NPASS Compound

Structure

NPC471055 OpenBabel07101718272D 34 36 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 4.3301 3.5000 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 3.4641 3.0000 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 2 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 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 -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 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 17 1 0 0 0 0 9 26 1 0 0 0 0 10 17 2 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 19 2 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 15 21 2 0 0 0 0 15 27 1 0 0 0 0 16 21 1 0 0 0 0 16 28 1 0 0 0 0 19 24 1 0 0 0 0 20 29 2 0 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 22 10 1 6 0 0 0 22 32 1 0 0 0 0 23 13 1 1 0 0 0 23 25 1 0 0 0 0 24 31 1 1 0 0 0 25 12 1 1 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 14 1 1 0 0 0 27 32 1 0 0 0 0 27 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.26
Volume:	495.592
LogP:	2.968
LogD:	2.773
LogS:	-3.479
# Rotatable Bonds:	8
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	5.826
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.656
MDCK Permeability:	7.61056289775297e-05
Pgp-inhibitor:	0.484
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.76
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	94.59169006347656%
Volume Distribution (VD):	1.307
Pgp-substrate:	7.093352317810059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.336
CYP2C9-inhibitor:	0.532
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.683
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	2.38
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.966
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.439
Carcinogencity:	0.823
Eye Corrosion:	0.018
Eye Irritation:	0.113
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: NPC471055

Natural Product ID:	NPC471055
*Common Name:**	Phorbaketal F
IUPAC Name:	[(2S,4'aR,6S,6'R,8'aR)-2-[(1E,4E)-6-hydroperoxy-2,6-dimethylhepta-1,4-dienyl]-4'-(hydroxymethyl)-4,7'-dimethylspiro[2,3-dihydropyran-6,2'-4a,5,6,8a-tetrahydrochromene]-6'-yl] acetate
Synonyms:	Phorbaketal F
Standard InCHIKey:	YGBUJACBKXHYOB-OUUYZIRMSA-N
Standard InCHI:	InChI=1S/C27H38O7/c1-17(8-7-9-26(5,6)34-30)10-22-11-18(2)14-27(32-22)15-21(16-28)23-13-24(31-20(4)29)19(3)12-25(23)33-27/h7,9-10,12,14-15,22-25,28,30H,8,11,13,16H2,1-6H3/b9-7+,17-10+/t22-,23-,24-,25-,27+/m1/s1
SMILES:	OOC(/C=C/C/C(=C/[C@@H]1CC(=C[C@@]2(O1)C=C(CO)[C@@H]1[C@H](O2)C=C([C@@H](C1)OC(=O)C)C)C)/C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2338624
PubChem CID:	71579368
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
NPT376	Cell Line	A498	Homo sapiens	IC50	>	50000.0	nM	PMID[470195]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[470195]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	50000.0	nM	PMID[470195]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[470195]

☑ 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 NPC471055 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	194
0.1-0.2	1428
0.2-0.3	5028
0.3-0.4	14005
0.4-0.5	11989
0.5-0.6	7678
0.6-0.7	2190
0.7-0.8	178
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471056
0.8222	Intermediate Similarity	NPC471054
0.8148	Intermediate Similarity	NPC477086
0.8148	Intermediate Similarity	NPC477087
0.8111	Intermediate Similarity	NPC472011
0.8049	Intermediate Similarity	NPC477085
0.8	Intermediate Similarity	NPC313658
0.8	Intermediate Similarity	NPC241054
0.8	Intermediate Similarity	NPC316138
0.7978	Intermediate Similarity	NPC471494
0.7912	Intermediate Similarity	NPC106051
0.7889	Intermediate Similarity	NPC311163
0.7882	Intermediate Similarity	NPC84360
0.7872	Intermediate Similarity	NPC256368
