NPASS Compound

Structure

NPC471057 OpenBabel07101718272D 32 34 0 0 1 0 0 0 0 0999 V2000 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 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 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 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 5.5000 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 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 0.8660 -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 -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 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 2 0 0 0 0 9 18 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 11 23 1 0 0 0 0 12 20 2 0 0 0 0 13 25 1 0 0 0 0 14 19 2 0 0 0 0 15 22 2 0 0 0 0 15 27 1 0 0 0 0 16 22 1 0 0 0 0 16 28 2 0 0 0 0 20 25 1 0 0 0 0 21 29 2 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 23 10 1 6 0 0 0 23 31 1 0 0 0 0 24 13 1 1 0 0 0 24 26 1 0 0 0 0 25 30 1 1 0 0 0 26 12 1 1 0 0 0 26 32 1 0 0 0 0 27 14 1 1 0 0 0 27 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.26
Volume:	475.375
LogP:	5.88
LogD:	3.931
LogS:	-4.624
# Rotatable Bonds:	7
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	5.541
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.569
MDCK Permeability:	4.781072857440449e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.593
Human Intestinal Absorption (HIA):	0.941
20% Bioavailability (F20%):	0.808
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	94.50785064697266%
Volume Distribution (VD):	2.248
Pgp-substrate:	6.3128814697265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.384
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.352

ADMET: Excretion

Clearance (CL):	4.759
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.516
Human Hepatotoxicity (H-HT):	0.989
Drug-inuced Liver Injury (DILI):	0.422
AMES Toxicity:	0.321
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.934
Carcinogencity:	0.141
Eye Corrosion:	0.139
Eye Irritation:	0.252
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC471057

Natural Product ID:	NPC471057
*Common Name:**	Phorbaketal J
IUPAC Name:	[(2S,4'aR,6S,6'R,8'aR)-2-[(1E)-2,6-dimethylhepta-1,5-dienyl]-4'-formyl-4,7'-dimethylspiro[2,3-dihydropyran-6,2'-4a,5,6,8a-tetrahydrochromene]-6'-yl] acetate
Synonyms:	Phorbaketal J
Standard InCHIKey:	JSCKLKJMTSHYBU-DAPVGVIPSA-N
Standard InCHI:	InChI=1S/C27H36O5/c1-17(2)8-7-9-18(3)10-23-11-19(4)14-27(31-23)15-22(16-28)24-13-25(30-21(6)29)20(5)12-26(24)32-27/h8,10,12,14-16,23-26H,7,9,11,13H2,1-6H3/b18-10+/t23-,24-,25-,26-,27+/m1/s1
SMILES:	O=CC1=C[C@@]2(O[C@H](/C=C(/CCC=C(C)C)C)CC(=C2)C)O[C@H]2[C@@H]1C[C@@H](OC(=O)C)C(=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2338626
PubChem CID:	71578199
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[525854]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	50000.0	nM	PMID[525854]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	50000.0	nM	PMID[525854]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[525854]

☑ 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 NPC471057 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	225
0.1-0.2	1638
0.2-0.3	6620
0.3-0.4	14088
0.4-0.5	11370
0.5-0.6	6766
0.6-0.7	1868
0.7-0.8	114
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471058
0.9195	High Similarity	NPC471059
0.8941	High Similarity	NPC471060
0.8315	Intermediate Similarity	NPC241054
0.8222	Intermediate Similarity	NPC106051
0.8222	Intermediate Similarity	NPC472011
0.8132	Intermediate Similarity	NPC471054
