NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	264.305
LogP:	1.331
LogD:	0.726
LogS:	-3.254
# Rotatable Bonds:	1
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	6.015
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805
MDCK Permeability:	2.054151991615072e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.777
20% Bioavailability (F20%):	0.734
30% Bioavailability (F30%):	0.625

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	62.21949005126953%
Volume Distribution (VD):	0.948
Pgp-substrate:	42.89450454711914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.527
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.248
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	8.451
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.147
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.649
Carcinogencity:	0.895
Eye Corrosion:	0.804
Eye Irritation:	0.553
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC77337

Natural Product ID:	NPC77337
*Common Name:**	SPZKJZJNPQNEKT-BMIGLBTASA-N
IUPAC Name:	n.a.
Synonyms:	14-Hydroxycretenolide; 14-Hydroxyhypocretenolide
Standard InCHIKey:	SPZKJZJNPQNEKT-BMIGLBTASA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-8-5-12(17)13-11(7-16)4-3-10-6-15(8,13)19-14(18)9(10)2/h5,10,16H,2-4,6-7H2,1H3/t10-,15+/m1/s1
SMILES:	OCC1=C2C(=O)C=C([C@]32C[C@@H](CC1)C(=C)C(=O)O3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL365306
PubChem CID:	15378302
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO32466	leontodon hispidus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425121]

☑ 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	26
Others	2

Activity Type	# Activity
Cell Line	19
Individual Protein	1
NON-MOLECULAR	7
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	1500.0	nM	PMID[505518]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	1300.0	nM	PMID[505518]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	900.0	nM	PMID[505518]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	1500.0	nM	PMID[505518]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	1300.0	nM	PMID[505518]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	1100.0	nM	PMID[505518]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	800.0	nM	PMID[505518]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	700.0	nM	PMID[505518]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1000.0	nM	PMID[505518]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	1900.0	nM	PMID[505518]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	2100.0	nM	PMID[505518]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	1800.0	nM	PMID[505518]
NPT2014	Cell Line	SW872	Homo sapiens	IC50	=	3100.0	nM	PMID[505518]
NPT2014	Cell Line	SW872	Homo sapiens	IC50	=	2200.0	nM	PMID[505518]
NPT2014	Cell Line	SW872	Homo sapiens	IC50	=	2800.0	nM	PMID[505518]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	=	600.0	nM	PMID[505518]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	=	900.0	nM	PMID[505518]
NPT133	Cell Line	ZR-75-1	Homo sapiens	IC50	=	1000.0	nM	PMID[505518]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	260.0	nM	PMID[505518]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	50.0	uM	PMID[505516]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	50.0	uM	PMID[505517]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2800.0	nM	PMID[505518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2600.0	nM	PMID[505518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1200.0	nM	PMID[505518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3200.0	nM	PMID[505518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2400.0	nM	PMID[505518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1800.0	nM	PMID[505518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	260.0	nM	PMID[505518]

