NPASS Compound

Structure

NPC273197 OpenBabel07101718192D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.9726 -2.6765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 -3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1092 -1.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4349 -1.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0215 -2.9855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2784 -2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8605 0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8387 0.6034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 -1.3383 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 11 2 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 8 19 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 13 6 1 6 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 19 1 0 0 0 0 15 20 2 0 0 0 0 16 11 1 1 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 5 1 6 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.14
Volume:	348.433
LogP:	1.055
LogD:	1.093
LogS:	-2.806
# Rotatable Bonds:	3
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	5.77
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.914
MDCK Permeability:	2.8669137464021333e-05
Pgp-inhibitor:	0.552
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	78.28974151611328%
Volume Distribution (VD):	1.63
Pgp-substrate:	30.879417419433594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.107
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.561
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.637
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.537
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	5.843
Half-life (T1/2):	0.53

ADMET: Toxicity

hERG Blockers:	0.163
Human Hepatotoxicity (H-HT):	0.793
Drug-inuced Liver Injury (DILI):	0.736
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.65
Maximum Recommended Daily Dose:	0.645
Skin Sensitization:	0.933
Carcinogencity:	0.739
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.188

Download Data

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

Natural Product: NPC273197

Natural Product ID:	NPC273197
*Common Name:**	HKQSOGUZSSFJSM-GTACMHHNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HKQSOGUZSSFJSM-GTACMHHNSA-N
Standard InCHI:	InChI=1S/C19H22O6/c1-9(2)17(21)24-14-8-19(5)15(20)7-12(25-19)10(3)6-13-16(14)11(4)18(22)23-13/h7,9,13-14,16H,3-4,6,8H2,1-2,5H3/t13-,14-,16+,19-/m1/s1
SMILES:	CC(C)C(=O)O[C@@H]1C[C@]2(C)C(=O)C=C(C(=C)C[C@@H]3[C@@H]1C(=C)C(=O)O3)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380785
PubChem CID:	73345841
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO29281	Helianthus angustifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO29281	Helianthus angustifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	9594.01	nM	PMID[520992]
NPT27	Others	Unspecified		IC50	=	25200.0	nM	PMID[520992]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	9590.0	nM	PMID[520992]