0.7957	Intermediate Similarity	NPC472010
0.7727	Intermediate Similarity	NPC281132
0.7647	Intermediate Similarity	NPC140287
0.7647	Intermediate Similarity	NPC476355
0.7609	Intermediate Similarity	NPC220478
0.7586	Intermediate Similarity	NPC97516
0.7586	Intermediate Similarity	NPC10572
0.75	Intermediate Similarity	NPC112457
0.75	Intermediate Similarity	NPC310981
0.7471	Intermediate Similarity	NPC123360
0.7449	Intermediate Similarity	NPC112654
0.7416	Intermediate Similarity	NPC270126
0.7412	Intermediate Similarity	NPC163003
0.74	Intermediate Similarity	NPC472012
0.7396	Intermediate Similarity	NPC65513
0.7391	Intermediate Similarity	NPC159635
0.7386	Intermediate Similarity	NPC141789
0.7386	Intermediate Similarity	NPC171204
0.7386	Intermediate Similarity	NPC187568
0.7386	Intermediate Similarity	NPC476028
0.7386	Intermediate Similarity	NPC41780
0.7374	Intermediate Similarity	NPC476768
0.7374	Intermediate Similarity	NPC257726
0.7374	Intermediate Similarity	NPC204054
0.7353	Intermediate Similarity	NPC132395
0.7353	Intermediate Similarity	NPC254202
0.7353	Intermediate Similarity	NPC471365
0.7353	Intermediate Similarity	NPC471364
0.7347	Intermediate Similarity	NPC473369
0.734	Intermediate Similarity	NPC471055
0.734	Intermediate Similarity	NPC471056
0.7303	Intermediate Similarity	NPC472960
0.7303	Intermediate Similarity	NPC93763
0.7303	Intermediate Similarity	NPC108816
0.73	Intermediate Similarity	NPC176845
0.7292	Intermediate Similarity	NPC101651
0.7292	Intermediate Similarity	NPC212679
0.7292	Intermediate Similarity	NPC220454
0.7292	Intermediate Similarity	NPC469372
0.7292	Intermediate Similarity	NPC469595
0.7292	Intermediate Similarity	NPC159748
0.7292	Intermediate Similarity	NPC80875
0.7283	Intermediate Similarity	NPC52609
0.7283	Intermediate Similarity	NPC1761
0.7283	Intermediate Similarity	NPC59097
0.7282	Intermediate Similarity	NPC470297
0.7253	Intermediate Similarity	NPC471325
0.7245	Intermediate Similarity	NPC269729
0.7245	Intermediate Similarity	NPC477129
0.7245	Intermediate Similarity	NPC477130
0.7228	Intermediate Similarity	NPC174314
0.7228	Intermediate Similarity	NPC476933
0.7222	Intermediate Similarity	NPC157441
0.7222	Intermediate Similarity	NPC178277
0.7216	Intermediate Similarity	NPC470373
0.7216	Intermediate Similarity	NPC470379
0.72	Intermediate Similarity	NPC84335
0.72	Intermediate Similarity	NPC38530
0.7191	Intermediate Similarity	NPC57744
0.7188	Intermediate Similarity	NPC284561
0.7174	Intermediate Similarity	NPC173609
0.7172	Intermediate Similarity	NPC274417
0.7158	Intermediate Similarity	NPC74139
0.7157	Intermediate Similarity	NPC473384
0.7143	Intermediate Similarity	NPC194871
0.7143	Intermediate Similarity	NPC471571
0.713	Intermediate Similarity	NPC12046
0.713	Intermediate Similarity	NPC194951
0.7128	Intermediate Similarity	NPC155873
0.7126	Intermediate Similarity	NPC269206
0.7126	Intermediate Similarity	NPC58956
0.7126	Intermediate Similarity	NPC295633
0.7115	Intermediate Similarity	NPC189616
0.7115	Intermediate Similarity	NPC119493
0.7115	Intermediate Similarity	NPC474898
0.7113	Intermediate Similarity	NPC328141
0.7113	Intermediate Similarity	NPC152467
0.7111	Intermediate Similarity	NPC128276
0.7097	Intermediate Similarity	NPC53867
0.7097	Intermediate Similarity	NPC40746
0.7097	Intermediate Similarity	NPC170377
0.7097	Intermediate Similarity	NPC169575
0.7087	Intermediate Similarity	NPC475320
0.7087	Intermediate Similarity	NPC235369
0.7087	Intermediate Similarity	NPC134077
0.7083	Intermediate Similarity	NPC473151
