NPASS Compound

Structure

NPC220478 OpenBabel07101718192D 28 29 0 0 1 0 0 0 0 0999 V2000 4.1683 -0.6165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6743 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1839 -1.1839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 2.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8931 -0.3699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2851 -2.9173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5510 -0.1832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9843 -1.8004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2345 -0.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 0.4833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6743 1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5004 -1.8675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5115 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 0.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6835 -0.6835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6679 -2.4840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8372 1.4500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7506 -2.8012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3486 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4177 -3.4177 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6016 -2.2338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4333 -1.6173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 15 23 1 6 0 0 0 16 22 1 0 0 0 0 17 24 2 0 0 0 0 17 28 1 0 0 0 0 18 25 2 0 0 0 0 19 22 1 6 0 0 0 19 23 1 0 0 0 0 20 10 1 1 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 5 1 6 0 0 0 23 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.24
Volume:	420.02
LogP:	3.092
LogD:	2.49
LogS:	-4.11
# Rotatable Bonds:	7
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	4.659
Fsp3:	0.696
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:	-4.805
MDCK Permeability:	2.155516813218128e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.824
30% Bioavailability (F30%):	0.838

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	85.7549819946289%
Volume Distribution (VD):	0.953
Pgp-substrate:	18.556087493896484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.346
CYP2C19-inhibitor:	0.815
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.613
CYP3A4-substrate:	0.618

ADMET: Excretion

Clearance (CL):	3.533
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.732
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.425
Skin Sensitization:	0.958
Carcinogencity:	0.083
Eye Corrosion:	0.419
Eye Irritation:	0.344
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC220478

Natural Product ID:	NPC220478
*Common Name:**	Plectrornatin A
IUPAC Name:	methyl (E,5R)-5-[(1S,2R,4aR,8aS)-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]-5-acetyloxy-3-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	DFFCAAPJUPLECN-XOHWVXQESA-N
Standard InCHI:	InChI=1S/C23H34O5/c1-14(11-21(26)27-7)10-20(28-17(4)24)23(6)15(2)8-9-22(5)16(3)12-18(25)13-19(22)23/h11-12,15,19-20H,8-10,13H2,1-7H3/b14-11+/t15-,19+,20-,22+,23+/m1/s1
SMILES:	C/C(=CC(=O)OC)/C[C@H]([C@@]1(C)[C@H](C)CC[C@@]2(C)C(=CC(=O)C[C@H]12)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482594
PubChem CID:	637442
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO7657	Plectranthus ornatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398532]
NPO7657	Plectranthus ornatus	Species	Lamiaceae	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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>=	125.0	ug.mL-1	PMID[465709]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>=	125.0	ug.mL-1	PMID[465709]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>=	125.0	ug.mL-1	PMID[465709]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	62.5	ug.mL-1	PMID[465709]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	62.5	ug.mL-1	PMID[465709]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	62.5	ug.mL-1	PMID[465709]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	62.5	ug.mL-1	PMID[465709]
