NPASS Compound

Structure

NPC469914 OpenBabel07101719522D 30 30 0 0 1 0 0 0 0 0999 V2000 -5.1962 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 2 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 -0.8660 0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 5 23 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 23 26 1 0 0 0 0 24 26 1 0 0 0 0 25 28 2 0 0 0 0 26 29 2 0 0 0 0 27 6 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.34
Volume:	482.816
LogP:	7.839
LogD:	6.253
LogS:	-4.665
# Rotatable Bonds:	14
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	3.879
Fsp3:	0.704
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.99
MDCK Permeability:	1.4665534763480537e-05
Pgp-inhibitor:	0.912
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.667
Plasma Protein Binding (PPB):	100.33556365966797%
Volume Distribution (VD):	4.654
Pgp-substrate:	2.2614142894744873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.516
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.838
CYP2C19-substrate:	0.482
CYP2C9-inhibitor:	0.575
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	7.186
Half-life (T1/2):	0.224

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.843
Skin Sensitization:	0.971
Carcinogencity:	0.033
Eye Corrosion:	0.552
Eye Irritation:	0.945
Respiratory Toxicity:	0.602

Download Data

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

Natural Product: NPC469914

Natural Product ID:	NPC469914
*Common Name:**	2-[(3R,7R,11R)-3-Hydroxy-3,7,11,15-Tetramethylhexadecyl]-6-Methylcyclohexa-2,5-Diene-1,4-Dione
IUPAC Name:	2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-6-methylcyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	YSJVXRLCNZMPFO-VHFRWLAGSA-N
Standard InCHI:	InChI=1S/C27H46O3/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6,30)17-15-24-19-25(28)18-23(5)26(24)29/h18-22,30H,7-17H2,1-6H3/t21-,22-,27-/m1/s1
SMILES:	C[C@H](CCC[C@@H](CCCC(C)C)C)CCC[C@](CCC1=CC(=O)C=C(C1=O)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258198
PubChem CID:	49765076
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
NPO33001	macroalgae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20801038]

☑ 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
MIC	3

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10000.0	nM	PMID[448244]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500000.0	nM	PMID[448244]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	500000.0	nM	PMID[448244]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500000.0	nM	PMID[448244]

