NPASS Compound

Structure

NPC469851 OpenBabel07101718292D 32 34 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 -5.2812 -1.8090 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 -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 -4.4152 -1.3090 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 -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 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 5 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 16 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 11 2 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 22 2 0 0 0 0 15 20 2 0 0 0 0 15 31 1 0 0 0 0 17 31 1 0 0 0 0 18 20 1 0 0 0 0 19 27 2 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 28 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 24 29 2 0 0 0 0 25 30 2 0 0 0 0 25 32 1 0 0 0 0 26 4 1 1 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	458.959
LogP:	3.378
LogD:	2.274
LogS:	-4.728
# Rotatable Bonds:	8
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	4.982
Fsp3:	0.385
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:	-4.784
MDCK Permeability:	1.1808158888015896e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	79.36579132080078%
Volume Distribution (VD):	0.589
Pgp-substrate:	9.625245094299316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.656
CYP1A2-substrate:	0.335
CYP2C19-inhibitor:	0.805
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.939
CYP2C9-substrate:	0.771
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.521

ADMET: Excretion

Clearance (CL):	1.135
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.892
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.954
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.954
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC469851

Natural Product ID:	NPC469851
*Common Name:**	Bulgarialactone A
IUPAC Name:	(9aR)-3-[(1Z,4E,6E,8E)-1-hydroxy-10-methyl-3-oxododeca-1,4,6,8-tetraenyl]-6,9a-dimethyl-5,6-dihydrofuro[3,2-g]isochromene-2,9-dione
Synonyms:
Standard InCHIKey:	ZEAIQOGZNMITAD-BLERJMGRSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-5-16(2)10-8-6-7-9-11-19(27)14-22(28)23-21-13-18-12-17(3)31-15-20(18)24(29)26(21,4)32-25(23)30/h6-11,13-17,28H,5,12H2,1-4H3/b7-6+,10-8+,11-9+,22-14-/t16?,17?,26-/m1/s1
SMILES:	CCC(/C=C/C=C/C=C/C(=O)/C=C(/C1=C2C=C3CC(C)OC=C3C(=O)[C@@]2(OC1=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215387
PubChem CID:	49864117
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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
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	=	18700.0	nM	PMID[544329]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	6870.0	nM	PMID[544329]
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	=	4120.0	nM	PMID[544329]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11450.0	nM	PMID[544329]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[544329]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[544329]

☑ 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 NPC469851 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	203
0.1-0.2	1070
0.2-0.3	4179
0.3-0.4	8383
0.4-0.5	15707
0.5-0.6	8954
0.6-0.7	3558
0.7-0.8	600
0.8-0.85	32
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9588	High Similarity	NPC469852
0.8911	High Similarity	NPC469853
0.8737	High Similarity	NPC32944
0.8737	High Similarity	NPC166110
0.8737	High Similarity	NPC32552
0.8737	High Similarity	NPC193396
0.8646	High Similarity	NPC248193
0.8526	High Similarity	NPC95364
0.8526	High Similarity	NPC142159
0.8411	Intermediate Similarity	NPC321496
0.8404	Intermediate Similarity	NPC291712
0.8365	Intermediate Similarity	NPC199107