☑ 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 NPC77337 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	174
0.1-0.2	1092
0.2-0.3	4553
0.3-0.4	9046
0.4-0.5	15240
0.5-0.6	7198
0.6-0.7	4451
0.7-0.8	920
0.8-0.85	22
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC476627
0.8556	High Similarity	NPC268298
0.8462	Intermediate Similarity	NPC129419
0.8404	Intermediate Similarity	NPC9812
0.837	Intermediate Similarity	NPC261607
0.837	Intermediate Similarity	NPC300312
0.837	Intermediate Similarity	NPC111114
0.8367	Intermediate Similarity	NPC100487
0.8367	Intermediate Similarity	NPC309190
0.8315	Intermediate Similarity	NPC261380
0.8315	Intermediate Similarity	NPC476628
0.8261	Intermediate Similarity	NPC106510
0.8261	Intermediate Similarity	NPC71533
0.8256	Intermediate Similarity	NPC472013
0.8256	Intermediate Similarity	NPC476624
0.8247	Intermediate Similarity	NPC116139
0.8247	Intermediate Similarity	NPC206079
0.8229	Intermediate Similarity	NPC64742
0.8229	Intermediate Similarity	NPC244411
0.8202	Intermediate Similarity	NPC243618
0.8202	Intermediate Similarity	NPC70424
0.8191	Intermediate Similarity	NPC469632
0.8163	Intermediate Similarity	NPC66110
0.8144	Intermediate Similarity	NPC280963
0.8132	Intermediate Similarity	NPC237540
0.8111	Intermediate Similarity	NPC165162
0.8061	Intermediate Similarity	NPC62670
0.8046	Intermediate Similarity	NPC469617
0.8041	Intermediate Similarity	NPC141191
0.8022	Intermediate Similarity	NPC261721
0.8021	Intermediate Similarity	NPC185553
0.8	Intermediate Similarity	NPC9868
0.8	Intermediate Similarity	NPC167219
0.8	Intermediate Similarity	NPC53685
0.7978	Intermediate Similarity	NPC85772
0.7957	Intermediate Similarity	NPC212598
0.7938	Intermediate Similarity	NPC169205
0.7917	Intermediate Similarity	NPC48803
0.7917	Intermediate Similarity	NPC474490
0.7917	Intermediate Similarity	NPC275960
0.7917	Intermediate Similarity	NPC193645
0.7917	Intermediate Similarity	NPC90121
0.7895	Intermediate Similarity	NPC135776
0.7879	Intermediate Similarity	NPC477950
0.7879	Intermediate Similarity	NPC475099
0.7872	Intermediate Similarity	NPC51486
0.7872	Intermediate Similarity	NPC145666
0.7865	Intermediate Similarity	NPC35089
0.7865	Intermediate Similarity	NPC10276
0.7849	Intermediate Similarity	NPC474471
0.7849	Intermediate Similarity	NPC153805
0.7849	Intermediate Similarity	NPC227379
0.7841	Intermediate Similarity	NPC470244
0.7841	Intermediate Similarity	NPC470239
0.7835	Intermediate Similarity	NPC184065
0.7826	Intermediate Similarity	NPC234038
0.7812	Intermediate Similarity	NPC65829
0.7802	Intermediate Similarity	NPC72464
0.7802	Intermediate Similarity	NPC472957
0.7802	Intermediate Similarity	NPC472958
0.7791	Intermediate Similarity	NPC89374
0.7789	Intermediate Similarity	NPC45579
0.7789	Intermediate Similarity	NPC472705
0.7778	Intermediate Similarity	NPC475309
0.7778	Intermediate Similarity	NPC474291
0.7778	Intermediate Similarity	NPC133844
0.7766	Intermediate Similarity	NPC295312
0.7755	Intermediate Similarity	NPC40812
0.7755	Intermediate Similarity	NPC477949
0.7755	Intermediate Similarity	NPC47834
0.7753	Intermediate Similarity	NPC233377
0.7753	Intermediate Similarity	NPC302426
0.7753	Intermediate Similarity	NPC223904
0.7742	Intermediate Similarity	NPC72513
0.7727	Intermediate Similarity	NPC299235
0.7727	Intermediate Similarity	NPC222210
0.7727	Intermediate Similarity	NPC63445
0.7717	Intermediate Similarity	NPC137033
0.7717	Intermediate Similarity	NPC125290
0.7708	Intermediate Similarity	NPC476049
0.7708	Intermediate Similarity	NPC469645
0.7708	Intermediate Similarity	NPC469692
0.77	Intermediate Similarity	NPC46998
0.77	Intermediate Similarity	NPC128733
0.77	Intermediate Similarity	NPC110443
0.77	Intermediate Similarity	NPC133907
0.77	Intermediate Similarity	NPC185141
0.7684	Intermediate Similarity	NPC476004
