NPASS Compound

Structure

NPC61783 OpenBabel07101718202D 33 37 0 0 0 0 0 0 0 0999 V2000 -1.3128 -1.0927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1788 -0.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4468 -0.5927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6256 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8951 -0.5412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2045 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3600 -1.4784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8362 -2.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1598 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3531 -2.0073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3128 -1.7802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3122 -0.4446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7629 -0.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3128 0.9073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7854 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3128 -2.6365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1788 0.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9509 -1.1432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7185 -2.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4468 0.4073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3253 -1.1432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4211 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9071 -2.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9352 -2.3316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7894 -2.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3679 -1.0466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2695 -0.5412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8745 -1.3959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1448 -3.3094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5712 -1.3862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 -1.4645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9668 -2.3916 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 17 1 0 0 0 0 3 20 2 0 0 0 0 4 5 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 9 1 0 0 0 0 6 19 1 0 0 0 0 7 10 2 0 0 0 0 7 18 1 0 0 0 0 8 11 2 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 13 2 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 20 33 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 23 25 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 28 2 0 0 0 0 26 31 1 0 0 0 0 27 33 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.16
Volume:	462.375
LogP:	6.217
LogD:	3.922
LogS:	-3.478
# Rotatable Bonds:	0
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.258
Synthetic Accessibility Score:	4.731
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.515
MDCK Permeability:	1.0333352292946074e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	101.06229400634766%
Volume Distribution (VD):	0.263
Pgp-substrate:	0.7338318228721619%

ADMET: Metabolism

CYP1A2-inhibitor:	0.818
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.402
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	10.453
Half-life (T1/2):	0.619

ADMET: Toxicity

hERG Blockers:	0.115
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.531
Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.97
Carcinogencity:	0.17
Eye Corrosion:	0.003
Eye Irritation:	0.88
Respiratory Toxicity:	0.132

Download Data

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

Natural Product: NPC61783

Natural Product ID:	NPC61783
*Common Name:**	Dihydroisoplagiochin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QUYHSAXCXCKFJP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H24O5/c29-24-10-7-18-5-4-17-2-1-3-20(14-17)33-27-13-12-26(31)28(32)21(27)9-6-19-8-11-25(30)23(16-19)22(24)15-18/h1-3,7-8,10-16,29-32H,4-6,9H2
SMILES:	c1cc2CCc3ccc(c(-c4cc(CCc5c(ccc(c5O)O)Oc(c1)c2)ccc4O)c3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518829
PubChem CID:	44581396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO32483	Plagiochila fruticosa	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19056262]
NPO32483	Plagiochila fruticosa	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO32483	Plagiochila fruticosa	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32479076]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[480208]