0.7826	Intermediate Similarity	NPC477748
0.7812	Intermediate Similarity	NPC98112
0.7755	Intermediate Similarity	NPC280991
0.7742	Intermediate Similarity	NPC202886
0.7742	Intermediate Similarity	NPC3952
0.7701	Intermediate Similarity	NPC139712
0.766	Intermediate Similarity	NPC477749
0.766	Intermediate Similarity	NPC471059
0.766	Intermediate Similarity	NPC472010
0.7634	Intermediate Similarity	NPC133450
0.7629	Intermediate Similarity	NPC91197
0.7629	Intermediate Similarity	NPC125551
0.7629	Intermediate Similarity	NPC239547
0.7629	Intermediate Similarity	NPC155319
0.7629	Intermediate Similarity	NPC96597
0.7629	Intermediate Similarity	NPC309503
0.759	Intermediate Similarity	NPC4299
0.7579	Intermediate Similarity	NPC109406
0.7553	Intermediate Similarity	NPC177668
0.7527	Intermediate Similarity	NPC248312
0.75	Intermediate Similarity	NPC238397
0.75	Intermediate Similarity	NPC86971
0.75	Intermediate Similarity	NPC471363
0.75	Intermediate Similarity	NPC321728
0.75	Intermediate Similarity	NPC201191
0.75	Intermediate Similarity	NPC47220
0.75	Intermediate Similarity	NPC186332
0.7475	Intermediate Similarity	NPC219285
0.7475	Intermediate Similarity	NPC477968
0.7475	Intermediate Similarity	NPC477971
0.7475	Intermediate Similarity	NPC161527
0.7475	Intermediate Similarity	NPC20113
0.7475	Intermediate Similarity	NPC228251
0.7475	Intermediate Similarity	NPC477972
0.7474	Intermediate Similarity	NPC471324
0.7474	Intermediate Similarity	NPC477574
0.7474	Intermediate Similarity	NPC206679
0.7474	Intermediate Similarity	NPC114172
0.7473	Intermediate Similarity	NPC266718
0.747	Intermediate Similarity	NPC101622
0.7447	Intermediate Similarity	NPC246028
0.7426	Intermediate Similarity	NPC7644
0.7426	Intermediate Similarity	NPC127933
0.7426	Intermediate Similarity	NPC7613
0.7426	Intermediate Similarity	NPC475889
0.7426	Intermediate Similarity	NPC134270
0.7396	Intermediate Similarity	NPC472195
0.7396	Intermediate Similarity	NPC238090
0.7396	Intermediate Similarity	NPC159092
0.7396	Intermediate Similarity	NPC472196
0.7391	Intermediate Similarity	NPC477747
0.7391	Intermediate Similarity	NPC477746
0.7391	Intermediate Similarity	NPC242233
0.7374	Intermediate Similarity	NPC203627
0.7368	Intermediate Similarity	NPC470817
0.7368	Intermediate Similarity	NPC220216
0.7363	Intermediate Similarity	NPC106912
0.7363	Intermediate Similarity	NPC263087
0.7363	Intermediate Similarity	NPC44261
0.7363	Intermediate Similarity	NPC27314
0.7363	Intermediate Similarity	NPC2379
0.7363	Intermediate Similarity	NPC31019
0.7353	Intermediate Similarity	NPC201880
0.7353	Intermediate Similarity	NPC264867
0.7353	Intermediate Similarity	NPC473207
0.7353	Intermediate Similarity	NPC81567
0.7353	Intermediate Similarity	NPC470321
0.734	Intermediate Similarity	NPC471058
0.734	Intermediate Similarity	NPC471057
0.7333	Intermediate Similarity	NPC112868
0.7326	Intermediate Similarity	NPC474280
0.732	Intermediate Similarity	NPC178949
0.732	Intermediate Similarity	NPC472416
0.732	Intermediate Similarity	NPC298973
0.732	Intermediate Similarity	NPC159698
0.732	Intermediate Similarity	NPC96736
0.732	Intermediate Similarity	NPC472360
0.732	Intermediate Similarity	NPC469491
0.732	Intermediate Similarity	NPC104925
0.7308	Intermediate Similarity	NPC224660
0.7308	Intermediate Similarity	NPC470024
0.7303	Intermediate Similarity	NPC477088
0.73	Intermediate Similarity	NPC472012
0.73	Intermediate Similarity	NPC324841
0.7294	Intermediate Similarity	NPC477084
0.7292	Intermediate Similarity	NPC124374
0.7292	Intermediate Similarity	NPC234335
0.7292	Intermediate Similarity	NPC476075
0.7292	Intermediate Similarity	NPC476084
0.7283	Intermediate Similarity	NPC186155
0.7283	Intermediate Similarity	NPC475035
0.7283	Intermediate Similarity	NPC160517
0.7283	Intermediate Similarity	NPC78673