☑ 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 NPC273197 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	242
0.1-0.2	1395
0.2-0.3	5293
0.3-0.4	10795
0.4-0.5	15135
0.5-0.6	6989
0.6-0.7	2336
0.7-0.8	496
0.8-0.85	3
0.85-0.9	6
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234339
0.9888	High Similarity	NPC172998
0.9667	High Similarity	NPC299396
0.9667	High Similarity	NPC301596
0.9158	High Similarity	NPC197835
0.9158	High Similarity	NPC291500
0.9158	High Similarity	NPC189609
0.9158	High Similarity	NPC140591
0.9158	High Similarity	NPC303653
0.8614	High Similarity	NPC38154
0.8333	Intermediate Similarity	NPC128429
0.8298	Intermediate Similarity	NPC469718
0.8298	Intermediate Similarity	NPC329857
0.8211	Intermediate Similarity	NPC20713
0.8172	Intermediate Similarity	NPC475703
0.8152	Intermediate Similarity	NPC215364
0.8085	Intermediate Similarity	NPC469631
0.8085	Intermediate Similarity	NPC469628
0.8085	Intermediate Similarity	NPC469653
0.8085	Intermediate Similarity	NPC475906
0.8085	Intermediate Similarity	NPC471047
0.8065	Intermediate Similarity	NPC284902
0.8065	Intermediate Similarity	NPC50637
0.8061	Intermediate Similarity	NPC476275
0.8043	Intermediate Similarity	NPC115786
0.8041	Intermediate Similarity	NPC140543
0.8041	Intermediate Similarity	NPC473330
0.8041	Intermediate Similarity	NPC474338
0.8041	Intermediate Similarity	NPC473316
0.8	Intermediate Similarity	NPC166919
0.7979	Intermediate Similarity	NPC160138
0.7959	Intermediate Similarity	NPC474947
0.7935	Intermediate Similarity	NPC272814
0.7935	Intermediate Similarity	NPC474703
0.7921	Intermediate Similarity	NPC474339
0.7921	Intermediate Similarity	NPC476270
0.7921	Intermediate Similarity	NPC164598
0.7917	Intermediate Similarity	NPC179394
0.7917	Intermediate Similarity	NPC312042
0.7917	Intermediate Similarity	NPC144133
0.7912	Intermediate Similarity	NPC301477
0.7912	Intermediate Similarity	NPC141810
0.7912	Intermediate Similarity	NPC281949
0.7912	Intermediate Similarity	NPC25684
0.7895	Intermediate Similarity	NPC475902
0.7889	Intermediate Similarity	NPC617
0.7872	Intermediate Similarity	NPC162071
0.7872	Intermediate Similarity	NPC107787
0.7872	Intermediate Similarity	NPC38576
0.7872	Intermediate Similarity	NPC279859
0.7864	Intermediate Similarity	NPC477510
0.7864	Intermediate Similarity	NPC471143
0.7857	Intermediate Similarity	NPC476267
0.7857	Intermediate Similarity	NPC477131
0.7835	Intermediate Similarity	NPC133698
0.7826	Intermediate Similarity	NPC173609
0.7812	Intermediate Similarity	NPC64913
0.7812	Intermediate Similarity	NPC242877
0.7812	Intermediate Similarity	NPC151770
0.7812	Intermediate Similarity	NPC295312
0.78	Intermediate Similarity	NPC471140
0.78	Intermediate Similarity	NPC471462
0.7789	Intermediate Similarity	NPC471739
0.7789	Intermediate Similarity	NPC231889
0.7778	Intermediate Similarity	NPC304886
0.7766	Intermediate Similarity	NPC130030
0.7766	Intermediate Similarity	NPC235792
0.7766	Intermediate Similarity	NPC78089
0.7755	Intermediate Similarity	NPC125674
0.7755	Intermediate Similarity	NPC228451
0.7755	Intermediate Similarity	NPC475838
0.7753	Intermediate Similarity	NPC123360
0.7745	Intermediate Similarity	NPC47880
0.7745	Intermediate Similarity	NPC477511
0.7745	Intermediate Similarity	NPC264477
0.7742	Intermediate Similarity	NPC318468
0.7732	Intermediate Similarity	NPC475855
0.7732	Intermediate Similarity	NPC475748
0.7732	Intermediate Similarity	NPC80875
0.7732	Intermediate Similarity	NPC62815
0.7723	Intermediate Similarity	NPC187268
0.7717	Intermediate Similarity	NPC471325
0.7717	Intermediate Similarity	NPC42470
0.7714	Intermediate Similarity	NPC470192
0.7708	Intermediate Similarity	NPC202672
0.77	Intermediate Similarity	NPC17585
0.7692	Intermediate Similarity	NPC264227
0.7692	Intermediate Similarity	NPC63649
0.7692	Intermediate Similarity	NPC178277
0.7692	Intermediate Similarity	NPC270126
0.7692	Intermediate Similarity	NPC472965
0.7684	Intermediate Similarity	NPC64153
0.7677	Intermediate Similarity	NPC469632
0.7677	Intermediate Similarity	NPC198853
0.7677	Intermediate Similarity	NPC474247
0.767	Intermediate Similarity	NPC474747
0.767	Intermediate Similarity	NPC149371