0.7684	Intermediate Similarity	NPC474761
0.7677	Intermediate Similarity	NPC261377
0.7677	Intermediate Similarity	NPC255592
0.7677	Intermediate Similarity	NPC83895
0.7677	Intermediate Similarity	NPC187761
0.7677	Intermediate Similarity	NPC308567
0.7674	Intermediate Similarity	NPC7382
0.7667	Intermediate Similarity	NPC470241
0.7667	Intermediate Similarity	NPC325031
0.766	Intermediate Similarity	NPC469631
0.766	Intermediate Similarity	NPC469653
0.766	Intermediate Similarity	NPC475906
0.766	Intermediate Similarity	NPC471047
0.766	Intermediate Similarity	NPC469628
0.7634	Intermediate Similarity	NPC316426
0.7634	Intermediate Similarity	NPC107787
0.7634	Intermediate Similarity	NPC116575
0.7634	Intermediate Similarity	NPC122502
0.7634	Intermediate Similarity	NPC475461
0.7634	Intermediate Similarity	NPC315395
0.7634	Intermediate Similarity	NPC305475
0.7629	Intermediate Similarity	NPC475832
0.7629	Intermediate Similarity	NPC475927
0.7629	Intermediate Similarity	NPC121825
0.7614	Intermediate Similarity	NPC472014
0.7614	Intermediate Similarity	NPC65603
0.7609	Intermediate Similarity	NPC156485
0.7609	Intermediate Similarity	NPC165287
0.7609	Intermediate Similarity	NPC14575
0.7609	Intermediate Similarity	NPC114979
0.7609	Intermediate Similarity	NPC191476
0.7609	Intermediate Similarity	NPC96259
0.7609	Intermediate Similarity	NPC115786
0.7609	Intermediate Similarity	NPC196487
0.7609	Intermediate Similarity	NPC141193
0.7604	Intermediate Similarity	NPC472814
0.7604	Intermediate Similarity	NPC284185
0.7604	Intermediate Similarity	NPC177037
0.76	Intermediate Similarity	NPC306856
0.76	Intermediate Similarity	NPC288876
0.7582	Intermediate Similarity	NPC89555
0.7579	Intermediate Similarity	NPC115179
0.7579	Intermediate Similarity	NPC5509
0.7579	Intermediate Similarity	NPC117405
0.7579	Intermediate Similarity	NPC32922
0.7579	Intermediate Similarity	NPC106040
0.7579	Intermediate Similarity	NPC307092
0.7579	Intermediate Similarity	NPC52198
0.7579	Intermediate Similarity	NPC205548
0.7576	Intermediate Similarity	NPC170143
0.7576	Intermediate Similarity	NPC213947
0.7576	Intermediate Similarity	NPC108475
0.7576	Intermediate Similarity	NPC474343
0.7573	Intermediate Similarity	NPC243998
0.7556	Intermediate Similarity	NPC47747
0.7553	Intermediate Similarity	NPC248602
0.7553	Intermediate Similarity	NPC478145
0.7553	Intermediate Similarity	NPC471738
0.7551	Intermediate Similarity	NPC170120
0.7551	Intermediate Similarity	NPC52044
0.7551	Intermediate Similarity	NPC476488
0.7551	Intermediate Similarity	NPC304886
0.7551	Intermediate Similarity	NPC272050
0.7551	Intermediate Similarity	NPC209355
0.7551	Intermediate Similarity	NPC469873
0.7551	Intermediate Similarity	NPC476487
0.7549	Intermediate Similarity	NPC472755
0.7549	Intermediate Similarity	NPC475871
0.7549	Intermediate Similarity	NPC110989
0.7549	Intermediate Similarity	NPC475945
0.7528	Intermediate Similarity	NPC108816
0.7528	Intermediate Similarity	NPC192006
0.7528	Intermediate Similarity	NPC127526
0.7528	Intermediate Similarity	NPC93763
0.7527	Intermediate Similarity	NPC78089
0.7527	Intermediate Similarity	NPC255307
0.7527	Intermediate Similarity	NPC470755
0.7527	Intermediate Similarity	NPC245434
0.7526	Intermediate Similarity	NPC115021
0.7526	Intermediate Similarity	NPC475912
0.7526	Intermediate Similarity	NPC475302
0.7525	Intermediate Similarity	NPC171759
0.7525	Intermediate Similarity	NPC474742
0.7525	Intermediate Similarity	NPC150923
0.7524	Intermediate Similarity	NPC47951
0.75	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC222011
0.75	Intermediate Similarity	NPC318468
0.75	Intermediate Similarity	NPC11620
0.75	Intermediate Similarity	NPC301969
0.75	Intermediate Similarity	NPC53867
0.75	Intermediate Similarity	NPC39588
0.75	Intermediate Similarity	NPC166554
0.75	Intermediate Similarity	NPC253144
0.75	Intermediate Similarity	NPC37607