☑ 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 NPC469914 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	178
0.1-0.2	1443
0.2-0.3	7753
0.3-0.4	15870
0.4-0.5	9219
0.5-0.6	5699
0.6-0.7	2152
0.7-0.8	369
0.8-0.85	11
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC61473
0.8261	Intermediate Similarity	NPC278895
0.8209	Intermediate Similarity	NPC477707
0.8133	Intermediate Similarity	NPC471409
0.8133	Intermediate Similarity	NPC275494
0.8116	Intermediate Similarity	NPC197089
0.8108	Intermediate Similarity	NPC186554
0.8108	Intermediate Similarity	NPC76966
0.7975	Intermediate Similarity	NPC251170
0.7975	Intermediate Similarity	NPC476412
0.7973	Intermediate Similarity	NPC251435
0.7945	Intermediate Similarity	NPC300940
0.7941	Intermediate Similarity	NPC477830
0.7922	Intermediate Similarity	NPC476809
0.7895	Intermediate Similarity	NPC207772
0.7895	Intermediate Similarity	NPC74410
0.7895	Intermediate Similarity	NPC62336
0.7887	Intermediate Similarity	NPC476614
0.7867	Intermediate Similarity	NPC470525
0.7867	Intermediate Similarity	NPC472305
0.7826	Intermediate Similarity	NPC7029
0.7821	Intermediate Similarity	NPC472684
0.7821	Intermediate Similarity	NPC119229
0.7821	Intermediate Similarity	NPC278459
0.7821	Intermediate Similarity	NPC44963
0.7821	Intermediate Similarity	NPC473217
0.7808	Intermediate Similarity	NPC469737
0.7792	Intermediate Similarity	NPC469617
0.7778	Intermediate Similarity	NPC10758
0.7778	Intermediate Similarity	NPC250928
0.7763	Intermediate Similarity	NPC257666
0.7763	Intermediate Similarity	NPC34110
0.7763	Intermediate Similarity	NPC471061
0.7763	Intermediate Similarity	NPC165711
0.7763	Intermediate Similarity	NPC266193
0.7763	Intermediate Similarity	NPC97377
0.7733	Intermediate Similarity	NPC474011
0.7733	Intermediate Similarity	NPC114236
0.7722	Intermediate Similarity	NPC302661
0.7722	Intermediate Similarity	NPC238991
0.7714	Intermediate Similarity	NPC474304
0.7714	Intermediate Similarity	NPC474329
0.7711	Intermediate Similarity	NPC472973
0.7703	Intermediate Similarity	NPC247586
0.7692	Intermediate Similarity	NPC2482
0.7692	Intermediate Similarity	NPC108955
0.7683	Intermediate Similarity	NPC476409
0.7681	Intermediate Similarity	NPC143168
0.7681	Intermediate Similarity	NPC53109
0.7662	Intermediate Similarity	NPC475994
0.7662	Intermediate Similarity	NPC189485
0.7662	Intermediate Similarity	NPC80088
0.7662	Intermediate Similarity	NPC253561
0.7662	Intermediate Similarity	NPC231739
0.7662	Intermediate Similarity	NPC19443
0.7632	Intermediate Similarity	NPC469646
0.7632	Intermediate Similarity	NPC151622
0.7632	Intermediate Similarity	NPC263582
0.7632	Intermediate Similarity	NPC7629
0.7632	Intermediate Similarity	NPC180886
0.7625	Intermediate Similarity	NPC64600
0.7625	Intermediate Similarity	NPC102197
0.7606	Intermediate Similarity	NPC100719
0.7606	Intermediate Similarity	NPC166791
0.7606	Intermediate Similarity	NPC322035
0.7606	Intermediate Similarity	NPC137163
0.7595	Intermediate Similarity	NPC477372
0.7595	Intermediate Similarity	NPC471898
0.7595	Intermediate Similarity	NPC189237
0.7595	Intermediate Similarity	NPC55869
0.7571	Intermediate Similarity	NPC234767
0.7571	Intermediate Similarity	NPC150162
0.7568	Intermediate Similarity	NPC288667
0.7568	Intermediate Similarity	NPC144627
0.7568	Intermediate Similarity	NPC84790
0.7534	Intermediate Similarity	NPC261398
0.7534	Intermediate Similarity	NPC67608
0.7532	Intermediate Similarity	NPC197659
0.7532	Intermediate Similarity	NPC276769
0.7531	Intermediate Similarity	NPC9868
0.7529	Intermediate Similarity	NPC472975
0.7529	Intermediate Similarity	NPC472978
0.75	Intermediate Similarity	NPC106851
0.75	Intermediate Similarity	NPC263161
0.75	Intermediate Similarity	NPC472256
0.75	Intermediate Similarity	NPC123912
0.75	Intermediate Similarity	NPC274927
0.75	Intermediate Similarity	NPC103486
0.75	Intermediate Similarity	NPC193347
0.7468	Intermediate Similarity	NPC164218
0.7468	Intermediate Similarity	NPC45495
0.7468	Intermediate Similarity	NPC469637
0.7468	Intermediate Similarity	NPC233377
0.7468	Intermediate Similarity	NPC472301
0.7468	Intermediate Similarity	NPC103634
0.7467	Intermediate Similarity	NPC35656
0.7439	Intermediate Similarity	NPC474537
