NPASS Compound

Structure

CID155198 OpenBabel06191715522D 23 24 0 0 1 0 0 0 0 0999 V2000 -3.9576 1.9212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3880 0.3150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3514 2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3114 2.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 -0.9518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1758 1.1758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7092 0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7819 0.7454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9273 0.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1030 1.4242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6061 -0.4304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4942 3.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3515 2.3515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3576 -1.3576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	4.802
LogD:	3.92
LogS:	-3.62
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.03
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.9002573026227765e-05
Pgp-inhibitor:	0.522
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	75.60657501220703%
Volume Distribution (VD):	1.509
Pgp-substrate:	12.432914733886719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.597
CYP2C19-inhibitor:	0.225
CYP2C19-substrate:	0.347
CYP2C9-inhibitor:	0.381
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.748
CYP2D6-substrate:	0.612
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	16.377
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.946
Carcinogencity:	0.426
Eye Corrosion:	0.691
Eye Irritation:	0.94
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC155198

Natural Product ID:	NPC155198
*Common Name:**	7,8-Seco-Para-Ferruginone
IUPAC Name:	2-[(1S,2S)-2-(3,6-dioxo-4-propan-2-ylcyclohexa-1,4-dien-1-yl)-2,6,6-trimethylcyclohexyl]acetaldehyde
Synonyms:
Standard InCHIKey:	JCLGBJLXHLKJPT-AZUAARDMSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-13(2)14-11-17(23)15(12-16(14)22)20(5)9-6-8-19(3,4)18(20)7-10-21/h10-13,18H,6-9H2,1-5H3/t18-,20+/m0/s1
SMILES:	CC(C)C1=CC(=O)C(=CC1=O)[C@@]1(C)CCCC(C)(C)[C@@H]1CC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455370
PubChem CID:	10018666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19148	Gouania tomentosa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21396	Spongia vermicularis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	20000.0	nM	PMID[536323]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	15000.0	nM	PMID[536323]

☑ 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 NPC155198 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	182
0.1-0.2	1894
0.2-0.3	10467
0.3-0.4	14807
0.4-0.5	8261
0.5-0.6	4874
0.6-0.7	1806
0.7-0.8	350
0.8-0.85	38
0.85-0.9	11
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC474562
0.9231	High Similarity	NPC290350
0.9231	High Similarity	NPC4370
0.8889	High Similarity	NPC127582
0.8806	High Similarity	NPC260474
0.8806	High Similarity	NPC188292
0.8769	High Similarity	NPC169275
0.8769	High Similarity	NPC52449
0.875	High Similarity	NPC115515
0.8732	High Similarity	NPC469796
0.8732	High Similarity	NPC469793
0.8714	High Similarity	NPC219232
0.8714	High Similarity	NPC211641
0.8714	High Similarity	NPC128346
0.8636	High Similarity	NPC251118
0.863	High Similarity	NPC90965
0.863	High Similarity	NPC170793
0.8615	High Similarity	NPC288253
0.8551	High Similarity	NPC2634
0.8551	High Similarity	NPC265782
0.8551	High Similarity	NPC251929
0.8529	High Similarity	NPC87141
0.8529	High Similarity	NPC310992
0.8514	High Similarity	NPC474509
0.8485	Intermediate Similarity	NPC285371
0.8485	Intermediate Similarity	NPC212210
0.8485	Intermediate Similarity	NPC475124
