NPASS Compound

Structure

NPC469853 OpenBabel07101718292D 33 35 0 0 1 0 0 0 0 0999 V2000 -4.3749 -7.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9929 -5.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7058 -7.0280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6984 -4.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7202 -5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3675 -5.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3457 -5.3338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9271 -4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0148 -6.0769 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5743 -3.9360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 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 4 1 0 0 0 0 2 16 1 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 10 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 22 2 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 32 1 0 0 0 0 17 20 2 0 0 0 0 18 28 2 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 30 2 0 0 0 0 25 31 2 0 0 0 0 25 33 1 0 0 0 0 26 3 1 1 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.2
Volume:	470.386
LogP:	1.828
LogD:	1.579
LogS:	-4.343
# Rotatable Bonds:	9
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	5.095
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.877
MDCK Permeability:	2.2738357074558735e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.17
Plasma Protein Binding (PPB):	84.35160064697266%
Volume Distribution (VD):	0.281
Pgp-substrate:	9.457927703857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.208
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.141
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.632

ADMET: Excretion

Clearance (CL):	2.018
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.675
Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.754
Carcinogencity:	0.921
Eye Corrosion:	0.004
Eye Irritation:	0.041
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC469853

Natural Product ID:	NPC469853
*Common Name:**	Bulgarialactone D
IUPAC Name:	(9aR)-6-(hydroxymethyl)-3-[(1Z,4E,6E,8E)-1-hydroxy-10-methyl-3-oxododeca-1,4,6,8-tetraenyl]-9a-methyl-4,5,6,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione
Synonyms:	Bulgarialactone D
Standard InCHIKey:	CKMBMKXIDJMFEL-DMCYUOPFSA-N
Standard InCHI:	InChI=1S/C26H30O7/c1-4-16(2)9-7-5-6-8-10-18(28)13-22(29)23-21-12-17-11-19(14-27)32-15-20(17)24(30)26(21,3)33-25(23)31/h5-10,13,16,19,27,29H,4,11-12,14-15H2,1-3H3/b6-5+,9-7+,10-8+,22-13-/t16?,19?,26-/m1/s1
SMILES:	CCC(C)C=CC=CC=CC(=O)C=C(C1=C2CC3=C(COC(C3)CO)C(=O)C2(OC1=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215389
PubChem CID:	49864118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32777	bulgaria inquinans icrm-184	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20655237]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[487800]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	17600.0	nM	PMID[487800]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[487800]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[487800]

☑ 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 NPC469853 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	209
0.1-0.2	1050
0.2-0.3	3862
0.3-0.4	7555
0.4-0.5	15564
0.5-0.6	9172
0.6-0.7	4342
0.7-0.8	885
0.8-0.85	55
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9307	High Similarity	NPC469852
0.8911	High Similarity	NPC469851
0.8491	Intermediate Similarity	NPC266514
0.84	Intermediate Similarity	NPC29798
0.84	Intermediate Similarity	NPC282644
0.8381	Intermediate Similarity	NPC118902
0.8381	Intermediate Similarity	NPC104161
0.8381	Intermediate Similarity	NPC469980
0.83	Intermediate Similarity	NPC193396
0.83	Intermediate Similarity	NPC32944
0.83	Intermediate Similarity	NPC166110