0.75	Intermediate Similarity	NPC473448
0.75	Intermediate Similarity	NPC316598
0.75	Intermediate Similarity	NPC215294
0.7476	Intermediate Similarity	NPC203659
0.7475	Intermediate Similarity	NPC242848
0.7475	Intermediate Similarity	NPC230800
0.7474	Intermediate Similarity	NPC475902
0.7474	Intermediate Similarity	NPC473658
0.7474	Intermediate Similarity	NPC476805
0.7474	Intermediate Similarity	NPC202672
0.7474	Intermediate Similarity	NPC281516
0.7473	Intermediate Similarity	NPC25684
0.7473	Intermediate Similarity	NPC171665
0.7473	Intermediate Similarity	NPC301477
0.7473	Intermediate Similarity	NPC78677
0.7473	Intermediate Similarity	NPC281949
0.7473	Intermediate Similarity	NPC59994

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 NPC77337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1458
0.2-0.3	3658
0.3-0.4	2542
0.4-0.5	919
0.5-0.6	294
0.6-0.7	115
0.7-0.8	11
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
0.7917	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5785	Approved
0.7527	Intermediate Similarity	NPD5363	Approved
0.7453	Intermediate Similarity	NPD6371	Approved
0.7447	Intermediate Similarity	NPD5786	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7204	Intermediate Similarity	NPD4269	Approved
0.717	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5362	Discontinued
0.7128	Intermediate Similarity	NPD7154	Phase 3
0.7097	Intermediate Similarity	NPD5369	Approved
0.7021	Intermediate Similarity	NPD6435	Approved
0.7021	Intermediate Similarity	NPD5209	Approved
0.7021	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.6989	Remote Similarity	NPD4252	Approved
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.6869	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6101	Approved
0.6847	Remote Similarity	NPD6053	Discontinued
0.6827	Remote Similarity	NPD4225	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6804	Remote Similarity	NPD1694	Approved
0.6796	Remote Similarity	NPD7839	Suspended
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7115	Discovery
0.6733	Remote Similarity	NPD7983	Approved
0.6733	Remote Similarity	NPD6411	Approved
0.6731	Remote Similarity	NPD6084	Phase 2
0.6731	Remote Similarity	NPD6083	Phase 2
0.67	Remote Similarity	NPD1695	Approved
0.6699	Remote Similarity	NPD5695	Phase 3
0.6697	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6633	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4822	Approved
0.6632	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4819	Approved
0.6632	Remote Similarity	NPD4821	Approved
0.6632	Remote Similarity	NPD4820	Approved
0.6606	Remote Similarity	NPD5739	Approved
0.6606	Remote Similarity	NPD6675	Approved
0.6606	Remote Similarity	NPD7128	Approved
0.6606	Remote Similarity	NPD6402	Approved
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD5693	Phase 1
0.6552	Remote Similarity	NPD7341	Phase 2
0.6545	Remote Similarity	NPD5701	Approved
0.6518	Remote Similarity	NPD7290	Approved
0.6518	Remote Similarity	NPD6883	Approved
0.6518	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD7638	Approved
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5696	Approved
0.6495	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4756	Discovery
0.6486	Remote Similarity	NPD6686	Approved
0.6486	Remote Similarity	NPD7320	Approved
0.6481	Remote Similarity	NPD5211	Phase 2
0.646	Remote Similarity	NPD8130	Phase 1
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6649	Approved
0.646	Remote Similarity	NPD6617	Approved
0.646	Remote Similarity	NPD6847	Approved
0.646	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD5331	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6421	Remote Similarity	NPD4268	Approved
0.6421	Remote Similarity	NPD4271	Approved
0.6408	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD8297	Approved