0.8472	Intermediate Similarity	NPC19907
0.8438	Intermediate Similarity	NPC472304
0.8438	Intermediate Similarity	NPC276764
0.8429	Intermediate Similarity	NPC54123
0.8406	Intermediate Similarity	NPC139397
0.8406	Intermediate Similarity	NPC256846
0.8382	Intermediate Similarity	NPC193770
0.8358	Intermediate Similarity	NPC268039
0.8333	Intermediate Similarity	NPC202118
0.8333	Intermediate Similarity	NPC197238
0.831	Intermediate Similarity	NPC474228
0.831	Intermediate Similarity	NPC303613
0.8286	Intermediate Similarity	NPC307176
0.8286	Intermediate Similarity	NPC260040
0.8281	Intermediate Similarity	NPC27610
0.8281	Intermediate Similarity	NPC56905
0.8281	Intermediate Similarity	NPC311852
0.8243	Intermediate Similarity	NPC228911
0.8209	Intermediate Similarity	NPC469662
0.8194	Intermediate Similarity	NPC20025
0.8194	Intermediate Similarity	NPC309852
0.8182	Intermediate Similarity	NPC60565
0.8182	Intermediate Similarity	NPC213152
0.8169	Intermediate Similarity	NPC304983
0.8169	Intermediate Similarity	NPC190035
0.8158	Intermediate Similarity	NPC90055
0.8133	Intermediate Similarity	NPC476177
0.8116	Intermediate Similarity	NPC475523
0.8082	Intermediate Similarity	NPC65650
0.8082	Intermediate Similarity	NPC476346
0.8056	Intermediate Similarity	NPC56747
0.8056	Intermediate Similarity	NPC180015
0.8056	Intermediate Similarity	NPC130016
0.8056	Intermediate Similarity	NPC251705
0.8056	Intermediate Similarity	NPC470044
0.8056	Intermediate Similarity	NPC109576
0.8056	Intermediate Similarity	NPC470045
0.8052	Intermediate Similarity	NPC470813
0.8028	Intermediate Similarity	NPC35734
0.8028	Intermediate Similarity	NPC159577
0.8028	Intermediate Similarity	NPC282593
0.8	Intermediate Similarity	NPC59436
0.8	Intermediate Similarity	NPC60772
0.8	Intermediate Similarity	NPC62336
0.7973	Intermediate Similarity	NPC263582
0.7973	Intermediate Similarity	NPC69408
0.7973	Intermediate Similarity	NPC470525
0.7973	Intermediate Similarity	NPC1254
0.7945	Intermediate Similarity	NPC474796
0.7945	Intermediate Similarity	NPC329866
0.7945	Intermediate Similarity	NPC255021
0.7945	Intermediate Similarity	NPC474797
0.7941	Intermediate Similarity	NPC6697
0.7937	Intermediate Similarity	NPC250539
0.7922	Intermediate Similarity	NPC149237
0.7922	Intermediate Similarity	NPC116797
0.7917	Intermediate Similarity	NPC115023
0.7917	Intermediate Similarity	NPC5701
0.7917	Intermediate Similarity	NPC305501
0.7917	Intermediate Similarity	NPC225467
0.7917	Intermediate Similarity	NPC234707
0.7917	Intermediate Similarity	NPC21944
0.7917	Intermediate Similarity	NPC133253
0.7887	Intermediate Similarity	NPC162867
0.7887	Intermediate Similarity	NPC61702
0.7887	Intermediate Similarity	NPC286814
0.7879	Intermediate Similarity	NPC259261
0.7875	Intermediate Similarity	NPC168248
0.7867	Intermediate Similarity	NPC472300
0.7846	Intermediate Similarity	NPC115385
0.7846	Intermediate Similarity	NPC192427
0.7838	Intermediate Similarity	NPC293803
0.7838	Intermediate Similarity	NPC473171
0.7826	Intermediate Similarity	NPC470329
0.7821	Intermediate Similarity	NPC103486
0.7808	Intermediate Similarity	NPC144947
0.7794	Intermediate Similarity	NPC32285
0.7794	Intermediate Similarity	NPC165695
0.7792	Intermediate Similarity	NPC2482
0.7792	Intermediate Similarity	NPC472478
0.7778	Intermediate Similarity	NPC23117
0.7763	Intermediate Similarity	NPC253561
0.7763	Intermediate Similarity	NPC189485
0.7763	Intermediate Similarity	NPC475994
0.7763	Intermediate Similarity	NPC80088
0.7761	Intermediate Similarity	NPC25853
0.775	Intermediate Similarity	NPC33881
0.7746	Intermediate Similarity	NPC39157
0.7746	Intermediate Similarity	NPC20610
0.7746	Intermediate Similarity	NPC82477
0.7746	Intermediate Similarity	NPC142754
0.7746	Intermediate Similarity	NPC296697
