NPASS Compound

Structure

CID68156 OpenBabel06191715402D 27 28 0 0 1 0 0 0 0 0999 V2000 -5.6740 -0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3868 -1.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2404 0.5773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5183 1.6061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7494 -0.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0485 0.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5191 0.1161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7395 0.2093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1215 1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3357 1.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6958 -0.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2622 0.7852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0267 0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6530 0.6161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8555 1.6987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9305 0.7971 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6666 2.1759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3555 2.5648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3427 -0.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8609 1.5942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 21 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 22 2 0 0 0 0 13 16 2 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 17 26 1 0 0 0 0 18 11 1 1 0 0 0 18 27 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 4 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.17
Volume:	388.945
LogP:	3.779
LogD:	3.407
LogS:	-3.682
# Rotatable Bonds:	8
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.508
Fsp3:	0.429
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:	-4.758
MDCK Permeability:	2.2787316993344575e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.081
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.115
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	92.61053466796875%
Volume Distribution (VD):	1.09
Pgp-substrate:	9.187121391296387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.697
CYP1A2-substrate:	0.753
CYP2C19-inhibitor:	0.688
CYP2C19-substrate:	0.653
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.343
CYP2D6-inhibitor:	0.779
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	6.39
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.953
Drug-inuced Liver Injury (DILI):	0.192
AMES Toxicity:	0.65
Rat Oral Acute Toxicity:	0.658
Maximum Recommended Daily Dose:	0.686
Skin Sensitization:	0.92
Carcinogencity:	0.918
Eye Corrosion:	0.014
Eye Irritation:	0.048
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC68156

Natural Product ID:	NPC68156
*Common Name:**	Caucanolide F
IUPAC Name:	2-[2-[(2R)-2-[(2S,3Z)-2-methoxy-2-methyl-3-(4-methyl-5-oxofuran-2-ylidene)propyl]-5-oxo-2H-furan-4-yl]ethyl]-3-methylbut-2-enal
Synonyms:	Caucanolide F
Standard InCHIKey:	MSDPTAGLGJLKRT-GQQAKVJGSA-N
Standard InCHI:	InChI=1S/C21H26O6/c1-13(2)16(12-22)7-6-15-9-18(27-20(15)24)11-21(4,25-5)10-17-8-14(3)19(23)26-17/h8-10,12,18H,6-7,11H2,1-5H3/b17-10-/t18-,21+/m0/s1
SMILES:	O=CC(=C(C)C)CCC1=C[C@H](OC1=O)C[C@@](/C=C/1OC(=O)C(=C1)C)(OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516681
PubChem CID:	11552520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO4312	Antillogorgia bipinnata	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087606]
NPO4312	Antillogorgia bipinnata	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252918]
NPO24654	Curculigo crassifolia	Species	Hypoxidaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18958422]
