NPASS Compound

Structure

CID116575 OpenBabel06191715472D 24 25 0 0 1 0 0 0 0 0999 V2000 -4.9917 -2.0825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8748 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5677 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5677 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 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 13 2 0 0 0 0 2 14 2 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 15 2 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 17 1 0 0 0 0 15 16 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 17 21 1 1 0 0 0 18 14 1 6 0 0 0 18 19 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	359.342
LogP:	2.477
LogD:	2.343
LogS:	-2.927
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	5.163
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.499
MDCK Permeability:	4.379712845548056e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.171
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.518
Plasma Protein Binding (PPB):	39.69587707519531%
Volume Distribution (VD):	0.625
Pgp-substrate:	54.619388580322266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.589
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.623
CYP3A4-inhibitor:	0.217
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	9.455
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.465
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.098
Carcinogencity:	0.961
Eye Corrosion:	0.022
Eye Irritation:	0.112
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC116575

Natural Product ID:	NPC116575
*Common Name:**	Blumiolide-B
IUPAC Name:	(4E,4aS,8S,11aR)-8-hydroxy-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7,11-dimethylidene-5,6,8,9,10,11a-hexahydro-4aH-cyclonona[c]pyran-1-one
Synonyms:	Blumiolide-B
Standard InCHIKey:	JSQQYBKNOUUYPJ-JBPXYRHBSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-13-7-9-16-15(6-5-11-20(3,4)23)12-24-19(22)18(16)14(2)8-10-17(13)21/h5-6,11,16-18,21,23H,1-2,7-10,12H2,3-4H3/b11-5+,15-6-/t16-,17+,18+/m1/s1
SMILES:	C=C1CC[C@@H]2/C(=CC=CC(C)(C)O)/COC(=O)[C@H]2C(=C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517297
PubChem CID:	11645658
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
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	Green Island, Taiwan	2002-MAY	PMID[16180809]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23536	Alsophila spinulosa	Species	Cyatheaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18067	Muehlenbeckia platyclada	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26130	Cordia latifolia	Species	Cordiaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	4.9	ug ml-1	PMID[526106]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.7	ug ml-1	PMID[526106]

☑ 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 NPC116575 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	181
0.1-0.2	903
0.2-0.3	3730
0.3-0.4	8673
0.4-0.5	15715
0.5-0.6	8035
0.6-0.7	4884
0.7-0.8	541
0.8-0.85	24
0.85-0.9	7
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC212598
0.963	High Similarity	NPC474369
0.9176	High Similarity	NPC115179
0.9176	High Similarity	NPC106040
0.9091	High Similarity	NPC272050
0.908	High Similarity	NPC476049
0.8824	High Similarity	NPC234038
0.881	High Similarity	NPC14575
0.881	High Similarity	NPC196487
0.8696	High Similarity	NPC475053
0.8642	High Similarity	NPC107668
0.8605	High Similarity	NPC198314
0.8571	High Similarity	NPC475936
0.8519	High Similarity	NPC12740
0.8519	High Similarity	NPC110461
0.8519	High Similarity	NPC61863
0.8506	High Similarity	NPC474765
0.8471	Intermediate Similarity	NPC53867
0.8462	Intermediate Similarity	NPC107476
0.8372	Intermediate Similarity	NPC474776
0.8372	Intermediate Similarity	NPC243618
0.8372	Intermediate Similarity	NPC70424