0.8365	Intermediate Similarity	NPC232969
0.8298	Intermediate Similarity	NPC281172
0.8182	Intermediate Similarity	NPC469632
0.8148	Intermediate Similarity	NPC66108
0.8125	Intermediate Similarity	NPC473145
0.81	Intermediate Similarity	NPC12727
0.8081	Intermediate Similarity	NPC29798
0.8081	Intermediate Similarity	NPC282644
0.8077	Intermediate Similarity	NPC271059
0.8077	Intermediate Similarity	NPC25666
0.8041	Intermediate Similarity	NPC472008
0.8036	Intermediate Similarity	NPC245320
0.8	Intermediate Similarity	NPC143210
0.7965	Intermediate Similarity	NPC31641
0.7965	Intermediate Similarity	NPC476815
0.7941	Intermediate Similarity	NPC208094
0.7938	Intermediate Similarity	NPC103743
0.7938	Intermediate Similarity	NPC476079
0.7938	Intermediate Similarity	NPC113370
0.7921	Intermediate Similarity	NPC295347
0.7917	Intermediate Similarity	NPC307112
0.7895	Intermediate Similarity	NPC16488
0.787	Intermediate Similarity	NPC38154
0.7864	Intermediate Similarity	NPC35717
0.7857	Intermediate Similarity	NPC469631
0.7857	Intermediate Similarity	NPC475906
0.7857	Intermediate Similarity	NPC260343
0.7857	Intermediate Similarity	NPC469628
0.7857	Intermediate Similarity	NPC469653
0.7857	Intermediate Similarity	NPC471047
0.7857	Intermediate Similarity	NPC475902
0.7835	Intermediate Similarity	NPC472009
0.7835	Intermediate Similarity	NPC316426
0.7835	Intermediate Similarity	NPC261721
0.7835	Intermediate Similarity	NPC315395
0.7822	Intermediate Similarity	NPC477241
0.781	Intermediate Similarity	NPC197835
0.781	Intermediate Similarity	NPC303653
0.781	Intermediate Similarity	NPC140591
0.781	Intermediate Similarity	NPC291500
0.781	Intermediate Similarity	NPC189609
0.78	Intermediate Similarity	NPC300312
0.78	Intermediate Similarity	NPC45579
0.78	Intermediate Similarity	NPC111114
0.78	Intermediate Similarity	NPC261607
0.7778	Intermediate Similarity	NPC327106
0.7767	Intermediate Similarity	NPC53844
0.7755	Intermediate Similarity	NPC472007
0.7745	Intermediate Similarity	NPC31021
0.7745	Intermediate Similarity	NPC471698
0.7732	Intermediate Similarity	NPC67081
0.7732	Intermediate Similarity	NPC471223
0.7714	Intermediate Similarity	NPC244456
0.7714	Intermediate Similarity	NPC224172
0.7714	Intermediate Similarity	NPC133907
0.7714	Intermediate Similarity	NPC472643
0.7714	Intermediate Similarity	NPC469657
0.7714	Intermediate Similarity	NPC110443
0.7714	Intermediate Similarity	NPC46998
0.7714	Intermediate Similarity	NPC128733
0.7714	Intermediate Similarity	NPC185141
0.7708	Intermediate Similarity	NPC475083
0.7706	Intermediate Similarity	NPC228477
0.7706	Intermediate Similarity	NPC137911
0.77	Intermediate Similarity	NPC224270
0.77	Intermediate Similarity	NPC166554
0.77	Intermediate Similarity	NPC265856
0.7699	Intermediate Similarity	NPC243298
0.7685	Intermediate Similarity	NPC266514
0.7677	Intermediate Similarity	NPC26078
0.7677	Intermediate Similarity	NPC473658
0.7664	Intermediate Similarity	NPC272528
0.7653	Intermediate Similarity	NPC234038
0.7647	Intermediate Similarity	NPC121825
0.7636	Intermediate Similarity	NPC89408
0.7634	Intermediate Similarity	NPC471225
0.7624	Intermediate Similarity	NPC472705
0.7619	Intermediate Similarity	NPC476299
0.7619	Intermediate Similarity	NPC174314
0.7619	Intermediate Similarity	NPC474012
0.7619	Intermediate Similarity	NPC54705
0.7615	Intermediate Similarity	NPC220155
0.7604	Intermediate Similarity	NPC85772
0.76	Intermediate Similarity	NPC307092
0.76	Intermediate Similarity	NPC212598
0.76	Intermediate Similarity	NPC51358
0.7596	Intermediate Similarity	NPC239895
0.7596	Intermediate Similarity	NPC20066
0.7593	Intermediate Similarity	NPC472645
0.7593	Intermediate Similarity	NPC1679
