NPASS Compound

Structure

NPC471054 OpenBabel07101718272D 30 32 0 0 1 0 0 0 0 0999 V2000 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 4.8660 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 0.0000 4.0000 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 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 16 1 0 0 0 0 8 24 1 0 0 0 0 9 16 2 0 0 0 0 10 17 1 0 0 0 0 10 20 1 0 0 0 0 11 18 2 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 20 9 1 6 0 0 0 20 29 1 0 0 0 0 21 12 1 1 0 0 0 21 23 1 0 0 0 0 22 27 2 0 0 0 0 23 11 1 1 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 25 13 1 1 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.24
Volume:	443.419
LogP:	2.681
LogD:	2.615
LogS:	-3.834
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	5.597
Fsp3:	0.56
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.556
MDCK Permeability:	1.6248348401859403e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.264
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.407
Plasma Protein Binding (PPB):	82.73267364501953%
Volume Distribution (VD):	1.178
Pgp-substrate:	8.20510196685791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.478
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.554
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	7.724
Half-life (T1/2):	0.525

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.699
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.954
Carcinogencity:	0.926
Eye Corrosion:	0.004
Eye Irritation:	0.174
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC471054

Natural Product ID:	NPC471054
*Common Name:**	Phorbaketal D
IUPAC Name:	(2S,4'aR,6S,8'aR)-2-[(1E,4E)-6-hydroxy-2,6-dimethylhepta-1,4-dienyl]-4'-(hydroxymethyl)-4,7'-dimethylspiro[2,3-dihydropyran-6,2'-5,8a-dihydro-4aH-chromene]-6'-one
Synonyms:	Phorbaketal D
Standard InCHIKey:	YJRDLHQRPAPWKM-VJWRZOPTSA-N
Standard InCHI:	InChI=1S/C25H34O5/c1-16(7-6-8-24(4,5)28)9-20-10-17(2)13-25(29-20)14-19(15-26)21-12-22(27)18(3)11-23(21)30-25/h6,8-9,11,13-14,20-21,23,26,28H,7,10,12,15H2,1-5H3/b8-6+,16-9+/t20-,21-,23-,25+/m1/s1
SMILES:	CC1=CC2(C=C(C3CC(=O)C(=CC3O2)C)CO)OC(C1)C=C(C)CC=CC(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2338623
PubChem CID:	71578202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640525]
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	Korean	n.a.	PMID[23360104]
NPO32454	monanchora sp.	Species	Crambeidae	Eukaryota	n.a.	at 1520 m depth off the shore of Gageo Island, southwestern Korea	2009-JUL	PMID[25455409]

☑ 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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	50000.0	nM	PMID[555938]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[555938]
NPT376	Cell Line	A498	Homo sapiens	IC50	>	50000.0	nM	PMID[555938]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[555938]

☑ 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 NPC471054 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	196
0.1-0.2	1218
0.2-0.3	5056
0.3-0.4	11253
0.4-0.5	14387
0.5-0.6	7475
0.6-0.7	2878
0.7-0.8	222
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC241054
0.9643	High Similarity	NPC106051
0.9643	High Similarity	NPC472011
0.931	High Similarity	NPC472010
0.8876	High Similarity	NPC471059
0.8817	High Similarity	NPC472012
0.8222	Intermediate Similarity	NPC471056
0.8222	Intermediate Similarity	NPC471055
0.8202	Intermediate Similarity	NPC471060
0.8132	Intermediate Similarity	NPC471058
0.8132	Intermediate Similarity	NPC471057
0.7614	Intermediate Similarity	NPC326753
0.7582	Intermediate Similarity	NPC44261
0.7556	Intermediate Similarity	NPC112868
0.75	Intermediate Similarity	NPC471061
0.7475	Intermediate Similarity	NPC266842
0.7471	Intermediate Similarity	NPC315552
0.7447	Intermediate Similarity	NPC300779
