NPASS Compound

Structure

NPC32944 OpenBabel07101718242D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.8615 -5.0949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -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 -2.8833 -4.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.9360 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 5.2812 -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 -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 3.5491 0.1910 0.0000 C 0 0 0 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 4.4152 -1.3090 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 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 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 2 0 0 0 0 6 7 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	3.965
LogD:	2.545
LogS:	-4.661
# Rotatable Bonds:	6
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.123
Fsp3:	0.381
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:	-4.928
MDCK Permeability:	2.169556319131516e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.631
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	87.44121551513672%
Volume Distribution (VD):	1.758
Pgp-substrate:	8.62558650970459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.914
CYP1A2-substrate:	0.795
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.422
CYP2C9-inhibitor:	0.875
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.502
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	1.428
Half-life (T1/2):	0.723

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.977
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.96
Carcinogencity:	0.917
Eye Corrosion:	0.003
Eye Irritation:	0.091
Respiratory Toxicity:	0.792

Download Data

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

Natural Product: NPC32944

Natural Product ID:	NPC32944
*Common Name:**	Rubropunctatin
IUPAC Name:	(9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]furo[3,2-g]isochromene-2,9-dione
Synonyms:	Rubropunctatin
Standard InCHIKey:	SULYDLFVUNXAMP-WKOQKXSESA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10-12H,4,6-7,9H2,1-3H3/b8-5+/t21-/m1/s1
SMILES:	CCCCCC(=O)C1=C2C=C3C=C(/C=C/C)OC=C3C(=O)[C@]2(C)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215465
PubChem CID:	6452445
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	>	50000.0	nM	PMID[455160]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	28200.0	nM	PMID[455160]
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	=	28200.0	nM	PMID[455160]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[455160]
NPT2	Others	Unspecified		IC50	=	9200.0	nM	PMID[455160]
NPT2	Others	Unspecified		IC50	=	40.0	nM	PMID[455160]