0.7667	Intermediate Similarity	NPC470240
0.7667	Intermediate Similarity	NPC476794
0.7653	Intermediate Similarity	NPC208886
0.7653	Intermediate Similarity	NPC184463
0.7653	Intermediate Similarity	NPC166110
0.7653	Intermediate Similarity	NPC131209
0.7653	Intermediate Similarity	NPC12172
0.7653	Intermediate Similarity	NPC32494
0.7653	Intermediate Similarity	NPC175842
0.7629	Intermediate Similarity	NPC307411
0.7629	Intermediate Similarity	NPC4986
0.7624	Intermediate Similarity	NPC471490
0.7609	Intermediate Similarity	NPC302426
0.76	Intermediate Similarity	NPC67584
0.7596	Intermediate Similarity	NPC475871
0.7596	Intermediate Similarity	NPC475945
0.7582	Intermediate Similarity	NPC128276
0.7576	Intermediate Similarity	NPC475657
0.7576	Intermediate Similarity	NPC59646
0.7576	Intermediate Similarity	NPC476300
0.7576	Intermediate Similarity	NPC81419
0.7576	Intermediate Similarity	NPC135776
0.7576	Intermediate Similarity	NPC179746
0.7576	Intermediate Similarity	NPC248193
0.7576	Intermediate Similarity	NPC212486
0.7576	Intermediate Similarity	NPC475912
0.7573	Intermediate Similarity	NPC474742
0.7573	Intermediate Similarity	NPC201718
0.7573	Intermediate Similarity	NPC133907
0.7573	Intermediate Similarity	NPC128733
0.7573	Intermediate Similarity	NPC46998
0.7573	Intermediate Similarity	NPC15993
0.7573	Intermediate Similarity	NPC110443
0.7573	Intermediate Similarity	NPC185141
0.7553	Intermediate Similarity	NPC170286
0.7553	Intermediate Similarity	NPC475947
0.7553	Intermediate Similarity	NPC250315
0.7553	Intermediate Similarity	NPC170377
0.7551	Intermediate Similarity	NPC474323
0.7551	Intermediate Similarity	NPC51004
0.7551	Intermediate Similarity	NPC49342
0.7551	Intermediate Similarity	NPC206614
0.7551	Intermediate Similarity	NPC251385
0.7549	Intermediate Similarity	NPC473326
0.7549	Intermediate Similarity	NPC208233
0.7549	Intermediate Similarity	NPC54843
0.7549	Intermediate Similarity	NPC279561
0.7528	Intermediate Similarity	NPC476355
0.7527	Intermediate Similarity	NPC255580
0.7527	Intermediate Similarity	NPC39411
0.7526	Intermediate Similarity	NPC224652
0.7525	Intermediate Similarity	NPC35498
0.7525	Intermediate Similarity	NPC213078
0.7525	Intermediate Similarity	NPC279621
0.7525	Intermediate Similarity	NPC230800
0.7524	Intermediate Similarity	NPC474741
0.7523	Intermediate Similarity	NPC66108
0.75	Intermediate Similarity	NPC305475
0.75	Intermediate Similarity	NPC127019
0.75	Intermediate Similarity	NPC471148
0.75	Intermediate Similarity	NPC470010
0.75	Intermediate Similarity	NPC470521
0.75	Intermediate Similarity	NPC320019
0.75	Intermediate Similarity	NPC324017
0.75	Intermediate Similarity	NPC470013
0.75	Intermediate Similarity	NPC475461
0.75	Intermediate Similarity	NPC261721
0.75	Intermediate Similarity	NPC323008
0.75	Intermediate Similarity	NPC262133
0.75	Intermediate Similarity	NPC476596
0.75	Intermediate Similarity	NPC150755
0.75	Intermediate Similarity	NPC121825
0.75	Intermediate Similarity	NPC190294
0.7476	Intermediate Similarity	NPC469551
0.7476	Intermediate Similarity	NPC477512
0.7475	Intermediate Similarity	NPC123177
0.7475	Intermediate Similarity	NPC30515
0.7475	Intermediate Similarity	NPC74103
0.7475	Intermediate Similarity	NPC193396
0.7475	Intermediate Similarity	NPC150978
0.7475	Intermediate Similarity	NPC32944
0.7475	Intermediate Similarity	NPC70595
0.7473	Intermediate Similarity	NPC171204
0.7473	Intermediate Similarity	NPC57744
0.7473	Intermediate Similarity	NPC476028
0.7473	Intermediate Similarity	NPC180290
0.7473	Intermediate Similarity	NPC65603
0.7473	Intermediate Similarity	NPC471225
0.7473	Intermediate Similarity	NPC141789
0.7473	Intermediate Similarity	NPC97516
0.7451	Intermediate Similarity	NPC161493
0.7449	Intermediate Similarity	NPC142159
0.7449	Intermediate Similarity	NPC95364
0.7449	Intermediate Similarity	NPC475971
0.7447	Intermediate Similarity	NPC471326
0.7447	Intermediate Similarity	NPC246076
0.7447	Intermediate Similarity	NPC221231
0.7444	Intermediate Similarity	NPC155587
0.7444	Intermediate Similarity	NPC193351
0.7444	Intermediate Similarity	NPC226669
0.7444	Intermediate Similarity	NPC138408
0.7429	Intermediate Similarity	NPC271059
0.7429	Intermediate Similarity	NPC472755