0.7282	Intermediate Similarity	NPC470763
0.7282	Intermediate Similarity	NPC470767
0.7282	Intermediate Similarity	NPC172867
0.7282	Intermediate Similarity	NPC252296
0.7273	Intermediate Similarity	NPC475332
0.7273	Intermediate Similarity	NPC474278
0.7273	Intermediate Similarity	NPC473244
0.7273	Intermediate Similarity	NPC40049
0.7263	Intermediate Similarity	NPC16265
0.7263	Intermediate Similarity	NPC470819
0.7263	Intermediate Similarity	NPC20946
0.7263	Intermediate Similarity	NPC261320
0.7255	Intermediate Similarity	NPC45897
0.7245	Intermediate Similarity	NPC471372
0.7245	Intermediate Similarity	NPC471362
0.7245	Intermediate Similarity	NPC472189
0.7234	Intermediate Similarity	NPC199382
0.7234	Intermediate Similarity	NPC131329
0.7229	Intermediate Similarity	NPC73603
0.7228	Intermediate Similarity	NPC20673
0.7216	Intermediate Similarity	NPC91654
0.7216	Intermediate Similarity	NPC474792
0.7216	Intermediate Similarity	NPC67398
0.7216	Intermediate Similarity	NPC99653
0.7212	Intermediate Similarity	NPC472390
0.7212	Intermediate Similarity	NPC475781
0.7212	Intermediate Similarity	NPC125423
0.7212	Intermediate Similarity	NPC109376
0.7212	Intermediate Similarity	NPC184512
0.7212	Intermediate Similarity	NPC88013
0.7209	Intermediate Similarity	NPC327383
0.7209	Intermediate Similarity	NPC185186
0.7204	Intermediate Similarity	NPC163606
0.7204	Intermediate Similarity	NPC67081
0.7204	Intermediate Similarity	NPC35933
0.7204	Intermediate Similarity	NPC471223
0.7191	Intermediate Similarity	NPC248775
0.7188	Intermediate Similarity	NPC469403
0.7184	Intermediate Similarity	NPC470768
0.7184	Intermediate Similarity	NPC473543
0.7174	Intermediate Similarity	NPC474809
0.7174	Intermediate Similarity	NPC471297
0.7174	Intermediate Similarity	NPC23748
0.7174	Intermediate Similarity	NPC69469
0.7174	Intermediate Similarity	NPC477667
0.7172	Intermediate Similarity	NPC94905
0.7172	Intermediate Similarity	NPC8954
0.7172	Intermediate Similarity	NPC57664
0.7172	Intermediate Similarity	NPC472995
0.7172	Intermediate Similarity	NPC171598
0.7172	Intermediate Similarity	NPC165632
0.7172	Intermediate Similarity	NPC211810
0.7172	Intermediate Similarity	NPC284194
0.7172	Intermediate Similarity	NPC221801
0.7172	Intermediate Similarity	NPC471765
0.7159	Intermediate Similarity	NPC469880
0.7159	Intermediate Similarity	NPC236228
0.7159	Intermediate Similarity	NPC229655
0.7159	Intermediate Similarity	NPC256720
0.7157	Intermediate Similarity	NPC470571
0.7157	Intermediate Similarity	NPC235369
0.7143	Intermediate Similarity	NPC105490
0.7143	Intermediate Similarity	NPC469697
0.7143	Intermediate Similarity	NPC135015
0.7143	Intermediate Similarity	NPC48548
0.7143	Intermediate Similarity	NPC311223
0.7143	Intermediate Similarity	NPC128795
0.7143	Intermediate Similarity	NPC315731
0.7143	Intermediate Similarity	NPC184208
0.7143	Intermediate Similarity	NPC473339
0.7143	Intermediate Similarity	NPC8538
0.7143	Intermediate Similarity	NPC217921
0.7143	Intermediate Similarity	NPC474922
0.7143	Intermediate Similarity	NPC471552
0.7143	Intermediate Similarity	NPC475944
0.7143	Intermediate Similarity	NPC88507
0.713	Intermediate Similarity	NPC470027
0.7129	Intermediate Similarity	NPC477716
0.7129	Intermediate Similarity	NPC477721
0.7129	Intermediate Similarity	NPC244878
0.7128	Intermediate Similarity	NPC471480
0.7128	Intermediate Similarity	NPC477668
0.7128	Intermediate Similarity	NPC61527
0.7115	Intermediate Similarity	NPC127609
0.7113	Intermediate Similarity	NPC472199
0.7113	Intermediate Similarity	NPC177641
0.7113	Intermediate Similarity	NPC302584
0.7113	Intermediate Similarity	NPC472197
0.7113	Intermediate Similarity	NPC476417
0.7111	Intermediate Similarity	NPC475210
0.7111	Intermediate Similarity	NPC226226
0.7111	Intermediate Similarity	NPC180725