☑ 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 NPC32944 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	223
0.1-0.2	1312
0.2-0.3	5316
0.3-0.4	11249
0.4-0.5	15901
0.5-0.6	6393
0.6-0.7	1996
0.7-0.8	279
0.8-0.85	14
0.85-0.9	5
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC193396
0.9765	High Similarity	NPC95364
0.9765	High Similarity	NPC142159
0.954	High Similarity	NPC166110
0.9432	High Similarity	NPC248193
0.9294	High Similarity	NPC281172
0.9186	High Similarity	NPC291712
0.8804	High Similarity	NPC12727
0.8737	High Similarity	NPC469851
0.8696	High Similarity	NPC143210
0.8681	High Similarity	NPC32552
0.8557	High Similarity	NPC271059
0.8557	High Similarity	NPC25666
0.8384	Intermediate Similarity	NPC469852
0.837	Intermediate Similarity	NPC224270
0.83	Intermediate Similarity	NPC469853
0.8211	Intermediate Similarity	NPC31021
0.8211	Intermediate Similarity	NPC471698
0.8173	Intermediate Similarity	NPC321496
0.798	Intermediate Similarity	NPC471699
0.7941	Intermediate Similarity	NPC232969
0.7941	Intermediate Similarity	NPC199107
0.7938	Intermediate Similarity	NPC318082
0.7835	Intermediate Similarity	NPC295347
0.7812	Intermediate Similarity	NPC29798
0.7812	Intermediate Similarity	NPC282644
0.7766	Intermediate Similarity	NPC475902
0.7727	Intermediate Similarity	NPC471225
0.7692	Intermediate Similarity	NPC475690
0.7684	Intermediate Similarity	NPC280833
0.7677	Intermediate Similarity	NPC208094
0.7634	Intermediate Similarity	NPC307112
0.7609	Intermediate Similarity	NPC288281
0.7579	Intermediate Similarity	NPC475906
0.7579	Intermediate Similarity	NPC469628
0.7579	Intermediate Similarity	NPC471047
0.7579	Intermediate Similarity	NPC469653
0.7579	Intermediate Similarity	NPC469631
0.7576	Intermediate Similarity	NPC301596
0.7576	Intermediate Similarity	NPC172998
0.7576	Intermediate Similarity	NPC299396
0.7573	Intermediate Similarity	NPC272528
0.7553	Intermediate Similarity	NPC261721
0.7553	Intermediate Similarity	NPC279859
0.7553	Intermediate Similarity	NPC38576
0.7528	Intermediate Similarity	NPC180290
0.7524	Intermediate Similarity	NPC327106
0.75	Intermediate Similarity	NPC329826
0.75	Intermediate Similarity	NPC471326
0.75	Intermediate Similarity	NPC469414
0.75	Intermediate Similarity	NPC221231
0.7475	Intermediate Similarity	NPC234339
0.7475	Intermediate Similarity	NPC273197
0.7475	Intermediate Similarity	NPC209355
0.7474	Intermediate Similarity	NPC476079
0.7474	Intermediate Similarity	NPC113370
0.7474	Intermediate Similarity	NPC103743
0.7471	Intermediate Similarity	NPC287878
0.7455	Intermediate Similarity	NPC243298
0.7449	Intermediate Similarity	NPC1108
0.7447	Intermediate Similarity	NPC189311
0.7423	Intermediate Similarity	NPC280592
0.7423	Intermediate Similarity	NPC213636
0.7423	Intermediate Similarity	NPC469372
0.7423	Intermediate Similarity	NPC253177
0.7419	Intermediate Similarity	NPC118423
0.7419	Intermediate Similarity	NPC16488
0.7412	Intermediate Similarity	NPC134385
0.7396	Intermediate Similarity	NPC473658
0.7396	Intermediate Similarity	NPC26078
0.7396	Intermediate Similarity	NPC241507
0.7396	Intermediate Similarity	NPC472302
0.7391	Intermediate Similarity	NPC42470
0.7374	Intermediate Similarity	NPC476596
0.7374	Intermediate Similarity	NPC38830
0.7368	Intermediate Similarity	NPC472009
0.7368	Intermediate Similarity	NPC234038
0.7368	Intermediate Similarity	NPC315395
0.7368	Intermediate Similarity	NPC316426
0.7368	Intermediate Similarity	NPC168248
0.7363	Intermediate Similarity	NPC150646
0.7363	Intermediate Similarity	NPC473981
0.7363	Intermediate Similarity	NPC473980
0.7353	Intermediate Similarity	NPC54705
0.7347	Intermediate Similarity	NPC471329
0.7347	Intermediate Similarity	NPC472705
0.7347	Intermediate Similarity	NPC45579
0.7347	Intermediate Similarity	NPC296114
0.734	Intermediate Similarity	NPC30486
0.7339	Intermediate Similarity	NPC326264
0.7333	Intermediate Similarity	NPC316324
0.7327	Intermediate Similarity	NPC134083
0.7326	Intermediate Similarity	NPC470693
0.7321	Intermediate Similarity	NPC245320
0.732	Intermediate Similarity	NPC307092
0.732	Intermediate Similarity	NPC284561
0.732	Intermediate Similarity	NPC51358
0.7312	Intermediate Similarity	NPC85772