0.7083	Intermediate Similarity	NPC226863
0.7083	Intermediate Similarity	NPC477128
0.7083	Intermediate Similarity	NPC477302
0.7075	Intermediate Similarity	NPC89171
0.7075	Intermediate Similarity	NPC476802
0.7075	Intermediate Similarity	NPC189075
0.7075	Intermediate Similarity	NPC275539
0.7071	Intermediate Similarity	NPC476415
0.7071	Intermediate Similarity	NPC71589
0.7071	Intermediate Similarity	NPC470697
0.7065	Intermediate Similarity	NPC141810
0.7065	Intermediate Similarity	NPC25684
0.7065	Intermediate Similarity	NPC301477
0.7065	Intermediate Similarity	NPC281949
0.7059	Intermediate Similarity	NPC470256
0.7053	Intermediate Similarity	NPC284902
0.7053	Intermediate Similarity	NPC150755
0.7048	Intermediate Similarity	NPC1679
0.7048	Intermediate Similarity	NPC469607
0.7045	Intermediate Similarity	NPC474758
0.7045	Intermediate Similarity	NPC294434
0.7045	Intermediate Similarity	NPC117746
0.7045	Intermediate Similarity	NPC259599
0.7045	Intermediate Similarity	NPC15499
0.7041	Intermediate Similarity	NPC141831
0.7033	Intermediate Similarity	NPC471299
0.7024	Intermediate Similarity	NPC248125
0.7021	Intermediate Similarity	NPC38569
0.7021	Intermediate Similarity	NPC163615
0.7019	Intermediate Similarity	NPC476770
0.701	Intermediate Similarity	NPC218927
0.701	Intermediate Similarity	NPC83423
0.701	Intermediate Similarity	NPC206001
0.701	Intermediate Similarity	NPC166919
0.7	Intermediate Similarity	NPC470240
0.7	Intermediate Similarity	NPC471698
0.7	Intermediate Similarity	NPC116177
0.7	Intermediate Similarity	NPC320630
0.7	Intermediate Similarity	NPC33473
0.7	Intermediate Similarity	NPC477922
0.7	Intermediate Similarity	NPC476794
0.7	Intermediate Similarity	NPC7563
0.699	Remote Similarity	NPC472637
0.699	Remote Similarity	NPC63249
0.6989	Remote Similarity	NPC10080
0.6989	Remote Similarity	NPC123908
0.6989	Remote Similarity	NPC35556
0.6981	Remote Similarity	NPC110496
0.6979	Remote Similarity	NPC231889
0.6979	Remote Similarity	NPC475703
0.6977	Remote Similarity	NPC476591
0.6977	Remote Similarity	NPC88877
0.697	Remote Similarity	NPC475657
0.697	Remote Similarity	NPC474185
0.6966	Remote Similarity	NPC244166
0.6957	Remote Similarity	NPC223904
0.6957	Remote Similarity	NPC474510
0.6952	Remote Similarity	NPC118911
0.6952	Remote Similarity	NPC476001
0.6947	Remote Similarity	NPC474547
0.6947	Remote Similarity	NPC110405
0.6947	Remote Similarity	NPC470755
0.6947	Remote Similarity	NPC99395
0.6947	Remote Similarity	NPC21469
0.6947	Remote Similarity	NPC197903
0.6947	Remote Similarity	NPC189311
0.6947	Remote Similarity	NPC177932
0.6941	Remote Similarity	NPC203335
0.6939	Remote Similarity	NPC475748
0.6939	Remote Similarity	NPC265856
0.6939	Remote Similarity	NPC232426
0.6939	Remote Similarity	NPC281942
0.6939	Remote Similarity	NPC473619
0.6939	Remote Similarity	NPC51004
0.6931	Remote Similarity	NPC477921
0.6923	Remote Similarity	NPC267231
0.6923	Remote Similarity	NPC471220
0.6923	Remote Similarity	NPC136289
0.6915	Remote Similarity	NPC474703
0.6915	Remote Similarity	NPC475947
0.6915	Remote Similarity	NPC131669
0.6915	Remote Similarity	NPC22611
0.6915	Remote Similarity	NPC272814
0.6915	Remote Similarity	NPC473390
0.6915	Remote Similarity	NPC16488
0.6915	Remote Similarity	NPC193198
0.6907	Remote Similarity	NPC215831
0.6907	Remote Similarity	NPC136879
0.6907	Remote Similarity	NPC475902
0.6897	Remote Similarity	NPC469660
0.6893	Remote Similarity	NPC475202
0.6893	Remote Similarity	NPC469402
0.6893	Remote Similarity	NPC470906
0.6893	Remote Similarity	NPC476299