0.8313	Intermediate Similarity	NPC474341
0.8295	Intermediate Similarity	NPC86005
0.8235	Intermediate Similarity	NPC325031
0.8214	Intermediate Similarity	NPC469617
0.8171	Intermediate Similarity	NPC475861
0.8161	Intermediate Similarity	NPC9868
0.8148	Intermediate Similarity	NPC135703
0.8118	Intermediate Similarity	NPC103634
0.8068	Intermediate Similarity	NPC261380
0.8046	Intermediate Similarity	NPC475842
0.8	Intermediate Similarity	NPC89128
0.7978	Intermediate Similarity	NPC315395
0.7978	Intermediate Similarity	NPC122502
0.7978	Intermediate Similarity	NPC316426
0.7959	Intermediate Similarity	NPC309190
0.7955	Intermediate Similarity	NPC72464
0.7955	Intermediate Similarity	NPC295799
0.7935	Intermediate Similarity	NPC475972
0.7931	Intermediate Similarity	NPC474252
0.7931	Intermediate Similarity	NPC89555
0.7912	Intermediate Similarity	NPC97577
0.7907	Intermediate Similarity	NPC233377
0.7901	Intermediate Similarity	NPC4299
0.7889	Intermediate Similarity	NPC477959
0.7889	Intermediate Similarity	NPC312561
0.7882	Intermediate Similarity	NPC267231
0.7882	Intermediate Similarity	NPC127526
0.7865	Intermediate Similarity	NPC255307
0.7865	Intermediate Similarity	NPC137033
0.7857	Intermediate Similarity	NPC271070
0.7841	Intermediate Similarity	NPC16488
0.7841	Intermediate Similarity	NPC250315
0.7826	Intermediate Similarity	NPC473448
0.7826	Intermediate Similarity	NPC281942
0.7826	Intermediate Similarity	NPC474761
0.7826	Intermediate Similarity	NPC476004
0.7826	Intermediate Similarity	NPC232426
0.7816	Intermediate Similarity	NPC112868
0.7816	Intermediate Similarity	NPC52861
0.7802	Intermediate Similarity	NPC227379
0.7802	Intermediate Similarity	NPC474471
0.7802	Intermediate Similarity	NPC153805
0.7791	Intermediate Similarity	NPC471537
0.7778	Intermediate Similarity	NPC202394
0.7778	Intermediate Similarity	NPC164393
0.7778	Intermediate Similarity	NPC475461
0.7778	Intermediate Similarity	NPC239162
0.7778	Intermediate Similarity	NPC305475
0.7778	Intermediate Similarity	NPC101622
0.7765	Intermediate Similarity	NPC320630
0.7765	Intermediate Similarity	NPC7563
0.7765	Intermediate Similarity	NPC116177
0.7765	Intermediate Similarity	NPC315394
0.7755	Intermediate Similarity	NPC478156
0.7753	Intermediate Similarity	NPC191476
0.7753	Intermediate Similarity	NPC114979
0.7753	Intermediate Similarity	NPC476804
0.7753	Intermediate Similarity	NPC82297
0.7742	Intermediate Similarity	NPC300312
0.7742	Intermediate Similarity	NPC36491
0.7742	Intermediate Similarity	NPC141831
0.7742	Intermediate Similarity	NPC219874
0.7742	Intermediate Similarity	NPC261607
0.7742	Intermediate Similarity	NPC111114
0.7727	Intermediate Similarity	NPC85772
0.7727	Intermediate Similarity	NPC474291
0.7717	Intermediate Similarity	NPC307092
0.7717	Intermediate Similarity	NPC295312
0.7717	Intermediate Similarity	NPC51358
0.7717	Intermediate Similarity	NPC256902
0.7717	Intermediate Similarity	NPC118193
0.7708	Intermediate Similarity	NPC208094
0.7708	Intermediate Similarity	NPC254496
0.7692	Intermediate Similarity	NPC160138
0.7684	Intermediate Similarity	NPC209355
0.7684	Intermediate Similarity	NPC304886
0.7674	Intermediate Similarity	NPC121200
0.7674	Intermediate Similarity	NPC4436
0.7674	Intermediate Similarity	NPC93763
0.7674	Intermediate Similarity	NPC108816
0.7667	Intermediate Similarity	NPC165162
0.766	Intermediate Similarity	NPC475912
0.7653	Intermediate Similarity	NPC244456
0.7653	Intermediate Similarity	NPC469657
0.7647	Intermediate Similarity	NPC279537
0.764	Intermediate Similarity	NPC473390
0.764	Intermediate Similarity	NPC44261
0.764	Intermediate Similarity	NPC23748
0.764	Intermediate Similarity	NPC475989
0.764	Intermediate Similarity	NPC131669
0.764	Intermediate Similarity	NPC11620
0.7634	Intermediate Similarity	NPC77337
0.7634	Intermediate Similarity	NPC469368