☑ 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 NPC61783 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	570
0.1-0.2	2057
0.2-0.3	6465
0.3-0.4	12683
0.4-0.5	3815
0.5-0.6	4226
0.6-0.7	6768
0.7-0.8	4999
0.8-0.85	664
0.85-0.9	388
0.9-0.95	58
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC20520
0.9407	High Similarity	NPC48956
0.9328	High Similarity	NPC256307
0.9328	High Similarity	NPC66840
0.9179	High Similarity	NPC131128
0.9179	High Similarity	NPC474134
0.9149	High Similarity	NPC150714
0.9149	High Similarity	NPC95652
0.913	High Similarity	NPC34431
0.913	High Similarity	NPC165026
0.913	High Similarity	NPC22317
0.913	High Similarity	NPC295719
0.913	High Similarity	NPC73505
0.9085	High Similarity	NPC263940
0.9085	High Similarity	NPC236202
0.9085	High Similarity	NPC204770
0.9085	High Similarity	NPC170103
0.9085	High Similarity	NPC82917
0.9085	High Similarity	NPC108811
0.9085	High Similarity	NPC58190
0.9085	High Similarity	NPC202742
0.9085	High Similarity	NPC18185
0.9085	High Similarity	NPC294558
0.9085	High Similarity	NPC70409
0.9085	High Similarity	NPC262911
0.9071	High Similarity	NPC173203
0.9071	High Similarity	NPC163508
0.9058	High Similarity	NPC55947
0.9021	High Similarity	NPC227516
0.9021	High Similarity	NPC20757
0.9014	High Similarity	NPC96576
0.9007	High Similarity	NPC15659
0.9007	High Similarity	NPC304894
0.9	High Similarity	NPC175838
0.9	High Similarity	NPC183709
0.8993	High Similarity	NPC259519
0.8986	High Similarity	NPC25111
0.8986	High Similarity	NPC73535
0.8986	High Similarity	NPC272157
0.8986	High Similarity	NPC474390
0.8986	High Similarity	NPC201145
0.8986	High Similarity	NPC6262
0.8986	High Similarity	NPC90615
0.8978	High Similarity	NPC473413
0.8958	High Similarity	NPC476969
0.8958	High Similarity	NPC211561
0.8955	High Similarity	NPC210655
0.8939	High Similarity	NPC133407
0.8939	High Similarity	NPC28476
0.8929	High Similarity	NPC178054
0.8921	High Similarity	NPC212942
0.8921	High Similarity	NPC79622
0.8921	High Similarity	NPC32630
0.8921	High Similarity	NPC127218
0.8921	High Similarity	NPC260741
0.8921	High Similarity	NPC29868
0.8921	High Similarity	NPC70682
0.8921	High Similarity	NPC319647
0.8921	High Similarity	NPC25966
0.8921	High Similarity	NPC245207
0.8913	High Similarity	NPC300846
0.8913	High Similarity	NPC476639
0.8913	High Similarity	NPC114155
0.8904	High Similarity	NPC476391
0.8897	High Similarity	NPC303144
0.8897	High Similarity	NPC218884
0.8897	High Similarity	NPC477612
0.8889	High Similarity	NPC281549
0.8881	High Similarity	NPC226331
0.8881	High Similarity	NPC46274
0.8873	High Similarity	NPC280092
0.8873	High Similarity	NPC12641
0.8873	High Similarity	NPC171932
0.8873	High Similarity	NPC93323
0.8873	High Similarity	NPC28440
0.8873	High Similarity	NPC45257
0.8873	High Similarity	NPC50250
0.8865	High Similarity	NPC59841
0.8865	High Similarity	NPC2613
0.8865	High Similarity	NPC475891
0.8865	High Similarity	NPC204347
0.8857	High Similarity	NPC308768
0.8857	High Similarity	NPC262189
0.8857	High Similarity	NPC12668
0.8849	High Similarity	NPC103976
0.8849	High Similarity	NPC276490
0.8849	High Similarity	NPC474282
0.8849	High Similarity	NPC326797
0.8849	High Similarity	NPC102904
0.8849	High Similarity	NPC107551
0.8849	High Similarity	NPC176051
0.8841	High Similarity	NPC283009
0.8841	High Similarity	NPC261873
0.8841	High Similarity	NPC111655
0.8841	High Similarity	NPC125579
0.8832	High Similarity	NPC11060