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 NPC273197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	1872
0.2-0.3	3851
0.3-0.4	2212
0.4-0.5	687
0.5-0.6	275
0.6-0.7	35
0.7-0.8	4
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
0.7629	Intermediate Similarity	NPD1695	Approved
0.75	Intermediate Similarity	NPD5282	Discontinued
0.7396	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6698	Approved
0.6863	Remote Similarity	NPD7838	Discovery
0.6863	Remote Similarity	NPD46	Approved
0.6737	Remote Similarity	NPD4756	Discovery
0.6735	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6371	Approved
0.67	Remote Similarity	NPD1694	Approved
0.6634	Remote Similarity	NPD4249	Approved
0.6609	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD2067	Discontinued
0.6574	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD4250	Approved
0.6566	Remote Similarity	NPD5209	Approved
0.6522	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6008	Approved
0.65	Remote Similarity	NPD7154	Phase 3
0.6476	Remote Similarity	NPD5693	Phase 1
0.6476	Remote Similarity	NPD7983	Approved
0.6404	Remote Similarity	NPD6686	Approved
0.6381	Remote Similarity	NPD5785	Approved
0.6381	Remote Similarity	NPD5692	Phase 3
0.6364	Remote Similarity	NPD6648	Approved
0.6346	Remote Similarity	NPD6672	Approved
0.6346	Remote Similarity	NPD5737	Approved
0.6321	Remote Similarity	NPD6050	Approved
0.6321	Remote Similarity	NPD5694	Approved
0.6296	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD5696	Approved
0.6264	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.6226	Remote Similarity	NPD5207	Approved
0.6214	Remote Similarity	NPD5363	Approved
0.6196	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD8039	Approved
0.6182	Remote Similarity	NPD6083	Phase 2
0.6182	Remote Similarity	NPD6084	Phase 2
0.6174	Remote Similarity	NPD5697	Approved
0.6174	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5369	Approved
0.6132	Remote Similarity	NPD6904	Approved
0.6132	Remote Similarity	NPD6673	Approved
0.6132	Remote Similarity	NPD6080	Approved
0.6126	Remote Similarity	NPD4225	Approved
0.6124	Remote Similarity	NPD7260	Phase 2
0.6121	Remote Similarity	NPD6899	Approved
0.6121	Remote Similarity	NPD7320	Approved
0.6121	Remote Similarity	NPD6881	Approved
0.6102	Remote Similarity	NPD6649	Approved
0.6102	Remote Similarity	NPD6650	Approved
0.6087	Remote Similarity	NPD6402	Approved
0.6087	Remote Similarity	NPD7128	Approved
0.6087	Remote Similarity	NPD5739	Approved
0.6087	Remote Similarity	NPD6675	Approved
0.6078	Remote Similarity	NPD6435	Approved
0.6077	Remote Similarity	NPD6845	Suspended
0.6068	Remote Similarity	NPD6372	Approved
0.6068	Remote Similarity	NPD6013	Approved
0.6068	Remote Similarity	NPD6373	Approved
0.6068	Remote Similarity	NPD6014	Approved
0.6068	Remote Similarity	NPD6012	Approved
0.6058	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6903	Approved
0.6034	Remote Similarity	NPD5701	Approved
0.6032	Remote Similarity	NPD7492	Approved
0.6019	Remote Similarity	NPD6110	Phase 1
0.6019	Remote Similarity	NPD5362	Discontinued
0.6018	Remote Similarity	NPD5344	Discontinued
0.6017	Remote Similarity	NPD7102	Approved
0.6017	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD7290	Approved
0.6017	Remote Similarity	NPD6883	Approved
0.6015	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5654	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD6011	Approved
0.5982	Remote Similarity	NPD7638	Approved
0.5981	Remote Similarity	NPD6101	Approved
0.5981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6054	Approved
