NPASS Compound

Structure

CID198314 OpenBabel06191715582D 24 25 0 0 1 0 0 0 0 0999 V2000 -2.0565 1.6310 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 -5.1377 -0.8695 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 -3.4392 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 -1.7071 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 -4.1463 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -1.7071 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 -4.7550 -1.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 0.7071 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 -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 -4.1463 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7465 -1.6628 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 14 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 15 2 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 9 19 1 0 0 0 0 10 20 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 20 1 0 0 0 0 13 21 2 0 0 0 0 15 16 1 0 0 0 0 16 8 1 1 0 0 0 16 17 1 0 0 0 0 17 14 1 6 0 0 0 17 18 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	359.342
LogP:	2.391
LogD:	2.299
LogS:	-3.622
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	4.567
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	2.705565930227749e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.17
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.521
Plasma Protein Binding (PPB):	75.28314208984375%
Volume Distribution (VD):	1.225
Pgp-substrate:	23.99540901184082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.583
CYP2C19-inhibitor:	0.246
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.837
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	3.165
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.166
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.931
Carcinogencity:	0.896
Eye Corrosion:	0.131
Eye Irritation:	0.201
Respiratory Toxicity:	0.844

Download Data

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

Natural Product: NPC198314

Natural Product ID:	NPC198314
*Common Name:**	Blumiolide-A
IUPAC Name:	(4E,4aS,7S,10aR)-4-[(E)-4-hydroxy-4-methylpent-2-enylidene]-7-methyl-10-methylidene-1-oxo-4a,5,6,8,9,10a-hexahydrocycloocta[c]pyran-7-carbaldehyde
Synonyms:	Blumiolide-A
Standard InCHIKey:	UDXXPMHZVKAWCF-IERAJXIUSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-14-7-10-20(4,13-21)11-8-16-15(6-5-9-19(2,3)23)12-24-18(22)17(14)16/h5-6,9,13,16-17,23H,1,7-8,10-12H2,2-4H3/b9-5+,15-6-/t16-,17+,20-/m1/s1
SMILES:	C=C1CC[C@](C)(CC[C@@H]2/C(=CC=CC(C)(C)O)/COC(=O)[C@@H]12)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462886
PubChem CID:	11493679
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]
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]
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]

☑ 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	=	4.6	ug ml-1	PMID[523411]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.3	ug ml-1	PMID[523411]