0.7589	Intermediate Similarity	NPC326264
0.7576	Intermediate Similarity	NPC471738
0.7573	Intermediate Similarity	NPC209355
0.757	Intermediate Similarity	NPC297281
0.757	Intermediate Similarity	NPC118902
0.757	Intermediate Similarity	NPC104161
0.757	Intermediate Similarity	NPC469980
0.757	Intermediate Similarity	NPC473144
0.757	Intermediate Similarity	NPC472755
0.7568	Intermediate Similarity	NPC304180
0.7568	Intermediate Similarity	NPC474315
0.7568	Intermediate Similarity	NPC179798
0.7553	Intermediate Similarity	NPC315765
0.7551	Intermediate Similarity	NPC470177
0.7551	Intermediate Similarity	NPC187529
0.7551	Intermediate Similarity	NPC261380
0.7549	Intermediate Similarity	NPC115021
0.7549	Intermediate Similarity	NPC469692
0.7549	Intermediate Similarity	NPC59646
0.7549	Intermediate Similarity	NPC469645
0.7547	Intermediate Similarity	NPC474742
0.7547	Intermediate Similarity	NPC472753
0.7547	Intermediate Similarity	NPC471699
0.7544	Intermediate Similarity	NPC471145
0.7525	Intermediate Similarity	NPC475879
0.7524	Intermediate Similarity	NPC300584
0.75	Intermediate Similarity	NPC325031
0.75	Intermediate Similarity	NPC318082
0.75	Intermediate Similarity	NPC301596
0.75	Intermediate Similarity	NPC299396
0.75	Intermediate Similarity	NPC172998
0.75	Intermediate Similarity	NPC309190
0.7478	Intermediate Similarity	NPC21326
0.7477	Intermediate Similarity	NPC149371
0.7477	Intermediate Similarity	NPC472754
0.7476	Intermediate Similarity	NPC470521
0.7475	Intermediate Similarity	NPC122502
0.7455	Intermediate Similarity	NPC264819
0.7455	Intermediate Similarity	NPC322903
0.7453	Intermediate Similarity	NPC472644
0.7453	Intermediate Similarity	NPC215253
0.7453	Intermediate Similarity	NPC469551
0.7453	Intermediate Similarity	NPC185253
0.7451	Intermediate Similarity	NPC175842
0.7451	Intermediate Similarity	NPC32494
0.7449	Intermediate Similarity	NPC14575
0.7449	Intermediate Similarity	NPC196487
0.7447	Intermediate Similarity	NPC315394
0.7447	Intermediate Similarity	NPC316324
0.7434	Intermediate Similarity	NPC56448
0.7434	Intermediate Similarity	NPC469454
0.7434	Intermediate Similarity	NPC469496
0.7434	Intermediate Similarity	NPC469463
0.7431	Intermediate Similarity	NPC266570
0.7431	Intermediate Similarity	NPC477125
0.7429	Intermediate Similarity	NPC134083
0.7429	Intermediate Similarity	NPC202705
0.7426	Intermediate Similarity	NPC280833
0.7426	Intermediate Similarity	NPC106040
0.7426	Intermediate Similarity	NPC115179
0.7407	Intermediate Similarity	NPC72151
0.7407	Intermediate Similarity	NPC475526
0.7407	Intermediate Similarity	NPC475945
0.7407	Intermediate Similarity	NPC329345
0.7407	Intermediate Similarity	NPC473283
0.7407	Intermediate Similarity	NPC475871
0.7404	Intermediate Similarity	NPC234339
0.7404	Intermediate Similarity	NPC91408
0.7404	Intermediate Similarity	NPC273197
0.74	Intermediate Similarity	NPC86005
0.74	Intermediate Similarity	NPC471739
0.74	Intermediate Similarity	NPC23622
0.74	Intermediate Similarity	NPC72513
0.7391	Intermediate Similarity	NPC243065
0.7387	Intermediate Similarity	NPC23497
0.7387	Intermediate Similarity	NPC20192
0.7383	Intermediate Similarity	NPC47880
0.7383	Intermediate Similarity	NPC206079
0.7379	Intermediate Similarity	NPC476049
0.7379	Intermediate Similarity	NPC475302
0.7368	Intermediate Similarity	NPC478122
0.7364	Intermediate Similarity	NPC475294
0.7364	Intermediate Similarity	NPC91034
0.7358	Intermediate Similarity	NPC141191
0.7358	Intermediate Similarity	NPC166770
0.7358	Intermediate Similarity	NPC316598
0.7358	Intermediate Similarity	NPC222011
0.7358	Intermediate Similarity	NPC306908
0.7358	Intermediate Similarity	NPC64742
0.7353	Intermediate Similarity	NPC469464