0.7634	Intermediate Similarity	NPC313670
0.7634	Intermediate Similarity	NPC214844
0.7634	Intermediate Similarity	NPC316228
0.7634	Intermediate Similarity	NPC475855
0.7629	Intermediate Similarity	NPC316598
0.7629	Intermediate Similarity	NPC64742
0.7614	Intermediate Similarity	NPC79277
0.7614	Intermediate Similarity	NPC14203
0.7614	Intermediate Similarity	NPC470241
0.7614	Intermediate Similarity	NPC475481
0.7614	Intermediate Similarity	NPC474894
0.7614	Intermediate Similarity	NPC42470
0.7614	Intermediate Similarity	NPC229584
0.7609	Intermediate Similarity	NPC24816
0.7609	Intermediate Similarity	NPC202672
0.7609	Intermediate Similarity	NPC26078
0.7609	Intermediate Similarity	NPC473658
0.7604	Intermediate Similarity	NPC195645
0.7604	Intermediate Similarity	NPC165332
0.7604	Intermediate Similarity	NPC180722
0.7604	Intermediate Similarity	NPC9812
0.759	Intermediate Similarity	NPC472254
0.7586	Intermediate Similarity	NPC470244
0.7586	Intermediate Similarity	NPC470239
0.7586	Intermediate Similarity	NPC475210
0.7582	Intermediate Similarity	NPC476982
0.7582	Intermediate Similarity	NPC311163
0.7582	Intermediate Similarity	NPC261721
0.7579	Intermediate Similarity	NPC475572
0.7579	Intermediate Similarity	NPC474035
0.7579	Intermediate Similarity	NPC81386
0.7579	Intermediate Similarity	NPC71589
0.7579	Intermediate Similarity	NPC53685
0.7576	Intermediate Similarity	NPC475091
0.7576	Intermediate Similarity	NPC473596
0.7576	Intermediate Similarity	NPC235369
0.7558	Intermediate Similarity	NPC316324
0.7558	Intermediate Similarity	NPC476439
0.7558	Intermediate Similarity	NPC281296
0.7558	Intermediate Similarity	NPC84360
0.7558	Intermediate Similarity	NPC40049
0.7556	Intermediate Similarity	NPC141193
0.7556	Intermediate Similarity	NPC96259
0.7553	Intermediate Similarity	NPC45579
0.7553	Intermediate Similarity	NPC30515
0.7553	Intermediate Similarity	NPC303697
0.7553	Intermediate Similarity	NPC470379
0.7553	Intermediate Similarity	NPC470373
0.7551	Intermediate Similarity	NPC474718
0.7529	Intermediate Similarity	NPC60718
0.7528	Intermediate Similarity	NPC123880
0.7528	Intermediate Similarity	NPC471159
0.7528	Intermediate Similarity	NPC229825
0.7527	Intermediate Similarity	NPC473564
0.7527	Intermediate Similarity	NPC218927
0.7527	Intermediate Similarity	NPC206001
0.7527	Intermediate Similarity	NPC284561
0.7527	Intermediate Similarity	NPC36668
0.7527	Intermediate Similarity	NPC268298
0.7527	Intermediate Similarity	NPC474032
0.7527	Intermediate Similarity	NPC118011
0.7526	Intermediate Similarity	NPC474343
0.7526	Intermediate Similarity	NPC40812
0.7526	Intermediate Similarity	NPC285513
0.75	Intermediate Similarity	NPC477085
0.75	Intermediate Similarity	NPC14961
0.75	Intermediate Similarity	NPC295347
0.75	Intermediate Similarity	NPC475678
0.75	Intermediate Similarity	NPC248602
0.75	Intermediate Similarity	NPC231599
0.75	Intermediate Similarity	NPC36954
0.75	Intermediate Similarity	NPC237540
0.75	Intermediate Similarity	NPC316138
0.75	Intermediate Similarity	NPC313658
0.75	Intermediate Similarity	NPC134067
0.75	Intermediate Similarity	NPC270013
0.75	Intermediate Similarity	NPC472469
0.7475	Intermediate Similarity	NPC116139
0.7475	Intermediate Similarity	NPC206079
0.7474	Intermediate Similarity	NPC475838
0.7474	Intermediate Similarity	NPC81419
0.7474	Intermediate Similarity	NPC125674
0.7474	Intermediate Similarity	NPC179746
0.7474	Intermediate Similarity	NPC228451
0.7473	Intermediate Similarity	NPC474547

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 NPC116575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1207
0.2-0.3	3362
0.3-0.4	2677
0.4-0.5	1198
0.5-0.6	428
0.6-0.7	107
0.7-0.8	12
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
0.8043	Intermediate Similarity	NPD5778	Approved
0.8043	Intermediate Similarity	NPD5779	Approved