NPT2578	Organism	Pichia guilliermondii	Meyerozyma guilliermondii	MIC	=	62.5	ug.mL-1	PMID[465709]

☑ 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 NPC220478 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	198
0.1-0.2	1229
0.2-0.3	4634
0.3-0.4	10614
0.4-0.5	11943
0.5-0.6	7283
0.6-0.7	5037
0.7-0.8	1636
0.8-0.85	112
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9176	High Similarity	NPC284561
0.8929	High Similarity	NPC189311
0.8916	High Similarity	NPC193198
0.8636	High Similarity	NPC212679
0.8636	High Similarity	NPC152467
0.8636	High Similarity	NPC469595
0.8636	High Similarity	NPC220454
0.8625	High Similarity	NPC65650
0.8621	High Similarity	NPC226863
0.8602	High Similarity	NPC310981
0.8588	High Similarity	NPC474359
0.8588	High Similarity	NPC149869
0.8587	High Similarity	NPC176845
0.8571	High Similarity	NPC471218
0.8556	High Similarity	NPC38830
0.8556	High Similarity	NPC470697
0.8537	High Similarity	NPC471220
0.8523	High Similarity	NPC5509
0.8488	Intermediate Similarity	NPC110405
0.8478	Intermediate Similarity	NPC38530
0.8478	Intermediate Similarity	NPC84335
0.8471	Intermediate Similarity	NPC22611
0.8444	Intermediate Similarity	NPC475657
0.8434	Intermediate Similarity	NPC471299
0.8434	Intermediate Similarity	NPC469620
0.8434	Intermediate Similarity	NPC469690
0.8427	Intermediate Similarity	NPC471818
0.8421	Intermediate Similarity	NPC132395
0.8421	Intermediate Similarity	NPC471364
0.8421	Intermediate Similarity	NPC471365
0.8409	Intermediate Similarity	NPC215831
0.8409	Intermediate Similarity	NPC477128
0.8372	Intermediate Similarity	NPC30486
0.8353	Intermediate Similarity	NPC268122
0.8353	Intermediate Similarity	NPC200513
0.8352	Intermediate Similarity	NPC477130
0.8352	Intermediate Similarity	NPC477129
0.8352	Intermediate Similarity	NPC148463
0.8352	Intermediate Similarity	NPC476415
0.8333	Intermediate Similarity	NPC189616
0.8333	Intermediate Similarity	NPC473944
0.8333	Intermediate Similarity	NPC195424
0.8315	Intermediate Similarity	NPC73995
0.8315	Intermediate Similarity	NPC177141
0.8298	Intermediate Similarity	NPC476933
0.8295	Intermediate Similarity	NPC312561
0.8295	Intermediate Similarity	NPC477228
0.8293	Intermediate Similarity	NPC40353
0.828	Intermediate Similarity	NPC474343
0.828	Intermediate Similarity	NPC110937
0.828	Intermediate Similarity	NPC254496
0.828	Intermediate Similarity	NPC285513
0.8261	Intermediate Similarity	NPC33473
0.8261	Intermediate Similarity	NPC295347
0.8261	Intermediate Similarity	NPC473369
0.8256	Intermediate Similarity	NPC118423
0.8256	Intermediate Similarity	NPC222358
0.8242	Intermediate Similarity	NPC476598
0.8242	Intermediate Similarity	NPC169343
0.8242	Intermediate Similarity	NPC476597
0.8242	Intermediate Similarity	NPC79117
0.8235	Intermediate Similarity	NPC25554
0.8235	Intermediate Similarity	NPC229584
0.8235	Intermediate Similarity	NPC14203
0.8235	Intermediate Similarity	NPC40228
0.8235	Intermediate Similarity	NPC282293
0.8229	Intermediate Similarity	NPC254202
0.8222	Intermediate Similarity	NPC198818
0.8222	Intermediate Similarity	NPC101651
0.8222	Intermediate Similarity	NPC232426
0.8222	Intermediate Similarity	NPC469372
0.8222	Intermediate Similarity	NPC476369
0.8222	Intermediate Similarity	NPC159748
0.8222	Intermediate Similarity	NPC476437
0.8222	Intermediate Similarity	NPC281942
0.8222	Intermediate Similarity	NPC8062
0.8211	Intermediate Similarity	NPC472643
0.8202	Intermediate Similarity	NPC24816
0.8202	Intermediate Similarity	NPC478259
0.8202	Intermediate Similarity	NPC478260
0.8202	Intermediate Similarity	NPC478261
0.8202	Intermediate Similarity	NPC472302
0.8193	Intermediate Similarity	NPC316500
0.8193	Intermediate Similarity	NPC472300
0.8191	Intermediate Similarity	NPC23364
0.8182	Intermediate Similarity	NPC195640