0.7353	Intermediate Similarity	NPC3436
0.7353	Intermediate Similarity	NPC77337
0.7347	Intermediate Similarity	NPC288281
0.7345	Intermediate Similarity	NPC221144
0.7339	Intermediate Similarity	NPC474741
0.7333	Intermediate Similarity	NPC242848
0.7333	Intermediate Similarity	NPC9812
0.7333	Intermediate Similarity	NPC473291

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 NPC469851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1364
0.2-0.3	3442
0.3-0.4	2649
0.4-0.5	1070
0.5-0.6	339
0.6-0.7	94
0.7-0.8	9
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
0.7447	Intermediate Similarity	NPD4756	Discovery
0.7379	Intermediate Similarity	NPD5779	Approved
0.7379	Intermediate Similarity	NPD5778	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5697	Approved
0.7019	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD7154	Phase 3
0.6991	Remote Similarity	NPD6881	Approved
0.6991	Remote Similarity	NPD6899	Approved
0.6952	Remote Similarity	NPD7983	Approved
0.6952	Remote Similarity	NPD6411	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD6013	Approved
0.69	Remote Similarity	NPD5209	Approved
0.6897	Remote Similarity	NPD6053	Discontinued
0.6881	Remote Similarity	NPD4225	Approved
0.687	Remote Similarity	NPD6883	Approved
0.687	Remote Similarity	NPD7290	Approved
0.687	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD5363	Approved
0.686	Remote Similarity	NPD8513	Phase 3
0.6852	Remote Similarity	NPD7839	Suspended
0.6842	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD5282	Discontinued
0.6814	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6847	Approved
0.681	Remote Similarity	NPD8130	Phase 1
0.681	Remote Similarity	NPD6617	Approved
0.681	Remote Similarity	NPD6869	Approved
0.681	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD5786	Approved
0.6765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD6882	Approved
0.6752	Remote Similarity	NPD8297	Approved
0.6727	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6699	Remote Similarity	NPD1694	Approved
0.6699	Remote Similarity	NPD1696	Phase 3
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD5211	Phase 2
0.6639	Remote Similarity	NPD6319	Approved
0.6638	Remote Similarity	NPD6372	Approved
0.6638	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5141	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4270	Approved
0.6569	Remote Similarity	NPD4269	Approved
0.6542	Remote Similarity	NPD6698	Approved
0.6542	Remote Similarity	NPD46	Approved
0.6542	Remote Similarity	NPD7838	Discovery
0.6535	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD5694	Approved
0.6471	Remote Similarity	NPD5369	Approved
0.6457	Remote Similarity	NPD8074	Phase 3
0.6446	Remote Similarity	NPD6274	Approved
0.6441	Remote Similarity	NPD6371	Approved
0.6429	Remote Similarity	NPD7492	Approved
0.6423	Remote Similarity	NPD7101	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.6408	Remote Similarity	NPD6435	Approved
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD5226	Approved
0.6396	Remote Similarity	NPD5222	Approved
0.6396	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6317	Approved
0.6389	Remote Similarity	NPD5692	Phase 3
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7260	Phase 2
0.6381	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6616	Approved
0.6373	Remote Similarity	NPD4821	Approved
0.6373	Remote Similarity	NPD4819	Approved
0.6373	Remote Similarity	NPD4252	Approved
0.6373	Remote Similarity	NPD4822	Approved
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4820	Approved
0.6372	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD6648	Approved
0.6372	Remote Similarity	NPD7640	Approved
0.6371	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD8039	Approved