NPO25544	Encyclia michuacana	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO24562	Saussurea petrovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4312	Antillogorgia bipinnata	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24562	Saussurea petrovii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3843	Rhododendron metternichii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25930	Cystoseira balearica	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26421	Urtica laetevirens	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24654	Curculigo crassifolia	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25544	Encyclia michuacana	Species	Orchidaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>=	50.0	ug.mL-1	PMID[505849]

☑ 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 NPC68156 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	201
0.1-0.2	1628
0.2-0.3	7609
0.3-0.4	18106
0.4-0.5	9977
0.5-0.6	3873
0.6-0.7	1183
0.7-0.8	114
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8442	Intermediate Similarity	NPC10572
0.8052	Intermediate Similarity	NPC474758
0.8026	Intermediate Similarity	NPC84038
0.7949	Intermediate Similarity	NPC469414
0.7949	Intermediate Similarity	NPC329826
0.7922	Intermediate Similarity	NPC474705
0.7857	Intermediate Similarity	NPC130030
0.7848	Intermediate Similarity	NPC123360
0.7838	Intermediate Similarity	NPC248125
0.7763	Intermediate Similarity	NPC470693
0.7722	Intermediate Similarity	NPC329852
0.7703	Intermediate Similarity	NPC220766
0.7683	Intermediate Similarity	NPC281132
0.7632	Intermediate Similarity	NPC218477
0.76	Intermediate Similarity	NPC191233
0.7595	Intermediate Similarity	NPC15499
0.7595	Intermediate Similarity	NPC117746
0.7595	Intermediate Similarity	NPC259599
0.7595	Intermediate Similarity	NPC476355
0.7595	Intermediate Similarity	NPC294434
0.7595	Intermediate Similarity	NPC470686
0.759	Intermediate Similarity	NPC42470
0.7586	Intermediate Similarity	NPC475739
0.7561	Intermediate Similarity	NPC178277
0.7534	Intermediate Similarity	NPC151648
0.7532	Intermediate Similarity	NPC232812
0.7531	Intermediate Similarity	NPC57744
0.75	Intermediate Similarity	NPC203335
0.7468	Intermediate Similarity	NPC287878
0.7442	Intermediate Similarity	NPC474424
0.7439	Intermediate Similarity	NPC128276
0.7436	Intermediate Similarity	NPC64234
0.7436	Intermediate Similarity	NPC37929
0.7416	Intermediate Similarity	NPC475995
0.7416	Intermediate Similarity	NPC474098
0.7412	Intermediate Similarity	NPC475947
0.7403	Intermediate Similarity	NPC276290
0.7391	Intermediate Similarity	NPC172998
0.7391	Intermediate Similarity	NPC301596
0.7391	Intermediate Similarity	NPC299396
0.7381	Intermediate Similarity	NPC471325
0.7375	Intermediate Similarity	NPC140287
0.7349	Intermediate Similarity	NPC270126
0.7349	Intermediate Similarity	NPC271632
0.7342	Intermediate Similarity	NPC112983
0.7342	Intermediate Similarity	NPC186531
0.7342	Intermediate Similarity	NPC163003
0.7342	Intermediate Similarity	NPC162571
0.7317	Intermediate Similarity	NPC476028
0.7317	Intermediate Similarity	NPC97516
0.7317	Intermediate Similarity	NPC171204
0.7317	Intermediate Similarity	NPC141789
0.7317	Intermediate Similarity	NPC471225
0.7317	Intermediate Similarity	NPC473825
0.7308	Intermediate Similarity	NPC476591
0.7308	Intermediate Similarity	NPC494
0.7308	Intermediate Similarity	NPC88877
0.7303	Intermediate Similarity	NPC64913
0.7303	Intermediate Similarity	NPC242877
0.7294	Intermediate Similarity	NPC173609
0.7284	Intermediate Similarity	NPC478194
0.7284	Intermediate Similarity	NPC478192
0.7284	Intermediate Similarity	NPC478191