0.64	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6409	Approved
0.64	Remote Similarity	NPD7146	Approved
0.64	Remote Similarity	NPD7334	Approved
0.64	Remote Similarity	NPD7521	Approved
0.64	Remote Similarity	NPD5330	Approved
0.64	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD4790	Discontinued
0.6373	Remote Similarity	NPD4753	Phase 2
0.6373	Remote Similarity	NPD5370	Suspended
0.6364	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6337	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7838	Discovery
0.6303	Remote Similarity	NPD6319	Approved
0.63	Remote Similarity	NPD1696	Phase 3
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6277	Remote Similarity	NPD8039	Approved
0.6275	Remote Similarity	NPD6672	Approved
0.6275	Remote Similarity	NPD5737	Approved
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD6079	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD6274	Approved
0.6239	Remote Similarity	NPD5223	Approved
0.6238	Remote Similarity	NPD4249	Approved
0.6238	Remote Similarity	NPD4519	Discontinued
0.6238	Remote Similarity	NPD4623	Approved
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6214	Remote Similarity	NPD6673	Approved
0.6214	Remote Similarity	NPD6080	Approved
0.6214	Remote Similarity	NPD5328	Approved
0.6214	Remote Similarity	NPD6904	Approved
0.6207	Remote Similarity	NPD4632	Approved
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD6317	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6179	Remote Similarity	NPD7507	Approved
0.6176	Remote Similarity	NPD4250	Approved
0.6176	Remote Similarity	NPD4251	Approved
0.6174	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5221	Approved
0.6168	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5222	Approved
0.6162	Remote Similarity	NPD4221	Approved
0.6162	Remote Similarity	NPD4223	Phase 3
0.6154	Remote Similarity	NPD5692	Phase 3
0.6147	Remote Similarity	NPD4700	Approved
0.6134	Remote Similarity	NPD6313	Approved
0.6134	Remote Similarity	NPD6314	Approved
0.6134	Remote Similarity	NPD6335	Approved
0.6132	Remote Similarity	NPD7748	Approved
0.6126	Remote Similarity	NPD6647	Phase 2
0.6126	Remote Similarity	NPD5174	Approved
0.6126	Remote Similarity	NPD5175	Approved
0.6117	Remote Similarity	NPD5208	Approved
0.6116	Remote Similarity	NPD8515	Approved
0.6116	Remote Similarity	NPD8517	Approved
0.6116	Remote Similarity	NPD8516	Approved
0.6116	Remote Similarity	NPD8513	Phase 3
0.6111	Remote Similarity	NPD5173	Approved
0.6098	Remote Similarity	NPD7492	Approved
0.6095	Remote Similarity	NPD7515	Phase 2
0.6095	Remote Similarity	NPD5694	Approved
0.6095	Remote Similarity	NPD6050	Approved
0.6091	Remote Similarity	NPD5344	Discontinued
0.6087	Remote Similarity	NPD4634	Approved
0.6083	Remote Similarity	NPD7101	Approved
0.6083	Remote Similarity	NPD7100	Approved
0.6078	Remote Similarity	NPD3618	Phase 1
0.6078	Remote Similarity	NPD6422	Discontinued
0.6078	Remote Similarity	NPD5279	Phase 3
0.6078	Remote Similarity	NPD5690	Phase 2
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6009	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.604	Remote Similarity	NPD4197	Approved
0.6038	Remote Similarity	NPD4202	Approved
0.6036	Remote Similarity	NPD7632	Discontinued
0.6033	Remote Similarity	NPD6054	Approved
0.6019	Remote Similarity	NPD4697	Phase 3
0.6018	Remote Similarity	NPD6008	Approved
0.6016	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD3667	Approved
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4754	Approved
0.598	Remote Similarity	NPD5329	Approved
0.5966	Remote Similarity	NPD6868	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5963	Remote Similarity	NPD7902	Approved
0.596	Remote Similarity	NPD4695	Discontinued
0.5952	Remote Similarity	NPD7736	Approved
0.5941	Remote Similarity	NPD4788	Approved
0.5935	Remote Similarity	NPD6370	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