0.6355	Remote Similarity	NPD5737	Approved
0.6355	Remote Similarity	NPD6672	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6348	Remote Similarity	NPD5175	Approved
0.6346	Remote Similarity	NPD5362	Discontinued
0.6346	Remote Similarity	NPD6110	Phase 1
0.6341	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.6341	Remote Similarity	NPD6335	Approved
0.6339	Remote Similarity	NPD4755	Approved
0.6339	Remote Similarity	NPD5173	Approved
0.633	Remote Similarity	NPD6050	Approved
0.6328	Remote Similarity	NPD7078	Approved
0.6321	Remote Similarity	NPD4249	Approved
0.632	Remote Similarity	NPD6016	Approved
0.632	Remote Similarity	NPD6015	Approved
0.6316	Remote Similarity	NPD5223	Approved
0.6311	Remote Similarity	NPD6868	Approved
0.6303	Remote Similarity	NPD4634	Approved
0.6303	Remote Similarity	NPD2067	Discontinued
0.6296	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7638	Approved
0.6281	Remote Similarity	NPD4632	Approved
0.6279	Remote Similarity	NPD7736	Approved
0.6273	Remote Similarity	NPD6399	Phase 3
0.627	Remote Similarity	NPD5988	Approved
0.627	Remote Similarity	NPD6370	Approved
0.6262	Remote Similarity	NPD4251	Approved
0.6262	Remote Similarity	NPD3573	Approved
0.6262	Remote Similarity	NPD4250	Approved
0.626	Remote Similarity	NPD6009	Approved
0.6228	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD4695	Discontinued
0.6214	Remote Similarity	NPD5368	Approved
0.6211	Remote Similarity	NPD3704	Approved
0.6211	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7331	Phase 2
0.619	Remote Similarity	NPD5983	Phase 2
0.6182	Remote Similarity	NPD5281	Approved
0.6182	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5284	Approved
0.6182	Remote Similarity	NPD6079	Approved
0.6179	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4268	Approved
0.6174	Remote Similarity	NPD5344	Discontinued
0.6168	Remote Similarity	NPD5279	Phase 3
0.6161	Remote Similarity	NPD5210	Approved
0.6161	Remote Similarity	NPD4629	Approved
0.6148	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6673	Approved
0.6147	Remote Similarity	NPD6904	Approved
0.6147	Remote Similarity	NPD5370	Suspended
0.6147	Remote Similarity	NPD6080	Approved
0.6147	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD4729	Approved
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4730	Approved
0.6134	Remote Similarity	NPD6686	Approved
0.6111	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6059	Approved
0.6106	Remote Similarity	NPD4697	Phase 3
0.6105	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7604	Phase 2
0.6094	Remote Similarity	NPD7829	Approved
0.6094	Remote Similarity	NPD7830	Approved
0.6083	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8293	Discontinued
0.6068	Remote Similarity	NPD6647	Phase 2
0.6064	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6909	Approved
0.6063	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7503	Approved
0.6063	Remote Similarity	NPD6908	Approved
0.6053	Remote Similarity	NPD7902	Approved
0.6038	Remote Similarity	NPD5332	Approved
0.6038	Remote Similarity	NPD5331	Approved
0.6036	Remote Similarity	NPD7515	Phase 2
0.6033	Remote Similarity	NPD5251	Approved
0.6033	Remote Similarity	NPD5247	Approved
0.6033	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5249	Phase 3
0.6033	Remote Similarity	NPD5250	Approved
0.6033	Remote Similarity	NPD5248	Approved
0.6019	Remote Similarity	NPD4519	Discontinued
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD4623	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD5280	Approved
0.6019	Remote Similarity	NPD4694	Approved
0.6019	Remote Similarity	NPD7521	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