0.7284	Intermediate Similarity	NPC478193
0.7284	Intermediate Similarity	NPC478195
0.7284	Intermediate Similarity	NPC478196
0.7283	Intermediate Similarity	NPC234339
0.7283	Intermediate Similarity	NPC273197
0.7273	Intermediate Similarity	NPC21998
0.7273	Intermediate Similarity	NPC194871
0.7262	Intermediate Similarity	NPC474510
0.725	Intermediate Similarity	NPC146583
0.7241	Intermediate Similarity	NPC215364
0.7237	Intermediate Similarity	NPC470688
0.7237	Intermediate Similarity	NPC131174
0.7229	Intermediate Similarity	NPC108816
0.7229	Intermediate Similarity	NPC93763
0.7215	Intermediate Similarity	NPC67183
0.7215	Intermediate Similarity	NPC315285
0.7209	Intermediate Similarity	NPC170377
0.7209	Intermediate Similarity	NPC475714
0.7209	Intermediate Similarity	NPC59097
0.72	Intermediate Similarity	NPC155849
0.72	Intermediate Similarity	NPC44343
0.72	Intermediate Similarity	NPC68110
0.72	Intermediate Similarity	NPC179087
0.72	Intermediate Similarity	NPC217940
0.72	Intermediate Similarity	NPC210303
0.7191	Intermediate Similarity	NPC469628
0.7191	Intermediate Similarity	NPC469653
0.7191	Intermediate Similarity	NPC260343
0.7191	Intermediate Similarity	NPC471047
0.7191	Intermediate Similarity	NPC475906
0.7191	Intermediate Similarity	NPC469631
0.7179	Intermediate Similarity	NPC470256
0.7179	Intermediate Similarity	NPC287705
0.7176	Intermediate Similarity	NPC325031
0.7176	Intermediate Similarity	NPC141810
0.7143	Intermediate Similarity	NPC175842
0.7143	Intermediate Similarity	NPC32494
0.7143	Intermediate Similarity	NPC32944
0.7143	Intermediate Similarity	NPC193396
0.7143	Intermediate Similarity	NPC471299
0.7126	Intermediate Similarity	NPC474865
0.7126	Intermediate Similarity	NPC475706
0.7125	Intermediate Similarity	NPC316185
0.7125	Intermediate Similarity	NPC133098
0.7111	Intermediate Similarity	NPC95364
0.7111	Intermediate Similarity	NPC142159
0.7093	Intermediate Similarity	NPC474028
0.7093	Intermediate Similarity	NPC474439
0.7089	Intermediate Similarity	NPC265574
0.7079	Intermediate Similarity	NPC475703
0.7079	Intermediate Similarity	NPC160138
0.7065	Intermediate Similarity	NPC59646
0.7051	Intermediate Similarity	NPC472266
0.7045	Intermediate Similarity	NPC281172
0.7045	Intermediate Similarity	NPC99395
0.7045	Intermediate Similarity	NPC197903
0.7037	Intermediate Similarity	NPC295633
0.7037	Intermediate Similarity	NPC269206
0.7037	Intermediate Similarity	NPC58956
0.7024	Intermediate Similarity	NPC267231
0.7024	Intermediate Similarity	NPC299235
0.7013	Intermediate Similarity	NPC182794
0.7013	Intermediate Similarity	NPC133904
0.7011	Intermediate Similarity	NPC169575
0.7011	Intermediate Similarity	NPC40746
0.701	Intermediate Similarity	NPC140591
0.701	Intermediate Similarity	NPC291500
0.701	Intermediate Similarity	NPC303653
0.701	Intermediate Similarity	NPC189609
0.701	Intermediate Similarity	NPC197835
0.7	Intermediate Similarity	NPC475902
0.7	Intermediate Similarity	NPC315597
0.7	Intermediate Similarity	NPC469660
0.6989	Remote Similarity	NPC470521
0.6988	Remote Similarity	NPC27205
0.6977	Remote Similarity	NPC281949
0.6977	Remote Similarity	NPC301477
0.6977	Remote Similarity	NPC275507
0.6977	Remote Similarity	NPC25684
0.6974	Remote Similarity	NPC132243
0.6966	Remote Similarity	NPC150755
0.6966	Remote Similarity	NPC284902
0.6966	Remote Similarity	NPC469861
0.6966	Remote Similarity	NPC130436
0.6966	Remote Similarity	NPC107787
0.6966	Remote Similarity	NPC469483
0.6966	Remote Similarity	NPC122502
0.6966	Remote Similarity	NPC291712
0.6966	Remote Similarity	NPC469860
0.6962	Remote Similarity	NPC474823
0.6962	Remote Similarity	NPC238223
0.6957	Remote Similarity	NPC32552