0.8182	Intermediate Similarity	NPC168248
0.8172	Intermediate Similarity	NPC328371
0.8172	Intermediate Similarity	NPC112654
0.8163	Intermediate Similarity	NPC475294
0.8161	Intermediate Similarity	NPC475100
0.8152	Intermediate Similarity	NPC476596
0.8152	Intermediate Similarity	NPC53685
0.8152	Intermediate Similarity	NPC84893
0.8144	Intermediate Similarity	NPC470297
0.8144	Intermediate Similarity	NPC118911
0.814	Intermediate Similarity	NPC327969
0.814	Intermediate Similarity	NPC321289
0.814	Intermediate Similarity	NPC178676
0.814	Intermediate Similarity	NPC186276
0.8132	Intermediate Similarity	NPC218301
0.8132	Intermediate Similarity	NPC65513
0.8132	Intermediate Similarity	NPC190442
0.8132	Intermediate Similarity	NPC141831
0.8132	Intermediate Similarity	NPC303697
0.8111	Intermediate Similarity	NPC174342
0.8111	Intermediate Similarity	NPC168131
0.8111	Intermediate Similarity	NPC280833
0.8111	Intermediate Similarity	NPC474844
0.8105	Intermediate Similarity	NPC471413
0.8105	Intermediate Similarity	NPC174314
0.8105	Intermediate Similarity	NPC117685
0.8105	Intermediate Similarity	NPC476274
0.8105	Intermediate Similarity	NPC472644
0.8105	Intermediate Similarity	NPC54705
0.809	Intermediate Similarity	NPC181327
0.8085	Intermediate Similarity	NPC476768
0.8085	Intermediate Similarity	NPC69385
0.8085	Intermediate Similarity	NPC208094
0.8081	Intermediate Similarity	NPC476479
0.8072	Intermediate Similarity	NPC180886
0.8072	Intermediate Similarity	NPC27205
0.8068	Intermediate Similarity	NPC177932
0.8068	Intermediate Similarity	NPC323765
0.8068	Intermediate Similarity	NPC65661
0.8068	Intermediate Similarity	NPC476678
0.8065	Intermediate Similarity	NPC134067
0.8065	Intermediate Similarity	NPC173875
0.8065	Intermediate Similarity	NPC183012
0.8065	Intermediate Similarity	NPC274417
0.8065	Intermediate Similarity	NPC318282
0.8065	Intermediate Similarity	NPC470974
0.8065	Intermediate Similarity	NPC174948
0.8065	Intermediate Similarity	NPC469995
0.8065	Intermediate Similarity	NPC470978
0.8049	Intermediate Similarity	NPC20025
0.8046	Intermediate Similarity	NPC12283
0.8046	Intermediate Similarity	NPC474193
0.8046	Intermediate Similarity	NPC470047
0.8046	Intermediate Similarity	NPC470046
0.8043	Intermediate Similarity	NPC271652
0.8043	Intermediate Similarity	NPC476416
0.8043	Intermediate Similarity	NPC229976
0.8043	Intermediate Similarity	NPC115021
0.8043	Intermediate Similarity	NPC471571
0.8041	Intermediate Similarity	NPC470954
0.8023	Intermediate Similarity	NPC327002
0.8023	Intermediate Similarity	NPC475665
0.8023	Intermediate Similarity	NPC471325
0.8022	Intermediate Similarity	NPC161638
0.8022	Intermediate Similarity	NPC273199
0.8022	Intermediate Similarity	NPC51486
0.8022	Intermediate Similarity	NPC328141
0.8021	Intermediate Similarity	NPC473384
0.8021	Intermediate Similarity	NPC224720
0.8021	Intermediate Similarity	NPC476478
0.8021	Intermediate Similarity	NPC476240
0.8021	Intermediate Similarity	NPC476223
0.8021	Intermediate Similarity	NPC93744
0.8021	Intermediate Similarity	NPC476888
0.8021	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC327674
0.8	Intermediate Similarity	NPC316598
0.8	Intermediate Similarity	NPC471717
0.8	Intermediate Similarity	NPC252295
0.8	Intermediate Similarity	NPC222011
0.8	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC196407
0.8	Intermediate Similarity	NPC197386
0.8	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC150646
0.8	Intermediate Similarity	NPC478056
0.798	Intermediate Similarity	NPC133422
0.7979	Intermediate Similarity	NPC58052
0.7979	Intermediate Similarity	NPC111684
0.7979	Intermediate Similarity	NPC29952
0.7978	Intermediate Similarity	NPC470051
0.7978	Intermediate Similarity	NPC322159
0.7978	Intermediate Similarity	NPC470050
0.7976	Intermediate Similarity	NPC187568
0.7976	Intermediate Similarity	NPC41780
0.7957	Intermediate Similarity	NPC184870
0.7957	Intermediate Similarity	NPC250075
0.7957	Intermediate Similarity	NPC269729