0.7439	Intermediate Similarity	NPC469948
0.7439	Intermediate Similarity	NPC29447
0.7439	Intermediate Similarity	NPC469993
0.7436	Intermediate Similarity	NPC478246
0.7436	Intermediate Similarity	NPC478247
0.7436	Intermediate Similarity	NPC179028
0.7436	Intermediate Similarity	NPC321514
0.7432	Intermediate Similarity	NPC94743
0.7432	Intermediate Similarity	NPC291062
0.7412	Intermediate Similarity	NPC476369
0.7412	Intermediate Similarity	NPC476437
0.7407	Intermediate Similarity	NPC49019
0.7407	Intermediate Similarity	NPC476082
0.7407	Intermediate Similarity	NPC278648
0.7407	Intermediate Similarity	NPC53733
0.7407	Intermediate Similarity	NPC11620
0.7403	Intermediate Similarity	NPC215481
0.7403	Intermediate Similarity	NPC271070
0.7403	Intermediate Similarity	NPC110725
0.7397	Intermediate Similarity	NPC146376
0.7397	Intermediate Similarity	NPC263382
0.7397	Intermediate Similarity	NPC125578
0.7391	Intermediate Similarity	NPC40206
0.7381	Intermediate Similarity	NPC158778
0.7381	Intermediate Similarity	NPC470524
0.7375	Intermediate Similarity	NPC116797
0.7375	Intermediate Similarity	NPC474353
0.7375	Intermediate Similarity	NPC90055
0.7375	Intermediate Similarity	NPC225515
0.7375	Intermediate Similarity	NPC478262
0.7375	Intermediate Similarity	NPC171665
0.7375	Intermediate Similarity	NPC226068
0.7375	Intermediate Similarity	NPC121984
0.7375	Intermediate Similarity	NPC275766
0.7375	Intermediate Similarity	NPC136150
0.7368	Intermediate Similarity	NPC470299
0.7368	Intermediate Similarity	NPC7382
0.7368	Intermediate Similarity	NPC160540
0.7361	Intermediate Similarity	NPC142423
0.7361	Intermediate Similarity	NPC308294
0.7356	Intermediate Similarity	NPC472976
0.7356	Intermediate Similarity	NPC472977
0.7349	Intermediate Similarity	NPC472974
0.7342	Intermediate Similarity	NPC84185
0.7342	Intermediate Similarity	NPC308038
0.7342	Intermediate Similarity	NPC66677
0.7342	Intermediate Similarity	NPC181195
0.7342	Intermediate Similarity	NPC113363
0.7342	Intermediate Similarity	NPC231431
0.7342	Intermediate Similarity	NPC308545
0.7342	Intermediate Similarity	NPC261125
0.7342	Intermediate Similarity	NPC215843
0.7342	Intermediate Similarity	NPC82488
0.7342	Intermediate Similarity	NPC170394
0.7342	Intermediate Similarity	NPC7232
0.7342	Intermediate Similarity	NPC471890
0.7342	Intermediate Similarity	NPC477371
0.7333	Intermediate Similarity	NPC160817
0.7333	Intermediate Similarity	NPC29328
0.7326	Intermediate Similarity	NPC45579
0.7317	Intermediate Similarity	NPC214043
0.7317	Intermediate Similarity	NPC72464
0.7317	Intermediate Similarity	NPC473246
0.7317	Intermediate Similarity	NPC144258
0.7317	Intermediate Similarity	NPC230527
0.7317	Intermediate Similarity	NPC96095
0.7317	Intermediate Similarity	NPC85774
0.7317	Intermediate Similarity	NPC7927
0.7317	Intermediate Similarity	NPC470812
0.7308	Intermediate Similarity	NPC472014
0.7308	Intermediate Similarity	NPC325946
0.7308	Intermediate Similarity	NPC266124
0.7308	Intermediate Similarity	NPC211279
0.7297	Intermediate Similarity	NPC477448
0.7297	Intermediate Similarity	NPC474060
0.7297	Intermediate Similarity	NPC262673
0.7297	Intermediate Similarity	NPC477449
0.7294	Intermediate Similarity	NPC41217
0.7294	Intermediate Similarity	NPC262043
0.7294	Intermediate Similarity	NPC86319
0.7294	Intermediate Similarity	NPC184663
0.7294	Intermediate Similarity	NPC275740
0.7286	Intermediate Similarity	NPC125312
0.7286	Intermediate Similarity	NPC174560
0.7284	Intermediate Similarity	NPC477270
0.7284	Intermediate Similarity	NPC320514
0.7284	Intermediate Similarity	NPC129080
0.7284	Intermediate Similarity	NPC477271
0.7284	Intermediate Similarity	NPC20262
0.7284	Intermediate Similarity	NPC256750
0.7284	Intermediate Similarity	NPC133844
0.7284	Intermediate Similarity	NPC477269
0.7284	Intermediate Similarity	NPC279186
0.7273	Intermediate Similarity	NPC77501
0.7273	Intermediate Similarity	NPC216791
0.7273	Intermediate Similarity	NPC472327
0.7273	Intermediate Similarity	NPC244166
0.7273	Intermediate Similarity	NPC89374
0.7273	Intermediate Similarity	NPC476795
0.7262	Intermediate Similarity	NPC136948
0.7262	Intermediate Similarity	NPC93778
0.7262	Intermediate Similarity	NPC471792
0.7262	Intermediate Similarity	NPC470523