0.6893	Remote Similarity	NPC475392
0.6893	Remote Similarity	NPC470761
0.6893	Remote Similarity	NPC475385
0.6893	Remote Similarity	NPC474012
0.6893	Remote Similarity	NPC473219
0.6889	Remote Similarity	NPC40353
0.6889	Remote Similarity	NPC235906
0.6889	Remote Similarity	NPC472959
0.6889	Remote Similarity	NPC27205
0.6882	Remote Similarity	NPC275507
0.6882	Remote Similarity	NPC24417
0.6882	Remote Similarity	NPC42470
0.6882	Remote Similarity	NPC79277

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 NPC471057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	2007
0.2-0.3	4100
0.3-0.4	1987
0.4-0.5	588
0.5-0.6	234
0.6-0.7	20
0.7-0.8	0
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
0.6947	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6635	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6698	Approved
0.66	Remote Similarity	NPD46	Approved
0.6569	Remote Similarity	NPD7900	Approved
0.6569	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8513	Phase 3
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6686	Approved
0.6429	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD8039	Approved
0.6381	Remote Similarity	NPD7902	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD6422	Discontinued
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8516	Approved
0.6346	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5778	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD5779	Approved
0.63	Remote Similarity	NPD3573	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6289	Remote Similarity	NPD5209	Approved
0.6283	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7507	Approved
0.6275	Remote Similarity	NPD5785	Approved
0.6273	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD7748	Approved
0.6238	Remote Similarity	NPD6903	Approved
0.6238	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6672	Approved
0.6238	Remote Similarity	NPD5737	Approved
0.6214	Remote Similarity	NPD6411	Approved
0.6168	Remote Similarity	NPD7638	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD6649	Approved
0.6132	Remote Similarity	NPD7839	Suspended
0.6129	Remote Similarity	NPD7319	Approved
0.6126	Remote Similarity	NPD5739	Approved
0.6126	Remote Similarity	NPD7128	Approved
0.6126	Remote Similarity	NPD6402	Approved
0.6126	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD7640	Approved
0.6106	Remote Similarity	NPD6372	Approved
0.6106	Remote Similarity	NPD6373	Approved
0.61	Remote Similarity	NPD5363	Approved
0.6098	Remote Similarity	NPD8074	Phase 3
0.6071	Remote Similarity	NPD5697	Approved
0.6061	Remote Similarity	NPD7154	Phase 3
0.6058	Remote Similarity	NPD7515	Phase 2
0.6058	Remote Similarity	NPD5693	Phase 1
0.6058	Remote Similarity	NPD7983	Approved
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.604	Remote Similarity	NPD5786	Approved
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1695	Approved
0.6019	Remote Similarity	NPD4225	Approved
0.6018	Remote Similarity	NPD6011	Approved
0.6018	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6847	Approved
0.5984	Remote Similarity	NPD7642	Approved
0.5981	Remote Similarity	NPD4697	Phase 3
0.5966	Remote Similarity	NPD7641	Discontinued
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5962	Remote Similarity	NPD7838	Discovery
0.596	Remote Similarity	NPD6435	Approved
0.5948	Remote Similarity	NPD8297	Approved
0.5941	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4756	Discovery
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5701	Approved