0.6957	Remote Similarity	NPC166110
0.6951	Remote Similarity	NPC315843
0.6951	Remote Similarity	NPC107654
0.6941	Remote Similarity	NPC264227
0.6941	Remote Similarity	NPC99651
0.6941	Remote Similarity	NPC63649
0.6941	Remote Similarity	NPC617
0.6941	Remote Similarity	NPC472965
0.6941	Remote Similarity	NPC473980
0.6941	Remote Similarity	NPC473981
0.6933	Remote Similarity	NPC79756
0.6932	Remote Similarity	NPC163093
0.6932	Remote Similarity	NPC115786
0.6923	Remote Similarity	NPC83423
0.6923	Remote Similarity	NPC315115
0.6914	Remote Similarity	NPC257618
0.6907	Remote Similarity	NPC469851
0.6905	Remote Similarity	NPC41780
0.6905	Remote Similarity	NPC180290
0.6905	Remote Similarity	NPC470240
0.6905	Remote Similarity	NPC320630
0.6905	Remote Similarity	NPC116177
0.6905	Remote Similarity	NPC7563
0.6905	Remote Similarity	NPC187568
0.6905	Remote Similarity	NPC316324
0.6905	Remote Similarity	NPC315394
0.6905	Remote Similarity	NPC476794
0.6897	Remote Similarity	NPC221231
0.6897	Remote Similarity	NPC11332
0.6897	Remote Similarity	NPC475690
0.6897	Remote Similarity	NPC73310
0.6897	Remote Similarity	NPC471326
0.6897	Remote Similarity	NPC473529
0.6897	Remote Similarity	NPC475159
0.6897	Remote Similarity	NPC180363
0.6897	Remote Similarity	NPC65930
0.6897	Remote Similarity	NPC35556
0.6897	Remote Similarity	NPC329829
0.6897	Remote Similarity	NPC94875
0.6897	Remote Similarity	NPC85772
0.6897	Remote Similarity	NPC473780
0.6897	Remote Similarity	NPC131002
0.6897	Remote Similarity	NPC473712
0.6897	Remote Similarity	NPC145914
0.6883	Remote Similarity	NPC53136

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 NPC68156 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	2058
0.2-0.3	4262
0.3-0.4	2020
0.4-0.5	509
0.5-0.6	108
0.6-0.7	9
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
0.7093	Intermediate Similarity	NPD5209	Approved
0.7013	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4756	Discovery
0.6471	Remote Similarity	NPD8039	Approved
0.6444	Remote Similarity	NPD7154	Phase 3
0.6389	Remote Similarity	NPD6927	Phase 3
0.6304	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1695	Approved
0.6146	Remote Similarity	NPD7838	Discovery
0.6146	Remote Similarity	NPD6698	Approved
0.6146	Remote Similarity	NPD46	Approved
0.6129	Remote Similarity	NPD1694	Approved
0.6076	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4249	Approved
0.6061	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD4251	Approved
0.5979	Remote Similarity	NPD5785	Approved
0.5957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2067	Discontinued
0.5914	Remote Similarity	NPD5362	Discontinued
0.5882	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6053	Discontinued
0.5789	Remote Similarity	NPD5363	Approved
0.5761	Remote Similarity	NPD4820	Approved
0.5761	Remote Similarity	NPD4821	Approved
0.5761	Remote Similarity	NPD4822	Approved
0.5761	Remote Similarity	NPD4819	Approved
0.5758	Remote Similarity	NPD7983	Approved
0.5753	Remote Similarity	NPD5343	Approved
0.5741	Remote Similarity	NPD6686	Approved
0.5728	Remote Similarity	NPD4225	Approved
0.5714	Remote Similarity	NPD4268	Approved
0.5714	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4271	Approved
0.57	Remote Similarity	NPD5779	Approved
0.57	Remote Similarity	NPD5778	Approved
0.5694	Remote Similarity	NPD3174	Discontinued
0.5673	Remote Similarity	NPD6648	Approved
0.5644	Remote Similarity	NPD5282	Discontinued
0.5638	Remote Similarity	NPD6435	Approved
0.5636	Remote Similarity	NPD6371	Approved
0.5612	Remote Similarity	NPD6903	Approved
0.56	Remote Similarity	NPD5693	Phase 1
0.56	Remote Similarity	NPD7637	Suspended

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