☑ 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 NPC198314 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	186
0.1-0.2	1004
0.2-0.3	4224
0.3-0.4	11790
0.4-0.5	13744
0.5-0.6	8027
0.6-0.7	3480
0.7-0.8	235
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8706	High Similarity	NPC474369
0.8605	High Similarity	NPC116575
0.8605	High Similarity	NPC234038
0.8588	High Similarity	NPC14575
0.8588	High Similarity	NPC196487
0.8415	Intermediate Similarity	NPC107668
0.8315	Intermediate Similarity	NPC212598
0.8315	Intermediate Similarity	NPC106040
0.8315	Intermediate Similarity	NPC115179
0.8072	Intermediate Similarity	NPC12740
0.8072	Intermediate Similarity	NPC110461
0.8043	Intermediate Similarity	NPC476049
0.7927	Intermediate Similarity	NPC135703
0.7912	Intermediate Similarity	NPC83423
0.7882	Intermediate Similarity	NPC474341
0.7872	Intermediate Similarity	NPC272050
0.7857	Intermediate Similarity	NPC61863
0.7791	Intermediate Similarity	NPC469617
0.7753	Intermediate Similarity	NPC70424
0.7753	Intermediate Similarity	NPC243618
0.7738	Intermediate Similarity	NPC228978
0.7727	Intermediate Similarity	NPC475936
0.7717	Intermediate Similarity	NPC284561
0.7692	Intermediate Similarity	NPC86005
0.764	Intermediate Similarity	NPC53867
0.7634	Intermediate Similarity	NPC214844
0.7629	Intermediate Similarity	NPC64742
0.7614	Intermediate Similarity	NPC14203
0.7614	Intermediate Similarity	NPC229584
0.7614	Intermediate Similarity	NPC325031
0.7604	Intermediate Similarity	NPC9812
0.76	Intermediate Similarity	NPC309190
0.7582	Intermediate Similarity	NPC122502
0.7576	Intermediate Similarity	NPC475091
0.7558	Intermediate Similarity	NPC316324
0.7556	Intermediate Similarity	NPC474776
0.7553	Intermediate Similarity	NPC45579
0.7553	Intermediate Similarity	NPC475972
0.7553	Intermediate Similarity	NPC472705
0.7551	Intermediate Similarity	NPC475053
0.7528	Intermediate Similarity	NPC85772
0.7527	Intermediate Similarity	NPC118011
0.7527	Intermediate Similarity	NPC36668
0.7526	Intermediate Similarity	NPC208094
0.75	Intermediate Similarity	NPC295347
0.75	Intermediate Similarity	NPC475678
0.75	Intermediate Similarity	NPC209355
0.75	Intermediate Similarity	NPC231599
0.75	Intermediate Similarity	NPC233377
0.75	Intermediate Similarity	NPC312561
0.7475	Intermediate Similarity	NPC116139
0.7475	Intermediate Similarity	NPC206079
0.7471	Intermediate Similarity	NPC267231
0.7471	Intermediate Similarity	NPC471220
0.7449	Intermediate Similarity	NPC244411
0.7447	Intermediate Similarity	NPC232426
0.7447	Intermediate Similarity	NPC51653
0.7447	Intermediate Similarity	NPC469372
0.7447	Intermediate Similarity	NPC281942
0.7444	Intermediate Similarity	NPC222358
0.7426	Intermediate Similarity	NPC239162
0.7419	Intermediate Similarity	NPC26078
0.7419	Intermediate Similarity	NPC473658
0.7419	Intermediate Similarity	NPC24816
0.7416	Intermediate Similarity	NPC475481
0.7416	Intermediate Similarity	NPC79277
0.74	Intermediate Similarity	NPC66110
0.74	Intermediate Similarity	NPC478156
0.7396	Intermediate Similarity	NPC475572
0.7396	Intermediate Similarity	NPC38830
0.7391	Intermediate Similarity	NPC220478
0.7391	Intermediate Similarity	NPC476982
0.7391	Intermediate Similarity	NPC315395
0.7391	Intermediate Similarity	NPC316426
0.7391	Intermediate Similarity	NPC168248
0.7391	Intermediate Similarity	NPC202394
0.7386	Intermediate Similarity	NPC471537
0.7374	Intermediate Similarity	NPC174314
0.7368	Intermediate Similarity	NPC141831
0.7368	Intermediate Similarity	NPC303697
0.7368	Intermediate Similarity	NPC36491
0.7363	Intermediate Similarity	NPC9868
0.7363	Intermediate Similarity	NPC474359
0.7363	Intermediate Similarity	NPC72464
0.7363	Intermediate Similarity	NPC295799
0.7363	Intermediate Similarity	NPC149869
0.7347	Intermediate Similarity	NPC254496
0.734	Intermediate Similarity	NPC307092
0.734	Intermediate Similarity	NPC51358
0.7333	Intermediate Similarity	NPC474252
0.7333	Intermediate Similarity	NPC123880
0.7333	Intermediate Similarity	NPC471159
0.7326	Intermediate Similarity	NPC475861
0.732	Intermediate Similarity	NPC107476
0.7312	Intermediate Similarity	NPC476079
0.7312	Intermediate Similarity	NPC181327
0.7312	Intermediate Similarity	NPC128644