0.8819	High Similarity	NPC262297
0.8819	High Similarity	NPC97937
0.8819	High Similarity	NPC275125
0.8819	High Similarity	NPC16269
0.8819	High Similarity	NPC21776
0.8819	High Similarity	NPC170239
0.8806	High Similarity	NPC5447
0.8806	High Similarity	NPC250432
0.8803	High Similarity	NPC47633
0.8803	High Similarity	NPC102044
0.8803	High Similarity	NPC85264
0.8794	High Similarity	NPC265075
0.8794	High Similarity	NPC35216
0.8794	High Similarity	NPC471389
0.8786	High Similarity	NPC105847
0.8786	High Similarity	NPC220344
0.8786	High Similarity	NPC22517
0.8786	High Similarity	NPC243996
0.8786	High Similarity	NPC132804
0.8786	High Similarity	NPC275061
0.8786	High Similarity	NPC218131
0.8786	High Similarity	NPC243759
0.8777	High Similarity	NPC472336
0.8777	High Similarity	NPC173660
0.8777	High Similarity	NPC202846
0.8777	High Similarity	NPC265433
0.8777	High Similarity	NPC472334
0.8777	High Similarity	NPC143139
0.8777	High Similarity	NPC162659
0.8777	High Similarity	NPC248727
0.8777	High Similarity	NPC205442
0.8777	High Similarity	NPC470802
0.8777	High Similarity	NPC234952
0.8777	High Similarity	NPC270456
0.8776	High Similarity	NPC322899
0.8776	High Similarity	NPC272552
0.8776	High Similarity	NPC226809
0.8776	High Similarity	NPC226108
0.8776	High Similarity	NPC46283
0.8776	High Similarity	NPC279406
0.8776	High Similarity	NPC44192
0.8776	High Similarity	NPC134911
0.8776	High Similarity	NPC469944
0.8768	High Similarity	NPC103967
0.8768	High Similarity	NPC106215
0.8759	High Similarity	NPC329836
0.8759	High Similarity	NPC6451
0.8759	High Similarity	NPC86655
0.8759	High Similarity	NPC202762
0.8759	High Similarity	NPC127624
0.875	High Similarity	NPC51840
0.875	High Similarity	NPC260397
0.875	High Similarity	NPC299221
0.875	High Similarity	NPC234488
0.875	High Similarity	NPC311680
0.875	High Similarity	NPC214860
0.875	High Similarity	NPC126291
0.875	High Similarity	NPC254000
0.8741	High Similarity	NPC63879
0.8741	High Similarity	NPC473108
0.8732	High Similarity	NPC107161
0.8731	High Similarity	NPC134431
0.8731	High Similarity	NPC156854
0.8725	High Similarity	NPC292385
0.8725	High Similarity	NPC125709
0.8723	High Similarity	NPC472092
0.8723	High Similarity	NPC472091
0.8723	High Similarity	NPC472090
0.8723	High Similarity	NPC160283
0.8723	High Similarity	NPC254759
0.8716	High Similarity	NPC20050
0.8716	High Similarity	NPC306267
0.8716	High Similarity	NPC224161
0.8714	High Similarity	NPC35550
0.8714	High Similarity	NPC242715
0.8714	High Similarity	NPC266006
0.8714	High Similarity	NPC200935
0.8714	High Similarity	NPC151656
0.8714	High Similarity	NPC56329
0.8714	High Similarity	NPC230919
0.8714	High Similarity	NPC211549
0.8714	High Similarity	NPC22902
0.8714	High Similarity	NPC266453
0.8705	High Similarity	NPC112939
0.8705	High Similarity	NPC256262
0.8705	High Similarity	NPC474206
0.8705	High Similarity	NPC151224
0.8705	High Similarity	NPC472337
0.8705	High Similarity	NPC158142
0.8705	High Similarity	NPC294884
0.8705	High Similarity	NPC241241
0.8705	High Similarity	NPC200557
0.8705	High Similarity	NPC164787
0.8705	High Similarity	NPC108198
0.8705	High Similarity	NPC10314
0.8705	High Similarity	NPC69029
0.8705	High Similarity	NPC470356
0.8705	High Similarity	NPC94750
0.8705	High Similarity	NPC195022
0.8705	High Similarity	NPC112246
0.8705	High Similarity	NPC121812
0.8705	High Similarity	NPC258780
0.8699	High Similarity	NPC318373
0.8699	High Similarity	NPC321657