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 NPC469914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2190
0.2-0.3	3997
0.3-0.4	1984
0.4-0.5	463
0.5-0.6	248
0.6-0.7	99
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9531	High Similarity	NPD7331	Phase 2
0.9375	High Similarity	NPD7341	Phase 2
0.7692	Intermediate Similarity	NPD4695	Discontinued
0.7681	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4221	Approved
0.75	Intermediate Similarity	NPD4223	Phase 3
0.7439	Intermediate Similarity	NPD5329	Approved
0.7349	Intermediate Similarity	NPD5690	Phase 2
0.7326	Intermediate Similarity	NPD6079	Approved
0.7317	Intermediate Similarity	NPD4197	Approved
0.7294	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD4519	Discontinued
0.7143	Intermediate Similarity	NPD4688	Approved
0.7143	Intermediate Similarity	NPD5280	Approved
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD4623	Approved
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4694	Approved
0.7123	Intermediate Similarity	NPD6108	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3133	Approved
0.7108	Intermediate Similarity	NPD3665	Phase 1
0.7108	Intermediate Similarity	NPD3666	Approved
0.7073	Intermediate Similarity	NPD4800	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD3617	Approved
0.6977	Remote Similarity	NPD4518	Approved
0.6941	Remote Similarity	NPD5279	Phase 3
0.6941	Remote Similarity	NPD3618	Phase 1
0.6914	Remote Similarity	NPD4195	Approved
0.6905	Remote Similarity	NPD4786	Approved
0.6897	Remote Similarity	NPD4753	Phase 2
0.6867	Remote Similarity	NPD3667	Approved
0.6829	Remote Similarity	NPD5368	Approved
0.6818	Remote Similarity	NPD4096	Approved
0.6813	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5222	Approved
0.6813	Remote Similarity	NPD5221	Approved
0.6774	Remote Similarity	NPD5286	Approved
0.6774	Remote Similarity	NPD4696	Approved
0.6774	Remote Similarity	NPD5285	Approved
0.6765	Remote Similarity	NPD3194	Approved
0.6765	Remote Similarity	NPD4266	Approved
0.6765	Remote Similarity	NPD3196	Approved
0.6765	Remote Similarity	NPD3195	Phase 2
0.6753	Remote Similarity	NPD4691	Approved
0.6742	Remote Similarity	NPD5281	Approved
0.6742	Remote Similarity	NPD5284	Approved
0.6742	Remote Similarity	NPD7515	Phase 2
0.6739	Remote Similarity	NPD4755	Approved
0.6739	Remote Similarity	NPD5173	Approved
0.6705	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6101	Approved
0.6703	Remote Similarity	NPD4629	Approved
0.6703	Remote Similarity	NPD5210	Approved
0.6702	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD4202	Approved
0.6632	Remote Similarity	NPD5226	Approved
0.6632	Remote Similarity	NPD5224	Approved
0.6632	Remote Similarity	NPD5211	Phase 2
0.6632	Remote Similarity	NPD5225	Approved
0.6632	Remote Similarity	NPD4633	Approved
0.663	Remote Similarity	NPD4697	Phase 3
0.663	Remote Similarity	NPD7614	Phase 1
0.6628	Remote Similarity	NPD5363	Approved
0.6627	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4137	Phase 3
0.6618	Remote Similarity	NPD3172	Approved
0.6596	Remote Similarity	NPD4700	Approved
0.6593	Remote Similarity	NPD7748	Approved
0.6588	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD5175	Approved
0.6562	Remote Similarity	NPD5174	Approved
0.6559	Remote Similarity	NPD6084	Phase 2
0.6559	Remote Similarity	NPD6083	Phase 2
0.6556	Remote Similarity	NPD6411	Approved
0.6552	Remote Similarity	NPD7334	Approved
0.6552	Remote Similarity	NPD7521	Approved
0.6552	Remote Similarity	NPD6684	Approved
0.6552	Remote Similarity	NPD5330	Approved
0.6552	Remote Similarity	NPD6409	Approved
0.6552	Remote Similarity	NPD7146	Approved
0.6548	Remote Similarity	NPD4692	Approved
0.6548	Remote Similarity	NPD4139	Approved
0.6548	Remote Similarity	NPD5369	Approved
0.6538	Remote Similarity	NPD4747	Approved
0.6522	Remote Similarity	NPD5695	Phase 3
0.6517	Remote Similarity	NPD6673	Approved
0.6517	Remote Similarity	NPD6080	Approved
0.6517	Remote Similarity	NPD6904	Approved