0.7312	Intermediate Similarity	NPC113370
0.7312	Intermediate Similarity	NPC474765
0.7312	Intermediate Similarity	NPC477959
0.7312	Intermediate Similarity	NPC103743
0.7303	Intermediate Similarity	NPC47747
0.7303	Intermediate Similarity	NPC103634
0.7303	Intermediate Similarity	NPC160582
0.73	Intermediate Similarity	NPC62670
0.73	Intermediate Similarity	NPC469657
0.73	Intermediate Similarity	NPC244456
0.7283	Intermediate Similarity	NPC307112
0.7283	Intermediate Similarity	NPC261380
0.7283	Intermediate Similarity	NPC470177
0.7283	Intermediate Similarity	NPC147921
0.7283	Intermediate Similarity	NPC65661
0.7273	Intermediate Similarity	NPC127526
0.7273	Intermediate Similarity	NPC474005
0.7273	Intermediate Similarity	NPC121200
0.7273	Intermediate Similarity	NPC93763
0.7273	Intermediate Similarity	NPC316598
0.7273	Intermediate Similarity	NPC108816
0.7263	Intermediate Similarity	NPC469595
0.7263	Intermediate Similarity	NPC469368
0.7263	Intermediate Similarity	NPC212679
0.7263	Intermediate Similarity	NPC220454
0.7262	Intermediate Similarity	NPC475310
0.7262	Intermediate Similarity	NPC4299
0.7255	Intermediate Similarity	NPC472868
0.7253	Intermediate Similarity	NPC16488
0.7253	Intermediate Similarity	NPC250315
0.7253	Intermediate Similarity	NPC475989
0.7253	Intermediate Similarity	NPC49208
0.7253	Intermediate Similarity	NPC170377
0.7253	Intermediate Similarity	NPC193198
0.7253	Intermediate Similarity	NPC23748
0.7253	Intermediate Similarity	NPC475842
0.7241	Intermediate Similarity	NPC474447
0.7241	Intermediate Similarity	NPC271070
0.7234	Intermediate Similarity	NPC477128
0.7234	Intermediate Similarity	NPC473151
0.7228	Intermediate Similarity	NPC235369
0.7228	Intermediate Similarity	NPC473596
0.7222	Intermediate Similarity	NPC52861
0.7222	Intermediate Similarity	NPC327002
0.7222	Intermediate Similarity	NPC40228
0.7222	Intermediate Similarity	NPC42470
0.7216	Intermediate Similarity	NPC53685
0.7216	Intermediate Similarity	NPC477129
0.7216	Intermediate Similarity	NPC167219
0.7216	Intermediate Similarity	NPC477130
0.7216	Intermediate Similarity	NPC476415
0.7204	Intermediate Similarity	NPC476104
0.7204	Intermediate Similarity	NPC239685
0.7204	Intermediate Similarity	NPC164393
0.72	Intermediate Similarity	NPC474718
0.72	Intermediate Similarity	NPC477720
0.7196	Intermediate Similarity	NPC56448
0.7191	Intermediate Similarity	NPC469620
0.7191	Intermediate Similarity	NPC158565
0.7191	Intermediate Similarity	NPC136033
0.7191	Intermediate Similarity	NPC469690
0.7191	Intermediate Similarity	NPC89128
0.7188	Intermediate Similarity	NPC111114
0.7188	Intermediate Similarity	NPC219874
0.7188	Intermediate Similarity	NPC261607
0.7188	Intermediate Similarity	NPC300312
0.7174	Intermediate Similarity	NPC82297
0.7174	Intermediate Similarity	NPC476804
0.7174	Intermediate Similarity	NPC31086
0.7174	Intermediate Similarity	NPC474865
0.7172	Intermediate Similarity	NPC170131
0.7172	Intermediate Similarity	NPC474343
0.7172	Intermediate Similarity	NPC47834
0.7172	Intermediate Similarity	NPC285513
0.7172	Intermediate Similarity	NPC202705
0.7159	Intermediate Similarity	NPC281296
0.7159	Intermediate Similarity	NPC7563
0.7159	Intermediate Similarity	NPC116177
0.7159	Intermediate Similarity	NPC320630
0.7159	Intermediate Similarity	NPC315394
0.7158	Intermediate Similarity	NPC5509
0.7158	Intermediate Similarity	NPC97577
0.7157	Intermediate Similarity	NPC475526
0.7157	Intermediate Similarity	NPC329345
0.7157	Intermediate Similarity	NPC473283
0.7143	Intermediate Similarity	NPC35556
0.7143	Intermediate Similarity	NPC101622
0.7143	Intermediate Similarity	NPC200513
0.7143	Intermediate Similarity	NPC94200
0.7143	Intermediate Similarity	NPC268122
0.7143	Intermediate Similarity	NPC89555
0.7143	Intermediate Similarity	NPC472469
0.7143	Intermediate Similarity	NPC471326
0.7143	Intermediate Similarity	NPC134067
0.7143	Intermediate Similarity	NPC221231
0.7129	Intermediate Similarity	NPC146822
0.7129	Intermediate Similarity	NPC474899
0.7129	Intermediate Similarity	NPC303559
0.7129	Intermediate Similarity	NPC474912
0.7128	Intermediate Similarity	NPC478145
0.7128	Intermediate Similarity	NPC125925
0.7128	Intermediate Similarity	NPC160138
0.7128	Intermediate Similarity	NPC199382