0.7447	Intermediate Similarity	NPC316138
0.7447	Intermediate Similarity	NPC313658
0.7429	Intermediate Similarity	NPC228477
0.7429	Intermediate Similarity	NPC137911
0.7416	Intermediate Similarity	NPC267231
0.7416	Intermediate Similarity	NPC108816
0.7416	Intermediate Similarity	NPC93763
0.74	Intermediate Similarity	NPC203627
0.7396	Intermediate Similarity	NPC265856
0.7391	Intermediate Similarity	NPC40746
0.7391	Intermediate Similarity	NPC2379
0.7391	Intermediate Similarity	NPC27314
0.7391	Intermediate Similarity	NPC263087
0.7391	Intermediate Similarity	NPC106912
0.7391	Intermediate Similarity	NPC31019
0.7391	Intermediate Similarity	NPC169575
0.7391	Intermediate Similarity	NPC16488
0.7379	Intermediate Similarity	NPC118911
0.7358	Intermediate Similarity	NPC37116
0.7353	Intermediate Similarity	NPC235369
0.7347	Intermediate Similarity	NPC476415
0.7347	Intermediate Similarity	NPC256368
0.734	Intermediate Similarity	NPC315395
0.734	Intermediate Similarity	NPC186332
0.734	Intermediate Similarity	NPC316426
0.734	Intermediate Similarity	NPC311163
0.734	Intermediate Similarity	NPC47220
0.732	Intermediate Similarity	NPC141831
0.732	Intermediate Similarity	NPC477749
0.7303	Intermediate Similarity	NPC116177
0.7303	Intermediate Similarity	NPC320630
0.7303	Intermediate Similarity	NPC7563
0.7297	Intermediate Similarity	NPC474179
0.7297	Intermediate Similarity	NPC475834
0.7292	Intermediate Similarity	NPC212598
0.7263	Intermediate Similarity	NPC103743
0.7263	Intermediate Similarity	NPC113370
0.7263	Intermediate Similarity	NPC476079
0.7255	Intermediate Similarity	NPC469851
0.7255	Intermediate Similarity	NPC244456
0.7255	Intermediate Similarity	NPC469657
0.7255	Intermediate Similarity	NPC472637
0.7245	Intermediate Similarity	NPC476416
0.7241	Intermediate Similarity	NPC316851
0.7238	Intermediate Similarity	NPC91034
0.7234	Intermediate Similarity	NPC470755
0.7234	Intermediate Similarity	NPC261380
0.7234	Intermediate Similarity	NPC471494
0.7234	Intermediate Similarity	NPC476426
0.7234	Intermediate Similarity	NPC242233
0.7234	Intermediate Similarity	NPC28887
0.7228	Intermediate Similarity	NPC316598
0.7228	Intermediate Similarity	NPC81483
0.7228	Intermediate Similarity	NPC169468
0.7228	Intermediate Similarity	NPC40182
0.7228	Intermediate Similarity	NPC61630
0.7228	Intermediate Similarity	NPC198422
0.7228	Intermediate Similarity	NPC307517
0.7222	Intermediate Similarity	NPC231739
0.7222	Intermediate Similarity	NPC236217
0.7216	Intermediate Similarity	NPC253186
0.7216	Intermediate Similarity	NPC3952
0.7216	Intermediate Similarity	NPC475855
0.7216	Intermediate Similarity	NPC144133
0.7216	Intermediate Similarity	NPC179394
0.7216	Intermediate Similarity	NPC281942
0.7216	Intermediate Similarity	NPC473455
0.7216	Intermediate Similarity	NPC232426
0.7207	Intermediate Similarity	NPC475913
0.7204	Intermediate Similarity	NPC473390
0.7204	Intermediate Similarity	NPC131669
0.7204	Intermediate Similarity	NPC475083
0.7204	Intermediate Similarity	NPC116543
0.7188	Intermediate Similarity	NPC60765
0.7184	Intermediate Similarity	NPC475320
0.7184	Intermediate Similarity	NPC201191
0.7184	Intermediate Similarity	NPC134077
0.7174	Intermediate Similarity	NPC325031
0.7174	Intermediate Similarity	NPC24417
0.7172	Intermediate Similarity	NPC298973
0.7172	Intermediate Similarity	NPC104925
0.7172	Intermediate Similarity	NPC2003
0.7172	Intermediate Similarity	NPC25701
0.7172	Intermediate Similarity	NPC475572
0.7172	Intermediate Similarity	NPC71589
0.717	Intermediate Similarity	NPC327106
0.7159	Intermediate Similarity	NPC114727
0.7159	Intermediate Similarity	NPC476590
0.7158	Intermediate Similarity	NPC475461
0.7158	Intermediate Similarity	NPC234038
0.7158	Intermediate Similarity	NPC305475
0.7156	Intermediate Similarity	NPC25909