0.7312	Intermediate Similarity	NPC268122
0.7308	Intermediate Similarity	NPC297281
0.7308	Intermediate Similarity	NPC473144
0.7292	Intermediate Similarity	NPC478145
0.7292	Intermediate Similarity	NPC125925
0.7292	Intermediate Similarity	NPC472007
0.729	Intermediate Similarity	NPC137911
0.729	Intermediate Similarity	NPC228477
0.729	Intermediate Similarity	NPC23497
0.7282	Intermediate Similarity	NPC168319
0.7282	Intermediate Similarity	NPC194028
0.7273	Intermediate Similarity	NPC476597
0.7273	Intermediate Similarity	NPC476598
0.7264	Intermediate Similarity	NPC266514
0.7263	Intermediate Similarity	NPC130030
0.7257	Intermediate Similarity	NPC473145
0.7257	Intermediate Similarity	NPC31641
0.7257	Intermediate Similarity	NPC476815
0.7255	Intermediate Similarity	NPC35717
0.7255	Intermediate Similarity	NPC264378
0.7253	Intermediate Similarity	NPC471220
0.7253	Intermediate Similarity	NPC128276
0.7253	Intermediate Similarity	NPC475699
0.7248	Intermediate Similarity	NPC66108
0.7245	Intermediate Similarity	NPC469595
0.7245	Intermediate Similarity	NPC212679
0.7245	Intermediate Similarity	NPC220454
0.7234	Intermediate Similarity	NPC475083
0.7234	Intermediate Similarity	NPC193198
0.7222	Intermediate Similarity	NPC89408
0.7222	Intermediate Similarity	NPC27205
0.7222	Intermediate Similarity	NPC123360
0.7222	Intermediate Similarity	NPC40353
0.7216	Intermediate Similarity	NPC472008
0.7212	Intermediate Similarity	NPC189609
0.7212	Intermediate Similarity	NPC197835
0.7212	Intermediate Similarity	NPC303653
0.7212	Intermediate Similarity	NPC140591
0.7212	Intermediate Similarity	NPC291500
0.7209	Intermediate Similarity	NPC218477
0.7204	Intermediate Similarity	NPC471325
0.7204	Intermediate Similarity	NPC474353
0.7204	Intermediate Similarity	NPC286229
0.72	Intermediate Similarity	NPC470697
0.72	Intermediate Similarity	NPC477130
0.72	Intermediate Similarity	NPC469632
0.72	Intermediate Similarity	NPC477129
0.7191	Intermediate Similarity	NPC476355
0.7188	Intermediate Similarity	NPC472863
0.7188	Intermediate Similarity	NPC203795
0.7184	Intermediate Similarity	NPC469551
0.7184	Intermediate Similarity	NPC215253
0.7184	Intermediate Similarity	NPC474012
0.7184	Intermediate Similarity	NPC185253
0.7184	Intermediate Similarity	NPC476299
0.7174	Intermediate Similarity	NPC63649
0.7174	Intermediate Similarity	NPC178277
0.7174	Intermediate Similarity	NPC264227
0.7174	Intermediate Similarity	NPC472965
0.7174	Intermediate Similarity	NPC471299
0.7174	Intermediate Similarity	NPC471740
0.7172	Intermediate Similarity	NPC20713
0.7158	Intermediate Similarity	NPC196487
0.7158	Intermediate Similarity	NPC14575
0.7158	Intermediate Similarity	NPC474359
0.7157	Intermediate Similarity	NPC38530
0.7157	Intermediate Similarity	NPC53844
0.7157	Intermediate Similarity	NPC2049
0.7157	Intermediate Similarity	NPC239895
0.7157	Intermediate Similarity	NPC84335
0.7143	Intermediate Similarity	NPC118902
0.7143	Intermediate Similarity	NPC104161
0.7143	Intermediate Similarity	NPC68156
0.7143	Intermediate Similarity	NPC41780
0.7143	Intermediate Similarity	NPC5509
0.7143	Intermediate Similarity	NPC469980
0.7143	Intermediate Similarity	NPC57744
0.7143	Intermediate Similarity	NPC187568
0.7143	Intermediate Similarity	NPC473825
0.713	Intermediate Similarity	NPC38154
0.7128	Intermediate Similarity	NPC173609
0.7128	Intermediate Similarity	NPC94200
0.7126	Intermediate Similarity	NPC232812
0.7115	Intermediate Similarity	NPC469657
0.7115	Intermediate Similarity	NPC224172
0.7115	Intermediate Similarity	NPC244456
0.7113	Intermediate Similarity	NPC478144
0.7113	Intermediate Similarity	NPC266957
0.7113	Intermediate Similarity	NPC181327
0.7113	Intermediate Similarity	NPC471739
0.7113	Intermediate Similarity	NPC72513
0.71	Intermediate Similarity	NPC165383
0.7093	Intermediate Similarity	NPC474619
0.7087	Intermediate Similarity	NPC166770
0.7083	Intermediate Similarity	NPC67081
0.7083	Intermediate Similarity	NPC96621
0.7083	Intermediate Similarity	NPC471223
0.7083	Intermediate Similarity	NPC470177
0.7083	Intermediate Similarity	NPC261380
0.708	Intermediate Similarity	NPC315974
0.7079	Intermediate Similarity	NPC474705
0.7071	Intermediate Similarity	NPC166554