0.7733	Intermediate Similarity	NPC180886
0.7727	Intermediate Similarity	NPC308108
0.7727	Intermediate Similarity	NPC170799
0.7727	Intermediate Similarity	NPC266295
0.7727	Intermediate Similarity	NPC30215
0.7727	Intermediate Similarity	NPC94991
0.7722	Intermediate Similarity	NPC118423
0.7722	Intermediate Similarity	NPC307258
0.7722	Intermediate Similarity	NPC470165
0.7714	Intermediate Similarity	NPC323005
0.7703	Intermediate Similarity	NPC159497
0.7703	Intermediate Similarity	NPC168975
0.7703	Intermediate Similarity	NPC238146
0.7703	Intermediate Similarity	NPC75485
0.7692	Intermediate Similarity	NPC99308
0.7692	Intermediate Similarity	NPC474085
0.7692	Intermediate Similarity	NPC121984
0.7681	Intermediate Similarity	NPC4638
0.7671	Intermediate Similarity	NPC181204
0.7662	Intermediate Similarity	NPC27817
0.7662	Intermediate Similarity	NPC152061
0.7662	Intermediate Similarity	NPC308038
0.7662	Intermediate Similarity	NPC472490
0.7656	Intermediate Similarity	NPC209431
0.7656	Intermediate Similarity	NPC100809
0.7647	Intermediate Similarity	NPC97322
0.7647	Intermediate Similarity	NPC475795
0.7639	Intermediate Similarity	NPC182815
0.7632	Intermediate Similarity	NPC97377
0.7632	Intermediate Similarity	NPC197659
0.7632	Intermediate Similarity	NPC325946
0.7632	Intermediate Similarity	NPC165711
0.7625	Intermediate Similarity	NPC476412
0.7625	Intermediate Similarity	NPC470812
0.7619	Intermediate Similarity	NPC22182
0.7612	Intermediate Similarity	NPC96551
0.7612	Intermediate Similarity	NPC285594
0.7606	Intermediate Similarity	NPC220210
0.7606	Intermediate Similarity	NPC20181
0.76	Intermediate Similarity	NPC255650
0.76	Intermediate Similarity	NPC114236
0.7595	Intermediate Similarity	NPC94200
0.7595	Intermediate Similarity	NPC268122
0.7595	Intermediate Similarity	NPC142683
0.759	Intermediate Similarity	NPC469546
0.759	Intermediate Similarity	NPC184663
0.759	Intermediate Similarity	NPC472983
0.7576	Intermediate Similarity	NPC208749
0.7576	Intermediate Similarity	NPC321568
0.7576	Intermediate Similarity	NPC281986
0.7576	Intermediate Similarity	NPC22019
0.7568	Intermediate Similarity	NPC474488
0.7564	Intermediate Similarity	NPC471514
0.7564	Intermediate Similarity	NPC472301
0.7564	Intermediate Similarity	NPC474956
0.7564	Intermediate Similarity	NPC108955
0.7564	Intermediate Similarity	NPC476809
0.7538	Intermediate Similarity	NPC200258
0.7538	Intermediate Similarity	NPC188789
0.7534	Intermediate Similarity	NPC246722
0.7534	Intermediate Similarity	NPC151045
0.7532	Intermediate Similarity	NPC275494
0.7532	Intermediate Similarity	NPC469996
0.7532	Intermediate Similarity	NPC82635
0.7532	Intermediate Similarity	NPC74410
0.7532	Intermediate Similarity	NPC471409
0.7531	Intermediate Similarity	NPC70685
0.7531	Intermediate Similarity	NPC133652
0.7531	Intermediate Similarity	NPC255174
0.7531	Intermediate Similarity	NPC476426
0.7531	Intermediate Similarity	NPC2709
0.7531	Intermediate Similarity	NPC189311
0.75	Intermediate Similarity	NPC110725
0.75	Intermediate Similarity	NPC41539
0.75	Intermediate Similarity	NPC268564
0.75	Intermediate Similarity	NPC191684
0.75	Intermediate Similarity	NPC14002
0.75	Intermediate Similarity	NPC40353
0.747	Intermediate Similarity	NPC473229
0.747	Intermediate Similarity	NPC206060
0.7468	Intermediate Similarity	NPC55869

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 NPC155198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2254
0.2-0.3	4393
0.3-0.4	1664
0.4-0.5	355
0.5-0.6	205
0.6-0.7	94
0.7-0.8	14
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8551	High Similarity	NPD4691	Approved
0.8406	Intermediate Similarity	NPD4137	Phase 3
0.8286	Intermediate Similarity	NPD4747	Approved
0.8194	Intermediate Similarity	NPD4058	Approved
0.8169	Intermediate Similarity	NPD5276	Approved