0.7955	Intermediate Similarity	NPC71626
0.7955	Intermediate Similarity	NPC31086
0.7955	Intermediate Similarity	NPC312660
0.7955	Intermediate Similarity	NPC320801
0.7955	Intermediate Similarity	NPC100391
0.7938	Intermediate Similarity	NPC137430
0.7938	Intermediate Similarity	NPC32577
0.7938	Intermediate Similarity	NPC155332
0.7938	Intermediate Similarity	NPC114540
0.7938	Intermediate Similarity	NPC80781
0.7938	Intermediate Similarity	NPC475320
0.7938	Intermediate Similarity	NPC136289
0.7938	Intermediate Similarity	NPC40918
0.7938	Intermediate Similarity	NPC476890
0.7938	Intermediate Similarity	NPC162973
0.7935	Intermediate Similarity	NPC49420

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 NPC220478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1500
0.2-0.3	3764
0.3-0.4	2326
0.4-0.5	861
0.5-0.6	304
0.6-0.7	168
0.7-0.8	38
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
0.8353	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6684	Approved
0.8182	Intermediate Similarity	NPD7521	Approved
0.8182	Intermediate Similarity	NPD5330	Approved
0.8182	Intermediate Similarity	NPD6409	Approved
0.8182	Intermediate Similarity	NPD7146	Approved
0.8182	Intermediate Similarity	NPD7334	Approved
0.8068	Intermediate Similarity	NPD1694	Approved
0.8	Intermediate Similarity	NPD6903	Approved
0.8	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD6672	Approved
0.8	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD7748	Approved
0.7766	Intermediate Similarity	NPD7900	Approved
0.7766	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5693	Phase 1
0.7738	Intermediate Similarity	NPD8039	Approved
0.7692	Intermediate Similarity	NPD3573	Approved
0.766	Intermediate Similarity	NPD6399	Phase 3
0.7553	Intermediate Similarity	NPD7515	Phase 2
0.7527	Intermediate Similarity	NPD6673	Approved
0.7527	Intermediate Similarity	NPD6080	Approved
0.7527	Intermediate Similarity	NPD6904	Approved
0.7526	Intermediate Similarity	NPD7902	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7374	Intermediate Similarity	NPD7639	Approved
0.7374	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD6050	Approved
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7353	Intermediate Similarity	NPD6008	Approved
0.7347	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD6084	Phase 2
0.734	Intermediate Similarity	NPD5328	Approved
0.734	Intermediate Similarity	NPD6051	Approved
0.732	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5695	Phase 3
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7263	Intermediate Similarity	NPD5785	Approved
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7234	Intermediate Similarity	NPD5208	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7212	Intermediate Similarity	NPD6899	Approved
0.7204	Intermediate Similarity	NPD6098	Approved
0.7188	Intermediate Similarity	NPD5694	Approved
0.7188	Intermediate Similarity	NPD6079	Approved
0.7174	Intermediate Similarity	NPD3668	Phase 3
0.7174	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD3666	Approved
0.7174	Intermediate Similarity	NPD3133	Approved
0.7174	Intermediate Similarity	NPD4786	Approved
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6101	Approved
0.7158	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD5209	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5701	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7111	Intermediate Similarity	NPD4695	Discontinued
0.7103	Intermediate Similarity	NPD6053	Discontinued
0.71	Intermediate Similarity	NPD5696	Approved
0.71	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD46	Approved
0.7083	Intermediate Similarity	NPD5207	Approved
0.7083	Intermediate Similarity	NPD6698	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7071	Intermediate Similarity	NPD7732	Phase 3
0.7048	Intermediate Similarity	NPD6686	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7021	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6617	Approved