0.7912	Intermediate Similarity	NPD6101	Approved
0.7912	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6411	Approved
0.764	Intermediate Similarity	NPD7154	Phase 3
0.764	Intermediate Similarity	NPD5362	Discontinued
0.7604	Intermediate Similarity	NPD7839	Suspended
0.7553	Intermediate Similarity	NPD7983	Approved
0.7447	Intermediate Similarity	NPD6698	Approved
0.7447	Intermediate Similarity	NPD46	Approved
0.7391	Intermediate Similarity	NPD5786	Approved
0.7333	Intermediate Similarity	NPD4270	Approved
0.7333	Intermediate Similarity	NPD4269	Approved
0.7326	Intermediate Similarity	NPD8039	Approved
0.7303	Intermediate Similarity	NPD4822	Approved
0.7303	Intermediate Similarity	NPD4819	Approved
0.7303	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4821	Approved
0.7303	Intermediate Similarity	NPD4820	Approved
0.7273	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5785	Approved
0.7222	Intermediate Similarity	NPD5369	Approved
0.7143	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4252	Approved
0.7097	Intermediate Similarity	NPD5363	Approved
0.7083	Intermediate Similarity	NPD7838	Discovery
0.7079	Intermediate Similarity	NPD4271	Approved
0.7079	Intermediate Similarity	NPD4268	Approved
0.7065	Intermediate Similarity	NPD5332	Approved
0.7065	Intermediate Similarity	NPD5331	Approved
0.7033	Intermediate Similarity	NPD4790	Discontinued
0.701	Intermediate Similarity	NPD7637	Suspended
0.6957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5368	Approved
0.6915	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4249	Approved
0.679	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4756	Discovery
0.6774	Remote Similarity	NPD5209	Approved
0.6771	Remote Similarity	NPD4250	Approved
0.6771	Remote Similarity	NPD4251	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6754	Remote Similarity	NPD8516	Approved
0.6754	Remote Similarity	NPD8515	Approved
0.6754	Remote Similarity	NPD8517	Approved
0.6754	Remote Similarity	NPD8513	Phase 3
0.6737	Remote Similarity	NPD1694	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6699	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6422	Discontinued
0.6667	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6053	Discontinued
0.6635	Remote Similarity	NPD5344	Discontinued
0.6606	Remote Similarity	NPD6371	Approved
0.6602	Remote Similarity	NPD7638	Approved
0.66	Remote Similarity	NPD6399	Phase 3
0.6574	Remote Similarity	NPD6686	Approved
0.6562	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7115	Discovery
0.6535	Remote Similarity	NPD5282	Discontinued
0.6526	Remote Similarity	NPD6695	Phase 3
0.65	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8074	Phase 3
0.6465	Remote Similarity	NPD5370	Suspended
0.6465	Remote Similarity	NPD1695	Approved
0.6458	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3667	Approved
0.6395	Remote Similarity	NPD7331	Phase 2
0.6387	Remote Similarity	NPD8273	Phase 1
0.6374	Remote Similarity	NPD8264	Approved
0.6373	Remote Similarity	NPD7748	Approved
0.6355	Remote Similarity	NPD6647	Phase 2
0.6353	Remote Similarity	NPD3197	Phase 1
0.6353	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6344	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD7515	Phase 2
0.6337	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5697	Approved
0.6327	Remote Similarity	NPD5279	Phase 3
0.6311	Remote Similarity	NPD5695	Phase 3
0.631	Remote Similarity	NPD368	Approved
0.6289	Remote Similarity	NPD4786	Approved
0.6279	Remote Similarity	NPD7341	Phase 2
0.6273	Remote Similarity	NPD6899	Approved
0.6273	Remote Similarity	NPD6881	Approved
0.6273	Remote Similarity	NPD6011	Approved
0.6264	Remote Similarity	NPD6926	Approved
0.6264	Remote Similarity	NPD6924	Approved
0.6263	Remote Similarity	NPD7524	Approved
0.6263	Remote Similarity	NPD7750	Discontinued
0.6263	Remote Similarity	NPD3573	Approved