0.65	Remote Similarity	NPD5733	Approved
0.65	Remote Similarity	NPD4058	Approved
0.6495	Remote Similarity	NPD5141	Approved
0.6484	Remote Similarity	NPD5133	Approved
0.6484	Remote Similarity	NPD5778	Approved
0.6484	Remote Similarity	NPD5779	Approved
0.6465	Remote Similarity	NPD6899	Approved
0.6465	Remote Similarity	NPD6881	Approved
0.6456	Remote Similarity	NPD5276	Approved
0.6437	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6413	Remote Similarity	NPD5282	Discontinued
0.6404	Remote Similarity	NPD5208	Approved
0.6404	Remote Similarity	NPD6903	Approved
0.6404	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6672	Approved
0.6392	Remote Similarity	NPD4754	Approved
0.6389	Remote Similarity	NPD287	Approved
0.6386	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7902	Approved
0.6374	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD6098	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6344	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6883	Approved
0.6337	Remote Similarity	NPD7290	Approved
0.6337	Remote Similarity	NPD7102	Approved
0.6324	Remote Similarity	NPD29	Approved
0.6324	Remote Similarity	NPD28	Approved
0.6322	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD5696	Approved
0.6304	Remote Similarity	NPD6399	Phase 3
0.63	Remote Similarity	NPD4729	Approved
0.63	Remote Similarity	NPD6011	Approved
0.63	Remote Similarity	NPD4730	Approved
0.63	Remote Similarity	NPD7320	Approved
0.63	Remote Similarity	NPD5128	Approved
0.6296	Remote Similarity	NPD4687	Approved
0.6289	Remote Similarity	NPD5091	Approved
0.6279	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4270	Approved
0.6279	Remote Similarity	NPD4269	Approved
0.6275	Remote Similarity	NPD6650	Approved
0.6275	Remote Similarity	NPD6847	Approved
0.6275	Remote Similarity	NPD6649	Approved
0.6275	Remote Similarity	NPD6869	Approved
0.6275	Remote Similarity	NPD6617	Approved
0.6275	Remote Similarity	NPD8130	Phase 1
0.6264	Remote Similarity	NPD6698	Approved
0.6264	Remote Similarity	NPD5692	Phase 3
0.6264	Remote Similarity	NPD46	Approved
0.6264	Remote Similarity	NPD5207	Approved
0.6264	Remote Similarity	NPD5785	Approved
0.6263	Remote Similarity	NPD4768	Approved
0.6263	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4243	Approved
0.625	Remote Similarity	NPD1694	Approved
0.6238	Remote Similarity	NPD6012	Approved
0.6238	Remote Similarity	NPD6014	Approved
0.6238	Remote Similarity	NPD6373	Approved
0.6238	Remote Similarity	NPD6372	Approved
0.6238	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8039	Approved
0.6214	Remote Similarity	NPD8297	Approved
0.6214	Remote Similarity	NPD6882	Approved
0.6207	Remote Similarity	NPD6110	Phase 1
0.6207	Remote Similarity	NPD7154	Phase 3
0.6207	Remote Similarity	NPD5362	Discontinued
0.62	Remote Similarity	NPD5701	Approved
0.6197	Remote Similarity	NPD342	Phase 1
0.6196	Remote Similarity	NPD5694	Approved
0.6196	Remote Similarity	NPD5693	Phase 1
0.6184	Remote Similarity	NPD3197	Phase 1
0.618	Remote Similarity	NPD6422	Discontinued
0.6176	Remote Similarity	NPD5251	Approved
0.6176	Remote Similarity	NPD4634	Approved
0.6176	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5249	Phase 3
0.6176	Remote Similarity	NPD5250	Approved
0.6176	Remote Similarity	NPD5135	Approved
0.6176	Remote Similarity	NPD5169	Approved
0.6176	Remote Similarity	NPD5247	Approved
0.6176	Remote Similarity	NPD5248	Approved
0.617	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5168	Approved
0.6133	Remote Similarity	NPD368	Approved
0.6117	Remote Similarity	NPD5216	Approved
0.6117	Remote Similarity	NPD5217	Approved
0.6117	Remote Similarity	NPD5215	Approved
0.6117	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5127	Approved
0.6105	Remote Similarity	NPD7732	Phase 3
0.6098	Remote Similarity	NPD6924	Approved
0.6098	Remote Similarity	NPD6926	Approved
0.6098	Remote Similarity	NPD4784	Approved
0.6098	Remote Similarity	NPD4785	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