0.7111	Intermediate Similarity	NPC470149

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 NPC471055 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1791
0.2-0.3	3852
0.3-0.4	2424
0.4-0.5	679
0.5-0.6	202
0.6-0.7	33
0.7-0.8	2
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
0.7551	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8513	Phase 3
0.6893	Remote Similarity	NPD5344	Discontinued
0.6842	Remote Similarity	NPD8517	Approved
0.6842	Remote Similarity	NPD8516	Approved
0.6842	Remote Similarity	NPD8515	Approved
0.6837	Remote Similarity	NPD46	Approved
0.6837	Remote Similarity	NPD6698	Approved
0.6837	Remote Similarity	NPD7838	Discovery
0.6796	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD7640	Approved
0.6727	Remote Similarity	NPD6053	Discontinued
0.6701	Remote Similarity	NPD4250	Approved
0.6701	Remote Similarity	NPD4251	Approved
0.67	Remote Similarity	NPD5778	Approved
0.67	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD7638	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6648	Approved
0.6627	Remote Similarity	NPD368	Approved
0.66	Remote Similarity	NPD7983	Approved
0.6598	Remote Similarity	NPD4249	Approved
0.6555	Remote Similarity	NPD8074	Phase 3
0.6514	Remote Similarity	NPD6686	Approved
0.6505	Remote Similarity	NPD7839	Suspended
0.6489	Remote Similarity	NPD4820	Approved
0.6489	Remote Similarity	NPD4821	Approved
0.6489	Remote Similarity	NPD4819	Approved
0.6489	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD7154	Phase 3
0.6452	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4271	Approved
0.6436	Remote Similarity	NPD7637	Suspended
0.6435	Remote Similarity	NPD7327	Approved
0.6435	Remote Similarity	NPD7328	Approved
0.641	Remote Similarity	NPD8033	Approved
0.6379	Remote Similarity	NPD7516	Approved
0.6327	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8377	Approved
0.6325	Remote Similarity	NPD8294	Approved
0.6289	Remote Similarity	NPD5362	Discontinued
0.6271	Remote Similarity	NPD8296	Approved
0.6271	Remote Similarity	NPD8380	Approved
0.6271	Remote Similarity	NPD8335	Approved
0.6271	Remote Similarity	NPD8379	Approved
0.6271	Remote Similarity	NPD8378	Approved
0.6238	Remote Similarity	NPD6051	Approved
0.6238	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6101	Approved
0.6224	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7115	Discovery
0.6207	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7632	Discontinued
0.6122	Remote Similarity	NPD5332	Approved
0.6122	Remote Similarity	NPD5331	Approved
0.6122	Remote Similarity	NPD6695	Phase 3
0.6117	Remote Similarity	NPD6411	Approved
0.6098	Remote Similarity	NPD342	Phase 1
0.6082	Remote Similarity	NPD4790	Discontinued
0.6075	Remote Similarity	NPD4225	Approved
0.6067	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7507	Approved
0.6058	Remote Similarity	NPD6399	Phase 3
0.6038	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4270	Approved
0.602	Remote Similarity	NPD4269	Approved
0.6019	Remote Similarity	NPD5785	Approved
0.6018	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6882	Approved
0.5982	Remote Similarity	NPD6412	Phase 2
0.5979	Remote Similarity	NPD7514	Phase 3
0.5979	Remote Similarity	NPD7332	Phase 2
0.5979	Remote Similarity	NPD4252	Approved
0.5965	Remote Similarity	NPD6371	Approved
0.596	Remote Similarity	NPD6110	Phase 1
0.5957	Remote Similarity	NPD8264	Approved
0.5957	Remote Similarity	NPD8039	Approved
0.5941	Remote Similarity	NPD5786	Approved
0.5938	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD6009	Approved
0.593	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7319	Approved
0.5918	Remote Similarity	NPD5369	Approved
0.5914	Remote Similarity	NPD4732	Discontinued
0.5909	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7750	Discontinued