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 NPC198314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1275
0.2-0.3	3599
0.3-0.4	2659
0.4-0.5	997
0.5-0.6	394
0.6-0.7	56
0.7-0.8	6
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
0.7738	Intermediate Similarity	NPD8039	Approved
0.7368	Intermediate Similarity	NPD6411	Approved
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7158	Intermediate Similarity	NPD6101	Approved
0.7158	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7839	Suspended
0.7065	Intermediate Similarity	NPD7154	Phase 3
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD7983	Approved
0.6957	Remote Similarity	NPD5209	Approved
0.6907	Remote Similarity	NPD6698	Approved
0.6907	Remote Similarity	NPD46	Approved
0.6842	Remote Similarity	NPD5786	Approved
0.6837	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4269	Approved
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4822	Approved
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4820	Approved
0.6737	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6596	Remote Similarity	NPD6435	Approved
0.6593	Remote Similarity	NPD4756	Discovery
0.6562	Remote Similarity	NPD5363	Approved
0.6559	Remote Similarity	NPD4252	Approved
0.6526	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD5331	Approved
0.6522	Remote Similarity	NPD4271	Approved
0.6522	Remote Similarity	NPD4268	Approved
0.6495	Remote Similarity	NPD6422	Discontinued
0.6489	Remote Similarity	NPD4790	Discontinued
0.6471	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD7838	Discovery
0.6392	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5368	Approved
0.6381	Remote Similarity	NPD6648	Approved
0.6381	Remote Similarity	NPD7639	Approved
0.6381	Remote Similarity	NPD7640	Approved
0.6373	Remote Similarity	NPD5282	Discontinued
0.6337	Remote Similarity	NPD5693	Phase 1
0.6337	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5694	Approved
0.6337	Remote Similarity	NPD5281	Approved
0.6327	Remote Similarity	NPD4249	Approved
0.6325	Remote Similarity	NPD8516	Approved
0.6325	Remote Similarity	NPD8517	Approved
0.6325	Remote Similarity	NPD8515	Approved
0.6325	Remote Similarity	NPD8513	Phase 3
0.6322	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5695	Phase 3
0.631	Remote Similarity	NPD4194	Approved
0.631	Remote Similarity	NPD4192	Approved
0.631	Remote Similarity	NPD4193	Approved
0.631	Remote Similarity	NPD4191	Approved
0.6306	Remote Similarity	NPD6371	Approved
0.6289	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7638	Approved
0.6273	Remote Similarity	NPD6686	Approved
0.6263	Remote Similarity	NPD4251	Approved
0.6263	Remote Similarity	NPD4250	Approved
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5692	Phase 3
0.6238	Remote Similarity	NPD5207	Approved
0.6224	Remote Similarity	NPD1696	Phase 3
0.6214	Remote Similarity	NPD7748	Approved
0.6207	Remote Similarity	NPD7331	Phase 2
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6672	Approved
0.6196	Remote Similarity	NPD8264	Approved
0.619	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6083	Phase 2
0.6186	Remote Similarity	NPD6695	Phase 3
0.6176	Remote Similarity	NPD6050	Approved
0.617	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7334	Approved
0.6162	Remote Similarity	NPD6684	Approved
0.6162	Remote Similarity	NPD5330	Approved
0.6162	Remote Similarity	NPD7146	Approved
0.6162	Remote Similarity	NPD7521	Approved
0.6162	Remote Similarity	NPD6409	Approved
0.6162	Remote Similarity	NPD4623	Approved
0.6162	Remote Similarity	NPD4519	Discontinued
0.6147	Remote Similarity	NPD5909	Discontinued
0.6139	Remote Similarity	NPD6051	Approved
0.6139	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1695	Approved
0.6132	Remote Similarity	NPD5696	Approved
0.6122	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3667	Approved
0.6066	Remote Similarity	NPD8074	Phase 3