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 NPC32944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1532
0.2-0.3	3664
0.3-0.4	2532
0.4-0.5	908
0.5-0.6	269
0.6-0.7	38
0.7-0.8	3
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
0.7528	Intermediate Similarity	NPD4756	Discovery
0.7128	Intermediate Similarity	NPD5209	Approved
0.6977	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8039	Approved
0.6907	Remote Similarity	NPD1694	Approved
0.6832	Remote Similarity	NPD5693	Phase 1
0.6832	Remote Similarity	NPD5694	Approved
0.6733	Remote Similarity	NPD5692	Phase 3
0.67	Remote Similarity	NPD5737	Approved
0.67	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6607	Remote Similarity	NPD2067	Discontinued
0.6569	Remote Similarity	NPD5785	Approved
0.6552	Remote Similarity	NPD7115	Discovery
0.6476	Remote Similarity	NPD5695	Phase 3
0.6471	Remote Similarity	NPD6904	Approved
0.6471	Remote Similarity	NPD6080	Approved
0.6471	Remote Similarity	NPD6673	Approved
0.6442	Remote Similarity	NPD5778	Approved
0.6442	Remote Similarity	NPD5779	Approved
0.6404	Remote Similarity	NPD3704	Approved
0.64	Remote Similarity	NPD5363	Approved
0.6381	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD7154	Phase 3
0.6355	Remote Similarity	NPD6084	Phase 2
0.6355	Remote Similarity	NPD6083	Phase 2
0.6339	Remote Similarity	NPD5697	Approved
0.6321	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5654	Approved
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5696	Approved
0.6292	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6011	Approved
0.6283	Remote Similarity	NPD6899	Approved
0.6283	Remote Similarity	NPD6881	Approved
0.6275	Remote Similarity	NPD3573	Approved
0.625	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5207	Approved
0.6238	Remote Similarity	NPD1696	Phase 3
0.6228	Remote Similarity	NPD6013	Approved
0.6228	Remote Similarity	NPD6012	Approved
0.6228	Remote Similarity	NPD6014	Approved
0.6224	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6053	Discontinued
0.6204	Remote Similarity	NPD5959	Approved
0.6195	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6411	Approved
0.6186	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD5330	Approved
0.6176	Remote Similarity	NPD6684	Approved
0.6176	Remote Similarity	NPD6098	Approved
0.6176	Remote Similarity	NPD7334	Approved
0.6176	Remote Similarity	NPD6409	Approved
0.6176	Remote Similarity	NPD7146	Approved
0.6174	Remote Similarity	NPD7290	Approved
0.6174	Remote Similarity	NPD7102	Approved
0.6174	Remote Similarity	NPD6883	Approved
0.6162	Remote Similarity	NPD5369	Approved
0.6154	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4225	Approved
0.6147	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6847	Approved
0.6121	Remote Similarity	NPD6617	Approved
0.6121	Remote Similarity	NPD6649	Approved
0.6121	Remote Similarity	NPD6869	Approved
0.6121	Remote Similarity	NPD8130	Phase 1
0.6121	Remote Similarity	NPD6650	Approved
0.6106	Remote Similarity	NPD5739	Approved
0.6106	Remote Similarity	NPD7128	Approved
0.6106	Remote Similarity	NPD6675	Approved
0.6106	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD4269	Approved
0.61	Remote Similarity	NPD4270	Approved
0.6095	Remote Similarity	NPD46	Approved
0.6095	Remote Similarity	NPD6698	Approved
0.6078	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD8297	Approved
0.6068	Remote Similarity	NPD6882	Approved
0.6066	Remote Similarity	NPD8513	Phase 3
0.6061	Remote Similarity	NPD4695	Discontinued
0.6061	Remote Similarity	NPD4252	Approved
0.6058	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6903	Approved
0.6053	Remote Similarity	NPD5701	Approved
0.6038	Remote Similarity	NPD7983	Approved
0.6038	Remote Similarity	NPD5284	Approved
0.6038	Remote Similarity	NPD5281	Approved
0.6019	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7320	Approved
0.5984	Remote Similarity	NPD6319	Approved
0.5981	Remote Similarity	NPD6399	Phase 3
0.5963	Remote Similarity	NPD7839	Suspended
0.5948	Remote Similarity	NPD6373	Approved