0.7945	Intermediate Similarity	NPD4687	Approved
0.7945	Intermediate Similarity	NPD5733	Approved
0.7746	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD287	Approved
0.7564	Intermediate Similarity	NPD4695	Discontinued
0.7407	Intermediate Similarity	NPD3133	Approved
0.7407	Intermediate Similarity	NPD3666	Approved
0.7407	Intermediate Similarity	NPD3665	Phase 1
0.7284	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8028	Phase 2
0.7229	Intermediate Similarity	NPD5279	Phase 3
0.7229	Intermediate Similarity	NPD7334	Approved
0.7229	Intermediate Similarity	NPD7146	Approved
0.7229	Intermediate Similarity	NPD7521	Approved
0.7229	Intermediate Similarity	NPD5330	Approved
0.7229	Intermediate Similarity	NPD6409	Approved
0.7229	Intermediate Similarity	NPD6684	Approved
0.7229	Intermediate Similarity	NPD3618	Phase 1
0.716	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4221	Approved
0.716	Intermediate Similarity	NPD4223	Phase 3
0.716	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6672	Approved
0.7059	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD5737	Approved
0.7024	Intermediate Similarity	NPD5690	Phase 2
0.7011	Intermediate Similarity	NPD6079	Approved
0.6988	Remote Similarity	NPD3668	Phase 3
0.6988	Remote Similarity	NPD4197	Approved
0.6988	Remote Similarity	NPD4786	Approved
0.6977	Remote Similarity	NPD4753	Phase 2
0.6977	Remote Similarity	NPD5328	Approved
0.6941	Remote Similarity	NPD3573	Approved
0.6905	Remote Similarity	NPD5329	Approved
0.6889	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD3617	Approved
0.6824	Remote Similarity	NPD4688	Approved
0.6824	Remote Similarity	NPD4690	Approved
0.6824	Remote Similarity	NPD4689	Approved
0.6824	Remote Similarity	NPD4693	Phase 3
0.6824	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4519	Discontinued
0.6824	Remote Similarity	NPD4138	Approved
0.6824	Remote Similarity	NPD4623	Approved
0.6824	Remote Similarity	NPD5280	Approved
0.6824	Remote Similarity	NPD5205	Approved
0.6824	Remote Similarity	NPD4694	Approved
0.6818	Remote Similarity	NPD7515	Phase 2
0.6778	Remote Similarity	NPD4629	Approved
0.6778	Remote Similarity	NPD5210	Approved
0.6757	Remote Similarity	NPD7331	Phase 2
0.6742	Remote Similarity	NPD4202	Approved
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD1694	Approved
0.6703	Remote Similarity	NPD5222	Approved
0.6703	Remote Similarity	NPD5221	Approved
0.6703	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.663	Remote Similarity	NPD5173	Approved
0.6593	Remote Similarity	NPD5695	Phase 3
0.6591	Remote Similarity	NPD6673	Approved
0.6591	Remote Similarity	NPD6080	Approved
0.6591	Remote Similarity	NPD6904	Approved
0.6585	Remote Similarity	NPD4195	Approved
0.6522	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5692	Phase 3
0.6517	Remote Similarity	NPD4096	Approved
0.6517	Remote Similarity	NPD5207	Approved
0.6489	Remote Similarity	NPD4696	Approved
0.6489	Remote Similarity	NPD5285	Approved
0.6489	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4788	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD7902	Approved
0.6452	Remote Similarity	NPD6083	Phase 2
0.6444	Remote Similarity	NPD6050	Approved
0.6444	Remote Similarity	NPD5694	Approved
0.6444	Remote Similarity	NPD5281	Approved
0.6444	Remote Similarity	NPD5284	Approved
0.6444	Remote Similarity	NPD5693	Phase 1
0.6437	Remote Similarity	NPD6098	Approved
0.6421	Remote Similarity	NPD5223	Approved
0.6413	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7341	Phase 2
0.6383	Remote Similarity	NPD5696	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD5225	Approved
0.6354	Remote Similarity	NPD5224	Approved
0.6354	Remote Similarity	NPD5211	Phase 2
0.6354	Remote Similarity	NPD5226	Approved
0.6354	Remote Similarity	NPD4633	Approved
0.6344	Remote Similarity	NPD7732	Phase 3