0.83	Intermediate Similarity	NPC32552
0.8286	Intermediate Similarity	NPC39996
0.8241	Intermediate Similarity	NPC264819
0.8224	Intermediate Similarity	NPC477125
0.8218	Intermediate Similarity	NPC248193
0.8173	Intermediate Similarity	NPC35717
0.8137	Intermediate Similarity	NPC121825
0.8108	Intermediate Similarity	NPC66108
0.81	Intermediate Similarity	NPC95364
0.81	Intermediate Similarity	NPC142159
0.8091	Intermediate Similarity	NPC89408
0.8077	Intermediate Similarity	NPC208094
0.8039	Intermediate Similarity	NPC469645
0.8039	Intermediate Similarity	NPC469692
0.8037	Intermediate Similarity	NPC271059
0.8037	Intermediate Similarity	NPC25666
0.8036	Intermediate Similarity	NPC321496
0.8019	Intermediate Similarity	NPC244456
0.8019	Intermediate Similarity	NPC46998
0.8019	Intermediate Similarity	NPC110443
0.8019	Intermediate Similarity	NPC185141
0.8019	Intermediate Similarity	NPC469657
0.8019	Intermediate Similarity	NPC128733
0.8019	Intermediate Similarity	NPC133907
0.8018	Intermediate Similarity	NPC317107
0.8	Intermediate Similarity	NPC475065
0.8	Intermediate Similarity	NPC38154
0.7982	Intermediate Similarity	NPC329048
0.7982	Intermediate Similarity	NPC330011
0.798	Intermediate Similarity	NPC472009
0.7946	Intermediate Similarity	NPC317687
0.7928	Intermediate Similarity	NPC29133
0.7925	Intermediate Similarity	NPC476299
0.7925	Intermediate Similarity	NPC474012
0.7913	Intermediate Similarity	NPC186525
0.7913	Intermediate Similarity	NPC50774
0.7913	Intermediate Similarity	NPC709
0.7909	Intermediate Similarity	NPC475418
0.7909	Intermediate Similarity	NPC473482
0.7909	Intermediate Similarity	NPC318363
0.7905	Intermediate Similarity	NPC20066
0.79	Intermediate Similarity	NPC472007
0.7895	Intermediate Similarity	NPC64318
0.7885	Intermediate Similarity	NPC295347
0.7879	Intermediate Similarity	NPC187529
0.7876	Intermediate Similarity	NPC469454
0.7876	Intermediate Similarity	NPC469496
0.7876	Intermediate Similarity	NPC469463
0.787	Intermediate Similarity	NPC472755
0.7857	Intermediate Similarity	NPC324683
0.7857	Intermediate Similarity	NPC470961
0.7857	Intermediate Similarity	NPC474315
0.7857	Intermediate Similarity	NPC179798
0.7857	Intermediate Similarity	NPC304180
0.785	Intermediate Similarity	NPC471699
0.785	Intermediate Similarity	NPC224172
0.785	Intermediate Similarity	NPC472753
0.7838	Intermediate Similarity	NPC228477
0.7838	Intermediate Similarity	NPC137911
0.783	Intermediate Similarity	NPC300584
0.783	Intermediate Similarity	NPC316598
0.783	Intermediate Similarity	NPC161855
0.7826	Intermediate Similarity	NPC183580
0.7826	Intermediate Similarity	NPC470492
0.7826	Intermediate Similarity	NPC140055
0.7826	Intermediate Similarity	NPC286528
0.7826	Intermediate Similarity	NPC20302
0.7826	Intermediate Similarity	NPC312824
0.7826	Intermediate Similarity	NPC470493
0.7826	Intermediate Similarity	NPC167606
0.7822	Intermediate Similarity	NPC472008
0.7818	Intermediate Similarity	NPC473284
0.781	Intermediate Similarity	NPC473291
0.7807	Intermediate Similarity	NPC67259
0.7807	Intermediate Similarity	NPC147912
0.78	Intermediate Similarity	NPC261721
0.78	Intermediate Similarity	NPC291712
0.78	Intermediate Similarity	NPC315395
0.78	Intermediate Similarity	NPC316426
0.7788	Intermediate Similarity	NPC469632
0.7788	Intermediate Similarity	NPC191620
0.7778	Intermediate Similarity	NPC31641
0.7778	Intermediate Similarity	NPC197835
0.7778	Intermediate Similarity	NPC473145
0.7778	Intermediate Similarity	NPC140591
0.7778	Intermediate Similarity	NPC303653
0.7778	Intermediate Similarity	NPC474370
0.7778	Intermediate Similarity	NPC189609
0.7778	Intermediate Similarity	NPC291500
0.7778	Intermediate Similarity	NPC476815
0.7778	Intermediate Similarity	NPC472754
0.7768	Intermediate Similarity	NPC5103
0.7767	Intermediate Similarity	NPC142838
0.7748	Intermediate Similarity	NPC322903