0.7143	Intermediate Similarity	NPC321728
0.7143	Intermediate Similarity	NPC32552
0.7143	Intermediate Similarity	NPC475210
0.7143	Intermediate Similarity	NPC470379
0.7143	Intermediate Similarity	NPC470373
0.7143	Intermediate Similarity	NPC139712
0.7143	Intermediate Similarity	NPC469852
0.7129	Intermediate Similarity	NPC170131
0.7129	Intermediate Similarity	NPC20066
0.7129	Intermediate Similarity	NPC76266
0.7129	Intermediate Similarity	NPC474194
0.7128	Intermediate Similarity	NPC96259
0.7128	Intermediate Similarity	NPC158756
0.7128	Intermediate Similarity	NPC70424
0.7128	Intermediate Similarity	NPC141193
0.7128	Intermediate Similarity	NPC476804
0.7128	Intermediate Similarity	NPC243618
0.7115	Intermediate Similarity	NPC473624
0.7115	Intermediate Similarity	NPC151516
0.7113	Intermediate Similarity	NPC206001
0.7113	Intermediate Similarity	NPC307092
0.7113	Intermediate Similarity	NPC218927
0.7113	Intermediate Similarity	NPC477748
0.7113	Intermediate Similarity	NPC268298
0.7113	Intermediate Similarity	NPC133450
0.7113	Intermediate Similarity	NPC51358
0.7113	Intermediate Similarity	NPC87306
0.7111	Intermediate Similarity	NPC474278
0.71	Intermediate Similarity	NPC170204
0.71	Intermediate Similarity	NPC214694
0.71	Intermediate Similarity	NPC227494
0.7097	Intermediate Similarity	NPC229825
0.7097	Intermediate Similarity	NPC474252
0.7097	Intermediate Similarity	NPC279186
0.7097	Intermediate Similarity	NPC85772
0.7093	Intermediate Similarity	NPC151481
0.7091	Intermediate Similarity	NPC474181
0.7087	Intermediate Similarity	NPC115862
0.7087	Intermediate Similarity	NPC476240
0.7087	Intermediate Similarity	NPC476223
0.7087	Intermediate Similarity	NPC63249
0.7087	Intermediate Similarity	NPC224720
0.7083	Intermediate Similarity	NPC45409
0.7083	Intermediate Similarity	NPC160138
0.708	Intermediate Similarity	NPC48692
0.7075	Intermediate Similarity	NPC475294
0.7075	Intermediate Similarity	NPC469853
0.7071	Intermediate Similarity	NPC288240
0.7071	Intermediate Similarity	NPC282644
0.7071	Intermediate Similarity	NPC61201
0.7071	Intermediate Similarity	NPC472196
0.7071	Intermediate Similarity	NPC273579
0.7071	Intermediate Similarity	NPC472195
0.7071	Intermediate Similarity	NPC295204
0.7071	Intermediate Similarity	NPC159092
0.7071	Intermediate Similarity	NPC162205
0.7071	Intermediate Similarity	NPC238090
0.7071	Intermediate Similarity	NPC109406
0.7071	Intermediate Similarity	NPC29798
0.7071	Intermediate Similarity	NPC476049
0.7071	Intermediate Similarity	NPC320552
0.7065	Intermediate Similarity	NPC162741
0.7065	Intermediate Similarity	NPC91332
0.7059	Intermediate Similarity	NPC473154
0.7059	Intermediate Similarity	NPC255592
0.7059	Intermediate Similarity	NPC308567
0.7059	Intermediate Similarity	NPC187761
0.7059	Intermediate Similarity	NPC106613
0.7059	Intermediate Similarity	NPC261377
0.7059	Intermediate Similarity	NPC478056
0.7059	Intermediate Similarity	NPC83895
0.7053	Intermediate Similarity	NPC11804
0.7053	Intermediate Similarity	NPC255307
0.7053	Intermediate Similarity	NPC307112
0.7053	Intermediate Similarity	NPC21469
0.7053	Intermediate Similarity	NPC473353
0.7053	Intermediate Similarity	NPC163606
0.7053	Intermediate Similarity	NPC165162
0.7041	Intermediate Similarity	NPC475879
0.7041	Intermediate Similarity	NPC166554
0.7041	Intermediate Similarity	NPC473448
0.7041	Intermediate Similarity	NPC202886
0.7041	Intermediate Similarity	NPC177668
0.7041	Intermediate Similarity	NPC327253
0.7041	Intermediate Similarity	NPC129419
0.7037	Intermediate Similarity	NPC89408
0.7037	Intermediate Similarity	NPC473627
0.7037	Intermediate Similarity	NPC29133
0.7033	Intermediate Similarity	NPC471465
0.7033	Intermediate Similarity	NPC196653

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 NPC471054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1599