0.5882	Remote Similarity	NPD7524	Approved
0.5882	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6435	Approved
0.5854	Remote Similarity	NPD7492	Approved
0.5849	Remote Similarity	NPD7748	Approved
0.5842	Remote Similarity	NPD5363	Approved
0.5842	Remote Similarity	NPD1694	Approved
0.5841	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7902	Approved
0.5826	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7525	Registered
0.5816	Remote Similarity	NPD6931	Approved
0.5816	Remote Similarity	NPD6930	Phase 2
0.5812	Remote Similarity	NPD8133	Approved
0.581	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7515	Phase 2
0.5806	Remote Similarity	NPD8451	Approved
0.5806	Remote Similarity	NPD6616	Approved
0.5789	Remote Similarity	NPD6881	Approved
0.5789	Remote Similarity	NPD6899	Approved
0.5789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6054	Approved
0.5784	Remote Similarity	NPD6422	Discontinued
0.5773	Remote Similarity	NPD7145	Approved
0.5773	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7829	Approved
0.5772	Remote Similarity	NPD7830	Approved
0.5769	Remote Similarity	NPD5370	Suspended
0.576	Remote Similarity	NPD8448	Approved
0.576	Remote Similarity	NPD7078	Approved
0.5758	Remote Similarity	NPD6902	Approved
0.5752	Remote Similarity	NPD5739	Approved
0.5752	Remote Similarity	NPD6402	Approved
0.5752	Remote Similarity	NPD7128	Approved
0.5752	Remote Similarity	NPD6675	Approved
0.5748	Remote Similarity	NPD8391	Approved
0.5748	Remote Similarity	NPD8392	Approved
0.5748	Remote Similarity	NPD8390	Approved
0.5738	Remote Similarity	NPD8444	Approved
0.5726	Remote Similarity	NPD8341	Approved
0.5726	Remote Similarity	NPD8299	Approved
0.5726	Remote Similarity	NPD8340	Approved
0.5726	Remote Similarity	NPD8342	Approved
0.5714	Remote Similarity	NPD6929	Approved
0.5714	Remote Similarity	NPD3168	Discontinued
0.5714	Remote Similarity	NPD7645	Phase 2
0.5714	Remote Similarity	NPD7736	Approved
0.5702	Remote Similarity	NPD5697	Approved
0.5691	Remote Similarity	NPD6370	Approved
0.569	Remote Similarity	NPD6421	Discontinued
0.569	Remote Similarity	NPD6883	Approved
0.569	Remote Similarity	NPD7290	Approved
0.569	Remote Similarity	NPD7102	Approved
0.5688	Remote Similarity	NPD6084	Phase 2
0.5688	Remote Similarity	NPD6083	Phase 2
0.5686	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD4632	Approved
0.567	Remote Similarity	NPD5776	Phase 2
0.567	Remote Similarity	NPD6925	Approved
0.567	Remote Similarity	NPD6932	Approved
0.5667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7500	Approved
0.566	Remote Similarity	NPD7087	Discontinued
0.5657	Remote Similarity	NPD5368	Approved
0.5656	Remote Similarity	NPD6059	Approved
0.5652	Remote Similarity	NPD7320	Approved
0.5652	Remote Similarity	NPD6011	Approved
0.5648	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD8328	Phase 3
0.5645	Remote Similarity	NPD7642	Approved
0.5641	Remote Similarity	NPD6869	Approved
0.5641	Remote Similarity	NPD6847	Approved
0.5641	Remote Similarity	NPD8130	Phase 1
0.5641	Remote Similarity	NPD6649	Approved
0.5641	Remote Similarity	NPD6617	Approved
0.5641	Remote Similarity	NPD6650	Approved
0.5635	Remote Similarity	NPD8293	Discontinued
0.5625	Remote Similarity	NPD7339	Approved
0.5625	Remote Similarity	NPD6942	Approved
0.5619	Remote Similarity	NPD1695	Approved
0.5614	Remote Similarity	NPD4211	Phase 1
0.5614	Remote Similarity	NPD6008	Approved
0.561	Remote Similarity	NPD6015	Approved
0.561	Remote Similarity	NPD6016	Approved
0.5603	Remote Similarity	NPD6014	Approved
0.5603	Remote Similarity	NPD6372	Approved
0.5603	Remote Similarity	NPD6012	Approved
0.5603	Remote Similarity	NPD6373	Approved
0.5603	Remote Similarity	NPD6013	Approved
0.56	Remote Similarity	NPD6898	Phase 1

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