0.625	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8451	Approved
0.625	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6224	Remote Similarity	NPD1696	Phase 3
0.6216	Remote Similarity	NPD6013	Approved
0.6216	Remote Similarity	NPD6014	Approved
0.6216	Remote Similarity	NPD6012	Approved
0.6211	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6931	Approved
0.6211	Remote Similarity	NPD7332	Phase 2
0.6211	Remote Similarity	NPD7514	Phase 3
0.6211	Remote Similarity	NPD6930	Phase 2
0.6198	Remote Similarity	NPD8448	Approved
0.619	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD8444	Approved
0.6182	Remote Similarity	NPD5701	Approved
0.6176	Remote Similarity	NPD5694	Approved
0.6176	Remote Similarity	NPD5693	Phase 1
0.6174	Remote Similarity	NPD2629	Approved
0.6167	Remote Similarity	NPD8299	Approved
0.6167	Remote Similarity	NPD8342	Approved
0.6167	Remote Similarity	NPD8341	Approved
0.6167	Remote Similarity	NPD8340	Approved
0.6162	Remote Similarity	NPD6684	Approved
0.6162	Remote Similarity	NPD4623	Approved
0.6162	Remote Similarity	NPD7521	Approved
0.6162	Remote Similarity	NPD4519	Discontinued
0.6162	Remote Similarity	NPD7334	Approved
0.6162	Remote Similarity	NPD6409	Approved
0.6162	Remote Similarity	NPD5330	Approved
0.6162	Remote Similarity	NPD7146	Approved
0.6161	Remote Similarity	NPD6420	Discontinued
0.6161	Remote Similarity	NPD7290	Approved
0.6161	Remote Similarity	NPD7102	Approved
0.6161	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD5909	Discontinued
0.6139	Remote Similarity	NPD6051	Approved
0.6139	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5696	Approved
0.6129	Remote Similarity	NPD6933	Approved
0.6126	Remote Similarity	NPD7320	Approved
0.6126	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3172	Approved
0.6122	Remote Similarity	NPD3666	Approved
0.6122	Remote Similarity	NPD3133	Approved
0.6122	Remote Similarity	NPD3665	Phase 1
0.6111	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD5211	Phase 2
0.6106	Remote Similarity	NPD6869	Approved
0.6106	Remote Similarity	NPD6649	Approved
0.6106	Remote Similarity	NPD6847	Approved
0.6106	Remote Similarity	NPD8130	Phase 1
0.6106	Remote Similarity	NPD6650	Approved
0.6106	Remote Similarity	NPD6617	Approved
0.6105	Remote Similarity	NPD6929	Approved
0.6091	Remote Similarity	NPD5048	Discontinued
0.6083	Remote Similarity	NPD7830	Approved
0.6083	Remote Similarity	NPD7829	Approved
0.6078	Remote Similarity	NPD5207	Approved
0.6078	Remote Similarity	NPD5692	Phase 3
0.6071	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6373	Approved
0.6071	Remote Similarity	NPD6372	Approved
0.6055	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6882	Approved
0.6053	Remote Similarity	NPD8297	Approved
0.6049	Remote Similarity	NPD3195	Phase 2
0.6049	Remote Similarity	NPD3196	Approved
0.6049	Remote Similarity	NPD3194	Approved
0.6049	Remote Similarity	NPD4266	Approved
0.6048	Remote Similarity	NPD8390	Approved
0.6048	Remote Similarity	NPD8392	Approved
0.6048	Remote Similarity	NPD8391	Approved
0.6042	Remote Similarity	NPD4695	Discontinued
0.604	Remote Similarity	NPD6672	Approved
0.604	Remote Similarity	NPD5737	Approved
0.604	Remote Similarity	NPD4518	Approved
0.604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6903	Approved
0.6036	Remote Similarity	NPD6685	Approved
0.602	Remote Similarity	NPD6110	Phase 1
0.6019	Remote Similarity	NPD6079	Approved
0.6019	Remote Similarity	NPD6050	Approved
0.6019	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5141	Approved
0.5984	Remote Similarity	NPD7507	Approved
0.5983	Remote Similarity	NPD7505	Discontinued
0.598	Remote Similarity	NPD4753	Phase 2
0.598	Remote Similarity	NPD5328	Approved
0.5979	Remote Similarity	NPD6902	Approved
0.5978	Remote Similarity	NPD4732	Discontinued

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