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6001	Approved
0.6296	Remote Similarity	NPD8039	Approved
0.6292	Remote Similarity	NPD4518	Approved
0.6289	Remote Similarity	NPD5174	Approved
0.6289	Remote Similarity	NPD5175	Approved
0.6277	Remote Similarity	NPD3495	Discontinued
0.6235	Remote Similarity	NPD4139	Approved
0.6235	Remote Similarity	NPD4692	Approved
0.6224	Remote Similarity	NPD5141	Approved
0.6216	Remote Similarity	NPD4194	Approved
0.6216	Remote Similarity	NPD4193	Approved
0.6216	Remote Similarity	NPD4192	Approved
0.6216	Remote Similarity	NPD4191	Approved
0.6196	Remote Similarity	NPD7631	Approved
0.6196	Remote Similarity	NPD5133	Approved
0.617	Remote Similarity	NPD7614	Phase 1
0.6136	Remote Similarity	NPD1696	Phase 3
0.6133	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4754	Approved
0.61	Remote Similarity	NPD5697	Approved
0.6087	Remote Similarity	NPD7609	Phase 3
0.6071	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5654	Approved
0.6053	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4729	Approved
0.604	Remote Similarity	NPD5128	Approved
0.604	Remote Similarity	NPD5168	Approved
0.604	Remote Similarity	NPD6881	Approved
0.604	Remote Similarity	NPD4730	Approved
0.604	Remote Similarity	NPD6011	Approved
0.604	Remote Similarity	NPD6899	Approved
0.6024	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5091	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD4767	Approved
0.598	Remote Similarity	NPD6012	Approved
0.598	Remote Similarity	NPD6014	Approved
0.598	Remote Similarity	NPD6013	Approved
0.5977	Remote Similarity	NPD5209	Approved
0.5972	Remote Similarity	NPD4219	Approved
0.5941	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD5701	Approved
0.5938	Remote Similarity	NPD5959	Approved
0.5922	Remote Similarity	NPD5169	Approved
0.5922	Remote Similarity	NPD5247	Approved
0.5922	Remote Similarity	NPD7290	Approved
0.5922	Remote Similarity	NPD5249	Phase 3
0.5922	Remote Similarity	NPD4634	Approved
0.5922	Remote Similarity	NPD5248	Approved
0.5922	Remote Similarity	NPD7102	Approved
0.5922	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5250	Approved
0.5922	Remote Similarity	NPD5135	Approved
0.5922	Remote Similarity	NPD5251	Approved
0.5922	Remote Similarity	NPD6883	Approved
0.5914	Remote Similarity	NPD6411	Approved
0.5904	Remote Similarity	NPD6942	Approved
0.5904	Remote Similarity	NPD8264	Approved
0.5904	Remote Similarity	NPD7339	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5875	Remote Similarity	NPD6923	Approved
0.5875	Remote Similarity	NPD6922	Approved
0.5865	Remote Similarity	NPD8130	Phase 1
0.5865	Remote Similarity	NPD5127	Approved
0.5865	Remote Similarity	NPD6650	Approved
0.5865	Remote Similarity	NPD5215	Approved
0.5865	Remote Similarity	NPD5216	Approved
0.5865	Remote Similarity	NPD5217	Approved
0.5865	Remote Similarity	NPD6847	Approved
0.5865	Remote Similarity	NPD6617	Approved
0.5865	Remote Similarity	NPD6649	Approved
0.5865	Remote Similarity	NPD6869	Approved
0.5825	Remote Similarity	NPD6373	Approved
0.5825	Remote Similarity	NPD6372	Approved
0.5824	Remote Similarity	NPD650	Approved
0.5816	Remote Similarity	NPD6404	Discontinued
0.5814	Remote Similarity	NPD7645	Phase 2
0.581	Remote Similarity	NPD6882	Approved
0.581	Remote Similarity	NPD8297	Approved
0.5806	Remote Similarity	NPD5785	Approved
0.5802	Remote Similarity	NPD7144	Approved
0.5802	Remote Similarity	NPD7143	Approved
0.58	Remote Similarity	NPD6052	Approved
0.5789	Remote Similarity	NPD5282	Discontinued
0.5784	Remote Similarity	NPD6614	Approved
0.5783	Remote Similarity	NPD6926	Approved
0.5783	Remote Similarity	NPD6924	Approved
0.5778	Remote Similarity	NPD5363	Approved
0.5778	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3171	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