0.6053	Remote Similarity	NPD6053	Discontinued
0.6042	Remote Similarity	NPD4695	Discontinued
0.6042	Remote Similarity	NPD7514	Phase 3
0.6042	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7332	Phase 2
0.604	Remote Similarity	NPD6903	Approved
0.604	Remote Similarity	NPD4518	Approved
0.604	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5697	Approved
0.6019	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7515	Phase 2
0.6019	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.5984	Remote Similarity	NPD7507	Approved
0.5984	Remote Similarity	NPD8451	Approved
0.5982	Remote Similarity	NPD6011	Approved
0.5982	Remote Similarity	NPD6899	Approved
0.5982	Remote Similarity	NPD6881	Approved
0.598	Remote Similarity	NPD6904	Approved
0.598	Remote Similarity	NPD6080	Approved
0.598	Remote Similarity	NPD5370	Suspended
0.598	Remote Similarity	NPD6673	Approved
0.596	Remote Similarity	NPD3668	Phase 3
0.596	Remote Similarity	NPD4786	Approved
0.5946	Remote Similarity	NPD5739	Approved
0.5946	Remote Similarity	NPD7128	Approved
0.5946	Remote Similarity	NPD6402	Approved
0.5946	Remote Similarity	NPD6675	Approved
0.5941	Remote Similarity	NPD7524	Approved
0.5941	Remote Similarity	NPD7750	Discontinued
0.5935	Remote Similarity	NPD8448	Approved
0.5929	Remote Similarity	NPD6014	Approved
0.5929	Remote Similarity	NPD6012	Approved
0.5929	Remote Similarity	NPD6013	Approved
0.5926	Remote Similarity	NPD3172	Approved
0.5922	Remote Similarity	NPD3672	Approved
0.5922	Remote Similarity	NPD3673	Approved
0.5914	Remote Similarity	NPD6924	Approved
0.5914	Remote Similarity	NPD6926	Approved
0.5909	Remote Similarity	NPD6647	Phase 2
0.5909	Remote Similarity	NPD7341	Phase 2
0.5905	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7900	Approved
0.5904	Remote Similarity	NPD4219	Approved
0.5902	Remote Similarity	NPD8341	Approved
0.5902	Remote Similarity	NPD8299	Approved
0.5902	Remote Similarity	NPD8342	Approved
0.5902	Remote Similarity	NPD8340	Approved
0.5897	Remote Similarity	NPD2629	Approved
0.5893	Remote Similarity	NPD5701	Approved
0.5882	Remote Similarity	NPD5208	Approved
0.5877	Remote Similarity	NPD6883	Approved
0.5877	Remote Similarity	NPD7290	Approved
0.5877	Remote Similarity	NPD7102	Approved
0.5876	Remote Similarity	NPD6931	Approved
0.5876	Remote Similarity	NPD6930	Phase 2
0.5873	Remote Similarity	NPD7260	Phase 2
0.5854	Remote Similarity	NPD4266	Approved
0.5854	Remote Similarity	NPD8273	Phase 1
0.5854	Remote Similarity	NPD3194	Approved
0.5854	Remote Similarity	NPD3195	Phase 2
0.5854	Remote Similarity	NPD3196	Approved
0.5849	Remote Similarity	NPD5654	Approved
0.5849	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5280	Approved
0.5842	Remote Similarity	NPD4694	Approved
0.5841	Remote Similarity	NPD7320	Approved
0.5841	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.584	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD7145	Approved
0.5826	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6650	Approved
0.5826	Remote Similarity	NPD8130	Phase 1
0.5826	Remote Similarity	NPD6617	Approved
0.5826	Remote Similarity	NPD6847	Approved
0.5826	Remote Similarity	NPD6649	Approved
0.5826	Remote Similarity	NPD6869	Approved
0.5825	Remote Similarity	NPD4753	Phase 2
0.5818	Remote Similarity	NPD5211	Phase 2
0.5818	Remote Similarity	NPD7632	Discontinued
0.5816	Remote Similarity	NPD6902	Approved
0.5812	Remote Similarity	NPD6010	Discontinued
0.581	Remote Similarity	NPD1088	Approved
0.5806	Remote Similarity	NPD4732	Discontinued
0.5804	Remote Similarity	NPD6008	Approved
0.58	Remote Similarity	NPD3665	Phase 1
0.58	Remote Similarity	NPD3666	Approved
0.58	Remote Similarity	NPD3133	Approved
0.5798	Remote Similarity	NPD7641	Discontinued
0.5795	Remote Similarity	NPD3197	Phase 1
0.5794	Remote Similarity	NPD8392	Approved
0.5794	Remote Similarity	NPD4697	Phase 3

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