0.7748	Intermediate Similarity	NPC220155
0.7748	Intermediate Similarity	NPC327106
0.7745	Intermediate Similarity	NPC218927
0.7745	Intermediate Similarity	NPC206001
0.7736	Intermediate Similarity	NPC471694
0.7736	Intermediate Similarity	NPC53844
0.7719	Intermediate Similarity	NPC56448
0.7714	Intermediate Similarity	NPC471698
0.7714	Intermediate Similarity	NPC209355
0.7712	Intermediate Similarity	NPC67569
0.7706	Intermediate Similarity	NPC159533
0.7706	Intermediate Similarity	NPC475945
0.7706	Intermediate Similarity	NPC475871
0.7706	Intermediate Similarity	NPC473624
0.7706	Intermediate Similarity	NPC475050
0.77	Intermediate Similarity	NPC281172
0.7692	Intermediate Similarity	NPC245320
0.7692	Intermediate Similarity	NPC264954
0.7692	Intermediate Similarity	NPC115021
0.7685	Intermediate Similarity	NPC474339
0.7685	Intermediate Similarity	NPC164598
0.7685	Intermediate Similarity	NPC472643
0.7677	Intermediate Similarity	NPC16488
0.7672	Intermediate Similarity	NPC471145
0.7672	Intermediate Similarity	NPC243065
0.767	Intermediate Similarity	NPC166554
0.767	Intermediate Similarity	NPC477684
0.767	Intermediate Similarity	NPC475879
0.767	Intermediate Similarity	NPC473448
0.767	Intermediate Similarity	NPC265856
0.767	Intermediate Similarity	NPC471399
0.7667	Intermediate Similarity	NPC470922
0.7667	Intermediate Similarity	NPC24651
0.7664	Intermediate Similarity	NPC306908
0.7658	Intermediate Similarity	NPC199107
0.7658	Intermediate Similarity	NPC67321
0.7658	Intermediate Similarity	NPC232969
0.7658	Intermediate Similarity	NPC187435
0.7647	Intermediate Similarity	NPC88326
0.7647	Intermediate Similarity	NPC23786
0.7647	Intermediate Similarity	NPC153700
0.7647	Intermediate Similarity	NPC477302
0.7647	Intermediate Similarity	NPC470265
0.7647	Intermediate Similarity	NPC136879
0.7642	Intermediate Similarity	NPC242848
0.7636	Intermediate Similarity	NPC296950
0.7636	Intermediate Similarity	NPC146731
0.7636	Intermediate Similarity	NPC472756
0.7624	Intermediate Similarity	NPC469483
0.7615	Intermediate Similarity	NPC473596
0.7615	Intermediate Similarity	NPC149371
0.7615	Intermediate Similarity	NPC474747
0.7607	Intermediate Similarity	NPC284707
0.7607	Intermediate Similarity	NPC315974
0.7596	Intermediate Similarity	NPC327760
0.7596	Intermediate Similarity	NPC114345
0.7596	Intermediate Similarity	NPC303697
0.7596	Intermediate Similarity	NPC303230
0.7596	Intermediate Similarity	NPC6099
0.7593	Intermediate Similarity	NPC472644
0.7589	Intermediate Similarity	NPC151393
0.7586	Intermediate Similarity	NPC270478
0.7583	Intermediate Similarity	NPC469789
0.7576	Intermediate Similarity	NPC474252
0.7573	Intermediate Similarity	NPC51358
0.7573	Intermediate Similarity	NPC307092
0.757	Intermediate Similarity	NPC239895
0.7568	Intermediate Similarity	NPC472749
0.7568	Intermediate Similarity	NPC472751
0.7568	Intermediate Similarity	NPC266570
0.7568	Intermediate Similarity	NPC1679
0.7568	Intermediate Similarity	NPC472645
0.7565	Intermediate Similarity	NPC122056
0.7563	Intermediate Similarity	NPC471999
0.7563	Intermediate Similarity	NPC472001
0.7563	Intermediate Similarity	NPC46570
0.7563	Intermediate Similarity	NPC472000
0.7549	Intermediate Similarity	NPC23622
0.7547	Intermediate Similarity	NPC12727
0.7547	Intermediate Similarity	NPC227494
0.7545	Intermediate Similarity	NPC472747
0.7545	Intermediate Similarity	NPC329345
0.7545	Intermediate Similarity	NPC472750
0.7545	Intermediate Similarity	NPC72151
0.7545	Intermediate Similarity	NPC473283
0.7545	Intermediate Similarity	NPC473144
0.7545	Intermediate Similarity	NPC297281
0.7545	Intermediate Similarity	NPC475526
0.7542	Intermediate Similarity	NPC476107
0.7541	Intermediate Similarity	NPC476008
0.7541	Intermediate Similarity	NPC471940
0.7525	Intermediate Similarity	NPC261380
0.7523	Intermediate Similarity	NPC47880
0.7523	Intermediate Similarity	NPC474742