0.5948	Remote Similarity	NPD6372	Approved
0.5943	Remote Similarity	NPD7838	Discovery
0.5935	Remote Similarity	NPD8516	Approved
0.5935	Remote Similarity	NPD8515	Approved
0.5935	Remote Similarity	NPD8517	Approved
0.5926	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7748	Approved
0.5926	Remote Similarity	NPD7900	Approved
0.5913	Remote Similarity	NPD6614	Approved
0.5905	Remote Similarity	NPD5208	Approved
0.5897	Remote Similarity	NPD6371	Approved
0.5891	Remote Similarity	NPD7260	Phase 2
0.5888	Remote Similarity	NPD7637	Suspended
0.5882	Remote Similarity	NPD5362	Discontinued
0.5877	Remote Similarity	NPD5909	Discontinued
0.5872	Remote Similarity	NPD4629	Approved
0.5872	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5210	Approved
0.587	Remote Similarity	NPD7331	Phase 2
0.5868	Remote Similarity	NPD6317	Approved
0.5865	Remote Similarity	NPD5280	Approved
0.5865	Remote Similarity	NPD4694	Approved
0.5865	Remote Similarity	NPD5279	Phase 3
0.5865	Remote Similarity	NPD5690	Phase 2
0.5862	Remote Similarity	NPD8779	Phase 3
0.5856	Remote Similarity	NPD7638	Approved
0.5854	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD1695	Approved
0.5849	Remote Similarity	NPD4753	Phase 2
0.5847	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5211	Phase 2
0.5826	Remote Similarity	NPD6008	Approved
0.582	Remote Similarity	NPD6313	Approved
0.582	Remote Similarity	NPD6314	Approved
0.582	Remote Similarity	NPD6335	Approved
0.5818	Remote Similarity	NPD5221	Approved
0.5818	Remote Similarity	NPD5222	Approved
0.5818	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD7640	Approved
0.5804	Remote Similarity	NPD6648	Approved
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5804	Remote Similarity	NPD7639	Approved
0.5794	Remote Similarity	NPD7492	Approved
0.5785	Remote Similarity	NPD6274	Approved
0.5785	Remote Similarity	NPD6868	Approved
0.5784	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4058	Approved
0.5772	Remote Similarity	NPD7100	Approved
0.5772	Remote Similarity	NPD7101	Approved
0.5766	Remote Similarity	NPD5173	Approved
0.5766	Remote Similarity	NPD7902	Approved
0.5752	Remote Similarity	NPD5223	Approved
0.575	Remote Similarity	NPD4632	Approved
0.5748	Remote Similarity	NPD6616	Approved
0.5743	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7515	Phase 2
0.5741	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5141	Approved
0.5738	Remote Similarity	NPD6009	Approved
0.5728	Remote Similarity	NPD6110	Phase 1
0.5726	Remote Similarity	NPD6686	Approved
0.5726	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4249	Approved
0.5714	Remote Similarity	NPD4519	Discontinued
0.5714	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4623	Approved
0.5703	Remote Similarity	NPD7078	Approved
0.5703	Remote Similarity	NPD8074	Phase 3
0.5702	Remote Similarity	NPD4633	Approved
0.5702	Remote Similarity	NPD5224	Approved
0.5702	Remote Similarity	NPD5225	Approved
0.5702	Remote Similarity	NPD5226	Approved
0.5701	Remote Similarity	NPD6051	Approved
0.5701	Remote Similarity	NPD5370	Suspended
0.57	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.568	Remote Similarity	NPD5983	Phase 2
0.568	Remote Similarity	NPD6015	Approved
0.568	Remote Similarity	NPD6016	Approved
0.5678	Remote Similarity	NPD2182	Approved
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD3668	Phase 3
0.5673	Remote Similarity	NPD4197	Approved
0.5667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4251	Approved
0.566	Remote Similarity	NPD4250	Approved
0.5659	Remote Similarity	NPD7736	Approved
0.5652	Remote Similarity	NPD5175	Approved
0.5652	Remote Similarity	NPD5174	Approved
0.5652	Remote Similarity	NPD6647	Phase 2
0.5636	Remote Similarity	NPD6001	Approved
0.5635	Remote Similarity	NPD6370	Approved
0.5635	Remote Similarity	NPD5988	Approved
0.5631	Remote Similarity	NPD3667	Approved
0.5631	Remote Similarity	NPD6435	Approved
0.563	Remote Similarity	NPD4634	Approved
0.563	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4755	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