remote Similarity	NPD6650	Approved
0.578	Remote Similarity	NPD6869	Approved
0.578	Remote Similarity	NPD8130	Phase 1
0.578	Remote Similarity	NPD6847	Approved
0.578	Remote Similarity	NPD6649	Approved
0.5778	Remote Similarity	NPD7145	Approved
0.5775	Remote Similarity	NPD634	Phase 3
0.5775	Remote Similarity	NPD4222	Approved
0.5773	Remote Similarity	NPD800	Approved
0.5773	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4753	Phase 2
0.5773	Remote Similarity	NPD5346	Phase 2
0.5773	Remote Similarity	NPD6904	Approved
0.5773	Remote Similarity	NPD6673	Approved
0.5773	Remote Similarity	NPD5347	Phase 2
0.5773	Remote Similarity	NPD6080	Approved
0.5769	Remote Similarity	NPD5211	Phase 2
0.5763	Remote Similarity	NPD8074	Phase 3
0.5761	Remote Similarity	NPD6902	Approved
0.5758	Remote Similarity	NPD1088	Approved
0.5755	Remote Similarity	NPD5048	Discontinued
0.5745	Remote Similarity	NPD7338	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data