0.7523	Intermediate Similarity	NPC207885

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 NPC469853 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	1348
0.2-0.3	3412
0.3-0.4	2613
0.4-0.5	1085
0.5-0.6	378
0.6-0.7	113
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7826	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD8513	Phase 3
0.7264	Intermediate Similarity	NPD7983	Approved
0.7196	Intermediate Similarity	NPD5778	Approved
0.7196	Intermediate Similarity	NPD5779	Approved
0.7193	Intermediate Similarity	NPD5697	Approved
0.719	Intermediate Similarity	NPD6319	Approved
0.7179	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD46	Approved
0.717	Intermediate Similarity	NPD6698	Approved
0.7131	Intermediate Similarity	NPD8516	Approved
0.7131	Intermediate Similarity	NPD8515	Approved
0.7131	Intermediate Similarity	NPD8517	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7071	Intermediate Similarity	NPD4756	Discovery
0.7069	Intermediate Similarity	NPD6012	Approved
0.7069	Intermediate Similarity	NPD6014	Approved
0.7069	Intermediate Similarity	NPD6013	Approved
0.7043	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD6371	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.7009	Intermediate Similarity	NPD7838	Discovery
0.6983	Remote Similarity	NPD6011	Approved
0.6957	Remote Similarity	NPD5739	Approved
0.6957	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD7128	Approved
0.6949	Remote Similarity	NPD8130	Phase 1
0.6949	Remote Similarity	NPD6869	Approved
0.6949	Remote Similarity	NPD6617	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6949	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6649	Approved
0.6949	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6101	Approved
0.6909	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5701	Approved
0.6891	Remote Similarity	NPD6882	Approved
0.6857	Remote Similarity	NPD5363	Approved
0.685	Remote Similarity	NPD8074	Phase 3
0.6842	Remote Similarity	NPD5211	Phase 2
0.6838	Remote Similarity	NPD7320	Approved
0.6838	Remote Similarity	NPD6686	Approved
0.6833	Remote Similarity	NPD4632	Approved
0.6827	Remote Similarity	NPD7154	Phase 3
0.6825	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD6411	Approved
0.6786	Remote Similarity	NPD6083	Phase 2
0.6786	Remote Similarity	NPD6084	Phase 2
0.678	Remote Similarity	NPD6372	Approved
0.678	Remote Similarity	NPD6373	Approved
0.6774	Remote Similarity	NPD6054	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.6757	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD5344	Discontinued
0.675	Remote Similarity	NPD6053	Discontinued
0.6724	Remote Similarity	NPD5141	Approved
0.6723	Remote Similarity	NPD4634	Approved
0.672	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD6015	Approved
0.6719	Remote Similarity	NPD7078	Approved
0.6698	Remote Similarity	NPD1694	Approved
0.6698	Remote Similarity	NPD1696	Phase 3
0.6695	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6604	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7503	Approved
0.6587	Remote Similarity	NPD5983	Phase 2
0.6585	Remote Similarity	NPD6274	Approved
0.6583	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5696	Approved
0.6571	Remote Similarity	NPD5209	Approved
0.6571	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4270	Approved
0.6571	Remote Similarity	NPD4269	Approved
0.656	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD5226	Approved
0.6552	Remote Similarity	NPD4633	Approved
0.6552	Remote Similarity	NPD5224	Approved
0.6552	Remote Similarity	NPD5225	Approved
0.6549	Remote Similarity	NPD7839	Suspended
0.6538	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6317	Approved
0.6529	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7640	Approved
0.6522	Remote Similarity	NPD7639	Approved
0.6515	Remote Similarity	NPD7260	Phase 2