0.5929	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4252	Approved
0.5918	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD6079	Approved
0.59	Remote Similarity	NPD5362	Discontinued
0.5889	Remote Similarity	NPD7331	Phase 2
0.5882	Remote Similarity	NPD6009	Approved
0.5865	Remote Similarity	NPD5328	Approved
0.5865	Remote Similarity	NPD6904	Approved
0.5865	Remote Similarity	NPD6051	Approved
0.5865	Remote Similarity	NPD6080	Approved
0.5865	Remote Similarity	NPD6673	Approved
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7829	Approved
0.5854	Remote Similarity	NPD7830	Approved
0.5854	Remote Similarity	NPD8328	Phase 3
0.5806	Remote Similarity	NPD7492	Approved
0.58	Remote Similarity	NPD4269	Approved
0.58	Remote Similarity	NPD4270	Approved
0.5789	Remote Similarity	NPD6412	Phase 2
0.578	Remote Similarity	NPD6083	Phase 2
0.578	Remote Similarity	NPD6084	Phase 2
0.5776	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6371	Approved
0.576	Remote Similarity	NPD8451	Approved
0.576	Remote Similarity	NPD6616	Approved
0.5758	Remote Similarity	NPD5368	Approved
0.5755	Remote Similarity	NPD6050	Approved
0.5743	Remote Similarity	NPD6110	Phase 1
0.5741	Remote Similarity	NPD5695	Phase 3
0.5738	Remote Similarity	NPD6054	Approved
0.5732	Remote Similarity	NPD6927	Phase 3
0.5728	Remote Similarity	NPD3618	Phase 1
0.5727	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD4271	Approved
0.5714	Remote Similarity	NPD8448	Approved
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4268	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD8390	Approved
0.5703	Remote Similarity	NPD8392	Approved
0.5703	Remote Similarity	NPD8391	Approved
0.5702	Remote Similarity	NPD6335	Approved
0.57	Remote Similarity	NPD5369	Approved
0.5691	Remote Similarity	NPD7503	Approved
0.569	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7732	Phase 3
0.5688	Remote Similarity	NPD5221	Approved
0.5688	Remote Similarity	NPD5222	Approved
0.5688	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD5285	Approved
0.5676	Remote Similarity	NPD6648	Approved
0.5676	Remote Similarity	NPD5286	Approved
0.5676	Remote Similarity	NPD4696	Approved
0.5669	Remote Similarity	NPD7736	Approved
0.5667	Remote Similarity	NPD6868	Approved
0.5667	Remote Similarity	NPD6274	Approved
0.5667	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5207	Approved
0.566	Remote Similarity	NPD5692	Phase 3
0.5656	Remote Similarity	NPD7100	Approved
0.5656	Remote Similarity	NPD7101	Approved
0.5652	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6001	Approved
0.5645	Remote Similarity	NPD6370	Approved
0.5636	Remote Similarity	NPD4755	Approved
0.5636	Remote Similarity	NPD5173	Approved
0.563	Remote Similarity	NPD4632	Approved
0.5625	Remote Similarity	NPD5344	Discontinued
0.5625	Remote Similarity	NPD5223	Approved
0.562	Remote Similarity	NPD6317	Approved
0.562	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5208	Approved
0.5615	Remote Similarity	NPD6845	Suspended
0.5614	Remote Similarity	NPD5141	Approved
0.561	Remote Similarity	NPD6059	Approved
0.5607	Remote Similarity	NPD5694	Approved
0.5607	Remote Similarity	NPD5281	Approved
0.5607	Remote Similarity	NPD8034	Phase 2
0.5607	Remote Similarity	NPD5284	Approved
0.5607	Remote Similarity	NPD8035	Phase 2
0.5604	Remote Similarity	NPD7341	Phase 2
0.56	Remote Similarity	NPD4820	Approved
0.56	Remote Similarity	NPD4819	Approved
0.56	Remote Similarity	NPD4821	Approved
0.56	Remote Similarity	NPD4695	Discontinued
0.56	Remote Similarity	NPD4822	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data