0.2-0.3	3899
0.3-0.4	2418
0.4-0.5	726
0.5-0.6	281
0.6-0.7	44
0.7-0.8	1
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
0.7576	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5785	Approved
0.6818	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7115	Discovery
0.6757	Remote Similarity	NPD6053	Discontinued
0.6724	Remote Similarity	NPD8513	Phase 3
0.6702	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5363	Approved
0.67	Remote Similarity	NPD46	Approved
0.67	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6607	Remote Similarity	NPD6882	Approved
0.6602	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8516	Approved
0.6581	Remote Similarity	NPD8515	Approved
0.6581	Remote Similarity	NPD8517	Approved
0.6569	Remote Similarity	NPD5779	Approved
0.6569	Remote Similarity	NPD5778	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD7838	Discovery
0.6531	Remote Similarity	NPD1694	Approved
0.6526	Remote Similarity	NPD4822	Approved
0.6526	Remote Similarity	NPD4819	Approved
0.6526	Remote Similarity	NPD4821	Approved
0.6526	Remote Similarity	NPD4820	Approved
0.6509	Remote Similarity	NPD7639	Approved
0.6509	Remote Similarity	NPD7640	Approved
0.6495	Remote Similarity	NPD7154	Phase 3
0.6489	Remote Similarity	NPD4271	Approved
0.6489	Remote Similarity	NPD4268	Approved
0.6465	Remote Similarity	NPD5786	Approved
0.6436	Remote Similarity	NPD6101	Approved
0.6436	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7638	Approved
0.6415	Remote Similarity	NPD4225	Approved
0.6408	Remote Similarity	NPD6399	Phase 3
0.6396	Remote Similarity	NPD6899	Approved
0.6396	Remote Similarity	NPD6881	Approved
0.6392	Remote Similarity	NPD4270	Approved
0.6392	Remote Similarity	NPD4269	Approved
0.6389	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD7839	Suspended
0.6372	Remote Similarity	NPD6650	Approved
0.6372	Remote Similarity	NPD6649	Approved
0.6372	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7331	Phase 2
0.6354	Remote Similarity	NPD4252	Approved
0.6327	Remote Similarity	NPD5362	Discontinued
0.6321	Remote Similarity	NPD7902	Approved
0.6311	Remote Similarity	NPD6079	Approved
0.6311	Remote Similarity	NPD8074	Phase 3
0.6311	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD6412	Phase 2
0.6306	Remote Similarity	NPD5697	Approved
0.6296	Remote Similarity	NPD5344	Discontinued
0.6289	Remote Similarity	NPD5369	Approved
0.6283	Remote Similarity	NPD6883	Approved
0.6283	Remote Similarity	NPD7102	Approved
0.6283	Remote Similarity	NPD7290	Approved
0.6283	Remote Similarity	NPD6371	Approved
0.6279	Remote Similarity	NPD368	Approved
0.6273	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD6011	Approved
0.6238	Remote Similarity	NPD4250	Approved
0.6238	Remote Similarity	NPD4251	Approved
0.6228	Remote Similarity	NPD6617	Approved
0.6228	Remote Similarity	NPD6869	Approved
0.6228	Remote Similarity	NPD8130	Phase 1
0.6228	Remote Similarity	NPD6847	Approved
0.6224	Remote Similarity	NPD6435	Approved
0.6224	Remote Similarity	NPD5209	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6211	Remote Similarity	NPD4756	Discovery
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD1696	Phase 3
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD7748	Approved
0.6186	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD8297	Approved
0.6168	Remote Similarity	NPD6084	Phase 2
0.6168	Remote Similarity	NPD6083	Phase 2
0.6167	Remote Similarity	NPD7503	Approved
0.6162	Remote Similarity	NPD5331	Approved
0.6162	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7515	Phase 2
0.6147	Remote Similarity	NPD5223	Approved
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4623	Approved
0.6139	Remote Similarity	NPD4519	Discontinued
0.6139	Remote Similarity	NPD4249	Approved
0.6139	Remote Similarity	NPD3618	Phase 1