0.6989	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6941	Remote Similarity	NPD4137	Phase 3
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4697	Phase 3
0.6889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6001	Approved
0.6867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4747	Approved
0.686	Remote Similarity	NPD4691	Approved
0.6842	Remote Similarity	NPD6422	Discontinued
0.6842	Remote Similarity	NPD5786	Approved
0.6842	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD5281	Approved
0.6837	Remote Similarity	NPD5284	Approved
0.6832	Remote Similarity	NPD5173	Approved
0.6832	Remote Similarity	NPD4755	Approved
0.6818	Remote Similarity	NPD5733	Approved
0.6804	Remote Similarity	NPD4753	Phase 2
0.68	Remote Similarity	NPD5654	Approved
0.6792	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7331	Phase 2
0.6774	Remote Similarity	NPD4223	Phase 3
0.6774	Remote Similarity	NPD4221	Approved
0.6774	Remote Similarity	NPD6435	Approved
0.6757	Remote Similarity	NPD6868	Approved
0.6747	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5329	Approved
0.6737	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5363	Approved
0.6733	Remote Similarity	NPD7614	Phase 1
0.6731	Remote Similarity	NPD7632	Discontinued
0.6731	Remote Similarity	NPD5211	Phase 2
0.6702	Remote Similarity	NPD5362	Discontinued
0.6702	Remote Similarity	NPD7154	Phase 3
0.6699	Remote Similarity	NPD5286	Approved
0.6699	Remote Similarity	NPD4696	Approved
0.6699	Remote Similarity	NPD5285	Approved
0.6699	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6335	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD4197	Approved
0.6629	Remote Similarity	NPD4058	Approved
0.6629	Remote Similarity	NPD4687	Approved
0.6607	Remote Similarity	NPD6274	Approved
0.6606	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5141	Approved
0.66	Remote Similarity	NPD4202	Approved
0.6596	Remote Similarity	NPD4270	Approved
0.6596	Remote Similarity	NPD4269	Approved
0.6591	Remote Similarity	NPD5276	Approved
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6577	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD5226	Approved
0.6571	Remote Similarity	NPD5225	Approved
0.6571	Remote Similarity	NPD4633	Approved
0.6571	Remote Similarity	NPD5224	Approved
0.6559	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5368	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6529	Remote Similarity	NPD7260	Phase 2
0.6525	Remote Similarity	NPD7507	Approved
0.6522	Remote Similarity	NPD3617	Approved
0.6509	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD4754	Approved
0.6509	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD8034	Phase 2
0.65	Remote Similarity	NPD8035	Phase 2
0.65	Remote Similarity	NPD7983	Approved
0.6495	Remote Similarity	NPD4689	Approved
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5280	Approved
0.6495	Remote Similarity	NPD4693	Phase 3
0.6495	Remote Similarity	NPD4688	Approved
0.6495	Remote Similarity	NPD4694	Approved
0.6495	Remote Similarity	NPD5205	Approved
0.6495	Remote Similarity	NPD4138	Approved
0.6495	Remote Similarity	NPD4690	Approved
0.6495	Remote Similarity	NPD5690	Phase 2
0.6491	Remote Similarity	NPD6313	Approved
0.6491	Remote Similarity	NPD6314	Approved
0.6489	Remote Similarity	NPD5369	Approved
0.6481	Remote Similarity	NPD6614	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD7341	Phase 2
0.6466	Remote Similarity	NPD6908	Approved
0.6466	Remote Similarity	NPD6909	Approved
0.6455	Remote Similarity	NPD6371	Approved
0.6437	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6858	Approved
0.6429	Remote Similarity	NPD7094	Approved
0.6422	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4756	Discovery
0.6408	Remote Similarity	NPD7839	Suspended
0.6404	Remote Similarity	NPD6009	Approved
0.6404	Remote Similarity	NPD5777	Approved
0.6392	Remote Similarity	NPD6082	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