0.6508	Remote Similarity	NPD6059	Approved
0.6496	Remote Similarity	NPD5174	Approved
0.6496	Remote Similarity	NPD5175	Approved
0.6491	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD7319	Approved
0.6486	Remote Similarity	NPD7637	Suspended
0.6486	Remote Similarity	NPD5693	Phase 1
0.6486	Remote Similarity	NPD5694	Approved
0.6484	Remote Similarity	NPD7604	Phase 2
0.6484	Remote Similarity	NPD8328	Phase 3
0.6481	Remote Similarity	NPD5786	Approved
0.648	Remote Similarity	NPD6335	Approved
0.648	Remote Similarity	NPD6313	Approved
0.648	Remote Similarity	NPD6314	Approved
0.6476	Remote Similarity	NPD5369	Approved
0.6466	Remote Similarity	NPD5223	Approved
0.6462	Remote Similarity	NPD8293	Discontinued
0.6446	Remote Similarity	NPD2067	Discontinued
0.6435	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD5222	Approved
0.6404	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5221	Approved
0.6397	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5692	Phase 3
0.6393	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6336	Discontinued
0.6385	Remote Similarity	NPD7507	Approved
0.6381	Remote Similarity	NPD4821	Approved
0.6381	Remote Similarity	NPD4252	Approved
0.6381	Remote Similarity	NPD4820	Approved
0.6381	Remote Similarity	NPD4819	Approved
0.6381	Remote Similarity	NPD4822	Approved
0.6381	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4700	Approved
0.6378	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6364	Remote Similarity	NPD6672	Approved
0.6357	Remote Similarity	NPD7830	Approved
0.6357	Remote Similarity	NPD7829	Approved
0.6355	Remote Similarity	NPD6110	Phase 1
0.6355	Remote Similarity	NPD5362	Discontinued
0.6348	Remote Similarity	NPD5173	Approved
0.6348	Remote Similarity	NPD7902	Approved
0.6339	Remote Similarity	NPD7515	Phase 2
0.6339	Remote Similarity	NPD5281	Approved
0.6339	Remote Similarity	NPD5284	Approved
0.6339	Remote Similarity	NPD6050	Approved
0.6333	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5279	Phase 3
0.632	Remote Similarity	NPD690	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6868	Approved
0.6316	Remote Similarity	NPD5210	Approved
0.6316	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4753	Phase 2
0.6281	Remote Similarity	NPD4730	Approved
0.6281	Remote Similarity	NPD4729	Approved
0.627	Remote Similarity	NPD7500	Approved
0.6262	Remote Similarity	NPD6435	Approved
0.6239	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4695	Discontinued
0.6214	Remote Similarity	NPD8039	Approved
0.6202	Remote Similarity	NPD6908	Approved
0.6202	Remote Similarity	NPD6909	Approved
0.6202	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6412	Phase 2
0.6195	Remote Similarity	NPD6079	Approved
0.619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2629	Approved
0.619	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD4268	Approved
0.6182	Remote Similarity	NPD3618	Phase 1
0.6182	Remote Similarity	NPD4249	Approved
0.6179	Remote Similarity	NPD5251	Approved
0.6179	Remote Similarity	NPD5249	Phase 3
0.6179	Remote Similarity	NPD5248	Approved
0.6179	Remote Similarity	NPD5250	Approved
0.6179	Remote Similarity	NPD5247	Approved
0.6161	Remote Similarity	NPD6080	Approved
0.6161	Remote Similarity	NPD6673	Approved
0.6161	Remote Similarity	NPD6904	Approved
0.6154	Remote Similarity	NPD8080	Discontinued
0.6148	Remote Similarity	NPD5128	Approved
0.6142	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4202	Approved
0.6138	Remote Similarity	NPD7236	Approved
0.6136	Remote Similarity	NPD8273	Phase 1
0.6129	Remote Similarity	NPD5216	Approved
0.6129	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5215	Approved
0.6129	Remote Similarity	NPD5217	Approved
0.6126	Remote Similarity	NPD3573	Approved
0.6126	Remote Similarity	NPD4251	Approved
0.6126	Remote Similarity	NPD4250	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