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 NPC61783 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	486
0.1-0.2	974
0.2-0.3	1936
0.3-0.4	2725
0.4-0.5	1534
0.5-0.6	858
0.6-0.7	543
0.7-0.8	86
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD1529	Clinical (unspecified phase)
0.8806	High Similarity	NPD1530	Clinical (unspecified phase)
0.8623	High Similarity	NPD1612	Clinical (unspecified phase)
0.8623	High Similarity	NPD1613	Approved
0.8613	High Similarity	NPD4907	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD4908	Phase 1
0.8273	Intermediate Similarity	NPD3027	Phase 3
0.8273	Intermediate Similarity	NPD4625	Phase 3
0.8088	Intermediate Similarity	NPD1610	Phase 2
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1548	Phase 1
0.7842	Intermediate Similarity	NPD4749	Approved
0.7834	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2801	Approved
0.7815	Intermediate Similarity	NPD1511	Approved
0.7791	Intermediate Similarity	NPD5844	Phase 1
0.7712	Intermediate Similarity	NPD1512	Approved
0.7643	Intermediate Similarity	NPD1934	Approved
0.7613	Intermediate Similarity	NPD1653	Approved
0.761	Intermediate Similarity	NPD7768	Phase 2
0.7607	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6166	Phase 2
0.7586	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6671	Approved
0.755	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7485	Intermediate Similarity	NPD6232	Discontinued
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7434	Intermediate Similarity	NPD6674	Discontinued
0.7419	Intermediate Similarity	NPD7447	Phase 1
0.7419	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6696	Suspended
0.7412	Intermediate Similarity	NPD8053	Approved
0.7412	Intermediate Similarity	NPD8054	Approved
0.7407	Intermediate Similarity	NPD6234	Discontinued
0.7388	Intermediate Similarity	NPD3021	Approved
0.7388	Intermediate Similarity	NPD3022	Approved
0.7386	Intermediate Similarity	NPD3750	Approved
0.7375	Intermediate Similarity	NPD8455	Phase 2
0.7362	Intermediate Similarity	NPD5494	Approved
0.7355	Intermediate Similarity	NPD7212	Phase 2
0.7355	Intermediate Similarity	NPD7213	Phase 3
0.7349	Intermediate Similarity	NPD7473	Discontinued
0.7343	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2983	Phase 2
0.7343	Intermediate Similarity	NPD2982	Phase 2
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7317	Intermediate Similarity	NPD7199	Phase 2
0.7299	Intermediate Similarity	NPD5283	Phase 1
0.7296	Intermediate Similarity	NPD4380	Phase 2
0.7294	Intermediate Similarity	NPD7549	Discontinued
0.7292	Intermediate Similarity	NPD8651	Approved
0.7289	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3882	Suspended
0.7279	Intermediate Similarity	NPD228	Approved
0.7273	Intermediate Similarity	NPD2981	Phase 2
0.7261	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1558	Phase 1
0.7237	Intermediate Similarity	NPD6099	Approved
0.7237	Intermediate Similarity	NPD6100	Approved
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7074	Phase 3
0.7205	Intermediate Similarity	NPD37	Approved
0.7203	Intermediate Similarity	NPD1611	Approved
0.7202	Intermediate Similarity	NPD7228	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.72	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6584	Phase 3
0.7192	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4966	Approved
0.7178	Intermediate Similarity	NPD4967	Phase 2
0.7178	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7164	Intermediate Similarity	NPD968	Approved
0.7162	Intermediate Similarity	NPD7095	Approved
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3749	Approved
0.7133	Intermediate Similarity	NPD3620	Phase 2
0.7133	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2935	Discontinued
0.7118	Intermediate Similarity	NPD7472	Approved
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7105	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4538	Approved
0.7103	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1091	Approved
0.7078	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD6797	Phase 2
0.7067	Intermediate Similarity	NPD6233	Phase 2
0.7063	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD6516	Phase 2
0.7059	Intermediate Similarity	NPD5960	Phase 3
0.7059	Intermediate Similarity	NPD5588	Approved
0.7059	Intermediate Similarity	NPD3748	Approved
0.7055	Intermediate Similarity	NPD7819	Suspended
0.7051	Intermediate Similarity	NPD7466	Approved
0.7051	Intermediate Similarity	NPD3892	Phase 2
0.705	Intermediate Similarity	NPD1398	Phase 1
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7035	Intermediate Similarity	NPD6559	Discontinued
0.7035	Intermediate Similarity	NPD7251	Discontinued
0.7032	Intermediate Similarity	NPD1549	Phase 2
0.7032	Intermediate Similarity	NPD7037	Approved
0.703	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7075	Discontinued
0.7025	Intermediate Similarity	NPD7390	Discontinued
0.7021	Intermediate Similarity	NPD7340	Approved
0.7012	Intermediate Similarity	NPD5402	Approved
0.7007	Intermediate Similarity	NPD4750	Phase 3
0.7006	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8099	Discontinued
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD8252	Approved
0.7	Intermediate Similarity	NPD8251	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6987	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6583	Phase 3
0.6986	Remote Similarity	NPD6582	Phase 2
0.6985	Remote Similarity	NPD2342	Discontinued
0.6981	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5535	Approved
0.6978	Remote Similarity	NPD7635	Approved
0.6975	Remote Similarity	NPD4675	Approved
0.6975	Remote Similarity	NPD4678	Approved
0.6974	Remote Similarity	NPD5735	Approved
0.6968	Remote Similarity	NPD3540	Phase 1
0.6968	Remote Similarity	NPD7266	Discontinued
0.6959	Remote Similarity	NPD8156	Discontinued
0.6951	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7157	Approved
0.6948	Remote Similarity	NPD1510	Phase 2
0.6939	Remote Similarity	NPD3225	Approved
0.6934	Remote Similarity	NPD2684	Approved
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4663	Approved
0.6928	Remote Similarity	NPD4097	Suspended
0.6918	Remote Similarity	NPD7041	Phase 2
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD943	Approved
0.6903	Remote Similarity	NPD5404	Approved
0.6903	Remote Similarity	NPD5405	Approved
0.6903	Remote Similarity	NPD5406	Approved
0.6903	Remote Similarity	NPD5408	Approved
0.6903	Remote Similarity	NPD3539	Phase 1
0.6901	Remote Similarity	NPD3751	Discontinued
0.6899	Remote Similarity	NPD6190	Approved
0.6897	Remote Similarity	NPD3496	Discontinued
0.6897	Remote Similarity	NPD7808	Phase 3
0.6893	Remote Similarity	NPD7906	Approved
0.6892	Remote Similarity	NPD2797	Approved
0.6887	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1652	Phase 2
0.686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4578	Approved
0.6857	Remote Similarity	NPD4577	Approved
0.6857	Remote Similarity	NPD7843	Approved
0.6855	Remote Similarity	NPD5058	Phase 3
0.6849	Remote Similarity	NPD1535	Discovery
0.6849	Remote Similarity	NPD3705	Approved
0.6848	Remote Similarity	NPD5929	Approved
0.6839	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6331	Phase 2
0.6832	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6072	Discontinued
0.6828	Remote Similarity	NPD4626	Approved
0.681	Remote Similarity	NPD4005	Discontinued
0.6805	Remote Similarity	NPD1247	Approved
0.6803	Remote Similarity	NPD1481	Phase 2
0.6803	Remote Similarity	NPD1608	Approved
0.68	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD1240	Approved
0.6795	Remote Similarity	NPD2796	Approved
0.6792	Remote Similarity	NPD2677	Approved
0.679	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6801	Discontinued
0.678	Remote Similarity	NPD8055	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