0.5968	Remote Similarity	NPD6319	Approved
0.5966	Remote Similarity	NPD6617	Approved
0.5966	Remote Similarity	NPD8130	Phase 1
0.5966	Remote Similarity	NPD6869	Approved
0.5966	Remote Similarity	NPD6847	Approved
0.5963	Remote Similarity	NPD6399	Phase 3
0.5946	Remote Similarity	NPD7839	Suspended
0.5938	Remote Similarity	NPD7078	Approved
0.5932	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7639	Approved
0.5929	Remote Similarity	NPD7640	Approved
0.5922	Remote Similarity	NPD4269	Approved
0.5922	Remote Similarity	NPD4270	Approved
0.592	Remote Similarity	NPD6016	Approved
0.592	Remote Similarity	NPD8516	Approved
0.592	Remote Similarity	NPD8515	Approved
0.592	Remote Similarity	NPD8517	Approved
0.592	Remote Similarity	NPD6015	Approved
0.592	Remote Similarity	NPD8513	Phase 3
0.5917	Remote Similarity	NPD6882	Approved
0.5917	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7900	Approved
0.5893	Remote Similarity	NPD5959	Approved
0.5891	Remote Similarity	NPD7736	Approved
0.5888	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5368	Approved
0.5882	Remote Similarity	NPD4695	Discontinued
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4822	Approved
0.5882	Remote Similarity	NPD4820	Approved
0.5882	Remote Similarity	NPD4819	Approved
0.5882	Remote Similarity	NPD4821	Approved
0.5873	Remote Similarity	NPD8080	Discontinued
0.5873	Remote Similarity	NPD5988	Approved
0.5873	Remote Similarity	NPD6370	Approved
0.5872	Remote Similarity	NPD5281	Approved
0.5872	Remote Similarity	NPD6411	Approved
0.5872	Remote Similarity	NPD5284	Approved
0.5868	Remote Similarity	NPD4632	Approved
0.5854	Remote Similarity	NPD6009	Approved
0.5854	Remote Similarity	NPD7115	Discovery
0.5851	Remote Similarity	NPD3704	Approved
0.5849	Remote Similarity	NPD5279	Phase 3
0.5849	Remote Similarity	NPD6098	Approved
0.5849	Remote Similarity	NPD5786	Approved
0.584	Remote Similarity	NPD6059	Approved
0.5833	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8293	Discontinued
0.5806	Remote Similarity	NPD7641	Discontinued
0.5794	Remote Similarity	NPD5983	Phase 2
0.5772	Remote Similarity	NPD6274	Approved
0.5772	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD6001	Approved
0.5752	Remote Similarity	NPD7902	Approved
0.5736	Remote Similarity	NPD7507	Approved
0.5728	Remote Similarity	NPD4252	Approved
0.5727	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7604	Phase 2
0.5702	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD2204	Approved
0.5699	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8074	Phase 3
0.569	Remote Similarity	NPD5211	Phase 2
0.5688	Remote Similarity	NPD4753	Phase 2
0.5686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4268	Approved
0.5686	Remote Similarity	NPD4271	Approved
0.5682	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7503	Approved
0.5669	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5286	Approved
0.5652	Remote Similarity	NPD5285	Approved
0.5652	Remote Similarity	NPD4696	Approved
0.5648	Remote Similarity	NPD3573	Approved
0.5635	Remote Similarity	NPD7101	Approved
0.5635	Remote Similarity	NPD7100	Approved
0.563	Remote Similarity	NPD6614	Approved
0.563	Remote Similarity	NPD6412	Phase 2
0.5625	Remote Similarity	NPD7748	Approved
0.5619	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD6336	Discontinued
0.5614	Remote Similarity	NPD4755	Approved
0.5606	Remote Similarity	NPD7319	Approved
0.56	Remote Similarity	NPD6317	Approved
0.56	Remote Similarity	NPD7500	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