0.6132	Remote Similarity	NPD5210	Approved
0.6132	Remote Similarity	NPD4629	Approved
0.6122	Remote Similarity	NPD4790	Discontinued
0.6117	Remote Similarity	NPD5370	Suspended
0.6117	Remote Similarity	NPD5328	Approved
0.6116	Remote Similarity	NPD6370	Approved
0.6106	Remote Similarity	NPD7320	Approved
0.6102	Remote Similarity	NPD6009	Approved
0.6102	Remote Similarity	NPD7500	Approved
0.61	Remote Similarity	NPD3666	Approved
0.61	Remote Similarity	NPD3133	Approved
0.61	Remote Similarity	NPD4786	Approved
0.61	Remote Similarity	NPD3665	Phase 1
0.6091	Remote Similarity	NPD5226	Approved
0.6091	Remote Similarity	NPD5225	Approved
0.6091	Remote Similarity	NPD4633	Approved
0.6091	Remote Similarity	NPD5224	Approved
0.6075	Remote Similarity	NPD5221	Approved
0.6075	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5222	Approved
0.6067	Remote Similarity	NPD7341	Phase 2
0.6067	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7642	Approved
0.6061	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3667	Approved
0.6055	Remote Similarity	NPD6648	Approved
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5282	Discontinued
0.6036	Remote Similarity	NPD5175	Approved
0.6036	Remote Similarity	NPD6647	Phase 2
0.6036	Remote Similarity	NPD5174	Approved
0.6033	Remote Similarity	NPD6015	Approved
0.6033	Remote Similarity	NPD6016	Approved
0.602	Remote Similarity	NPD5368	Approved
0.602	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD4755	Approved
0.6019	Remote Similarity	NPD5173	Approved
0.6018	Remote Similarity	NPD5701	Approved
0.6018	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5281	Approved
0.6	Remote Similarity	NPD8039	Approved
0.5984	Remote Similarity	NPD5988	Approved
0.5981	Remote Similarity	NPD5695	Phase 3
0.598	Remote Similarity	NPD7334	Approved
0.598	Remote Similarity	NPD5330	Approved
0.598	Remote Similarity	NPD6684	Approved
0.598	Remote Similarity	NPD6409	Approved
0.598	Remote Similarity	NPD7521	Approved
0.598	Remote Similarity	NPD7146	Approved
0.5977	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD6616	Approved
0.5968	Remote Similarity	NPD7507	Approved
0.5963	Remote Similarity	NPD5696	Approved
0.5962	Remote Similarity	NPD4753	Phase 2
0.5952	Remote Similarity	NPD342	Phase 1
0.595	Remote Similarity	NPD6059	Approved
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7632	Discontinued
0.5943	Remote Similarity	NPD4202	Approved
0.5935	Remote Similarity	NPD7829	Approved
0.5935	Remote Similarity	NPD7830	Approved
0.5934	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4697	Phase 3
0.5922	Remote Similarity	NPD3573	Approved
0.592	Remote Similarity	NPD7078	Approved
0.5917	Remote Similarity	NPD7641	Discontinued
0.5917	Remote Similarity	NPD6335	Approved
0.5909	Remote Similarity	NPD4700	Approved
0.5882	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7736	Approved
0.5868	Remote Similarity	NPD7101	Approved
0.5868	Remote Similarity	NPD7100	Approved
0.5865	Remote Similarity	NPD6672	Approved
0.5865	Remote Similarity	NPD5737	Approved
0.5865	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6903	Approved
0.5859	Remote Similarity	NPD7260	Phase 2
0.5854	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7623	Phase 3
0.5849	Remote Similarity	NPD5693	Phase 1
0.5847	Remote Similarity	NPD4632	Approved
0.5843	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8264	Approved
0.5833	Remote Similarity	NPD6317	Approved
0.5827	Remote Similarity	NPD7319	Approved
0.5826	Remote Similarity	NPD4730	Approved
0.5826	Remote Similarity	NPD4729	Approved
0.5825	Remote Similarity	NPD6422	Discontinued
0.5825	Remote Similarity	NPD5690	Phase 2
0.5825	Remote Similarity	NPD5279	Phase 3
0.5825	Remote Similarity	NPD3574	Clinical (unspecified phase)

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